JP2005171093A - 半導体リソグラフィー用共重合体の製造方法及び該方法により得られる半導体リソグラフィー用共重合体 - Google Patents
半導体リソグラフィー用共重合体の製造方法及び該方法により得られる半導体リソグラフィー用共重合体 Download PDFInfo
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- JP2005171093A JP2005171093A JP2003413438A JP2003413438A JP2005171093A JP 2005171093 A JP2005171093 A JP 2005171093A JP 2003413438 A JP2003413438 A JP 2003413438A JP 2003413438 A JP2003413438 A JP 2003413438A JP 2005171093 A JP2005171093 A JP 2005171093A
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- Prior art keywords
- copolymer
- polymerization
- semiconductor lithography
- monomer
- solution
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 74
- 238000001459 lithography Methods 0.000 title claims abstract description 53
- 239000004065 semiconductor Substances 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 124
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 115
- 239000002904 solvent Substances 0.000 claims abstract description 62
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000001301 oxygen Substances 0.000 claims abstract description 30
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 8
- 239000000243 solution Substances 0.000 claims description 81
- -1 acrylate ester Chemical class 0.000 claims description 47
- 239000003112 inhibitor Substances 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 24
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- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 150000002596 lactones Chemical group 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical compound CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 2
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical compound O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 claims description 2
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 16
- 239000003513 alkali Substances 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- 239000012986 chain transfer agent Substances 0.000 description 12
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 12
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- 239000000758 substrate Substances 0.000 description 11
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 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 7
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 7
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- 238000002360 preparation method Methods 0.000 description 7
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- 238000001914 filtration Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- YNGIFMKMDRDNBQ-UHFFFAOYSA-N 3-ethenylphenol Chemical compound OC1=CC=CC(C=C)=C1 YNGIFMKMDRDNBQ-UHFFFAOYSA-N 0.000 description 3
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000002292 Radical scavenging effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical group C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 2
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- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- SNRUBQQJIBEYMU-NJFSPNSNSA-N dodecane Chemical group CCCCCCCCCCC[14CH3] SNRUBQQJIBEYMU-NJFSPNSNSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
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- 230000001376 precipitating effect Effects 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 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
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZESXUEKAXSBANL-UHFFFAOYSA-N trifluoromethyl prop-2-enoate Chemical compound FC(F)(F)OC(=O)C=C ZESXUEKAXSBANL-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
Abstract
【課題】半導体製造の微細なパターン形成に用いられるレジスト膜形成用組成物等の塗膜形成用組成物に好適に用いられる半導体リソグラフィー用共重合体の製造方法と、この製造方法で得られる、ハイポリマーを含まず、保存安定性に優れ、半導体リソグラフィーに用いたときにレジストパターンの欠陥が極めて少ない共重合体の提供。
【解決手段】本発明は、重合溶媒中、重合開始剤の存在下にエチレン性二重結合を有する2種類以上のモノマーをラジカル重合させて半導体リソグラフィー用共重合体を製造する方法であって、モノマーを含む溶液中に重合抑制成分としてモノマーに対して20モルppm以上の重合禁止剤又は400モルppm以上の酸素を共存させ、この溶液によりラジカル重合させることを特徴とする半導体リソグラフィー用共重合体の製造方法及び該製造方法で製造された半導体リソグラフィー用共重合体に関する。
【選択図面】なし
Description
Pn ∝[M]/[R・] … (1)
(ここで、Pnは生成するポリマーの分子量、[M]はモノマー濃度、[R・]はラジカル濃度を表す。)
(1)重合禁止剤量の定量方法
モノマー溶液中の重合禁止剤濃度は、HPLCにより定量した。分析条件及び定量方法は以下の通りである。
検出器: UV254nm
カラム: GLサイエンス Inertsil ODS−3V
移動相: アセトニトリル/水=9/1(容量比)
試 料: モノマー溶液0.1gをアセトニトリル1mlに溶解して試料を調製した。
定 量: ビスフェノールAを内部標準物質として内部標準法にて定量した。
モノマー溶液の溶存酸素量は、溶存酸素計にて測定した。測定装置及び測定条件は以下の通りである。
装 置: オービスフェア model 3650
測定条件:温度25〜30℃、通液速度50ml/min
共重合体中のハイポリマーは、GPCにより定量した。分析条件及び定量方法は以下の通りである。
装 置: 東ソー製GPC8020
検出器: 示差屈折率(RI)検出器
カラム: 昭和電工製KF−804L(×3本)
試 料: 重合終了後の重合液をサンプリングし、得られたポリマー溶液が1%となるようにテトラヒドロフランで希釈して試料を調製した。
定 量: GPCに、上記試料を15μl注入し、目的とするポリマーのピーク面積Apを求め、次いで上記試料を150μl注入し、ハイポリマーピークの面積Ahを求めた。この結果から次の計算式(2)に基づいてポリマー中のハイポリマー含有量(%)を算出した。
Ah
ハイポリマーの含有量(%)=――――――――――×100 … (2)
(Ap×10+Ah)
共重合体の15%プロピレングリコールメチルエーテルアセテート(以下、「PGMEA」と記す。)溶液を0.05μmのメンブレンフィルターでろ過し、3ヶ月間室温にて保管後の液中パーティクルを測定した。
装 置: リオン社製KS−40B
評 価: パーティクルサイズ0.2μm以上の異物が100個/ml未満の場合を○、1000個/ml以上の場合を×とした。
比較例1〜3
Claims (12)
- 重合溶媒中、重合開始剤の存在下にエチレン性二重結合を有する2種類以上のモノマーをラジカル重合させて半導体リソグラフィー用共重合体を製造する方法であって、モノマーを含む溶液中に重合抑制成分として、モノマーに対して20モルppm以上の重合禁止剤又は400モルppm以上の酸素を共存させ、この溶液によりラジカル重合させることを特徴とする半導体リソグラフィー用共重合体の製造方法。
- モノマーを含む溶液が重合開始剤を含み、該溶液中に共存させる重合禁止剤の量が、前記溶液中の重合開始剤に対して0.1モル%以上である請求項1に記載の半導体リソグラフィー用共重合体の製造方法。
- 重合禁止剤がハイドロキノン、ベンゾキノン、カテコール、フェノチアジン、N−ニトロソフェニルヒドロキシアミン、2,2,6,6−テトラメチルピペリジン−1−オキシルフリーラジカル及びこれらの誘導体から選ばれる1種以上の化合物である請求項1又は2に記載の半導体リソグラフィー用共重合体の製造方法。
- モノマーを含む溶液が重合開始剤を含み、該溶液中に共存させる酸素の量が、前記溶液中の重合開始剤に対して2モル%以上である請求項1に記載の半導体リソグラフィー用共重合体の製造方法。
- 半導体リソグラフィー用共重合体が、アクリル酸エステル系モノマー及び/又はメタクリル酸エステル系モノマーの少なくとも一種を共重合して得られる共重合体である請求項1から4のいずれかに記載の半導体リソグラフィー用共重合体の製造方法。
- 半導体リソグラフィー用共重合体が、酸を作用させることによりアルカリ溶液への溶解性が変化する構造を含むものである請求項1から5のいずれかに記載の半導体リソグラフィー用共重合体の製造方法。
- 半導体リソグラフィー用共重合体が、脂環構造を含むものである請求項1から6のいずれかに記載の半導体リソグラフィー用共重合体の製造方法。
- 脂環構造が、シクロペンタン環、シクロヘキサン環、イソボルナン環、ノルボルナン環、アダマンタン環、トリシクロデカン環、テトラシクロドデカン環から選ばれる構造である請求項7に記載の半導体リソグラフィー用共重合体の製造方法。
- 半導体リソグラフィー用共重合体が、ラクトン構造を含むものである請求項1から8のいずれかに記載の製造方法。
- 請求項1から9のいずれかに記載の製造方法により得られることを特徴とする半導体リソグラフィー用共重合体。
- 分子量10万以上の高分子量成分の含有率が0.1%以下である請求項10に記載の半導体リソグラフィー用共重合体。
- 請求項10又は11に記載の共重合体を含むことを特徴とする半導体リソグラフィー用組成物。
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TW093137156A TW200530272A (en) | 2003-12-11 | 2004-12-02 | A preparation process of copolymer for semiconductor lithography and a copolymer for semiconductor lithography available by this process |
US11/005,914 US7045582B2 (en) | 2003-12-11 | 2004-12-06 | Preparation process of copolymer for semiconductor lithography and a copolymer for semiconductor lithography available by this process |
KR1020040103216A KR101124184B1 (ko) | 2003-12-11 | 2004-12-08 | 반도체 리소그래피용 공중합체의 제조 방법 및 상기방법으로 수득가능한 반도체 리소그래피용 공중합체 |
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TW507116B (en) * | 2000-04-04 | 2002-10-21 | Sumitomo Chemical Co | Chemically amplified positive resist composition |
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- 2004-12-02 TW TW093137156A patent/TW200530272A/zh unknown
- 2004-12-06 US US11/005,914 patent/US7045582B2/en active Active
- 2004-12-08 KR KR1020040103216A patent/KR101124184B1/ko active IP Right Grant
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JP2008163319A (ja) * | 2006-12-06 | 2008-07-17 | Maruzen Petrochem Co Ltd | 半導体リソグラフィー用共重合体とその製造方法 |
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JP2009126887A (ja) * | 2007-11-20 | 2009-06-11 | Fujifilm Corp | シリコーン樹脂の製造方法 |
JP2010202698A (ja) * | 2009-02-27 | 2010-09-16 | Maruzen Petrochem Co Ltd | 半導体リソグラフィー用共重合体の製造方法 |
JP2010270260A (ja) * | 2009-05-22 | 2010-12-02 | Maruzen Petrochem Co Ltd | フォトレジスト用共重合体ならびにその製造方法および保存方法 |
WO2011126101A1 (en) * | 2010-04-07 | 2011-10-13 | Fujifilm Corporation | Curable composition for imprints and producing method of polymerizable monomer for imprints |
JP2012246496A (ja) * | 2012-08-24 | 2012-12-13 | Mitsubishi Rayon Co Ltd | 重合体の製造方法、およびレジスト組成物の製造方法 |
JP2014196512A (ja) * | 2014-07-14 | 2014-10-16 | 三菱レイヨン株式会社 | 重合体の製造方法、およびレジスト組成物の製造方法 |
Also Published As
Publication number | Publication date |
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KR20050058203A (ko) | 2005-06-16 |
US7045582B2 (en) | 2006-05-16 |
US20050131184A1 (en) | 2005-06-16 |
KR101124184B1 (ko) | 2012-03-27 |
TW200530272A (en) | 2005-09-16 |
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