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WO1996004351A1 - Procede de preparation de melanges a cristaux liquides - Google Patents

Procede de preparation de melanges a cristaux liquides Download PDF

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Publication number
WO1996004351A1
WO1996004351A1 PCT/EP1995/003002 EP9503002W WO9604351A1 WO 1996004351 A1 WO1996004351 A1 WO 1996004351A1 EP 9503002 W EP9503002 W EP 9503002W WO 9604351 A1 WO9604351 A1 WO 9604351A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
mixture
groups
mixtures
compound
Prior art date
Application number
PCT/EP1995/003002
Other languages
German (de)
English (en)
Inventor
Karl Siemensmeyer
Karl-Heinz Etzbach
Paul Delavier
Frank Meyer
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to JP8506181A priority Critical patent/JPH10503541A/ja
Priority to EP95927740A priority patent/EP0773980A1/fr
Priority to KR1019970700795A priority patent/KR970704855A/ko
Publication of WO1996004351A1 publication Critical patent/WO1996004351A1/fr

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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
    • 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
    • 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
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • 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
    • 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
    • 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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro 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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines
    • 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
    • C09K2019/0448—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 end chain group being a polymerizable end group, e.g. -Sp-P or acrylate

Definitions

  • the invention relates to a process for the preparation of mixtures of liquid-crystalline compounds, characterized in that at least one of the starting components consists of a mixture of at least two compounds and this mixture is reacted with at least one further starting component to form a statistical mixture by methods known per se .
  • liquid-crystalline materials generally do not have the properties desired for the application. It is only by mixing different liquid-crystalline and, if desired, also non-liquid-crystalline compounds that it is possible to extend the property spectrum of the liquid-crystalline material e.g. with regard to the liquid crystal phase temperatures, electro-optical switching times, birefringence or viscosity for the intended application. Mixtures which contain a large number of different compounds, usually significantly more than ten, are generally required for applications in electro-optics, be it in the field of neic or ferroelectric phases. Liquid crystalline compounds exist with very different structures, but the components do not differ very drastically in many mixtures.
  • the process is particularly suitable for the preparation of mixtures of liquid-crystalline compounds of the general formula I.
  • R is hydrogen or -CC 4 alkyl
  • a 2 is a group of the definition of A 1 , the conditions for m being replaced by corresponding conditions for n and
  • M is a mesogenic group consisting of 2 to 5 saturated or unsaturated five- to seven-membered carbocyclic or heterocyclic groups, which are represented by the same or different bridge members of the definition of Y 1 - Y 4 are connected.
  • These compounds can contain polymerizable radicals Z 1 or Z 2 .
  • Preferred radicals Z 1 or Z 2 are, for example
  • N : N : C S, 0 - CS N,
  • radicals R are hydrogen or -CC 4 alkyl groups and may be the same or different.
  • Bridge members are oxygen, —0 — CO— and
  • the groups A 1 or A 2 can be hydrogen or -C-C 3 o-alkyl groups.
  • radicals A 1 and A 2 are: Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-E hylhexyl, isooctyl, nonyl, isononyl , Decyl, isodecyl, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl.
  • isooctyl, isononyl, isodecyl and isotridecyl are trivial designations and come from the alcohols obtained after oxosynthesis (cf. Ulimann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. AI, pages 290 to 293, and Vol. A 10, pages 284 and 285)).
  • alkyl groups with 1 to 18 carbon atoms are preferred, particularly preferably with 4 to 12 carbon atoms.
  • Linear alkyl groups are also preferred.
  • alkyl groups can also be interrupted by oxygen in ether function or by non-adjacent imino or C 1 -C 4 alkylimino groups.
  • Examples of such groups A 1 and A 2 are:
  • a 1 and A 2 can furthermore be halogen, preferably fluorine, chlorine and bromine.
  • one of the radicals A 1 or A 2 is a halogen or another radical of small size such as cyano, nitro, methyl, ethyl or propyl
  • the other radical A 1 or A 2 is preferably a longer-chain alkyl or alkylene radical.
  • a 1 or A 2 is a C 2 -C 0 alkylene group which can be interrupted by oxygen in ether function or by non-adjacent imino or C 4 -C 4 alkylimino groups .
  • radicals T and Y 5 may be the same or different.
  • R is preferably 1 or 2.
  • radicals T can also be ring systems substituted by fluorine, chlorine, bromine, cyano, hydroxy or nitro.
  • Preferred radicals T are:
  • mesogenic groups M are, for example
  • R 1 , R 2 and R 3 are hydrogen, 0CH 3 , CH 3 , F, Cl or Br,
  • HY 2 MYH Ha by methods known per se with, if only one compound Ila is used, a plurality of purple compounds or, if more than one compound Ila is used, at least one purple compound
  • X 1 is hydroxyl, amino, carboxyl or another condensable group or halogen or another leaving group
  • M 1 and M 2 constituents of the mesogenic groups M, consisting of 1 to 2 saturated or unsaturated five- to seven-membered carbocyclic or heterocyclic groups, in the event that M 1 and / or M 2 consists of two such groups, these are connected by a bridge link of the definition of Y 1 ,
  • X 3 is halogen or OH
  • the three variants a), b) and c) have in common that at least one of the starting components consists of more than one compound, but these compounds have the homologous structures indicated.
  • the multiple starting components preferably consist of 2 to 10, particularly preferably 3 to 8, different homologous compounds.
  • the quantitative ratios of the compounds within a multiple component depend on the properties that are to be achieved for the liquid-crystalline mixture. It is advantageous to optimize the desired properties by varying the proportions.
  • the individual compounds are generally used in amounts of 1 to 99 mol%, preferably 5 to 95 mol%, particularly preferably 10 to 90 mol%, based on the sum of the compounds of a component.
  • Ila and lila, IIb and Illb or Ilc and IIIc are generally used in a ratio of 20: 1 to 1:20, preferably in a ratio of 5: 1 to 1: 5, particularly preferably in an approximate range stoichiometric ratio.
  • the reactions are generally carried out in the presence of a solvent.
  • a solvent particularly suitable solvents are moderately polar aprotic solvents such as pyridine, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, acetone, methylethyl ketone or propyl ethyl ketone.
  • the reactions are advantageously carried out at temperatures from 10 ° C. to 150 ° C., preferably between 30 and 100 ° C., particularly preferably between 40 and 80 ° C. In general, atmospheric pressure is used.
  • the properties of the resulting liquid-crystalline mixtures are shaped by the number, the proportions and the structural differences of the compounds used.
  • a particularly suitable structural variation is, for example, the use of compounds with different lengths of groups A 1 or A 2 or different substitution patterns.
  • Variants a), b) and c) differ in that synthesis step in which a statistical mixture of different compounds is generated by using multiple starting components.
  • the statistical mixture is obtained by reacting the mesogenic group substituted by Y 2 H and Y 3 H with a compound IIIa
  • X 1 is a condensable group such as, for example, hydroxyl, amino or carboxyl, or a group which easily escapes in a nucleophilic substitution reaction, such as Br, J or tosylate.
  • a condensation reaction can be carried out according to generally known methods, for example with the aid of carbodiimides or other condensation agents, and is particularly suitable for producing an ester or amide bond.
  • the statistical mixture is generated when the mesogenic group M is built up, a central part M 2 of the mesogenic group M, which is doubly substituted with carboxyl or acid halide groups, serving as a starting component.
  • the second component carries on the molecular parts M 1 hydroxyl, mercapto, amino or alkylamino groups, which can react in a known manner with the carboxyl or acid halide groups of M 2 .
  • the statistical mixture is also generated when the mesogenic group M is built up, but the reactive groups of M 1 and M 2 are interchanged in comparison to variant b).
  • the method according to the invention is suitable e.g. for the preparation of the compounds IV
  • a 3 is a C 1 -C 2 -alkylene group which can be interrupted by oxygen in ether function or by non-adjacent imino or C 1 -C 4 -alkyl imino groups,
  • radicals Z 1 , Y 1 , Y 2 , Y 3 , A 1 , A 3 and M and the variables and s, since they occur 6 times in the formula, can be the same or different.
  • group M which is particularly preferred here is substituted triphenylene radicals.
  • a statistical mixture of different compounds IV is produced by mixing several compounds IVa
  • the reaction can be carried out according to the same methods as described for the reaction of Ila with purple.
  • Another possibility for influencing the properties of the liquid-crystalline mixtures is the hydrogenation of the statistically generated mixture.
  • the hydrogenation can be carried out according to generally known methods. Hydrogenation is particularly suitable for Transformation of aromatic ring structures within the mesogenic group M into saturated ring structures.
  • the mixtures produced according to the invention have no disadvantages compared to conventionally produced mixtures, since they also behave practically like individual compounds with regard to the cleaning options, in particular in chromatography processes such as HPLC and MPLC.
  • the process according to the invention also makes it possible to produce mixtures which are not accessible by conventional means or can only be obtained with great effort, since the synthesis effort according to the conventional process of single-component synthesis, e.g. with the variation of several feed components increases exponentially with the complexity of the mixture.
  • the method according to the invention enables easily complex mixtures with properties optimized for the application, e.g. with regard to viscosity, switching time, phase state ranges, birefringence or dielectric anisotropy.
  • phase transition temperatures were determined in a Mettler microscope heating table (FP800 / 84) in connection with a Leitz polarizing microscope (Ortholux-Pol-II).
  • the percentages for the compositions of the mixtures all relate to percentages by mass. Any deviating information is given as a unit.
  • 1,2-dichloroethane is mixed with 5 7.21 g (0.054 mol) of aluminum chloride. While cooling with ice water, 3.7 g (0.047 mol) of acetyl chloride and then the hydrogenation product dissolved in dichloroethane are carefully added dropwise to this suspension in such a way that the internal temperature always remains at approximately 20 ° C. After stirring at room temperature overnight, the contents of the flask are carefully poured onto ice water and dissolved aluminum hydroxide is brought into solution with a little concentrated hydrochloric acid. The organic layer is then separated off and the aqueous phase is extracted twice more with 1,2-dichloroethane.
  • the product mixture formed is converted into the carboxylic acid by a subsequent haloform reaction.
  • the carboxylic acid function is then converted into the nitrile group via the amide and subsequent dehydration with P0C1 3 . 5 Yield: 7.8 g
  • reaction mixture is poured onto water and the organic phase is separated off.
  • the organic phase is shaken out with half-concentrated HCl and then with sodium carbonate solution and then dried with sodium sulfate.
  • 94.7 g of mixture 3 were obtained after concentration.
  • reaction mixture is added to a mixture of ice and concentrated hydrochloric acid and the organic phase is separated off. This is neutralized and then shaken out several times with a potassium hydroxide solution. Finally, the organic phase 45 is neutralized, dried with sodium sulfate and the solvent deducted.
  • the mixture contains, statistically linked, 43% hexyloxy and 57% ethyl acrylate side chains.
  • the mixture has a discotically liquid-crystalline phase.

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

Abstract

L'invention concerne un procédé de préparation de mélanges de composés à cristaux liquides, selon lequel au moins un des constituants de départ se compose d'un mélange d'au moins deux composés et ce mélange est mis à réagir, selon des méthodes connues en soi, avec au moins un autre constituant de départ, pour former un mélange statique.
PCT/EP1995/003002 1994-08-05 1995-07-28 Procede de preparation de melanges a cristaux liquides WO1996004351A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP8506181A JPH10503541A (ja) 1994-08-05 1995-07-28 液晶混合物の製造方法
EP95927740A EP0773980A1 (fr) 1994-08-05 1995-07-28 Procede de preparation de melanges a cristaux liquides
KR1019970700795A KR970704855A (ko) 1994-08-05 1995-07-28 액정 혼합물의 제조 방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4427766A DE4427766A1 (de) 1994-08-05 1994-08-05 Verfahren zur Herstellung flüssigkristalliner Mischungen
DEP4427766.0 1994-08-05

Publications (1)

Publication Number Publication Date
WO1996004351A1 true WO1996004351A1 (fr) 1996-02-15

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003002 WO1996004351A1 (fr) 1994-08-05 1995-07-28 Procede de preparation de melanges a cristaux liquides

Country Status (6)

Country Link
EP (1) EP0773980A1 (fr)
JP (1) JPH10503541A (fr)
KR (1) KR970704855A (fr)
CN (1) CN1158142A (fr)
DE (1) DE4427766A1 (fr)
WO (1) WO1996004351A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996024647A1 (fr) * 1995-02-06 1996-08-15 Merck Patent Gmbh Composes mesogeniques bireactifs et intermediaires associes
WO1998047979A1 (fr) * 1997-04-22 1998-10-29 Basf Aktiengesellschaft Procede de preparation de composes polymerisables a cristaux liquides
RU2189281C2 (ru) * 1996-04-19 2002-09-20 Берингер Ингельхайм Фарма Кг Двухкамерный контейнер для дозируемых аэрозолей, не содержащих пропеллента
US6695977B2 (en) 2000-12-11 2004-02-24 Basf Aktiengesellschaft Use of chiral, uncharged metal compounds as dopants for liquid-crystalline materials
US7258902B2 (en) 2002-07-01 2007-08-21 Basf Aktiengesellschaft Chiral 3,4-dihydro-2H-pyran compounds
US7264749B2 (en) 2002-04-29 2007-09-04 Basf Aktiengesellschaft Alkyne compounds
US8608977B2 (en) 2008-06-17 2013-12-17 Basf Se Polymerizable chiral compounds comprising 2,6-naphthyl and isomannitol units, and use thereof as chiral dopants
WO2014050426A1 (fr) * 2012-09-25 2014-04-03 富士フイルム株式会社 Composition de cristaux liquides, procédé de production de la composition, et film associé
JP2016510820A (ja) * 2013-10-01 2016-04-11 エルジー・ケム・リミテッド 液晶組成物
WO2019141833A1 (fr) 2018-01-22 2019-07-25 Merck Patent Gmbh Matériaux diélectriques
WO2020078938A1 (fr) 2018-10-18 2020-04-23 Merck Patent Gmbh Matériaux copolymères diélectriques
WO2020078939A1 (fr) 2018-10-18 2020-04-23 Merck Patent Gmbh Matériaux copolymères diélectriques
WO2025061815A1 (fr) 2023-09-22 2025-03-27 Merck Patent Gmbh Matériaux de copolymère diélectrique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7420502B2 (ja) * 2019-07-24 2024-01-23 住友化学株式会社 重合性液晶混合組成物、位相差板、楕円偏光板および有機ｅｌ表示装置

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EP0270243A1 (fr) * 1986-11-07 1988-06-08 Chisso Corporation Composés optiquement actifs
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DE2333534A1 (de) * 1972-07-03 1974-01-24 Eastman Kodak Co Verfahren zur herstellung einer nematischen, fluessig-kristallinen mischung
DE2701591A1 (de) * 1977-01-15 1978-07-27 Merck Patent Gmbh Hexahydroterphenylderivate
EP0270243A1 (fr) * 1986-11-07 1988-06-08 Chisso Corporation Composés optiquement actifs
EP0431934A2 (fr) * 1989-12-06 1991-06-12 ECP ENICHEM POLIMERI S.r.l. Mélanges de cristaux liquides pyramidaux orientés longitudinalement et procédé pour leur préparation

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DAVID M. COLLARD: "Structure-property relationships for the thermal phase behavior of dicotic liquid crystals: the effect of branching and unsaturation in the side chains of disklike molecules", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 113, no. 23, 1991, WASHINGTON, DC US, pages 8577 - 8583 *
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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996024647A1 (fr) * 1995-02-06 1996-08-15 Merck Patent Gmbh Composes mesogeniques bireactifs et intermediaires associes
RU2189281C2 (ru) * 1996-04-19 2002-09-20 Берингер Ингельхайм Фарма Кг Двухкамерный контейнер для дозируемых аэрозолей, не содержащих пропеллента
WO1998047979A1 (fr) * 1997-04-22 1998-10-29 Basf Aktiengesellschaft Procede de preparation de composes polymerisables a cristaux liquides
US6695977B2 (en) 2000-12-11 2004-02-24 Basf Aktiengesellschaft Use of chiral, uncharged metal compounds as dopants for liquid-crystalline materials
US7264749B2 (en) 2002-04-29 2007-09-04 Basf Aktiengesellschaft Alkyne compounds
US7258902B2 (en) 2002-07-01 2007-08-21 Basf Aktiengesellschaft Chiral 3,4-dihydro-2H-pyran compounds
US8608977B2 (en) 2008-06-17 2013-12-17 Basf Se Polymerizable chiral compounds comprising 2,6-naphthyl and isomannitol units, and use thereof as chiral dopants
JP2014198813A (ja) * 2012-09-25 2014-10-23 富士フイルム株式会社 液晶組成物およびその製造方法ならびにフィルム
WO2014050426A1 (fr) * 2012-09-25 2014-04-03 富士フイルム株式会社 Composition de cristaux liquides, procédé de production de la composition, et film associé
KR20150045479A (ko) 2012-09-25 2015-04-28 후지필름 가부시키가이샤 액정 조성물 및 그 제조 방법 그리고 필름
US9464228B2 (en) 2012-09-25 2016-10-11 Fujifilm Corporation Liquid crystal composition, method for manufacturing the same, and film
JP2016510820A (ja) * 2013-10-01 2016-04-11 エルジー・ケム・リミテッド 液晶組成物
WO2019141833A1 (fr) 2018-01-22 2019-07-25 Merck Patent Gmbh Matériaux diélectriques
US11959007B2 (en) 2018-01-22 2024-04-16 Merck Patent Gmbh Dielectric materials
WO2020078938A1 (fr) 2018-10-18 2020-04-23 Merck Patent Gmbh Matériaux copolymères diélectriques
WO2020078939A1 (fr) 2018-10-18 2020-04-23 Merck Patent Gmbh Matériaux copolymères diélectriques
US11834598B2 (en) 2018-10-18 2023-12-05 Merck Patent Gmbh Dielectric copolymer materials
US11999893B2 (en) 2018-10-18 2024-06-04 Merck Patent Gmbh Dielectric copolymer materials
WO2025061815A1 (fr) 2023-09-22 2025-03-27 Merck Patent Gmbh Matériaux de copolymère diélectrique

Also Published As

Publication number Publication date
EP0773980A1 (fr) 1997-05-21
KR970704855A (ko) 1997-09-06
DE4427766A1 (de) 1996-02-08
CN1158142A (zh) 1997-08-27
JPH10503541A (ja) 1998-03-31

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