JP5808565B2 - 液晶化合物および液晶媒体 - Google Patents
液晶化合物および液晶媒体 Download PDFInfo
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- JP5808565B2 JP5808565B2 JP2011090983A JP2011090983A JP5808565B2 JP 5808565 B2 JP5808565 B2 JP 5808565B2 JP 2011090983 A JP2011090983 A JP 2011090983A JP 2011090983 A JP2011090983 A JP 2011090983A JP 5808565 B2 JP5808565 B2 JP 5808565B2
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- 150000001875 compounds Chemical class 0.000 title claims description 103
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 10
- -1 boronate ester Chemical class 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical class OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 230000008840 asymmetric binding Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012071 phase Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 28
- 210000004027 cell Anatomy 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 6
- QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000003446 memory effect Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- 0 *c1cc(N)c(C(N)(N)Oc2ccc(-c3cc(N)c(*)c(N)c3)c(N)c2)c(NIc2c(*)c(N)cc(*)c2)c1 Chemical compound *c1cc(N)c(C(N)(N)Oc2ccc(-c3cc(N)c(*)c(N)c3)c(N)c2)c(NIc2c(*)c(N)cc(*)c2)c1 0.000 description 2
- CNSDDCYIKORYGV-UHFFFAOYSA-N 5-(4-butoxy-2-fluorophenyl)-2-[[4-[3,5-difluoro-4-(trifluoromethyl)phenyl]-3-fluorophenoxy]-difluoromethyl]-1,3-difluorobenzene Chemical group FC1=CC(OCCCC)=CC=C1C1=CC(F)=C(C(F)(F)OC=2C=C(F)C(=CC=2)C=2C=C(F)C(=C(F)C=2)C(F)(F)F)C(F)=C1 CNSDDCYIKORYGV-UHFFFAOYSA-N 0.000 description 2
- 230000005374 Kerr effect Effects 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
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- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QOIWHSKYUNIFCV-UHFFFAOYSA-N (2-fluoro-4-propylphenyl)boronic acid Chemical compound CCCC1=CC=C(B(O)O)C(F)=C1 QOIWHSKYUNIFCV-UHFFFAOYSA-N 0.000 description 1
- QQZQZZKHAQDOQS-UHFFFAOYSA-N 1-bromo-4-butoxy-2-fluorobenzene Chemical compound CCCCOC1=CC=C(Br)C(F)=C1 QQZQZZKHAQDOQS-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical class CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical class CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- XDLMGMZRCJUFSK-UHFFFAOYSA-N 2-[[4-[3,5-difluoro-4-(trifluoromethyl)phenyl]-3-fluorophenoxy]-difluoromethyl]-1,3-difluoro-5-(2-fluoro-4-propylphenyl)benzene Chemical group FC1=CC(CCC)=CC=C1C1=CC(F)=C(C(F)(F)OC=2C=C(F)C(=CC=2)C=2C=C(F)C(=C(F)C=2)C(F)(F)F)C(F)=C1 XDLMGMZRCJUFSK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- QOYKICGXKHSHNN-UHFFFAOYSA-N 5-bromo-2-[[4-[3,5-difluoro-4-(trifluoromethyl)phenyl]-3-fluorophenoxy]-difluoromethyl]-1,3-difluorobenzene Chemical group C=1C=C(C=2C=C(F)C(=C(F)C=2)C(F)(F)F)C(F)=CC=1OC(F)(F)C1=C(F)C=C(Br)C=C1F QOYKICGXKHSHNN-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FDEYNQHYWGZWRS-UHFFFAOYSA-N CC(CC1)CCC1c1ccc(C)cc1 Chemical compound CC(CC1)CCC1c1ccc(C)cc1 FDEYNQHYWGZWRS-UHFFFAOYSA-N 0.000 description 1
