DE3511615A1 - Positive polysilan-photoresistmaterialien und verfahren zu deren verwendung - Google Patents
Positive polysilan-photoresistmaterialien und verfahren zu deren verwendungInfo
- Publication number
- DE3511615A1 DE3511615A1 DE19853511615 DE3511615A DE3511615A1 DE 3511615 A1 DE3511615 A1 DE 3511615A1 DE 19853511615 DE19853511615 DE 19853511615 DE 3511615 A DE3511615 A DE 3511615A DE 3511615 A1 DE3511615 A1 DE 3511615A1
- Authority
- DE
- Germany
- Prior art keywords
- polysilane
- methyl
- alkyl
- propyl
- 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.)
- Withdrawn
Links
- 229920000548 poly(silane) polymer Polymers 0.000 title claims description 104
- 238000000034 method Methods 0.000 title claims description 60
- 239000000463 material Substances 0.000 title claims description 26
- 229920002120 photoresistant polymer Polymers 0.000 title description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 229920000642 polymer Polymers 0.000 claims description 49
- 230000005855 radiation Effects 0.000 claims description 39
- 239000000758 substrate Substances 0.000 claims description 33
- -1 n-dodecyl Chemical group 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 229920001519 homopolymer Polymers 0.000 claims description 17
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 16
- 230000036211 photosensitivity Effects 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 238000004377 microelectronic Methods 0.000 claims description 6
- 238000000059 patterning Methods 0.000 claims description 6
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003504 photosensitizing agent Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 4
- 230000002165 photosensitisation Effects 0.000 claims 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- 230000002427 irreversible effect Effects 0.000 claims 1
- 239000010410 layer Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 239000012634 fragment Substances 0.000 description 14
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 13
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 230000001965 increasing effect Effects 0.000 description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000006862 quantum yield reaction Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 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 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000003628 erosive effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical class Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 2
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical group C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SGIKAVNBVLFQSG-UHFFFAOYSA-N 1,1-diethyl-2,2-dimethylhydrazine Chemical class CCN(CC)N(C)C SGIKAVNBVLFQSG-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000012691 depolymerization reaction Methods 0.000 description 1
- YUYHCACQLHNZLS-UHFFFAOYSA-N dichloro-cyclohexyl-methylsilane Chemical compound C[Si](Cl)(Cl)C1CCCCC1 YUYHCACQLHNZLS-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- DDIMPUQNMJIVKL-UHFFFAOYSA-N dimethyl-bis(trimethylsilyl)silane Chemical compound C[Si](C)(C)[Si](C)(C)[Si](C)(C)C DDIMPUQNMJIVKL-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical group C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000005274 electronic transitions Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- BCSGKKPVRAKXLL-UHFFFAOYSA-N ethyl(methyl)silane Chemical group CC[SiH2]C BCSGKKPVRAKXLL-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 208000017983 photosensitivity disease Diseases 0.000 description 1
