WO2006132015A1 - 新規化合物及び液晶組成物 - Google Patents
新規化合物及び液晶組成物 Download PDFInfo
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- WO2006132015A1 WO2006132015A1 PCT/JP2006/305025 JP2006305025W WO2006132015A1 WO 2006132015 A1 WO2006132015 A1 WO 2006132015A1 JP 2006305025 W JP2006305025 W JP 2006305025W WO 2006132015 A1 WO2006132015 A1 WO 2006132015A1
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- liquid crystal
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 105
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 105
- 239000000203 mixture Substances 0.000 title claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 4
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 210000002858 crystal cell Anatomy 0.000 claims description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000011737 fluorine Substances 0.000 abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000460 chlorine Substances 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 description 28
- 239000012071 phase Substances 0.000 description 25
- 150000002440 hydroxy compounds Chemical class 0.000 description 21
- -1 monofluoromethyl Chemical group 0.000 description 21
- 230000003287 optical effect Effects 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- NRIQRAMCXSJILE-UHFFFAOYSA-N (2,4-difluoro-3-methoxyphenyl)boronic acid Chemical compound COC1=C(F)C=CC(B(O)O)=C1F NRIQRAMCXSJILE-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000007704 transition Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004305 biphenyl Substances 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
- 230000003098 cholesteric effect Effects 0.000 description 4
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DHWWNFMRCDVWCF-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-2-en-1-ol Chemical compound OC(F)(F)C(F)=C(F)F DHWWNFMRCDVWCF-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- DXKZQNUSKZOLTC-UHFFFAOYSA-N 1,3,5-trichloro-2-[chloro-(2,4,6-trichlorophenoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1OP(Cl)(=O)OC1=C(Cl)C=C(Cl)C=C1Cl DXKZQNUSKZOLTC-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 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 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 238000000926 separation method Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 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 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
- C07C15/16—Polycyclic non-condensed hydrocarbons containing at least two phenyl groups linked by one single acyclic carbon atom
-
- 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
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
-
- 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
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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Definitions
- the present invention relates to a specific novel compound having lateral substitution, and a liquid crystal composition containing the compound.
- the compounds are useful as liquid crystal compounds, and the liquid crystal compositions are particularly suitable for use in electro-optical display devices.
- ⁇ n Optical (refractive index) anisotropy
- ⁇ ⁇ dielectric anisotropy
- ⁇ ⁇ Optical (refractive index) anisotropy
- ⁇ ⁇ ⁇ dielectric anisotropy
- ⁇ ⁇ dielectric anisotropy
- a large number of display methods and drive methods have been devised for liquid crystal display.
- a display method for example, dynamic scattering type (DS type), guest 'host type (GH type), twisted nematic type ( ⁇ type), super twisted nematic type (STN type), thin film transistor type (TFT type) Ferroelectric liquid crystal (FLC), polymer dispersed liquid crystal (PDL C), and the like are known.
- a driving method a static driving method, a time division driving method, an active matrix driving method, a two-frequency driving method, and the like are known.
- a liquid crystal material is generally Since stability is required, a fluorine-based compound having excellent stability is used as a liquid crystal material.
- Liquid crystal display devices are required to have various performances such as a wide operating temperature range, a low operating voltage, a high speed response, a high contrast ratio, a wide viewing angle, and chemical stability.
- materials that can satisfy these characteristics alone are liquid crystal materials excellent in one or two or more properties and non-liquid crystal materials mixed to form a liquid crystal composition.
- Mutuality, sex It is in the state of satisfying various required performances by compensating for performance. For this reason, in the development of liquid crystal materials or non-liquid crystal materials, studies are generally being made to develop more excellent one or more properties among all the various properties.
- the performance required for liquid crystal display elements includes low voltage drive and high speed response in battery drive, high definition display and high speed response in OA equipment etc., low temperature response or wide operating temperature range in automobile display etc. In particular, it is desirable to improve the response speed, as in the case of high-speed response.
