JPH11323341A - Electro-optical liquid crystal system - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid crystal system which is excellent in UV and temperature stabilities and useful for a large area displaying system by blending a dielectrically-positive liquid-crystal mixture and optionally an optically- transparent medium and applying it between two electrodes optionally fixed on a supporting sheet. SOLUTION: This system contains a liquid crystal mixture containing at leas tone compound of formula I. In the formula, Q<1> is a group of formula II; Rings A1-2 are each trans-1,4-cyclohexylene or (2- or 3-foluoro)-1,4-phenylene and one of A1 and A2, if A2 exists, is a pyridine-2,5-diyl, a pyrimidine-2,5-diyl or the like; Z1-2 are each a single bonding, -CH2 CH2 -, -COO-, -OCO-, -C=C- or -CH2 O-; X, Y are each H, F or Cl and at least one of them is Cl; and W is CN or NCS and if W is CN, the concentration of the compound of formula I in the system is less than 50 wt.%, and one of X and Y is F or one of Z<1> -Z<2> is -CH2 CH2 -. R<1> is a 1-12C alkyl; and m is 0-2.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention comprises: a dielectrically positive liquid crystal mixture and also an optically transparent medium between two electrodes optionally provided on a support sheet, the liquid crystal molecules being switched off. One of the indices of refraction of the liquid-crystal mixture essentially corresponds to the refractive index n _{M of the} matrix, and / or the mass of the liquid-crystal mixture is determined by the mass of the optically transparent medium. An electro-optic liquid crystal system having a divided value greater than or equal to 1.5 and having a reduced transmittance in one of the two switching states compared to the other state, independent of the polarization of the incident light, and for use in this system Liquid crystal mixture to be prepared.

[0002]

BACKGROUND OF THE INVENTION Depending on the mass of a liquid crystal mixture in a system, this mixture can be embedded in an optically transparent medium in the form of more or less demarcated liquid crystal microdroplets, or else the optical A transparent medium can form a somewhat cohesive continuous phase, for example present in the form of particles.
The continuous phase is also obtained, for example, when the optically transparent medium forms a sponge-like three-dimensional network whose pores through which the liquid crystal is arranged are more or less united with one another. Here, the expressions liquid crystal microdroplets demarcate one another, but need not be spherical at all, but may be irregularly shaped and / or deformed small liquid crystal segments. It represents.

When the optically transparent medium contains liquid crystal microdroplets, the medium is hereinafter referred to as a matrix. On the other hand, if there is even a slight continuous phase of the liquid crystal, this medium is described by the expression of a network structure.

[0004] NCAP (nematic curvilinear aligned)
phases, curvilinear array nematic phase) and PDLC (po
lymer dispersed liquid crystal
A film is an example of an electro-optic liquid crystal system in which liquid crystals are embedded in a matrix in the form of microdroplets. NCAP films are usually obtained by intimately mixing an encapsulated polymeric material such as polyvinyl alcohol, a liquid crystal mixture and a vehicle material such as water in a colloid mill. Thereafter, the vehicle substance is removed, for example, by drying. A suitable method is US Pat. No. 4,435,047.
It is described in. On the other hand, for example, US Pat.
8,900, Mol. Cryst, Liq. Cryst. Nonlin. Opti
c, 157 (1988) 427-441, WO 89/0
The preparation of PDLC films as described in 6264 and EP 0,272,582 involves first homogeneously mixing a liquid crystal mixture with the monomers or oligomers of the matrix-forming substance. Next, the mixture is polymerized and phase separation occurs [so-called PIPS (polymerization-i
nduced phase separation).
Furthermore, TIPS (temperature-induced phase separa)
, temperature-induced phase separation) and SIPS (solvent-induced)
phase separation, solvent-induced phase separation) [Mol. Cryst, Liq. Cryst. Inc. Nonli
n. Opt., 157 (1988) 427].

The PN (polymer network) system described in EP 0,313,053 has a sponge network structure of an optically transparent medium. The content of the liquid-crystal mixture in the light-modulating layer material is generally greater than 60%, in particular 70-90%, in such systems. PN
In order to produce a system, a mixture of a liquid crystal, a monomer or oligomer of a substance forming a three-dimensional network structure and a polymerization initiator, especially a photopolymerization initiator, is usually provided with an electrode.
After being introduced between the support plates, polymerization is performed, for example, by irradiating light.

Liquid crystals generally have a positive dielectric anisotropy Δε and a relatively high optical anisotropy. In a microdroplet matrix system, one of the indices of refraction of the liquid crystal, usually the ordinary index of refraction n _0, is selected to somewhat match the index of refraction n _M of the polymer matrix. In the case of the network structure system, there is no need to adjust the refractive index at all because the ratio of the liquid crystal normally present in the light modulation layer is very high, but this adjustment is performed to increase the light transmittance and contrast. be able to. An electrically switchable light scattering effect is seen in these electro-optical liquid crystal systems.

If no voltage is applied to the electrodes between which the matrix or network is normally arranged in a sandwich, the light incident on the randomly arranged liquid crystal molecules is greatly scattered and the system becomes opaque. When a voltage is applied, the liquid crystal molecules are aligned parallel to the electric field and perpendicular to the E vector of the transmitted light.

[0008] When microdroplet matrix systems, when a voltage is applied, light and n ₀ and n _M is incident perpendicularly to match are considered isotropic medium optically, and the system is transparent appear. Matching is necessary to prevent light scattering at the matrix / liquid crystal droplet phase interface. EP0,2
72,585, describes another embodiment in which the refractive index n _X in the liquid crystal in the case of a completely statistical orientation is aligned with the refractive index n _M of the matrix. In this case, the system is transparent in an electric field-free state, and changes to an opaque state by applying a voltage.

In the case of the network structure system, since the scattering at the network / liquid crystal phase interface is clearly not so remarkable because the ratio of the liquid crystal in the light modulating layer material is high, no refractive index matching is required at all. . When switched on, the system appears transparent even without index matching. In the case of a network structure system, it is preferable to use a liquid crystal having a high optical anisotropy in order to achieve the lowest possible transmittance without switching on.

[0010] WO 89/09807 states that in order to avoid the haze ("haze", especially "off-axis haze") often observed when the system is in the transparent state, an optically anisotropic,
For example, it has been proposed to use liquid crystalline polymer matrix materials. In this type of system, the refractive indices of the liquid crystal and the optically anisotropic matrix can be adapted to each other such that the transparent state is obtained either when a voltage is applied or when the switch is switched off.

An electro-optical liquid crystal system according to the preamble of claim 1 comprises:
In particular, it has been proposed for large area display systems, architectural applications (windows, partitions, awnings, etc.) and automobiles (windows, sunroofs, etc.). These systems are also suitable for regulating temperature by controlling the shielding of sunlight. These can be switched on by applying a DC or AC voltage.

These systems are particularly intended for "outdoor" applications and are therefore characterized by a high clearing point, a high Δε, a wide nematic range, an advantageous temperature dependence of the electro-optical parameters and a high UV and temperature stability. Liquid crystal mixture is required.

Examples of other applications include the following.

A GH display system whose spectrum ranges from a simple segment display to a display that can be applied to the desired electrode pattern using conventional printing techniques.
Applications: cars, large displays, bulletin boards, clocks.

A display with a high information content controlled by an active or passive matrix.

A projection system.

Switches.

Again, particularly high Δε, high electrical resistance,
There is a need for liquid crystal mixtures having advantageous values of electro-optic parameters and their temperature dependence, advantageous values of viscosity and high UV and temperature stability.

In microdroplet matrix systems, LC mixtures consisting of alkyl or alkoxy cyanobiphenyls and terphenyls have hitherto been customarily used. Thus, for example, US Pat. No. 4,688,900 and EP 0,272,585 describe the use of the liquid-crystal mixture E8 (from BDH, Poole, United Kingdom). This liquid crystal mixture has a high optical anisotropy Δn value of 0.247 and 54 mm
^It is characterized by a relatively high flow viscosity η value of ² / sec (20 ° C.), but at the same time has a relatively low clearing point of only 72 ° C. When a polynuclear polyphenyl compound is added to this mixture to increase the clearing point, the flow viscosity η becomes higher and the optical anisotropy Δn remains unchanged or becomes higher. High Δn values on the one hand ensure high light scattering in the opaque state, but on the other hand cause haze of the system (“haze”, in particular “off-axis haze”) when switched on, and thus a deterioration of the electro-optical properties . Indeed, in systems controlled by a relatively low frequency AC voltage, a high flow viscosity η is desirable to obtain a flicker-free display. However, on the other hand, in high information content matrix displays, liquid crystal mixtures with relatively low viscosities are necessary to achieve fast switching times.

Liquid-crystal mixtures E7 used in US Pat. No. 4,671,618, which likewise consist of alkyl and alkoxy cyanobiphenyls and terphenyls
(Made by BDH, Poole, UK) clearly has a relatively low flow viscosity of η = 39 mm ² / s and an optical anisotropy Δn of Δn = 0.225 and somewhat lower than E8, but at the same time the clearing point T _c It is quite low at 60.5 ° C. The dielectric anisotropy Δε of mixture E7 is 13.8, so Δε = 15.
6 slightly lower than E8. In order to obtain the lowest possible threshold voltage, even higher values of Δε are advantageous.

EP 0,313,053 proposes liquid-crystal mixtures based on 2- (4-cyanophenyl) pyridines for a network structure system. Liquid crystal mixtures of this kind have relatively high values for the dielectric anisotropy Δε, and thus relatively low threshold voltages and high or very high values for the optical anisotropy Δn, but at the same time these liquid crystals It is characterized by a relatively high viscosity η, a relatively low clearing point _Tc and an inadequate operating temperature range for many applications. In addition, cyanophenylpyridine compounds have particularly lower UV and temperature stability than cyanooligophenyl compounds.

The liquid crystals used so far have a wide nematic phase range, a high clearing point, a very high heat and a high nematic phase which can be optimized for the respective application and high Δε.
It satisfactorily satisfies the requirements for V stability, absence of smectic phases up to low temperatures, optical anisotropy Δn and flow viscosity η.

In addition, conventional liquid crystals often have too low a miscibility with the monomers and / or oligomers of the polymers used to form the matrix or network. This significantly impairs the production of PN systems and, in the case of microdroplet matrix systems, especially PI
It significantly limits the use of PS technology. Furthermore, these liquid crystals are often characterized by excessively high solubility in the matrix or network forming polymer. A further disadvantage of the prior liquid crystals is that, in many cases, these liquid crystals have undesired values of electro-optical parameters such as, for example, the slope of the electro-optical curve and / or electro-optical properties for the respective application, for example a threshold voltage. The purpose is to show the temperature dependence of the parameters.

Therefore, it is more suitable for specific requirements. And there is still a great need for electro-optical liquid crystal systems that do not have the above-mentioned disadvantages or only to a relatively small extent.

[0025]

SUMMARY OF THE INVENTION Accordingly, the present invention is based on the object of obtaining an electro-optical liquid crystal system and a liquid crystal which do not have the drawbacks mentioned for the prior art systems or which have only a relatively small extent. Met. Other objects of the present invention will become readily apparent to those skilled in the art from the following detailed description.

[0026]

Means for Solving the Problems Equation 1

[0027]

Embedded image (Where Q ¹ is

[0028]

Embedded image Wherein ring A ¹ and ring A ² independently of one another, are trans-1,4-cyclohexylene, 1,4-phenylene,
-Fluoro-1,4-phenylene, 3-fluoro-1,
4-phenylene and A ¹ and one of A ² , if present, are pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydro It is also pyran-2,5-diyl or naphthalene-2,6-diyl, wherein Z ¹ and Z ² are each independently a single bond, —CH ₂ CH ₂ —, —COO—, —
OCO—, —C≡C—, —CH ₂ O— or a combination of two or more of these bridge members, wherein Y and X are each independently H or F; One is also Cl and W is -CN or -NCS,
(1) the concentration of the compound of the formula I in the system is 5
0% by weight, and (2) any one of Y and X
One is F, or (3) ^one of Z ¹ and Z ² is —CH ₂ CH ₂ —, and R ¹ and R ² are, independently of one another, one of them or non-adjacent 2 One CH ₂ group is an alkyl having 1 to 12 C atoms, and m is 0, 1 or 2). It has been found that the object of the present invention can be achieved when a contained liquid crystal mixture is used in a system.

The invention therefore comprises: a dielectrically positive liquid crystal mixture and also an optically transparent medium between two electrodes, optionally provided on a support sheet, wherein the liquid crystal molecules are switched off. One of the indices of refraction of the liquid crystal mixture essentially corresponds to the refractive index n _M of the optically isotropic transparent medium, or the index of refraction of the liquid crystal mixture is optically equal. The intrinsic refractive index of the isotropic transparent medium and / or the mass of the liquid crystal mixture divided by the mass of the optically transparent medium is greater than or equal to 1.5; Regardless, the invention relates to an electro-optical liquid crystal system which has a reduced transmission in one of the two switching states compared to the other, and wherein the liquid crystal contains one or more compounds of the formula I.

[0030]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The construction of an electro-optical liquid crystal system according to the invention corresponds to the usual manner of construction of this type of system. in this case,
The term conventional mode of construction is to be interpreted broadly and includes all applications and modifications.

Therefore, for example, PDLC or NC
In the case of AP, a matrix formed by a transparent medium that finely disperses or finely encapsulates a liquid crystal mixture is disposed between conductive electrodes in a sandwich shape.

The electrodes are provided in particular on a support sheet, for example of glass, plastic or the like. However, if desired, the electrodes can be provided directly on the matrix and the use of a support can be omitted.

In the case of the network system, the liquid crystal is placed in the pores of a sponge-like three-dimensional network, or an optically transparent medium is placed in the liquid crystal in the form of small, for example, spherical particles. The network structure is usually arranged between supports provided with electrodes to prevent liquid crystal from escaping.

Since both the network system and the microdroplet matrix system can function reflectively or transmissively, at least one electrode and, if present, its associated support are transparent. Both systems usually do not include a polarizer. The result is a distinctly higher transmission.
Furthermore, no orientation phase is required. This is a considerable technical simplification in the production of these systems compared to conventional liquid crystal systems such as, for example, TN or STN cells.

The matrix or three-dimensional network structure is
In particular, they are based on isotropic thermoplastic resins, thermosetting resins and elastomers. Depending on the intended use,
The resulting system can be flexible, elastic or rigid.

Systems based on thermoplastic polymers can easily be deformed by the action of mechanical stress at temperatures above the glass temperature of the matrix. This can be used, for example, in a microdroplet matrix system to solidify the drops into a particular deformed shape by cooling the matrix to a temperature below the glass temperature. further,
For example, the matrix can be mechanically stretched at a temperature above the glass temperature or oriented by the action of an electric or magnetic field. This orientation is carried out at a temperature below the glass temperature, making the matrix optically anisotropic.

The plastic and / or elastic system is preferably based on thermoplastics and / or elastomers, but it is preferable to use thermosetting resins for producing rigid systems. These can be mechanically deformed, for example, during curing, so that, for example, the shape and arrangement of the microdroplets is constant in the cured matrix.

Materials which are particularly suitable for the production of the matrix or the network are well described in the literature. For example, US 4,435,047 or Liquid Crystals, 3 , (1988) 1543.
For example, a water-soluble polymer such as polyvinyl alcohol PVA or a latex emulsion has been proposed. On the other hand, US 4,672,618, US 4,673
255, US 4,688,900, WO 85/0426
2 and Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt.
157 (1988) 427 list, for example, thermally cured synthetic resins such as epoxy resins and polyurethanes as suitable matrix materials. E
P 0,272,585 describes matrix or network materials based on photocurable vinyl compounds, and WO 89/06264 proposes copolymerization of polyfunctional acrylates containing polyfunctional mercaptans. Other details of polymers particularly suitable for matrix systems are described, for example, in EP 0,165,063, EP 0,345,
029, EP0,357,234 or EP0,20
5,261.

Regarding the network system, many three-dimensional crosslinkable monomers such as, for example, di- and triacrylates
0,313,053.

However, further transparent substances such as inorganic oxide glass bodies (US Pat. No. 4,814,211) and other inorganic substances (for example, JP-A-63-303)
325) Alternatively, other materials can also be used for the matrix and network system.

The above materials are merely illustrative of the invention and do not limit the invention in any way. In principle, all transparent substances which make it possible to produce the abovementioned matrix or network according to the preamble of claim 1 can be used.

Preferred embodiments of the electro-optical liquid crystal system according to the present invention are NCAP films, PDLC films and microdroplet matrix systems produced by an improved method. Methods for producing these films are described, for example, in US
4,688,900, US4,673,255, US
4,671,618, WO85 / 0426, US4,4
35,047, EP 0,272,595, Mol. Cry
St. Liq. Cryst. Inc. Nonlin. Opt., 157 (198
8) 427, Liquid Crystals, 3 , (198
8) 1543, EP0,165,063, EP0,34
5,029, EP0,357,234 and EP0,2
05,261.

A further preferred embodiment of the electro-optical liquid crystal system according to the invention is a network system whose manufacture is described in EP 0,313,053. In the present invention, arrangements in which transparent media are individually dispersed in liquid crystals, for example, in the form of spherical particles, as described in GB 1,442,360, also belong to the network system.

However, embodiments in which the transparent medium has an intermediate structure between the network structure on the one hand and the microdroplet matrix structure on the other hand are also included in the present invention.

Further, other embodiments not specifically described herein are also included in the present invention.

The thickness d of the electro-optical system is usually chosen to be as small as possible to achieve the lowest possible threshold voltage V _th . Thus, layer thicknesses of 0.8 mm and 1.6 mm have been reported, for example, in US Pat. No. 4,435,047, with values between 10 μm and 300 μm being considered in US Pat.
00 and the values from 5 μm to 30 μm correspond to EP 0,313,
This is shown as layer thickness at 053. Only in exceptional cases, the electro-optical system according to the invention has a layer thickness d significantly greater than a few mm, but preferably the layer thickness is d ≦ 2 mm.

The threshold voltage is also affected by the size of the microdroplets or the mesh width of the mesh structure. In general, a relatively small microdroplet results in a relatively high threshold voltage V _th but with a shorter switching time t _on or t _off (US Pat. No. 4,673,255). Experimental methods that affect average droplet size are described, for example, in US Pat. L. Mol. Cryst. Liq. Cryst. In West
Inc. Nonlin. Opt., 157 (1988) 427. US 4,673,255 is 0.1 μm to 8
Although an average droplet diameter of μm is indicated, for example, a matrix consisting of a glass body has pores with a diameter of 15 to 2,000 °. With respect to the mesh width of the PN-based network structure, the preferable range of 0.5 μm to 2 μm is EP0,31.
3,053.

However, an essential difference between the electro-optical liquid crystal system of the present invention and the conventional conventional one is that a different liquid crystal mixture is used.

The liquid-crystal mixtures according to the invention comprise at least one compound of the formula I
Contains species of compounds.

The compounds of the formula I are of the sub-formula I2, I3 and I
4:

[0051]

Embedded image 2, 3, and 4 cyclically dielectrically positive or dielectrically neutral compounds.

In the compounds of the formulas I2 to I4, X and Y are, independently of one another, H, F or Cl, in particular H
Or F. The compounds of the formulas I3 and I4 preferably contain no more than two, in particular no more than one heterocycle.
In the compounds of the formulas I3 and I4, one of the bridges Z ¹ and Z ² is preferably a single bond.

In the compounds of the formula I and of the sub-formulas of the compounds I2 to I4, R ¹ and, if present, R ² are, independently of one another, one or two non-adjacent CH _2-
1 which can be replaced by O- or -CH = CH-
It is an alkyl having 原子 12 C atoms.

If R ¹ and / or R ² if present is an alkyl group and / or an alkoxy group, this can be straight-chain or branched. This group is straight-chain and preferably has 1, 2, 3, 4, 5, 6 or 7 C atoms and is thus methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, Preferably it is propoxy, butoxy, pentoxy, hexoxy or heptoxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, octoxy, nonoxy, decoxy, undecoxy or dodecoxy.

Oxaalkyl is straight-chain 2-oxapropyl (= methoxymethyl), 2-oxabutyl (= ethoxymethyl) or 3-oxabutyl (= 2-methoxyethyl), 2-, 3- or 4-oxapentyl,
-, 3-, 4- or 5-oxahexyl, 2-3
-, 4-, 5- or 6-oxaheptyl, 2-3
-, 4-, 5-, 6- or 7-oxaoctyl, 2
-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, or 2-, 3-, 4-, 5-, 6-, 7-,
Preferably it is 8- or 9-oxadecyl.

R ¹ and / or R ² if present are
If one CH ₂ group is an alkyl group is replaced by -CH = CH-, this may be a straight or branched chain. This group is preferably straight-chain and has 2 to 10 C atoms. Thus, this group is especially vinyl, 1- or 2-propenyl, 1-, 2- or 3
-Butenyl, 1-, 2-, 3- or 4-pentenyl,
1-, 2-, 3-, 4- or 5-hexenyl, 1-, 2
-, 3-, 4-, 5- or 6-heptenyl, 1-, 2
-, 3-, 4-, 5-, 6- or 7-octenyl,
1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-
Nonenyl, or 1-, 2-, 3-, 4-, 5-, 6-,
7-, 8- or 9-decenyl.

In the compounds of the formula I, the radicals R ¹ and / or R ² if present can be straight-chain or branched, but are preferably straight-chain. The compound of formula I with a branched alkyl or alkoxy group also has better solubility in common liquid-crystal substrates, and is important in some cases, but if it is optically active, ,
It is particularly important as a chiral dopant. An electro-optical system according to the preamble of claim 1 wherein the liquid crystal contains one or more chiral components is described in DE 39 11 255.1.

Branching groups of this kind generally contain one or less chain branches. Preferred branching groups are isopropyl, 2-
Butyl (= 1-methylpropyl), isobutyl (= 2-
Methylpropyl), 2-methylbutyl, isopentyl (= 3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 2-octyl, isopropoxy, 2-methylpropoxy, 2-methyl Butoxy, 3-methylbutoxy, 2
-Methylpentoxy, 3-methylpentoxy, 2-ethylhexoxy, 2-methylhexoxy, 2-octyloxy, 2-oxa-3-methylbutyl, 3-oxa-4
-Methylpentyl, 4-methylhexyl, 2-nonyl,
6-methyloctoxy, 2-methyl-3-oxapentyl and 2-methyl-3-oxahexyl.

The compounds of the formula I are described in the literature [eg Houben-Weyl, published by Georg-Thieme publisher Stuttgart, "Methoden der Organischen Chemie". , Vo
l. IX, p. And a reaction method suitable for the above-mentioned reaction, particularly in accordance with a known method. In this regard, it is also possible to use alternatives which are known per se, but which are not explained here in further detail.

Particular preference is given to a small group of compounds of the subformula Ia.

[0061]

Embedded image (Wherein ring A ³ and ring A ⁴ are independently 1,4-
Cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and X ¹ is H or F, and a combination of the following numbers 1-5: but n, applies to Z ³ and Z ^4: number n Z ² Z ³ 1 0 single bond _{- 2 0 -CH 2 CH 2 -} - 3 1 -CH 2 CH 2 - single bond 4 1 single bond -CH ₂ CH ₂ -51 single bond single bond For the sake of simplicity, in the following, Cyc is trans-
1,4-cyclohexylene, Phe is 1,4-phenylene, and Phe. 2F is 2-fluoro-1,4
-Phenylene, Phe. 3F is 3-fluoro-
1,4-phenylene; Phe. F2 is 2,3-difluoro-1,4-phenylene; Phe. 3F5
F is 3,5-difluoro-1,4-phenylene,
Phe. F is 2- or 3-difluoro-1,4-phenylene, Pyr is pyrimidine-2,5-diyl, Pyd is pyridine-2,5-diyl, Di
o is 1,3-dioxane-2,5-diyl and Thp is tetrahydrofuran-2,5-diyl. The acronyms Pyr, Pyd, Dio and Thp in each case comprise the two possible positional isomers and the acronyms Phe. 2Cl, Phe. 3Cl, Ph
e. 3Cl5Cl and Phe. The meaning of Cl is clear from the meaning of the individual fluorinated 1,4-phenylene groups.

The compounds of the subformula Ia are of the following subformula Ia
Compounds of 2-1 to 1a2-6 include preferred bicyclic compounds.

R ¹ -Phe-Phe.3F-CN Ia2-1 R ¹ -Phe-Phe.3F5F-CN Ia2-2 R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F-CN Ia2-3 R ^1- Cyc-CH ₂ CH ₂ -Phe.3F5F-CN Ia2-4 R ¹ -Cyc-Phe.3F-CN Ia2-5 R ¹ -Cyc-Phe.3F5F-CN Ia2-6 Subformula Ia2-1 to Ia2-6 In the compound of the formula, R ¹
Has the meaning given for the compounds of the formula I. R ¹ is 1
Preference is given to alkyl, alkenyl or alkoxy having 10, in particular 1 to 8, C atoms. n-alkoxyalkyl compounds, especially n-methoxyalkyl, n-
Alkoxyethyl and n-alkoxymethyl compounds are more preferred. Formulas Ia2-2, Ia2-4 and Ia
Liquid crystal media containing the compounds of 2-6 have particularly advantageous values for the dielectric anisotropy. The lower formulas Ia2-1 and Ia
In compounds 2-2, Phe may be laterally fluorinated independently of one another in each case.

Compounds of sub-formula Ia have the following sub-formula Ia
3-1 to Ia3-16, and preferably includes tricyclic compounds.

R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe.3F-CN Ia3-1 R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-2 R ¹ -Cyc-Cyc- CH ₂ CH ₂ -Phe.3F-CN Ia3-3 R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-4 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-CN Ia3-5 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F5F-CN Ia3-6 R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe.3F-CN Ia3-7 R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe.3F5F-CN Ia3-8 R ¹ -Phe-Phe-Phe.3F-CN Ia3-9 R ¹ -Phe-Phe-Phe.3F5F-CN Ia3-10 R ¹ -Cyc-Phe- Phe.3F-CN Ia3-11 R ¹ -Cyc-Phe-Phe.3F5F-CN Ia3-12 R ¹ -Cyc-Cyc-Phe.3F-CN Ia3-13 R ¹ -Cyc-Cyc-Phe.3F5F-CN Ia3-14 R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe.3F-CN Ia3-15 R ¹ -Phe-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-16 R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe.3F-CN Ia3-17 R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-18 In the compounds of the lower formulas Ia3-1 to Ia3-18,
¹ has the meaning given for the compound of formula I and R ¹ is 1 to
Preferably it is n-alkyl, n-alkenyl or n-alkoxy having 10 C atoms, more preferably 1 to 1
N-alkoxymethyl having 8 C atoms or n-
It is also alkoxyethyl.

R ¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentoxymethyl, Formula Ia3-1 which is methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl or pentoxyethyl
The compound of Ia3-18 is a particularly preferred compound.

In the compounds of the subformulae Ia3-1 to Ia3-18, the Phe groups may in each case independently of one another be laterally fluorinated, in particular monofluorinated.

Formulas Ia, Ia2-1 to Ia2-6 and I
Most of the compounds a3-1 to Ia3-18 are known, and preferably DE3,209,178, JP62
−103,057, DE3,929,418, JP63
-216,858, DE3,401,320, EP0,
119,756, DE3,632,411, EP0,2
05,998, in particular DE 3,929,
418.

Formula Ia, specifically, Formulas Ia2-1 to Ia2-
Liquid crystal mixtures containing the compounds of formulas 6 and Ia3-1 to Ia3-18 are particularly suitable for use in the electro-optical system according to the invention, and also have advantageous values for the birefringence Δn and the flow viscosity η, high stability It is characterized by low miscibility with the polymers used for the matrix, and particularly advantageous values for the wide mesogenic range, relatively high clearing points and dielectric anisotropy, the threshold voltage and the temperature dependence of the electro-optical parameters.

The liquid crystals used in the electro-optical liquid crystal system according to the invention are from 1 to 40%, in particular from 5 to 30%, of the lower formulas Ia, in particular the lower formulas Ia2-1 to Ia2-6 and Ia3-1 to Ia3-.
Preferably, it contains 18 compounds. These liquid crystals have 1 to 5, in particular 1 to 3, lower formulas Ia, in particular lower formulas Ia2-1 to Ia2-6 and Ia3-1 to Ia3-.
Preferably, it contains 18 compounds.

The liquid-crystal mixtures are particularly preferably based on compounds of the following formulas II to IV in addition to the compounds of the lower formula Ia.

TW ¹ -Phe-CN II RW ¹ -Cyc-CN III TV-Phe-CN IV (wherein R is, in each case independently of one another, one or two non-adjacent CH ₂ groups To -O-, -CO
- an alkyl group having 1 to 15 C atoms that may also be replaced with and / or -CH = CH, W ¹
Is Phe. (F) -Y ¹ or Cyc-Y ¹ , Y ¹ is a single bond, —COO— or —OCO—, and V is pyridine-1,5-diyl or pyrimidine-.
2,5-diyl, and T is R, R-Phe. (F)-
Y ¹ or R-Cyc-Y ¹ , and Ph
e. (F) is 1,4-phenylene, 2-fluoro-1,
4-phenylene or 3-fluoro-1,4-phenylene). In the compounds of the formulas II to IV, the terminal group P
he-CN is preferably such that Y ¹ is —COO— or —OCO—
Where F can be mono- or difluorinated at 3 and / or 5 sites.

The compounds of the formulas II to IV are known or described in the literature [for example, Hoven-Weyl, published by Georg-Sime, Stuttgart, "Methods of Organic Chemistry", Vol. IX, p. 867 et seq.], And under any known reaction conditions suitable for the above reaction. In this regard, it is also possible to use alternatives which are known per se, but which are not explained here in further detail.

The subformulae Ia, in particular the subformulae Ia2-1 to Ia2, in the liquid crystal mixture used in the electro-optical liquid crystal system according to the invention
-6 and a component mixture of one or more compounds selected from the group of compounds of Ia3-1 to Ia3-16 and one or more compounds selected from the group of compounds of formulas II to IV have a content of 15 % To 100%, especially 25% to 100%
%. Subformula Ia, especially subformula Ia2
-1 to Ia2-6 and one of Ia3-1 to Ia3-16
In addition to one or more compounds, this component mixture comprises the following compounds II1-II25, III1-III3 and IV1-
It is particularly preferred to include one or more compounds selected from the subgroup of IV8.

R-Cyc-Phe-CN II1 R-Cyc-COO-Phe-CN II2 R-Cyc-COO-Phe.3F-CN II3 R-Cyc-COO-Phe.3F5F-CN II4 R-Phe-Phe -CN II5 R-Phe-COO-Phe-CN II6 R-Phe-COO-Phe.3F-CN II7 R-Phe-COO-Phe.3F5F-CN II8 R-Cyc-Phe-Phe-CN II9 R-Cyc -COO-Phe-Phe-CN II10 R-Cyc-Phe-COO-Phe-CN II11 R-Cyc-COO-Phe-Phe.3F-CN II12 R-Cyc-COO-Phe-Phe.3F5F-CN II13 R -Cyc-Phe-COO-Phe.3F-CN II14 R-Cyc-Phe-COO-Phe.3F5F-CN II15 R-Phe-Phe-Phe-CN II16 R-Phe-Phe.3F-Phe-CN II17 R -Phe-Phe.2F-Phe-CN II18 R-Phe-COO-Phe-Phe-CN II19 R-Phe-COO-Phe-Phe.3F-CN II20 R-Phe-COO-Phe-Phe.3F5F-CN II21 R-Phe-Phe-COO-Phe-CN II22 R-Phe-Phe-COO-Phe.3F-CN II23 R-Phe-Phe-COO-Phe.3F5F-CN II24 R-Cyc-Cyc-CN III1 R -Cyc-COO-Cyc-CN III2 R-Cyc-OCO-Cyc-CN III3 R-Pyd-Phe-CN IV1 R-Pyr-Phe-CN IV2 R-Pyd-Phe-Phe-CN IV3 R-Pyr-Phe -Phe-CN IV4 R-Phe-Pyd-Phe-CN IV5 R-Phe-Pyr-Phe-CN IV6 R-Cyc-Pyr-Phe-CN IV7 R-Cyc-Pyd-Phe-CN IV8 Subformula Ia, especially Selected from compounds of the subformulae Ia2-1 to Ia2-6 and Ia3-1 to Ia3-16 Even without the addition one compound, one or more compounds selected from compounds of subformula II1~II24 and subformula I
Component mixtures containing at least one compound selected from the compounds V1 to IV8 are very particularly preferred.

Preference is given to liquid-crystal mixtures based on the following component mixtures T (Ia) 1-4, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 types,
It preferably contains 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

Mixture Formula Mass in Component Mix [%] T (Ia) 1 Ia 5-75 II 6-75 T (Ia) 2 Ia 5-55 II 5-65 III 5-29 T (Ia) 3 Ia 5 -75 IV 5-63 T (Ia) 4 Ia 5-55 II 5-49 IV 5-50, especially 5-31 The system of the invention is such that the liquid-crystal mixture is based on the following group of compounds: Is also particularly preferred.

R-Cyc-Phe-CN II1 R-Phe-Phe-CN II5 R-Cyc-Phe-Phe-CN II9 R-Phe-Phe-Phe-CN II16 This system increases the dielectric anisotropy Characterized in that the liquid-crystal mixture contains 5 to 60% of one or more compounds of the following formula:

R-Phe.2F-Phe-CN II25 R-Phe.3F-Phe-CN II25a R ¹ -Phe-Phe.3F-CN Ia2-1 R ¹ -Phe-Phe-Phe.3F-CN Ia3- 9 R-Phe-Phe.2F-Phe-CN II18 R-Phe-Phe.3F-Phe-CN II17 R-Cyc-Phe.2F-Phe-CN II26 R-Cyc-Phe.3F-Phe-CN II27 R -Phe.F-Phe.F-Phe-CN II28 (wherein, the meanings of R ¹ and R are as described above, and R is preferably an alkyl group having 2 to 7 C atoms. Such mixtures are preferred and are the subject of the present invention.

In the following, the compounds II1, II5, I
This liquid-crystal mixture component based on I9 and II16 is sometimes referred to as component (i), while the compound II2
5, Ia2-1, Ia3-9, II17, II18, I
Components based on I26, II27, II28 and II25a are sometimes referred to as component (ii). These liquid-crystal mixtures may consist only of components (i) and (ii), but it is also possible for the liquid-crystal mixture to contain other components (iii) and (iv). Component (iii) is
Other nematics or nematics which are selected such that the birefringence Δn and / or ordinary refractive index n ₀ and / or other refractive indices and / or other parameters of the liquid crystal are specifically optimized for the respective application Contains forming substances. Nematic or nematic forming substances which can also preferably be used for component (iii) are further listed below. Component (iv) comprises, for example, chiral dopants for reducing the cholesteric phase and / or polychromatic dyes and / or other additives for modifying other properties of the liquid crystal mixture, for example, conductivity. I have. In this regard, compounds of component (iv) can be both mesophase-forming and non-mesophase-forming.

The mass of the component (i) in the liquid crystal is 10 to 80.
%, Especially 15-70%, more particularly 15-65%. If the liquid crystal mixture is to have a high birefringence of Δn> 0.24, component (i) may comprise 4-alkyl and / or 4-alkoxy-4′-cyanocobiphenyls and / or 4-alkyl and / or 4-alkoxy-4 "-cyanosa-phenyls and / or
Or 4- (trans-4-alkyl or trans-
4-alkoxycyclohexyl) -4′-cyanobiphenyls. On the other hand, the liquid crystal mixture
When having a birefringence of 3 ≦ Δn ≦ 0.22,
Component (i) preferably contains 4- (trans-4-alkyl or trans-4-alkoxycyclohexyl) benzonitrile in addition to one or more of the high Δn compounds of component (i) just described. .

