JP5885017B2 - アゾベンゼン誘導体及びこれを含有する液晶組成物 - Google Patents
アゾベンゼン誘導体及びこれを含有する液晶組成物 Download PDFInfo
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- JP5885017B2 JP5885017B2 JP2011238727A JP2011238727A JP5885017B2 JP 5885017 B2 JP5885017 B2 JP 5885017B2 JP 2011238727 A JP2011238727 A JP 2011238727A JP 2011238727 A JP2011238727 A JP 2011238727A JP 5885017 B2 JP5885017 B2 JP 5885017B2
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 67
- 239000000203 mixture Substances 0.000 title claims description 45
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000001153 fluoro group Chemical group F* 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- -1 naphthalene-1,4-diyl Chemical group 0.000 claims description 71
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 description 70
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 22
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 21
- 239000004210 ether based solvent Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000004215 Carbon black (E152) Substances 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
- 150000002430 hydrocarbons Chemical class 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000002798 polar solvent Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 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 9
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 238000007710 freezing Methods 0.000 description 8
- 230000008014 freezing Effects 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229940043279 diisopropylamine Drugs 0.000 description 7
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000001879 copper Chemical class 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000003849 aromatic solvent Substances 0.000 description 5
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 5
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- IGSDYWXQTJHVKV-UHFFFAOYSA-N C(CC)C1=CC2=CC(=C(C(=C2C=C1)F)C#C)F Chemical compound C(CC)C1=CC2=CC(=C(C(=C2C=C1)F)C#C)F IGSDYWXQTJHVKV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- PXBSRIKPLOVDTP-UHFFFAOYSA-N CCCC1=CC=C(C=C(C=C2)C(C=C3)=CC=C3N=NC(C=CC(OCC)=C3)=C3C#C)C2=C1 Chemical compound CCCC1=CC=C(C=C(C=C2)C(C=C3)=CC=C3N=NC(C=CC(OCC)=C3)=C3C#C)C2=C1 PXBSRIKPLOVDTP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- WZJAGVBCHHWJBR-UHFFFAOYSA-N 5,7-difluoronaphthalen-2-ol Chemical compound FC1=CC(F)=CC2=CC(O)=CC=C21 WZJAGVBCHHWJBR-UHFFFAOYSA-N 0.000 description 2
- QJZZDXNJRJOHEV-UHFFFAOYSA-N C(CC)C=1C=C2C=C(C=C(C2=CC=1)F)F Chemical compound C(CC)C=1C=C2C=C(C=C(C2=CC=1)F)F QJZZDXNJRJOHEV-UHFFFAOYSA-N 0.000 description 2
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- NMLNVPZCBGTRGK-UHFFFAOYSA-N CC#CC1=CC2=CC(=CC(=C2C=C1)F)F Chemical compound CC#CC1=CC2=CC(=CC(=C2C=C1)F)F NMLNVPZCBGTRGK-UHFFFAOYSA-N 0.000 description 2
