KR20150013898A - 바이메소제닉 화합물 및 메소제닉 매질 - Google Patents
바이메소제닉 화합물 및 메소제닉 매질 Download PDFInfo
- Publication number
- KR20150013898A KR20150013898A KR1020147036288A KR20147036288A KR20150013898A KR 20150013898 A KR20150013898 A KR 20150013898A KR 1020147036288 A KR1020147036288 A KR 1020147036288A KR 20147036288 A KR20147036288 A KR 20147036288A KR 20150013898 A KR20150013898 A KR 20150013898A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- groups
- liquid crystal
- group
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 134
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 73
- -1 Naphthalene-2,6-diyl Chemical group 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000006850 spacer group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 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
- 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 4
- 230000036961 partial effect Effects 0.000 claims description 4
- 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
- 229920001577 copolymer Chemical group 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 95
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- 239000012071 phase Substances 0.000 description 42
- 239000000463 material Substances 0.000 description 36
- 239000000758 substrate Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 19
- 230000005684 electric field Effects 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 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
- 230000003287 optical effect Effects 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 10
- 230000003098 cholesteric effect Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000000819 phase cycle Methods 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000011295 pitch Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 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
- 239000004988 Nematic liquid crystal Substances 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
- 239000004642 Polyimide Substances 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- VJHGSLHHMIELQD-UHFFFAOYSA-N nona-1,8-diene Chemical compound C=CCCCCCC=C VJHGSLHHMIELQD-UHFFFAOYSA-N 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-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
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 230000000996 additive effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- JHAYEQICABJSTP-UHFFFAOYSA-N decoquinate Chemical group N1C=C(C(=O)OCC)C(=O)C2=C1C=C(OCC)C(OCCCCCCCCCC)=C2 JHAYEQICABJSTP-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- 239000003480 eluent Substances 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 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
- 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
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000002958 pentadecyl 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])C([H])([H])[H] 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 125000002889 tridecyl 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])[H] 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 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
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- 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 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
- MHMRKNHYHPORRR-UHFFFAOYSA-N 2-bromo-1-fluoro-3-iodobenzene Chemical compound FC1=CC=CC(I)=C1Br MHMRKNHYHPORRR-UHFFFAOYSA-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YLRJKFZBCDDWHU-UHFFFAOYSA-N 3-hydroxy-2-(2-hydroxyphenyl)benzonitrile Chemical compound OC1=CC=CC=C1C1=C(O)C=CC=C1C#N YLRJKFZBCDDWHU-UHFFFAOYSA-N 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
- RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XFJKIBSUVGPQNT-UHFFFAOYSA-N C(C)(C)(C)OC(=O)NC(Cl)NC(=O)OC(C)(C)C Chemical compound C(C)(C)(C)OC(=O)NC(Cl)NC(=O)OC(C)(C)C XFJKIBSUVGPQNT-UHFFFAOYSA-N 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000009477 glass transition Effects 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
- 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
- 239000008240 homogeneous mixture Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 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
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 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
- 238000000527 sonication Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K19/02—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
- C09K19/52—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
- C09K19/04—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 |
|---|---|---|---|
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| KR20150013898A true KR20150013898A (ko) | 2015-02-05 |
Family
ID=48577675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147036288A Ceased KR20150013898A (ko) | 2012-05-25 | 2013-05-07 | 바이메소제닉 화합물 및 메소제닉 매질 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20150090935A1 (enExample) |
| EP (1) | EP2855627B1 (enExample) |
| JP (1) | JP6600255B2 (enExample) |
| KR (1) | KR20150013898A (enExample) |
| CN (1) | CN104364347B (enExample) |
| TW (1) | TWI630262B (enExample) |
| WO (1) | WO2013174478A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6240171B2 (ja) * | 2012-05-25 | 2017-11-29 | 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 |
| EP2870218B1 (en) * | 2012-07-06 | 2018-05-02 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| CN104411798B (zh) * | 2012-07-06 | 2017-05-24 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| US9644144B2 (en) * | 2012-08-29 | 2017-05-09 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| WO2015074738A1 (en) * | 2013-11-22 | 2015-05-28 | 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 |
| WO2015096879A1 (en) * | 2013-12-23 | 2015-07-02 | 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 |
| EP3169749B1 (en) * | 2014-07-17 | 2018-12-26 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| 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 |
| EP3218446B1 (en) * | 2014-11-11 | 2018-07-04 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| JP6841758B2 (ja) * | 2014-12-17 | 2021-03-10 | 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性媒体 |
| KR20170097154A (ko) * | 2014-12-19 | 2017-08-25 | 메르크 파텐트 게엠베하 | 광 변조 소자 |
| 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 |
| 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 |
| 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 |
| WO2017067630A1 (en) * | 2015-10-23 | 2017-04-27 | Merck Patent Gmbh | Light modulation element |
| EP3383970B1 (en) * | 2015-12-02 | 2021-03-31 | Merck Patent GmbH | Liquid crystal medium and liquid crystal device |
| 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 |
| WO2019030150A1 (en) | 2017-08-08 | 2019-02-14 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM AND LIQUID CRYSTAL DEVICE |
| WO2019030153A1 (en) | 2017-08-08 | 2019-02-14 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM AND LIQUID CRYSTAL DEVICE |
| DE112018005004T5 (de) | 2017-10-25 | 2020-07-16 | Merck Patent Gmbh | Flüssigkristallmedium und Flüssigkristallvorrichtung |
| WO2019081561A1 (en) | 2017-10-25 | 2019-05-02 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM AND LIQUID CRYSTAL DEVICE |
| 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 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE19781752T1 (de) | 1996-07-01 | 1999-09-02 | Merck Patent Gmbh | Chirale Dotierstoffe |
| 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 |
| WO2004037879A2 (en) * | 2002-10-24 | 2004-05-06 | 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 |
| KR101257119B1 (ko) * | 2004-12-23 | 2013-04-22 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 및 플렉소일렉트릭 장치 |
| KR101547358B1 (ko) * | 2006-06-09 | 2015-08-25 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| KR101106528B1 (ko) * | 2009-06-30 | 2012-01-20 | 금오공과대학교 산학협력단 | 이 메소젠 구조를 갖는 액정화합물 |
-
2013
- 2013-05-07 EP EP13727515.2A patent/EP2855627B1/en not_active Not-in-force
- 2013-05-07 KR KR1020147036288A patent/KR20150013898A/ko not_active Ceased
- 2013-05-07 US US14/403,201 patent/US20150090935A1/en not_active Abandoned
- 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
- 2013-05-07 CN CN201380026565.0A patent/CN104364347B/zh active Active
- 2013-05-24 TW TW102118499A patent/TWI630262B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW201404870A (zh) | 2014-02-01 |
| CN104364347B (zh) | 2017-12-01 |
| US20150090935A1 (en) | 2015-04-02 |
| EP2855627A1 (en) | 2015-04-08 |
| JP6600255B2 (ja) | 2019-10-30 |
| JP2015523334A (ja) | 2015-08-13 |
| TWI630262B (zh) | 2018-07-21 |
| CN104364347A (zh) | 2015-02-18 |
| WO2013174478A1 (en) | 2013-11-28 |
| EP2855627B1 (en) | 2017-09-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102014557B1 (ko) | 바이메소제닉 화합물 | |
| JP6600255B2 (ja) | ビメソゲン化合物およびメソゲン媒体 | |
| JP6523953B2 (ja) | ビメソゲン化合物およびメソゲン媒体 | |
| JP6523952B2 (ja) | ビメソゲン化合物およびメソゲン媒体 | |
| JP6523951B2 (ja) | ビメソゲン化合物およびメソゲン媒体 | |
| KR20150021954A (ko) | 메소젠성 매질 및 액정 디스플레이 | |
| CN104583366B (zh) | 双介晶化合物和介晶介质 | |
| JP6463363B2 (ja) | メソゲン化合物およびメソゲン媒体 | |
| KR20160088425A (ko) | 메소젠성 매질 및 액정 디스플레이 | |
| JP6419713B2 (ja) | ビメソゲン化合物およびメソゲン媒体 | |
| KR20170082590A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| KR20170036713A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| KR20160089446A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| KR20170095986A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| KR20160102275A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| JP6441323B2 (ja) | 化合物およびメソゲン媒体 | |
| KR20170095311A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| KR20170097115A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20141224 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20180503 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20191213 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20200420 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20191213 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |