KR100536540B1 - 화학 증폭 포지티브형 레지스트 재료 - Google Patents
화학 증폭 포지티브형 레지스트 재료 Download PDFInfo
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- KR100536540B1 KR100536540B1 KR10-2001-0011374A KR20010011374A KR100536540B1 KR 100536540 B1 KR100536540 B1 KR 100536540B1 KR 20010011374 A KR20010011374 A KR 20010011374A KR 100536540 B1 KR100536540 B1 KR 100536540B1
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- 239000000126 substance Substances 0.000 title description 10
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- 238000003199 nucleic acid amplification method Methods 0.000 title description 3
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 72
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 11
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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- 239000000758 substrate Substances 0.000 description 18
- 239000007983 Tris buffer Substances 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
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- 238000003756 stirring Methods 0.000 description 8
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- XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 description 6
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- 239000011248 coating agent Substances 0.000 description 6
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
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- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 5
- RLTPXEAFDJVHSN-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 RLTPXEAFDJVHSN-UHFFFAOYSA-N 0.000 description 5
- WVSYONICNIDYBE-UHFFFAOYSA-M 4-fluorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(F)C=C1 WVSYONICNIDYBE-UHFFFAOYSA-M 0.000 description 5
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- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
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- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 5
- QDHFHIQKOVNCNC-UHFFFAOYSA-M butane-1-sulfonate Chemical compound CCCCS([O-])(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-M 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 5
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 5
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 4
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 4
- JQSAQAUHGZWVOX-UHFFFAOYSA-N 1-ethenyl-4-(1-phenylmethoxypropoxy)benzene Chemical compound C=1C=C(C=C)C=CC=1OC(CC)OCC1=CC=CC=C1 JQSAQAUHGZWVOX-UHFFFAOYSA-N 0.000 description 4
- IKMBXKGUMLSBOT-UHFFFAOYSA-M 2,3,4,5,6-pentafluorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F IKMBXKGUMLSBOT-UHFFFAOYSA-M 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
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- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
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- 238000009792 diffusion process Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
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- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 4
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000000233 ultraviolet lithography Methods 0.000 description 4
- FMEBJQQRPGHVOR-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)CCCC1 FMEBJQQRPGHVOR-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZKJNETINGMOHJG-UHFFFAOYSA-N 1-prop-1-enoxyprop-1-ene Chemical class CC=COC=CC ZKJNETINGMOHJG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- QTIUDCKTDDTUJM-UHFFFAOYSA-N 4-ethenylphenol;styrene Chemical compound C=CC1=CC=CC=C1.OC1=CC=C(C=C)C=C1 QTIUDCKTDDTUJM-UHFFFAOYSA-N 0.000 description 3
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 3
- UZOPBVPWPWOJGF-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-2-methylidenepent-4-enoic acid Chemical compound OC(=O)C(=C)CC=CC1=CC=C(O)C=C1 UZOPBVPWPWOJGF-UHFFFAOYSA-N 0.000 description 3
- PAPNRQCYSFBWDI-UHFFFAOYSA-N DMP Natural products CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
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- 239000004793 Polystyrene Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 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 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000010550 living polymerization reaction Methods 0.000 description 3
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- 239000012046 mixed solvent Substances 0.000 description 3
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- QARNHIBOPBXNSX-UHFFFAOYSA-N prop-1-enoxymethylbenzene Chemical compound CC=COCC1=CC=CC=C1 QARNHIBOPBXNSX-UHFFFAOYSA-N 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
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- 230000007017 scission Effects 0.000 description 3
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- HENPLGIMUIZOJQ-UHFFFAOYSA-N tris[3-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound CC(C)(C)OC1=CC=CC([S+](C=2C=C(OC(C)(C)C)C=CC=2)C=2C=C(OC(C)(C)C)C=CC=2)=C1 HENPLGIMUIZOJQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
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- 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
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- G—PHYSICS
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- 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
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- G—PHYSICS
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- 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
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
Claims (5)
- (A) 광산발생제(B) 하기 화학식 1로 표시되는 치환기를 갖고, 산의 작용으로 알칼리 현상액에 대한 용해성이 변화하는 수지를 포함하는 화학 증폭 포지티브형 레지스트 재료.<화학식 1>Ph(CH2)nOCH(CH2CH3)-상기 식에서,Ph는 페닐기를 나타내고,n은 1 또는 2이다.
