KR100500750B1 - 화학적으로증폭된포지티브포토레지스트 - Google Patents
화학적으로증폭된포지티브포토레지스트 Download PDFInfo
- Publication number
- KR100500750B1 KR100500750B1 KR1019960061565A KR19960061565A KR100500750B1 KR 100500750 B1 KR100500750 B1 KR 100500750B1 KR 1019960061565 A KR1019960061565 A KR 1019960061565A KR 19960061565 A KR19960061565 A KR 19960061565A KR 100500750 B1 KR100500750 B1 KR 100500750B1
- Authority
- KR
- South Korea
- Prior art keywords
- luminous flux
- substituted
- unsubstituted
- formula
- photoresist composition
- 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 - Lifetime
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 64
- 230000004907 flux Effects 0.000 claims abstract description 73
- 239000000203 mixture Substances 0.000 claims abstract description 69
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 33
- 239000011230 binding agent Substances 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000003607 modifier Substances 0.000 claims description 25
- 150000003839 salts Chemical group 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 21
- -1 nitrobenzyl ester compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000011247 coating layer Substances 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000003893 lactate salts Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000008054 sulfonate salts Chemical group 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- 238000004377 microelectronic Methods 0.000 claims description 3
- 150000004714 phosphonium salts Chemical class 0.000 claims description 3
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 claims 4
- 229920000800 acrylic rubber Polymers 0.000 claims 2
- 150000004010 onium ions Chemical class 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 29
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 19
- 239000000975 dye Substances 0.000 description 16
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 16
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 11
- 235000012431 wafers Nutrition 0.000 description 11
- 230000005855 radiation Effects 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229940116333 ethyl lactate Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000005250 alkyl acrylate group Chemical group 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 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
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 150000003871 sulfonates Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- STVHWCAGWWIJHM-UHFFFAOYSA-M tert-butyl(phenyl)iodanium;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate Chemical compound CC(C)(C)[I+]C1=CC=CC=C1.C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C STVHWCAGWWIJHM-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- TZIQWQARHPGHIG-UHFFFAOYSA-N anthrarobin Chemical class C1=CC=CC2=CC3=C(O)C(O)=CC=C3C(O)=C21 TZIQWQARHPGHIG-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 150000002990 phenothiazines Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- REAVCZWUMGIGSW-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetrabutylazanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCC[N+](CCCC)(CCCC)CCCC REAVCZWUMGIGSW-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000000654 additive Substances 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
- 230000000903 blocking effect Effects 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000004148 curcumin Substances 0.000 description 2
- 229940109262 curcumin Drugs 0.000 description 2
- 235000012754 curcumin Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012955 diaryliodonium Substances 0.000 description 2
