Liquid crystal medium and liquid crystal displays containing same and compounds thereof - Patents.com

Abstract

To provide a liquid-crystalline medium that shows improved contrast and / or response times, and a liquid-crystal display comprising the liquid-crystalline medium and compounds.SOLUTION: The present disclosure provides a liquid-crystalline medium having a nematic phase, containing one or more compounds of formula D and one or more additional compounds, and its use in an electro-optical display, particularly in an active-matrix display based on the IPS or FFS effect.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to new liquid crystal media, in particular for use in liquid crystal displays, and to these liquid crystal displays, in particular those using the IPS (in plane switching) or preferably the FFS (fringe field switching) effect using dielectrically positive liquid crystals. The last FFS effect using dielectrically positive liquid crystals is often also called the XB-FFS (extra brightness FFS) effect.

[0002] In this effect, dielectrically positive liquid crystals are used, which simultaneously have a high dielectric constant parallel to the molecular director and a high dielectric constant perpendicular to the molecular director, thereby resulting in a large average dielectric constant and a high dielectric ratio, and preferably at the same time a relatively small dielectric anisotropy. The liquid crystal medium may additionally contain dielectrically negative compounds, dielectrically neutral compounds, or both. The liquid crystal medium is used in a uniform (i.e. planar) initial alignment. The liquid crystal medium according to the invention contains compounds which have a positive dielectric anisotropy and at the same time have a large dielectric constant parallel and perpendicular to the molecular director.

[0003] The media are distinguished by a particularly good rendition of the black state, which is mainly due to the very low scattering in them, which is brought about by their particularly high elastic constants.

[0004] Higher elastic constants can also lead to higher values ​​of rotational viscosity (γ1) and, as a consequence, higher values ​​of the elastic constant for twist deformation (k 22 ) to rotational viscosity (γ1) (γ1 / k 22 ), leading to higher values ​​of k 22 is the elastic constant of the splay deformation, k 11 Since it is almost proportional to (k 22 The value of is typically k 11 ), which is roughly half the value of γ1 and k 11This can be easily and conveniently approximated by determining

[0005] The contrast of an LC display can on the other hand be improved by a higher transmission, which in the FFS cell layout requires a higher ε ⊥ This can be achieved by:

[0006] And on the other hand, it can be improved by a better dark state. The latter, i.e. the dark state, is strongly influenced by the scattering parameters, among others. Here, liquid crystal media with a high elastic modulus reduce scattering and thus improve the contrast of LCDs. This also leads to their excellent performance in displays according to the invention.

[0007] 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.

[0008] However, recently, IPS and especially FFS displays using dielectrically negative liquid crystals have been widely adopted. FFS displays using dielectrically negative liquid crystals are also sometimes called UB-FFS (ultra bright FFS). Such displays are disclosed in US Patent Application Publication No. 2013 / 0207038. These displays are characterized by a significantly increased transmittance compared to the previously used IPS and FFS displays, which were dielectrically positive liquid crystals. However, these displays using conventional dielectrically negative liquid crystals have the significant disadvantage of requiring a higher operating voltage 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.

[0009] The liquid crystal medium used in HB-FFS (high brightness FFS) has a dielectric anisotropy of 0.5 or more, preferably 1.5 or more. The liquid crystal media used in each HB-FFS, which contain both dielectrically negative and dielectrically positive liquid crystal compounds that are mesogenic compounds, are disclosed, for example, in US Patent Application Publication No. 2013 / 0207038 (Patent Document 1). These media have a dielectric anisotropy of ε ⊥ and ε av. The value of is already quite large, but the ratio (ε ⊥ / Δε) is relatively small.

[0010] According to the present application, however, an IPS or FFS effect with a homogeneously aligned, dielectrically positive liquid crystal medium is preferred.

[0011] The industrial application of this effect in electro-optical display elements requires LC phases that satisfy a number of requirements, of particular importance here being chemical resistance to moisture, air and physical influences such as heat, radiation in the infrared, visible and ultraviolet range, direct current (DC) and alternating current (AC) electric fields.

[0012] Furthermore, industrially usable LC phases are required to have a liquid crystal mesophase within a suitable temperature range and low viscosity.

[0013] The series of compounds having liquid crystal mesophases disclosed to date does not include a single compound that fulfills all these requirements, therefore, to obtain a material usable as an LC phase, a mixture of 2 to 25 compounds, preferably 3 to 18 compounds, is generally prepared.

[0014] Matrix liquid-crystal displays (MLC displays) are known. Nonlinear elements that can be used to individually switch the individual pixels are, for example, active elements (i.e. transistors). Note that 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.

[0015] Two technologies are distinguished: TFTs containing compound semiconductors, e.g. CdSe or metal oxides, e.g. ZnO, and TFTs based on polycrystalline silicon, especially amorphous silicon. The latter technology is currently of greatest commercial importance worldwide.

[0016] One glass plate of the display has a TFT matrix on its inside, while the other holds 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. The technology can also be extended to full-colour displays, in which a mosaic of red, green and blue filters is arranged so that a filter element faces each of the switchable pixels.

[0017] The TFT displays most used so far are usually operated in transmission with crossed polarizers and backlit. For television applications ECB (or VAN) cells or FFS cells are used, while monitors usually use IPS cells or TN (twisted nematic) cells, and for notebooks, laptops and mobile applications usually TN, VA or FFS cells.

[0018] 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).

[0019] 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. In addition to problems related to the angular dependence of contrast and response times, MLC displays also suffer from problems resulting from the liquid crystal mixture not having a sufficiently high specific resistance [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.The resistivity of the liquid crystal mixture generally decreases over the life of an MLC display due to interactions with the internal surfaces of the display, so a high (initial) resistance is very important for a display that must have an acceptable resistance value over long periods of operation.

[0020] 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.

[0021] Here, the most important designs can be mentioned: MVA (multi-domain vertical alignment, e.g. Yoshide, H. et al., Article 3.1: “MVA LCD for Notebook or Mobile PCs”, SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6-9 (Non-Patent Document 4) and Liu, CT et al., Article 15.1: “A 46-inch TFT-LCD HDTV Technology”, 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, Article 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 )), and 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).

[0022] In a general way, the techniques are compared, for example, in Souk Jun, SID Seminar 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 yet to be satisfactorily solved, especially in switching grey levels (grey shades).

[0023] ECB displays, such as ASV displays, use liquid crystal media with negative dielectric anisotropy (Δε), whereas TN and to date all conventional IPS displays use liquid crystal media with positive dielectric anisotropy. However, there is currently an increasing demand for IPS and FFS displays which use dielectrically negative liquid crystal media.

[0024] In this type of liquid crystal display, liquid crystal is used as a dielectric whose optical properties change reversibly upon application of a voltage.

[0025] In general, in displays, i.e. also in displays due to these effects already mentioned, the operating voltage must be as low as possible, so that liquid-crystalline media are used which generally consist mainly of liquid-crystalline compounds, all of which have the same sign of dielectric anisotropy and the highest possible value of dielectric anisotropy. Generally, 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.

[0026] In the media used by the present application, since liquid crystal displays are generally intended to have the lowest possible address voltages, 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.

[0027] US 2013 / 0207038 A1 discloses liquid crystal media for HB-FFS displays and proposes to improve the performance of FFS displays using liquid crystals with positive dielectric anisotropy by additionally incorporating dielectrically negative liquid crystals. However, this approach requires compensating for the negative contribution of the added compounds to the overall dielectric anisotropy value of the resulting medium. This requires increasing the concentration of dielectrically positive materials, which reduces the amount of dielectrically neutral compounds available for use as diluents in the mixture, or alternatively requires the use of compounds with stronger positive dielectric anisotropy. All of these approaches have the important drawback of increasing the response time of the liquid crystals in the display.