- the response speed ( ⁇ ) is known to be proportional to the product of the viscosity () of the liquid crystal material and the square of the cell thickness (d). That is, the following equation holds.
- the retardation related to the contrast ratio of the liquid crystal display element [optical (refractive index) anisotropy of liquid crystal material (
- the product of ⁇ ⁇ ) and cell thickness (d) needs to be set to a specific value, and in order to reduce the cell thickness, a liquid crystal material having a large ⁇ ⁇ ⁇ ⁇ is required. That is, in order to achieve high-speed response, development of a liquid crystal material having a low viscosity and a large ⁇ is desired.
- the threshold voltage of a field effect liquid crystal display device using a liquid crystal composition with positive dielectric anisotropy ( ⁇ ) is inversely proportional to the square root of ⁇ of the composition. It is done.
- liquid crystal materials having a low threshold voltage have been required mainly for twisted nematic ( ⁇ ) liquid crystal elements, and liquid crystal materials having large positive ⁇ have been required for this purpose. It becomes important.
- the low temperature storage stability of a liquid crystal material is usually evaluated by the lower limit temperature indicating the liquid crystal state, and the lower the value is, the lower the storage temperature indicates the liquid crystal state at a lower temperature. In this case, low temperature storage stability is required.
- Compounds having a fluoroalkyl (oxy) group as a terminal group have positive dielectric anisotropy, and in particular, the high resistivity, high voltage holding ratio (VHR), low releasability required for an active matrix drive system. It is known as a liquid crystal material that expresses ion density and the like, and attempts have been made to introduce fluoroalkyl (oxy) groups into compounds. For example, Various compounds having fluoroalkyl groups have been proposed in Patent Documents 1 to 9 and the like. Further, Patent Document 10 proposes an electro-optical display device using a compound having a fluoroalkyl group, and Patent Documents 11 and 12 etc.
- the active matrix liquid crystal display used has been proposed. Moreover, the applicant has proposed a compound having a fluoroallyloxy group as a terminal group in Patent Document 13.
- the compound is a liquid crystal material having characteristics of low viscosity and high dielectric anisotropy ( ⁇ ).
- Patent Document 1 Japanese Patent Application Laid-Open No. 55.
- Patent Document 2 Japanese Patent Application Laid-Open No. 55 • 40660
- Patent Document 3 Japanese Patent Application Laid-Open No. 61 ⁇ 197563
- Patent Document 4 Japanese Patent Application Laid-Open No. 56 ⁇ 12322
- Patent Document 5 Japanese Patent Application Laid-Open No. 58 • —154532
- Patent Document 6 Japanese Patent Application Laid-Open No. 58- — 177939
- Patent Document 7 Japanese Patent Application Laid-Open No. 58-- 210045
- Patent Document 8 Japanese Patent Application Laid-Open No. 59- — Japanese Patent Publication No. 78129
- Patent Document 9 Japanese Patent Application Publication No. 6-500343
- Patent Document 10 Japanese Patent Application Publication No. 1 503 145
- Patent Document 11 Japanese Patent Application Publication No. 3-502942
- Patent Document 12 Japanese Patent Application Laid-Open No. 10-67989
- Patent Document 13 International Publication No. 2004/058676 pamphlet
- an object of the present invention is to provide a novel compound which can be used as a liquid crystal material which can cope with high-speed response in which the optical (refractive index) anisotropy ( ⁇ ) is high and the liquid crystal phase expression temperature range is wide. It is to provide. Means to solve the problem
- the present invention has been made based on the above-mentioned findings, and provides a compound represented by the following general formula (I).
- Ri is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and the alkyl group may have an unsaturated bond, and any —CH 2 — in the alkyl group is And R 1 may be substituted with one O—, —CO—, one COO— or —S i H 2 —, and part or all of the hydrogen atoms may be substituted by a halogen atom or a cyano group.
- Z u and Z 2 are each independently —COO—, —OCO—, one CH 2 0 —, —OCH 2 —, —CH 2 CH 2 —, —CH CHCH—, or a single bond, And any hydrogen atom in Z 2 may be substituted by a fluorine atom.
- n is a number of 1 or 2, and when m is 2, rings A and Z 2 having repetition may be different from each other.
- n is a number of 0 or 1.
- X 2 each independently represent an alkyl group having 1 to 3 carbon atoms, an alkoxy group or a hydrogen atom, and when one of ⁇ 2 is a hydrogen atom, the other is always a hydrogen atom Absent.
- ⁇ Pi ⁇ 2 are each independently a hydrogen atom, a fluorine atom or a chlorine atom.
- Q is a saturated or unsaturated alkyl group having 1 to 8 carbon atoms in which all or part of the hydrogen atoms are substituted with halogen atoms.
- L is an oxygen atom or a single bond
- the present invention also provides a liquid crystal composition containing the above-described compound.
- the present invention also provides an electro-optical display device formed by sealing the above liquid crystal composition in a liquid crystal cell.
- Q represents that all or part of hydrogen atoms are fluorine, chlorine, bromine, iodine It represents a saturated or unsaturated alkyl group having 1 to 8 carbon atoms (ie, an alkyl group, an alkenyl group or an alkynyl group) substituted with an equal halogen atom.
- Q is preferably a saturated or unsaturated fluoroalkyl group having 8 or more carbon atoms in which all or a part of hydrogen atoms are substituted by fluorine atoms.
- Preferred specific examples of the group represented by Q include monofluoromethyl, difluoromethyl, trifluoromethyl, 2, 2, 2 _ trifluoroetyl, 1, 2, 2 _ trifno reo ro chinole, 1, 2, 2 And 2_trifluorovinylmethoxymethyl, perfluoroethyl, perfluoropropyl, perfluoroaryl and the like.
- one L_Q in the general formula (I) is represented by the following partial structural formula (II).
- a compound in which _L_Q is represented by the following partial structural formula (II) is used, a lower viscosity liquid crystal composition having a particularly wide liquid crystal phase development temperature range can be obtained.
- R in the general formula (I) is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- the alkyl group may have an unsaturated bond (ie, R is an alkyl having 1 to 8 carbon atoms).
- any -CH- in the alkyl group may be
- All hydrogen atoms may be substituted by halogen atoms such as fluorine, chlorine, bromine and iodine, or by cyano groups.
- R Specific examples of the group represented by R include methyl, monofluoromethyl and diphenyl.
- a non-substituted alkyl group or alkenyl group having 2 to 5 carbon atoms is preferable because a non-substituted alkyl group or alkenyl group such as -Layer wide layer, particularly preferred because a liquid crystal composition can be obtained.
- any hydrogen atom in the ring A may be substituted with a halogen atom such as fluorine, chlorine, bromine or iodine, a cyano group, an alkyl group or an alkoxy group, .
- a halogen atom such as fluorine, chlorine, bromine or iodine
- a cyano group such as cyano group
- an alkyl group or an alkoxy group a halogen atom
- Preferred examples of the alkyl group include those having 1 to 3 carbon atoms such as methylol, ethyl, propyl or isopropyl.
- the alkoxy group those having a carbon atom number of! To 3 such as methoxy, ethoxy, propoxy or isopropoxy are preferably mentioned.
- ring A examples include cyclic groups as exemplified below, but the present invention is not limited by these cyclic groups.
- X and X in the general formula (I) each independently represent the number of carbon atoms:! To 3 al
- the other is not necessarily a hydrogen atom. 1 to 3 carbon atoms represented by X and X
- alkyl group examples include methylol, ethyl, propyl and isopropyl.
- alkoxy group having 1 to 3 carbon atoms examples include methoxy, ethoxy, propoxy and isopropoxy.
- Preferred examples of the compound of the present invention represented by the above general formula (I) include the following compounds No .:! To 24: power S, and the present invention is not limited to these compounds Les.
- R in the following compound No .:! To 24 is the same as the case in the general formula (I).
