TW200419309A - Polymer compound, resist composition and dissolution inhibitor agent containing the polymer compound - Google Patents
Polymer compound, resist composition and dissolution inhibitor agent containing the polymer compound Download PDFInfo
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- TW200419309A TW200419309A TW092130281A TW92130281A TW200419309A TW 200419309 A TW200419309 A TW 200419309A TW 092130281 A TW092130281 A TW 092130281A TW 92130281 A TW92130281 A TW 92130281A TW 200419309 A TW200419309 A TW 200419309A
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- polymer compound
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- item
- patent application
- alicyclic group
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- 229920000642 polymer Polymers 0.000 title claims abstract description 117
- 150000001875 compounds Chemical class 0.000 title claims abstract description 95
- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 238000004090 dissolution Methods 0.000 title claims abstract description 29
- 239000003112 inhibitor Substances 0.000 title claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 title abstract description 5
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 94
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 10
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 16
- 238000010521 absorption reaction Methods 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- -1 perfluoroadamantyl Chemical group 0.000 claims description 12
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 238000010586 diagram Methods 0.000 claims 1
- 229920005601 base polymer Polymers 0.000 abstract description 4
- 238000005530 etching Methods 0.000 abstract description 4
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 70
- 229920005989 resin Polymers 0.000 description 70
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Substances CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000000206 photolithography Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- JVZRCNQLWOELDU-UHFFFAOYSA-N 4-Phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000001228 spectrum 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
- SJHOVWZLTATEIX-UHFFFAOYSA-N (2,2,3,4,4,5,6,6,8,8,9,9,10,10-tetradecafluoro-7-hydroxy-1-adamantyl) prop-2-enoate Chemical compound FC1(F)C(C2(F)F)(F)C(F)(F)C3(F)C(F)(F)C1(O)C(F)(F)C2(OC(=O)C=C)C3(F)F SJHOVWZLTATEIX-UHFFFAOYSA-N 0.000 description 3
- 0 C*CC(C(C)(C)C*(*(C)C)C(OC(CCO1)C1=O)=C)C(OC(C)(*C1)C2CC1CC(C)C2)=C Chemical compound C*CC(C(C)(C)C*(*(C)C)C(OC(CCO1)C1=O)=C)C(OC(C)(*C1)C2CC1CC(C)C2)=C 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 3
- 239000012953 triphenylsulfonium Substances 0.000 description 3
- 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 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229920005568 monocyclic polymer Polymers 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- QDEMGMGYWDCWSD-UHFFFAOYSA-N (2,2,3,4,4,5,6,6,7,8,8,9,9,10,10-pentadecafluoro-1-adamantyl) 2-methylprop-2-enoate Chemical compound FC1(F)C(C2(F)F)(F)C(F)(F)C3(F)C(F)(F)C2(F)C(F)(F)C1(OC(=O)C(=C)C)C3(F)F QDEMGMGYWDCWSD-UHFFFAOYSA-N 0.000 description 1
- YRPLSAWATHBYFB-UHFFFAOYSA-N (2-methyl-2-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)(OC(=O)C=C)C2C3 YRPLSAWATHBYFB-UHFFFAOYSA-N 0.000 description 1
- DKDKCSYKDZNMMA-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1(O)CC2(OC(=O)C=C)C3 DKDKCSYKDZNMMA-UHFFFAOYSA-N 0.000 description 1
- IAPRPQQYWNMCRH-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonic acid 1-phenyl-9H-fluorene Chemical compound FC(C(C(C(S(=O)(=O)O)(F)F)(F)F)(F)F)(F)F.C1(=CC=CC=C1)C1=CC=CC=2C3=CC=CC=C3CC12 IAPRPQQYWNMCRH-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-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
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical class COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- CDDDRVNOHLVEED-UHFFFAOYSA-N 1-cyclohexyl-3-[1-[[1-(cyclohexylcarbamoylamino)cyclohexyl]diazenyl]cyclohexyl]urea Chemical compound C1CCCCC1(N=NC1(CCCCC1)NC(=O)NC1CCCCC1)NC(=O)NC1CCCCC1 CDDDRVNOHLVEED-UHFFFAOYSA-N 0.000 description 1
- BJDAMZSSOUGLRQ-UHFFFAOYSA-N 2,2,3,4,4,5,6,6,7,8,8,9,9,10,10-pentadecafluoroadamantan-1-ol Chemical compound FC1(F)C(C2(F)F)(F)C(F)(F)C3(F)C(F)(F)C1(O)C(F)(F)C2(F)C3(F)F BJDAMZSSOUGLRQ-UHFFFAOYSA-N 0.000 description 1
- JTDRRMWAIZNBDU-UHFFFAOYSA-N 2,3,4,4,5,6,6,7,8,8,9,9,10,10-tetradecafluoroadamantane-1,2-diol Chemical compound FC1(F)C(C2(F)F)(F)C(F)(F)C3(F)C(O)(F)C1(O)C(F)(F)C2(F)C3(F)F JTDRRMWAIZNBDU-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- FHBWGXDQIOWTCK-UHFFFAOYSA-N 2-methylpentanenitrile Chemical compound CCCC(C)C#N FHBWGXDQIOWTCK-UHFFFAOYSA-N 0.000 description 1
- ZASNZEIYVSFMMG-UHFFFAOYSA-N 3-(1-adamantyl)-2-methylprop-2-enoic acid Chemical compound C1C(C2)CC3CC2CC1(C=C(C)C(O)=O)C3 ZASNZEIYVSFMMG-UHFFFAOYSA-N 0.000 description 1
- JNVFIMNBBVDEPV-UHFFFAOYSA-N 4-butylbenzenesulfonic acid Chemical compound CCCCC1=CC=C(S(O)(=O)=O)C=C1 JNVFIMNBBVDEPV-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GGHUOZPRWICFQC-UHFFFAOYSA-M C1(=CC=CC=C1)[Fe](I)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)[Fe](I)C1=CC=CC=C1 GGHUOZPRWICFQC-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
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- QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 238000009825 accumulation Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
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- ISQINHMJILFLAQ-UHFFFAOYSA-N argon hydrofluoride Chemical compound F.[Ar] ISQINHMJILFLAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
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- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HWEQKSVYKBUIIK-UHFFFAOYSA-N cyclobuta-1,3-diene Chemical compound C1=CC=C1 HWEQKSVYKBUIIK-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
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- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- CUPFNGOKRMWUOO-UHFFFAOYSA-N hydron;difluoride Chemical compound F.F CUPFNGOKRMWUOO-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- ROMWNDGABOQKIW-UHFFFAOYSA-N phenyliodanuidylbenzene Chemical compound C=1C=CC=CC=1[I-]C1=CC=CC=C1 ROMWNDGABOQKIW-UHFFFAOYSA-N 0.000 description 1
- VBOGDLCGFBSZKS-UHFFFAOYSA-N phenylsulfanylbenzene;trifluoromethanesulfonic acid Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[SH+]C1=CC=CC=C1 VBOGDLCGFBSZKS-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
-
- 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
- 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
-
- 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
- Y10S430/108—Polyolefin or halogen containing
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002349167A JP4233314B2 (ja) | 2002-11-29 | 2002-11-29 | レジスト組成物および溶解制御剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200419309A true TW200419309A (en) | 2004-10-01 |
| TWI311235B TWI311235B (enExample) | 2009-06-21 |
Family
ID=32463017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092130281A TW200419309A (en) | 2002-11-29 | 2003-10-30 | Polymer compound, resist composition and dissolution inhibitor agent containing the polymer compound |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7326512B2 (enExample) |
| JP (1) | JP4233314B2 (enExample) |
| KR (1) | KR100629124B1 (enExample) |
| AU (1) | AU2003302653A1 (enExample) |
| TW (1) | TW200419309A (enExample) |
| WO (1) | WO2004050725A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7488847B2 (en) | 2002-12-11 | 2009-02-10 | Asahi Glass Company, Limited | Fluorinated adamantane and its derivatives |
| AU2003289036A1 (en) | 2002-12-11 | 2004-06-30 | Asahi Glass Company, Limited | Fluorinated adamantane derivatives |
| JP2007525543A (ja) * | 2003-02-20 | 2007-09-06 | プロメラス， エルエルシー | フォトレジスト組成物のための溶解速度調整剤 |
| US7232641B2 (en) * | 2003-10-08 | 2007-06-19 | Shin-Etsu Chemical Co., Ltd. | Polymerizable compound, polymer, positive-resist composition, and patterning process using the same |
| EP1757575A4 (en) * | 2004-06-16 | 2008-05-07 | Asahi Glass Co Ltd | FLUORADAMANTANDERIVAT |
| WO2005123650A1 (ja) | 2004-06-16 | 2005-12-29 | Asahi Glass Company, Limited | 新規なフッ素化されたアダマンタン誘導体 |
| JP4191103B2 (ja) * | 2004-07-02 | 2008-12-03 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
| JP2006085081A (ja) * | 2004-09-17 | 2006-03-30 | Daikin Ind Ltd | 微細パターン形成方法およびそれに用いるレジスト組成物 |
| EP1942091A4 (en) * | 2005-10-28 | 2011-04-27 | Asahi Glass Co Ltd | NEW FLUORADAMANTANDERIVAT, FLUOROUS POLYMER AND MANUFACTURING PROCESS |
| JPWO2007119803A1 (ja) * | 2006-04-13 | 2009-08-27 | 旭硝子株式会社 | イマージョンリソグラフィー用レジスト材料 |
| WO2007122977A1 (ja) | 2006-04-20 | 2007-11-01 | Asahi Glass Company, Limited | イマージョンリソグラフィー用レジスト保護膜材料 |
| EP2014639A1 (en) * | 2006-04-28 | 2009-01-14 | Idemitsu Kosan Co., Ltd. | Fluorine-containing adamantane derivative, fluorine-containing adamantane derivative having polymerizable group, resin composition containing the same, and antireflection film |
| CN101489969A (zh) * | 2006-07-11 | 2009-07-22 | 旭硝子株式会社 | 具有被高度氟化的降冰片烷结构的含氟化合物、含氟聚合物及制造方法 |
| JP4666190B2 (ja) * | 2008-10-30 | 2011-04-06 | 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 |
| JP4987837B2 (ja) * | 2008-11-13 | 2012-07-25 | 東京応化工業株式会社 | 高分子化合物 |
| JP5193121B2 (ja) | 2009-04-17 | 2013-05-08 | 東京エレクトロン株式会社 | レジスト塗布現像方法 |
| JP5386236B2 (ja) | 2009-06-01 | 2014-01-15 | 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 |
| JP6065862B2 (ja) * | 2013-04-10 | 2017-01-25 | 信越化学工業株式会社 | パターン形成方法、レジスト組成物、高分子化合物及び単量体 |
