KR101868648B1 - 티오펜 유도체를 함유하는 액정 매질 - Google Patents
티오펜 유도체를 함유하는 액정 매질 Download PDFInfo
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- KR101868648B1 KR101868648B1 KR1020137004966A KR20137004966A KR101868648B1 KR 101868648 B1 KR101868648 B1 KR 101868648B1 KR 1020137004966 A KR1020137004966 A KR 1020137004966A KR 20137004966 A KR20137004966 A KR 20137004966A KR 101868648 B1 KR101868648 B1 KR 101868648B1
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 38
- 150000003577 thiophenes Chemical class 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 117
- -1 cyclohexane-1,4-diyl Chemical group 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 description 51
- 210000004027 cell Anatomy 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- 230000004044 response Effects 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 0 *c(cc1)ccc1-c(cc1)ccc1-c1cc(F)c(*c2cc(*)c(*)c(F)c2)c(*)c1 Chemical compound *c(cc1)ccc1-c(cc1)ccc1-c1cc(F)c(*c2cc(*)c(*)c(F)c2)c(*)c1 0.000 description 4
- GDBVVTJSGDEUPR-UHFFFAOYSA-N 2-[2,6-difluoro-4-(4-propylphenyl)phenyl]-5-propylthiophene Chemical compound S1C(CCC)=CC=C1C1=C(F)C=C(C=2C=CC(CCC)=CC=2)C=C1F GDBVVTJSGDEUPR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- HYRYQZIGBWDHAD-UHFFFAOYSA-N 2-bromo-5-ethylthiophene Chemical compound CCC1=CC=C(Br)S1 HYRYQZIGBWDHAD-UHFFFAOYSA-N 0.000 description 3
- AZMSRFANKVHIEG-UHFFFAOYSA-N 2-bromo-5-propylthiophene Chemical compound CCCC1=CC=C(Br)S1 AZMSRFANKVHIEG-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- MSYHVNATNGNOOY-UHFFFAOYSA-N 1,3-difluoro-5-(4-propylphenyl)benzene Chemical group C1=CC(CCC)=CC=C1C1=CC(F)=CC(F)=C1 MSYHVNATNGNOOY-UHFFFAOYSA-N 0.000 description 2
- GVUIYZFTYBCCKJ-UHFFFAOYSA-N 2-(4-ethylphenyl)-1,3-difluorobenzene Chemical group C1=CC(CC)=CC=C1C1=C(F)C=CC=C1F GVUIYZFTYBCCKJ-UHFFFAOYSA-N 0.000 description 2
- RJHFYYMQAHTWPW-UHFFFAOYSA-N 2-[2,6-difluoro-4-(4-propylcyclohexyl)phenyl]-5-ethylthiophene Chemical compound C1CC(CCC)CCC1C(C=C1F)=CC(F)=C1C1=CC=C(CC)S1 RJHFYYMQAHTWPW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KOLJRVLDEBMHMC-UHFFFAOYSA-N [2,6-difluoro-4-(4-propylphenyl)phenyl]boronic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC(F)=C(B(O)O)C(F)=C1 KOLJRVLDEBMHMC-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 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
- 239000000470 constituent Substances 0.000 description 2
- 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
- 229910052740 iodine Inorganic materials 0.000 description 2
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920001690 polydopamine Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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- 238000010561 standard procedure Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
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- 229930192474 thiophene Natural products 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DOSCGNSNJRXJMT-UHFFFAOYSA-N 1-fluoro-2-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=CC=C1F DOSCGNSNJRXJMT-UHFFFAOYSA-N 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- YJSNJQSUPJYSSV-UHFFFAOYSA-N 2-[2,6-difluoro-4-(4-propylphenyl)phenyl]-5-ethylthiophene Chemical compound C1=CC(CCC)=CC=C1C(C=C1F)=CC(F)=C1C1=CC=C(CC)S1 YJSNJQSUPJYSSV-UHFFFAOYSA-N 0.000 description 1
- MVMCNZDNEINZLE-UHFFFAOYSA-N 2-[3-fluoro-4-(4-pentylphenyl)phenyl]-5-hexylthiophene Chemical compound S1C(CCCCCC)=CC=C1C1=CC=C(C=2C=CC(CCCCC)=CC=2)C(F)=C1 MVMCNZDNEINZLE-UHFFFAOYSA-N 0.000 description 1
- WVSFYQJOKNIGRU-UHFFFAOYSA-N 2-bromo-1,3-difluoro-5-(4-propylphenyl)benzene Chemical group C1=CC(CCC)=CC=C1C1=CC(F)=C(Br)C(F)=C1 WVSFYQJOKNIGRU-UHFFFAOYSA-N 0.000 description 1
- WJSIEDBETVAKKL-UHFFFAOYSA-N 2-bromo-5-ethenylthiophene Chemical compound BrC1=CC=C(C=C)S1 WJSIEDBETVAKKL-UHFFFAOYSA-N 0.000 description 1
- KIPWOOKIXYCLST-UHFFFAOYSA-N 2-ethyl-5-[4-(4-ethylphenyl)-2,6-difluorophenyl]thiophene Chemical compound S1C(CC)=CC=C1C1=C(F)C=C(C=2C=CC(CC)=CC=2)C=C1F KIPWOOKIXYCLST-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ATMCJRZDWVJJKE-UHFFFAOYSA-N CCCc1ccc(-c(c(F)cc(-c2ccc(CC)cc2)c2)c2F)[s]1 Chemical compound CCCc1ccc(-c(c(F)cc(-c2ccc(CC)cc2)c2)c2F)[s]1 ATMCJRZDWVJJKE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HBXFIXSFKULBOG-UHFFFAOYSA-N Cc1cc(F)c(C)c(F)c1 Chemical compound Cc1cc(F)c(C)c(F)c1 HBXFIXSFKULBOG-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229940123457 Free radical scavenger Drugs 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
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
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- 102100033075 Prostacyclin synthase Human genes 0.000 description 1
- 101710179550 Prostacyclin synthase Proteins 0.000 description 1
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- 206010047571 Visual impairment Diseases 0.000 description 1
- RRGPKFMHXDCBIH-UHFFFAOYSA-N [2,5-difluoro-4-(4-propylcyclohexyl)phenyl]boronic acid Chemical compound C1CC(CCC)CCC1C1=CC(F)=C(B(O)O)C=C1F RRGPKFMHXDCBIH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
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- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
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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 1
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- DGLRDKLJZLEJCY-UHFFFAOYSA-L disodium hydrogenphosphate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O DGLRDKLJZLEJCY-UHFFFAOYSA-L 0.000 description 1
- QPMAGMWYRUSFJP-UHFFFAOYSA-N disodium;(5-hexylthiophen-2-yl)oxy-dioxidoborane Chemical compound [Na+].[Na+].CCCCCCC1=CC=C(OB([O-])[O-])S1 QPMAGMWYRUSFJP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 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 1
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
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- 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 1
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- 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 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
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 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 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 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 1
- 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 1
- 239000008096 xylene Substances 0.000 description 1
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- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K2019/0466—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 the linking chain being a -CF2O- chain
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- 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
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3025—Cy-Ph-Ph-Ph
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010032617 | 2010-07-29 | ||
| DE102010032617.8 | 2010-07-29 | ||
| PCT/EP2011/003271 WO2012013281A1 (de) | 2010-07-29 | 2011-07-01 | Flüssigkristallines medium enthaltend thiophenderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140002608A KR20140002608A (ko) | 2014-01-08 |
| KR101868648B1 true KR101868648B1 (ko) | 2018-06-18 |
Family
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| KR1020137004966A Active KR101868648B1 (ko) | 2010-07-29 | 2011-07-01 | 티오펜 유도체를 함유하는 액정 매질 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8906261B2 (enExample) |
| EP (1) | EP2598604B1 (enExample) |
| JP (1) | JP5788508B2 (enExample) |
| KR (1) | KR101868648B1 (enExample) |
| CN (2) | CN107011920B (enExample) |
| DE (1) | DE102011106314A1 (enExample) |
| TW (1) | TWI513803B (enExample) |
| WO (1) | WO2012013281A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI462992B (zh) * | 2011-04-18 | 2014-12-01 | Daxin Materials Corp | 液晶化合物 |
| CN103562347B (zh) * | 2011-06-01 | 2016-08-17 | 默克专利股份有限公司 | 液晶介质和液晶显示器 |
| DE102015003602A1 (de) * | 2015-03-18 | 2016-09-22 | Merck Patent Gmbh | Flüssigkristalines Medium |
| JP6801835B2 (ja) * | 2015-07-09 | 2020-12-16 | ミメトゲン ファーマシュウティカルズ インコーポレイテッドＭｉｍｅｔｏｇｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | β−ターンペプチド模倣環状塩の液相合成及び結晶化 |
| JP2021512209A (ja) * | 2018-01-24 | 2021-05-13 | 日東電工株式会社 | ５員複素環を含む液晶組成物、リバースモードポリマー分散液晶素子、および関連する選択的可視化デバイス |
| CN110229679B (zh) * | 2018-03-06 | 2020-11-17 | 北京八亿时空液晶科技股份有限公司 | 一种液晶介质的自配向添加剂及其制备方法与应用 |
| KR20210025634A (ko) * | 2018-06-29 | 2021-03-09 | 메르크 파텐트 게엠베하 | 티오펜 화합물, 액정 매질 및 이를 포함하는 액정 디스플레이 |
| EP3763802B1 (en) * | 2018-07-12 | 2023-09-06 | Merck Patent GmbH | Thiophene compound, liquid-crystalline medium and liquid-crystal display comprising the same |
| CN112143507B (zh) | 2019-06-28 | 2025-03-18 | 默克专利股份有限公司 | Lc介质 |
| TWI892896B (zh) * | 2019-12-20 | 2025-08-01 | 德商馬克專利公司 | 液晶介質及含彼之液晶顯示器 |
| JP2021187742A (ja) * | 2020-05-26 | 2021-12-13 | Jnc株式会社 | 化合物、液晶組成物および液晶表示素子 |
| CN112266794B (zh) * | 2020-09-30 | 2022-09-09 | 北京八亿时空液晶科技股份有限公司 | 一种含噻吩的液晶化合物及其制备方法和应用 |
| CN115197716A (zh) | 2021-04-13 | 2022-10-18 | 默克专利股份有限公司 | 液晶介质 |
| TW202311501A (zh) * | 2021-05-12 | 2023-03-16 | 德商馬克專利公司 | 液晶介質及電子組件 |
| CN118974206A (zh) | 2022-03-25 | 2024-11-15 | 默克专利股份有限公司 | 液晶介质 |
| JP2025513057A (ja) * | 2022-04-12 | 2025-04-22 | 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 | 液晶媒体 |
| EP4261269B1 (en) | 2022-04-12 | 2025-10-29 | Merck Patent GmbH | Liquid-crystalline medium |
| WO2025000508A1 (en) * | 2023-06-30 | 2025-01-02 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN117448010B (zh) | 2023-09-26 | 2025-10-14 | Tcl华星光电技术有限公司 | 液晶组合物及显示面板 |
| CN117603708B (zh) * | 2023-09-27 | 2025-11-21 | 惠州华星光电显示有限公司 | 液晶组合物及显示面板 |
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|---|---|---|---|---|
| JPH04217973A (ja) * | 1990-07-16 | 1992-08-07 | Canon Inc | 液晶性化合物、これを含む液晶組成物およびこれを利用した液晶素子、表示装置 |
| JPH06321821A (ja) * | 1993-05-17 | 1994-11-22 | Canon Inc | 液晶性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示方法および表示装置 |
| JP2007084487A (ja) * | 2005-09-22 | 2007-04-05 | Adeka Corp | チオフェン化合物、該化合物を含有してなる液晶組成物、及び液晶素子 |
| WO2009129915A1 (de) * | 2008-04-24 | 2009-10-29 | Merck Patent Gmbh | Thiophenderivate und diese enthaltende fk-medien |
| KR20110117250A (ko) * | 2009-02-19 | 2011-10-26 | 메르크 파텐트 게엠베하 | 티오펜 유도체 및 이를 함유하는 액정 매질 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3022818C2 (de) | 1980-06-19 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Flüssigkristall-Anzeigeelement |
| WO2006022040A1 (ja) * | 2004-08-27 | 2006-03-02 | National Institute Of Advanced Industrial Science And Technology | １，４−ジチエニルベンゼン誘導体 |
| WO2010094455A1 (de) | 2009-02-19 | 2010-08-26 | Merck Patent Gmbh | Thiophen-verbindungen für flüssigkristalline medien |
-
2011
- 2011-07-01 WO PCT/EP2011/003271 patent/WO2012013281A1/de not_active Ceased
- 2011-07-01 DE DE102011106314A patent/DE102011106314A1/de not_active Withdrawn
- 2011-07-01 KR KR1020137004966A patent/KR101868648B1/ko active Active
- 2011-07-01 JP JP2013520992A patent/JP5788508B2/ja active Active
- 2011-07-01 EP EP11728788.8A patent/EP2598604B1/de active Active
- 2011-07-01 CN CN201610948046.5A patent/CN107011920B/zh active Active
- 2011-07-01 US US13/812,743 patent/US8906261B2/en active Active
- 2011-07-01 CN CN201180036766XA patent/CN103038312A/zh active Pending
- 2011-07-28 TW TW100126834A patent/TWI513803B/zh active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04217973A (ja) * | 1990-07-16 | 1992-08-07 | Canon Inc | 液晶性化合物、これを含む液晶組成物およびこれを利用した液晶素子、表示装置 |
| JPH06321821A (ja) * | 1993-05-17 | 1994-11-22 | Canon Inc | 液晶性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示方法および表示装置 |
| JP2007084487A (ja) * | 2005-09-22 | 2007-04-05 | Adeka Corp | チオフェン化合物、該化合物を含有してなる液晶組成物、及び液晶素子 |
| WO2009129915A1 (de) * | 2008-04-24 | 2009-10-29 | Merck Patent Gmbh | Thiophenderivate und diese enthaltende fk-medien |
| KR20110117250A (ko) * | 2009-02-19 | 2011-10-26 | 메르크 파텐트 게엠베하 | 티오펜 유도체 및 이를 함유하는 액정 매질 |
| KR101675175B1 (ko) * | 2009-02-19 | 2016-11-10 | 메르크 파텐트 게엠베하 | 티오펜 유도체 및 이를 함유하는 액정 매질 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013537571A (ja) | 2013-10-03 |
| KR20140002608A (ko) | 2014-01-08 |
| JP5788508B2 (ja) | 2015-09-30 |
| WO2012013281A1 (de) | 2012-02-02 |
| EP2598604B1 (de) | 2015-11-25 |
| CN107011920B (zh) | 2021-06-22 |
| US20130119312A1 (en) | 2013-05-16 |
| TW201213516A (en) | 2012-04-01 |
| EP2598604A1 (de) | 2013-06-05 |
| US8906261B2 (en) | 2014-12-09 |
| DE102011106314A1 (de) | 2012-02-02 |
| TWI513803B (zh) | 2015-12-21 |
| CN107011920A (zh) | 2017-08-04 |
| CN103038312A (zh) | 2013-04-10 |
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