DE69807913T2 - Thermisch aushärtbare polyester-antireflexionsschichten für mehrlagenresistverfahren - Google Patents
Thermisch aushärtbare polyester-antireflexionsschichten für mehrlagenresistverfahrenInfo
- Publication number
- DE69807913T2 DE69807913T2 DE69807913T DE69807913T DE69807913T2 DE 69807913 T2 DE69807913 T2 DE 69807913T2 DE 69807913 T DE69807913 T DE 69807913T DE 69807913 T DE69807913 T DE 69807913T DE 69807913 T2 DE69807913 T2 DE 69807913T2
- Authority
- DE
- Germany
- Prior art keywords
- composition
- polyester resin
- reflective coating
- mixture
- resin
- 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
- 238000000034 method Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 9
- 229920000728 polyester Polymers 0.000 title description 20
- 239000000203 mixture Substances 0.000 claims description 97
- 239000006117 anti-reflective coating Substances 0.000 claims description 72
- 239000004645 polyester resin Substances 0.000 claims description 52
- 229920001225 polyester resin Polymers 0.000 claims description 48
- 238000000576 coating method Methods 0.000 claims description 40
- 229920002120 photoresistant polymer Polymers 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000011248 coating agent Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 28
- 239000011347 resin Substances 0.000 claims description 28
- 229910001868 water Inorganic materials 0.000 claims description 27
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 24
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 22
- 229920003180 amino resin Polymers 0.000 claims description 21
- -1 poly(hydroxystyrene) Polymers 0.000 claims description 21
- 229920001187 thermosetting polymer Polymers 0.000 claims description 21
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 17
- 239000003431 cross linking reagent Substances 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- 239000003377 acid catalyst Substances 0.000 claims description 14
- 239000010410 layer Substances 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229940116333 ethyl lactate Drugs 0.000 claims description 9
- 239000004065 semiconductor Substances 0.000 claims description 9
- 238000002835 absorbance Methods 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000011247 coating layer Substances 0.000 claims description 7
- 229920000877 Melamine resin Polymers 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- NGFUWANGZFFYHK-UHFFFAOYSA-N 1,3,3a,4,6,6a-hexahydroimidazo[4,5-d]imidazole-2,5-dione;formaldehyde Chemical group O=C.N1C(=O)NC2NC(=O)NC21 NGFUWANGZFFYHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229920003232 aliphatic polyester Polymers 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims description 3
- 238000004377 microelectronic Methods 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 2
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 2
- 238000001393 microlithography Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 230000031700 light absorption Effects 0.000 claims 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000004971 Cross linker Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000013557 residual solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000003021 water soluble solvent Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- 239000000975 dye Substances 0.000 description 43
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 39
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 17
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 15
- 230000003197 catalytic effect Effects 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 13
- 235000012141 vanillin Nutrition 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 235000012431 wafers Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000001020 plasma etching Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000011229 interlayer Substances 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 150000003934 aromatic aldehydes Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000010908 decantation Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 description 3