| US10274847B2 (en) * | 2017-09-19 | 2019-04-30 | Taiwan Semiconductor Manufacturing Co., Ltd. | Humidity control in EUV lithography |
| WO2019221243A1 (ja) * | 2018-05-18 | 2019-11-21 | Ａｇｃ株式会社 | 含フッ素ポリマーの製造方法および含フッ素イオン交換ポリマーの製造方法 |
| KR102810176B1 (ko) * | 2023-05-23 | 2025-05-23 | 인하대학교 산학협력단 | 주쇄 절단형 고불소화 고분자 포토레지스트, 이의 제조방법 및 이의 용도 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3776729A (en) * | 1971-02-22 | 1973-12-04 | Ibm | Photosensitive dielectric composition and process of using the same |
| US5283148A (en) * | 1992-09-18 | 1994-02-01 | Minnesota Mining And Manufacturing Company | Liquid toners for use with perfluorinated solvents |
| GB9400016D0 (en) * | 1994-01-04 | 1994-03-02 | Minnesota Mining & Mfg | 2-Fluoroacrylate ester polymers and use thereof as optical materials |
| JP3766245B2 (ja) | 1999-12-16 | 2006-04-12 | 株式会社ルネサステクノロジ | パタン形成方法および半導体装置の製造方法 |
| JP2001328964A (ja) | 2000-05-19 | 2001-11-27 | Tokyo Ohka Kogyo Co Ltd | 新規多環式不飽和炭化水素誘導体及びその製造方法 |
| JP2002040648A (ja) * | 2000-07-28 | 2002-02-06 | Sony Corp | 露光方法 |
| TW527523B (en) | 2000-12-04 | 2003-04-11 | Shinetsu Chemical Co | Polymer, resist composition and patterning process |
| JP2002196495A (ja) | 2000-12-22 | 2002-07-12 | Sumitomo Chem Co Ltd | 化学増幅型ポジ型レジスト組成物 |
| US6730452B2 (en) * | 2001-01-26 | 2004-05-04 | International Business Machines Corporation | Lithographic photoresist composition and process for its use |
| TWI300790B (en) | 2001-02-28 | 2008-09-11 | Shinetsu Chemical Co | Polymers, Resist Compositions and Patterning Process |
| JP3904064B2 (ja) | 2001-02-28 | 2007-04-11 | 信越化学工業株式会社 | 高分子化合物、レジスト材料及びパターン形成方法 |
| JP4524940B2 (ja) | 2001-03-15 | 2010-08-18 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
| TWI226973B (en) * | 2001-03-19 | 2005-01-21 | Fuji Photo Film Co Ltd | Positive resist composition |
| JP3912482B2 (ja) * | 2001-03-30 | 2007-05-09 | 信越化学工業株式会社 | 化学増幅ポジ型レジスト材料及びパターン形成方法 |
| JP3763403B2 (ja) * | 2001-06-05 | 2006-04-05 | セントラル硝子株式会社 | 高分子化合物、レジスト材料及びパターン形成方法 |
| JP4173352B2 (ja) * | 2001-12-25 | 2008-10-29 | 出光興産株式会社 | パーフルオロアダマンチルアクリル酸エステル類及びその中間体 |
| TWI264442B (en) | 2002-03-25 | 2006-10-21 | Shinetsu Chemical Co | Novel esters, polymers, resist compositions and patterning process |
| JP4186051B2 (ja) * | 2002-03-25 | 2008-11-26 | 信越化学工業株式会社 | 新規なエステル化合物、高分子化合物、レジスト材料及びパターン形成方法 |
-
2002
- 2002-11-29 JP JP2002349167A patent/JP4233314B2/ja not_active Expired - Fee Related
-
2003
- 2003-10-30 TW TW092130281A patent/TW200419309A/zh not_active IP Right Cessation
- 2003-11-28 US US10/501,459 patent/US7326512B2/en not_active Expired - Lifetime
- 2003-11-28 KR KR1020047017510A patent/KR100629124B1/ko not_active Expired - Fee Related
- 2003-11-28 WO PCT/JP2003/015247 patent/WO2004050725A1/en not_active Ceased
- 2003-11-28 AU AU2003302653A patent/AU2003302653A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7326512B2 (en) | 2008-02-05 |
| KR100629124B1 (ko) | 2006-09-27 |
| KR20040106428A (ko) | 2004-12-17 |
| WO2004050725A1 (en) | 2004-06-17 |
| AU2003302653A1 (en) | 2004-06-23 |
| JP4233314B2 (ja) | 2009-03-04 |
| JP2004182796A (ja) | 2004-07-02 |
| US20050130056A1 (en) | 2005-06-16 |
| TWI311235B (enExample) | 2009-06-21 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |