DE69119571T2 - Diazosensibilisatoren von fluorenthaltenden Estern - Google Patents
Diazosensibilisatoren von fluorenthaltenden EsternInfo
- Publication number
- DE69119571T2 DE69119571T2 DE69119571T DE69119571T DE69119571T2 DE 69119571 T2 DE69119571 T2 DE 69119571T2 DE 69119571 T DE69119571 T DE 69119571T DE 69119571 T DE69119571 T DE 69119571T DE 69119571 T2 DE69119571 T2 DE 69119571T2
- Authority
- DE
- Germany
- Prior art keywords
- photosensitizer
- fluorinated
- composition
- hydrogen
- composition according
- 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 - Fee Related
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 15
- 229910052731 fluorine Inorganic materials 0.000 title claims description 3
- 239000011737 fluorine Substances 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 title description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 81
- 229920002120 photoresistant polymer Polymers 0.000 claims description 36
- 239000004952 Polyamide Substances 0.000 claims description 22
- 229920002647 polyamide Polymers 0.000 claims description 22
- 239000003504 photosensitizing agent Substances 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 229920003986 novolac Polymers 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 6
- -1 hexafluoroisopropylidene group Chemical group 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 12
- 230000005855 radiation Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 206010034972 Photosensitivity reaction Diseases 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- 230000036211 photosensitivity Effects 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PRBPSTYDUVSNOK-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenoxy]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1OC1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 PRBPSTYDUVSNOK-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 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
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 206010034960 Photophobia Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 2
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- ZAASRHQPRFFWCS-UHFFFAOYSA-P diazanium;oxygen(2-);uranium Chemical compound [NH4+].[NH4+].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[U].[U] ZAASRHQPRFFWCS-UHFFFAOYSA-P 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 208000013469 light sensitivity Diseases 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YCRYSVKEWAWTGI-UHFFFAOYSA-N p,p'-Methoxychlor olefin Chemical compound C1=CC(OC)=CC=C1C(=C(Cl)Cl)C1=CC=C(OC)C=C1 YCRYSVKEWAWTGI-UHFFFAOYSA-N 0.000 description 2
- 238000002161 passivation Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- MDIAVSZFIQWYST-UHFFFAOYSA-N 2-amino-6-fluorophenol Chemical compound NC1=CC=CC(F)=C1O MDIAVSZFIQWYST-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007687 exposure technique Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000005468 ion implantation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000002534 radiation-sensitizing agent Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000010792 warming 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
- G03F7/16—Coating processes; Apparatus therefor
-
- 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
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/107—Polyamide or polyurethane
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (13)
1. Photosensibilisator-Zusammensetzung, die einen
fluorierten Diazoester, welcher die
Hexafluorisopropylidengruppe enthält, umfaßt, wobei der Photosensibilisator
das Reaktionsprodukt eines Hexafluorbisphenols mit der
folgenden Formel:
wobei R ausgewählt wird aus Wasserstoff, einer Methyl-,
Ethyl- und Phenylgruppe;
oder eines Bishexafluorethers mit der folgenden Formel:
wobei R ausgewählt wird aus Wasserstoff, einer Methyl-,
Ethyl- und Phenylgruppe;
mit einem Diazosulfonylchlorid ist.
2. Photosensibilisator-Zusammensetzung gemäß Anspruch 1,
wobei der Photosensibilisator ein Reaktionsprodukt
eines Diazosulfonylchlorids mit einem
Hexafluorbisphenol ist, wobei R Wasserstoff ist.
3. Photosensibilisator-Zusammensetzung gexnäß Anspruch 1,
wobei der Photosensibilisator ein Reaktionsprodukt
eines Diazosulfonylchlorids mit einem Bishexafluorether
ist, wobei R Wasserstoff ist.
4. Photosensibilisator-Zusammensetzung gemäß Anspruch 1,
wobei der Diazogehalt von 50 bis 100 % beträgt.
5. Positive photosensitive Zusammensetzung, welche eine
Photosensibilisator-Zusammensetzung gemäß einem der
Ansprüche 1 bis 4 und ein fluoriertes Hydroxypolyamid
umfaßt.
6. Photosensitive Zusammensetzung gemäß Anspruch 5, wobei
die Photosensibilisator-Zusammensetzung in einer
Konzentration von 0,5 bis 50 % vorhanden ist.
