CA2493926A1 - Fluorinated polymers, photoresists and processes for microlithography - Google Patents
Fluorinated polymers, photoresists and processes for microlithography Download PDFInfo
- Publication number
- CA2493926A1 CA2493926A1 CA002493926A CA2493926A CA2493926A1 CA 2493926 A1 CA2493926 A1 CA 2493926A1 CA 002493926 A CA002493926 A CA 002493926A CA 2493926 A CA2493926 A CA 2493926A CA 2493926 A1 CA2493926 A1 CA 2493926A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- fluorine
- containing copolymer
- repeat unit
- unit derived
- 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.)
- Abandoned
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 12
- 229920002313 fluoropolymer Polymers 0.000 title abstract description 4
- 238000001393 microlithography Methods 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 17
- -1 alkyl hydroxymethylacrylate Chemical compound 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- ZEFPSJCRLPUDJQ-UHFFFAOYSA-N (2-hydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(O)C2(OC(=O)C=C)C3 ZEFPSJCRLPUDJQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- SVBJTBWVTZLHIZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)prop-2-enoate Chemical compound CC(C)(C)OC(=O)C(=C)CO SVBJTBWVTZLHIZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920001577 copolymer Polymers 0.000 claims description 54
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 40
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 239000012530 fluid Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 238000004090 dissolution Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 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 claims description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006347 bis(trifluoromethyl)hydroxymethyl group Chemical group [H]OC(*)(C(F)(F)F)C(F)(F)F 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 abstract description 19
- 239000000463 material Substances 0.000 abstract description 6
- 238000001459 lithography Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 32
- 241000630665 Hada Species 0.000 description 29
- 239000002253 acid Substances 0.000 description 25
- 238000011161 development Methods 0.000 description 18
- 238000003384 imaging method Methods 0.000 description 14
- 235000012431 wafers Nutrition 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003158 alcohol group Chemical group 0.000 description 6
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 6
- 229910001634 calcium fluoride Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000012527 feed solution Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- NYZSKEULTVZUAW-UHFFFAOYSA-N 2,2-bis(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1(C(F)(F)F)CO1 NYZSKEULTVZUAW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 2
- VLLPVDKADBYKLM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;triphenylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VLLPVDKADBYKLM-UHFFFAOYSA-M 0.000 description 2
- DAVVKEZTUOGEAK-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOC(=O)C(C)=C DAVVKEZTUOGEAK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- GJIDOLBZYSCZRX-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical class OCOC(=O)C=C GJIDOLBZYSCZRX-UHFFFAOYSA-N 0.000 description 2
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- 150000002848 norbornenes Chemical class 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- ZKVMMSGRDBQIOQ-UHFFFAOYSA-N 1,1,2-trichloro-1-fluoroethane Chemical compound FC(Cl)(Cl)CCl ZKVMMSGRDBQIOQ-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- LHCUYYJTVIYFEQ-UHFFFAOYSA-N 1-azido-3-(3-azidophenyl)sulfonylbenzene Chemical compound [N-]=[N+]=NC1=CC=CC(S(=O)(=O)C=2C=C(C=CC=2)N=[N+]=[N-])=C1 LHCUYYJTVIYFEQ-UHFFFAOYSA-N 0.000 description 1
- JYAPXNDXKHBOOP-UHFFFAOYSA-N 2-(1-cyanobutyldiazenyl)-2,4-dimethylpentanenitrile Chemical compound CCCC(C#N)N=NC(C)(C#N)CC(C)C JYAPXNDXKHBOOP-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- RFJVDJWCXSPUBY-UHFFFAOYSA-N 2-(difluoromethylidene)-4,4,5-trifluoro-5-(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)=C1OC(F)(F)C(F)(C(F)(F)F)O1 RFJVDJWCXSPUBY-UHFFFAOYSA-N 0.000 description 1
- JAIXJKPOHMMBKS-UHFFFAOYSA-N 2-chloro-1,1,3,4,4,5,6,6,6-nonafluoro-5-(trifluoromethyl)hex-1-ene Chemical compound FC(C(C(F)(F)F)(C(C(C(=C(F)F)Cl)F)(F)F)F)(F)F JAIXJKPOHMMBKS-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 241000272165 Charadriidae Species 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- MARDFMMXBWIRTK-UHFFFAOYSA-N [F].[Ar] Chemical compound [F].[Ar] MARDFMMXBWIRTK-UHFFFAOYSA-N 0.000 description 1
- VFQHLZMKZVVGFQ-UHFFFAOYSA-N [F].[Kr] Chemical compound [F].[Kr] VFQHLZMKZVVGFQ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- VIQRCOQXIHFJND-UHFFFAOYSA-N bicyclo[2.2.2]oct-2-ene Chemical compound C1CC2CCC1C=C2 VIQRCOQXIHFJND-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000012267 brine Substances 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
- 150000001721 carbon Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 229940057404 di-(4-tert-butylcyclohexyl)peroxydicarbonate Drugs 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 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
- 229920001519 homopolymer Polymers 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000005389 semiconductor device fabrication Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
- C08F114/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F114/18—Monomers containing fluorine
-
- 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
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/186—Monomers containing fluorine with non-fluorinated comonomers
-
- 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
- G03F7/0395—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 a backbone with alicyclic moieties
-
- 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
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39889902P | 2002-07-26 | 2002-07-26 | |
| US60/398,899 | 2002-07-26 | ||
| PCT/US2003/022912 WO2004011509A1 (en) | 2002-07-26 | 2003-07-23 | Fluorinated polymers, photoresists and processes for microlithography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2493926A1 true CA2493926A1 (en) | 2004-02-05 |
Family
ID=31188514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002493926A Abandoned CA2493926A1 (en) | 2002-07-26 | 2003-07-23 | Fluorinated polymers, photoresists and processes for microlithography |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20050203262A1 (enExample) |
| EP (1) | EP1551887A4 (enExample) |
| JP (1) | JP4303202B2 (enExample) |
| KR (1) | KR20050030639A (enExample) |
| CN (1) | CN1678646A (enExample) |
| AU (1) | AU2003254112A1 (enExample) |
| CA (1) | CA2493926A1 (enExample) |
| TW (1) | TW200403262A (enExample) |
| WO (1) | WO2004011509A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| KR100960838B1 (ko) * | 2004-04-27 | 2010-06-07 | 도오꾜오까고오교 가부시끼가이샤 | 액침 노광 프로세스용 레지스트 보호막 형성용 재료, 및 이보호막을 이용한 레지스트 패턴 형성 방법 |
| US7507522B2 (en) * | 2004-05-20 | 2009-03-24 | E. I. Dupont De Nemours And Company | Photoresists comprising polymers derived from fluoroalcohol-substituted polycyclic monomers |
| US7960087B2 (en) * | 2005-03-11 | 2011-06-14 | Fujifilm Corporation | Positive photosensitive composition and pattern-forming method using the same |
| US8530148B2 (en) * | 2006-12-25 | 2013-09-10 | Fujifilm Corporation | Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method |
| JP4554665B2 (ja) | 2006-12-25 | 2010-09-29 | 富士フイルム株式会社 | パターン形成方法、該パターン形成方法に用いられる多重現像用ポジ型レジスト組成物、該パターン形成方法に用いられるネガ現像用現像液及び該パターン形成方法に用いられるネガ現像用リンス液 |
| US8637229B2 (en) | 2006-12-25 | 2014-01-28 | Fujifilm Corporation | Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method |
| EP2138898B1 (en) | 2007-04-13 | 2014-05-21 | FUJIFILM Corporation | Method for pattern formation, and use of resist composition in said method |
| US8603733B2 (en) | 2007-04-13 | 2013-12-10 | Fujifilm Corporation | Pattern forming method, and resist composition, developer and rinsing solution used in the pattern forming method |
| US8034547B2 (en) | 2007-04-13 | 2011-10-11 | Fujifilm Corporation | Pattern forming method, resist composition to be used in the pattern forming method, negative developing solution to be used in the pattern forming method and rinsing solution for negative development to be used in the pattern forming method |
| KR100989567B1 (ko) | 2007-05-15 | 2010-10-25 | 후지필름 가부시키가이샤 | 패턴형성방법 |
| US8476001B2 (en) | 2007-05-15 | 2013-07-02 | Fujifilm Corporation | Pattern forming method |
| JP4617337B2 (ja) * | 2007-06-12 | 2011-01-26 | 富士フイルム株式会社 | パターン形成方法 |
| KR101705670B1 (ko) | 2007-06-12 | 2017-02-10 | 후지필름 가부시키가이샤 | 네가티브 톤 현상용 레지스트 조성물 및 이것을 사용한 패턴형성방법 |
| JP4590431B2 (ja) | 2007-06-12 | 2010-12-01 | 富士フイルム株式会社 | パターン形成方法 |
| US8617794B2 (en) | 2007-06-12 | 2013-12-31 | Fujifilm Corporation | Method of forming patterns |
| US8632942B2 (en) | 2007-06-12 | 2014-01-21 | Fujifilm Corporation | Method of forming patterns |
| KR101768929B1 (ko) * | 2010-09-30 | 2017-08-17 | 디아이씨 가부시끼가이샤 | 함불소 중합성 수지, 그것을 사용한 활성 에너지선 경화형 조성물 및 그 경화물 |
| CN102070755B (zh) * | 2010-11-09 | 2013-01-09 | 浙江理工大学 | 一种三嵌段氟化聚合物及制备方法 |
| JP6148112B2 (ja) * | 2013-04-02 | 2017-06-14 | リソテック ジャパン株式会社 | 光透過度測定方法 |
| DE102014118490B4 (de) | 2014-12-12 | 2022-03-24 | tooz technologies GmbH | Anzeigevorrichtungen |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3444148A (en) * | 1964-10-05 | 1969-05-13 | Du Pont | Copolymers of selected polyfluoroper-haloketone adducts with other selected ethylenic compounds |
| KR100263906B1 (ko) * | 1998-06-02 | 2000-09-01 | 윤종용 | 백본이 환상구조를 가지는 감광성 폴리머 및 이를 포함하는 레지스트 조성물 |
| EP1183571B1 (en) * | 1999-05-04 | 2010-06-02 | E.I. Du Pont De Nemours And Company | Fluorinated photoresists and processes for microlithography |
| US6872503B2 (en) * | 2000-05-05 | 2005-03-29 | E. I. Du Pont De Nemours And Company | Copolymers for photoresists and processes therefor |
| US20030022097A1 (en) * | 2000-05-05 | 2003-01-30 | Arch Specialty Chemicals, Inc | Tertiary-butyl acrylate polymers and their use in photoresist compositions |
| WO2002031596A1 (en) * | 2000-10-12 | 2002-04-18 | University Of North Carolina At Chapel Hill | Co2-processes photoresists, polymers, and photoactive compounds for microlithography |
| US6838225B2 (en) * | 2001-01-18 | 2005-01-04 | Jsr Corporation | Radiation-sensitive resin composition |
-
2003
- 2003-07-23 WO PCT/US2003/022912 patent/WO2004011509A1/en not_active Ceased
- 2003-07-23 CA CA002493926A patent/CA2493926A1/en not_active Abandoned
- 2003-07-23 AU AU2003254112A patent/AU2003254112A1/en not_active Abandoned
- 2003-07-23 CN CNA03817569XA patent/CN1678646A/zh active Pending
- 2003-07-23 JP JP2004524696A patent/JP4303202B2/ja not_active Expired - Fee Related
- 2003-07-23 US US10/521,412 patent/US20050203262A1/en not_active Abandoned
- 2003-07-23 KR KR1020057001370A patent/KR20050030639A/ko not_active Withdrawn
- 2003-07-23 EP EP03771715A patent/EP1551887A4/en not_active Withdrawn
- 2003-07-25 TW TW092120427A patent/TW200403262A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003254112A1 (en) | 2004-02-16 |
| TW200403262A (en) | 2004-03-01 |
| WO2004011509A1 (en) | 2004-02-05 |
| US20050203262A1 (en) | 2005-09-15 |
| CN1678646A (zh) | 2005-10-05 |
| KR20050030639A (ko) | 2005-03-30 |
| JP4303202B2 (ja) | 2009-07-29 |
| EP1551887A4 (en) | 2008-07-02 |
| JP2005533907A (ja) | 2005-11-10 |
| EP1551887A1 (en) | 2005-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |