JP6394798B2 - ブロック共重合体 - Google Patents
ブロック共重合体Info
- Publication number
- JP6394798B2 JP6394798B2 JP2017517260A JP2017517260A JP6394798B2 JP 6394798 B2 JP6394798 B2 JP 6394798B2 JP 2017517260 A JP2017517260 A JP 2017517260A JP 2017517260 A JP2017517260 A JP 2017517260A JP 6394798 B2 JP6394798 B2 JP 6394798B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- block copolymer
- block
- atom
- carbon atoms
- 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.)
- Active
Links
- 229920001400 block copolymer Polymers 0.000 title claims description 123
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 49
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 37
- 125000004450 alkenylene group Chemical group 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 33
- 125000004419 alkynylene group Chemical group 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000004434 sulfur atom Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229920006254 polymer film Polymers 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 20
- -1 —S (═O) 2 — Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 17
- 125000000304 alkynyl group Chemical group 0.000 description 17
- 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 16
- 239000000178 monomer Substances 0.000 description 16
- 238000001654 grazing-incidence X-ray scattering Methods 0.000 description 14
- 238000002441 X-ray diffraction Methods 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 150000002738 metalloids Chemical group 0.000 description 12
- 238000005191 phase separation Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005530 etching Methods 0.000 description 6
- 230000005660 hydrophilic surface Effects 0.000 description 6
- 230000005661 hydrophobic surface Effects 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
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- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002086 nanomaterial Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000003878 thermal aging Methods 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- LVJZCPNIJXVIAT-UHFFFAOYSA-N 1-ethenyl-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(C=C)C(F)=C1F LVJZCPNIJXVIAT-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 239000002070 nanowire Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 2
- IDSLBLWCPSAZBL-UHFFFAOYSA-N 2-cyanopropan-2-yl benzenecarbodithioate Chemical compound N#CC(C)(C)SC(=S)C1=CC=CC=C1 IDSLBLWCPSAZBL-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000446313 Lamella Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 238000000089 atomic force micrograph Methods 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000002073 nanorod Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
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- 239000012985 polymerization agent Substances 0.000 description 2
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- 230000007261 regionalization Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QCOOBRZXUXNIJP-UHFFFAOYSA-N 1-(silylamino)silylhexane Chemical compound C(CCCCC)[SiH2]N[SiH3] QCOOBRZXUXNIJP-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- QRAZRBGYBYIGRL-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)phenol Chemical compound C1CC(CCCCC)CCC1C1=CC=C(O)C=C1 QRAZRBGYBYIGRL-UHFFFAOYSA-N 0.000 description 1
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
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- 125000003368 amide group Chemical group 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
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- 230000005484 gravity Effects 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
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- 230000000007 visual effect Effects 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B81—MICROSTRUCTURAL TECHNOLOGY
- B81C—PROCESSES OR APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OR TREATMENT OF MICROSTRUCTURAL DEVICES OR SYSTEMS
- B81C1/00—Manufacture or treatment of devices or systems in or on a substrate
- B81C1/00388—Etch mask forming
- B81C1/00428—Etch mask forming processes not provided for in groups B81C1/00396 - B81C1/0042
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/002—Processes for applying liquids or other fluent materials the substrate being rotated
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Description
本明細書において用語アルコキシ基は、特に規定しない限り、炭素数1〜20、炭素数1〜16、炭素数1〜12、炭素数1〜8または炭素数1〜4のアルコキシ基を意味し得る。前記アルコキシ基は直鎖型、分枝型または環状アルコキシ基であり得、任意的に一つ以上の置換基によって置換され得る。
第2Fブロックは下記の化学式12で表示され得る。
3nm−1〜5nm−1=nq/(2×π)
数式1でnは前記鎖形成原子の数であり、qは、前記ブロック共重合体に対するX線回折分析でピークが観察される最も小さい散乱ベクター(q)であるか、あるいは最も大きいピーク面積のピークが観察される散乱ベクター(q)である。また、数式1でπは、円周率を意味する。
NMR分析は三重共鳴5mm探針(probe)を有するVarian Unity Inova(500MHz)分光計を含むNMR分光計を使って常温で遂行した。NMR測定用溶媒( CDCl3)に分析対象物質を約10mg/ml程度の濃度に希釈させて使用し、化学的移動はppmで表現した。
br=広い信号、s=単一線、d=二重線、dd=二重二重線、t=三重線、dt=二重三重線、q=四重線、p=五重線、m=多重線。
数平均分子量(Mn)および分子量分布はGPC(Gel permeation chromatography)を使って測定した。5mLバイアル(vial)に実施例または比較例のブロック共重合体またはマクロ開始剤などの分析対象物を入れ、約1mg/mL程度の濃度になるようにTHF(tetrahydro furan)に希釈する。その後、Calibration用標準試料と分析しようとする試料をsyringe filter(pore size:0.45μm)を通じて濾過させた後測定した。分析プログラムはAgilent technologies社のChemStationを使用し、試料のelution timeをcalibration curveと比較して重量平均分子量(Mw)および数平均分子量(Mn)をそれぞれ求め、その比率(Mw/Mn)で分子量分布(PDI)を計算した。GPCの測定条件は下記の通りである。
機器:Agilent technologies社の1200 series
カラム:Polymer laboratories社のPLgel mixed B 2個使用
溶媒:THF
カラム温度:35℃
サンプル濃度:1mg/mL、200L注入
標準試料:ポリスチレン(Mp:3900000、723000、316500、52200、31400、7200、3940、485)
単量体(A)の合成
下記の化学式AでRはメチル基であり、Xは−C(=O)−X1−であり、前記でX1は酸素原子であり、Yは−Q−Pで表示される置換基がパラ位置に置換されているフェニレン基であり、前記でQは−K−C(=O)−X2−であり、Kはエチレン基であり、X2は酸素原子であり、Pは直鎖ヘキシル基である単量体(A)は次の方式で合成した。para−クマリック酸(p−Coumaric acid)(10g)、1−ヘキサンオール(6.2g)およびpara−トルエンスルホン酸(10.5g)を100mLの1、4−ジオキサンが入っているフラスコに入れて105℃で還流させながら反応させた。反応完了後ジクロロメタンを混合し、シリカカラムを通じてpara−トルエンスルホン酸を除去した。その後、酢酸エチルおよびヘキサンを利用してシリカカラムで精製し、残存する1−ヘキサンオールを減圧蒸留で除去して液状のpara−クマリック酸ヘキシル(8.3g、収得率55%)を得た。
1H−NMR(CDCl3):δ7.61(d、1H);δ7.41(d、2H);δ6.83(d、2H);δ6.28(d、1H);5.47(s、1H);δ4.17(t、2H);δ1.68(tt、2H);δ1.38(tt、2H);δ1.31(m、4H);δ0.88(t、3H)。
1H−NMR(CDCl3):δ7.67(d、1H);δ7.55(d、2H);δ7.16(d、2H);δ6.41(d、1H);δ6.36(s、1H);δ5.78(s、1H);δ4.20(t、2H);δ2.06(s、3H);δ1.70(tt、2H);δ1.40(tt、2H);δ1.33(m、4H);δ0.91(t、3H)。
フラスコに前記単量体(A)、RAFT試薬(CPDB、2−cyanoprop−2−yl−benzodithioate)および熱開始剤(AIBN、azobisisobutyronitrile)を20:1:0.5(単量体(A):RAFT試薬:熱開始剤)の当量比率で入れてアニソール(anisole)で希釈して約30重量%の固形分濃度の溶液を製造した。引き続き製造された溶液を窒素雰囲気の約70℃で2時間程度反応させた後、メタノールに沈殿させて重合体(A)を得た。前記重合体(A)の数平均分子量(Mn)と分子量分布(Mw/Mn)はそれぞれ8,100と1.35であった。
実施例1の化学式AでRはメチル基であり、Xは−C(=O)−X1−で、X1は酸素原子であり、Yは−Q−Pで表示される置換基がパラ位置に置換されているフェニレンであり、Qはシクロヘキシレン基であり、Pは前記シクロヘキシレン基のパラ位置に置換されている直鎖ペンチル基である単量体(B)は、次の方法で合成した。4−(トランス−4−ペンチルシクロヘキシル)フェノール(15.0g)およびメタクリル酸(5.8g)をフラスコに入れて400mLのジクロロメタンに溶かした。製造された溶液にジシクロヘキシルカルボジイミド(DCC)(13.8g)およびN、N−ジメチルアミノピリジン(DMAP)(3.0g)を添加して反応させた。反応後でジクロロメタンを除去して酢酸エチルおよびヘキサンを利用したシリカカラムで精製して溶媒を除去して白色固体の単量体(B)(16.7g、収得率87%)を得た。
1H−NMR(CDCl3):δ7.21(d、2H);δ7.02(d、2H);δ6.33(s、1H);δ5.73(s、1H);δ2.47(t、1H);δ2.06(s、3H);δ1.88(t、4H);1.43(q、2H);δ1.33−1.21(m、8H);δ1.04(q、2H);δ0.90(t、3H)
フラスコに前記単量体(B)、RAFT試薬(CPDB、2−cyanoprop−2−yl−benzodithioate)および熱開始剤(AIBN、azobisisobutyronitrile)を15:1:0.1(単量体(B):RAFT試薬:熱開始剤)の当量比率で入れてアニソール(anisole)で希釈して約22重量%の固形分濃度の溶液を製造した。その後混合液を窒素雰囲気の70℃で約3時間の間反応させてマクロ開始剤を収得した。前記マクロ開始剤の数平均分子量(Mn)と分子量分布(Mw/Mn)はそれぞれ7,400と1.35であり、DSC分析時に約50℃で溶融点を示した。
実施例2で合成されたブロック共重合体(B)を使って自己組織化された高分子膜を形成し、その結果を確認した。具体的に共重合体を溶媒に約1.0重量%の濃度に溶解させて製造されたコート液をシリコンウェハ上に3000rpmの速度で60秒の間スピンコートし、約220℃での熱的熟成(thermal annealing)を通じて自己組織化されたブロック共重合体を含む膜を形成した。図1は前記のように形成された高分子膜のAFMイメージであり、図2はSEMイメージである。
Claims (16)
- 下記の化学式1で表示される単位を有する第1ブロック及び下記の化学式2で表示される第2ブロックを含む、ブロック共重合体:
- 化学式1のXが−C(=O)−O−または−O−C(=O)−である、請求項1に記載のブロック共重合体。
- 化学式1のYは−Q−Pで表示される置換基が少なくとも一つ置換されている炭素数6〜12のアリール基である、請求項1に記載のブロック共重合体。
- 化学式1のYは−Q−Pで表示される置換基が少なくとも一つ置換されているフェニル基であり、前記−Q−Pで表示される置換基は、前記化学式1のX位置を基準として前記フェニル基のパラ位置に置換されている、請求項1に記載のブロック共重合体。
- 置換基−Q−PのQは−K−C(=O)−O−または−O−C(=O)−K−であり、前記でKは炭素数2〜20のアルキレン基である、請求項1に記載のブロック共重合体。
- 置換基−Q−PのQは炭素数3〜12のシクロアルキレン基である、請求項1に記載のブロック共重合体。
- 置換基−Q−PのPは炭素数3〜30のアルキル基である、請求項1に記載のブロック共重合体。
- 化学式2でX 2 は、単一結合、酸素原子、硫黄原子または−S(=O) 2 −であり、Wは3個以上のハロゲン原子で置換された炭素数6〜12のアリール基である、請求項1に記載のブロック共重合体。
- 化学式3のX 2 は、単一結合、酸素原子、硫黄原子または−S(=O) 2 −である、請求項9に記載のブロック共重合体。
- R1〜R5が含むハロゲン原子の数は4個以上である、請求項9に記載のブロック共重合体。
- R1〜R5が含むハロゲン原子の数は5個以上である、請求項9に記載のブロック共重合体。
- ハロゲン原子はフッ素原子である、請求項1に記載のブロック共重合体。
- 自己組織化された請求項1に記載のブロック共重合体を含む、高分子膜。
- 自己組織化された請求項1に記載のブロック共重合体を含む高分子膜を基板上に形成することを含む、高分子膜の形成方法。
- 基板および前記基板上に形成されており、自己組織化された請求項1に記載のブロック共重合体を含む高分子膜を有する積層体で前記ブロック共重合体の第1ブロックまたはそれとは異なるブロックを選択的に除去する過程を含む、パターン形成方法。
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EP3078690B1 (en) | 2013-12-06 | 2021-01-27 | LG Chem, Ltd. | Block copolymer |
WO2015084133A1 (ko) | 2013-12-06 | 2015-06-11 | 주식회사 엘지화학 | 블록 공중합체 |
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CN107075053B (zh) | 2014-09-30 | 2019-05-21 | 株式会社Lg化学 | 嵌段共聚物 |
JP6538157B2 (ja) | 2014-09-30 | 2019-07-03 | エルジー・ケム・リミテッド | ブロック共重合体 |
JP6505212B2 (ja) | 2014-09-30 | 2019-04-24 | エルジー・ケム・リミテッド | ブロック共重合体 |
CN107077066B9 (zh) | 2014-09-30 | 2021-05-14 | 株式会社Lg化学 | 制造图案化基底的方法 |
EP3202798B1 (en) | 2014-09-30 | 2022-01-12 | LG Chem, Ltd. | Block copolymer |
WO2016053010A1 (ko) | 2014-09-30 | 2016-04-07 | 주식회사 엘지화학 | 블록 공중합체 |
EP3202802B1 (en) | 2014-09-30 | 2022-11-23 | LG Chem, Ltd. | Block copolymer |
WO2016053011A1 (ko) | 2014-09-30 | 2016-04-07 | 주식회사 엘지화학 | 블록 공중합체 |
KR101880212B1 (ko) | 2014-09-30 | 2018-07-20 | 주식회사 엘지화학 | 블록 공중합체 |
US10703897B2 (en) | 2014-09-30 | 2020-07-07 | Lg Chem, Ltd. | Block copolymer |
CN107078026B (zh) | 2014-09-30 | 2020-03-27 | 株式会社Lg化学 | 图案化基底的制备方法 |
EP3202799B1 (en) | 2014-09-30 | 2021-08-25 | LG Chem, Ltd. | Block copolymer |
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US20170226235A1 (en) | 2017-08-10 |
EP3202798A4 (en) | 2018-04-25 |
WO2016053001A1 (ko) | 2016-04-07 |
US10295908B2 (en) | 2019-05-21 |
EP3202798A1 (en) | 2017-08-09 |
EP3202798B1 (en) | 2022-01-12 |
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CN107075056B (zh) | 2019-10-08 |
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