- 231100000434 photosensitization Toxicity 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000555 poly(dimethylsilanediyl) polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000005476 size effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009718 spray deposition Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical group C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
-
- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0754—Non-macromolecular compounds containing silicon-to-silicon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Polymers (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/597,005 US4588801A (en) | 1984-04-05 | 1984-04-05 | Polysilane positive photoresist materials and methods for their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3511615A1 true DE3511615A1 (de) | 1985-10-17 |
Family
ID=24389661
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3546801A Expired - Lifetime DE3546801C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-04-05 | 1985-03-29 | |
| DE19853511615 Withdrawn DE3511615A1 (de) | 1984-04-05 | 1985-03-29 | Positive polysilan-photoresistmaterialien und verfahren zu deren verwendung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3546801A Expired - Lifetime DE3546801C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-04-05 | 1985-03-29 |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3817306A1 (de) * | 1987-05-21 | 1988-12-01 | Toshiba Kawasaki Kk | Polysilanverbindung und diese enthaltende lichtempfindliche beschichtungsmasse |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61226748A (ja) * | 1985-03-30 | 1986-10-08 | Japan Synthetic Rubber Co Ltd | Ｘ線レジスト |
| JPH0642075B2 (ja) * | 1985-12-27 | 1994-06-01 | 株式会社東芝 | 感光性組成物 |
| US4822716A (en) * | 1985-12-27 | 1989-04-18 | Kabushiki Kaisha Toshiba | Polysilanes, Polysiloxanes and silicone resist materials containing these compounds |
| US5198520A (en) * | 1985-12-27 | 1993-03-30 | Kabushiki Kaisha Toshiba | Polysilanes, polysiloxanes and silicone resist materials containing these compounds |
| JPS62222247A (ja) * | 1986-03-24 | 1987-09-30 | Mitsubishi Electric Corp | ポジ型フオトレジスト材料 |
| JPH01503237A (ja) * | 1986-04-14 | 1989-11-02 | ザイグラー，ジョン エム | ポリシランの合成方法 |
| US4987202A (en) * | 1986-04-14 | 1991-01-22 | Zeigler John M | Methods for the synthesis of polysilanes |
| US4761464A (en) * | 1986-09-23 | 1988-08-02 | Zeigler John M | Interrupted polysilanes useful as photoresists |
| US4820788A (en) * | 1986-10-31 | 1989-04-11 | John M. Zeigler | Poly(silyl silane)homo and copolymers |
| US5039593A (en) * | 1986-10-31 | 1991-08-13 | Zeigler John K | Poly(silyl silane) homo and copolymers |
| US4772525A (en) * | 1987-05-01 | 1988-09-20 | Xerox Corporation | Photoresponsive imaging members with high molecular weight polysilylene hole transporting compositions |
| FR2616152B1 (fr) * | 1987-06-03 | 1991-08-30 | Inst Rech Appliquee Polym | Nouveaux polysilanes, polysilanes modifies correspondants, leur preparation et leur application dans des compositions reticulables |
| US4758488A (en) * | 1987-08-24 | 1988-07-19 | Xerox Corporation | Stabilized polysilylenes and imaging members therewith |
| JPH0196222A (ja) * | 1987-10-08 | 1989-04-14 | Uki Gosei Kogyo Co Ltd | １，２，２−トリメチル−１−（置換フェニル）ポリジシランおよびその製造法 |
| US5082872A (en) * | 1987-11-12 | 1992-01-21 | Dow Corning Corporation | Infusible preceramic polymers via ultraviolet treatment in the presence of a reactive gas |
| JP2543122B2 (ja) * | 1988-02-09 | 1996-10-16 | 松下電器産業株式会社 | 感光性重合体とその製造方法及びパタ―ン形成方法 |
| US5173452A (en) * | 1989-02-15 | 1992-12-22 | Dobuzinsky David M | Process for the vapor deposition of polysilanes photoresists |
| JP2737225B2 (ja) * | 1989-03-27 | 1998-04-08 | 松下電器産業株式会社 | 微細パターン形成材料およびパターン形成方法 |
