DD289524A5 - LIQUID CRYSTALLINE CYCLOPROPYL ALKYL OR ALKENYL HETEROCYCLES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN LIQUID CRYSTALLINE MIXTURES - Google Patents
LIQUID CRYSTALLINE CYCLOPROPYL ALKYL OR ALKENYL HETEROCYCLES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN LIQUID CRYSTALLINE MIXTURES Download PDFInfo
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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Abstract
Description
/N "Ti/ N "Ti
3. Verwendung der Cyclopropyl- oder alkenyl-Heterocyclen der allgemeinen Formel (I) nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß sie als Komponente in Flüssigkeitsmischungen eingesetzt werden.3. Use of the cyclopropyl or alkenyl heterocycles of the general formula (I) according to claim 1 or 2, characterized in that they are used as a component in liquid mixtures.
4. Verwendung nach Anspruch 3, dadurch gekennzeichnet, daß die Flüssigkristallmischung nematisch, insbesondere chiral-nematisch ist.4. Use according to claim 3, characterized in that the liquid-crystal mixture is nematic, in particular chiral nematic.
5. Verwendung nach Anspruch 3, dadurch gekennzeichnet, daß die Flüssigkristallmischung smektisch, insbesondere chiral-smektisch, bevorzugt ferroelektrisch ist.5. Use according to claim 3, characterized in that the liquid-crystal mixture is smectic, in particular chiral-smectic, preferably ferroelectric.
6. Flüssigkristalline Mischung, dadurch gekennzeichnet, daß sie mindestens einen Cyclopropylalkyl- oder -alkenyl-Heterocyclus der allgemeinen Formel (I) nach Anspruch 1 oder 2 enthält.6. A liquid-crystalline mixture, characterized in that it contains at least one cyclopropylalkyl or alkenyl heterocycle of the general formula (I) according to claim 1 or 2.
Anwendungsgebiet der ErfindungField of application of the invention
Die Erfindung betrifft Verfahren zur Herstellung flüssigkristalliner Cyclopropylalkyl- oder -alkenyl-Heterocyclen und ihre Verwendung in flüssigkristallinen Mischungen.The invention relates to processes for the preparation of liquid-crystalline cyclopropylalkyl or alkenyl heterocycles and their use in liquid-crystalline mixtures.
Charakteristik des bekannten Standes der TechnikCharacteristic of the known state of the art
Die ungewöhnliche Kombination von anisotropem und fluidem Verhalten der Flüssigkristalle hat zu ihrer Verwendung in einer Vielzahl von elektrooptischen Schalt- und Anzeigevorrichtungen geführt. Dabei können ihre elektrischen, magnetischen, elastischen und/oder thermischen Eigenschaften zu Orientierungsänderungen benutzt werden. Optische Effekte lassen sich dann beispielsweise mit Hilfe der Doppelbrechung, der Einlagerung dichroitisch absorbierender Farbstoffmoleküle !„guest-host mode") oder der Lichtstreuung erzielen.The unusual combination of anisotropic and fluid behavior of the liquid crystals has led to their use in a variety of electro-optical switching and display devices. Their electrical, magnetic, elastic and / or thermal properties can be used for orientation changes. Optical effects can then be achieved, for example, with the aid of birefringence, the incorporation of dichroic dye molecules ("guest-host mode") or light scattering.
Zur Erfüllung der ständig steigenden Praxisanforderungen auf den verschiedenen Anwendungsgebieten besteht laufend ein Bedarf an neuem verbesserten Flüssigkristall („liquid crystal")-Mischungen und somit auch an einer Vielzahl mesogoner Verbindungen unterschiedlichster Struktur. Dies gilt sowohl für die Gebiete, bei denen nematische LC-Phasen (z. B. TN = „twisted nematic", ΤΓΝ = „supertwisted nematic", SBE = „suportwisted birefringence effect", ECB » „electrically birefringence") verwendet werden, als auch für solche mit smoktischen LC-Phasen (z. B. ferroelektrische, clektrokline). Viele der für LC-Mischungen geeigneten Verbindungen lassen sich durch ein Aufbauprinzip (Bauschema) beschreiben (siehe z.B. J. Am. Chem. Soc. 108,4736 [19861, Struktur I; Science 231,350 [1986|, Fig. 1 A; J. Am. Chem. Soc. 108,5210 (1986), Fig.3), bei dem Kerne aus cyclischen Verbindungen - Aromaten, Heteroaromaten, aber auch gesättigte Ringsysteme - mit geradkettigen oder in der Kette durch kleine Gruppen (z. B. Methyl, Chlor) substituierten und somit verzweigten Alkylseitenketten verknüpft sind. 'In order to meet the ever increasing practical demands in the various fields of application, there is a constant demand for new improved liquid crystal mixtures and thus also for a large number of mesogonous compounds of various structures, including those in which nematic LC phases are involved (eg TN = "twisted nematic", ΤΓΝ = "supertwisted nematic", SBE = "suportwisted birefringence effect", ECB "" electrically birefringence "), as well as for those with smoktic LC phases (e.g. Many of the compounds suitable for LC mixtures can be described by a structural principle (construction scheme) (see, for example, J. Am. Chem. Soc., 108, 4736 [19861, structure I, Science 231, 350 [1986], FIG 1 A, J. Am. Chem. Soc., 108, 5210 (1986), Fig. 3), in which cores of cyclic compounds - aromatics, heteroaromatics, but also saturated ring systems - with straight-chain or in the chain du small groups (eg. As methyl, chlorine) substituted and thus branched alkyl side chains are linked. '
Verbindungen, die eine terminal-cyclopropyl-substituierte Alkylkette als Teilstrukturelement aufweisen, sind z. B. aus den US-A 3948961,3966,969 und 4014922 (Henrick et al.) bekannt. Die Verbindungen sollen als Insektizide geeignet sein, über flüssigkristallines Verhalten wird nicht berichtet. Die in diesen Veröffentlichungen aufgeführten Verbindungen unterscheiden sich von den nachfolgend definierten insbesondere dadurch, daß sie mit dem Molekülrest immer über eine Esterfunktion verknüpft sind und in diesem Molekülrest zwar aromatische, aber keine heteroaromatischen Ringsysteme aufweisen, In der EP-A 0 244129 werden 2,2-Dimethylcyclopropan-Derivate beschrieben, die optisch-aktiv sind und über eine -CO-O-CH]-, O-CO- oder-CHj-Rrücke (am rechten Ende des jeweiligen Brückenglieds befindet sich der Cyclopropylring) mit einem der bekannten mesogenen Reste verbunden sind. Diese Verbindungen sollen als Komponenten für ferroelektrische LC-Mischungen (spontane Polarisation bis zu 11 nC/cm2) geeignet sein.Compounds which have a terminal cyclopropyl-substituted alkyl chain as a partial structural element are, for. From US-A-3,948,961, 3,966,969 and 4,014,922 (Henrick et al.). The compounds should be suitable as insecticides, liquid crystalline behavior is not reported. The compounds listed in these publications differ from those defined below in particular in that they are always linked to the molecule radical via an ester function and indeed have aromatic but not heteroaromatic ring systems in this molecular radical. In EP-A 0 244129, 2,2 -Dimethylcyclopropan derivatives described which are optically active and via a -CO-O-CH] -, O-CO- or CHj-Rue (at the right end of the respective bridge member is the cyclopropyl ring) with one of the known mesogenic radicals are connected. These compounds should be suitable as components for LC ferroelectric mixtures (spontaneous polarization up to 11 nC / cm 2 ).
Ziel der ErfindungObject of the invention
Mit der Erfindung wird ein Verfahren zur Herstellung neuer flüssigkristalliner Cyclopropylalkyl- oder -alkenyl-Heterocyclen bereitgestellt, die chemisch- photochemisch und thermisch stabil sind und über eine gute Mischungskompatibilität verfügen.The invention provides a process for the preparation of novel liquid-crystalline cyclopropylalkyl or alkenyl heterocycles which are chemically photochemically and thermally stable and have good compatibility with mixtures.