[0028] Liquid-crystalline media with positive dielectric anisotropy for IPS and FFS displays have already been disclosed. Some examples are given below.

[0029] Chinese Patent Publication No. 104232105 (Patent Document 2), WO 2014 / 192390 (Patent Document 3) and WO 2015 / 007131 (Patent Document 4) disclose liquid crystal media with positive dielectric anisotropy, some of which have a fairly high dielectric constant in the direction perpendicular to the director.

[0030] Obviously, the phase range of the liquid crystal mixture must be sufficiently wide for the intended application of the display.

[0031] 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 been repeatedly 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.

[0032] Unpublished German patent application No. 10 2019 00 18 87.7 (Patent Document 5) discloses, among other things, compounds of the formula: [ka]

[0033] Adequate stability of the medium against extreme loads, especially UV exposure and heat, is very particularly important, which can be crucial for display applications, especially in portable devices, such as mobile phones for example.

[0034] In addition to the relatively poor transmission and relatively long response time of MLC displays, previously disclosed MLC displays have further disadvantages, such as the relatively low contrast of MLC displays, the relatively high viewing angle dependence, and the difficulty in reproducing grayscales (grey shades) in these displays, especially when viewed from oblique viewing angles, as well as inadequate VHR and inadequate lifetime of MLC displays. Desirable improvements in the transmission and response time of displays are needed to improve the energy efficiency of MLC displays and to improve the ability of individual MLC displays to accommodate fast moving images.

[0035] 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 relatively low threshold voltage, which allow for the production of various gray levels (gray shading), and in particular, have good and stable VHR.

[0036] The present invention aims to provide MLC displays based on the ECB, IPS or FFS effect, which are free of or have reduced defects as indicated above, and at the same time have very high resistivity values, for monitor and television applications, but also for mobile applications, such as telephones and navigation systems, for which it must be ensured that they can operate at extremely high and extremely low temperatures, in particular for mobile telephones and navigation systems. [Prior art documents] [Patent documents]

[0037] [Patent Document 1] US Patent Application Publication No. 2013 / 0207038 [Patent Document 2] China Patent Application Publication No. 104232105 [Patent Document 3] International Publication No. 2014 / 192390 [Patent Document 4] International Publication No. 2015 / 007131 [Patent Document 5] German Patent Application No. 10 2019 00 18 87.7 [Non-Patent Document]

[0038] [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., Proc. Eurodisplay, Vol. 84, September 1984, "Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays", 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 (hereinafter omitted)", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6 - 9 [Non-Patent Document 5] Liu, CT 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] Souk Jun, SID Seminar 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 Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 106-109 Summary of the Invention [Means for solving the problem]

[0039] Surprisingly, it is preferred that at least one compound, preferably two or more compounds of the formula D, preferably of the sub-formulae D-1 to D-9, D-5', D-5", D-6' and D-6", particularly preferably of the sub-formulae D-1 and / or D-5 and / or D6, more preferably of the formula D-6, in particular of the formulae D-6-1 and / or D-6-3 and / or D-6-4, preferably additionally selected from the group of compounds of the formulae II and III, the former preferably being combined with one or more compounds, preferably two or more compounds of the formulae II-1 and / or II-2 and / or with one or more compounds of the formulae IV and / or It has been found that by using a nematic liquid crystal medium comprising one or more compounds, preferably two or more compounds selected from group V and preferably one or more compounds selected from group VII to IX, all formulas as defined herein below, in a display element it is possible to achieve liquid crystal displays, in particular in IPS and FFS displays, which have low threshold voltages, a sufficiently broad nematic phase, favourable birefringence (Δn) together with short response times and at the same time high transmittance, high contrast, good stability against degradation by heat and UV exposure, a stable and high VHR.

[0040] In a further preferred embodiment the liquid crystal medium comprises one or more compounds selected from the group of compounds of the formulae I and B, preferably selected from the group of compounds of the sub-formulae I-1 and I-2 and B-1 and B-2, respectively, particularly preferably from the sub-formulae I-1 and / or I-2 and B-1 and / or B-2, most preferably of the formulae I-2, B-1 and B-2, most preferably of both the formulae I-1 and I-2 and the formulae B-1 and / or B-2.

[0041] This type of medium can be used in particular for electro-optical displays with active matrix addressing, for IPS or FFS displays.

[0042] The medium according to the invention preferably additionally comprises one or more compounds selected from the group of compounds of formulae II and III, preferably one or more compounds of formula II, more preferably additionally one or more compounds of formula III, most preferably additionally one or more compounds selected from the group of compounds of formulae IV and V, and also preferably one compound selected from the group of compounds of formulae VI to IX (all formulae as defined below).

[0043] The mixtures according to the invention show a very wide nematic phase range with a clearing point above 70° C., very favourable values ​​of the capacity threshold, relatively high values ​​of the retention, and at the same time a good low-temperature stability and a very low rotational viscosity at −20° C. and −30° C. The mixtures according to the invention are furthermore distinguished by a good ratio of clearing point to rotational viscosity and a relatively high positive dielectric anisotropy.

[0044] It has now surprisingly been found that by using certain selected liquid crystal media, FFS type LCDs using liquid crystals of 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. ) is high, and the dielectric constant (ε ⊥ ) is high, and in particular the ratio of these latter two values ​​(ε ⊥ / Δε) is relatively high.

[0045] Preferably, the liquid-crystalline media according to the invention have on the one hand a value of the dielectric anisotropy of ≧1.5, preferably ≧2.5. On the other hand, they preferably have a dielectric anisotropy of ≦26, preferably ≦15, most preferably ≦10.

[0046] In a preferred embodiment, the liquid crystal medium according to the present invention preferably has a positive dielectric anisotropy in the range of 1.5 to 20.0, more preferably in the range of 2.0 to 15.0, most preferably in the range of 2.0 to 12.0.

[0047] The liquid crystal medium of the present invention comprises a) one or more compounds of formula D, preferably in a concentration ranging from 1% to 40%, more preferably in a concentration ranging from 2% to 30%, particularly preferably in a concentration ranging from 3% to 20%, and one or more additional compounds selected from the group of compounds according to the following conditions b) to f): Includes.

[0048] [ka]

[0049] During the ceremony, R D is H, an alkyl group having 1 to 15 C atoms (one or more CH groups in these groups may be replaced independently by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -(CO)-O-, -O-(C=O)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably cyclopropylene or 1,3-cyclopentylene), alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, preferably alkyl or alkenyl (one -CH2- group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably cyclopropylene or 1,3-cyclopentenylene, in such a way that the O atoms are not directly linked to each other, and one or more H atoms may be replaced by halogen), Y D1 , Y D2 , Y D3 and Y D4 are the same or different and represent H, F or Cl, with the proviso that Y D1 and Y D2 At least one of them is not H, and preferably Y D3 is F, preferably Y D1 , Y D2 and Y D3 is F, X Drepresents F, Cl, CN, NCS, SF5, fluorinated alkyl, alkoxy, alkenyl or alkenyloxy, each having up to 5 C atoms, preferably F, CF3, OCF3 or NCS, most preferably F, CF3 or OCF3, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group. b) one or more preferably dielectrically positive compounds selected from the group of the compounds of formulae II and III, preferably compounds having a dielectric anisotropy greater than 3, preferably one or more compounds of formula II.

[0050] [ka]

[0051] [ka]

[0052] During the ceremony, R 2 represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably an alkyl or alkenyl, [ka] L 21 and L 22 represents H or F, preferably L 21 represents F, X 2represents 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 represents 0, 1, 2 or 3, preferably 1 or 2, particularly preferably 2, R 3 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 n-alkyl, cyclopropyl, cyclopentyl or alkenyl, [ka] L 31 and L 32 are each independently H or F, preferably L 31 represents 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, and is 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, n is 0, 1, 2 or 3, preferably 1, 2 or 3, particularly preferably 1, with the proviso that each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group; With the proviso that compounds of formula D are excluded from compounds of formula III.

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

[0054] [ka]

[0055] During the ceremony, R 41 and R 42 are each independently a group represented by R 2 has the meaning given above for R 41 represents alkyl, R 42 represents alkyl or alkoxy, or R 41 represents alkenyl, R 42 represents alkyl; [ka] Z 41 and Z 42 are independent of each other, and Z 41 when occurring 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 represent a single bond; p represents 0, 1 or 2, preferably 0 or 1; R 51 and R 52 are, independently of each other, R 41 and R 42has one of the meanings given for, preferably denotes 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 alkoxyalkyl having 2 to 7 C atoms, preferably having 2 to 4 C atoms, alkenyl or alkenyloxy, preferably alkenyloxy, [ka] Preferably [ka] Preferably [ka] And if it exists [ka] Z 51 ~Z 53 each independently of one another is -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, most preferably 1; However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0056] d) Again as an optional component, preferably alternatively or in addition to an essential component, it also contains one or more dielectrically negative compounds selected from the group of compounds of formulae VI to IX.

[0057] [ka]

[0058] During the ceremony, R 61 represents 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 an alkenyl group having 2 to 7 C atoms, preferably a linear alkenyl group, particularly preferably a group having 2 to 5 C atoms, or 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, l represents 0 or 1; R 71 represents 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 an unsubstituted alkenyl group having 2 to 7 C atoms, preferably a linear alkenyl group, particularly preferably a group having 2 to 5 C atoms, R 72 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably having 2 to 5 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, preferably having 1, 2, 3 or 4 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, preferably having 2, 3 or 4 C atoms, [ka] R 81 represents 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 an alkenyl group having 2 to 7 C atoms, preferably a linear alkenyl group, particularly preferably a group having 2 to 5 C atoms, R 82 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably having 2 to 5 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, preferably having 1, 2, 3 or 4 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, preferably having 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-, o represents 0 or 1; R 91 and R 92 are, independently of each other, 72 has the meaning given to R 91 preferably represents an alkyl group having 2 to 5 C atoms, preferably having 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; (p+q) preferably represents 0 or 1, [ka] Alternatively, preferably, p=q=1, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0059] e) one or more compounds of formula B, preferably selected from the group of compounds of formulae B-1 and B-2, again as an optional component, preferably as an essential component, preferably in a concentration within the range of 1% to 60%, more preferably within the range of 2% to 40%, particularly preferably within the range of 3% to 35%.

[0060] [ka]

[0061] 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, X 1 represents F, Cl, a fluorinated alkyl, a fluorinated alkenyl, a fluorinated alkoxy or a fluorinated alkenyloxy (the latter four groups preferably having 1 to 4 C atoms), more preferably F, Cl, CF3 or OCF3, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0062] f) Again optionally, but preferably essentially, either alternatively or additionally, one or more compounds of formula I.

[0063] [ka]

[0064] During the ceremony [ka] [ka] [ka] Preferably, [ka] n represents 0 or 1; R 11 and R 12 each independently preferably represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably an alkyl, alkoxy, alkenyl or alkenyloxy, most preferably an alkyl, alkoxy or alkenyloxy, or R 11 is R 1 or R 12 isX 1 represents R 1 represents preferably alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, preferably alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, X 1 represents F, Cl, a fluorinated alkyl, a fluorinated alkenyl, a fluorinated alkoxy or a fluorinated alkenyloxy (the latter four groups preferably having 1 to 4 C atoms), more preferably F, Cl, CF3 or OCF3, with the proviso that each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group; Compounds of formula B are excluded.

[0065] Throughout this application, 1,3-cyclopentenylene is a moiety selected from the group of formulae:

[0066] [ka]

[0067] Preferably, the medium according to the present application comprises one or more compounds selected from the group of compounds of formulae D-1 to D-9, preferably of formula D-3 and / or of formula D-5 and / or of formula D-6, most preferably of formula D-6.

[0068] [ka]

[0069] [ka]

[0070] During the ceremony, R D and X D have the respective meanings given above, preferably R D represents an alkyl group having 1 to 15, preferably 1 to 7, most preferably 1 to 5 C atoms, preferably an n-alkyl, or an alkenyl group having 2 to 15, preferably 2 to 7, most preferably 2 to 5 C atoms, preferably vinyl or 1-E-alkenyl, X D represents F, Cl, CF3, OCF3 or NCS, most preferably F, CF3 or OCF3, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0071] Examples of preferred compounds of formula D in which the phenyl ring is substituted with an alkyl group are those selected from the group of compounds of formula D5', D5", D-6' and D-6".

[0072] [ka]

[0073] wherein the parameters have the respective meanings given above, including their respective preferred meanings.

[0074] The present invention also relates to compounds of formulae D-1 to D-5 and D5', D5", D-6' and D-6", and preferably X D is not F, and preferably X D represents F, Cl, CF3 or OCF3.

[0075] The liquid-crystalline media according to the invention preferably have a nematic phase.

[0076] Throughout this application, R D In the definition of alkyl, it is meant 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.

[0077] When alkyl means a branched alkyl group, it preferably means 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. The most preferred of these groups are 2-hexyl and 2-octyl.

[0078] In particular, R D In the present application, each branched group leading to a chiral compound is also referred to as a chiral group. 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.

[0079] Particularly preferred chiral groups are, for example, 2-butyl (=1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular 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-methylbutyryloxy, 3-methylvaleroyloxy, 4-methylhexanoyloxy, 2-chloropropionyloxy, 2-chloro-3-methylbutyryloxy, 2-chloro-4-methylvaleroyloxy, 2-chloro-3-methylvaleroyloxy, 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-octyloxy, 1,1,1-trifluoro-2-octyl, and 2-fluoromethyloctyloxy. Highly preferred are 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.

[0080] Throughout this application, R D In the definition alkenyl means an alkenyl group which may be linear or branched, preferably linear, and preferably has 2, 3, 4, 5, 6 or 7 or 8 C atoms. It is preferably vinyl, 1-E-alkenyl or 3-E-alkenyl, and it is most preferably vinyl, 1-E-propenyl, 1-E-butenyl, 1-E-pentenyl, 3-butenyl or 3-E-pentenyl.

[0081] In certain preferred embodiments of the present invention, the medium is selected from the group of compounds of formulae D-6-1, D-6-2, D-6-3, D-6-4 and D-6-5, and preferably comprises one or more compounds of formulae D-6-1 and / or D-6-3 and / or D-6-4.

[0082] [ka]

[0083] wherein R D has the respective meaning given above, and However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0084] Among these compounds especially those of formulae D-6-1, D-6-3 and D-6-4, preferably such compounds of formulae D-6-3 and D-6-4, are part of the invention.

[0085] The compounds of general formula D are prepared in a manner known per se, precisely under known and suitable reaction conditions for said reactions, as described in the literature (for example in standard works such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart, etc.), whereby variants known per se, but not mentioned in more detail here, can be used.

[0086] If desired, the starting material can also be formed in situ by not isolating it from the reaction mixture but instead immediately converting it further to a compound of general formula D.

[0087] Preferred synthetic routes to compounds according to the invention are shown in the schemes below and further illustrated by the examples. By selection of appropriate starting materials, the synthesis can be tailored to specific desired compounds of general formula I.

[0088] Compounds of formula D, particularly formula D-6, are synthesized as shown in Scheme 1.

[0089] <Scheme 1> [ka]

[0090] R in the formula D and X D have the respective meanings given in formula D and subformulas therein.

[0091] Another object of the present invention is therefore the compounds of formula D-III and their use in the process for the synthesis of compounds of formula D.

[0092] [ka]

[0093] in which the occurring groups and parameters have the meanings given above for formula D and its subformulas, including their respective preferred meanings; and However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0094] A further object of the present invention is a process for the synthesis of compounds of formula D via compounds of formula D-III, preferably according to the synthetic route depicted in Scheme 1 above.

[0095] The reactions described should be considered as illustrative only: to obtain compounds of formula D, those skilled in the art can carry out corresponding variations of the described syntheses or follow other suitable synthetic routes.

[0096] Compounds of the general formula D may be advantageously used in liquid-crystalline media. The invention therefore also relates to a liquid-crystalline medium comprising two or more liquid-crystalline compounds, including one or more compounds of the general formula D.

[0097] 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.

[0098] The 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 which comprises a polymerized component and a low molecular weight component, wherein the polymerized component is 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 wherein the low molecular weight component is a liquid crystal mixture according to the invention as described above and below.

[0099] The displays according to the invention are preferably addressed by active matrix LCD (AMD for short), preferably by a matrix of thin-film transistors (TFT), however the liquid crystals according to the invention can also be used advantageously in displays with other known addressing methods.

[0100] The present 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 D, preferably selected from the group of the compounds of the formulae D-1 to D-9, D-5', D-5", D-6' and D-6", most preferably selected from the group of the compounds of the formulae D-6-1 to D-6-5, with one or more low molecular weight liquid-crystalline compounds or liquid-crystalline mixtures and, optionally, further liquid-crystalline compounds and / or additives.

[0101] Above and below, the following meanings apply:

[0102] Unless otherwise indicated, the term "FFS" is used to refer to FFS and SG-FFS displays.

[0103] The term "mesogenic group" is known to those skilled in the art and described in the literature and denotes a group which, by virtue of the anisotropy of its attractive and repulsive interactions, essentially contributes to the occurrence of a liquid-crystalline (LC) phase in low molecular weight or polymeric substances. Compounds containing mesogenic groups (mesogenic compounds) do not necessarily have an LC phase by themselves. It is also possible that mesogenic compounds show liquid-crystalline phase behavior only after mixing with other compounds and / or after polymerization. Typical mesogenic groups are, for example, rigid rod-like or disc-like shaped units. A review of the terms and definitions used in relation to mesogens or liquid-crystalline 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, p. 6340-6368.

[0104] 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, p. 6340-6368. Unless otherwise indicated, the term "spacer group" or "spacer" above and below refers to a flexible group that connects the mesogenic group and the polymerizable group(s) in the polymerizable mesogenic compound.

[0105] 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 exclusively 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.

[0106] Particular preference is given to liquid-crystal mixtures or liquid-crystal media which have a nematic phase, especially at room temperature.

[0107] In a preferred embodiment of the present invention, the liquid-crystalline medium comprises one or more compounds, preferably having a dielectrically positive, preferably a dielectric anisotropy of 3 or more, 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.

[0108] [ka]

[0109] [ka]

[0110] 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 stands for F, [ka] In the case of formulas II-1 and II-2, X 2 preferably denotes F or OCF3, particularly preferably F, and in the case of formula II-2: [ka]

[0111] However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0112] [ka]

[0113] [ka]

[0114] in which the parameters have the meanings given in formula III, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0115] The medium according to the invention may also 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.

[0116] [ka]

[0117] In the formula, the parameters have the respective meanings given above, and the parameter L 31 and L 32 represent, independently of each other and of the other parameters, H or F, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0118] The liquid crystal medium is preferably L 21 and L 22 and / or L 23 and L 24 and wherein both represent F.

[0119] In a preferred embodiment the liquid crystal medium is L 21 , L 22 , L 23 and L 24all of which represent F.

[0120] The liquid crystal medium preferably comprises one or more compounds of formula II-1, which are preferably selected from the group of the compounds of the formulae II-1a to II-1e, preferably one or more compounds of the formulae II-1a and / or II-1b and / or II-1d, preferably compounds of the formulae II-1a and / or II-1d or II-1b and / or II-1d, most preferably compounds of the formula II-1d.

[0121] [ka]

[0122] In the formula, the parameters have the respective meanings given above, and L 25 and L 26 stand, independently of each other and of the other parameters, for H or F, preferably In formulae II-1a and II-1b, L 21 and L 22 Both of these 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 of these represent F, In formula II-1e, L 21 , L 22 and L 25 represents F, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0123] 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 each of the formulae II-2a and / or II-2h and / or II-2j.

[0124] [ka]

[0125] [ka]

[0126] [ka]

[0127] 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 are H, and particularly preferably, L 26 represents H, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0128] The liquid crystal medium is preferably L 21 and L 22 Both represent F and / or L 23 and L 24 and wherein both of these are F.

[0129] In a preferred embodiment the liquid crystal medium is L 21 , L 22 , L 23 and L 24In particular, the present invention includes compounds selected from the group of compounds of formulae II-2a to II-2k, in which all of

[0130] Particularly preferred compounds of formula II-2 are those of the following formulae, particularly preferred compounds are those of formulae II-2a-1 and / or II-2h-1 and / or II-2k-2:

[0131] [ka]

[0132] [ka]

[0133] In the formula, R 2 and X 2 has the meaning given above, and X 2 preferably represents F, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0134] The liquid crystal 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.

[0135] [ka]

[0136] [ka]

[0137] wherein the parameters have the meanings given above, preferably wherein the parameters have the respective meanings given above, and the parameter L 33 and L 34 stand for H or F, independently of each other and of the other parameters, and the parameter L 35 and L 36 represent, independently of each other and of the other parameters, H or F, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0138] The liquid crystal medium is preferably one or more compounds of the formula III-1c, preferably selected from the group of the compounds of the formulae III-1c-1 to III-1c-5, preferably from the group 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.

[0139] [ka]

[0140] In the formula, R 3 has the meaning given above, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0141] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1f, which are preferably selected from the group 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, more preferably from the group of the compounds of the formulae III-1f-3 and / or III-1f-6, more preferably from the group of the compounds of the formula III-1f-6.

[0142] [ka]

[0143] In the formula, R 3 has the meaning given above, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0144] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1g, which are preferably selected from the group 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.

[0145] [ka]

[0146] In the formula, R 3 has the meaning given above, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0147] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1h, which are preferably selected from the group 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.

[0148] [ka]

[0149] where the parameters have the meanings given above and X 3 preferably represents F, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0150] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1i, which are preferably selected from the group 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.

[0151] [ka]

[0152] where the parameters have the meanings given above and X 3 preferably represents F, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0153] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1j, which are preferably selected from the group 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.

[0154] [ka]

[0155] where the parameters have the meanings given above, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0156] The liquid crystal medium preferably comprises one or more compounds of the formula III-2. The compounds of the formula III-2 are preferably selected from the group of the compounds of the formulae III-2a and III-2b, preferably from the group of the compounds of the formula III-2b.

[0157] [ka]

[0158] In the formula, the parameters have the respective meanings given above, and the parameter L 33 and L 34 represent, independently of each other and of the other parameters, H or F, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0159] The liquid crystal medium preferably comprises one or more compounds of the formula III-2a, which are preferably selected from the group of the compounds of the formulae III-2a-1 to III-2a-6.

[0160] [ka]

[0161] In the formula, R 3 has the meaning given above, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0162] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-2b, which are preferably selected from the group 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.

[0163] [ka]

[0164] In the formula, R 3 has the meaning given above, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0165] Alternatively or in addition to the compounds of formula III-1 and / or III-2, the medium according to the invention may contain one or more compounds of formula III-3.

[0166] [ka]

[0167] wherein the parameters have the respective meanings given above in formula III, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0168] These compounds are preferably selected from the group of compounds of formulae III-3a and III-3b.

[0169] [ka]

[0170] In the formula, R 3 has the meaning given above, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0171] The liquid-crystalline media according to the invention preferably comprise one or more dielectrically neutral compounds which are preferably selected from the group of the compounds of the formulae VI, VII, VIII and IX and have a dielectric anisotropy in the range from -1.5 to 3.

[0172] 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. Corresponding highly deuterated compounds can, for example, be detected and recognized. This can be very useful in some cases, especially in the case of compounds of formula I.

[0173] In this application, Alkyl is particularly preferably linear alkyl, in particular CH3-, C2H5-, n-C3H7-, n-C4H9- or n-C5H 11 - represents 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-.

[0174] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula VI, in each case selected from the group of compounds of the formulae VI-1 and VI-2, preferably one or more compounds of the formulae VI-1 and one or more compounds of the formulae VI-2, respectively.

[0175] [ka]

[0176] wherein the parameters have the respective meanings given above in formula VI, preferably In formula VI-1, R 61 and R 62each 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 61 preferably denotes vinyl, 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, R 62 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, or an unsubstituted alkoxy group, preferably having 1 to 6 C atoms, particularly preferably having 2 or 4 C atoms, most preferably an ethoxy group.

[0177] 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 and one or more compounds of the formula VII-2, respectively.

[0178] [ka]

[0179] wherein the parameters have the respective meanings given above in formula VII, preferably R 71 represents vinyl, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, n-propyl or n-pentyl, R 72 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, or an unsubstituted alkoxy group, preferably having 1 to 6 C atoms, particularly preferably having 2 or 4 C atoms, most preferably an ethoxy group, However, each ring, preferably the phenylene ring, may each be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0180] 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:

[0181] [ka]

[0182] 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:

[0183] [ka]

[0184] 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:

[0185] [ka]

[0186] 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:

[0187] [ka]

[0188] In addition to the compound of formula B or its preferred sub-formulas, the medium according to the invention preferably comprises one or more dielectrically negative compounds selected from the group of the compounds of the 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%.

[0189] 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.

[0190] [ka]

[0191] wherein the parameters have the respective meanings given above in formula VIII, preferably R 81 represents the 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, 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.

[0192] In formulas VIII-1 and VIII-2, R 82 preferably denotes alkoxy having 2 or 4 C atoms, most preferably ethoxy, and in formula VIII-3 preferably denotes alkyl, preferably methyl, ethyl or n-propyl, most preferably methyl.

[0193] In a further preferred embodiment the medium comprises one or more compounds of formula IV, preferably of formula IVa.

[0194] [ka] During the ceremony, R 41 stands for 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 a group having 2, 3, 4 or 5 C atoms, R 42 represents 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, both of which preferably have 2 to 5 C atoms, the unsubstituted alkenyl group preferably having 2, 3 or 4 C atoms, more preferably a vinyl group or a 1-propenyl group, in particular a vinyl group.

[0195] 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 formula IV-1.

[0196] [ka]

[0197] During the ceremony, alkyl and alkyl' independently 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.

[0198] 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.

[0199] In a further preferred embodiment, the medium comprises one or more compounds of formula V.

[0200] In a further preferred embodiment, the medium comprises one or more compounds of formula I, selected from the group of compounds of formulae I-1 and I-2.

[0201] [ka]

[0202] [ka]

[0203] During the ceremony, R 11 and R 12 each independently of the other preferably represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably an alkyl, alkoxy, alkenyl or alkenyloxy, most preferably an alkoxy or alkenyloxy, 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 or alkenyl, X 1stands for F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy (the latter four groups preferably have 1 to 4 C atoms), preferably F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably CF3 or OCF3.

[0204] In a further preferred embodiment the medium comprises one or more compounds of formula B, which are preferably selected from the group of compounds of formula B-1 and B-2:

[0205] [ka]

[0206] [ka]

[0207] During the ceremony, 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 or alkenyl, X 1 stands for F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy (the latter four groups preferably have 1 to 4 C atoms), preferably F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably CF3 or OCF3.

[0208] The medium according to the invention preferably comprises the following compounds in the total concentrations indicated below: 1 to 30% by weight of one or more compounds selected from the group of compounds of formula D, from 0 to 30% by weight of one or more compounds selected from the group of compounds of formula I, preferably of formulae I-1 and I-2, most preferably of formula I-2, and / or from 2 to 60% by weight of one or more compounds selected from the group of compounds of formula II, preferably of formulae II-1 and II-2, and / or 1 to 60% by weight of one or more compounds of formula III, and / or 20 to 80% by weight of one or more compounds of formula IV, and / or 0 to 25% by weight of one or more compounds of formula V, and / or 0 to 25% by weight of one or more compounds of formula VI, and / or 0 to 20% by weight of one or more compounds of formula VII, and / or 0 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, and / or 0 to 30% by weight of one or more compounds selected from the group of compounds of formula B

[0209] However, the total content of all compounds of formula D, formulae I to IX and formula B present in the medium is preferably 95% or more, more preferably 97% or more, and most preferably 100%.

[0210] The latter condition applies to all media according to this application.

[0211] In a further preferred embodiment, the medium according to the invention comprises, in addition to the compounds of formula D or the preferred sub-formulas thereof and 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%.

[0212] In a particularly preferred embodiment, the medium according to the invention comprises one or more compounds of formula D in a total concentration ranging from 3% to 50%, preferably from 5% to 30%, and 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 in a total concentration ranging from 3% to 30%; and / or one or more compounds of formula I in a total concentration ranging from 3% to 50%, preferably from 5% to 30%, and / or Contains one or more compounds of formula B in a total concentration in the range of ≧3% to ≦50%, preferably ≧5% to ≦30%.

[0213] Preferably, the concentration of the compound of formula D in the medium according to the present invention is in the range of 1% to 50%, more preferably 2% to 40%, and most preferably 3% to 35%.

[0214] In a preferred embodiment of the present invention, the concentration of the compound of formula II in the medium 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.

[0215] In a preferred embodiment of the present invention, the concentration of the compound of formula VII in the medium 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.

[0216] In a preferred embodiment of the present invention, the concentration of the compound of formula VII-1 in the medium is in the range of 1% to 40%, more preferably 2% to 35%, or 15% to 25%.

[0217] 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 ≧1% to ≦40%, more preferably ≧5% to ≦35%, and most preferably ≧10% to ≦30%.

[0218] 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 3% to 40%, and most preferably 5% to 35%.

[0219] 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 2% to 40%, and most preferably 3% to 35%.

[0220] 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 device.

