TWI227378B - Chemically amplified positive resist composition - Google Patents
Chemically amplified positive resist composition Download PDFInfo
- Publication number
- TWI227378B TWI227378B TW089127065A TW89127065A TWI227378B TW I227378 B TWI227378 B TW I227378B TW 089127065 A TW089127065 A TW 089127065A TW 89127065 A TW89127065 A TW 89127065A TW I227378 B TWI227378 B TW I227378B
- Authority
- TW
- Taiwan
- Prior art keywords
- derived
- meth
- adamantyl
- resin
- dihydroxy
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 29
- -1 dihydroxy-1-adamantyl Chemical group 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 31
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 13
- 239000003513 alkali Substances 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 230000004888 barrier function Effects 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 4
- 150000002596 lactones Chemical group 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000000052 vinegar Substances 0.000 claims description 2
- 235000021419 vinegar Nutrition 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 4
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- 239000000178 monomer Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 description 5
- 206010034972 Photosensitivity reaction Diseases 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 230000036211 photosensitivity Effects 0.000 description 5
- DCTVCFJTKSQXED-UHFFFAOYSA-N (2-ethyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(CC)(OC(=O)C(C)=C)C2C3 DCTVCFJTKSQXED-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000007514 bases Chemical class 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000001312 dry etching Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000001459 lithography Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HFLCKUMNXPOLSN-UHFFFAOYSA-N (3,5-dihydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3(O)CC2(O)CC1(OC(=O)C(=C)C)C3 HFLCKUMNXPOLSN-UHFFFAOYSA-N 0.000 description 3
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 3
- LFJJGHGXHXXDFT-GSVOUGTGSA-N (3r)-3-bromooxolan-2-one Chemical compound Br[C@@H]1CCOC1=O LFJJGHGXHXXDFT-GSVOUGTGSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000002079 cooperative effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- QSUJHKWXLIQKEY-ZCFIWIBFSA-N [(3R)-2-oxooxolan-3-yl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)O[C@@H]1CCOC1=O QSUJHKWXLIQKEY-ZCFIWIBFSA-N 0.000 description 2
- IYKFYARMMIESOX-UHFFFAOYSA-N adamantanone Chemical compound C1C(C2)CC3CC1C(=O)C2C3 IYKFYARMMIESOX-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- GLLLWZSBUMRTCD-UHFFFAOYSA-N chloro trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OCl GLLLWZSBUMRTCD-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- GYXAHUXQRATWDV-UHFFFAOYSA-N (1,3-dioxoisoindol-2-yl) trifluoromethanesulfonate Chemical compound C1=CC=C2C(=O)N(OS(=O)(=O)C(F)(F)F)C(=O)C2=C1 GYXAHUXQRATWDV-UHFFFAOYSA-N 0.000 description 1
- OKRLWHAZMUFONP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)ON1C(=O)CCC1=O OKRLWHAZMUFONP-UHFFFAOYSA-N 0.000 description 1
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O MCJPJAJHPRCILL-UHFFFAOYSA-N 0.000 description 1
- 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
- QXTKWWMLNUQOLB-UHFFFAOYSA-N (4-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QXTKWWMLNUQOLB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- OESYNCIYSBWEQV-UHFFFAOYSA-N 1-[diazo-(2,4-dimethylphenyl)sulfonylmethyl]sulfonyl-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1C OESYNCIYSBWEQV-UHFFFAOYSA-N 0.000 description 1
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 1
- ULGCVKBNCOLUAV-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)sulfonyl-diazomethyl]sulfonylbenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(Cl)C=C1 ULGCVKBNCOLUAV-UHFFFAOYSA-N 0.000 description 1
- ZBZAGZCFEOTODC-UHFFFAOYSA-N 1-tert-butyl-4-[(4-tert-butylphenyl)sulfonyl-diazomethyl]sulfonylbenzene Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 ZBZAGZCFEOTODC-UHFFFAOYSA-N 0.000 description 1
- DZPKGHCUNRKJJO-UHFFFAOYSA-N 2,4,6-tris(chloromethyl)-1,3,5-trioxane Chemical compound ClCC1OC(CCl)OC(CCl)O1 DZPKGHCUNRKJJO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LFEQNZNCKDNGRM-UHFFFAOYSA-N 2-ethylhexyl butanoate Chemical compound CCCCC(CC)COC(=O)CCC LFEQNZNCKDNGRM-UHFFFAOYSA-N 0.000 description 1
- JKOZWMQUOWYZAB-UHFFFAOYSA-N 2-methyladamantan-2-ol Chemical compound C1C(C2)CC3CC1C(C)(O)C2C3 JKOZWMQUOWYZAB-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VMFXHPWUODXYPV-HXUWFJFHSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)[C@]1(C(=O)OCC1)OC=CC Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)[C@]1(C(=O)OCC1)OC=CC VMFXHPWUODXYPV-HXUWFJFHSA-N 0.000 description 1
- ITACPBQXJFHNDU-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1OC(OC(O1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl Chemical compound ClC1=CC=C(C=C1)C1OC(OC(O1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl ITACPBQXJFHNDU-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MWMWRSCIFDZZGW-RXMQYKEDSA-N [(3R)-2-oxooxolan-3-yl] prop-2-enoate Chemical compound C=CC(=O)O[C@@H]1CCOC1=O MWMWRSCIFDZZGW-RXMQYKEDSA-N 0.000 description 1
- QFKJMDYQKVPGNM-UHFFFAOYSA-N [benzenesulfonyl(diazo)methyl]sulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=CC=C1 QFKJMDYQKVPGNM-UHFFFAOYSA-N 0.000 description 1
- GLGXSTXZLFQYKJ-UHFFFAOYSA-N [cyclohexylsulfonyl(diazo)methyl]sulfonylcyclohexane Chemical compound C1CCCCC1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCCC1 GLGXSTXZLFQYKJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RASLIQQQAJRCPM-UHFFFAOYSA-N n-methylprop-1-en-1-amine Chemical compound CNC=CC RASLIQQQAJRCPM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-M octane-1-sulfonate Chemical compound CCCCCCCCS([O-])(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-M 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- ULAQISQDFQAUCH-UHFFFAOYSA-N trifluoromethanesulfonic acid hydroiodide Chemical compound I.OS(=O)(=O)C(F)(F)F ULAQISQDFQAUCH-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36472699A JP4453138B2 (ja) | 1999-12-22 | 1999-12-22 | 化学増幅型ポジ型レジスト組成物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI227378B true TWI227378B (en) | 2005-02-01 |
Family
