JPWO2011111683A1 - エレクトロクロミック材料とその製造方法 - Google Patents
エレクトロクロミック材料とその製造方法 Download PDFInfo
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- JPWO2011111683A1 JPWO2011111683A1 JP2012504461A JP2012504461A JPWO2011111683A1 JP WO2011111683 A1 JPWO2011111683 A1 JP WO2011111683A1 JP 2012504461 A JP2012504461 A JP 2012504461A JP 2012504461 A JP2012504461 A JP 2012504461A JP WO2011111683 A1 JPWO2011111683 A1 JP WO2011111683A1
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- 239000000463 material Substances 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 88
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000000732 arylene group Chemical group 0.000 claims abstract description 12
- 125000000962 organic group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 229920001400 block copolymer Polymers 0.000 claims abstract description 3
- 239000000412 dendrimer Substances 0.000 claims abstract description 3
- 229920000736 dendritic polymer Polymers 0.000 claims abstract description 3
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 3
- -1 boronic acid ester Chemical class 0.000 claims description 71
- 239000000178 monomer Substances 0.000 claims description 50
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- 238000006880 cross-coupling reaction Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
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- 125000005620 boronic acid group Chemical group 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
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- 238000005658 halogenation reaction Methods 0.000 claims description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 description 57
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- 238000011161 development Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 22
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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- 239000002019 doping agent Substances 0.000 description 10
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- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
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- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 6
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 5
- AJRKAJXERLIXNM-UHFFFAOYSA-N 2-methyl-4-(sulfanylmethyl)-1,3-thiazole-5-carbaldehyde Chemical compound CC1=NC(CS)=C(C=O)S1 AJRKAJXERLIXNM-UHFFFAOYSA-N 0.000 description 5
- JAFLQJGIOUUPCF-UHFFFAOYSA-N 2-methyl-6-[9-methyl-6-(2-methylthieno[3,4-d][1,3]thiazol-6-yl)carbazol-3-yl]thieno[3,4-d][1,3]thiazole Chemical compound C=12SC(C)=NC2=CSC=1C(C=C1C2=C3)=CC=C1N(C)C2=CC=C3C1=C2SC(C)=NC2=CS1 JAFLQJGIOUUPCF-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- WCUUOYNIEQTQIO-UHFFFAOYSA-N ethyl 2,4-dimethyl-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C=1OC(C)=NC=1C WCUUOYNIEQTQIO-UHFFFAOYSA-N 0.000 description 5
- BXOIIRQIGYJTTB-UHFFFAOYSA-N ethyl 2,4-dimethyl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C)=NC=1C BXOIIRQIGYJTTB-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- XJHAYGTUZUMPBX-UHFFFAOYSA-N thieno[3,4-d][1,3]thiazole Chemical compound S1C=C2SC=NC2=C1 XJHAYGTUZUMPBX-UHFFFAOYSA-N 0.000 description 5