7. Positive photosensitive Zusammensetzung gemäß Anspruch
oder 6, wobei das fluorierte Hydroxypolyamid das
Reaktionsprodukt eines Säurechlorides mit
Hexafluor-2,2-bis(3-amino-4-hydroxyphenyl)propan umfaßt.
8. Positive photosensitive Zusammensetzung gemäß Anspruch
5, 6 oder 7, wobei das fluorierte Hydroxypolyamid ein
Polyamid mit der folgenden Struktur umfaßt:
wobei "X" ausgewählt wird aus S, SO&sub2;, einer direkten
Verbindung, O, R-C-R und C=O; "Y" ausgewählt wird aus
S, SO&sub2;, einer direkten Verbindung, einer Phenylgruppe,
oder
und "R" CF&sub3;, eine niedere
Alkyl- oder Phenylgruppe ist, vorausgesetzt daß wenigstens
eine von entweder X" oder "Y" eine "R"-haltige Gruppe
ist, in welcher "R" CF&sub3; ist.
9. Positive photosensitive zusammensetzung gemäß Anspruch
5, 6 oder 7, wobei das fluorierte Hydroxypolyamid ein
Polyamid mit der folgenden Struktur umfaßt:
wobei
(1) R eine vierwertige aromatische Komponente der
folgenden Formel ist:
(2) R' eine einwertige Komponente ist, welche
unabhängig ausgewählt wird aus:
X Wasserstoff oder ein Substituent ist, welcher
unabhängig ausgewählt wird aus: einer substituierten oder
unsubstituierten niederen Alkylgruppe mit 1 bis 8
Kohlenstoffen und einer substituierten oder
unsubstituierten Phenylgruppe; z unabhängig ausgewählt wird aus
Chlor, Brom, Fluor, Iod und einer niederen Alkylgruppe
mit 1 bis 6 Kohlenstoffen; n unabhängig 0 bis 1 ist;
und (3) R" ausgewählt wird aus einer substituierten
oder unsubstituierten Alkylen-, alicyclischen oder
Arylenkomponente.
10. Flüssige positive Photoresist-Zusammensetzung, welche
die Photosensibilisator-Zusammensetzung aus einem der
Ansprüche 1 bis 4, ein Binderharz und ein Lösungsmittel
umfaßt.
11. Photoresist-Zusammensetzung aus Anspruch 10, wobei das
Binderharz ein Novolakharz umfaßt.
12. Photoresist-Zusammensetzung aus Anspruch 10, wobei das
Binderharz ein Polyhydroxystyrolharz umfaßt.
13. Photoresist-zusammensetzung aus Anspruch 10, 11 oder
12, wobei das Lösungsmittel ausgewählt wird aus der
Gruppe bestehend aus: Methylethylketon,
Propylenglycolmethylether, Propylenglycolmethyletheracetat,
Cyclopentanon, Aceton, N-Methylpyrrolidon und
gamma-Butyrolacton.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/628,549 US5260162A (en) | 1990-12-17 | 1990-12-17 | Photosensitizer compositions containing diazo fluorinated esters of hexafluoro-bis-phenols or bis-hexafluoroethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69119571D1 DE69119571D1 (de) | 1996-06-20 |
| DE69119571T2 true DE69119571T2 (de) | 1996-11-28 |
Family
ID=24519372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69119571T Expired - Fee Related DE69119571T2 (de) | 1990-12-17 | 1991-12-16 | Diazosensibilisatoren von fluorenthaltenden Estern |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5260162A (de) |
| EP (1) | EP0493923B1 (de) |
| JP (1) | JP2960810B2 (de) |
| KR (1) | KR100214323B1 (de) |
| DE (1) | DE69119571T2 (de) |
| HK (1) | HK155596A (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3202253B2 (ja) * | 1991-03-29 | 2001-08-27 | 株式会社東芝 | 露光用マスクの製造方法及び露光用マスク |
| TW421731B (en) * | 1994-10-24 | 2001-02-11 | Clariant Finance Bvi Ltd | Positive photoresist composition, photo-sensitive element comprising it, methods of using it, and photosensitizer therein |
| JP3190967B2 (ja) * | 1996-12-16 | 2001-07-23 | 住友ベークライト株式会社 | アルカリ性水溶液及び感光性樹脂組成物のパターン形成方法 |
| US6207356B1 (en) | 1996-12-31 | 2001-03-27 | Sumitomo Bakelite Company Limited | Method for the pattern-processing of photosensitive resin composition |
| EP0852341B1 (de) * | 1997-01-03 | 2001-08-29 | Sumitomo Bakelite Company Limited | Verfahren zur Bebilderung einer photoempfindlichen Harzzusammensetzung |
| US6515101B1 (en) * | 1998-09-25 | 2003-02-04 | Iowa State University Research Foundation, Inc. | High performance fluorinated polymers and methods |
| TW527363B (en) * | 1999-09-08 | 2003-04-11 | Shinetsu Chemical Co | Polymers, chemical amplification resist compositions and patterning process |
| US6670090B1 (en) * | 2002-09-03 | 2003-12-30 | Industrial Technology Research Institute | Positive working photosensitive composition, article and process for forming a relief pattern |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130248C (de) * | 1959-01-21 | |||
| DE1543721A1 (de) * | 1966-07-27 | 1969-09-11 | Kalle Ag | Naphthochinondiazidsulfosaeureester und Verfahren zu seiner Herstellung und Verfahren zur Herstellung eines den Ester enthaltenden lagerfaehigen lichtempfindlichen Materials |
| US3669658A (en) * | 1969-06-11 | 1972-06-13 | Fuji Photo Film Co Ltd | Photosensitive printing plate |
| DE3100077A1 (de) * | 1981-01-03 | 1982-08-05 | Hoechst Ag, 6000 Frankfurt | Lichtempfindliches gemisch, das einen naphthochinondiazidsulfonsaeureester enthaelt, und verfahren zur herstellung des naphthochinondiazidsulfonsaeureesters |
| DE3421526A1 (de) * | 1984-06-08 | 1985-12-12 | Hoechst Ag, 6230 Frankfurt | Perfluoralkylgruppen aufweisende copolymere, sie enthaltende reproduktionsschichten und deren verwendung fuer den wasserlosen offsetdruck |
| DE3421471A1 (de) * | 1984-06-08 | 1985-12-12 | Hoechst Ag, 6230 Frankfurt | Perfluoralkylgruppen aufweisende 1,2-naphthochinondiazidverbindungen und reproduktionsmaterialien, die diese verbindungen enthalten |
| US4626492A (en) * | 1985-06-04 | 1986-12-02 | Olin Hunt Specialty Products, Inc. | Positive-working o-quinone diazide photoresist composition containing a dye and a trihydroxybenzophenone compound |
| US5037720A (en) * | 1987-07-21 | 1991-08-06 | Hoechst Celanese Corporation | Hydroxylated aromatic polyamide polymer containing bound naphthoquinone diazide photosensitizer, method of making and use |
| DE3724791A1 (de) * | 1987-07-27 | 1989-02-09 | Merck Patent Gmbh | Positiv-fotoresist-zusammensetzungen |
| US5037949A (en) * | 1987-11-24 | 1991-08-06 | Hoechst Celanese Corp. | Polymers prepared from 4,4'-bis[2-(amino (halo) phenoxyphenyl) hexafluoroisopropyl]diphenyl ether |
| EP0384892A1 (de) * | 1989-02-23 | 1990-08-29 | Ciba-Geigy Ag | Photoresist-Zusammensetzungen |
| US5114826A (en) * | 1989-12-28 | 1992-05-19 | Ibm Corporation | Photosensitive polyimide compositions |
-
1990
- 1990-12-17 US US07/628,549 patent/US5260162A/en not_active Expired - Lifetime
-
1991
- 1991-12-16 EP EP91311673A patent/EP0493923B1/de not_active Expired - Lifetime
- 1991-12-16 DE DE69119571T patent/DE69119571T2/de not_active Expired - Fee Related
- 1991-12-17 JP JP3353453A patent/JP2960810B2/ja not_active Expired - Fee Related
- 1991-12-17 KR KR1019910023226A patent/KR100214323B1/ko not_active IP Right Cessation
-
1996
- 1996-08-15 HK HK155596A patent/HK155596A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69119571D1 (de) | 1996-06-20 |
| KR100214323B1 (ko) | 1999-08-02 |
| JP2960810B2 (ja) | 1999-10-12 |
| JPH0627663A (ja) | 1994-02-04 |
| HK155596A (en) | 1996-08-23 |
| US5260162A (en) | 1993-11-09 |
| EP0493923A1 (de) | 1992-07-08 |
| KR920013028A (ko) | 1992-07-28 |
| EP0493923B1 (de) | 1996-05-15 |
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