ID=18482519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089127065A TWI227378B (en) | 1999-12-22 | 2000-12-18 | Chemically amplified positive resist composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6495306B2 (enExample) |
| JP (1) | JP4453138B2 (enExample) |
| KR (1) | KR100750815B1 (enExample) |
| DE (1) | DE10063064A1 (enExample) |
| GB (1) | GB2358256B (enExample) |
| TW (1) | TWI227378B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100498440B1 (ko) * | 1999-11-23 | 2005-07-01 | 삼성전자주식회사 | 백본이 환상 구조를 가지는 감광성 폴리머와 이를포함하는 레지스트 조성물 |
| JP4529245B2 (ja) * | 1999-12-03 | 2010-08-25 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
| JP4329214B2 (ja) * | 2000-03-28 | 2009-09-09 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
| JP4576737B2 (ja) * | 2000-06-09 | 2010-11-10 | Ｊｓｒ株式会社 | 感放射線性樹脂組成物 |
| JP2002030118A (ja) * | 2000-07-14 | 2002-01-31 | Tokyo Ohka Kogyo Co Ltd | 新規コポリマー、ホトレジスト組成物、および高アスペクト比のレジストパターン形成方法 |
| US6727039B2 (en) * | 2000-09-25 | 2004-04-27 | Fuji Photo Film Co., Ltd. | Positive photoresist composition |
| TW538316B (en) * | 2001-01-19 | 2003-06-21 | Sumitomo Chemical Co | Chemical amplifying type positive resist composition |
| JP2002357905A (ja) * | 2001-03-28 | 2002-12-13 | Sumitomo Chem Co Ltd | レジスト組成物 |
| EP1267210B1 (en) | 2001-06-12 | 2018-02-21 | FUJIFILM Corporation | Positive resist composition |
| US6844133B2 (en) * | 2001-08-31 | 2005-01-18 | Shin-Etsu Chemical Co., Ltd. | Polymer, resist composition and patterning process |
| JP3841399B2 (ja) | 2002-02-21 | 2006-11-01 | 富士写真フイルム株式会社 | ポジ型レジスト組成物 |
| US7160669B2 (en) * | 2002-10-16 | 2007-01-09 | Sumitomo Chemical Company, Limited | Chemical amplification type resist composition |
| KR20050094828A (ko) * | 2002-12-26 | 2005-09-28 | 도오꾜오까고오교 가부시끼가이샤 | 포지티브형 레지스트 조성물 및 레지스트 패턴 형성 방법 |
| JP4434762B2 (ja) | 2003-01-31 | 2010-03-17 | 東京応化工業株式会社 | レジスト組成物 |
| JP2005099646A (ja) | 2003-03-28 | 2005-04-14 | Tokyo Ohka Kogyo Co Ltd | 液浸露光プロセス用レジスト組成物および該レジスト組成物を用いたレジストパターン形成方法 |
| JP2004333548A (ja) * | 2003-04-30 | 2004-11-25 | Tokyo Ohka Kogyo Co Ltd | ポジ型ホトレジスト組成物およびレジストパターン形成方法 |
| JP4772288B2 (ja) | 2003-06-05 | 2011-09-14 | 東京応化工業株式会社 | ホトレジスト組成物用樹脂、ホトレジスト組成物、およびレジストパターン形成方法 |
| JP2005010488A (ja) * | 2003-06-19 | 2005-01-13 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物 |
| JP4092571B2 (ja) * | 2003-08-05 | 2008-05-28 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| US20060240355A1 (en) * | 2003-09-25 | 2006-10-26 | Tomoyuki Ando | Positive resist composition and resist laminate for low-acceleration electron beam and mehod of pattern formation |
| US7488565B2 (en) * | 2003-10-01 | 2009-02-10 | Chevron U.S.A. Inc. | Photoresist compositions comprising diamondoid derivatives |
| JP4188265B2 (ja) * | 2003-10-23 | 2008-11-26 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
| JP2005164633A (ja) * | 2003-11-28 | 2005-06-23 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物及びレジストパターン形成方法 |
| JP4279237B2 (ja) * | 2004-05-28 | 2009-06-17 | 東京応化工業株式会社 | ポジ型レジスト組成物及びレジストパターン形成方法 |
| JP2005344009A (ja) * | 2004-06-03 | 2005-12-15 | Shin Etsu Chem Co Ltd | レジスト材料用高分子化合物及びその製造方法並びに化学増幅ポジ型レジスト材料 |