- RPMUDXVQHUECRE-UHFFFAOYSA-N CC1COC(C)OC1 Chemical compound CC1COC(C)OC1 RPMUDXVQHUECRE-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N COC(C(c1ccccc1)=O)(c1ccccc1)OC Chemical compound COC(C(c1ccccc1)=O)(c1ccccc1)OC KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- 241000238097 Callinectes sapidus Species 0.000 description 1
- AEPBEAPSBGPTCW-UHFFFAOYSA-N Cc(ccc(-c1cnc(C)cc1)c1)c1F Chemical compound Cc(ccc(-c1cnc(C)cc1)c1)c1F AEPBEAPSBGPTCW-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
- WJAVYWPXOXAOBS-UHFFFAOYSA-N Cc1cc(F)c(C)cc1 Chemical compound Cc1cc(F)c(C)cc1 WJAVYWPXOXAOBS-UHFFFAOYSA-N 0.000 description 1
- RHOOLJLEYYXKTK-UHFFFAOYSA-N Cc1cnc(C)nc1 Chemical compound Cc1cnc(C)nc1 RHOOLJLEYYXKTK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 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 1
- 125000005620 boronic acid group Chemical class 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- 238000011049 filling Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 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
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 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
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
-
- 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
- C09K19/0275—Blue phase
-
- 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
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- 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
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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
- 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
- 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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- 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
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Description
L1は、HまたはF、好ましくは、Hを表し、
R1は、1〜15個のC原子を有する無置換のアルキル基を表し、ただし加えて、この基における1個以上のCH2基は、それぞれ互いに独立に、O原子が互いに直接連結しないようにして、−C≡C−、−CH=CH−、−CF=CF−、−CF=CH−、−CH=CF−、−(CO)O−、−O(CO)−、−(CO)−または−O−により置き換えられていてもよく、および
R2は、CF3またはOCF3、好ましくは、CF3を表す。
X1またはX2は、−B(OH)2、ボロン酸エステルまたはボロン酸塩を表し、他の基は、Cl、Br、Iまたは−O(SO2)CF3を表す。好ましい遷移金属はパラジウムである。
R1は、それぞれの場合において互いに独立に、1〜15個のC原子を有する無置換のアルキル基(ただし加えて、この基における1個以上のCH2基は、それぞれ互いに独立に、O原子が互いに直接連結しないようにして、−C≡C−、−CH=CH−、−CF=CF−、−CF=CH−、−CH=CF−、−(CO)O−、−O(CO)−、−(CO)−または−O−により置き換えられていてもよい。)、好ましくは、2〜7個のC原子を有する直鎖状のアルキル基を表し、
A2、A3は、互いに独立に、
Z2、Z3は、互いに独立に、単結合、CF2O、CH2CH2、CF2CH2、CF2CF2、CFHCFH、CFHCH2、(CO)O、CH2O、C≡C、CH=CH、CF=CH、CF=CFを表し、ただし、非対称な結合単位(例えば、CF2O)は両方の可能な方向のどちらを向いていてもよく、
X1は、F、Cl、CN、または、1〜3個のC原子を有しFにより一置換または多置換されているアルキル、アルケニル、アルケニルオキシ、アルキルアルコキシまたはアルコキシを表し、および
L1〜L4は、HまたはFを表す。
THF テトラヒドロフラン
MTBE メチルtert−ブチルエーテル
SiO2 クロマトグラフィー用のシリカゲル
以下の例は、本発明をどのようにも制限することなく説明する。
液晶ベース混合物(ホスト)の成分を記載するために、以下の頭字語を使用する。添え字nは1〜9の値を採用する。以下の化合物は、本発明による液晶媒体の調製に適切である。
<表A:LC成分のための頭字語>
サンプルを重合する前に、約10ミクロンの厚みおよび2×2.5cmの面積を有するテストセルにおいて媒体の相特性を決定する。毛細管現象によって75℃の温度で充填を行う。加熱ステージを備える偏光顕微鏡下で1℃/分の加熱速度において、未重合の媒体を測定する。約1.5mW/cm2の有効出力を有するUVランプ(Honle社、Bluepoint 2.1、365nm干渉フィルター)を使用して、180秒間の照射によって媒体の重合を行う。重合は、電気光学的テストセル内において直接行う。最初に、媒体がブルー相I(BP−I)内にある温度において重合を行う。複数の段階的工程において重合を行い、これにより徐々に重合が完了する結果となる。一般に、重合中に、ブルー相の温度範囲が変化する。従って、それぞれの段階的工程間において、媒体が引き続きブルー相内にあるように温度を適合させる。実際には、このことは、それぞれ約5秒以上の照射操作後に偏光顕微鏡下においてサンプルを観察することによって行うことができる。サンプルがより暗くなる場合、このことは、等方相への転移を意味する。それに応じて、次の段階的工程のための温度を下げる。示される照射強度において最大の安定化の結果となる全照射時間は、典型的には180秒である。最適化された照射/温度プログラムに従って、更なる重合を行うことができる。あるいは、特に、重合前に既に十分に広いブルー相が存在している場合、1回の照射工程において重合を行うこともできる。
上記の重合およびブルー相の安定化後、ブルー相の相幅を決定する。引き続き、この範囲内、および、必要であればこの範囲外の種々の温度において、電気光学的特性の解析を行う。
Claims (26)
- L1が水素原子を表すことを特徴とする請求項1に記載の化合物。
- R2が基CF3を表すことを特徴とする請求項1または2に記載の化合物。
- R 2 が基OCF 3 を表すことを特徴とする請求項1または2に記載の化合物。
- R1が1〜12個のC原子を有する直鎖状のアルキル基を表すことを特徴とする請求項1〜4のいずれか1項に記載の化合物。
- R1が3個のC原子を有する直鎖状のアルキル基を表すことを特徴とする請求項1〜5のいずれか1項に記載の化合物。
- R 1 が2〜5個のC原子を有する直鎖状のアルキル基を表すことを特徴とする請求項1〜4のいずれか1項に記載の化合物。
- R 1 が2〜5個のC原子を有する直鎖状のアルコキシ基を表すことを特徴とする請求項1〜4のいずれか1項に記載の化合物。
- ブルー相を示す液晶媒体で動作する液晶ディスプレイにおいて使用することを特徴とする請求項1〜10のいずれか1項に記載の化合物。
- 液晶媒体はポリマー安定化されていることを特徴とする請求項11に記載の化合物。
- 請求項1〜12のいずれか1項に記載の式Iの1種類以上の化合物を含むことを特徴とする液晶媒体。
- 2種類以上の式Iの化合物を含むことを特徴とする請求項14に記載の液晶媒体。
- 液晶媒体の全体を基礎として10〜50質量%の式Iの化合物を含むことを特徴とする請求項14または15に記載の液晶媒体。
- 式IIおよびIIIの化合物より選択される1種類以上の化合物を追加的に含むことを特徴とする請求項14〜16のいずれか1項に記載の液晶媒体。
R1は、互いに独立に、1〜15個のC原子を有する無置換のアルキル基(ただし加えて、この基における1個以上のCH2基は、それぞれ互いに独立に、O原子が互いに直接連結しないようにして、−C≡C−、−CH=CH−、−CF=CF−、−CF=CH−、−CH=CF−、−(CO)O−、−O(CO)−、−(CO)−または−O−により置き換えられていてもよい。)、好ましくは、2〜7個のC原子を有する直鎖状のアルキル基を表し、
A2、A3は、互いに独立に、
Z2、Z3は、互いに独立に、単結合、CF2O、CH2CH2、CF2CH2、CF2CF2、CFHCFH、CFHCH2、(CO)O、CH2O、C≡C、CH=CH、CF=CH、CF=CFを表し、ただし、非対称な結合単位は両方の可能な方向のどちらを向いていてもよく、
X1は、F、Cl、CN、または、1〜3個のC原子を有しFにより一置換または多置換されているアルキル、アルケニル、アルケニルオキシ、アルコキシアルキルまたはアルコキシを表し、および
L1〜L4は、HまたはFを表す。) - 1種類以上の重合性化合物(モノマー)を更に含むことを特徴とする請求項14〜20のいずれか1項に記載の液晶媒体。
- ブルー相を示すことを特徴とする請求項14〜21のいずれか1項に記載の液晶媒体。
- ポリマー安定化されていることを特徴とする請求項22に記載の液晶媒体。
- 液晶媒体における、または、電気光学的ディスプレイにおける請求項1〜12のいずれか1項に記載の式Iの化合物の使用。
- 請求項14〜21のいずれか1項に記載の液晶媒体を含有する電気光学的ディスプレイ装置。
- 液晶ブルー相の領域において完全または部分的に動作することを特徴とする請求項25に記載の電気光学的ディスプレイ装置。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014522432A (ja) * | 2011-06-01 | 2014-09-04 | 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 | 液晶媒体および液晶ディスプレイ |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102216424B (zh) * | 2008-11-19 | 2014-05-07 | Jnc株式会社 | 光等向性的液晶介质与光元件 |
EP2399972B1 (en) * | 2010-06-25 | 2015-11-25 | Merck Patent GmbH | Liquid-crystalline medium and liquid-crystal display having high twist |
EP2568032B1 (en) * | 2011-09-06 | 2014-11-26 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
CN103781877B (zh) * | 2011-09-06 | 2017-12-12 | 默克专利股份有限公司 | 液晶介质和液晶显示器 |
KR20130057396A (ko) * | 2011-11-23 | 2013-05-31 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 액정 조성물 및 액정 표시 장치 |
JP2013155157A (ja) * | 2012-01-31 | 2013-08-15 | Dic Corp | 化合物 |
JP6166352B2 (ja) * | 2012-04-20 | 2017-07-19 | 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ィスプレイ |
JP2013241401A (ja) * | 2012-04-26 | 2013-12-05 | Agc Seimi Chemical Co Ltd | 液晶化合物の製造方法、およびその中間体 |
JP2014005380A (ja) * | 2012-06-25 | 2014-01-16 | Dic Corp | 液晶組成物 |
KR20150090161A (ko) * | 2012-11-27 | 2015-08-05 | 메르크 파텐트 게엠베하 | 렌즈 소자 |
JP5975081B2 (ja) | 2013-09-30 | 2016-08-23 | ダイキン工業株式会社 | 含フッ素ビアリール化合物の製造方法 |
US9938464B2 (en) * | 2013-12-30 | 2018-04-10 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
US10160930B2 (en) * | 2014-03-14 | 2018-12-25 | Merck Patent Gmbh | Electro-rheological fluid and haptic device |
TWI648381B (zh) | 2014-07-03 | 2019-01-21 | 日商捷恩智股份有限公司 | 液晶組成物、光元件、混合物、化合物、高分子/液晶複合材料以及液晶組成物及高分子/液晶複合材料的用途 |
CN105586050B (zh) * | 2014-10-20 | 2018-01-30 | 江苏和成显示科技股份有限公司 | 液晶组合物及液晶显示器件 |
CN105586055B (zh) * | 2014-10-20 | 2018-07-24 | 江苏和成显示科技有限公司 | 液晶组合物及其液晶显示器件 |
CN104496766B (zh) * | 2014-12-11 | 2017-02-08 | 西安彩晶光电科技股份有限公司 | 一类含有2,3,5,6‑四氟苯基和三氟甲氧基的二氟甲氧基化合物及其制备方法与应用 |
CN106146251A (zh) * | 2015-03-27 | 2016-11-23 | 北京欣奕华科技有限公司 | 化合物及其制备方法 |
WO2017020989A1 (en) * | 2015-07-31 | 2017-02-09 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
EP3124573B1 (en) * | 2015-07-31 | 2018-03-28 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001003051A (ja) * | 1999-04-19 | 2001-01-09 | Chisso Corp | 液晶組成物および液晶表示素子 |
JP5225531B2 (ja) * | 2000-12-19 | 2013-07-03 | 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 | 負のdc異方性の四環式化合物および液晶媒体 |
JP4300714B2 (ja) | 2001-04-27 | 2009-07-22 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
DE10243776B4 (de) * | 2001-09-29 | 2017-11-16 | Merck Patent Gmbh | Flüssigkristalline Verbindungen |
DE10150198A1 (de) * | 2001-10-12 | 2003-04-24 | Merck Patent Gmbh | Flüssigkristallines Medium |
JP4104350B2 (ja) | 2002-03-05 | 2008-06-18 | Agcセイミケミカル株式会社 | ジフルオロベンジルブロミド誘導体およびジフルオロベンジルエーテル誘導体の製造方法 |
ATE374232T1 (de) * | 2002-11-27 | 2007-10-15 | Merck Patent Gmbh | Flüssigkristalline verbindungen |
DE102004008638A1 (de) | 2003-03-05 | 2004-09-16 | Merck Patent Gmbh | Flüssigkristallines Medium |
JP2006169174A (ja) * | 2004-12-16 | 2006-06-29 | Asahi Glass Co Ltd | ジフルオロメチルエーテル誘導体の製造方法 |
DE102007009944B4 (de) * | 2006-03-15 | 2016-04-28 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung |
DE502007004625D1 (de) * | 2006-09-13 | 2010-09-16 | Merck Patent Gmbh | Fluorphenyl-Verbindungen für flüssigkristalline Mischungen |
KR101435236B1 (ko) * | 2007-01-24 | 2014-08-28 | 제이엔씨 석유 화학 주식회사 | 액정성 화합물, 액정 조성물 및 액정 표시 소자 |
JP5470757B2 (ja) * | 2007-08-29 | 2014-04-16 | Jnc株式会社 | 光学的に等方性の液晶媒体及び光素子 |
US7879413B2 (en) | 2007-08-29 | 2011-02-01 | Chisso Corporation | Optically isotropic liquid crystal medium and optical device |
ATE527333T1 (de) * | 2008-03-11 | 2011-10-15 | Merck Patent Gmbh | Flüssigkristallines medium und flüssigkristallanzeige |
CN102216424B (zh) * | 2008-11-19 | 2014-05-07 | Jnc株式会社 | 光等向性的液晶介质与光元件 |
JP5625461B2 (ja) * | 2009-05-19 | 2014-11-19 | Jnc株式会社 | クロロフルオロベンゼン化合物、光学的等方性の液晶媒体および光素子 |
DE102011013006A1 (de) * | 2010-03-23 | 2011-09-29 | Merck Patent Gmbh | Flüssigkristalline Verbindungen und flüssigkristalline Medien |
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