- 238000004626 scanning electron microscopy Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- 229920003274 CYMEL® 303 LF Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 239000006115 industrial coating Substances 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 238000013365 molecular weight analysis method Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910000676 Si alloy Inorganic materials 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- XJDFBLQCLSBCGQ-UHFFFAOYSA-N anthracene-1-carbaldehyde Chemical compound C1=CC=C2C=C3C(C=O)=CC=CC3=CC2=C1 XJDFBLQCLSBCGQ-UHFFFAOYSA-N 0.000 description 1
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 description 1
- 230000003667 anti-reflective effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- KKUHEYQOENDTJV-UHFFFAOYSA-N dimethylaminooxymethanol Chemical group CN(C)OCO KKUHEYQOENDTJV-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- MSYLJRIXVZCQHW-UHFFFAOYSA-N formaldehyde;6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound O=C.NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 MSYLJRIXVZCQHW-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 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
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- 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
- Y10S430/109—Polyester
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Materials For Photolithography (AREA)
- Paints Or Removers (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/954,425 US5935760A (en) | 1997-10-20 | 1997-10-20 | Thermosetting polyester anti-reflective coatings for multilayer photoresist processes |
| PCT/US1998/022143 WO1999021058A1 (en) | 1997-10-20 | 1998-10-20 | Thermosetting polyester anti-reflective coatings for multilayer photoresist processes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69807913D1 DE69807913D1 (de) | 2002-10-17 |
| DE69807913T2 true DE69807913T2 (de) | 2003-01-30 |
Family
ID=25495407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69807913T Expired - Fee Related DE69807913T2 (de) | 1997-10-20 | 1998-10-20 | Thermisch aushärtbare polyester-antireflexionsschichten für mehrlagenresistverfahren |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US5935760A (enExample) |
| EP (1) | EP1025462B1 (enExample) |
| JP (2) | JP4374483B2 (enExample) |
| KR (1) | KR20010031185A (enExample) |
| CN (1) | CN1276883A (enExample) |
| CA (1) | CA2305461A1 (enExample) |
| DE (1) | DE69807913T2 (enExample) |
| TW (1) | TW446738B (enExample) |
| WO (1) | WO1999021058A1 (enExample) |
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| JP3852889B2 (ja) | 1998-09-24 | 2006-12-06 | 富士写真フイルム株式会社 | フォトレジスト用反射防止膜材料組成物 |
| US6316165B1 (en) * | 1999-03-08 | 2001-11-13 | Shipley Company, L.L.C. | Planarizing antireflective coating compositions |
| US6890448B2 (en) * | 1999-06-11 | 2005-05-10 | Shipley Company, L.L.C. | Antireflective hard mask compositions |
| AU6790000A (en) * | 1999-08-26 | 2001-03-19 | Brewer Science, Inc. | Improved fill material for dual damascene processes |
| US20040034134A1 (en) | 1999-08-26 | 2004-02-19 | Lamb James E. | Crosslinkable fill compositions for uniformly protecting via and contact holes |
| KR20030009326A (ko) * | 1999-11-30 | 2003-01-29 | 브레우어 사이언스 인코포레이션 | 중합체 반사 방지 코팅에 사용하기 위한 비방향족 발색단 |
| JP3795333B2 (ja) * | 2000-03-30 | 2006-07-12 | 東京応化工業株式会社 | 反射防止膜形成用組成物 |
| US6323310B1 (en) * | 2000-04-19 | 2001-11-27 | Brewer Science, Inc. | Anti-reflective coating compositions comprising polymerized aminoplasts |
| TW556047B (en) | 2000-07-31 | 2003-10-01 | Shipley Co Llc | Coated substrate, method for forming photoresist relief image, and antireflective composition |
| KR101287032B1 (ko) | 2000-08-17 | 2013-07-17 | 롬 앤드 하스 일렉트로닉 머트어리얼즈, 엘.엘.씨 | 내에칭성 반사방지 코팅 조성물 |
| US20020162031A1 (en) * | 2001-03-08 | 2002-10-31 | Shmuel Levin | Method and apparatus for automatic control of access |
| TW576859B (en) * | 2001-05-11 | 2004-02-21 | Shipley Co Llc | Antireflective coating compositions |
| TW591341B (en) * | 2001-09-26 | 2004-06-11 | Shipley Co Llc | Coating compositions for use with an overcoated photoresist |
| US20090001524A1 (en) * | 2001-11-26 | 2009-01-01 | Siegele Stephen H | Generation and distribution of a fluorine gas |
| US20030121796A1 (en) * | 2001-11-26 | 2003-07-03 | Siegele Stephen H | Generation and distribution of molecular fluorine within a fabrication facility |
| US20040151656A1 (en) * | 2001-11-26 | 2004-08-05 | Siegele Stephen H. | Modular molecular halogen gas generation system |
| US20040037768A1 (en) * | 2001-11-26 | 2004-02-26 | Robert Jackson | Method and system for on-site generation and distribution of a process gas |
| US20030215736A1 (en) * | 2002-01-09 | 2003-11-20 | Oberlander Joseph E. | Negative-working photoimageable bottom antireflective coating |
| US7070914B2 (en) * | 2002-01-09 | 2006-07-04 | Az Electronic Materials Usa Corp. | Process for producing an image using a first minimum bottom antireflective coating composition |
| US6844131B2 (en) | 2002-01-09 | 2005-01-18 | Clariant Finance (Bvi) Limited | Positive-working photoimageable bottom antireflective coating |
| US8012670B2 (en) | 2002-04-11 | 2011-09-06 | Rohm And Haas Electronic Materials Llc | Photoresist systems |
| US7217491B2 (en) * | 2002-06-07 | 2007-05-15 | Battelle Memorial Institute | Antireflective coatings |
| US20040067437A1 (en) * | 2002-10-06 | 2004-04-08 | Shipley Company, L.L.C. | Coating compositions for use with an overcoated photoresist |
| JP4171920B2 (ja) * | 2002-10-09 | 2008-10-29 | 日産化学工業株式会社 | リソグラフィー用反射防止膜形成組成物 |
| US7038328B2 (en) | 2002-10-15 | 2006-05-02 | Brewer Science Inc. | Anti-reflective compositions comprising triazine compounds |
| KR20040044368A (ko) | 2002-11-20 | 2004-05-28 | 쉬플리 캄파니, 엘.엘.씨. | 다층 포토레지스트 시스템 |
| EP1422565A3 (en) * | 2002-11-20 | 2005-01-05 | Shipley Company LLC | Multilayer photoresist systems |
| US7264913B2 (en) * | 2002-11-21 | 2007-09-04 | Az Electronic Materials Usa Corp. | Antireflective compositions for photoresists |
| US7008476B2 (en) * | 2003-06-11 | 2006-03-07 | Az Electronic Materials Usa Corp. | Modified alginic acid of alginic acid derivatives and thermosetting anti-reflective compositions thereof |
| US20050026084A1 (en) * | 2003-07-31 | 2005-02-03 | Garza Cesar M. | Semiconductor device and method for elimination of resist linewidth slimming by fluorination |
| DE102004004865B4 (de) | 2004-01-30 | 2008-01-10 | Qimonda Ag | Antireflexschicht, die mit einem Photoresist beschichtet ist, enthaltend Polymere auf der Basis von Zimtsäure für die 157 nm Photolithographie |
| US20050214674A1 (en) * | 2004-03-25 | 2005-09-29 | Yu Sui | Positive-working photoimageable bottom antireflective coating |
| US7081511B2 (en) | 2004-04-05 | 2006-07-25 | Az Electronic Materials Usa Corp. | Process for making polyesters |
| US20060057491A1 (en) * | 2004-05-18 | 2006-03-16 | Rohm And Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
| JP4835854B2 (ja) * | 2004-07-02 | 2011-12-14 | 日産化学工業株式会社 | ハロゲン原子を有するナフタレン環を含むリソグラフィー用下層膜形成組成物 |
| US7691556B2 (en) * | 2004-09-15 | 2010-04-06 | Az Electronic Materials Usa Corp. | Antireflective compositions for photoresists |
| US20060057501A1 (en) * | 2004-09-15 | 2006-03-16 | Hengpeng Wu | Antireflective compositions for photoresists |
| EP1691238A3 (en) * | 2005-02-05 | 2009-01-21 | Rohm and Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
| TWI340296B (en) * | 2005-03-20 | 2011-04-11 | Rohm & Haas Elect Mat | Coating compositions for use with an overcoated photoresist |
| WO2006115074A1 (ja) * | 2005-04-19 | 2006-11-02 | Nissan Chemical Industries, Ltd. | エチレンジカルボニル構造を有するポリマーを含むリソグラフィー用反射防止膜形成組成物 |
| EP1762895B1 (en) * | 2005-08-29 | 2016-02-24 | Rohm and Haas Electronic Materials, L.L.C. | Antireflective Hard Mask Compositions |
| US7553905B2 (en) * | 2005-10-31 | 2009-06-30 | Az Electronic Materials Usa Corp. | Anti-reflective coatings |
| US7638262B2 (en) * | 2006-08-10 | 2009-12-29 | Az Electronic Materials Usa Corp. | Antireflective composition for photoresists |
| US8017296B2 (en) * | 2007-05-22 | 2011-09-13 | Az Electronic Materials Usa Corp. | Antireflective coating composition comprising fused aromatic rings |
| US20090042133A1 (en) * | 2007-08-10 | 2009-02-12 | Zhong Xiang | Antireflective Coating Composition |
| US8088548B2 (en) * | 2007-10-23 | 2012-01-03 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions |
| US7989144B2 (en) * | 2008-04-01 | 2011-08-02 | Az Electronic Materials Usa Corp | Antireflective coating composition |
| US7932018B2 (en) * | 2008-05-06 | 2011-04-26 | Az Electronic Materials Usa Corp. | Antireflective coating composition |
| US8221965B2 (en) * | 2008-07-08 | 2012-07-17 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
