TWI224130B - Chiral compounds III - Google Patents
Chiral compounds III Download PDFInfo
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- TWI224130B TWI224130B TW090116198A TW90116198A TWI224130B TW I224130 B TWI224130 B TW I224130B TW 090116198 A TW090116198 A TW 090116198A TW 90116198 A TW90116198 A TW 90116198A TW I224130 B TWI224130 B TW I224130B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 113
- -1 diagnostics Substances 0.000 claims abstract description 72
- 238000011049 filling Methods 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 230000002079 cooperative effect Effects 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 93
- 239000000203 mixture Substances 0.000 abstract description 93
- 239000002019 doping agent Substances 0.000 abstract description 34
- 229920000642 polymer Polymers 0.000 abstract description 12
- 239000002537 cosmetic Substances 0.000 abstract description 7
- 239000000049 pigment Substances 0.000 abstract description 7
- 229920000106 Liquid crystal polymer Polymers 0.000 abstract description 6
- 230000003287 optical effect Effects 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
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- 229920003002 synthetic resin Polymers 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 33
- 230000003098 cholesteric effect Effects 0.000 description 21
- 239000000758 substrate Substances 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 12
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- 125000000524 functional group Chemical group 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 6
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 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 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 3
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 3
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- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 210000000941 bile Anatomy 0.000 description 3
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- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 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 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 239000003292 glue Substances 0.000 description 3
- 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 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- SMHSPYVJAUGNOI-UHFFFAOYSA-N 2-cyclohexyl-1,4-dioxane Chemical compound C1CCCCC1C1OCCOC1 SMHSPYVJAUGNOI-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- WLNDDIWESXCXHM-UHFFFAOYSA-N 2-phenyl-1,4-dioxane Chemical group C1OCCOC1C1=CC=CC=C1 WLNDDIWESXCXHM-UHFFFAOYSA-N 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- OWVIRVJQDVCGQX-VSGBNLITSA-N [(4r,5r)-5-[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-diphenylmethanol Chemical class C=1C=CC=CC=1C(O)([C@H]1[C@@H](OC(O1)(C)C)C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OWVIRVJQDVCGQX-VSGBNLITSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
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- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 2
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- 150000002500 ions Chemical class 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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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 2
- 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 2
- 125000005447 octyloxy 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])O* 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Cosmetics (AREA)
- Hydrogenated Pyridines (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
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| EP00115249 | 2000-07-13 |
Publications (1)
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| TWI224130B true TWI224130B (en) | 2004-11-21 |
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|---|---|---|---|
| TW090116198A TWI224130B (en) | 2000-07-13 | 2001-06-29 | Chiral compounds III |
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| EP (1) | EP1299375B1 (enExample) |
| JP (1) | JP5111715B2 (enExample) |
| CN (1) | CN1264835C (enExample) |
| AT (1) | ATE273968T1 (enExample) |
| AU (1) | AU2001281885A1 (enExample) |
| DE (1) | DE60105032T2 (enExample) |
| TW (1) | TWI224130B (enExample) |
| WO (1) | WO2002006265A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI648382B (zh) * | 2013-07-31 | 2019-01-21 | 日商半導體能源研究所股份有限公司 | 二氧戊環衍生物、液晶組成物、液晶元件及液晶顯示裝置 |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001096494A1 (en) * | 2000-06-09 | 2001-12-20 | Kent Displays, Inc. | Chiral additives for cholesteric displays |
| US7081282B2 (en) | 2001-07-02 | 2006-07-25 | Merck Patent Gmbh | Optically variable marking |
| DE10257711B4 (de) | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
| DE60332784D1 (de) * | 2002-02-13 | 2010-07-15 | Merck Patent Gmbh | Verfahren zur Herstellung von einem anisotropen Polymerfilm auf einem Substrat mit einer strukturierten Oberfläche |
| JP2007530470A (ja) | 2004-03-25 | 2007-11-01 | 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 ハフトング | 液晶化合物、液晶媒体および液晶ディスプレイ |
| KR101447290B1 (ko) | 2004-12-17 | 2014-10-06 | 메르크 파텐트 게엠베하 | 액정 시스템 및 액정 디스플레이 |
| US7782438B2 (en) * | 2006-06-13 | 2010-08-24 | Kent State University | Fast switching electro-optical devices using banana-shaped liquid crystals |
| US8574454B2 (en) | 2006-12-22 | 2013-11-05 | Rolic Ag | Patternable liquid crystal polymer comprising thio-ether units |
| EP2065361B1 (de) | 2007-11-30 | 2014-12-17 | Merck Patent GmbH | Polymerisierbare Verbindungen |
| ATE528377T1 (de) | 2008-03-05 | 2011-10-15 | Merck Patent Gmbh | Flüssigkristallines medium und flüssigkristallanzeige mit verdrehtem garn |
| 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 |
| ATE541913T1 (de) | 2009-02-13 | 2012-02-15 | Merck Patent Gmbh | Chirale reaktionsfähige mesogenmischung |
| DE102010012900A1 (de) | 2009-04-23 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| DE102011011836A1 (de) | 2010-03-09 | 2011-09-15 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| 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 |
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| DE102012003796A1 (de) | 2011-03-18 | 2012-09-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
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| US10450509B2 (en) | 2011-06-01 | 2019-10-22 | Merck Patent Gmbh | Liquid crystal medium and liquid display |
| WO2013008657A1 (en) * | 2011-07-08 | 2013-01-17 | Semiconductor Energy Laboratory Co., Ltd. | Liquid crystal composition, liquid crystal element, and liquid crystal display device |
| EP2739705B1 (en) | 2011-08-01 | 2015-08-19 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| EP2753675B1 (en) | 2011-09-06 | 2018-05-02 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| EP2568032B1 (en) | 2011-09-06 | 2014-11-26 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| 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 |
| US9862887B2 (en) | 2012-04-20 | 2018-01-09 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| EP2708587B1 (en) | 2012-09-18 | 2015-07-15 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| EP2904068B1 (en) | 2012-10-02 | 2016-10-12 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| US9612445B2 (en) | 2012-11-27 | 2017-04-04 | Merck Patent Gmbh | Lens element |
| CN105121596B (zh) | 2013-04-19 | 2021-03-12 | 默克专利股份有限公司 | 介晶化合物、液晶介质和液晶显示器 |
| EP3090033B1 (en) | 2013-12-30 | 2018-07-04 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| JP7025839B2 (ja) | 2014-02-13 | 2022-02-25 | 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 | 反応性メソゲンベースのポリマー粒子 |
| JP2017524046A (ja) | 2014-07-18 | 2017-08-24 | 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 | 液晶媒体およびそれを含む高周波コンポーネント |
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| US20190127642A1 (en) | 2016-04-13 | 2019-05-02 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| JP2019531373A (ja) | 2016-08-24 | 2019-10-31 | 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 |
| EP3312257B1 (en) | 2016-10-18 | 2019-11-20 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| EP3529331B1 (en) | 2016-10-24 | 2020-10-07 | Merck Patent GmbH | Liquid-crystalline medium |
| KR20190077034A (ko) | 2016-10-31 | 2019-07-02 | 메르크 파텐트 게엠베하 | 액정 매질을 포함하는 나노캡슐 |
| WO2018166999A1 (en) | 2017-03-16 | 2018-09-20 | 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 |
| EP3612615B1 (en) | 2017-04-20 | 2024-10-16 | Merck Patent GmbH | Light modulation element |
| KR20190039639A (ko) | 2017-10-05 | 2019-04-15 | 메르크 파텐트 게엠베하 | 작용화된 폴리비닐 알콜을 포함하는 조성물 및 액정 매질을 함유하는 나노캡슐 |
| CN111433322A (zh) | 2017-12-06 | 2020-07-17 | 默克专利股份有限公司 | 用于切换元件的液晶介质 |
| 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 |
| EP3739020B1 (en) | 2018-05-16 | 2023-08-23 | Merck Patent GmbH | Liquid-crystalline medium |
| US12102781B2 (en) * | 2018-06-29 | 2024-10-01 | Biosense Webster (Israel) Ltd. | Reinforcement for irrigated electrophysiology balloon catheter with flexible-circuit electrodes |
| US12458436B2 (en) | 2018-07-30 | 2025-11-04 | Biosense Webster (Israel) Ltd. | Flexible-circuit tip for a split-tip catheter |
| DE102019008592A1 (de) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Komponenten für die Hochfrequenztechnik und Flüssigkristallmedium |
| US12460134B2 (en) | 2018-12-12 | 2025-11-04 | Merck Patent Gmbh | Polymerizable liquid crystal ink formulations |
| US20220073822A1 (en) | 2018-12-13 | 2022-03-10 | Merck Patent Gmbh | Liquid-crystal medium |
| 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 |
| WO2020152206A1 (en) | 2019-01-25 | 2020-07-30 | Merck Patent Gmbh | Liquid-crystalline medium |
| IL274057B2 (en) | 2019-04-30 | 2024-03-01 | Merck Patent Gmbh | Isothiocyantotoluenes |
| WO2020229434A1 (en) | 2019-05-15 | 2020-11-19 | Merck Patent Gmbh | Method for preparing a liquid crystal-based switching element |
| GB2589659B (en) | 2019-05-28 | 2023-04-05 | Merck Patent Gmbh | Compositions comprising polymerizable oligoethyleneglycol derivatives and nanocapsules containing a liquid-crystalline medium |
| CN114008176A (zh) | 2019-06-17 | 2022-02-01 | 默克专利股份有限公司 | 基于液晶的光阀 |
| US11739265B2 (en) | 2019-08-28 | 2023-08-29 | Merck Patent Gmbh | Aromatic isothiocyanates |
| US11964933B2 (en) | 2019-10-10 | 2024-04-23 | Merck Patent Gmbh | Fluorinated aromatic compounds |
| CN114829543B (zh) | 2019-12-10 | 2024-09-10 | 默克专利股份有限公司 | 芳香族异硫氰酸酯 |
| EP3839008B1 (en) | 2019-12-17 | 2023-07-26 | Merck Patent GmbH | Liquid crystal medium |
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| 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 |
| US12114905B2 (en) | 2021-08-27 | 2024-10-15 | Biosense Webster (Israel) Ltd. | Reinforcement and stress relief for an irrigated electrophysiology balloon catheter with flexible-circuit electrodes |
| WO2023036746A1 (en) | 2021-09-08 | 2023-03-16 | Merck Patent Gmbh | Liquid-crystal medium |
| EP4306615A1 (en) | 2022-07-11 | 2024-01-17 | Merck Patent GmbH | Liquid-crystal medium |
| EP4669720A1 (en) | 2023-02-24 | 2025-12-31 | Merck Patent GmbH | DIHYDRONAPTHALENE DERIVATIVES |
| 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 |
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| WO2025196107A1 (en) | 2024-03-22 | 2025-09-25 | Merck Patent Gmbh | Indene derivatives |
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Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02155932A (ja) * | 1988-12-07 | 1990-06-15 | Nippon Paint Co Ltd | 複合化粒子ならびにその製法 |
| DE19611101A1 (de) * | 1996-03-21 | 1997-09-25 | Basf Ag | Chirale Verbindungen |
| GB9812800D0 (en) | 1998-06-12 | 1998-08-12 | Rolic Ag | Optically active compounds |
| DE69907579T2 (de) * | 1998-07-15 | 2004-04-01 | Merck Patent Gmbh | Polymerisierbare mesogene Fluorphenylene |
| WO2001096494A1 (en) * | 2000-06-09 | 2001-12-20 | Kent Displays, Inc. | Chiral additives for cholesteric displays |
-
2001
- 2001-06-25 US US10/332,807 patent/US7041345B2/en not_active Expired - Lifetime
- 2001-06-25 CN CNB018127274A patent/CN1264835C/zh not_active Expired - Lifetime
- 2001-06-25 WO PCT/EP2001/007218 patent/WO2002006265A1/en not_active Ceased
- 2001-06-25 AT AT01960377T patent/ATE273968T1/de not_active IP Right Cessation
- 2001-06-25 AU AU2001281885A patent/AU2001281885A1/en not_active Abandoned
- 2001-06-25 EP EP01960377A patent/EP1299375B1/en not_active Expired - Lifetime
- 2001-06-25 DE DE60105032T patent/DE60105032T2/de not_active Expired - Lifetime
- 2001-06-25 JP JP2002512169A patent/JP5111715B2/ja not_active Expired - Fee Related
- 2001-06-29 TW TW090116198A patent/TWI224130B/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI648382B (zh) * | 2013-07-31 | 2019-01-21 | 日商半導體能源研究所股份有限公司 | 二氧戊環衍生物、液晶組成物、液晶元件及液晶顯示裝置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004504314A (ja) | 2004-02-12 |
| JP5111715B2 (ja) | 2013-01-09 |
| CN1264835C (zh) | 2006-07-19 |
| AU2001281885A1 (en) | 2002-01-30 |
| WO2002006265A1 (en) | 2002-01-24 |
| CN1441797A (zh) | 2003-09-10 |
| DE60105032D1 (de) | 2004-09-23 |
| EP1299375B1 (en) | 2004-08-18 |
| EP1299375A1 (en) | 2003-04-09 |
| US20030189189A1 (en) | 2003-10-09 |
| ATE273968T1 (de) | 2004-09-15 |
| US7041345B2 (en) | 2006-05-09 |
| DE60105032T2 (de) | 2005-08-18 |
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