WO2016070708A1 - Cristal liquide fluoré contenant une liaison en pont de difluorométhoxy et sa composition - Google Patents

Cristal liquide fluoré contenant une liaison en pont de difluorométhoxy et sa composition Download PDF

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Publication number
WO2016070708A1
WO2016070708A1 PCT/CN2015/092175 CN2015092175W WO2016070708A1 WO 2016070708 A1 WO2016070708 A1 WO 2016070708A1 CN 2015092175 W CN2015092175 W CN 2015092175W WO 2016070708 A1 WO2016070708 A1 WO 2016070708A1
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WIPO (PCT)
Prior art keywords
liquid crystal
difluoro
fluorine
difluorophenyl
crystal compound
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PCT/CN2015/092175
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English (en)
Chinese (zh)
Inventor
闻建勋
李继响
王建新
杜宏军
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福建省邵武市永晶化工有限公司
上海天问化学有限公司
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Publication of WO2016070708A1 publication Critical patent/WO2016070708A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen 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
    • C09K19/08—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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • 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
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • 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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • 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

Definitions

  • the present invention is a fluorine-containing liquid crystal containing a difluoromethoxy (CF 2 O) bridge in a molecular structure and a composition thereof, and a composition formed with other liquid crystals can be used for a TFT type liquid crystal display.
  • CF 2 O difluoromethoxy
  • the number of fluorine atoms in the molecule is proportional to the viscosity.
  • the increase in the number of fluorine atoms in the liquid crystal molecules lowers the temperature range of the liquid crystal phase. It is extremely difficult to suppress the change in the temperature of the liquid crystal phase while suppressing the rise of the viscosity, and it is difficult to control the change of ⁇ alone.
  • the object of the present invention is to provide a fluorine-containing liquid crystal containing a bridge of difluoromethoxy (CF 2 O) and a composition thereof, a process for the preparation thereof and an application thereof.
  • Their composition with other liquid crystals can be used for a TFT type liquid crystal display.
  • This work developed a fluorine-containing compound containing CF 2 O, which is characterized by the use of different terminal rings.
  • CF 3 - on the benzene ring since the introduction of CF 3 - on the benzene ring not only increases the polarity, but also contributes to the improvement of fat solubility, and avoids group analysis at low temperatures.
  • the method using difluorodibromomethane as a raw material has a simple process.
  • the high-temperature and high-polarity bicyclohexyltetracyclofluoro liquid crystal (CN 2012100088035.6) in the inventor's patent was successfully utilized.
  • the fluorine-containing liquid crystal compound containing CF 2 O bridge of the present invention has the following structure:
  • n 1, 2, 3, 4, 5 or 6.
  • the fluorine-containing liquid crystal compound containing a CF 2 O bridge of the present invention can be obtained by the following methods, respectively:
  • diethyl malonate and n-alkyl bromide form an n-alkyl substituted diethyl malonate, which is then reduced to substituted propylene glycol by lithium aluminum hydride, and then reacted with 3,5-difluorobenzaldehyde to obtain B7.
  • B8 is reacted with 3,4,5-trifluorophenol to obtain the target compound difluoro-[(5-alkyl-1,3-dioxa-cyclohexyl).
  • alkyl group means methyl, ethyl, propyl, butyl, pentyl or hexyl
  • Preferred alkyl means methyl, ethyl, propyl, butyl or pentyl.
  • n 1, 2, 3, 4, 5 or 6.
  • 3,5-difluorobromobenzene is used as a format reagent to react with n-propanal to form C3, and C3 is dehydrated and hydrogenated to obtain 3,5-difluoro-n-propylbenzene C5, C5 after hydrogen extraction by n-butyllithium and Reaction of fluorodibromomethane to obtain compound C6, C6 is reacted with 3,5-difluorophenol, and then hydrogen is extracted by n-butyllithium and then reacted with 3,4,5-trifluorobenzeneboronic acid by Suzuki coupling reaction: in absolute ethanol And at reflux temperature, compound C8 difluoro-[4-n-propyl- 2,6-difluorophenyl]-(3,5-difluoro-4-iodophenoxy)methane, compound C93,4,5 -trifluorophenylboronic acid, catalytic amount of Pd(PPh 3 ) 4 and potassium carbonate for 1 - 5 hours
  • the compounds C8 and C10 are reacted by Sonogashira to form the target product difluoro-[4-n-propyl-1,3-difluorophenyl]-[(2,3,4,5,6-pentafluorophenyl).
  • Ethynyl]-3,5-difluorophenoxy]methane compound C8 difluoro-[4-n-propyl- 2,6-difluorophenyl]- in the presence of solvent triethylamine at reflux temperature (3,5-difluoro-4-iodophenoxy)methane, compound C10 pentafluorophenylacetylene, catalytic amount of Pd(PPh 3 ) 2 Cl 2 and CuI, reacting for 1 - 5 hours; said compound C8 Fluoro-[4-n-propyl- 2,6-difluorophenyl]-(3,5-difluoro-4-isophenoxy)methane, pentafluorophenylacetylene, Pd(PPh 3 ) 2 Cl 2 and The CuI molar ratio is 1:1 ⁇ 3: 0.05 ⁇ 0.5: 0.05 ⁇ 0.5.
  • n 1, 2, 3, 4, 5 or 6.
  • D4 difluoro-bromo-(4-alkylphenyl-2,6-difluorophenyl)-methane and D83-fluoro-4-tetrafluoromethylphenol form the target compound difluoro in potassium carbonate and DMF- [4-n-Actylphenyl-2,6-difluorophenyl]-(3-fluoro-4-trifluoromethylphenyl)methane:
  • Compound D4 II in an organic polar solvent at 90-100 ° C Fluoro-bromo-(4-alkylphenyl-2,6-difluorophenyl)-methane and compound D83-fluoro-4-tetrafluoromethylphenol, anhydrous potassium carbonate and tetrabutylammonium bromide 1 1-4 hours; the compound D4 and the compound D8, the molar ratio of tetrabutylammonium bromide to anhydrous potassium carbonate is 1:1 - 3
  • the liquid crystal compound of the invention not only has simple synthesis method, easy availability of raw materials, simple process, but also increases polarity, good fat solubility, avoids group analysis at low temperature, and can be combined with other liquid crystal compounds, and can be used for TFT liquid crystal. monitor.
  • the liquid is dripped in 10 minutes, heated under reflux for 2 hours, cooled, and slowly added to 250 mL of a saturated ammonium chloride solution (bumping too quickly), and a precipitate is formed first, and the precipitate is further added dropwise.
  • the mixture was extracted twice with methyl tert-butyl ether.
  • the temperature was lowered to below -78 °C, LDA was added dropwise, and the reaction was continued for 10 minutes.
  • the low temperature reaction was continued for 2 hours, and the temperature was automatically raised to -60 ° C.
  • Elemental iodine was added dropwise, and the reaction was continued at -60 ° C for 1.5 hours.
  • the organic layer was dried, and the organic phase was dried. It was spin-dried and passed through a column with petroleum ether to give the product 0.98 g, yield 70%.
  • the homologue synthesis method is the same,
  • the homologue synthesis method is the same,
  • IR (KBr, ⁇ max , cm ⁇ 1 ): 3390, 3316, 1630, 1574, 1515, 1415, 1319, 1138, 1043, 904, 841, 812, 684, 608.
  • a composition comprising twelve effective active liquid crystal compounds in the following table can be used for a TFT type liquid crystal display.
  • the liquid crystal composition was prepared by mixing according to the weight ratio set in the text.
  • the physical properties of the composition were: clearing point, 92 ° C; ⁇ n, (0.1053, 20 ° C) ; threshold voltage Vth, 1.48v; ⁇ , 8.13 (25 ° C). Suitable for use in IPS liquid crystal display devices.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

La présente invention se rapporte à un cristal liquide fluoré contenant une liaison en pont de difluorométhoxy (CF2O) et sa composition ainsi que son procédé de préparation et son utilisation. Dans le procédé de la présente invention, du difluorodibromométhane est utilisé en tant que matière première; non seulement le procédé de synthèse est simple et pratique, la matière première est facilement disponible, et le processus est simple, mais également le cristal liquide fluoré résultant présente une polarité élevée et une bonne solubilité dans les lipides, évitant la précipitation des composants du cristal liquide fluoré à basse température, et la composition du cristal liquide fluoré avec d'autres composés de cristaux liquides peut être utilisée pour des affichages à cristaux liquides de type TFT.
PCT/CN2015/092175 2014-11-06 2015-10-19 Cristal liquide fluoré contenant une liaison en pont de difluorométhoxy et sa composition WO2016070708A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201410621417.X 2014-11-06
CN201410621417.XA CN104449762B (zh) 2014-11-06 2014-11-06 含有二氟甲氧基桥键的含氟液晶及其组合物

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Families Citing this family (10)

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Publication number Priority date Publication date Assignee Title
CN104449762B (zh) * 2014-11-06 2016-09-14 福建省邵武市永晶化工有限公司 含有二氟甲氧基桥键的含氟液晶及其组合物
JP2018526507A (ja) * 2015-08-26 2018-09-13 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Ｍｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 液晶媒体
CN106281356B (zh) * 2016-07-19 2018-11-02 福建永晶科技股份有限公司 含有二氟甲氧基桥键与二噁基的含氟液晶及其组合物
CN106244168B (zh) * 2016-07-19 2018-10-02 福建永晶科技股份有限公司 含有二氟甲氧基桥键及多氟联苯基的含氟液晶及其组合物
CN106244169B (zh) * 2016-07-29 2017-05-31 福建永晶科技有限公司 三环超氟液晶化合物的应用
CN108003893B (zh) * 2016-11-02 2021-08-03 石家庄诚志永华显示材料有限公司 一种高垂直介电液晶化合物、液晶组合物、液晶显示器件
CN110607178B (zh) * 2018-06-15 2021-04-09 北京八亿时空液晶科技股份有限公司 一种液晶化合物及其制备方法与应用
CN110628439A (zh) * 2018-06-22 2019-12-31 北京八亿时空液晶科技股份有限公司 一种高性能液晶化合物及其制备方法与应用
CN110699092A (zh) * 2018-07-10 2020-01-17 北京八亿时空液晶科技股份有限公司 一种含有二氟甲氧基桥键的液晶化合物及制备方法与应用
CN109735346A (zh) * 2019-01-29 2019-05-10 上海天问化学有限公司 含有三联苯的二氟亚甲基醚的四环液晶化合物

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US6497929B1 (en) * 1999-10-25 2002-12-24 Chisso Corporation Liquid crystal composition and liquid crystal display device
EP1482018A1 (fr) * 2003-05-27 2004-12-01 MERCK PATENT GmbH Aldéhydes avec un pont difluorooxyméthylène
WO2013150826A1 (fr) * 2012-04-02 2013-10-10 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
CN103351873A (zh) * 2013-06-25 2013-10-16 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
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