| KR100997502B1 (ko) * | 2008-08-26 | 2010-11-30 | 금호석유화학 주식회사 | 개환된 프탈릭 언하이드라이드를 포함하는 유기 반사 방지막 조성물과 이의 제조방법 |
| US8455176B2 (en) * | 2008-11-12 | 2013-06-04 | Az Electronic Materials Usa Corp. | Coating composition |
| US20100119979A1 (en) * | 2008-11-13 | 2010-05-13 | Rahman M Dalil | Antireflective Coating Composition Comprising Fused Aromatic Rings |
| US20100119980A1 (en) * | 2008-11-13 | 2010-05-13 | Rahman M Dalil | Antireflective Coating Composition Comprising Fused Aromatic Rings |
| US20100151392A1 (en) * | 2008-12-11 | 2010-06-17 | Rahman M Dalil | Antireflective coating compositions |
| US8614042B2 (en) * | 2009-04-23 | 2013-12-24 | Kao Corporation | Electrophotographic toner |
| US20100316949A1 (en) * | 2009-06-10 | 2010-12-16 | Rahman M Dalil | Spin On Organic Antireflective Coating Composition Comprising Polymer with Fused Aromatic Rings |
| US8632948B2 (en) * | 2009-09-30 | 2014-01-21 | Az Electronic Materials Usa Corp. | Positive-working photoimageable bottom antireflective coating |
| US8551686B2 (en) * | 2009-10-30 | 2013-10-08 | Az Electronic Materials Usa Corp. | Antireflective composition for photoresists |
| US8486609B2 (en) | 2009-12-23 | 2013-07-16 | Az Electronic Materials Usa Corp. | Antireflective coating composition and process thereof |
| KR101172763B1 (ko) | 2010-12-24 | 2012-08-09 | 금호석유화학 주식회사 | 공중합체, 이의 제조방법 및 이를 포함하는 레지스트 조성물 |
| US8623589B2 (en) | 2011-06-06 | 2014-01-07 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions and processes thereof |
| CN103387775A (zh) * | 2013-08-22 | 2013-11-13 | 吴江市冰心文教用品有限公司 | 一种隔热防水颜料 |
| EP3318337A1 (en) * | 2016-11-03 | 2018-05-09 | PPG Industries Ohio, Inc. | A coating composition and coating system |
| KR102417180B1 (ko) * | 2017-09-29 | 2022-07-05 | 삼성전자주식회사 | Duv용 포토레지스트 조성물, 패턴 형성 방법 및 반도체 소자의 제조 방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5866947A (ja) * | 1981-10-16 | 1983-04-21 | Mita Ind Co Ltd | 電子写真用感光体 |
| US5234990A (en) * | 1992-02-12 | 1993-08-10 | Brewer Science, Inc. | Polymers with intrinsic light-absorbing properties for anti-reflective coating applications in deep ultraviolet microlithography |
| US5607824A (en) * | 1994-07-27 | 1997-03-04 | International Business Machines Corporation | Antireflective coating for microlithography |
| US5693691A (en) * | 1995-08-21 | 1997-12-02 | Brewer Science, Inc. | Thermosetting anti-reflective coatings compositions |
| US5886102A (en) * | 1996-06-11 | 1999-03-23 | Shipley Company, L.L.C. | Antireflective coating compositions |
| JP3053072B2 (ja) * | 1996-09-10 | 2000-06-19 | 東京応化工業株式会社 | レジスト積層体及びそれを用いたパターン形成方法 |
| US5733714A (en) * | 1996-09-30 | 1998-03-31 | Clariant Finance (Bvi) Limited | Antireflective coating for photoresist compositions |
-
1997
- 1997-10-20 US US08/954,425 patent/US5935760A/en not_active Expired - Fee Related
-
1998
- 1998-10-20 DE DE69807913T patent/DE69807913T2/de not_active Expired - Fee Related
- 1998-10-20 TW TW087117300A patent/TW446738B/zh not_active IP Right Cessation
- 1998-10-20 WO PCT/US1998/022143 patent/WO1999021058A1/en not_active Ceased
- 1998-10-20 KR KR1020007004121A patent/KR20010031185A/ko not_active Ceased
- 1998-10-20 CN CN98810404A patent/CN1276883A/zh active Pending
- 1998-10-20 EP EP98952384A patent/EP1025462B1/en not_active Expired - Lifetime
- 1998-10-20 CA CA002305461A patent/CA2305461A1/en not_active Abandoned
- 1998-10-20 JP JP2000517316A patent/JP4374483B2/ja not_active Expired - Lifetime
-
1999
- 1999-06-08 US US09/328,316 patent/US6042990A/en not_active Expired - Fee Related
- 1999-06-08 US US09/328,305 patent/US6080530A/en not_active Expired - Lifetime
-
2008
- 2008-11-17 JP JP2008293674A patent/JP4374502B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2305461A1 (en) | 1999-04-29 |
| US6042990A (en) | 2000-03-28 |
| EP1025462B1 (en) | 2002-09-11 |
| EP1025462A4 (en) | 2001-01-17 |
| TW446738B (en) | 2001-07-21 |
| EP1025462A1 (en) | 2000-08-09 |
| DE69807913D1 (de) | 2002-10-17 |
| JP2009048210A (ja) | 2009-03-05 |
| US5935760A (en) | 1999-08-10 |
| US6080530A (en) | 2000-06-27 |
| JP2001521187A (ja) | 2001-11-06 |
| KR20010031185A (ko) | 2001-04-16 |
| JP4374502B2 (ja) | 2009-12-02 |
| CN1276883A (zh) | 2000-12-13 |
| WO1999021058A1 (en) | 1999-04-29 |
| JP4374483B2 (ja) | 2009-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |