Liquid crystal medium and liquid crystal displays containing same and compounds - Patent Application 20070122997

Abstract

A liquid crystal medium and a liquid crystal display comprising the same and the compound are provided. The present invention relates to a liquid-crystalline medium having a nematic phase and comprising one or more compounds of the formula X, to the use of the liquid-crystalline medium in electro-optical displays, in particular active matrix displays based on the IPS or FFS effect, to displays of this type containing liquid-crystalline media of this type, to the use of compounds of the formula X to improve the transmission and / or response time of liquid-crystalline media comprising one or more additional mesogenic compounds, and to compounds of the formula X. TIFF2022538487000243.tif46166 (wherein the parameters have the meanings given in the specification.)

Description

[Technical Field]

[0001] The present invention relates to novel liquid-crystalline media, in particular for use in liquid-crystal displays, and to these liquid-crystal displays, in particular those using IPS (in-plane switching) or preferably FFS (fringe field switching) effects using dielectrically positive liquid crystals. The latter is also often called the SG-FFS (super grip FFS) effect and also XB-FFS (extra brightness FFS). In this effect, dielectrically positive liquid crystals are used, which simultaneously have a high dielectric constant parallel to and perpendicular to the molecular director, leading to a large average dielectric constant and a high dielectric ratio. The liquid-crystalline medium may additionally contain dielectrically negative compounds, dielectrically neutral compounds or both. The liquid-crystalline medium is used in a uniform (i.e. planar) initial alignment. The liquid-crystalline medium according to the invention comprises compounds which have a positive dielectric anisotropy and simultaneously have a large dielectric constant parallel to and perpendicular to the molecular director. [Background technology]

[0002] The media are distinguished by particularly high transmittance and reduced response times in each display, which are caused by a unique combination of physical properties, particularly the dielectric properties of the media, and in particular the (ε ⊥ / ε av. ) and the dielectric ratio of the medium (ε ⊥ / Δε), which in turn leads to excellent media performance in displays according to the invention.

[0003] IPS and FFS displays, which use dielectrically positive liquid crystals, are well known in the art and have been widely adopted in various types of displays, such as desktop monitors and TV sets, as well as for portable applications.

[0004] Recently, however, IPS and especially FFS displays using dielectrically negative liquid crystals have been widely adopted. FFS displays using dielectrically negative liquid crystals are sometimes called UB-FFS (ultra bright FFS). Such displays are disclosed in U.S. Patent Application Publication No. 2013 / 0207038. These displays are characterized by significantly increased transmittance compared to previously used IPS and FFS displays using dielectrically positive liquid crystals. However, these displays using dielectrically negative liquid crystals have the significant disadvantage of requiring higher operating voltages than the respective displays using dielectrically positive liquid crystals. The liquid crystal medium used in UB-FFS has a dielectric anisotropy of -0.5 or less, preferably -1.5 or less.

[0005] HB-FFS (high brightness FFS) has a dielectric anisotropy of 0.5 or more, preferably 1.5 or more. Media containing both dielectrically negative and dielectrically positive mesogenic liquid crystal compounds are disclosed, for example, in U.S. Patent Application Publication No. 2013 / 0207038 (Patent Document 1). These media have a dielectric anisotropy of ε ⊥ and ε av. The value of ε is already quite large, but the ratio (ε ⊥ / Δε) is relatively small.

[0006] According to the present application, however, an IPS or FFS effect with a dielectrically positive liquid crystal medium in homogeneous alignment is preferred.

[0007] The industrial application of this effect in electro-optical display elements requires LC phases that satisfy a number of requirements, among which are particularly important chemical resistance to moisture, air, and physical influences such as heat, infrared, visible and ultraviolet radiation, direct current (DC) and alternating current (AC) electric fields.

[0008] Furthermore, commercially usable LC phases are required to have a liquid crystal mesophase within a suitable temperature range and low viscosity.

[0009] The series of compounds having liquid crystal mesophases disclosed to date does not include a single compound that fulfills all of these requirements, and therefore, to obtain a material that can be used as an LC phase, a mixture of 2 to 25 compounds, preferably 3 to 18 compounds, is generally prepared.

[0010] Matrix liquid crystal displays (MLC displays) are known. Nonlinear elements that can be used to switch each individual pixel are, for example, active elements (i.e., transistors). The term "active matrix" is used when thin-film transistors (TFTs) are generally used, and the TFTs are typically arranged on a glass plate as a substrate.

[0011] Two technologies are distinguished: TFTs containing compound semiconductors such as CdSe or metal oxides such as ZnO, and TFTs based on polycrystalline silicon, especially amorphous silicon. The latter technology is currently of greatest commercial importance worldwide.

[0012] One glass plate of the display has a TFT matrix on its inside, while the other glass plate carries a transparent counter electrode on its inside. Compared to the size of the pixel electrodes, the TFTs are very small and have virtually no adverse effect on the image. This technology can also be extended to full-color displays, in which a mosaic of red, green, and blue filters is arranged so that a filter element faces each switchable pixel.

[0013] The most widely used TFT displays to date are usually operated in transmission with crossed polarizers and are backlit. For television applications, ECB (or VAN) or FFS cells are used, while monitors usually use IPS or TN (twisted nematic) cells, and notebooks, laptops and mobile applications usually use TN, VA or FFS cells.

[0014] The term MLC display is used herein to cover any matrix display with integrated non-linear elements, i.e. displays which, in addition to the active matrix, also comprise passive elements such as varistors or diodes (MIM, i.e. metal-insulator-metal). This type of MLC display is particularly suitable for television applications, monitors and notebooks, or for high-density information displays, for example in automobile manufacturing or aircraft cabins. In addition to problems related to the angular dependence of contrast and response time, MLC displays also suffer from problems due to the liquid crystal mixture not having a sufficiently high resistivity [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay, Vol. 84, September 1984, A210-288, "Matrix LCD Controlled by Double Stage Diode Rings", p. 141ff, Paris (Non-Patent Document 1); STROMER, M., Proc. Eurodisplay, Vol. 84, September 1984, "Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays", p. 145ff, Paris (Non-Patent Document 2)]. As the resistance decreases, the contrast of the MLC display deteriorates. Because the resistivity of the liquid crystal mixture generally decreases over the lifetime of an MLC display due to interactions with the display's internal surfaces, a high (initial) resistance is crucial for the display to have acceptable resistance values ​​over long periods of operation.

[0015] In addition to IPS displays (e.g., Yeo, S.D., Paper 15.3: "An LC Display for the TV Application," SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 758 and 759 (Non-Patent Document 3)) and the long-known TN displays, more recently displays using the ECB effect have been established as the so-called VAN (Vertically Aligned Nematic) displays, which are currently one of the three most important types of liquid crystal displays, especially for television applications.

[0016] Here, the most important designs can be mentioned: MVA (Multi-Domain Vertical Alignment, e.g., Yoshide, H. et al., Paper 3.1: "MVA LCD for Notebook or Mobile PCs (omitted)", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6-9 (Non-Patent Document 4) and Liu, C.T. et al., Paper 15.1: "A 46-inch TFT-LCD HDTV Technology (omitted)", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 750-753 (Non-Patent Document 5)), PVA (Patterned Vertical Alignment, e.g., Kim, Sang Soo, Paper 15.4: "Super PVA Sets New State-of-the-Art for LCD-TV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 760-763 (Non-Patent Document 6), ASV (Advanced Super View, e.g., Shigeta, Mitsuhiro and Fukuoka, Hirofumi, Paper 15.2: "Development of High Quality LCDTV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 754-757 (Non-Patent Document 7)). More recent versions of the VA effect are the so-called PAVA (Photo-Alignment VA) and PSVA (Polymer-Stabilized VA).

[0017] In a general way, the technologies are compared, for example, in the SID Seminar in Souk in June 2004, Seminar M-6: "Recent Advances in LCD Technology", Seminar Lecture Notes, M-6 / 1 to M-6 / 26 (Non-Patent Document 8) and Miller, Ian, SID Seminar 2004, Seminar M-7: "LCD-Television", Seminar Lecture Notes, M-7 / 1 to M-7 / 32 (Non-Patent Document 9). Although the response time of modern ECB displays has already been significantly improved by overdrive addressing methods, e.g., Kim, Hyeon Kyeong et al., Paper 9.1: "A57-in. Wide UXGA TFT-LCD for HDTV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 106-109 (Non-Patent Document 10), achieving video-compatible response times remains a problem that has not yet been satisfactorily solved, especially in switching grayscales (grey-out).

[0018] ECB displays, such as ASV displays, use liquid crystal media with negative dielectric anisotropy (Δε), while TN and all conventional IPS displays to date use liquid crystal media with positive dielectric anisotropy. However, there is currently an increasing demand for IPS and FFS displays that use dielectrically negative liquid crystal media.

[0019] In this type of liquid crystal display, liquid crystal is used as a dielectric whose optical properties change reversibly upon application of a voltage.

[0020] In general, in displays, i.e., in displays due to these effects, the operating voltage must be as low as possible, so liquid-crystalline media are used that are generally mainly composed of liquid-crystalline compounds that all have the same sign of dielectric anisotropy and the highest possible value of dielectric anisotropy.In general, relatively small amounts of neutral compounds are used, and compounds with a dielectric anisotropy of the opposite sign to that of the medium are avoided as much as possible.Thus, for example, in the case of liquid-crystalline media with negative dielectric anisotropy for ECB or UB-FFS displays, compounds with negative dielectric anisotropy are mainly used.The individual liquid-crystalline media used generally consist mainly, and more usually essentially, of liquid-crystalline compounds with negative dielectric anisotropy.

[0021] In the media used by the present application, since liquid crystal displays are generally intended to have as low an address voltage as possible, significant amounts of dielectrically positive liquid crystal compounds and generally only very small amounts of dielectrically negative compounds, or even no dielectrically negative compounds, are typically used, while in some cases small amounts of dielectrically neutral compounds can be beneficially used.

[0022] US Patent Application Publication No. 2013 / 0207038 (Patent Document 1) discloses liquid crystal media for HB-FFS displays and proposes improving the performance of FFS displays using liquid crystals with positive dielectric anisotropy by incorporating additional dielectrically negative liquid crystals. However, this approach requires compensating for the negative overall dielectric anisotropy value of the resulting medium due to the contribution of the added compound. This requires increasing the concentration of the dielectrically positive material, which reduces the amount of dielectrically neutral compound available as a diluent in the mixture, or alternatively requires the use of compounds with stronger positive dielectric anisotropy. Both of these alternatives have the significant drawback of increasing the response time of the liquid crystal in the display.

[0023] Liquid-crystalline media with positive dielectric anisotropy for IPS and FFS displays have already been disclosed. Some examples are given below.

[0024] CN104232105A, WO2014 / 192390A and WO2015 / 007173A disclose liquid crystal media of positive dielectric anisotropy, some of which have a fairly high dielectric constant perpendicular to the director.

[0025] Obviously, for the intended application of the display the nematic phase range of the liquid crystal mixture must be sufficiently wide.

[0026] Furthermore, the response time of the liquid-crystalline medium in the display must be improved, i.e., shortened. This is particularly important in displays for television and multimedia applications. In order to improve the response time, it has repeatedly been proposed in the past to optimize the rotational viscosity (γ1) of the liquid-crystalline medium, i.e., to achieve a medium with the lowest possible rotational viscosity. However, the results achieved here are inadequate for many applications, and it would therefore be desirable to find further optimization methods.

[0027] Adequate stability of the medium against external stresses, in particular UV exposure and heat, is very particularly important, which can be crucial for display applications, especially in mobile devices, such as mobile phones.

[0028] In addition to the relatively poor transmittance and relatively long response time of MLC displays, previously disclosed MLC displays have further drawbacks, such as their relatively low contrast, relatively high viewing angle dependence, and difficulty in reproducing grayscales (gray-out) in these displays, especially when viewed from oblique viewing angles, as well as their inadequate VHR and inadequate lifetime. To improve the energy efficiency of MLC displays and to improve the ability of individual MLC displays to accommodate fast-moving images, desirable improvements in the transmittance and response time of the displays are needed.

[0029] Therefore, there continues to be a strong demand for MLC displays that have very high resistivity, as well as a wide operating temperature range, short response time, and low threshold voltage, which allow for the generation of various gray levels (gray shading), and in particular, good and stable VHR. [Prior art documents] [Patent documents]

[0030] [Patent Document 1] US Patent Application Publication No. 2013 / 0207038 [Patent Document 2] Chinese Patent Application Publication No. 104232105 [Patent Document 3] International Publication No. 2014 / 192390 [Patent Document 4] International Publication No. 2015 / 007173 [Non-patent literature]

[0031] [Non-Patent Document 1] TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay, Vol. 84, September 1984, A210-288, "Matrix LCD Controlled by Double Stage Diode Rings", pp. 141ff, Paris [Non-patent document 2] STROMER, M., "Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays", Proc. Eurodisplay, Vol. 84, September 1984, pp. 145ff, Paris [Non-patent document 3] Yeo, S.D., Paper 15.3: "An LC Display for the TV Application," SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 758 and 759 [Non-patent document 4] Yoshide, H. et al., Paper 3.1: "MVA LCD for Notebook or Mobile PCs (omitted)," SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6-9 [Non-patent document 5] Liu, C.T. et al., Paper 15.1: "A 46-inch TFT-LCD HDTV Technology (omitted)," SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 750-753 [Non-patent document 6] Kim, Sang Soo, Paper 15.4: "Super PVA Sets New State-of-the-Art for LCD-TV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 760-763 [Non-Patent Document 7] Shigeta, Mitsuhiro and Fukuoka, Hirofumi, Paper 15.2: "Development of High Quality LCDTV," SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 754-757 [Non-patent document 8] SID Seminar at Souk, June 2004, Seminar M-6: "Recent Advances in LCD Technology", Seminar Lecture Notes, M-6 / 1~M-6 / 26 [Non-Patent Document 9] Miller, Ian, SID Seminar 2004, Seminar M-7: "LCD-Television", Seminar Lecture Notes, M-7 / 1~M-7 / 32 [Non-Patent Document 10] Kim, Hyeon Kyeong et al., Paper 9.1: "A57-in.Wide UXGA TFT-LCD for HDTV Applications," SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 106-109 Summary of the Invention [Problem to be solved by the invention]

[0032] The present invention aims to provide MLC displays based on the ECB, IPS or FFS effect that do not have or have reduced defects as indicated above and at the same time have very high resistivity values, not only for monitor and television applications but also for mobile applications, such as telephones and navigation systems, in particular mobile phones and navigation systems, where it must also be ensured that they can operate at very high and very low temperatures. [Means for solving the problem]

[0033] Surprisingly at least one compound, preferably two or more compounds of formula X (preferably selected from the group of compounds of sub-formulae X-1 and X-2, particularly preferably of sub-formulae X-1-1 and / or X-2-2 and / or X-2-3 and / or X-2-4 and / or X-2-5, more preferably of both formulae X-1 and X-2), and preferably additionally one or more compounds selected from the group of compounds of the formulae I, B and S (preferably selected from the group of compounds of sub-formulae I-1, I-2, I-3 and I-4, and B-1, and B-2 and S-1 and S-2, respectively, particularly preferably selected from the group of compounds of sub-formulae I-1 and / or I-2 and / or I-3 and / or I-4 and / or B-1 and / or B-2 and / or S-1 and / or S-2, most preferably selected from the group of compounds of formulae I-2, I-4, B-1, B-2 and S-2, most preferably selected from the group of compounds of both formulae I-1 and I-2 and formulae B-1 and / or B-2), and preferably additionally with at least one compound, preferably two or more compounds, selected from the group of compounds of formulae II and III (the compounds of formula II are preferably II-1 and / or II-2), and / or at least one compound, preferably two or more compounds, selected from the group of formula IV and / or V, and Preferably, one or more compounds selected from the group of formulae VII to IX (all formulas as defined hereinafter) in these display elements, It has been found that it is possible to achieve liquid crystal displays, particularly in IPS and FFS displays, that have low threshold voltages, sufficiently broad nematic phases, favorably relatively low birefringence (Δn) along with short response times, and at the same time have high transmittance, good stability against degradation by heat and UV exposure, and a stable, high VHR.

[0034] This type of medium can be used in particular for electro-optical displays with active matrix addressing, for IPS or FFS displays.

[0035] Therefore, the present invention provides a dielectric constant perpendicular to the director for a dielectric anisotropy of 2.0 or less (ε ⊥ / Δε) and a high dielectric constant (ε) perpendicular to the director, preferably 3.8 or more, preferably 4.5 or more, most preferably 6.0 or more. ⊥) and relates to a liquid-crystalline medium based on a mixture of polar compounds, comprising one or more compounds having the formula

[0036] A ratio of the dielectric constant perpendicular to the director to the dielectric anisotropy greater than or equal to 1.0 indicates that the dielectric constant perpendicular to the director (ε ⊥ ) versus the dielectric constant parallel to the director (ε ∥ ) ratio, i.e., the ratio (ε ∥ / ε ⊥ ) is equivalent to

[0037] The medium according to the invention preferably additionally comprises: one or more compounds selected from the group of compounds of formula II and III, preferably one or more compounds of formula II, More preferably, in addition, one or more compounds of formula III and Most preferably additionally one or more compounds selected from the group of compounds of formula IV and V, Again preferably, one compound selected from the group of compounds of formulae VI to IX (All expressions are defined below).

[0038] The mixtures according to the invention exhibit a very wide nematic phase range with a clearing point above 70° C., very favorable values ​​of the capacity threshold, relatively high values ​​of retention, and at the same time good low-temperature stability at −20° C. and −30° C. and very low rotational viscosity. The mixtures according to the invention are furthermore distinguished by a good ratio of clearing point and rotational viscosity and a relatively high positive dielectric anisotropy.

[0039] It has now been surprisingly found that by using certain selected liquid crystal media, FFS type LCs using liquid crystals with positive dielectric anisotropy can be realized. These media are characterized by a particular combination of physical properties. The most crucial of these are the dielectric properties of the medium, here the average dielectric constant (ε av. ) and the dielectric constant (ε ⊥ ) is high, and in particular, the ratio of these latter two values ​​(ε ⊥ / Δε) is relatively high.

[0040] The liquid-crystalline media according to the invention on the one hand preferably have values ​​of the dielectric anisotropy of 1.5 or more, more preferably 3.5 or more, more preferably 4.5 or more. On the other hand, they preferably have a dielectric anisotropy of 26 or less.

[0041] The liquid-crystalline media according to the invention on the one hand preferably have a value of the dielectric constant perpendicular to the director of 1.5 or more, more preferably 2 or more, more preferably 6 or more, and on the other hand preferably 20 or less.

[0042] Preferably, the liquid crystal media according to the invention have a dielectric ratio (ε ⊥ / Δε).

[0043] In a preferred embodiment, the liquid crystal medium according to the present invention has a positive dielectric anisotropy preferably in the range of 1.5 to 20.0, more preferably in the range of 3.0 to 8.0, most preferably in the range of 4.0 to 7.0.

[0044] In a preferred embodiment, the liquid-crystalline medium according to the present invention may be identical to the preferred embodiments described above. In a preferred embodiment, the liquid-crystalline medium has a dielectric constant (ε ) perpendicular to the director of the liquid-crystalline molecules of 5.0 or more, more preferably 6.0 or more, more preferably 7.0 or more, more preferably 8.0 or more, more preferably 9.0 or more, most preferably 10.0 or more. ⊥ ) DETAILED DESCRIPTION OF THE INVENTION

[0045] The liquid crystal medium of the present invention has a dielectric anisotropy of 0.5 or more, preferably 1.5 or more, and a dielectric ratio (ε ⊥ / Δε),

[0046] a) It contains one or more compounds of formula X at a concentration preferably in the range of 1% to 60%, more preferably in the range of 5% to 40%, and particularly preferably in the range of 8% to 35%.

[0047] [ka]

[0048] During the ceremony, R 1X and R 2X each independently represent H or an alkyl group having 1 to 15 C atoms, provided that one or more CH groups in these groups are not directly linked to O atoms, and are selected from -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] may be replaced independently by -O-, -CO-O- or -O-CO-, in which one or more H atoms may be replaced by halogen; Preferably R 1X preferably represents alkyl or alkoxy having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms, more preferably alkyl or alkoxy having 2 to 5 C atoms or alkenyl having 2 to 5 C atoms, Instead preferably R 2X is X X represents [ka] each occurrence being the same or different and representing a group selected from the group a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and decalin-2,6-diol, wherein one or more non-adjacent CH groups are optionally replaced by -O- and / or -S-, and wherein one or more H atoms are optionally replaced by F; b) the group consisting of 1,4-phenylene and 2,6-naphthylene, wherein one or two CH groups may be replaced by N, and, in addition, one or more H atoms may be replaced by L; c) the group consisting of 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, thiophene-2,5-diyl, selenophene-2,5-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, each of which may be mono- or polysubstituted by L; d) the group consisting of bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl and spiro[3.3]heptane-2,6-diyl, wherein one or more H atoms may be replaced by F; L are the same or different and represent a halogen, cyano, alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl group having 1 to 7 C atoms, with the proviso that one or more H atoms may be replaced by F or Cl; Z X are the same or different in each occurrence and represent a single bond, -CF2O-, -OCF2-, -CH2CH2-, -CF2CF2-, -C(O)O-, -OC(O)-, -C2O-, -OCH2-, -CF=CH-, -CH=CF-, -CF=CF-, -CH=CH- or -C≡C-; Y 1 represents Cl, CF3, CHF2, OCF3, CN or NCS, preferably Cl, CF3 or OCF3, more preferably CF3 or OCF3, Y 2 represents H, F, Cl, CF or CHF, preferably F, Preferably Y 1 and Y 2 On the other hand, preferably Y 1 is CF3 or OCF3, and the other represents H, F, Cl, CF3, OCF3 or CHF2, and X X represents F, Cl, CN, NCS, SF5, fluorinated alkyl, alkoxy, alkenyl or alkenyloxy, each having up to 5 C atoms, preferably F, CF3, OCF3 or NCS, and n represents 0, 1 or 2, preferably 0 or 1, and most preferably 1.

[0049] Preferably, the compound contains one or more additional compounds selected from the group of compounds satisfying the following conditions b) to f):

[0050] b) One or more dielectrically positive compounds selected from the group of compounds of formulae II and III, each preferably having a dielectric anisotropy of 3 or more, preferably one or more compounds of formula II.

[0051] [ka]

[0052] During the ceremony, R 2 represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, [ka] [ka] L 21 and L 22 represents H or F, preferably L 21 represents F, X 2 represents halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, preferably F, Cl, -OCF3, -O-CH2CF3, -O-CH=CH2, -O-CH=CF2 or -CF3, very preferably F, Cl, -O-CH=CF2 or -OCF3, m is 0, 1 or 3, preferably 1 or 2, particularly preferably 2, R 3represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, [ka] [ka] L 31 and L 32 represent independently H or F, preferably L 31 represents F, X 3 represents halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, F, Cl, -OCF3, -OCHF2, -O-CH2CF3, -O-CH=CF2, -O-CH=CH2 or -CF3, very preferably F, Cl, -O-CH=CF2, -OCHF2 or -OCF3, Z 3 represents -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CHO- or a single bond, preferably -CH2CH2-, -COO-, trans-CH=CH- or a single bond, very preferably -COO-, trans-CH=CH- or a single bond, and n is 0, 1, 2 or 3, preferably 1, 2 or 3, and particularly preferably 1.

[0053] c) optionally one or more preferably dielectrically neutral compounds selected from the group of compounds of formulae IV and V

[0054] [ka]

[0055] During the ceremony, R 41 and R42 are, independently of each other, R in formula II 2 has the meaning given above for R 41 represents alkyl, and R 42 represents alkyl or alkoxy, or R 41 represents alkenyl, and R 42 represents alkyl, [ka] [ka] Z 41 and Z 42 are independent of each other, and Z 41 appears twice, they also independently represent -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CHO-, -CF2O-, -C≡C- or a single bond, preferably one or more of them represents a single bond, and p represents 0, 1 or 2, preferably 0 or 1, and R 51 and R 52 are, independently of each other, R 41 and R 42 has one of the meanings given to Alkyl having 1 to 7 C atoms, preferably n-alkyl, particularly preferably n-alkyl having 1 to 5 C atoms, or Alkoxy having 1 to 7 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy having 2 to 5 C atoms, or represents an alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms, preferably having 2 to 4 C atoms, preferably alkenyloxy; [ka] Preferably [ka] represents [ka] [ka] Z 51 ~Z 53 are each, independently of one another, -CH-CH-, -CH-O-, -CH=CH-, -C≡C-, -COO- or a single bond, preferably -CH-CH-, -CH-O- or a single bond, particularly preferably a single bond, i and j each independently represent 0 or 1; (i+j) preferably represents 0, 1 or 2, more preferably 0 or 1, and most preferably 1.

[0056] d) Again optionally, preferably essentially, either alternatively or additionally, one or more dielectrically negative compounds selected from the group of formulae VI to IX.

[0057] [ka]

[0058] During the ceremony, R 61 teeth, unsubstituted alkyl groups having 1 to 7 C atoms, preferably linear alkyl groups, more preferably n-alkyl groups, most preferably propyl or pentyl; unsubstituted alkenyl groups having 2 to 7 C atoms, preferably linear alkenyl groups, particularly preferably those having 2 to 5 C atoms; an unsubstituted alkoxy group having 1 to 6 C atoms, or represents an unsubstituted alkenyloxy group having 2 to 6 C atoms, R 62 represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms, and l represents 0 or 1; R71 teeth, an unsubstituted alkyl group having 1 to 7 C atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, or represents an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably a linear alkenyl group, particularly preferably one having 2 to 5 carbon atoms, R 72 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, preferably 1, 2, 3 or 4 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, preferably 2, 3 or 4 C atoms, and [ka] R 81 teeth, an unsubstituted alkyl group having 1 to 7 C atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, or represents an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably a linear alkenyl group, particularly preferably one having 2 to 5 carbon atoms, R 82 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, preferably 1, 2, 3 or 4 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, preferably 2, 3 or 4 C atoms, [ka] Z 8 represents -(C=O)-O-, -CH2-O-, -CF2-O- or -CH2-CH2-, preferably -(C=O)-O- or -CH2-O-, and o represents 0 or 1, R 91 and R92 are, independently of each other, 72 has the meaning given to R 91 represents an alkyl group having preferably 2 to 5 C atoms, more preferably 3 to 5 C atoms, R 92 preferably represents an alkyl or alkoxy group having 2 to 5 C atoms, more preferably an alkoxy group having 2 to 4 C atoms or an alkenyloxy group having 2 to 4 C atoms, [ka] p and q each independently represent 0 or 1, and (p+q) preferably represents 0 or 1, [ka] Alternatively, preferably, p=q=1.

[0059] e) Optionally, but preferably essentially, one or more compounds selected from the group of compounds of formula B and / or S, preferably of formulae B-1 and B-2, S-1 and S-2, preferably in a concentration ranging from 1% to 60%, more preferably from 5% to 40%, particularly preferably from 8% to 35%.

[0060] [ka]

[0061] During the ceremony, [ka] [ka] n represents 1 or 2, preferably 1; R 1preferably represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl, alkoxy, alkenyl or alkenyloxy, more preferably alkyl, alkenyl, alkoxy or alkenyloxy, most preferably alkyl, and X 1 represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms and more preferably representing F, Cl, CF3 or OCF3.

[0062] [ka]

[0063] During the ceremony, [ka] [ka] n represents 1 or 2, preferably 1; R 1 preferably represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl, alkoxy, alkenyl or alkenyloxy, more preferably alkyl, alkenyl, alkoxy or alkenyloxy, most preferably alkyl, and X 1 represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms and more preferably representing F, Cl, CF3 or OCF3.

[0064] f) again optionally and preferably essentially, either alternatively or additionally, one or more compounds of formula I.

[0065] [ka]

[0066] During the ceremony, [ka] [ka] represents [ka] Preferably [ka] represents n represents 0 or 1, R 11 and R 12 each independently of one another preferably represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkyl, alkoxy or alkenyloxy, and R 11 Instead, use R 1 represents R 12 Instead of X 1 represents R 1 preferably denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, and X 1represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms and more preferably representing F, Cl, CF3 or OCF3, This group excludes compounds of formulae B and S.

[0067] The present invention also relates to compounds of formula X:

[0068] Preferably, the medium according to the present application comprises one or more compounds of formula X selected from the group of preferred compounds of sub-formulae X-1 and X-2 thereof.

[0069] [ka]

[0070] wherein the parameters have the respective meanings given above in formula X, preferably [ka] Represents.

[0071] In one preferred embodiment, the medium according to the present application comprises one or more compounds of formula X-1 selected from the group of preferred compounds of sub-formulae X-1-1 to X-1-4 thereof.

[0072] [ka]

[0073] where the parameters have the respective meanings given above.

[0074] In one preferred embodiment, the medium according to the present application comprises one or more compounds of formula X-1 selected from the group of preferred compounds of sub-formulae X-2-1 to X-2-6 thereof.

[0075] [ka]

[0076] where the parameters have the respective meanings given above.

[0077] The liquid-crystalline media according to the present application preferably have a nematic phase.

[0078] This application and in particular R 1 Throughout the definition, alkyl means an alkyl group, which may be linear or branched. Each of these groups is preferably linear and preferably has 1, 2, 3, 4, 5, 6, 7 or 8 C atoms, and is therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0079] When alkyl denotes a branched alkyl group, it preferably denotes 2-alkyl, 2-methylalkyl or 2-(2-ethyl)-alkyl, preferably 2-butyl (=1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular 2-methylbutyl, 2-methylbutoxy, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl and 2-dodecyl. Of these groups, 2-hexyl and 2-octyl are most preferred.

[0080] Branched groups, especially R, each of which results in a chiral compound 1 are also referred to in this application as chiral groups. Particularly preferred chiral groups are 2-alkyl, 2-alkoxy, 2-methylalkyl, 2-methylalkoxy, 2-fluoroalkyl, 2-fluoroalkoxy, 2-(2-ethyn)-alkyl, 2-(2-ethyn)-alkoxy, 1,1,1-trifluoro-2-alkyl and 1,1,1-trifluoro-2-alkoxy.

[0081] Particularly preferred chiral groups are 2-butyl (=1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular, for example, 2-methylbutyl, 2-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 2-ethylhexoxy, 1-methylhexoxy, 2-octyloxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpentyl, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl, 2-dodecyl, 6-methoxyoctoxy, 6-methyloctoxy, 6-methyloctanoyloxy, 5-methylheptyloxycarbonyl, 2-methyl butyryloxy, 3-methylvaleroyloxy, 4-methylhexanoyloxy, 2-chloropropionyloxy, 2-chloro-3-methylbutyryloxy, 2-chloro-4-methylvaleryloxy, 2-chloro-3-methylvaleryloxy, 2-methyl-3-oxapentyl, 2-methyl-3-oxahexyl, 1-methoxypropyl-2-oxy, 1-ethoxypropyl-2-oxy, 1-propoxypropyl-2-oxy, 1-butoxypropyl-2-oxy, 2-fluorooctyloxy, 2-fluorodecyloxy, 1,1,1-trifluoro-2-octyl, 1,1,1-trifluoro-2-octyl, and 2-fluoromethyloctyloxy. 2-Hexyl, 2-octyl, 2-octyloxy, 1,1,1-trifluoro-2-hexyl, 1,1,1-trifluoro-2-octyl and 1,1,1-trifluoro-2-octyloxy are highly preferred.

[0082] Preferably, the compound of formula B is selected from the group of compounds of formula B-1 and B-2.

[0083] [ka]

[0084] During the ceremony, R 1preferably denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, and X 1 represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms and preferably representing F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably OCF3 or CF3.

[0085] Preferably, the compound of formula S is selected from the group of compounds of formula S-1 and S-2.

[0086] [ka]

[0087] During the ceremony, R 1 preferably denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, and X 1 represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms and preferably representing F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably OCF3 or CF3.

[0088] Preferably, the compound of formula I is selected from the group of compounds of formula I-1, I-2, I-3 and I-4.

[0089] [ka]

[0090] During the ceremony, R 11 and R 12 each independently represents preferably alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkyl, alkoxy or alkenyloxy, R 1 preferably denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, and X 1 represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms and preferably representing F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably OCF3 or CF3.

[0091] The compounds of general formula X can be prepared in a manner known per se, precisely under known reaction conditions suitable for said reactions, as described in the literature (for example, standard works such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart). Here, use can be made of modifications known per se but not mentioned in detail here.

[0092] It is also possible, if desired, to form the starting material in situ by not isolating it from the reaction mixture but instead immediately converting it further to a compound of general formula X.

[0093] Preferred synthetic routes to compounds according to the invention are shown in the schemes below and further illustrated by the examples: The synthesis can be tailored to particular desired compounds of general formula X by the selection of appropriate starting materials.

[0094] <Scheme 1>

[0095] [ka]

[0096] where the parameters R, Y1, Y2 and X are the parameters R in the above formula. 1X , Y, Y and X X and Hal is halogen, preferably Br or I, provided that the 1,4-phenylene moiety of the halide, e.g., bromide, may optionally be substituted with one or two F atoms.

[0097] <Scheme 2>

[0098] [ka]

[0099] where the parameters R, Y1, Y2 and X are the parameters R in the above formula. 1X , Y, Y and X X have the respective meanings given to them.

[0100] <Scheme 3>

[0101] [ka]

[0102] where the parameters R, Y1, Y2 and X are the parameters R in the above formula. 1X , Y 1 , Y 2 and X Xwherein Hal is halogen, preferably Br or I, provided that the 1,4-phenylene moiety of the bromide may optionally be substituted by one or two F atoms.

[0103] <Scheme 4>

[0104] [ka]

[0105] where the parameters R, Y1, Y2 and X are the parameters R in the above formula. 1X , Y1, Y2 and X X wherein Hal is halogen, preferably Br or I, provided that each one 1,4-phenylene moiety of the bromide may optionally be substituted by one or two F atoms.

[0106] A further object of the present invention is to provide a compound of formula 1-Hal-2-Y 2 -3-Y 1 The method for synthesizing compounds of formula X from compounds of formula 1-4-X-phenyl is preferably according to the synthetic routes shown in Schemes 2 and 3 above. In a key step of the synthesis, the building block 1-Hal-2-Y 2 -3-Y 1 The 4-X-phenyl can be reacted with a ketone via a metal-mediated coupling reaction to give the respective tertiary alcohol, which can be subsequently dehydrated to the corresponding strylene derivative, which can undergo hydrogenation in the next step. Alternatively, the building block 1-Hal-2-Y 2 -3-Y 1 The -4-X-phenyl is reacted with an aromatic boronic acid derivative, preferably in a Suzuki coupling reaction, to give the corresponding biphenyl derivative, which is capable of undergoing hydrogenation.

[0107] The reactions described should be considered as illustrative only: those skilled in the art will be able to carry out corresponding modifications of the described syntheses and follow other suitable synthetic routes to obtain compounds of formula X.

[0108] The compounds of the general formula X can be used in liquid-crystalline media.The invention therefore also relates to a liquid-crystalline medium which contains one or more compounds of the general formula X and which contains two or more liquid-crystalline compounds.

[0109] The invention furthermore relates to liquid-crystal displays, in particular IPS or FFS displays, particularly preferably FFS or SG-FFS displays, which contain a liquid-crystalline medium according to the invention.

[0110] The present invention further relates to a liquid crystal display of the IPS or FFS type comprising a liquid crystal cell consisting of two substrates, at least one of which is transparent to light and at least one of which has an electrode layer, and a liquid crystal medium layer arranged between the substrates and comprising a polymerized component and a low molecular weight component, the polymerized component being obtainable by polymerizing one or more polymerizable compounds in the liquid crystal medium between the substrates of the liquid crystal cell, preferably under application of a voltage, and the low molecular weight component being a liquid crystal mixture according to the invention as described above and below.

[0111] The displays according to the invention are preferably addressed by active matrix (AMD, short for Active Matrix LCD), preferably by thin-film transistors (TFT), however the liquid crystals according to the invention can also be used to advantage in displays with other known addressing methods.

[0112] The invention further relates to a process for the preparation of a liquid-crystalline medium according to the invention by mixing one or more compounds of formula X, preferably one or more compounds selected from the group of the compounds of formulae XA and XB, with one or more low molecular weight liquid-crystalline compounds or liquid-crystalline mixtures and, optionally, with further liquid-crystalline compounds and / or additives.

[0113] Above and below, the following meanings apply:

[0114] Unless otherwise clearly indicated, the term "FFS" is used to refer to FFS and SG-FFS displays.

[0115] The term "mesogenic group" is known to those skilled in the art and described in the literature and refers to a group that essentially contributes to the generation of a liquid crystal (LC) phase in low-molecular-weight or polymeric substances due to the anisotropy of its attractive and repulsive interactions. A compound containing a mesogenic group (mesogenic compound) does not necessarily have an LC phase by itself. It is also possible for a mesogenic compound to exhibit liquid crystal phase behavior only after mixing with other compounds and / or polymerization. Typical mesogenic groups are, for example, rigid rod- or disc-shaped units. A review of the terms and definitions used in relation to mesogens or liquid crystal compounds is given in Pure Appl. Chem., Vol. 73 (No. 5), p. 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem., 2004, Vol. 116, pp. 6340-6368.

[0116] The term "spacer group" or "spacer" for short, also referred to as "Sp" above and below, is known to those skilled in the art and described in the literature, see, for example, Pure Appl. Chem., Vol. 73 (No. 5), p. 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340-6368. Unless otherwise indicated, the term "spacer group" or "spacer" above and below refers to a flexible group connecting the mesogenic group and the polymerizable group(s) in the polymerizable mesogenic compound.

[0117] For the purposes of the present invention, the term "liquid crystal medium" is intended to denote a medium comprising a liquid crystal mixture and one or more polymerizable compounds, such as, for example, reactive mesogens. The term "liquid crystal mixture" (or "host mixture") is intended to denote a liquid crystal mixture consisting only of non-polymerizable low molecular weight compounds, preferably two or more liquid crystal compounds and optionally further additives, such as, for example, chiral dopants or stabilizers.

[0118] Particular preference is given to liquid-crystalline mixtures or liquid-crystalline media which have a nematic phase, especially at room temperature.

[0119] In a preferred embodiment of the present invention, the liquid-crystalline medium comprises one or more dielectrically positive compounds selected from the group of compounds of the formulae II-1 and II-2 and / or selected from the group of compounds of the formulae III-1 and III-2 and having a dielectric anisotropy of 3 or more.

[0120] [ka]

[0121] wherein the parameters have the respective meanings given above in Formula II, and L 23 and L 24 are each independently H or F, preferably L 23 represents F, and [ka] In the case of formula II-1 and II-2, X 2 preferably represents F or OCF3, particularly preferably F, and In the case of formula II-2, [ka]

[0122] [ka]

[0123] wherein the parameters have the meanings given in Formula III.

[0124] The medium according to the invention may contain, instead of or in addition to the compounds of formula III-1 and / or III-2, one or more compounds of formula III-3.

[0125] [ka]

[0126] wherein the parameters have the respective meanings given above, and the parameter L 31 and L 32 represent H or F, independently of each other and other parameters.

[0127] The liquid crystal medium is preferably L 21 and L 22 and / or L 23 and L 24 and wherein both represent F.

[0128] In a preferred embodiment the liquid crystal medium is L 21 , L 22 , L 23 and L 24 and II-1 and II-2, wherein all of the above represent F.

[0129] The liquid-crystalline medium preferably comprises one or more compounds of formula II-1, which are preferably selected from the group of compounds of formulae II-1a to II-1e, preferably one or more compounds of formulae II-1a and / or II-1b and / or II-1d, preferably II-1a and / or II-1d or II-1b and / or II-1d, most preferably compounds of formula II-1d.

[0130] [ka]

[0131] wherein the parameters have the respective meanings given above, and L 25 and L 26 represent, independently of each other and of other parameters, H or F, Preferably, In formulae II-1a and II-1b, L 21 and L 22 Both represent F, In formulae II-1c and II-1d, L 21 and L 22 Both represent F and / or L 23 and L 24 both represent F, and In Formula II-1e, L 21 , L 22 and L 25 represents F.

[0132] The liquid-crystalline medium preferably comprises one or more compounds of the formula II-2, preferably selected from the group of the compounds of the formulae II-2a to II-2k, preferably one or more compounds of the formulae II-2a and / or II-2h and / or II-2j

[0133] [ka]

[0134] [ka]

[0135] [ka]

[0136] wherein the parameters have the respective meanings given above, and L 25 ~L 28 are each independently H or F, preferably L 27 and L 28 Both of these represent H, and particularly preferably, L 26 represents H.

