CA2111632A1 - Source of photochemically generated acid for microelectronic photoresists - Google Patents
Source of photochemically generated acid for microelectronic photoresistsInfo
- Publication number
- CA2111632A1 CA2111632A1 CA002111632A CA2111632A CA2111632A1 CA 2111632 A1 CA2111632 A1 CA 2111632A1 CA 002111632 A CA002111632 A CA 002111632A CA 2111632 A CA2111632 A CA 2111632A CA 2111632 A1 CA2111632 A1 CA 2111632A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- ch2os
- moiety
- lower alkyl
- acid
- 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.)
- Abandoned
Links
- 239000002253 acid Substances 0.000 title claims abstract description 38
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 37
- 238000004377 microelectronic Methods 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- -1 -CH2OS(=O)2-Q Chemical group 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 230000005855 radiation Effects 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- UWQPDVZUOZVCBH-UHFFFAOYSA-N 2-diazonio-4-oxo-3h-naphthalen-1-olate Chemical group C1=CC=C2C(=O)C(=[N+]=[N-])CC(=O)C2=C1 UWQPDVZUOZVCBH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- BEVCCTWDTKAVFR-UHFFFAOYSA-N 2-diazonio-4-oxo-3h-naphthalen-1-olate;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.C1=CC=C2C(=O)C(=[N+]=[N-])CC(=O)C2=C1 BEVCCTWDTKAVFR-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000576 coating method Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 229920003176 water-insoluble polymer Polymers 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 239000004065 semiconductor Substances 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- YSZIOXAEADAJLX-UHFFFAOYSA-N phthalazine-1,4-dione Chemical group C1=CC=C2C(=O)N=NC(=O)C2=C1 YSZIOXAEADAJLX-UHFFFAOYSA-N 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 2
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- 229920001577 copolymer Polymers 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 235000012431 wafers Nutrition 0.000 description 10
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000005691 triesters Chemical class 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 229940116333 ethyl lactate Drugs 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- BWRBVBFLFQKBPT-UHFFFAOYSA-N (2-nitrophenyl)methanol Chemical compound OCC1=CC=CC=C1[N+]([O-])=O BWRBVBFLFQKBPT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000003608 radiolysis reaction Methods 0.000 description 3
- 230000000306 recurrent effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000002348 vinylic group Chemical group 0.000 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 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000010943 off-gassing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- KGWYICAEPBCRBL-UHFFFAOYSA-N 1h-indene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C=CC2=C1 KGWYICAEPBCRBL-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- PWSJRIAOUKLSMX-UHFFFAOYSA-N Cl[N+](Cl)=[N-] Chemical compound Cl[N+](Cl)=[N-] PWSJRIAOUKLSMX-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 101100504379 Mus musculus Gfral gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940118056 cresol / formaldehyde Drugs 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- MTVMXNTVZNCVTH-UHFFFAOYSA-N ethane-1,2-diol;2-(2-hydroxyethoxy)ethanol Chemical compound OCCO.OCCOCCO MTVMXNTVZNCVTH-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/71—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/026,923 US5308744A (en) | 1993-03-05 | 1993-03-05 | Source of photochemically generated acids from diazonaphthoquinone sulfonates of nitrobenzyl derivatives |
| US08/026,923 | 1993-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2111632A1 true CA2111632A1 (en) | 1994-09-06 |
Family
ID=21834576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002111632A Abandoned CA2111632A1 (en) | 1993-03-05 | 1993-12-16 | Source of photochemically generated acid for microelectronic photoresists |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5308744A (https=) |
| EP (1) | EP0614120B1 (https=) |
| JP (2) | JP2622231B2 (https=) |
| KR (1) | KR940021519A (https=) |
| CN (1) | CN1095060A (https=) |
| AT (1) | ATE151895T1 (https=) |
| CA (1) | CA2111632A1 (https=) |
| DE (1) | DE69402592T2 (https=) |
| TW (1) | TW268106B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5314782A (en) * | 1993-03-05 | 1994-05-24 | Morton International, Inc. | Deep UV sensitive resistant to latent image decay comprising a diazonaphthoquinone sulfonate of a nitrobenzyl derivative |
| DE59504286D1 (de) * | 1994-09-12 | 1998-12-24 | Siemens Ag | Photolithographische strukturerzeugung |
| CA2306478A1 (en) | 1997-10-16 | 1999-04-22 | Sun Chemical Corporation | Photoneutralization of ph sensitive aqueous polymeric dispersions and methods for using same |