- 제1항에 있어서, (B)성분의 수지가 하기 화학식 2aa 또는 2ab의 단위를 갖는 알칼리 가용성 수지의 페놀성 수산기 및(또는) 카르복실기의 수소 원자 중 일부 또는 전부를 상기 화학식 1로 표시되는 치환기로 보호한 수지인 화학 증폭 포지티브형 레지스트 재료.<화학식 2aa><화학식 2ab>상기 식에서,R4는 수소 원자 또는 메틸기를 나타내고,R5는 탄소수 1 내지 8의 직쇄상, 분지상 또는 환상의 알킬기를 나타내며,x는 0 또는 양의 정수이고, y는 양의 정수로서, x+y≤5를 만족하는 수이며,M, N은 양의 정수로서, 0<N/(M+N)≤0.5를 만족하는 수이다.
- 제1항에 있어서, (B)성분의 수지가 하기 화학식 2ac를 갖는 분지형의 알칼리 가용성 수지의 페놀성 수산기의 수소 원자 중 일부를 상기 화학식 1로 표시되는 치환기로 보호한 수지인 화학 증폭 포지티브형 레지스트 재료.<화학식 2ac>상기 식에서,ZZ는 CH2, CH(OH), CR5(OH), C=O, C(OR5)(OH)로부터 선택되는 2가의 유기기, 또는 -C(OH)=로 표시되는 3가의 유기기를 나타내고,E는 각각 동일하거나 다를 수 있는 양의 정수이고, K는 양의 정수로서, K/(K+E)=0.001 내지 0.1을 만족하는 수이며,XX는 1 또는 2이고,R4, R5, x, y는 상기와 동일한 의미를 나타낸다.
- 제1항 내지 제3항 중 어느 한 항에 있어서, (B)성분의 수지가 또한 산불안정기를 갖는 수지인 화학 증폭 포지티브형 레지스트 재료.
- 제1항 내지 제3항 중 어느 한 항에 있어서, (B)성분의 수지가 또한 하기 화학식 4 내지 7로 표시되는 기, 탄소수 4 내지 20의 3급 알킬기, 각 알킬기가 각각 탄소수 1 내지 6의 트리알킬실릴기, 탄소수 4 내지 20의 옥소알킬기로부터 선택되는 산불안정기를 갖는 수지인 화학 증폭 포지티브형 레지스트 재료.<화학식 4><화학식 5><화학식 6><화학식 7>상기 식에서,R10, R11은 수소 원자 또는 탄소수 1 내지 18의 직쇄상, 분지상 또는 환상의 알킬기를 나타내고, R12는 탄소수 1 내지 18의 산소 원자 등의 헤테로 원자를 가질 수 있는 1가의 탄화수소기를 나타내고, R10과 R11, R10과 R12, R11과 R12는 환을 형성할 수 있으며, 환을 형성하는 경우 R10, R11, R12는 각각 탄소수 1 내지 18의 직쇄상 또는 분지상의 알킬렌기를 나타내고,R13은 탄소수 4 내지 20의 3급 알킬기, 각 알킬기가 각각 탄소수 1 내지 6의 트리알킬실릴기, 탄소수 4 내지 20의 옥소알킬기 또는 상기 화학식 4로 표시되는 기이고, z는 0 내지 6의 정수이며,R14는 탄소수 1 내지 8의 직쇄상, 분지상 또는 환상의 알킬기 또는 탄소수 6 내지 20의 치환될 수 있는 아릴기를 나타내고, h는 0 또는 1이고, i는 0, 1, 2, 3 중 어느 하나이고, 2h+i=2 또는 3을 만족하는 수이며,R15는 탄소수 1 내지 8의 직쇄상, 분지상 또는 환상의 알킬기 또는 탄소수 6 내지 20의 치환될 수 있는 아릴기를 나타내고, R16 내지 R25는 각각 독립적으로 수소 원자 또는 탄소수 1 내지 15의 헤테로 원자를 포함할 수 있는 1가의 탄화수소기를 나타내고, R16 내지 R25는 서로 환을 형성할 수 있으며, 그 경우 탄소수 1 내지 15의 헤테로 원자를 포함할 수 있는 2가의 탄화수소기를 나타내고, 또한 R16 내지 R25는 인접하는 탄소에 결합하는 것들이 직접 결합하여 이중 결합을 형성할 수 있다.
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US5989462A (en) * | 1997-07-31 | 1999-11-23 | Q2100, Inc. | Method and composition for producing ultraviolent blocking lenses |
US6949329B2 (en) * | 2001-06-22 | 2005-09-27 | Matsushita Electric Industrial Co., Ltd. | Pattern formation method |
JP2003233190A (ja) * | 2001-10-09 | 2003-08-22 | Shipley Co Llc | 混合フォト酸レイビル基を有するポリマーおよび該ポリマーを含むフォトレジスト |
US20030232273A1 (en) * | 2001-10-09 | 2003-12-18 | Shipley Company, L.L.C. | Acetal/alicyclic polymers and photoresist compositions |
JP2004334060A (ja) * | 2003-05-12 | 2004-11-25 | Shin Etsu Chem Co Ltd | 化学増幅型レジスト用光酸発生剤及びそれを含有するレジスト材料並びにパターン形成方法 |
US20080008956A1 (en) * | 2006-06-23 | 2008-01-10 | Eastman Kodak Company | Positive-working imageable members with branched hydroxystyrene polymers |
JP5286236B2 (ja) | 2009-11-30 | 2013-09-11 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、それを用いて形成した膜及びそれを用いたパターン形成方法 |
US9921480B2 (en) * | 2016-02-10 | 2018-03-20 | Taiwan Semiconductor Manufacturing Co., Ltd | Extreme ultraviolet photoresist |
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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 |
DE3750275T3 (de) | 1986-06-13 | 1998-10-01 | Microsi Inc | Lackzusammensetzung und -anwendung. |
JP2578646B2 (ja) | 1988-07-18 | 1997-02-05 | 三洋電機株式会社 | 非水系二次電池 |
JP3030672B2 (ja) | 1991-06-18 | 2000-04-10 | 和光純薬工業株式会社 | 新規なレジスト材料及びパタ−ン形成方法 |
DE69218393T2 (de) * | 1991-12-16 | 1997-10-16 | Matsushita Electric Ind Co Ltd | Resistmaterial |
JPH06308437A (ja) | 1993-04-26 | 1994-11-04 | Nippon Telegr & Teleph Corp <Ntt> | 光制御素子 |
US5558971A (en) | 1994-09-02 | 1996-09-24 | Wako Pure Chemical Industries, Ltd. | Resist material |
JP2942167B2 (ja) | 1994-09-02 | 1999-08-30 | 和光純薬工業株式会社 | レジスト材料及びこれを用いたパターン形成方法 |
EP0780732B1 (en) * | 1995-12-21 | 2003-07-09 | Wako Pure Chemical Industries Ltd | Polymer composition and resist material |
ATE199985T1 (de) * | 1996-02-09 | 2001-04-15 | Wako Pure Chem Ind Ltd | Polymer und resistmaterial |
JP3198915B2 (ja) * | 1996-04-02 | 2001-08-13 | 信越化学工業株式会社 | 化学増幅ポジ型レジスト材料 |
US6281318B1 (en) * | 1997-03-04 | 2001-08-28 | Mitsui Chemicals, Inc. | Poly{1-(1-alkoxyalkoxy)-4-(1-methylethenyl)benzene} having narrow molecular weight distribution, its preparation process, and preparation process of poly{4-methylethenyl)phenol} having narrow molecular weight distribution |
TW552475B (en) * | 1999-06-09 | 2003-09-11 | Wako Pure Chem Ind Ltd | A resist composition |
KR100557615B1 (ko) * | 2000-10-23 | 2006-03-10 | 주식회사 하이닉스반도체 | 레지스트 플로우 공정용 포토레지스트 조성물 |
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US6682869B2 (en) | 2004-01-27 |
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