- 125000005520 diaryliodonium group Chemical group 0.000 description 2
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 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
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 2
- YNJQKNVVBBIPBA-UHFFFAOYSA-M tetrabutylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC YNJQKNVVBBIPBA-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-UHFFFAOYSA-N 0.000 description 1
- JWGBOHJGWOPYCL-UHFFFAOYSA-N 1-(10H-phenothiazin-2-yl)ethanone Chemical compound C1=CC=C2NC3=CC(C(=O)C)=CC=C3SC2=C1 JWGBOHJGWOPYCL-UHFFFAOYSA-N 0.000 description 1
- ZXKHOVDDJMJXQP-UHFFFAOYSA-N 1-ethenylcyclohexan-1-ol Chemical class C=CC1(O)CCCCC1 ZXKHOVDDJMJXQP-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- WQVIVQDHNKQWTM-UHFFFAOYSA-N 1-tert-butyl-4-iodobenzene Chemical compound CC(C)(C)C1=CC=C(I)C=C1 WQVIVQDHNKQWTM-UHFFFAOYSA-N 0.000 description 1
- ZWBANJRSWNLUEP-UHFFFAOYSA-N 2,2,2-trichloro-1,1-bis(2-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=CC=C1Cl ZWBANJRSWNLUEP-UHFFFAOYSA-N 0.000 description 1
- OLPZCIDHOZATMA-UHFFFAOYSA-N 2,2-dioxooxathiiran-3-one Chemical class O=C1OS1(=O)=O OLPZCIDHOZATMA-UHFFFAOYSA-N 0.000 description 1
- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- KKYIFEXCKMEZOJ-UHFFFAOYSA-N 4-methoxyphenol;1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl.COC1=CC=C(O)C=C1 KKYIFEXCKMEZOJ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- AHJKRLASYNVKDZ-UHFFFAOYSA-N DDD Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 AHJKRLASYNVKDZ-UHFFFAOYSA-N 0.000 description 1
- UCNVFOCBFJOQAL-UHFFFAOYSA-N DDE Chemical group C=1C=C(Cl)C=CC=1C(=C(Cl)Cl)C1=CC=C(Cl)C=C1 UCNVFOCBFJOQAL-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 150000003895 L-lactate salts Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- NGJBFULTZUWFJQ-UHFFFAOYSA-N [4,4-dichloro-2-(trichloromethyl)cyclohexa-1,5-dien-1-yl]-phenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=C(C(Cl)(Cl)Cl)CC(Cl)(Cl)C=C1 NGJBFULTZUWFJQ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- MJYSISMEPNOHEG-UHFFFAOYSA-N anthracen-9-ylmethyl 2-methylprop-2-enoate Chemical compound C1=CC=C2C(COC(=O)C(=C)C)=C(C=CC=C3)C3=CC2=C1 MJYSISMEPNOHEG-UHFFFAOYSA-N 0.000 description 1
- LDLODAMOCOQVPP-UHFFFAOYSA-N anthracene;prop-2-enoic acid Chemical compound OC(=O)C=C.C1=CC=CC2=CC3=CC=CC=C3C=C21 LDLODAMOCOQVPP-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- DNFSNYQTQMVTOK-UHFFFAOYSA-N bis(4-tert-butylphenyl)iodanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DNFSNYQTQMVTOK-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- FSOSHTGTHMEAAD-UHFFFAOYSA-N butane-1,4-diamine;dihydrate Chemical compound O.O.NCCCCN FSOSHTGTHMEAAD-UHFFFAOYSA-N 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012952 cationic photoinitiator Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MCSLBZGLEIGWTI-UHFFFAOYSA-N n-[2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethyl]acetamide Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(NC(=O)C)C1=CC=C(Cl)C=C1 MCSLBZGLEIGWTI-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- DCUJJWWUNKIJPH-UHFFFAOYSA-N nitrapyrin Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=N1 DCUJJWWUNKIJPH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002843 nonmetals Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002991 phenoxazines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006009 resin backbone Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- YBNLWIZAWPBUKQ-UHFFFAOYSA-N trichloro(trichloromethylsulfonyl)methane Chemical compound ClC(Cl)(Cl)S(=O)(=O)C(Cl)(Cl)Cl YBNLWIZAWPBUKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- Y10S430/111—Polymer of unsaturated acid or ester
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/567,630 | 1995-12-05 | ||
| US08/567,630 US5879856A (en) | 1995-12-05 | 1995-12-05 | Chemically amplified positive photoresists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR970049038A KR970049038A (ko) | 1997-07-29 |
| KR100500750B1 true KR100500750B1 (ko) | 2006-01-27 |
Family
ID=24267981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960061565A Expired - Lifetime KR100500750B1 (ko) | 1995-12-05 | 1996-12-04 | 화학적으로증폭된포지티브포토레지스트 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US5879856A (enExample) |
| EP (1) | EP0783136B1 (enExample) |
| JP (1) | JP3963987B2 (enExample) |
| KR (1) | KR100500750B1 (enExample) |
| DE (1) | DE69624085T2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150035867A (ko) * | 2007-03-12 | 2015-04-07 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 페놀계 폴리머 및 이를 포함하는 포토레지스트 |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0537524A1 (en) * | 1991-10-17 | 1993-04-21 | Shipley Company Inc. | Radiation sensitive compositions and methods |
| JPH08110638A (ja) * | 1994-10-13 | 1996-04-30 | Hitachi Chem Co Ltd | 感光性樹脂組成物およびレジスト像の製造法 |
| US6077643A (en) * | 1997-08-28 | 2000-06-20 | Shipley Company, L.L.C. | Polymers and photoresist compositions |
| JP3955385B2 (ja) * | 1998-04-08 | 2007-08-08 | Ａｚエレクトロニックマテリアルズ株式会社 | パターン形成方法 |
| US7704668B1 (en) | 1998-08-04 | 2010-04-27 | Rohm And Haas Electronic Materials Llc | Photoresist compositions and methods and articles of manufacture comprising same |
| US6127089A (en) * | 1998-08-28 | 2000-10-03 | Advanced Micro Devices, Inc. | Interconnect structure with low k dielectric materials and method of making the same with single and dual damascene techniques |
| US6280911B1 (en) * | 1998-09-10 | 2001-08-28 | Shipley Company, L.L.C. | Photoresist compositions comprising blends of ionic and non-ionic photoacid generators |
| US20040081912A1 (en) * | 1998-10-05 | 2004-04-29 | Tatsuro Nagahara | Photosensitive polysilazane composition and method of forming patterned polysilazane film |
| GR1003420B (el) * | 1999-05-26 | 2000-09-01 | Υλικα και διεργασιες μικρολιθογραφιας με βαση πολυακρυλικους υδροξυαλκυλεστερες | |
| US6582891B1 (en) | 1999-12-02 | 2003-06-24 | Axcelis Technologies, Inc. | Process for reducing edge roughness in patterned photoresist |
| JP2001183833A (ja) * | 1999-12-27 | 2001-07-06 | Sumitomo Chem Co Ltd | レジスト組成物 |
| KR20010082831A (ko) * | 2000-02-21 | 2001-08-31 | 구본준, 론 위라하디락사 | 액정표시장치의 제조방법 |
| WO2002069042A1 (en) * | 2001-02-21 | 2002-09-06 | Arch Specialty Chemicals, Inc. | Wet etch compatible deep uv photoresist compositions |
| US6936398B2 (en) | 2001-05-09 | 2005-08-30 | Massachusetts Institute Of Technology | Resist with reduced line edge roughness |
| KR20090036153A (ko) * | 2001-05-11 | 2009-04-13 | 롬 앤드 하스 일렉트로닉 머트어리얼즈, 엘.엘.씨 | 후막 포토레지스트 및 그의 사용방법 |
| US6743563B2 (en) * | 2001-08-15 | 2004-06-01 | Shipley Company, L.L.C. | Photoresist compositions |
| US7666579B1 (en) * | 2001-09-17 | 2010-02-23 | Serenity Technologies, Inc. | Method and apparatus for high density storage of analog data in a durable medium |
| TW200403522A (en) * | 2002-03-01 | 2004-03-01 | Shipley Co Llc | Photoresist compositions |
| TW200401164A (en) * | 2002-03-01 | 2004-01-16 | Shipley Co Llc | Photoresist compositions |
| US20040170925A1 (en) * | 2002-12-06 | 2004-09-02 | Roach David Herbert | Positive imageable thick film compositions |
| US20040131970A1 (en) * | 2003-01-07 | 2004-07-08 | Meagley Robert P. | Photodefinable polymers for semiconductor applications |
| US7402373B2 (en) * | 2004-02-05 | 2008-07-22 | E.I. Du Pont De Nemours And Company | UV radiation blocking protective layers compatible with thick film pastes |
| TWI322334B (en) | 2004-07-02 | 2010-03-21 | Rohm & Haas Elect Mat | Method for processing a photoresist composition in an immersion photolithography process and system and organic barrier composition used therein |
| US7175944B2 (en) * | 2004-08-31 | 2007-02-13 | Micron Technology, Inc. | Prevention of photoresist scumming |
| JP4789599B2 (ja) | 2004-12-06 | 2011-10-12 | ローム・アンド・ハース・エレクトロニック・マテリアルズ，エル．エル．シー． | フォトレジスト組成物 |
| KR101143005B1 (ko) * | 2004-12-14 | 2012-05-08 | 삼성전자주식회사 | 마스크 및 이를 이용한 반도체 소자의 제조 방법 및 박막트랜지스터 표시판의 제조 방법 |
| EP1691238A3 (en) | 2005-02-05 | 2009-01-21 | Rohm and Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
| EP1762895B1 (en) | 2005-08-29 | 2016-02-24 | Rohm and Haas Electronic Materials, L.L.C. | Antireflective Hard Mask Compositions |
| EP1829942B1 (en) | 2006-02-28 | 2012-09-26 | Rohm and Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
| TWI598223B (zh) | 2006-03-10 | 2017-09-11 | 羅門哈斯電子材料有限公司 | 用於光微影之組成物及製程 |
| EP2420892A1 (en) | 2006-10-30 | 2012-02-22 | Rohm and Haas Electronic Materials LLC | Compositions and processes for immersion lithography |
| JP4355725B2 (ja) * | 2006-12-25 | 2009-11-04 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
| TWI374478B (en) | 2007-02-13 | 2012-10-11 | Rohm & Haas Elect Mat | Electronic device manufacture |
| US20080248331A1 (en) | 2007-04-06 | 2008-10-09 | Rohm And Haas Electronic Materials Llc | Coating composition |
| KR101347284B1 (ko) * | 2007-09-28 | 2014-01-07 | 삼성전자주식회사 | 광산발생제 및 이를 포함하는 화학증폭형 레지스트 조성물 |
| EP2056162B1 (en) | 2007-11-05 | 2016-05-04 | Rohm and Haas Electronic Materials LLC | Process for immersion lithography |
| JP2009199061A (ja) | 2007-11-12 | 2009-09-03 | Rohm & Haas Electronic Materials Llc | オーバーコートされたフォトレジストと共に用いるためのコーティング組成物 |
| JP4577354B2 (ja) * | 2007-12-18 | 2010-11-10 | Ｊｓｒ株式会社 | ポジ型感放射線性樹脂組成物およびネガ型感放射線性樹脂組成物 |
| US9519216B2 (en) * | 2008-02-04 | 2016-12-13 | Fujifilm Electronic Materials U.S.A., Inc. | Positive photosensitive resin compositions |
| EP2189847A3 (en) | 2008-11-19 | 2010-07-21 | Rohm and Haas Electronic Materials LLC | Compositions comprising hetero-substituted carbocyclic aryl component and processes for photolithography |
| EP2189846B1 (en) | 2008-11-19 | 2015-04-22 | Rohm and Haas Electronic Materials LLC | Process for photolithography applying a photoresist composition comprising a block copolymer |
| EP2189845B1 (en) | 2008-11-19 | 2017-08-02 | Rohm and Haas Electronic Materials LLC | Compositions and processes for photolithography |
| EP2784584A1 (en) | 2008-11-19 | 2014-10-01 | Rohm and Haas Electronic Materials LLC | Compositions comprising sulfonamide material and processes for photolithography |
| US8575245B2 (en) * | 2008-12-23 | 2013-11-05 | Novomer, Inc. | Tunable polymer compositions |
| EP2204392A1 (en) | 2008-12-31 | 2010-07-07 | Rohm and Haas Electronic Materials LLC | Compositions and processes for photolithography |
| EP2204694A1 (en) | 2008-12-31 | 2010-07-07 | Rohm and Haas Electronic Materials LLC | Compositions and processes for photolithography |
| TW201106101A (en) * | 2009-06-01 | 2011-02-16 | Fujifilm Electronic Materials | Chemically amplified positive photoresist composition |
| US10180627B2 (en) | 2009-06-08 | 2019-01-15 | Rohm And Haas Electronic Materials Llc | Processes for photolithography |