| EP0445306B1 (en) * | 1989-09-27 | 1995-06-28 | Canon Kabushiki Kaisha | Novel polysilane composition |
| US5130397A (en) * | 1990-02-13 | 1992-07-14 | The United States Of America As Represented By The United States Department Of Energy | Hybrid sol-gel optical materials |
| US5061604A (en) * | 1990-05-04 | 1991-10-29 | Minnesota Mining And Manufacturing Company | Negative crystalline photoresists for UV photoimaging |
| US5204226A (en) * | 1991-03-04 | 1993-04-20 | International Business Machines Corporation | Photosensitizers for polysilanes |
| JPH0643655A (ja) * | 1991-03-04 | 1994-02-18 | Internatl Business Mach Corp <Ibm> | レジスト画像の生成プロセス及び電子デバイス |
| JP3251614B2 (ja) * | 1991-03-29 | 2002-01-28 | 株式会社東芝 | ポリシラン |
| KR950002875B1 (ko) * | 1991-07-08 | 1995-03-27 | 가부시키가이샤 도시바 | 감광성 조성물 |
| JPH05320354A (ja) * | 1992-05-18 | 1993-12-03 | Nippon Dow Corning Kk | 短波長吸収帯を有するポリシラン |
| IL105925A (en) * | 1992-06-22 | 1997-01-10 | Martin Marietta Corp | Ablative process for printed circuit board technology |
| WO1995006900A1 (fr) * | 1993-09-03 | 1995-03-09 | Hitachi, Ltd. | Procede et appareil de realisation de motifs |
| JP3274918B2 (ja) * | 1993-10-20 | 2002-04-15 | 日本ペイント株式会社 | ポリシラン系感光性樹脂組成物およびそれを用いるパターン形成方法 |
| US5776764A (en) * | 1993-10-20 | 1998-07-07 | Nippon Paint Co., Ltd. | Polysilane type photosensitive resin composition and method for forming pattern using the same |
| JP2970391B2 (ja) * | 1994-03-08 | 1999-11-02 | 信越化学工業株式会社 | 導電性重合体組成物 |
| US5830972A (en) * | 1995-04-10 | 1998-11-03 | Sumitomo Chemical Company, Limited | Polysilane, its production process and starting materials therefor |
| US5962581A (en) * | 1995-04-28 | 1999-10-05 | Kabushiki Kaisha Toshiba | Silicone polymer composition, method of forming a pattern and method of forming an insulating film |
| US6007963A (en) * | 1995-09-21 | 1999-12-28 | Sandia Corporation | Method for extreme ultraviolet lithography |
| US7306529B2 (en) * | 2005-10-07 | 2007-12-11 | Callaway Golf Company | Multi-layer golf ball |
| US7871933B2 (en) * | 2005-12-01 | 2011-01-18 | International Business Machines Corporation | Combined stepper and deposition tool |
| US7875408B2 (en) | 2007-01-25 | 2011-01-25 | International Business Machines Corporation | Bleachable materials for lithography |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE840764C (de) * | 1949-06-15 | 1952-06-09 | Dow Corning | Verfahren zur Herstellung von Organopolysilanen |
| US2606879A (en) * | 1949-06-15 | 1952-08-12 | Dow Corning | Organopolysilanes |
| DE1236506B (de) * | 1965-08-02 | 1967-03-16 | Bayer Ag | Verfahren zur Herstellung von Organodikaliumsilanen |
| US4324901A (en) * | 1981-04-29 | 1982-04-13 | Wisconsin Alumni Research Foundation | Soluble polysilastyrene and method for preparation |
| US4414059A (en) | 1982-12-09 | 1983-11-08 | International Business Machines Corporation | Far UV patterning of resist materials |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2554976A (en) * | 1948-09-01 | 1951-05-29 | Gen Electric | Polymers of polymethylsilylenes and method of preparing the same |
| US2612511A (en) * | 1948-09-22 | 1952-09-30 | Socony Vacuum Oil Co Inc | Preparation of hexaalkoxydisilanes |
| GB671774A (en) * | 1949-06-15 | 1952-05-07 | Dow Corning Ltd | Improvements in or relating to organopolysilanes |
| JPS51126300A (en) * | 1975-04-26 | 1976-11-04 | Res Inst Iron Steel Tohoku Univ | Method for manufacturing an organoo silicon polymer having silicon and carbon atoms as main skeleton component |
| US4276424A (en) * | 1979-12-03 | 1981-06-30 | Petrarch Systems | Methods for the production of organic polysilanes |
| JPS6046131B2 (ja) * | 1980-11-11 | 1985-10-14 | 宇部興産株式会社 | ポリカルボシランの製造法 |
