JPS63502756A - Nematic liquid crystal phase - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] nematic liquid crystal phase The present invention provides novel nematic compounds containing at least one chiral (optically active) compound. liquid crystal phase (LC phase) (hereinafter, the general term ``nematic'' is telic).

Necessity of an LC phase forming a helical structure with a fixed rotation direction for liquid crystal displays is increasing. Therefore, if such materials are used, e.g. (Schadt-Helfrich) effect, cholesteric-nematic phase change effect, birefringence effect, SBE effect (Mo1.Cryst, Liq.

Cryst, 123.30:3-319 (1985); DE-A-3, 423,993) and White-Taylor. Requested for cell purposes.

An important issue in this connection is creating a suitable temperature function of this helical pitch. This function particularly concerns electro-optic effects and special aspects thereof.

In the case of liquid crystal display elements based on twisted nematic cells, they are not affected by temperature. The pitch is appropriate to avoid "reverse twist". Furthermore, the spiral pitch If the current decreases with increasing temperature, the threshold voltage of the twisted nematic cell changes with temperature. It was possible to show that it is possible to achieve compensation for the vibrations (P, R, Gerb er: Physics Letters 78A, page 285 (1980) reference〕. Compensation of threshold voltage fluctuation causes twist pitch to sharply decrease as temperature increases This is also true for phase change effects (A.

G5b14unsch, G, Heppke and F, 0estreich Journal de Physique by er 40.773 pages (197 9 years)].

Generally, the LC phases used for these purposes are doped to create a helical structure. A mixture of non-chiral liquid crystal compounds containing a chiral compound added thereto. Ru.

Almost all known chiral doping materials give rise to helical structures, which Their pitch increases sharply with temperature over a wide range. different Using two suitable doping materials with different rotational direction and relative temperature dependence. achieve the often required negative increase in temperature dependence by using (DB-A-2, 827, 471). These multiple doping substances The disadvantages of the method used are, among others, the ability to maintain an accurate concentration ratio of the two chiral compounds. and be restricted to a limited temperature range, and also doping substances. is required at a high total concentration (A, 'G6bl-Wunsch, G , Heppke and F. Oestreicher, supra).

Therefore, it cannot be used for outdoor purposes.

Therefore, the present invention provides temperature-independent electro-optical parameters, in particular temperature-independent electro-optical parameters. In this LC phase, the doping substance pitch temperature over a wide temperature range for indoor and outdoor applications due to the addition of We find an LC phase in which a negative increase in dependence is simultaneously accompanied by high torsional forces. It is based on the purpose of publishing.

These objectives are achieved according to the invention by using the nematic phase C phase described below. This is achieved by

The subject of the invention is at least two liquid crystals containing at least one chiral compound. It is a nematic liquid crystal phase containing compounds, and there are many chiral compounds and one chiral phase. It is a compound that has a chiral center, and this chiral center has two cyclic mesogenic groups. A nematic characterized by being a member of a bridge containing an even number of bridge elements between them. It is in the liquid crystal phase.

Another subject of the invention is that the chiral compound is a compound corresponding to formula I: This type of nematic phase is characterized by: R'-X'-CHR' (Cut)p-X'-R' I [wherein XI and Xt are -CO-O-1-O-CO-1-CB, -CO- 0-1-CO-0-CB, -1-CH, 0-1-0CHt-1-CHtCHt- 1-〇- or a single bond, and RI and R1 each independently represent Formula -(A'-Z), -(A'') represents a group represented by -Y, and A1 and A'' are each, independently of the other, represents 1,4-phenylene and is present in this group One or more CFI groups may be replaced by N, or AI and A! each represents 1,4-cyclohexylene, and One CI, group or two non-adjacent CH, groups present are 10- and (or or) -S-, or AI and A'' may be replaced by each is 1,4-bicyclo(2,2,2)octylene, and these groups has one or more FsCQSBrSCN and (or ) alkyl group (this alkyl group has up to 12 C atoms and one CH present, a group or two non-adjacent CHs.

(optionally replaced by an O atom), 2 is -c o-o-1-o-co-1CH*CHt-1OCHt-1-CH,0-1-C I=N-1-N=CI (-1-N=N-1-N(0)=N- or represents a single bond , m represents 0, l or 2, n represents 1 or 2, Y represents 12 C atoms represents a straight-chain or branched alkyl group having up to One C1, group or two non-adjacent CI, groups replaced by 0 atoms or Y represents FlCQs Br or CN and p is 0 or 1, and Ro represents an alkyl group having up to 5 C atoms. , or Ro represents halogen, CN, phenyl group or cyclohexyl group , provided that the number of members of the -X'-CHRo-(CHt)-X''- bridge is an even number. and also at least one of the x1 group and the Xt group represents a single bond. ].

A temperature-compensated LC phase or LC display element is one that is substantially temperature-insensitive. L having electro-optical parameters, in particular a threshold voltage that is virtually independent of temperature. It should be understood to mean C-phase or LC display elements respectively.

This temperature independence is generally limited to the steady-state temperature range of the application, i.e. -40 to +100°, especially =20 to +80°. In this case, electric light In the temperature range of 120 to +80°, the chemical parameters are at most per 1°C. ±0.15%, preferably at most ±0.1% per 1°C, Electro-optic parameters are usually described as being substantially temperature-independent.

The required strength of temperature independence varies depending on the intended use. This is obvious to those skilled in the art.

In particular, the novel nematic LC phase of the present invention has a relatively high, especially substantially temperature-free A dependent twist is generated within the phase by the chiral doping material of the present invention. It is special in the fact that it is These properties are important for example in TN cells or This is a very advantageous property for use in SBE cells. The new cell of the present invention The torsion force is less temperature-dependent compared to previously known phases. In the temperature range consisting of One can even see a decrease in the generated pitch accompanying temperature changes.

Throughout this specification, x', x'', R', R'', A', A'', 21m -, ns, Ys, p and Ro have the above meanings unless otherwise specified. Ru.

In the compound of formula I, -X'-CHR'-(CH,)p-xl- bridge is preferably BarCo-0-C)IRo-C)l! - represents a group, and furthermore, Preferably CH, -CO-0-CHR0--CHR'-C representing the following group O-0-CH,--O-CO-C)IRo-CH,--CHRo-CH,-CO -0--CH2-OC)IRo-CH2--CHR'-CHt-0-CO--O CR, -C) IR'-CH, --CHR'-CH, -〇-CH, --CHt　C FI　t-CHR'　-C8t　--CUR'　-CHt　-CHt　-0-- O-CHR'--CI'lR'-Cut-Cut-CHz--CHRo-CH, --CHR'-0- At the same time, the group R0 is preferably methyl, and also preferably Preferably ethyl, propyl, isopropyl, butyl, F, C (!1BrSCN , phenyl or cyclohexyl.

Generally, in formula I, during crosslinking, an ester group (X' or x2=-co-o-1 -0-CO-1-CH, -CO-0- or -co-o-cut -) The corresponding compounds are preferred.

The group R1 is preferably Y-Pyr-Phe- and the group R1 is preferably - It is Phg-Y.

Furthermore, R1 and R2 preferably represent the following groups: Y-Phe- (R' can also be this group or Y-Phe-COO- Phe-Y-Pyr-Y-Cy-COO-Cy-Y-Dio-Y-Phe-OC O-Phe-Y-Phe-Phe-Y-Cy-OCO-Phe-Y-Phe-C y-Y-Phe-OCO-Cy-Y-Cy-Phe-Y-Cy-OCO-Cy- Y-Cy-Cy-Y-Phe-CH20-Phe-Y-Phe-Dio-Y-C y-CHzO-Phe-Y-Dio-Phe-Y-Phe-CHtO-Cy-Y -Cy-Dio-Y-Phe-CH, 0-Py-Y-Dio-Cy-Y-Phe -CHtO-Pyr-Y-Phe-Py-Y-Phe-CHtCHt-Phe- Y-Py-Phe-Y-Cy-CHtCHt-Phe-Y-Cy-Py-Y-P he-CHtCHt-Cy-Y-Py-Cy-Y-Cy-CHtCH2-Cy- Y-Phe-Pyr-Y-Phe-CHtCHt-Py-Y-Pyr-Phe- (R' can also be this group or Y-Py-CHtCHt-Phe- Y-Cy-Pyr-Y-Phe-CHtCHt-Pyr-Y-Pyr-Cy-Y -Pyr-CHtCHt-Phe-Y-Tr 1-Phe-Y-Tri-CHx One CHt-Phe-Y-Phe-Tri-Y-Phe-CHtCHt-Tri Throughout the specification, Phe represents 1,4-phenylene, this group being unsubstituted. or has a fluorine atom as a substituent, Cy is 1,4-cyclohexylene py represents pyridine-2,5-diyl, Pyr represents pyrimidine-2 ,5-diyl, and Dio represents 1,3-dioxane-2,5-diyl. , Tri represents 1,2,4-triazine-3,6,-diyl, and The substituents in cy and Dio are preferably present in the trans position, respectively. Ru.

In formula I, one or more radicals Dio, radicals PY.

All corresponding compounds containing the group Pyr or the group Tri include positional isomers. can be done. Therefore, for example, the formula Y-Dio-bridge member-R' (1, R' = Y-Dio) is 2-Y-5-(R”-bridge member)-1,3,-dioxane and 2(R”-bridge member)-5-Y-1,3-dioxane, preferably Subformula Y-Pyr-Phe-CO-0-CHR'-CHz-Phe-Y (I ce, see below) and subformula 5-Y-2 (PheCo-0-CHR'-CH tPhe-Y)-pyrimidine and also the isomer 2-Y-5-(-Phe-Co -0-CHR'-CHt-Phe-Y)-pyrimidine.

In particular, the compounds of formula I preferably contain 2 to 4 rings in the molecule. Compounds represented by the following subformula 1a=Im are included: Y-A″-Bridge member-A’-Y　I　a Y-A"-ku AI-Bridge member-A"-Y I bY-A'-A"-Bridge member-A" -Y　cY-A″-Bridge member-A’-Z-A’-Y　dY-A″-Bridge member 1 “-A”-Y IeY-A”-Z-A’-i Bridge member-A’-Z-A”-Y I fY-A"-Z-A'-Bridge member-A'-A"-Y IgY-A"-A"-Bridge Member-A'-Z-A''-Y　hY-A''-A''-Bridge member-A''-A''-Y　l 1Y-A”-Bridge member-A’-Z-A’-Z-A”-Y I jY-A’-Bridge member -A"-Z-A"-A"Y-Y I kY-A"-Z-A'-Z-A'-Bridge member -A”-Y　IY-A”-A”-Z-A’-Bridge member-A”-Y　I　m molecule When there are two Y, A', A2, and two groups in can be the same or different.

Compounds represented by sub-formulas Ia-Ic are preferred, particularly those represented by the following sub-formula I aa= Compounds represented by I ad and also represented by the following subformula 1 ca = I an Preferred compounds are: Y-Phe-CHR'-Co-0-Cut-Cy-Y I aaY-Cy-CHRo-Co-0-Cut-Cy-Y I abY-Phe -CHR'-Co-0-Cut-Phe-Y I acY-Cy-CURo-C o-0-CHt-Phe-Y　I　adY-Phe-Phe-Co-0-C)I R'-CH, -Phe-Y　caY-Phe-Phe-Co-0-CHR' -CHt-Cy-Y　I　cbY-Phe-Cy-Co-0-CHR'-CHt -Phe-Y　I　ccY-Phe-Cy-Co-0-CHR'-CHt-Cy -Y　cdY-Pyr-Phe-Co-0-CHR'-CH, -Phe-Y I ceY-Pyr-Phe-Co-0-CHRo-CHt-Cy-Y I cfY-Pyr-Phe-CHR'-CH, -Co-0-Phe-Y Icg Y-Pyr-Phe-CHR'-CH, -CO-0-Cy-Y I ahY-P yr-Phe-CH, -CHR'-Co-0-Phe-Y I ciY-Pyr -Phe-CHt-CHR'-Co-0-Cy-Y　I　cjY-Cy-Cy- CB, -Co-0-CHR'-Phe-Y IckY-Cy-Cy-CH, - Co-0-CHR'-Cy-Y I clY-Cy-Phe-Cut-CHR' -Phe-Y　I　cmY-Cy-Phe-CHt-CRRo-Cy-Y　I　 cn Among these, the compound represented by the formula Ice is particularly preferred.

In the compounds represented by the formulas described herein, Y preferably represents an alkyl group. I, furthermore, an alkoxy group, another oxaalkyl group, a CN group or an F can represent a group. an alkyl group and one CHt group present in this group is replaced by an O atom (“alkoxy” or “oxaalkyl”) ” group) or similarly, two non-adjacent CH, groups are replaced by 0 atoms. (“alkoxyalkoxy” or “dioxaalkyl” group) is a straight chain or branched. Preferably these groups are linear , 2.3.4.5.6 or 7 C atoms and therefore preferably ethyl, propylene Pill, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy 2-oxapropyl, pentoxy, hexoxy, heptoxy, 2-oxapropyl (=methoxymethoxy) ethyl), 2-oxbutyl (-ethoxymethyl) or 3-oxbutyl (=2 -methoxyethyl), 2-13- or 4-oxapentyl, 2-13-14- or 5-oxahexyl, 2-13-14-15- or 6-oxaheptyl It also represents methyl, octyl, nonyl, decyl, methoxy, octoxy. cy, thornoxy, decoxy, 2-13-14-15-16- or 7-oxaoc Chil, 2-13-14-15-16-17- or 8-oxanonyl, 2-13 -14-15-16-17-18- or 9-oxadecyl, 1,3-dioxa Butyl (=methoxymethoxy), 1.3-11.4- or 2.4-dioxa Pentyl, 1.3-11.4-11.5-12.4-12.5- or 3.5- Dioxahexyl, 1.3-1 l.

4-11.5-1l, 6-12.4-12.5-12.6-13.5-13゜6 - or 4,6-thioxaheptyl.

In the formula ■ and also in the formula Ia=Im, corresponding compounds with a branched side group Y Things can be important. This type of branched group generally has at most one branch chain. has. Preferred branched Y groups are isopropyl, 2-butyl (=1-methylbutyl). (2-methylpropyl), isobutyl (=2-methylpropyl), 2-methylbutyl, isopene methyl (=3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2- Ethylhexyl, 2-propylpentyl, isopropoxy, 2-methylpropoxy cy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentoxy, 3-methyl Tylpentoxy, 2-ethylhexoxy, 1-methylhexoxy, l-methylhexoxy ptoxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpentyl be.

A' and A' are each, independently of each other, preferably Cy, Phe, P yr or Dio; suitably the compound of formula I contains at most one group D io, a group py or a group Pyr.

Z is preferably a single bond, -CO-O- or -〇-Co-, and also - A cutcut- group is preferred.

The compound represented by the formula Hoden der Organischen Chemie (Georg-T Hieme Publishers, Stuttgart City Publications). in particular by methods known per se, such as those suitable for the reactions mentioned. manufactured under known reaction conditions. This is known per se and will not be explained in detail here. Variants not disclosed may also be used at the same time.

If desired, the starting materials can be reacted further immediately without isolating them from the reaction mixture. in situ in such a way as to convert it into a compound of formula I. You can also do it.

Generally, one type of raw material for producing the compound represented by formula ■ is a chiral compound. It is a thing.

Therefore, the compound represented by formula I is defined as H atom present in the molecule in formula I. has one or more reducible groups and/or C-C bonds instead of It can be produced by reducing the corresponding compound.

Reducible groups are preferably carbonyl groups, especially keto groups, and also For example, free or esterified hydroxy groups or aromatic Halogen atoms bonded to aromatic groups can be considered.

A suitable starting material for this reduction is a cyclohexane ring in formula I. can contain a hexene ring or a cyclohexanone ring, and/or -CHP CI (instead of the 2- group can contain a -CH=CH- group and/or -C can contain 100- groups instead of H2- groups and/or free instead of H atoms OH groups or OH groups that have been functionalized (e.g. their p-toluenesulfonate nate form).

The reduction is carried out, for example, at a temperature of about 0° to about 200° and a pressure of about 1 to 200 bar. Alcohols such as methanol, ethanol or isopropanol Ethers such as cole, tetrahydrofuran (THF) or dioxane , esters such as ethyl acetate, carboxylic acids such as acetic acid or cyclohexane It can be carried out by catalytic hydrogenation in an inert solvent such as a hydrocarbon such as Wear. Suitable catalysts are in particular noble metals such as Pt or Pd, which are (e.g. PtO2, Pd0), on a support (e.g. charcoal, calcium carbonate). Pd on lithium or strontium carbonate) or can be used in finely divided form. Wear.

Ketone compounds can also be prepared by Clemmensen's method (in which anine, alum anine, or tin and hydrochloric acid, especially in an aqueous-alcoholic solution or For use at temperatures of approximately 80-120° in a heterogeneous phase containing water/toluene. or by the Wolff-Kishner method (in this method, Radin, especially in the presence of an alkali such as KOH or NaOH, is in high boiling solvents such as glycol or triethylene glycol. (used at temperatures between 00 and 200°), and in formula I, a produces the corresponding compound with alkyl group and/or -CHtCHt- bridge can do.

Furthermore, reduction with complex hydrides can be used.

- As an example, an arylsulfonyloxy group can be reductively separated using LiA (21, In particular, the p-)luenesulfonyloxymethyl group is Temperatures from 0 to 100° in an inert solvent such as methyl ether or THF can be reduced to a methyl group. The double bond is NaBH+ or tributyl- Tin hydride can be hydrogenated using methanol (CN groups present Even if you do. Therefore, the corresponding cyclohexane derivative, for example l- Produced from cyanocyclohexene derivatives.

Ester compounds of formula I (wherein XI, X2 and/or z=-c o-o- or -0-CO-) represents the corresponding carboxylic acid compound, e.g. formula R'- COOH, R'-CHR'-CHt-C0OH, R'-CHR'-COOH, R "-C00H1R"-Cl, -CHR'-COOI(, Y-A"-COOH or is a compound represented by R"X'-CHR'-(CHt)--X"-A'-COOH (or reactive derivatives thereof) with the formula R'-OH, R'-CHR'-CB, -O n.

R”-OB, R’-CHt-CHR’-0HSR”-CTltOH, R’X "-CHR' (CHt)p-X"-A'-On or Y-A'-OR produced by esterification with an alcohol compound or phenol compound. can be done.

Suitable reactive derivatives of said carboxylic acid compounds are in particular acid halide compounds, especially carboxylic acid compounds. lorides and bromides, and also acid anhydrides, e.g. Mixed acid anhydrides, azide compounds or esters as shown by o-0-COCH* ter compounds, especially alkyl ester compounds having 1 to 4 C atoms in the alkyl group , and furthermore, Na.

Salts such as K, Cs or Ag salts.

The reactive derivatives of the alcohol compounds or phenolic compounds include, in particular, R'-OM or R''-CH, -CHR'-OM (in each formula, M is a monovalent metal, preferably or an alkali metal such as Na or K), and or corresponding halides, such as formula R'Br1R'-CH, -CHR'-Br or A compound represented by R''-CURo-Br is considered.

Esterification is advantageously carried out in the presence of an inert solvent. In particular, diethyl ether ether, di-n-butyl ether, THF, dioxane or anisole. ether, ketones such as acetone, butanone or cyclohexanone, DM Amides such as F or phosphoric acid hexamethyltriamide, benzene, toluene or or hydrocarbons such as xylene, dichloromethane or tetrachloroethylene. halogenated hydrocarbons such as dimethyl sulfoxide or sulfolane. Eel sulfoxide is very suitable. Water-immiscible solvents can be used advantageously at the same time. , whereby the water produced during esterification can be distilled off by azeotropic distillation. In case Therefore, as a solvent for esterification, an excess of an organic base, such as pyridine, quinoline, etc. Alternatively, triethylamine can also be used. Esterification also requires no solvent for example by simply heating the reaction components in the presence of sodium acetate. You can also do this. The reaction temperature is usually -50 to +250°, preferably -250° It is 0@~+801. At these temperatures, the esterification reaction generally takes between 15 minutes and 48 minutes. Completed after hours.

The reaction conditions for esterification mostly depend on the type of raw materials used in each case. Depends on the class. That is, free carboxylic acids and free alcohols are generally strong acids, such as in the presence of mineral acids such as hydrochloric acid or sulfuric acid, or dicyclohexyl carbodi The reaction is carried out in the presence of a water separating agent such as an imide. The preferred reaction method is acid anhydride or in particular by reacting an acid chloride with an alcohol, preferably in a basic medium. Yes, in this case alkali metals like sodium hydroxide or potassium hydroxide hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate or bicarbonate Carbonates or bicarbonates of alkali metals such as potassium, sodium acetate or or alkali metal acetates such as potassium acetate, or alkaline metal acetates such as calcium hydroxide. Potassium earth metal hydroxides, or triethylamine, pyridine, lutidine, coli Of particular interest are organic bases such as gin or quinoline. Another suitable S If the compound is esterified, it can be treated with an ethanolic solution of sodium hydroxide or potassium hydroxide. Sodium alcoholate or potassium alcoholate or sodium into potassium ferulate or potassium ferulate, respectively, and the product is simply converted into then in acetone or diethyl ether with sodium bicarbonate or Suspend with stirring with potassium carbonate, add diethyl ether, A solution of the acid chloride or acid anhydride in acetone or DMF, preferably about - This method consists of adding at a temperature of 25° to +20°. Furthermore, even if The alcohol phase is used to esterify salts such as alkali metal salts of carboxylic acids. It is also possible to react with appropriate halide compounds, such as bromides.

Furthermore, compounds of formula I can be prepared by organometallic synthesis. Wear. That is, for example, an organometallic of the formula R''-MgBr or R'Li A compound of the formula R'-X'-CHR'-(CHt)p-Br, for example, a halide compound such as romide and preferably a catalyst such as L+tCuCQa. and react at about 10-30° in an inert solvent such as T) (F). be able to.

The LC phase according to the invention consists of 2 to 18 components, preferably 3 to 15 components, A chiral compound of the type specified by, preferably a compound of formula ■ Contains at least one type. The other components are preferably nematic or nematogenic. substances, especially azoxybenzene compounds, benzylideneaniline compounds, and biphenyls. nyl compounds, terphenyl compounds, phenyl or cyclohexyl benzoates compound, phenylcyclohexanecarboxylate compound or cyclohexyl Cyclohexane carboxylate compounds, phenylcyclohexane compounds, lohexyl biphenyl compound, cyclohexylcyclohexane compound, cycloto xylnaphthalene compound, 1,4-his(cyclohexyl)benzene compound, 4 ．． 4'-bis(cyclohexyl)biphenyl compound, phenylpyrimidine compound or cyclohexylpyrimidine compounds, phenyldioxane compounds or cyclohexylpyrimidine compounds, lohexyldioxane compounds, optionally halogenated stilbene compounds compounds, benzyl phenyl ether compounds, tolan compounds and substituted silicon Selected from known substances from the group of cutaneous acid compounds.

The most important compound suitable as a component of such an LC phase can be represented by the following formula: Has the characteristics of: R'-L-G-E-R' II [In the formula, and E are 1,4-disubstituted benzene and cyclohexane rings, respectively, 4.4'-Disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane Clohexane series, 2,5-disubstituted pyrimidine and 1,3-dioxane ring, 2. 6-disubstituted naphthalenes, di- and tetrahydronaphthalenes, quinazolines and Carbocyclic or heterocyclic ring systems from the group formed from tetrahydroquinazolines and G is -CH:CH--N(0)=N- -CH=CQ--CH=N(0)- -CH=N--COO-Phe-COO- or C-C single bond, Q is ha represents chlorine, preferably chlorine, or -CN, and R3 and R4 are Each carbon atom 1811i! Alkyl, alkyl having up to I, preferably up to 8 alkoxy, alkanoyloxy or alkoxycarbonyloxy; Or one of these bases also CN1NC, NO! , CFa, NC3, F, C& There can also be a BRTE].

In most of these compounds, R3 and R' are different from each other and these groups in most cases is an alkyl or alkoxy group. that which is included A variety of other substituents are also conventional. Such substances or mixtures thereof are It is commercially available. All of these substances can be prepared by methods known from the literature.

The LC phase according to the invention is composed of a particular type of chiral compound, preferably of formula I. Preferably 0.05 to 35%, particularly 0.1 to 1% of one or more compounds Contained in an amount of 0%.

A particularly preferred LC phase according to the invention for liquid crystal dielectrics is one of the compounds of the formula Or it contains 0.1 to 3% of two or more types. Contains only one compound of formula I Particularly preferred are dielectrics that

The LC phase according to the invention is prepared in a manner known per se. In general, the ingredients are mutually , preferably at elevated temperature.

The liquid crystal phase according to the present invention can be made by using suitable additives. It can be modified for use in all types of LC display elements.

Such additives are known to those skilled in the art and are described in detail in the literature.

For example, to improve conductivity, conductive salts, preferably ethyl dimethyl dode Cylammonium 4-hexoxybenzoate, tetrabutylammonium tetate A complex salt of raphenylboranate or crown ether can be added, and a colored guest Dichroic dyes can be added to create the host system, or dielectric anisotropy, viscosity and and/or substances can be added to alter the orientation of the nematic phase. like this For example, the substances described in West German Published Patent Application No. 2,209,172, 2.240,864, 2,321,632, 2,338,281 , No. 2,450,088, No. 2,537,430, No. 2,853,7 No. 28 and No. 2,902.177.

The compounds of formula I can also be used, optionally without the addition of further components, It can be used as a liquid crystal phase for temperature indicators. Preferably suitable for this purpose The compound has two ring structural groups in at least one of the group R1 or the group R1.

The following is intended to explain the invention without limiting it. This entire specification Throughout, all temperatures are given in °C. The abbreviations have the following meanings: m, p, - melting point, c, p, - clearing point, [α] - [α] parable with c = 1 in CH2CCt. number of % Values are in % by weight. The term "finished in the usual manner" has the following meanings: and water immiscible, such as CHtC12t-diethyl ether or toluene. Add a solvent, shake, separate the phases, wash the organic phase, Dry over O4, then evaporate and chromatograph the residue on silica gel. and/or crystallization.

Example of preparation of a compound of formula I: Example 1 p-(5-hebutylpyrimidin-2-yl)benzoic acid 2.989, (-)-1- p-hebutoxyphenyl-2-propatol 2.59 (rαJ--3,15° : This compound is obtained from (R)-propylene oxide and CtH+5MgBr. ], dicyclohexylcarbodiimide 2.3g, 4-dimethylaminopyridi Stir a mixture of 0.2g of water and 25s+12 dichloromethane at 20° for 48 hours. do. Cool in a water bath, separate the dicyclohexyl urea produced, and evaporate the filtrate. Concentrate by evaporation and then silica gel using toluene/ethyl acetate (98:2). 1-p-hebutoxyphenyl-2- Propyl (-)-p-(5-hebutylpyrimidin-2-yl)benzoate is obtained. M, p, 80° (recrystallized from ethanol); [α]--80.6°.

Similarly, by esterification, l-hebutoxyphenyl-2-propyl(+) -p-(5-hebutylpyrimidin-2-yl)benzoate and the following: The (+)- and (-)-forms of the ester are obtained.

Esters of the following acids: t-p-methoxyphenyl-2-propyl ester 1-p-ethoxyphenyl- 2-propyl ester t-p-propoxyphenyl-2-propyl ester 1-p-butoxyphenyl-2-propyl ester 1-p-pentoxyphenyl -2-propyl ester t-p-hexoxyphenyl-2-propyl ester t-p-heptoxyphenyl-2-propyl ester t-p-lactoxyphenyl-2-propyl ester t-p-Thornoxyphenyl-2-propyl estert-p-Thecoxyphenyl- 2-propyl ester acid: p-(5-propylpyrimidin-2-yl)benzoic acid p-(5-butylpyrimidine) p-(5-pentylpyrimidin-2-yl)benzoic acid p-(5-pentylpyrimidin-2-yl)benzoic acid -(5-hexylpyrimidin-2-yl)benzoic acid p-(5-hebutylpyrimidine) p-(5-octylpyrimidin-2-yl)benzoic acid p-(5-octylpyrimidin-2-yl)benzoic acid -(5-nonylpyrimidin-2-yl)benzoic acid 5-propylpicric acid 5-butylpicolinic acid 5-pentylpicolinic acid 5-hexylpicolinic acid 5-Hebutylpicolinic acid 5-octylpicolinic acid 5-nonylpicolinic acid 5-methoxypicolinic acid 5-ethoxypicolinic acid 5-propoxypicolinic acid 5-butoxypicolinic acid 5-pentoxypicolinic acid 5-hexoxypicolinic acid 5-hebutoxypicolinic acid 6-propylnicotinic acid 6-butylnicotinic acid 6-pentylnicotinic acid 6-hexylnicotinic acid 6-pentylnicotinic acid 6-octylnicotinic acid 6-nonylnicotinic acid 6-methoxypicolinic acid 6-ethoxynicotinic acid 6-propoxynicotinic acid 6-butoxynicotinic acid 6-Pentoxynicotinic acid 6-hexoxypicolinic acid 6-hebutoxynicotinic acid 5-(p-butylphenyl)picolinate 5-(p-propylphenyl)picolinic acid Acid 5-(p-pentylphenyl)picric acid 5-(p-hexylphenyl)pic 5-(p-hebutylphenyl) phosphate 5-(p-octylphenyl) picrate 5-(p-nonylphenyl)picric acid 5-(p-methoxyphenyl picrate) ) Picric acid 5-(p-propoxyphenyl)picric acid 5-(p-butoxyphenyl) 5-(p-pentoxyphenyl)picric acid 5-(p-pentoxyphenyl)picric acid xoxyphenyl)picolinic acid 5-(p-hebutoxyphenyl)picric acid 6- (p-propylphenyl)nicotinic acid 6-(p-butylphenyl)nicotinic acid 6-(p-pentylphenyl)nicotinic acid 6-(p-hexylphenyl)nicotinic acid 6-(p-heptylphenyl)nicotinic acid 6-(p-octylphenyl)nicotinic acid 6-(p-nonylphenyl) cotinic acid 6-(p-methoxyphenyl) nicotinic acid Nicotinic acid 6-(p-ethoxyphenyl) Nicotinic acid 6-(p-propoxyphenyl) nicotinic acid 6-(p-butoxyphenyl)nicotinic acid 6-(p-pentyl) xyphenyl) nicotinic acid 6-(p-hexoxyphenyl) nicotinic acid 6-(p -hebutoxyphenyl)nicotinic acid p-(5-propyl-2-pyridyl)benzoin Acid p-(5-butyl-2-pyridyl)benzoic acid p-(5-pentyl-2-pyridyl) ) p-(5-hexyl-2-pyridyl)benzoate p-(5-hebutyl benzoate) -2-pyridyl)benzoic acid p-(5-octyl-2-pyridyl)benzoic acid p-( 5-nonyl-2-pyridyl)benzoic acid p-(5-methoxy-2-pyridyl)benzoic acid p-(5-ethoxy-2-pyridyl)benzoic acid p-(5-propoxy-2- p-(5-butoxy-2-pyridyl)benzoic acid p-(5-pyridyl)benzoic acid p-(5-hexoxy-2-pyridyl)benzoic acid p-(5-hebutoxy-2-pyridyl)benzoate p-(2-propyl-5- pyridyl)benzoic acid p-(2-butyl-5-pyridyl)benzoic acid p-(2-pene thyl-5-pyridyl)benzoic acid p-(2-hexyl-5-pyridyl)benzoic acid p -(2-hbutyl-5-pyridyl)benzoic acid p-(2-hectyl-5-pyridyl) ) benzoic acid p-(2-nonyl-5-pyridyl)benzoic acid p-(2-methoxy-5 -pyridyl)benzoic acid p-(2-ethoxy-5-pyridyl)benzoic acid p-(2- Propoxy-5-pyridyl)benzoic acid p-(2-butoxy-5-pyridyl)benzoic acid p-(2-pentoxy-5-pyridyl)benzoic acid p-(2-hexoxy-5 -pyridyl)benzoic acid p-(2-hebutoxy-5-pyridyl)benzoic acid p-(pyridyl)benzoic acid p-(2-hebutoxy-5-pyridyl)benzoic acid Lance-4-propylcyclohexyl)benzoic acid p-()Lance-4-butylcyclohexyl)benzoic acid p-(trans-4-pentylcyclohexyl)benzoic acid p-(trans-4-hexylcyclohexyl)benzoic acid p-(trans-4-hebutylcyclohexyl)benzoic acid p-()Lance-4-octylcyclohexyl)benzoic acid p-(trans-4-nonylcyclot-xyl)benzoic acid p-()Lance-4-methoxycyclohexyl)benzoic acid p-()Lance-4-ethoxycyclohexyl)benzoic acid p-()Lance-4-propylcyclohexyl)benzoic acid p-(trans-4-butoxycyclohexyl)benzoic acid p-()Lance-4-pentoxycyclohexyl)benzoic acid p-()Lance-4-hexoxycyclohexyl)benzoic acid p-()Lance-4-heptoxycyclohexyl)benzoic acid trans-4-()trans-4-propylcyclohexyl)cyclohexane Rubonic acid trans-4-(trans-4-butylcyclohexyl)cyclohexanecarbo acid trans-4-()trans-4-pentylcyclohexyl)cyclohexanecal bonic acid trans-4-(trans-4-hexylcyclohexyl)cyclohexanecal bonic acid trans-4-(trans-4-hebutylcyclohexyl)cyclohexanecal bonic acid trans-4-(trans-4-octylcyclohexyl)cyclohexanecal bonic acid trans-4-(trans-4-nonylcyclohexyl)cyclohexanecarbo acid trans-4-(trans-4-methoxycyclohexyl)cyclohexanecal bonic acid trans-4-(trans-4-ethoxycyclohexyl)cyclohexanecal bonic acid trans-4-()trans-4-propoxycyclohexyl)cyclohexane Rubonic acid trans-4-(trans-4-butoxycyclohexyl)cyclohexanecal bonic acid trans-4-()trans-4-pentoxycyclohexyl)cyclohexane Rubonic acid trans-4-(trans-4-hexoxycyclohexyl)cyclohexane Rubonic acid trans-4-(trans-4-hebutoxycyclohexyl)cyclohexane Rubonic acid 2-(trans-4-propylcyclohexyl)-1,3-dioxane-5-ka Rubonic acid 2-() lance-4-butylcyclohexyl)-1,3-dioxane-5-ka Rubonic acid 2-(trans-4-pentylcyclohexyl)-1,3-dioxane-5-ka Rubonic acid 2-(trans-4-hexylcyclohexyl)-1,3-dioxane-5-carboxylic acid Rubonic acid 2-(trans-4-hebutylcyclohexyl)-1,3-dioxane-5-carboxylic acid Rubonic acid 2-(trans-4-octylcyclohexyl)-1,3=dioxane-5-ka Rubonic acid 2-(trans-4-nonylcyclohexyl)-1,3-dioxane-5-cal bonic acid 2-() lance-4-methoxycyclohexyl)-1,3-dioxane-5-ka Rubonic acid 2-(trans-4-ethoxycyclohexyl)-1,3-dioxane-5-carboxylic acid Rubonic acid 2-(trans-4-propoxycyclohexyl)-1,3-dioxane-5- carboxylic acid 2-(trans-4-butoxycyclohexyl)-1,3-dioxane-5-carboxylic acid Rubonic acid 2-(trans-4-pentoxycyclohexyl)-1,3-dioxane-5- carboxylic acid 2-(trans-4-hexoxycyclohexyl)-1,3-dioxane-5- carboxylic acid 2-(trans-4-hebutoxycyclohexyl)-1,3-dioxane-5- carboxylic acid 2-Fluoro-4-(trans-4-propylcyclohexyl)benzoic acid 2-Fluoro-4-()lanth-4-butylcyclohexyl)benzoic acid 2-Fluoro-4-()lanth-4-pentylcyclohexyl)benzoic acid 2-Fluoro-4-()lanth-4-hexylcyclohexyl)benzoic acid 2-Fluoro-4-(trans-4-heptylcyclohexyl)benzoic acid 2-Fluoro-4-(trans-4-octylcyclohexyl)benzoic acid 2-Fluoro-4-(trans-4-nonylcyclohexyl)benzoic acid 2-Fluoro-4-()lanth-4-methoxycyclohexyl)benzoic acid 2-Fluoro-4-(trans-4-ethoxycyclohexyl)benzoic acid 2-Fluoro-4-() lance-4-propoxycyclohexyl)benzoic acid 2-Fluoro-4-()lanth-4-butoxycyclohexyl)benzoic acid 2-Fluoro-4-() lance-4-pentoxycyclohexyl)benzoic acid 2-Fluoro-4-()lanth-4-hexoxycyclohexyl)benzoic acid 2-Fluoro-4-(trans-4-hebutoxycyclohexyl)benzoic acid trans-4-propylcyclohexanecarboxylic acid trans-4-butylcyclo trans-hexanecarboxylic acid-4-pentylcyclohexanecarboxylic acid trans- -4-hexylcyclohexanecarboxylic acid trans-4-hebutylcyclohexane trans-4-octylcyclohexanecarboxylic acid trans-4-octylcyclohexanecarboxylic acid Nonylcyclohexanecarboxylic acid trans-4-methoxycyclohexanecarboxylic acid trans-4-ethoxycyclohexanecarboxylic acid trans-4-propoxycarboxylic acid Cyclohexanecarboxylic acid trans-4-butoxycyclohexanecarboxylic acid trans-4-pentoxycyclohexanecarboxylic acid trans-4-hexoxy Cyclohexanecarboxylic acid trans-4-heptoxycyclohexanecarboxylic acid 5-(p-propylbenzoxy)picolinic acid 5-(p-butylbenzoxy)pico 5-(p-pentylbenzoxy) phosphoric acid 5-(p-hexylbenzoxy) picolinate c) 5-(p-hebutylbenzoxy) picolinate 5-(p-octyl) benzoxy)picric acid 5-(p-nonylbenzoxy)picolinic acid 5-(p-methane) Toxybenzoxy)picric acid 5-(p-ethoxybenzoxy)picric acid 5- (p-propoxybenzoxy)picolinic acid 5-(p-butoxybenzoxy)pic 5-(p-pentoxybenzoxy) phosphoric acid 5-(p-hexoxybenzoxy) 5-(p-heptoxybenzoxy)picric acid 6-(p-zoxy)picric acid ropylbenzoxy) nicotinic acid 6-(p-butylbenzoxy) nicotinic acid 6-( p-pentylbenzoxy)nicotinic acid 6-(p-hexylbenzoxy)nicotine Acid 6-(p-hebutylbenzoxy)nicotinic acid 6-(p-octylbenzoxy) Nicotinic acid 6-(p-nonylbenzoxy) Nicotinic acid 6-(p-methoxybenzo xy) nicotinic acid 6-(p-ethoxybenzoxy) nicotinic acid 6-(p-pro poxybenzoxy)nicotinic acid 6-(p-butoxybenzoxy)nicotinic acid 6 -(p-pentoxybenzoxy)nicotinic acid 6-(p-hexoxybenzoxy) Nicotinic acid 6-(p-hebutoxybenzoxy) Nicotinic acid 5-(p-propylphate) 5-(p-butylphenethyl)picric acid 5-(p-pene 5-(p-hexylphenethyl)picolinate 5-( 5-(p-octylphenethyl)picolinate Acid 5-(p-nonylphenethyl)picrate 5-(p-methoxyphenethyl)picrate 5-(p-ethoxyphenethyl) cholate 5-(p-propoxyphene) picrate 5-(p-butoxyphenethyl)picolinate 5-(p-pene) Toxiphenethyl) picolinic acid 5-(p-hexoxyphenethyl) picolinic acid 5 -(p-hebutoxyphenethyl)picolinic acid p-[2-(trans-4-propylene) (cyclohexyl)ethyl]benzoic acid p-[2-(trans-4-butylcyclohexyl)ethyl]benzoic acid p-(2-()lanse-4-pentylcyclohexyl)ethyl]benzoic acid p-(2-()trans-4-hexylcyclohexyl)ethyl]benzoic acid p-(2-()lans-4-hebutylcyclohexyl)ethyl]benzoic acid p-[:2-()rance-4-octylcyclohexyl)ethyl]benzoic acid p-(2-()lanth-4-nonylcyclohexyl)ethyl]benzoic acid p-(2-()trans-4-methoxycyclohexyl)ethyl]benzoic acid p-[2-()trans-4-ethoxycyclohexyl)ethyl]benzoic acid p-[:2-()rance-4-propoxycyclohexyl)ethyl]benzoic acid p-(2-()trans-4-butoxycyclohexyl)ethyl]benzoic acid p-[2-()rance-4-pentoxycyclohexyl)ethyl]benzoic acid p-(2-()lans-4-hexoxycyclohexyl)ethyl]benzoic acid p-[2-(trans-4-hebutoxycyclohexyl)ethyl]benzoic acid 2-Fluoro-4-(2-()lans-4-propylcyclohexyl)ethyl] benzoic acid 2-Fluoro-4-(2-()lans-4-butylcyclohexyl)ethyl]an Zozoic acid 2-Fluoro-4-(2-()lans-4-pentylcyclohexyl)ethyl] benzoic acid 2-Fluoro-4-[2-() lance-4-hexylcyclohexyl)ethyl] benzoic acid 2-Fluoro-4-(2-()lans-4-heptylcyclohexyl)ethyl] benzoic acid 2-Fluoro-4-(2-()lans-4-octylcyclohexyl)ethyl] benzoic acid 2-Fluoro-4-C2-()lanth-4-nonylcyclohexyl)ethyl]an Zozoic acid 2-Fluoro-4-(2-()lans-4-methoxycyclohexyl)ethyl] benzoic acid 2-Fluoro-4-(2-()lans-4-ethoxycyclohexyl)ethyl] benzoic acid 2-Fluoro-4-(2-()lans-4-propoxycyclohexyl)ethyl 〕benzoic acid 2-Fluoro-4-(2-()lans-4-butoxycyclohexyl)ethyl] benzoic acid 2-Fluoro-4-(2-()lans-4-pentoxycyclohexyl)ethyl 〕benzoic acid 2-Fluoro-4-(2-()lans-4-hexoxycyclohexyl)ethyl 〕benzoic acid 2-Fluoro-4-[2-()lans-4-heptoxycyclohexyl)ethyl 〕benzoic acid p-(trans-4-propylcyclohexylcarbonyloxy)benzoic acid p-(trans-4-butylcyclohexylcarbonyloxy)benzoic acid p-(trans-4-pentylcyclohexylcarbonyloxy)benzoic acid p-(trans-4-hexylcyclohexylcarbonyloxy)benzoic acid p-(trans-4-hebutylcyclohexylcarbonyloxy)benzoic acid p-()Lance-4-octylcyclohexylcarbonyloxy)benzoic acid p-(trans-4-nonylcyclohexylcarbonyloxy)benzoic acid p-(trans-4-methoxycyclohexylcarbonyloxy)benzoic acid p-(trans-4-ethoxycyclohexylcarbonyloxy)benzoic acid p-()Lance-4-propoxycyclohexylcarbonyloxy)benzoic acid p-(trans-4-butoxycyclohexylcarbonyloxy)benzoic acid p-(trans-4-pentoxycyclohexylcarbonyloxy)benzoic acid p-()Lance-4-hexoxycyclohexylcarbonyloxy)benzoic acid p-(trans-4-hebutoxycyclohexylcarbonyloxy)benzoic acid p-()Lance-4-propylcyclohexylmethoxy)benzoic acid p-(trans-4-butylcyclohexylmethoxy)benzoic acid p-()Lance-4-pentylcyclohexylmethoxy)benzoic acid p-(trans-4-hexylcyclohexylmethoxy)benzoic acid p-()Lance-4-hebutylcyclohexylmethoxy)benzoic acid p-()Lance-4-octylcyclohexylmethoxy)benzoic acid p-(trans-4-nonylcyclohexylmethoxy)benzoic acid p-()Lance-4-methoxycyclohexylmethoxy)benzoic acid p-()Lance-4-ethoxycyclohexylmethoxy)benzoic acid p-()Lance-4-propoxycyclohexylmethoxy)benzoic acid p-(trans-4-butoxycyclohexylmethoxy)benzoic acid p-(trans-4-pentoxycyclohexylmethoxy)benzoic acid p-()Lance-4-hexoxycyclohexylmethoxy)benzoic acid p-(trans-4-hebutoxycyclohexylmethoxy)benzoic acid trans-4-(2-()trans-4-propylcyclohexyl)ethylkoshik trans-4-C2-()trans-4-butylcyclohexanecarboxylic acid sil)ethylcocyclohexanecarboxylic acid trans-4-(2-()trans-4 -pentylcyclohexyl)ethylcocyclohexanecarboxylic acid trans-4- [2-(trans-4-hexylcyclohexyl)ethylcocyclohexanecal trans-4-(2-()trans-4-heptylcyclohexyl)ethyl bonate trans-4-C2-()trans-4-octyl cocyclohexanecarboxylic acid chlorohexyl)ethylcocyclohexanecarboxylic acid trans-4-[:2-( ) lance-4-nonylcyclohexyl)ethylcocyclohexanecarboxylic acid lance-4-C2-()lance-4-methoxycyclohexyl)ethylcocyclohe xanecarboxylic acid trans-4-C2-()trans-4-ethoxycyclohexy trans-4-(2-()trans-4-)ethylcocyclohexanecarboxylic acid propoxycyclohexyl)ethylcocyclohexanecarboxylic acid trans-4- (2-() lance-4-butoxycyclohexyl)ethylcocyclohexanecal trans-4-C2-()trans-4-pentoxycyclohexyl)ethyl bolic acid rucocyclohexanecarboxylic acid trans-4-(2-()trans-4-hexoxy) cyclohexyl)ethylcocyclohexanecarboxylic acid trans-4-C2-( ) lance-4-heptoxycyclohexyl)ethylcocyclohexanecarboxylic acid p-[2-(2-propyl-pyrimidin-5-yl)ethyl]benzoic acid p-[2-(2-butyl-pyrimidin-5-yl)ethyl]benzoic acid p-(2-(2-pentyl-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-hexyl-pyrimidin-5-yl)ethyl)benzoic acid p-[2-(2-heptyl-pyrimidin-5-yl)ethyl]benzoic acid p-(2-(2-octyl-pyrimidin-5-yl)ethyl)benzoic acid p'-(2-(2-nonyl-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-methoxy-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-ethoxy-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-propoxy-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-butoxy-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-pentoxy-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-hexoxy-pyrimidin-5-yl)ethyl)benzoic acid p-(2-(2-hebutoxy-pyrimidin-5-yl)ethyl)benzoic acid Example 2 3.16 g of p-(5-hebutylpyrimidin-2-yl)benzoyl chloride was (+)-1-p-heptoxyphenyl-2-propertool in lysine 15 2. 59 [(α]-+ 3.15°, this compound has (S)-propylene oxide and and Ctl (obtained from +5MgBr) with stirring at 0°, then After heating to 20” at 20°, the mixture is stirred at 20° for 16 hours. Water/toluene After customary work-up with t-p-hebutoxyphenyl-2- Propyl(+)-p-(5-hebutylpyrimidin-2-yl)-benzoate obtained; [α]=+Similarly to Example 1, the corresponding trans-4-propyl lohexyl 3-(p-(5-hebutylpyrimidin-2-yl)-phenyl]buty rate is (+)-3-(p-(5-hebutylpyrimidin-2-yl)phenyl ] Butyric acid [This compound is 3-(p-(5-hebutylpyrimidin-2-yl)phenol) Nyl-2-butenoic acid was hydrogenated over 5% Pd-C in THF, then (+) - Obtained by racemic separation using ephedrine; [α) + 3.3 °] and trans-4-propylcyclohexanol.

Similarly, 3-(p-(5-hebutylpyrimidin-2-yl)phenyl]butyric acid The following corresponding ester compounds are obtained in the (+)- and (-)-forms of trans-4-(trans-4-pentylcyclohexyl)cyclohexyl trans-4-(trans-4-butylcyclohexyl)cyclohexyl trans-4-pentylcyclohexyl p-pentylphenyl p-pentoxyphenyl 4'-hebutyl-4-biphenylyl 2-pentyl-5-pyridyl Example 4 (-)-3-Cp-(5-hebutylpyrimidin-2-yl)-phenyl]butyric acid Corresponding using 5occz of 1.79 dissolved in diethyl ether 10x& The solution was converted to acid chloride, and the solution was dissolved in 15 m of diethyl ether (p-pentyl Add dropwise to a solution of 1.649 g of phenol and 3 ff of pyridine (!) while stirring at 0''. and add. Stirring was continued for another hour at Oo, then for 16 hours at 20°, then The corresponding p-pentylphenyl 3-[:p-(5 -hebutylpyrimidin-2-yl) phenyltobutyrate is obtained.

Similarly, 3-[p-(5-hebutylpyrimidin-2-yl)phenyl]butyric acid The following corresponding ester compounds are obtained in the (+)- and (=)- forms: Lopylphenyl p-hebutoxyphenyl trans-4-pentylcyclohexyl-methyltrans-4-()trans-4 -propylcyclopyl-2-propyl-5-pyridyl 5-butyl-2-pyridyl Example 5 all-) lance-4-(4-propylcyclohexyl)cyclohexyl acetic acid 3.97 g of cesium salt, (+)-1-furomo-1-p-pentylphenylethane A mixture of 2.559 O and DMF30 was stirred at 60° for 16 hours, then normally Perform finishing treatment (water/hexane). Corresponding 1-p-pentylphenyleth Chiltrans-4-()trans-4-propylcyclohexyl)cyclohexane Acetate is obtained.

Similarly, the t-p-pentylphenylethyl ester of the following acid compound is (+) Obtained in - form and (-)- form: 2-(trans-4-pentylcyclohexyl)propionic acid trans-4-pentylcyclohexanecarboxylic acid trans-4-pentylcyclohexanecarboxylic acid trans-4-pentylcyclohexanecarboxylic acid trans-4-()trans-4-pentylcyclohexyl)cyclohexyl acetate lohexane acetic acid p~(trans-4-pentylcyclot-xyl)phenylacetic acid Example 6 Similarly to Example 1, the corresponding p-nonylphenyl 3-(p-5-hebutylpyriminyl Zin-2-ylphenyl)-2-methylpropionate is (-)-3-(p-5 -hebutylpyrimidin-2-ylphenyl)-2-methylpropionic acid ([α] -2,3°: This compound is 3-(p-5-heptylpyrimidin-2-ylphenate) Nyl)-2-methylacrylic acid was hydrogenated over 5% Pd-C in THF and then (obtained by racemic resolution using (+)-ephedrine) and Obtained from p-nonylphenol.

The following p-nonylphenyl ester of 2-methylpropionic acid is in (+)-form and and (-)-form, which can also be obtained by esterification: 3-(p-()lance-4-propylcyclohexyl)3-()lance-4-pe cyclohexyl)-3-(p-(2-heptyl-5-pyridyl)phenyl ]3-(2-hebutyl-5-pyridyl)-3-(p-(3-year-old ctyl-1,2, 4-)Ryazin-6-yl)phenyl]- 3-[p-(6-octyl-1,2,4-)riazin-3-yl)phenyl]- p-()Lance-4-propylcyclohexyl)bromobenzene 2.69g, M A Grignard solution prepared from g 0.249 and THFIOJ2 was (+)-1-Bromo-2-p-pentylphenylpropane while stirring at 2. 7Li.

Add dropwise to the mixture of LitCuC1246Gmg and THF30xC.

After stirring for 16 hours at 20°, decomposition with hydrochloric acid is carried out and then concentrated by evaporation. The corresponding 1-(p-) lance-4-pro pyrucyclohexyl)phenyl-2-p-pentylphenylpropane is obtained.

The 2-p-pentylphenyl listed below using the corresponding Grignard compound Propane compounds are similarly obtained in the (decade)- and (-)-forms: 1-(p-trans-4-butylcyclohexylphenyl)- 1-(p-trans-4-pentylcyclohexylphenyl)- 1-(p-) trans-4- corresponding to trans-5-propyl-1,3-dioxa Pentylcyclohexylmethyl 2-() lance-4-pentylcyclohexyl ) propionate was prepared in the same manner as in Example 4 to form (-) -2-() lance-4-pentyl from cyclohexylpropionic acid via the corresponding chloride of this acid to trans-4 -obtained using pentylcyclohexylmethanol.

The following equivalents of 2-(trans-4-pentylcyclohexyl)propionic acid Ester compounds are obtained analogously in (+)- and (-)-forms: p-pro pirbenzil p-hebutoxybenzyl p-(5-hebutylpyrimidin-2-yl)benzyl trans-4-pentylcyclohexylmethyl trans-4-(trans-4- propylcyclohexyl)cyclohexylmethyl 2-propyl-5-pyridylmethyl 5-butyl-2-pyridylmethyl Example 9 l-(4'-octoxybiphenyl-4-yl)-2-propyl(+)-to p- Xylbenzoate, M, p: 67°, [α] + 66.0° (c = 5% , in dichloromethane) as in Example 1, p-hexylbenzoic acid and! -(4 ’-cytoxybiphenyl-4-yl)propan-2-ol (this compound has 5 -(-)-propylene oxide).

Examples of nematic liquid crystal phases: Example A p-trans-4-propylcyclohexylbenzonitrile 15.8% p-) Lance-4-butylcyclohexylbenzonitrile 9.8% Trans-t-p-ethoxyphenyl-4-propylcyclohexane 10.9 % trans, trans-4-propylcyclohexyl-4'-propoxycyclohexyl Xane 8.8% trans, trans-4-pentylcyclohexyl-4'-methane Toxycyclohexane 7.8% trans, trans-4-pentylcyclohexane Sil-4'-ethoxycyclohexane 7.8% trans-4-propylcyclo Hexyltrans, trans-4-propylcyclohexylcyclohexane-4 '-Carboxylate 3.9% trans-4-pentylcyclohexyltrans, trans-4-propylcyclo lohexylcyclohexane-4'-carboxylate 3.9% trans-4-propylcyclohexyltrans, trans-4-butylcyclo Hexylcyclohexane-4'-carboxylate 3.9% trans-4-pentylcyclohexyltrans, trans-4-butylcyclo Hexylcyclohexane-4'-carboxylate 2.9% 2-Fluoro-4,4'-()lance-4-propylcyclohexyl)biphenylene Le 3.9% 2-fluoro-4-()lance-4-pentylcyclohexyl)-4'-()l (4-propylcyclohexyl)biphenyl 5.9% 2-Fluoro-4,4'-()lans-4-(pentylcyclohexyl)biphe Nil 2.9% 4.4'-bis-(trans-4-(propylcyclohexyl)biphenyl 3 ．． 9% 4-(trans-4-pentylcyclohexyl)-4'yl 5.9% and t-p-hebutoxyphenyl-2-propyl(-)-p-(5-hebutylpyrimi Zin-2-yl)benzoate 2.0% The mixture of M, p,: <-40°; C, p,: 105.4°; HTP: 11. 17ts-' (at 0°), 11.24 (at 20°), 11.1 7 (at 40°).

Example B p-trans-4-propylcyclohexylbenzonitrile 22.8% p-trans-4-pentylcyclohexylbenzonitrile 34.2% p-) Lance-4-heptylcyclohexylbenzonitrile 23.8% 4-cyano'-4'-() lance-4-pentylcyclohexyl)biphenyl 14.2% and 1-p-hebutoxyphenyl-2-propyl(-)-p-(5 -hebutylpyrimidin-2-yl)benzoate 5.0% The mixture has M, p, knee 5°, and c, p, : 69.7°.

Example C p-trans-4-ethylcyclohexylbenzonitrile 13% p-) Lance-4-propylcyclohexylbenzonitrile 16% p-trans-4-butylcyclohexylbenzonitrile 12% 4-ethyl-4'-cyanobiphenyl 9% 4-propyl-4'-cyanobiphenyl 8% trans-1-p-methoxyphenyl-4-propylcyclohexane 14% 4-ethyl-4'-() lance-4-propylcyclohexyl)biphenyl 1 2% 4-ethyl-4'-() lance-4-pentylcyclohexyl)biphenyl 8 % 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-pro Pyrcyclohexyl) biphenyl 7% and t-p-hebutoxyphenyl-2-propyl(-)-p-(5-hebutylpyry Midin-2-yl)-benzoate 1% Nz”N3X To j!E INTERNATIO:JAL 5EARCHR EPORT ON international search report

Claims (2)

[Claims] 1. Contains at least two types of liquid crystal components, including at least one type of chiral compound It is a nematic liquid crystal phase in which there are many chiral compounds in one chiral It is a compound with a chiral center, and this chiral center has two cyclic mesogenic properties. A nematic material characterized by being a crosslinking component containing an even number of crosslinking members between the bases. liquid crystal phase. 2. The chiral compound has formula I R1-X1-CHR0~(CH2)p-X2-R2 I [wherein X1 and X2 are -CO-O-, -〇-CO-, -CH2CO-O- , -CO-O-CH2, -CH2O-, -OCH2-, -CH2CH2, -O- or represents a single bond, and R1 and R2 are each independently a group -(A1- Z)m-(A2)n-Y, where A1 and A2 are each independently, 1,4-phenylene, one or more CH groups present in this group may be replaced by N, or A1 and A2 are each 1, represents 4-cyclohexylene, one CH2 group present in this group or the adjacent The two CH2 groups that are not Alternatively, A1 and A2 may each be 1,4-bicyclo[2,2, 2] represents octylene, and these groups also have one or two substituents The above F, Cl, Br, CN and/or alkyl group (this alkyl group is C up to 12 atoms, and one CH2 group present in this group or the adjacent The two CH2 groups that are not present may be replaced by O atoms). and Z is -CO-O, -O-CO-, -CH2CH2-, -OCH2-, -CH2O-, -CH=N-, -N=CH-, -N=N-, -N(O)=N- or a single bond, m represents 0, 1 or 2, n represents 1 or 2, Y represents a straight-chain or branched alkyl group having up to 12 C atoms; One CH2 group or two non-adjacent CH2 groups present in this group are O radicals. or Y may be replaced by F, Cl, Br or CN. , p represents 0 or 1, and R0 is an alkali having up to 5 C atoms. represents a kill group or R0 is a halogen, CN, phenyl group or cyclo Represents a hexyl group, provided that -X1CHR0-(CH2)p-X2- in the bridge The number of members is an even number, and also at least of X1 and X2 groups One represents a single bond] A nematic phase according to claim 1, characterized in that it corresponds to.