| KR101855112B1 (ko) | 2009-06-22 | 2018-05-04 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 광산 발생제 및 이를 포함하는 포토레지스트 |
| TWI541226B (zh) * | 2010-11-15 | 2016-07-11 | 羅門哈斯電子材料有限公司 | 鹼反應性光酸產生劑及包含該光酸產生劑之光阻劑 |
| JP5961363B2 (ja) | 2010-11-15 | 2016-08-02 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | ラクトン光酸発生剤、これを含む樹脂およびフォトレジスト |
| JP2012113302A (ja) | 2010-11-15 | 2012-06-14 | Rohm & Haas Electronic Materials Llc | 塩基反応性成分を含む組成物およびフォトリソグラフィーのための方法 |
| JP6144005B2 (ja) | 2010-11-15 | 2017-06-07 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 糖成分を含む組成物およびフォトリソグラフィ方法 |
| EP2472320A2 (en) | 2010-12-30 | 2012-07-04 | Rohm and Haas Electronic Materials LLC | Compositions comprising base-reactive component and processes for photolithography |
| EP2511766B1 (en) | 2011-04-14 | 2013-07-31 | Rohm and Haas Electronic Materials LLC | Topcoat compositions for photoresist and immersion photolithography process using them |
| JP5846889B2 (ja) * | 2011-12-14 | 2016-01-20 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、化合物 |
| TWI527792B (zh) | 2012-06-26 | 2016-04-01 | 羅門哈斯電子材料有限公司 | 光酸產生劑、含該光酸產生劑之光阻劑及含該光阻劑之經塗覆物件 |
| JP5913241B2 (ja) | 2012-09-15 | 2016-04-27 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 複数の酸発生剤化合物を含むフォトレジスト |
| US9067909B2 (en) | 2013-08-28 | 2015-06-30 | Rohm And Haas Electronic Materials Llc | Photoacid generator, photoresist, coated substrate, and method of forming an electronic device |
| US9046767B2 (en) | 2013-10-25 | 2015-06-02 | Rohm And Haas Electronic Materials Llc | Photoacid generator, photoresist, coated substrate, and method of forming an electronic device |
| TWI646397B (zh) | 2015-10-31 | 2019-01-01 | 南韓商羅門哈斯電子材料韓國公司 | 與外塗佈光致抗蝕劑一起使用的塗料組合物 |
| US11448964B2 (en) | 2016-05-23 | 2022-09-20 | Rohm And Haas Electronic Materials Korea Ltd. | Coating compositions for use with an overcoated photoresist |
| CN109928904A (zh) | 2017-11-30 | 2019-06-25 | 罗门哈斯电子材料有限责任公司 | 两性离子化合物和包括其的光致抗蚀剂 |
| KR102820594B1 (ko) * | 2019-06-06 | 2025-06-16 | 제이에스알 가부시키가이샤 | 감방사선성 수지 조성물, 레지스트 패턴 형성 방법 및 화합물 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0412457A1 (en) * | 1989-08-08 | 1991-02-13 | Tosoh Corporation | Solubilization-inhibitor and positive resist composition |
| EP0462391A2 (en) * | 1990-06-19 | 1991-12-27 | Shipley Company Inc. | Acid hardened photoresists |
| EP0505094A1 (en) * | 1991-03-19 | 1992-09-23 | Minnesota Mining And Manufacturing Company | Speed stabilised positive-acting photoresist compositions |
| US5164278A (en) * | 1990-03-01 | 1992-11-17 | International Business Machines Corporation | Speed enhancers for acid sensitized resists |
| US5252427A (en) * | 1990-04-10 | 1993-10-12 | E. I. Du Pont De Nemours And Company | Positive photoresist compositions |
| US5258257A (en) * | 1991-09-23 | 1993-11-02 | Shipley Company Inc. | Radiation sensitive compositions comprising polymer having acid labile groups |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189323A (en) | 1977-04-25 | 1980-02-19 | Hoechst Aktiengesellschaft | Radiation-sensitive copying composition |
| US4442197A (en) | 1982-01-11 | 1984-04-10 | General Electric Company | Photocurable compositions |
| US4491628A (en) * | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
| ATE37242T1 (de) | 1984-02-10 | 1988-09-15 | Ciba Geigy Ag | Verfahren zur herstellung einer schutzschicht oder einer reliefabbildung. |
| DK241885A (da) | 1984-06-01 | 1985-12-02 | Rohm & Haas | Fotosensible belaegningssammensaetninger, termisk stabile belaegninger fremstillet deraf og anvendelse af saadanne belaegninger til dannelse af termisk stabile polymerbilleder |
| US4618233A (en) | 1985-05-20 | 1986-10-21 | Shipley Company Inc. | Scanning wedge method for determining characteristics of a photoresist |
| US4603101A (en) | 1985-09-27 | 1986-07-29 | General Electric Company | Photoresist compositions containing t-substituted organomethyl vinylaryl ether materials |
| CA1307695C (en) | 1986-01-13 | 1992-09-22 | Wayne Edmund Feely | Photosensitive compounds and thermally stable and aqueous developablenegative images |
| US4968581A (en) | 1986-02-24 | 1990-11-06 | Hoechst Celanese Corporation | High resolution photoresist of imide containing polymers |
| US4810613A (en) | 1987-05-22 | 1989-03-07 | Hoechst Celanese Corporation | Blocked monomer and polymers therefrom for use as photoresists |
| DE3721741A1 (de) | 1987-07-01 | 1989-01-12 | Basf Ag | Strahlungsempfindliches gemisch fuer lichtempfindliche beschichtungsmaterialien |
| DE3817011A1 (de) | 1988-05-19 | 1989-11-30 | Basf Ag | Strahlungsempfindliches gemisch und verfahren zur herstellung von reliefmustern |
| EP0366590B2 (en) | 1988-10-28 | 2001-03-21 | International Business Machines Corporation | Highly sensitive positive photoresist compositions |
| US5403695A (en) * | 1991-04-30 | 1995-04-04 | Kabushiki Kaisha Toshiba | Resist for forming patterns comprising an acid generating compound and a polymer having acid decomposable groups |
| EP0537524A1 (en) * | 1991-10-17 | 1993-04-21 | Shipley Company Inc. | Radiation sensitive compositions and methods |
| JP2654892B2 (ja) * | 1992-07-27 | 1997-09-17 | 日本電信電話株式会社 | ポジ型レジスト材料 |
| JP3148426B2 (ja) * | 1992-12-25 | 2001-03-19 | クラリアント インターナショナル リミテッド | パターン形成用材料 |
| US5393642A (en) * | 1992-12-31 | 1995-02-28 | The University Of North Carolina At Charlotte | Ionic modification of organic resins and photoresists to produce photoactive etch resistant compositions |
| KR100355254B1 (en) * | 1993-02-15 | 2003-03-31 | Clariant Finance Bvi Ltd | Positive type radiation-sensitive mixture |
| DE4408318C2 (de) * | 1993-03-12 | 1999-09-09 | Toshiba Kk | Positiv arbeitende Lichtempfindliche Zusammensetzung |
| US5344742A (en) * | 1993-04-21 | 1994-09-06 | Shipley Company Inc. | Benzyl-substituted photoactive compounds and photoresist compositions comprising same |
| KR960015081A (ko) * | 1993-07-15 | 1996-05-22 | 마쯔모또 에이이찌 | 화학증폭형 레지스트 조성물 |
| JP3203995B2 (ja) * | 1993-12-24 | 2001-09-04 | ジェイエスアール株式会社 | 感放射線性樹脂組成物 |
| US5663035A (en) * | 1994-04-13 | 1997-09-02 | Hoechst Japan Limited | Radiation-sensitive mixture comprising a basic iodonium compound |
| US5558971A (en) * | 1994-09-02 | 1996-09-24 | Wako Pure Chemical Industries, Ltd. | Resist material |
-
1995
- 1995-12-05 US US08/567,630 patent/US5879856A/en not_active Expired - Lifetime
-
1996
- 1996-11-12 EP EP96118111A patent/EP0783136B1/en not_active Expired - Lifetime
- 1996-11-12 DE DE69624085T patent/DE69624085T2/de not_active Expired - Fee Related
- 1996-12-04 KR KR1019960061565A patent/KR100500750B1/ko not_active Expired - Lifetime
- 1996-12-05 JP JP32508396A patent/JP3963987B2/ja not_active Expired - Lifetime
-
1998
- 1998-08-04 US US09/128,797 patent/US6300035B1/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0412457A1 (en) * | 1989-08-08 | 1991-02-13 | Tosoh Corporation | Solubilization-inhibitor and positive resist composition |
| US5164278A (en) * | 1990-03-01 | 1992-11-17 | International Business Machines Corporation | Speed enhancers for acid sensitized resists |
| US5252427A (en) * | 1990-04-10 | 1993-10-12 | E. I. Du Pont De Nemours And Company | Positive photoresist compositions |
| EP0462391A2 (en) * | 1990-06-19 | 1991-12-27 | Shipley Company Inc. | Acid hardened photoresists |
| EP0505094A1 (en) * | 1991-03-19 | 1992-09-23 | Minnesota Mining And Manufacturing Company | Speed stabilised positive-acting photoresist compositions |
| US5258257A (en) * | 1991-09-23 | 1993-11-02 | Shipley Company Inc. | Radiation sensitive compositions comprising polymer having acid labile groups |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150035867A (ko) * | 2007-03-12 | 2015-04-07 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 페놀계 폴리머 및 이를 포함하는 포토레지스트 |
| KR101967193B1 (ko) * | 2007-03-12 | 2019-04-09 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 페놀계 폴리머 및 이를 포함하는 포토레지스트 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0783136B1 (en) | 2002-10-02 |
| KR970049038A (ko) | 1997-07-29 |
| EP0783136A2 (en) | 1997-07-09 |
| JP3963987B2 (ja) | 2007-08-22 |
| US6300035B1 (en) | 2001-10-09 |
| DE69624085T2 (de) | 2003-06-18 |
| JPH09179303A (ja) | 1997-07-11 |
| US5879856A (en) | 1999-03-09 |
| DE69624085D1 (de) | 2002-11-07 |
| EP0783136A3 (en) | 1998-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100500750B1 (ko) | 화학적으로증폭된포지티브포토레지스트 | |
| JP4249810B2 (ja) | 染色されたフォトレジストとその方法及びそれからなる工業製品 | |
| KR100568887B1 (ko) | 포토레지스트 조성물, 이를 사용하는 포토레지스트 릴리프 상의 제조방법 및 포토레지스트로 피복된 제품 | |
| KR100980771B1 (ko) | 이온성 및 비이온성 감광산 생성원의 혼합물을 포함하는 감광성 내식막 조성물 | |
| US6048672A (en) | Photoresist compositions and methods and articles of manufacture comprising same | |
| JP4421707B2 (ja) | フォトレジスト組成物、その方法及びそれらを含有してなる工業製品 | |
| KR20010040033A (ko) | 페놀릭/알리시클릭 코폴리머 및 포토레지스트 | |
| US5976770A (en) | Dyed photoresists and methods and articles of manufacture comprising same | |
| KR100944727B1 (ko) | 포토애시드에 불안정한 중합체 및 이를 포함하는포토레지스트 | |
| JPH10268519A (ja) | 新規なポリマー及びそれを含有するフォトレジスト組成物 | |
| JP4695242B2 (ja) | ヒドロキシフェニルコポリマー及びそれらを含有するフォトレジスト | |
| JP2000298348A (ja) | 短い波長での画像形成に特に適したフォトレジスト組成物 | |
| JPH08227151A (ja) | 放射線感受性組成物中に使用する光酸発生組成物 | |
| JP3772335B2 (ja) | 感放射線性樹脂組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19961204 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20011203 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19961204 Comment text: Patent Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20040730 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20050331 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20050704 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20050705 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20080702 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20090630 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20100628 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20110617 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20120620 Start annual number: 8 End annual number: 8 |
|
| FPAY | Annual fee payment |
Payment date: 20130620 Year of fee payment: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20130620 Start annual number: 9 End annual number: 9 |
|
| FPAY | Annual fee payment |
Payment date: 20140630 Year of fee payment: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20140630 Start annual number: 10 End annual number: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20150619 Year of fee payment: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20150619 Start annual number: 11 End annual number: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20160616 Year of fee payment: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20160616 Start annual number: 12 End annual number: 12 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |