CN104364347B - 双介晶化合物和介晶介质 - Google Patents
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 144
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 51
- 229910052731 fluorine Inorganic materials 0.000 claims description 43
- -1 piperidin-1, 4-diyl Chemical group 0.000 claims description 42
- 125000004429 atom Chemical group 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000006850 spacer group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 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 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000005757 tetralin-2,6-ylene group Chemical group [H]C1=C([*:2])C([H])=C2C(=C1[H])C([H])([H])C([H])([*:1])C([H])([H])C2([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 98
- 230000005611 electricity Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 89
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- 238000006243 chemical reaction Methods 0.000 description 33
- 239000000463 material Substances 0.000 description 32
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000000047 product Substances 0.000 description 16
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- 230000015572 biosynthetic process Effects 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 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 14
- 230000003098 cholesteric effect Effects 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 238000000819 phase cycle Methods 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 7
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- 239000002244 precipitate Substances 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 210000002421 cell wall Anatomy 0.000 description 5
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- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 239000012074 organic phase Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000010008 shearing Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000000527 sonication Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- FSTKSTMFMLANPA-UHFFFAOYSA-N 1,1-dibromononane Chemical compound CCCCCCCCC(Br)Br FSTKSTMFMLANPA-UHFFFAOYSA-N 0.000 description 2
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 description 2
- RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 2
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 2
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- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 239000008346 aqueous phase Substances 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 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
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 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 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 230000006698 induction Effects 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- 235000010445 lecithin Nutrition 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 2
- 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 2
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- NTJBWZHVSJNKAD-UHFFFAOYSA-N triethylazanium;fluoride Chemical compound [F-].CC[NH+](CC)CC NTJBWZHVSJNKAD-UHFFFAOYSA-N 0.000 description 2
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- VMRXHUXZVZRLSS-UHFFFAOYSA-N 2-butyl-1-methyl-3-phenylbenzene Chemical group CCCCC1=C(C)C=CC=C1C1=CC=CC=C1 VMRXHUXZVZRLSS-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
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- ZRMIETZFPZGBEB-UHFFFAOYSA-N N#Cc(cc1)ccc1-c(cc1)ccc1O Chemical compound N#Cc(cc1)ccc1-c(cc1)ccc1O ZRMIETZFPZGBEB-UHFFFAOYSA-N 0.000 description 1
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- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
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- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- SHNJHLWLAGUBOV-UHFFFAOYSA-N sodium;oxido(oxo)borane;octahydrate Chemical compound O.O.O.O.O.O.O.O.[Na+].[O-]B=O SHNJHLWLAGUBOV-UHFFFAOYSA-N 0.000 description 1
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- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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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
- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0258—Flexoelectric
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0208—Twisted Nematic (T.N.); Super Twisted Nematic (S.T.N.); Optical Mode Interference (O.M.I.)
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
-
- 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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP12004081.1 | 2012-05-25 | ||
| EP12004081 | 2012-05-25 | ||
| PCT/EP2013/001353 WO2013174478A1 (en) | 2012-05-25 | 2013-05-07 | Bimesogenic compounds and mesogenic media |
Publications (2)
| Publication Number | Publication Date |
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| CN104364347A CN104364347A (zh) | 2015-02-18 |
| CN104364347B true CN104364347B (zh) | 2017-12-01 |
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| CN201380026565.0A Active CN104364347B (zh) | 2012-05-25 | 2013-05-07 | 双介晶化合物和介晶介质 |
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| EP (1) | EP2855627B1 (enExample) |
| JP (1) | JP6600255B2 (enExample) |
| KR (1) | KR20150013898A (enExample) |
| CN (1) | CN104364347B (enExample) |
| TW (1) | TWI630262B (enExample) |
| WO (1) | WO2013174478A1 (enExample) |
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| EP2855631B1 (en) * | 2012-05-25 | 2017-09-20 | Merck Patent GmbH | Mesogenic media and liquid crystal display |
| WO2014005670A1 (en) * | 2012-07-06 | 2014-01-09 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| WO2014005672A1 (en) * | 2012-07-06 | 2014-01-09 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| CN104583366B (zh) * | 2012-08-29 | 2017-06-23 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| US20160289561A1 (en) * | 2013-11-22 | 2016-10-06 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| JP6657088B2 (ja) * | 2013-11-22 | 2020-03-04 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | メソゲン媒体および液晶ディスプレイ |
| EP3087157B1 (en) * | 2013-12-23 | 2017-09-06 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| US9932381B2 (en) | 2014-06-18 | 2018-04-03 | Sanofi | Exendin-4 derivatives as selective glucagon receptor agonists |
| JP2017528429A (ja) * | 2014-07-17 | 2017-09-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ビメソゲン化合物およびメソゲン媒体 |
| CN104087311B (zh) * | 2014-07-21 | 2015-12-30 | 西安近代化学研究所 | 一种双介晶基元液晶化合物 |
| CN105487157A (zh) * | 2014-08-13 | 2016-04-13 | 南京晶多新材料科技有限公司 | 一种兼作散射偏光片的电控调光膜的构造和应用 |
| JP2017534923A (ja) * | 2014-11-06 | 2017-11-24 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ | 光変調素子 |
| CN107075371B (zh) * | 2014-11-11 | 2021-03-12 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| EP3234067B1 (en) * | 2014-12-17 | 2018-08-22 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| US20170351130A1 (en) * | 2014-12-19 | 2017-12-07 | Merck Patent Gmbh | Light modulation element |
| CN106281359B (zh) * | 2015-06-04 | 2019-02-15 | 江苏和成显示科技有限公司 | 液晶组合物及其显示器件 |
| CN106281355B (zh) * | 2015-06-04 | 2019-02-15 | 江苏和成显示科技有限公司 | 液晶介质及其应用 |
| CN106281360B (zh) * | 2015-06-04 | 2019-02-15 | 江苏和成显示科技有限公司 | 液晶组合物及其应用 |
| US20180305619A1 (en) * | 2015-10-23 | 2018-10-25 | Merck Patent Gmbh | Light modulation element |
| KR20180088705A (ko) * | 2015-12-02 | 2018-08-06 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 장치 |
| CN105549290B (zh) * | 2016-02-01 | 2019-07-23 | 京东方科技集团股份有限公司 | 显示面板和显示装置 |
| JP2019533037A (ja) | 2016-09-14 | 2019-11-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体および液晶デバイス |
| WO2018104279A1 (en) | 2016-12-08 | 2018-06-14 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal device |
| US11434426B2 (en) | 2017-03-13 | 2022-09-06 | Kent State University | Fast flexoelectro-optic switching based on bimesogen-doped and polymer-stabilized vertical standing helix mode |
| DE112018004045T5 (de) | 2017-08-08 | 2020-05-14 | Merck Patent Gmbh | Flüssigkristallmedium und flüssigkristallvorrichtung |
| CN110997870B (zh) | 2017-08-08 | 2023-08-22 | 默克专利股份有限公司 | 液晶介质及液晶器件 |
| DE112018005688T5 (de) | 2017-10-25 | 2020-07-09 | Merck Patent Gmbh | Flüssigkristallmedium und flüssigkristallvorrichtung |
| DE112018005004T5 (de) | 2017-10-25 | 2020-07-16 | Merck Patent Gmbh | Flüssigkristallmedium und Flüssigkristallvorrichtung |
| TWI800577B (zh) | 2017-12-18 | 2023-05-01 | 德商馬克專利公司 | 液晶化合物及液晶介質 |
| WO2019179962A1 (en) | 2018-03-22 | 2019-09-26 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN111983867A (zh) * | 2019-05-24 | 2020-11-24 | 江苏集萃智能液晶科技有限公司 | 一种双稳态调光器件 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS6322865A (ja) * | 1986-04-11 | 1988-01-30 | ザ・ボ−ド オブ トラスティ−ズ オブ ザ ユニヴァ−シティ オブ イリノイ | 電気特性および磁気特性を改良した重合体 |
| DE4000451B4 (de) | 1990-01-09 | 2004-12-09 | Merck Patent Gmbh | Elektrooptisches Flüssigkristallschaltelement |
| JP3075807B2 (ja) * | 1991-10-14 | 2000-08-14 | 汪芳 白井 | 液晶材料 |
| EP1061404A1 (en) | 1992-09-18 | 2000-12-20 | Hitachi, Ltd. | A liquid crystal display device |
| JPH08295645A (ja) * | 1995-04-28 | 1996-11-12 | Nippon Oil & Fats Co Ltd | 液晶化合物 |
| JP3692430B2 (ja) * | 1995-06-28 | 2005-09-07 | 大日本インキ化学工業株式会社 | ４−（２−シクロヘキシルプロピル）ベンゼン誘導体 |
| GB2329636B (en) | 1996-07-01 | 2000-07-19 | Merck Patent Gmbh | Chiral dopants |
| DE19649056A1 (de) * | 1996-11-27 | 1998-05-28 | Basf Ag | Polymerisierbare Oligomesogene |
| JPH10237002A (ja) * | 1997-02-26 | 1998-09-08 | Japan Energy Corp | 新規な非対称ツイン化合物及びこれを含む液晶組成物 |
| DE19834162A1 (de) | 1997-08-13 | 1999-02-18 | Merck Patent Gmbh | Chirale Verbindungen |
| EP0971016B1 (en) | 1998-07-08 | 2003-05-21 | MERCK PATENT GmbH | Mesogenic estradiols |
| GB2356629B (en) * | 1999-10-04 | 2004-09-22 | Merck Patent Gmbh | Bimesogenic Compounds and Flexoelectric Devices |
| JP2002128743A (ja) * | 2000-10-19 | 2002-05-09 | Dainippon Ink & Chem Inc | 重合性液晶化合物 |
| JP4766291B2 (ja) * | 2001-06-27 | 2011-09-07 | Ｄｉｃ株式会社 | 重合性液晶化合物、組成物、及び光学異方体 |
| GB0225662D0 (en) * | 2001-11-16 | 2002-12-11 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| ATE314446T1 (de) * | 2002-10-08 | 2006-01-15 | Merck Patent Gmbh | Flüssigkristallines medium und flüssigkristallanzeige |
| AU2003301561A1 (en) * | 2002-10-24 | 2004-05-13 | South Dakota School Of Mines And Technology | Monomers containing at least one biaryl unit and polymers and derivatives prepared therefrom |
| JP4342170B2 (ja) * | 2002-12-17 | 2009-10-14 | 三井化学株式会社 | 液晶組成物および液晶素子 |
| JP4246145B2 (ja) * | 2003-12-18 | 2009-04-02 | シャープ株式会社 | 表示素子および表示装置 |
| GB0402006D0 (en) * | 2004-01-30 | 2004-03-03 | Dow Corning Ltd | Liquid crystal materials |
| DE602005006845D1 (de) * | 2004-12-23 | 2008-06-26 | Merck Patent Gmbh | Bimesogene verbindungen und flexoelektrische vorrichtungen |
| US8377519B2 (en) * | 2006-06-09 | 2013-02-19 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| KR101106528B1 (ko) * | 2009-06-30 | 2012-01-20 | 금오공과대학교 산학협력단 | 이 메소젠 구조를 갖는 액정화합물 |
-
2013
- 2013-05-07 CN CN201380026565.0A patent/CN104364347B/zh active Active
- 2013-05-07 EP EP13727515.2A patent/EP2855627B1/en not_active Not-in-force
- 2013-05-07 US US14/403,201 patent/US20150090935A1/en not_active Abandoned
- 2013-05-07 KR KR1020147036288A patent/KR20150013898A/ko not_active Ceased
- 2013-05-07 WO PCT/EP2013/001353 patent/WO2013174478A1/en not_active Ceased
- 2013-05-07 JP JP2015513036A patent/JP6600255B2/ja not_active Expired - Fee Related
- 2013-05-24 TW TW102118499A patent/TWI630262B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US20150090935A1 (en) | 2015-04-02 |
| TW201404870A (zh) | 2014-02-01 |
| WO2013174478A1 (en) | 2013-11-28 |
| KR20150013898A (ko) | 2015-02-05 |
| EP2855627A1 (en) | 2015-04-08 |
| TWI630262B (zh) | 2018-07-21 |
| CN104364347A (zh) | 2015-02-18 |
| JP6600255B2 (ja) | 2019-10-30 |
| JP2015523334A (ja) | 2015-08-13 |
| EP2855627B1 (en) | 2017-09-20 |
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