- the method for producing the compound of the present invention is not particularly limited, and for example, a preferred example of the compound wherein the _L_Q moiety is a group represented by the partial structural formula ( ⁇ ) is It can be produced according to the reaction formula shown in [Formula 7].
- Compounds in which the _L_Q moiety is a group other than the group represented by the partial structural formula (II) can also be produced according to the reactions shown in the following reaction formulas and the examples described later.
- X is an iodine atom or bromine
- C represents an atom, monofluorosulfonic acid, etc.
- examples of the base (BASE) used in the above reaction include metal oxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as lithium hydride and sodium hydride; Cetyldimethylamine, propyldimethylamine, N, N'-dimethylbiperazine, pyridine, picoline, 1,8-diazabiscyclo (5.4.0) undecene 1 (DBU), benzyldimethylamine, 2 And amines such as — (dimethylaminoethyl) phenol (DMP-10), 2,4,6-tris (dimethyoleaminomethyl) phenone (DMP-30), and the like.
- metal oxides such as sodium hydroxide and potassium hydroxide
- metal hydrides such as lithium hydride and sodium hydride
- examples of the solvent (solv.) Used in the above reaction include toluene, N, N-dimethylformamide (DMF), 1, 3-dimethylimidazolidinone (DMI), tetrahydrofuran (THF), tolylamine and the like. .
- the use amount of the hydroxy compound (1) and the perfluoro compound (2) shown in the reaction formula of the above [Chemical formula 7] is preferably 20 / :! to 1/20, in mass ratio (the former / the latter). More preferably, it is in the range of 1/1 to 1/10.
- the amount of the base is hydroxy compound (1), preferably 0.1:! ⁇ 5.0 mol%, more preferably from 1.0 to 2 0 mole 0/0..
- the amount of the solvent used may be any amount, but preferably 10 to 500 parts by mass with respect to 100 parts by mass of the total of hydroxy compound (1) and perfluoro compound (2). Use appropriately in the range.
- the compound of the present invention is useful as a liquid crystal compound, and can be combined with various known liquid crystal materials and / or non-liquid crystal materials to form a liquid crystal composition. Next, the liquid crystal composition and the electro-optical display element of the present invention will be described.
- the liquid crystal composition of the present invention contains the compound of the present invention represented by the above general formula (I) in an arbitrary amount.
- the content of the compound of the present invention represented by the general formula (I) is preferably 1% by mass or more, and particularly preferably 5% by mass or more.
- the upper limit of the content of the compound of the present invention is not particularly limited, and the liquid crystal composition may be composed of only the compound of the present invention depending on the intended properties, but various known liquid crystal materials may be used.
- the content of the compound of the present invention is preferably at most 30% by mass in order to sufficiently exert the effect of using each material.
- the kind and blending amount of the liquid crystal material and the non-liquid crystal material to be combined with the compound of the present invention are: twist angle, pretilt angle, dielectric anisotropy ( ⁇ ⁇ ), optical ( Refractive index) Anisotropy ( ⁇ ), specific resistance value, temperature range at which liquid crystal phase appears, viscosity, rotational viscosity, average dielectric constant, voltage holding ratio, and various other desired characteristic values, and liquid crystal composition It selects suitably according to the kind etc. of alignment film used for an optical display element.
- R 2 represents a hydrogen atom, or an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkenyl group, an alkenyloxy group, an alkynyl group, an alkynyloxy group, an alkoxyalkyl group, an alkanoxy group Group or an alkoxycarboyl group, which may be substituted with a halogen atom, a cyano group or the like,
- W 2 represents a cyano group or a halogen atom, or a group similar to the group represented by R 2.
- Wi, W 3 and W 4 represent a hydrogen atom, a halogen atom or a cyano group.
- p is 0, 1 or 2;
- the ring B, the ring C and the ring D each independently represent a benzene ring, a cyclohexane ring, a cyclohexene ring, a pyrimidine ring or a dioxane ring.
- Specific examples of the compound represented by the general formula (III) include the compounds represented by the following [Formula 9].
- R, W, W, W and W in each of the following compounds are the said general formula (III).
- liquid crystal composition of the present invention known chiral agents can be used in combination.
- caustic agents include compounds shown in [Chemical formula 10] and [chemical formula 11].
- R 3 and R 4 each independently represent an alkyl group, an alkoxy group, an alkylcarboalkoxy group or an alkoxy group), which may be interrupted by an ether group, It may be substituted by a halogen atom and / or a cyano group, or may have an unsaturated bond.
- Ring E, ring F and ring G are each independently 1, 4-phenylene, trans-1, 4-cyclohexylene, 2- or 3-fluoro-1, 4-monophenylene or 1, 4 represents 1-cyclohexenylene, which may be substituted by a halogen atom and / or a cyano group.
- q 0, 1 or 2;
- R 5 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkyl group, an alkoxy carpenyl group, an aryl group which may have a substituent, an aryloxy group, a aryl group or an aryl group
- a hydrogen atom in these groups may be replaced by a halogen atom
- an ethylene group may be replaced by an ethenylene group or an ethynylene group.
- R 6 represents an alkyl group or an alkenyl group.
- Ring H represents a fused ring having only one double bond without sharing with other rings, and may be substituted by an alkyl group and Z or an alkoxy group.
- chiral agent examples include the compounds represented by [Chemical Formula 12].
- chiral agents can be used alone or in combination of two or more kinds. In that case, a combination of different twist directions of the helix or a combination of same twist directions may be used. Also, for example, as proposed in Japanese Patent Application Laid-Open No. 7-258641, the temperature dependence of the ability to rotate the cholesteric phase is positive. It is also possible to combine one with one that makes the temperature dependence of the ability to rotate the cholesteric phase negative.
- the pitch of the liquid crystal composition S is adjusted to be in the range of 0.2 to 300 ⁇ .
- liquid crystal composition of the present invention may be benzotriazole-based, benzofuranone-based, triazine-based, benzoate-based or oxanilide-based for the purpose of imparting excellent stability to light and heat over a long period of time.
- UV absorbers such as cyanoacrylates; hindered amine light stabilizers; and antioxidants such as phenols, phosphoruss, and sulfurs can also be added.
- compounds such as surfactants can be added to the liquid crystal composition of the present invention in order to obtain an antistatic effect.
- the compound include, for example, JP-A-59-4676, JP-A-4-36384, JP-A-4-180993, JP-A-11-212070 and JP-A-8-337779. Examples thereof include compounds proposed in JP-A-9-67577, and JP-A-2003-342580.
- the liquid crystal composition of the present invention can be suitably used particularly for an electro-optical display element.
- the liquid crystal composition of the present invention can be enclosed in a liquid crystal cell to form various electro-optical display devices S.
- the electro-optical display device of the present invention in which the liquid crystal composition of the present invention is sealed in a liquid crystal cell is the same as the conventional electro-optical display device except that the liquid crystal composition of the present invention is used as the liquid crystal composition. is there.
- the electro-optical display device of the present invention includes, for example, a dynamic scattering type (DS), a guest 'host type (GH), a twisted nematic type ( ⁇ ), a super twisted nematic type (STN), a thin film transistor type (TFT) Thin film diode type (TFD), ferroelectric liquid crystal type (FLC), antiferroelectric liquid crystal type (AFLC), polymer dispersed liquid crystal type (PDLC), vertical alignment (VA), in-plane switching (IPS), cholesteric nematic It is possible to apply various display modes such as phase transition type, and also to apply various drive modes such as static drive mode, time division drive mode, active matrix drive mode, and two-frequency drive mode. it can.
- DS dynamic scattering type
- GH guest 'host type
- ⁇ twisted nematic type
- STN super twisted nematic type
- TFT thin film transistor type
- TFT Thin film diode type
- FLC ferroelectric liquid crystal type
- An electro-optical display element formed using the liquid crystal composition of the present invention includes a clock, a calculator, a measuring instrument, an automobile instrument, a copying machine, a camera, an A-device, a portable personal computer, a mobile phone, etc. for It can be used on the way.
- a clock a calculator
- a measuring instrument an automobile instrument
- a copying machine a camera
- an A-device a portable personal computer
- a mobile phone etc.
- monitors with large display areas, large screen televisions, or PDAs for portable use It is suitably used in applications such as personal computers and mobile phones.
- the compound of the present invention is the electro-optical element or the liquid crystal composition proposed therein: It can be used in combination with objects.
- the obtained liquid layer was washed with an aqueous solution of sodium hydrogen carbonate, neutralized and then dehydrated with magnesium sulfate to obtain 8. 1 g of brown liquid crystal.
- the brown liquid crystal was purified with a silica gel column (developing solution: hexane / ethyl acetate) to obtain 7.6 g of a yellow transparent liquid (yield 58.8%, purity 99.8%).
- the obtained yellow transparent liquid was confirmed to be the target intermediate 1: 3_methyl_4'-propyl-1- [1, -biphenyl] -4- trifluoromethylsulfonate (2).
- the oily liquid was subjected to silica gel column purification (developing solution: hexane Z ethyl acetate) to obtain a yellowish white transparent viscous substance 7. Og (yield 92.2%, purity 98%).
- the obtained yellow-white transparent viscous solid is the target intermediate 3: 3, 5-difluoro- 2'-methyl- 4 methoxy- 1 4 "-propyl- [1, 1 ': 4', ⁇ '- terphenyl] ( It confirmed that it was 3).
- phase transition temperature of this compound was confirmed by polarized light microscopy, and the result was as shown in [Formula 18].
- Example 2 Using the compound No. 1 obtained in Example 1, a liquid crystal composition was prepared according to the formulation shown in Table 1 below, and the optical (refractive index) anisotropy and low temperature storage stability of the liquid crystal composition were measured. The results are shown below.
- Cryogenicity The lowest temperature that has not changed for two weeks in screw tubes, in units [at]
- the liquid crystal composition using the compound of the present invention has a larger optical (refractive index) anisotropy ( ⁇ ) than the liquid crystal composition using the comparison compound. Low temperature storage is also excellent.
- Example 2 Using the compound No. 1 obtained in Example 1, a liquid crystal composition was prepared according to the formulation shown in Table 2 below, and the optical (refractive index) anisotropy and low temperature storage stability of the liquid crystal composition were measured. The results are shown below.
- ⁇ ⁇ Optical (refractive index) anisotropy (25 t ;, 5 8 9 nm)
- the liquid crystal composition using the compound of the present invention is larger in optical (refractive index) anisotropy ( ⁇ ) than the liquid crystal composition using the comparative compound. Furthermore, low temperature storage stability is also excellent.
- a liquid crystal composition was prepared using the compound No. 1 obtained in Example 1 according to the formulation shown in Table 3 below, and the optical (refractive index) anisotropy, low temperature storage stability, nematic anisotropy of the liquid crystal composition. Tropic phase transition temperature and dielectric anisotropy were measured. The results are shown below.
- T NI Nematic-isotropic phase transition temperature, unit []
- the liquid crystal composition using the compound of the present invention is different from the liquid crystal composition using the comparison compound in optical (refractive index) anisotropy ( ⁇ ) and dielectric constant
- the directionality ( ⁇ ⁇ ) is large.
- the compound of the present invention is equivalent to the comparative compound 2 in the effect of improving the low temperature storage stability, but greatly improves the nematic-aisotropic phase transition temperature ( ⁇ ).
- R and R in the table each represent a saturated alkyl group having 1 to 8 carbon atoms which is not substituted by a halogen atom.
- a liquid crystal composition comprising the compound of the present invention having lateral substitution has high optical (refractive index) anisotropy ( ⁇ ), and thus meets the need for high-speed response to liquid crystal display elements. I can do it.
- the liquid crystal composition is excellent in low-temperature storage stability and has a wide liquid crystal phase expression temperature range.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
Claims
Priority Applications (4)
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CN2006800203762A CN101193846B (zh) | 2005-06-09 | 2006-03-14 | 新型化合物和液晶组合物 |
US11/921,892 US7785675B2 (en) | 2005-06-09 | 2006-03-14 | Compound and liquid crystal composition |
DE112006001453T DE112006001453T5 (de) | 2005-06-09 | 2006-03-14 | Neue Verbindung und Flüssigkristall-Zusammensetzung |
GB0723847A GB2441918B (en) | 2005-06-09 | 2006-03-14 | Chemical compounds and liquid-crystal compositions comprising the compounds |
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JP2005-169480 | 2005-06-09 | ||
JP2005169480A JP4776279B2 (ja) | 2005-06-09 | 2005-06-09 | 新規化合物及び液晶組成物 |
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US (1) | US7785675B2 (ja) |
JP (1) | JP4776279B2 (ja) |
KR (1) | KR20080015859A (ja) |
CN (1) | CN101193846B (ja) |
DE (1) | DE112006001453T5 (ja) |
GB (1) | GB2441918B (ja) |
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WO (1) | WO2006132015A1 (ja) |
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US20100171074A1 (en) * | 2009-01-08 | 2010-07-08 | Daily Polymer Corp. | Liquid crystal mixture |
US20100237286A1 (en) * | 2009-03-18 | 2010-09-23 | Daily Polymer Corp. | Liquid crystal mixture |
EP2496544B1 (en) | 2009-11-05 | 2014-08-20 | Fibrostatin, S.L. | Gpbp inhibition using q2 peptidomimetics |
CN102337139A (zh) * | 2011-08-02 | 2012-02-01 | 江苏和成化学材料有限公司 | 液晶组合物和含有该液晶组合物的液晶显示器件 |
CN102643653B (zh) * | 2012-03-21 | 2013-07-31 | 北京八亿时空液晶科技股份有限公司 | 一种液晶组合物 |
US9822301B2 (en) * | 2013-12-16 | 2017-11-21 | Dic Corporation | Alkenyl ether compound and a liquid crystal composition using the same |
CN104003852B (zh) * | 2014-06-06 | 2016-04-06 | 北京八亿时空液晶科技股份有限公司 | 一种含有三或四联苯结构的液晶化合物及其应用 |
KR102301504B1 (ko) | 2015-01-12 | 2021-09-14 | 삼성디스플레이 주식회사 | 액정 조성물 및 이를 포함하는 액정 표시 장치 |
KR102668909B1 (ko) | 2016-08-11 | 2024-05-24 | 티씨엘 차이나 스타 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 | 액정 표시 장치 및 이에 포함되는 액정 조성물 |
KR102639180B1 (ko) | 2016-08-25 | 2024-02-23 | 삼성디스플레이 주식회사 | 액정 표시 장치 및 이에 포함되는 액정 조성물 |
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2005
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-
2006
- 2006-03-14 CN CN2006800203762A patent/CN101193846B/zh active Active
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- 2006-03-14 US US11/921,892 patent/US7785675B2/en not_active Expired - Fee Related
- 2006-03-14 KR KR1020077029426A patent/KR20080015859A/ko not_active Application Discontinuation
- 2006-03-14 WO PCT/JP2006/305025 patent/WO2006132015A1/ja active Application Filing
- 2006-03-14 GB GB0723847A patent/GB2441918B/en not_active Expired - Fee Related
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JP2006342104A (ja) | 2006-12-21 |
GB0723847D0 (en) | 2008-01-23 |
CN101193846B (zh) | 2012-05-30 |
CN101193846A (zh) | 2008-06-04 |
KR20080015859A (ko) | 2008-02-20 |
GB2441918A (en) | 2008-03-19 |
TWI371441B (ja) | 2012-09-01 |
JP4776279B2 (ja) | 2011-09-21 |
TW200643002A (en) | 2006-12-16 |
US20090103041A1 (en) | 2009-04-23 |
US7785675B2 (en) | 2010-08-31 |
DE112006001453T5 (de) | 2008-11-06 |
GB2441918B (en) | 2010-06-16 |
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