KR20150036406A - 바이메소제닉 화합물 및 메소제닉 매질 - Google Patents
바이메소제닉 화합물 및 메소제닉 매질 Download PDFInfo
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- KR20150036406A KR20150036406A KR1020157003132A KR20157003132A KR20150036406A KR 20150036406 A KR20150036406 A KR 20150036406A KR 1020157003132 A KR1020157003132 A KR 1020157003132A KR 20157003132 A KR20157003132 A KR 20157003132A KR 20150036406 A KR20150036406 A KR 20150036406A
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000006850 spacer group Chemical group 0.000 claims description 16
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- 238000002834 transmittance Methods 0.000 description 3
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
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- MRQYTJXVULSNIS-UHFFFAOYSA-N 4-bromo-3-fluorophenol Chemical compound OC1=CC=C(Br)C(F)=C1 MRQYTJXVULSNIS-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
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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 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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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
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- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
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- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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- C07C255/55—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
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- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/30—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
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- 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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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
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- 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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- 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
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
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- Liquid Crystal Substances (AREA)
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| PCT/EP2013/001773 WO2014005672A1 (en) | 2012-07-06 | 2013-06-14 | Bimesogenic compounds and mesogenic media |
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| EP2870218B1 (en) | 2012-07-06 | 2018-05-02 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| CN104487542B (zh) * | 2012-07-06 | 2016-10-12 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| US9644144B2 (en) * | 2012-08-29 | 2017-05-09 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| WO2015074738A1 (en) * | 2013-11-22 | 2015-05-28 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| EP3169749B1 (en) * | 2014-07-17 | 2018-12-26 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| EP3218446B1 (en) | 2014-11-11 | 2018-07-04 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| JP6841758B2 (ja) * | 2014-12-17 | 2021-03-10 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ビメソゲン化合物およびメソゲン性媒体 |
| US20170342324A1 (en) * | 2014-12-19 | 2017-11-30 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| EP3234065B1 (en) * | 2014-12-19 | 2018-09-26 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| CN107109223B (zh) * | 2014-12-30 | 2021-03-23 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| WO2017067630A1 (en) * | 2015-10-23 | 2017-04-27 | Merck Patent Gmbh | Light modulation element |
| EP3383970B1 (en) | 2015-12-02 | 2021-03-31 | Merck Patent GmbH | Liquid crystal medium and liquid crystal device |
| CN109072078A (zh) * | 2016-05-12 | 2018-12-21 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| JP2019533037A (ja) | 2016-09-14 | 2019-11-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体および液晶デバイス |
| WO2018104279A1 (en) | 2016-12-08 | 2018-06-14 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal device |
| WO2019030150A1 (en) | 2017-08-08 | 2019-02-14 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM AND LIQUID CRYSTAL DEVICE |
| WO2019030153A1 (en) | 2017-08-08 | 2019-02-14 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM AND LIQUID CRYSTAL DEVICE |
| DE112018005004T5 (de) | 2017-10-25 | 2020-07-16 | Merck Patent Gmbh | Flüssigkristallmedium und Flüssigkristallvorrichtung |
| WO2019081561A1 (en) | 2017-10-25 | 2019-05-02 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM AND LIQUID CRYSTAL DEVICE |
| TWI800577B (zh) | 2017-12-18 | 2023-05-01 | 德商馬克專利公司 | 液晶化合物及液晶介質 |
| WO2019179962A1 (en) | 2018-03-22 | 2019-09-26 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN110467926B (zh) * | 2018-05-10 | 2023-10-31 | 江苏集萃智能液晶科技有限公司 | 液晶组合物及其液晶显示器 |
Family Cites Families (30)
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| EP1061404A1 (en) | 1992-09-18 | 2000-12-20 | Hitachi, Ltd. | A liquid crystal display device |
| JP3015998B2 (ja) * | 1993-08-31 | 2000-03-06 | キヤノン株式会社 | 液晶性化合物、それを含む液晶組成物、該液晶組成物を用いた液晶素子、液晶装置、並びに表示方法 |
| DE19781752T1 (de) | 1996-07-01 | 1999-09-02 | Merck Patent Gmbh | Chirale Dotierstoffe |
| TW473536B (en) * | 1996-12-16 | 2002-01-21 | Chisso Corp | Difluorophenyl derivatives, liquid-crystal compounds, and liquid-crystal composition |
| DE19834162A1 (de) | 1997-08-13 | 1999-02-18 | Merck Patent Gmbh | Chirale Verbindungen |
| EP0971016B1 (en) | 1998-07-08 | 2003-05-21 | MERCK PATENT GmbH | Mesogenic estradiols |
| GB2356629B (en) | 1999-10-04 | 2004-09-22 | Merck Patent Gmbh | Bimesogenic Compounds and Flexoelectric Devices |
| GB0225662D0 (en) * | 2001-11-16 | 2002-12-11 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| EP1408098B1 (en) * | 2002-10-08 | 2005-12-28 | MERCK PATENT GmbH | Liquid crystalline medium and liquid crystal display |
| JP4442179B2 (ja) * | 2002-10-10 | 2010-03-31 | チッソ株式会社 | アリルエーテル化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 |
| EP1477547B1 (en) * | 2003-05-09 | 2006-06-14 | MERCK PATENT GmbH | Liquid crystalline medium and liquid crystal display |
| JP4514508B2 (ja) * | 2003-10-29 | 2010-07-28 | 株式会社Adeka | 液晶組成物及びｓｔｎ型液晶素子 |
| GB0402006D0 (en) * | 2004-01-30 | 2004-03-03 | Dow Corning Ltd | Liquid crystal materials |
| KR101257119B1 (ko) * | 2004-12-23 | 2013-04-22 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 및 플렉소일렉트릭 장치 |
| JP2007002132A (ja) * | 2005-06-24 | 2007-01-11 | Chisso Corp | 液晶組成物および液晶表示素子 |
| KR101547358B1 (ko) * | 2006-06-09 | 2015-08-25 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| EP2351741B1 (en) * | 2008-10-21 | 2016-11-30 | JNC Corporation | Pentacyclic liquid crystal compound having nitrogen-containing heterocyclic ring, liquid crystal composition, and liquid crystal display device |
| JP5672043B2 (ja) * | 2010-04-05 | 2015-02-18 | Jnc株式会社 | ５環化合物、液晶組成物および液晶表示素子 |
| JP6280366B2 (ja) * | 2010-05-06 | 2018-02-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体および液晶ディスプレイ |
| US9389462B2 (en) * | 2010-09-28 | 2016-07-12 | Dic Corporation | Liquid crystal display device and useful liquid crystal composition |
| KR102014557B1 (ko) * | 2011-07-05 | 2019-08-26 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 |
| EP2855627B1 (en) * | 2012-05-25 | 2017-09-20 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| JP6240171B2 (ja) * | 2012-05-25 | 2017-11-29 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | メソゲン媒体および液晶ディスプレイ |
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| EP2870218B1 (en) * | 2012-07-06 | 2018-05-02 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| US9644144B2 (en) * | 2012-08-29 | 2017-05-09 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| CN104822800B (zh) * | 2012-12-10 | 2018-03-30 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
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- 2013-06-14 KR KR1020157003132A patent/KR20150036406A/ko not_active Abandoned
- 2013-06-14 US US14/413,091 patent/US20150175883A1/en not_active Abandoned
- 2013-06-14 WO PCT/EP2013/001773 patent/WO2014005672A1/en not_active Ceased
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2018
- 2018-09-13 US US16/130,581 patent/US20190010400A1/en not_active Abandoned
- 2018-10-26 JP JP2018201810A patent/JP2019048832A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN104411798A (zh) | 2015-03-11 |
| WO2014005672A1 (en) | 2014-01-09 |
| JP2019048832A (ja) | 2019-03-28 |
| EP2870217B1 (en) | 2016-07-20 |
| US20190010400A1 (en) | 2019-01-10 |
| TWI589678B (zh) | 2017-07-01 |
| JP2015527304A (ja) | 2015-09-17 |
| CN104411798B (zh) | 2017-05-24 |
| US20150175883A1 (en) | 2015-06-25 |
| TW201406933A (zh) | 2014-02-16 |
| EP2870217A1 (en) | 2015-05-13 |
| JP6523953B2 (ja) | 2019-06-05 |
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