[0137] The liquid crystal medium is preferably L 21 and L 22 Both represent F and / or L23 and L 24 and both represent F.

[0138] In a preferred embodiment the liquid crystal medium is L 21 , L 22 , L 23 and L 24 and wherein all of the following are F:

[0139] Particularly preferred compounds of formula II-2 are those of the following formulae, particularly preferred are compounds of formulae II-2a-1 and / or II-2h-1 and / or II-2k-2:

[0140] [ka]

[0141] [ka]

[0142] In the formula, R 2 and X 2 has the meaning indicated above, and X 2 preferably represents F.

[0143] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1, which are preferably selected from the group consisting of the compounds of the formulae III-1a to III-1j, preferably from the group consisting of the compounds of the formulae III-1c, III-1f, III-1g and III-1j

[0144] [ka]

[0145] [ka]

[0146] wherein the parameters have the meanings given above, preferably wherein the parameters have the respective meanings indicated above, Parameter L 35 and L 36 represent, independently of each other and of other parameters, H or F, Parameter L 35 and L 36 represent H or F, independently of each other and other parameters.

[0147] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1c, which are preferably selected from the group consisting of the compounds of the formulae III-1c-1 to III-1c-5, preferably from the group consisting of the compounds of the formulae III-1c-1 and / or III-1c-2, most preferably from the group of the compounds of the formula III-1c-1

[0148] [ka]

[0149] In the formula, R 3 has the meaning given above.

[0150] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1f, which are preferably selected from the group consisting of the compounds of the formulae III-1f-1 to III-1f-6, preferably from the group of the compounds of the formulae III-1f-1 and / or III-1f-2 and / or III-1f-3 and / or III-1f-6, preferably from the group of the compounds of the formulae III-1f-3 and / or III-1f-6, preferably from the group of the compounds of the formula III-1f-6

[0151] [ka]

[0152] In the formula, R 3has the meaning given above.

[0153] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1g, which are preferably selected from the group consisting of the compounds of the formulae III-1g-1 to III-1g-5, preferably from the group of the compounds of the formula III-1g-3

[0154] [ka]

[0155] In the formula, R 3 has the meaning given above.

[0156] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1h, which compounds are preferably selected from the group consisting of the compounds of the formulae III-1h-1 to III-1h-3, preferably from the group of the compounds of the formula III-1h-3

[0157] [ka]

[0158] where the parameters have the meanings given above and X 3 preferably represents F.

[0159] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1i, which are preferably selected from the group consisting of the compounds of the formulae III-1i-1 and III-1i-2, preferably from the group of the compounds of the formula III-1i-2

[0160] [ka]

[0161] where the parameters have the meanings given above and X 3 preferably represents F.

[0162] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1j, which are preferably selected from the group consisting of the compounds of the formulae III-1j-1 and III-1j-2, preferably from the group of the compounds of the formula III-1j-1

[0163] [ka]

[0164] where the parameters have the meanings given above.

[0165] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-2, which are preferably selected from the group of compounds of the formulae III-2a and III-2b, preferably compounds of the formula III-2b.

[0166] [ka]

[0167] wherein the parameters have the respective meanings given above, and Parameter L 31 ~L 34 represent H or F, independently of each other and other parameters.

[0168] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-2a, which compounds are preferably selected from the group of the compounds of the formulae III-2a-1 to III-2a-6:

[0169] [ka]

[0170] In the formula, R 3 has the meaning given above.

[0171] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-2b, which are preferably selected from the group consisting of the compounds of the formulae III-2b-1 to III-2b-4, preferably from the group of the compounds of the formula III-2b-4

[0172] [ka]

[0173] In the formula, R 3 has the meaning given above.

[0174] Alternatively or in addition to the compounds of formula III-1 and / or III-2, the medium according to the invention may also comprise one or more compounds of formula III-3.

[0175] [ka]

[0176] wherein the parameters have the respective meanings given above in Formula III.

[0177] These compounds are preferably selected from the group of compounds of formulae III-3a and III-3b:

[0178] [ka]

[0179] In the formula, R 3 has the meaning given above.

[0180] The liquid-crystalline media according to the invention preferably comprise one or more dielectrically neutral compounds preferably selected from the group of the compounds of the formulae VI, VII, VIII and IX, preferably having a dielectric anisotropy in the range from -1.5 to 3.

[0181] In the present application, all elements include their respective isotopes. In particular, one or more H in a compound may be replaced by D, which is also particularly preferred in some embodiments. Correspondingly, highly deuterated corresponding compounds can, for example, allow the detection and recognition of said compounds. This can be very useful in some cases, especially in the case of compounds of formula I.

[0182] In this application, Alkyl is particularly preferably straight-chain alkyl, in particular CH3-, C2H5-, n-C3H7-, n-C4H9- or n-C5H 11 - represents and Alkenyl particularly preferably denotes CH2=CH-, E-CH3-CH=CH-, CH2=CH-CH2-CH2-, E-CH3-CH=CH-CH2-CH2- or E-(n-C3H7)-CH=CH-.

[0183] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of formula VI, preferably one or more compounds of formula VI-2, in each case selected from the group of compounds of formulae VI-1 and VI-2, most preferably one or more compounds of formula VI-1 and one or more compounds of formula VI-2, respectively.

[0184] [ka]

[0185] wherein the parameters have the respective meanings given above in formula VI, preferably, in particular In formula VI-1, R 61 and R 62 each independently of the other denotes methoxy, ethoxy, propoxy, butoxy or pentoxy, preferably ethoxy, butoxy or pentoxy, more preferably ethoxy or butoxy, most preferably butoxy, In formula VI-2, R 61preferably denotes the vinyl group, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl and n-propyl or n-pentyl, and R 62 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, an unsubstituted alkoxy group having preferably 1 to 6 C atoms, particularly preferably 2 to 4 C atoms, and most preferably an ethoxy group.

[0186] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula VII selected in each case from the group of compounds of the formulae VII-1 to VII-3, preferably one or more compounds of the formula VII-1, respectively, and one or more compounds of the formula VII-2, respectively.

[0187] [ka]

[0188] wherein the parameters have the respective meanings given above in formula VII, preferably R 71 represents a vinyl group, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, n-propyl or n-pentyl, and R 72 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, an unsubstituted alkoxy group having preferably 1 to 6 C atoms, particularly preferably 2 to 4 C atoms, and most preferably an ethoxy group.

[0189] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula VI-1, which are in each case selected from the group of compounds of the following formulae:

[0190] [ka]

[0191] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula VI-2, which are in each case selected from the group of compounds of the following formulae:

[0192] [ka]

[0193] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula VII-1, which are in each case selected from the group of compounds of the following formulae:

[0194] [ka]

[0195] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula VII-2, which are in each case selected from the group of compounds of the following formulae:

[0196] [ka]

[0197] In addition to the compound of formula B or its preferred sub-formulae, the medium according to the invention preferably comprises one or more compounds, preferably dielectrically neutral, selected from the group of the compounds of formulae VI and VII, preferably in a total concentration in the range from ≧5% to ≦90%, preferably from ≧10% to ≦80%, particularly preferably from ≧20% to ≦70%.

[0198] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula VIII selected in each case from the group of compounds of the formulae VIII-1 to VIII-3, preferably one or more compounds of the formula VIII-1 respectively and / or one or more compounds of the formula VIII-3 respectively.

[0199] [ka]

[0200] wherein the parameters have the respective meanings given above in formula VIII, preferably R 81 represents a vinyl radical, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, ethyl, n-propyl or n-pentyl, alkyl, preferably ethyl, n-propyl or n-pentyl, and R 82 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 1 to 5 C atoms, or an unsubstituted alkoxy group having 1 to 6 C atoms.

[0201] In formulas VIII-1 and VIII-2, R 82 preferably denotes alkoxy having 2 or 4 C atoms, most preferably ethoxy, In Formula VIII-3, R 82 preferably represents alkyl, preferably methyl, ethyl or n-propyl, most preferably methyl.

[0202] In a further preferred embodiment, the medium comprises one or more compounds of formula IV, preferably formula IVa.

[0203] [ka]

[0204] During the ceremony, R 41 represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, preferably an n-alkyl group, particularly preferably an n-alkyl group having 2, 3, 4 or 5 C atoms, and R 42represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkenyl group having 2 to 7 C atoms or an unsubstituted alkoxy group having 1 to 6 C atoms, preferably an unsubstituted alkenyl group having 2 to 7 C atoms, preferably an unsubstituted alkenyl group having 2, 3 or 4 C atoms, more preferably a vinyl group or a 1-propyl group, in particular a vinyl group.

[0205] In a particularly preferred embodiment, the medium comprises one or more compounds of formula IV selected from the group of compounds of formulae IV-1 to IV-4, preferably one or more compounds of formula IV-1.

[0206] [ka]

[0207] During the ceremony, alkyl and alkyl' denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, alkenyl and alkenyl' independently denote alkenyl having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably having 2 C atoms, alkenyl' preferably denotes alkenyl having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably having 2 to 3 C atoms, Alkoxy represents alkoxy having 1 to 5 C atoms, preferably having 2 to 4 C atoms.

[0208] In a particularly preferred embodiment, the medium according to the invention comprises one or more compounds of formula IV-1 and / or one or more compounds of formula IV-2.

[0209] In a further preferred embodiment, the medium comprises one or more compounds of formula V:

[0210] Preferably, the medium according to the invention comprises the following compounds in the total concentrations indicated below: 1 to 60% by weight of one or more compounds selected from the group of compounds of formula X, and 1 to 60% by weight of one or more compounds selected from the group of compounds of formula B, and 0 to 60% by weight of one or more compounds of formula I, preferably selected from the group of compounds of formulae I-1 and I-2, most preferably I-2, and / or 5 to 60% by weight of one or more compounds of formula II, preferably selected from the group of compounds of formula II-1 and II-2, and / or 5 to 25% by weight of one or more compounds of formula III, and / or 5 to 45% by weight of one or more compounds of formula IV, and / or 5 to 25% by weight of one or more compounds of formula V, and / or 5 to 25% by weight of one or more compounds of formula VI, and / or 5 to 20% by weight of one or more compounds of formula VII, and / or 5 to 30% by weight of one or more compounds of formula VIII, preferably selected from the group of compounds of formulae VIII-1 and VIII-2, and / or 0 to 60% by weight of one or more compounds of formula IX, However, the total content of all compounds of formulae X, B and I to IX present in the medium is preferably 95% or more, more preferably 97% or more, and most preferably 100%.

[0211] The latter condition is preferred for all of the media according to the present application.

[0212] In a further preferred embodiment, the medium according to the invention comprises, in addition to the compounds of formula X or its preferred sub-formulas and in addition to the compounds of formulae II and / or III and / or VI and / or VII and / or VIII and / or IX and / or I and / or B, one or more dielectrically neutral compounds preferably selected from the group of the compounds of formulae IV and V, preferably in a total concentration in the range from ≧5% to ≦90%, preferably from ≧10% to ≦80%, particularly preferably from ≧20% to ≦70%.

[0213] In a particularly preferred embodiment, the medium according to the invention comprises: one or more compounds of formula X in a total concentration ranging from 3% to 50%, preferably from 5% to 30%, and one or more compounds of formula B in a total concentration ranging from 3% to 50%, preferably from 5% to 30%, and one or more compounds of formula I in a total concentration ranging from 3% to 50%, preferably from 5% to 30%, and / or one or more compounds of formula II in a total concentration ranging from 5% to 50%, preferably from 10% to 40%, and / or one or more compounds of formula VII-1 in a total concentration ranging from 5% to 30%; and / or One or more compounds of formula VII-2 at a total concentration in the range of 3% to 30%. Includes:

[0214] Preferably, the concentration of the compound of formula X in the medium according to the present invention is in the range of 1% to 60%, more preferably 5% to 40%, most preferably 8% to 35%.

[0215] Preferably, the concentration of the compound of formula B in the medium according to the present invention is in the range of 1% to 60%, more preferably 5% to 40%, most preferably 8% to 35%.

[0216] Preferably, the concentration of the compound of formula S in the medium according to the present invention is in the range of 1% to 60%, more preferably 5% to 40%, most preferably 8% to 35%.

[0217] In a preferred embodiment of the present invention, the concentration of the compound of formula I in the medium according to the present invention is in the range of 1% to 60%, more preferably 5% to 40%, and most preferably 8% to 35%.

[0218] In a preferred embodiment of the present invention, the concentration of the compound of formula II in the medium according to the present invention is in the range of 3% or more and 60% or less, more preferably 5% or more and 55% or less, more preferably 10% or more and 50% or less, and most preferably 15% or more and 45% or less.

[0219] In a preferred embodiment of the present invention, the concentration of the compound of formula VII in the medium according to the present invention is in the range of 2% or more and 50% or less, more preferably 5% or more and 40% or less, more preferably 10% or more and 35% or less, and most preferably 15% or more and 30% or less.

[0220] In a preferred embodiment of the present invention, the concentration of the compound of formula VII-1 in the medium is within the range of 1% by weight to 40% by weight, more preferably 2% by weight to 35% by weight or 15% by weight to 25% by weight.

[0221] In a preferred embodiment of the present invention, the concentration of the compound of formula VII-2 in the medium, if present, is in the range of from 1 to 40% by weight, more preferably from 5 to 35% by weight, and most preferably from 10 to 30% by weight.

[0222] The present invention also relates to electro-optical displays or electro-optical components containing a liquid-crystalline medium according to the invention, preferably electro-optical displays based on the VA, ECB, IPS or FFS effect, in particular those addressed by an active matrix addressing system.

[0223] The invention thus likewise relates to the use of the liquid-crystalline media according to the invention in electro-optical displays or electro-optical components, and further The present invention relates to a process for preparing a liquid-crystalline medium according to the present invention, characterized in that one or more compounds of formula B are mixed with one or more compounds of formula I, preferably one or more compounds of formula I-1 and / or I-2, preferably one or more compounds of formula I-2, and / or one or more compounds of formula II, preferably one or more compounds of formula II-1 and / or II-2, with one or more compounds of formula VII, preferably one or more compounds of formula VII-1 and / or VII-2, particularly preferably one or more compounds of two or more, preferably three or more different formulae II-1, II-2, VII-1 and VII-2, very preferably all four of these, and preferably one or more further compounds selected from the group of the compounds of the formulae IV and V, more preferably one or more compounds of both formulae IV and V.

[0224] In a further preferred embodiment, the medium comprises one or more compounds of formula IV selected from the group of compounds of formula IV-2 and IV-3:

[0225] [ka]

[0226] During the ceremony, alkyl and alkyl' independently denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, Alkoxy represents alkoxy having 1 to 5 C atoms, preferably having 2 to 4 C atoms.

[0227] In a further preferred embodiment, the medium comprises one or more compounds of formula V selected from the group of compounds of formulae V-1 and V-2, preferably formula V-1.

[0228] [ka]

[0229] wherein the parameters have the meanings given above in formula V, preferably R 51 represents alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms, R 52 represents alkyl having 1 to 7 C atoms, alkenyl having 2 to 7 C atoms or alkoxy having 1 to 6 C atoms, preferably alkyl or alkenyl, particularly preferably alkyl.

[0230] In a further preferred embodiment, the medium comprises one or more compounds of formula V-1 selected from the group of compounds of formula V-1a and V-1b:

[0231] [ka]

[0232] During the ceremony, alkyl and alkyl' independently denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, Alkenyl represents alkenyl having 2 to 7 C atoms, preferably having 2 to 5 C atoms.

[0233] In addition, the present invention relates to a method for reducing the wavelength dispersion of a liquid-crystalline medium comprising one or more compounds of formula II and optionally one or more compounds selected from the group of compounds of formulae VII-1 and VII-2 and / or one or more compounds of formula IV and / or one or more compounds of formula V, characterized in that one or more compounds of formula B are used in the medium.

[0234] In addition to the compounds of formulae X, B and I-IX, other constituents may also be present, for example in amounts of up to 45%, but preferably up to 35%, in particular up to 10%, of the total mixture.

[0235] The medium according to the present invention may also optionally contain dielectrically positive components, the total concentration of which is preferably 20% or less, more preferably 10% or less, based on the total medium.

[0236] In a preferred embodiment, the liquid-crystalline media according to the invention comprise a total amount of 1% to 20%, preferably 2% to 15%, particularly preferably 3% to 12%, of a compound of formula X; and / or 1% to 20%, preferably 2% to 15%, particularly preferably 3% to 12%, of a compound of formula B; and / or 1% to 20%, preferably 2% to 15%, particularly preferably 3% to 12%, of a compound of formula S; and / or 1% to 20%, preferably 2% to 15%, particularly preferably 3% to 12%, of a compound of formula I; and / or 20% to 50%, preferably 25% to 45%, particularly preferably 30% to 40%, of compounds of formula II and / or III, and / or 0% to 35%, preferably 2% to 30%, particularly preferably 3% to 25%, of compounds of formula IV and / or V; and / or 5% to 50%, preferably 10% to 45%, more preferably 15% to 40% of compounds of formula VI and / or VII and / or VIII and / or IX Includes:

[0237] The liquid crystal media according to the invention may comprise one or more chiral compounds.

[0238] Particularly preferred embodiments of the present invention satisfy one or more of the following conditions, where the acronyms (abbreviations) are explained in Tables A-C and the compounds are exemplified in Table D:

[0239] Preferably, the medium according to the invention meets one or more of the following conditions:

[0240] i. The liquid-crystalline medium has a birefringence of 0.060 or more, particularly preferably 0.070 or more.

[0241] ii. The liquid-crystalline medium has a birefringence of less than or equal to 0.200, particularly preferably less than or equal to 0.180.

[0242] iii. The liquid crystal medium has a birefringence in the range of 0.090 or more and 0.160 or less.

[0243] iv. The liquid-crystalline medium comprises one or more particularly preferred compounds of formula X, preferably selected from (sub) formulae X-1 and X-2, most preferably from (sub) formula(s) X-1-1 and / or X-2-2 and / or X-2-3, X-2-4 and / or X-2-5.

[0244] v. The liquid-crystalline medium comprises one or more particularly preferred compounds of formula B, preferably selected from (sub) formulae B-1 and B-2, most preferably (sub) formula B-2.

[0245] vi. The liquid crystal medium comprises one or more particularly preferred compounds of formula S, preferably selected from (sub) formulae S-1 and S-2, most preferably (sub) formula S-2.

[0246] vii. The liquid crystal medium comprises one or more particularly preferred compounds of formula I, preferably selected from (sub) formulae I-1 and I-2, most preferably (sub) formula I-2.

[0247] viii. The total concentration of compounds of formula II in the mixture as a whole is at least 25%, preferably at least 30%, preferably in the range of at least 25% to at most 49%, particularly preferably in the range of at least 29% to at most 47%, and very particularly preferably in the range of at least 37% to at most 44%.

[0248] ix. The liquid-crystalline medium comprises one or more compounds of formula IV selected from the group of compounds of the following formulae: CC-nV and / or CC-n-Vm and / or CC-VV and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably compounds of CC-3-V, preferably in a concentration of up to 60%, particularly preferably up to 50%, and may additionally comprise CC-3-V1, preferably in a concentration of up to 15%, and / or CC-4-V, preferably in a concentration of up to 40%, particularly preferably up to 30%.

[0249] x. The medium contains a compound of formula CC-nV, preferably CC-3-V, preferably in a concentration of 1% to 60%, more preferably 3% to 35%.

[0250] xi. The total concentration of compounds of formula CC-3-V in the entire mixture is preferably 15% or less, preferably 10% or less, or 20% or more, preferably 25% or more.

[0251] xii. The total concentration of the compounds of the formula Y-nO-Om in the entire mixture is 2% or more and 30% or less, preferably 5% or more and 15% or less.

[0252] xiii. The total concentration of the compounds of formula CY-n-Om in the entire mixture is 5% or more and 60% or less, preferably 15% or more and 45% or less.

[0253] xiv. The total concentration of compounds of formula CCY-n-Om and / or CCY-nm, preferably CCY-n-Om, in the entire mixture is 5% to 40%, preferably 1% to 25%.

[0254] xv. The total concentration of the compounds of formula CLY-n-Om in the entire mixture is 5% or more and 40% or less, preferably 10% or more and 30% or less.

[0255] xvi. The liquid-crystalline medium comprises one or more compounds of the formula IV, preferably of the formula IV-1 and / or IV-2, preferably in a total concentration of at least 1%, in particular at least 2%, very particularly preferably at least 3% to at most 50%, preferably at most 35%.

[0256] xvii. The liquid-crystalline medium comprises one or more compounds of the formula V, preferably of the formula V-1 and / or V-2, in a total concentration of preferably 1% or more, in particular 2% or more, very particularly preferably 15% or more and 35% or less, preferably 30% or less.

[0257] xviii. The total concentration of the compound of formula CCP-Vn, preferably CCP-V-1, in the whole mixture is preferably 5% or more and 30% or less, preferably 15% or more and 25% or less.

[0258] ixi. The total concentration of compounds of formula CCP-V2-n, preferably CCP-V2-1, in the whole mixture is preferably 1% to 15%, preferably 2% to 10%.

[0259] The invention further relates to an electro-optical display with active matrix addressing based on the VA, ECB, IPS, FFS or UB-FFS effect, characterized in that it contains a liquid-crystalline medium according to the invention as dielectric.

[0260] The liquid crystal mixture preferably has a nematic phase range with a temperature range of at least 70°C.

[0261] The rotational viscosity γ1 is preferably 350 mPa·sec or less, more preferably 250 mPa·sec or less, in particular 150 mPa·sec or less.

[0262] The mixtures according to the invention are suitable for all IPS and FFS-TFT applications which use dielectrically positive liquid crystal media, such as for example SG-FFS.

[0263] The liquid-crystalline media according to the invention preferably consist essentially entirely of 4 to 15, in particular 5 to 12 and particularly preferably not more than 10 compounds, which are preferably selected from the group of the compounds of the formulae X, B, I, II, III, IV, V, VI, VII, VIII and IX.

[0264] The liquid crystal media according to the invention may also contain more than 18 compounds, in which case the media preferably contain from 18 to 25 compounds.

[0265] In a preferred embodiment, the liquid crystal media according to the invention consist predominantly, preferably consist essentially and most preferably consist substantially completely of compounds which do not contain cyano groups.

[0266] In a preferred embodiment, the liquid-crystalline medium according to the invention comprises compounds selected from the group of compounds of the formulae X, B, I, II, and II, IV and V and VI to IX, preferably selected from the formulae XA, XB, B-1, B-2, I-1, I-2, II-1, II-2, III-1, III-2, IV, V, VII-1, VII-2, VIII and IX; the medium preferably consists predominantly, particularly preferably consists essentially and very particularly preferably consists substantially completely of compounds of said formulae.

[0267] The liquid-crystalline media according to the present invention preferably have a nematic phase in each case at least from -10°C to 70°C, particularly preferably from -20°C to 80°C, very particularly preferably from -30°C to 85°C, and most preferably from -40°C to 90°C.

[0268] In this document, the expression "having a nematic phase" means, on the one hand, that no smectic phase or crystallization is observed at low temperatures at the corresponding temperatures, and, on the other hand, that heating from the nematic phase does not result in clearing. Low-temperature studies are carried out in a flow viscometer at the corresponding temperatures and are confirmed by storage for at least 100 hours in test cells with a layer thickness corresponding to the electro-optical application. A medium is considered stable at this temperature if its storage stability at a temperature of -20°C in the corresponding test cell is 1000 hours or more. At temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At higher temperatures, the clearing point is measured conventionally in capillary tubes.

[0269] In a preferred embodiment, the liquid-crystalline media according to the invention are characterized by a moderately low range of optical anisotropy values: the birefringence values ​​are preferably in the range from ≧0.075 to ≦0.130, particularly preferably in the range from ≧0.085 to ≦0.120, and very particularly preferably in the range from ≧0.090 to ≦0.115.

[0270] In this embodiment, the liquid-crystalline medium according to the present invention has a positive dielectric anisotropy and a relatively high absolute value of the dielectric anisotropy Δε, Δε being in the range of ≧2.0 to ≦20, more preferably ≦15, more preferably ≧3.0 to ≦10, particularly preferably ≧4.0 to ≦9.0, and very particularly preferably ≧4.5 to ≦8.0.

[0271] The liquid crystal medium according to the present invention preferably has a relatively low threshold voltage (V0) in the range of 1.0V to 5.0V, preferably 2.5V or less, preferably 1.2V to 2.2V, particularly preferably 1.3V to 2.0V.

[0272] In a further preferred embodiment, the liquid-crystalline media according to the invention preferably have a relatively high value of the average dielectric constant (ε av. ≡(ε ∥ +2ε ⊥ ) / 3) and ε av.is preferably in the range of 8.0 or more and 25.0 or less, preferably 8.5 or more and 20.0 or less, even more preferably 9.0 or more and 19.0 or less, particularly preferably 10.0 or more and 18.0 or less, and very particularly preferably 11.0 or more and 16.5 or less.

[0273] In addition, the liquid-crystalline media according to the invention have high values ​​of VHR in a liquid-crystal cell.

[0274] In freshly filled cells at 20°C, these VHR values ​​are greater than or equal to 95%, preferably greater than or equal to 97%, particularly preferably greater than or equal to 98%, very particularly preferably greater than or equal to 99%, and after 5 minutes in an oven in a cell at 100°C, the VHR is greater than or equal to 90%, preferably greater than or equal to 93%, particularly preferably greater than or equal to 96%, very particularly preferably greater than or equal to 98%.

[0275] Here, in general, liquid-crystalline media with low addressing voltages or threshold voltages have a lower VHR than liquid-crystalline media with high addressing voltages or threshold voltages and vice versa.

[0276] Also, with the media according to the invention, these preferred values ​​of the individual physical properties are preferably maintained in each case and in each combination.

[0277] In this application, the term "compound" is also referred to as "compound(s)" and refers to both a compound and multiple compounds, unless otherwise specified.

[0278] In a preferred embodiment, the liquid-crystalline medium according to the invention has one or more compounds of formula X, and one or more compounds of formula B, preferably selected from the group of formulae CB-nF, CB-n-OT, CB-nT, LB-nF, LB-n-OT and LB-nT, more preferably selected from the group of formulae CB-n-OT, CB-nT, LB-n-OT and LB-nT, preferably selected from the group of formulae CB-n-OT, CB-nT, and / or one or more compounds of formula I, preferably selected from the group of formulae B-nO-Om, B(S)-nO-Om, B-nO-OT, B-nO-T, Bn-OT and BnF, more preferably selected from the group of formulae B-nO-OT, B-nO-T, Bn-OT and BnF, and / or one or more compounds of formula II, preferably selected from the group of formulae PUQU-nF, CDUQU-nF, APUQU-nF and PGUQU-nF, and / or one or more compounds of formula III, preferably selected from the group of formulae CCP-n-OT, CGG-nF and CGG-n-OD, and / or one or more compounds of formula IV and / or V, preferably selected from the group of formulae CC-nV, CCP-nm, CCP-Vn, CCP-V2-n and CGP-nn, and / or one or more compounds of formula VI, preferably selected from the group of formulae Yn-Om, Y-nO-Om and / or CY-n-Om, preferably selected from the group of compounds of formulae Y-3-O1, Y-4O-O4, CY-3-O2, CY-3-O4, CY-5-O2 and CY-5-O4, and / or Optionally, but preferably essentially, one or more compounds of formula VII-1, preferably selected from the group of compounds of formula CCY-nm and CCY-n-Om, preferably of formula CCY-n-Om, preferably selected from the group of compounds of formula CCY-3-O2, CCY-2-O2, CCY-3-O1, CCY-3-O3, CCY-4-O2, CCY-3-O2 and CCY-5-O2, and / or Optionally, but preferably essentially, one or more compounds of formula VII-2, preferably of formula CLY-n-Om, preferably selected from the group of compounds of formula CLY-2-O4, CLY-3-O2, CLY-3-O3, and / or one or more compounds of formula VIII, preferably selected from the group of formulae CZY-n-On and CCOY-nm, and / or one or more compounds of formula IX, preferably selected from the group of formulae PYP-nm, PYP-n-mVl and PYP-n-mVl, preferably selected from the group of formulae PYP-2-3, PYP-2-4, PYP-2-5, PYP-2-V and PYP-2-2V1, and / or one or more compounds selected from the group of formulae PGP-nm, PGP-nV, PGP-n-Vm, PGP-n-mV and PGP-n-mVl, preferably selected from the group of formulae PGP-2-3, PGP-2-4, PGP-2-5, PGP-1-V, PGP-2-V and PGP-2-2Vl, and / or Optionally, but preferably essentially, one or more compounds of formula IV, preferably selected from the group of the formulae CC-nV, CC-n-Vm, CC-n-mVl and CC-nV-Vm, preferably selected from the group of the formulae CC-3-V, CC-3-V1, CC-4-V, CC-5-V, CC-3-2V1 and CC-VV, particularly preferably selected from the group of the compounds CC-3-V, CC-3-V1, CC-4-V, CC-3-2V1 and CC-VV, very particularly preferably compound CC-3-V, and optionally additionally compound(s) CC-4-V and / or CC-3-V1 and / or CC-3-2V1 and / or CC-VV, and / or Optionally, but preferably essentially, one or more compounds of formula V, preferably selected from formulae CCP-V-1 and / or CCP-V2-1 Includes:

[0279] In a particularly preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of formula IX:

[0280] Compounds of formula IX are particularly preferred where p=q=1 and ring A 9 When is 1,4-phenylene, it is also very suitable as a stabilizer in liquid crystal mixtures. In particular, compounds of formula IX stabilize the VHR of the mixture against UV exposure.

[0281] In a preferred embodiment, the liquid-crystalline medium according to the invention comprises one or more compounds of the formula IX selected from the group of the compounds of the formulae IX-1 to IX-4, very particularly preferably of the formulae IX-1 to IX-3, most preferably of the formula IX-1.

[0282] [ka]

[0283] wherein the parameters have the meanings given in formula IX.

[0284] In a further preferred embodiment, the medium comprises one or more compounds of formula IX-3, preferably of formula IX-3-a.

[0285] [ka]

[0286] During the ceremony, Alkyl and alkyl' each independently denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms.

[0287] When compounds of formula IX are used in liquid crystal media according to the present application, the compounds of formula IX are preferably present in a concentration of at most 20% by weight, more preferably at most 10% by weight, most preferably at most 5% by weight, and each individual or (homologous) compound of formula IX is preferably present in a concentration of at most 10% by weight, more preferably at most 5% by weight.

[0288] For the purposes of the present invention, unless otherwise indicated in particular cases, the following definitions apply in connection with the identification of the components of the compositions: "Comprises": The concentration of the component in question in the composition is preferably 5% by weight or more, particularly preferably 10% by weight or more, very particularly preferably 20% by weight or more. "Consists predominantly of": The concentration of the component in question in the composition is preferably 50% by weight or more, particularly preferably 55% by weight or more, very particularly preferably 60% by weight or more. "Consists essentially of": The concentration of the component in question in the composition is preferably 80% by weight or more, particularly preferably 90% by weight or more, very particularly preferably 95% by weight or more. "Consists essentially completely of": The concentration of the component in question in the composition is preferably 98% by weight or more, particularly preferably 99% by weight or more, very particularly preferably 100.0% by weight.

[0289] The above definitions apply both to the medium as a composition having components that may be components and compounds of the composition, and also to the medium having components and compounds. As far as the concentration of the individual compounds relative to the medium as a whole is concerned, the term "comprises" means that the concentration of the compound in question is preferably 1% by weight or more, particularly preferably 2% by weight or more, and very particularly preferably 4% by weight or more.

[0290] In the present invention, "≦" means less than or equal to, preferably less than, and "≧" means greater than or equal to, preferably greater than. In the present invention, [ka] represents trans-1,4-cyclohexylene, [ka] represents 1,4-cyclohexylene, preferably trans-1,4-cyclohexylene, and [ka] represents 1,4-phenylene.

[0291] In the present invention, the expression "dielectrically positive compound" refers to a compound with Δε > 1.5, the expression "dielectrically neutral compound" refers to a compound with -1.5 ≦ Δε ≦ 1.5, and the expression "dielectrically negative compound" refers to a compound with Δε < -1.5, all at a temperature of 20°C and a frequency of 1 kHz. Herein, the dielectric anisotropy of a compound is determined by dissolving 10% by weight of the compound in a liquid crystal host and determining the capacitance of the resulting mixture at 1 kHz in at least one test cell with a cell thickness of 20 μm, homeotropic surface alignment, and homogeneous surface alignment, respectively. The measurement voltage is typically between 0.5 V and 1.0 V, but is always lower than the capacitance threshold of each liquid crystal mixture under consideration.

[0292] The host mixture used for the dielectrically positive and dielectrically neutral compounds is ZLI-4792, and the host mixture used for the dielectrically negative compounds is ZLI-2857, both manufactured by Merck, Germany. The value for each compound studied is obtained from the change in the dielectric constant of the host mixture after adding the compound studied and is extrapolated to 100% for the compound used. The compound studied is dissolved in the host mixture in an amount of 10%. If the solubility of the substance is too low for this purpose, the concentration is halved in steps until the study can be carried out at the desired temperature.

[0293] If necessary, the liquid-crystalline media according to the present invention may also contain further additives, such as stabilizers and / or pleochroic, e.g., dichroic dyes and / or chiral dopants, in the usual amounts. The total amount of these additives used is preferably from 0 to 10% by weight, particularly preferably from 0.1 to 6% by weight, based on the total amount of the mixture. The concentration of each compound used is preferably from 0.1 to 3% by weight. The concentrations of these and similar additives are generally not taken into account when specifying the concentration and concentration range of the liquid-crystalline compounds in the liquid-crystalline media.

[0294] In a preferred embodiment, the liquid-crystalline medium according to the present invention comprises a polymer precursor, which in turn comprises one or more reactive compounds, preferably reactive mesogens, and optionally further additives, such as polymerization initiators and / or polymerization retarders, in the usual amounts. The total amount of these additives used is preferably from 0 to 10% by weight, particularly preferably from 0.1 to 2% by weight, based on the total amount of the mixture. The concentrations of these and similar additives are generally not taken into account when specifying the concentration and concentration range of the liquid-crystalline compounds in the liquid-crystalline medium.

[0295] The composition comprises a number of compounds, preferably from 3 to 30, particularly preferably from 6 to 20, and very particularly preferably from 10 to 16, which are mixed in a conventional manner. Generally, the desired amount of the component used in the smaller amount is dissolved in the component that constitutes the main component of the mixture. This can be effectively achieved by increasing the temperature. Observing the completion of the dissolution operation is particularly easy if the selected temperature is above the clearing point of the main component. However, it is also possible to prepare liquid crystal mixtures in other conventional ways, for example, using premixes or in so-called "multi-bottle systems."

[0296] The mixtures according to the invention exhibit a very wide nematic phase range with a clearing point above 65° C., very favorable values ​​of the capacitance threshold and relatively high values ​​of the voltage holding ratio (VHR), and at the same time very good low-temperature stability at −30° C. and −40° C. Furthermore, the mixtures according to the invention are distinguished by a low rotational viscosity γ1.

[0297] It goes without saying for those skilled in the art that media according to the invention for use in VA, IPS, FFS or PALC displays may also comprise compounds in which, for example, H, N, O, Cl or F is replaced by the corresponding isotopes.

[0298] The structure of the liquid crystal display according to the invention corresponds to a conventional configuration, for example as described in EP-A-0 240 379.

[0299] With suitable additives, the liquid crystal phase according to the invention can be modified for use in any type of display disclosed to date, for example IPS and FFS LCD displays.

[0300] Table E below lists dopants that can be added to the mixtures according to the invention. When the mixture contains one or more dopants, the dopants are used in an amount of 0.01% to 4% by weight, preferably 0.1% to 1.0% by weight.

[0301] Stabilisers which can be added to the mixtures according to the invention, preferably in amounts of 0.01% to 6% by weight, in particular 0.1% to 3% by weight, are listed in Table F below.

[0302] For the purposes of the present invention, all concentrations are given in % by weight unless expressly stated otherwise and relate to the corresponding mixture as a whole or to each mixture component relative to the whole unless expressly stated otherwise. In this context, the term "mixture" describes a liquid-crystalline medium.

[0303] Unless otherwise expressly indicated, all temperature values ​​given herein, such as melting points T(C,N), smectic (S) to nematic (N) phase transitions T(S,N) and clearing points T(N,I), are given in degrees Celsius (°C), and correspondingly all temperature differences are given in degrees difference (° or degrees).

[0304] Unless expressly indicated otherwise in the present invention, the term "threshold voltage" relates to the capacitive threshold (V0), also known as the Freederickss threshold.

[0305] Unless otherwise expressly indicated in each case, all physical properties are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", November 1997, Merck KGaA, Germany, applying a temperature of 20°C, Δn is determined at 436 nm, 589 nm and 633 nm, and Δε is determined at 1 kHz.

[0306] The electro-optical properties, such as the threshold voltage (V) (capacitive measurement), as well as the switching behavior, were determined in a test cell manufactured by Merck Japan. The test cell had a soda-lime glass substrate and a polyimide alignment layer (SE-1211 and diluent). ** The liquid crystals were constructed in an ECB or VA configuration with 26 (mixed in a 1:1 ratio, both manufactured by Nissan Chemical Industries, Ltd., Japan), and the alignment layers were rubbed perpendicular to each other, resulting in a homeotropic alignment of the liquid crystals. The surface area of ​​the transmission was 1 cm, with a substantially square ITO electrode. 2 is.

[0307] Unless otherwise stated, no chiral dopants are added to the liquid crystal mixtures used, but the liquid crystal mixtures used according to the invention are also suitable for applications where this type of doping is required.

[0308] The rotational viscosity is determined using a rotating permanent magnet method, and the flow viscosity is determined in a modified Ubbelohde viscometer. The liquid crystal mixtures ZLI-2293, ZLI-4792, and MLC-6608 are all products of Merck KGaA, Germany. The rotational viscosity values ​​determined at 20°C are 161 mPa·s, 133 mPa·s, and 186 mPa·s, respectively, and the flow viscosity (ν) is 21 mm 2 ·s -1 , 14mm 2 ·s -1 and 27mm 2 ·s -1 is.

[0309] For practical purposes, the refractive index dispersion of a material is conventionally characterized as follows, and will be used throughout this application unless otherwise stated. Birefringence values ​​are determined at temperatures of 20°C or 25°C and at several fixed wavelengths using a modified Abbe refractometer with a homeotropically aligned surface on the side of the prism in contact with the material. Birefringence values ​​are determined at specific wavelengths of 436 nm (selected spectral lines of a low-pressure mercury lamp), 589 nm (sodium D-line), and 633 nm (helium-neon laser) using an attenuator / diffuser combination to prevent eye damage to the observer. In the table below, Δn is given at 589 nm, and Δ(Δn) is given by Δ(Δn) = Δn(436 nm) - Δn(633 nm).

[0310] Unless otherwise clearly indicated, the following symbols are used: V Capacitive threshold voltage at 20℃ [V] n e Anomalous refractive index at 20°C and 589nm Normal refractive index at 20°C and 589nm Δn Optical anisotropy at 20°C and 589 nm λ Wavelength λ [nm] Δn(λ) Optical anisotropy measured at 20°C and wavelength λ Δn(Δn) Δn(20℃, 436nm)-Δn(20℃, 633nm) The change in optical anisotropy defined as Δn(Δn * ) Δ(Δn) / Δn(20℃, 589nm) The "relative change in optical anisotropy" is defined as follows: ε ⊥ Permittivity perpendicular to the director at 20°C and 1kHz ε ∥ Dielectric constant parallel to the director at 20°C and 1kHz Δε Dielectric anisotropy at 20°C and 1kHz T(N,I) or cl.p. Clearing point [℃] ν Flow viscosity measured at 20℃ (mm 2 ·s -1 ) γRotational viscosity measured at 120℃ (mPa·s) k 11 Elastic constant for "splay" deformation at 20°C [pN] k 22 Elastic constant for "twist" deformation at 20°C [pN] k 33 Elastic constant for "bend" deformation at 20°C [pN] Low temperature stability of the phase (nematic phase) determined in an LTS test cell VHR Voltage Holding Ratio ΔVHR Decrease in voltage holding ratio S rel Relative stability of VHR.

[0311] The following examples are intended to illustrate the present invention without limiting it. However, the following examples will provide those skilled in the art with the preferred compounds to be used, their respective concentrations and their combinations with each other, as well as preferred mixing concepts. In addition, the following examples illustrate the feasible properties and property combinations.

[0312] In the present invention and particularly in the following examples, the structures of the liquid crystal compounds are represented by acronyms, and are converted to chemical formulas according to Tables A to C below. n H 2n+1 , C m H 2m+1 and C l H 2l+1 or CnH2n, CmH2m and C l H 2lare linear alkyl or alkenyl groups with carbon numbers n, m, and l in each case. Preferably, n, m, and l are each, independently of one another, 1, 2, 3, 4, 5, 6, or 7. Table A shows the codes for the ring structural elements of the core structure of the compounds, Table B lists the linking groups, and Table C lists the meaning of the codes for the left and right terminal groups of the molecule. The initial letter consists of the code for the ring structural element with any linking groups, followed by a first hyphen and the code for the left terminal group, and a second hyphen and the code for the right terminal group. Table D shows examples of structural descriptions of compounds with their respective abbreviations.

[0313] <Table A: Ring structure elements>

[0314] [Table 1]

[0315] [Table 2]

[0316] [Table 3]

[0317] <Table B: Crosslinking Units>

[0318] [Table 4]

[0319] <Table C: Terminal group>

[0320] [Table 5]

[0321] where n and m each represent an integer and the three dots "..." are spaces for other abbreviations from the table.

[0322] In addition to the compound of formula B, the mixture according to the invention preferably comprises one or more of the compounds mentioned below.

[0323] The following abbreviations are used: (n, m, k and l are each independently an integer, preferably 1 to 9, preferably 1 to 7; k and l can be 0, preferably 0 to 4, more preferably 0 or 2, most preferably 2; n is preferably 1, 2, 3, 4 or 5; in the combination "-nO-", n is 1, 2, 3 or 4, preferably 2 or 4; m is preferably 1, 2, 3, 4 or 5; in the combination "-Om", m is 1, 2, 3 or 4, preferably 2 or 4. The combination "-lVm" is preferably "2V1".)

[0324] Exemplary and Preferred Compounds of Formula X

[0325] [Table 6]

[0326] [Table 7]

[0327] [Table 8]

[0328] High ε ⊥ Exemplary and preferred compounds of formula B having the formula

[0329] [Table 9]

[0330] High ε ⊥ Exemplary and preferred compounds of Formula I have the formula:

[0331] [Table 10]

[0332] [Table 11]

[0333] [Table 12]

[0334] [Table 13]

[0335] Exemplary and Preferred Dielectrically Positive Compounds

[0336] [Table 14]

[0337] [Table 15]

[0338] [Table 16]

[0339] [Table 17]

[0340] [Table 18]

[0341] [Table 19]

[0342] [Table 20]

[0343] [Table 21]

[0344] Exemplary and Preferred Dielectrically Neutral Compounds

[0345] [Table 22]

[0346] [Table 23]

[0347] [Table 24]

[0348] [Table 25]

[0349] [Table 26]

[0350] Exemplary and Preferred Dielectrically Negative Compounds

[0351] [Table 27]

[0352] [Table 28]

[0353] [Table 29]

[0354] [Table 30]

[0355] [Table 31]

[0356] [Table 32]

[0357] [Table 33]

[0358] [Table 34]

[0359] Table E lists chiral dopants that are preferably used in the mixtures according to the invention.

[0360]

[0361] [Table 35]

[0362] [Table 36]

[0363] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds selected from the group of compounds of Table E.

[0364] Table F lists stabilizers that can be preferably used in the mixtures according to the invention in addition to the compounds of formula B. In Table F, the parameter n represents an integer ranging from 1 to 12. In particular, the phenol derivatives shown below act as antioxidants and can therefore be used as additional stabilizers.

[0365]

[0366] [Table 37]

[0367] [Table 38]

[0368] [Table 39]

[0369] [Table 40]

[0370] [Table 41]

[0371] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds selected from the group of compounds of Table F, in particular one or more compounds selected from the group of compounds of the following two formulae:

[0372] [Table 42] [Example]

[0373] The following examples illustrate the present invention without limiting it in any way. However, the physical properties clarify for those skilled in the art the achievable properties and the extent to which they can be modified. Thus, in particular, the various property combinations that can be preferably achieved are well defined for those skilled in the art.

[0374] <Synthesis example>

[0375] The following abbreviations are used: BuLi n-Butyllithium Concentrated dist. distilled MTB ether tert-butyl methyl ether THF tetrahydrofuran

[0376] <Synthesis Example 1> Synthesis of 1,3-difluoro-4-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-2-(trifluoromethyl)benzene

[0377] [ka]

[0378] <Step 1.1> 1-[2,4-difluoro-3-(trifluoromethyl)phenyl]-4-(4-propylcyclohexyl)cyclohexanol

[0379] [ka]

[0380] Under a nitrogen atmosphere at -50°C, BuLi (8.5 mL, 15% in n-hexane, 13.5 mmol) was slowly added to a solution of 1-bromo-2,4-difluoro-3-(trifluoromethyl)benzene (1, CAS 1263377-74-7) (3.4 g, 13.0 mmol) in diethyl ether (50 mL). The mixture was stirred for 1 hour, and then a solution of 4-(4-propylcyclohexyl)cyclohexanone (2, CAS 82832-73-3) (3.0 g, 13.5 mmol) in 20 mL of diethyl ether was slowly added. The reaction mixture was stirred for 1 hour and then allowed to warm to room temperature. Unless explicitly stated otherwise throughout this application, room temperature and ambient temperature are used interchangeably and refer to a temperature of about 20°C, typically (20±1°C). The reaction mixture was quenched with distilled water and hydrochloric acid (2 M). The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo to give 1-[2,4-difluoro-3-(trifluoromethyl)phenyl]-4-(4-propylcyclohexyl)cyclohexanol (3) as a yellow oil.

[0381] <Step 1.2> 1,3-Difluoro-4-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-2-(trifluoromethyl)benzene

[0382] [ka]

[0383] A mixture of 1-[2,4-difluoro-3-(trifluoromethyl)phenyl]-4-(4-propylcyclohexyl)cyclohexanol (3) (5.5 g, 11 mmol) and concentrated sulfuric acid (0.1 g, 1.0 mmol) (isomeric mixture) in xylene (40 mL) was heated at reflux temperature with a Dean-Stark trap for 1 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (solvent: n-heptane). The crude product was subsequently recrystallized from ethanol to yield colorless crystals of 1,3-difluoro-4-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-2-(trifluoromethyl)benzene (4).

[0384] Compound (4) has the following phase properties: Tg -68℃ K 39℃ I.

[0385] <Synthesis Example 2> Synthesis of 1,3-difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethyl)benzene

[0386] [ka]

[0387] <Step 2.1> 1-(4-bromophenyl)-4-propyl-cyclohexanol

[0388] [ka]

[0389] Under a nitrogen atmosphere, at -50 °C, BuLi (100 mL, 15% in n-hexane, 159 mmol) is slowly added to a solution of 1,4-dibromobenzene (1, CAS 106-37-6) (35.0 g, 148 mmol) in diethyl ether (650 mL). The mixture is stirred for 1 h, and then a solution of 4-propylcyclohexanone (2, CAS 40649-36-3) (21.0 g, 150 mmol) in 50 mL of diethyl ether is slowly added. The reaction mixture is stirred for 1 h and then allowed to warm to room temperature. The reaction mixture is quenched with distilled water and hydrochloric acid (2 M). The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo to give 1-(4-bromophenyl)-4-propylcyclohexanol (3) as a yellow oil.

[0390] <Step 2.2> 1-Bromo-4-(4-propylcyclohexen-1-yl)benzene

[0391] [ka]

[0392] A mixture of 1-(4-bromophenyl)-4-propyl-cyclohexanol (3) (47.2 g, 259 mmol) and toluene-4-sulfonic acid monohydrate (1.5 g, 8.7 mmol) in toluene (500 mL) is heated at reflux temperature for 90 min with a Dean-Stark trap. Then it is cooled to room temperature and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent: n-heptane / toluene) to give 1-bromo-4-(4-propylcyclohexen-1-yl)benzene (4) as a colorless solid.

[0393] <Step 2.3> [4-(4-propylcyclohexen-1-yl)phenyl]boronic acid

[0394] [ka]

[0395] Under a nitrogen atmosphere, at −65° C., BuLi (74 mL, 15% in n-hexane, 118 mmol) is slowly added to a solution of 1-bromo-4-(4-propylcyclohexen-1-yl)benzene (4) (30.0 g, 107 mmol) in THF (470 mL). The mixture is stirred for 1 h, and a solution of trimethyl borate (5, CAS 121-43-7) (12.5 g, 120 mmol) in THF (30 mL) is slowly added. The reaction mixture is stirred for 1 h, and then it is warmed to 5° C. The reaction mixture is quenched with distilled water and acidified with hydrochloric acid (2 M). The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is suspended in n-heptane, heated to 50° C., cooled to 5° C., and filtered under vacuum to give [4-(4-propylcyclohexen-1-yl)phenyl]boronic acid (6) as a colorless solid.

[0396] <Step 2.4> 1,3-Difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethyl)benzene

[0397] [ka]

[0398] A mixture of 4-(4-propylcyclohexen-1-yl)phenyl]boronic acid (6) (6.4 g, 26 mmol), 1-bromo-2,4-difluoro-3-(trifluoromethyl)benzene (7) (CAS 1263377-74-17 (6.0 g, 23.0 mmol), bis(dibenzylideneacetone)-palladium(0) (15 mg, 26 μmol), and tris-(o-tolyl)phosphine (40 mg, 131 μmol) in acetone (100 mL) was heated to reflux under a nitrogen atmosphere, followed by the dropwise addition of sodium hydroxide solution (2 N, 23 mL, 46 mmol). The reaction mixture is heated at reflux for 3 hours. It is then cooled to room temperature and diluted with MTB ether and distilled water. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with distilled water and brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent: heptane). The crude product is then recrystallized from ethanol and heptane, resulting in colorless crystals of 1,3-difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethyl)benzene.

[0399] Compound (8) has the following phase properties: K 80℃ I.

[0400] <Synthesis Example 3> Synthesis of 1,3-difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethoxy)benzene

[0401] [ka]

[0402] <Step 3.1> 1,3-Difluoro-4-iodo-2-(trifluoromethoxy)benzene

[0403] [ka]

[0404] To a solution of 1,3-difluoro-2-(trifluoromethoxy)benzene (1) (15.0 g, 76 mmol) in THF (120 mL) is slowly added BuLi (49.0 mL, 1.6 M in n-hexane, 78 mmol) under a nitrogen atmosphere at -70 °C. The reaction mixture is stirred at -70 °C for 1 h. Then, a solution of iodine (CAS 7553-56-2) (19.5 g, 77 mmol) in THF (80 mL) is slowly added at -70 °C. After 30 min, the reaction mixture is warmed to room temperature and quenched with diluted aqueous sodium bisulfite solution. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with distilled water and brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent: pentane) and vacuum distillation to give 1,3-difluoro-2-(trifluoromethoxy)benzene (2) as a colorless oil.

[0405] <Step 3.2> 1,3-Difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethoxy)benzene

[0406] [ka]

[0407] A mixture of 4-(4-propylcyclohexen-1-yl)phenyl]boronic acid (3) (5.9 g, 24 mmol), 1,3-difluoro-4-iodo-2-(trifluoromethoxy)benzene (2) (8.5 g, 23 mmol), bis(dibenzylideneacetone)-palladium(0) (15 mg, 26 μmol), and tris-(o-tolyl)phosphine (40 mg, 131 μmol) in acetone (100 mL) is heated to reflux under a nitrogen atmosphere, followed by the dropwise addition of sodium hydroxide solution (2 N, 23 mL, 46 mmol). The reaction mixture is heated at reflux for 3 hours. It is then cooled to room temperature and diluted with MTB ether and distilled water. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with distilled water and brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent: heptane). The crude product is then recrystallized from ethanol and heptane, resulting in colorless crystals of 1,3-difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethoxy)benzene.

[0408] Compound (4) has the following phase properties: K 75℃ SmA 50℃ I.

[0409] <Compound examples>

[0410] <Example 1>(1)

[0411] [ka]

[0412] Phase order:T g -76℃ K 4 I;Δn=0.0220;Δε=3.3.

[0413] <Compound example 2> (2)

[0414] [ka]

[0415] Phase sequence: T g -81℃ K 8℃ I.

[0416] <Compound Example 3>(3)

[0417]

change

[0418] <Compound Example 4>(4)

[0419]

change

[0420] <Compound Example 5>(5)

[0421]

change

[0422] Phase sequence: T g -68℃ K 39℃ I;Δn=0.0707;Δε=3.8;γ1=217mPa·s.

[0423] <Compound Example 6>(6)

[0424]

change

[0425] Phase sequence: K 38℃ N(-4℃)I; Δn=0.0701; Δε=3.9; γ1=251mPa·s.

[0426] <Compound Example 7>(7)

[0427]

change

[0428] Phase sequence: K 59℃ I; Δn=0.0951; Δε=4.4; γ1=215mPa·s.

[0429] <Compound Example 8>(8)

[0430]

change

[0431] Phase sequence: K 92℃ I; Δn=0.0971; Δε=4.0; γ1=210mPa·s.

[0432] <Compound Example 9>(9)

[0433]

change

[0434] Phase sequence: K 80℃ I; Δn=0.1383; Δε=6.0; γ1=275mPa·s.

[0435] <Compound Example 10>(10)

[0436]

change

[0437] Phase sequence: K 75℃ S A (50℃) I;Δn=0.1363;Δε=5.9;γ1=273mPa·s.

[0438] <Example 11>(11)

[0439]

change

[0440] Phase sequence: K 103℃ S A (83℃) I;Δn=0.1830;Δε=6.9;γ1=222mPa·s.

[0441] <Example 12> (12)

[0442] [ka]

[0443] Phase sequence: K 96℃ S A 101℃ I;Δn=0.1810;Δε=6.3;γ1=209mPa·s.

[0444] <Example 13> (13)

[0445] [ka]

[0446] Phase sequence: K 155℃ I.

[0447] <Example 14> (14)

[0448] [ka]

[0449] Phase sequence: K 123℃ I.

[0450] Analogous to the above examples, the following exemplary compounds of formula X and its respective subformulas are obtained:

[0451] In the tables below, the following abbreviations are used for the end groups:

[0452] [Table 43]

[0453] [ka]

[0454] Table 44

[0455] Table 45

[0456] Table 46

[0457]

change

[0458] Table 47

[0459] Table 48

[0460] Table 49

[0461]

change

[0462] Table 50

[0463] Table 51

[0464] Table 52

[0465]

change

[0466] Table 53

[0467] Table 54

[0468]

change

[0469] Table 55

[0470] Table 56

[0471] Table 57

[0472]

change

[0473] Table 58

[0474] Table 59

[0475] Table 60

[0476]

change

[0477] Table 61

[0478] Table 62

[0479] Table 63

[0480]

change

[0481] Table 64

[0482] Table 65

[0483]

change

[0484] Table 66

[0485] Table 67

[0486] [Table 68]

[0487] [Table 69]

[0488] [Table 70]

[0489] [Table 71]

[0490] <Mixture example> Exemplary mixtures are disclosed below.

[0491] <Comparative example A> The following mixture (CE-A) is prepared and studied:

[0492] [Table 72]

[0493]

[0494] [Table 73]

[0495] <Table 1 (continued)>

[0496] [Table 74]

[0497] <Table 1 (continued)>

[0498] [Table 75]

[0499] <Table 1 (continued)>

[0500] [Table 76]

[0501] These mixtures, mixtures A-1 to A-12, have good dielectric ratios (ε ⊥ / Δε), good ratio (γ1 / k 11 ) and are characterized by very good transmittance in FFS displays and exhibit very short response times. Furthermore, they exhibit excellent low-temperature stability down to temperatures of at least -20°C.

[0502] <Example 1> The following mixture (M-1) is prepared and studied:

[0503] [Table 77]

[0504] This mixture, mixture M-1, has a dielectric ratio (ε ⊥ / Δε), 4.71 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmittance and good response times in FFS displays and has very good low temperature stability.

[0505] <Example 2> The following mixture (M-2) is prepared and studied:

[0506] [Table 78]

[0507] This mixture, mixture M-2, has a dielectric ratio (ε ⊥ / Δε), 4.64 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good low temperature stability.

[0508] <Example 3> The following mixture (M-3) is prepared and studied:

[0509] [Table 79]

[0510] This mixture, mixture M-3, has a dielectric ratio (ε ⊥ / Δε), 4.68 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmittance and good response times in FFS displays and has very good low temperature stability.

[0511] <Example 4> The following mixture (M-4) is prepared and studied:

[0512] [Table 80]

[0513] This mixture, mixture M-4, has a dielectric ratio (ε ⊥ / Δε) and are characterized by very good transmittance in FFS displays and have very good low temperature stability.

[0514] <Example 5> The following mixture (M-5) is prepared and studied:

[0515] [Table 81]

[0516] This mixture, Mixture M-5, has a dielectric ratio (ε ⊥ / Δε), 4.51 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good low temperature stability.

[0517] <Example 6> The following mixture (M-6) is prepared and studied:

[0518] [Table 82]

[0519] This mixture, Mixture M-6, has a dielectric ratio (ε ⊥ / Δε) and are characterized by very good transmittance in FFS displays and have very good low temperature stability.

[0520] <Example 7> The following mixture (M-7) is prepared and studied:

[0521] [Table 83]

[0522] This mixture, Mixture M-7, has a dielectric ratio (ε ⊥ / Δε), 4.40 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good low temperature stability.

[0523] <Example 8> The following mixture (M-8) is prepared and studied:

[0524] [Table 84]

[0525] This mixture, Mixture M-8, has a dielectric ratio (ε ⊥ / Δε), 5.21 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good low temperature stability.

[0526] <Example 9> The following mixture (M-9) is prepared and studied:

[0527] [Table 85]

[0528] This mixture, Mixture M-9, has a dielectric ratio (ε ⊥ / Δε), 5.40 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good low temperature stability.

[0529] <Example 10> The following mixture (M-10) is prepared and studied:

[0530] [Table 86]

[0531] This mixture, Mixture M-10, has a dielectric ratio (ε ⊥ / Δε), 4.44 mPa·s / pN ratio (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good low temperature stability.

[0532] <Example 11> The following mixture (M-11) is prepared and studied:

[0533] [Table 87]

[0534] This mixture, mixture M-11, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0535] <Example 12> The following mixture (M-12) is prepared and studied:

[0536] [Table 88]

[0537] This mixture, mixture M-12, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0538] <Example 13> The following mixture (M-13) is prepared and studied:

[0539] [Table 89]

[0540] This mixture, mixture M-13, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0541] <Example 14> The following mixture (M-14) is prepared and studied:

[0542] [Table 90]

[0543] This mixture, mixture M-14, is characterized by very good transmission in FFS displays and has very good low temperature stability.

[0544] <Example 15> The following mixture (M-15) is prepared and studied:

[0545] [Table 91]

[0546] This mixture, mixture M-15, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0547] <Example 16> The following mixture (M-16) is prepared and studied:

[0548] [Table 92]

[0549] This mixture, mixture M-16, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0550] <Example 17> The following mixture (M-17) is prepared and studied:

[0551] [Table 93]

[0552] This mixture, mixture M-17, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0553] <Example 18> The following mixture (M-18) is prepared and studied:

[0554] [Table 94]

[0555] This mixture, mixture M-18, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0556] <Example 19> The following mixture (M-19) is prepared and studied:

[0557] [Table 95]

[0558] This mixture, mixture M-19, is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0559] <Example 20> The following mixture (M-20) is prepared and studied:

[0560] [Table 96]

[0561] This mixture, mixture M-20, is characterized by good properties.

[0562] <Example 21> The following mixture (M-21) is prepared and studied:

[0563] [Table 97]

[0564] This mixture, mixture M-21, is characterized by good properties.

[0565] <Example 22> The following mixture (M-22) is prepared and studied:

[0566] [Table 98]

[0567] This mixture, mixture M-22, is characterized by good properties.

[0568] <Example 23> The following mixture (M-23) is prepared and studied:

[0569] [Table 99]

[0570] This mixture, mixture M-23, is characterized by good properties.

[0571] <Example 24> The following mixture (M-24) is prepared and studied:

[0572] [Table 100]

[0573] This mixture, mixture M-24, is characterized by good properties.

Claims

1. A liquid-crystalline medium having a nematic phase and a dielectric anisotropy (Δε) of 0.5 or more, characterized in that it comprises one or more compounds selected from the group consisting of compounds of the formulae CLX-nF, CLX 0 -nF, LPX-nF or LPX 0 -nF. 【Chemistry 1】 (In the formula, n represents an integer of 1 to 9.

2. A liquid-crystalline medium having a nematic phase and a dielectric anisotropy (Δε) of greater than or equal to 0.5, characterized in that it comprises one or more compounds selected from the group consisting of compounds of the formulae CLX-n-F, CLX 0 -n-F, LPX-n-F, LPX 0 -n-F, PX-n-F or PX 0 -n-F and one or more additional compounds selected from the group consisting of compounds of the formulae CLP-n-m, CLP-V-n or CLP-n-T. 【Chemistry 2】 【Transformation 3】 (In the formula, n represents an integer of 1 to 9. 【Chemistry 4】 (In the formula, n and m each independently represent an integer of 1 to 9.

3. 3. The medium according to claim 1 or 2, characterized in that it comprises one or more compounds of formula B and / or formula S. 【Transformation 5】 (In the formula, 【Transformation 6】 【Transformation 7】 n represents 1 or 2; R １ represents alkyl, alkoxy, fluorinated alkyl, fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, and X １ represents F, Cl, a fluorinated alkyl, a fluorinated alkenyl, a fluorinated alkoxy, or a fluorinated alkenyloxy. 【Transformation 8】 (In the formula, 【Chemistry 9】 【Chemistry 10】 n represents 1 or 2; R １ represents alkyl, alkoxy, fluorinated alkyl, fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, and X １ represents F, Cl, a fluorinated alkyl, a fluorinated alkenyl, a fluorinated alkoxy, or a fluorinated alkenyloxy.

4. A medium according to any one of claims 1 to 3, characterized in that it contains one or more compounds of formula I. 【Chemistry 11】 (In the formula, 【Chemistry 12】 【Chemistry 13】 represents 【Chemistry 14】 represents n represents 0 or 1; R １１ and R １２ each independently represent alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, alkenyl having 2 to 7 C atoms, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, and R １１ Instead of R １ represents R １２ Instead of X １ represents R １ represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, and X １ represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy; However, compounds of formulas B and S defined in claim 3 are excluded.

5. A medium according to any one of claims 1 to 4, characterized in that it comprises one or more compounds selected from the group of compounds of formulae II and III: 【Chemistry 15】 (In the formula, R ２ represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, 【Chemistry 16】 L ２１ and L ２２ represents H or F, X ２ represents halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, m represents 0, 1, 2 or 3; R ３ represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, 【Chemistry 17】 L ３１ and L ３２ are each independently H or F, X ３ is halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, F, Cl, —OCF ３ , -OCHF ２ , —O—CH ２ CF ３ , —O—CH═CF ２ , —O—CH═CH ２ Or -CF ３ represents Z ３ is -CH ２ CH ２ -, -CF ２ CF ２ -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH ２ represents O— or a single bond, and n represents 0, 1, 2 or 3.

6. 6. Liquid-crystalline medium according to claim 5, characterized in that it comprises one or more dielectrically neutral compounds selected from the group of the formulae IV and V [Chemistry 18] (In the formula, R ４１ and R ４２ are independently of each other, in formula II, R ２ has the meaning given in claim 5, 【Chemistry 19】 Z ４１ and Z ４２ are, independently of each other, and Z ４１ occurs twice, they also independently represent -CH ２ CH ２ -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH ２ O-, -CF ２ represents O—, —C≡C— or a single bond; p represents 0, 1 or 2; R ５１ and R ５２ are, independently of each other, R ４１ and R ４２ has one of the meanings given to 【Chemistry 20】 Z ５１ ~Z ５３ are each independently —CH ２ -CH ２ -, -CH ２ represents —O—, —CH═CH—, —C≡C—, —COO— or a single bond, and i and j each independently represent 0 or 1; However, the compounds of formulae CLP-nm, CLP-Vn and CLP-nT defined in claim 2 and the compound of formula III defined in claim 5 are excluded.

7. 7. Liquid-crystalline medium according to claim 1, characterized in that it comprises one or more compounds selected from the group of the formulae VI to IX 【Chemistry 21】 (In the formula, R ６１ represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkenyl group having 2 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, R ６２ represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms, and l represents 0 or 1; R ７１ represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, R ７２ represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, 【Chemistry 22】 R ８１ represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, R ８２ represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, 【Chemistry 23】 Z ８ is -(C=O)-O-, -CH ２ —O—, —CF ２ —O— or —CH ２ -CH ２ represents -, o represents 0 or 1; R ９１ and R ９２ are, independently of each other, ７２ has the meaning given to 【Chemistry 24】 p and q each independently represent 0 or 1.

8. The medium according to any one of claims 3 to 7, characterized in that the total concentration of the compounds of formula B in the whole medium is ≥ 1% and ≤ 60%.

9. 9. The medium according to claim 1, further comprising one or more chiral compounds and / or stabilizers.

10. Electro-optical displays or electro-optical components, characterized in that they contain a liquid-crystalline medium according to any one of claims 1 to 9.

11. 11. Display according to claim 10, characterized in that it is based on the IPS or FFS mode.

12. 12. A display according to claim 10 or 11, characterized in that it contains an active matrix addressable device.

13. Use of a medium according to any one of claims 1 to 9 in an electro-optical display or electro-optical component.

14. A process for preparing a liquid-crystalline medium according to claim 2, characterized in that one or more compounds selected from the group consisting of compounds of the formulae CLX-n-F, CLX 0 -n-F, LPX-n-F, LPX 0 -n-F, PX-n-F or PX 0 -n-F are mixed with one or more additional mesogenic compounds selected from the group consisting of compounds of the formulae CLP-n-m, CLP-V-n or CLP-n-T and optionally one or more adjuvants.

15. A compound selected from the group consisting of compounds of formula CLX-nF, CLX 0 -nF, LPX-nF or LPX 0 -nF. 【Chemistry 25】 (In the formula, n represents an integer of 1 to 9.

16. A method for preparing a compound selected from the group consisting of compounds of formula CLX-nF, CLX 0 -nF, LPX-nF or LPX 0 -nF, comprising the steps of: ２ -3-Y １ -4-X-phenyl with a ketone via a metal-mediated coupling reaction to give the respective tertiary alcohol followed by subsequent dehydration to the strylene derivative, or ２ -3-Y １ -4-X-phenyl with an aromatic boronic acid derivative to give the corresponding biphenyl derivative. 【Chemistry 26】 (In the formula, n represents an integer of 1 to 9. with the proviso that the building block 1-Hal-2-Y 2 -3-Y 1 -4-X-phenyl is 【Chemistry 27】 And, In the formula, Hal represents Br or I, Y 1 represents CF 3 or OCF 3 , Y 2 represents F, and X represents F.

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