- 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 4
- WPKOSARROZVVHH-UHFFFAOYSA-N 2-methyl-4-(sulfanylmethyl)-1,3-oxazole-5-carbaldehyde Chemical compound CC1=NC(CS)=C(C=O)O1 WPKOSARROZVVHH-UHFFFAOYSA-N 0.000 description 4
- SZXIDIBDWKBMGJ-UHFFFAOYSA-N 2-methylthieno[3,4-d][1,3]oxazole Chemical compound S1C=C2OC(C)=NC2=C1 SZXIDIBDWKBMGJ-UHFFFAOYSA-N 0.000 description 4
- FXZIBQSURGURTB-UHFFFAOYSA-N 6-bromo-2-methylthieno[3,4-d][1,3]thiazole Chemical compound S1C(Br)=C2SC(C)=NC2=C1 FXZIBQSURGURTB-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- LHOWRPZTCLUDOI-UHFFFAOYSA-K iron(3+);triperchlorate Chemical compound [Fe+3].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O LHOWRPZTCLUDOI-UHFFFAOYSA-K 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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])[H] 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002900 organolithium compounds Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000008093 supporting effect Effects 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical compound [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical class S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/1514—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
- G02F1/1516—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising organic material
- G02F1/15165—Polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
Q2−W−Q2 ・・・(4)
(式中、Wは、アリーレン基又は2価の複素芳香環基であり、Q2は、−MgCl、−MgBr、−MgI、−ZnCl、−ZnBr、−ZnI、−Sn(R1)3(R1は、夫々独立して炭素数1〜20のアルキル基又はアルコキシ基である)、ボロン酸基及びボロン酸エステル基から選ばれる1種である)で示される化合物とを、クロスカップリング反応させる工程、又は、塩基存在下で、下記化学式(2)
Q4−W−Q4 ・・・(6)
(式中、Wは、前記と同じであり、Q4は、夫々独立してハロゲン原子である)
で示される化合物とクロスカップリング反応させる工程によって、下記化学式(7)
チオアセトアミドと2−クロロアセト酢酸エチルとを用いた下記化学式(8)に示されるエチル2,4−ジメチル−1,3−チアゾール−5−カルボキシレートの合成を以下に示す。以下式中のエチル基をEtと略記する。
1H−NMR(500MHz、CDCl3、TMS)δ:4.30(2H,dd)、2.69(3H,s)、2.67(3H,s)、1.36(3H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:4.91(2H,s)、4.35(2H,dd)、2.71(3H,s)、1.38(3H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:4.33(2H,dd)、4.16(2H,d)、2.69(3H,s)、2.20(1H,t)、1.37(3H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:9.87(1H,s)、4.07(2H,s)、2.77(3H,s)、2.20(1H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:7.45(1H,d)、7.16(1H,d)、2.73(3H,s)
13C−NMR(500MHz、CDCl3、TMS)δ:173.46、159.94、134.62、109.73、109.34、21.21
1H−NMR(500MHz、CDCl3、TMS)δ:7.15(1H,s)、2.73(3H、s)
1H−NMR(500MHz、CDCl3、TMS)δ:7.05(2H,s)、8.76(2H,d)、8.26(2H,d)、7.47(2H,s)3.90(3H,s)、2.82(6H,s)
化学式(13)で示される6−ブロモ−2−メチルチエノ[3,4−d][1,3]チアゾールと5,7−ジトリブチルスズ−2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシンとを用いたスティルクロスカップリング反応による、下記化学式(15)に示される2−メチル−6−[7−(2−メチルチエノ[3,4−d][1,3]チアゾール−6−イル)−2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシン−5−イル]チエノ[3,4−d][1,3]チアゾールの合成を以下に示す。
1H−NMR(500MHz、CDCl3、TMS)δ:7.36(2H,s)、4.37(2H,m)、4.29(2H,m)、2.74(6H,s)
アセトアミドと2−クロロアセト酢酸エチルとを用いることによる、下記化学式(16)に示されるエチル2,4−ジメチル−1,3−オキサゾール−5−カルボキシレートの合成を以下に示す。
1H−NMR(500MHz、CDCl3、TMS)δ:4.38(2H,dd)、2.49(3H,s)、2.43(3H,s)、1.39(3H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:4.64(2H,s)、4.41(2H,dd)、2.53(3H,s)、1.42(3H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:4.40(2H,dd)、3.90(2H,d)、2.52(3H,s)、2.09(1H,t)、1.40(3H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:9.84(1H,s)、3.89(2H,d)、2.56(3H,s)、2.20(1H,t)
1H−NMR(500MHz、CDCl3、TMS)δ:6.98(1H,d)、6.69(1H,d)、2.70(3H,s)
1H−NMR(500MHz、CDCl3、TMS)δ:6.68(1H,s)、2.70(3H,s)
1H−NMR(500MHz、CDCl3、TMS)δ:6.89(2H,s)、4.37(2H,m)、4.29(2H,m)、2.71(6H,s)
実施例1で得られた9−メチル−3,6−ビス(2−メチルチエノ[3,4−d][1,3]チアゾール−6−イル)−9H−カルバゾールを0.1Mテトラブチルアンモニウムパークロレート/プロピレンカーボネート溶液に0.01Mの濃度で溶解させ、モノマー含有電解液を調整した。
実施例2で得られた2−メチル−6−[7−(2−メチルチエノ[3,4−d][1,3]チアゾール−6−イル)−2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシン−5−イル]チエノ[3,4−d][1,3]チアゾールを用いて、前記実施例4の手法と同様にして、発色時及び消色時のそれぞれにおいてUV−Visスペクトルを測定することにより、当該重合体のエレクトロクロミック特性を評価した。
実施例3で得られた2−メチル−6−[7−(2−メチルチエノ[3,4−d][1,3]オキサゾール−6−イル)−2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシン−5−イル]チエノ[3,4−d][1,3]オキサゾールを用いて、前記実施例4の手法と同様にして、発色時及び消色時のそれぞれにおいてUV−Visスペクトルを測定することにより、当該重合体のエレクトロクロミック特性を評価した。
実施例1で得られた9−メチル−3,6−ビス(2−メチルチエノ[3,4−d][1,3]チアゾール−6−イル)−9H−カルバゾールを0.36mmolと、10mlのイオン交換水中の18%ポリ(スチレンスルホン酸)水溶液を830mgとを室温下、攪拌しているところに、113.0mg(0.48mmol)の(NH4)2S2O8及び2mgのFe2(SO4)3を添加した。1時間を超えて、酸化重合を実施した。重合後、当該水溶液を、イオン交換カラムにより精製して、π電子系共役重合体/ポリ(スチレンスルホン酸)水性分散液を得た。得られた水性分散液を用いて、1,000rpmにおいてジオマテック株式会社製のITOガラス基板上にπ電子系共役重合体/ポリ(スチレンスルホン酸)混合物をスピンコーティングすることにより、エレクトロクロミック特性評価のためのフィルムを調製した。
実施例2で得られた2−メチル−6−[7−(2−メチルチエノ[3,4−d][1,3]チアゾール−6−イル)−2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシン−5−イル]チエノ[3,4−d][1,3]チアゾールを用いて、前記実施例7の手法と同様にして、発色時及び消色時のそれぞれにおいてUV−Visスペクトルを測定することにより、当該重合体のエレクトロクロミック特性を評価した。
化学式(12)で示される2−メチルチエノ[3,4−d][1,3]チアゾールを用いて、前記実施例4の手法と同様にして、発色時及び消色時のそれぞれにおいてUV−Visスペクトルを測定することにより、当該重合体のエレクトロクロミック特性を評価した。
化学式(12)で示される2−メチルチエノ[3,4−d][1,3]チアゾールと9−メチル−9H−カルバゾールとを、モル比で1:1として混合し、その混合物を0.1Mテトラブチルアンモニウムパークロレート/プロピレンカーボネート溶液に0.01Mの濃度で溶解させ、モノマー含有電解液を調整した。当該モノマー含有電解液を用いて前記実施例4の手法と同様にして、発色時及び消色時のそれぞれにおいてUV−Visスペクトルを測定することにより、当該重合体のエレクトロクロミック特性を評価した。
化学式(12)に示される2−メチルチエノ[3,4−d][1,3]チアゾールと2,3−ジヒドロチエノ[3,4−b]−1,4−ジオキシンとを、モル比で1:1として混合し、その混合物を0.1Mテトラブチルアンモニウムパークロレート/プロピレンカーボネート溶液に0.01Mの濃度で溶解させ、モノマー含有電解液Aを調整した。一方、前記化学式(15)に示される2−メチル−6−[7−(2−メチルチエノ[3,4−d][1,3]チアゾール−6−イル)−2,3−ジヒドロチエノ[3,4−b][1,4]ジオキシン−5−イル]チエノ[3,4−d][1,3]チアゾールを0.1Mテトラブチルアンモニウムパークロレート/プロピレンカーボネート溶液に0.01Mの濃度で溶解させ、モノマー含有電解液Bを調整した。
Claims (3)
- 下記化学式(2)
で示される化合物をハロゲン化して、得られた下記化学式(3)
で示される化合物と、下記化学式(4)
Q2−W−Q2 ・・・(4)
(式中、Wは、アリーレン基又は2価の複素芳香環基であり、Q2は、−MgCl、−MgBr、−MgI、−ZnCl、−ZnBr、−ZnI、−Sn(R1)3(R1は、夫々独立して炭素数1〜20のアルキル基又はアルコキシ基である)、ボロン酸基及びボロン酸エステル基から選ばれる1種である)
で示される化合物とを、クロスカップリング反応させる工程、
又は、
塩基存在下で、下記化学式(2)
で示される化合物と、MgCl2、MgBr2、MgI2、ZnCl2、ZnBr2、ZnI2、Sn(R2)3Cl、Sn(R2)3Br、Sn(R2)3I(R2は、夫々独立して炭素数1〜20のアルキル基又はアルコキシ基である)、ボロン酸及びボロン酸エステルから選ばれる1種とを、反応させることにより、下記化学式(5)
で示される化合物を得たのち、下記化学式(6)
Q4−W−Q4 ・・・(6)
(式中、Wは、前記と同じであり、Q4は、夫々独立してハロゲン原子である)
で示される化合物とクロスカップリング反応させる工程によって、
下記化学式(7)
で示されるモノマー成分を調製した後、重合して、π電子系共役重合体にして、それを含む請求項1に記載のエレクトロクロミック材料にすることを特徴とするエレクトロクロミック材料の製造方法。 - 溶媒中において、前記モノマー成分を、ポリアニオン及び酸化剤の存在下又は接触下で化学重合させることにより、前記重合させて、前記π電子系共役重合体にし、
又は、
前記モノマー成分と電解質とを含有する混合物に、電流を供給して電解重合させることにより、前記重合させて前記電子系共役重合体にすることを特徴とする請求項2に記載のエレクトロクロミック材料の製造方法。
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