| JP2007003619A (ja) * | 2005-06-21 | 2007-01-11 | Fujifilm Holdings Corp | 感光性組成物、該感光性組成物を用いたパターン形成方法及び該感光性組成物に用いる化合物 |
| US7927779B2 (en) * | 2005-06-30 | 2011-04-19 | Taiwan Semiconductor Manufacturing Companym, Ltd. | Water mark defect prevention for immersion lithography |
| JP4695941B2 (ja) * | 2005-08-19 | 2011-06-08 | 富士フイルム株式会社 | 液浸露光用ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
| US7776510B2 (en) * | 2007-06-13 | 2010-08-17 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, compound and acid generator |
| JP5523854B2 (ja) * | 2009-02-06 | 2014-06-18 | 住友化学株式会社 | 化学増幅型フォトレジスト組成物及びパターン形成方法 |
| JP5884728B2 (ja) * | 2010-04-01 | 2016-03-15 | 三菱瓦斯化学株式会社 | アダマンチル（メタ）アクリル系モノマー及びそれを繰り返し単位に含む（メタ）アクリル系重合体 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3546679B2 (ja) * | 1997-01-29 | 2004-07-28 | 住友化学工業株式会社 | 化学増幅型ポジ型レジスト組成物 |
| KR100538968B1 (ko) * | 1997-02-18 | 2006-07-11 | 후지 샤신 필름 가부시기가이샤 | 포지티브감광성조성물 |
| JP3948795B2 (ja) * | 1997-09-30 | 2007-07-25 | ダイセル化学工業株式会社 | 放射線感光材料及びそれを用いたパターン形成方法 |
| JP3972438B2 (ja) * | 1998-01-26 | 2007-09-05 | 住友化学株式会社 | 化学増幅型のポジ型レジスト組成物 |
| JP3738562B2 (ja) * | 1998-02-19 | 2006-01-25 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
| EP1000924A4 (en) * | 1998-05-25 | 2005-01-05 | Daicel Chem | ACID SENSITIVE COMPOUND AND RESIN COMPOSITION FOR PHOTORESIN |
| JP4434358B2 (ja) * | 1998-05-25 | 2010-03-17 | ダイセル化学工業株式会社 | フォトレジスト用化合物およびフォトレジスト用樹脂組成物 |
| EP1443363B1 (en) * | 1998-05-25 | 2013-07-10 | Daicel Chemical Industries, Ltd. | Photoresist composition |
| JP3810957B2 (ja) * | 1998-08-06 | 2006-08-16 | 株式会社東芝 | レジスト用樹脂、レジスト組成物およびそれを用いたパターン形成方法 |
| JP3876571B2 (ja) * | 1998-08-26 | 2007-01-31 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
| CN1190706C (zh) * | 1998-08-26 | 2005-02-23 | 住友化学工业株式会社 | 一种化学增强型正光刻胶组合物 |
| US6303266B1 (en) * | 1998-09-24 | 2001-10-16 | Kabushiki Kaisha Toshiba | Resin useful for resist, resist composition and pattern forming process using the same |
| JP3890380B2 (ja) * | 1999-05-28 | 2007-03-07 | 富士フイルム株式会社 | 遠紫外線露光用ポジ型フォトレジスト組成物 |
| JP4585636B2 (ja) * | 1999-09-30 | 2010-11-24 | ダイセル化学工業株式会社 | アクリル系単量体の重合方法 |
| JP2002006501A (ja) * | 1999-11-09 | 2002-01-09 | Sumitomo Chem Co Ltd | 化学増幅型レジスト組成物 |
-
1999
- 1999-12-22 JP JP36472699A patent/JP4453138B2/ja not_active Expired - Fee Related
-
2000
- 2000-12-18 DE DE10063064A patent/DE10063064A1/de not_active Withdrawn
- 2000-12-18 TW TW089127065A patent/TWI227378B/zh not_active IP Right Cessation
- 2000-12-20 KR KR1020000079000A patent/KR100750815B1/ko not_active Expired - Lifetime
- 2000-12-20 GB GB0031072A patent/GB2358256B/en not_active Expired - Fee Related
- 2000-12-21 US US09/741,438 patent/US6495306B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001183836A (ja) | 2001-07-06 |
| US6495306B2 (en) | 2002-12-17 |
| GB0031072D0 (en) | 2001-01-31 |
| JP4453138B2 (ja) | 2010-04-21 |
| DE10063064A1 (de) | 2001-06-28 |
| GB2358256B (en) | 2001-12-12 |
| US20010014428A1 (en) | 2001-08-16 |
| KR100750815B1 (ko) | 2007-08-22 |
| KR20010062537A (ko) | 2001-07-07 |
| GB2358256A (en) | 2001-07-18 |
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| MK4A | Expiration of patent term of an invention patent |