| JP3285086B2 (ja) | 1999-05-20 | 2002-05-27 | 日本電気株式会社 | 化学増幅型レジスト組成物 |
| CN1318410C (zh) * | 2002-06-28 | 2007-05-30 | 北京师范大学 | 重氮萘醌系光－热活性化合物及其合成方法 |
| US7354692B2 (en) * | 2005-05-09 | 2008-04-08 | International Business Machines Corporation | Photoresists for visible light imaging |
| US9977339B2 (en) | 2014-01-27 | 2018-05-22 | Tokyo Electron Limited | System and method for shifting critical dimensions of patterned films |
| US9645495B2 (en) * | 2014-08-13 | 2017-05-09 | Tokyo Electron Limited | Critical dimension control in photo-sensitized chemically-amplified resist |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3046121A (en) * | 1949-07-23 | 1962-07-24 | Azoplate Corp | Process for the manufacture of printing plates and light-sensitive material suttablefor use therein |
| NL95407C (https=) * | 1954-08-20 | |||
| JPS5562444A (en) * | 1978-11-02 | 1980-05-10 | Konishiroku Photo Ind Co Ltd | Photosensitive composition |
| DE3038605A1 (de) * | 1980-10-13 | 1982-06-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von reliefkopien |
| DE3144499A1 (de) * | 1981-11-09 | 1983-05-19 | Hoechst Ag, 6230 Frankfurt | Lichtempfindliches gemisch und daraus hergestelltes lichtempfindliches kopiermaterial |
| US4491628A (en) * | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
| EP0155231B2 (de) * | 1984-03-07 | 1997-01-15 | Ciba-Geigy Ag | Verfahren zur Herstellung von Abbildungen |
| EP0239423B1 (en) * | 1986-03-28 | 1996-03-20 | Japan Synthetic Rubber Co., Ltd. | Positive type radiation-sensitive resin composition |
| US4837121A (en) * | 1987-11-23 | 1989-06-06 | Olin Hunt Specialty Products Inc. | Thermally stable light-sensitive compositions with o-quinone diazide and phenolic resin |
| JP2623309B2 (ja) * | 1988-02-22 | 1997-06-25 | ユーシービー ソシエテ アノニム | レジストパターンを得る方法 |
-
1993
- 1993-03-05 US US08/026,923 patent/US5308744A/en not_active Expired - Fee Related
- 1993-12-16 CA CA002111632A patent/CA2111632A1/en not_active Abandoned
- 1993-12-17 TW TW082110734A patent/TW268106B/zh active
-
1994
- 1994-01-06 DE DE69402592T patent/DE69402592T2/de not_active Expired - Fee Related
- 1994-01-06 AT AT94300058T patent/ATE151895T1/de active
- 1994-01-06 EP EP94300058A patent/EP0614120B1/en not_active Expired - Lifetime
- 1994-01-20 JP JP448294A patent/JP2622231B2/ja not_active Expired - Lifetime
- 1994-02-07 KR KR1019940002202A patent/KR940021519A/ko not_active Ceased
- 1994-03-04 CN CN94102680A patent/CN1095060A/zh active Pending
-
1996
- 1996-10-02 JP JP8261806A patent/JPH09120158A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0614120B1 (en) | 1997-04-16 |
| EP0614120A1 (en) | 1994-09-07 |
| JP2622231B2 (ja) | 1997-06-18 |
| JPH09120158A (ja) | 1997-05-06 |
| JPH06256292A (ja) | 1994-09-13 |
| CN1095060A (zh) | 1994-11-16 |
| US5308744A (en) | 1994-05-03 |
| KR940021519A (ko) | 1994-10-19 |
| DE69402592T2 (de) | 1997-07-24 |
| TW268106B (https=) | 1996-01-11 |
| ATE151895T1 (de) | 1997-05-15 |
| DE69402592D1 (de) | 1997-05-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4250182B2 (ja) | 染色されたフォトレジストとその方法及びそれからなる工業製品 | |
| JP2714378B2 (ja) | レジスト組成物およびその使用 | |
| US6844131B2 (en) | Positive-working photoimageable bottom antireflective coating | |
| US5550004A (en) | Chemically amplified radiation-sensitive composition | |
| CA2027628A1 (en) | Positive acting photoresist | |
| JP2000206694A (ja) | ネガ型レジスト組成物 | |
| US5234791A (en) | Radiation-curable composition and radiation-sensitive recording material prepared therefrom for use with high-energy radiation | |
| US5314782A (en) | Deep UV sensitive resistant to latent image decay comprising a diazonaphthoquinone sulfonate of a nitrobenzyl derivative | |
| EP0881540B1 (en) | Photoresist composition | |
| JP3192505B2 (ja) | 半導体素子製造用パターン形成方法 | |
| JPH11265061A (ja) | 色素含有感光性耐食膜および方法ならびにこれを含む工業製品 | |
| US5298364A (en) | Radiation-sensitive sulfonic acid esters and their use | |
| JP2878150B2 (ja) | レジスト用塗布液およびこれを用いたレジスト材料 | |
| US5308744A (en) | Source of photochemically generated acids from diazonaphthoquinone sulfonates of nitrobenzyl derivatives | |
| JP3846809B2 (ja) | アリールヒドラゾ染料を含有する底部反射防止膜 | |
| JPH11149161A (ja) | 新規なポリマーを含有する放射線感光性組成物 | |
| EP0410794A2 (en) | Maleimide containing, negative working deep UV photoresist | |
| US5563018A (en) | (1,2-naphthoquinone 2-diazide) sulfonic acid esters, radiation-sensitive mixture prepared therewith and radiation-sensitive recording material | |
| JP3781471B2 (ja) | 反射防止組成物及びこれを用いる感光膜の形成方法 | |
| JPH0496067A (ja) | ポジ型フォトレジスト組成物 | |
| KR20000048574A (ko) | 아릴히드라조 염료를 포함하는 감광성 조성물 | |
| JPH11349760A (ja) | 新規なポリマーを含有する放射線感光性組成物 | |
| JPS60147731A (ja) | 感光性樹脂組成物 | |
| JPH09197673A (ja) | 感放射線性樹脂組成物 | |
| JPS6165236A (ja) | 感光性組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |