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WO1995010496A1 - 2,3,4-trifluorobenzenes et leur utilisation dans des melanges a cristaux liquides - Google Patents

2,3,4-trifluorobenzenes et leur utilisation dans des melanges a cristaux liquides Download PDF

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Publication number
WO1995010496A1
WO1995010496A1 PCT/EP1994/003209 EP9403209W WO9510496A1 WO 1995010496 A1 WO1995010496 A1 WO 1995010496A1 EP 9403209 W EP9403209 W EP 9403209W WO 9510496 A1 WO9510496 A1 WO 9510496A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
trans
formula
trifluorobenzene
phenyl
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.)
Ceased
Application number
PCT/EP1994/003209
Other languages
German (de)
English (en)
Inventor
Hubert Schlosser
Dietmar Jungbauer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Merck Patent GmbH
Original Assignee
Hoechst AG
Merck Patent GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE4334362A external-priority patent/DE4334362A1/de
Priority claimed from DE4409724A external-priority patent/DE4409724B4/de
Application filed by Hoechst AG, Merck Patent GmbH filed Critical Hoechst AG
Publication of WO1995010496A1 publication Critical patent/WO1995010496A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • 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
    • 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • 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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • 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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
    • 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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone

Definitions

  • Optical effects can be achieved, for example, with the help of birefringence, the incorporation of dichroic dye molecules (guest host mode) or light scattering.
  • thermodynamic and electro-optical variables such as phase sequence and electro-optical variables
  • Phase temperature range refractive index, birefringence and dielectric anisotropy, switching time, threshold voltage, steepness of the electro-optical
  • electromagnetic radiation as well as the materials with which they are associated during and after the manufacturing process (e.g.
  • Liquid crystal mixtures are suitable.
  • the invention therefore relates to new 2,3,4-trifluorobenzene derivatives of the formula (I).
  • R 1 methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl; where X is -CH 2 -O- or -O-CH 2 -.
  • the substances according to the invention are distinguished by low melting points and broad nematic phases.
  • Preferred subclasses of the compounds of the formula (I) according to the invention are those of the formulas (Ia) to (Ig):
  • R 1 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl.
  • the compounds according to the invention are chemically and photochemically stable. They are characterized by low melting points, broad nematic phases and surprisingly high positive values for dielectric anisotropy.
  • the compounds according to the invention can be prepared by methods known per se from the literature (see, for example, Houben-Weyl, methods of
  • bromine-2,3,4-trifluorobenzene (II) with organometallic derivatives of R 1 -M, for example Grignard, lithium and zinc derivatives, or
  • Light modulators elements for image processing, signal processing or generally in the field of nonlinear optics are suitable. This also applies to compounds that have no liquid-crystalline phases as the pure substance.
  • the compounds of formula (I) are for introduction or
  • the invention therefore also relates to the use of compounds of the formula (I) in liquid-crystal mixtures.
  • the invention further relates to liquid crystal mixtures which contain one or more compounds of the formula (I).
  • the liquid crystal mixtures according to the invention generally consist of 2 to 20, preferably 2 to 15 components, including at least one, preferably 1 to 5, particularly preferably 1 to 3, compounds of the formula (I).
  • the LC mixtures according to the invention can be nematic or chiral nematic, for example.
  • the liquid crystal mixtures generally contain 0.1 to 70 mol%, preferably 0.5 to 50 mol%, in particular 1 to 25 mol%.
  • constituents of the mixtures according to the invention are preferably selected from the known compounds with nematic or
  • cholesteric phases include, for example, biphenyls, terphenyls, phenylcyclohexanes, bicyclohexanes, cyclohexylbiphenyls, mono-, di- and
  • Trifluorophenyls Generally, there are those available commercially
  • Phenylcyclohexanes as described for example in DE-A 4 108 448.
  • Liquid-crystalline mixtures which contain compounds of the general formula (I) are particularly suitable for use in electro-optical switching and display devices (displays). Such switching and
  • Display devices generally have, inter alia, the following
  • a liquid-crystalline medium e.g. made of glass or plastic
  • carrier plates e.g. made of glass or plastic
  • transparent electrodes at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • polarizers polarizers
  • thin color filter layers for color displays.
  • Other possible components are antireflection, passivation, compensation and barrier layers as well as electrically non-linear elements, such as thin-film transistors (TFT) and metal-insulator-metal (MIM) elements.
  • TFT thin-film transistors
  • MIM metal-insulator-metal
  • phase transition temperatures are determined with the help of a polarizing microscope on the basis of the texture changes.
  • the melting point is determined with a DSC device
  • Glass transition (Tg) takes place in ° C and the values are between the phase names in the phase sequence.
  • Parentheses are set, or the phase sequence is given ascending and descending in temperature.
  • Electro-optical investigations are carried out using methods known from the literature (e.g. B. Bahadur: Liquid Crystals Application and Uses, Vol. I, World Scientific, Singapore, 1990).
  • nematic liquid crystals pure or in a mixture
  • the values for the optical and dielectric anisotropy and the electro-optical characteristic are recorded at a temperature of 20 ° C.
  • Liquid crystals which do not have a nematic phase at 20 ° C. are mixed in 10% by weight in ZLI-1565 and / or in 10% by weight in ZLI-4792 (commercial nematic liquid crystal mixtures from E. Merck, Darmstadt) and the values are extrapolated from the results of the mixture.
  • Electro-optical characteristics are determined on the basis of the transmission of a measuring cell.
  • the cell is positioned between crossed polarizers in front of a light source.
  • There is a light detector behind the cell the sensitivity of which is optimized by filters for the visible area of the light. Analogous to the gradual increase in the voltage applied to the cell, the change in transmission is recorded. Values such as threshold voltage and slope are determined from this.
  • the optical anisotropy is determined using an Abb ⁇ refractometer (from Zeiss). To orient the liquid crystal, a
  • Orientation layer obtained from a 1% by weight lecithin-methanol solution.
  • the electrical variable HR (holding ratio) is in accordance with the
  • Measuring cell attached to the turntable of a polarizing microscope between crossed analyzer and polarizer. To determine the contrast, the measuring cell is positioned by turning so that a photodiode is minimal Indicates light passage (dark state). The microscope illumination is controlled so that the photodiode shows the same light intensity for all cells. After a switching operation, the light intensity (bright state) changes, and the contrast is calculated from the ratio of the light intensity of these states.
  • Example 6 The following are prepared as in Example 5: Example 6:
  • triphenylphosphine are at 0 ° C in 30 ml
  • Tetrahydrofuran was mixed with 1.31 g (7.5 mmol) of diethyl azodicarboxylate and stirred at room temperature for 0.5 h. Thereafter, 1.1 g (7.50 mmol) of 2,3,4-trifluorophenol and 1.64 g (7.50 mmol) of 4- (trans-4-ethylcyclohexyl) benzyl alcohol are added and the mixture is stirred at room temperature for 18 h. After evaporation of the solvent and chromatography on silica gel with hexane, 1.86 g of product are obtained.
  • the mixture has the phase sequence without addition of the substance according to the invention
  • Example 5 The substance according to the invention from Example 5 is compared with a 2,3,4-trifluorobenzene derivative from DE-A 39 06 052:
  • Phase sequence comparative example X 81 (42) S B (65) N 1 1 1
  • the substance according to the invention is distinguished by a broader nematic phase, a lower melting point and the absence of a higher-order smectic phase.
  • the substance according to the invention shows a significantly stronger positive
  • dielectric anisotropy which is more favorable, for example, for use in TN, STN and TFT-TN cells.

Landscapes

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

Abstract

Les 2,3,4-trifluorobenzènes de formule (I), dans laquelle R1 représente méthyle, éthyle, propyle, butyle, pentyle, hexyle, hepthyl, octyle, nonyle ou décyle et M représente (a), (b), (c), (d), (e) ou bien (f), où X représente -CH¿2?-O- ou bien -O-CH2-, conviennent comme composants de mélanges à cristaux liquides nématiques.
PCT/EP1994/003209 1993-10-08 1994-09-26 2,3,4-trifluorobenzenes et leur utilisation dans des melanges a cristaux liquides Ceased WO1995010496A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEP4334362.7 1993-10-08
DE4334362A DE4334362A1 (de) 1993-10-08 1993-10-08 2,3,4-Trifluorbenzole und ihre Verwendung in Flüssigkristallmischungen
DEP4409724.7 1994-03-22
DE4409724A DE4409724B4 (de) 1994-03-22 1994-03-22 2,3,4-Trifluorbenzole zur Verwendung in Flüssigkristallmischungen

Publications (1)

Publication Number Publication Date
WO1995010496A1 true WO1995010496A1 (fr) 1995-04-20

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WO (1) WO1995010496A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5651919A (en) * 1994-06-23 1997-07-29 Citizen Watch Co., Ltd. Benzyl ether derivative and composition containing the same
CN111094512A (zh) * 2017-09-08 2020-05-01 默克专利股份有限公司 液晶介质和包含其的液晶显示器

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051738A1 (fr) * 1980-11-10 1982-05-19 MERCK PATENT GmbH Dérivés de cyclohexyl-biphényle contenant du fluor, diélectriques les contenant et élément indicateur électro-optique
WO1985004874A1 (fr) * 1984-04-16 1985-11-07 Merck Patent Gmbh Composes anisotropes et melanges de cristaux liquides avec ceux-ci
DE3906052A1 (de) * 1988-03-10 1989-09-21 Merck Patent Gmbh Dihalogenbenzolderivate
DE4101468A1 (de) * 1990-01-23 1991-07-25 Merck Patent Gmbh Fluessigkristallines medium
WO1993001253A1 (fr) * 1991-07-04 1993-01-21 MERCK Patent Gesellschaft mit beschränkter Haftung Milieu cristallin liquide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051738A1 (fr) * 1980-11-10 1982-05-19 MERCK PATENT GmbH Dérivés de cyclohexyl-biphényle contenant du fluor, diélectriques les contenant et élément indicateur électro-optique
WO1985004874A1 (fr) * 1984-04-16 1985-11-07 Merck Patent Gmbh Composes anisotropes et melanges de cristaux liquides avec ceux-ci
DE3906052A1 (de) * 1988-03-10 1989-09-21 Merck Patent Gmbh Dihalogenbenzolderivate
DE4101468A1 (de) * 1990-01-23 1991-07-25 Merck Patent Gmbh Fluessigkristallines medium
WO1993001253A1 (fr) * 1991-07-04 1993-01-21 MERCK Patent Gesellschaft mit beschränkter Haftung Milieu cristallin liquide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5651919A (en) * 1994-06-23 1997-07-29 Citizen Watch Co., Ltd. Benzyl ether derivative and composition containing the same
CN111094512A (zh) * 2017-09-08 2020-05-01 默克专利股份有限公司 液晶介质和包含其的液晶显示器
KR20200051741A (ko) * 2017-09-08 2020-05-13 메르크 파텐트 게엠베하 액정 매질 및 이를 포함하는 액정 디스플레이
EP3679111B1 (fr) * 2017-09-08 2023-11-01 Merck Patent GmbH Milieu cristallin liquide et écran à cristaux liquides comportant ledit milieu
CN111094512B (zh) * 2017-09-08 2024-01-09 默克专利股份有限公司 液晶介质和包含其的液晶显示器
KR102788755B1 (ko) * 2017-09-08 2025-04-01 메르크 파텐트 게엠베하 액정 매질 및 이를 포함하는 액정 디스플레이

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