Darlegung des Wesens der Erfindung r Explanation of the essence of the invention r
Aufgabe der vorliegenden Erfindung ist es, neue mesogene Verbindungen zur Verfügung zu stellen, die mit vielen anderen Komponenten zu unterschiedlichsten LC-Mischungen kombiniert werden können. Die nachstehend definierten Verbindungen lösen diese Aufgabe: Flüssigkristalline Cyclopropylalkyl- oder -alkenyl-Heterocyclen der allgemeinen Formel (I)The object of the present invention is to provide novel mesogenic compounds which can be combined with many other components to form a wide variety of LC mixtures. The compounds defined below solve this problem: liquid-crystalline cyclopropylalkyl or alkenyl heterocycles of the general formula (I)
R y\. R N/V*R y \. RN / V *
in der bedeuten:in which mean
R' geradkettiges oder verzweigtes (mit oder ohne asymmetrisches C-Atom) Alkyl oder Alkenyl mit 2 bisR 'is straight-chain or branched (with or without asymmetric carbon atom) alkyl or alkenyl with 2 to
16 C-Atomen, wobei auch eine oderzweinicht-benachbarte-CHj-Gruppendurch-O-,-S-,-CO-,-CO-O-, -O-CO-oder-O-CO-O- ersetzt sein können und wobei auch H durch F ersetzt sein kann, odor einer der nachfolgenden Re^ .e16 C atoms, wherein one or two adjacent CHj groups may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, and where also H can be replaced by F, or one of the following formulas
R2-C-C0-0 R?wi__^-C0-0 R-T^ ^^CO-OR2-C-C0-0 R? Wi __ ^ - C0-0 R -T ^ ^^ CO-O
Cl R5 R O"Cl R 5 R O "
HHHHHH
r2_c_o_CO R2-C-C0-0 R2-C-CH2-0r2_c_o_CO R2-C-R 2 -C-C0-0 CH2-0
♦i *> *'♦ i *> * '
CN P ClCN P Cl
R2-C-CH2-CH2-0 r3 R 2 -C-CH 2 -CH 2 -O r3
Cl R4 GCl R 4 G
A1, A2, A3 gieich oder verschieden 1,4-Phenylen, trans-1,4-Cyclohexylen, Pyrazin-2,5-diyl, Pyridazin-3,6-diyl,A 1 , A 2 , A 3 or different 1,4-phenylene, trans-1,4-cyclohexylene, pyrazine-2,5-diyl, pyridazine-3,6-diyl,
Pyridin-2,5-diyl, Pyrimidin-2,5-diyl, (1,3,4)-Thiadiazol-2,5-diyl M1, M2 gleich oder verschieden CO-0,0-CO, CO-S, S-CO, CH2-0,0-CH2 Pyridine-2,5-diyl, pyrimidine-2,5-diyl, (1,3,4) -thiadiazole-2,5-diyl M 1 , M 2 are the same or different CO-0,0-CO, CO-S , S-CO, CH 2 -0.0-CH 2
G geradkettiges oder verzweigtes Alkylen mit 1 bis 16 C-Atomen oder Alkenylen mit 2 bis 16 C-Atomen, bei demG is straight-chain or branched alkylene having 1 to 16 C atoms or alkenylene having 2 to 16 C atoms, in which
auch eine oder zwei nicht-benachbarte -CHj-Gruppen durch -0-,-S-, -0-CO-, -CO-O-, -S-CO- oder-CO-S-ersetzt sein könnenalso one or two non-adjacent -CHj groups may be replaced by -O-, -S-, -O-CO-, -CO-O-, -S-CO- or -CO-S-
R2, R3, R4 H oder geradkettigos oder verzweigtes Alkyl mit 1 bis 16 odor Alkenyl mit 2 bis 16 C-Atomen, bei dem auch eineR 2 , R 3 , R 4 H or geradkettigos or branched alkyl having 1 to 16 odor alkenyl having 2 to 16 carbon atoms, in which also a
-CHj-Gruppe durch-0-,-CO-O-oder-0-CO-ersetzt sein kann-CHj group can be replaced by -0 -, -CO-O or -0-CO
j,k, I, m, η Null oder 1j, k, I, m, η is zero or 1
mit folgenden Maßgaben: a) j + I + η = 2 oder 3, b) eine der Gruppierungen A1, A', A11 ist nicht 1,4-Phenylenodortrans-1,4-Cyclohexylen, und c) wenn R2 = H sind R3 und R4 nicht gleichzeitig CH3 und G ist nicht CO-O-CHj, 0-CO oder OCHj. Bevorzugt sind solche Verbindungen, bei denen in der allgemeinen Formel (I) die Gruppierung (-AMjl-M'lkf-A'lK-M'lmi-A^n-bedeutet:with the following provisos: a) j + I + η = 2 or 3, b) one of the groupings A 1 , A ', A 11 is not 1,4-phenylenedoyltrans-1,4-cyclohexylene, and c) when R 2 = H, R 3 and R 4 are not simultaneously CH 3 and G is not CO-O-CHj, O-CO or OCHj. Preference is given to those compounds in which, in the general formula (I), the grouping (-AMjl-M'lkf-A'lK-M'lmi-A ^ n-means:
Die neuen Cyclopropylalkyl- oder -alkenyl-Heterocyclen sind chomisch, photochemisch und thermisch stabil und verfügen über eine gute Mischungskompatibilität. Im Vergleich zu den entsprechenden n-Alkyl-Homologen besitzen sie oftmals einen niedrigeren Wert für die optische Anisotropie Δη und führen in Mischungen häufig zu niedrigeren Schmelzpunkten.The new cyclopropylalkyl or alkenyl heterocycles are chomically, photochemically and thermally stable and have a good compatibility with mixtures. In comparison to the corresponding n-alkyl homologs, they often have a lower value for the optical anisotropy Δη and often lead to lower melting points in mixtures.
Eine weitere Lösung der gestellten Aufgabe ist eine Flüssigkristal1 Mischung mit einem Gehalt an mindestens einer flüssigkristallinen Verbindung, die als flüssigkristalline Verbindung mindestens eine Verbindung der allgemeinen Formel (I) enthält.Another solution of the problem is a Flüssigkristal 1 mixture containing at least one liquid crystal compound containing at least one compound of the general formula (I) as the liquid crystalline compound.
Die Fluss, jkristall-Mischungen bestehen aus 2 bis 20, vorzugsweise 2 bis 15 Komponenten, darunter mindestens einer der erfindungsgemäß beanspruchten Verbindungen. Die anderen Bestandteile werden vorzugsweise ausgewählt aus den bekannten Verbindungen mit nematischen, cholesterischen und/oder geneigt-smektischen Phasen, dazu gehören beispielsweise Schiffsche Basen, Biphenyle, Terphenyle, Phenylcyclohexane, Cyclohexylbiphenyle, Pyrimidine, Zimtsäureester, Choiesterinester, verschieden überbrückte, terminai-polare mehrkernige Ester von p-Alkylbenzoesäuren. Im allgemeinen liegen die im Handel erhältlichen Flü jsigkristall-Mischungen bereits vor der Zugabe der erfindungsgemäßen Verbindung(en) als Gemische verschiedenster Komponenten vor, von denen mindestens eine mesogen ist, d. h. als Verbindung, in derivatisierter Form oder im Gemisch mit bestimmten Cokomponenten eine Flüssigkristall-Phase zeigt [= mindestens eine enantiotrope (Klärtemperatur > Schmelztemperatur) odermonotrope (Klärtemperatur < Schmelztemperatur) Mesophasenbildung erwartenThe flow, jkristall mixtures consist of 2 to 20, preferably 2 to 15 components, including at least one of the compounds claimed according to the invention. The other ingredients are preferably selected from the known compounds having nematic, cholesteric and / or tilted smectic phases, including, for example, Schiff bases, biphenyls, terphenyls, phenylcyclohexanes, cyclohexylbiphenyls, pyrimidines, cinnamic acid esters, cholesterol esters, various bridged, terminai-polar polynuclear esters of p-alkylbenzoic acids. In general, the commercially available liquid crystal mixtures are already present before the addition of the compound (s) according to the invention as mixtures of various components, of which at least one is mesogenic, ie. H. as a compound, in derivatized form or in admixture with certain co-components a liquid crystal phase shows [= at least one enantiotropic (clearing temperature> melting temperature) or monotropic (clearing temperature <melting temperature) mesophase formation expect
läßt].leaves].
Von der oder den erfindungsgemäßen Verbindung(en) enthalten die Flüssigkristall-Mischungen im allgemeinen 0,01 bisOf the compound (s) of the invention, the liquid crystal mixtures generally contain from 0.01 to
70Gew.-%, insbesondere 0,05 bis 50Gew-%.70% by weight, in particular 0.05 to 50% by weight.
Die erfindungsgemäßen Heterocyclen können nach an sich bekannten Standardreaktionen aus mesogenen monofunktionellreaktionsfähigen Grundkörpern durch Verknüpfung mit ebenfalls monofunktionell-reaktionsfähigen Cyclopropylalkyl-Verbindungen hergestellt werden, wobei die Synthese beider Komponenten als bekannt vorausgesetzt werden kann.The heterocycles according to the invention can be prepared by standard reactions known per se from mesogenic monofunctionally reactive basic bodies by linking with likewise monofunctionally reactive cyclopropylalkyl compounds, wherein the synthesis of both components can be assumed to be known.
So können beispielsweise mesogene Hydroxy- oder Mercaptoverbindungen mit Cyclopropyl-alkanolen in Anwesenheit von Triphenylphosphin/Azodicarbonsäurediester (Mitsunobu-Reaktion, z. B. in J. Chem. Soc. Perkin Trans. 1975,461) verknüpft werden. Es können auch die separat oder intermediär erzeugten Alkali- oder Erdalkalisalze dieser mesogenen Hydroxy- oder Mercapto-Verbindungen mit Halogen-, Toluolsulfonyloxy- oder Methylsulfonyloxy-cyclopropylalkyl-Verbindungen umgesetzt werden (Williamson-Reaktion,z.B. in Patai, The Chemistry of the Ether Linkage, Interscience Publishers, New York 1967,Thus, for example, mesogenic hydroxy or mercapto compounds can be linked to cyclopropylalkanols in the presence of triphenylphosphine / azodicarboxylic acid diester (Mitsunobu reaction, eg in J. Chem. Soc. Perkin Trans. 1975, 461). It is also possible to react the alkali metal or alkaline earth metal salts of these mesogenic hydroxyl or mercapto compounds, prepared either separately or as intermediates, with halogenated, toluenesulfonyloxy or methylsulfonyloxy-cyclopropylalkyl compounds (Williamson reaction, for example in Patai, The Chemistry of the Ether Linkage. Interscience Publishers, New York 1967,
S. 446-468).P. 446-468).
Es können aber auch mesogene Carbonsäuren mit Cyclopropylalkoholen unter Kondensationsbedingungen (z. B. in March, Advanced Organic Chemistry, 2nd Ed., McGraw-Hill Kogakuska Ltd., Tokyo 1977, S.363-365) umgesetzt werden. In gleicher Weise ist dies auch mit mesogenen Hydroxy- oder Mercapto-Verbindungen und Cyclopropyl-alkansäureo möglich.However, it is also possible to react mesogenic carboxylic acids with cyclopropyl alcohols under condensation conditions (eg in March, Advanced Organic Chemistry, 2nd Ed., McGraw-Hill Kogakuska Ltd., Tokyo 1977, pp. 363-365). In the same way, this is also possible with mesogenic hydroxy or mercapto compounds and cyclopropyl-alkanoic acid.
Die zur Verknüpfung erforderlichen Cyclopropylalky !-Verbindungen werden nach Standardmethoden hergestellt, es wird dazu auf die vorstehend erwähnten Veröffentlichungen (US-A) von Henrick et al. verwiesen.The cyclopropylalky! Compounds required for linking are prepared by standard methods. Reference is made to the abovementioned publications (US-A) by Henrick et al. directed.
Ausführungsbeispieleembodiments
In den nachfolgenden Beispielen verhalten sich Gew.-Teile zu Vol.-Teilen wie kg zu ιIn the following examples, parts by weight to vol. Parts such as kg behave to ι
Beispiel 1 5-Heptyloxy-2-I4-(9-cyclopropyl-nonyl)oxy-phenyl)-pyrimidinExample 1 5-Heptyloxy-2-I4- (9-cyclopropyl-nonyl) oxy-phenyl) -pyrimidine
Zur Lösung von 0,52Vol.-Teilen Diethylazodicarboxylat und 0,85Gew.-Teilen Triphonylphosphin· in 20Vol.-Teilen Tetrahydrofuran werden 0,5Gew.-Teile 9-Cyclopropyl-nonanol und 0,95Gew.-Teile 4-(5-Heptyloxypyrimidin-2-yl)-phenol gegeben. Nach einer Reaktionszeit von 24 h wird das Lösemittel abdestilliert und der Rückstand chromatogi aphisch (SiO2/ CH]CI2) gereinigt. Nach Uinkristallisation aus 2-Propanol werden O,52Gew.-Teile farblose Kristalle erhalten. Phasenfolge: K56,4SC71,3SA83,4 N85.1 I0.5 part by weight of 9-cyclopropyl-nonanol and 0.95 part by weight of 4- (5-heptyloxypyrimidine -2-yl) -phenol. After a reaction time of 24 hours, the solvent is distilled off and the residue is purified chromatographically (SiO 2 / CH 2 Cl 2 ). After recrystallization from 2-propanol O, 52Gew.-parts are obtained colorless crystals. Phase sequence: K56.4S C 71.3S A 83.4 N85.1 I
Beispiel 2 5-Hexyl-2-[4-(9-cyclopropyl-nonyl)oxy-phenyl]pyrimidinExample 2 5-Hexyl-2- [4- (9-cyclopropyl-nonyl) oxy-phenyl] pyrimidine
Die nachfolgenden Synthesen werden nach den Angaben des Beispiels 1 mit entsprechender Mengenanpassung durchgeführt. Phasenfolge: K44 NThe following syntheses are carried out according to the procedure of Example 1 with appropriate quantity adjustment. Phase sequence: K44 N
Beispiel 3 S-Octyl^-H-O-cyclopropyl-nonyDoxy-phenyllpyrimidinExample 3 S-Octyl-H-O-cyclopropyl-nony-Doxy-phenyl-pyrimidine
Phasenfolge: K41,3Sc51 SA57,6N60,2ln || 1,616η 11,486Δη = 0,13 (bei45°C, 589nm) Meßmethode: Eine wichtige Kenngröße für die Güte des Kontrastes eines LC-Displays ist die optische Doppelbrechung Δη = η Il - η 1 · η Il bzw. η X sind die Brechungsindices für parallel bzw. senkrecht zum Direktor η polarisiertes Licht. Beide Brechungsindices sind temperatur- und wellenlängenabhängig mit dem Abbo-Refraktometer bestimmbar.Phase sequence: K41,3Sc51 S A 57,6N60,2ln || 1.616η 11.486Δη = 0.13 (at 45 ° C, 589nm) Measuring Method: An important parameter for the quality of the contrast of an LC display is the optical birefringence Δη = η Il-η 1 · η Il or η X are the refractive indices for parallel or perpendicular to the director η polarized light. Both refractive indices can be determined by temperature and wavelength depending on the abbo refractometer.
Beispiel 4 5-Octyloxy-2-[4-(9-cyclopropyl-nonyl)oxy-phenyl]pyrimidinExample 4 5-Octyloxy-2- [4- (9-cyclopropyl-nonyl) oxy-phenyl] pyrimidine
VWV-oVWV-o
Phasenfolge: K69,2 SC75,8 SA90,2 IPhase sequence: K69.2 S C 75.8 S A 90.2 I
Beispiele 5-Nonyl-2-[4-(9-cy~lopropyl-nonyl)oxy-phenyl]pyrimidinExamples 5-nonyl-2- [4- (9-cypropyl-nonyl) oxy-phenyl] pyrimidine
Phasenfolge: K52.8 SC56,8 SA67,21Phase sequence: K52.8 S C 56.8 S A 67.21
Beispiele 5-Decyl-2-(4-(9-cyclopropyl-nonyl)oxy-phenyl]pyrimidinExamples 5-Decyl-2- (4- (9-cyclopropyl-nonyl) oxy-phenyl] pyrimidine
Phasenfolge: K44 SC64,9 SA67,71Phase sequence: K44 S C 64.9 S A 67.71
Beispiel 7 B-Undecyl^-H-O-cyclopropyl-nonyDoxy-phenyllpyrimidinExample 7 B-undecyl-H-O-cyclopropyl-nony-Doxy-phenyl-pyrimidine
Phasenfolge: K48Sc70,2 Sa 71,81Phase sequence: K48S c 70.2 Sa 71.81
Beispiele 5-Und6cyloxy-2-[4-(9-cyclopropyl-nonyl)oxy-phenyll-pyrimidinExamples 5-und6cyloxy-2- [4- (9-cyclopropyl-nonyl) oxy-phenyll-pyrimidine
Phasenfolge: K68SC951Phase sequence: K68S C 951
Beispiel 9 o-Dodecyl^-H-O-cyclopropyl-nonyOoxy-phenyllpyrimidinExample 9 o-Dodecyl-H-O-cyclopropyl-nonyloxy-phenyl-pyrimidine
Phasenfolge: K52SC72,31Phase sequence: K52S C 72.31
Beispiel 10 2-Decylthio-5-[4-(9-cyclopropyl-nonyl)oxy-phenyl]pyrimidinExample 10 2-Decylthio-5- [4- (9-cyclopropyl-nonyl) oxy-phenyl] pyrimidine
Phasenfolge: K67,5 [38 S2 57 Sc 65] IPhase sequence: K67.5 [38 S 2 57 S c 65] I
Beispiel 11 5-(9-Cyclopropyl-nonyl)oxy-2-(4-heptyloxy-phenyl)pyrimidinExample 11 5- (9-Cyclopropyl-nonyl) oxy-2- (4-heptyloxyphenyl) pyrimidine
Phasenfolge: K64.7 Sc 91 IPhase sequence: K64.7 S c 91 I
Beispiel 12 5-(9-Cyclopropyl-nonyl)oxy-2-(4-octyloxy-phenyl)pyrimidinExample 12 5- (9-Cyclopropyl-nonyl) oxy-2- (4-octyloxyphenyl) pyrimidine
Phasenfolge: K63,7 Sc 93,21Phase sequence: K63.7 S c 93.21
Beispiel 13 S-Octyl^-H-^S-fßSJ^-dimethylcyclopropyU-S-methylpentyOoxy-phenyllpyrimidinExample 13 S-Octyl ^ -H- ^ S-fssSJ ^ -dimethylcyclopropyU-S-methylpentyOoxy-phenyllpyrimidine
Phasenfolge: K [-21,5 SA16] 18,51 [a)ls: -5,2 (c = 5, CH2CI2 Meßmethode: Versetzt man ein (nicht-chir .es) Lösemittel mit einer kleinen Menge einer chiralen Verbindung, so wird die Ebene des linear polarisierten Lichts um den (charakteristischen) Winkel α gedreht; dieser Winkel wird wie folgt angegeben: [ajj (c = x, LM), wobei die Symbole folgende Bedeutung haben: χ = Konzentration der Lösung in g/l, LM = Lösemittel, D = 589nm (NaD-Linie), T = Temperatur der Lösung. Der Drehwinkel wird in einem Polarimeter nach 10cm Durchgang des Lichts bestimmt.Phase sequence: K [-21.5 S A 16] 18.51 [a ] s : -5.2 (c = 5, CH 2 Cl 2 Method of measurement: If a (non- chiral) solvent is added with a small amount Quantity of a chiral compound, the plane of the linearly polarized light is rotated by the (characteristic) angle α, this angle is given as follows: [ajj (c = x, LM), where the symbols have the following meaning: χ = concentration of Solution in g / l, LM = solvent, D = 589nm (NaD line), T = temperature of the solution The angle of rotation is determined in a polarimeter after 10 cm of passage of the light.
Beispiel 14 (2S,Example 14 (2S,
Phasenfolge: K (38 Sc 40 SA 44,3] 48,51 Mg6 = -2;0 (c = 4, CH2CI2)Phase sequence: K (38 S c 40 S A 44.3] 48.51 Mg 6 = -2; 0 (c = 4, CH 2 Cl 2 )
Beispiel 15 S-Octyl^-H-ie-cyclopropyl-hexyDoxy-phenyllpyrimidinExample 15 S-Octyl-H-he-cyclopropyl-hexy-Doxy-phenyl-pyrimidine
Phasenfolge: K39 Sc 46 SA50 N 59,51Phase order: K39 S c 46 S A 50 N 59.51
Beispiel 16 5-Decyl-2-[4-(6-cyclopropyl-hexyl)oxy-phenyl)pyrimidinExample 16 5-Decyl-2- [4- (6-cyclopropylhexyl) oxyphenyl) pyrimidine
Phasenfolge: K42 Sc60 SA651Phase sequence: K42 S c 60 S A 651
Beispiel 17 ö-Heptyloxy^-H-lß-cyclopropyl-hexyDoxy-phenyllpyrimidinExample 17 ö-Heptyloxy-H-l, -cyclopropyl-hexy-Doxy-phenyl-pyrimidine
Phasenfolge: K54SC72SA78N88IPhase sequence: K54S C 72S A 78N88I
Beispiel 1." 5-Octyloxy-2-[4-(6-cyclopropyl-hexyl)oxy-phenyl)pyrimidinExample 1. "5-Octyloxy-2- [4- (6-cyclopropylhexyl) oxyphenyl) pyrimidine
hat Sc/SA-Übergang bei 81, SA/N-Übergang bei 89 und Klärpunkt bei 920C.has S c / S A transition at 81, S A / N transition at 89 and clear point at 92 ° C.
Beispiel 19 5-(6-Cyclopropyl-hexyl)oxy-2-(4-nonyloxy-phenyl)pyrimidinExample 19 5- (6-Cyclopropylhexyl) oxy-2- (4-nonyloxyphenyl) pyrimidine
Phasenfolge: K56,5SC79 SA85 N89.51Phase sequence: K56.5S C 79 S A 85 N89.51
Beispiel 20 5-(6-Cyclopropyl-hexyl)oxy-2-(4-undecyioxcy-phenyl)pyrimidinExample 20 5- (6-Cyclopropyl-hexyl) oxy-2- (4-undecycloxyphenyl) pyrimidine
Phasenfolge: K57,5 Sc76,5 SA86,7 N87 IPhase sequence: K57.5 S c 76.5 S A 86.7 N87 I
Beispiel 21 5-(6-Cyclopropyl-hexyl)oxy-2-(4-dodecyloxy-phenyl)pyrimidinExample 21 5- (6-Cyclopropyl-hexyl) oxy-2- (4-dodecyloxyphenyl) pyrimidine
Phasenfolge: K61 SC77 SA871Phase sequence: K61 S C 77 S A 871
trans-2- ( 9-I4-(5-Octyl-pyrimidin-2-yl)phenyloxy]nonyl > -cyclopropancarbonsäureethylesterTrans-2- (9-I4- (5-octyl-pyrimidin-2-yl) -phenyloxy] nonyl> -cyclopropanecarboxylic acid ethyl ester
Phasenfolge: K (11 Sc 36 SA)Phase sequence: K (11 S c 36 S A )
Beispiel 23 5-Octyl-2-I4-(7-cyclopropyl-heptyl)oxy-phonyl]pyrimidinExample 23 5-Octyl-2-I4- (7-cyclopropylheptyl) oxy-phonyl] pyrimidine
Phasenfolge: K33 Sc 45,5 SA 54,6 N58,41Phase sequence: K33 S c 45.5 S A 54.6 N 58.41
Beispiel 24 5-(7-Cyclopropyl-heptyl)oxy-2-(4-nonyloxy-phenyl)pyrimidinExample 24 5- (7-Cyclopropylheptyl) oxy-2- (4-nonyloxyphenyl) pyrimidine
Phasenfolge: K60 Sc 87,9 SA 90,41Phase sequence: K60 S c 87.9 S A 90.41
Beispiel 25 5-(7-Cyclopropyl-heptyl)oxy-2-(4-undecyloxy-phenyl)pyrimidinExample 25 5- (7-Cyclopropylheptyl) oxy-2- (4-undecyloxyphenyl) pyrimidine
Phasenfolge: K53,4 Sc 87,6 SA90,51Phase sequence: K53.4 S c 87.6 S A 90.51
Baispiel 26 5-(7-Cyclopropyl-heptyl)oxy-2-(4-dodecyloxy-phenyl)pyrimidinExample 26 5- (7-Cyclopropyl-heptyl) oxy-2- (4-dodecyloxyphenyl) pyrimidine
Phasenfolge: K67.4 SC88,1 SA90,51Phase sequence: K67.4 S C 88.1 S A 90.51
Beispiel 27 5-Octyloxy-2-[4-(7-cyclopropyl-heptyl)oxy-phenyl]pyrimidinExample 27 5-Octyloxy-2- [4- (7-cyclopropylheptyl) oxy-phenyl] pyrimidine
Phasenfolge: K60 SC78,2 SA90 N90.21Phase sequence: K60 S C 78.2 S A 90 N90.21
Beispiel 28 2-Octylthio-5-[4-(7-cyclopropyl-heptyl)oxy-phenyl)pyrimidinExample 28 2-Octylthio-5- [4- (7-cyclopropylheptyl) oxy-phenyl] pyrimidine
Phasenfolge: K (41 S3 42 SC55,5] 61,6 SA62,21Phase sequence: K (41 S 3 42 S C 55.5] 61.6 S A 62.21
Beispiel 29 5-Octyl-2-|4-(11-cyclopropyl-5-oxa-undecyl)oxy-phenyl)-pyrimidinExample 29 5-Octyl-2- | 4- (11-cyclopropyl-5-oxa-undecyl) oxy-phenyl) -pyrimidine
Phasenfolge: K [16Sc 25,6 N31) 40,91Phase sequence: K [16S c 25.6 N31] 40.91
Beispiel 30 5-(9-Cyclopropyl-nonyl)oxy-2-(4-(trans-4-pentyl-cyclohexyl)-carbonyloxy-phenyllpyrimidinExample 30 5- (9-Cyclopropyl-nonyl) oxy-2- (4- (trans-4-pentyl-cyclohexyl) -carbonyloxy-phenyl-pyrimidine
Phasenfolge: K [76S284,3] 86,5 Sc 129,2 N1791Phase sequence: K [76S 2 84.3] 86.5 S c 129.2 N1791
5-(6-Cyclopropyl-5-oxa-hexyl)oxy-2-(4-nonyloxy-phenyl)-pyrimidin5- (6-cyclopropyl-5-oxa-hexyl) oxy-2- (4-nonyloxy-phenyl) -pyrimidin
Phasenfolge: K (58 SC58,4 N72] 72,41Phase order: K (58 S C 58.4 N72] 72.41
Beispiel 32 5-Octyl-2-(4-(6-cyclopropyl-5-oxa-hexyl)oxy-phenyl|-pyrimidinExample 32 5-Octyl-2- (4- (6-cyclopropyl-5-oxa-hexyl) oxy-phenyl | -pyrimidine
Phasenfolge: K (-4 SC22] 28,5 N40.2 IPhase sequence: K (-4 S C 22] 28.5 N 40.2 I
Beispiel 33 5-(9-Cyclopropyl-nonyl)oxy-2-(4-undecyloxy-phenyl)pyrimidinExample 33 5- (9-Cyclopropyl-nonyl) oxy-2- (4-undecyloxyphenyl) pyrimidine
Phasenfolge: K55 Sc 94,21Phase sequence: K55 S c 94,21
Beispiel 34 5-(9-Cyclopropyl-nonyl)oxy-2-(4-dodecyloxy-phenyl)pyrimidinExample 34 5- (9-Cyclopropyl-nonyl) oxy-2- (4-dodecyloxyphenyl) pyrimidine
Phasenfolge: K63SC 94,2 IPhase sequence: K63S C 94.2 I
Beispiel 35 S-Decyl^-M-^-cyclopropyl-heptyDoxy-phenyllpyrimidinExample 35 S-Decyl ^ -M - ^ - cyclopropylheptyDoxy-phenyllpyrimidine
Phasenfolge: K40,3Sc61 SA66,2!Phase sequence: K40.3S c 61 S A 66.2!
Beispiel 36 5-(7-Cyclopropyl-heplyl)oxy-2-(4-octyloxy-phenyl)pyrimidinExample 36 5- (7-Cyclopropyl-heplyl) oxy-2- (4-octyloxyphenyl) pyrimidine
Phasenfolge: K56,5 3C89,1 SA91,6IPhase sequence: K56.5 3 C 89.1 S A 91.6 I
Beispiel 37 5-Dodecyl-2-[4-(11-cyclopropyl-undecyl)oxy-phenyl)pyrimidinExample 37 5-Dodecyl-2- [4- (11-cyclopropyl-undecyl) oxy-phenyl) pyrimidine
Phasenfolge: K72 Sc 95,31Phase sequence: K72 S c 95.31
Beispiel 38 5-Decyl-2-|4-(11-cyclopropyl-undecyl)oxy-phenyl]pyrimidinExample 38 5-Decyl-2- | 4- (11-cyclopropyl-undecyl) oxy-phenyl] pyrimidine
Phasenfolge: K51.7 SC65,6 SA67,3 IPhase sequence: K51.7 S C 65.6 S A 67.3 I
Beispiel 39 5-(7-Cyclopropyl-heptyl)oxy-2-(4-hexyloxy-phenyl)pyrimidinExample 39 5- (7-Cyclopropylheptyl) oxy-2- (4-hexyloxyphenyl) pyrimidine
Phasenfolge: K51.8 Sc 86,5 SA89,6 N 89,8 IPhase sequence: K51.8 S c 86.5 S A 89.6 N 89.8 I
Beispiel 40 5-Octyl-2-[4-(8-cyclopropyl-octyl)oxy-phenyllpyrimidinExample 40 5-Octyl-2- [4- (8-cyclopropyl-octyl) oxy-phenyl-pyrimidine
Phasenfolge:K35Sc51,5SA55,5N61,2lPhase sequence: K35S c 51.5S A 55.5N61.2l
Beispiel 41 5-(8-Cyclopropyl-octyl)oxy-2-(4-nonyloxy-phenyl)pyrimidinExample 41 5- (8-Cyclopropyl-octyl) oxy-2- (4-nonyloxyphenyl) pyrimidine
Phasenfolge: K56,2 SC91,8 SA931Phase sequence: K56.2 S C 91.8 S A 931
Betspiel 42 5-(8-Cyclopropyl-octyl)oxy-2-(4-undecyloxy-phonyl)pyrimidinBetspiel 42 5- (8-Cyclopropyl-octyl) oxy-2- (4-undecyloxy-phonyl) pyrimidine
Phasenfolge: K53,6SC92,3SA93,11Phase sequence: K53.6S C 92.3S A 93.11
5-(8-Cyclopropyl-octyl)oxyj2-(4-dodecyloxy-phenyl)pyrimidin5- (8-cyclopropyl-octyl) oxyj2- (4-dodecyloxy-phenyl) pyrimidine
Phasenfolge: K54,9SC92,3SA93IPhase sequence: K54,9S C 92,3S A 93I
Beispiel 44 5-Octyloxy-2-[4-(8-cyclopropyl-octyl)oxy-phenyl]pyrimidinExample 44 5-octyloxy-2- [4- (8-cyclopropyl-octyl) oxy-phenyl] pyrimidine
Phasenfolge: K51 SC79,2SA91 N91.6IPhase sequence: K51 S C 79.2 S A 91 N91.6I
2-Octylthio-5-|4-(8-cyolopropyl-octyl)oxy-pheriyl)pyrimidin2-octylthio-5- | 4- (8-cyolopropyl-octyl) oxy-pheriyl) pyrimidine
Phasenfolge: K [42,2 SC59,5 SA62,5| 64,7 IPhase sequence: K [42.2 S C 59.5 S A 62.5 | 64.7 l
Beispiel 46 5-(8-Cyclopropyl-octyl)oxy-2-(4-hexyloxy-phenyl)pyrimidinExample 46 5- (8-Cyclopropyl-octyl) oxy-2- (4-hexyloxyphenyl) pyrimidine
Phasenfolge: K54.1 SC88,2 SA90,81Phase sequence: K54.1 S C 88.2 S A 90.81
Beispiel 47 5-(8-Cyclopropyl-octyl)oxy-2-(4-octyloxy-phenyl)pyrimidinExample 47 5- (8-Cyclopropyl-octyl) oxy-2- (4-octyloxyphenyl) pyrimidine
Phasenfolge: K56,4 SC91,7 SA92,9!Phase sequence: K56.4 S C 91.7 S A 92.9!
Beispiel 48 5-(11-Cyclopropyl-undecyl)oxy-2-(4-dodecyloxy-phenyl)pyrimidinExample 48 5- (11-Cyclopropyl-undecyl) oxy-2- (4-dodecyloxyphenyl) pyrimidine
Phasenfolge: K54,6SC73,81Phase sequence: K54.6S C 73.81
Beispiel 49 3-(9-Cyclopropyl-nonyl)oxy-6-(4-octyloxy-phenyl)pyrida2inExample 49 3- (9-Cyclopropyl-nonyl) oxy-6- (4-octyloxyphenyl) pyrida2in
Phasenfolge: K [82 S0 95,7) 1001Phase sequence: K [82 S 0 95.7] 1001
Beispiel 50 5-Decyl-2-[4-(8-cyclopropyl-octyl)oxy-phenyl]pyrimidinExample 50 5-Decyl-2- [4- (8-cyclopropyl-octyl) oxy-phenyl] pyrimidine
Phasenfolge: K42.3 SC62,5 SA67,21Phase sequence: K42.3 S C 62.5 S A 67.21
Beispiel 51 B-Octyloxy^-H-teyclopropylmethyDoxy-phenyllpyrimidinExample 51 B-Octyloxy-H-tecyclopropylmethyDoxy-phenyl-pyrimidine
Phasenfolge: K59 SC62,8 SA72,9 N73,61Phase sequence: K59 S C 62.8 S A 72.9 N73.61
Beispiel 52 2-(9-Cyclopropyl-nonyl)oxy-5-[4-(9-cyclopropyl-nonyloxy)-phenyl|pyrimidinExample 52 2- (9-Cyclopropyl-nonyl) oxy-5- [4- (9-cyclopropyl-nonyloxy) -phenyl-pyrimidine
Phasenfolge: K [79,3 Se79,5] 89,41Phase sequence: K [79.3 S e 79.5] 89.41
Beispiel 53 2-(9-Cyclopropyl-nonyl)oxy-5-(4-decyloxyphenyl)pyrimidinExample 53 2- (9-Cyclopropyl-nonyl) oxy-5- (4-decyloxyphenyl) pyrimidine
Phasenfolge: K (70 S3 70,55 SC84 SA87,6]Phase sequence: K (70 S 3 70.55 S C 84 S A 87.6]
Beispiel 54 trans-2-Hexyl-cyclopropancarbonsäure-[4-(2-octylthiopyrimidin-5-yl]phenyl-esterExample 54 trans-2-hexyl-cyclopropanecarboxylic acid [4- (2-octylthiopyrimidin-5-yl] phenyl ester
Phasenfolge: K40,51Phase sequence: K40.51
Beispiel 55 5-{8-Cyclopropyl-octyl)oxy-2-(4-decyloxy-phenyl)pyrimidinExample 55 5- {8-Cyclopropyl-octyl) oxy-2- (4-decyloxy-phenyl) pyrimidine
Phasenfolge: K58,5 SC91,6 SA921Phase sequence: K58.5 S C 91.6 S A 921
Beispiel 56 5-(8-Cyclopropyl-octyl)oxy-2-[4-butyloxy-phenyl)pyrimidinExample 56 5- (8-Cyclopropyl-octyl) oxy-2- [4-butyloxyphenyl) pyrimidine
Phasenfolge: K55,4SC81 SA87,8IPhase sequence: K55,4S C 81 S A 87,8I
Beispiel 57 (R)-[4-{2-(9-Cyclopropyl-nonyl)oxy-pyrimidin-5-yl)]phenyl-2,2-dimethyl-1,3-dioxolan-4-carbonsäureesterExample 57 (R) - [4- {2- (9-Cyclopropyl-nonyl) oxy-pyrimidin-5-yl)] -phenyl-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid ester
Phasenfolge: K841Phase sequence: K841
°: + 5,46 (C = 2, CH2CI2)°: + 5.46 (C = 2, CH 2 Cl 2 )
Beispiel 58 (25,35)-[4-(2-(9-Cyclopropyl-nonyl)oxy-pyrimidin-5-yl)l-phenyl-2-chlor-3-methyl-pentanoatExample 58 (25,35) - [4- (2- (9-Cyclopropyl-nonyl) oxy-pyrimidin-5-yl) -l-phenyl-2-chloro-3-methylpentanoate
Phasenfolge: K811 [a]§°: + 1,2 (C = 2, CH2CI2)Phase sequence: K811 [a] § °: + 1,2 (C = 2, CH 2 CI 2 )
Beispiel 59 5-Octyl-2-[4-(4-cyclopropyl-butyl)oxy-phenyllpyrimidinExample 59 5-Octyl-2- [4- (4-cyclopropylbutyl) oxy-phenyllpyrimidine
Phasenfolge: K [16 SC37 SA43,6] 45 N561Phase sequence: K [16 S C 37 S A 43.6] 45 N561
Beispiel 60 5-Decyl-2-[4-(4-cyclopropyl-butyl)oxy-phenyl]pyrimidinExample 60 5-Decyl-2- [4- (4-cyclopropyl-butyl) oxy-phenyl] pyrimidine
Phasenfolge: K [47 Sc 48] 64 N881Phase sequence: K [47 S c 48] 64 N881
Beispiel 61 5-(4-Cylopropyl-butyl)oxy-2-(4-hexyloxy-phenyl)pyrimidinExample 61 5- (4-Cylopropyl-butyl) oxy-2- (4-hexyloxyphenyl) pyrimidine
Phasenfolge: K [47 Sc 48] 64 N881Phase sequence: K [47 S c 48] 64 N881
Beispiel 62 ö-Octyl^-M-iS-cyclopropyl-pentyDoxy-phenyllpyrimidinExample 62 δ-Octyl-M-iS-cyclopropyl-pentydoxy-phenyl-pyrimidine
Phasenfolge: K [18 Sc 34] 38 SA51 NPhase sequence: K [18 S c 34] 38 S A 51 N
Beispiel 63 B-Decyl^-H-lB-cyclopropyl-pentylloxy-phenyllpyrimidinExample 63 B-Decyl-H-lB-cyclopropyl-pentyl-oxy-phenyl-pyrimidine
Phasenfolge: K48 SC53 SA621Phase sequence: K48 S C 53 S A 621
Beispiel 64 5-(5-Cyclopropyl-pentyl)oxy-2-(4-hexyloxy-phenyl)pyrimidinExample 64 5- (5-Cyclopropyl-pentyl) oxy-2- (4-hexyloxyphenyl) pyrimidine
Phasenfolge: K53SC73 SA75 N861Phase sequence: K53S C 73 S A 75 N861
Beispiel 65 5-(7-Cyclopropyl-heptyl)oxy-2-(4-decyloxy-phenyl)pyrimidinExample 65 5- (7-Cyclopropylheptyl) oxy-2- (4-decyloxy-phenyl) pyrimidine
N/N /
K)^yK) ^ y
Phasenfolge: K55/7 Sc90 SA92,51Phase sequence: K55 / 7 S c 90 S A 92.51
Beispieles trans-2-Hexyl-Cyclopropylcarbonsäure-[4-(5-octyl-pyrimidin-2-yl]phenyl-esterExample trans-2-hexyl-cyclopropylcarboxylic acid [4- (5-octyl-pyrimidin-2-yl] -phenyl ester
Phasenfolge: K44IPhase sequence: K44I
Beispiel 67 (2R,3R)-3-Propyl-oxiran-2-carbonsäure-[4-(2-(9-cyclopropylnonyl)oxy-pyrimidin-5-yl)]phenyl-esterExample 67 (2R, 3R) -3-propyl-oxirane-2-carboxylic acid [4- (2- (9-cyclopropylnonyl) oxy-pyrimidin-5-yl)] phenyl ester
Phasenfolge: K751 [a]g°: - 9,6 (c = 2, CH2CI2)Phase sequence: K751 [a] g °: - 9.6 (c = 2, CH 2 Cl 2 )
Beispiel 68 (2S)-2-Fluor-3-methyl-butansäure-[4-<2-(9-cyclopropyl-nonyloxy)-pyrimidin-5-yl)]phenyl-esterExample 68 (2S) -2-Fluoro-3-methyl-butanoic acid [4- <2- (9-cyclopropyl-nonyloxy) -pyrimidin-5-yl)] -phenyl-ester
Phasenfolge: X (63 SA64] 781 [alg°: - 1,0 (c = 2, CH2CI2)Phase sequence: X (63 S A 64] 781 [alg °: - 1.0 (c = 2, CH 2 Cl 2 )
Beispiel 69 2-{4-Hexyloxy-phenyl)-5-I4-(6-cyclopropyl-hexyloxy)phenyl]-pyrimidinExample 69 2- {4-Hexyloxy-phenyl) -5-I4- (6-cyclopropyl-hexyloxy) -phenyl] -pyrimidine
Phasenfolge: X [77 S4103] 110 S3129 SC189 SA1981Phase sequence: X [77 S 4 103] 110 S 3 129 S C 189 S A 1981
Beispiel 70 5-(4-Cyclopropyl-bulyloxy)-2-[4-(5-oxa-nonyloxy)phenyl]-pyrimidinExample 70 5- (4-Cyclopropyl-bulyloxy) -2- [4- (5-oxa-nonyloxy) -phenyl] -pyrimidine
Phasenfolge: K42 SC45SA47 N641Phase sequence: K42 S C 45S A 47 N641
Beispiel 71. B-IB-Cyclopropyl-pentyloxyl^-W-IB-oxa-nonyloxylphenyllpyrimidinExample 71. B-IB-cyclopropyl-pentyloxyl-W-IB-oxa-nonyloxy-phenyl-pyrimidine
Phasenfolge: X39 SC63 SA65 NPhase sequence: X39 S C 63 S A 65 N
Beispiel 72 B-ie-Cyclopropyl-hexyloxyl-a-H-fS-oxa-nonyloxylphenyllpyrimidinExample 72 B-ie-cyclopropylhexyloxyl-a-H-fS-oxa-nonyloxy-phenyl-pyrimidine
Phasenfolge: X46SC66 SA67 NEC IPhase sequence: X46S C 66 S A 67 NEC I
Beispiel 73 5-(7-Cyclopropyl-heptyloxy)-2-I4-(5-oxa-nonyloxy)phenyl]pyrimidinExample 73 5- (7-Cyclopropyl-heptyloxy) -2-I4- (5-oxa-nonyloxy) -phenyl] -pyrimidine
Phasenfolge: K43SC731Phase sequence: K43S C 731
Beispiel 74 5-Cyclopropylmethyloxy-2-(4-octyloxyphenyl)pyrimidinExample 74 5-Cyclopropylmethyloxy-2- (4-octyloxyphenyl) pyrimidine
Phasenfolge: K63 N641Phase sequence: K63 N641
Beispiel 75 B-Octyl^-H-ie-cyclopropyl-hexyloxylphenyllpyrimidinExample 75 B-Octyl-H-he-cyclopropyl-hexyloxy-phenyl-pyrimidine
Phasenfolge: K37 SC46 SA50 N591Phase sequence: K37 S C 46 S A 50 N591
Beispiel 76 5-Octyloxy-2-t4-(6-cyclopropyl-hexyloxy)phenyl|pyrimidinExample 76 5-Octyloxy-2-t4- (6-cyclopropylhexyloxy) phenyl | pyrimidine
Phasenfolge: K56Sc80SA88N91 IPhase sequence: K56S c 80S A 88N91 I
5-(6-Cyclopropyl-hexyloxy)-2-(4-octyloxyphenyl)pyrimidin5- (6-cyclopropyl-hexyloxy) -2- (4-octyloxyphenyl) pyrimidine
Phasenfolge: K56SC78 SA84 N891Phase sequence: K56S C 78 S A 84 N891
Beispiel 7B 2-[4-(7-Cyclopropyl-heptyloxy)phenyl]-5-octyl-pyridinExample 7B 2- [4- (7-Cyclopropylheptyloxy) phenyl] -5-octylpyridine
Phasenfolge: K49 S2 63 SC721Phase sequence: K49 S 2 63 S C 721
Beispiel 79 2-|4-(11-Cyclopropyl-undecyloxy)phenyl]-G-octyl-pyridinExample 79 2- | 4- (11-Cyclopropyl undecyloxy) phenyl] -G-octylpyridine
Phasenfolge: K57 S2 63 SC721Phase sequence: K57 S 2 63 S C 721
Beispiel 80 2-(trans-4-Pentyl-cyclohexyl)-5-[4-(11-cyclopropyl-undecyloxy)-phenyll-1,3,4-thiadiazolExample 80 2- (trans-4-pentyl-cyclohexyl) -5- [4- (11-cyclopropyl-undecyloxy) -phenyl-1,3,4-thiadiazole
Phasenfolge: K111SC113 SA156 N157 IPhase sequence: K111S C 113 S A 156 N157 I
Beispiel 81 7-Cyclopropyl-heptansäure-[4-(5-octyl-pyrimidin-2-yl)phenyl-esterExample 81 7-Cyclopropyl-heptanoic acid [4- (5-octyl-pyrimidin-2-yl) -phenyl ester
Phasenfolge: K [36 Sc40,5 SA44 N46]Phase sequence: K [36 S c 40.5 S A 44 N46]
Beispiel 82 7-Cyclopropyl-heptansäure-[4-(5-decyl-pyrimidin-2-yllphenyl-esterExample 82 7-Cyclopropyl-heptanoic acid [4- (5-decyl-pyrimidin-2-yl-phenyl-ester
Phasenfolge: K48SC57IPhase sequence: K48S C 57I
Beispiel 83 7-Cyclopropyl-heptansäure-I4-(5-octyloxy-pyrimidin-2-yl)-phenyl-esterExample 83 7-Cyclopropyl-heptanoic acid-I4- (5-octyloxypyrimidin-2-yl) -phenyl ester
Phasenfolge: K62 SC77 SA84 N 84,31 Anwendungsbeispiel 1Phase sequence: K62 S C 77 S A 84 N 84.31 Application example 1
Eine Mischung bestehend aus 55mol-% Verbindung nach Beispiel 6 und 45mol-% Verbindung nach Beispiel 3 zeigt dieA mixture consisting of 55 mol% compound of Example 6 and 45 mol% compound of Example 3 shows the
Phasenfolge K31 SC58 SA641Phase sequence K31 S C 58 S A 641
Eine Mischung bestehend aus 67 mol-% Verbindung nach Beispiel 6 und 33mol-% Verbindung nach Beispiel 11 zeigt die Phasenfolge K35 SC74 SA781A mixture consisting of 67 mol% of the compound of Example 6 and 33 mol% of the compound according to Example 11 shows the phase sequence K35 S C 74 S A 781
Eine Mischung bestehend aus 20mol-% der Verbindung nach Beispiel 6,25,15 mol-% (der jeweils bekannten Mischungskomponente) 5-Octyloxy-2-(4-decyloxy-phenyl)-pyrimidin, 11 mol-% 5-Octyloxy-2-(4-octyloxy-phenyl)-pyrimidin, 20mol-% 5-Octyloxy-2-(4-hexyloxy-phenyl)-pyrimidin und 23,85mol-% 5-Octyloxy-2-(4-butyloxy-phcnyl)pyrimidin zeigt die Phasenfolge K 11,5 SC72 SA88 N 901.A mixture consisting of 20 mol% of the compound according to Example 6,25,15 mol% (of the respectively known compound component) of 5-octyloxy-2- (4-decyloxy-phenyl) -pyrimidine, 11 mol% of 5-octyloxy-2 - (4-octyloxy-phenyl) -pyrimidine, 20mol% of 5-octyloxy-2- (4-hexyloxy-phenyl) -pyrimidine and 23.85mol% of 5-octyloxy-2- (4-butyloxy-phenyl) pyrimidine the phase sequence K 11.5 S C 72 S A 88 N 901.
Anwendungsbeispiel 4 Eine Mischung aus 60mol-% Verbindung nach Beispiel 56 und 40 mol-% Verbindung nach Beispiel 55 zeigt die Phasenfolge K34 Sc82SA90l.Use Example 4 A mixture of 60 mol% of the compound of Example 56 and 40 mol% of the compound of Example 55 shows the phase sequence K34 S c 82S A 901.
Eine Mischung aus 62 mol-% Verbindung nach Beispiel 43 und 38 mol-% Verbindung nach Beispiel 37 zeigt die Phasenfolge K48 Sc93l.A mixture of 62 mol% of the compound of Example 43 and 38 mol% of the compound according to Example 37 shows the phase sequence K48 Sc93l.
Eine Mischung aus 57 mol-% Verbindung nach Beispiel 43 und 43mol-% Verbindung .tach Beispiel 65 zeigt die Phasenfolge K36 Sc90SA92l.A mixture of 57 mol% of the compound of Example 43 and 43 mol% of compound .tach Example 65 shows the phase sequence K36 S c 90S A 92l.
Anwendungsbeispiel 7 Eine Mischung aus 60mol-% Verbindung nach Beispiel 27 und 40mol-% Verbindung nach Beispiel 47 zeigt die Phasenfolge K33 SC85SA91I.Use Example 7 A mixture of 60 mol% of the compound of Example 27 and 40 mol% of the compound of Example 47 shows the phase sequence K33 S C 85S A 91I.
Eine Mischung aus 45mol-% Verbindung nach Beispiel 24 und 55mol-% Verbindung nach Beispiel 71 zeigt die Phasenfolge K Sc70SA77N79l.A mixture of 45 mol% of the compound of Example 24 and 55 mol% of the compound of Example 71 shows the phase sequence KS c 70S A 77N79l.
Eine Mischung aus 30mol-% Verbindung nach Beispiel 65 und 70mol-% Verbindung nach Beispiel 71 zeigt die Phasenfolge K25 Sc70SA73N75l.A mixture of 30 mol% of the compound of Example 65 and 70 mol% of the compound according to Example 71 shows the phase sequence K25 S c 70S A 73N75l.
Anwandungsbelsplel 10 Eine Mischung aus 40mol-% Verbindung nach Beispiel 76 und 60mol-% Verbindung nach Beispiel 56 zeigt die Phasenfolge K35Panel 10 A mixture of 40 mol% of the compound of Example 76 and 60 mol% of the compound of Example 56 shows the phase sequence K35
Eine Mischung aus 65 mol-% Verbindung nach Beispiel 71 und 35mol-% Verbindung nach Beispiel 56 zeigt die Phasenfolge K17 SC69SA73N74I.A mixture of 65 mol% of the compound of Example 71 and 35 mol% of the compound of Example 56 shows the phase sequence K17 S C 69S A 73N74I.
Die Anwendungsbeispiele 10 und 11 weisen gegenüber einer Vergleicl,^,mischung (binäre Mischung mit Verbindungen vergleichbarer Kettenlänge ohne Cyclopropyl-Rest) aus 40mol-% 5-Octyloxy-2-(4-octyloxy-phenyl)pyrimidin und 60mol-% 5-Octyloxy-2-(4-hexyloxy-phenyl)pyrimidin mit der Phasenfolge K39 Sc90 SA98 N1001 sowohl einen niedrigeren Schmelzpunkt als auch eine größere Schmelzpunktdepression auf.Application Examples 10 and 11 show a comparison (binary mixture with compounds of comparable chain length without cyclopropyl radical) of 40 mol% of 5-octyloxy-2- (4-octyloxyphenyl) pyrimidine and 60 mol% of 5-octyloxy -2- (4-hexyloxyphenyl) pyrimidine having the phase sequence K39 S c 90 S A 98 N1001 has both a lower melting point and a higher melting point depression.
Ausführungsbeispiel 12 Eine Mischung aus 50mol-% 5-Dodecyloxy-2-(4-octyloxy-phenyl)pyrimidin und 50 mol-% der Verbindung nach Beispiel 24 weist die Phasenfolge K33 SC96I auf. Gegenüber den Vergleichsmischungen (binäre Mischungen vergleichbarer Kettenlängen ohne Cyclopropyl-Rest) aus 39mol-% 5-Decyloxy-2-(4-octyloxyphenyl)pyrimidin und 61 mol-% 5-Octyloxy-2-(4-decyloxyphenyOpyrimidin mit der Phasenfolge K39 SC94 SA1001 oder aus 60mol-% 5-Octyloxy-2-(4-decyloxy-phenyl)pyrimidin und 40mol-% 5-Octyloxy-2-(4-dodecyloxy-phenyl)pyrimidin mit der Phasenfolge K40 SC86 SA97I sowohl einen niedrigeren Schmelzpunkt als auch eine größere Schmelzpunktdepression auf.Exemplary Embodiment 12 A mixture of 50 mol% of 5-dodecyloxy-2- (4-octyloxyphenyl) pyrimidine and 50 mol% of the compound of Example 24 has the phase sequence K33 S C 96I. Compared with the comparison mixtures (binary mixtures of comparable chain lengths without cyclopropyl radical) from 39 mol% of 5-decyloxy-2- (4-octyloxyphenyl) pyrimidine and 61 mol% of 5-octyloxy-2- (4-decyloxyphenyOpyrimidin with the phase sequence K39 S C 94 S A 1001 or from 60mol% 5-octyloxy-2- (4-decyloxy-phenyl) pyrimidine and 40mol% 5-octyloxy-2- (4-dodecyloxyphenyl) pyrimidine having the phase sequence K40 S C 86 S A 97I has both a lower melting point and a higher melting point depression.
Anwendungsbeispiel 13 Eine Mischung aus 30 mol-% 5-Octyloxy-2-(4-ethyloxy-phenyl)pyrimidin 6mol-%5-Dodecyloxy-2-(4-butyloxy-phenyl)pyrimidin 15mol-% Verbindung nach Beispiel 19mol-% Verbindung nach Beispiel 20mol-% Verbindung nach Beispiel 10mol-% Verbindung nach Beispiel weist die Phasenfolge K 8 S0 68 SA 85 N 87 auf.Use Example 13 A mixture of 30 mol% 5-octyloxy-2- (4-ethyloxyphenyl) pyrimidine 6 mol% 5-dodecyloxy-2- (4-butyloxyphenyl) pyrimidine 15 mol% compound according to Example 19 mol% compound Example 20mol% compound according to Example 10mol% compound according to Example has the phase sequence K 8 S 0 68 S A 85 N 87.
Anwendungsbeispiel 14 Eine ferroelektrische Multikomponentenmischung die 10mol-% der Verbindung nach Beispiel 62 in ""Felix 001*'enthält, weist folgende Phasenfolge auf K -5 SJ72 SJ78 N»93I.Application Example 14 A ferroelectric multicomponent mixture containing 10 mol% of the compound according to Example 62 in "Felix 001 *" has the following phase sequence on K -5 SJ72 SJ78 N »93I.
* (C.Escher, H.-R. Dubai, W.Hemmerling, I.Müller, D.Ohlendorf und R.Wingen, vorgetragen auf .1st International Symposium on Ferroelectric Liquid Crystals, Arcachon, Bordeaux-France, 21.-23.Sept. 1987", handelsübliche Mischung der Hoechst Aktiengesellschaft mit der Phasenfolge K-7S;79SJf.83N'99l) * (C.Escher, H.R. Dubai, W.Hemmerling, I.Müller, D.Ohlendorf and R.Wingen, presented at .1st International Symposium on Ferroelectric Liquid Crystals, Arcachon, Bordeaux-France, 21.-23 .Sept., 1987, commercial mixture of Hoechst Aktiengesellschaft with the phase sequence K-7S; 79SJf.83N'99l)
Die Mischung ist nach konventionellen Methoden gut orientierbar und ist bislabil. Bei 250C zeigt die Mischung eine spontane Polarisation von -δ,βηΟ/οιη2 und weist folgende Schaltzeiten auf:The mixture is easily orientable by conventional methods and is bis-labile. At 25 0 C the mixture exhibits a spontaneous polarization of -δ, βηΟ / οιη 2 and has the following switching times:
To-90 = 213μβ τ,ο-βο= 90msTo-90 = 213μβ τ, ο-βο = 90ms
Die Viskosität der Mischung liegt bei 65mPas und der doppelte effektive Tiltwinkel ist 18°.The viscosity of the mixture is 65mPas and the double effective tilt angle is 18 °.
Anwendungsbeispiel 15 Eine ferroelektrisch^ Mischung aus 85,5mol-% der Mischung aus Anwendungsbeispiel 13 mit 0,5mol-% trans-4-Pentylcyclohexancarbonsäure-|4-(5-docyl)pyrimidin-2-yl]phenyl-ester und 5mol-% 4-(2-((S) •7-Methyl-nonyloxy)pyrimidin-5-yl]-phenyl-(2S,3S)-2-chlor-3-methyl-pentansäureester weist die Phasenfolge K5 SJ72 SX83 N* 881 auf. Die Mischung ist nach konventionellen Methoden gut orientierbar und ist bistabil. Bei 25°C zeigt die Mischung eine spontaneApplication Example 15 A ferroelectric mixture of 85.5 mol% of the mixture from Application Example 13 with 0.5 mol% of trans-4-pentylcyclohexanecarboxylic acid [4- (5-docyl) pyrimidin-2-yl] phenyl and 5 mol% 4- (2 - ((S) .7-Methyl-nonyloxy) pyrimidin-5-yl] -phenyl- (2S, 3S) -2-chloro-3-methyl-pentanoic acid ester has the phase sequence K5 SJ72 SX83 N * 881 The mixture is well orientable by conventional methods and is bistable, at 25 ° C the mixture shows a spontaneous
Polarisation von -8,2nC/cm2 und weist folgende Schaltzeiten auf:Polarization of -8.2nC / cm 2 and has the following switching times:
T.o-90 = 139ps Tio-90 = 66 msT.o-90 = 139ps Tio-90 = 66ms
Die Viskosität der Mischung liegt bei 280mPas und der doppelte effektive Tiltwinkel beträgt 17°.The viscosity of the mixture is 280mPas and the double effective tilt angle is 17 °.
Claims (2)
j, k, I, m, η Null oder 116 C atoms, in which also a -CH 2 group may be replaced by -O-, -CO-O or -O-CO-
j, k, I, m, η is zero or 1
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DE3718174A1 (en) * | 1987-05-29 | 1988-12-15 | Hoechst Ag | USE OF OPTICALLY ACTIVE OXIRAN-2-CARBONIC ACID ESTERS AS DOPING AGENTS IN LIQUID CRYSTAL MIXTURES, THESE CONTAINING LIQUID CRYSTAL MIXTURES AND NEW OPTICALLY ACTIVE OXIRAN-2-CARBONIC ACID ESTERS |
US5407599A (en) * | 1987-11-25 | 1995-04-18 | Hoechst Aktiengesellschaft | Cyclopropylaklyl or -alkenyl or heterocyclic compounds, process for their preparation and their use in liquid-crystalline mixtures |
DE3915804A1 (en) * | 1989-05-13 | 1990-11-15 | Hoechst Ag | CYCLOPROPYL ALKYL OR ALKENYL COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN LIQUID CRYSTALLINE MIXTURES |
DE3925971A1 (en) * | 1989-08-05 | 1991-02-07 | Hoechst Ag | LIQUID CRYSTALLINES, ESPECIALLY FERROELECTRIC LIQUID CRYSTALLINE MIXTURES AND THEIR USE IN ELECTROOPTICAL DEVICES |
JPH04501864A (en) * | 1989-09-05 | 1992-04-02 | メルク・パテント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Phenylcyclohexane compound and liquid crystal phase |
US5064564A (en) * | 1989-12-22 | 1991-11-12 | Dainippon Ink And Chemicals, Inc. | Optically active compound, intermediate therefor, process for producing the intermediate, and liquid-crystal composition |
JPH03193774A (en) * | 1989-12-22 | 1991-08-23 | Canon Inc | Optically active liquid crystal compound, liquid crystal composition containing same and liquid crystal element using this composition |
US5128061A (en) * | 1990-08-14 | 1992-07-07 | Optical Shields, Inc. | Phenyl-pyrimidine liquid crystal materials |
DE4030579A1 (en) * | 1990-09-27 | 1992-04-02 | Hoechst Ag | CYCLOHEXYLPHENYLPYRIMIDINES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN LIQUID CRYSTALLINE MIXTURES |
US5695683A (en) * | 1993-09-30 | 1997-12-09 | Hoechst Aktiengesellschaft | Ferroelectric liquid crystal mixture |
JPH0931064A (en) * | 1995-07-17 | 1997-02-04 | Rolic Ag | Alkoxyalkoxylated nitrogen-containing heterocyclic compound derivative |
DE10145780B4 (en) | 2001-09-17 | 2012-10-04 | Merck Patent Gmbh | Fluorinated cyclopenta [a] naphthalenes and their use in liquid crystal mixtures and displays |
DE10145778B4 (en) | 2001-09-17 | 2012-07-19 | Merck Patent Gmbh | Fluorinated anthracenes and their use in liquid crystal mixtures and in liquid crystal displays |
DE10145779B4 (en) | 2001-09-17 | 2012-11-15 | Merck Patent Gmbh | Fluorinated cyclopenta [b] naphthalenes and their use in liquid crystal mixtures |
US9923148B2 (en) | 2002-10-30 | 2018-03-20 | Udc Ireland Limited | Electroluminescent device |
AU2003274050A1 (en) | 2002-10-30 | 2004-05-25 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
CN105219399B (en) * | 2014-12-12 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal compounds and liquid crystal compound containing cyclopropyl |
CN104650923B (en) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal composition and its application |
CN104593009A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and application thereof in liquid crystal display |
CN107177360A (en) * | 2015-02-15 | 2017-09-19 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropy liquid crystal medium and its application containing cyclopropyl |
CN104593003B (en) * | 2015-02-15 | 2017-01-04 | 石家庄诚志永华显示材料有限公司 | Liquid crystal media |
CN104593012A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition |
CN104593010A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and application thereof |
CN104650928A (en) * | 2015-02-15 | 2015-05-27 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition containing cyclopropyl compound |
CN104593007B (en) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal composition and its application |
CN104593005B (en) * | 2015-02-15 | 2017-01-11 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition containing dioxane structure |
CN104593004B (en) * | 2015-02-15 | 2017-05-24 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition |
CN104650925B (en) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | Liquid crystal media |
CN107267158A (en) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropy liquid crystal medium and its application containing cyclopropyl |
CN104593001A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and application thereof |
CN104593013B (en) * | 2015-02-15 | 2016-12-07 | 石家庄诚志永华显示材料有限公司 | A kind of liquid crystal media |
CN104593008B (en) * | 2015-02-15 | 2017-01-04 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal composition and application thereof |
CN107286952B (en) * | 2016-04-01 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal compounds of cyclopropyl base class negative dielectric anisotropic and its application |
CN107286951B (en) * | 2016-04-01 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal compounds of cyclopropyl base class negative dielectric anisotropic and its application |
CN107345142B (en) * | 2016-05-06 | 2020-02-21 | 北京八亿时空液晶科技股份有限公司 | Negative dielectric anisotropy liquid crystal composition containing naphthalene ring and application thereof |
CN107400516B (en) * | 2016-05-19 | 2019-01-29 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal compounds of cyclopropyl base class negative dielectric anisotropic and its application |
CN107523314B (en) * | 2016-06-20 | 2019-09-20 | 北京八亿时空液晶科技股份有限公司 | One kind containing the negative dielectric liquid crystal composition of cyclopropyl ethers and its application |
CN107586545B (en) * | 2016-07-06 | 2019-08-23 | 北京八亿时空液晶科技股份有限公司 | A kind of fast-response negative dielectric anisotropy liquid crystal composition and its application |
CN109097066B (en) * | 2017-06-20 | 2021-12-21 | 江苏和成显示科技有限公司 | Smectic phase liquid crystal composition and application thereof in liquid crystal display device |
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- 1988-11-23 DD DD88322084A patent/DD289524A5/en not_active IP Right Cessation
- 1988-11-24 NO NO88885236A patent/NO885236L/en unknown
- 1988-11-24 BR BR888806184A patent/BR8806184A/en not_active Application Discontinuation
- 1988-11-24 JP JP63294826A patent/JPH0751563B2/en not_active Expired - Lifetime
- 1988-11-24 KR KR1019880015462A patent/KR970011278B1/en not_active IP Right Cessation
-
1989
- 1989-06-14 NO NO892472A patent/NO892472D0/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE3852931D1 (en) | 1995-03-16 |
KR890008111A (en) | 1989-07-08 |
NO892472D0 (en) | 1989-06-14 |
NO892472L (en) | 1989-05-26 |
KR970011278B1 (en) | 1997-07-09 |
JPH0751563B2 (en) | 1995-06-05 |
NO885236D0 (en) | 1988-11-24 |
BR8806184A (en) | 1989-08-15 |
ATE117996T1 (en) | 1995-02-15 |
DE3839330A1 (en) | 1989-06-08 |
EP0318423A2 (en) | 1989-05-31 |
CN1022409C (en) | 1993-10-13 |
NO885236L (en) | 1989-05-26 |
EP0318423A3 (en) | 1990-08-08 |
CN1039019A (en) | 1990-01-24 |
EP0318423B1 (en) | 1995-02-01 |
JPH01165573A (en) | 1989-06-29 |
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