WO1996006073A1 - Materiaux a cristaux liquides - Google Patents

Materiaux a cristaux liquides Download PDF

Info

Publication number
WO1996006073A1
WO1996006073A1 PCT/PL1995/000016 PL9500016W WO9606073A1 WO 1996006073 A1 WO1996006073 A1 WO 1996006073A1 PL 9500016 W PL9500016 W PL 9500016W WO 9606073 A1 WO9606073 A1 WO 9606073A1
Authority
WO
WIPO (PCT)
Prior art keywords
trans
formulae
denote
compounds
mixture
Prior art date
Application number
PCT/PL1995/000016
Other languages
English (en)
Other versions
WO1996006073B1 (fr
Inventor
Vladimir Bezborodov
Roman Dabrowski
Dimitri Trokhimets
Jerzy Dziaduszek
Genadi Sasnovski
Valery Lapanik
Original Assignee
Wojskowa Akademia Techniczna
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 PL30474894A external-priority patent/PL304748A1/xx
Priority claimed from PL31002795A external-priority patent/PL310027A1/xx
Application filed by Wojskowa Akademia Techniczna filed Critical Wojskowa Akademia Techniczna
Publication of WO1996006073A1 publication Critical patent/WO1996006073A1/fr
Publication of WO1996006073B1 publication Critical patent/WO1996006073B1/fr

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
    • C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/18—Polycyclic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
    • 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
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • 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
    • 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
    • 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
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the invention is applicable to information display technology and concerns liquid crystals which are laterally substituted derivatives of cyclohexane or cyclohexene, mixtures containing them and a liquid crystal display utilizing said mixtures.
  • Liquid crystal compounds containing a cyclohexane ring in their molecules, and to a lesser degree, those with a cyclohexene ring are utilized as components of mixtures applicable to different kinds of displays. This is due to their low viscosity and high chemical stability.
  • liquid crystalline materials of this type are disclosed in PL 147527, PL 137996, PL 153286, PL 153287, PL 138287, PL 157205, PL 15551, DE 2636684, DE 4111824, DE 4023107, DE 411998, DE 4018651 , DE 4035509, JP 91:220145, JP 91:246270, JP 91 :182190, EP 458176, GB 2253402, WO 91:10716.
  • Fluorine containing compounds are characterized by high chemical stability.
  • the introduction of fluorine or chlorine in the lateral position of the molecule causes the decrease of ⁇ ⁇ ratio, what promotes the increase of the steepness of the electrooptical characteristic both in the TN and STN effects.
  • GB 2248059 dis ⁇ closes compounds substituted with fluorine.
  • R. Eidenschink Mol. Cryst. Liq. Cryst., 123, 57, (1985)
  • DE 4111765 discloses compounds with a hydroxy group in 1 or 4 position of a cyclohexane ring.
  • JP 92:13645, JP 92:13796 disclose a cyclohexanecarboxylic acid containing a -CF 3 substituent in the position 2 or 3; or 2 and 3.
  • Patents JP 92:279244, JP 92:327548 and JP 93:58926 concern difluoro geminal cyclohexane derivatives.
  • Patent application DE 4227772 describe also cyclohexene derivatives containing a perfluoroalkil group in position 1 and neighboring fluor atom in position 2 of cyclohexene ring.
  • Liquid crystal compounds according to the present invention are being obtained by the transformation of 3,6-disubstituted cyclohex-2-en-1-ones, formula 21. Synthesis of these starting compounds is described in our concurrent application and it is shown in scheme 1. The manufacture process consists in heating acetoacetate acid ester of formula 19 with hydrochlo- ride of ⁇ -dimethylaminoethyl ketones (20) in the presence an alkaline hydroxide.
  • cyclohex-2-en-1-one (formula 21) is transformed onto 2,5-disubstituted cyclohexan-1-one (formula 22) by the reduction with hydrogen in the presence of palladium catalyzer (advanta ⁇ geously 10% Pd/C).
  • the reduction is carried in alcohols or ethers advantageously in a mixture of isopropyl alcohol and dioxane (1:1).
  • a base advantageously NaOH or KOH
  • 2,5- disubstituted cyclohexan-1-ones as the mixture of two isomers, with predominance of trans- isomer, is formed.
  • the trans to cis ratio is 4:1 or higher.
  • trans to cis isomer ratio is 2:1 or lower.
  • 2,5-Disubstituted cyclohexan-1-ones are transformed into compounds being the subject of the present invention as shown in scheme 2 and 3.
  • the mixture of cis and trans isomers of compounds 22 may sometimes be used but in some cases the use of cis or trans isomers is
  • Fluorosubstituted compounds of formulae 1a1 and 1a2 are obtained by heating ketone of formula 22 with diethylaminosulphur trifluoride in a solvent such as methy ⁇ lene chloride or benzene and the resulting difluoroderivative of formula 23 (scheme 2) is treated with a base, advantageously KOH or with alcoholate, advantageously sodium or potassium tert-butylate.
  • isomeric compounds 1a1 and 1a2 are separated by crystallization or they are used in a form of the isomeric mixtures.
  • Compound of formulae 1b1 and 1b2 (scheme 2) are obtained from ketone 22 by treating it with acetone cyanohydrin in the presence of tertiary amines or alkaline metals carbonates in a solvent such as dioxane or tetrahydrofurane and resulting compound 24 is treated with POCI 3 in the presence of a tertiary aliphatic amine or pyridine.
  • Isomeric com ⁇ pounds 1b1 and 1b2 are separated by crystallization or used in a form of the isomeric mixtures.
  • the chlorine substituted compounds (formulae 1c1 and 1c2 in scheme 2) are obtained by heating ketone of formula 22 with PCI 5 , PCI 3 or POCI 3 in a hydrocarbon or chlorocarbon, advantageously in hexane or benzene.
  • the resulting intermediate of 25, without separation, is heated with water-alcohol solution of a base (advantageously NaOH or KOH).
  • Isomeric com ⁇ pounds 1 d and 1 c2 are separated by crystallization or used in a form of the isomeric mixtures.
  • Compound of formulae 1d1 and 1d2 (scheme 2) are obtained from ketone 22 by treating it with a Grignard reagent (for example CH 3 Mgl) in anhydrous ethereal solution, then the product 26 is heated in the presence of catalytic amount of acids, advantageously p- toluenesulfonic, in toluene solution.
  • a Grignard reagent for example CH 3 Mgl
  • acids advantageously p- toluenesulfonic
  • the ratio in which constitutional isomers 1a1 and 1a2 or 1b1 and 1b2 or 1c1 and c2 or 1d1 and 1d2 or 1e1 and 1e2 are formed may be changed from 0 to 1 and it depends on the character of substituent in the compounds of formulae 23-26, conditions of the reaction, the temperature and a solvent and base used. These constitutional isomers may be separated into pure forms by crystallization. It is not always necessary and not always an optimal way be ⁇ cause the yield of the product is decreased when the crystallization procedure is repeated.
  • SUBSTITUTE SHEET composition of the isomeric compounds may be obtained easily by mixing isomeric mixtures of different composition.
  • the compounds 1a2, 1b2, 1c2, 1d2, 1e2 exist in a form of cis and trans isomers, and only the trans isomer exhibits liquid-crystalline properties and is much less soluble.
  • the second constitutional isomers 1a1, 1b1, 1c1 , 1d1, 1e1 exist only in one geometric form. This fact enables the separation of constitutional isomer 1a1 or 1b1 , 1c1 , 1d1 , 1e1 from its constitutional isomer 1a2 or 1b2 and so on.
  • the mixture of constitutional isomers 1a1 and 1a2 or 1a3 and similar ones may be used for the preparation of compounds with cyclohexane ring of the formulae 1a, 1b, 1c, 1d, 1e being subject of this invention. This is done by the reduction of the mentioned mixture of isomers with hydrogen in presence of the catalyzer (palladium on carbon in concentration 5 to 10%) as it is shown in scheme 3. Lateral group Y, is located in cyclohexane ring both in an axial and equatorial position.
  • the compound of formula 1a (scheme 4) is obtained by the reduction of the compound of formula 22 with sodium borohydride and the treatment of the resulting hydroxy derivative 27 with diethylaminosulphur trifluoride (DAST) in a low-boiling solvent, advantageously in methy ⁇ lene chloride, at temperature below 20°C.
  • DAST diethylaminosulphur trifluoride
  • Liquid crystal compounds according to the present invention make it possible to create mixtures with low conductivity and different values of an optical anisotropy ( ⁇ n) and of the ratio ⁇ / ⁇ x .
  • these compounds in their molecules contain benzene rings, especially when these rings follow one another (biphenyl moiety) then liquid crystal mixtures containing them have higher values of ⁇ n.
  • Mixtures with high values of an optical anisotropy can be used in setups utilizing the condition of second and further transi ⁇ tion minima and also in PDLC displays, in which the liquid crystal mixture is dispersed in polymers.
  • the lateral substituents control the value of ⁇ ⁇ x ratio and by proper selection of mixture components from the compounds according to the present invention one influences the value of ⁇ / ⁇ ratio in mixtures and in this way controls the steepness of the electrooptical characteristic of a display (the dependence of light transmission upon the voltage at the display electrodes).
  • the object of the invention are also liquid crystalline mixtures containing at least two compounds, at least one of them is a compound of general formula 1,
  • R ⁇ -A -Z 1 -A 2 -Z 2 -A 3 -R 2 1 in which R, and R 2 are the same or different and represent a terminal group Y-(CH 2 ) n -(O) m -(CH 2 ) fc -(0) r (CH 2 ) p - or Y-(CH 2 ) n -CH CH-(CH 2 ) p -, where Y is an H, F, or Cl atom or CN, OCF 3 group, n, p and k assume values from 0 to 7, while m and I denote 0 or 1; Z, denotes a ring of formula chosen from the set comprising formulae from 2 to 9, Z 2 denotes a single bond or a ring chosen from the set comprising formulae from 2 to 9 and a position of cyclohex ⁇ ene rings Z 1 and Z 2 in relation to other neighboring rings is always such that their double bond is not conjugated with an aromatic ring; Y
  • SUBSTITUTE SHEET an H or F atom, while B and B, denote a single bond or a CH 2 -CH 2 , C ⁇ C, CH CH, OCH 2 or CH 2 0 bridge group.
  • Mixtures according to the invention contain exclusively compounds of formula 1 or compounds 1 together with other known liquid crystalline compounds and/or nonliquid crystal ⁇ line compounds such as solvents and/or optically active compounds and/or dichroic dyes and/or polymers.
  • mixtures containing two- and three-ring compounds which are the object of the invention show low or intermediate clearing temperatures.
  • the presence of four-ring or five-ring compounds of the present invention, advantageously compounds of formulae 1.38+1.67 and 1 76 ⁇ 1.94 in mixtures, causes that the mesophase range of nematic mixture may be broader than 150°C.
  • the mixtures according to the present invention are useful for an active matrix because they are characterized by high resistivity (>10 13 ⁇ -cm), a broad range of nematic phase, short switching times and high contrast. These mixtures are useful for displays working at the first transmission minimum and allow to obtain good contrast in a broad range of view angle. They have also excellent steepness in STN mode. High chemical stability and resistivity of these mixtures enables keeping electrical parameters determining the performance of a display to be stable.
  • the present invention relates also to a display consisting of two parallel plates, at least one of which is made of transparent material, supporting the electrodes, aligning and/or isolat ⁇ ing layers and/or colored filters, between which the liquid crystalline according to the present invention is used.
  • the liquors were collected and then refluxed with active carbon (10 g). After filtration of the solution the alcohol was partially evaporated. The concentrated solution was cooled and a mixture cis and trans isomers in ratio 1 :5 (5 g) was obtained. The residual oil after evaporation of the liquor (10 g) contains cis isomer of purity 95%.
  • Mass spectrum 379 (M + ), 336, 281 , 229, 201 , 117, 91, 69, 41, 28.
  • Mass spectrum 370 (M + ), 352, 281 , 228, 130, 117, 91, 69.
  • Mass spectrum 364 (M * ), 307, 279, 237, 193, 180, 152, 91.
  • 4-(trans-4-octylcyclohexyl)benzeneisothiocyanate 18 is characterized by the following parameters:
  • 4-butylcyclohexylethyl-22)cyclohex-1-en 3 is characterized by the following parameters: T N ., 50°C
  • Mixture D of the following composition was prepared wt %
  • Mixture F of the following composition was prepared: wt %

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)

Abstract

Nouveaux composés de formule R1-A1-Z1-A2-Z2-A3-R2 dans laquelle Z1 et Z2 sont des liaisons cyclohexane et cyclohexène à liaison latérale substituée, selon les formules (2), (3), (4), (5), (6), (7), (8) et (9). Ces composés sont utiles comme composants de mélanges cristallins liquides pour des applications d'affichage.
PCT/PL1995/000016 1994-08-18 1995-08-18 Materiaux a cristaux liquides WO1996006073A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
PLP.304748 1994-08-18
PL30474894A PL304748A1 (en) 1994-08-18 1994-08-18 Liquid-crystalline compounds, mixes containing them and lc display employing such mixes
PL31002795A PL310027A1 (en) 1995-08-16 1995-08-16 Derivatives of cyclohexane and liquid crystal mixes containing them
PLP.310027 1995-08-16

Publications (2)

Publication Number Publication Date
WO1996006073A1 true WO1996006073A1 (fr) 1996-02-29
WO1996006073B1 WO1996006073B1 (fr) 1996-03-14

Family

ID=26653129

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/PL1995/000016 WO1996006073A1 (fr) 1994-08-18 1995-08-18 Materiaux a cristaux liquides

Country Status (1)

Country Link
WO (1) WO1996006073A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19607996B4 (de) * 1996-03-04 2008-07-03 Merck Patent Gmbh Flüssigkristallines Medium enthaltend mindestens ein substituiertes Cyclohex-3-en-yl-Derivat
DE19723276B4 (de) * 1997-06-04 2008-11-27 Merck Patent Gmbh Flüssigkristallines Medium enthaltend Cyclohexan-Derivate
TWI448450B (zh) * 2008-06-09 2014-08-11 Jnc Corp 具有環已烷環之５環液晶化合物、液晶組成物以及液晶顯示元件
JPWO2014168260A1 (ja) * 2013-04-11 2017-02-16 住友化学株式会社 光学異方層形成用組成物
US20180046033A1 (en) * 2016-08-11 2018-02-15 Samsung Display Co., Ltd. Liquid crystal display and liquid crystal composition comprised thereof
CN114106850A (zh) * 2021-12-17 2022-03-01 苏州汉朗光电有限公司 一种正性液晶组合物及其在液晶显示装置中的应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986005486A1 (fr) * 1985-03-22 1986-09-25 MERCK Patent Gesellschaft mit beschränkter Haftung Derives de cyclohexane
WO1986005484A1 (fr) * 1985-03-22 1986-09-25 MERCK Patent Gesellschaft mit beschränkter Haftung Derives de cyclohexane
JPH05310616A (ja) * 1992-05-15 1993-11-22 Dainippon Ink & Chem Inc フルオロシクロヘキセン誘導体
DE4227772A1 (de) * 1992-08-23 1994-02-24 Merck Patent Gmbh 2-Fluor-perfluoralkylcyclohexen-Derivate
WO1995004790A1 (fr) * 1993-08-06 1995-02-16 Merck Patent Gmbh Derives de 2-fluorocyclohexene

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986005486A1 (fr) * 1985-03-22 1986-09-25 MERCK Patent Gesellschaft mit beschränkter Haftung Derives de cyclohexane
WO1986005484A1 (fr) * 1985-03-22 1986-09-25 MERCK Patent Gesellschaft mit beschränkter Haftung Derives de cyclohexane
JPH05310616A (ja) * 1992-05-15 1993-11-22 Dainippon Ink & Chem Inc フルオロシクロヘキセン誘導体
DE4227772A1 (de) * 1992-08-23 1994-02-24 Merck Patent Gmbh 2-Fluor-perfluoralkylcyclohexen-Derivate
WO1995004790A1 (fr) * 1993-08-06 1995-02-16 Merck Patent Gmbh Derives de 2-fluorocyclohexene

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
L.A. KARAMYSHEVA: "Liquid crystalline phenylcyclohexanes with a lateral methyl substituent", MOLECULAR CRYSTALS AND LIQUID CRYSTALS (INC. NONLINEAR OPTICS ), vol. 191, 1990, READING GB, pages 259 - 267, XP000206510 *
PATENT ABSTRACTS OF JAPAN vol. 18, no. 122 (C - 1173) 28 February 1994 (1994-02-28) *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19607996B4 (de) * 1996-03-04 2008-07-03 Merck Patent Gmbh Flüssigkristallines Medium enthaltend mindestens ein substituiertes Cyclohex-3-en-yl-Derivat
DE19723276B4 (de) * 1997-06-04 2008-11-27 Merck Patent Gmbh Flüssigkristallines Medium enthaltend Cyclohexan-Derivate
TWI448450B (zh) * 2008-06-09 2014-08-11 Jnc Corp 具有環已烷環之５環液晶化合物、液晶組成物以及液晶顯示元件
JPWO2014168260A1 (ja) * 2013-04-11 2017-02-16 住友化学株式会社 光学異方層形成用組成物
US20180046033A1 (en) * 2016-08-11 2018-02-15 Samsung Display Co., Ltd. Liquid crystal display and liquid crystal composition comprised thereof
US10459292B2 (en) * 2016-08-11 2019-10-29 Samsung Display Co., Ltd. Liquid crystal display and liquid crystal composition comprised thereof
CN114106850A (zh) * 2021-12-17 2022-03-01 苏州汉朗光电有限公司 一种正性液晶组合物及其在液晶显示装置中的应用
CN114106850B (zh) * 2021-12-17 2022-11-18 重庆汉朗精工科技有限公司 一种正性液晶组合物及其在液晶显示装置中的应用

Similar Documents

Publication Publication Date Title
JP2927542B2 (ja) ハロゲン化ベンゼン誘導体および液晶相
EP1482019B1 (fr) Dérivés de pyrane
KR0153476B1 (ko) 페닐사이클로헥산 및 액정 매질
CA2046590A1 (fr) Derives de substitution en 1,4 de 2,6-difluorobenzene; milieu cristallise liquide
US5389295A (en) Benzene derivatives, and a liquid crystal medium
KR19980032457A (ko) 비스알케닐비사이클로헥산 및 액정 매질
US4434073A (en) Perhydrophenanthrene derivatives, their preparation, and their use in liquid-crystalline dielectrics and electro-optical display elements
JPH08507771A (ja) １，２，２，２‐テトラフルオロエチルエーテル化合物及び液晶媒質
JP5152947B2 (ja) ２−フルオロナフタレン誘導体である新規液晶性化合物とそれを含有する液晶組成物
US5213710A (en) Benzene derivatives and a liquid-crystalline medium
KR100563351B1 (ko) 사이클로헥산유도체및액정매질
KR100266245B1 (ko) 사이클로헥산 유도체 및 이를 함유하는 액정 조성물
EP1482020A1 (fr) Dérivés de pyrane avec une double liaison exocyclique
WO1996006073A1 (fr) Materiaux a cristaux liquides
US5494606A (en) 1,3-dioxane derivatives, and liquid-crystalline medium
KR0166067B1 (ko) 디사이클로헥실에틸렌 유도체
US5641432A (en) Dicyclohexylethylene derivative
KR100549883B1 (ko) 플루오로시클로헥산유도체및액정매질
JPH08510220A (ja) 部分的に弗素化されたベンゼン誘導体及び液晶媒質
DE4203719A1 (de) Benzolderivate und fluessigkristallines medium
CH652118A5 (de) Fluessigkristall-verbindungen.
JP2927957B2 (ja) フェニルシクロヘキサン類および液晶媒体
EP0471287A1 (fr) Dérivés d'alkoxypropènes
WO1998011173A1 (fr) Materiaux pour cristaux liquides
JP4478842B2 (ja) デカヒドロナフタレン誘導体

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CH CN DE GB JP KR

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642