[go: up one dir, main page]

WO1995009827A1 - 3,4 difluorobenzenes et leur utilisation dans des melanges de cristaux liquides - Google Patents

3,4 difluorobenzenes et leur utilisation dans des melanges de cristaux liquides Download PDF

Info

Publication number
WO1995009827A1
WO1995009827A1 PCT/EP1994/003125 EP9403125W WO9509827A1 WO 1995009827 A1 WO1995009827 A1 WO 1995009827A1 EP 9403125 W EP9403125 W EP 9403125W WO 9509827 A1 WO9509827 A1 WO 9509827A1
Authority
WO
WIPO (PCT)
Prior art keywords
diyl
formula
liquid crystal
atoms
trans
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/EP1994/003125
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.)
Merck Patent GmbH
Original Assignee
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
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of WO1995009827A1 publication Critical patent/WO1995009827A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C09K19/04—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
    • 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
    • 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 to the materials with which they are associated during and after the manufacturing process (e.g.
  • Liquid crystal mixtures and thus on a large number of mesogenic and non-mesogenic compounds of different structures, which enable the mixtures to be adapted to the most varied of applications. This applies both to the areas where nematic LC phases are used in
  • Liquid crystal mixtures are suitable.
  • the present invention therefore relates to new ones
  • a 1 , A 2 , A 3 are the same or different 1, 4-phenylene, pyridine-2,5-diyl,
  • Pyrimidine-2,5-diyl in which one or two H atoms can be replaced by F, trans-1, 4-cyclohexylene, 1, 3-dioxane-2,5-diyl or naphthalene-2,6-diyl;
  • X is -CH 2 -O- or -O-CH 2 -; k, I, m, n, o, p are zero or one, provided that the sum k + m + o is greater than zero.
  • R 1 is a straight-chain alkyl having 1 to 15 carbon atoms
  • a 1 , A 2 , A 3 are identical or different 1, 4-phenylene, in which one or two H atoms can be replaced by F, or trans-1, 4-cyclohexylene;
  • M 1 , M 2 are identical or different -CH 2 CH 2 -, -C ⁇ C-, -CH 2 -O-, -O-CH 2 -, -CO-O- or -O-CO-;
  • X is -CH 2 -O- or -O-CH 2 -;
  • k, I, m, n, o, p are zero or one, provided that the sum k + m + o is greater than zero.
  • R 1 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl.
  • the substances according to the invention are distinguished by particularly low melting points. In mixtures, they have an advantageous, for example lowering, effect on the glass transition temperature. This is favorable for a low viscosity and its low temperature dependence.
  • the compounds according to the invention can be prepared according to
  • the preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. Use can also be made of variants which are known per se and are not mentioned here in detail.
  • Dioxane derivatives are useful by reacting an appropriate aldehyde (or one of its reactive derivatives) with one
  • Sulfuric acid, benzene or p-toluenesulfonic acid at temperatures between about 20 ° C and about 150 ° C, preferably between 80 ° C and 120 ° C.
  • Acetals are primarily suitable as reactive derivatives of the starting materials.
  • the aldehydes are through Oxidation of corresponding alcohols or by reduction of nitriles or corresponding carboxylic acids or their derivatives, the diols obtainable by reduction of corresponding diesters.
  • Esters of the formula (I) can also be correspondingly esterified
  • Carboxylic acids (or their reactive derivatives) with alcohols or
  • the acid halides especially the chlorides and bromides
  • the anhydrides for example also mixed anhydrides, azides or esters, in particular alkyl esters with 1-4 C atoms in the alkyl group.
  • Reactive derivatives of the alcohols or phenols mentioned include, in particular, the corresponding metal alcoholates or phenolates,
  • an alkali metal such as sodium or potassium.
  • esterification is advantageously carried out in the presence of an inert solvent.
  • an inert solvent particularly suitable are ethers, such as diethyl ether,
  • Hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as carbon tetrachloride, dichloromethane or tetrachlorethylene and sulfoxides such as dimethyl sulfoxide or sulfolane.
  • Ethers of the formula (I) are more appropriate by etherification
  • Hydroxy compounds preferably corresponding phenols, are available, the hydroxyl compound expediently first in a corresponding
  • Metal derivative for example by treatment with NaH, NaNH 2 , NaOH, KOH, Na 2 CO 3 or K 2 CO 3 is converted into the corresponding alkali metal alcoholate or alkali metal phenolate.
  • This can then be reacted with the corresponding alkyl halide, sulfonate or dialkyl sulfate, advantageously in an inert solvent such as acetone, 1, 2-dimethoxyethane, DMF or dimethyl sulfoxide, or with an excess of aqueous or aqueous-alcoholic NaOH or KOH at temperatures between about 20 and 100 ° C.
  • the compounds of the general formula (I) according to the invention are chemically and photochemically stable. They have low melting points and generally broad liquid-crystalline phases, in particular broad nematic ones. Compounds of the formula (I) can be used, for example, for the preparation of nematic or chiral nematic liquid-crystal mixtures
  • 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, for example, nematic, chiral nematic, smectic and / or ferroelectric.
  • the compound or compounds of formula (I) according to the invention contain the
  • Liquid crystal mixtures in general 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
  • Liquid crystal mixtures before the addition of the invention Compound (s) as mixtures of various components, at least one of which is mesogenic.
  • Suitable further constituents of nematic or chiral nematic liquid crystal mixtures according to the invention are, for example, 4-fluorobenzenes, as for example in EP-A 494 368, WO 92/06 148, EP-A 460 436, DE-A 4 111 766, DE-A 4 1 12 024, DE-A 4 1 12 001, DE-A 4 100 288, DE-A 4 101 468, EP-A 423 520, DE-A 392 3064, EP-A 406 468, EP-A 393 577, EP -A 393 490, - 3,4-difluorobenzenes, as described for example in DE-A 4 108 448, EP-A 507 094 and EP-A 502 407, - 3,4,5-trifluorobenzenes, as for example in DE- A 4 108 448, EP-A
  • 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 according to methods known from the literature (for example B. Bahadur: Liquid Crystals Application and Uses, Vol. I, World Scientific, Singapore, 1990).
  • 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 20% 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
  • 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. Then 0.98 g (7.50 mmol) of 3,4-difluorophenol and 0.92 g (5.00 mmol) of trans-4-pentylcyclohexylmethanol are added and the mixture is stirred at room temperature for 18 h. After evaporating the
  • Table 1 shows application examples. The substances from Examples 1 and 8 are used as pure substance and in a mixture (10% by weight) with ZLI 1565
  • Example 8 the substance from Example 8 is compared with a reference substance in the commercial nematic liquid crystal mixture ZLI-4792 (E. Merck, Darmstadt). It turns out that the substance according to the invention is able to lower the higher-order smectic phase considerably, quite in contrast to the reference substance.
  • electro-optical threshold voltages are increased less by the substance from Example 8, which is also advantageous.

Landscapes

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

Abstract

L'invention concerne des dérivés de 3,4-difluorobenzènes de formule (I) où les symboles et les indices ont la notation suivante: R1 désigne H, un alkyle linéaire ou ramifié (avec ou sans atome de C asymétrique) ayant entre 1 et 15 atomes de C, où un ou deux groupes CH¿2? non adjacents peuvent être remplacés par -O-, -CH=CH-, -C C-, cyclopropane-1,2-diyle ou -Si(CH3)2- et où un ou plusieurs atomes de H du reste alkyle peuvent être substitués par F; A?1, A2 et A3¿ sont identiques ou différents et désignent 1,4-phénylène, pyridine-2,5-diyle, pyrimidine-2,5-diyle dans lesquels un ou deux atomes de H peuvent être remplacés par F, trans 1,4-cyclohexylène, 1,3-dioxane-2,5-diyle ou naphtalène-2,6-diyle; M1 et M2 sont identiques ou différents et désignent -CH¿2?CH2-, -CH=CH-, -C C-, -CH2CH2CH2CH2-, -CH2CH2CH2-O-, -O-CH2CH2CH2-, -CH2CH2-CO-O-, -O-CO-CH2CH2-, -CH2-O-, -O-CH2, -CO-O- ou -O-CO-; X désigne -CH2-O- ou -O-CH2-; k, l, m, n, o, p valent zéro ou un, à condition que la somme k+m+o soit supérieure à zéro. Les substances produites selon l'invention se caractérisent par des points de fusion extrêmement bas. Dans des mélanges, elles agissent de manière particulièrement avantageuse, par ex. en abaissant la température de transition vitreuse, ce qui permet d'obtenir une faible viscosité et une variabilité réduite de celle-ci avec la température.
PCT/EP1994/003125 1993-10-05 1994-09-19 3,4 difluorobenzenes et leur utilisation dans des melanges de cristaux liquides Ceased WO1995009827A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4333838.0 1993-10-05
DE4333838A DE4333838A1 (de) 1993-10-05 1993-10-05 3,4-Difluorbenzole und ihre Verwendung in Flüssigkristallmischungen

Publications (1)

Publication Number Publication Date
WO1995009827A1 true WO1995009827A1 (fr) 1995-04-13

Family

ID=6499393

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/003125 Ceased WO1995009827A1 (fr) 1993-10-05 1994-09-19 3,4 difluorobenzenes et leur utilisation dans des melanges de cristaux liquides

Country Status (2)

Country Link
DE (1) DE4333838A1 (fr)
WO (1) WO1995009827A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0775718A2 (fr) 1995-11-22 1997-05-28 Union Carbide Chemicals & Plastics Technology Corporation Procédé de production des compositions d'élastomères de granulats d'élastomères et polymères
US5728782A (en) * 1996-12-06 1998-03-17 Union Carbide Chemicals & Plastics Technology Corporation Gas phase anionic polymerization of dienes and vinyl-substituted aromatic compounds
US6444605B1 (en) 1999-12-28 2002-09-03 Union Carbide Chemicals & Plastics Technology Corporation Mixed metal alkoxide and cycloalkadienyl catalysts for the production of polyolefins

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102019006512A1 (de) 2019-09-13 2020-08-06 Georg Egger Rein durch Muskelkraft betriebenes Fahrzeug

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0315014A2 (fr) * 1987-11-06 1989-05-10 F. Hoffmann-La Roche Ag Dérivés halogénés du benzène
EP0423520A2 (fr) * 1989-10-19 1991-04-24 MERCK PATENT GmbH Composition liquide cristalline pour utilisation dans une cellule nématique torsadée
EP0471287A1 (fr) * 1990-08-15 1992-02-19 F. Hoffmann-La Roche Ag Dérivés d'alkoxypropènes
JPH05125008A (ja) * 1991-10-30 1993-05-21 Asahi Denka Kogyo Kk トランスシクロヘキサンジメチル誘導体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0315014A2 (fr) * 1987-11-06 1989-05-10 F. Hoffmann-La Roche Ag Dérivés halogénés du benzène
EP0423520A2 (fr) * 1989-10-19 1991-04-24 MERCK PATENT GmbH Composition liquide cristalline pour utilisation dans une cellule nématique torsadée
EP0471287A1 (fr) * 1990-08-15 1992-02-19 F. Hoffmann-La Roche Ag Dérivés d'alkoxypropènes
JPH05125008A (ja) * 1991-10-30 1993-05-21 Asahi Denka Kogyo Kk トランスシクロヘキサンジメチル誘導体

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 17, no. 489 (C - 1106) 6 September 1993 (1993-09-06) *
S.M.KELLY: "Four unit linking group", LIQUID CRYSTALS, vol. 10, no. 2, August 1991 (1991-08-01), LONDON GB, pages 273 - 287 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0775718A2 (fr) 1995-11-22 1997-05-28 Union Carbide Chemicals & Plastics Technology Corporation Procédé de production des compositions d'élastomères de granulats d'élastomères et polymères
US5728782A (en) * 1996-12-06 1998-03-17 Union Carbide Chemicals & Plastics Technology Corporation Gas phase anionic polymerization of dienes and vinyl-substituted aromatic compounds
US6444605B1 (en) 1999-12-28 2002-09-03 Union Carbide Chemicals & Plastics Technology Corporation Mixed metal alkoxide and cycloalkadienyl catalysts for the production of polyolefins

Also Published As

Publication number Publication date
DE4333838A1 (de) 1995-04-06

Similar Documents

Publication Publication Date Title
EP0837851B1 (fr) Derives de phenanthrene fluores et leur utilisation dans des melanges a cristaux liquides
DE19500768C2 (de) Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen
EP1028935B1 (fr) Derives fluores de phenanthrene et leur utilisation dans des melanges a cristaux liquides
WO1995032261A1 (fr) Fluoroalkylethinylbenzenes et difluoroalkylethinylbenz et leur utilisation dans des melanges a cristaux liquides
WO1995010498A1 (fr) 3,4-trifluorobenzene et leur utilisation dans des melanges a cristaux liquides
DE4331679C2 (de) Spiro[5,5]undecane, diese enthaltende Flüssigkristallmischung und diese enthaltende Schalt- und/oder Anzeigevorrichtung
WO1995013257A1 (fr) 2,6-difluorobenzenes et leur utilisation dans des melanges a cristaux liquides
WO1995009827A1 (fr) 3,4 difluorobenzenes et leur utilisation dans des melanges de cristaux liquides
DE4336265A1 (de) 3-Trifluormethylbenzole und ihre Verwendung in Flüssigkristallmischungen
EP0743971B1 (fr) Derives de phenanthridine et leur utilisation dans des melanges de cristaux liquides
WO1995009829A1 (fr) 2,4-difluorobenzenes et leur utilisation dans des melanges a cristaux liquides
WO1995011890A1 (fr) 6-fluorobenzothiazoles et leur utilisation dans des melanges a cristaux liquides
DE4336391A1 (de) 3,5-Bis(trifluormethyl)benzole und ihre Verwendung in Flüssigkristallmischungen
DE4430668B4 (de) Derivate des 4,4-Difluorcyclohexans und 4,4-Difluor-1-cyclohexens und ihre Verwendung in Flüssigkristallmischungen
WO1995009828A1 (fr) 2,4,5-trifluorobenzenes et leur utilisation dans des melanges de cristaux liquides
WO1995011214A1 (fr) Benzenes de 4-trifluoromethyle et leurs utilisation dans des melanges a cristaux liquides
WO1995013999A1 (fr) 3,5-difluorobenzenes et leur utilisation dans des melanges de cristaux liquides
DE4409724B4 (de) 2,3,4-Trifluorbenzole zur Verwendung in Flüssigkristallmischungen
DE4333837B4 (de) 4-Fluorbenzole und ihre Verwendung in Flüssigkristallmischungen
WO1995010495A1 (fr) 2,3,4,5-tetrafluorobenzene et leur utilisation dans des melanges a cristaux liquides
DE19627899A1 (de) Verbindungen mit mehrfach methylverzweigten Seitenketten und deren Verwendung in Flüssigkristallmischungen
DE4333862A1 (de) 4-Fluor-3-trifluormethylbenzole und ihre Verwendung in Flüssigkristallmischungen
DE4338267A1 (de) 3-Fluorbenzole und ihre Verwendung in Flüssigkristallmischungen
DE4423898C2 (de) 2,6-Difluorbenzole und ihre Verwendung in Flüssigkristallmischungen
DE4334362A1 (de) 2,3,4-Trifluorbenzole und ihre Verwendung in Flüssigkristallmischungen

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CN JP KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase