GB2510066A - Liquid-crystalline medium - Google Patents

Abstract

A liquid-crystalline medium, characterised in that it contains one or more compounds of the formula IA, and at least one compound selected from the group of compounds of the formula IIA and IIB, in which RA, R2A, R2B, ring A, XA, Y1-6, L1-2, Z2', o, (0)CvH2v+1 and v have the meanings indicated in Claim 1, and to the use thereof for electro-optical purposes, in particular for shutter glasses, 3D applications, in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS and PS-VA-IPS displays.

Description

Liquid-crystalline medium The present invention relates to a liquid-crystalline medium (LC medium), to the use thereof for electro-optical purposes, and to LC displays containing this medium.

Liquid crystals are used principally as dielectrics in display devices, since the optical properties of such substances can be modified by an applied voltage. Electro-optical devices based on liquid crystals are extremely well known to the person skilled in the art and can be based on various effects. Examples of such devices are cells having dynamic scattering, DAP (deformation of aligned phases) cells, guest/host cells, TN cells having a twisted nematic structure, STN (supertwisted nematic) cells, SBE (super-birefringence effect) cells and OMI (optical mode interference) cells. The commonest display devices are based on the Schadt-Helfrich effect and have a twisted nematic structure.

The liquid-crystal materials must have good chemical and thermal stability and good stability to electric fields and electromagnetic radiation. Furthermore, the liquid-crystal materials should have low viscosity and produce short addressing times, low threshold voltages and high contrast in the cells.

They should furthermore have a suitable mesophase, for example a nematic or cholesteric mesophase for the above-mentioned cells, at the usual operating temperatures, i.e. in the broadest possible range above and below room temperature. Since liquid crystals are generally used as mixtures of a plurality of components, it is important that the components are readily miscible with one another. Further properties, such as the electri-cal conductivity, the dielectric anisotropy and the optical anisotropy, have to satisfy various requirements depending on the cell type and area of application. For example, materials for cells having a twisted nematic structure should have positive dielectric anisotropy and low electrical conductivity.

For example, for matrix liquid-crystal displays with integrated non-linear elements for switching individual pixels (MLC displays), media having large positive dielectric anisotropy, broad nematic phases, relativelylow birefringence, very high specific resistance, good UV and temperature stability and low vapour pressure are desired.

Matrix liquid-crystal displays of this type are known. Examples of non-linear elements which can be used to individuafly switch the individual pixels are active elements (i.e. transistors). The term ?active matrix is then used, where a distinction can be made between two types: 1. MOS (metal oxide semiconductor) or other diodes on silicon wafers as substrate.

2. Thin-film transistors FFTs) on a glass plate as substrate.

The use of single-crystal silicon as substrate material restricts the display size, since even modular assembly of various part-displays results in problems at the joints.

In the case of the more promising type 2, which is preferred, the electro-optical effect used is usually the TN effect. A distinction is made between two technologies: TFTs comprising compound semiconductors, such as, for example, CdSe, or TVFs based on polycrystalline or amorphous silicon. Intensive work is being carried out worldwide on the latter technology.

The TFT matrix is applied to the inside of one glass plate of the display, while the other glass plate carries the transparent counterelectrode on its inside. Compared with the size of the pixel electrode, the ITT is very small and has virtually no adverse effect on the image. This technology can also be extended to frilly colour-capable displays, in which a mosaic of red, green and blue filters is arranged in such a way that a filter element is opposite each switchable pixel.

The TFT displays usually operate as TN cells with crossed polarisers in transmission and are backlit.

The term MLC displays here encompasses any matrix display with integrated non-linear elements, i.e., besides the active matrix, also displays with passive elements, such as varistors or diodes (MTM = metal-insulator-metal).

MLC displays of this type are particularly suitable for TV applications (for example pocket televisions) or for high-information displays for computer applications (laptops) and in automobile or aircraft constmction. Besides problems regarding the angle dependence of the contrast and the response times, difficulties also arise in MLC displays due to insufficiently high specific resistance of the liquid-crystal mixtures [TOGASHI, S., SEKI- GUCHI, K., TANABE, H., YAMAIYIOTO, E., SORtMACHI, K., TAJIMA, E., WATA-NABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, pp. 14t ff, Paris; STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, pp. 145 if, Paris]. With decreasing resistance, the contrast of an MLC display deteriorates, and the problem of after-image elimination may occur. Since the specific resistance of the liqu d-crystal mixture generally drops over the life of an MLC display owing to interaction with the interior surfaces of the display, a high (initial) resistance is very important in order to obtain acceptable lifetimes. Tn particular in the case of low-volt mixtures, it was hitherto impossible to achieve very high specific resistance values. It is further more important that the specific resistance exhibits the smallest possible increase with increasing temperature and after heating and/or UV exposure. The low-temperature properties of the mixtures from the prior art are also particularly disadvantageous. It is demanded that no crystallisation and/or smectic phases occur, even at low temperatures, and the temperature dependence of the viscosity is as low as possible. The MLC displays from the prior art thus do not satisfy today's requirements.

Besides liquid-crystal displays which use baclclighting, i.e. are operated transmissively and if desired transfiectively, reflective liquid-crystal displays are also particularly interesting. These reflective liquid-crystal displays use the ambient light for information display. They thus consume significantly less energy than backlit liquid-crystal displays having a corresponding size and resolution. Since the TN effect is characterised by very good contrast, reflective displays of this type can even be read well in bright ambient conditions. This is already known of simple reflective TN disp'ays, as used, for examp'e, in watches and pocket cathulators. However, the princip'e can also be applied to high-quality, higher-resolution active matrix-addressed disp'ays, such as, for example, Fri displays. Here, as ab'eady in the transmissive 1FF-TN displays which are generally conventional, the use of liquid crystals of low birefringence (An) is necessary in order to achieve low optical retardation (d -An). This low optical retardation results in usually acceptable low viewing-angle dependence of the contrast (cf. DE 30 22 818). Tn reflective displays, the use of liquid crystals of low birefringence is even more important than in transmissive displays since the effective byer thickness through which the light passes is approximately twice as large in reflective displays as in transmissive displays having the same layer thickness.

in order to achieve 3D effects by means of shutter glasses, fast-switching mixtures having low rotational viscosities and correspondingly high optical anisotropy (An), in particular, are employed. Electro-optical lens systems, by means of which a 2-dimensional representation of a display can be switched to a 3-dimensional autostereoscopic representation, can be achieved using mixtures having high optical anisotropy (An).

Thus, there continues to be a great demand for MLC displays having very high specific resistance at the same time as a large working-temperature range, short response times, even at low temperatures, and a low threshold voltage which do not exhibit these disadvantages or only do so to a lesser extent.

in the case of TN (Schadt-Helfrich) cells, media are desired which facilitate the following advantages in the cells: -extended nematic phase range (in particular down to low temperatures) -switchabiBty at extremely thw temperatures (outdoor use, automobiles, avionics) -increased resistance to UV radiation (longer life) -low threshold voltage -high transmittance.

The media available from the prior art do not enable these advantages to be achieved while simultaneously retaining the other parameters.

in the case of supertwisted (STN) cells, media are desired which facilitate greater multiplexability and/or lower threshold voltages and/or broader nematic phase ranges (in particular at low temperatures). To this end, a further widening of the available parameter latitude (clearing point, smectic-nematic transition or melting point, viscosity, dielectric parameters, elastic parameters) is urgently desired.

in particular in the case of LC displays for TV and video applications (for example LCD-TVs, monitors, PDAs, notebooks, games consoles), a significant reduction in the response times is desired. This requires LC mixtures having low rotational viscosities and high dielectric anisotropies. At the same time, the LC media should have high dearing points, preferably »= 70°C.

The invention has the object of providing media, in particular for MLC, FFS, IPS, TN, positive VA or STh displays of this type, which do not exhibit the disadvantages indicated above or only do so to a lesser extent and preferably have fast response times and low rotational viscosities at the same time as a high clearing point, as well as high dielectric anisotropy and a low threshold voltage and a high transmittance.

Nowadays, fringe-field switching (FFS) mode is especially interesting for the small and medium size displays for the use in tablet and smart phone displays. The reason why the FFS mode is widely adapted for smart and medium size displays is the wide viewing angle, the high transmittance the low operating characteristics compared to the well-known modes of the prior art. LC mixtures of the prior art are characterized in that they consist of compounds with positive dielectric anisotropy and optionally of neutral compounds.

It has now been found that the LC mixtures having positive dielectric anisotropy (+Ae) can be improved if the LC media additionally contain one or more compounds selected from the compounds of the formula IJA, JIB and tIC having negative values for the dielectric anisotropy (-AE). The mixtures according to the invention have a very high light efficiency, show very high transmittance, low values for the rotational viscosity y1 and thus are suitable for all kind of applications in theTh, TPS, FFS and VA modes, especially in the FFS mode.

The compounds of the formulae TA in combination with at least one compound selected from the group of compounds of the formula HA, IIB and I1C result in LC mixtures having the desired properties indicated above.

The invention relates to a liquid-crystalline medium having a positive dielectric anisotropy, characterised in that it contains one or more compounds of the formula IA RACF2O *XA IA and at least one compound selected from the group of compounds of the formula TIA, JIB and ITC, I 2 R2AZ2(O)CH21 hA 2 I

ITB

6 54 3 R2C(O)CVH2V+l lic, in which RA, RZ4, R211 and R2c each, independenfly of one another, denote H, an alkyl or alkenyl radical having lip to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals maybe replaced by-O-, -S-, , -CC-, -CF2O-, -OCF2-, -OC-O-or -0-CO-in such a way that 0 atoms are not linked directly to one another, denotes -@ -Q--Q--Cj c ]jdenotes -®--Q--Q--C) Q Oor X' denotes F, Cl, CN, SF5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having lip to 6 C atoms, yi-O each, independently of one another, denote H or F, I) and L2 each, independently of one another, denote F, Cl, CF3 or CHF2, L3-6 each, independently of one another, denote H, F, Cl, CF3 or CHF2, but at least two of L3-6 denote F, Cl, CF3 or CHF2 Z2 and Z2' each, independently of one another, denote a single bond, -CH2CH2-, -CH=CH-, -CC-, -CF2O-, -OCF2-, -CH2O-, -OCHr, C00, OCO, C2F4, -CF=CF-, -CH=CHCH2O-, p denotes 1 or 2, and, in the case where Z2 = single bond, p may also denote o and q each, independently of one another, denote o or 1, (O)CH2+1 denotes OCH2+1 or CH2+1, and v denotes 1 to 6.

Surprisingly, it has been found that mixtures containing the compounds of the formulae IA and at least one compound of the formula tIA, I1B or IIC have high dielectric anisotropy & and at the same time have an advantageous rotational viscosity yi/clearing point ratio. They are therefore particularly suitable for achieving liquid-crystal mixtures having lowy1, high transmittance and a relatively high clearing point. tn addition, the compounds of the formulae 1A, HA, JIB and JIC exhibit good solubility in LC media. LC media according to the invention comprising compounds of the formulae IA and at least one compound of the formula IIA, IJB and/or JIC have a low rotational viscosity, fast response times, a high clearing point, very high positive dielectric anisotropy, relatively high birefringence and a broad nematic phase range and a high transmittance. They are therefore particularly suitab'e for mobile telephones, T\T and video applications, most preferably for smart phones and tablet PC.

The compounds of the formulae IA, HA, JIB and IIC have a broad range of applications.

Depending on the choice of substituents, they can serve as base materials of which liquid-crystalline media are predominantly composed; however, liquid-crystalline base materials from other classes of compound can also be added to the compounds of the formulae 1A and JIA, JIB, IJC in order, for example, to modi' the dielectric and/or optical anisotropy of a dielectric of this type and/or to optimise its transmittance, threshold voltage and/or its viscosity.

In the pure state, the compounds of the formulae IA, hA, IJB and IIC are colourless and form liquid-crystalline mesophases in a temperature range which is favourably located for electro-optical use. They are stable chemically, thermafly and to light.

The compounds of the formulae IA, hA, JIB and IIC are prepared by methods known per se, as described in the literature (for example in the standard works, such as 1-louben- Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), to be precise under reaction conditions which are known and suitable for the said reactions. Use can also be made here of variants known per se, which are not mentioned here in greater detail.

The compounds of the formulae IA, hA, JIB and IIC are known, for example, from WO 2004/048501 A, EP 0 786 445, EP 0 364 538, US 5,273,680.

if RA, R2A,R2B and R2C in the formulae above and below denote an alkyl radical and/or an alkoxy radical, this maybe straight-chain or branched. It is preferably straight-chain, has 2,3,4,5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy. RA and RB each preferably denote straight-chain alkyl having 2-6 C atoms.

Oxaalkyl preferably denotes straight-chain 2-oxapropyl (= methoxymethyfl, 2- (= ethoxymethyl) or 3-oxablityl (= 2-methoxyethyl), 2-, 3-or 4-oxapentyl, 2-, 3-, 4-or -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, 2-, 3-, 4-, 5-, 6-, 7-, 8-or 9-oxadecyl.

if RA, R2A,R2B and R2C denote an alkyl radical in which one CH2 group has been replaced by -CH=CH-, this may be straight-chain or branched. It is preferably straight-chain and has 2 to 10 C atoms. Accordingly, it denotes, in particular, vinyl, prop-i-or -2-enyl, but- 1-, -2-or -3-enyl, pent-i-, -2-, -3-or -4-enyl, hex-i-, -2-, -3-, -4-or --enyl, hept-i-, -2-, -3-, -4-, -5-or -6-enyl, oct-i-, -2-, -3-, -4-, -5-, -6-or -7-enyl, non-i-, -2-, -3-, -4-, -5-, -6-, -7-or -8-enyl, dec-i-, -2-, -3-, -4-, -5-, -6-, -v-, -8-or -9-enyl.

TfRA, R2A,R2B and R2C denote an alkyl or alkenyl radical which is at least monosubstituted by halogen, this radical is preferably straight-chain, and halogen is preferably F or Cl. In the case of polysubstitution, halogen is preferably F. The resultant radicals also include perfluorinated radicals. In the case of monosubstitution, the fluorine or chlorine substituent may be in any desired position, but is preferably in the o-position.

in the formulae above and below, XA is preferably F, Cl or a mono-or polyfluorinated alkyl or alkoxy radical having 1, 2 or 3 C atoms or a mono-or polyfluorinated alkenyl radical having 2 or 3 C atoms. X" is particularly preferably F, Cl, CF3, CHF2. OCF3, OCHF2, OCFHCF3, OCFHCHF2, OCFHCHF2, OCF2CH3, OCF2CHF2, OCF2CHF2, OCF2CF2CI-1F2, OCF2CF2CI-1F2, OCFI-ICF2CF3, OCFHCF2CHF2, OCF2CF2CF3, OCF2CF2CC1F2, OCC1FCF2CF3, OCH=CF2 or CH=CF2, very particularly preferably F or OCF3, furthermore CF3, OCF=CF2, OCHF2 or OCH=CF2.

Particular preference is given to compounds of the formulae TA in which X' denotes F or OCF1, preferably F. Preferred compounds of the formula TA are those in which Y' denotes F, those in which Y2 denotes F, those in which Y3 denotes H, those in which Y4 denotes H andY denotes F, and those in which Y andY each denote H. Preferred compounds of the formula TA are selected from the following sub-formulae: -10 -Y7 Y5 Yl L&-i 8 6 o CF2O 0 XA

Y Y Y Y

RA C FO XA L&-2 RA C F0 XA L&-3 Y5 Yl

A

R H 0 0 CF20-\f---X Y6 Y2 Y5 Y3 Yl A A IA-5 R -\ -ç0-CF2O Y6 Y2 in which Ri', X1\ and -have the above indicated meanings and Y7 and 8 each, independently denote H or F. -11 -Particulañy preferred compounds of the formu'a TA are selected from the following formulae: TA-ia IA-ib RASCF2OXA TA-ic RACF2OXA RASCF2OXA TA-ic TAif -12-RASCF2O4XA -2a

F

RACF2OXA 2b

F F

RASCF2OXA IA-2c RACF2OXA -2d

F

RAScF2oXA TA-2e RACF2OXA -2f

F

-13 -RACF2OXA -2g RACF2OXA -2h

F

RACF2OXA -2i

F F

F20 XA IA-3a

F

RA 4 XA TA-3b

F F

R C F20 XA -3C -14-RA C F20 XA a-3d

F

RA c 2o xA -3e RA C FO XA TA-3f

F

RA C F20 XA TA-3g RA c o xA -3h

F

RA C F20 XA 3i

F F

-15 -RA____K-__(__CF2O ____XA JA-4a TA-4b IA-4c 5XA JA-4d RACF2O XA TA-5a RACF2O 4XA -5b -i6 -RACF2O XA -5c RACF2O*XA -5d RAcF2o 4XA TA-5e in which RA and XA have the meanings indicated in Claim 1. W preferably denotes straight-chain aky1 having ito 6 C atoms, in particular ethyl, propyl and pentyl, furthermore butyl and akeny1 having 2 to 6 C atoms. X' preferably denotes F, OCF3, OCHFCF3, OCF2CHFCF3, OCH=CF2, most preferably F or OCF7.

Very paiticular preference is given to the compound of the sub-formula IA-ib, IA-2i, JA- 3b and IA-5e.

Tn the compounds of the formu'ae TTA and JIB, Z2 may have identical or different meanings. Tn the compounds of the formula JIB, Z2 and Z2 may have identical or different meanings.

in the compounds of the formulae JIA, JIB and J1C, Rk, R2B and R2C each preferaNy denote aky having 1-6 C atoms, in particular CH3, C2H5, n-C3H7, n-C4H9, n-C5H11. -17-

In the compounds of the formulae TTA, TTB and TIC, U, L2, L3, L4, U and L6 preferably denote Lt = L2 = F and U = L6 = F and U=L4=T-I, furthermore L' = F and L2 = Cl or L1 = Cl and U = F, U = L4= F and L6 = F and L5 = I-I. Za and Z2 in the formulae TIA and ITB preferably each, independently of one another, denote a single bond, furthermore a -CH2O-or -C2H4-bridge.

if in the formula IIB Z2 = -C2H4-, -CH2O-, -COO-or -CH=CH-, Z2 is preferably a sing'e bond or, if Z2 = -C2H4-, -CH2O-, -COO-or -CH=CH-, Z2 is preferably a single bond. in the compounds of the formulae TTA and TIB, (O)CvH2;+i preferably denotes OCH2+1, furthermore CvH2+1. In the compounds of the formula TIC, (O)CH2±1 preferably denotes H2±1. In the compounds of the formula IIC, U and L4 preferably each denote F. Preferred compounds of the formulae TIA, IIB and IIC are indicated below: aIkyIaIkyI* HA-i aIkyIOaIkyI* aIkyIaIkyI* aIkyIOaIkyI* -i8 -aIkyIaIkyI* I-5 aIkyIOaIkyI* I-6 aIkyI____9____aIkyI* ITA-7 ITA-8 TTA-9 aIkyIOaIkyI* TTA-io hA-n -19 -aIkyIOaIkyI* I-12

F F

aIkyIC2H4aIkyI* TTA-13

F F

aIkyIC2H4OaIkyI* I14 aIkyIC2H4aIkyI* I15 aIkyIC2H4CaIkyI* 1i6

F CI

aIkyIC2H4aIkyI* 117

F CI

aIkyIC2H4OaIkyI* 118 -20 -

F F 9

F F

ITA-20 aIkyICF2(O)aIkyI* TTA-21

F F

aIkyIOCF2(O)aIkyI* TTA-22

F F

aIkyICH=CHCH2(O)aIkyI* I23 alkyl ( (H) CF2O(O)aIkyI* I-24 alkyl ( 0) CF2O(O)aIkyI* TTA-25 aIkyICH2O (O)aIkyI* I-26 aIkyIOCH2(O)aIkyI* TTA-27

F F

TTA-28

F F

HA-29 aIkenyIaIkyI* TTA-3o aIkenyIOaIkyI* I-31 aIkenyIaIkyI* TTA-32 -22 -aIkenyIOaIkyI* 133 TTA-34 aIkenyIOaIkyI* TTA-35 ITA-36 aIkenyIOaIkyI* TTA-37 TTA-38 aIkenyIQaIkyI* I-39 -23 -aIkenyIC2H4aIkyI* I4o aIkenyIC2H4OaIkyI* 141

F F

aIkyICH=CH(O)aIkyI* 142

F F

aIkyICO(O)aIkyI* 143 aIkyIaIkyI* TTA-44 aIkyIOaIkyI* TTA-45 aIkyIaIkyI* I-46 aIkyIOaIkyI* I-47 aIkyIaIkyI* I-48 aIkyIOaIkyI* 149 aIkyIaIkyI* I5o aIkyIOaIkyI* TTA-51

F F

alkyl 0 alkyl* TTA-52

F F

alkyl 0 OaIkyI* IIA-53 -25 -aIkyIaIkyI* I-54 aIkyIOaIkyI* I-55 11A56 aIkyIOaIkyI* I-57 ITA-58 aIkyIOaIkyI* 159 aIkyIaIkyI* I-6o aIkyIOaIkyI* I-6i JIA-62 JIA-63

F F

aIkyIOOaIkyI* J-64

F F J-65

JIB-i JIB-2 IIB-3 HB-4

F CI HB-5

F CI

IIB-6

F F

TTB-7

F F

TTB-8

F F HB-9

F F

HB-io

F F

JIB-il

F F

JIB-12 aIkyIOaIkyI* JIB-13

F CI

TTB-14 aIkenyIaIkyI* TTB-15 aIkenyIOaIkyI* IIB-i6 I1C-i TTC-2 aIkyI* IIC-3 o-alkyr 11C4 IIC-5 11C6 in which alkyl and alkyP< each, independently of one another, denote a straight-chain alkyl radica' having 1-6 C atoms and alkeny denotes a straight-chain alkenyl radical having 2-6 C atoms, in particifiar CH2=CH, CH2=CHCH2, CH2=CHC2H4, CH3CHCH, CH3CH=CHCH2 and CH3CH=CHC2H4.

Particulañy preferred mixtures according to the invention contain one or more compounds of the formulae TTA-2, TTA-8, TTA-14, TIA-26, TIA-29, TTA-35, TTA-45, TIA-57, ITB-2, TTB-n, TTB-i6 and TIC-i.

The proportion of compounds of the formulae TIA, ltB and/or TiC in the mixture as a whole is preferably 3-40 %, preferably 5-30 % by weight, most preferably 3-20 %, by weight.

Particularly preferred media according to the invention contain at least one compound of the formula IIC-i, aIkyI__Ø______Ø__aIkyI*, in which akyl and alkyl* have the meanings indicated above, preferably in amounts of »= 3 % by weight, in particular »= 5 % by weight and particularly preferaNy 5-15 % by weight.

Preferred mixtures contain one or more compounds of the formula TIA-64 and/or IIA-65: C2H5OOC3H7 I-64a C2H5OOC4H9 I-64b C2H5OOC5H11 I-64C C2H5OOC6H13 164d C3H7OOC3H7 1-64e C3H7OOC4H9 I-64f C3H7OOC5H11 164g C3H7OOC6H13 1-64h C4H9OOC4H9 ITA-641 C4H9OOC5H11 C4H9OOC6H13 I-64k C5H11 OOC5H11 ITA-641 C5H11 OOC6H13 ITA-64m C6H13OOC6H13 I-64n C3H7OOCH2CH=CH2 ITA65a C4H9OOCH2CH=CH2 ITA-65b -33 -C5H11OOCH2CH=CH2 165c C5H13OOCH2CH=CH2 165d C3H7OOCH2CH=CHCH3 ITA65e C4H9OOCH2CH=CHCH3 16f C5H11OOCH2CH=CHCH3 165g C5H13OOCH2CH=CHCH3 165h C3H7OOCH2CH=CHC2H5 165i C4H9OOCH2CH=CHC2H5 -C5H11OOCH2CH=CHC2H5 I65k C6H13OOCH2CH=CHC2H5 1TA651.

Preferred mixtures contain at least one compound of the formula IIA-64a to IJA-64n.

Preferred mixtures contain at least one or more tolan compound(s) of the formula JIB-Ti and TIB-T2,

F F

JIB-Ti R23 0 ___ 0 (0)CH2÷1

F F

IJB-T2.

R2B (H_ (o) ç0(0)cH2+1 The mixtures according to the invention additionally can contain at least one compound of the formula To-i -35 -R1 (o) (o) OR2 To-i in which R' has the meaning for R' and R2 has the meaning of (O)CH2+1. R' preferably denotes straight-chain alkyl having i-6 C atoms. R2 preferably denotes alkoxy having 1-5 C atoms, in particular 0C2H5, 0C3H7, 0C4H9, 0C5H11, furthermore OCH3.

The compounds of the formulae TTB-Ti and TIB-T2 are preferably employed in concentrations of 3 -25 % by weight, in particifiar 5 -is % by weight based on the total mixture.

Further preferred embodiments of the mixture according to the invention are indicated below: -The medium additionally contains one or more compounds of the formfflae Ill and/or IV, ROCF2OXO 111 R° Y Y2 in which R0 denotes a halogenated or unsubstituted akyl or alkoxy radica' having ito 15 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by -CC-, -CF2O-, -0-, , -<)()-, -CH=CH-, -C0-0-or -0-CO-in such a way that 0 atoms are not linked directly to one another, X denotes F, Cl, CN, SF5, SCN, NCS, a halogenated akyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical having up to 6 C atoms, each, independently of one another, denote H or F, and each, independently of one another, denote or -The compounds of the formula til are preferably selected from the following formulae: ROCF2OXO TITa ROCF2OXO Tub RObCF2O4XO Ilic ROCF2OXO TiTd Tile R°bCF2OX° TITf in which R° and X° have the meanings indicated above.

R0 preferably denotes alkyl having 1 to 6 C atoms. X° preferably denotes F. Particular preference is given to compounds of the formulae lila and iITb, in particular compounds of the formu'ae ITTa and TTib in which X denotes F. -The compounds of the formula IV are preferably selected from the following formulae: R°CF2O 4X0 Wa ROCF2O4XO IVb R°CF2OX° R°CF2OX° IVd C FO 4 lYe in which R° and X' have the meanings indicated above.

R° preferably denotes alkyl having 1 to 6 C atoms. X° preferably denotes F, OCF3 or CF3.

Particular preference is given to compounds of the formulae Wa and lye, in particular compounds of the formula IVa; -The medium additionally contains one or more compounds selected from the following formulae: R° R° z°---x° vi R° Z0* X° R° -(--.---Z0____ VIII x° in which R° denotes a halogenated or unsubstituted aWyl or alkoxy radica' having ito 15 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by - -40 -CC-, -CF2O-, -0-, -0-, ----, -CH=CH-, -CO-O-or -0-CO-in such a way that 0 atoms are not linked directly to one another, X denotes F, Cl, CN, SF5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radica', a halogenated alkoxy radical or a halogenated alkenyloxy radical having lip to 6 C atoms.

y-4 each, independently of one another, denote H or F, Z° denotes -C2H4-, -(CH2)4-, -CH=CH-, -CF=CF-, -C2F4-, -CH2CF2-, -CF2CH2-, -CH2O-, -OCT-I2-, -COO-or -OCF2, and in formula VT and VII additionally a single bond and in formifia VT and TX additionally -CF2O-, r denotes o or 1, and s denotes o or i; -The compounds of the formula V are preferab'y selected from the following formulae: F Va -(---(--(5- -4'-R° _( fDs_oh x° Vc R° x° Vd in which R° and X° have the meanings indicated above.

R° preferably denotes alkyl having ito 6 C atoms. X° preferably denotes F, CF3 or OCF3, furthermore UCF=CF2, OCH=CF2 or C; -The compounds of the formula VJ are preferably selected from the following formulae: VTa VTb VIc VId -42 -VIe R° _( I-o__{o--F VIf VTg ROCO x° Vlh in which Re and Xe have the meanings indicated above.

R° preferably denotes alkyl having 1 to 6 C atoms. Xo preferably denotes F, CF3 or OCF3, furthermore OCHF2, CF3, OCF=CF2 and OCH=CF2; -The compounds of the formula VII are preferably selected from the following formulae: VITa -43 -VITh VIIc Vild in which R° and X have the meanings indicated above.

R° preferably denotes a1ky having 1 to 6 C atoms. X preferably denotes F, furthermore OCF3, CF3, CF=CF2, OCF=CF2, OCHF2 and OCH=CF2; -The compounds of the formula VIII are preferably selected from the following formulae: R° -44 -R° Vilib R° CH2CH2 X° VUK in which R° and X have the meanings indicated above.

R° preferably denotes alkyl having 1 to 6 C atoms. X° preferably denotes F, furthermore OCF3, OCI-1F2 and OCH=CF2.

-The medium additionally contains one or more compounds selected from the following formulae: x

XII

L

XIII

alkenyl H I-I 0 -45 -in which X has the meanings indicated above, and L denotes H or F, "alkyl' denotes C,6-a1ky, R' denotes C1o-a1ky, C16-alkoxy or C2.-i-a1keny1, and "alkenyl" and "a1keny1" each, independently of one another, denote C25-alkenyl.

-The compounds of the formulae X-XIII are preferably selected from the following formulae: aIkyI____r__(O)aIkyI* Xa xb Xc xd Xe -46 -XIa XTTa F XllIa in which "alkyl" and alkyl* has the meaning indicated above and (O)alkyl denotes alkyl or 0-alkyl (=alkoxy).

Particular preference is given to the compounds of the formulae Xa, Xb, Xc, XIa, XIb, XIIa and XITTa. Tn the formulae X and XI, "alkyl" preferably, independently of one another, denotes n-C3H7, n-C4H9 or n-C5H,1, in particular n-C3H7.

-The medium additionally contains one or more compounds selected from the following formulae: xv in which L1 and L2 have the meanings indicated above, and R1 and R2 each, independenUy of one another, denote n-alkyl, alkoxy, oxaaficyl, fluoroalkyl or alkenyl, each having tip to 6 C atoms, and preferably each, independently of one another, denote alkyl having ito 6 C atoms; in the compounds of the formula XIV, at east one of the radicals R' and R2 preferably denotes akenyl having 2 to 6 C atoms or R' and R2 each independently denote akyl.

-The medium contains one or more compounds of the formula XTV in which at least one of the radicals R' and R2 denotes alkenyl having 2 to 6 C atoms.

Preferred compounds of the formifia XIV are compounds of the following formulae: XIVa al kyl XWb aIkyI__KT__KJ__\ XWc XIVd -48 -aIkyI_®___aIkyI* XIVe in which "alkyl" and "alkyl" has the meaning indicated above; especially preferred are the compounds of the formula XWd and XWe.

-The medium contains one or more compounds of the following formula ROCF2O4XO in which R° has the meanings ofW, X° has the meanings ofX' andYl andY2 each, independently denote H or F, and each, independently of one another, or -The compounds of the formula XVI are preferably selected from the following formulae: R o0* C F20 4 XVIa -49 -C F20 4 o XVIb RO C F20 4 XVIc RO c F20 4 0 C FO 4 XVTe C F20 4 xo in which R° and X have the meanings indicated above.

R° preferably denotes alkyl having 1 to 6 C atoms. X preferably denotes F, furthermore OCF3. Particularly preferred compounds of the formulae XVI are those in which Y' denotes F and y2 denotes H or F, preferably F. The mixture according to the invention particularly preferably contains at least one compound of the formula XVIII -50 - -The medium contains one or more compounds of the formula XVII,

XVII

in which R1 and R2 have the meanings indicated above. L is H or F, preferaNy F. Preferably R1 and R2 each, independenfly of one another, denote alkyl having 1 to 6 C atoms or in the case that L=F R' denotes alkyl and R2 denotes alkenyl or R' denotes alkenyl and R2 denotes alkyl.

Particularly preferred compounds of the formula XVII are those of the sub-formulae alkyl alkyl* X\TIIa alkyl ___< 3____ alkyl* TIT-b

F

XVIT-c alkyl 0 0 0 alkenyl alkenyl alkyl XVII-d alkenyl alkenylt XVII-e alkenyl alkenyl* in which alkyl and alkyt< each, independently of one another, denote a straight-chain alkyl radical having i-6 C atoms, in particular ethyl, propyl and pentyl, alkenyl and a1kenyP each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms, in particu'ar CH2=CHC2H4, CH3CH=CHC2H4, CH2=CH and CH3CH=CH.

Particular preference is given to the compounds of the formulae XVTT-b and XVTT-c. very particular preference is given to the compounds of the formulae C2H5 -<j9__/j j__ O')_ C4H9 -52 -C2H5 -(j--K5--('7'J_-C3H7 C H3 C2H5 C31H7 CH3 -@-4-@-\ C2H5 C3H7 -The medium contains one or more compounds of the following formu'ae: R1 R2 XVIIIa R1 R2 XVIIIb in which RI and R2 have the meanings indicated above and preferably each, independently of one another, denote alkyl having ito 6 C atoms. L denotes H or F; -The medium additionally contains one or more compounds selected from the following formu'ae: 0 x° XIX C2 X° R° xo XX' xo XXII R° 02 H4 X° XXIIT R° xo XXIV in which R° and X° each, independently of one another, have one of the meanings indicated above, and 1-4 each, independently of one another, denote H or F. X° is preferably F, Cl, CF3, OCF3 or OCHF2. R° preferably denotes akyl, alkoxy, oxaalky, fluoroalkyl or alkenyl, each having up to 6 C atoms. -55 -

The mixture according to the invention particularly preferably contains one or more compounds of the formuth XXTV-a, R° -KII---KII---KIS--KII F XXW-a in which R° has the meanings indicated above. R0 preferably denotes straight-chain akyl, in particular ethy', n-propyl, n-butyl and n-pentyl and very particularly preferably n-propyl.

The compound(s) of the formula XXIV, in particular of the formula XXIV-a, is (are) preferably employed in the mixtures according to the invention in amounts of 0.5-20 % by weight, particularly preferably 1-15 % by weight.

-The medium additionally contains one or more compounds of the formula XXV,

XXV

in which R°, X° and Y-6 have the meanings indicated above, s denotes 0 or 1, and __/i" denotes __KIE::::._ or Tn the formula XXV, X may also denote an alky radical having 1-6 C atoms or an akoxy radical having 1-6 C atoms. The alkyl or akoxy radica' is preferably straight-chain; R° preferably denotes alkyl having 1 to 6 C atoms. X° preferaNy denotes F; -The compounds of the formula XXV are preferably selected from the following formulae: XXVa X XXVc

RD

x° XXI Ye X XXI\Tg Xxvii in which R°, X° and Y' have the meanings indicated above. R° preferably denotes aWyl having 1 to 6 C atoms. X° preferaNy denotes F, and Y' is preferably F; Y1 F F -is preferably

F

OCF3, OCF3,OCF3, CF3, OCF=CF2,OCF=CF2 OCF=CF2, CF3, CF3, OCHF2,OCHF2, OCHF2, CI, CI or CI.

-R° is straight-chain alkyl or alkenyl having 2 to 6 C atoms; -The medium contains one or more compounds of the following formulae: R1 X° XXVI R1 X° XXVII in which Ri and X' have the meanings indicated above. R' preferably denotes alkyl having ito 6 C atoms. X preferably denotes F or Cl. In the formula XXVT, X very particularly preferably denotes Cl.

-The medium contains one or more compounds of the following formulae: X° x° XXIX -(J xxix C F2 X° in which R° and X° have the meanings indicated above. R° preferably denotes alkyl having 1 to 6 C atoms. X° preferaNy denotes F. The medium according to the invention particularly preferably contains one or more compounds of the formula XXX in which X° preferably denotes F. The compound(s) of the formulae XXVIII to XXX is (are) preferably employed in the mixtures according to the invention in amounts of 1-20 % by weight, particularly preferably 1-15 % by weight. Particularly preferred mixtures comprise at least one compound of the formula XXX.

-The medium contains one or more compounds of the following pyrimidine or pyridine compounds of the formulae R° KIIN>GKI X° M-1 -6o-R° M-2 FF M-3 in which R° andXo have the meanings indicated above. R° preferably denotes alkyl having ito 6 C atoms. X° preferably denotes F. The medium according to the invention particularly preferably contains one or more compounds of the formua M-i, in which X preferably denotes F. The compound(s) of the formulae NI-i to M-3 is (are) preferaNy employed in the mixtures according to the invention in amounts of i-20 % by weight, particularly preferably 1-15 % by weight.

Further particular preferred embodiments are indicated below: -The medium contains two or more compounds of the formula IA, in particular of the formula IA-ib; -The medium contains 2-50 % by weight, preferably 3-40 % by weight, particularly preferably 5-15 % by weight, of compounds of the formula IA; -The medium contains 3-4° % byweight, particularly preferably 5-15 % by weight, of at least one compound of the formula TV; -The medium contains 5-30 % by weight, particularly preferably 5-25 % by weight, of compounds of the formulae Vii; -6i- -The medium contains 20-70 % by weight, particulady preferably 25-65 % by weight, of compounds of the formulae X-XW; -The medium contains 3-40 % by weight, particularly preferably 5-30 % by weight, of compounds of the formula XVI1; -The medium contains 1-20 % by weight, particularly preferably 2-15 % by weight, of compounds of the formula XVI1I; -The medium contains at least two compounds of the formulae F20 F lA-b-i IA-b-2 C5H1 F20 F lA-b-3.

-The medium contains at least two compounds of the formulae

F F

C2H5 0 0 CF2O 0 F lB-c-i

F F

F F

C3H7 0 0 CF2O 0 F IB-c-2

F F

F F

0 0 CF2O 0 F IB-c-3.

F F

-The medium contains at least two compounds of the formula IA and at least two compounds of the formula JIB; -The medium contains at least one compound of the formula IA and at east one compound of the form&a JIB and at least one compound of the formula JIC; -The medium contains at least two compounds of the formula IA and at least two compounds of the formu'a JIB and at least one compound of the formula Wa; -The medium contains »= 20 % by weight, preferably »= 25 %, especially preferred »= 30 %, by weight, of one or more compounds of the formula IA and one or more compounds of the formula JIB; -The medium contains »= 20 % by weight, preferably »= 25 %, especially preferred »= 30 %, by weight, of one or more compounds of the formula IA and one or more compounds of the formula JIB; -The medium contains »= 20 % by weight, preferably »= 24 % by weight, preferably 25-60 % by weight, of compounds of the formula Xb, in particular the compound of the formula Xb-i, Xb-i.

-63 - -The medium contains at least one compound of the formula XIb-i and at least one compound of the formula Xc-i, Xe-i.

-The medium contains at kast one compound of the formu'a DPCU-n-F; -The medium contains at east one compound of the formifia CDUQU-n-F; -The medium contains at kast one compound of the formu'a PUQU-n-F; -The medium contains at least one compound of the formula APUQILJ-n-F and at least on compound of the formuh PGUQU-n-F and at least one compound of the formula DPGU-n-F; -The medium contains at least one compound of the formula PPGU-n-F.

-The medium contains at least one compound of the formula PGP-n-m, preferably two or three compounds.

-The medium contains at least one compound of PGP-n-2V having the following formu'a CH21 wherein n is 1-6, preferably 2, 3, 4 or 5.

-The medium contains at kast one compound of the formu'a PYP-n-m, preferably in amounts of 1-20 wt% based on the total mixture. -64 -

-The medium contains afleast one compound of the formula TTA, JIB and JJC; -The medium contains afleast one compound of the formula PY-n-Om, preferably in amounts of 1-20 wt.% based on the total mixture; -The medium contains at least one compound of the formula CY-n-Om; preferably in amounts of 1-20 wt% based on the total mixture; -The medium contains at least one compound of the formula Y-nO-Om, preferably in amounts of 1-20 wt.% based on the total mixture; -The medium contains at least one compound of the formula PYP-n-m, preferably in amounts of 1-20 wt.% based on the total mixture; It has been found that »= 20 % by weight, preferably »= 25 % by weight, of compounds of the formulae IA mixed with conventional liquid-crystal materials, but in particular with one or more compounds of the formulae JIT to XXXJ, results in a significant increase in the light stability and in low birefringence va'ues, with broad nematic phases with low smectic-nematic transition temperatures being observed at the same time, improving the shelf life. At the same time, the mixtures exhibit relatively low threshold voltages, very good values for the VHR on exposure to IJV, and very high clearing points.

The term "alkyl" or "alkyP" in this application encompasses straight-chain and branched alkyl groups having i-6 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl and hexyl. Groups having 2-5 carbon atoms are generally preferred.

The term "alkenyl" or "alkenyP<" encompasses straight-chain and branched alkenyl groups having 2-6 carbon atoms, in particular the straight-chain groups. Preferred akenyl groups are C2-C7-1E-alkenyl, C4-C6-3E-alkenyl, in particular C2-C-iE-alkenyL Examples of particularly preferred alkenyl groups are vinyl, 1B-propenyl, iE-butenyl, 1E-pentenyl, iE-hexeny, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 4-pentenyl, 4Z-hexenyl, -6 - 4E-hexenyl and -hexeny1. Groups having tip to 5 carbon atoms are generally preferred, in particular CH2=CH, CH3CH=CH.

The term "fluoroalkyl" preferably encompasses straight-chain groups having a terminal fluorine, i.e. fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoroperityl, 6-fluorohexyl and 7-fluoroheptyl. However, other positions of the fluorine are not excluded.

The term "oxaalkyl' or "alkoxy" preferably encompasses straight-chain radica's of the formula CH211÷1-O-(CH2)1, in which n and m each, independently of one another, denote ito 6. m may also denote o. Preferably, n = iand m = i-6 or m = o and n = 1-3.

Through a suitable choice of the meanings of R0 and X°, the addressing times, the threshold vollage, the steepness of the transmission characteristic lines, etc., can be modified in the desired manner. For example, iE-alkenyl radicals, 3E-alkenyl radicals, 2E-alkenyloxy radicals and the like generally result in shorter addressing times, improved nematic tendencies and a higher ratio between the elastic constants k33 (bend) and k1 (splay) compared vith alkyl and alkoxy radica's. 4-Alkenyl radicals, 3-alkenyl radicals and the like generally give lower threshold voltages and lower values of k33/k1 compared with alkyl and alkoxy radicals. The mixtures according to the invention are distinguished, in particular, by high Ac values and thus have significantly faster response times than the

mixtures from the prior art.

The optimum mixing ratio of the compounds of the above-mentioned formfflae depends substantially on the desired properties, on the choice of the components of the above-mentioned formulae and on the choice of any further components that may be present.

Suitable mixing ratios within the range indicated above can easily be determined from case to case.

The total amount of compounds of the above-mentioned formulae in the mixtures according to the invention is not crucial. The mixtures can therefore comprise one or more further components for the purposes of optimisation of various properties.

However, the observed effect on the desired improvement in the properties of the mixture is generafly greater, the higher the total concentration of compounds of the above-mentioned formulae.

in a particulady preferred embodiment, the media according to the invention comprise compounds of the formulae III to LX (preferably ill, Iv, V, VI and, VII, in particular lila and IVa) in which X° denotes F, OCF3, OCHF2, CF3, OCF2CHFCF3, OCHFCF3, CF2H, OCH=CF2, OCF=CF2 or OCF2CF2H. A favourable synergistic action with the compounds of the formu'ae TA and hA-TIC results in particularly advantageous properties. In particular, mixtures comprising compounds of the formulae IA and at least one compound of the formula hA, JIB and TIC in combination with at least one compound of the formula lIla and/or Wa are distinguished by their low threshold voltage.

The individual compounds of the above-mentioned formulae and the sub-formulae thereof which can be used in the media according to the invention are either known or can be prepared analogously to the known compounds.

The invention also relates to electro-optical displays, such as, for example, STN or MLC displays, having two plane-parall& outer plates, which, together with a frame, form a cell, integrated non-linear álements for switching individual pixáls on the outer p'ates, and a nematic liquid-crystal mixture having positive dielectric anisotropy and high specific resistance located in the cell, which contain media of this type, and to the use of these media for electro-optical purposes.

The liquid-crystal mixtures according to the invention enable a significant broadening of the available parameter latitude. The achievable combinations of clearing point, viscosity at low temperature, thermal and UV stability and high optica' anisotropy are far superior

to previous materials from the prior art.

The mixtures according to the invention are pardcularly suitable for TV, monitor, mobile applications, smart phones, tablet PC and PDA. Furthermore, the mixtures according to the invention can be used in TN-TVI FFS, VA-TPS, OCB and TPS displays.

The dielectric anisotropy Ae of the liquid-crystal mixtures according to the invention at °C is preferably »= +, particularly preferably »= +8, especially preferably »= 12.

The birefringence An of the liquid-crystal mixtures according to the invention at 20°C is preferably »= 0.09, particularly preferably »= o.io.

The liquid-crystalline medium according to the invention preferably has a nematic phase from «= -20 °C to »= 70 °C, particularly preferably from «= -o °C to »= 8o °C, very particularly preferably from «= -40 °C to »= 90°C.

LC mixtures with this nematic phase range at the same time allow rotational viscosities y of «= 110 mPas, particularly preferably «= 100 mPas, and thus excellent MLC displays having fast response times can be achieved. The rotational viscosities are determined at °C.

The expression "have a nematic phase" here means on the one hand that no smectic phase and no crystaflisation are observed at low temperatures at the corresponding temperature and on the other hand that clearing still does not occur on heating from the nematic phase. The investigation at low temperatures is carried out in a flow viscometer at the corresponding temperature and checked by storage in test cells having a layer thickness corresponding to the electro-optical use for at least 100 hours. If the storage stability at a temperature of -20 DC in a corresponding test cell is 1000 h or more, the medium is referred to as stable at this temperature. At temperatures of -30 °C and -40 °C, the corresponding times are 500 h and 250 h respectively. At high temperatures, the clearing point is measured by conventional methods in capillaries.

The liquid-crystal media according to the invention have relatively low values for the threshold voltage (V0). They are preferably in the range from 1.7 V to 3.0 V, particularly preferably «= 2.5 V and very particularly preferably «= 2.3 \7* In addition, the liquid-crystal media according to the invention have high vahies for the vohage holding ratio in liquid-crystal cells.

In general, liquid-crystal media having a low addressing voltage or threshold voltage exhibit a lower voltage holding ratio than those having a higher addressing vohage or threshold vollage and vice versa.

For the present invention, the term "dielectrically positive mixture or compounds" denotes mixUires or compounds having a Ac> 1.5, the term "didectrically neutral compounds denotes those having -1.5 «= Ac «= i. and the term "dielectrically negative compounds" denotes those having Ac c -1.5. The dielectric anisotropy of the compounds is determined hereby dissolving 10 % of the compounds in a liquid-ciystalline host and determining the capacitance of the resultant mixture in at least one test cell in each case having a layer thickness of 20 jim with homeotropic and with homogeneous surface align-ment at 1 kHz. The measurement voltage is typically 0.5 V to 1.0 V, but is always lower than the capacitive threshold of the respective liquid-crystal mixture investigated.

All temperature values indicated for the present invention are in °C.

It goes without saying that, through a suitable choice of the components of the mixtures according to the invention, it is a'so possib'e for higher clearing points (for examp'e above 100 °C) to be achieved at higher threshold voltages or lower clearing points to be achieved at lower threshold vohages with retention of the other advantageous propeities.

At viscosities corresponding'y increased only slightly, it is likese possible to obtain mixtures having a higher AE and thus low thresholds. The MLC displays according to the invention preferably operate at the first Gooch and Tarry transmission minimum [C.H.

Gooch and H.A. Tarry, Electron. Lea. 10, 2-4, 1974; C.H. Gooch and H.A. Tarry, AppI.

Phys., Vol. 8, 1575-1584, 1975], where, besides particularly favourable electro-optical propeities, such as, for example, high steepness of the characteristic line and low angle dependence of the contrast (German patent 30 22818), tower dielectric anisotropy is sufficient at the same threshold voltage as in an analogous display at the second mini-mum. This enables significantly higher specific resistance values to be achieved using the mixtures according to the invention at the first minimum than in the case of mixtures comprising cyano compounds. Through a suitable choice of the individual components and their proportions by weight, the person skilled in the art is able to set the birefringence necessary for a pre-specified layer thickness of the MLC display using sim-pe routine methods.

Measurements of the voltage holding ratio (HR) [S. Matsumoto et al., Liquid Crystals, 1320 (1989); K. Niwa et al., Proc. SID Conference, San Francisco, .June 1984, P. 304 (1984); G. Weber et al., Liquid Crystals, 1381 (1989)] have shown that mixtures according to the invention comprising compounds of the formulae TA and lB exhibit a significantly smaller decrease in the HR on UV exposure than analogous mixtures comprising cyanophenylcyclohexanes of the formula R CN or Esters of the formula R -O CN instead of the compounds of the formulae IA, hA and I1B and IIC.

The light stability and UV stability of the mixtures according to the invention are considerably belier, i.e. they exhibit a significantly smaller decrease in the HR on exposure to light or UV.

The construction of the MLC display according to the invention from polarisers, electrode base plates and surface-treated electrodes corresponds to the usual design for displays of this type. The term usual design is broadly drawn here and also encompasses all derivatives and modifications of the MLC display, in particular including matrix display elements based on poly-Si TFTs or MIM.

A significant difference between the displays according to the invention and the hitherto conventional displays based on the twisted nematic cell consists, however, in the choice of the liquid-crystal parameters of the liquid-crystal layer.

The liquid-crystal mixtures which can be used in accordance with the invention are prepared in a manner conventional per se, for example by mixing one or more -70 -compounds of the formulae TA with the compound(s) of the formula ITA, TTB and/or TIC with one or more mesogenic compounds, preferably at least one compound of the formulae TIT to XXX and optionally with suitable additives. Tn general, the desired amount of the components used in lesser amount is dissolved in the components making up the principal constituent, advantageously at elevated temperature. It is also possible to mix solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, and to remove the solvent again, for example by distillation, after thorough mixing.

The dielectrics may also comprise further additives known to the person skilled in the art and described in the literature, such as, for example, liv stabilisers, such as Tinuvin®, e.g. Tinuvin® 770, from Ciba Chemicals, antioxidants, e.g. TEMPOL, microparticles, free-radical scavengers, nanoparticles, etc. For example, 0-15 % of pleochroic dyes or chiral dopants can be added. Suitable stabilisers and dopants are mentioned below in Tables C andD.

Polymerisable compounds, so-called reactive mesogens (RMs), for example as disclosed in U.s. 6,861,107, may furthermore be added to the mixtures according to the invention in concentrations of preferably 0.12-5 % by weight, particularly preferably 0.2-2 % by weight, based on the mixture. These mixtures may optionally also comprise an initiator, as described, for example, in U.S. 6,781,665. The initiator, for example Trganox-1076 from Ciba, is preferably added to the mixture comprising polymerisable compounds in amounts of 0-i %. Mixtures of this type can be used for so-called polymer-stabilised (PS) modes, in which polymerisation of the reactive mesogens is intended to take place in the liquid-crystalline mixture, for example for PS-IFS, PS-FFS, PS-TN, PS-VA-TPS. The prerequisite for this is that the liquid-crystal mixture does not itself comprise any polymerisable components.

In a preferred embodiment of the invention, the polymerisable compounds are selected from the compounds of the formula M

M

-71 -in which the individual radicals have the following meanings: RMa and RMb each, independenfly of one another, denote F, P-Sp-, H, halogen, SF5, NO2, an a1ky, alkenyl or akyny group, where at least one of the radicals RMa and RMb preferably denotes or contains a group P or P-Sp-, P denotes a polymerisable group, Sp denotes a spacer group or a sing'e bond, AMI and AM2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably having 4 to 25 ring atoms, preferably C atoms, which may a'so encompass or contain fused rings, and which may optionally be mono-or L denotes F, P-Sp-, OH, CH2OH, F, Cl, Br, t, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, C(=O)N(Rx)2, C(=O)Y1, C(=O)Rx, N(Rx)2, optionally substituted silyl, optionally substituted aryl having 6 to C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyoxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F, Cl, P or P-Sp-, preferably F, P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, an alkyl, alkenyl or alkynyl group, denotes halogen, ZMI denotes -0-, -5-, -CO-, -CO-O-, -OCO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2)1-, -CF2CH2-, -CH2CF2-, -(CF2)111-, -CH=CH-, -CF=CF-, -CC-, -CH=CH-, -COO-, -OCO-CH=CH-, CR°R°° or a single bond, -72 -R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms, denotes F, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may be replaced by -0-, -5-, -CO-, -CO-O-, -0-CO-, -0-C0-0-in such a way that 0 and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms maybe replaced by F, Cl, For P-Sp-, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to C atoms, ml denotes 0, 1, 2, 3 or 4, and ni denotes 1,2,3 or 4, where at least one, preferably one, two or three, partici1larlypreferaNy one or two, from the group RM2, RMb and the snbstituents L present denotes a group F or P-Sp-or contains at least one gronp P or P-Sp-.

Particularly preferred compounds of the formula Mare those in which R" and RMb each, independenfly of one another, denote F, F-Sp-, H, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, SF5 or straight-chain or branched alkyl having ito 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by C(Ro)=C(Roo), -CC-, -N(R°°)-, -0-, -S-, -CO-, -CO-0-, -0-CO-, -o-co-o-in such a way that 0 and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I, CN, F or P-Sp-, where -73 -at least one of the radicals and RMb preferably denotes or contains a group P or P-Sp-, AM1 and A each, independenfly of one another, denote 1,4-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diy, coumarine, flavone, where, in addition, one or more CU groups in these groups may be replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CU2 groups maybe replaced by 0 and/or S, 1,4- cyclohexenylene, bicyclo[i. 1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane- 1,4-diyl, spiro[3.3]heptane-2,6-diy, piperid ine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indane-2,5-diyl or octahydro-4,7-methanoindane-2,5-diyl, where all these groups may be unsubstituted or mono-or L denotes P, P-Sp-, OH, CH2OH, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, C(=O)N(Rx)2, C(=O)Y1, C(=O)Rx, -N(R")2, optionally substituted silyl, optionally substituted aryl having 6 to C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxy carbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms maybe rep'aced by F, Cl, For P-Sp-, P denotes a polymerisable group, denotes halogen, denotes P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having ito 25 C atoms, in which, in addition, one or more non- adjacent Cl-I2 groups maybe replaced by -0-, -S-, -CO-, -CO-O-, -0-CO-, -O-CO-O-in such a way that 0 and/or S atoms are not linked directly to one another, and in which, in addition, one or more H -74 -atoms may be rep'aced by F, Cl, P or P-Sp-, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionafly substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms.

Very particular preference is given to compounds of the formula M in which one of RMa and RMI) or both denote(s) P or P-Sp-.

Suitable and preferred RMs for use in liquid-crystalline media and PS mode displays according to the invention are selected, for example, from the following formulae: (L) Mi P1-Sp1 C Sp2-P2 L) M2 PI-SpI 0 0 Sp2-P2 (11r /Th\ M3 Sp2-P2 S p3-P3 SSP2P2 M4 M5 -75 -Plsplsp2P2 M6 M7 M8 L) plsplz1sp2P2 M9 Mm L) Mn P1 splz244 Sp2-2 __L_ M12 P1-Sp1 0 -76 -Sp2-P2 M13 sp2-P2 Pl_spl M14 M15 Miô 3p2-P2 Sp1-F1 M17 P2-Sp2 Sp2 P2 Sp1-P1 Mi8 P1-Sp1 -77 -pls1o M19 Sp2-P2 M2o P2-sP2 -P2-Sp2 0 M21 M22 X2 sp2 p2 M23 P1-Sp1-X1 I X3-Sp3-P3 -78 -M24 P1-Sp1-X1 X2-Sp2-P2 M25 P1-Sp1-X1 (L) 1L)r M26 l) Q p2 P M27 M28 M29 -79 -p L__y2 M3o p3 plsplsp2P2 M31 p1sp1sp2P2 M32 p1sp1sp2p2 M33 JJJSP P M34 P1sp1sp2P2 M35 P1SP1SP2P2 M36 M37 -8o-P2S2JQ/C M38 Sp1-P2 P1-Sp1 Sp2-P2 ___X) K sp2P2 P1-Sp1 O-Sp1-F1 M4o F1-5p1-O M41 O-Sp1-F1 M42 0 O-Sp1-P1 Pl_spl_0."0_spl_Pl M43 F1-S P1-5p1-0 O-Sp1-F1 II'I M44 O-Sp1-P1 F -Sp -0 in which the individual radicals have the following meanings: p' and p each, independently of one another, denote a po1ymerisabe group, preferably having one of the meanings indicated above and below for F, particularly preferably an acrylate, methacrylate, fluoroacrylate, oxetane, vinyloxy or epoxy group, Sp1 and Sp2 each, independently of one another, denote a single bond or a spacer group, preferably having one of the meanings indicated above and below for Sp, and particularly preferably -(CH2)1-, -(CH2j1-O-, -(CH2)1-CO-O-or -(CHj1-O-CO-O-, in which pi is an integer from 1 to 12, and where the linking of the last-mentioned groups to the adjacent ring takes place via the 0 atom, where one of the radicals P1Sp1 and P2Sp2 may also denote R, Wa denotes H, F, Cl, CN or straight-chain or branched alkyl having ito C atoms, in which, in addition, one or more non-adjacent CF2 groups may each be replaced, independently of one another, by -C(R°)=C(R°°)-, -CC-, -N(R°)-, -0-, -S-, -CO-, -C0-0-, -0-CO-, -O-C0-O-in such a waythat 0 and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, CN or P'-Sp'-, particularly preferably straight-chain or branched, optionally mono-or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy having i to 12 C atoms (where the alkenyl and alkynyl radicals have at least two C atoms and the branched radicals have at least three C atoms), R0, R00 each, independently of one another and on each occurrence identically or differently, denote H or akyl having ito 12 C atoms, R and R each, independently of one another, denote H, F, CH3 or CF3, Z denotes -0-, -CO-, C(RYRz) or -CF2CF2-, Z2 and r each, independently of one another, denote -CO-O-, -0-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-or -(CH2)ir, where n is 2, 3 or 4, L on each occurrence, identically or differently, denotes F, Cl, CN, or straight-chain or branched, optionally mono-or poly fluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxy carbonyl or alkylcarbonyloxy having 1 to 12 C atoms, preferably F, L' and L" each, independently of one another, denote H, F or Cl, r denotes 0, 1, 2,3 or 4, s denotes 0, 1, 2 or 3, t denotes 0, 1 or 2, and x denotes o or 1.

Suitable polymerisable compounds are listed, for example, in Table E. The liquid-crystalline media in accordance with the present application preferably comprise in total 0.01 to 10 %, preferably 0.2 to 4.0 %, particularly preferably 0.2 to 2.0 %, of polymerisable compounds.

Particular preference is given to the polymerisable compounds of the formula M. The present invention thus also relates to the use of the mixtures according to the invention in electro-optical displays and to the use of the mixtures according to the invention in shntter glasses, in particular for 3D applications, and in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-TPS, FF5, PS-FFS and PS-VA-IPS displays.

The following examples are intended to exphuin the invention without limiting it. Above and below, per cent data denote per cent by weight; all temperatures are indicated in degrees Celsius.

Throughout the patent application, 1,4-cyclohexylene rings and 1,4-phenylene rings are depicted as follows: or or Besides the compounds of the formula IA and at least one compound selected from the compounds of the formula JIA, JIB and tIC, the mixtures according to the invention preferably contain one or more of the compounds from Tab'e A indicated below.

in the present application and in the examples below, the structures of the liquid-crystal compounds are indicated by means of acronyms, the transformation into chemical formube taking place in accordance with Table A. All radicals CnH2n+1 and CmH2m+1 are straight-chain alkyl radicals having n and m C atoms respectively; n, m and k are integers and preferably denote 0, 1, 2, 3,4, 5, 6, 7, 8, 9, 10, 11 or 12. The coding in TaNe B is self-evident. tn Table A, only the acronym for the parent structure is indicated. In individual cases, the acronym for the parent structure is followed, separated by a dash, by a code for the substituents Ri, R2, Lix and La: Code for R1*, R2* L L2* R2* L'-L2*, L3* nm CH211+1 H H nOm CH211+1 OCmH2ni+i H H nO. m 0C11H211+1 C1H2111±1 H H n C11H211+1 CN H H nN.F CH2÷1 CN F H nN.F.F C11H211+1 CN F F nF CH211+1 F H H nCl C1H2,+1 Cl H H nOF 0C11H211+1 F H H nF.F CH2+1 F F H nF.F.F C1H2+1 F F F nOCF3 CH2,÷, OCF3 H H nOCF3.F C11H211+1 OCF3 F H n-Vm C1H2÷1 -CH=CH-C1H21÷1 H H nV-Vm C11H211+1-CH=CH--CH=CH-C1H2111+1 H H The following abbreviations are used: (n, m, m', z: each, independently of one another, 1, 2, 3, 4, 5 or 6; (O)C11H2111± denotes OC111H21+1 or C1H21+1) Preferred mixture components are shown in Tables A and B.

Table A L1 L1

Rl* Rl* L2

PYP PYRP R1 R1

BCH CBC

R1 R1 R2*

CCH CCP L1

CC R2* R1 t_9_c2 H4-<'--C e c n

CPTP CEPTP L1 L1

-(Q9J----4(9.-C2H4--R2* __(9_ C2H4___@___ R2 L2

ECCP CECP R1

R1 c -3--R2

CH

R1 COO

PIT CCPC

R1COOR2* Rl* C2H4 R2

CP BECH

-(.-----C2H4--R2 *

EBCH CPC

R2* R' * C2H4 F B FET-nF * FF R2* R' * -CGG WI] * -K R2* CEll

Table B

In the following formulae, n and m each, independently of one another, denote 0, 1, 2, 3, 4, 5, 6, , 8, 9, 10, 11 or 12, in particular 2, 3,5, furthermore 0, 4, 6.

F

CH2÷1 0 0 OCH=CF2

F

APIJ-n-OXF CH21 -KI}----jj-CF2O--F ACQU-n-F CCP-nOCF3

F F

CH2÷1 0 0 CF2 0 F

F F

APIJQU-n-F CmH2m+ CF-121 F BCH-n.Fm CFU-n-F CH2÷1 F CH21 F BCH-nF.F.F CCP-nF.F.F CH2÷1 CmH2mi CBC-nmF CH21 -K-K-C2Hz OH2 CH21 K'Kj coo-(--F ECCP-nm CCZU-n-F CH21 CmH2mi CH21 F PGP-n-m CGU-n-F C F2 F C1RJQU-n-F CH2÷1 F _ç F CDU-n-F DCEJ-n-F CH21 FF F OH2÷1 -K--KIi:--coo--00F3 CGG-n-F CPZG-n-OT C H __29-cD'--KID*-_ C H n 211-ti m 2m+ CC-nV-Vm f_CnH2n_®_&__®_CH21 /__cID.__KID.__cII$:_ CCP-Vn-m CCG-V-F C H CmH2m CH21 _Kr\ID.__KIDP_% n 2n-t-1 CCP-nV-m CC-n-V CH2÷1 -KIED.--KIE:::'-CF2O---CH21 -.---i$---. CmH2mi CCQU-n-F CC-n-Vm CH2÷1 F CLUQU-n-F a n 2n+1 m 2mM CPPC-nV-Vm -9'-CF2 F CCQG-n-F CQU-n-F ___,f_Ø_®_CmFH2mi CP-iV-m CP-2V-m CP-V2-m CH2÷1 F F Dec-U-n-F CWCU-n-F CH2÷1 Cl2mn+1 CPGP-n-m C2F4 F CWCG-n-F CnH2n+i-®____&__CH2O_____&__CIrH2rn+l CCOC-n-m CH2,1 -F CPTU-n-F GPTU-n-F CH2÷1CF2O *F PQU-n-F PUQU-n-F PGTJ-n-F CGZP-n-OT CflH2fl÷__®_®____ CnH2n,i___®__Q_CF2O____F CCGU-n-F CCQG-n-F -93 -

F F F F

CflH2fl+_)-®___F CriH2ni_>__®_______OCFs DPGTJ-n-F DPGU-n-OT CUQTJ-n-F CCCQJJ-n-F

F

CGIJQU-n-F criH2n+l__®-_®__OCFs CPGU-n-OT

F

PYP-nF -94 -

F

CPGU-n-F __Jf-KI>-\__()__()__OCF CnH2n,i__-__-__-@CI CVCPiWOT GOP-n-Cl C H _ I)°mC H H3C-(-J_CflH2fl__\ H n 2ri+1 in 2m-f-m 2m+1 PP-nV-Vm PP-i-nVm CH2,1C2F4 CF2OF CWCQU-n-F PPGU-n-F PGTJQU-n-F -95 -CflH2fl÷______@_CF2O__F CflH2fl+-_)-_®-_®_F GPQU-n-F MPP-n-F

F F F F

CflH2fl+T->___CF2O__F MUQU-n-F NUQEJ-n-F CnH2n+i__®______®_(CH2)__\_ in 2rTH-1 PGP-n-kVm CflH2fl÷i-®__@_(CH2)___% H Fr 2i11-'-l PP-n-kVm CnF-12ni---®---®-CI PCH-nCl GP-n-C1 GOP-n-F PGIGI-n-F PGIJ-n-OXF CPU-n-OXF AIK-n-F CmH2mi BCH-nm CH2 CmH2mi BCH-nmF CH2,1 -KT-K(--K'--CmH2mi BCN-nm CH21 0CmH2m+i CY-n-Om CH21 CY(P,C1)n-Om CH21 OF OCmH2mi CY(C1,F)-n-Om CH2÷1 FF OCmH2m+i CCY-n-Om CH21 CCY(F,C1)n-Om CH21 OF OCmH2mi CCY(C1,F)-n-Om FF CmH2mi CCY-n-m FF CH21 CCY-V-m 4;;-crH2r_Kr>__( )_(J_ CH1 CCY-Vn-m CH21 OCmH2mCH=CH2 CCY-n-OmV CmH2m+i CBC-nm CmH2ni CCP-V-m CmH2n+i CCP-n-m FF (O)CmH2mi CPYP-n-(O)m FFFF CrnH2m+i CYYC-n-m CflH2fl+O (O)CmH2mi CCYY-n-(O)m CflH2fl1O-C2H4-CH=CH2 CCY-n-02V CH21 CCH-nOm -100 -CH21 CmH2mi CY-n-m CH2÷1 CmH2mi CCH-nm CC-n-Vi CC-2V-V2 CVC-n-m CH2÷1 COO OCH2 CP-nOmFF COO----CH2 CH-nm CEY-V-n CVY-V-n

FF

CY-V-On CH21 OCH2CH=CH2 CY-n-OiV

F F

CH

OC=CH2 CY-n-OC(C113)=CH2 -102-CCN-nm OCH=CH2 CY-n-OV CCPC-nm CflH2fl1 (CH2)zOCmH2mi CCY-n-zOm CflH2fl÷1 OCmH2mi CPY-n-Om CmH2m+i CPY-n-m -103 -CPY-V-Om CH21 CF2OH(O)CmH2m.i CQY-n-(O)m CH241 OCF2(O)CmH2m+i CQ1Y-n-(O)m CH21 CF2O(O)CmH2mi CCQY-n-(O)m CH21 OCF2(O)CmH2m+i CCQIY-n-(O)m CH21 CF2O(O)CmH2m+i CPQY-n-(O)m OCF2(O)CniH2mi CPQIY-n-(O)m C H2)______5__0)C H2 I CPYG-n-(O)m CCY-V-Om CCY-V2-(O)m CCY-1V2-(O)m -105 -CCY-3V-(O)m CnH2n+i-<_H> ___ CCVC-n-V C H2 (O)C H2 CPYG-n-(O)m CY-nV-(O)m CH2÷1 CENaph-n-Om -io6 -CH21 OCmH2mi COchrom-n-Om CH21 CmH2mi COChrom-n-m CH21 OCmH2mi CCOChrom-n-Om CH21 CmH2mi CCOChrom-n-m

F F

CH21 OCmH2m+i CONaph-n-Om -107-

F F

CH21 OCmH2mi CCONaph-n-Om

F F

CCNaph-n-Om

F F

CNaph-n-Om

F F CH21

CETNaph-n-Om

F F

CH2÷1 OCmH2m+1 CTNaph-n-Om -io8 -CflH2fl+I___®___cI F CK-n-F CH2OCH21 CLY-n-Om C H2 H2 CLY-n-m CnH2n+iCH2i LYLI-n-m CnH2ni_______CCH2i CYLI-n-m CH21 (O)CmH2ni LY-n-(O)m -109 -

F F

CH21 K'T COYOICC-n-m C H2÷ COYOIC-n-V

F F

CCOY-V-02V rcoo CCOY-V-03V

F F

CH21 CH2O OCmH2mi COY-n-Om

F F

CH21 CH2O OCmH2m+i CCOY-n-Om -110 -CH21 COO OCH1 D-nOmFF CH21 PCH-nrn CH2÷1 OCmH2m+i PCH-nOrn CnH2i/)__J>__CH2i PP-n-rn CnH2niCmH2m PYP-n-rnV CnH2niCmH2nii PYP-n-m -111 -CnH2niOCmH2mi PYP-n-Om cflH2fll___-b____®____b___CflH2Fr+l YPY-n-m CH2OCH2-CH=CH2 YPY-n-mV CH2÷1 OOCmH2mi Y-nO-Om CnH2n+iCmH2mi PY-n-m CnH2niOCmH2mi PY-n-Om -112 -CflH2fl÷1 (O)CmH2mi C-DFDBF-n-(O)m F 0 F CH21 (0) 0 0 (0)CH21 DFDBC-n(O)-(O)m F 0 F CH2÷1 (0) 0 0 (0)CmH2m+i DFDBC-n(O)-(O)m Particular preference is given to liquid-ciystalline mixtures which, besides the compounds of the formulae TA and TB, comprise at least one, two, three, four or more compounds from Table B. -113 -

Table C

Table C indicates possible dopants which are generally added to the mixtures according to the invention. The mixtures preferably comprise 0-10 % by weight, in particular 0.01-5 % by weight and particularly preferably 0.01-3 % by weight of dopants.

C2H5-CH-CH2O--_{__(__CN C2H5-CH-CH2__-®__®_CN CH3 CH3 C15 CB15 C6H1CH:O C6H CH-C6H1. H3

CM 21 R/S-811 C3H7 -(9-f-(-CH2-CH-C2H, C5H1 CH-C2H5 CM44 CM45 C8H 70 -K-----: - H3C 1çH3 H C2H5 C8H CM47 CN -114 -C3H7__Ø_____OcH-C6H13 * C5H1

F

R/S-2o11 R/S-3o11 C5Hi__&__@___OCH-CsHIa R/S-4o11 R/S-5o11 R/S-io ii

Table D

Stabilisers, which can be added, for example, to the mixtures according to the invention in amounts of 0-10 % by weight, are mentioned below.

HO-CH2-QH HO,-c-O H -115 -

OH

fl = 1, 2, 3, 4, 5, 6 or 7 CH21 Ti = 1, 2,3,4,5,6 or 7 CflH2.1O4H HOCH2H H37C18-COO-C2H4H -116 -

HOMH

CH2÷1 OH Ti = 1, 2,3,4,5,6 or 7 HO) IOH 01-I 0 flo -117->L)f NyN HO NtN

N HOJt <NyN

H

OH

N

OH

-118 -CIt OCN:N g Oc HOr N<?

HO

-119 -C-) = N) m C) z çio

-I

0 0 /\ 0 I U, C) 0

I o

I

CH21 H fl = 1, 2, 3, 4, 5, 6 or 7 H_N>OH H_N>OMo H_N>NHCOCH3 HON>OH HO_N>OMe HONNHCOCH3

OH I 7

Table E

P&ymerisable compounds, which can be added, for example, to the mixtures according to the invention in amounts of 0.01 -1 % by weight, are mentioned below. It may atho be necessary to add an initiator for the polymerisation, preferably in amounts of o -1 %.

-121 -0'-< RM-i cO-O-o RM2 RM-3 o-c2°< RM-5 O_4cD-' RM-6 t0 _o-cQ-----RM-7 O< -122 -\ -RM-9 no RMio 0 RM-n o RM-12

-

F F FO RM-13 0 F

F F FOj o RM-14 /0 F F 0 \ RM-15

F

0 RM-i6 -123 ->cb&< RMi8 IbKIft< RW20 RM21 FF0 RM22 RW23 RW24 FFO( RM25 FFOj RM26 RW27 RW28 FX RM29 FFFFO RM3o RW31 FFFFO RW32 -125 -o o RM-33 )LJ)o

-

o RM-34 0 0 0 \ P_QcI_,_ O< RM-35 RW36 \ RM-37 c&iOL RW38 0" RM-39 no -126 - -: _rII,_rX° \ RM-41 no RW42 F 0 \ ,o-J-i-J---o" RM-43 o RM-44 F 0 \ ,o_3-_Q_/_ o< RM-45 no o RM-46 0-0-0 F F 0 \ o< RM-47 no -127-

F F RM-48

-o_.,._ o a RM-49 o 0 RM-5o o 0 RM-51 0 0 0 0 RM-52 N RM-53 N RM-54 I___0 0 -128 - ___-JzjJ--oYij RM-6 RM-57 0 RM-58 RM-59 RW6o o RM-6i 0 rj50O 0 -129 -7 o RM-62 H0 RM63 RW64 H0 -130 -RM-66 o FxfJI5%fI. F oo I o( RM-67 0oGo 00 I I RM-68 0 0 0 0

I I

o RM-69 RM-7o RM71 at RM-72 0t a RM-73 ktj#& ow0 RM-74 aKI9KI-RM-75 RM-76 a RM-77 -132 -

V oTh.

o.Q o.qo oO 0=1 °=1 0oo (3 to I 0t

I I I 00 00

-C 00

I // a 4

5R OCR OT 1: 1 Co CO 00 00 cJl I') RM-86 F.. 0 ° o<' The following mixture examples are intended to explain the invention without limiting it.

Above and below, percentage data denote per cent by weight. All temperatures are indicated in degrees Celsius. m.p. denotes melting point, cLp. = clearing point.

Furthermore, C = crystalline state, N = nematic phase, S = smectic phase and I = isotropic phase. The data between these symbols represent the transition temperatures. Furthermore, -An denotes the optical anisotropy at 589 nm and 20°C, -y denotes the rotational viscosity (mPa-s) at 20°C, -AE denotes the dielectric anisotropy at 20°C and 1 kHz (Ac = EM -c_, where c11 denotes the dielectric constant parallel to the longitudinal axes of the molecules and c1 denotes the dielectric constant perpendicular thereto), -V10 denotes the voltage (V) for 10 % transmission (viewing angle perpendicular to the plate surface), (threshold voltage), determined in a TN cell (90 degree twist) at the 1st minimum (i.e. at ad-An value of 0.5 pm) at 20°C, -V0 denotes the capacitively determined Freedericks threshold voltage in an antiparallel-rubbed cell at 20 °C.

-135 -All physical properdes are determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals", status Nov. 1997, Merck KGaA, Germany, and app'y for a temperature of 20 °C, un'ess explicitly indicated otherwise.

Examples

Mixture Mi CC-3-V 16.87% Clearing Point [°C]: 82.0 CC-3-V1 4.26 % An [589 nm, 20°C]: 0.108 CCQU-2-F 6.39 % Ac [1kHz, 20°C]: 9.3 CCQU-3-F 9.23 % c_ [i kHz, 20°C]: 8.37 CCP-2F.F.F 4.26% K1 [20 °C]: 12.5 PUQU-3-F 11.36 % 1(3 [20 °C] 13.4 CCP-V-i 9.94 % y [20 °C, mPas]: 112 APUQU-3-F 8.52% LTS Bulk -25 °C > ioooh PCUQU-3-F 5.68 % LTS Bulk -30°C > 1000 h CY-3-02 6.96% CY-5-02 1.015 % CLY-3-02 2.03 % CCY-3-02 2.90 % CCY-3-03 1.305 % CCY-4-02 1.16 % CPY-2-02 2.90 % CPY-3-02 2.32 % PYP-2-3 1.74 % PYP-2-4 1.16 % -136 -Mixture M2 CY-3-02 8.50 % Clearing Point [°C]: 8o.o CCY-3-02 6.00 % An [589 nm, 20°C]: 0.109 CPY-2-02 6.oo % As [1kHz, 20°C]: 9.5 PYP-2-3 3.00% e_ [i kHz, 20°C]: 8.97 CC-3-V 30.50% K1 [20 °C]: 12.5 CLY-3-02 5.00 % K3 [20 °C]: 13.5 CCQIJ-3-F 11.50 % 71 [20 °C, mPas]: 105 APUQIJ-2-F 8.so % APUQU-3-F 8.oo % PGUQU-3-F 7.50 % PUQU-3-F 5.50 % Mixture M3 CCY-3-02 5.00 % Clearing Point [°C]: 78.5 CPY-2-02 8.oo % An [589 nm, 20°C]: 0.109 CC-3-V 31.00 % As [i kHz, 20°C]: 9.7 CLY-3-02 8.oo % c_ [i kHz, 20°C]: 9.58 CCQU-3-F 7.50% K, [20 °C]: 12.6 APUQU-2-F 11.50 % IC [20 °C]: 13.2 APUQU-3-F 12.00 % y [20 °C, mPas]: 105 DPGIJ-4-F 3.00 % PUQU-3-F 5.50 % PY-3-02 5.50 % Y-40-04 3.00 % Mixture M4 CC-3-V 34.00 % Clearing Point [°C]: 77.5 CCQU-2-F 5.50 % An [589 nm, 20°C]: 0.107 CCQU-3-F 9.50 % As [1kHz, 20°C]: 9.6 APUQU-2-F 11.00 % e_ [i kHz, 20°C]: 8.03 APUQU-3-F 11.00 % K1 [20 °C]: 12.2 PUQU-3-F 3.00 % K3 [20 °C]: 12.4 PY-3-02 4.00 % 71 [20 °C, mPas]: 87 PYP-2-3 6.o % CLY-3-02 7.00 % CPY-2-02 2.50 % BCH-3F.F.F 6.oo % Mixture Ms CY-3-02 5.50 % Clearing Point [°C]: 78.5 CCY-3-02 4.50 % An [589 nm, 20°C]: 0.109 CPY-2-02 5.50 % As [i kHz, 20°C]: 9.3 PYP23 3.00% c_ [i kHz, 20°C]: 8.95 CC-3-V 30.50% K, [20 °C]: 12.4 CLY-3-02 7.00 % IC [20 °C]: 13.4 CCQU-3-F 8.oo % y [20 °C, mPas]: 103 APUQIJ-2-F 12.00 % APUQU-3-F 12.00 % PUQU-3-F 5.50 % BCH-3F.F.F 3.50 % PY-3-02 3.00 % -138 -Mixture M6 CCY-3-02 5.00 % Clearing Point [°C]: 78.0 CPY-2-02 8.00 % An [589 nm, 20°C]: 0.109 CC-3-V 31.00% AE[lkHz,20°C]: 9.9 CLY-3-02 8.00% e_ [i kHz, 20°C]: 9.55 CCQU-3-F 8.oo % K1 [20 °C]: 12.5 APUQU-2-F 11.50 % K3 [20 °C]: 13.3 APUQU-3-F 12.00 % 71 [20 °C, mPas]: 104 PCUQU-3-F 3.00 % PUQU-3-F 5.50 % PY-3-02 5.50 % Y-40-04 2.50 % Mixture M7 CC-3-V 34.50 % Clearing Point [°C]: 78.5 CCQU-3-F 9.50 % An [589 nm, 20°C]: 0.109 APUQU-2-F 8.oo % AE [i kHz, 20°C]: 9.5 APUQIJ-3-F 10.00 % c_ [i kHz, 20°C]: 7.93 PUQU-3-F 7.50% K, [20 °C]: 12.3 PYP-2-3 4.50 % IC [20 °C]: 12.7 CLY-3-02 8.oo % y [20 °C, mPas]: 88 CPY-2-02 6.o % BCH-3F.F.F 11.50 % -139 -Mixture M8 CC-3-V 33.00 % Clearing Point [°C]: 77.5 CCQU-3-F 8.50 % An [589 nm, 20°C]: 0.109 APUQU-2-F 10.00 % As [1kHz, 20°C]: 9.5 APUQU-3-F 10.00 % e_ [i kHz, 20°C]: 8.25 PUQU-3-F 5.50 % K1 [20 °C]: 12.1 PYP-2-3 4.00 % K3 [20 °C]: 12.8 CLY-3-02 8.00 % 71 [20 °C, mPas]: 90 CPY-2-02 7.50 % BCH-3F.F.F 12.00 % Y-40-04 1.50 % Mixture Mg CCY-3-02 5.00 % Clearing Point [°C]: 79.5 CPY-2-02 8.00 % An [589 nm, 20°C]: 0.109 CC-3-V 31.00 % As [i kHz, 20°C]: 9.4 CLY-3-02 8.oo % s_ [i kHz, 20°C]: 9.36 CCQU-3-F 7.50% K1 [20 °C]: 12.6 APUQU-2-F 11.50 % IC [20 °C]: 13.4 APUQU-3-F 12.00 % 71 [20 °C, mPas]: 104 CPGU-3-OT 3.00 % PUQU-3-F 6.oo % PY-3-02 5.00 % Y-40-04 3.00 % -140 -Mixture Mb CCY-3-02 5.00 % Clearing Point [°C]: 77.0 CPY-2-02 8.00 % An [589 nm, 20°C]: 0.109 CC-3-V 27.00 % As [1kHz, 20°C]: 9.4 PCH-301 5.00% e_ [i kHz, 20°C]: 9.49 CLY-3-02 8.oo % K1 [20 °C]: 12.1 CCQU-3-F 8.oo % K3 [20 °C]: 12.9 APUQU-2-F 11.50 % 7i [20 °C, mPas]: 107 APIJQIJ-3-F 11.50 % DPGU-4-F 3.00 % PUQU-3-F 5.50 % PY-3-02 4.50 % Y-40-04 3.00 % Mixture Mn APUQU-2-F 8.o % Clearing Point [°C]: 78.0 APUQU-3-F 8.oo % An [589 nm, 20°C]: 0.107 CC3V 44.50 % As [i kHz, 20°C]: 9.8 CCP-30CF3 7.50% s [i kHz, 20°C]: 6.8i CCP-V-i 7.00 % K, [20 °C]: 12.3 DPGU-4-F 3.50 % K3 [20 °C]: 13.4 PGP-2-2V 3.50 % y [20 °C, mPas]: 66 PCUQU-4-F 5.00 % PUQU-3-F 8.o % PYP-2-3 4.00 % -141 -Mixture M12 APUQIJ-2-F 8.50 % Clearing Point [°C]: 78.0 APUQU-3-F 8.00 % An [589 nm, 20°C]: 0.107 CC-3-V 44.50 % As [1kHz, 20°C]: 9.7 CCP-30CF3 7.50% e [i kHz, 20°C]: 6.94 CCP-V-i 6.oo % K1 [20 °C]: 12.4 DPGU-4-F 3.50 % K3 [20 °C]: 13.4 PGP-2-2V 2.50 % 71 [20 °C, mPas]: 66 PCUQU-4-F 5.00 % PUQU-3-F 8.50 % PYP-2-3 4.00 % CPY-2-02 2.00 % Mixture M13 CY-3-02 6.50 % Clearing Point [°C]: 77.0 CLY-3-02 6.00 % An [589 nm, 20°C]: 0.111 CCY-3-02 8.oo % As [i kHz, 20°C]: 9.5 CPY202 7.00% c_ [i kHz, 20°C]: 9.88 CPY-3-02 5.50 % K, [20 °C]: 12.1 CC-3-V 27.00 % IC [20 °C]: 13.2 PUQU-3-F 15.00 % y [20 °C, mPas]: 114 APUQIJ-2-F 10.00 % APUQU-3-F 10.00 % CCQU-3-F 4.00 % Y-40-04 1.00 % -142 -Mixture M14 CC-3-V 34.50 % Clearing Point [°C]: 76.5 PGP-2-2V 4.50 % Ac [1kHz, 20°C]: 19.4 PGU-2-F 3.50% c_ [i kHz, 20°C]: n.o6 PCU-3-F 6.50 % APUQU-2-F 8.oo % APUQLJ-3-F 8.oo % PCUQU-3-F 4.00 % PCUQU-4-F 8.oo % PGUQU--F 8.oo % DPGIJ-4-F 6.oo % BCH-3F.F.F 6.oo % PY-3-02 3.00 % Mixture Mis CC-3-V 31.50 % Clearing Point [°C]: 75.0 PCP-2-2V 4.50 % Ac [i kHz, 20°C]: 19.9 PCU-2-F 3.50% c_ [i kHz, 20°C]: 11.57 PGU-3-F 6.50% K1 [20 °C]: 12.2 APUQU-2-F 8.oo % K3 [20 °C]: 11.5 APLJQIJ-3-F 8.oo % PGUQU-3-F 4.00 % PGUQU-4-F 8.oo % PGUQU--F 8.oo % DPGU-4-F 6.oo % BCH-3F.F.F 6.oo % PY-3-02 6.oo % -143 -Mixture Mi6 CC-3-V 25.50 % Clearing Point [°C]: 71.5 PGP-2-2V 4.50 % Ac [1kHz, 20°C]: 21.0 PGU-2-F 3.50% c_ [i kHz, 20°C]: 12.66 PCU-3-F 6.50 % APUQU-2-F 8.oo % APUQLJ-3-F 8.oo % PCUQU-3-F 4.00 % PCUQU-4-F 8.oo % PGUQU--F 8.oo % DPGIJ-4-F 6.oo % BCH-3F.F.F 6.oo % PY-3-02 12.00 % Mixture Mr CC-3-V 19.50 % Clearing Point [°C]: 67.5 PCP-2-2V 4.50 % Ac [i kHz, 20°C]: 22.4 PCU-2-F 3.50% c_ [i kHz, 20°C]: 13.92 PGU-3-F 6.50% K1 [20 °C]: 13.1 APUQU-2-F 8.oo % K3 [20 °C]: 12.7 APLJQIJ-3-F 8.oo % PGUQU-3-F 4.00 % PGUQU-4-F 8.oo % PGUQU--F 8.oo % DPGU-4-F 6.oo % BCH-3F.F.F 6.oo % PY-3-02 18.00 % -144 -Mixture Mi8 CC-3-V 13.50 % Clearing Point [°C]: 64.0 PGP-2-2V 4.50 % Ac [1kHz, 20°C]: 24.3 PGU-2-F 3.50% c_ [i kHz, 20°C]: 15.31 PCU-3-F 6.50 % APUQU-2-F 8.oo % APUQLJ-3-F 8.oo % PCUQU-3-F 4.00 % PCUQU-4-F 8.oo % PGUQU--F 8.oo % DPGIJ-4-F 6.oo % BCH-3F.F.F 6.oo % PY-3-02 24.00 % Mixture Mig CC-3-V 25.50 % Clearing Point [°C]: 8o.o PCP-2-2V 7.00 % An [589 nm, 20°C]: 0.155 PCU-3-F 2.00 % Ac [i kHz, 20°C]: 22.4 APUQU-2-F 8.oo % c_ [i kHz, 20°C]: 12.95 APUQU-3-F 8.o % K1 [20 °C]: 14.5 PGUQU-3-F 5.00 % K3 [20 °C]: 15.7 PCUQU-4-F 9.00 % y [20 °C, mPas]: 145 PGUQU--F 9.00 % DPGU-4-F 8.oo % BCH-3F.F.F 6.00 % PY-3-02 12.00 % -145 -Mixture M2o CC-3-V 25.50 % Clearing Point [°C]: 78.0 CCP-V-i 7.00 % An [589 nm, 20°C]: 0.139 PGU-3-F 2.00 % As [1kHz, 20°C]: 20.1 APUQU-2-F 10.00 % e_ [i kHz, 20°C]: 12.18 APUQU-3-F 10.50% K1 [20 °C]: 12.6 PGUQU-3-F 4.00 % K3 [20 °C]: 12.6 PGUQU-4-F 9.00 % 7i [20 °C, mPas]: 127 PCUQU--F 9.00 % DPGU-4-F 5.00 % BCH-3F.F.F 6.oo % PY-3-02 12.00 % Mixture M21 CC-3-V 31.50 % Clearing Point [°C]: 75.0 PGP-2-2V 4.50 % An [589 nm, 20°C]: 0.138 PGU-2-F 3.50 % As [i kHz, 20°C]: 19.2 PGU-3-F 6.50% c_ [i kHz, 20°C]: 11.33 APUQU-2-F 8.oo % K, [20 °C]: 11.5 APUQU-3-F 8.oo % K [20 °C]: 11.4 PGUQU-3-F 4.00 % y [20 °C, mPas]: 109 PGUQU-4-F 8.oo % PCUQU--F 8.oo % DPGU-4-F 6.oo % BCH-3F.F.F 6.oo % CY-3-02 6.oo % -146 -Mixture M22 CC-3-V 25.50 % Clearing Point [°C]: 79.5 PGP-2-2V 7.00 % An [589 nm, 20°C]: 0.141 PGU-3-F 2.00 % As [1kHz, 20°C]: 20.3 APUQU-2-F 10.50% e_ [i kHz, 20°C]: 12.37 APUQU-3-F 11.00 % K1 [20 °C]: 12.4 PGUQU-3-F 4.00 % K3 [20 °C]: 12.4 PGUQU-4-F 8.00 % 7i [20 °C, mPas]: 133 PCUQU--F 7.00 % DPGU-4-F 7.00 % BCH-3F.F.F 6.oo % CY-3-02 12.00 % Mixture M23 CC-3-V 19.50 % Clearing Point [°C]: 68.0 PGP-2-2V 4.50 % An [589 nm, 20°C]: 0.142 PGU-2-F 3.50 % As [i kHz, 20°C]: 19.8 PGU-3-F 6.50% c_ [i kHz, 20°C]: 13.10 APUQU-2-F 8.oo % K, [20 °C]: 10.7 APUQU-3-F 8.00 % IC [20 °C]: 10.5 PGUQU-3-F 4.00 % y [20 °C, mPas]: 135 PGUQU-4-F 8.oo % PCUQU--F 8.oo % DPGU-4-F 6.oo % BCH-3F.F.F 6.oo % CY-3-02 i8.oo % -147 -Mixture M24 CC-3-V 37.50 % Clearing Point [°C]: 77.0 PGU-2-F 3.50 % AE [1kHz, 20°C]: 18.7 PGU-3-F 6.50% E_ [i kHz, 20°C]: 10.64 APUQU-2-F 8.00 % APUQU-3-F 8.00 % PGUQU-3-F 4.00 % PCUQU-4-F 8.oo % PCUQU--F 8.oo % DPGU-4-F 6.oo % BCH-3F.F.F 6.oo % PYP-2-3 4.50 % Mixture M25 CC-3-V 31.50 % Clearing Point [°C]: 84.0 PGP-2-2V 4.50 % Aa [i kHz, 20°C]: 21.1 PGU2F 3.50% E_ [i kHz, 20°C]: 11.47 PGU-3-F 6.50 % y [20 °C, mPas]: 121 APUQU-2-F 8.oo % APUQU-3-F 8.oo % PGUQU-3-F 4.00 % PCUQU-4-F 8.oo % PGUQU--F 8.oo % DPGIJ-4-F 6.oo % BCH-3F.F.F 6.oo % PYP-2-3 6.00 % -148 -Mixture M26 CC-3-V 35.00 % Ckaring Point [°C]: 8o CC-3-V1 11.00% an [589 nm, 20°C]: 0.1058 CCP-V-i 4.50 % aE [i kHz, 20°C]: 5.4 PCP-2-2V 10.00 % c1 [i kflz, 20 °C]: 3.8 CCP-30CF3 8.oo % K1 [20 °C]: 13.2 APUQU-2-F 7.00 % K3 [20 °C]: 14.4 APUQU-3-F 8.oo % 7i [20 °C, mPas]: 69 PCUQU-3-F 3.00 % V0 [V]: CPGTJ-3-OT 3.00 % CY-3-02 10.00 % Mixture M27 CC-3-V 44.50% Clearing Point [°C]: 79.5 CC-3-V1 9.00 % An [589 nm, 20°C]: 0.1057 CCF-V-i 8.oo % Ac [1kHz, 20°C]: 5.7 CCP-30CF3 4.50 % c_ [i kHz, 20 °C]: 3.3 PGP-2-3 3.00 % K1 [20 °C]: 13.3 APUQU-3-F 6.00 % yi [20 °C, mPas]: 60 PGUQU-3-F 4.50 % V0 [\T] 1.65 PGUQU-4-F 7.00 % CPCU-3-OT 5.00 % PY-3-02 5.00 % -149 -Mixture M28 CC-3-V 41.00% Clearing Point [°C]: 78.5 CC-3-V1 5.50 % An [589 nm, 20°C]: 0.1054 CCP-V-i 11.50 % Ac [1kHz, 20°C]: 5.7 PCP-2-4 2.00 % c [i kHz, 20 °C]: 3.8 CCP-30CF3 6.50 % K1 [20 °C]: 13.0 APUQU-3-F 6.50 % K3 [20 °C] 14.2 PGUQU-3-F 3.00 % 7i [20 °C, mPa*s]: 63 PCUQU-4-F 9.00 % V0 [V] 1.59 CPGTJ-3-OT 5.00 % PY-3-02 10.00 % Mixture M29 CC-3-V 33.50% Clearing Point [°C]: 79.5 CCP-V-i 12.50 % An [589 nm, 20°C]: 0.1077 PGF-2-2V 6.o % Ac [1kHz, 20°C]: 5.5 CCP-3-1 7.00 % c_ [i kHz, 20 °C]: 4.3 CCP-3-3 6.oo % K1 [20 °C]: 12.8 CCF-30CF3 2.00 % 1(3 [20 °C] 13.7 APUQU-3-F 8.00 % yi [20 °C, mPas]: 69 PGUQU-3-F 3.00 % V0 [\T] 1.61 PGUQU-4-F 7.00 % CPCU-3-OT 5.00 % Y-40-04 10.00 % -150 -Mixture Mo CC-3-V 39.50 % Clearing Point [°C]: 84.9 CC-3-V1 2.50 % An [589 nm, 20°C]: 0.1086 CCP-30CF3 8.oo % AE [1kHz, 20°C]: 8.3 CCP-V-i 14.00% e [i kHz, 20 °C]: 3.2 CCP-V2-1 2.50% K1 [20 °C]: 13.0 CPGU-3-OT 1.50 % K3 [20 °C] 14.9 DPGU-4-F 4.00 % 71 [20 °C, mPas]: 69 PCUQU-3-F 8.oo % V3 [VI 1.32 PGUQU-4-F 4.50 % PPGIJ-3-F 1.00 % PUQU-3-F 11.50 % PYP-2-3 3.00 % Mixture Mi APUQU-3-F 4.00 % Clearing Point [°C]: 84.4 CC-3-V 42.00 % An [589 nm, 20°C]: 0.1090 CC-3-V1 4.00 % Ac [i kHz, 20°C]: 8.6 CCP-3-1 s.oo% c1[lkHz,20°C]: 3.4 CCP-30CF3 9.00 % K1 [20 °C]: 13.4 CUP-V-i 6.00 % K3 [20 °C] 14.4 DPGIJ-4-F 5.00 % 71 [20 °C, mPas]: 70 PCU-2-F 6.oo % V3 [V] 1.32 PGUQU-3-F 8.oo % PCUQU-4-F 7.00 % PPGU-3-F 1.00 % PY-3-02 3.00 % Mixture M2 BCH-32 1.00 % Clearing Point [°C]: 84.5 CBC-33 3.00 % An [589 nm, 20°C]: 0.1082 CC-3-V 42.50 % AE [1kHz, 20°C]: 8.2 CC-3-V1 7.00 % e [i kHz, 20 °C]: 3.4 CCP-30CF3 9.50% K1 [20 °C]: 13.3 CPGU-3-OT 6.50 % K3 [20 °C] 14.5 CY-5-02 4.00 % 71 [20 °C, mPas]: 71 DPGIJ-4-F 5.00 % V0 [VI 1.34 PGU-2-F 1.00 % PGU-3-F 3.00 % PCUQU-3-F 6.oo % PCUQU-4-F 5.00 % PPGU-3-F 1.00 % PUQU-3-F 5.50% Mixture Mgg APIJQIJ-2-F 4.00 % Clearing Point [°C]: 74.5 APUQU-3-F 8.oo % An [589 nm, 20°C]: 0.1212 BCH-3F.F.F 4.00 % AE [i kHz, 20°C]: 10.9 CBC33 2.00% E_ [i kHz, 20°C]: 11.57 CC-3-V 45.50 % K1 [25 °C]: 11.1 CCP-V-i 2.00 % 1(3 [25 °C]: 11.5 PGP-2-2V 5.00 % 7i [25 °C, mPa-s]: 55 PCU-2-F 8.oo % PGUQU-3-F 8.oo % PGUQU-4-F 7.00 % PPGU-3-F 1.00 % PYP-2-3 2.50 % -152 -Mixture Mg4 CC-3-V 38.00 % Clearing Point [°C]: 78 CC-3-V1 2.00 % An [589 nm, 20°C]: 0.1059 CCP-V-i 12.00 % As [1kHz, 20°C]: 5.0 CCP-3-1 3.00% e_ [i kHz, 20°C]: 4.3 CCP-30CF3 8.oo % K1 [20 °C]: 13.1 APUQU-3-F 8.oo % K3 [20 °C]: 14.2 PGUQU-3-F 3.50 % 71 [20 °C, mPas]: 63 PCUQU-4-F 5.50 % V0 [V] 1.67 CPGTJ-3-OT 5.00 % PY-3-02 15.00 % Mixture M35 APUQU-2-F 8.50 % Clearing Point [°C]: 75.5 APUQU-3-F 8.00 % An [589 nm, 20°C]: 0.1005 CC-3-V 44.50 % As [i kHz, 20°C]: 9.6 CCP-30CF3 7.50% s_ [i kHz, 20°C]: 3.8 CCP-V-i 8.oo % K1 [20 °C]: 12.6 DPGU-4-F 3.50 % IC [20 °C]: 13.8 PCUQU-4-F 3.50 % 71 [20 °C, mPas]: 6 PUQU-3-F 5.50 % COY-3-02 8.oo % PY-3-02 3.00 % -153 -Mixture M6 CC-3-V 8.00 % Clearing Point [°C]: 102.5 CPGP-5-2 5.00 % An [589 nm, 20°C]: 0.1995 CPGP-4-3 5.00 % As [1kHz, 20°C]: 5.1 CPCP-5-3 5.00% e_ [i kHz, 20°C]: 4.0 PCH-3o1 10.00 % PGTGT-3-F 6.oo % PGP-2-2V 16.00 % PGF-2-3 5.00 % PGP-2-4 5.00 % PGP-2-5 10.00 % PCUQU-4-F 6.oo % PCUQU--F 2.00 % Pp-1-2V1 4.00 % PUQU-3-F 10.00 % Y-40-04 3.00 % Mixture Mg7 CC-3-V 29.50 % Clearing Point [°C]: 80 CC-3-V1 6.00 % An [589 nm, 20°C]: 0.1056 CCP-V-i 12.00 % As [1kHz, 20°C]: 6.i CCP-3-1 5.00% e_ [i kHz, 20°C]: 4.3 CCP-30CF3 8.oo % K1 [20 °C]: 13.7 CCP-oCF3 2.00 % K3 [20 °C]: 14.8 APUQU-2-F 8.oo % 7. [20 °C, mPas]: 74 APIJQIJ-3-F 8.oo % V0 [V] 1.57 PGUQU-3-F 3.00 % PGUQU-4-F 3.50 % PY-3-02 15.00 % Mixture M8 APUQU-2-F 6.oo % Clearing Point [°C]: 79.5 APUQU-3-F 6.oo % An [589 nm, 20°C]: 0.1094 CC-3-V 40.00 % As [i kHz, 20°C]: 11.5 CCP-30CF3 9.00 % s [i kHz, 20°C]: 4.5 CCP-V-i 1.00 % K1 [20 °C]: 12.2 CPCU-3-OT 5.50 % 1(3 [20 °C]: 13.0 CCQU3F 1.00 % 7i [20 °C, mPas]: 8 CY-3-02 10.00 % V0 [V] 1.08 PGUQU-3-F 4.50 % PGUQU-4-F 8.oo % PGUQU-s-F 5.00 % DPGU-4-F 4.00 % -155 -Mixture gg CC-3-V 50.00 % Clearing Point [°C]: 79.5 CC-3-V1 6.50 % An [589 nm, 20°C]: 0.1053 PUQU-3-F 1.00 % As [i kHz, 20°C]: 5.9 APUQU-2-F 1.00% s_ [i kHz, 20°C]: 4.1 APUQU-3-F 9.00% K1 [20 °C]: 12.9 PGUQU-3-F 5.00 % K3 [20 °C]: 14.8 PGUQU-4-F 9.00 % 71 [20 °C, mPas]: 66 CPY-2-02 1.50 % V0 [V] 44.93 CPY-3-02 14.50 % PYP-2-4 2.50 % Mixture M40 CC-3-V 51.00 % Clearing Point [°C]: 79.5 CC-3-V1 4.00 % An [589 nm, 20°C]: 0.1089 PUQU-3-F 1.00 % As [i kHz, 20°C]: 5.9 APUQU-3-F 7.50% s_ [i kHz, 20°C]: 4.2 PGUQU-3-F 5.00% K1 [20 °C]: 12.8 PCUQU-4-F 9.00 % IC [20 °C]: 14.6 PCUQU--F 2.50 % 71 [20 °C, mPas]: 67 CPY202 1.50 % V0 V] 45.11 CPY-3-02 14.50 % PYP-2-4 4.00 % -i6 -Mixture M41 CC-3-V 52.00 % Clearing Point [°C]: 79.0 CC-3-V1 3.00 % An [589 nm, 20°C]: 0.1058 CCP-30CF3 1.00 % As [1kHz, 20°C]: 4.9 PUQU-3-F 1.50% e_ [i kHz, 20°C]: 4.2 APUQU-3-F 9.00% K1 [20 °C]: 12.7 PGUQU-3-F 5.00 % K3 [20 °C]: 14.5 PGUQU-4-F 6.o % 71 [20 °C, mPas]: 6 CPY-2-02 2.00 % V0 [V] 1.69 CPY-3-02 15.00 % PYP-2-4 5.00 % Mixture M42 CC-3-V 41.00 % Clearing Point [°C]: 79.0 CC-3-V1 7.00 % An [589 nm, 20°C]: 0.1055 CCP-V-i 5.00 % As [1kHz, 20°C]: 5.1 CCP-30CF3 8.oo% e_[lkHz,2o°C]: 4.1 APUQU-3-F 9.00% K1 [20 °C]: 13.4 PCUQU-3-F 5.00% 1K [20 °C]: 14.6 PGUQU-4-F 3.00 % y [20 °C, mPas]: 65 CPGU-3-OT 5.00 % \T [V] 1.70 CPY-2-02 3.00 % CPY-3-02 3.00 % PY-3-02 9.00 % PYP-2-4 2.00 % -157-Mixture M4g APUQIJ-2-F 6.00 % Clearing Point [°C]: 80.2 APUQU-3-F 6.00 % An [589 nm, 25°C]: 0.1043 BCH-32 4.50% As [1kHz, 25°C]: 8.4 CC-3-V 31.00 % e_ [i kHz, 25 °C]: 4.0 CC-3-V1 3.50 % K1 [25 °C]: ii.6 CCP-3-1 3.50% K3 [25 °C]: 13.1 CCP-V-i 18.00 % 7i [25 °C, mPas]: 60 CDUQU-3-F 4.00 % V0 [V] 1.24 PGP-2-2V 2.00 % PGUQU-3-F 5.50 % PCUQU-4-F 5.00 % PPGU-3-F 0.50 % PUQU-3-F 4.50 % Y-40-04 6.oo % Mixture M44 BCH-3F.F.F 10.00 % Clearing Point [°C]: 85.4 CC-3-V 23.50 % An [589 nm, 20°C]: 0.1071 CC-3-V1 7.00 % As [1kHz, 20°C]: 6.8 CCGU3F 5.00% s_ [i kHz, 20°C]: 3.5 CCP-30CF3 9.00 % K1 [20 °C]: 13.4 CCP-3F.F.F 8.oo % 1(3 [20 °C]: 14.8 CCPV1 11.00 % ii [20 °C, mPas]: 83 CCP-V2-1 3.00 % V0 [V] 1.48 DPGU-4-F 3.00 % PGP-2-2V 3.00 % PPGIJ-3-F 1.00 % PUQU-3-F 10.50 % PY-3-02 6.00 % -is8 -Mixture M45 CC-3-V 33.00 % Clearing Point [°C]: 84.8 CCP-3-1 6.00 % An [589 nm, 20°C]: 0.1182 CCP-30CF3 4.00 % As [1kHz, 20°C]: 8.5 CCP-V-i 13.50% e_ [i kHz, 20°C]: 3.9 CDUQU-3-F 1.00% K1 [20 °C]: 12.8 CPGP-5-2 2.00 % K3 [20 °C]: 14.8 CPGU-3-OT 4.50 % 7i [20 °C, mPas]: 82 DPGIJ-4-F 5.00 % V0 [V] 1.29 PGU-2-F 3.00 % PGUQU-3-F 7.00 % PPGU-3-F 1.00 % PUQU-3-F 12.00 % PY-3-02 8.oo % Mixture M46 BCH-3F.F.F 8.oo % Clearing Point [°C]: 85.5 CC-3-V 22.00 % An [589 nm, 20°C]: 0.1028 CC-3-V1 7.00 % AE [1kHz, 20°C]: 6.8 CCGU-3-F 7.00% s_ [i kHz, 20°C]: 3.6 CCP-30CF3 9.00 % K1 [20 °C]: 13.2 CCP-3F.F.F 8.oo % 1(3 [20 °C]: 14.9 CCP-V-i 12.00 % y [o °C, mPas]: 83 CCP-V2-1 2.00 % V0 [V] 1.47 CCGU-3-F 4.50 % PCP-2-2V 2.00 % PPGU-3-F 1.00 % PUQU-3-F 11.50 % PY-3-02 6.oo % -159 -Mixture M47 PUQU-3-F 12.00 % Clearing Point [°C]: 86.3 APUQU-3-F 6.00 % An [589 nm, 25°C]: 0.1194 PGUQU-3-F 5.00% As [1kHz, 25°C]: 6.9 PCUQU-4-F 5.00 % e_ [i kHz, 25 °C]: 3.8 CC-3-V 28.00 % K1 [25 °C]: 13.3 CC-3-V1 5.00% K3 [25 °C]: 14.2 CCP-V-i 12.00 % 71 [25 °C, mPa-s]: 70 CCP-V2-1 12.00 % V0 [V] 1.45 PYP-2-3 10.00 % CPY-3-02 2.00 % PY-3-02 3.00 % Mixture M48 APUQU-3-F 6.00 % Clearing Point [°C]: 115.1 CBC-33 4.00 % An [589 nm, 25°C]: 0.1211 CBC-53F 3.25 % As [i kHz, 25°C]: .8 CC-3-V 27.25 % c_ [i kHz, 25 °C]: 3.2 CC-3-V1 7.00 % CCCU-3-F 6.oo % CCP-3-1 4.00 % CCP-V-i 12.00 % CPCP-5-2 3.75 % PGP-2-3 5.00 % PCP-2-4 4.75 % PUQU-3-F 11.75 % CCY-3-02 5.25 % -i6o -Mixture M4g APUQIJ-2-F 6.00 % Clearing Point [°C]: 80.4 APUQU-3-F 5.50 % An [589 nm, 25°C]: 0.1038 CC-3-V 32.00% As [1kHz, 25°C]: 11.4 CCP-3-1 7.00 % e_ [i kHz, 25 °C]: 4.1 CCP-30CF3 7.00 % K1 [25 °C]: 11.4 CCP-V-i 6.oo % K3 [25 °C]: 11.7 CDUQU-3-F 8.00% 7i [25 °C, mPas]: 71 CPCU-3-OT 5.00% V0 [V] i.o6 DPGU-4-F 4.00 % PGU-2-F 2.50 % PCUQU-3-F 4.00 % PPGU-3-F 0.50 % PUQU-3-F 6.o % Y-40-04 6.oo % Mixture Mso BCH-32 1.00 % Clearing Point [°C]: 85.7 CC-3-V 35.00 % An [589 nm, 20°C]: 0.1104 CC-3-V1 5.00% As [1kHz, 20°C]: 8.4 CCP-30CF3 8.50 % s [i kHz, 20°C]: 3.6 CCP-V-i 15.00% K1 [20 °C]: 13.2 DPGU4F 6.oo % \Tc, [V] 1.33 PCU-2-F 6.oo % PGUQU-3-F 5.00 % PGUQU-4-F 5.00 % PPGU-3-F 1.00 % PUQU-3-F 5.00 % Y-40-04 3.00 % -161 -Clauses: The following clauses are not claims but represent different embodiments of the present invention.

1. Liquid-crystalline medium having a positive anisotropy, characterised in that it contains one or more compounds of the formula IA, RA C F20 4XA and at least one compound selected from the group of compounds of the formula hA, tIB and I1C, 1 2 R2AZ2(O)CH2+1 TTA 2 1

IIB

6 54 3 R2C(O)CVH2V+I TIC, in which RA, Rk, R2B and R2C each, independently of one another, denote H, an alkyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals maybe replaced by -0-, -S-, -K- -CF2O-, -OCF2-, -OC-0-or -0-CO-in such a way that 0 atoms are not linked directly to one another, denotes 0 -0--C)-or denotes -cli, 0' -Cl)--' C> or X" denotes F, Cl, CN, SF5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms, and -163 - (-6 each, independently of one another, denote H or F. Li and L2 each, independenfly of one another, denote F, Cl, CF3 or CHF2, each, independenfly of one another, denote H, F, C, CF3 or CHF2, but at least two of L6 denote F, Cl, CF3 or CHF2 Z2 and Z2 each, independently of one another, denote a single bond, -CH2CH2-, -CH=CH-, -CC-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CH=CHCH2O-, p denotes 1 or 2, and, in the case where Z2 = single bond, p may also denote o, o and q each, independently of one another, denote o or 1, (O)CVH2V±1 denotes OCVH2V+l or CH2+,, and v denotes 1 to 6.

2. Liquid-crystalline medium according to Glause 1, characterised in that it contains one or more compounds sekcted from the compounds of the formulae IA-i to 1A-, RAOC F20 XA L&-i -164 -RAC F20 XA L&-2 RA F20 XA IA-3 RAC F20 XA Y5 Y3 Yl IA-5 F20 Y4 Y in which RA, XA and -have the above indicated meanings according to Clause i and Y7 and Y each, independently denote H or F. 3. Liquid-crystalline medium according to Clause 1 or 2, characterised in that it contains one or more compounds selected from the compounds of the formulae TA-ia to IA-4d, -165 -RACF2O4XA -1a

F

RACF2O4XA ib

F F

RACF2OXA IA-ic RACF2OXA IA-id

F

RACF2OXA IA-ic RACFOXA a-if

F

-i66 -RACF2O4XA -2a

F

RACF2O4XA -2b

F F

RACF2OXA IA-2c RACF2OXA IA-2d

F

RACF2OXA IA-2e RACFOXA -2f

F

RACF2OXA L&-2g RACF2OXA L&-2h

F

RACF2O*XA L&-2i

F F

F20 4XA IA-3a

F

RACF2O 4XA TA-3b

F F

RA F20 XA L&-3 -i68 -

F F

RA_(J 0>-K IS-(IE--F20 XA IA-Ed

F

F F F

RA F20

F F F

RA_C:>-5-__ci--c F20 -_6i;--J--_ XA IA-3f

F

RACF2O XA IA-3g RA C F20 xA 3h

F

RA C F20 XA 3i

F F

-169 -IA-4a IA-4b IA-4c IA-4d in which RA and X' have the meanings indicated in Clause 1.

4. Liquid-crystalline medium according to one or more of Clauses 1 to 3, characterised in that X in formula IA denotes F, OCF3, OCHF2, CF3, OCHF2, OCHFCF3, OCF2CHFCF3, CF=CF2, CH=CF2, OCF=CF2 or OCH=CF2.

5. Liquid-crystafline medium according to one or more of Clauses ito 4, characterised in that it contains one or more compounds of the formula TTA-i to ITC-6, -170 -

F F

aIkyI___)___b__aIkyI* HA-i

F F

ITA-2 aIkyIaIkyI* aIkyIOaIkyI* 14

F CI

aIkyI___KT_____aIkyI* ITA-5

F CI

ITA-6 IJA-7 -17i -

F F

IJA-8 aIkyI__4______-aIkyI* ITA-9 IJA-io

F CI hA-u

F CI

ITA-12

F F

aIkyIC2H4aIkyI* IL&13

F F

aIkyIC2H4OaIkyI* 1-14 -172 -aIkyIC2H4aIkyI* IL&-15 aIkyIC2H4OaIkyI* I-i6

F CI

aIkyIC2H4aIkyI* I17

F CI

aIkyIC2H4OaIkyI* Ii8

F F

IIA-19

F F

ITA-2o

F F

aIkyICF2(O)aIkyI* ITA21 -173 -

F F

aIkyIOCF2(O)aIkyI* 122

F F

aIkyICH=CHCH2(O)aIkyI* I-23 alkyl ( ® ) CF2O(O)aIkyI* 1-24 alkyl ( ® ) CF2O(O)aIkyI* 1-25

F F

aIkyICH2O (O)aIkyI* 1TA26

F F

aIkyIOCH2(O)aIkyI* 127

F F 1-28

-174 -aIkenyIOaIkyI* IL&29 aIkenyIaIkyI* 130 aIkenyIOaIkyI* I-31 aIkenyIaIkyI* I-32 aIkenyIOaIkyI* IL&-33 1TA34 aIkenyIOaIkyI* -175 -aIkenyIaIkyI* 1-36 aIkenyIOaIkyI* I-37 IJA-38 aIkenyIOaIkyI* I-39

F F

aIkenyIC2H4aIkyI* I-4o

F F

aIkenyIC2H4OaIkyI* I-41

F F

aIkyICH=CH(O)aIkyI* 1-42 -176 -aIkyICO(O)aIkyI* 1-43

F F

aIkyI___Q______aIkyI* 144

F F

IJA-45 aIkyIaIkyI* I-46 aIkyIOaIkyI* 147

F CI

aIkyI__-D___b__aIkyI* IJA-48

F CI 49

-177 -

F F

aIkyI___Q___b__aIkyI* IJA-50

F F

aIkYI___CQ_____OaIkYI* ITA-51

F F

aIkyI__()_____aIkyI* IJA-52

F F

aIkyIOaIkyI* 153

F F

aIkyI___K___j__aIkyI* IIA-54

F F

aIkyI___<D___b__OaIkyI* IJA-55 IIA-56 -178 -

F F

IJA-57 aIkyI___1___G___b__aIkyI* ITA-58 IJA-59

F F ITA6o

aIkyIQaIkyI* I-6i IIA-62 IIA-63 -179 -

F F

aIkyIOOaIkyI* IL&-64 JIB-i IIB-2 JIB-3 JIB-4 IIB-5 aIkyIOaIkyI* JIB-6 -iSo -

F F

aIkyI___CH=CH_(_____(O)aIkyI* 11B7 aIkyIC2H(O)aIkyI* ITB-8

F F

IIB-9 aIkyICF2O(Q)aIkyI* IIB-io aIkyIOaIkyI* IIB-ii aIkyIaIkyI* IIB-12 aIkyIOaIkyI* IIB-13 -i8i-aIkyIOaIkyI* IIB-14 IIB-15 aIkenyIOaIkyI* IIB-i6 ITC-i IIC-2 aIkyI* ITC-3 IIC-4 -182 -IIC-5 aIkenyIOaIkyI* IIC-6 in which alkyl and alkyP each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms and alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms.

6. Liquid-crystalfi ne medium according to one or more of Clauses ito 5, characterised in that it additionally contains one or more compounds selected from the formulae III and/or IV, ROCF20XO Y3 Yl

IV

06 0 CF2O 0 X° Y Y2 in which R° denotes a halogenated or unsubstituted alkyl or alkoxy radical having ito 15 C atoms, where, in addition, one or more CH2 groups in these -183 -radicals may each be replaced, independently of one another, by -CC-, -CF2O-, -CH=CH-, -c-, -ØC)-, -0-, -C0-0-or -0-CO-in such a way that 0 atoms are not linked directly to one another, X° denotes F, Cl, CN, SF5, SCN, NCS, a halogenated akyl radical, a halogenated alkenyl radica', a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having lip to 6 C atoms, and y-each, independenfly of one another, denote H or F, and each, independently of one another, denote or 7. Liquid-crystalline medium according to one or more of Clauses ito 6, characterised in that it additionally contains one or more compounds selected from the formu'ae V to lix, R° xo V

VI

R° ZO* X° R° -{--(j9---Z0___ 0 x° Ix in which denotes a halogenated or unsubstituted alkyl or alkoxy radical having ito 15 C atoms, where, in addition, one or more CF2 groups in these radicals may each be replaced, independently of one another, by -CC-, -CF2O-, -0-, -c-, -CH=CH-, -C0-O-or -0-CO-in such a way that 0 atoms are not linked directly to one another, denotes F, Cl, CN, SF5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radica', a halogenated alkoxy radical or a halogenated alkenyloxy radical having lip to 6 C atoms, y-4 each, independently of one another, denote H or F, -185 -Z denotes -C2H4-, -(CH2)4-, -CH=CH-, -CF=CF-, -C2F4-, -CH2CF2-, -CF2CH2-, -CH2O-, -OCH2-, -COO-or -OCF2-, in formula VT and VIT also a single bond and in formula VT and IX also -CF2O-, r denotes o or 1, and s denotes 0 or 1.

8. Liquid-crystalline medium according to one or more of Clauses ito 7, characterised in that it additionally contains one or more compounds selected from the formu'ae X to XITT,

X

aIkenyI__K'__K_aIkenyI* XT aIkenyI---_----R KIT

L

XTTT

alkeriyl H H 0 X° in which X has the meanings indicated in Clause 7, and L denotes H or F, "alkyl" denotes C16-alkyl, -i86 -denotes C16-alky, CFb-alkoxy or C26-alkenyi, and "alkenyF and alkenyl*fl each, independently of one another, denote C2i-alkenyl.

9. Liquid-crystalline medium according to one or more of Clauses 1 to 8, characterised in that it additionally contains one or more compounds of the formula XW,

XIV

in which R' and R2 each, independenfly of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or aIkeny, each having up to 6 C atoms.

10. Liquid-crystalline medium according to one or more of Clauses 1 to 9, characterised in that it additionally contains one or more compounds of the formula XVII,

XVII

in which R' and R2 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms, and L denotes H or F. ii. Liquid-crystalline medium according to one or more of Clauses ito 10, characterised in that it contains one or more compounds selected from the group of the compounds of the formulae XXVTTI to XXXI, )O(VII1 X° cIx -C xc C F2 X° in which R0 and X have the meanings indicated in Clause 7.

12. Liquid-crystalline medium according to one or more of Clauses ito ii, characterised in that it contains one or more compounds selected from the group of the compounds of the formulae Xix, XX, XXt, Xxii, Xxiii and xxiv, R° ° XIX -i88 -02H R° xc

X XXIIT R° X°

in which R° and X have the meanings indicated in Clause 7, and Y'4 each, independently of one another, denote H or F. -189 - 13. Liquid-crystalline medium according to one or more of Clauses ito 12, characterised in that it contains »= 20% by weight of the compound of the formula Xb, al kyl in which alkyl has the meaning indicated in Clause 5.

14. Liquid-crystalline medium according to one or more of Clauses ito 13, characterised in that it contains at least two compounds of the formula IA and at least two compounds of the formu'a TIA.

15. Liquid-crystalfi ne medium according to one or more of Clauses ito 14, characterised in that it contains in tota' »= 20 % by weight of compounds of the formula IA and compounds of the formula TTB, based on the mixture.

16. Liquid-crystalline medium according to one or more of Clauses ito 15, characterised in that it contains in total »= 20 % by weight of compounds of the formula IA and compounds of the formula TIC, based on the mixture.

17. Liquid-crystalline medium according to one or more of Clauses ito 16, characterised in that it has a dielectric anisotropy (Ac) of> i.5 at 20 °C and 1kHz.

i8. Liquid-crystalline medium according to one or more of Clauses ito 17, characterised in that it additionally contains one or more additive(s) selected from the group of the Uvstabilisers, dopants and antioxidants.

19. Liquid-crystalline medium according to one or more of Clauses i to 18, characterised in that it additionally contains one or more poymerisabe compounds.

-190 - 20. Process for the preparation of a liquid-crystalline medium according to one or more of Clauses ito 19, characterised in that one or more compounds of the formula TA and one or more compounds selected from the group of compounds of the formula TIA, tIB and TIC as defined in Clause 1, are mixed with one or more mesogenic compounds and optionally also with one or more additives and/or at least one polymerisable compound.

21. Use of a liquid-crystalline medium according to one or more of Clauses 1 to 19 for electro-optical purposes.

22. Use of the liquid-crystalline medium according to Clause 21 in shutter glasses, for 3D applications, in TN, PS-TN, STh, TN-TFT, OCB, IPS, PS-IPS, FF5, PS-FFS and PS-VA-TPS displays.

23. E1ectro-optica liquid-crystal display containing a liquid-crystalline medium according to one or more of Clauses ito 19.

-191 -

Claims (10)

1. Claims: Liquid-crystalline medium having a positive anisotropy, characterised in that it contains one or more compounds of the formula IA, RA C F20 4XA and at least one compound selected from the group of compounds of the formula TIA and JIB, 1 2TTAR2BZ2(O)CH+1 JIB in which RA, RZ\, and R211 each, independently of one another, denote H, an a1ky or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may be replaced by -0-, -S-, , -CC-, -CF2O-, -OCF2-, -0C-0-or -0-CO-in such a way that 0 atoms are not linked directly to one another, denotes -K5i'J--Q -(a)-' C) or X" denotes F, Cl, CN, SF5, SCN, NCS, a halogenated athyl radical, a halogenated alkeny radical, a halogenated alkoxy radical or a halogenated alkenythxy radical, each having up to 6 C atoms, and each, independenfly of one another, denote H or F. LI and L2 each, independently of one another, denote F, Cl, CF3 or CHF2, -193 -Z2 denotes a single bond, -CH2CH2-, -CH=CH-, -CC-, -CF2O-, -OCF2-, -CH2O-, -OCT-I2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CH=CHCH2O-, o denotesoori, (O)CH2±1 denotes OCH2+1 or CH2+,, and v denotes 1 to 6.
2. 2. Liquid-crystalline medium according to Claim 1, characterised in that it contains one or more compounds selected from the compounds of the formulae IA-i to JA-5, RAOC F20 XA IA-i RAC F20 XA RA F20 -K:-XA -194 -Y5 YlAR -\J--\f---\)--CF2O -(fi--X Ye Y4 Y2 Y3 Yl A A IA-5 R -\ -CF2O Ye V4 V2 in which RA, XA and yl-6 have the above indicated meanings according to Claim 1 and Y7 andY8 each, independently denote H or F.
3. 3. Liquid-crystalline medium according to Claim i or 2, characterised in that it contains one or more compounds selected from the compounds of the formulae TA-ia to IA-4d, IA-ia RACF2OXA IA-ic -195 -F F IA-idFF F F IA-leF F F IA-ifFF F F IA-2aFF F F IA-2bF FF F IA-2c-196 -RACF2OXA -2dFRACF2OXA -2e RACF2OXA IA-2fF IA-2gRACF2OXA TA-2hFRACFO*XA L&-2iF FF F FRA_(J 0>-K IS-(IE--F20 __Q__ XA IA-3 aFF F FRA_/J 0>-KIES--KI--c F20 xA 3bF FF F -f-X TA-3cF F __XA IA-3dFF F FRA C F20 XA 3eF F FRA_<>__K___CF2O IA-3fF-198 -RA F20 XA -3g RA F20 XA -3hF FRA__:>--_ci--c F20 XA JA3i IA-4a RACF2OXA IA-4b IA-4c -199 -F F F IA-4d

   Fin which RA and XA have the meanings indicated in Claim 1.
4. 4. Liquid-crystalline medium according to one or more of Claims 1 to 3, characterised in that X' in formula IA denotes F, OCF3, OCHF2, CF3, OCHF2, OCHFCF3, OCF2CHFCF3, CF=CF2, CH=CF2, OCF=CF2 or OCH=CF2.
5. 5. Liquid-crystalline medium according to one or more of Claims 1 to 4, characterised in that the compound of formula IA is selected from formula APIJQU-n-F, PUQU-n-F or PGIJQU-n-F,F FCnH2n+i__()__®___ CF2O-Ø--FF FF FPUQU-n-FF FCflH2fl+l__Ø_____CF2O__ F PGIJQIJ-n-FF Fwherein n denotes 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

   -200 -
6. 6. Liquid-crystalUne medium according to one or more of Claims ito 5, characterised in that it contains one or more compounds of the formula TTA- 23 to TIB-i4, FF IIA-23 FCI TIA-24 CI</F IIA-25 aIkyI__CF2O(f)_(O)aIkyI* aIkyIOOaIkyI* TIA-64 aIkyIOaIkyI* JIB-il aIkyIaIkyI* IIB-12 aIkyIOaIkyI* I1B-i aIkyIOaIkyI* IIB-14 in which aky and a&yP each, independenfly of one another, denote a straight-chain alkyl radical having 1-6 C atoms and a1keny denotes a straight-chain a1keny radical having 2-6 C atoms.
7. 7. Liquid-crystafline medium according to any one of Claims ito 5, characterised in that the compound of formula TIA and TTB are selected from formula Y-nO-Om and PY-n-Om respectively,F FCH2÷1 OOCmH2mi Y-nO-Om CnH2n+iOCmH2mi PY-n-Om wherein n and m each, independently of one another, denotes 0,1,2,3,4,5, 6, , 8, 9, 10, 11 or 12.-202 -
8. 8. Liquid-crystafline medium according to one or more of Claims ito 7, characterised in that it additionally contains one or more compounds of formula TTC, 6 54 3 R2O(O)CVH2VI llC, in which R2C denotes H. an ailcyl or alkenyl radical having up to 15 C atoms which is unsubstituted. monosubstituted hy CN or CR3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals niay be replaced by -0-, -S-, -K3---CC-. -CF2O-, -OCF2-, -OC-0-or -0-Co-in such a way that 0 atoms are not linked directly to one another.

   U-6 each, independenfly of one another, denote H, F, Cl, CF3 or CHF2, but at least two of U-6 denote F, Cl, CF3 or CHF2, (O)CH2÷1 denotes OCH2+1 or CH2+1, and v denotes I to 6.
9. 9. Liquid-crystalline medium according to Claim 8, characterised in that the compound of formula IIC is selected from formula TIC-i to IIC-6, aIkyI___(J___b___®__aIkyI* IIC-i IIC-2 aIkyI________aIkYI* IIC-3 IIC-4 aIkenYI__Ø_____5_aIkYI IIC-5 aIkenyIOaIkyI* IIC-6 in which alkyl and alkyl* each, independently of one another, denote a straight-chain aky radical having i-6 C atoms and alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms.
10. 10. Liquid-crystalline medium according to one or more of Claims 1 to 9, characterised in that it additionally contains one or more compounds selected from the formulae III and/or IV, ROCF204XO " vs vs w 06 0 CF2O 0 X° Y Y2 in which R° denotes a halogenated or unsubstituted alkyl or alkoxy radical having ito 15 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by -CC-, -CF2O-, -CH=CH-, -0-, -0-, -CO-0-or -0-CO-in such a way that 0 atoms are not linked di recfly to one another, X° denotes F, Cl, CN, SF5, SCN, NCS, a halogenated athyl radical, a halogenated a1keny radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having tip to 6 C atoms, and \Ii-6 each, independently of one another, denote H or F, and each, independently of one another, denote or -205 -ii. Liquid-crystalline medium according to one or more of Claims ito 10, characterised in that it additionally contains one or more compounds selected from the formulae Vto DC, R° -f-K-fr(--KT-xo V x° VI R° xo VIt R° ZO* X° -KiD-- x° Ix in which R0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having ito 15 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by -CC-, -CF2O-, -0-, -K, , -CH=CH-, -C0-0-or -0-CO-in such a way that 0 atoms are not linked directly to one another, X denotes F, Cl, CN, SF5, SCN, NCS, a halogenated athy] radical, a halogenated alkeny radical, a halogenated alkoxy radical or a halogenated alkenythxy radical having up to 6 C atoms, Y14 each, independently of one another, denote H or F, Z° denotes -C2H4-, -(CH2)4-, -CH=CH-, -CF=CF-, -C2F4-, -CH2CF2-, -CF2CH2-, -CH2O-, -OCH2-, -COO-or -OCF2-, in formula VI and Vii also a single bond and in formula VI and IX also -CF2O-, r denotes o or 1, and s denotes o or 1.12. Liquid-crystalline medium according to one or more of Claims ito ii, characterised in that it additionally contains one or more compounds selected from the formulae X to XTTT, aIkyI-----R' x XILXIIIalkenyl H I-I 0 X° in which X° has the meanings indicated in Claim ii, and L denotes H or F, "alkyl" denotes CEO-alkyl, denotes C16-alkyl, CFo-alkoxy or C26-alkenyl, and "alkenyl" and a1keny1* each, independently of one another, denote C26-alkenyL 13. Liquid-crystalline medium according to one or more of Claims 1 to 12, characterised in that it additionally contains one or more compounds of the formula XIV,R XIVin which Ri and R2 each, independenfly of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalky] or aIkeny, each having up to 6 C atoms.14. Liquid-crystalline medium according to one or more of Claims ito 13, characterised in that it additionally contains one or more compounds of the formula XVI, ROC F20 *XO WI in which R° denotes H, an alkyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstitutcd by CM or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may be rep'aced by -0-. -S-, , -CC-, -CF2O-, -OCF2-, -OC-0-or -0-CO-in such a way that 0 atoms are not linked directly to one another and, X° denotes F, Cl, CM, SF5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms, and Y and Y2 each, independently denote H or F, and -and -KI9'---retdenddh1tb of one another, or 15. Liquid-crystafline medium according to Claim 14, characterised in that the compound of formula XVI is selected from formula XVTa to XVIf, Ro* C F20 4 x° C F20 4 o XVIb ROCF2O4XO XVIc RO C F20 4 x° C F20 4 0 XVIe C F20 4 o XVIf in which, denotes H, an akyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at east monosubstituted by halogen, where, in addition, one or more CH2 groups in these radica's maybe replaced by -0-, -S-, -CC-, -CF2O-, -OCF2-, -OC-O-or -0-CO-in such a way that 0 atoms are not linked directly to one another, and X° denotes denotes F, Cl, GN, SF5, SCN, NCS, a halogenated alkyl radical, a haogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyoxy radical, each having up to 6 C atoms, and yl and y each, independently of one another, denote H or F. i6. Liquid-crystalline medium according to one or more of Claims ito 15, characterised in that it additionally contains one or more compounds of the formula XVII, R1-Ø@_R2 XVII in which R' and R2 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or aIkeny, each having up to 6 C atoms, and L denotes H or F. 17. Liquid-crystafline medium according to one or more of Claims ito 16, characterised in that it contains one or more compounds selected from the group of the compounds of the formulae XXVIII to XXXI,XXVIII XXIXR° -( :-EE--c C F2 X° in which R° and X have the meanings indicated in Claim

    ii.i8. Liquid-crystalline medium according to one or more of Claims ito 17, characterised in that it contains one or more compounds selected from the group of the compounds of the formu'ae XIX, XX, XXI, XXII, XXIII and XXIV, R° -(--(9--(--(j-0 R° C2H x R° 0 XXI XR° XXIV in which R° and X° have the meanings indicated in Claim ii, and y4 each, independently of one another, denote H or F. 19. Liquid-crystalline medium according to one or more of Claims ito 18, characterised in that it contains »= 20% by weight of the compound of the formula Xb, Xb in which alkyl has the meaning indicated in Claim 6.20. Liquid-crystalline medium according to one or more of Claims ito 19, characterised in that it contains at least two compounds of the formula IA and at least two compounds of the formula hA.21. Liquid-crystalline medium according to one or more of Claims ito 20, characterised in that it contains in total »= 20 % by weight of compounds of the formula IA and compounds of the formula JIB, based on the mixture.22. Liquid-crystalline medium according to Claim 8 or Claim 9, characterised in that it contains in tota' »= 20 % by weight of compounds of the formula JA and compounds of the formula IIC, based on the mixUire.23. Liquid-crystalline medium according to one or more of Claims ito 22, characterised in that it has a dielectric anisotropy (Ac) of> i.5 at 20 °C and 1kHz.24. Liquid-crystalline medium according to one or more of Claims ito 23, characterised in that it additionally contains one or more additive(s) selected from the group of the UV stabilisers, dopants and antioxidants.25. Liquid-crystalline medium according to one or more of Claims i to 24, characterised in that it additionally contains one or more polyrnerisable compounds.26. Process for the preparation of a liquid-crystalline medium according to one or more of Claims ito 25, characterised in that one or more compounds of the formula IA and one or more compounds selected from the group of compounds of the formala hA and JIB as defined in Claim i, are mixed with one or more mesogenic compounds and optionafly also with one or more additives and/or at east one polymerisable compound.27. Use of a liquid-crystalline medium according to one or more of Claims i to 25 for electro-optical purposes.28. Use of the liquid-crystafline medium according to Claim 27 in shutter glasses, for 3D applications, in TN, PS-TN, STN, TN-TFT, OCB, tPS, PS-JPS, FF5, PS-FFS and PS-VA-IPS displays.29. Electro-optical liquid-crystal display containing a liquid-crystalline medium according to one or more of Claims ito 25.-215 -