DE60130338T2 - Chirale verbindungen ii - Google Patents
Chirale verbindungen ii Download PDFInfo
- Publication number
- DE60130338T2 DE60130338T2 DE60130338T DE60130338T DE60130338T2 DE 60130338 T2 DE60130338 T2 DE 60130338T2 DE 60130338 T DE60130338 T DE 60130338T DE 60130338 T DE60130338 T DE 60130338T DE 60130338 T2 DE60130338 T2 DE 60130338T2
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- Germany
- Prior art keywords
- chiral
- sup
- compounds
- formula
- liquid
- 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.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 149
- 239000000203 mixture Substances 0.000 claims abstract description 104
- -1 diagnostics Substances 0.000 claims abstract description 60
- 239000007788 liquid Substances 0.000 claims abstract description 48
- 239000002019 doping agent Substances 0.000 claims abstract description 40
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 32
- 239000000049 pigment Substances 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 13
- 230000003287 optical effect Effects 0.000 claims abstract description 9
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 229920000106 Liquid crystal polymer Polymers 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000000853 adhesive Substances 0.000 claims abstract description 4
- 230000001070 adhesive effect Effects 0.000 claims abstract description 4
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 4
- 239000000057 synthetic resin Substances 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 230000003098 cholesteric effect Effects 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000006850 spacer group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 claims description 3
- 238000013500 data storage Methods 0.000 claims description 3
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- AAFJXZWCNVJTMK-KVTDHHQDSA-N (1S,2S)-1,2-bis[(2R)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@@H]1[C@@H](O)[C@H](O)[C@@H]2OC2)O1 AAFJXZWCNVJTMK-KVTDHHQDSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IHPDTPWNFBQHEB-UHFFFAOYSA-N hydrobenzoin Chemical compound C=1C=CC=CC=1C(O)C(O)C1=CC=CC=C1 IHPDTPWNFBQHEB-UHFFFAOYSA-N 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
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- 230000008025 crystallization Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- QGJIFOZQMCBQIP-UHFFFAOYSA-N (2-hydroxy-2-phenylethyl) acetate Chemical compound CC(=O)OCC(O)C1=CC=CC=C1 QGJIFOZQMCBQIP-UHFFFAOYSA-N 0.000 description 2
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical class C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 2
- 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 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/323—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a binaphthyl
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/325—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/326—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
-
- 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
- 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
- C09K2323/031—Polarizer or dye
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00115251 | 2000-07-13 | ||
| EP00115251 | 2000-07-13 | ||
| PCT/EP2001/007215 WO2002006195A1 (en) | 2000-07-13 | 2001-06-25 | Chiral compounds ii |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60130338D1 DE60130338D1 (de) | 2007-10-18 |
| DE60130338T2 true DE60130338T2 (de) | 2008-05-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60130338T Expired - Lifetime DE60130338T2 (de) | 2000-07-13 | 2001-06-25 | Chirale verbindungen ii |
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| Country | Link |
|---|---|
| US (1) | US7318950B2 (enExample) |
| EP (1) | EP1299335B1 (enExample) |
| JP (1) | JP5317382B2 (enExample) |
| CN (1) | CN1206197C (enExample) |
| AT (1) | ATE372314T1 (enExample) |
| AU (1) | AU2001281884A1 (enExample) |
| DE (1) | DE60130338T2 (enExample) |
| WO (1) | WO2002006195A1 (enExample) |
Families Citing this family (116)
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| JP2003161835A (ja) | 2001-07-02 | 2003-06-06 | Merck Patent Gmbh | 光学可変マーキング |
| DE10257711B4 (de) | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
| US6699532B2 (en) * | 2002-06-25 | 2004-03-02 | Mitsubishi Gas Chemical Company, Inc. | Optically active compound and liquid crystal composition containing the compound |
| DE10253606A1 (de) * | 2002-11-15 | 2004-05-27 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
| TW585898B (en) | 2002-12-26 | 2004-05-01 | Ind Tech Res Inst | Liquid crystal compounds with optical activities having high helical twisting power, method for preparing the same, and liquid crystal composition containing the compounds |
| ATE353319T1 (de) | 2003-08-20 | 2007-02-15 | Axys Pharm Inc | Acetylenderivate als inhibitoren von histondeacetylase |
| DE112005000732T5 (de) | 2004-03-25 | 2008-09-04 | Merck Patent Gmbh | Flüssigkristallverbindungen, Flüssigkristallmedium und Flüssigkristallanzeige |
| US7943418B2 (en) * | 2004-09-16 | 2011-05-17 | Etamota Corporation | Removing undesirable nanotubes during nanotube device fabrication |
| US7462890B1 (en) | 2004-09-16 | 2008-12-09 | Atomate Corporation | Nanotube transistor integrated circuit layout |
| US7776307B2 (en) * | 2004-09-16 | 2010-08-17 | Etamota Corporation | Concentric gate nanotube transistor devices |
| US7345296B2 (en) * | 2004-09-16 | 2008-03-18 | Atomate Corporation | Nanotube transistor and rectifying devices |
| CN103254904B (zh) | 2004-12-17 | 2016-11-09 | 默克专利股份有限公司 | 液晶体系和液晶显示器 |
| JP2006273978A (ja) * | 2005-03-29 | 2006-10-12 | 21 Aomori Sangyo Sogo Shien Center | ビナフチル基をもつ化合物を含む液晶組成物 |
| CA2644917A1 (en) * | 2006-03-15 | 2007-09-20 | Trustees Of Tufts College | Fluorinated carbohydrates and their use in tumor visualization, tissue engineering, and cancer chemotherapy |
| EP1911828B1 (de) | 2006-10-12 | 2010-09-01 | Merck Patent GmbH | Flüssigkristallanzeige |
| EP2094815B1 (en) | 2006-12-22 | 2012-06-27 | Rolic AG | Patternable liquid crystal polymer comprising thio-ether units |
| US20080272361A1 (en) * | 2007-05-02 | 2008-11-06 | Atomate Corporation | High Density Nanotube Devices |
| EP2065361B1 (de) | 2007-11-30 | 2014-12-17 | Merck Patent GmbH | Polymerisierbare Verbindungen |
| WO2009088882A2 (en) * | 2007-12-31 | 2009-07-16 | Atomate Corporation | Edge-contacted vertical carbon nanotube transistor |
| EP2098584B1 (en) | 2008-03-05 | 2011-10-12 | Merck Patent GmbH | Liquid-crystalline medium and liquid-crystal display having high twist |
| JP2011525482A (ja) * | 2008-06-17 | 2011-09-22 | ビーエーエスエフ ソシエタス・ヨーロピア | ２，６−ナフチル単位とイソマンニトール単位とを含有する重合性キラル化合物、およびそのキラルドーパントとしての使用 |
| US8426626B2 (en) | 2008-10-28 | 2013-04-23 | Fujifilm Corporation | Compound having asymmetric carbon atom, oxidation-reduction reaction causing portion, and liquid crystal substituent |
| US8545720B2 (en) | 2008-12-22 | 2013-10-01 | Merck Patent Gmbh | Liquid-crystal display |
| DE102010006691A1 (de) | 2009-02-06 | 2010-10-28 | Merck Patent Gmbh | Flüssigkristallines Medium und Flüssigkristallanzeige |
| EP2218764B1 (en) | 2009-02-13 | 2012-01-18 | Merck Patent GmbH | Chiral reactive mesogen mixture |
| US8176924B2 (en) * | 2009-03-11 | 2012-05-15 | Kent Displays Incorporated | Color changing artificial fingernails |
| DE102010012900A1 (de) | 2009-04-23 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| US8168084B2 (en) | 2009-12-18 | 2012-05-01 | Vanderbilt University | Polar nematic compounds |
| DE102011011836A1 (de) | 2010-03-09 | 2011-09-15 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| JP2011225520A (ja) | 2010-04-02 | 2011-11-10 | Jnc Corp | 重合性基を有する光学活性化合物ならびにその重合体 |
| DE102011015546A1 (de) | 2010-04-26 | 2012-01-26 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| EP2399972B1 (en) | 2010-06-25 | 2015-11-25 | Merck Patent GmbH | Liquid-crystalline medium and liquid-crystal display having high twist |
| WO2012084200A1 (en) | 2010-12-21 | 2012-06-28 | Stichting Dutch Polymer Institute | Process for coating a curved article |
| TWI443180B (zh) | 2010-12-23 | 2014-07-01 | Ind Tech Res Inst | 對掌性雙萘基化合物 |
| DE102012003796A1 (de) | 2011-03-18 | 2012-09-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
| GB2503629B (en) | 2011-03-29 | 2019-04-17 | Merck Patent Gmbh | Liquid-crystalline medium |
| EP2714844B1 (de) | 2011-05-27 | 2016-12-28 | Merck Patent GmbH | Polymerisierbare verbindungen und ihre verwendung in flüssigkristallmedien und flüssigkristallanzeigen |
| US10450509B2 (en) | 2011-06-01 | 2019-10-22 | Merck Patent Gmbh | Liquid crystal medium and liquid display |
| JP6266513B2 (ja) | 2011-08-01 | 2018-01-24 | 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 |
| EP2568032B1 (en) | 2011-09-06 | 2014-11-26 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| JP6386378B2 (ja) | 2011-09-06 | 2018-09-05 | 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 |
| DE102012024126A1 (de) | 2011-12-20 | 2013-06-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
| EP2623927A1 (en) | 2012-02-02 | 2013-08-07 | Stichting Dutch Polymer Institute | Optical strain sensor |
| 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 |
| EP2708587B1 (en) | 2012-09-18 | 2015-07-15 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| US9822305B2 (en) | 2012-10-02 | 2017-11-21 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| US9612445B2 (en) | 2012-11-27 | 2017-04-04 | Merck Patent Gmbh | Lens element |
| EP2964653A4 (en) * | 2013-03-05 | 2016-11-30 | Archer Daniels Midland Co | ISOHEXIDE MONOTRIFLATES AND METHOD FOR SYNTHESIS THEREOF |
| US9279084B2 (en) * | 2013-03-15 | 2016-03-08 | Opsec Security Group, Inc. | Security device using liquid crystals |
| US9809749B2 (en) | 2013-04-19 | 2017-11-07 | Merck Patent Gmbh | Mesogenic compound, liquid-crystal medium and liquid crystal display |
| WO2015101405A1 (en) | 2013-12-30 | 2015-07-09 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| WO2015120950A1 (en) | 2014-02-13 | 2015-08-20 | Merck Patent Gmbh | Reactive mesogen based polymer particles |
| CN106104331B (zh) * | 2014-03-20 | 2019-04-30 | 富士胶片株式会社 | 组合物、光反射膜、增亮膜、背光单元及液晶显示装置 |
| EP3169750A1 (en) | 2014-07-18 | 2017-05-24 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| EP2990460B1 (de) | 2014-08-22 | 2019-04-03 | Merck Patent GmbH | Flüssigkristallines medium |
| DE102015015108A1 (de) | 2014-12-17 | 2016-06-23 | Merck Patent Gmbh | Flüssigkristallines Medium |
| JP6961485B2 (ja) | 2014-12-29 | 2021-11-05 | 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 | 液晶媒体およびそれを含む高周波数素子 |
| EP3240861B1 (en) | 2014-12-30 | 2019-03-13 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| EP3124573B1 (en) | 2015-07-31 | 2018-03-28 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| WO2017137145A1 (en) | 2016-02-08 | 2017-08-17 | Merck Patent Gmbh | Liquid-crystalline medium and high-frequency components comprising same |
| EP3443050B1 (en) | 2016-04-13 | 2020-01-29 | Merck Patent GmbH | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| KR20190042636A (ko) | 2016-08-24 | 2019-04-24 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| EP3312257B1 (en) | 2016-10-18 | 2019-11-20 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| KR20190075994A (ko) | 2016-10-24 | 2019-07-01 | 메르크 파텐트 게엠베하 | 액정 매질 |
| KR20190077034A (ko) | 2016-10-31 | 2019-07-02 | 메르크 파텐트 게엠베하 | 액정 매질을 포함하는 나노캡슐 |
| JP6866625B2 (ja) * | 2016-12-08 | 2021-04-28 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| KR101827801B1 (ko) | 2017-02-23 | 2018-02-09 | 한국화학연구원 | 아이소헥사이드 다이안하이드라이드 단량체, 이로부터 제조된 폴리이미드 및 이들의 제조방법 |
| US20210115337A1 (en) | 2017-03-16 | 2021-04-22 | Merck Patent Gmbh | Liquid-crystalline medium |
| WO2018189068A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| KR20190139987A (ko) | 2017-04-20 | 2019-12-18 | 메르크 파텐트 게엠베하 | 광 변조 소자 |
| KR20190039639A (ko) | 2017-10-05 | 2019-04-15 | 메르크 파텐트 게엠베하 | 작용화된 폴리비닐 알콜을 포함하는 조성물 및 액정 매질을 함유하는 나노캡슐 |
| JP7420717B2 (ja) | 2017-12-06 | 2024-01-23 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | スイッチング要素に使用するための液晶媒体 |
| EP3720925B1 (en) | 2017-12-06 | 2023-02-15 | Merck Patent GmbH | Window element |
| EP3502210B1 (en) | 2017-12-20 | 2020-09-09 | Merck Patent GmbH | Liquid-crystal medium |
| EP3543314B1 (en) | 2018-03-23 | 2020-09-09 | Merck Patent GmbH | Liquid-crystalline medium |
| EP3543313B1 (en) | 2018-03-23 | 2020-10-07 | Merck Patent GmbH | Liquid-crystalline medium |
| CN110483472A (zh) * | 2018-05-15 | 2019-11-22 | 石家庄诚志永华显示材料有限公司 | 手性化合物、包含该手性化合物的液晶组合物、光学各向异性体及液晶显示器件 |
| EP3739020B1 (en) | 2018-05-16 | 2023-08-23 | Merck Patent GmbH | Liquid-crystalline medium |
| DE102019008592A1 (de) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Komponenten für die Hochfrequenztechnik und Flüssigkristallmedium |
| KR20210102363A (ko) | 2018-12-12 | 2021-08-19 | 메르크 파텐트 게엠베하 | 중합성 액정 잉크 제형 |
| CN113195501A (zh) | 2018-12-13 | 2021-07-30 | 默克专利股份有限公司 | 液晶介质 |
| CN113195683B (zh) | 2018-12-19 | 2025-01-10 | 默克专利股份有限公司 | 用于切换元件的切换层 |
| KR102803509B1 (ko) | 2019-01-25 | 2025-05-09 | 메르크 파텐트 게엠베하 | 액정 매질 |
| IL274057B2 (en) | 2019-04-30 | 2024-03-01 | Merck Patent Gmbh | Isothiocyantotoluenes |
| CN113874469B (zh) | 2019-05-15 | 2024-09-10 | 默克专利股份有限公司 | 制备基于液晶的切换元件的方法 |
| GB2589659B (en) | 2019-05-28 | 2023-04-05 | Merck Patent Gmbh | Compositions comprising polymerizable oligoethyleneglycol derivatives and nanocapsules containing a liquid-crystalline medium |
| KR20220024586A (ko) | 2019-06-17 | 2022-03-03 | 메르크 파텐트 게엠베하 | 액정-기반 광 밸브 |
| TWI868205B (zh) | 2019-08-28 | 2025-01-01 | 德商馬克專利公司 | 芳香性異硫氰酸酯 |
| CN110669529A (zh) * | 2019-09-10 | 2020-01-10 | 苏州大学 | 彩色液晶材料及其应用 |
| EP4041846B1 (en) | 2019-10-10 | 2024-04-17 | Merck Patent GmbH | Fluorinated aromatic compounds |
| WO2021116080A1 (en) | 2019-12-10 | 2021-06-17 | Merck Patent Gmbh | Aromatic isothiocyanates |
| EP3839008B1 (en) | 2019-12-17 | 2023-07-26 | Merck Patent GmbH | Liquid crystal medium |
| WO2021233797A1 (en) | 2020-05-18 | 2021-11-25 | Merck Patent Gmbh | Liquid-crystalline medium |
| WO2022003001A1 (en) | 2020-07-03 | 2022-01-06 | Merck Patent Gmbh | Liquid crystal medium |
| EP3933009B1 (en) | 2020-07-03 | 2023-08-16 | Merck Patent GmbH | Liquid crystal medium |
| WO2022002997A1 (en) | 2020-07-03 | 2022-01-06 | Merck Patent Gmbh | Liquid crystal medium |
| WO2022008474A1 (en) | 2020-07-08 | 2022-01-13 | Merck Patent Gmbh | Optical component |
| EP3940040B1 (en) | 2020-07-16 | 2024-10-16 | Merck Patent GmbH | Liquid-crystalline medium |
| EP4204515A1 (en) | 2020-08-28 | 2023-07-05 | Merck Patent GmbH | Aromatic isothiocyanates |
| CN114525139B (zh) | 2020-10-07 | 2025-07-25 | 默克专利股份有限公司 | 液晶介质 |
| JP2023547643A (ja) | 2020-10-28 | 2023-11-13 | 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 | 芳香族イソチオシアネート類 |
| US12077703B2 (en) | 2020-12-16 | 2024-09-03 | Merck Patent Gmbh | Heteroaromatic isothiocyanates |
| CN116583577B (zh) | 2020-12-17 | 2025-10-21 | 默克专利股份有限公司 | 杂芳族异硫氰酸酯 |
| US11802243B2 (en) | 2021-02-26 | 2023-10-31 | Merck Patent Gmbh | Liquid-crystal medium |
| CN117043304A (zh) | 2021-03-31 | 2023-11-10 | 默克专利股份有限公司 | 芳族异硫氰酸酯 |
| WO2022229124A1 (en) | 2021-04-29 | 2022-11-03 | Merck Patent Gmbh | Liquid crystal medium |
| TW202317855A (zh) | 2021-08-06 | 2023-05-01 | 德商馬克專利公司 | 用於窗元件之切換層 |
| WO2023036746A1 (en) | 2021-09-08 | 2023-03-16 | Merck Patent Gmbh | Liquid-crystal medium |
| JP7390676B1 (ja) * | 2022-05-17 | 2023-12-04 | パナソニックＩｐマネジメント株式会社 | 非線形光吸収材料、記録媒体、情報の記録方法及び情報の読出方法 |
| CN119422086A (zh) | 2022-06-21 | 2025-02-11 | 富士胶片株式会社 | 图像记录物及图像记录物的制造方法、以及装饰成型体 |
| EP4306615A1 (en) | 2022-07-11 | 2024-01-17 | Merck Patent GmbH | Liquid-crystal medium |
| CN120787252A (zh) | 2023-02-24 | 2025-10-14 | 默克专利股份有限公司 | 二氢萘衍生物 |
| WO2024260902A1 (en) | 2023-06-20 | 2024-12-26 | Merck Patent Gmbh | Liquid crystal medium |
| WO2025061649A1 (en) | 2023-09-20 | 2025-03-27 | Merck Patent Gmbh | Liquid crystal medium |
| US20250154412A1 (en) | 2023-11-08 | 2025-05-15 | Merck Patent Gmbh | Liquid crystal medium |
| WO2025196107A1 (en) | 2024-03-22 | 2025-09-25 | Merck Patent Gmbh | Indene derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3675136D1 (de) * | 1985-09-30 | 1990-11-29 | Hoechst Ag | Chirale phenolester mesogener carbonsaeuren und ihre verwendung als dotierstoff in fluessigkristal-phasen. |
| DE3534780A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Chirale phenolester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| US5585036A (en) * | 1988-03-04 | 1996-12-17 | Displaytech, Inc. | Liquid crystal compounds containing chiral 2-halo-2-methyl ether and ester tails |
| EP0415220B1 (de) * | 1989-09-01 | 1994-02-02 | F. Hoffmann-La Roche Ag | Chirale Dotierstoffe für Flüssigkristalle |
| JP3187611B2 (ja) * | 1993-05-17 | 2001-07-11 | キヤノン株式会社 | 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 |
| GB2298202B (en) | 1995-02-24 | 1998-09-16 | Merck Patent Gmbh | Chiral polymerizable binaphthol derivatives |
| US5702637A (en) * | 1995-04-19 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| CN1108325C (zh) * | 2000-03-12 | 2003-05-14 | 吉林大学 | 手性环状预聚物的合成 |
-
2001
- 2001-06-25 JP JP2002512102A patent/JP5317382B2/ja not_active Expired - Fee Related
- 2001-06-25 EP EP01960376A patent/EP1299335B1/en not_active Expired - Lifetime
- 2001-06-25 WO PCT/EP2001/007215 patent/WO2002006195A1/en not_active Ceased
- 2001-06-25 DE DE60130338T patent/DE60130338T2/de not_active Expired - Lifetime
- 2001-06-25 CN CNB018127266A patent/CN1206197C/zh not_active Expired - Lifetime
- 2001-06-25 AU AU2001281884A patent/AU2001281884A1/en not_active Abandoned
- 2001-06-25 AT AT01960376T patent/ATE372314T1/de not_active IP Right Cessation
- 2001-06-25 US US10/332,806 patent/US7318950B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60130338D1 (de) | 2007-10-18 |
| EP1299335A1 (en) | 2003-04-09 |
| CN1206197C (zh) | 2005-06-15 |
| US7318950B2 (en) | 2008-01-15 |
| ATE372314T1 (de) | 2007-09-15 |
| US20030178601A1 (en) | 2003-09-25 |
| EP1299335B1 (en) | 2007-09-05 |
| AU2001281884A1 (en) | 2002-01-30 |
| WO2002006195A1 (en) | 2002-01-24 |
| JP2004504285A (ja) | 2004-02-12 |
| JP5317382B2 (ja) | 2013-10-16 |
| CN1441765A (zh) | 2003-09-10 |
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