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- SCTSIWKMCWEJLG-UHFFFAOYSA-N CCCC1=CC2=C(C=C1)C=C(C=C2)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)CC)C#C Chemical compound CCCC1=CC2=C(C=C1)C=C(C=C2)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)CC)C#C SCTSIWKMCWEJLG-UHFFFAOYSA-N 0.000 description 2
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- FZSOTMOLZQZUET-UHFFFAOYSA-N CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)CC)C#C)F Chemical compound CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)CC)C#C)F FZSOTMOLZQZUET-UHFFFAOYSA-N 0.000 description 2
- HURNOOLWDSPLFQ-UHFFFAOYSA-N CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)O)C#C)F Chemical compound CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)O)C#C)F HURNOOLWDSPLFQ-UHFFFAOYSA-N 0.000 description 2
- OUGZYRCTBJFFOY-UHFFFAOYSA-N CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)OCC)C#C)F Chemical compound CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=CC=C(C=C3)N=NC4=C(C=C(C=C4)OCC)C#C)F OUGZYRCTBJFFOY-UHFFFAOYSA-N 0.000 description 2
- HPOUVMJMDMJYSX-UHFFFAOYSA-N CCCC1=CC2=CC(=C(C(=C2C=C1)F)I)F Chemical compound CCCC1=CC2=CC(=C(C(=C2C=C1)F)I)F HPOUVMJMDMJYSX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- WZSVOUYPNAGMPC-UHFFFAOYSA-N (4-ethoxyphenyl)-phenyldiazene Chemical compound C1=CC(OCC)=CC=C1N=NC1=CC=CC=C1 WZSVOUYPNAGMPC-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- LQBNOHAXLHRIQW-UHFFFAOYSA-N 2-propylnaphthalene Chemical compound C1=CC=CC2=CC(CCC)=CC=C21 LQBNOHAXLHRIQW-UHFFFAOYSA-N 0.000 description 1
- APGNXGIUUTWIRE-UHFFFAOYSA-N 4-Pentylphenylacetylene Chemical compound CCCCCC1=CC=C(C#C)C=C1 APGNXGIUUTWIRE-UHFFFAOYSA-N 0.000 description 1
- LJEFFYXFXYFSOA-UHFFFAOYSA-N 4-[(4-ethylphenyl)diazenyl]phenol Chemical compound C1=CC(CC)=CC=C1N=NC1=CC=C(O)C=C1 LJEFFYXFXYFSOA-UHFFFAOYSA-N 0.000 description 1
- HOUVATQQKYAEBB-UHFFFAOYSA-N 5,7-difluoro-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1CC(=O)CC2=CC(F)=CC(F)=C21 HOUVATQQKYAEBB-UHFFFAOYSA-N 0.000 description 1
- AWQKULXTGASLSW-UHFFFAOYSA-N 6-propylnaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(CCC)=CC=C21 AWQKULXTGASLSW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GEJZXSULJLAGQU-UHFFFAOYSA-N CCC1=CC(=C(C=C1)N=NC2=CC=CC=C2)C#C Chemical compound CCC1=CC(=C(C=C1)N=NC2=CC=CC=C2)C#C GEJZXSULJLAGQU-UHFFFAOYSA-N 0.000 description 1
- CJOSRKVMMBFUJL-UHFFFAOYSA-N CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=C(C=CC(=C3C#C)N=NC4=CC=CC=C4)CC)F Chemical compound CCCC1=CC2=CC(=C(C(=C2C=C1)F)C3=C(C=CC(=C3C#C)N=NC4=CC=CC=C4)CC)F CJOSRKVMMBFUJL-UHFFFAOYSA-N 0.000 description 1
- WLWFMBFGSVXEEE-UHFFFAOYSA-N CCCCCC1=CC=C(C=C1)C#CC2=CC=C(C=C2)N=NC3=CC=C(C=C3)OCCC Chemical compound CCCCCC1=CC=C(C=C1)C#CC2=CC=C(C=C2)N=NC3=CC=C(C=C3)OCCC WLWFMBFGSVXEEE-UHFFFAOYSA-N 0.000 description 1
- FFWJDKGIWCXWQH-UHFFFAOYSA-N CCCCCC1=CC=C(C=C1)C2=CC=C(C=C2)N=NC3=C(C=C(C=C3)OCCC)C#C Chemical compound CCCCCC1=CC=C(C=C1)C2=CC=C(C=C2)N=NC3=C(C=C(C=C3)OCCC)C#C FFWJDKGIWCXWQH-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 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
- RRHNGIRRWDWWQQ-UHFFFAOYSA-N n-iodoaniline Chemical compound INC1=CC=CC=C1 RRHNGIRRWDWWQQ-UHFFFAOYSA-N 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
- 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
- 239000011306 natural pitch Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005651 substituted 1,4-phenylene group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Description
Z1は単結合、−OCH2−、−CH2O−、−C2H4−、−C4H8−、−COO−、−OCO−、−CH=CH−、−CF=CF−、−CF2O−、−OCF2−、−CF2CF2−又は−C≡C−を表し、A1は1,4−フェニレン基、ナフタレン−1,4−ジイル基又はナフタレン−2,6−ジイル基を表し、A1中の水素原子はそれぞれ独立してハロゲン原子に置換されていてもよく、A1中の非隣接の1個又は2個以上の−CH=は−N=で置き換えられていてもよく、X1、X2、X3、X4、X5及びX6はそれぞれ独立して水素原子又はハロゲン原子を表し、mは0又は1を表す。)で表される化合物を提供する。
La、Lb及びLcは連結基であって、それぞれ独立的に単結合、エチレン基(−CH2CH2−)、1,2−プロピレン基(−CH(CH3)CH2−及び−CH2CH(CH3)−)、1,4−ブチレン基、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=CH−、−CH=CF−、−CF=CH−、−CF=CF−、−C≡C−又は−CH=NN=CH−を表すが、単結合、エチレン基、1,4−ブチレン基、−COO−、−OCF2−、−CF2O−、−CF=CF−又は−C≡C−が好ましく、単結合又はエチレン基が特に好ましい。また、一般式(A2)においてはその少なくとも1個が、一般式(A3)においてはその少なくとも2個が単結合を表すことが好ましい。
次に(C3)におけるより好ましい形態は以下の一般式(C3a)〜(C3f)で表すことができる。
(製法1)一般式(7)
(製法2)製法1で得られる一般式(9)で表される化合物と、一般式(14)
・相転移温度:温度調節ステージを備えた偏光顕微鏡で測定
・化合物の構造:核磁気共鳴スペクトル(NMR)、質量スペクトル(MS)等により確認 TN−Iはネマチック相を示す上限の温度を表す。
DMF:N,N−ジメチルホルムアミド
TMS:トリメチルシリル基
Tf:トリフルオロメタンスルホニル基
Et:エチル基
Pr:n−プロピル基
Bu:n−ブチル基
Pen:n−ペンチル基
(実施例1) 4-(6-プロピル-1,3-ジフルオロナフタレ’ン-2-イル)エチニル-4’-エチルアゾベンゼンの製造
14.7gのトリフルオロメタンスルホン酸 4’-エチルアゾベンゼン-4-イル (4-エチル-4’-ヒドロキシアゾベンゼン(Chemical Communication, 2010, 46, 2587-2589 に記載の方法と同様にして得た)を用いて、前記トリフルオロメタンスルホン酸 5,7−ジフルオロナフタレン-2-イルの場合と同様にして得た)、0.33gのヨウ化銅(I)、1.0gのテトラキス(トリフェニルホスフィン)パラジウム(0)を50mLのDMF、20mLのトリエチルアミンに混合し、75℃に加熱し、ここへ得られた9.9gの2-プロピル-6-エチニル-5,7-ジフルオロナフタレンをDMF30mLに溶解させて滴下し、更に7時間攪拌した。室温まで冷却後、反応混合物にトルエン、および系が酸性となるまで10%塩酸を加えて攪拌し、有機相を分取した。水相をトルエンにて抽出後、有機相を合わせ、飽和重曹水、飽和食塩水にて洗浄し、無水硫酸ナトリウムにて乾燥し、溶媒を減圧留去した。カラムクロマトグラフィー、再結晶(アセトン、メタノール)により精製し、9.5gの4-(6-プロピル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-エチルアゾベンゼンを得た。
同様にして以下の化合物を得た。
4-(6-プロピル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-プロピルアゾベンゼン
4-(6-エチル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-プロピルアゾベンゼン
4-(6-エチル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-エチルアゾベンゼン
(実施例2) 4-(6-プロピル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-エトキシアゾベンゼンの製造
4-(6-プロピル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-プロポキシアゾベンゼン