| JPS59125729A (ja) * | 1982-12-13 | 1984-07-20 | Fujitsu Ltd | ドライ現像ポジ型レジスト組成物 |
| US4783516A (en) * | 1983-03-31 | 1988-11-08 | Union Carbide Corporation | Polysilane precursors containing olefinic groups for silicon carbide |
| US4464460A (en) * | 1983-06-28 | 1984-08-07 | International Business Machines Corporation | Process for making an imaged oxygen-reactive ion etch barrier |
| CA1225511A (en) * | 1983-09-30 | 1987-08-18 | Thomas C. Williams | Branched polysilahydrocarbon precursors for silicon carbide |
| JPS60119550A (ja) * | 1983-12-02 | 1985-06-27 | Nippon Telegr & Teleph Corp <Ntt> | パタン形成材料及びパタン形成方法 |
-
1984
- 1984-04-05 US US06/597,005 patent/US4588801A/en not_active Expired - Lifetime
-
1985
- 1985-03-12 GB GB08506369A patent/GB2156834B/en not_active Expired
- 1985-03-14 CA CA000476525A patent/CA1230444A/en not_active Expired
- 1985-03-15 AU AU40016/85A patent/AU570883B2/en not_active Ceased
- 1985-03-29 DE DE3546801A patent/DE3546801C2/de not_active Expired - Lifetime
- 1985-03-29 NL NL8500934A patent/NL8500934A/nl not_active Application Discontinuation
- 1985-03-29 DE DE19853511615 patent/DE3511615A1/de not_active Withdrawn
- 1985-04-02 SE SE8501646A patent/SE461220B/sv not_active IP Right Cessation
- 1985-04-02 FR FR8504976A patent/FR2562548B1/fr not_active Expired
- 1985-04-03 CH CH1492/85A patent/CH665646A5/de not_active IP Right Cessation
- 1985-04-04 KR KR1019850002289A patent/KR920003796B1/ko not_active Expired
- 1985-04-04 IT IT20237/85A patent/IT1200605B/it active
- 1985-04-04 JP JP60071886A patent/JPS60228542A/ja active Granted
-
1987
- 1987-09-30 JP JP62247757A patent/JPS63184746A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE840764C (de) * | 1949-06-15 | 1952-06-09 | Dow Corning | Verfahren zur Herstellung von Organopolysilanen |
| US2606879A (en) * | 1949-06-15 | 1952-08-12 | Dow Corning | Organopolysilanes |
| DE1236506B (de) * | 1965-08-02 | 1967-03-16 | Bayer Ag | Verfahren zur Herstellung von Organodikaliumsilanen |
| US4324901A (en) * | 1981-04-29 | 1982-04-13 | Wisconsin Alumni Research Foundation | Soluble polysilastyrene and method for preparation |
| US4414059A (en) | 1982-12-09 | 1983-11-08 | International Business Machines Corporation | Far UV patterning of resist materials |
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| Title |
|---|
| J. Polym. Sci., Polym. Chem. Ed., 1984, Bd. 22, S.159-170 * |
| J. Polym. Sci., Polym. Chem. Ed., 1984, Bd. 22, S.225-238 * |
| J. Polym. Sci., Polym. Letters Ed., 1983, Bd. 21, S.819-822 * |
| J.Organomet.Chem., 1975, Bd. 88, S. 65 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3817306A1 (de) * | 1987-05-21 | 1988-12-01 | Toshiba Kawasaki Kk | Polysilanverbindung und diese enthaltende lichtempfindliche beschichtungsmasse |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2562548A1 (fr) | 1985-10-11 |
| NL8500934A (nl) | 1985-11-01 |
| CA1230444A (en) | 1987-12-15 |
| AU4001685A (en) | 1985-10-10 |
| US4588801A (en) | 1986-05-13 |
| GB8506369D0 (en) | 1985-04-11 |
| KR920003796B1 (ko) | 1992-05-14 |
| FR2562548B1 (fr) | 1988-10-14 |
| AU570883B2 (en) | 1988-03-24 |
| JPH0379377B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-12-18 |
| IT1200605B (it) | 1989-01-27 |
| GB2156834A (en) | 1985-10-16 |
| GB2156834B (en) | 1988-05-25 |
| SE8501646D0 (sv) | 1985-04-02 |
| KR850007488A (ko) | 1985-12-04 |
| IT8520237A0 (it) | 1985-04-04 |
| SE8501646L (sv) | 1985-10-06 |
| JPS63184746A (ja) | 1988-07-30 |
| JPS60228542A (ja) | 1985-11-13 |
| DE3546801C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-11-12 |
| SE461220B (sv) | 1990-01-22 |
| CH665646A5 (de) | 1988-05-31 |
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