Preferred formulas II25, II25a and I
In the laterally fluorinated biphenyls of a2-1, R ¹ is preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy and heptoxy.

Further, the component (ii) has the formula Ia3-9,
It is preferred to include laterally monofluorinated tricyclic compounds of I17, II18, II26 and II27. In these compounds, R ¹ is preferably alkyl, alkoxy or alkoxyalkyl having ¹ to 7 C atoms, in particular 2 to 7 C atoms, especially 2 to 5 C atoms.

If a liquid crystal mixture having a high clearing point is to be obtained, component (i) preferably comprises the tricyclic compounds of the formulas II9 and II16 and / or component (ii) is of the formula Ia3- 9, II17, II18, II2
It is preferred to include the tricyclic compounds of 6, II27 and II28. At least one of formulas II9 and II
16 compounds and at least one compound of the formula Ia3-9, I
Liquid crystal mixtures comprising the compounds I17, II18 and II26-28 are particularly preferred because these mixtures generally have a high clearing point with relatively high or high values for Δε.

The liquid-crystal mixture containing components (i) and (ii) should have a clearing point of T _c > 75 ° C., in particular T _c > 80 ° C., and more particularly T _c > 85 ° C. preferable.

Formulas II25, II25a, Ia2-1, I
The laterally fluorinated compounds a3-9, II18, II17 and II26-28 usually have very good solubility in component (i) and the modified mixture.
The solubility of the laterally fluorinated terphenyls of the formulas Ia3-9, II18, II17 and II26-28 in the liquid-crystal mixture is generally substantially better than the solubility of the non-fluorinated terphenyls of the formula II16. is there.

One or more of the formulas II25, II25a, Ia
2-1, Ia3-9, II18, II17 and II2
6-28, especially formulas Ia2-1, Ia3-9, II18,
II17, II25, II25a and II26-27
The liquid-crystal mixtures containing the laterally fluorinated compounds are characterized by better UV and temperature stability than the mixtures E7 and E8 known from the prior art, or also the corresponding mixtures.

Liquid-crystal mixtures which also contain components (i) and (ii) and, if desired, other components (iii) and (iv) and electro-optical systems containing these have advantageous properties. In particular, these mixtures have a high or relatively high dielectric anisotropy and / or a high clearing point with high or relatively high birefringence. Formula II1, II
5, II9, II16, II25, II25a, Ia2
-1, Ia3-9, II18, II17, II26, I
The compounds I27 and II28 are sufficiently stable to heat and radiation energy for most applications and very stable to chemicals. Liquid-crystal mixtures containing these compounds are very nematic, especially even at low temperatures, and have advantageous values for η. Electro-optical systems operated with these mixtures have advantageous values for the electro-optical parameters and their temperature dependence, high contrast and low angle dependence of the contrast and also good manufacturability.

These liquid crystal mixtures are represented by the lower formula Ib

[0090]

Embedded image [Where Q ² is

[0091]

Embedded image Or

[0092]

Embedded image And one of ring A ⁵ and ring A ⁶ is

[0093]

Embedded image (Where V ¹ is N or CH) and the other, if present, is trans-1,4-cyclohexylene or 1,4-phenylene, X ² and Y ²
Are independently H or F, and P is 0 or 1
And Z ⁵ and Z ⁶ are, independently of one another, a single bond or CH ₂ CH ₂ , and R ¹ has the meaning given in the claims]. Further preferred is an electro-optical liquid crystal system according to the invention comprising the compound

A particularly preferred liquid crystal mixture is X ² or Y ²
A compound of subformula Ib, wherein at least one of F is F

[0095]

Embedded image Is a mixture containing at least one of the following.

Compounds of the subformula IbF are of the formula IbF2
-1 to IbF2-8 include bicyclic compounds which are monofluorinated laterally or difluorinated laterally.

R ¹ -Pyd-Phe.3F-CN IbF2-1 R ¹ -Pyd-Phe.3F5F-CN IbF2-2 R ¹ -Pyr-Phe.3F-CN IbF2-3 R ¹ -Pyr-Phe.3F5F -CN IbF2-4 R ¹ -Pyd-CH ₂ CH ₂ -Phe.3F-CN IbF2-5 R ¹ -Pyd-CH ₂ CH ₂ -Phe.3F5F-CN IbF2-6 R ¹ -Pyr-CH ₂ CH ₂ -Phe.3F-CN IbF2-7 R ¹ -Pyr-CH ₂ CH ₂ -Phe.3F5F-CN IbF2-8 In a compound of the formula IbF2-1 to IbF2-8, R ¹
Is preferably alkyl or alkoxy having 1 to 10, especially 1 to 8 C atoms, furthermore n-alkoxyalkyl, especially n-alkoxymethyl and n-alkoxyethyl. Formulas IbF2-4 and IbF2- having a 3,5-difluoro-4-cyanophenyl group
4, liquid crystals containing compounds of IbF2-6 and / or IbF2-8 have particularly advantageous values for the dielectric anisotropy. R ¹ is methyl, ethyl, n-propyl, n-
Butyl, n-pentyl, n-hexyl, n-heptyl,
n-octyl, n-nonyl, n-decyl, n-methoxy, n-ethoxy, n-propoxy, n-butoxy, n
-Pentoxy, n-hexoxy, n-heptoxy, n-
Compounds of the formulas IbF2-1 to IbF2-8 which are octoxy, n-nonoxy, n-decoxy or n-undecoxy are particularly highly preferred compounds.

The compounds of the formula IbF can be obtained by laterally mono- or difluorinated compounds of the formulas IbF3-1 to IbF3-36
Further preferred is a tricyclic compound.

R ¹ -Pyd-Phe-Phe.3F-CN IbF3-1 R ¹ -Pyr-Phe-Phe.3F-CN IbF3-2 R ¹ -Pyd-Phe-Phe.3F5F-CN IbF3-3 R ¹ -Pyr-Phe-Phe.3F5F-CN IbF3-4 R1-Phe-Pyd-Phe.3F-CN IbF3-5 R1-Phe-Pyd-Phe.3F5F-CN IbF3-6 R1-Phe-Pyr-Phe.3F -CN IbF3-7 R1-Phe-Pyr-Phe.3F5F-CN IbF3-8 R1-Cyc-Pyd-Phe.3F-CN IbF3-9 R1-Cyc-Pyd-Phe.3F5F-CN IbF3-10 R ^1- Cyc-Pyr-Phe.3F-CN IbF3-11 R ¹ -Cyc-Pyr-Phe.3F5F-CN IbF3-12 R ¹ -Pyd-Phe-CH ₂ CH ₂ -Phe.3F-CN IbF3-13 R ^1- Pyd-Phe-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-14 R ¹ -Pyr-Phe-CH ₂ CH ₂ -Phe.3F-CN IbF3-15 R ¹ -Pyr-Phe-CH ₂ CH ₂ -Phe .3F5F-CN IbF3-16 R ¹ -Phe-Pyd-CH ₂ CH ₂ -Phe.3F-CN IbF3-17 R ¹ -Phe-Pyd-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-18 R ^1- Phe-Pyr-CH ₂ CH ₂ -Phe.3F-CN IbF3-19 R ¹ -Phe-Pyr-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-20 R ¹ -Cyc-Pyd-CH ₂ CH ₂ -Phe .3F-CN IbF3-21 R ¹ -Cyc-Pyd-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-22 R ¹ -Cyc-Pyr-CH ₂ CH ₂ -Phe.3F-CN IbF3-23 R ^1- Cyc-Pyr-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-24 R ¹ -Pyd-CH ₂ CH ₂ -Phe-Phe.3F-CN IbF3-25 R ¹ -Pyd-CH ₂ CH ₂ -Phe-Phe .3F5F-CN IbF3-26 R ¹ -Pyr-CH ₂ CH ₂ -Phe-Phe.3F-CN IbF3-27 R ¹ -Pyr-CH ₂ CH ₂ -Phe-Phe.3F5F-CN IbF3-28 R ¹ -Phe-CH ₂ CH ₂ -Pyd-Phe.3F-CN IbF3 -29 R ¹ -Phe-CH ₂ CH ₂ -Pyd-Phe.3F5F-CN IbF3-30 R ¹ -Phe-CH ₂ CH ₂ -Pyr-Phe.3F-CN IbF3-31 R ¹ -Phe-CH ₂ CH ₂ -Pyr-Phe.3F5F-CN IbF3-32 R ¹ -Cyc-CH ₂ CH ₂ -Pyd-Phe.3F-CN IbF3-33 R ¹ -Cyc-CH ₂ CH ₂ -Pyd-Phe.3F5F-CN IbF3 -34 R ¹ -Cyc-CH ₂ CH ₂ -Pyr-Phe.3F IbF3-35 R ¹ -Cyc-CH ₂ CH ₂ -Pyr-Phe.3F5F IbF3-36 In a compound of the formula IbF3-1 to IbF3-36, R
¹ is n-alkyl having ¹ to 10 C atoms or n
-Alkoxy, preferably 1-8 C
It is also n-alkoxymethyl or n-alkoxyethyl having an atom. Preferred Formulas IbF3-1 to IbF3
The compound of −36 has a high or relatively high value for the dielectric anisotropy Δε. In this case, the structural element

[0100]

Embedded image Formulas IbF3-6, IbF3-8, IbF3 containing
-9, IbF3-12, IbF3-30, IbF3-3
2, The difluorinated compounds of IbF3-34 and IbF3-36 are characterized by particularly very high values for Δε.

The compound of formula IbF is described in DE 3,209,17
8, DE 4,002,609, DE 4,001,02
2, DE4,012,014, DE4,012,023
And 3,315,295.

Formula IbF, especially Formula IbF2-1 to IbF2
-8 and liquid crystal mixtures containing one or more compounds of IbF3-1 to IbF3-36 and electro-optical systems filled with these liquid crystal mixtures have advantageous values for birefringence Δn and flow viscosity η, high stability, It is characterized by low miscibility with the polymers used for the matrix, a wide mesogenic range, a relatively high clearing point and especially advantageous values for the dielectric anisotropy, the threshold voltage and the temperature dependence of the electro-optical parameters.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
３０30% of the formula IbF, in particular the formulas IbF2-1 to IbF2-
8 and IbF3-1 to IbF3-36. In this case, the liquid crystal mixture is 1 to 5
Species, in particular 1 to 3, of the formulas IbF, in particular formulas IbF2-1 to IbF
It preferably contains the compounds bF2-8 and IbF3-1 to IbF3-36.

Formula IbF, especially IbF2-1 to IbF2-
8 and one or more compounds selected from the compound group of IbF3-1 to IbF3-36 and further compounds II1 to I
Liquid crystal mixtures comprising at least one compound selected from the group of I28, III1 to III3 and IV1 to IV8 are particularly preferred. Formulas IbF, especially formulas IbF2-1 to IbF2-8 and Ib, in the liquid-crystal mixtures according to the invention
The mass of the component mixture consisting of at least one compound of F3-1 to IbF3-36 and also one or more compounds of the formulas II1 to II28, III1 to III3 and IV1 to IV8 is from 15% to 100%, in particular 25% Preferably it is 100%. Formula IbF, especially Formula IbF2-1 to IbF
In addition to at least one compound selected from the compounds bF2-8 and IbF3-1 to IbF3-36, a component mixture T (IbF3) containing at least one compound selected from the compound group shown in each case, ) 1-T
(IbF) 8 is very particularly preferred. T (IbF) 1: IbF R-Phe-Phe. (F) -X (where X = CN, F or Cl) T (IbF) 2: IbF R-Cyc-Phe-COO-Phe. (F)- X (however, X = CN, F or Cl) T (IbF) 3: IbF R-Phe-COO-Phe. (F) -X (where X = CN, F or C)
l) T (IbF) 4: IbF R-Cyc- (CH ₂ CH ₂ ) _u -Phe. (F) -X (where X = CN, F or Cl and u = 0 or 1) T (IbF) 5 : IbF R-Cyc-Cyc- (CH ₂ CH ₂ ) _u -Phe. (F) -X (where X = CN,
F or Cl and u = 0 or 1) T (IbF) 6: IbF R-Cyc- (CH ₂ CH ₂ ) _u -Phe-Phe. (F) -X (where X = CN,
F or Cl and u = 0 or 1) T (IbF) 7: IbF R-Phe-Phe-Phe. (F) -X (where X = CN, F or C)
l) T (IbF) 8: IbF R-Phe-Phe-COO-Phe. (F) -X, where X = CN, F or Cl At least one of each of the compounds of the formulas mentioned in each case Component mixture T comprising the following compounds:
Liquid crystal mixtures based on (IbF) 9-13 are preferred. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture contains 2 to 38, preferably 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 10
0%. The mass of the component mixture in the liquid crystal of the present invention is 10
% To 100%, especially between 15% and 100%, more particularly between 25% and 100%.

Mixture Formula Formula Mass in component mixture [%] T (IbF) 9 IbF 5-75 II 5-80, especially 6-65 T (IbF) 10 IbF 5-75, especially 5-48 IV 5-63 T (IbF) 11 IbF 5-55 II 5-65, especially 5-52 III 5-29 T (IbF) 12 IbF 5-55, especially 6-45 II 5-65, especially 5-49 IV 5-50 T ( IbF) 13 IbF 5-55, in particular II 5-75, especially 5-64 III 5-37, especially 5-25 IV 5-42 compounds of the formula Ib in which the terminal group -O-CN is not fluorinated

[0106]

Embedded image And a liquid crystal mixture containing at least one of the following.

These compounds of the subformula IbN are represented by the following formulas IV1-IV2 and IbN2-1-IbN2-2
Including cyclic compounds.

R ¹ -Pyd-Phe-CN IV1 R ¹ -Pyr-Phe-CN IV2 R ¹ -Pyd-CH ₂ CH ₂ -Phe-CN IbN2-1 R ¹ -Pyr-CH ₂ CH ₂ -Phe-CN IbN2-2 R1 in the compounds of the formulas IV1 to IV2 and IbN2-1 to IbN2-2 is alkyl or alkoxy having ¹ to 10, in particular 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds.

Compounds wherein R ¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, hexoxy or octoxy are represented by the formulas IV1 to IV2 and IbN2-1
To IbN2-2. Compounds of the formulas IV1 to IV2 and IbN2, in particular the compounds of the formula IV2
And IbN2-2 have high or relatively high values for the dielectric anisotropy Δε. The liquid crystal medium of the present invention comprises compounds IV1 to IV2 and IbN2-1 to IbN
Which compound of 2-2 is preferably contained mainly depends on the intended use of the electro-optical system of the present invention. Thus, for example, while the compounds of formulas IV1 and IV2 have a relatively high clearing point, especially a relatively high optical anisotropy, the compounds of formulas IbN2-1 and IbN2-2
For example, it is characterized by a relatively low flow viscosity.

Liquid crystal mixtures containing compounds of the formulas IV1 and / or IV2 are particularly preferred for matrix systems, but are less suitable for network systems. On the other hand, compounds IbN2-1 to IbN2-2 are generally particularly preferred as a mixture component of a matrix and a network structure.

Compounds of formula IbN are of the following formulas IV3-IV
8 and IbN3-1 to IbN3-18 tricyclic compounds.

R ¹ -Pyd-Phe-Phe-CN IV3 R ¹ -Pyr-Phe-Phe-CN IV4 R ¹ -Pyd-Cyc-Phe-CN IbN3-1 R ¹ -Pyr-Cyc-Phe-CN IbN3- 2 R ¹ -Phe-Pyd-Phe-CN IV5 R ¹ -Phe-Pyr-Phe-CN IV6 R ¹ -Cyc-Pyd-Phe-CN IV8 R ¹ -Cyc-Pyr-Phe-CN IV7 R ¹ -Pyd- Phe-CH ₂ CH ₂ -Phe-CN IbN3-3 R ¹ -Pyr-Phe-CH ₂ CH ₂ -Phe-CN IbN3-4 R ¹ -Pyd-Cyc-CH ₂ CH ₂ -Phe-CN IbN3-5 R ¹ -Pyr-Cyc-CH ₂ CH ₂ -Phe-CN IbN3-6 R ¹ -Phe-Pyd-CH ₂ CH ₂ -Phe-CN IbN3-7 R ¹ -Phe-Pyr-CH ₂ CH ₂ -Phe-CN IbN3-8 R ¹ -Cyc-Pyd-CH ₂ CH ₂ -Phe-CN IbN3-9 R ¹ -Cyc-Pyr-CH ₂ CH ₂ -Phe-CN IbN3-10 R ¹ -Pyd-CH ₂ CH ₂ -Phe -Phe-CN IbN3-11 R ¹ -Pyr-CH ₂ CH ₂ -Phe-Phe-CN IbN3-12 R ¹ -Pyd-CH ₂ CH ₂ -Cyc-Phe-CN IbN3-13 R ¹ -Pyr-CH ₂ CH ₂ -Cyc-Phe-CN IbN3-14 R ¹ -Phe-CH ₂ CH ₂ -Pyd-Phe-CN IbN3-15 R ¹ -Phe-CH ₂ CH ₂ -Pyr-Phe-CN IbN3-16 R ^1- _{cyc-CH 2 CH 2 -Pyd-} Phe-CN IbN3-17 R 1 -Cyc-CH 2 CH 2 -Pyr-Phe-CN IbN3-18 formula IV3~IV8 and IbN3-1~IbN3-18
R ¹ is methyl, ethyl, propyl,
Butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoroxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxy Preferably it is ethyl or propoxyethyl.

The compound of the formula IbN is described in DE 3,600,05
2, DE 3,315,295, SU1,063,10
0, SU1, 063, 101, SU1, 069, 41
3, SU1,171,456, GB2,118,93
4, EP 0,097,033 and DE 3,411,5
Preferably, it is produced by the method described in 71.

Formulas IbN and IV, especially Formula IbN2-1
A liquid crystal mixture containing at least one compound selected from the group consisting of 〜IbN2-2, IbN3-1 to IbN3-18 and compounds IV1 to IV8 has an advantageous value regarding optical anisotropy Δn, high stability, and is used for a matrix. It is characterized by a low miscibility for the polymer to be prepared, a wide mesogenic range, a relatively high clearing point and advantageous values for the dielectric anisotropy and an advantageous temperature dependence of the electro-optical parameters. These mixtures are preferred.

The liquid crystal mixture of the present invention is 1 to 40%, especially 5%
３０30% of formulas IbN and IV, especially formula IbN2-1
IbN2-2, IbN3-1 to IbN3-18 and IbN2-2
It preferably contains the compounds V1 to IV8. In this case, the liquid crystal mixture comprises 1 to 5, in particular 1 to 3, compounds of the formula IbN
And IV, especially the formulas IbN2-1 to IbN2-2, Ib
It preferably contains the compounds N3-1 to IbN3-18 and IV1 to IV8.

Preferred compounds of the formulas IV3 to IV4 have a high or relatively high value for the dielectric anisotropy Δε. In this case, the structural element

[0117]

Embedded image IV6, IV7, IbN3-8, IbN containing
The compounds 3-16 and IbN3-18 are characterized by high values for Δε.

Particularly preferred compounds are those of the formulas IV3, IV, which are characterized by a relatively high dielectric anisotropy and a high optical anisotropy.
4, IV5, IV6, IbN3-3, IbN3-4, I
bN3-7, IbN3-8, IbN3-11, IbN3
-12, IbN3-15 and IbN3-16. Liquid crystal mixtures containing these preferred compounds are particularly preferred.

Liquid-crystal mixtures containing compounds of the formulas IV3, IV4, IV5, IV6 and / or IV7 are sometimes not very suitable for network systems. On the other hand, liquid crystal mixtures of this kind are generally particularly suitable for application in matrix systems.

Formulas IbN, especially IbN2-1 to IbN2-
2, IbN3-1 to IbN3-18 and IV1 to IV
And at least one compound selected from the group consisting of:
Liquid crystal mixtures comprising one or more compounds selected from the group of III-II28 and III1-III3 are particularly preferred. Formulas IbN and IV in the liquid-crystal mixtures used according to the invention, in particular formulas IbN2-1 to IbN2-
2, IbN3-1 to IbN3-18 and IV1 to IV
8 and at least one compound of the formulas II1 to II2
Preferably, the weight of the component mixture consisting of 8 and at least one compound from III1 to III3 is from 15% to 100%, in particular from 25% to 100%.

The following component mixture T (IbN) containing at least one compound from each of the indicated substance groups:
Is particularly suitable for application to matrix systems, but is less suitable for networked systems. R has the meaning described above. T (IbN) 1: IV5 R-Phe- (COO) ₁ -Phe. (F) -X (where X = F, CN and 1 = 0 or 1) T (IbN) 2: IV7 R-Phe-Phe . (F) -X (where X = F, CN) T (IbN) 3: IV6 R-Phe-Phe. (F) -X (where X = F, CN) T (IbN) 4: IV3 R -Phe-Phe. (F) -X (where X = F, CN) T (IbN) 5: IV4 R-Phe-Phe-Y-Phe. (F) -X (where X = F, CN and _{Y = COO, -CH 2 CH 2} - or a single bond) T (IbN) 6: IV2

[0122]

Embedded image (However, X = F, CN,

[0123]

Embedded image Or Phe and l = 0 or 1) T (IbN) 7: . IV2 R-Cyc-CH 2 CH 2 -Phe-Phe (F) -X ( However, X = F, CN) T (IbN) 8: IV1 R- (Cyc) ₁ -Phe-COO-Phe. (F) -X (where X = F, CN and 1 = 0 or 1) Further, selected from the group of IbN and IV compounds shown in each case. The following component mixtures, each containing at least one compound, are less preferred for network systems.

[0124] The component mixtures T (IbN) 9 to T (IbN) 12 are preferably applied to a matrix system.

The following component mixtures T each containing at least one compound from the abovementioned substance groups:
Liquid crystal mixtures containing one or more of (IbN) 13-18 are sometimes not very suitable for application to network systems.
In contrast, these liquid-crystal mixtures can generally be used favorably for application in matrix systems.

[0126] On the other hand, liquid crystal mixtures of this kind can often be modified by adding further compounds so that they are suitable for application in a network system.

Therefore, the above component mixture T (IbN)
In addition to 1 to 18, liquid-crystal mixtures containing, for example, one or more compounds selected from the group of compounds of the formulas Ia, IbF, Ic, Id and Ie, particularly preferred sub-formulas, are generally applicable to network systems. Are suitable.

In addition to the above-mentioned component mixtures, liquid-crystal mixtures containing one or more compounds of the formula If, particularly preferred lower formulas, are also particularly suitable for application to the network system. The mass of the compound of formula If in these liquid-crystal mixtures is preferably at least 5%, in particular at least 7.5%, more particularly at least 10%.

The liquid-crystal mixtures used according to the invention, which contain one or more of the component mixtures T (IbN) 1 to 18, are generally particularly preferably applied to matrix systems.

Compounds IV1, IV2, IV3, IV4,
At least one compound selected from the group of IV5 and IV6 and further compounds II5, II6, II7, II
9, II11, II14, II16, II22 and I
Liquid crystal mixtures containing at least one compound selected from the group of I23 are generally even less preferred for application in network systems, but such mixtures are particularly suitable for application in matrix systems. . On the other hand, such a mixture of components is further combined with formulas Ia, Ic, Id,
The liquid-crystal mixtures used according to the invention containing Ie and IbF, one or more compounds selected from the group of particularly preferred sub-formulas, are generally preferably applied to network systems. This also applies to liquid-crystal mixtures containing one or more compounds of the formula If, in particular the preferred subformulae. The mass of the compound of the formula If in the liquid crystal mixture is preferably at least 5%, in particular at least 10%, more particularly at least 12.5%.

Formulas IbN2-1, IbN2-2 and Ib
Liquid crystal mixtures containing at least one compound from N3-3 to IbN3-18 are particularly preferred for network systems and also for matrix systems.

Furthermore, the compounds of the formula IbN, in particular IbN2-1, IbN
In addition to bN2-2 and one or more compounds of IbN3-1 to IbN3-18 and IV1 to IV8, the following compound groups II2, II4, II3, II8, II10, II
15, II17, II18, II19, II25, II
26, II27, II28, III1, III2, II
I3, II12, II13, II20, II21, II
24, at least one selected from IV7 and IV8
Liquid-crystal mixtures containing certain compounds are very particularly suitable for use in electro-optical systems according to the preamble of claim 1.

Preference is given to liquid-crystal mixtures based on the following component mixtures T (IbF) 19 to 23, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. Ingredient mixture is 2-3
It contains 8, preferably 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

Mixture Formula Formula Mass in component mixture [%] T (IbN) 19 IbN 5-75 II 6-90, especially 11-75 T (IbN) 20 IbN 5-55 IV 5-75, especially 5-52 III 5-29 T (IbN) 21 IbN 5-75 IV 5-63 T (IbN) 22 IbN 5-50 II 5-75, especially 10-65 III 5-37 IV 5-42 T (IbN) 23 IbN 5- 50 II 5-72, especially 5-65 IV 5-46 Their liquid-crystalline mixtures are of the formula Ic

[0135]

Embedded image [Where Q ³ is

[0136]

Embedded image Or

[0137]

Embedded image And one of ring A ⁷ or ring A ⁸ is

[0138]

Embedded image (Where T ¹ is —CH ₂ — or —O—) and the other, if present, is trans-1,4-
Cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, wherein Z ⁷ and Z ⁸ are each independently a single bond, —COO—, OCO— or —CH ₂ CH ₂ —, X ³ is F or Cl, r and q are each independently 0 or 1,

[0139]

Embedded image Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; and

[0140]

Embedded image Is 2-chloro-1,4-phenylene or 3-
Chloro-1,4-phenylene, and R ¹ has the meaning given in claim 1]. The electro-optical liquid-crystal systems according to the invention comprising at least one compound of the formula (1) are more particularly suitable.

Compounds of the formula Ic have the meaning that Z ⁷ and X ³ have the meanings given above and Phe. (X) is Phe, Phe.
F or Phe. The following formulas IcT2 and I which are Cl
Includes bicyclic tetrahydropyran derivatives and dioxane derivatives of cD2.

R ¹ -Thp-Z ⁷ -Phe. (X) -CN IcT2 R ¹ -Dio-Z ⁷ -Phe. (X) -CN IcD2 R ¹ of compounds of formulas IcT2 and IcD2 are ¹ to 10,
Particularly, it is preferably an alkyl or alkoxy having 1 to 8 C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds. Further, R is also preferably alkenyl having 1 to 7 C atoms. R is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy,
Compounds which are ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy or octoxy are of the formula I
Particularly highly preferred compounds of cT2 and IcD2.

In the compounds of the formulas IcT2 and IcD2, Z is --CH ₂ CH _2- , --COO--, --OCO-- or a single bond, in particular --CH ₂ CH _2- , --COO-- or a single bond, more particularly —COO— or a single bond. The phenyl ring is monosubstituted by X ³ F or Cl (r =
1) can be substituted or unsubstituted. Unsubstituted compounds and compounds having an F atom at two or three sites or a Cl atom at three sites are preferred.

Formulas IcT2-1 to IcT2-5 and Ic
The following small group of compounds of D2-1 to IcD2-6 are particularly preferred.

R-Thp-Phe-CN IcT2-1 R-Thp-Phe.3F-CN IcT2-2 R-Thp-Phe.3Cl-CN IcT2-3 R-Thp-COO-Phe. (F) -CN IcT2-4 R-Thp-CH ₂ CH ₂ -Phe. (F) -CN IcT2-5 R-Dio-Phe-CN IcD2-1 R-Dio-Phe.3F-CN IcD2-2 R-Dio-Phe. 3Cl-CN IcD2-3 R-Dio-COO-Phe.3F-CN IcD2-4 R-Dio-COO-Phe.3Cl-CN IcD2-5 R-Dio-CH ₂ CH ₂ -Phe. (F) -CN IcD2-6 Formulas IcT2-1 to IcT2-5 and IcD2-1 to IcD2-1
Liquid crystal mixtures containing one or more compounds selected from the group of preferred compounds of cD2-6 are particularly preferred. Compounds IcT2-1, IcT2-2, IcT2-4, IcT2
A mixture containing a compound selected from the group of -5, IcD2-1, IcD2-2, IcD2-4 and IcD2-6 is a particularly highly preferred liquid crystal mixture.

The compound of the formula Ic is furthermore represented by the following formula IcT3-1
To IcT3-8 and IcD3-1 to IcD3-8
Including cyclic tetrahydropyran derivatives and dioxane derivatives.

R ¹ -Phe. (F) -Thp-Z ⁷ -Phe. (X) -CN IcT3-1 R ¹ -Cyc-Thp-Z ⁷ -Phe. (X) -CN IcT3-2 R ^1- Thp-Phe. (F) -Z ⁷ -Phe. (X) -CN IcT3-3 R ¹ -Thp-Cyc-Z ⁷ -Phe. (X) -CN IcT3-4 R ¹ -Phe. (F)- Z ⁸ -Thp-Phe. (X) -CN IcT3-5 R ¹ -Cyc-Z ⁸ -Thp-Phe. (X) -CN IcT3-6 R ¹ -Thp-Z ⁸ -Phe. (F) -Phe . (X) -CN IcT3-7 R ¹ -Thp-Z ⁸ -Cyc-Phe. (X) -CN IcT3-8 R ¹ -Phe. (F) -Dio-Z ⁷ -Phe. (X) -CN IcD3-1 R ¹ -Cyc-Dio-Z ⁷ -Phe. (X) -CN IcD3-2 R ¹ -Dio-Phe. (F) -Z ⁷ -Phe. (X) -CN IcD3-3 R ^1- Dio-Cyc-Z ⁷ -Phe. (X) -CN IcD3-4 R ¹ -Phe. (F) -Z ⁸ -Dio-Phe. (X) -CN IcD3-5 R ¹ -Cyc-Z ⁸ -Dio -Phe. (X) -CN IcD3-6 R ¹ -Dio-Z ⁸ -Phe. (F) -Phe. (X) -CN IcD3-7 R ¹ -Dio-Z ⁸ -Cyc-Phe. (X) -CN IcD3-8 Formulas IcT3-1 to IcT3-8 and IcD3-1 to IcD3-1
In preferred compounds of cD3-8, R ¹ is methyl,
Ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy,
Heptoxy, octoxy, nonoxy, decoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxymethoxyethyl,
Ethoxyethyl, propoxyethyl, 2-pentenyl,
3-pentenyl, 4-pentenyl, 2-hexenyl, 3
Preferably it is -hexenyl, 4-hexenyl or 5-hexenyl. In the compounds of formula IcT3-1~IcT3-8 and IcD3-1～IcD3-8, Z is -COO -, - OCO -, - CH 2 CH 2 - or a single bond, preferably -COO -, - CH ₂ CH _2- or a single bond, more particularly a single bond.

Phe. Formulas IcT3-1 to IcT, wherein (F) is a 2- or 3-fluoro-1,4-phenylene group
Compounds 3-8 and IcD3-1 to IcD3-8 generally have relatively lower viscosities η as compared to non-laterally substituted compounds.

The following small group of tricyclic compounds is particularly highly preferred.

R ¹ -Phe-Thp-Phe-CN IcT3-1a R ¹ -Phe-Thp-Phe.3F-CN IcT3-1b R ¹ -Phe-Dio-Phe-CN IcD3-1a R ¹ -Phe-Dio -Phe.3F-CN IcD3-1b R ¹ -Cyc-Thp-Phe-CN IcT3-2a R ¹ -Cyc-Dio-Phe-CN IcD3-2a R ¹ -Thp-Phe-Phe-CN IcT3-3a R ¹ -Dio-Phe-Phe-CN IcD3-3a R 1 -Dio-Phe-Phe.3F-CN IcD3-3b Z is -COO- or -CH ₂ CH ₂ - in which formula IcT3
-1, IcD3-1, IcT3-3, IcD3-3, I
cT3-5, IcD3-5, IcT3-6 and IcD
3-6 tetrahydropyrans and dioxanes are more particularly particularly preferred.

Formulas IcT2, IcD2, IcT3 and I
The compounds of cD3 have advantageous values for the flow viscosity η and the optical anisotropy Δn and especially high values for the dielectric anisotropy Δε. Structural element

[0152]

Embedded image Or

[0153]

Embedded image Formulas IcT2, IcD2, IcT3 and IcD3 comprising
Have particularly very high values for Δε.

Compounds of formula IcT or IcD are of the type DE3,
447,359, DE3,306,960, GB89
It is preferably prepared by the method described in US Pat. No. 2,583.7 and DE 3,146,249.

Formulas IcT2, IcD2, IcT3 and I
cD3, more particularly the preferred formulas IcT2-1 to Ic
T2-5, IcD2-1 to IcC2-6, IcT3-1
a-1b, IcD3-1a-1b, IcT3-2a, I
cD3-2a, IcT3-3a and IcD3-3a-
Liquid crystal mixtures containing at least one compound of 3b have advantageous values for the birefringence Δn and the flow viscosity η, high stability, low miscibility with the polymers used for the matrix, wide mesogenic range, relatively high clearing points,
And especially advantageous values for the dielectric anisotropy and the temperature dependence of the electro-optical parameters.

The liquid-crystal mixtures used in the electro-optical liquid-crystal systems according to the invention preferably contain from 1 to 40%, in particular from 5 to 30%, of the compounds of the formulas IcT and IcD, particularly preferred subformulae. In this case, the liquid crystal mixture has the formulas IcT and Ic
It is preferred to contain D, in particular from 1 to 5, especially from 1 to 3, compounds of the particularly preferred sub-formula.

Formulas IcT2, IcD2, IcT3 and I
cD3, particularly preferred formulas IcT2-1 to IcT2-5,
IcD2-1 to IcC2-6, IcT3-1a to 1b,
IcD3-1a-1b, IcT3-2a, IcD3-2
a, one or more compounds selected from the group of compounds IcT3-3a and IcD3-3a-3b, and further compounds I
I1-II28, III1-III3 and IV1-I
A mixture containing one or more compounds selected from the group V8 is a particularly preferred liquid crystal mixture. Formulas IcT2, IcD2, I in the liquid-crystal mixtures used according to the invention
cT3 and IcD3, in particular at least one compound of the preferred sub-formulas indicated, and additionally formulas II1-II28,
The mass of the component mixture consisting of at least one compound of III1-III3 and IV1-IV8 is between 15% and 1%.
It is preferably 00%, especially 25% to 100%.

The following component mixtures containing at least one compound from group A below and at least one compound from group B below are particularly preferred.

Group A Group B IcD2-1, IcD2-2, IcD2-4, II1, II4, II5, II6, IcD2-6, IcD3-1a, II9, II11, II16, I117, IcD3-1b, IcD3-2a , II22, II23, II26, II27, IcD3-3a, IcD3-3b II28, III1, III2, IV1, IV2, IV3, IV4, IV5, IV6, IV7, IV8, II3, II7 The following component mixtures T each containing at least one compound from the group
Liquid crystal mixtures based on (Ic) 1 to 5 are preferred. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is from 2 to 38, preferably 2
It contains ~ 35, especially 2-25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystal of the present invention is 10% to 10%.
0%, especially 15% to 100%, more particularly 25% to
Between 100%.

Mixture Formula Mass in component mixture [%] T (Ic) 1 Ic 5-75, especially 5-55 II 6-85, especially 6-65 T (Ic) 2 Ic 5-75, especially 5-55 IV 5-80, especially 5-13 T (Ic) 3 Ic 5-50 II 5-72, especially 10-65 IV 5-65, especially 5-46 T (Ic) 4 Ic 5-55 II 5-52 III 5-29 T (Ic) 5 Ic 5-50 II 5-75, especially 10-75 III 5-37 IV 5-42 Their liquid-crystalline mixtures are of the formula Id

[0161]

Embedded image (In the formula, ring A ⁹ is 1,4-phenylene or trans-
1,4-cyclohexylene, and ring A ¹⁰ is 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or trans-1,4-
Cyclohexylene, Z ⁹ is a single bond, -COO-,
-OCO- or -CH ₂ CH ₂ - and is, Z ¹⁰ represents a single bond, -COO- or -CH ₂ CH ₂ - and is, s is 0 or 1, and R ¹ is meanings given above) More preferred are electro-optical liquid crystal systems comprising one or more compounds of the formula:

The liquid crystal has the formula IdE2-1 and IdE3-1
1 selected from the following subgroups of compounds:
Systems containing more than one compound are particularly preferred systems.

R ¹ -Cyc-CH ₂ CH ₂ -Phe-CN IdE2-1 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe-CN IdE3-1 R ¹ -Phe-CH ₂ CH ₂ -Cyc-Phe -CN IdE3-2 R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe-CN IdE3-3 R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe-CN IdE3-4 R ¹ -Phe-Cyc-CH ₂ CH ₂ -Phe-CN IdE3-5 R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe-CN IdE3-6 R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe-CN IdE3-7 R ¹ -Phe- CH ₂ CH ₂ -Phe-Phe-CN IdE3-8, wherein R ¹ has the meaning given above.

In the bicyclic compound of the formula IdE2-1,
R ¹ is preferably n-alkyl or n-alkoxy having ¹ to 10 C atoms, in particular 1 to 8 C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds.

In the tricyclic compounds of the formulas IdE3-1 to IdE3-8, R ¹ is an n having ¹ to 10 C atoms.
-Alkyl or n-alkoxy, preferably
Furthermore, n-alkoxy having 1 to 6 C atoms
It is also an alkoxymethyl or n-alkoxyethyl.

R ¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl , Butoxymethyl, methoxymethyl, ethoxymethyl or propoxymethyl.

The compounds of the formulas IdE2 and IdE3 are
2,636,684, DE2,922,236, EP
0,102,047, EP0,129,177, DE
3,040,362, DE 3,317,597 and U
It is preferable to produce by the method described in S4,035,056.

Formulas IdE2-1 and IdE3-1 to Id
Liquid-crystal mixtures containing at least one compound selected from the compounds of E3-8 have advantageous values for the dielectric anisotropy Δε, high stability, low miscibility with the polymers used for the matrix, and a particularly wide mesogenic range , Characterized by a relatively high clearing point and advantageous values for birefringence.

The liquid-crystal mixtures used in the electro-optical liquid-crystal systems according to the invention preferably contain from 1 to 40%, in particular from 5 to 30%, of the compounds of the formula Id, particularly preferred lower formulas. In this case, the liquid crystal mixture is of the formula Id, particularly the preferred subformulas 1 to
It preferably contains five, especially one to three, compounds.

Formulas IdE2-1 and IdE3-1 to Id
A particularly preferred liquid crystal mixture is a mixture containing at least one compound selected from the group of compounds of E3-8 and at least one compound selected from the group of compounds II1 to II28, III1 to III3, and IV1 to IV8. It is. Formulas IdE2-1 and Id in liquid crystal mixtures according to the invention
At least one compound of E3-1 to IdE3-8 and further compounds of formulas II1 to II28, III1 to III3 and I
The weight of the component mixture consisting of at least one compound of V1 to IV8 is from 15% to 100%, in particular from 25% to 100%
%.

The following component mixtures, T (IdE), containing at least one compound each selected from the group of compounds indicated in each case, are particularly suitable for application to matrix systems, Especially very suitable to apply to. The following component mixtures, which comprise one or more compounds selected in each case from the group of compounds indicated, are very particularly suitable for application to matrix systems. For application to both matrix systems and especially network systems, at least one compound of the formula IdE2-1 and one or more selected from the group of compounds II1, II3-II5, II7-II28 and IV1-IV6 And a liquid crystal mixture containing the compound of formula (1). The properties of these mixtures can generally be further improved by the addition of one or more compounds selected from the compounds of the formulas Ia, IbF, Ic, Id and If, especially preferred subformulae.

Furthermore, the following component mixtures T (IdE) 17 to 17 each containing at least one compound of the formulas indicated in each case within the indicated mass percent range:
T (IdE) 19 is very particularly preferred. In this case, the sum of the masses of the component mixtures is 100% for each component mixture.
It is. On the other hand, the mass of the component mixture in the liquid crystal mixture used in the system of the present invention is 10% to 100%, particularly 10% to 9%.
0%, more particularly 15% to 85%.

Mixture Formula Mass in component mixture [%] T (IdE) 17 IdE3 5-35 II1- II28 6-60 T (IdE) 18 IdE3 5-35 IV1- IV8 5-45 T (IdE) 19 IdE2 and And / or IdE3 4-32 II1-II28 5-58 IV1- IV8 5-37 The liquid crystal mixtures thereof have the formulas Ie4-1 to Ie4-4

[0174]

Embedded image (Wherein ring A ¹¹ is in each case independently of one another
1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or trans-1,4-cyclohexylene, the rings A ¹² being in each case independently of one another ,

[0175]

Embedded image Or

[0176]

Embedded image And t is 0 or 1, and

[0177]

Embedded image Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and R ¹ is
Further preferred is an electro-optical liquid crystal system comprising one or more tetracyclic compounds selected from the group of the carbonitrile (meaning indicated in the above).

Formulas Ie4-1a to Ie4-1 shown below
g, Ie4-2a to Ie4-2k, Ie4-3a to Ie
Compounds of 4-3f and Ie4-4a to Ie4-4l are particularly preferred.

R ¹ -Phe-Phe-Phe-CH ₂ CH ₂ -Phe-CN Ie4-1a R ¹ -Phe-Phe-Phe.2F-CH ₂ CH ₂ -Phe-CN Ie4-1b R ¹ -Phe- Phe-Phe.3F-CH ₂ CH ₂ -Phe-CN Ie4-1c R ¹ -Phe-Phe-Phe-CH ₂ CH ₂ -Phe.F-CN Ie4-1d R ¹ -Phe-Phe-Cyc-CH ₂ CH ₂ -Phe-CN Ie4-1e R ¹ -Cyc-Phe-Phe. (F) -CH ₂ CH ₂ -Phe. (F) -CN Ie4-1f R ¹ -Cyc-Cyc-Phe. (F)- CH ₂ CH ₂ -Phe-CN Ie4-1g R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe. (F) -Phe. (F) -CN Ie4-2a R ¹ -Phe-CH ₂ CH ₂ -Cyc -Phe-Phe-CN Ie4-2b R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.2F-Phe-CN Ie4-2c R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-Phe-CN Ie4-2d R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe-Phe. (F) -CN Ie4-2e R ¹ -Cyc-CH ₂ CH ₂ -Phe-Cyc-Phe-CN Ie4-2f R ^1- Cyc-CH ₂ CH ₂ -Cyc-Phe-Phe-CN Ie4-2g R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe.2F-Phe-CN Ie4-2h R ¹ -Cyc-CH ₂ CH ₂ -Cyc -Phe.3F-Phe-CN Ie4-2i R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe-Phe. (F) -CN Ie4-2k R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe. F) -CH ₂ CH ₂ -Phe-CN Ie4-3a R ¹ -Phe-CH ₂ CH ₂ -Cyc-Phe. (F) -CH ₂ CH ₂ -Phe-CN Ie4-3b R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe-CH ₂ CH ₂ -Phe-CN Ie4-3c R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.2F-CH ₂ CH ₂ -Phe-CN Ie4 -3d R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-CH ₂ CH ₂ -Phe-CN Ie4-3e R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe. (F) -CH ₂ CH ₂ -Phe-CN Ie4-3f R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe-Phe-CN Ie4-4a R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe.2F-Phe-CN Ie4-4b R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe.3F-Phe-CN Ie4-4c R ¹ -Phe-Phe-CH ₂ CH ₂ -Cyc-Phe-CN Ie4-4d R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe. (F) -Phe-CN Ie4-4e R ¹ -Cyc-Phe-CH ₂ CH ₂ -Cyc-Phe-CN Ie4-4f R ¹ -Phe-Cyc-CH ₂ CH ₂ -Phe- Phe-CN Ie4-4g R ¹ -Phe-Cyc-CH ₂ CH ₂ -Cyc-Phe-CN Ie4-4h R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe-Cyc-CN Ie4-4i R ¹ -Cyc -Phe-CH ₂ CH ₂ -Phe.2F-Cyc-CN Ie4-4k R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe.3F-Cyc-CN Ie4-4l Formulas Ie4-1a to Ie4-1g, Ie4 -2a to Ie4
-2k, Ie4-3a to Ie4-3f and Ie4-4
R ¹ of the compounds a to Ie 4-4l is 1 to 10, especially 1 to
It is preferably an alkyl or alkoxy having 8 C atoms. n-alkoxyalkyl compounds, especially n
-Alkoxymethyl and n-alkoxyethyl compounds are more preferred.

The compounds of the formulas Ie4-1 to Ie4-4 are
It is preferably produced by the methods described in DE 3,401,320 and DE 2,617,593.

Formulas Ie4-1 to Ie4-4, especially compounds of the formula Ie4
-1a to Ie4-1g, Ie4-2a to Ie4-2k,
Ie4-3a to Ie4-3f and Ie4-4a to Ie
Liquid crystal mixtures containing one or more compounds selected from the group of 4-4 l are preferred. Formula Ie4-1, Ie4
-2 and Ie4-4, especially formulas Ie4-1a to Ie4-
1g, Ie4-2a to Ie4-2k and Ie4-4a
Liquid crystal mixtures containing one or more compounds selected from the group consisting of -Ie4-4l are particularly preferred.

The compounds of the formulas Ie4-1 to Ie4-4 have high clearing points and relatively high values for the flow viscosity η.

To lower the flow viscosity, the formula Ie4-
The 1,4-phenylene group of the compound of 1 to Ie4-4 is represented by X =
Lateral mono-substitution with F or Cl, especially F, is also possible. The substituted compounds have the following structural features S1-S
3

[0184]

Embedded image It is particularly preferred to have one of the following:

The liquid crystal of the present invention accounts for 2 to 40%, especially 5 to 30%.
% Of Formulas Ie4-1a to Ie4-1g, Ie4-2a to Ie
e4-2k, Ie4-3a to Ie4-3f and Ie4
-4a to Ie4-41 preferably contain a compound selected from the group of tetracyclic carbonitriles. In this case, the liquid crystal preferably contains 1 to 5, especially 1 to 3, compounds of the formula Ie4 and the preferred sub-formulae.

The choice of the compounds of the formulas Ie4-1 to Ie4-4, particularly preferred lower formulas, is made in view of the particular embodiment of the electro-optical system of the invention which is desired in each case. For example, if a high viscosity and high clearing point liquid crystal medium having high optical anisotropy is required, the medium may be, for example, particularly Ie4
-1a, Ie4-2a, Ie4-3a and / or I
e4-4a including one or more laterally unsubstituted compounds. On the other hand, a high clearing point medium having a relatively low viscosity and a relatively low optical anisotropy is represented by the formula Ie4-1
g, Ie4-2h-2k, Ie4-3f and / or Ie4-4i-4l preferably comprise one or more laterally mono-substituted compounds. Formulas Ie4-1 to Ie4-1
Ie4-3, especially formulas Ie4-1a to Ie4-1g, Ie
4-2a to Ie4-2k, Ie4-3a to Ie4-3f
And Ie4-4a to Ie4-4l, more particularly formulas Ie4-1a to Ie4-1g, Ie4-2a to Ie4-
2k and one or more compounds selected from the compound group of Ie4-4a to Ie4-4l and further compounds II1 to I
A mixture containing at least one compound selected from the group consisting of I28, III1 to III3 and IV1 to IV8 is a particularly preferred liquid crystal mixture. In the liquid-crystal mixtures used according to the invention, at least one compound of the formulas 1e4-1 to Ie4-4, particularly preferred subformulas, and furthermore formula II
1 to II28, III1 to III3 and IV1 to IV
The weight of the component mixture consisting of at least one compound of No. 8 is preferably from 15% to 100%, in particular from 25% to 100%.

In addition to the compounds of the formulas Ie4-1 to Ie4-4, in particular at least one compound selected from the group of compounds of the subformulae of these compounds, the compounds of the formulas II1 to II6, II
7, II9, II11, II14, II16, II2
3, the following component mixture T containing one or more compounds selected from II22 and the compounds IV1-IV8
(Ie4) is very particularly preferred.

Preference is given to liquid-crystal mixtures based on the following component mixtures T (Ie4) 1-3, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 types,
It preferably contains 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

Mixture Formula Mass in component mixture [%] T (Ie4) 1 Ie4 5-75, especially 5-45 II 6-65 T (Ie4) 2 Ie4 5-75, especially 5-35 IV 5-63 T (Ie4) 3 Ie4 5-55, especially 5-25 II 5-53 IV 5-50 Their liquid-crystal mixtures are of the formula If

[0190]

Embedded image (Wherein at least one of ring A ¹³ and, if present, ring A ¹⁴ is 1,4-phenylene, 2-fluoro-1,4
-Phenylene, 3-fluoro-1,4-phenylene, trans-1,4-cyclohexylene, pyridine-2,5
-Diyl, pyrimidine-2,5-diyl or 1,3-
Dioxane-2,5-diyl and the other, if present, trans-1,4-cyclohexylene,
1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and Z
¹¹ and Z ¹² are in each case independently of one another a single bond, -C≡C, -CH ₂ CH _2- , -COO-, -OCO
-Or a combination of two or more of these bridge members;
v is 0, 1 or 2, a is 0 or 1,

[0191]

Embedded image Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene,

[0192]

Embedded image Is 3,5-difluoro-1,4-phenylene, and T ² is —Cl, —F, —CF ₃ , —OCF ₃ , —OC
Further preferred is an electro-optical liquid crystal system comprising one or more compounds of HF ₂ or NCS and R ¹ has the meaning given in claim 1).

In the following, Phe. (F, 2) is a 1,4-phenylene group which is not laterally substituted, a 1,4-phenylene group which is laterally monosubstituted at 2 or 3 positions, or a 1,4-phenylene group which is laterally disubstituted at 3 and 5 positions. 4-phenylene group.

The following compounds wherein T ² is --NCS are of the formula I
Preferred compounds of f.

[0195]

Embedded image Compounds of formula IfI are preferably of the following formulas IfI2-1 to IfI
2-4 bicyclic compounds.

R ¹ -Phe-Z ¹¹ -Phe-NCS IfI2-1 R ¹ -Cyc-Z ¹¹ -Phe-NCS IfI2-2 R ¹ -Pyr-Z ¹¹ -Phe-NCS IfI2-3 R ¹ -Pyd- Z ¹¹ -Phe-NCS IfI2-4 R ¹ is preferably a linear group, more preferably 1 to 10, especially 1 to 8
Preference is given to alkyl or alkoxy having 3 C atoms. n-alkoxyalkyl compounds, in particular n-
Alkoxymethyl and n-alkoxyethyl compounds are more preferred.

In the compounds of the formulas IfI2-1 to IfI2-4, Z ¹¹ is preferably a single bond, --CH ₂ CH _2- , COO or OCO. Z is a single bond or COO,
In particular, liquid-crystal mixtures containing one or more compounds of the formula IfI2-3 or IfI2-4, which are single bonds, have a dielectric anisotropy Δ
It has a particularly advantageous value for ε.

Compounds of the formula IfI2-1 and IfI2-2 are particularly preferred. Formulas IfI2-1a-1b and If
The following small group of bicyclic compounds of I2-2a-2b are particularly highly preferred.

R-Phe-Phe. (F) -NCS IfI2-1a R-Phe-Phe. (F) -NCS IfI2-1b R-Cyc-Phe. (F) -NCS IfI2-2a R-Cyc-CH _{2 CH 2 -Phe. (F)} -NCS IfI2-2b in addition to the compound which is not fluorinated laterally of one or more formulas IfI2-2a, at least one selected from the group of compounds of formula II5, IV1 and IV2 Liquid crystal mixtures containing compounds of the formula are particularly suitable for matrix systems,
Not very suitable for network structures.

The compounds of the formula IfI are of the following formulas IfI3-1 to IfI3-1
It further includes a tricyclic compound of fI3-20.

R ¹ -Phe-Phe-Z ¹² -Phe. (F) -NCS IfI3-1 R ¹ -Phe-Cyc-Z ¹² -Phe. (F) -NCS IfI3-2 R ¹ -Phe-Pyr- Z ¹² -Phe. (F) -NCS IfI3-3 R ¹ -Phe-Pyd-Z ¹² -Phe. (F) -NCS IfI3-4 R ¹ -Cyc-Phe-Z ¹² -Phe. (F) -NCS IfI3-5 R ¹ -Cyc-Cyc-Z ¹² -Phe. (F) -NCS IfI3-6 R ¹ -Cyc-Pyr-Z ¹² -Phe. (F) -NCS IfI3-7 R ¹ -Cyc-Pyd- Z ¹² -Phe. (F) -NCS IfI3-8 R ¹ -Pyr-Phe-Z ¹² -Phe. (F) -NCS IfI3-9 R ¹ -Pyd-Phe-Z ¹² -Phe. (F) -NCS IfI3-10 R ¹ -Phe-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-11 R ¹ -Phe-Z ¹¹ -Cyc-Phe. (F) -NCS IfI3-12 R ¹ -Phe-Z ¹¹ -Pyr-Phe. (F) -NCS IfI3-13 R ¹ -Phe-Z ¹¹ -Pyd-Phe. (F) -NCS IfI3-14 R ¹ -Cyc-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-15 R ¹ -Cyc-Z ¹¹ -Cyc-Phe. (F) -NCS IfI3-16 R ¹ -Cyc-Z ¹¹ -Pyr-Phe. (F) -NCS IfI3-17 R ¹ -Cyc-Z ¹¹ -Pyd-Phe. (F) -NCS IfI3-18 R ¹ -Pyr-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-19 R ¹ -Pyd-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-20 In compounds of the formula IfI3-1 to IfI3-20, R
¹ is n-alkyl having ¹ to 10 C atoms or n
-Alkoxy, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 8 C atoms. R ¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl IfI3-1 to IfI, which is methoxyethyl, ethoxyethyl or propoxyethyl
The compound of 3-20 is a particularly preferred compound.

Formulas IfI3-1, IfI3-5, IfI3
Compounds of -11 and If13-15 are particularly preferred.
Z ¹¹ and Z ¹² are each independently a single bond or CO 2
O, in particular compounds of the formula IfI3 which are single bonds and of the formula If
The compounds of I3-13 have particularly advantageous values for Δε, especially when the terminal 1,4-phenylene group is fluorinated at three sites.

Formulas IfI3-1a, IfI3-1b, If
Very particular preference is given to the following subgroups of tricyclic compounds of I3-5a, IfI3-5b, IfI3-11a and IfI3-15a.

(F) -NCS IfI3-1a R-Phe-Phe-CH ₂ CH ₂ -Phe. (F) -NCS IfI3-1b R-Cyc-Phe-Phe. (F ) -NCS IfI3-5a R-Cyc-Phe-CH ₂ CH ₂ -Phe. (F) -NCS IfI3-5b R-Cyc-Cyc-Phe. (F) -NCS IfI3-6a R-Cyc-Cyc-CH ₂ CH ₂ -Phe. (F) -NCS IfI3-6b R-Phe-CH ₂ CH ₂ -Phe-Phe. (F) -NCS IfI3-11a R-Cyc-CH ₂ CH ₂ -Phe-Phe. (F ) -NCS IfI3-15a Compounds of formula IfI are described in EP 0,169,327, JP 61
189263, EP0, 126, 883, EP0, 2
15,800, DE327,115,10, EP0,2
42,716, DE3,545,345, EP0,22
7,004, EP 0,272,580 and DE 3,9
It is preferably produced by the method described in US Pat.

The choice of the compounds of formula IfI, particularly the preferred subformulae, is made in view of the particular embodiments of the electro-optical system of the present invention. For example, if a liquid crystal medium with a high or relatively high optical viscosity is required, the medium may be of the formula IfI2-1, IfI2-3, IfI3-, especially where Z is a single bond.
1, IfI3-3, IfI3-9, IfI3-11, I
fI3-13 and / or IfI3-19. Particularly preferred compounds are the terminal 1,
A compound in which a 4-phenyl group or another 1,4-phenylene group is laterally fluorine-substituted at two or three sites, particularly three sites. One skilled in the art will appreciate the pooled formula IfI
Other embodiments can be selected from the compounds of the present invention without inventive assistance.

Liquid-crystal mixtures containing one or more compounds of the formula IfI, particularly preferred subformulae, have advantageous values for the birefringence Δn and the dielectric anisotropy Δε, high stability, low miscibility with the polymers used for the matrix. And particularly advantageous values for the wide mesogenic range, relatively high clearing point, dielectric anisotropy and flow viscosity η.

These liquid crystal mixtures have a content of 1 to 40%, especially 5 to 40%.
It preferably comprises 〜30% of the compounds of the formula IfI, particularly the preferred subformulae. In this case, the liquid crystal mixture has the formula If
It is preferred that I contain 1 to 5, especially 1 to 3, compounds of the particularly preferred sub-formula.

Formulas IfI, especially Formulas IfI2-1 to IfI2
-4 and IfI3-1 to IfI3-20, more particularly the compounds IfI2-1a, IfI2-1b, IfI2-2.
a, IfI2-2b, IfI3-1a, IfI3-1
b, IfI3-5a, IfI3-5b, IfI3-11
a and 1 selected from the compound group of IfI3-15a
At least one compound and further compounds II1-II28, II
Mixtures containing one or more compounds selected from the group of I1-III3 and IV1-IV8 are particularly preferred. Formula IfI in the liquid crystal mixture used according to the invention
2 and IfI3, in particular at least one compound of the preferred subformulae of these compounds, and also of formulas II1-II
28, the mass of the component mixture consisting of at least one compound of III1-III3 and IV1-IV8 is 15
% To 100%, preferably 25% to 100%.

In addition to the at least one laterally non-fluorinated compound selected from the group of compounds of the formulas IfI2-2a, IfI3-5a and IfI3-6a, the compounds of the formula II
5, at least one selected from the group consisting of IV1 and IV2
Liquid crystal mixtures containing certain compounds are generally particularly suitable for matrix systems, but are often less suitable for network systems. However, the properties of such component mixtures are characterized by at least one selected from the group of compounds of the formulas Ia, Ic, Id, Ie, IfF, IfCl and IfCl.
The addition of a species, preferably three or more compounds, is often clearly improved and also preferred for networks.

Compounds of Formulas IfI2-1b and IfI3-6b and Formulas
At least one compound selected from the group consisting of laterally fluorinated compounds of IfI2-1a and IfI3-6a, and further II1, II3, II2, II5, II9, II11, II14, II16, I
Liquid crystal mixtures containing compounds selected from the group of compounds I22, II23 and IV1 to IV8 are particularly suitable for matrix systems and very particularly suitable for network systems.

Furthermore, the following component mixtures, each containing at least one compound from the indicated group of compounds, are particularly suitable for both matrix systems and network systems. T (IfI) 1:. IfI2-1a R-Phe- (COO) z - (. Phe (F)) y -Phe (F) -X 4 ( ^{however, X 4 = CN, F,} Cl, OCF 3 or CF ₃ and z and y are independently 0 or 1) T (IfI) 2: IfI2-1a R-Cyc- (CH ₂ CH ₂ ) _z -Phe. (F) -X ⁴ (where X ⁴ = CN, F, Cl, OCF ₃ or CF ₃ , and z = 0 or 1) T (IfI) 3: IfI2-1a R-Pyr- (Phe) _z -Phe. (F) -X ⁴ (where z = 0 or 1,
And X ⁴ = CN, F or Cl) T (IfI) 4: IfI2-1a R-Pyd- (Phe) _z -Phe. (F) -X ⁴ (where z = 0 or 1,
And X ⁴ = CN, F or Cl) T (IfI) 5: IfI2-1b R-Phe-(COO) _z- (Phe. (F)) _y -Phe. (F) -X ⁴ (where X ⁴ = CN, F, Cl, OCF ₃ or CF ₃ , and z and y are independently 0 or 1) T (IfI) 6: IfI2-1b R-Cyc- (CH ₂ CH ₂ ) _z -Phe. F) -X ⁴ (where X ⁴ = CN, F, Cl, OCF ₃ or CF ₃ , and z
= 0 or 1) T (IfI) 7: . IfI2-1b R-Pyr- (Phe) z- Phe (F) -X 4 ( however, z = 0 or 1, and X ⁴ = CN, F or Cl) T (IfI) 8: IfI2-1b R-Pyd- (Phe) _z -Phe. (F) -X ⁴ (where z = 0 or 1,
And X ⁴ = CN, F or Cl) T. (IfI) 9 :. IfI2-2a R-Phe- (COO) z - (Phe (F)) y -Phe (F) -X 4 ( however, X ⁴ = CN, F, Cl, OCF ₃ or CF ₃ , and z and y are independently 0 or 1) T (IfI) 10: IfI2-2a R-Cyc- (CH ₂ CH ₂ ) _z -Phe. F) -X ⁴ (where X ⁴ = CN, F, Cl, OCF ₃ or CF ₃ , and z = 0 or 1) T (IfI) 11: IfI2-2a R-Pyr- (Phe) z-Phe. (F) -X ⁴ (where z = 0 or 1, and X ⁴ = CN, F or Cl) T (IfI) 12: IfI2-2a R-Pyd- (Phe) _z -Phe. (F) -X ⁴ (However, z = 0 or 1,
And X ⁴ = CN, F or Cl) T (IfI) 13: IfI2-5a R-Phe (COO) _z- (Phe. (F)) _y -Phe. (F) -X ⁴ (where X ⁴ = CN, F, Cl, OCF ₃ or CF ₃ , and z and y are independently 0 or 1) T (IfI) 14: IfI2-5a R-Cyc- (CH ₂ CH ₂ ) _z -Phe. ) -X ⁴ (where X ⁴ = CN, F, Cl, OCF ₃ or CF ₃ , and z = 0 or 1) T (IfI) 15: IfI2-5a R-Pyr- (Phe) _z -Phe. F) -X ⁴ (where z = 0 or 1, and X ⁴ = CN, F or Cl) T (IfI) 16: IfI2-5a R-Pyd- (Phe) _z -Phe. (F) -X ⁴ (However, z = 0 or 1,
And X ⁴ = CN, F or Cl) compounds wherein T ² is —U—F

[0212]

Embedded image Wherein U is a single bond, —CF ₂ —, —OCF ₂ or —OCHF—, and R ¹ has the meaning indicated in claim 1.
Are more preferred compounds.

The compounds of the formula IfF are preferably represented by the following formulas IfF2-1 to IfF
2-4 bicyclic compounds.

[0214]

Embedded image In the compounds of the formulas IfF2-1 to IfF2-4, R ¹ is preferably a linear group, preferably an alkyl or alkoxy having 1 to 10, especially 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds. Z
¹¹ is preferably —CH ₂ CH ₂ —, —COO— or a single bond, particularly a single bond or —CH ₂ CH ₂ —, and more particularly a single bond. Ring A ^{1 3} is Cyc, Phe. (F), is preferably Pyr or Pyd.

The compounds of the formula IfF are represented by the following small group of preferred compounds of the formula I:
It further includes tricyclic compounds of fF3-1 to IfF3-8.

[0216]

Embedded image In the compounds of formulas IfF3-1 to IfF3-8, R ¹ is 1 to 10
It is preferably n-alkyl or n-alkoxy having C atoms, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 8 C atoms.

R ¹ is methyl, ethyl, propyl, butyl,
Pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexosyl, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl or propoxyethyl Compounds of the formulas IfF3-1 to IfF3-8 are particularly highly preferred compounds. Z ¹¹ and Z ¹² in the compounds of the formulas IfF3-1 to IfF3-8 are each independently of one another —CH ₂ CH ₂ —, —COO—, a single bond or two or more of these bridge members Preference is given to a combination, in particular —CH ₂ CH ₂ — or a single bond.

The compound of the formula IfF is DE 3,102,017, JP
57 -140,747, DE3,233,641, DE2,9
37,911, EP0,097,033, DE3,509,26
0, DE3,732,284, DE3,928,783, EP0,
194,153, JP58-126,839, JP58-21
0,045, WO85 / 04874, DE3,315,29
5, EP0,193,191, JP63-280,063, DE
3,825,428, DE3,929,525, DE4,024,
760, DE 4,009,907, DE 4,007,040, DE
4,012,051, DE3,939,116, PCT / EP90
/ 00186, WO 90/08775, DE 3,929,76
4, DE4,004,650, DE4,013,854 and DE
It is preferably produced by the method described in 3,913,554.

Phe. (F, 2) = Phe.3F or Phe.3F5F
Formula of one or more of formulas IfF2-1 to IfF2-4 and IfF3-1 to IfF3-8
The liquid crystal mixture containing the compound has a good dielectric anisotropy Δε
It is preferable because it has an advantageous value. Ph. (F, 2) = Phe. 3F
Or Phe.3F5F and ring A ¹³Or if it exists
Ring A¹⁴But

[0220]

Embedded image Or

[0221]

Embedded image A mixture containing compounds of the formulas IfF2-1 to IfF2-4 and IfF3-1 to IfF3-8, which are

(F) is Phe, Phe. 3F or Phe. 3F5F
Bicyclic compounds of the formulas IfF2-1 to IfF2-4 are particularly preferred. The bicyclic compounds of formulas IfF2-1 to IfF2-4, wherein Phe. (F) is Phe.2F, are characterized by good miscibility with other liquid crystals and are therefore particularly preferred. Liquid crystal mixtures containing these preferred compounds are preferred.

A liquid crystal mixture containing one or more of the following particularly preferred bicyclic compounds is more particularly preferred.

R ¹ -Cyc-Phe-F IfF2-1a R ¹ -Cyc-Phe. 2F-F IfF2-1b R ¹ -Cyc-Phe. 3F-F IfF2-1c R ¹ -Cyc-Phe. 3F5F-F IfF2-1d R ¹ --Cyc--CH ₂ CH ₂ --Phe--F IfF2-1e R ¹ --Cyc--CH ₂ CH ₂ --Phe.2F--F IfF2-1f R ¹ --Cyc--CH ₂ CH ₂ --Phe.3F -F IfF2-1g R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F5F-F IfF2-1h R ¹ -Pyr-Phe-F IfF2-1i R ¹ -Pyr-Phe.2F-F IfF2-1K R ^1- Pyr-Phe. 3F-F IfF2-1L ¹ -Pyr-Phe. 3F5F-F IfF2-1M R ¹ -Pyd-Phe-F IfF2-1N R ¹ -Pyd-Phe. 2F-F IfF2-1O R ^1- Pyd-Phe. 3F-F IfF2-1p R ¹ -Pyd-Phe. 3F5F-F IfF2-1q R-Dio-Phe-F IfF2-1r R-Dio-Phe.2F-F IfF2-1s R-Dio-Phe .3F-F IfF2-1t R-Dio-Phe.3F5F-F IfF2-1uR ¹ -Cyc-Phe-CF ₃ IfF2-2a R ¹ -Cyc-Phe.2F-CF ₃ IfF2-2B R ¹ -Cyc- Phe.3F-CF ₃ IfF2-2c R ¹ -Cyc-Phe.3F5F-CF ₃ IfF2-2d R ¹ -Cyc-CH ₂ CH ₂ -Phe-CF ₃ IfF2-2E R ¹ -Cyc-CH ₂ CH ₂ ―Phe.2F―CF ₃ IfF2―2f R ¹ ―Cyc―CH ₂ CH ₂ ―Phe.3F―CF ₃ IfF2―2g R ¹ ―Cyc―CH ₂ CH ₂ ―Phe.3F5F―CF ₃ IfF2―2h R ¹ -Pyr-Phe-CF ₃ IfF2-2i R ¹ -Pyr-Phe.2F-CF ₃ IfF2-2k R ¹ -Pyr-Phe.3F-CF ₃ IfF2-2l R ¹ -Pyr-Phe.3F5F-CF ^{_{3 IfF2-2m R 1 -Pyd-Phe-}} CF 3 IfF2-2n R 1 -Pyd-Phe. 2F-CF 3 IfF2-2o R 1 -Pyd-Phe. 3F-CF 3 IfF2-2p R 1 -Pyd-Phe 3F5F-CF ₃ IfF2-2q R-Dio-Phe-CF ₃ IfF2-2r R-Dio-Phe.2F-CF ₃ IfF2-2s R-Dio-Phe.3F-CF ₃ IfF2-2t R-Dio-Phe .3F5F-CF ₃ IfF2-2uR ¹ -Cyc-Phe-OCF ₃ IfF2-3a R ¹ -Cyc-Phe.2F-OCF ₃ IfF2-3b R ¹ -Cyc-Phe.3F-OCF ₃ IfF2-3c R ¹ -Cyc-Phe.3F5F-OCF ₃ IfF2-3d R ¹ -Cyc-CH ₂ CH ₂ -Phe-OCF ₃ IfF2-3e R ¹ -Cyc-CH ₂ CH ₂ -Phe.2F-OCF ₃ IfF2-3f R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F-OCF ₃ IfF2-3g R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F5F-OCF ₃ IfF2-3h R ¹ -Pyr-Phe-OCF ₃ IfF2-3i R ¹ _{-Pyr-Phe. 2F-OCF 3} IfF2 ^{3k R 1 -Pyr-Phe. 3F} -OCF 3 IfF2-3l R 1 -Pyr-Phe. 3F5F-OCF 3 IfF2-3m R 1 -Pyd-Phe-OCF 3 IfF2-3n R 1 -Pyd-Phe. 2F- ^{_{OCF 3 IfF2-3o R 1 -Pyd-Phe}} . 3F-OCF 3 IfF2-3p R 1 -Pyd-Phe. 3F5F-OCF 3 IfF2-3q R-Dio-Phe-OCF 3 IfF2-3r R-Dio-Phe. 2F-OCF ₃ IfF2-3s R-Dio-Phe.3F-OCF ₃ IfF2-3t R-Dio-Phe.3F5F-OCF ₃ IfF2-3u R ¹ -Cyc-Phe-OCHF ₂ IfF2-4a R ¹ -Cyc- _{Phe. 2F-OCHF 2 IfF2-4b R} 1 -Cyc-Phe. 3F-OCHF 2 IfF2-4c R 1 -Cyc-Phe. 3F5F-OCHF 2 IfF2-4d R 1 -Cyc-CH 2 CH 2 -Phe-OCHF _{^{2 IfF2-4e R 1 -Cyc-CH 2}} CH 2 -Phe. 2F-OCHF 2 IfF2-4f R 1 -Cyc-CH 2 CH 2 -Phe. 3F-OCHF 2 IfF2-4g R 1 -Cyc-CH 2 CH ₂ -Phe.3F5F-OCHF ₂ IfF2-4h R ¹ -Pyr-Phe-OCHF ₂ IfF2-4i R ¹ -Pyr-Phe.2F-OCHF ₂ IfF2-4k R ¹ -Pyr-Phe.3F-OCHF ₂ IfF2- 4l R ¹ ―Pyr―Phe.3F5F―OCHF ₂ IfF2―4m R ¹ ―Pyd―Phe―OCHF ₂ IfF2―4n R ¹ ―Pyd―Phe. 2F―OCHF ₂ IfF2―4o R ¹ ―Pyd―Phe 3F-OCHF ₂ IfF2-4p R ¹ -Pyd-Phe. 3F5F-OCHF ₂ IfF2-4q R-Dio-Phe-OCHF ₂ IfF2-4r R-Dio-Phe.2F-OCHF ₂ IfF2-4s R-Dio- Phe.3F-OCHF ₂ IfF2-4t R-Dio-Phe.3F5F-OCHF ₂ IfF2-4u The following small group of tricyclic compounds is more preferred.

[0225] R¹―Phe―Phe―Z¹²―Phe. (F, 2) ―F IfF3 ―1a R¹―Phe―Phe―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2a R¹―Phe―Phe―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3a R¹―Phe―Phe―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4a R¹―Cyc―Phe―Z¹²―Phe. (F, 2) ―F IfF3 ―1b R¹―Cyc―Phe―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2b R¹―Cyc―Phe―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3b R¹―Cyc―Phe―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4b R¹―Cyc―Cyc―Z¹²―Phe. (F, 2) ―F IfF3 ―1c R¹―Cyc―Cyc―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2c R¹―Cyc―Cyc―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3c R¹―Cyc―Cyc―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4c R¹―Pyd―Phe―Z¹²―Phe. (F, 2) ―F IfF3 ―1d R¹―Pyd―Phe―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2d R¹―Pyd―Phe―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3d R¹―Pyd―Phe―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4d R¹―Pyr―Phe―Z¹²―Phe. (F, 2) ―F IfF3 ―1e R¹―Pyr―Phe―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2e R¹―Pyr―Phe―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3e R¹―Pyr―Phe―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4e R¹―Phe―Pyd―Z¹²―Phe. (F, 2) ―F IfF3 ―1f R¹―Phe―Pyd―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2f R¹―Phe―Pyd―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3f R¹―Phe―Pyd―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4f R¹―Phe―Pyr―Z¹²―Phe. (F, 2) ―F IfF3 ―1g R¹―Phe―Pyr―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2g R¹―Phe―Pyr―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3g R¹―Phe―Pyr―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4g R¹―Cyc―Dio―Z¹²―Phe. (F, 2) ―F IfF3 ―1h R¹―Cyc―Dio―Z¹²―Phe. (F, 2) ―CF_Three IfF3 ―2h R¹―Cyc―Dio―Z¹²―Phe. (F, 2) ―OCF_Three IfF3 ―3h R¹―Cyc―Dio―Z¹²―Phe. (F, 2) ―OCHF_Two IfF3 ―4h R¹―Phe―Z¹¹―Phe―Phe. (F, 2) ―F IfF3 ―5a R¹―Phe―Z¹¹―Phe―Phe. (F, 2) ―CF_Three IfF3 ―6a R¹―Phe―Z¹¹―Phe―Phe. (F, 2) ―OCF_Three IfF3 ―7a R¹―Phe―Z¹¹―Phe―Phe. (F, 2) ―OCHF_Two IfF3 ―8a R¹―Cyc―Z¹¹―Phe―Phe. (F, 2) ―F IfF3 ―5b R¹―Cyc―Z¹¹―Phe―Phe. (F, 2) ―CF_Three IfF3 ―6b R¹―Cyc―Z¹¹―Phe―Phe. (F, 2) ―OCF_Three IfF3 ―7b R¹―Cyc―Z¹¹―Phe―Phe. (F, 2) ―OCHF_Two IfF3-8b In these compounds, Phe. (F, 2) is particularly Phe, Ph
e. 3F or Phe. 3F5F. Z¹²Is -COO-
And formulas IfF3 -1a to 1h, 2a where Phe. (F, 2) is Phe.2F
~ 2h, 3a ~ 3h and 3a ~ 3h and 4a ~ 4h compounds
Preferred. Z ¹²Ga-CH_TwoCH_Two-Or a single bond
And Phe. (F, 2) are Phe, Phe.2F, Phe.3F or Phe.3
Formula IfF3-1a which is F5F, especially Phe, Phe.3F and Phe.3F5F
~ 1h, 2a ~ 2h, 3a ~ 3h and 4a ~ 4h
Preferred. Formulas IfF-5a, 6a, 7a, 8a, 5b, 6b, 7b and
In the compound of 8b, Z¹¹Ha-CH_TwoCH_Two-Or-COO
―, Especially ―CH_TwoCH_Two-Is preferable. These preferred
Liquid crystal mixtures containing one or more of the following compounds are particularly advantageous
Characteristics.

Liquid crystal mixtures containing at least one of the following preferred tricyclic compounds are more particularly preferred.

R ¹ -Phe-Phe-Phe-F IfF3-1a1 R ¹ -Phe-Phe-Phe. 2F-F IfF3-1a2 R ¹ -Phe-Phe-Phe. 3F-F IfF3-1a3 R ¹ -Phe ―Phe―Phe. 3F5F―F IfF3―1a4 R ¹ ―Phe―Phe―Phe―CF ₃ IfF3―1a5 R ¹ ―Phe―Phe―Phe. 3F―CF ₃ IfF3―1a6 R ¹ ―Phe―Phe―Phe― ^{_{OCF 3 IfF3-1a7 R 1 -Phe-Phe}} -Phe. 3F-OCF 3 IfF3-1a8 R 1 -Cyc-Phe-Phe-F IfF3-1b1 R 1 -Cyc-Phe-Phe. 2F-F IfF3-1b2 R ^{1 -Cyc-Phe-Phe. 3F} -F IfF3-1b3 R 1 -Cyc-Phe-Phe. 3F5F-F IfF3-1b4 R 1 -Cyc-Phe-Phe-CF 3 IfF3-1b5 R 1 -Cyc-Phe- Phe. 3F-CF ₃ IfF3-1b6 R ¹ -Cyc-Phe-Phe-OCF ₃ IfF3-1b7 R ¹ -Cyc-Phe-Phe.3F-OCF ₃ IfF3-1B8 R ¹ -Cyc-Cyc-Phe-F IfF3 --1c1 R ¹ --Cyc--Cyc--Phe.2F--F IfF3-1c2 R ¹ --Cyc--Cyc--Phe.3F--F IfF3-1c3 R ¹ --Cyc--Cyc--Phe.3F5F--F IfF3-1C4 R ^1- Cyc-Cyc-Phe-CF ₃ IfF3-1C5 R ¹ -Cyc-Cyc-Phe.3F-CF ₃ IfF3-1C6 R ¹ -Cyc-Cyc-Phe-OCF ₃ IfF3-1C7 R ^1- Cyc-Cyc -Phe.3F-OCF ₃ IfF3-1c8 R ¹ -Pyd-Phe-Phe-F IfF3-1D1 R ¹ -Pyd-Phe-Phe.2F-F IfF3-1D2 R ¹ -Pyd-Phe-Phe. ^{3F-F IfF3-1d3 R 1 -Pyd-} Phe-Phe. 3F5F-F IfF3-1d4 R 1 -Pyd-Phe-Phe-CF 3 IfF3-1d5 R 1 -Pyd-Phe-Phe. 3F-CF 3 IfF3- 1d6 R ¹ -Pyd-Phe-Phe-OCF ₃ IfF3-1D7 R ¹ -Pyd-Phe-Phe.3F-OCF ₃ IfF3-1D8 R ¹ -Pyr-Phe-Phe-F IfF3-1E1 R ¹ -Pyr-Phe -Phe.2F-F IfF3-1E2 R ¹ -Pyr-Phe-Phe.3F-F IfF3-1E3 R ¹ -Pyr-Phe-Phe.3F5F-F IfF3-1E4 R ¹ -Pyr-Phe-Phe-CF ₃ IfF3-1E5 R ¹ -Pyr-Phe-Phe.3F-CF ₃ IfF3-1E6 R ¹ -Pyr-Phe-Phe-OCF ₃ IfF3-1E7 R ¹ -Pyr-Phe-Phe.3F-OCF ₃ IfF3-1E8 Formula Liquid crystal mixtures containing IfF, one or more compounds of the particularly preferred sub-formulae, have a wide mesogenic range, relatively high clearing points, advantageous values for birefringence and flow viscosity, low for the polymers used in the matrix. Hydratable, and particularly characterized by advantageous values and high UV and temperature stability with respect to the dielectric anisotropy.

The liquid crystal mixture is 1 to 40%, especially 5 to 30%
Of the formula IfF, especially preferred sub-formulae. In this case, the liquid crystal mixture has 1 to 5 kinds, particularly 1 to 5 kinds.
It preferably comprises three compounds of the formula IfF, particularly preferred subformulae.

Formulas IfF, especially formulas IfF2-1 to IfF2-4 and IfF3-
1-IfF3-8, more particularly one or more compounds selected from the group of compounds of the preferred sub-formula, and furthermore formulas II1-II2
A mixture containing at least one compound selected from the group consisting of 8, III1 to III3 and V1 to VI8 is a particularly preferred liquid crystal mixture. In the liquid-crystal mixtures used according to the invention, the compounds of the formula IfF, in particular the compounds IfF2 and IfF3, more particularly at least one compound of the preferred sub-formula, and additionally the compounds of the formula II1
To II28, III1 to III3 and at least one compound of IV1 to IV8 has a mass of 15% to 100%
%, Especially 25% to 100%.

Liquid crystal mixtures based on the following component mixtures, each containing at least one compound from the substance groups indicated in each case, are particularly suitable for application in matrix systems, but in particular in liquid crystal mixtures: If the mass of the formula IfF of formula (I), especially preferred sub-formulas or other terminally fluorinated compounds, is less than 10%, especially less than 5%, they are less suitable for network systems. T (IfF) 1: R-Cyc- (COO) _c -Phe-CC-Phe. (F) -F (where c = 0 or 1) IV2 T (IfF) 2: R-Cyc- (COO) _c -Phe-CC-Phe. (F) -F (c = 0 or 1) III T (IfF) 3: IfF2-1i or IfF3-1e1 R-Cyc-Cyc-Phe. (F) -X ⁵ ( However, X ⁵ = F or CN) T (IfF) 3: . R-Cyc-Cyc-Phe (F) -X 5 R 1 -Pyr- (Phe) c -Phe-R 1 ( except, X ⁵ = F Or CN and c = 0 or 1) T8 (IfF) 4: IfF2-1i, IfF3-1e1 or LfF3-1d1 IV1 or IV2 On the other hand, a liquid crystal mixture containing this kind of component mixture is a mixture of these components. The mass of the formula IfF, particularly preferred sub-formula compounds or other terminally fluorinated compounds, contained therein is greater than 5%, in particular greater than 10%,
More specifically, when it is 12.5% or more, it is generally preferable for application to a network structure system. One of the above component mixtures and further compounds Ia, Ic, Id, Ie, IfCl. F, I
Liquid-crystal mixtures containing g, Ih or Ii, one or more compounds selected from the group of particularly preferred sub-formulas, are also preferred for application in both matrix systems and network systems. In these mixtures, the mass of the terminally fluorinated compound can be up to 5%. U
= -CF _2, -OCF ₂ or at least one compound further of formula IfF is -OCHF II1~II28, III1~III3 and I
Liquid crystal mixtures containing at least one compound selected from the group of compounds V1 to IV8 are also preferred for application to both matrix systems and network systems.

In addition, the following component mixtures, each containing at least one compound from the indicated substance group, are suitable for both matrix systems and network systems. T (IfF) 5: R ¹ -Cyc- (CH ₂ CH ₂ ) _d -Phe. (F, 2) -X ⁶ (However,
X ⁶ = F, CF ₃ or OCF _3, and d = 0 or OCF _3, and d = 0 or 1) II5 or II16 T (IfF) 6: R 1 -Cyc- (CH 2 CH 2) d -Phe. (F, 2) -X ⁶ (However,
X ⁶ = F, CF ₃ or OCF ₃ , and d = 0 or 1) IV1, IV2, IV3, IV4, IV5, IV6, IV7 or IV8 T (IfF) 7: R ¹ -Cyc-CH ₂ CH ₂ ) _d -Phe. (F, 2) -X ⁶ (However, X
⁶ = F, CF ₃ or OCF _3, and d = 0 or 1) II3, II4, II14, II19, II2, II20, II22 or II23 T (IfF) 8: R 1 -Cyc-CH 2 CH 2) d - Phe. (F, 2) -X ⁶ (However, X
⁶ = F, CF ₃ or OCF ₃ , and d = 0 or 1) II1 or II9 T (IfF) 9: R ¹ -Pyr-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) II6 or II16 T (IfF) 10: R ¹ -Pyr-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) IV1, IV2, IV3, IV4, IV5, IV6, IV7 or IV8 T (IfF) 11: R ¹ -Pyr-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) II3, II4, II14, II19, II2, II20, II22 or II23 T (IfF) 12: R ¹ -Pyd-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) II1 or II9 T (IfF) 13: R ¹ -Pyd-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) II5 or II16 T (IfF) 14: R ¹ -Pyd-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) IV1, IV2, IV3, IV4, IV5 or IV6 T (IfF) 15: R ¹ -Pyd-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) II3, II4, II14, II19, II2, II20, II22 or II23 T (IfF) 16: R ¹ -Dio-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) III1, III2 or II3 T (IfF) 17: R ¹ -Dio-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) II5 or II16 T (IfF) 18: R ¹ -Dio-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) IV1, IV2, IV3, IV4, IV7 or IV8 T (IfF) 19: R ¹ -Dio-Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃
Or OCF ₃ ) II1 or II9 T (IfF) 20: R ¹ -Cyc-Cyc- (CH ₂ CH ₂ ) _d -Phe. (F, 2) -X ⁶ (where X ⁶ = F, CF ₃ or OCF ₃ and d = 0 or 1) II5 or II16 T (IfF) 21: R ¹ -Cyc-Cyc- (CH ₂ CH ₂ ) _d -Phe. (F, 2) -X ⁶ (where X ⁶ = F , CF ₃ or OCF _3, and d = 0 or 1) IV1, IV2, IV3, IV4, IV5, IV6, IV7 or IV8 T (IfF) 22: R 1 -Cyc-Cyc- (CH 2 CH 2) d - Phe. (F, 2) -X ⁶ (where X ⁶ = F, CF ₃ or OCF ₃ , and d = 0 or 1) II3, II4, II14, II19, II2, II20, II22 or II23 T (IfF) 23: R ¹ -Cyc-Cyc- (CH ₂ CH ₂ ) _d -Phe. (F, 2) -X ⁶ (where X ⁶ = F, CF ₃ or OCF ₃ , and d = 0 or 1) II1 or II9 T (IfF) 24: R ¹ -Pyd-Phe -Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃ , OCF ₃ or OCHF ₂ ) II5 or II16 T (IfF) 25: R ¹ -Pyd-Phe -Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃ , OCF ₃ or OCHF ₂ ) II1 or II9 T (IfF) 26: R ¹ -Pyd-Phe -Phe. (F ) -X ⁶ (however, X ⁶ = F, CF ₃ , OCF ₃ or OCHF ₂ ) IV1, IV2, IV3 or IV4 T (IfF) 27: R ¹ -Pyr-Phe -Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃ , OCF ₃ or OCHF ₂ ) II5 or II16 T (IfF) 28: R ¹ -Pyr-Phe -Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃ , OCF ₃ Or OCHF ₂ ) II1 or hII19 T (IfF) 29: R ¹ -Pyr-Phe -Phe. (F) -X ⁶ (where X ⁶ = F, CF ₃ , OCF ₃ or OCHF ₂ ) IV1, IV2, IV3 , IV4, IV5 or IV6 in each case the following component mixture T (I) containing at least one compound from the group of compounds of the formula mentioned:
fF) Liquid crystal mixtures based on 30 to 35 are preferred. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is from 2 to 38, preferably 2
It contains ~ 35, especially 2-25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystal of the present invention is 10% to 10%.
0%, especially 15% to 100%, more particularly 25% to
Between 100%.

Mixture formula Mass in component mixture [%] T (IfF) 30 IfF 5-75, especially 5-55 I1 5-85, especially 6-65 T (IfF) 31 IfF 5-55 III 2-29 T (IfF) 32 IfF 5-75, especially 5-60 IV 5-63 T (IfF) 33 IfF 5-55 II 5-65, especially 5-52 III 5-29 T (IfF) 34 IfF 5-50 II 5 5-72 IV, especially 5-52 IV 5-56, especially 5-46 T (IfF) 35 IfF 5-50 II 5-75, especially 5-47 III 5-37, especially 5-15 IV 5-50, especially 5 -42 A compound wherein T ² is Cl and v is 0

[0233]

Embedded image (Where R ¹ has the meaning described above) is a more preferred formula
It is a compound of If.

The compounds of the formula IfCl have the lower formulas IfCl2-1 to IfCl2-8
And the following preferred bicyclic and tricyclic compounds of IfCl3-1 to IfCl3-47.

R ¹ -Phe-Phe-Cl IfCl2-1 R ¹ -Pyr-Phe-Cl IfCl2-2 R ¹ -Cyc-Phe-Cl IfCl2-3 R ¹ -Phe-C≡C-Phe-Cl IfCl2- 4 R ¹ -Phe-COO-Phe-Cl IfCl2-5 R ¹ -Phe-OOC-Phe-Cl IfCl2-6 R ¹ -Pyd-Phe-Cl IfCl2-7 R ¹ -Cyc-COO-Phe-Cl IfCl2- 8 R ¹ -Phe-Phe-Phe-Cl IfCl3-1 R ¹ -Cyc-Phe-Phe-Cl IfCl3-2 R ¹ -Cyc-Cyc-Phe-Cl IfCl3-3 R ¹ -Phe-Cyc-Phe-Cl IfCl3-4 R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe-Cl IfCl3-5 R ¹ -Phe-COO-Phe-Phe-Cl IfCl3-6 R ¹ -Phe-Phe- CH ₂ CH ₂ -Phe- Cl IfCl3-7 R ¹ -Phe-Phe-COO-Phe-Cl IfCl3-8 R ¹ -Phe-Phe-OOC-Phe-Cl IfCl3-9 R ¹ -Cyc- CH ₂ CH ₂ -Phe-Phe-Cl IfCl3 -10 R ¹ -Cyc-COO-Phe-Phe-Cl IfCl3-11 R ¹ --Cyc- Phe- CH ₂ CH ₂ -Cl IfCl3-12 R ¹ -Cyc- Phe- C≡C-Phe-Cl IfCl3 -13 R ¹ -Cyc- CH ₂ CH ₂ --Phe- C≡C-Phe-Cl IfCl3-14 R ¹ -Cyc- Ph-COO-Phe- Cl IfCl3-15 R ¹ -Cyc- Phe-OOC-Phe -Cl IfCl3-16 R ¹ -Cyc- CH ₂ CH ₂ -Phe-COO-Phe-Cl IfCl3-17 R ¹ -Phe-Cyc-COO-Phe- Cl IfCl3 -18 R ¹ -Phe-COO-Cyc-Phe -Cl IfCl3 -19 R ¹ -Phe-OOC-Cyc-Phe-Cl IfCl3 -20 R ¹ -Cyc- Cyc-CH ₂ CH ₂ -Phe-C l IfCl3 -21 R ¹ --Cyc- Cyc-COO-P he-C l IfCl3 -22 R ¹ -Cyc- Cyc-OOC-Phe-C l IfCl3 -23 R ¹ -Cyc- CH ₂ CH ₂ -Cyc-COO-Phe- IfCl3 -24 R ¹ -Cyc- CH ₂ CH ₂ -Cyc- Phe-C l IfCl3-25 R ¹ -Cyc-COO-Cyc-Phe-C l IfCl3 -26 R ¹ -Cyc-OOC-Cyc-Phe-C l IfCl3-27 R ¹ -Phe-COO- Phe-COO -Phe-C l IfCl3-28 R ¹ -Phe-COO- Phe-OOC -Phe-C l IfCl3-29 R ¹ -Phe-OOC- Phe-COO -Phe-C l IfCl3-30 R ^1- Phe-OOC- Phe-OOC-Phe-C l IfCl3-31 R ¹ -Cyc-COO- Phe-COO -Phe-C l IfCl3-32 R ¹ -Cyc-COO- Phe-OOC -Phe-C l IfCl3- 33 R ¹ -Cyc-OOC- Phe-OOC -Phe-C l IfCl3-34 R ¹ -Cyc-OOC- Phe-COO-Phe-C l IfCl3-35 R ¹ -Cyc-COO- Cyc-COO -Phe- C l IfCl3-36 R ¹ -Cyc-OOC- Cyc-COO-Phe-C l IfCl3-37 R ¹ -Cyc-COO- Cyc-OOC -Phe-C l IfCl3-38 R ¹ -Cyc-OOC- Cyc- OOC -Phe-C l IfCl3-39 R-Pyr-Phe-PheCl IfCl340 R-Pyd-Phe-Phe-Cl IfCl3-41 R-Phe-Pyr-Phe-Cl IfCl3-42 R-Phe-Pyd-Phe-Cl IfCl3-43 R-Cyc-Pyr-Phe-Cl IfCl3-44 R-Cyc-Pyd-Phe-Cl IfCl3-45 R-Pyr-CH ₂ CH ₂ -Phe-Phe-Cl IfCl3-46 R-Pyd-Ch ₂ in the compounds of the CH ₂ -Phe-Phe-Cl IfCl3-47 formula IfCl2 and IfCl3, R ¹ is a straight-chain group 1-10 preferably that, alkyl, that is alkenyl or alkoxy particularly preferably having 1 to 8 C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds.

R ¹ is methyl, ethyl, propyl, butyl,
Bentil, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, butoxy, pentoxy, hexosyl, heptoxy, octoxy, methoxymethyl,
Ethoxymethyl, propoxymethyl, butoxymethyl,
Formulas IfCl2-1 to IfCl2-8 and IfCl3-1 to IfCl3-47 which are methoxyethyl, ethoxyethyl or propoxyethyl
Are particularly highly preferred compounds.

Formula IfCl and preferred subformulas IfCl2-2 to IfC
The compounds l2-8 and IfCl3-1 to IfCl3-37 are mostly known, for example JP60 / 260679A2; JP5
9/81375 A2; EP 0,123,907; JP58 / 7
9938A2; DE 3,136,624; Marsate (Ma
lthete), Mol. Cryst. Liq. Cryst. 23 , 233 (197
3); Marsate et al., J. Phys. Colloq., 37, C31 (1
976); JP Vanmeter, etc., Mol. Cryst. L
iq. Cryst., 22 , 271 (1973); ME Newbert (Neub
ert) et al., Mol. Cryst. Liq. Cryst., 135 , 283 (1986);
JP / 56 / 120641A2; EP 152,014; DE3,
139,130; HJ Muller et al., Mol. Cryst.
Liq. Cryst., 92 , 63 (1983); JP61 / 225147A.
2: JP57 / 183727A2: DE 3,139,130;
GW Gray (Gray) and JW Goodby (Goodby), Mo
l. Cryst. Liq. Cryst., 37 , 157 (1976); JP57 /
18538A2; Takatsu et al., Mol. Cryst.
Liq. Cryst., 100 345 (1983); DE 3,233,64.
1: GB 2,071,1131; SM Kelly and
Hp. Sshad, Helv. Chim. Acta, 68 , 1444.
(1985); USP 4,726,910; R. Dabroski (Dabro
wski) et al., Moll Cryst. Liq. Crysyt. 107 , 411 (1984);
JP56 / 120641A2; JP57 / 31645A2; J
P60 / 41638A2; JP 59 / 29640A2; DE3,
317,507; GB 2,070,593; JP57 / 541
48A2; H. Takatsu et al., Mol. Cryst. Liq. Cryst., 10
8 , 157 (1984); JP59 / 113081A2; EP10.
2,047 ,; JP. Banmeter, Mol.Cryst. Liq. C
ryst., 22 , 285 (1973); H.-J. Deutsche
r) et al., J. Prakt. Chem., 321 , 47 (1979); H.-J. Deitcher et al., J. Parkt. Chem., 321 , 969 (1979); JP
58 / 4745A2.

Compounds of formula IfCl1, especially compounds of formulas IfCl2-1 to IfCl2-
Liquid crystal mixtures containing one or more compounds selected from the group of preferred compounds of 8 and IfCl3-1 to IfCl3-47 are advantageous values for birefringence Δn and dielectric anisotropy, high stability, relatively simple It is characterized by manufacturability, low miscibility with the polymers used for the matrix, and especially advantageous values for the wide mesogenic range, relatively high clearing points and the temperature dependence of the flow viscosities and electro-optical parameters.

The liquid crystal mixture of the present invention comprises 1 to 40%, especially 5%
It preferably contains 〜30% of the compounds of the formula IfCl, particularly the preferred subformulae. In this case, the liquid crystal mixture has the formula IfCl,
It is preferred to contain from 1 to 5 and especially from 1 to 3 compounds of the particularly preferred sub-formula.

Formulas IfCl, especially Formulas IfCl2-1 to IfCl2-8 and If
One or more compounds selected from the group of compounds Cl3-1 to IfCl3-47 and further formulas II1-II28, III1-III3 and IV1-IV
A mixture containing at least one compound selected from the group consisting of eight compounds is a particularly preferred liquid crystal mixture. In the liquid-crystal mixtures used according to the invention, the compounds of the formula IfCl, particularly preferred at least one compound of the sub-formula, and also the compounds of the formulas II1-II2
8, the mass of the component mixture comprising at least one of the compounds III1 to III3 and IV1 to IV8 is preferably from 15% to 100%, particularly preferably from 25% to 100%.

Mixtures containing at least one compound from Group C below and at least one compound from Group D below are particularly preferred liquid crystal mixtures.

Group C Group D IfCl2-1, IfCl2-2, II1, II2, II3, II4, IfCl2-3, IfCl2-7, II5, II6, II7, II8, IfCl2-8, IfCl3-1, II9, II10 , II11, II15, IfCl3-2, IfCl3-3, II16, II17, II21, II22, IfCl3-40, IfCl3-41, II23, II25, II26, II27, IfCl3-42, IfCl3-43, II28, III1, III2 , IV1, IfCl3-44, IfCl3-45, IV2, IV3, IV4, IV5, IfCl3-46, IfCl3-47 IV6, IV7, IV8 In each case, at least one compound from the group of compounds of the stated formula The following component mixture T (IC
l) Liquid crystal mixtures based on 1-3 are preferred. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 kinds, preferably 2 to 3 kinds.
It contains 5, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%.
The mass of the component mixture in the liquid crystal of the present invention is 10% to 100%.
%, Especially 15% to 100%, more particularly 25% to 1%
00%.

Mixture formula Mass in component mixture [%] T (ICl) 1 ICl 5-55 II 5-57, especially 5-65 T (ICl) 2 ICl 5-50 IV 5-75, especially 5-70 T (ICl) 3 ICl 5-45, especially 5-40 II 5-55 IV 5-53

[0244]

Embedded image Is a compound of formula If is Phe.3F-Cl or Phe.3F5F

[0245]

Embedded image (Where R ¹ is as defined above, and X ⁷ is F or H
Is a more preferred compound.

The compound of formula IfCl.F has the formula

[0247]

Embedded image And bicyclic and tricyclic compounds.

In the bicyclic compound of the formula IfCl.F2, the ring A ¹³
Is Phe, Phe.F, Cyc, Pyr, Pyd or Dio, especially Phe, Cyc,
Preferably it is Pyd or Dio. Z ¹¹ is a single bond, -COO
-, -OCO- or -CH ₂ CH ₂ -, in particular a single bond, -CH ₂ CH ₂ - or -COO-.

Particular preference is given to the following subgroups of bicyclic compounds of the formulas IfCl.F2-1 to IfCl.F2-19.

R-Phe-Phe.3F-Cl IfCl.F2-1 R-Phe-.3F-Phe.3F-Cl IfCl.F2-2 R-Cyc-Phe.3F-Cl IfCl.F2-3 R- Pyr-Phe.3F-Cl IfCl.F2-4 R-Pyd-Phe.3F-Cl IfCl.F2-5 R-Dio-Phe.3F-Cl IfCl.F2-6 R-Phe-CH ₂ CH ₂ -Phe .3F-Cl IfCl.F2-7 R-Phe-COO-Phe.3F-Cl IfCl.F2-8 R-Cyc-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F2-9 R-Cyc-COO- Phe.3F-Cl IfCl.F2-10 R-Cyc-OCO-Phe.3F-Cl IfCl.F2-11 R-Phe-Phe.3F5F-Cl IfCl.F2-12 R-Cyc-Phe.3F5F-Cl IfCl .F2-13 R-Pyr-Phe.3F5F-Cl IfCl.F2-14 R-Pyd-Phe.3F5F-Cl IfCl.F2-15 R-Dio-Phe.3F5F-Cl IfCl.F2-16 R-Phe- CH ₂ CH ₂ -Phe.3F5F-Cl IfCl.F2-17 R-Phe-COO-Phe.3F5F-Cl IfCl.F2-18 R-Cyc-CH ₂ CH ₂ -Phe.3F5F-Cl IfCl.F2-19 In tricyclic compounds of the formula IfCl.F3, Z ¹¹ and Z ¹² are
A single bond independently of one another, -COO-, -COC- or -CH ₂ CH ₂
And one of the bridging radicals Z ¹¹ and Z ¹² is preferably a single bond.

Ring A ¹³ and ring A ¹⁴ are independently of each other Phe,
It is preferably Phe.F, Cyc, Pyr, Pyd or Dio,
If one of the rings A ¹³ and ring A ¹⁴ is a heterocyclic compound, the other ring is Phe, Phe.F or Cyc, it is preferred in particular Phe or Cyc.

Particular preference is given to the following subgroups of tricyclic compounds of the formulas IfCl.F3-1 to IfCl.F3-38.

R ¹ -Phe-Phe.F-Phe.3F-Cl IfCl.F3-1 R ¹ -Phe-Phe-Phe.3F-Cl IfCl.F3-2 R ¹ -Cyc-Phe-Phe.F- Phe.3F-Cl IfCl.F3-3 R ¹ -Cyc-Cyc-Phe.3F-Cl IfCl.F3-4 R ¹ -Phe-Pyr-Phe.3F-Cl IfCl.F3-5 R ¹ -Phe-Pyd -Phe.3F-Cl IfCl.F3-6 R ¹ -Dio-Cyc-Phe.3F-Cl IfCl.F3-7 R ¹ -Dio-Phe-Phe.3F-Cl IfCl.F3-8 R ¹ -Pyr- Phe-Phe.3F-Cl IfCl.F3-9 R ¹ -Pyd-Phe-Phe.3F-Cl IfCl.F3-10 R ¹ -Cyc-Pyr-Phe.3F-Cl IfCl.F3-11 R ¹ -Cyc -Pyd-Phe.3F-Cl IfCl.F3-12 R ¹ -Phe.F-Pyd-Phe.3F-Cl IfCl.F3-13 R ¹ -Pyd-Phe.F-Phe.3F-Cl IfCl.F3- 14 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-Cl IfCl.F3-15 R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-16 R ¹ -Dio- Cyc-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-17 R ¹ -Dio-Phe-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-18 R ¹ -Phe-Phe.F-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-19 R ¹ -Phe-COO-Phe.F-Phe.3F-Cl IfCl.F3-20 R ¹ -Phe-COO-Phe-COO-Phe.3F-Cl IfCl.F3-21 R ¹ -Cyc-COO-Phe-Phe.3F-Cl IfCl.F3-22 R ¹ -Cyc-Phe-COO-Phe.3F-Cl IfCl.F3-23 R ¹ -Cyc-COO- Cyc-Phe.3F-Cl IfCl.F3-24 R ¹ -CyC-Cyc-COO-Phe.3F-Cl IfCl.F3-25 R ¹ -Phe-Phe-Phe.3F5F-Cl IfCl.F3-26 R ¹ - Cyc-Phe-Phe.3F5F-Cl IfCl.F3-27 R ¹ -Cyc-Cyc-Phe.3F5F-Cl IfCl.F3-28 R ¹ -Pyr-Phe-Phe.3F5F-Cl IfCl.F3-29 R ¹ -Pyd-Phe-Phe.3F5F-Cl IfCl.F3-30 R ¹ -Phe-Pyr-Phe.3F5F-Cl IfCl.F3-31 R ¹ -Phe-Pyd-Phe.3F5F-Cl IfCl.F3-32 R ¹ -Doi-Phe-Phe.3F5F-Cl IfCl.F3-33 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F5F-Cl IfCl.F3-34 R ¹ -Cyc-Cyc-CH ₂ CH _2- Phe.3F5F-Cl IfCl.F3-35 R ¹ -Phe-Phe-COO-Phe.3F5F-Cl IfCl.F3-36 R ¹ -Cyc-COO-Phe.3F5F-Cl IfCl.F3-37 R ¹ -Cyc -CyC-COO-Phe.3F5F-Cl IfCl.F3-38 In the compounds of formula IfCl.F, particularly preferred sub-formulas IfCl.F2-1 to IfCl.2-19 and IfCl.3-1 to IfCl.F3-38 , R ¹ is 1 to
Preference is given to alkyl, alkoxy, alkoxyalkyl and alkenyl having 10 C atoms.

R ¹ is methyl, ethyl, propyl, butyl,
It is preferably pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, deoxy, methoxyethyl, ethoxyethyl, or propoxyethyl.

The compounds of formulas IfCl.F2 and IfCl.F3 are DE3,
Preferably, it is prepared by the method described in US Pat.

Formulas IfCl.F, especially Formulas IfCl.F2-1 to IfCl.F2-19
And a liquid crystal mixture containing one or more compounds selected from the group of compounds of IfCl.F3-1 to IfCl.F3-38 is birefringent,
It is characterized by advantageous values for clearing point and viscosity, and especially for Δε, high UV and temperature stability and high resistivity. These mixtures are preferred.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 〜30% of the compound of the formula IfCl.F, particularly preferred subformulae. In this case, the liquid crystal mixture has the formula IfC
It preferably contains 1F, particularly preferred 1 to 5, especially 1 to 3, sub-compounds.

Those skilled in the art will recognize a limited group of compounds of the formula IfCl.F without inventive assistance such that the liquid crystal and the filled electro-optics are optimized within certain limits for a particular application. In particular, the formulas IfCl.F2-1 to IfCl.F2-9 and IfCl.F3-1 to I
It can always be selected from a small group of compounds fCl.3-1 to IfCl.F3-38. If it is desired that the liquid crystal mixture has a high or even very high birefringence, for example,
For example, IfCl.F2-1, IfCl.F2-2, IfCl.F2-4, IfCl.F2-
5, IfCl.F2-7, IfCl.F2-8, IfCl.F2-12, IfCl.F2-1
4, IfCl.F2-15, IfCl.F2-17, IfCl.F2-18, IfCl.F3-
1, IfCl.F3-2, IfCl.F3-5, IfCl.F3-6, IfCl.F3-9,
IfCl.F3-10, IfCl.F3-13, IfCl.F3-14, IfCl.F3-1
9, IfCl.F3-20, IfCl.F3-21, IfCl.F3-26, IfCl.F3-
29, IfCl.F3-30, IfCl.F31, IfCl.F3-32 and IfCl.F
It is preferred to select a compound of the formula IfCl.F, which does not have a saturated ring system such as 3-36, especially preferred sub-formulae compounds.

Furthermore, compounds having a pyridine or pyrimidine ring and / or a Phe.3F5F-Cl group can be advantageously used, for example, in order for the mixture to have a relatively high or high Δε.

Compounds of formula IfCl.F, especially compounds of formulas IfCl.F2-1 to IfC
l.F2-19 and one or more compounds selected from the group of preferred compounds of IfCl.F3-1 to IfCl.F3-38 and further compounds
A mixture containing at least one compound selected from the group consisting of II1 to II27, III1 to III3 and IV1 to IV8 is a particularly preferred liquid crystal mixture.

In the liquid-crystal mixtures used according to the invention, at least one compound of the formula IfCl.F, a particularly preferred sub-formula, and furthermore at least one compound of the formulas II1-II27, III1-III3 and IV1-IV8 The weight of the resulting component mixture is preferably between 15% and 100%, in particular between 25% and 100%.

The following mixture T (IfCl.) Containing at least one compound of each of the indicated compound groups:
F) is particularly preferred and is suitable for application in both matrix and network systems.

T (IfCl.F) 1: IfCl.F2-1 and / or IfCl.F2-12 II1 T (IfCl.F) 2: IfCl.F2-1 and / or IfCl.F2-12 II5 T (IfCl.F .F) 3: IfCl.F2-1 and / or IfCl.F2-12 IV1 T (IfCl.F) 4: IfCl.F2-1 and / or IfCl.F2-12 IV2 T (IfCl.F) 5: IfCl. .F2-3 and / or IfCl.F2-13 II1 T (IfCl.F) 6: IfCl.F2-3 and / or IfCl.F2-13 II5 T (IfCl.F) 7: IfCl.F2-3 and / or Or IfCl.F2-13 III1 T (IfCl.F) 8: IfCl.F2-3 and / or IfCl.F2-13 IV1 T (IfCl.F) 9: IfCl.F2-3 and / or IfCl.F2-13 IV2 T (IfCl.F) 10: IfCl.F2-4 II1 T (IfCl.F) 11: IfCl.F2-4 II5 T (IfCl.F) 12: IfCl.F2-4 IV4 T (IfCl.F) 13 : IfCl.F2-4 IV5 T (IfCl.F) 14: IfCl.F2-5 II1 T (IfCl.F) 15: IfCl.F2-5 II5 T (IfCl.F) 16: IfCl.F2-5 IV4 T (IfCl.F) 17: IfCl.F2-5 IV5 T (IfCl.F) 18: IfCl.F3-3 and / or IfCl.F3-27 II1 T (IfCl.F) 19: IfCl.F3-3 and / or Or IfCl.F3-27 II5 T (IfCl.F) 20: IfCl.F3-3 and / or IfCl.F3-27 IV1 T (IfCl.F) 21: I fCl.F3-3 and / or IfCl.F3-27 IV5 T (IfCl.F) 22: IfCl.F3-3 and / or IfCl.F3-27 II4 T (IfCl.F) 23: IfCl.F3-4 and And / or IfCl.F3-28 II1 T (IfCl.F) 24: IfCl.F3-4 and / or IfCl.F3-28 II4 or II5 T (IfCl.F) 25: IfCl.F3-4 and / or IfCl. F3-28 II6 T (IfCl.F) 26: IfCl.F3-4 and / or IfCl.F3-28 III1 T (IfCl.F) 27: IfCl.F3-4 and / or IfCl.F3-28 IV1 T ( IfCl.F) 28: IfCl.F3-4 and / or IfCl.F3-28 IV2 In addition to the dielectrically positive component A consisting of a dielectrically positive compound with Δε> 2, −2 ≦ Δε ≦ + 2 Further preferred is a liquid crystal mixture comprising a dielectrically neutral component B consisting of a compound of formula (I) and optionally a dielectrically negative component C consisting of a compound of Δε <−2.

Assuming that the mass of the dielectrically positive compound in the liquid crystal is a, the mass of the dielectrically neutral compound is b, and the mass of the dielectrically negative compound is c, a is ≧ 30.
%, Especially> 50%. When the dielectrically positive component A is based on carbonitrile in particular, the liquid crystal has a dielectrically neutral component to suppress the formation of a dimer having an antiparallel correlated dipole moment. It is preferred to include. The value obtained by dividing the mass of the dielectrically positive component by the mass of the dielectrically neutral component is 35 ≧ a / b ≧ 0.5, especially 15
It is preferred that ≧ a / b ≧ 1.

On the other hand, the liquid crystal has F, Cl,
When the main component is a liquid crystal compound having CF ₃ , OCF ₃ , OCHF ₂ or NCS, the content of a dielectrically neutral compound may be small or zero. b is ≦ 45%, especially ≦ 35%,
More particularly, it is preferred that ≦ 25%.

Since a low switching voltage is usually desirable, the content of dielectrically negative compounds is generally low. c is ≦ 10
%. Particularly preferred is ≦ 5%, and liquid crystal mixtures with c ≦ 3% are generally particularly preferred.

Formulas Ig R ¹ -Q ⁴ -COO-Q ⁵ -R ² Ig wherein Q ⁴ and Q ⁵ are each independently of the other

[0268]

Embedded image Or

[0269]

Embedded image And one of Q ⁴ and Q ⁵ is

[0270]

Embedded image Or

[0271]

Embedded image And R ¹ and R ² independently of one another in each case have the meanings indicated in claim 1). Liquid crystals which comprise one or more dielectrically neutral compounds according to claim 1 are preferred.

The compounds of the formula Ig are preferably of the following formulas Ig2-1 and I
g2-2 bicyclic compound.

R ¹ -Phe-COO-Phe-R ² Ig2-1 R ¹ -Cyc-COO-Phe-R ² Ig2-2 In compounds of formula Ig2-1 and Ig2-2, R ¹ and R
² are preferably, independently of one another, an alkyl or alkoxy having 1 to 10, in particular 1 to 8 C atoms,
Furthermore, it is n-alkoxyalkyl, especially n-alkoxymethyl and n-alkoxyethyl. One of the two 2,4-phenylene groups of the compound of the formula Ig2-1 and the 1,4-phenylene group of the compound of the formula Ig2-2 are substituted by Cl or F at two or three positions, in particular by F at three positions. be able to.

Particularly preferred compounds are those of the following formula:

R ¹ -Phe-COO-Phe-alkyl or alkoxy Ig2-1a R ¹ -Phe-COO-Phe.3F-alkyl or alkoxy Ig2-1b R ¹ -Phe-COO-Phe.2F-alkyl or alkoxy Ig2 -1c R ¹ -Phe-COO-Phe.3F-Alkoxymethyl Ig2-1d R ¹ -Cyc-COO-Phe-alkyl or alkoxy Ig2-2a R ¹ -Cyc-COO-Phe.2F-Alkyl or alkoxy Ig2-2b R ¹ -Cyc-COO-Phe.3F-alkyl or alkoxy Ig2-2c Compounds of the formula Ig are those in which one of the groups Q1 and Q2 is 1,4-phenylene or trans-1,4-cyclohexylene and the other is

[0276]

Embedded image Or

[0277]

Embedded image Embedded image

Preferred compounds are those of the following formula:

R ¹ -Phe-COO-Phe. (F) -Phe.R ² Ig3-1 R ¹ -Phe-Phe-COO-Phe. (F) .R ² Ig3-2 R ¹ -Cyc-Phe. (F) -COO-Phe. (F) -R ² Ig3-3 R ¹ -Cyc-COO-Phe-COO-Phe. (F) -R ² Ig3-4 R ¹ -Phe-COO-Phe. (F ) -COO-Phe-R ² Ig3-5 R ¹ -Cyc-Cyc-COO-Phe. (F) -R ² Ig3-6 R ¹ -Phe-COO-Cyc-Cyc-R ² Ig3-7 R ^1- Cyc--OCO-Phe-Cyc-R ² Ig3-8 R ¹ -Cyc-COO-Phe. (F) -Phe-R ² Ig3-9 R ¹ -Phe. (F) -Phe-COO-Cyc-R ² Ig3-10 In compounds of the sub-formula Ig3-1 to Ig3-10, R ¹ and R
² are preferably independently n-alkyl or n-alkoxy having 1 to 10 C atoms, furthermore 1
Also n-alkoxymethyl and n-alkoxyethyl having ８8 C atoms. Compounds of formula Ig3-1 to Ig3-10 can have one of the 1,4-phenylene groups laterally monosubstituted by X = F or Cl. In this case, it is preferred that three sites be replaced by F.

R ¹ and R ² independently of one another are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, methoxymethyl, ethoxymethyl, propoxymethyl , Butoxymethyl, pentoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, or pentoxyethyl of the formula Ig3-1, Ig3-2, Ig3-3, Ig3-5, Ig3-6, Ig3-
8, laterally unsubstituted or monosubstituted compounds of Ig3-9 and Ig3-10 are particularly preferred.

The compounds of the formula Ig are such that the radicals Q ¹ and Q ² are in each case independently of one another

[0282]

Embedded image Or

[0283]

Embedded image Embedded image

Preferred compounds are those of the following formulas Ig4-1 to Ig4-10.

R ¹ -Phe-Phe-COO-Phe. (F) -Phe-R ² Ig4-1 R ¹ -Phe. (F) -Phe-COO-Cyc-Phe-R ² Ig4-2 R ^1- Phe-Phe. (F) -COO-Phe-COO-Phe-R ² Ig4-3 R ¹ -Phe-Phe. (F) -COO-Cyc-Cyc-R ² Ig4-4 R ¹ -Cyc-Phe- COO-Phe. (F) -Phe-R ² Ig4-5 R ¹ -Cyc-Phe-COO-Phe. (F) -COO-Phe. (F) -R ² Ig4-6 R ¹ -Cyc-Phe- COO-Cyc-Cyc-R ² Ig4-7 R ¹ -Cyc-Phe. (F) -COO-Phe-Cyc-R ² Ig4-8 R ¹ -Cyc-Cyc-COO-Phe-Cyc-R ² Ig4- ^{9 R 1 -Cyc-COO-Phe} -COO-Phe. (F) R 1 and R ² in the compounds of -Phe-R ² Ig4-10 formula Ig4-1~Ig4-10 are independently from each other methyl, ethyl , Propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl,
Preference is given to methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl or propoxyethyl. Formula Ig4-1, Ig4-3, Ig4-4
And compounds in which the terminal group of Ig4-10 is symmetrically substituted. Compounds of formulas Ig4-1 to Ig4-10 can have one of the 1,4-phenylene groups laterally mono-substituted by F or Cl. In this case, it is preferable to substitute 2 or 3 sites with F. Further preferred are compounds of the formula Ig4-9.

Compounds of the formula Ig are described, for example, in DE 2,167,25
2, DE2,800,553, DE2,536,046, DE2,
Prepared by transesterification of appropriately substituted phenols or phenoxides with appropriately substituted carboxylic acids or reactive carboxylic acid derivatives as described in 123,175 and DE 2,139,628. preferable.

Formula Ig, especially Ig2-1, Ig2-2, Ig2-1a-1d, Ig
Liquid crystal mixtures containing one or more compounds selected from the group consisting of 2-2a to 2c, Ig3-1 to Ig3-10 and Ig4-1 to Ig4-10 are advantageous values for Δε, high stability, easy It is characterized by good manufacturability, low miscibility with the polymers used for the matrix, and especially favorable values for the wide mesogenic range, relatively high clearing points and birefringence and flow viscosity.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 30% of a compound of the formula Ig, particularly the preferred subformulae. In this case, the liquid-crystal mixture preferably contains compounds of the formula Ig, particularly preferably 1 to 5, especially 1 to 3, of the lower formulas.

Formulas Ig, particularly preferred Formulas Ig2-1 to Ig2-2, Ig2-
1a-1d, Ig2-2a-2c, Ig3-1-Ig3-10 and Ig4-1-Ig4
Particularly preferred is a liquid crystal mixture containing one or more compounds selected from the compound group of -10 and one or more compounds selected from the group of compounds II1 to II28, III1 to III3, and IV1 to IV8.

In the liquid-crystal mixtures used according to the invention, at least one compound of the formula Ig, particularly a preferred sub-formula, and furthermore the compounds of the formulas II1-II28, III1- and III3 and IV1-IV8
Is preferably from 15% to 100%, especially from 25% to 100%.

Liquid crystal mixtures based on component mixtures consisting of at least one laterally unsubstituted compound of the formula Ig2-1 and one or more compounds of the formula IV1 are highly preferred for matrix systems, on the contrary. This is not very desirable for network structures. However, besides the compounds of these formulas, formulas Ia, Ic, Id, Ie, IfF, IfCl, IfCl.F, Ih
Alternatively, liquid-crystal mixtures containing Ii, at least one compound selected from the group of particularly preferred sub-formulas, are generally also preferred for the network system.

Particular preference is also given to the following subgroups of component mixtures T (Ig), each containing at least one compound from the substance groups indicated in each case.

T (Ig) 1: Ig2-1a, Ig2-1b and / or Ig
2-1c II1, II5, II6, IV1, IV2, IV3 and / or IV
4 T (Ig) 2: Ig2-2a, Ig2-2b and / or Ig2-2c II1, II5, II6, III1, III2, IV1, IV2, IV3 and / or IV4 T (Ig) 3: Ig3-1, Ig3 -3, Ig3-6, Ig3-9 and / or Ig
3-10 II1, II2, II3, II4, II5, II6, IV1 and / or IV2 The following component mixtures T (I) each containing at least one compound from the group of compounds of the formulas mentioned in each case:
g) Liquid crystal mixtures based on 4 to 6 are preferred. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 kinds, preferably 2 to 3 kinds.
It contains 5, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%.
The mass of the component mixture in the liquid crystal of the present invention is 10% to 100%.
%, Especially 15% to 100%, more particularly 25% to 1%
00%.

Mixture formula Mass in component mixture [%] T (Ig) 4 Ig 5-75 II 6-65 T (Ig) 5 Ig 5-75 IV 5-75, especially 5-63 T (Ig) 6 Ig 5-55, especially 5-50 II 5-72, especially 5-53 IV 5-50, especially 5-44 Formula Ih R ¹ -Q ⁶ -C≡C-Q ⁷ -R ² Ih (wherein at least one of the radicals R ¹ and R ² have the meaning indicated in claim 1, 2 radicals R ¹ and one of R ² is F, Cl, OCF
₃ , also OCHF ₂ or CF ₃ , wherein Q ⁶ and Q ⁷ are each, independently of one another,

[0295]

Embedded image Or

[0296]

Embedded image And Q ⁶ is

[0297]

Embedded image Or

[0298]

Embedded image And Q ⁷ is

[0299]

Embedded image Are also preferred liquid crystal mixtures.

The compounds of formula Ih are preferably of the following formulas I2h-1 to I2h-3
And bicyclic compounds which are preferred.

R ¹ -Phe-C≡C-Phe-R ² Ih2-1 R ¹ -Pyr-C≡C-Phe-R ² Ih2-2 R ^1- Pyd-C≡C-Phe-R ² Ih2-3 In compounds of the formulas Ih2-1 to Ih2-3 having two non-polar groups, R ¹ and R ² independently of one another are 1 to 10, in particular 1 It is preferably an alkyl or alkoxy having up to 8 C atoms, furthermore n-alkoxyalkyl, especially
Also n-alkoxymethyl and n-alkoxyethyl. One of the 1,4-phenylene groups contained in the compounds of the formulas Ih2-1 to Ih2-3 can be substituted at two or three positions by Cl or F, in particular by F.

The following compounds are particularly preferred.

R ¹ -Phe-C≡C-Phe-alkyl Ih2-1a R ¹ -Phe-C≡C-Phe.2F-alkyl or alkoxy Ih2-1b R ¹ -Phe-C≡C-Phe.3F- Alkyl or alkoxy Ih2-1c R ¹ -Pyr-C≡C-Phe.3F-alkyl or alkoxy Ih2-2a R ¹ -Pyd-C≡C-Phe.3F-alkyl or alkoxy Ih2-3a groups R ¹ and R ² One is F, Cl, OCF ₃ , OCHF ₂ or C
F _3, compounds of formula Ih2-2~Ih2-3 more preferably in particular F or Cl. These compounds have relatively high values for optical and dielectric anisotropy and are characterized by relatively low values for viscosity η. One of the two 1,4-phenylene groups can be replaced at two or three positions by Cl or F, especially by F at three positions.

The following compounds of the formula Ih2 are particularly preferred.

R ¹ -Phe-C≡C-Phe-R ² Ih2-1d R ¹ -Phe.3F-C≡C-Phe-R ² Ih2-1e R ¹ -Phe.2F-C≡C-Phe- R ² Ih2-1f R ¹ -Phe-C≡C-Phe.2F-R ² Ih2-1g R ¹ -Phe-C≡C-Phe.3F-R ² Ih2-1h R ¹ -Phe-C≡C- Pyr-R ² Ih2-2b R ¹ -Phe-C≡C-Pyd-R ² Ih2-3b R ¹ -Pyr-C≡C-Phe-R ² Ih2-2c R ¹ -Pyd-C≡C-Phe- R ² Ih2-3c (where R ¹ is F, Cl, OCF ₃ , OCHF ₂ , or CF ₃ ;
And R ² is alkyl or alkoxy having 1 to 7 C atoms) The compounds of the formula I have the following sub-formulae Ih3-1 to
Including tricyclic compounds which are preferably compounds of Ih3-10.

R ¹ -Phe-C≡C-Phe-Phe-R ² Ih3-1 R ¹ -Phe. (F) -C≡C-Phe-Cyc-R ² Ih3-2 R ¹ -Pyr-C≡ C-Phe-Phe-R ² Ih3-3 R ¹ -Pyd-C≡C-Phe-Phe-R ² Ih3-4 R ¹ -Pyr-C≡C-Phe-Cyc-R ² Ih3-5 R ^1- Pyd-C≡C-Phe-Cyc-R ² Ih3-6 R ¹ -Cyc-CH ₂ CH ₂ -Phe-C≡C-Phe-R ² Ih3-7 R ¹ -Cyc-CH ₂ CH ₂ -Phe- C≡C-Pyd-R ² Ih3-8 R ¹ -Cyc-CH ₂ CH ₂ -Phe-C≡C-Pyr-R ² Ih3-9 R ¹ -Cyc-COO-Phe-C≡C-Phe. in the compounds of F) -R ² Ih3-10 subformula Ih3-1~Ih23-10, R ¹ and R ² of compounds having two nonpolar, independently of one another 1 to 1
Those which are n-alkyl or n-alkoxy having 0 C atoms are preferred, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 8 C atoms. Formula Ih3 having a polar group F, Cl, OCHF ₂ , OCF ₃ or CF ₃
Compounds of -1 to Ih3-10 (where the other group is an alkyl group or alkoxy having 1 to 8 C atoms) are preferred. The compounds of the formulas Ih3-1 to Ih3-10 have in each case one of the 1,4-phenylene groups present in the molecule X = F or Cl
Can be laterally mono-substituted. The following monosubstituted formulas Ih3-1a-1d, Ih3-2a-2b, Ih3-5a and Ih3-6a
6b are particularly preferred.

R ¹ -Phe-C≡C-Phe-Phe.3F-R ² Ih3-1a R ¹ -Phe-C≡C-PhePhe.3Cl-R ² Ih3-1b R ¹ -Phe-C≡C- Phe.3F-Phe-R ² Ih3-1c R ¹ -Phe-C≡C-Phe.3Cl-Phe-R ² Ih3-1d R ¹ -Phe-C≡C-Phe.3F-Cyc-R ² Ih3- 2a R ¹ -Phe-C≡C-Phe.3Cl-Cyc-R ² Ih3-2b R ¹ -Pyr-C≡C-Phe-Phe.FR ² Ih3-5a R ¹ -Pyd-C≡C-Phe- Phe.FR ² Ih3-6a R ¹ -Pyd-C≡C-Phe.F-Phe-R ² Ih3-6b (However, in the compounds of the formulas Ih3-1a to 1d, Ih3-5a and Ih3-6a to 6b, In particular R2 and compounds of the formula Ih3-2a-2b, in particular where R1 is a polar group)
Includes tetracyclic compounds which are preferably compounds of the following subformulae Ih4-1 to Ih4-5:

R ¹ -Phe-Phe-C≡C-Phe. (F) -Phe. (F) -R ² Ih4-1 R ¹ -Phe-Phe. (F) -C≡C-Phe-Cyc- R ² Ih4-2 R ¹ -Cyc-Phe-C≡C-Phe. (F) -Cyc-R ² Ih4-3 R ¹ -Cyc-CH ₂ CH ₂ -Phe-C≡C-Phe. (F) -Cyc-R ² Ih4-4 R ¹ -CyC-CH ₂ CH ₂ -Phe-C≡C-Phe. (F) -Cyc-R ² Ih4-5 In the compounds of the formulas Ih4-1 to Ih4-5, One of R ¹ and R ² is preferably polar, and the other is methyl, ethyl,
Preferably it is propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl or propoxymethyl. Symmetrically substituted compounds of the formulas Ih4-1 and Ih4-3 having two non-polar groups are more preferred. The compounds of the formulas Ih4-1 to Ih4-5 are 1,
One of the 4-phenylene groups can be laterally mono-substituted by F or Cl. In this case, substitution at three sites is preferred.

The compound of formula Ih has the formula DE 2,226,376, GB
2,155,465, GB2,189,785, DE3,711,
306, JP61-260,031, DE3,710,069,
JP02-062,861, JP63-060,972, EP0,2
It is preferably prepared by the methods described in US Pat. No. 55,700 and EP 0,276,067.

Compound Ih, particularly preferred compounds Ih2-1 to Ih2
-3, Ih2-1a-1h, Ih2-2a-2c, Ih2-3a-3c, Ih3-1-Ih3
-10, Ih3-1a to 1d, Ih3-2a to 2b, Ih3-5a, Ih3-6a to 6b and a liquid crystal mixture containing one or more compounds selected from the group of compounds Ih4-1 to Ih4-5 are: Wide mesogenic range,
It is characterized by a relatively high clearing point, a high stability, a low miscibility with the polymer used for the matrix, and advantageous values and birefringence, especially with regard to dielectric anisotropy and viscosity.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 30% of a compound of the formula Ih, particularly the preferred subformulae. In this case, the liquid-crystal mixture preferably contains the compounds of the formula Ih, in particular of the preferred subformulas 1 to 5, in particular 1 to 3.

At least one compound selected from the group of compounds of the formula Ih, particularly preferred lower formulas, and further compounds
Liquid crystal mixtures containing one or more compounds selected from the group of II1-II28, III1-III3 and IV1-IV8 are particularly preferred.

In the liquid-crystal mixtures used according to the invention, at least one compound of the formula Ih, particularly a preferred sub-formula, and additionally the compounds of the formulas II1-II28, III1- and III3 and IV1-IV8
Is preferably from 15% to 100%, especially from 25% to 100%.

Liquid-crystal mixtures based on component mixtures consisting of at least one compound of the formula Ih2-1 and also at least one compound of the formulas IV1 and / or IV2 are generally particularly preferably applied to matrix systems. However, they are often not very suitable for application to network structures. The same applies to liquid crystals based on component mixtures containing at least one compound of the formulas Ih3-10 and / or Ih3-2 and at least one compound of the formula IV4. However, the properties of such mixtures are compounds Ia, Ic, Id, I
e, IfF, IfCl, IfCl.F, Ig and II1 to II28, which can be improved by adding at least one compound selected from the group of particularly preferred subformulae compounds, so that their mixtures also have a network structure Found that it can be applied to

The liquid-crystal mixtures based on the component mixtures T (Ih) of the following subgroups, each containing at least one compound from the group of compounds of the formulas indicated in each case, are of the matrix and network systems: Preferred for both. The following table further shows the preferred masses of these compounds in the component mixture.

Mixture formula Mass in component mixture [%] T (Ih) 1 Ih 5-75 II 6-65 T (Ih) 2 Ih 5-75 IV 5-63 T (Ih) 3 Ih 5-55, especially 5 to 50 II 5 to 72, in particular 5 to 53 IV 5 to 50, in particular 5 to 46 In each case at least one compound from the group of compounds indicated in each case, a mixture of the following subgroups is a matrix system: And particularly preferred for network systems. T (Ih) 4: Ih2-1a, Ih2-1b and / or Ih2-1c II1, II2, II3, II5, II6, II8, II9, IV1 and / or IV2 T (Ih) 5: Ih2-2a, 2b and And / or 2c II1, II2, II3, II5, II6, II8, II9, IV1, IV2, IV3 and / or IV4 T (Ih) 6: Ih2-3a, 3b and / or 3c II1, II2, II3, II5, II6 , II8, II9, IV1, IV2, IV3
And / or IV4 T (Ih) 7: Ih3-2 II1, II2, II3, II5, II6, II8, II9, II10, II11, II1
3, II14, II15, II16, II21, II22 and / or II23 T (Ih) 8: Ih3-3 II1, II2, II3, II5, II6, II8, II9, II10, and / or
Or II11 T (Ih) 9: Ih3-4 II1, II2, II3, II5, II6, II8, II9, II10, and / or
Or II11 formula Ii R ¹ -Q ⁸ -CH ₂ CH ₂ -Q ⁹ -R ² Ii wherein R ¹ and R ² are each independently of the meaning given in claim 1, and Q ⁸ And Q ⁹ independently of one another in each case trans-1,4-cyclohexylene, 1,4-phenylene, 4,4′-biphenylyl, 4,4′-cyclohexylphenyl, 4,4′-phenyl Cyclohexyl or trans-, trans-
4,4'-bicyclohexylyl, provided that one of the 1,4-phenylene groups present in the molecule can be replaced by fluorine or chlorine. Liquid crystal mixtures are more preferred.

Compounds of formula Ii are preferably of the following formulas Ii2-1 and Ii:
i2-2 bicyclic compounds.

R ¹ -Phe-CH ₂ CH ₂ -Phe-R ² Ii2-1 R ¹ -Cyc-CH ₂ CH ₂ -Phe-R ² Ii2-2 R ¹ and R ² of the compound of formula Ii2 are Independently 1 to 1
Preference is given to alkyl or alkoxy having 0, especially 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds. One of the two 1,4-phenylene groups can be replaced at two or three positions by Cl or F, especially by F at three positions.

The compound of the following formula is particularly preferred.

Alkyl or alkoxy-Phe-CH ₂ CH ₂ -Phe-R ² Ii2-1a alkyl or alkoxy-Phe.3F-CH ₂ CH ₂ -Phe-R ² Ii2-1b alkoxymethyl-Phe.2F-CH ₂ CH ₂ -Phe-R ² Ii2-1c alkyl or arbor -Cyc-CH ₂ CH ₂ -Phe-R ² Ii2-2a The compound of formula I is a compound of the following sub-formulae Ii3-1 to Ii3-5 And preferably includes tricyclic compounds of subformula Ii3.

R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe -R ² Ii3-1 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe -R ² Ii3-2 R ¹ -Phe-CH ₂ CH ₂ ^{-Phe-Cyc- R 2 Ii3-3 R 1} -Phe-Cyc-CH 2 CH 2 -Phe- R 2 Ii3-4 R 1 -Cyc-CH 2 CH 2 - Phe-Cyc- R 2 Ii3-5 R 1 in the compounds of _{-Cyc-Cyc-CH 2 CH 2} -Phe- R 2 Ii3-6 formula Ii3-1~Ii3-6, R ¹ and R ^2, n having 1 to 10 C atoms independently of one another -Alkyl or n-alkoxy, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 8 C atoms. Compounds of formulas Ii3-1 to Ii3-6 are 1,4-
One of the phenylene groups can be laterally mono-substituted with X = F or Cl. Compounds of formulas Ii3-1 to Ii3-6 which are not substituted with lateral and Phe.
Or 1,4- which is laterally monosubstituted by Cl
Formulas Ii3-1a-1b, Ii3-2a, Ii3-3a, I
Particularly preferred are laterally monosubstituted compounds of i3-6a and Ii3-5a.

R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe.3X-R ² Ii3-1a R ¹ -Phe-CH ₂ CH ₂ -Phe.X-Phe-R ² Ii3-1b R ¹ -Cyc- CH ₂ CH ₂ -Phe-Phe.2X-R ² Ii3-2a R ¹ -Phe-CH ₂ CH ₂ -Phe.X-Cyc-R ² Ii3-3a R ¹ -Cyc-CH ₂ CH ₂ -Phe.2F -Cyc-R ² Ii3-5a R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe.FR ² Ii3-6a Laterally monosubstituted compounds of formulas Ii3-1 to Ii3-6 are generally the corresponding unsubstituted compounds Characterized by lower flow viscosity.

Q ⁸ and Q ⁹ are each independently of the other

[0324]

Embedded image Or

[0325]

Embedded image It further includes certain tetracyclic compounds.

R ¹ -Phe-Phe -CH ₂ CH ₂ -Phe. (F) -Phe-R ² Ii4-1 R ¹ -Phe-Phe -CH ₂ CH ₂ -Phe. (F) -Cyc-R ² Ii4-2 R ¹ -Phe-Cyc -CH ₂ CH ₂ -Phe. (F) -Phe. (F) -R ² Ii4-3 R ¹ -Phe-Cyc -CH ₂ CH ₂ -Phe. (F)- Cyc-R ² Ii4-4 R ¹ -Cyc-Phe. (F) -CH ₂ CH ₂ -Phe-Cyc-R ² Ii4-5 R ¹ -Cyc-Cyc -CH ₂ CH ₂ -Phe. (F)- Phe-R ² Ii4-6 The groups R ¹ and R ^{2 in} the compounds of the formulas Ii4-1 to Ii4-6, independently of one another, are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, It is preferably decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl or propoxyethyl. The compounds of the formulas Ii4-1 to Ih4-6 can have one of the 1,4-phenylene groups laterally monosubstituted by F or Cl. In this case, 3
Site substitution is preferred. These monosubstituted tetracyclic compounds are characterized by a high clearing point and a relatively low flow viscosity η.

Compounds of formula Ii are described in EP-0,084,194, J
P61-087,777, GB2,201,415 and DE
It is preferably produced by the method described in 3,237,367.

Formula Ii, particularly preferred Formulas Ii2-1, Ii2-2, Ii2-
1a-1c, Ii2-2a, Ii3-1-Ii3-5, Ii3-1a-1b, Ii3-2a,
A liquid crystal mixture containing one or more compounds selected from the group consisting of Ii3-6a, Ii3-3a, Ii3-5a and Ii4-1 to Ii4-5 has high stability and low miscibility with the polymer used for the matrix. It is characterized by advantageous properties with regard to the properties and especially the wide mesogenic range, the relatively high clearing point and the optical anisotropy Δn and the flow viscosity η.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 30% of the compounds of the formula Ii, particularly the preferred subformulae. In this case, the liquid-crystal mixture preferably contains 1 to 5, especially 1 to 3, compounds of the formula Ii, particularly preferred lower formulas.

At least one compound selected from the group of compounds of the formula Ii, particularly the lower formulas, and additionally the compounds of the formulas II1-II2
Liquid crystal mixtures containing one or more compounds selected from the group consisting of 8, III1-III3 and IV1-IV8 are particularly preferred.

In the liquid-crystal mixtures used according to the invention, at least one compound of the formula Ii, particularly preferred sub-formulas, and furthermore the formulas II1-II28, III1- and III3 and IV1-IV8
Is preferably from 15% to 100%, especially from 25% to 100%. These component mixtures are preferred for network systems and matrix systems.

The liquid crystal mixtures according to the invention have the formula I, in particular the formulas Ia to Ia
It contains one or more compounds selected from the compound group of i. In this case, preference is generally given to liquid-crystal mixtures which, in addition to one or more compounds of the formula I, in particular of the formulas Ia to Ii, additionally comprise one or more compounds selected from the group of the compounds II to IV.

More preferred are liquid crystal mixtures containing at least one compound each from two different compounds selected from the compounds of the formulas Ia to Ii.

Particular preference is given to the component mixtures T (Ii) of the following subgroups, each containing at least one compound from the group of compounds of the formulas indicated in each case: T (Ii) 1: Ii2-1 II1, II2, II3, II5, II9, II16, II17, II18, IV1, IV2,
IV3, IV4, IV5 or IV6 T (Ii) 2: Ii2-2 II1, II3, II4, II5, II9, IV1, IV2, IV3, IV4, IV7 or IV8 T (Ii) 3: Ii3-2 II1, II2, II5, II6, II7, II8, II9, III1, IV1, IV2, IV3
Or IV4 T (Ii) 4: Ii3-5 II1, II5, IV1, IV2, IV3 or IV4 T (Ii) 5: Ii3-6 II1, II5, II9, II25, II26, II27, II28, III1, IV1, IV
2, IV3, or IV4 T (Ii) 6: Ii3-1a or Ii3-16 II1, II5, II16, II17, II18, II25, II26, II27, II6,
II28, IV1 or IV2 T (Ii) 7: Ii4-5 II1, II5, II6, II7, II8, II16, II17, IV1, IV2, IV3
Or IV4 T (Ii) 8: Ii4-6 II1, II2, II5, II6, II7, II8, II11, IV1 or IV2 each containing at least one compound from the group of compounds of the formulas mentioned in each case Component mixture T (I
i) Liquid crystal mixtures based on 9-13 are preferred. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 kinds, preferably 2 to 3 kinds.
It contains 5, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%.
The mass of the component mixture in the liquid crystal of the present invention is 10% to 100%.
%, Especially 15% to 100%, more particularly 25% to 1%
00%.

Mixture Formula Mass in component mixture [%] T (Ii) 9 Ii 5-75, especially 5-55 II 6-85, especially 6-65 T (Ii) 10 Ii 5-75, especially 5-55 IV 5-85, especially 5-63 T (Ii) 11 Ii 5-55 II 5-52 III 5-29 T (Ii) 12 Ii 5-55, especially 5-50 II 5-72, especially 5-53 IV 5 to 50, especially 5 to 46 T (Ii) 13 Ii 5 to 50 II 5 to 75, especially 5 to 47 III 5 to 37, especially 1 to 15 IV 5 to 42 Particular preference is given to liquid-crystal mixtures which contain at least one compound from the group of compounds indicated in the case of and which contain one or more of these component mixtures.

[0336] One skilled in the art will appreciate that this limited preferred component mixture T (I) 1-T (I) is such that the liquid crystal mixture is optimized for a particular application.
You can immediately select from a group of 22. For example, T
(I) 1 has a particularly high dielectric anisotropy, but the component mixture T
(I) 16 to T (I) 18 have a particularly high stability, and the component mixtures T (I) 4, T (I) 11 and T (I) 19 are characterized by a relatively high clearing point. Choosing the appropriate component mixture is not difficult for one skilled in the art and does not require any inventive assistance.

At least one compound from each of the two compound groups selected from compound groups Ia to Ii and a compound of the formula
Liquid crystal mixtures containing at least one compound selected from the group consisting of II1-II28, III1-III3 and IV1-IV8 are more particularly preferred. In this case, one of the preferred component mixtures T (I) to T (I) 22 and formulas II1, II2, II3,
II4, II5, II6, II7, II8, II9, II10, II12, II13, I
I16, II17, II18, II19, II20, II21, II25, II27, II2
Liquid crystal mixtures containing compounds selected from the compounds of 8, III1, III2, IV1, IV2, IV3, IV4, IV5 and IV6 are particularly highly preferred.

In addition to one or more compounds selected from the group of compounds Ia, Ib, Ic, Id, Ie, If, Ig and Ii and at least one compound selected from the group of compounds of the formulas II to IV, Ih *

[0339]

Embedded image (Wherein, R ³ is an alkyl group having 1 to 10 C atoms that can also replace the CH ₂ group with —O— or —CH = CH—, and Z ¹³ is a single bond, —COO— or — CH ₂ CH ₂ ―
X ⁷ and X ⁸ are independently CH or N, L ¹ and L ² are independently H or F,
And Y ³ are F, Cl, CF ₃ , OCF ₃ or OCHF ₂ )
Selected from the group of compounds: Still more preferably, a liquid crystal mixture containing another compound.

The compounds of the formula Ih * have polar groups F, Cl, CF ₃ , OCF ₃ or OCHF ₂ and fall into some of the compounds of the formula Ih. The compounds specified below are more preferred compounds.

R ³ -Phe-C≡C-Phe.3F5F-Y ³ Ih * 2-1 R ³ -Pyd-C≡C-Phe.3F5F-Y ³ Ih * 2-2 R ³ -Pyr-C≡ C-Phe.3F5F-Y ³ Ih * 2-3 R ³ -Cyr-Pyr-C≡C-Phe.3F5F-Y ³ Ih * 3-1 R ³ -Cyc-Pyd-C≡C-Phe. (F , 2) -Y ³ Ih * 3-2 R ³ -Cyc-CH2CH2-Pyr-C≡C-Phe. (F, 2) -Y ³ Ih * 3-3 R ³ -Cyc-COO-Pyd-C≡ C-Phe. (F, 2) -Y ³ Ih * 3-4 In addition to at least one compound of the formulas Ia to Ig and at least one compound of the formulas II to IV, a compound of the formula Ih
Preferred liquid-crystal mixtures containing at least one compound of * are one of the preferred compounds just described and / or of the formula
Ih2-1 to Ih2-2, Ih2-1a to 1h, Ih2-2a to 2c, Ih2-3a to 3c,
Ih3-1 to Ih3-10, Ih3-1a to 1d, Ih3-2a to 2b, Ih3-5a, Ih3
-6a-6b and one of the preferred compounds Ih4-1-Ih4-5.

These mixtures are distinguished by high stability and high birefringence, and are particularly suitable for application in matrix systems and very particularly suitable for network systems.

In this case, the mass of the compounds selected from the group of compounds of the formulas Ih and Ih * is greater than 5%, in particular 7.5%
As mentioned above, it is particularly preferred that it is more than 10%, and more particularly it is more than 20%. The third essential component of these liquid crystal mixtures is

[0344]

Embedded image Very particular preference is given to the compounds of the formula wherein L ¹ and Y ³ have the meanings given above.

At least one compound of the formula II,
Particular preference is also given to mixtures based on a component mixture containing at least one compound of the formula IV8 and at least one compound of the formula Ih *. In this case, the following subgroups of component mixtures, each containing at least one compound from each of the groups E, F, and G, are particularly preferred. In this case, the weight of the compounds from each group in the component mixture is preferably in the indicated weight percentage range.

[0346]

[Table 1] The sum of the masses of the compounds from groups E, F and G in the component mixture is 100%, and the mass of the component mixture in the liquid crystal mixture that can be used according to the invention is between 25 and 10%.
It is preferably 0%.

Compounds Ia, Ib, Ic, Ie, Ig, Ih and Ii
In addition to one or more compounds selected from and at least one compound selected from the group of compounds of formulas II-IV,

[0348]

Embedded image (Wherein ring A ¹⁵ is trans-1,4-cyclohexylene or 1,4-phenylene, and R ³ , Z ¹³ , X ⁷ , X ⁸ ,
L ¹ , e and Y ³ are as defined above). Still more preferably, a liquid crystal mixture containing another compound. The compounds of the formula If * mean a preferred small group of compounds selected from the compounds of the formulas IfF, IfCl and IfCl.F. The mass of the compounds of the formula If * in at least three-component liquid-crystal mixtures of this kind can be greater than 5%, in particular greater than 10%, more than 20% and particularly preferably up to 55%. Liquid crystal mixtures of this kind have advantageous properties and are distinguished by particularly high stability and advantageous values of the optical parameters. Liquid crystal mixtures containing at least one compound of the formulas Ia to Ie and Ig to Ii and at least one of the following preferred compounds in addition to the compounds of the formulas II to IV are very particularly preferred.

[0349] ^{R 3 -Phe-Phe. (F} ) -FR 3 -Phe-Phe. (F) -Cl R 3 -Pyd-Phe-F R 3 -Pyd-Phe.3F-FR 3 -Pyd-Phe- Cl R ³ -Pyd-Phe.3F-Cl R ³ -Pyr-Phe-F R ³ -Pyr-Phe.3F-FR ³ -Pyr-Phe-Cl R ³ -Pyr-Phe.3F-Cl-first The essential component has a mass in the component mixture of 10% to
At least one compound of the formulas Ia to Ie, which is 90%, wherein the second essential component is the basket II1, II2, II3, II4, II5, II
6, II7, II8, II9, II16, II17, II18, II25, II26, II2
7, II28, III1, III2, IV1, IV2, IV3, IV4, VI7 and
Comprising one or more compounds selected from the group of IV8, wherein the mass of this component in the component mixture is from 5 to 80%, and wherein the third essential component is one of the preferred bicyclic compounds described above.
One or more and / or following compounds R ³ -Cyc-Phe-Phe. (F) -FR ³ -Cyc-Phe-Phe. (F) -Cl R ³ -Phe-Pyr-Phe. (F) -FR ³ -Phe-Pyr-Phe. (F) -Cl R ³ -Phe-Pyr-Phe. (F) -CF ₃ R ³ -Phe-Pyd-Phe. (F) -FR ³ -Phe-Pyr-Phe. ( ^{F) -Cl R 3 -Phe-Pyr} -Phe. (F) -OCF include one or more _3, the weight of component a mixture of 5% to 6
5%, especially 10% to 65%, more particularly 12.5%
Particularly preferred are component mixtures that are ~ 65%.

The total weight of the component mixtures is 100%, and the weight of the component mixture in the optimum mixture is 25 to 10%.
It is preferably 0%.

In addition to one or more compounds selected from the group of compounds of formulas Ia-Ie and Ig-Ii and one or more compounds selected from the group of compounds of formulas II-IV,

[0352]

Embedded image (Wherein ring A ¹⁶ is trans-1,4-cyclohexylene,
A liquid crystal mixture comprising at least one compound of 1,4-phenylene or 3-fluoro-1,4-phenylene, and Z ¹³ , L ¹ , Y ³ , R ³ and e are as defined above. Is more particularly preferred. Compounds of formula If ** have the formula If
A preferred subgroup of compounds selected from the compounds F, IfCl and IfCl.F.

In addition to the compounds of the formulas Ia to Ie and Ig to Ii,
Liquid-crystal mixtures containing compounds of the formulas I to IV and further of the compound of the formula If ** are characterized by favorable properties, in particular high stability, an advantageous operating temperature range and an advantageous threshold voltage. Preferably, the mass of the compound of the formula If ** in these liquid-crystal mixtures is more than 5%, in particular more than 10%, more particularly more than 15%. The following small group of compounds of the formula If ** are very particularly preferred.

[0354] ^{R 3 -Cyc-COO-Phe.} (F) -Y 3 If ** 2-1 R 3 -Phe-COO-Phe. (F) -Y 3 If ** 2-2 R 3 -Cyc- (F) -Y ³ If ** 3-1 R ³ -Cyc-Phe-COO-Phe. (F) -Y ³ If ** 3-2 The following liquid-crystal mixtures, each containing at least one compound from the groups I and K respectively in the indicated mass range, are very particularly preferred.

[0355]

[Table 2] In this case, the total mass in the component mixture is preferably 100%, and the mass of the component mixture in the liquid crystal mixture used according to the present invention is preferably from 10 to 85%.

The liquid crystals according to the invention can be prepared, in addition to the compounds of the formula I according to the invention, particularly preferred sub-formulas, more particularly preferred liquid-crystal mixtures, as well as nematic or nematic-forming (mono- or isotropic) substances, in particular azoxybenzene , Benzylidene anilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl esters of cyclohexanecarboxylic acid, phenyl or cyclohexyl esters of cyclohexylbenzoic acid, phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid Benzoic acid, cyclohexanecarboxylic acid or cyclohexylcyclohexanecarboxylic acid cyclohexylphenyl esters, phenylcyclohexanes, cyclohexylbiphenyls, Phenylcyclohexylcyclohexanes, cyclohexylcyclohexanes, cyclohexylcyclohexylcyclohexenes, 1,4-bis-cyclohexylbenzenes, 4,4′-bis-cyclohexylbiphenyls, phenyl or cyclohexylpyrimidines, phenyl or cyclohexylpyridines, phenyl or Cyclohexyldioxane, phenyl- or cyclohexyl-1,3-dithiane,
1,2-diphenylethanes, 1,2-dicyclohexylethanes, 1-phenyl-2-cyclohexylethanes, 1-cyclohexyl-2- (4-phenylcyclohexyl) ethanes, 1-cyclohexyl-2-biphenylethanes It is preferably selected from the group consisting of 1,1-phenyl-2-cyclohexylphenylethanes, optionally halogenated stilbenes, benzylphenyl ethers, tolanes and substituted cinnamic acids. Further components may be included. The 1,4-phenylene group of these compounds can also be fluorinated.

In these compounds, both terminal groups are preferably in each case independently of one another alkyl, alkenyl, alkoxy, alkenyloxy or alkanoyloxy having up to 8 C atoms. In most of these compounds, R 'and Rmo are different from one another, and one of these groups is usually alkyl or alkenyl.

However, if one and / or both terminal groups are polar groups —CN, —NCS, —F, —Cl or (O) _i CX _k
It can also be H _{3-k where} i is 0 or 1, k is 1, 2 or 3, and X is F or Cl. If only one of the terminal groups is one of the polar groups mentioned above, the other is preferably alkyl or alkenyl.

Many substances of this type, or alternatively mixtures thereof, are commercially available. All these substances are obtained by methods known according to the literature or according to them.

The liquid crystals used in the electro-optical liquid crystal system according to the invention preferably contain 1% to 10%, in particular 10% to 100%, more particularly 20% to 100% of the compound of the formula I. . In this case, 1 to 20, especially 1 to 15, formulas
Liquid crystal mixtures containing the compounds of I are preferred. If the liquid-crystal compounds of the formula I are selected from only one subgroup of the formulas Ia to Ii, the liquid-crystal mixture preferably contains 1 to 5, in particular 1 to 3, compounds of this sub-formula of the formula I.

The liquid crystal mixtures according to the invention have the formulas I, II, III and
Preferably, it is based on a compound selected from the group IV. The mass of compounds selected from the group of the formulas I, II, III and IV in the liquid-crystal mixture is from 5% to 100%, in particular from 10% to 1%.
It is preferably 00%, more particularly 15% to 98%. The liquid crystal mixtures according to the invention have the formulas I, II, III, VI and V
It is preferable to contain 2 to 40 compounds, particularly 2 to 38 compounds, more particularly 2 to 35 compounds selected from the group of

The dielectric anisotropy of the liquid crystal mixture used is positive Δ
ε> 0, preferably Δε> 3.

When the value of the dielectric anisotropy Δε is small, a very high threshold voltage is observed. Particularly preferred values are Δε>
5 and Δε> 8 are very particularly preferred.

Liquid crystal mixtures based on compounds having a medium polarity of 3 ≦ Δε ≦ 20 (* 1), in particular 3 ≦ Δε ≦ 15 (* 2), have particularly advantageous properties,
In particular, they have been found to have high temperature and UV stability and high specific resistance. Mixtures of this kind are also particularly suitable for systems with a high information content controlled by means of active or passive matrices, and more particularly for systems which have to withstand relatively high operating temperatures (for example systems for use in the field). ing. Preferably, the mass of the moderately polar compound in the liquid crystal mixture is at least 50%, in particular at least 60%, more particularly at least 65%.

Particularly, W = —F, —Cl, —CF ₃ , —OCF ₃ ,
-OCHF ₂ or NCS, especially W is -F, -Cl, -CF ₃ , -OCF ₃
Or a compound of formula I which is -OCHF ₂ has a preferred range (*
Often have a dielectric constant within 1) or (* 2), while W
Liquid crystal compounds with = -CN often have excessively high dielectric constants, which proved to be less suitable for such mixtures. Less than 15% by weight of compounds with terminal carbonitrile groups in liquid-crystal mixtures based on compounds of moderate polarity,
In particular, it is preferably at most 10%. For example, if a highly polar additive with Δε> 20 is required to lower the threshold voltage, one end group has the meaning indicated for R ¹ and the other end group has

[0366]

Embedded image (However, W is -F, -Cl, -CF ₃ , -OCF ₃ or -O
It is preferred to use the compound represented by CHF ₂ and Y is H or F).

Compounds where W = —Cl are generally characterized by a higher birefringence Δn than the corresponding compounds where W = —F,
Thus, for example, it is often preferred when high birefringence is desired to enhance scattering in opaque conditions.

The present invention provides those skilled in the art with a limited group of particularly preferred compounds of the formula I, in particular of the formulas Ia to Ii, and particularly preferred liquid-crystal component mixtures. Formula I, in particular one of the formulas Ia to Ii
A liquid-crystal mixture containing at least one compound, more particularly at least one of the abovementioned component mixtures, corresponds to the requirements mentioned at the outset set for use in an electro-optical system according to the preamble of claim 1, It has particularly high advantageous properties, to a high degree, and much better than the liquid-crystal mixtures conventionally named for these systems. In this case, based on the detailed description, those skilled in the art will recognize that birefringence Δn and / or ordinary refractive index n ₀ and / or other refractive indices and / or viscosity and / or dielectric anisotropy and / or Or further parameters of the clearing point and / or liquid crystal and / or threshold voltage and / or further parameters of the system and / or their temperature dependence and / or operating temperature range and / or monomers or oligomers for polymerization And / or from the preferred liquid crystal compounds and liquid crystal mixtures of the group described without inventive assistance to optimize the solubility of the liquid crystal in the coarse matrix or the coarse network and / or the further parameters of the liquid crystal and the system. But you can choose.

If, for example, a high clearing point is required, the person skilled in the art will recognize that the mass of the bicyclic compound in the liquid-crystal mixture should not be too high, It is preferable to select from among them. Moreover, one skilled in the art, for example, 4-ring compounds of formula Ie4-1~Ie4-4 Alternatively, for example, as ^{R 2 -Phe-Phe-Cyc-} R 3 R 2 -Cyc-Phe-Phe-Cyc-R 3 Other high transparent point imparting substances can be added to the liquid crystal.

In these compounds, R ² and R ³ are
Preference is in each case, independently of one another, of alkyl, methoxy, alkoxycarbonyl or alkanoyloxy having 1 to 15 C atoms.

Additives of this kind are known to those skilled in the art and can be selected without problems from the above-listed substances. In this case, the person skilled in the art is particularly aware of Δn and / or n ₀
Or other refractive indices and / or Δε to be adjusted in certain embodiments of the electro-optic system of the present invention and / or Δε and / or further physical parameters that are important to the particular application are acceptable and / or slightly less. It is preferred to choose the concentration of such additives such that they have only a negligible effect.

When the system of the present invention is controlled using, for example, an AC voltage, it is necessary to use a highly viscous liquid crystal mixture. Otherwise, a flickering display will result, especially at low or medium frequencies. To increase the viscosity, those skilled in the art can add highly viscous liquid crystal compounds to the liquid crystal mixture. Preferably, these compounds are selected from the group of compounds of the formula I, in particular of the formulas Ia to Ii, but they can also be employed from the abovementioned substance groups. In particular, DE 3,919,9
As described at 42, polymers having one or more side groups can be added to increase the viscosity. On the other hand, when the electro-optical system is used, for example, as a matrix display with a high information content, a high-viscosity liquid crystal mixture is used.
Particularly suitable for achieving short switching times.

In this case, the person skilled in the art should be aware of the formula I, in particular the subformula Ia, so that the content of tri- and tetracyclic compounds is not too high.
It is preferable to select from the group of compounds of ~ Ii. If it is necessary to use a high content of tri- and tetracyclic compounds to achieve a high clearing point, one skilled in the art generally chooses laterally fluorinated or chlorinated compounds of formulas Ia-Ii. However, those skilled in the art can also select from the above list of substances having a low viscosity such as R ² -Cyc-Phe.3F-Phe-R ³ and add them to the liquid crystal mixture of the present invention. it can. By way of example, R ² and R ³ of this compound are preferably as defined above.

Those skilled in the art will recognize that important parameters of the liquid crystal mixture such as, for example, Δε and especially when using viscosity reducing agents, such as _Tc , are acceptable and / or low and / or low.
Alternatively, the substances used to improve the viscosity and their concentration are selected so as to have a negligible effect.

If desired, one skilled in the art can take into account that other parameters, in particular the solubility of the liquid crystal mixture in the polymer used for the matrix, do not unduly change with its addition, for example:

[0376]

Embedded image A high nematic forming substance such as

In the case of liquid-crystal mixtures containing compounds of the formulas II to IV, the person skilled in the art can vary the relative amounts of these compounds in the mixture, for example to improve the birefringence. For mixtures having very high Δn, for example, formula II1,
Compounds of the formula II16, IV3 or IV4 can be used in particular, while for liquid-crystal mixtures with relatively low Δn values, for example, the compounds of the formula I
Compounds II1 to III3 are preferred. Of course, the person skilled in the art will be able to make a preferred choice from the compounds of the formula I without difficulty with regard to the desired Δn value. For mixtures having a relatively high or high Δn, for example, compounds of the formula Ig are generally preferred, while for liquid crystal mixtures of the invention having a relatively low or low Δn, two or more saturated rings Compounds of the system are generally particularly suitable.

To achieve low threshold voltages, liquid crystal mixtures with very high dielectric anisotropy Δε are generally required. Those skilled in the art will recognize from the group of compounds of the formula I, in particular the formulas Ia to Ii, that furthermore the formula II
To IV and a group of preferred component mixtures. To increase Δε, the person skilled in the art can, for example, add compounds of the formula II6 to the liquid-crystal mixture. These compounds are extremely strong dielectrically positive compounds. For example, the propyl homolog (alkyl = C ₃ H ₇ )
= 50. One skilled in the art will select the concentration of such additives so that the liquid crystal mixture is most compatible with the particular embodiment of the electro-optic system. In particular, care is taken to affect the Δ and / or n ₀ and / or one or more further indices of refraction of the liquid crystal in an acceptable and / or negligible and / or negligible manner.

Those skilled in the art will recognize from the group of compounds of the formula I, in particular the formulas Ia to Ii, that the liquid-crystal mixtures are to be optimized for particular applications,
Furthermore, the properties of the liquid-crystal mixtures according to the invention can be modified for certain applications by optimizing them, if necessary, from the group of compounds of the formulas II to IV and the group of preferred component mixtures, and to optimize them within a certain range. be able to.

However, liquid crystals containing compounds of the formula I, in particular of the formulas Ia to Ii, and in particular of a liquid crystal mixture containing one or more compounds of the formulas II to IV, are used in the electro-optical liquid crystal system according to the invention. It is important that they are particularly suitable for Mixtures containing one or more of the preferred component mixtures are especially very suitable liquid-crystal mixtures.

The liquid-crystal mixtures according to the invention, which contain one or more compounds of the formula I, in particular of the formulas Ia to Ii, can be used without the other parameters of the mixture changing at the same time unduly and without their use in electro-optical systems. Also meant are "stable structure mixtures" which are particularly suitable for application to electro-optical systems, which can generally be optimized by the methods and / or additives described above for specific requirements without significant adverse changes. is there.

The liquid-crystal mixtures according to the invention are particularly suitable for use in electro-optical systems according to the preamble of claim 1. Thus, considerable commercial importance exists in the liquid crystals of the present invention and the electro-optical systems of the present invention.

The liquid-crystal mixtures according to the invention can be modified by further additives so that they can be used in all electro-optical systems according to the preamble of claim 1.

Additives of this kind are known to the person skilled in the art and are described in detail in the literature. Thus, for example, by adding a multicolor dye, a colored electro-optical system can be manufactured,
Alternatively, certain substances can be added to improve the temperature dependence of the dielectric anisotropy, optical anisotropy, viscosity and / or electro-optical parameters of the liquid crystal. Such substances are described, for example, in H. Kelker and R. Kelker. Hats
z), `` Handbook of Liquid Crystal
s) ", Chemical Publishers, Weinheim (1980), and
DE-OS 2,209,127,2,240,864,2,32
1,632,2,338,281,2,450,088,2,
637,430, 2,853,728 and 2,902,1
77.

An electro-optical liquid crystal system in which a polychromatic dye is added to a liquid crystal mixture in a range of 0 to 25% by weight, particularly 0 to 20% by weight, and more particularly 0 to 15% by weight is preferable.

Furthermore, as described, for example, in DE 4,007,039, chiral mesogenic or non-mesogenic compounds are added to the liquid-crystal mixtures according to the invention in order to increase scattering in the opaque state and / or It can affect the slope of the electro-optic curve. The liquid crystal of the present invention preferably contains 0 to 15%, particularly 0 to 10% of a chiral additive.

The electro-optical liquid crystal system of the present invention can be switched by applying a DC or AC voltage.
However, it is preferred to use an AC voltage with an effective AC voltage amplitude of 1 to 24 volts and an AC voltage frequency of 10 Hz to 10 kHz. Amplitude of 2 to 220 volts and 20
Frequencies of up to 120 Hz are particularly preferred. It is very particularly preferred that the amplitude of the AC voltage is between 2 and 130 V.

The liquid-crystal mixtures which can be used according to the invention are prepared in a manner customary per se. In general, the desired amount of the components, which are used in small amounts, are conveniently dissolved in the main constituent components at an elevated temperature. It is also possible to mix solutions of these components in an organic solvent, such as acetone, chloroform or methanol, and to remove the solvent again after sufficient mixing, for example by distillation.

[0389]

The following examples illustrate the invention but do not limit it.

The symbols in the examples have the following meanings.

K: crystalline solid S: smectic phase (indicating the type of phase), N: nematic phase, I: isotropic phase.

The number between the two symbols indicates the transition temperature based on ° C.

The indicated% is% by weight.

Example 1 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-
4-butylcyclohexylbenzonitrile; 20% p
-Trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) ) Biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 5.6% of 4 -(Trans-4-pentylcyclohexyl) -4 '
-Cyanobiphenyl; 20% of 1- (4- (4-pentylphenyl) phenyl) -2- (3-fluoro-4-cyanophenyl) ethane.

B) The above-mentioned electro-optical liquid crystal system is produced by the following various methods 1.1 to 1.3 and 2. 1. Microdroplet matrix system NOA65 [Norland] adhesive, which can cure the liquid crystal mixture of 1.1a) by UV irradiation
And stir at room temperature in a ratio of 1.6: 1 until a clear solution is obtained. This solution is introduced between two transparent glass support plates provided with an electrode layer together with a spacer (20 μm). The glass support plate is pressed from both sides to obtain a uniform film with a thickness of 20 μm. This is cured by UV irradiation for one minute.

The liquid crystal mixture of 1.2a) was epicoated (Epicoat).
kote) 828 and Capcure 3-80
0 [Miller Stephenson Company
henson Company) at room temperature in a ratio of 1: 1: 1 until a clear solution is obtained. Solution is about 1/2
The stirring time should be as short as possible, since it will already harden at room temperature after a certain time. Use this solution as a spacer (20 μm)
And between the two transparent glass support plates provided with the electrode layers. Pressing the glass support plate from both sides, 20μm
To obtain a film having a uniform thickness. The film can be heated to a temperature of up to 100 ° C. to accelerate the curing process.

5 g of the liquid crystal mixture of 1.3 a) was added to 20% of PVA
Stir at 2000 rpm for 2 minutes at room temperature with 15 g of aqueous solution. The obtained solution is degassed for 24 hours, and applied together with a spacer (20 μm) on a glass support plate provided with an electrode layer to form a thin layer. After drying the assembly at 85 ° C. for 1 hour, a second glass support plate provided with an electrode layer is applied thereon to obtain a uniform film having a thickness of 20 μm. The system thus obtained is dried at 85 ° C. for a further 24 hours. 2. Using the liquid crystal mixture of the network system a) as a polymerizable compound as trimethylolpropane triacrylate and 2-hydroxy-2-methyl-1-phenylpropane as a photopolymerization initiator.
80: 19.8 with 1-On (Darocure 1173, a product of E. Merck, Darmstadt):
Stir at a ratio of 0.2. This is introduced together with a spacer having a thickness of 20 μm between two glass support plates provided with an electrode layer. To cure the polymer, the resulting system is passed through a radiation field of a halogen lamp (70 W / cm) at a constant speed (3 m / min).

Method b) The electro-optical systems produced according to 1.1 to 1.3 and 2 are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. I do.

Example 2 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
9% p-trans-4-propylcyclohexylbenzonitrile; 7% p-trans-4-butylcyclohexylbenzonitrile; 12.5% p-trans-4-
Pentylcyclohexylbenzonitrile; 7.5% p-
Trans-4-heptylcyclohexylbenzonitrile; 3.5% of 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 8% of 4-pentyl-4 "-cyanotel Phenyl; 4% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 11% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl;
5% of 1- (4- (4-pentylphenyl) phenyl)
-2- (4-cyanophenyl) ethane; 3.5% of 1-
(4- (4-pentylphenyl) phenyl) -2- (3
-Fluoro-4-cyanophenyl) ethane; 3.5% of 1- (4- (4-propylphenyl) phenyl) -2-
(3-fluoro-4-cyanophenyl) ethane; 2.5
% Of 4-propyl-4'-cyanobiphenyl; 7.5%
4-ethyl-4'-cyanobiphenyl; 17% of 4-
Pentyl-4'-cyanobiphenyl.

Clearing point Tc = 93 ° C. Viscosity η = 38 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.20 (20 ° C., 589 nm) Dielectric anisotropy Δε = 15.2 (20 ° C., 1 kHz) b) The electro-optical liquid crystal system is manufactured by the method described in Examples 1, 1.1 to 1.3 and 2.

Example 3 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
1% of 4-ethyl-4'-cyanobiphenyl; 5% of 4
-Propyl-4'-cyanobiphenyl; 10% of 4-heptyl-4'-cyanobiphenyl; 37% of 4-pentyl-4'-cyanobiphenyl; 12% of 4-octoxy-4'-cyanobiphenyl; 15% 4-pentyl 3 ", 5" -difluoro-4 "-cyanoterphenyl;
10% of 4-pentyl 3 ', 5'-difluoro-4 "-
Cyanotelphenyl.

Dielectric anisotropy Δε = 20.0 (20 ° C., 1 kHz) Optical anisotropy Δn = 0.233 (20 ° C., 589 nm) b) The above electro-optical liquid crystal system was used in Examples 1, 1.1 to 1 .3 and 2.

Example 4 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 28% of 2- (4-cyanophenyl) -5-
Ethylpyridine; 28% of 2- (4-cyanophenyl)
-5-propylpyridine; 29% of 2- (4-cyanophenyl) -5-pentylpyridine; 15% of 4-pentyl 3 ", 5" -difluoro-4 "-cyanoterphenyl; b) the electro-optical liquid crystal. The system is prepared by the method described in Example 1, b).

Example 5 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 19% of 2- (4-cyanophenyl) -5-
Ethylpyrimidine; 19% of 2- (4-cyanophenyl) -5-butylpyrimidine; 19% of 2- (4-cyanophenyl) -5-pentylpyrimidine; r-4-cyanophenyl) ethane; 12% of 4 -Pentyl-4'-cyanobiphenyl.

B) The electro-optical liquid crystal system described in Example 1, b)
It is manufactured by the method described in (1).

Example 6 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5-
Ethyl pyrimidine; 20% of 2- (4-cyanophenyl) -5-propylpyrimidine; 20% of 2- (4-cyanophenyl) -5-pentylpyrimidine; 20% of 4
-Pentyl 3 ", 5" -difluoro-4 "-cyanoterphenyl; 20% of 4-pentyl-4'-cyanobiphenyl.

B) The electro-optical liquid crystal system described in Example 1, b)
It is manufactured by the method described in (1).

Example 7 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 1- (trans-4- (trans-
4-propylcyclohexyl) cyclohexyl-2-
(3-fluoro-4-cyanophenyl) ethane; 14.
4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4
-Pentylcyclohexylbenzonitrile; 12% p
-Trans-4-heptylcyclohexylbenzonitrile; 5.6% of 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-Cyanotelphenyl; 6.4% trans-4-butylcyclohexylcarboxylate 4- (trans-4-propylcyclohexyl) phenyl; 5.6% of 4- (trans-
4-pentylcyclohexyl) -4'-cyanobiphenyl.

B) The electro-optical liquid-crystal systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. .

Example 8 a) A liquid crystal mixture consisting of the following compounds has the following physical data: 43% of 4-pentyl-4'-cyanobiphenyl; 17% of 4-propoxy-4'- Cyanobiphenyl; 13% of 4-pentoxy-4'-cyanobiphenyl; 17% of 4-octoxy-4'-cyanobiphenyl; 10% of 4-pentyl-4 "-cyanotelphenyl.

Birefringence Δn = 0.246 (589 ° C. at 20 ° C.)
m) Threshold voltage V [90.0.20] = 1.44 V The threshold voltage has a cell spacing of d = 7 μm, and a TN cell placed between orthogonal polarizers (twist angle Ψ = π / 4) Measured in

B) A liquid crystal mixture comprising the following compounds has the following physical properties.

30% of 4-pentyl-4'-cyanobiphenyl; 15% of 4-ethyl-4'-cyanobiphenyl; 20% of 4- (propylphenyl) -3-fluoro-4'-cyanobiphenyl; % Of 4-propyl-2
-Fluoro-4'-cyanobiphenyl; 15% of 4-pentyl-2-fluoro-4'-cyanobiphenyl; 10
% Of 4-pentyl-4 "-fluoro-4" -cyanoterphenyl.

Birefringence Δn = 0.246 Threshold Voltage V [90.0.20] = 1.26 V The threshold voltage has a cell spacing of d = 7 μm, and a TN cell placed between orthogonal polarizers ( The measurement was performed at a twist angle Ψ = π / 4).

The advantageous properties of the mixtures according to the invention are described in Example 8a).
It is clear from the comparison of the results of (b) and (b).

C) An electro-optical system was produced by the method described in Example 1b) using a mixture of Examples 8a) and b). The system prepared with the liquid crystal mixture of Example 8b) has advantageous properties over the system prepared with the mixture of 8a), and is characterized by a particularly low threshold voltage.

Example 9 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 20% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 15% of 4-pentyl- 4'-cyanobiphenyl; 15% of 4-ethyl-
4'-cyanoterphenyl; 5% of 4-pentyl-4 "
-Cyanotelphenyl; 15% of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 1
0% of 4-propyl-2-fluoro-4'-cyanobiphenyl; 15% of 4-pentyl-2-fluoro-4'-
Cyanobiphenyl; 5% of 4- (trans-4-pentylcyclohexyl) -4′-cyanobiphenyl.

Birefringence Δn = 0.218 (20 ° C., 589 nm) Ordinary ray refractive index n0 = 1.522 (20 ° C., 589 nm) Dielectric anisotropy Δε = 16.71 (20 ° C., 1 kHz) Threshold Voltage V [90.0.20] = 1.33 V The threshold voltage was measured with a TN cell (twist angle ψ = π / 4) having a cell spacing of d = 7 μm and placed between orthogonal polarizers.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 10 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 12% of 4-ethyl-4-cyanobiphenyl; 4% of 4-propyl-4-cyanobiphenyl 29.6% of 4-pentyl-4-cyanobiphenyl; 8.8% of 4-propoxy-4-cyanobiphenyl; 8.0% of 4-pentyl-4 "-cyanoterphenyl; 20.0% of 4- (4-propylphenyl) -3-
Fluoro-4'-cyanobiphenyl; 5.6% of 4-
(4-heptylphenyl) phenylcarboxylic acid 4- (4
-Cyanophenyl) phenyl; 12% of 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl.

Birefringence Δn = 0.286 (20 ° C., 589 nm) Ordinary refractive index n0 = 1.530 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13.5 (20 ° C., 1 kHz) Threshold Voltage V [90.0.20] = 1.66 V Absorption coefficient γ = 1.629 (λ: 350 nm) γ = 0.130 (λ: 360 nm) γ = 0.006 (λ: 370 nm) Clearing point N 113 I The extinction coefficient is given by the formula

[0422]

(Equation 1) (Where A is the absorbance, l is the thickness of the liquid crystal layer where the light crosses, in cm, and CW is 100 ml of solution
(The mass of the liquid crystal expressed in grams per unit).

The threshold voltage was measured as described in Example 9a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 11 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 14% of 4-ethyl-4-cyanobiphenyl; 5% of 4-propyl-4-cyanobiphenyl 33.0% 4-bentyl-4-cyanobiphenyl; 12.0% 4-propoxy-4-cyanobiphenyl; 10.0% 4-pentyl-4 "-cyanotelphenyl; 23.0% 4- (4-propylphenyl) -3
-Fluoro-4'-cyanobiphenyl; 3.0% of 4-
(4-heptylphenyl) phenylcarboxylic acid 4- (4
-Cyanophenyl) phenyl.

Birefringence Δn = 0.287 (20 ° C., 589 nm) Ordinary ray refractive index n0 = 1.533 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14.1 (20 ° C., 1 kHz) Threshold Voltage V [90.0.20] = 1.60 V Clearing point N 96 I The threshold voltage was measured as described in Example 9a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Example 12 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 35.0% of 4-pentyl-4'-
Cyanobiphenyl; 12.0% of 4-propoxy-4 '
-Cyanobiphenyl; 14.0% of 4-pentoxy-
4'-cyanobiphenyl; 6.0% of 4-pentyl-
4 "-cyanoterphenyl; 23.0% of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 3.0% of 4- (4-heptylphenyl) phenylcarboxylic acid 4- ( 4-cyanophenyl) phenyl;
7.0% of 4-octoxy-4'cyanobiphenyl.

Birefringence Δn = 0.280 (20 ° C.,
589 nm) Ordinary ray refractive index n0 = 1.527 (20 ° C.) Dielectric anisotropy Δε = 13.0 (20 ° C., 1 kHz) Threshold voltage V [90.0.20] = 1.71 V Clearing point N 97 I The threshold voltage was measured as described in Example 9a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 13 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 32.0% of 4-pentyl-4'-
Cyanobiphenyl; 12.0% of 4-propoxy-4 '
-Cyanobiphenyl; 13.0% 4-pentoxy-
4'-cyanobiphenyl; 8.0% of 4-pentyl-
4 "-cyanoterphenyl; 22.0% of 4- (4-propylphenyl) -4-fluoro-4'-cyanobiphenyl; 3.0% of 4- (4-heptylphenyl) phenylcarboxylic acid 4- ( 4-cyanophenyl) phenyl;
5.0% of 4-octoxy-4'-cyanobiphenyl;
5.0% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

Birefringence Δn = 0.284 (20 ° C., 589 nm) Ordinary refractive index n0 = 1.526 (20 ° C., 589 nm) Clearing point N 108 I b) Produced by the method described in Example 1b). Electro-optical systems are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 14 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 33.0% of 4-pentyl-4'-
Cyanobiphenyl; 12.0% of 4-propoxy-4 '
-Cyanobiphenyl; 14.0% of 4-pentoxy-
4'-cyanobiphenyl; 10.0% of 4-pentyl-
4 "-cyanoterphenyl; 23.0% of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 3.0% of 4- (4-heptylphenyl) phenylcarboxylic acid 4- ( 4-cyanophenyl) phenyl;
5.0% of 4-octoxy-4'cyanobiphenyl.

Birefringence Δn = 0.288 (20 ° C., 589 nm) Ordinary refractive index n0 = 1.528 (20 ° C., 589 nm) Clearing point N 105 I b) Produced by the method described in Example 1b). Electro-optical systems are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 15 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 30.0% of 4-hexyl-4'-
Cyanobiphenyl; 10.0% of 4-pentoxy-4 '
-Cyanobiphenyl; 7.0% of 4-octoxy-4 '
-Cyanobiphenyl; 5.0% of 4-pentyl-4 "-
15.0% of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl;
5.0% 4- (trans-4-pentylcyclohexyl) benzo tolyl; 8.0% 1-propoxy-trans-4- (trans-4-propylcyclohexyl)
Cyclohexane; 20.0% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

Birefringence Δn = 0.2293 (20 ° C., 589 n
m) ordinary ray refractive index n0 = 1.5151 (20 ° C., 589 n)
m) Clearing point N 102 I b) The electro-optical system produced by the method described in Example 1 b) has a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. Features.

Example 16 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 32.0% of 4-pentyl-4'-
Cyanobiphenyl; 12.0% of 4-propoxy-4 '
-Cyanobiphenyl; 13.0% 4-pentoxy-
4'-cyanobiphenyl; 6.0% of 4-pentyl-
4 "-cyanoterphenyl; 23.0% of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 3.0% of 4- (4-heptylphenyl) phenylcarboxylic acid 4- ( 4-cyanophenyl) phenyl;
5.0% of 4-octoxy-4'-cyanobiphenyl;
6.0% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

Birefringence Δn = 0.283 (20 ° C., 589 nm) Refractive index n0 = 1.564 (20 ° C., 589 nm) Dielectric anisotropy Δε = 12.8 (20 ° C., 1 kHz) Threshold Voltage V [90.0.20] = 1.73V Clearing point N 108 I The threshold voltage was measured as described in Example 9a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Example 17 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 10.0% of 4-pentoxy-4 '
-Cyanobiphenyl.

7.0% 4-octoxy-4'-cyanobiphenyl; 31.0% 4-hexyl-4'-cyanobiphenyl; 12.0% 4- (trans-4-pentylcyclohexyl) benzonitrile 20.0% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 15.0% of 4- (4-propylphenyl) -3-fluoro-4'cyanobiphenyl; 5.0
% 4-pentyl-4 "-cyanoterphenyl.

Birefringence Δn = 0.2373 (589 ° C. at 20 ° C.)
m) ordinary ray refractive index n0 = 1.5183 (20 ° C., 589 n)
m) Dielectric anisotropy Δε = 14.0 Clearing point N 105 I b) The electro-optical system produced by the method described in Example 1 b) has advantages over a wide operating temperature range, electro-optical parameters and their temperature dependence. Values and particularly low threshold voltages.

Example 18 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 20.0% of 4- (trans-4-)
Pentylcyclohexyl) benzonitrile; 15.0%
4- (trans-4-propylcyclohexyl) benzonitrile; 10.0% of 4- (trans-4-butylcyclohexyl) benzonitrile; 10.0% of 4-pentyl-4'-cyanobiphenyl; 10.0 9.% 4-ethyl-4'-cyanobiphenyl; 7.0% 4-propyl-4-cyanobiphenyl; 10.0% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 0% of 4- (4-propylphenyl)-
3-fluoro-4'-cyanobiphenyl; 8.0% of 4
-Pentyl-4 "-cyanoterphenyl.

Birefringence Δn = 0.0242 (20 ° C., 589 n
m) ordinary ray refractive index n0 = 1.5132 (20 ° C., 589 n)
m) Dielectric anisotropy Δε = 14.8 (20 ° C., 1 kHz) Clearing point N 81 I b) The electro-optical system manufactured by the method described in Example 1b) has a wide operating temperature range, electro-optical parameters and , And particularly low threshold voltages.

Example 19 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 30.0% of 4-pentyl-4'-
15.0% 4-ethyl-4'-cyanobiphenyl; 20.0% 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 1
0.0% 4-propyl-2-fluoro-4'-cyanobiphenyl; 15.0% 4-pentyl-2-fluoro-4'-cyanobiphenyl; 10.0% 4-pentyl-3 "-. Fluoro-4 "-cyanoterphenyl.

Birefringence Δn = 0.246 (20 ° C., 589 nm) Threshold voltage V [90.0.20] = 1.26 V Clearing point N 62 I The threshold voltage was as shown in Example 9a). It was measured.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Example 20 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 25.0% of 4-pentyl-4'-
15.0% 4-ethyl-4'-cyanobiphenyl; 18.0% 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 1
0.0% 4-propyl-2-fluoro-4′-cyanobiphenyl; 10.0% 4-pentyl-2-fluoro-4′-cyanobiphenyl; 10.0% 4-pentyl-3 ″, 5% -difluoro-4 "-cyanoterphenyl; 6.0% of 4-nonyl-3" -fluoro-4 "-cyanoterphenyl; 6.0% of 1- [trans-4-.
(Trans-4-propylcyclohexyl) cyclohexyl] -2- [4- (4-cyanophenyl) phenyl]
Ethane.

Birefringence Δn = 0.258 (20 ° C., 589 nm) Threshold voltage V [90.0.20] = 1.33 V Dielectric anisotropy Δε = 19.7 (20 ° C., 1 kHz) Clearing point The N 82 I threshold voltage was measured as described in Example 9a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 21 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of 2- (3-fluoro-4-cyanophenyl) -5-pentylpyrimidine.

Viscosity η = 34 mm 2 / sec (20
° C) Optical anisotropy Δn = 0.15 (20 ° C, 589 nm) Dielectric anisotropy Δε = 17.8 (20 ° C, 1 kHz) b) Electro-optical system manufactured by the method described in Example 1b) Are characterized by a wide operating temperature range, advantageous values for the electro-optic parameters and their temperature dependence, and especially low threshold voltages.

Example 22 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
3. 2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 ′-(trans-4 ′ (trans-4-propylcyclohexyl) biphenyl; 8%
4-pentyl-4 "-cyanoterphenyl; 6.4%
Trans-4-butylcyclohexylcarboxylic acid 4-
(Trans-4-propylcyclohexyl) phenyl;
5.6% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% 2- (4-cyanophenyl) -5-propylpyridine.

Clearing point TC = 80 ° C. Viscosity η = 33 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 15.5 (20 ° C., 1 kHz) B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 23 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.5% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 6.4% trans- 4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 20% of 2- (4-cyanophenyl)
-5-pentylpyrimidine.

Clearing point TC = 82 ° C. Viscosity η = 34 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 16.1 (20 ° C., 1 kHz) B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 24 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
17% of 1-difluoromethoxy-2-fluoro-4-
[Trans-4- (trans-4-ethylcyclohexyl) cyclohexyl] benzene; 17% 1-difluoromethoxy-2-fluoro-4- [trans-4- (trans-4-butylcyclohexyl) cyclohexyl]
Benzene; 17% 1-difluoromethoxy-2-fluoro-4- [trans-4- (trans-4-pentylcyclohexyl) cyclohexyl] benzene; 11% 1-difluoromethoxy-4- [trans-4- (trans -4-pentylcyclohexyl) cyclohexyl]
Benzene; 6% of 1- (trans-4-propylcyclohexyl) -2- (4-difluoromethoxyphenyl)
Ethane; 6% 1- (trans-4-pentylcyclohexyl) -2- (4-difluoromethoxyphenyl) ethane; 6% 1-difluoromethoxy-4- (trans-4-pentylcyclohexyl) benzene; 8% 4-
Propyl-4'-difluoromethoxybiphenyl; 12
% Of 4- (trans-4-propylcyclohexyl)-
4'-difluoromethoxybiphenyl.

Clearing point TC = 87 ° C. Viscosity η = 19 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.0985 (20 ° C., 589 n
m) Dielectric anisotropy Δε = 6.3 (20 ° C., 1 kHz) b) An electro-optical liquid crystal system is manufactured by the method described in Examples 1b), 1.1 to 1.3 and 2.

Method b) The electro-optical systems produced according to 1.1 to 1.3 and 2 have good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltage And good contrast as well as particularly high stability.

Example 25 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5
-Propylpyridine; 20% 2- (4-cyanophenyl) -5-butylpyridine; 20% 2- (4-cyanophenyl) -5-pentylpyridine; 25% 4-pentyl-4'-cyanobiphenyl 15% of 4-pentyl-4 "-cyanoterphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 26 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5
-Propylpyridine; 20% of 2- (4-cyanophenyl) -5-butylpyridine; 20% of 2- (4-cyanophenyl) -5-pentylpyridine; 20% of 4-pentyl-2-fluoro-4. '-Cyanobiphenyl; 10%
1- (4- (4-pentylphenyl) phenyl) -2
-(3-fluoro-4-cyanophenyl) ethane; 10
% 4-pentyl-4'-cyanoterphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 27 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 30% of 2- (4-cyanophenyl) -5
-Propylpyridine; 30% of 2- (4-cyanophenyl) -5-butylpyridine; 20% of 2- (4-cyanophenyl) -5-pentylpyridine; 10% of 2- (4
-Cyanophenyl) -5- (4-pentylphenyl) pyridine; 10% 1- (4- (5-pentylpyridinyl-2) phenyl) -2- (3-fluoro-4-cyanophenyl) ethane.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 28 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 30% of 2- (4-cyanophenyl) -5
-Propylpyridine; 30% of 2- (4-cyanophenyl) -5-butylpyridine; 20% of 2- (4-cyanophenyl) -5-pentylpyridine; 10% of 1- (4
-(4-pentylphenyl) phenyl) -2- (3-fluoro-4-cyanophenyl) ethane; 10% 1-
(4-pentylphenyl) -2- (4- (4-cyanophenyl) phenyl) ethane.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Example 29 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5
-Ethylpyrimidine; 20% of 2- (4-cyanophenyl) -5-propylpyrimidine; 20% of 2- (4-cyanophenyl) -5-pentylpyrimidine; 20% of 4
-Pentyl-3 ", 5" -difluoro-4 "-cyanoterphenyl; 20% of 2-fluoro-4-pentyl-
4'-cyanobiphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 30 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
10.0% 2- (4-cyanophenyl) -5-propyl-1,3-dioxane; 15.0% 2- (4-cyanophenyl) -5-butyl-1,3-dioxane; 1
5.0% of 2- (4-cyanophenyl) -5-pentyl-1,3-dioxane; 20.0% of 4- (trans-
14. 4-propylcyclohexyl) benzonitrile;
0% of 4- (trans-4-pentylcyclohexyl)
Benzonitrile; 10.0% 4- (trans-4-heptylcyclohexyl) benzonitrile; 5.0% 4
-(Trans-4-propylcyclohexyl) -4'-
(Trans-4-propylcyclohexyl) biphenyl; 5.0% of 4- (trans-4-pentylcyclohexyl) -4 ′-(trans-4-pentylcyclohexyl) biphenyl; 5.0% of 4- (trans-4) -Pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl.

Clearing point TC = 76 ° C. Viscosity η = 34 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.131 (20 ° C., 589 nm) Dielectric anisotropy Δε = 17 (1 kHz, 20 ° C.) b The electro-optical systems produced by the method described in example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 31 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
15.0% 2- (4-cyanophenyl) -5-propyl-1,3-dioxane; 10.0% 2- (4-cyanophenyl) -5-butyl-1,3-dioxane; 1
5.0% of 2- (4-cyanophenyl) -5-pentyl-1,3-dioxane; 15.0% of 2- (4-cyanophenyl) -5-propylpyridine; 15.0% of 2-
(4-cyanophenyl) -5-butylpyridine;
0% 2- (4-cyanophenyl) -5-pentylpyridine; 5.0% 4- (trans-4-propylcyclohexyl) -4 ′-(trans-4-propylcyclohexyl) biphenyl; 5.0% 4- (trans-4-
Pentylcyclohexyl) -4 ′-(trans-4-pentylcyclohexyl) biphenyl; 5.0% of 4-
(Trans-4-pentylcyclohexyl) -4′-
(Trans-4 '-(trans-4-propylcyclohexyl) biphenyl.

Clearing point TC = 68 ° C. Viscosity η = 45 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.131 (20 ° C., 589 nm) Dielectric anisotropy Δε = 17 (1 kHz, 20 ° C.) b The electro-optical systems produced by the method described in example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 32 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
15% of 2- (4-cyanophenyl) -5-propyl-
1,3-dioxane; 15% of 2- (4-cyanophenyl) -5-butyl-1,3-dioxane; 15% of 2-
(4-cyanophenyl) -5-pentyl-1,3-dioxane; 20% of 4-pentyl-4'-cyanobiphenyl; 20% of 4'-heptyl-4'-cyanobiphenyl; 5% of 4- ( Trans-4-propylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 5% of 4- (trans-4-pentylcyclohexyl) -4'-(trans-4-pentylcyclohexyl) biphenyl; 5% 4- (trans-4
-Pentylcyclohexyl) -4 '-(trans-4-
Propylcyclohexyl) biphenyl.

Clearing point TC = 72 ° C. Viscosity η = 38 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.166 (589 nm, 20 ° C.) Dielectric anisotropy Δε = 20 (1 kHz, 20 ° C.) b The electro-optical systems produced by the method described in example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 33 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
10% of 2- (4-cyanophenyl) -5-propyl-
1,3-dioxane; 10% 2- (4-cyanophenyl) -5-butyl-1,3-dioxane; 15% 2-
(4-cyanophenyl) -5-pentyl-1,3-dioxane; 5% of 2- (4-cyanophenyl) -5-pentylpyrimidine; 10% of 2- (4-cyanophenyl)
-5-heptylpyrimidine; 15% of 4- (trans-
4-propylcyclohexyl) benzonitrile; 10%
4- (trans-4-pentylcyclohexyl) benzonitrile; 10% 4- (trans-4-heptylcyclohexyl) benzonitrile; 5% 4- (trans-4-propylcyclohexyl) -4 '-(trans-
4-propylcyclohexyl) biphenyl; 5% of 4-
(Trans-4-pentylcyclohexyl) -4′-
(Trans-4-propylcyclohexyl) biphenyl; 5% of 4- (trans-4-pentylcyclohexyl) -4 ′-(trans-4-propylcyclohexyl) biphenyl.

Clearing point TC = 76 ° C. Viscosity η = 38 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.15 (589 nm, 20 ° C.) Dielectric anisotropy Δε = 21 (1 kHz, 20 ° C.) b The electro-optical systems produced by the method described in example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 34 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 1- (4- (4-pentylphenyl) phenyl) -2- (4-cyanophenyl) ethane;
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

B) The electro-optical system produced by the method described in Example 1 b) is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 35 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% 1- (trans-4-pentylcyclohexyl) -2- (4-cyanophenyl) ethane.

Clearing point TC = 80 ° C. Viscosity η = 29 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.14 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.8 (20 ° C., 1 kHz) B) The electro-optical systems produced by the method described in Example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, as well as especially low threshold voltages and high It is characterized by contrast.

Example 36 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
21.2% 2- (4-cyanophenyl) -5-propylpyridine; 21.2% 2- (4-cyanophenyl)
-5-butylpyridine; 21.2% of 2- (4-cyanophenyl) -5-pentylpyridine; 21.2% of 2-
(4-cyanophenyl) -5- (4-pentylphenyl) pyridine; 5.0% 4-propoxy-4'-fluorotran; 5.0% 4-butoxy-4'-fluorotran; 5.0 % 4-pentoxy-4'-fluorotolan.

Clearing point TC = 75 ° C. Viscosity η = 58 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.2627 (20 ° C., 589 n
m) ordinary ray refractive index n0 = 1.5277 (20 ° C., 589 n)
m) Dielectric anisotropy Δε = 22.6 (20 ° C., 1 kHz) b) The electro-optical system manufactured by the method described in Example 1b) has good manufacturability, a wide operating temperature range, electro-optical parameters, and Are characterized by an advantageous value for the temperature dependence of, a low threshold voltage and a high contrast.

Example 37 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.9% p-trans-4-propylcyclohexylbenzonitrile; 13.7% p-trans-4- Butylcyclohexylbenzonitrile; 2
2.5% p-trans-4-pentylcyclohexylbenzonitrile; 14.5% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4-
(Trans-4-pentylcyclohexyl) -4′-
(Trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate 5.6% of 4- (trans-4-pentylcyclohexyl) -4′-cyanobiphenyl;
0% of 1- [4- (trans-4- (trans-4-propylcyclohexyl) cyclohexyl] phenyl]-
2- (4-cyanophenyl) ethane.

B) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and good High contrast.

Example 38 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of 3- (4-isothiocyanatophenyl) -5-pentylpyrimidine.

Clearing point TC = 83 ° C. Viscosity η = 28 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.18 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14.6 (20 ° C., 1 kHz) B) electro-optical systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltages and good contrast It is characterized by.

Example 39 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.2% p-trans-4-propylcyclohexylbenzonitrile; 12.6% p-trans-4- Butylcyclohexylbenzonitrile; 2
2.5% p-trans-4-pentylcyclohexylbenzonitrile; 13.5% p-trans-4-heptylcyclohexylbenzonitrile; 6.3% 4-
(Trans-4-pentylcyclohexyl) -4′-
(Trans-4-propylcyclohexyl) biphenyl; 5.4% of 4-pentyl-4 "-cyanoterphenyl; 7.2% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate 6.3% 4- (trans-4-pentylcyclohexyl) -4′-cyanobiphenyl; 10%
1- (trans-4-pentylcyclohexyl-4-
Isothiocyanatobenzene.

B) An electro-optical liquid crystal system is manufactured by the method described in Examples 1b), 1.1 to 1.3 and 2.

The electro-optical systems produced by this method are characterized by good manufacturability, wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltage and high contrast.

Example 40 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 12% of 1- (trans-4-propylcyclohexyl) -4-isothiocyanatobenzene;
8% of 1- (trans-4-butylcyclohexyl)-
4-isothiocyanatobenzene.

Clearing point TC = 80 ° C. Viscosity η = 24 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.8 (20 ° C., 1 kHz) B) An electro-optical liquid crystal system is produced by the method described in Examples 1b), 1.1 to 1.3 and 2.

The electro-optical systems produced by this method are characterized by good manufacturability, wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltage and high contrast.

Example 41 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 10% of 4- (trans-4-propylcyclohexyl) -4'-difluoromethoxybiphenyl; 10% of 4- (trans-4-pentylcyclohexyl)- 4'-difluoromethoxybiphenyl.

Clearing point TC = 102 ° C. Viscosity η = 31 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.4 (20 ° C., 1 kHz) B) electro-optical systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltages and good contrast It is characterized by.

Example 42 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.2% p-trans-4-propylcyclohexylbenzonitrile; 12.6% p-trans-4- Butylcyclohexylbenzonitrile; 2
2.5% p-trans-4-pentylcyclohexylbenzonitrile; 5.4% 4-pentyl-4 "-cyanoterphenyl; 7.2% trans-4-butylcyclohexylcarboxylic acid 4- (trans- 4-propylcyclohexyl) phenyl; 6.3% of 4- (trans-
4-pentylcyclohexyl) -4'-cyanobiphenyl; 10% 4-pentyl-4 "-difluoromethoxyterphenyl; 13.5% p-trans-4-heptylcyclohexylbenzonitrile; 6.3% 4- (Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexylbiphenyl.

B) The electro-optical system produced by the method described in Example 1b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltage and high It is characterized by contrast.

Example 43 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of 1- (trans-4-pentylcyclohexyl) -4-fluorobenzene.

Viscosity η = 20 mm2 / sec (20 ° C.) Optical anisotropy Δn = 0.12 (20 ° C., 589 nm) Dielectric anisotropy Δε = 10.2 (20 ° C., 1 kHz) b) Example 1b The electro-optical systems produced by the method described under (1) are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and good contrast.

Example 44 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of 2- (4- (3,4-difluorophenyl) phenyl) -5-heptylpyrimidine.

Clearing point TC = 97 ° C. Viscosity η = 48 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 12.9 (20 ° C., 1 kHz) B) electro-optical systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltages and good contrast It is characterized by.

Example 45 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
5% of 4- (trans-4-pentylcyclohexyl)
11.4'-chlorobiphenyl; 17.1% p-trans-4-propylcyclohexylbenzonitrile;
3% p-trans-4-butylcyclohexylbenzonitrile; 23.8% p-trans-4-pentylcyclohexylbenzonitrile; 14.3% 4- (trans-4-heptylcyclohexyl) benzonitrile;
6.7% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6.7% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl 5.7
% 4-pentyl-4 "-cyanoterphenyl; 7.6
% Trans-4-butylcyclohexylcarboxylic acid 4%
-(Trans-4-propylcyclohexyl) phenyl.

Clearing point TC = 95 ° C. Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.6 (20 ° C., 1 kHz) Flow viscosity η = 31 mm 2 / sec (20 ° C) b) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Example 46 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
20% 1- (trans-4-pentylcyclohexyl) -4-chlorobenzenel; 14.4% p-trans-4-propylcyclohexylbenzonitrile; 1
1.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-
4-heptylcyclohexylbenzonitrile; 5.6%
4- (trans-4-pentylcyclohexyl)-
4'-cyanobiphenyl; 5.6% of 4- (trans-
4-pentylcyclohexyl) -4 ′-(trans-4
-Propylcyclohexyl) biphenyl; 4.8% of 4
-Pentyl-4 "-cyanoterphenyl; 6.4% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate.

Clearing point TC = 69 ° C. Optical anisotropy Δn = 0.13 (20 ° C., 589 nm) Dielectric anisotropy Δε = 10.8 (20 ° C., 1 kHz) Flow viscosity η = 21 mm 2 / sec (20 ° C) b) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Example 46b a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
5.0% of 2-fluoro-4- (trans-4-pentylcyclohexyl) -3 ", 4"-difluoroterphenyl; 8.0% of 1- [4- (2-fluoro-4-propylphenyl) -Phenyl] -2- (4-fluorophenyl) ethane; 11.0% of 1- [4- (2-fluoro-4-pentylphenyl) -phenyl] -2- (4-fluorophenyl) ethane; 0% of 1- {4- [4-
(Trans-4-propylcyclohexyl) -2-fluorophenyl] -phenyl} -2- (3,4-difluorophenyl) ethane; 7.0% of 1- {4- [4- (trans-4-pentylcyclohexyl) ) -2-Fluorophenyl] -phenyl} -2- (3,4-difluorophenyl) ethane; 2.0% of 1- {4- [4- (trans-4-propylcyclohexyl) -2-fluorophenyl] -Phenyl {-2- (3-fluorophenyl) ethane; 6.0% of 1- {4- [4- (trans-4-pentylcyclohexyl) -2-fluorophenyl] -phenyl} -2- (3- Fluorophenyl) ethane; 1
0.0% of 4- (trans-4-ethylcyclohexyl) -3 ′, 4′-difluorobiphenyl; 10.0%
Of 1- (4-pentylphenyl) -2- [4- (3,4
-Difluorophenyl) -phenyl] ethane; 10.0
% Of 4- (trans-4-propylcyclohexyl)-
3 ', 4'-difluorobiphenyl; 10.0% of 4-
(Trans-4-pentylcyclohexyl) -3 ′,
4'-difluorobiphenyl; 7.0% of 4- (trans-4-ethylcyclohexyl) -3 ', 4', 5'-
Trifluorobiphenyl; 7.0% of 4- (trans-
4-pentylcyclohexyl) -3 ′, 4 ′, 5′-trifluorobiphenyl; clearing point TC = 97 ° C. optical anisotropy Δn = 0.1660 (20 ° C., 589 n
m) ordinary ray refractive index n0 = 1.5115 (20 ° C., 589 n)
m) Dielectric anisotropy Δε = 7.6 (20 ° C., 1 kHz) b) The electro-optical system produced by the method described in Example 1b) has a wide operating temperature range, advantageous values for electro-optical parameters, and especially Characterized by high UV stability.

Example 47 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
12.1% of 3-fluoro-4-chlorophenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate; 9.9% of trans-4-
(Trans-4-pentylcyclohexyl) cyclohexylcarboxylic acid 3-fluoro-4-chlorophenyl;
9.0% of 3-fluoro-4-chlorophenyl trans-4-propylcyclohexylcarboxylate; 9.0% of 3-fluoro-4-pentylcyclohexylcarboxylate
Fluoro-4-chlorophenyl; 10.0% 2-fluoro-4-pentylphenyl trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate; 10.0% trans-4- (trans-4-propyl) Cyclohexyl) cyclohexylcarboxylic acid 2-
Fluoro-4-pentylphenyl; 10.0% 2-fluoro-4-pentylphenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate; 15.0% 4- (trans-4-propylcyclohexyl) ) Benzonitrile; 10.0% 4- (trans-4-pentylcyclohexyl) benzonitrile; 5.0% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl .

Viscosity η = 30.4 mm 2 / sec (20 ° C.) Birefringence Δn = 0.11 (20 ° C., 589 nm) Clearing point N 114.9 I b) Electricity produced by the method described in Example 1b) The optics are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Example 48 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
12.1% of 3-fluoro-4-chlorophenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate; 9.9% of trans-4-
(Trans-4-pentylcyclohexyl) cyclohexylcarboxylic acid 3-fluoro-4-chlorophenyl;
9.0% of 3-fluoro-4-chlorophenyl trans-4-propylcyclohexylcarboxylate; 9.0% of 3-fluoro-4-pentylcyclohexylcarboxylate
Fluoro-4-chlorophenyl; 8.0% trans-
2-fluoro-4-pentylphenyl 4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate; 7.0% 2-fluoro-4-pentylphenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate 7.0% of Trans-4
-(Trans-4-propylcyclohexyl) cyclohexyl carboxylate 2-fluoro-4-propylphenyl; 15.0% 4- (trans-4-propylcyclohexyl) benzonitrile; 13.0% 4- (trans-4) -Pentylcyclohexyl) benzonitrile;
2.0% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 8.0% 4-pentylphenyl trans-4-propylcyclohexylcarboxylate.

Viscosity η = 25.9 mm 2 / sec (20 ° C.) Birefringence Δn = 0.10 (20 ° C., 589 nm) Clearing point N 94.2 I b) Electricity produced by the method described in Example 1b) The optics are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Example 49 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% 4- Pentyl-
4 "-cyanoterphenyl; 6.4% trans-4-
Butylcyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.6% of 4-
(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6% 4-propylphenyl-4-heptyl benzoate; 7% 4-pentylphenyl-4-heptyl benzoate; 7.0% benzoic acid 4-heptylphenyl-4-heptyl.

Clearing point TC = 77 ° C. Viscosity η = 34 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.14 (20 ° C., 589 nm) b) Electro-optic produced by the method described in Example 1b) The system is characterized by a wide operating temperature range, advantageous values for the electro-optic parameters and their temperature dependence, and in particular a low threshold voltage.

Example 50 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 12% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 20% of 4-propyl-4'-cyano Biphenyl; 13% of 4-pentyl-
4'-cyanobiphenyl; 20% of 4- (trans-4
-Pentylcyclohexyl) -4'-cyanobiphenyl; 15% of 4-propyl-3'-fluoro-4 "-cyanoterphenyl; 20% of 4-pentoxy-4'-fluorotran.

B) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltage and high It is characterized by contrast.

Example 51 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
18% of 4-cyano-4 '-(trans-4-pentylcyclohexyl) biphenyl; 35% of 4-cyano-
4'-hexylbiphenyl; 22% of 4-cyano-4 '
9% 4-cyano-4 "-pentylterphenyl; 5% 4-cyano-4'-yl-biphenyl-4-heptyl-4'-yl-biphenylcarboxylate; 5% 4- 6% of 1- (trans-4-propylcyclohexyl) -2- (4-pentyl-2-fluoro-4'-cyano-4'-nonoxybiphenyl;
Yl-biphenyl) ethane.

Clearing point TC = 100 ° C. Viscosity η = 55 mm 2 / sec (20 ° C.) Dielectric anisotropy Δε = 14.1 (20 ° C., 589 nm) Optical anisotropy Δn = 0.24 (20 ° C., 1 kHz) B) The electro-optical systems produced by the method described in Example 1 b) have a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, and low threshold voltages, good manufacturability and high contrast. It is characterized by.

Example 52 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
25% 2- (4-cyanophenyl) -5-propylpyridine; 25% 2- (4-cyanophenyl) -5-butylpyridine; 25% 2- (4-cyanophenyl)-
5-pentylpyridine; 25% of 2- (4-cyanophenyl) -5- (pentylphenyl) pyridine.

Clearing point TC = 85 ° C. Viscosity η = 70 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.269 (20 ° C., 589 nm) Dielectric anisotropy Δε = 24.1 (20 ° C., 1 kHz) B) The electro-optical liquid-crystal systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high It is characterized by contrast.

Example 53 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
17.5% 2- (4-cyanophenyl) -5-propylpyridine; 17.5% 2- (4-cyanophenyl)
17.5% of 2- (4-cyanophenyl) -5-pentylpyridine; 17.5% of 2-
(4-cyanophenyl) -5- (4-pentylphenyl) pyridine; 15.0% of 1- [4- (4-propylphenyl) phenyl-2- (3-fluoro-4-cyanophenyl) ethane; 0.0% of 1- [4- (4-pentylphenyl) phenyl-2- (3-fluoro-4-cyanophenyl) ethane.

Clearing point TC = 94 ° C. Optical anisotropy Δn = 0.272 (20 ° C., 589 nm) Dielectric anisotropy Δε = 25.6 (20 ° C., 1 kHz) b) Described in Example 1b) The electro-optical liquid crystal systems produced by the method are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high contrast.

Example 54 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
22.5% 2- (4-cyanophenyl) -5-propylpyridine; 22.5% 2- (4-cyanophenyl)
22.5% of 2- (4-cyanophenyl) -5-pentylpyridine; 22.5% of 2-
(4-cyanophenyl) -5- (4-pentylphenyl) pyridine; 10.0% of 1- (4-propylphenyl) phenyl-2- [4- (3-fluoro-4-cyanophenyl) phenyl] ethane .

Clearing point TC = 82 ° C. Viscosity η = 74 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.260 (20 ° C., 589 nm) Dielectric anisotropy Δε = 25 (20 ° C., 1 kHz) b The electro-optical liquid-crystal systems produced by the method described in Example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high contrast. Features.

Example 55 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 22.5
% Of 2- (4-cyanophenyl) -5-propylpyridine; 22.5% of 2- (4-cyanophenyl) -5-butylpyridine; 22.5% of 2- (4-cyanophenyl) -5 -Pentylpyridine; 22.5% of 2- (4-
Cyanophenyl) -5- (4-pentylphenyl) pyridine; 10.0% of 4-pentyl-3 ", 5" -difluoro-4 "-cyanoterphenyl.

Clearing point TC = 84 ° C. Viscosity η = 75 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.266 (20 ° C., 589 nm) Dielectric anisotropy Δε = 26 (20 ° C., 1 kHz) b The electro-optical liquid-crystal systems produced by the method described in Example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high contrast. Features.

Example 56 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical properties: 20.0
% Of 2- (4-cyanophenyl) -5-propylpyridine; 20.0% of 2- (4-cyanophenyl) -5-butylpyridine; 20.0% of 2- (4-cyanophenyl) -5 -Pentylpyridine; 20.0% of 2- (4-
Cyanophenyl) -5- (4-pentylphenyl) pyridine; 10.0% of 2- (3-fluoro-4-cyanophenyl) -5-propylpyrimidine; 10.0% of 2-
(3-Fluoro-4-cyanophenyl) -5-pentylpyrimidine.

Clearing point TC = 71 ° C. Viscosity η = 68 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.253 (20 ° C., 589 nm) Dielectric anisotropy Δε = 29.5 (20 ° C., 1 kHz) B) The electro-optical liquid-crystal systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high It is characterized by contrast.

Example 57 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0
11.% p-trans-4-propylcyclohexylbenzonitrile; 10.0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl; 6.0% 4- (trans-4-pentylcyclohexyl-). 4'-
(Trans-4-propylcyclohexyl) biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate 20.0% of 1- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] -2- (3-fluoro-4-cyanophenyl) ethane.

Clearing point TC = 98 ° C. Viscosity η = 39 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.139 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14 (20 ° C., 1 kHz) b The electro-optical liquid-crystal systems produced by the method described in example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and angles of contrast. It is characterized by low dependence.

Example 58 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0
11.% p-trans-4-propylcyclohexylbenzonitrile; 10.0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl; 6.0% 4- (trans-4-pentylcyclohexyl-). 4'-
(Trans-4-propylcyclohexyl) biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate 20.0% of 1- (trans-4-pentylcyclohexyl) -2- (3-fluoro-4-phenyl) ethane.

Clearing point TC = 76 ° C. Viscosity η = 30 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.130 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13 (20 ° C., 1 kHz) b The electro-optical liquid-crystal systems produced by the method described in example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and angles of contrast. It is characterized by low dependence.

Example 59 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0
11.% p-trans-4-propylcyclohexylbenzonitrile; 10.0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl; 6.0% 4- (trans-4-pentylcyclohexyl-). 4'-
(Trans-4-propylcyclohexyl) biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate 20.0% of 4-pentyl-4'-chlorobiphenyl.

Clearing point TC = 74 ° C. Viscosity η = 27 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.150 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11 (20 ° C., 1 kHz) b The electro-optical liquid-crystal systems produced by the method described in example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and angles of contrast. It is characterized by low dependence.

Example 60 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 16.0
12.% p-trans-4-propylcyclohexylbenzonitrile; 13.0% p-trans-4-butylcyclohexylbenzonitrile; 23.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl; 6.0% 4- (trans-4-pentylcyclohexyl) -4 '
-(Trans-4-propylcyclohexyl) biphenyl; 6.0% of 4-pentyl-4 "-cyanoterphenyl; 7.0% of 4- (trans-4-propylcyclohexyl) trans-4-butylcyclohexylcarboxylate Phenyl; 5.0% 4- (trans-4-propylcyclohexyl) -4'-methoxytran; 5.0%
4- (trans-4-propylcyclohexyl)-
4'-ethoxytran.

Clearing point TC = 106 ° C. Viscosity η = 30 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.163 (20 ° C., 589 nm) Dielectric anisotropy Δε = 10.5 (20 ° C., 1 kHz) B) The electro-optical liquid-crystal systems produced by the method described in Example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and contrast. Is characterized by having a small angle dependency.

Example 61 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0
11.% p-trans-4-propylcyclohexylbenzonitrile; 10.0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl; 6.0% 4- (trans-4-pentylcyclohexyl-). 4'-
(Trans-4-propylcyclohexyl) biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate 20.0% of 4- (trans-4-propylcyclohexyl) -3 ′, 4 ′, 5′-trifluorobiphenyl.

Clearing point TC = 82 ° C. Viscosity η = 32 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.138 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13.5 (20 ° C., 1 kHz) B) The electro-optical liquid-crystal systems produced by the method described in Example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and contrast. Is characterized by having a small angle dependency.

Example 62 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0
11.% p-trans-4-propylcyclohexylbenzonitrile; 10.0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6.0%
4- (trans-4-pentylcyclohexyl)-
4 '-(trans-4-propylcyclohexyl) biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propyl) trans-4-butylcyclohexylcarboxylate Cyclohexyl) phenyl; 10.0% 1- (trans-4-
(Trans-4-propylcyclohexyl) cyclohexyl) -2- (4-cyanophenyl) ethane; 10.0
% Of 1- (trans-4- (trans-4-pentylcyclohexyl) cyclohexyl) -2- (4-cyanophenyl) ethane.

Clearing point TC = 111 ° C. Viscosity η = 36 mm 2 / sec (20 ° C.) Dielectric anisotropy Δε = 11.8 (20 ° C., 1 kHz) b) Electricity produced by the method described in Example 1b) Optical liquid crystal systems are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and low angle dependence of the contrast.

Example 63 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0
11.% p-trans-4-propylcyclohexylbenzonitrile; 10.0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl; 6.0% 4- (trans-4-pentylcyclohexyl) -4 '
-(Trans-4-propylcyclohexyl) biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) trans-4-butylcyclohexylcarboxylate Phenyl; 10.0% 1- (4-propylphenyl) -2- [4- (2-fluoro-4-pentylphenyl) phenyl] ethane; 10.0% 1- (4-pentylphenyl) -2 -[4- (2-Fluoro-4-propylphenyl) phenyl] ethane.

Clearing point TC = 85 ° C. Viscosity η = 29 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.146 (20 ° C., 589 nm) b) Electricity produced by the method described in Example 1b) Optical liquid crystal systems are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and low angle dependence of the contrast.

Example 64 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 34.6
12. 5% of 4-pentyl-4'-cyanobiphenyl;
5% of 4-propoxy-4'-cyanobiphenyl; 1
0.35% 4-pentoxy-4'-cyanobiphenyl; 13.5% 4-octoxy-4'-cyanobiphenyl; 10.0% 4- (trans-4-pentylcyclohexyl) -4'-cyano Biphenyl; 9.0% of 4
-[2- (p-propylphenyl) ethyl] -4'-cyanobiphenyl; and 9.0% of 4- [2- (p-pentylphenyl) ethyl] -4'-cyanobiphenyl.

NI 84 ° C. Δn 0.247 (20 ° C., 589 nm) b) The electro-optical liquid crystal system manufactured by the method described in Example 1b) has good manufacturability, a wide operating temperature range, and electro-optics. It is characterized by advantageous values for the parameters and their temperature dependence, good contrast and low angular dependence of the contrast.

Example 65 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
20% of 4-pentyl-4'-cyanobiphenyl; 23
% 2- (4-cyanophenyl) -5-pentylpyridine; 17% 4-propoxy-4'-cyanobiphenyl; 13% 4-pentoxy-4'-cyanobiphenyl; 17% 4-octoxy-4. '-Cyanobiphenyl; 10.0% of 4-pentyl-4 "-cyanoterphenyl.

Clearing Point TC = 70.4 ° C. Viscosity η = 61 mm 2 / sec (20 ° C.) Threshold Voltage V [90.0.20] = 1.31 V The threshold voltage is measured as described in Example 9a. .

B) An electro-optical liquid crystal system is manufactured by the method described in Example 1 b).

Example 66 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
12% 2- (4-cyanophenyl) -5-propylpyridine; 15% 2- (4-cyanophenyl) -5-pentylpyridine; 18% 4-pentyl-4′-cyanobiphenyl; 9% 4-propoxy-4'-cyanobiphenyl; 9% of 4-pentyl-4 "-cyanobiphenyl; 22% of 4-propyl-2'-fluoro-4"-cyanoterphenyl; 15% of 4- (trans- 4-pentylcyclohexyl) -4'-cyanobiphenyl.

Clearing point TC = 114 ° C. Viscosity η = 86.6 mm 2 / sec (20 ° C.) Threshold voltage V [90.0.20] = 1.69V The threshold voltage is measured as described in Example 9a. .

B) An electro-optical liquid crystal system is manufactured by the method described in Example 1 b).

Example 67 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
12% 2- (4-cyanophenyl) -5-propylpyridine; 15% 2- (4-cyanophenyl) -5-pentylpyridine; 5% 4-cyanobiphenyl; 8.5
% 4-ethyl-4'-cyanobiphenyl; 8.5% 4-propyl-4'-cyanobiphenyl; 20% 4-
Pentyl-4'-cyanobiphenyl; 17% of 4-propyl-2'-fluoro-4 "-cyanotelphenyl; 9
% 4-pentyl-4 "-cyanoterphenyl.

Clearing Point TC = 69.6 ° C. Viscosity η = 51 mm 2 / sec (20 ° C.) Threshold Voltage V [90.0.20] = 1.29V The threshold voltage is measured as described in Example 9a. .

B) An electro-optical liquid crystal system is manufactured by the method described in Example 1 b).

Example 68 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 14.0% of 4-ethyl-4'-cyanobiphenyl; 15.0% of 4-butyl 41.9% 4-hexyl-4'-cyanobiphenyl; 2.5% 4-methoxy-4'-cyanobiphenyl; 12.0% 4-propoxy-4'-cyano Biphenyl; 7.6% 4-pentyl-4 "-cyanoterphenyl; 3.0% 4- (4-cyanophenyl) phenyl 4- (4-pentylphenyl) benzoate;
4.0% of 4- (4-heptylphenyl) benzoic acid 4-
(3-cyanophenyl) phenyl.

Birefringence Δn = 0.232 (20 ° C., 589 nm) Ordinary ray refractive index n0 = 1.766 (20 ° C., 589 nm) Dielectric anisotropy Δε = 15.8 (20 ° C., 1 kHz) Threshold Voltage V [10.0.20] = 1.23V Clearing point TC = 64 ° C. The threshold voltage has a cell interval of 7 μm, and a TN cell placed between orthogonal polarizers (twist angle ψ = π / 4) Was measured.

B) The electro-optical system produced by the method described in Example 1 b) is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and a particularly low threshold voltage.

Example 69 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 34.0% of 4-pentyl-4'-
Cyanobiphenyl; 10.0% of 4-propoxy-4 '
-Cyanobiphenyl; 13.0% of 4-ethyl-4'-
Cyanobiphenyl; 10.0% of 4-pentoxy-4 '
-Cyanobiphenyl; 13.0% of 4- (4-pentylphenyl) -4'-cyanophenyl; 10.0% of 4-
Octoxy-4'-cyanobiphenyl; 10.0% of 1
-(Trans-4- (trans-4-propylcyclohexyl) cyclohexyl-4- (4-cyanophenyl)
Phenyl) ethane.

Birefringence Δn = 0.243 (20 ° C., 589 nm) Ordinary refractive index n0 = 1.765 (20 ° C., 589 nm) Clearing point TC = 91 ° b) Production by the method described in Example 1b) The described electro-optical system is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and in particular a low threshold voltage.

Example 70 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 20.0% of 1- {4- [2-fluoro-4- (trans-4-pentyl) Cyclohexyl)
Phenyl] phenyl} -2- (4-fluorophenyl)
Ethane; 10.0% of 1- {4- [2-fluoro-4-
(Trans-4-pentylcyclohexyl) phenyl]
Phenyl} -2- (4-fluorophenyl) ethane; 3
0.0% of 1- {4- [2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 30.0% of 1- [4- (2-fluoro-4-pentyl) Phenyl) phenyl] -2- (4-chlorophenyl) ethane; 10.0% of 1- [4- (trans-4-
Propylcyclohexyl) phenyl] -2- (4-fluorophenyl) ethane; clearing point TC = 104 ° C. optical anisotropy Δn = 0.189 (20 ° C., 589 nm) b) prepared by the method described in Example 1b) The resulting electro-optical liquid crystal systems have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, low contrast angle dependence, and especially high UV stability It is characterized by.

Example 71 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 17.5% of 1- {4- [2-fluoro-4- (trans-4-pentyl) Cyclohexyl)
Phenyl] phenyl} -2- (4-fluorophenyl)
Ethane; 8.5% of 1- {4- [2-fluoro-4-
(Trans-4-pentylcyclohexyl) phenyl]
Phenyl {-2- (4-chlorophenyl) ethane; 2
5.5% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl) ethane; 25.5% 1- [4- (2-fluoro-4-) Pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% of 1- [4- (trans-4-propylcyclohexyl) phenyl] -2- (4-fluorophenyl) ethane; 8.5% Of 1- [4- (trans-4-pentylcyclohexyl) phenyl] -2- (4
-Fluorophenyl) ethane; 8.5% of 1- [4-
(Trans-4-propylcyclohexyl) phenyl]
-2- (4-Chlorophenyl) ethane.

Clearing point TC = 98 ° C. Optical isomer Δn = 0.176 (20 ° C., 589 nm) Dielectric anisotropy Δε = 5.0 (20 ° C., 1 kHz) b) By the method described in Example 1b) The electro-optical liquid crystal systems produced have good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, good contrast, low contrast angle dependence, and especially high UV stability Characteristic.

Example 72 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 17% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl)] Phenyl] phenyl {-2- (4-fluorophenyl) ethane; 8.5% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl} -2- (4- Chlorophenyl) ethane; 25.5%
1- [4- (2-fluoro-4-pentylphenyl)
Phenyl] -2- (4-fluorophenyl) ethane; 2
5.5% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% 1- [4- (trans-4-propylcyclohexyl) Phenyl] -2- (4-fluorophenyl) ethane; 7.8% of 1- (trans-4-pentylcyclohexyl) -1-chlorobenzene; 7.2% of 4
-(Trans-4-heptylcyclohexyl) -1-chlorobenzene.

Clearing point TC = 87 ° C. Optical isomer Δn = 0.171 (20 ° C., 589 nm) b) The electro-optical liquid crystal system produced by the method described in Example 1b) has good productivity and wide operating temperature. It is characterized by advantageous values for the range, the electro-optic parameters and their temperature dependence, good contrast, low angle dependence of the contrast, and especially high UV stability.

Example 73 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 10% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl)] Phenyl] phenyl {-2- (4-fluorophenyl) ethane; 10% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl} -2- (4-chlorophenyl) Ethane; 20% of 1
-[4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl) ethane; 10%
1- [4- (2-fluoro-4-pentylphenyl)
Phenyl] -2- (4-chlorophenyl) ethane;
% Of 4- (trans-4-pentylcyclohexyl)-
1-chlorobenzene; 10% 4- (trans-4-pentylcyclohexyl) -1-chlorobenzene; 15%
4-propyl-2'-fluoro-4 "-ethylterphenyl; 15% of 4-ethyl-2'-fluoro-4"-
Propyl terphenyl.

Clearing point TC = 75 ° C. Optical anisotropy Δn = 0.142 (20 ° C., 589 n
m) b) The electro-optical liquid crystal system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, contrast. Are characterized by a small angular dependence and a particularly high UV stability.

Example 74 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 16.9% of 1- {4- [2-fluoro-4- (trans-4-pentyl) Cyclohexyl)
Phenyl] phenyl} -2- (4-fluorophenyl)
Ethane; 8.5% of 1- {4- [2-fluoro-4-
(Trans-4-pentylcyclohexyl) phenyl]
Phenyl {-2- (4-chlorophenyl) ethane; 2
5.3% of 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl) ethane; 25.3% of 1- [4- (2-fluoro-4-) Pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% of 1- [4- (trans-4-propylcyclohexyl) phenyl] -2- (4-fluorophenyl) ethane; 15.5% 1- [trans-4
-(Trans-4-propylcyclohexyl) cyclohexyl] -2- (4-chlorophenyl) ethane.

Clearing Point TC = 112 ° C. Optical Anisotropy Δn = 0.178 (20 ° C., 589 n
m) b) The electro-optical liquid crystal system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, contrast. Are characterized by a small angular dependence and a particularly high UV stability.

Example 75 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 17% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl)] Phenyl] phenyl {-2- (4-fluorophenyl) ethane; 8.5% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl} -2- (4- Chlorophenyl) ethane; 25.5%
1- [4- (2-fluoro-4-pentylphenyl)
Phenyl] -2- (4-fluorophenyl) ethane; 2
5.5% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% 1- [4- (trans-4-propylcyclohexyl) Phenyl) phenyl] -2- (4-fluorophenyl) ethane; 7.6% of 4- (trans-4)
-Pentylcyclohexyl) -1-fluorobenzene;
7.4% of 4- (trans-4-hexylcyclohexyl) -1-fluorobenzene; clearing point TC = 80 ° C. optical anisotropy Δn = 0.172 (20 ° C., 589 n
m) b) The electro-optical liquid crystal system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, contrast. Are characterized by a small angular dependence and a particularly high UV stability.

Example 76 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
3. 2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate 4- (trans-4-propylcyclohexyl) biphenyl;
5. 8% of 4-pentyl-4 "-cyanoterphenyl;
4% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 5.6% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6% of 4- 4-propylphenyl heptylbenzoate 7% 4-pentylphenyl 4-heptylbenzoate 4-heptylphenyl 4-heptylbenzoate 7%.

Clearing point TC = 77.5 ° C. Viscosity η = 34 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.14 (20 ° C., 589 nm) b) Manufactured by the method described in Example 1b). Electro-optical systems are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 77 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 1- (trans-4- (trans-4-propylcyclohexyl) -2- (3-fluoro-4) -Phenyl) ethane; 14.4% p-trans-
4-propylcyclohexylbenzonitrile; 11.2
% P-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% trans-4- (Trans-4-pentylcyclohexyl)
4- (trans-4-propylcyclohexyl) phenyl cyclohexylcarboxylate; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4
-Butylcyclohexylcarboxylic acid 4- (trans-4
-Propylcyclohexyl) phenyl; 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 78 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters:
14.5% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 1
2% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% trans-4- (trans-4
4- (trans-4-propylcyclohexyl) phenyl 4-pentylcyclohexyl) cyclohexylcarboxylate; 6.4% 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 5.6% 4 -(Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 4.8
% 4-pentyl-4 "-cyanoterphenyl; 20%
2- (4-cyanophenyl) -5-pentylpyrimidine.

Clearing point TC = 82.5 ° C. Viscosity η = 34 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 16.1 (20 ° C.) B) The electro-optical system produced by the method described in Example 1 b) is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 79 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical properties: 10.0
% Of 2- (4-cyanophenyl) -5-propyltolu-
1,3-dioxane; 15.0% of 2- (4-cyanophenyl) -5-butyltolu-1,3-dioxane; 1
5.0% 2- (4-cyanophenyl) -5-pentyltolu-1,3-dioxane; 20.0% 4- (trans-4-propylcyclohexyl) benzonitrile; 1
5.0% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 10.0% of 4- (trans-4
-Heptylcyclohexyl) benzonitrile; 5.0%
Of trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylic acid 4- (trans-4-
Propylcyclohexyl) phenyl; 5.0% trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate 4- (trans-4-pentylcyclohexyl) phenyl; 5.0% trans-4-
(Trans-4-pentylcyclohexyl) cyclohexyl carboxylate 4- (trans-4-propylcyclohexyl) phenyl.

Clearing point TC = 76 ° C. Viscosity η = 34 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.131 (20 ° C., 589 nm) Dielectric anisotropy Δε = 17 (1 kHz, 20 ° C.) b The electro-optical liquid-crystal systems produced by the method described in Example 1b) are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. And

Example 80 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.9% p-trans-4-propylcyclohexylbenzonitrile; 13.7% p-trans-4- Butylcyclohexylbenzonitrile; 2
2.5% p-trans-4-pentylcyclohexylbenzonitrile; 14.5% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4-
4- (trans-4-propylcyclohexyl) phenyl (trans-4-pentylcyclohexyl) cyclohexylcarboxylate; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexyl 4- (trans-4-propylcyclohexyl) phenyl carboxylate; 5.6% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 10.0% of 1- [4- [trans-4 -(Trans-4-propylcyclohexyl) cyclohexyl]
Phenyl] -2- (4-cyanophenyl) ethane. b)
The electro-optical system produced by the method described in Example 1b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence,
And good contrast.

Example 81 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 14.4
% P-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4
-Pentylcyclohexylbenzonitrile; 12% p
-Trans-4-heptylcyclohexylbenzonitrile; 5.6% of 4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylic acid 4- (trans-4
-Propylcyclohexyl) phenyl; 4.8% of 4-
Pentyl-4 "-cyanoterphenyl; 6.4% 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 5.6
% Of 4- (trans-4-pentylcyclohexyl)-
4'-cyanobiphenyl; 10% of 4- (trans-4
-Propylcyclohexyl) -4'-difluoromethoxybiphenyl; 10% of 4- (trans-4-pentylcyclohexyl) -4'-difluoromethoxybiphenyl; clearing point TC = 102.3 ° C Viscosity η = 31 mm2 / sec (20 ° C ) Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.4 (20 ° C., 1 kHz) b) The electro-optical system manufactured by the method described in Example 1b) is as follows. It is characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optic parameters and their temperature dependence, low threshold voltages and good contrast.

Example 82 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0
11.% p-trans-4-propylcyclohexylbenzonitrile; 10.0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile;
0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6.0%
Trans-4-butylcyclohexylcarboxylic acid 4-
(Trans-4-propylcyclohexyl) phenyl;
5.0% 4-pentyl-4 "-cyanoterphenyl;
6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate; 20.0
% Of 1- (trans-4-pentylcyclohexyl)-
2- (3-fluoro-4-phenyl) ethane.

Clearing point TC = 76.3 ° C. Viscosity η = 30 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.130 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13 (20 ° C., 1 kHz) B) The electro-optical system produced by the method described in Example 1b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and angle of contrast. It is characterized by low dependence.

Example 83 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical properties: 25% of 2- (4-cyanophenyl) -5-propylpyridine;
25% 2- (4-cyanophenyl) -5-butylpyridine; 25% 2- (4-cyanophenyl) -5-pentylpyridine; 25% 2- (4-cyanophenyl)-
5- (4-pentylphenyl) pyridine.

Clearing point TC = 85 ° C. Viscosity η = 70 mm 2 / sec (20 ° C.) Optical anisotropy Δn = 0.269 (20 ° C., 589 nm) Dielectric anisotropy Δε = 24.1 (1 kHz, 20 ° C.) B) Examples 1b), 1.1, 1.2, 1.3 and 2) ordinary ray refractive index n0 = 1.529 (20 ° C., 589 nm)
The electro-optical system is manufactured by the method described in (1). However, in a method according to 1.1, the liquid crystal versus NOA 65
Was chosen to be 1: 1 and a 10 μm spacer was used.

In FIG. 1, the relative transmittance of the electro-optical system manufactured by the method described in Examples 1b) and 1.1 was measured by applying an applied voltage [sine wave AC voltage (effective value), frequency: 100 Hz].
As a function of This system is characterized by a particularly good contrast and a low threshold voltage.

Example 84 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 15% p-trans-4-propylcyclohexylbenzonitrile; 15% p-trans-4
-Butylcyclohexylbenzonitrile; 20% p-
Trans-4-pentylcyclohexylbenzonitrile; 10% 2- (4-cyanophenyl) -5-pentylpyridine; 15% 2- (4-cyanophenyl) -5.
-(4-pentylphenyl) pyridine; 7.5% of 4-
Ethoxy-4'-fluorotolan; 7.5% 4-butoxy-4'-fluorotolan. b) The electro-optical systems produced by the method described in Example 1b) are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters, low threshold voltages, and especially high stability.

Example 85 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 17.5% of 4-propyl-4'-cyanobiphenyl; 17.5% of 4-butyl-4'- 17.5% of 4-pentyl-4'-cyanobiphenyl; 17.5% of 2- (4-cyanophenyl)-
5- (4-pentylphenyl) pyridine; 15.0% of 4- (trans-4-propylcyclohexyl) -4'-
Trifluoromethoxytran; 15.0% 4-propyl-4'-trifluoromethoxytran. b) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, good manufacturability, advantageous values for the electro-optical parameters, low threshold voltages, and especially high stability. .

Example 86 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 15% p-trans-4-propylcyclohexylbenzonitrile; 15% p-trans-4
-Butylcyclohexylbenzonitrile; 15% p-
Trans-4-pentylcyclohexylbenzonitrile; 15% p-trans-4-heptylcyclohexylbenzonitrile; 10% 2- (3,4-difluorophenyl) -5-propylpyrimidine; 10% 2-
(4-fluorophenyl) -5-pentylpyrimidine;
10% 1- [4- (4-propylphenyl) phenyl] -2- (4-cyanophenyl) ethane; 10% 1
-[4- (4-pentylphenyl) phenyl] -2-
(4-cyanophenyl) ethane. b) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, good manufacturability, advantageous values for the electro-optical parameters, low threshold voltages, and especially high stability. .

Example 87 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 15% p-trans-4-propylcyclohexylbenzonitrile; 15% p-trans-4
-Butylcyclohexylbenzonitrile; 15% p-
Trans-4-pentylcyclohexylbenzonitrile; 15% p-trans-4-heptylcyclohexylbenzonitrile; 10% 1- (5-propylpyridinyl-2) -2- (4-cyanophenyl) ethane;
% Of 1- (5-pentylpyridinyl-2) -2- (4-
Cyanophenyl) ethane; 8% of 4-fluorophenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate; 8% of trans-4-
4-fluorophenyl (trans-4-pentylcyclohexyl) cyclohexyl carboxylate; 4% 3,4-difluorophenyl trans-4- (trans-4-pentylcyclohexyl) cyclohexyl carboxylate.

B) The electro-optical system produced by the method described in Example 1 b) has a wide operating temperature range, good manufacturability, advantageous values for electro-optical parameters, low threshold voltages, and especially high stability. Features.

Example 88 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical properties: 17.5
% Of 2- (4-cyanophenyl) -5-propylpyridine; 17.5% of 2- (4-cyanophenyl) -5-butylpyridine; 17.5% of 2- (4-cyanophenyl) -5. -Pentylpyridine; 17.5% of 2- (4-
Cyanophenyl) -5- (4-pentylphenyl) pyridine; 15.0 1- [4- (4-propylphenyl)
Phenyl] -2- (4-cyanophenyl) ethane; 1
5.0- [1- (4- (4-pentylphenyl) phenyl] -2- (4-cyanophenyl) ethane; clearing point TC = 94 ° C. optical anisotropy Δn = 0.2722 (20 ° C., 589 n
m) Dielectric anisotropy Δε = 25.6 (20 ° C., 1 kHz) b) The electro-optical system manufactured by the method described in Example 1b) has a wide operating temperature range, good manufacturability, and electro-optical parameters. It is characterized by advantageous values and especially low threshold voltages.

Example 89 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 20.0
% Of 2- (4-cyanophenyl) -5-propylpyridine; 20.0% of 2- (4-cyanophenyl) -5-butylpyridine; 20.0% of 2- (4-cyanophenyl) -5 -Pentylpyridine; 20.0% of 2- (4-
Cyanophenyl) -5- (4-pentylphenyl) pyridine; 10.0% of 4- (trans-4-propylcyclohexyl) -3 ′, 4′-difluorobiphenyl;
0.0% of 4- (trans-4-pentylcyclohexyl) -3 ′, 4′-difluorobiphenyl; clearing point TC = 86 ° C. optical anisotropy Δn = 0.2436 (20 ° C., 589 n
m) ordinary ray refractive index n0 = 1.5259 (20 ° C., 589 n)
m) Dielectric anisotropy Δε = 21.8 (1 kHz, 20 ° C.) b) Examples 1b), 1.1, 1.2, 1.3 and 2
The electro-optical system is manufactured by the method described in (1). However, in a method according to 1.1, the liquid crystal versus NOA 65
Was chosen to be 1: 1 and a 10 μm spacer was used.

In FIG. 2, the relative transmittance of the electro-optical system manufactured by the method described in Examples 1b) and 1.1 was measured by applying an applied voltage [sine wave AC voltage (effective value), frequency: 100 Hz].
As a function of

This system is characterized by a low threshold voltage, advantageous values for the gradient of the electro-optical properties and high UV stability.

[Brief description of the drawings]

FIG. 1 is a diagram showing a relative transmittance of an electro-optical system as an example of an electro-optical liquid crystal containing a liquid crystal mixture of the present invention (Example 83) as a function of voltage.

FIG. 2 is a diagram showing the relative transmittance of an electro-optical liquid crystal system containing another example of the liquid crystal mixture of the present invention (Example 89) as a function of voltage.

 ──────────────────────────────────────────────────続 き Continuation of front page (71) Applicant 591032596 Frankfurter Str. 250, D-64293 Darmstadt, Federal Republic of Germany (72) Inventor Coats, David United Kingdom B.H.21 3 S-Double Dawset Wimborne Marley Sop w. Set Pool Parkstone Ring Wood Road 244 (72) Inventor Smith, Graham United Kingdom 178 AX Dossett Pool Canford Heath Henbury Close 10 (72) Inventor Finkenzeller, Ulrich Germany Day 6831 Plankstadt Waltopfert 74 (72) Inventor Reifenrad, Volker DE-6101 Rossdorf Järnstraße 18 (72) Inventors Hitich, Reinha DOO Germany Day -6101 Modauta Lumpur 1 Am Kirchberg 11 (72) inventor Wilhelm, Stefan Germany Day -6100 Darumushi Yutatto August - Bebel - Strand Rase 11

Claims (30)

[Claims] 1. A method comprising the steps of: (a) providing a dielectrically positive liquid crystal mixture and optionally an optically transparent medium between two electrodes arbitrarily provided on a support sheet; Is ordered and one of the refractive indices of the liquid crystal mixture is the refractive index n _{M of the} matrix
And / or the mass of the liquid crystal mixture divided by the mass of the optically transparent medium is greater than or equal to 1.5 and, independent of the polarization of the incident light, one of the two switching states In an electro-optical liquid crystal system having a reduced transmittance as compared to the other state, the liquid crystal mixture is of the formula I (Wherein Q ¹ is Wherein ring A ¹ and ring A ² are independently trans-1,4
-Cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene and A ¹ and, if present, one of A ² are pyridine-2 , 5-diyl, pyrimidine-2,5
-Diyl, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl or naphthalene-
Z ¹ and Z ² are each independently a single bond, —CH ₂ CH ₂
-, - COO -, - OCO -, - C≡C -, - CH 2 O
Or a combination of two or more of these bridging groups, Y and X are, independently of one another, H or F, and one of X and Y is also Cl, and W is -CN or -NCS. However, when W is -CN, (1) the concentration of the compound of formula I in the system is less than 50% by weight; (2) either one of Y and X is F, or ( 3) Any ^one of Z ¹ and Z ² is —CH ₂ CH ₂ —, and R ¹ and R ² are each independently of one or two non-adjacent CH ₂ groups —O— or Alkyl having 1 to 12 C atoms, which can also be replaced by -CH = CH-, and m is 0, 1 or 2). Electro-optical liquid crystal system. 2. The system according to claim 1, wherein the liquid crystal mixture is embedded in an optically transparent medium in the form of bounded sections. 3. The system according to claim 1, wherein the liquid crystal mixture forms a coherent continuous phase in an optically transparent medium. 4. The system according to claim 2, wherein the system is a PDLC system. 5. The system according to claim 2, wherein the system is an NCAP system. 6. The PN system according to claim 3, wherein:
The system described in 1. 7. The liquid-crystal mixture of the formula Ia (Wherein, ring A ³ and ring A ⁴ are, independently of each other, 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4
-Phenylene or 3-fluoro-1,4-phenylene, and X ¹ is H or F, and the following number combinations 1 to 5 apply to n, Z ³ and Z ⁴ : number n Z ³ Z ⁴ 1 0 single bond _{- 2 0 -CH 2 CH 2 -} - 3 1 -CH 2 CH 2 - single bond 4 1 single bond -CH ₂ CH ₂ - 5 1 contain one or more compounds of a single bond single bond The system according to any one of claims 1 to 6, wherein 8. The compound of claim Ia wherein: Is Or The system of claim 7, wherein 9. The liquid crystal mixture comprises the following compound group: Wherein ring C is trans-1,4-cyclohexylene or 1,4-phenylene, and R ¹ has the meaning given in claim 1) and is based on a dielectric anisotropic In order to increase the property, (Wherein, Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and ring D is trans-1,4-cyclohexylene, 1,4-
Phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and o is 0 or 1, and R ¹ has the meaning given in claim 1). 8. The system according to claim 1, comprising 5 to 60% by weight of said compound. 10. The liquid crystal mixture of the formula Ib Wherein Q ² is Or And one of ring A ⁵ and ring A ⁶ is Where V ¹ is N or H, and the other, if present, is trans-1,4-cyclohexylene or 1,4-phenylene; and X ² and Y ² are independent of each other H is F or F, P is 0 or 1, and Z ⁵ and Z ⁶ are, independently of one another, a single bond or —CH ₂ CH ₂ —;
¹ a system according to any one of claims 1 to 7, characterized in that it contains one or more compounds of the meaning indicated in Claim 1. 11. The system according to claim 10, wherein at least one of X ² and Y ² is F. 12. The system according to claim 10, wherein X ² = Y ² = H. 13. The liquid crystal mixture of the formula Ic [Wherein Q ³ is Or Wherein one of ring A ⁷ or ring A ⁸ is (Where T ¹ is —CH ₂ — or —O—) and the other, if present, is trans-1,4-
Cyclohexylene or 1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4
-Phenylene, Z ⁷ and Z ⁸ are each independently a single bond, -COO-,
—OCO— or —CH ₂ CH ₂ —, r and q independently of one another are 0 or 1, X ³ is F or Cl, and Is 2-fluoro- or 2-chloro-1,4-phenylene or 3-fluoro- or 3-chloro-1,4-phenylene, and R ¹ has the meaning given in claim 1] The system according to any one of claims 1 to 7, comprising the above compound. 14. The liquid crystal mixture of the formula Id (Wherein ring A ⁹ is 1,4-phenylene or trans-1,4-
Ring A ¹⁰ is 1,4-phenylene, 2-fluoro-1,4-
Phenylene, 3-fluoro-1,4-phenylene or trans-1,4-cyclohexylene, wherein Z ⁹ is a single bond, —COO—, —OCO— or —CH ₂ C
H ₂ —, Z ¹⁰ is a single bond, —COO— or —CH ₂ CH ₂ —, and s is 0 or 1, and R ¹ is as defined in claim 1). The system according to any one of claims 1 to 7, comprising at least one compound. 15. The liquid crystal mixture of the formula IdE2-1 and IdE3-1 to IdE3-8. (In the formula, R ¹ has the meaning given in claim 1) System according to claim 14, characterized in that it contains one or more compounds selected from the group of compounds. 16. The liquid crystal mixture of the formulas Ie4-1 to Ie4-1.
4-4 (Wherein ring A ¹¹ is in each case independently of one another 1,4-
Phenylene, 2-fluoro-1,4-phenylene, 3-
Fluoro-1,4-phenylene or trans-1,4
-Cyclohexylene, wherein ring A ¹² is, independently of one another in each case, Or T is 0 or 1; and Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and R ¹ is
The system according to any of the preceding claims, characterized in that it comprises one or more tetracyclic compounds selected from the group of the carbononitriles of the meaning given in (1). 17. A compound of the formula If (Wherein at least one of ring A ¹³ and, if present, ring A ¹⁴ is 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, trans-
1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or 1,3-dioxane-2,5-diyl and the other, if present, trans-1,4. -Cyclohexylene, 1,4-
Phenylene, Z ¹¹ and Z ¹² are each independently of one another a single bond, —C≡C, —CH ₂ CH ₂ —, —COO—, —OC
O- or a combination of two or more of these bridge members; v is 0, 1 or 2; a is 0 or 1; Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; Is 3,5-difluoro-1,4-phenylene, and T ² is —Cl, —F, —CF ₃ , —OCF ₃ , —OC
A HF ₂ or NCS, and the system of R ¹ is according to any one of claims 1 to 7, characterized in that it contains one or more compounds of a is) meanings indicated in Claim 1 . 18. The system according to claim 17, wherein T ² is NCS. 19. The system according to claim 17, wherein T ² is —F, —CF ₃ , —OCF _3, or —OCHF ₂ . 20. The system according to claim 17, wherein T ² is Cl. 21. The system according to claim 20, wherein v is 1 or 2. 22. The liquid crystal mixture as claimed in claim 1, wherein the liquid crystal mixture further comprises a dielectrically positive compound A comprising Δε ≧ 2,
2. A method according to claim 1, further comprising a dielectrically neutral compound B comprising a compound of .ltoreq..DELTA..epsilon. + 2, and optionally a dielectrically negative component C of a compound of .DELTA..epsilon. <-2. A system according to any one of claims 7 to 13. 23. The liquid crystal mixture of the formula IgR ¹ -Q ⁴ -COO-Q ⁵ -R ² I
g wherein Q ⁴ and Q ⁵ are each independently of the other Or And one of Q ⁴ and Q ⁵ is Or And R ¹ and R ² , in each case independently of one another, have the meaning given in claim 1) comprising one or more compounds of the formulas ¹ to 7
The system according to any one of the preceding claims. 24. The liquid-crystal mixture of the formula IhR ¹ -Q ⁶ -C≡CQ ⁷ -R ² Ih wherein at least one of the radicals R ¹ and R ² has the meaning given in claim 1 And one of the two groups R ¹ and R ² is F, Cl, OCF ₃ , O
CHF ₂ or CF ₃ , and the radicals Q ⁶ or Q ⁷ are in each case independently of one another Or And Q ⁶ is Or And Q ⁷ is The system according to any one of claims 1 to 7, characterized in that it comprises one or more compounds of the formula: 25. The liquid crystal mixture of the formula Ii R ¹ -Q ⁸ -CH ₂ CH ₂ -Q ⁹ -R ² Ii wherein R ¹ and R ² are each independently of one another as defined in claim 1. And Q ⁸ and Q ⁹ are in each case independently of one another trans-1,4-cyclohexylene, 1,4-phenylene, 4,4′-biphenylyl,
4,4'-cyclohexylphenyl or 4,4'-phenylcyclohexyl (provided that 1,4
8. The system according to claim 1, wherein one of the 4-phenylene groups can be replaced by fluorine or chlorine). 26. The liquid crystal mixture according to any one of compounds II to IV T-W ¹ -Phe-CN II R-W ¹ -Cyc-CN III TV-Phe-CN IV (wherein R is Independently of one another, one or two non-adjacent CH ₂ groups can also be replaced by —O—, —CO— and / or —CH ＝ CH
An alkyl group having 5 C atoms, W ¹ is Phe. (F) -Y ¹ or Cyc-Y ^1, Y ¹ is a single bond, a -COO- or -OCO-, V is pyridine -2,5-diyl or pyrimidine-2,
T is R, R-Phe. (F) -Y ¹ or R-Cyc
Is -Y ^1, and Phe. (F) 1 to is selected from 1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene)
The system according to any one of claims 1 to 7, further comprising one or more compounds. 27. The system according to claim 1, wherein the liquid crystal mixture has a dielectric anisotropy of ΔΔ> 3. 28. The liquid crystal display device according to claim 1, wherein the liquid crystal mixture contains a polychromatic dye.
The system described in the paragraph. 29. The system according to claim 1, wherein the liquid crystal mixture contains a doping component. 30. A liquid crystal which is equivalent to the liquid crystal mixture according to claim 1 or 7.