KR20150036407A - 바이메소제닉 화합물 및 메소제닉 매질 - Google Patents
바이메소제닉 화합물 및 메소제닉 매질 Download PDFInfo
- Publication number
- KR20150036407A KR20150036407A KR20157003134A KR20157003134A KR20150036407A KR 20150036407 A KR20150036407 A KR 20150036407A KR 20157003134 A KR20157003134 A KR 20157003134A KR 20157003134 A KR20157003134 A KR 20157003134A KR 20150036407 A KR20150036407 A KR 20150036407A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- liquid crystal
- group
- compounds
- groups
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 138
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 76
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- -1 piperidine-1,4-diyl Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000006850 spacer group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 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 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 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
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 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
- 125000005843 halogen group Chemical group 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
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 description 122
- 239000012071 phase Substances 0.000 description 44
- 239000000463 material Substances 0.000 description 32
- 210000004027 cell Anatomy 0.000 description 30
- 239000000758 substrate Substances 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 230000003287 optical effect Effects 0.000 description 23
- 230000005684 electric field Effects 0.000 description 22
- 230000003098 cholesteric effect Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000011295 pitch Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 239000000377 silicon dioxide Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000004044 response Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 230000007704 transition Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 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
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- ZXZBMGGWHWRHPS-UHFFFAOYSA-N cyanato(phenyl)borinic acid Chemical compound N#COB(O)C1=CC=CC=C1 ZXZBMGGWHWRHPS-UHFFFAOYSA-N 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
- 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
- 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
- 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
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 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
- 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
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000003573 thiols Chemical class 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
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-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
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- SUODCTNNAKSRHB-UHFFFAOYSA-N 2-ethylhexyl 3-sulfanylpropanoate Chemical compound CCCCC(CC)COC(=O)CCS SUODCTNNAKSRHB-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
- FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- QCNUKEGGHOLBES-UHFFFAOYSA-N CCCC(CC1)CCC1C(O)=O Chemical compound CCCC(CC1)CCC1C(O)=O QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 1
- HIXBGYMAKLHYPY-UHFFFAOYSA-N CCCCC(CC)COC(CCSc(cc1)ccc1-c(cc1)ccc1C#N)=O Chemical compound CCCCC(CC)COC(CCSc(cc1)ccc1-c(cc1)ccc1C#N)=O HIXBGYMAKLHYPY-UHFFFAOYSA-N 0.000 description 1
- JTUXHRXCSSYALW-UHFFFAOYSA-N CCCCC(CC)COC(CCSc(cc1)ccc1Br)=O Chemical compound CCCCC(CC)COC(CCSc(cc1)ccc1Br)=O JTUXHRXCSSYALW-UHFFFAOYSA-N 0.000 description 1
- 0 CCCNC(CC1)CC2C1C(*)(*)C2 Chemical compound CCCNC(CC1)CC2C1C(*)(*)C2 0.000 description 1
- SOSHQYYQGJQAHW-QAPCUYQASA-N CC[C@@H]([C@H](C)c1ccccc1)c(cccc1)c1C#C Chemical compound CC[C@@H]([C@H](C)c1ccccc1)c(cccc1)c1C#C SOSHQYYQGJQAHW-QAPCUYQASA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- SIHJSPXCUPKUHH-UHFFFAOYSA-N N#Cc(cc1)ccc1-c(cc1)ccc1SC(CCCCCCCCCC(Sc(cc1)ccc1-c(cc1F)ccc1F)=O)=O Chemical compound N#Cc(cc1)ccc1-c(cc1)ccc1SC(CCCCCCCCCC(Sc(cc1)ccc1-c(cc1F)ccc1F)=O)=O SIHJSPXCUPKUHH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001660687 Xantho Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 230000036755 cellular response Effects 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
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000009977 dual effect Effects 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000013067 intermediate product Substances 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
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000011368 organic material Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 230000000007 visual effect Effects 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
- C09K19/04—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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
- C07C329/20—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to carbon atoms of six-membered aromatic rings
-
- 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
-
- 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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/28—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and sulfur atoms as chain links, e.g. thioesters
-
- 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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
-
- 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)
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12005046.3 | 2012-07-06 | ||
| EP12005046 | 2012-07-06 | ||
| PCT/EP2013/001772 WO2014005671A1 (en) | 2012-07-06 | 2013-06-14 | Bimesogenic compounds and mesogenic media |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150036407A true KR20150036407A (ko) | 2015-04-07 |
Family
ID=48669856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20157003134A Abandoned KR20150036407A (ko) | 2012-07-06 | 2013-06-14 | 바이메소제닉 화합물 및 메소제닉 매질 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20150203756A1 (enExample) |
| EP (1) | EP2870219B1 (enExample) |
| JP (1) | JP6523952B2 (enExample) |
| KR (1) | KR20150036407A (enExample) |
| CN (1) | CN104487542B (enExample) |
| TW (1) | TWI586791B (enExample) |
| WO (1) | WO2014005671A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014005672A1 (en) * | 2012-07-06 | 2014-01-09 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| WO2014005670A1 (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 |
| CN105555917B (zh) * | 2013-09-12 | 2019-03-01 | 默克专利股份有限公司 | 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| WO2019121368A1 (en) * | 2017-12-18 | 2019-06-27 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal device |
| GB2583668A (en) * | 2017-12-18 | 2020-11-04 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal device |
| WO2019179962A1 (en) * | 2018-03-22 | 2019-09-26 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN110467926B (zh) * | 2018-05-10 | 2023-10-31 | 江苏集萃智能液晶科技有限公司 | 液晶组合物及其液晶显示器 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2516382A1 (de) * | 1974-04-18 | 1975-11-06 | Ciba Geigy Ag | Phenyl-aralkyl-aether, -thioaether und -amine |
| JPS54119476A (en) * | 1978-03-10 | 1979-09-17 | Ishihara Sangyo Kaisha Ltd | 4-(5-fluoromethyl-2-pyridyloxy)phenoxyalkanecarbocyic acid derivatives and their preparation |
| DE3040632A1 (de) * | 1980-10-29 | 1982-05-27 | Merck Patent Gmbh, 6100 Darmstadt | Cyclohexylphenylderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| JPS63137985A (ja) * | 1986-11-28 | 1988-06-09 | Canon Inc | 強誘電性液晶素子 |
| JPS6436683A (en) * | 1987-07-31 | 1989-02-07 | Canon Kk | Ferroelectric liquid crystal element |
| DE4000451B4 (de) | 1990-01-09 | 2004-12-09 | Merck Patent Gmbh | Elektrooptisches Flüssigkristallschaltelement |
| EP1061404A1 (en) | 1992-09-18 | 2000-12-20 | Hitachi, Ltd. | A liquid crystal display device |
| GB2329636B (en) | 1996-07-01 | 2000-07-19 | Merck Patent Gmbh | Chiral dopants |
| 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 |
| JP4336925B2 (ja) * | 1999-08-16 | 2009-09-30 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| GB2356629B (en) * | 1999-10-04 | 2004-09-22 | Merck Patent Gmbh | Bimesogenic Compounds and Flexoelectric Devices |
| JP3750725B2 (ja) * | 1999-10-06 | 2006-03-01 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| GB0225662D0 (en) * | 2001-11-16 | 2002-12-11 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| JP2003306433A (ja) * | 2002-02-18 | 2003-10-28 | Ishihara Sangyo Kaisha Ltd | ピリジン誘導体またはその塩ならびにそれらを含有するサイトカイン産生抑制剤 |
| US6875780B2 (en) * | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| US7244763B2 (en) * | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| EP1477547B1 (en) * | 2003-05-09 | 2006-06-14 | MERCK PATENT GmbH | Liquid crystalline medium and liquid crystal display |
| SG145752A1 (en) * | 2003-09-19 | 2008-09-29 | Janssen Pharmaceutica Nv | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
| TW200538433A (en) * | 2004-02-24 | 2005-12-01 | Irm Llc | Immunosuppressant compounds and compositiions |
| 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 |
| US8669283B2 (en) * | 2008-02-26 | 2014-03-11 | Ludwig-Maximilians-Universitat Munchen | Beta-lactones as antibacterial agents |
| JP5423352B2 (ja) * | 2009-11-26 | 2014-02-19 | Ｊｓｒ株式会社 | 感放射線性樹脂組成物、液晶表示素子の層間絶縁膜、保護膜及びスペーサーならびにそれらの形成方法 |
| EP2729549B1 (en) * | 2011-07-05 | 2016-12-07 | Merck Patent GmbH | Bimesogenic compounds |
| JP5797132B2 (ja) * | 2012-03-07 | 2015-10-21 | 富士フイルム株式会社 | 化合物、液晶組成物、高分子材料およびフィルム |
| EP2855631B1 (en) * | 2012-05-25 | 2017-09-20 | Merck Patent GmbH | Mesogenic media and liquid crystal display |
| WO2014005672A1 (en) * | 2012-07-06 | 2014-01-09 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| WO2014005670A1 (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 |
| WO2014090372A1 (en) * | 2012-12-10 | 2014-06-19 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
-
2013
- 2013-06-14 KR KR20157003134A patent/KR20150036407A/ko not_active Abandoned
- 2013-06-14 EP EP13730120.6A patent/EP2870219B1/en not_active Not-in-force
- 2013-06-14 WO PCT/EP2013/001772 patent/WO2014005671A1/en not_active Ceased
- 2013-06-14 US US14/413,064 patent/US20150203756A1/en not_active Abandoned
- 2013-06-14 CN CN201380035212.7A patent/CN104487542B/zh active Active
- 2013-06-14 JP JP2015518884A patent/JP6523952B2/ja not_active Expired - Fee Related
- 2013-07-05 TW TW102124298A patent/TWI586791B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP6523952B2 (ja) | 2019-06-05 |
| CN104487542B (zh) | 2016-10-12 |
| JP2015527303A (ja) | 2015-09-17 |
| EP2870219A1 (en) | 2015-05-13 |
| EP2870219B1 (en) | 2016-05-25 |
| US20150203756A1 (en) | 2015-07-23 |
| CN104487542A (zh) | 2015-04-01 |
| WO2014005671A1 (en) | 2014-01-09 |
| TW201402790A (zh) | 2014-01-16 |
| TWI586791B (zh) | 2017-06-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102014557B1 (ko) | 바이메소제닉 화합물 | |
| JP6523952B2 (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 | |
| KR20150013898A (ko) | 바이메소제닉 화합물 및 메소제닉 매질 | |
| CN104583366B (zh) | 双介晶化合物和介晶介质 | |
| JP6523951B2 (ja) | ビメソゲン化合物およびメソゲン媒体 | |
| CN104822800B (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 | |
| KR20150021954A (ko) | 메소젠성 매질 및 액정 디스플레이 | |
| KR20170082590A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| JP6513664B2 (ja) | ビメソゲン化合物およびメソゲン媒体 | |
| KR20170101280A (ko) | 바이메소젠성 화합물 및 메소젠성 매질 | |
| KR20170036713A (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: 20150205 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20180614 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: 20200115 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20200521 |
|
| PC1904 | Unpaid initial registration fee |