4-(6-エチル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-プロポキシアゾベンゼン
4-(6-エチル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-エトキシアゾベンゼン
(実施例3) 4-(6-プロピルナフタレン-2-イル)エチニル-4’-エチルアゾベンゼンの製造
同様にして以下の化合物を得た。
4-(6-プロピル-ナフタレン-2-イル)エチニル-4’-プロピルアゾベンゼン
4-(6-エチル-ナフタレン-2-イル)エチニル-4’-プロピルアゾベンゼン
4-(6-エチル-ナフタレン-2-イル)エチニル-4’-エチルアゾベンゼン
(実施例4) 4-(6-プロピルナフタレン-2-イル)エチニル-4’-エトキシアゾベンゼンの製造
4-(6-プロピル-ナフタレン-2-イル)エチニル-4’-プロポキシアゾベンゼン
4-(6-エチル-ナフタレン-2-イル)エチニル-4’-プロポキシアゾベンゼン
4-(6-エチル-ナフタレン-2-イル)エチニル-4’-エトキシアゾベンゼン
(比較例1)4-(4-ペンチルフェニル)エチニル-4’-プロポキシアゾベンゼンの製造
(実施例5) 液晶組成物の調製−1
以下の組成からなるホスト液晶組成物(H)
屈折率異方性(Δn):0.1024
この母体液晶(H)90%と、実施例1で得られた4-(6-プロピル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-エチルアゾベンゼン10%からなる液晶組成物を調製した。
(実施例6) 液晶組成物の調製−2
母体液晶(H)90%と、実施例2で得られた4-(6-プロピル-1,3-ジフルオロナフタレン-2-イル)エチニル-4’-エトキシアゾベンゼン 10%からなる液晶組成物を調製した。
(実施例7) 液晶組成物の調製−3
母体液晶(H)90%と、実施例3で得られた4-(6-プロピルナフタレン-2-イル)エチニル-4’-エチルアゾベンゼン 10%からなる液晶組成物を調製した。
(実施例8) 液晶組成物の調製−4
母体液晶(H)90%と、実施例4で得られた4-(6-プロピルナフタレン-2-イル)エチニル-4’-エトキシアゾベンゼン 10%からなる液晶組成物を調製した。
(比較例2)液晶組成物の調製−5
母体液晶(H)90%と、比較例1で得られた4-(4-ペンチルフェニルエチニル)-4’-プロポキシアゾベンゼン10%からなる液晶組成物を調製した。
Claims (20)
- 一般式(1)
- 一般式(1)において、X1、X2、X3、X4、X5及びX6の1個又は2個以上がハロゲン原子である請求項1記載の化合物。
- 一般式(1)において、X1、X2、X3、X4、X5及びX6の1個又は2個以上がフッ素原子である請求項1記載の化合物。
- 一般式(1)において、X1、X2、X3、X4、X5及びX6の2個以上がフッ素原子である請求項1記載の化合物。
- 一般式(1)において、X1、X3、X4及びX6の2個以上がフッ素原子である請求項1記載の化合物。
- 一般式(1)において、X3及びX4がフッ素原子である請求項1記載の化合物。
- 一般式(1)において、R1及びR2がそれぞれ独立してR3−Z4−(式中、R3は炭素原子数1〜12のアルキル基又は炭素原子数2〜12のアルケニル基を表し、基中の1個又は2個以上の水素原子は独立してフッ素原子に置換されていてもよく、Z4は−CH=CH−又は−C≡C−を表す。)である請求項1〜6のいずれか1項に記載の化合物。
- 一般式(1)において、存在するA1、A2、A3、A4、A5及びA6のうち1個が一般式(2)で表されるナフタレン−2,6−ジイル基であり、他がそれぞれ独立して無置換であるか1個以上のフッ素原子により置換されていてもよい1,4−フェニレン基である請求項1〜7のいずれか1項に記載の化合物。
- 一般式(1)において、m、n及びpが0である請求項1〜8のいずれか1項に記載の化合物。
- 一般式(1)において、R1及びR2の少なくとも一つが炭素原子数1〜12のアルキル基、炭素原子数2〜12のアルケニル基、炭素原子数1〜12のアルコキシ基、炭素原子数2〜12のアルケニルオキシ基又はR3−Z4−である請求項7〜9のいずれか1項に記載の化合物。
- 一般式(1)において、R1及びR2がそれぞれ独立して炭素原子数1〜12のアルキル基、炭素原子数2〜12のアルケニル基、炭素原子数1〜12のアルコキシ基、炭素原子数2〜12のアルケニルオキシ基又はR3−Z4−である請求項7〜9のいずれか1項に記載の化合物。
- 一般式(1)において、R1又はR2のどちらか一方がフッ素原子又はシアノ基である請求項1〜10のいずれか1項に記載の化合物。
- 請求項1〜12のいずれか1項に記載の一般式(1)で表される化合物を1種以上含有することを特徴とする液晶組成物。
- 請求項13記載の液晶組成物を用いた液晶表示素子。
- 請求項13記載の液晶組成物を用いたコレステリック液晶表示素子。
- 一般式(3)
Z1は単結合、−OCH2−、−CH2O−、−C2H4−、−C4H8−、−COO−、−OCO−、−CH=CH−、−CF=CF−、−CF2O−、−OCF2−、−CF2CF2−又は−C≡C−を表し、A1は1,4−フェニレン基、ナフタレン−1,4−ジイル基又はナフタレン−2,6−ジイル基を表し、A1中の水素原子はそれぞれ独立してハロゲン原子に置換されていてもよく、A1中の非隣接の1個又は2個以上の−CH=は−N=で置き換えられていてもよく、X1、X2、X3、X4、X5及びX6はそれぞれ独立して水素原子又はハロゲン原子を表し、mは0又は1を表す。)で表される化合物。 - 一般式(3)において、X1、X2、X3、X4、X5及びX6の2個以上がフッ素原子である請求項16記載の化合物。
- 一般式(3)において、X1、X2、X3、X4、X5及びX6の2個以上がフッ素原子である請求項16記載の化合物。
- 一般式(3)において、X3及びX4がフッ素原子である請求項16記載の化合物。
- 請求項16〜19のいずれか一項に記載の一般式(3)で表される化合物を用いることを特徴とする、請求項1〜12のいずれか一項に記載の一般式(1)で表される化合物の製造方法。
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