[0221] The invention thus likewise relates to the use of a liquid-crystalline medium according to the invention in electro-optical displays or electro-optical components and furthermore to a process for the preparation of a liquid-crystalline medium according to the invention, characterized in that one or more compounds of formula B are mixed with one or more compounds of formula I, preferably with one or more compounds of sub-formulae I-1 and / or I-2, preferably with one or more compounds of formula II, preferably with one or more compounds of formula II-1 and / or II-2, with one or more compounds of formula VII, preferably with one or more compounds of formula VII-1 and / or VII-2, particularly preferably with one or more compounds from two or more, preferably three or more different formulae of the formulae II-1, II-2, VII-1 and VII-2, very preferably with one or more compounds from all these four formulae, and preferably with one or more further compounds selected from the group of the compounds of the formulae IV and V, more preferably with one or more compounds of both formulae IV and V.

[0222] In a further preferred embodiment, the medium comprises one or more compounds of formula IV selected from the group of compounds of formulae IV-2 and IV-3:

[0223] [ka]

[0224] [ka]

[0225] 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.

[0226] 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 of formula V-1.

[0227] [ka]

[0228] [ka]

[0229] in which 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 formulae V-1a and V-1b:

[0231] [ka] TIFF0007672817000077.tif45166In formula, alkyl and alkyl' independently denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, Alkenyl represents an alkenyl having 2 to 7 C atoms, preferably having 2 to 5 C atoms.

[0232] 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 the formula II, and optionally one or more compounds selected from the group of the compounds of the formulae VII-1 and VII-2 and / or one or more compounds of the formula IV and / or one or more compounds of the formula V, characterized in that one or more compounds of the formula B are used in the medium.

[0233] In addition to the compounds of formulae D, I-IX and B, 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.

[0234] The medium according to the invention may also contain dielectrically positive compounds, the total concentration of which is preferably less than or equal to 20%, more preferably less than or equal to 10%, based on the total medium.

[0235] In a preferred embodiment, the liquid-crystalline media according to the invention are present in a total amount, based on the entire mixture, of 1% to 30%, preferably 2% to 25%, particularly preferably 3% to 20%, of a compound of formula D, and / or 1% to 20%, preferably 1% to 15%, particularly preferably 2% to 12%, of a compound of formula B, and / or - 0% to 20%, preferably 0% to 15%, particularly preferably 0% to 12%, of a compound of formula I, and / or 3% to 50%, preferably 4% to 45%, particularly preferably 5% to 40%, of compounds of the formulae II and / or III, and / or 0% to 35%, preferably 2% to 30%, particularly preferably 3% to 25%, of compounds of formulae IV and / or V, and / or Contains 5% to 50%, preferably 10% to 45%, and more preferably 15% to 40% of compounds of formulae VI and / or VII and / or VIII and / or IX.

[0236] The liquid crystal media according to the invention may contain one or more chiral compounds.

[0237] Particularly preferred embodiments of the present invention satisfy one or more of the following conditions: Here, the acronyms (abbreviations) are explained in Tables A to C and exemplified in Table D.

[0238] Preferably, the medium according to the invention meets one or more of the following conditions:

[0239] i) The liquid-crystalline medium has a birefringence of 0.060 or more, particularly preferably 0.070 or more.

[0240] ii) The liquid-crystalline medium has a birefringence of 0.200 or less, particularly preferably 0.180 or less.

[0241] iii) The liquid crystal medium has a birefringence in the range of 0.090 or more and 0.160 or less.

[0242] iv) The liquid-crystalline medium comprises one or more compounds of formula D, preferably selected from the (sub) formulae D-1 to D-9, D-5', D-5", D-6' and D-6", most preferably the particularly preferred compounds of the (sub) formulae D-6-1 to D-6-5.

[0243] v) The liquid crystal medium comprises one or more compounds of formula B, preferably selected from the (sub) formulae B-1 and B-2, most preferably the particularly preferred compounds of formula (sub) B-2.

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

[0245] vii) The total concentration of compounds of formula II in the entire mixture is at least 25%, preferably at least 30%, preferably in the range from ≥ 25% to ≤ 49%, particularly preferably in the range from ≥ 29% to ≤ 47%, very particularly preferably in the range from ≥ 37% to ≤ 44%.

[0246] viii) The liquid-crystalline medium comprises one or more compounds of the formula IV selected from the group of the compounds CC-nV and / or CC-n-Vm and / or CC-VV and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably compounds CC-3-V, preferably in a concentration of up to 60%, particularly preferably up to 50%, and optionally additionally 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%.

[0247] ix) The medium comprises a compound of formula CC-nV, preferably CC-3-V, preferably in a concentration of ≧1% to ≦60%, more preferably in a concentration of ≧3% to ≦35%.

[0248] x) 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.

[0249] xi) 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.

[0250] xii) 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.

[0251] xiii) 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%.

[0252] xiv) The total concentration of the compounds of formula CLY-n-Om in the entire mixture is 5% to 40%, preferably 10% to 30%.

[0253] xv) 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 ≥1%, in particular ≥2%, very particularly preferably ≥3% to ≤50%, preferably ≤35%.

[0254] xvi) The liquid-crystalline medium comprises one or more compounds of the formula V, preferably of the formula V-1 and / or V-2, preferably in a total concentration of at least 1%, in particular at least 2%, very particularly preferably at least 15% to at most 35%, preferably at most 30%.

[0255] xvii) The total concentration of compounds of formula CCP-Vn, preferably CCP-V-1, in the entire mixture is preferably 5% to 30%, preferably 15% to 25%.

[0256] xiii) The total concentration of compounds of formula CCP-V2-n, preferably CCP-V2-1, in the entire mixture is preferably ≧1%-≦15%, preferably ≧2%-≦10%.

[0257] The invention furthermore relates to an electro-optical display with active matrix addressing based on the VA, ECB, IPS, FFS or UB-FFS effect, characterised in that it contains a liquid-crystalline medium according to the invention as dielectric.

[0258] The liquid crystal mixture preferably has a nematic phase range with a temperature range of at least 70°C.

[0259] The rotational viscosity γ1 is preferably 350 mPa·s or less, preferably 250 mPa·s or less, in particular 150 mPa·s or less.

[0260] 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, XB-FFS.

[0261] 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 D, B, I, II, III, IV, V, VI, VII, VIII and IX.

[0262] The liquid crystal medium according to the invention may also contain more than 18 compounds. In this case, the medium preferably contains from 18 to 25 compounds.

[0263] In a preferred embodiment the liquid crystal media according to the invention comprise in a large proportion, preferably consist essentially and most preferably consist substantially completely of compounds which do not contain cyano groups.

[0264] In a preferred embodiment the liquid crystal media according to the invention comprise compounds selected from the group of the compounds of the formulae D, B, I, II, and II, IV and V and VI to IX, preferably selected from the group of the compounds of the formulae D-1 to D-9, D-5', D-5", D-6' and D-6", 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; they preferably consist predominantly, particularly preferably consist essentially and very particularly preferably consist substantially completely of compounds of said formulae.

[0265] The liquid crystal 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.

[0266] In this document, the expression "having a nematic phase" means, on the one hand, that no smectic phase and no crystallization are observed at low temperatures at the corresponding temperatures, and, on the other hand, that no clearing still occurs when heated from the nematic phase. The low-temperature studies are carried out in a flow viscometer at the corresponding temperatures and are checked by storage for at least 100 hours in test cells with layer thicknesses corresponding to electro-optical applications. If the storage stability at a temperature of -20°C in the corresponding test cells is 1,000 hours or more, the medium is considered stable at this temperature. At temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the clearing point is measured by conventional methods in capillaries.

[0267] In a preferred embodiment, the liquid-crystalline media according to the invention are characterized by a medium to low range value of the optical anisotropy: the birefringence value is 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.

[0268] In this embodiment, the liquid crystal medium according to the present invention has a positive dielectric anisotropy Δε, which is in the range from ≧2.0 to ≦20, more preferably ≦15, more preferably ≧2.0 to ≦10, particularly preferably ≧2.0 to ≦9.0, very particularly preferably ≧2.5 to ≦8.0.

[0269] 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 or less, particularly preferably 1.3V to 2.0V or less.

[0270] In addition, the liquid-crystalline media according to the invention have high values ​​of VHR in a liquid-crystal cell.

[0271] Here, in general, liquid-crystal media with a low addressing voltage or threshold voltage have a lower VHR than liquid-crystal media with a higher addressing voltage or threshold voltage and vice versa.

[0272] Also, these preferred values ​​of the individual physical properties are preferably in each case maintained in combination with one another by the media according to the invention.

[0273] In this application, the term "compound" is also referred to as "compound (single or multiple)" and refers to both a single compound and multiple compounds, unless otherwise specified.

[0274] In a preferred embodiment the liquid-crystalline medium according to the invention has one or more compounds of formula D, and one or more compounds of formula B, preferably selected from the group of the formulae CB-nF, CB-n-OT, CB-nT, LB-nF, LB-n-OT and LB-nT, more preferably selected from the group of the formulae CB-n-OT, CB-nT, LB-n-OT and LB-nT, preferably selected from the group of the formulae CB-n-OT, CB-nT, and / or one or more compounds of formula II, preferably of the 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 the 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 the formulae Yn-Om, Y-nO-Om and / or CY-n-Om, preferably selected from the group of the compounds of the 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 as an essential component, one or more compounds of the formula VII-1, preferably selected from the group of the compounds of the formulae CCY-nm and CCY-n-Om, preferably selected from the group of the compounds of the formulae CCY-n-Om, preferably selected from the group of the compounds of the formulae 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 essential, one or more compounds of the formula VII-2, preferably of the formula CLY-n-Om, preferably selected from the group of the compounds of the formulae 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 the formulae PYP-nm, PYP-n-mVl and PYP-n-mVl, preferably selected from the group of the 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-2-2V1, and / or optionally, but preferably as essential components, one or more compounds of the formula IV, preferably those selected from the group of the compounds of the formulae CC-nV, CC-n-Vm, CC-n-mVl and CC-nV-Vm, preferably those selected from the group of the compounds of the formulae CC-3-V, CC-3-V1, CC-4-V, CC-5-V, CC-3-2V1 and CC-VV, particularly preferably those selected from the group of the compounds of CC-3-V, CC-3-V1, CC-4-V, CC-3-2V1 and CC-VV, very particularly preferably the compound CC-3-V and, as optional components, additionally, those of the formulae CC-4-V and / or CC-3-V1 and / or CC-3-2V1 and / or CC-VV, and / or Optionally, but preferably as an essential component, one or more compounds of formula V, preferably selected from the group of formulae CCP-V-1 and / or CCP-V2-1 Includes.

[0275] In a particular preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of formula IX.

[0276] 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, the compounds of formula IX stabilize the VHR of the mixture against UV exposure.

[0277] In a preferred embodiment, the liquid crystal 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.

[0278] [ka]

[0279] wherein the parameters have the meanings given in formula IX.

[0280] In a further preferred embodiment, the medium comprises one or more compounds of formula IX-3, preferably of formula IX-3-a.

[0281] [ka]

[0282] During the ceremony, Alkyl and alkyl' each independently represent alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms.

[0283] 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%, more preferably at most 10%, most preferably at most 5%, and each of the individual homologous compounds of formula IX is preferably present in a concentration of at most 10%, more preferably at most 5%.

[0284] For the purposes of this invention, unless otherwise indicated in particular cases, the following definitions apply with respect to the identification of the components of the compositions.

[0285] "Comprises": The concentration of the component of interest in the composition is preferably 5% or more, particularly preferably 10% or more, very particularly preferably 20% or more.

[0286] "Consists primarily of": The concentration of the component of interest in the composition is preferably 50% or more, particularly preferably 55% or more, very particularly preferably 60% or more.

[0287] "Consists essentially of": The concentration of the component of interest in the composition is preferably 80% or more, particularly preferably 90% or more, very particularly preferably 95% or more.

[0288] "Consists essentially completely of": The concentration of the component of interest in the composition is preferably 98% or more, particularly preferably 99% or more, very particularly preferably 100.0%.

[0289] This applies both to the medium as a composition with components which may be groups of compounds and individual compounds of the composition, and also to groups of compounds with their respective components and compounds. As far as the concentration of the individual compounds in relation to the medium as a whole is concerned, the term "comprising" means that the concentration of the compound(s) or compounds(s) in question is preferably 1% or more, particularly preferably 2% or more, very particularly preferably 4% 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.

[0291] In the present invention, [ka] represents trans-1,4-cyclohexylene, [ka] represents a mixture of both cis- and trans-1,4-cyclohexylene, [ka] represents 1,4-phenylene.

[0292] In the present invention, the expression "dielectrically positive compound" means a compound with Δε>1.5, the expression "dielectrically neutral compound" means a compound with -1.5≦Δε≦1.5, and the expression "dielectrically negative compound" means a compound with Δε<-1.5. The dielectric anisotropy of a compound is determined here by dissolving 10% 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 and in each case with homeotropic and homogeneous surface alignment. The measuring voltage is typically between 0.5 V and 1.0 V, but always below the capacitance threshold of the respective liquid crystal mixture under consideration.

[0293] The host mixture used for the dielectrically positive and dielectrically neutral compounds is ZLI-4792, and for the dielectrically negative compounds is ZLI-2857, both from Merck, Germany. The value for each compound studied is obtained from the change in the dielectric constant of the host mixture after the compound studied is added 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 reduced stepwise by half until the study can be carried out at the desired temperature.

[0294] The liquid crystal medium according to the invention may also contain further additives, such as, for example, stabilizers and / or pleochroic, e.g. dichroic dyes and / or chiral dopants, in the usual amounts, if necessary. The amount of these additives used is preferably in total 0% to 10%, particularly preferably 0.1% to 6%, based on the amount of the entire mixture. The concentration of each compound used is preferably 0.1% to 3%. The concentrations of these and similar additives are generally not taken into account when specifying the concentration and concentration range of the liquid crystal compounds in the liquid crystal medium.

[0295] In a preferred embodiment, the liquid-crystalline medium according to the invention comprises a polymer precursor, which comprises one or more reactive compounds, preferably reactive mesogens, and optionally further additives, such as, for example, polymerization initiators and / or polymerization retarders, in the usual amounts. The amount of these additives used is preferably in total 0% to 10%, particularly preferably 0.1% to 2%, based on the amount of the entire mixture. The concentrations of these and similar additives are generally not taken into account when specifying the concentrations and concentration ranges of the liquid-crystalline compounds in the liquid-crystalline medium.

[0296] The composition consists of a number of compounds, preferably from 3 to 30, particularly preferably from 6 to 20, very particularly preferably from 10 to 16, which are mixed in a conventional manner. In general, the desired amount of the compound used in a smaller amount is dissolved in the compound that constitutes the main component of the mixture. This is advantageously carried out at elevated temperature. If the selected temperature is above the clearing point of the main component, it is particularly easy to observe the completion of the dissolving operation. However, it is also possible to prepare the liquid crystal mixture in other conventional ways, for example using premixtures or from the so-called "multi-bottle system".

[0297] The mixtures according to the invention show a very wide nematic phase range with a clearing point above 65° C., very favorable values ​​of the capacity threshold and relatively high values ​​of the retention, and at the same time a 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.

[0298] It will be appreciated by 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.

[0299] The structure of the liquid crystal display according to the invention corresponds to a conventional configuration, for example as described in EP 0 240 379 A1.

[0300] The liquid crystal phase according to the invention can be modified by suitable additives for use in any type of display disclosed to date, for example IPS and FFS LCD displays.

[0301] Table E below lists possible dopants that can be added to the mixture according to the invention. When the mixture contains one or more dopants, the dopants are used in an amount of 0.01% to 4%, preferably 0.1% to 1.0%.

[0302] Stabilizers which may be added to the mixtures according to the invention, preferably in amounts of 0.01% to 6%, in particular 0.1% to 3%, are given in Table F below.

[0303] 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 the mixture components as a whole, unless expressly stated otherwise. In this context, the term "mixture" denotes a liquid-crystalline medium.

[0304] Unless expressly indicated otherwise, all temperature values ​​given in this application, e.g. 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 all temperature differences are given in degrees difference (° or degrees), respectively.

[0305] In the present invention, unless expressly indicated otherwise, the term "threshold voltage" relates to the capacitive threshold (V0), also known as the Freederickss threshold.

[0306] Unless expressly indicated otherwise in each case, all physical properties are determined or have been determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals", November 1997, Merck, Germany, applying a temperature of 20° C., Δn being determined at 436 nm, 589 nm and 633 nm and Δε being determined at 1 kHz.

[0307] The electro-optical properties, such as the threshold voltage (V0) (capacitive measurement), as well as the switch behavior, are determined in test cells manufactured at Merck Japan. The test cells have a soda-lime glass substrate and a polyimide alignment layer (SE-1211 and diluent). ** The alignment layers are rubbed perpendicular to each other, which results in a homeotropic alignment of the liquid crystal. The surface area of ​​the transparent, substantially square ITO electrode is 1 cm. 2 It is.

[0308] Unless stated otherwise, no chiral dopants are added to the liquid crystal mixtures used, but the liquid crystal mixtures are also particularly suitable for applications where this type of doping is required.

[0309] 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, Germany, and 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 It is.

[0310] For practical purposes, the dispersion of a material is conventionally characterized as follows, and will be used throughout this application unless expressly stated otherwise: The birefringence values ​​are determined at a temperature of 20° C. and at several fixed wavelengths using a modified Abbe refractometer with a homeotropic alignment surface on the side of the prism in contact with the material. The birefringence values ​​are determined at specific values ​​of wavelengths 436 nm (respectively selected spectral lines of a low pressure mercury lamp), 589 nm (sodium D line) and 633 nm (He-Ne laser) using an attenuator / diffuser combination to prevent damage to the observer's eyes. In the table below, Δn is given at 589 nm and Δ(Δn) is given by Δ(Δn)=Δn(436 nm)-Δn(633 nm).

[0311] Unless otherwise stated, the following symbols are used: V0 Capacitive threshold voltage at 20℃ [V] n e Anomalous refractive index at 20℃ and 589nm n0Normal refractive index at 20℃ 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 Δ(Δn) is the change in optical anisotropy defined as Δn(20℃, 436nm)-Δn(20℃, 633nm) Δ(Δn *) "Relative change in optical anisotropy" defined as follows: Δ(Δn) / Δn(20℃, 589nm) ε ⊥ Permittivity perpendicular to the director at 20℃ and 1kHz ε ∥ Permittivity parallel to the director at 20°C and 1kHz Δε Dielectric anisotropy at 20℃ and 1kHz T(N,I) or clp. 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℃ [pN]

number

number

[0312] The following examples are intended to illustrate the present invention without limiting it. However, the following examples provide the skilled artisan with the preferred mixing concepts, together with the preferred compounds, their respective concentrations and their combinations with each other. In addition, the following examples illustrate the feasible properties and property combinations.

[0313] In the present invention and the following examples, the structures of liquid crystal compounds are represented by their initial letters, and the conversion to chemical formulas is performed according to Tables A to C below. n H 2n+1 , C m H 2m+1 and C l H 2l+1 or C n H 2n , C m H 2m and C l H 2l are linear alkyl or alkenyl groups having n, m and l C atoms, respectively. 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 elements of the core structure of the compounds, Table B lists the bridging 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 elements with optionally present 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 exemplary structures of the compounds with their respective abbreviations.

[0314] <Table A: Ring elements>

[0315] [Table 1]

[0316] [Table 2]

[0317] [Table 3]

[0318] <Table B: Cross-linking units>

[0319] [Table 4]

[0320] <Table C: Terminal group>

[0321] [Table 5]

[0322] where n and m each represent an integer and the three dots "..." are spaces for other abbreviations from the table.

[0323] In addition to the compound of formula B the mixture according to the invention preferably comprises one or more of the compounds mentioned below.

[0324] The following abbreviations are used: (n, m, k and l are each independently an integer, preferably 1 to 9, preferably 1 to 7, and k and l may be 0, preferably 0 to 4, more preferably 0 or 2, and most preferably 2; n is preferably 1, 2, 3, 4 or 5; in the combination "-nO-", it is preferably 1, 2, 3 or 4, more preferably 2 or 4; m is preferably 1, 2, 3, 4 or 5; in the combination "-Om", it is preferably 1, 2, 3 or 4, more preferably 2 or 4. The combination "-lVm" is preferably "2V1".)

[0325] Exemplary Preferred Compounds of Formula D

[0326] [Table 6]

[0327] Further compounds

[0328] [Table 7]

[0329] High ε ⊥ Exemplary preferred compounds of formula B having the formula

[0330] [Table 8]

[0331] High ε ⊥ Exemplary preferred compounds of formula I having the formula

[0332] [Table 9]

[0333] [Table 10]

[0334] [Table 11]

[0335] [Table 12]

[0336] Exemplary Preferred Dielectrically Positive Compounds

[0337] [Table 13]

[0338] [Table 14]

[0339] [Table 15]

[0340] [Table 16]

[0341] [Table 17]

[0342] [Table 18]

[0343] [Table 19]

[0344] [Table 20]

[0345] Exemplary Preferred Dielectrically Neutral Compounds

[0346] [Table 21]

[0347] [Table 22]

[0348] [Table 23]

[0349] [Table 24]

[0350] [Table 25]

[0351] [Table 26]

[0352] Exemplary Preferred Dielectrically Negative Compounds

[0353] [Table 27]

[0354] [Table 28]

[0355] [Table 29]

[0356] [Table 30]

[0357] [Table 31]

[0358] [Table 32]

[0359] [Table 33]

[0360] [Table 34]

[0361] [Table 35]

[0362] Table E lists chiral dopants which are preferably used in the mixtures according to the invention.

[0363] [Table 36]

[0364] [Table 37]

[0365] [Table 38]

[0366] 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.

[0367] Table F shows stabilizers which 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.

[0368]

[0369] [Table 39]

[0370] [Table 40]

[0371] [Table 41]

[0372] [Table 42]

[0373] [Table 43]

[0374] 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:

[0375] [Table 44] EXAMPLES

[0376] The following examples explain the present invention without limiting it in any way. However, the physical properties clarify for the skilled person the properties that can be achieved and the extent to which they can be modified. Thus, in particular, the combinations of various properties that can be preferably achieved are well defined for the skilled person.

[0377] <Synthesis Example> <Synthesis Example 1>: Synthesis of 2-[4-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane

[0378] [ka]

[0379] <Step 1.1>: 4-(5-propyl-1,3-dioxane-2-yl)cyclohexanone

[0380] [ka]

[0381] Toluene-4-sulfonic acid monohydrate (6.4 g, 32 mmol) is added to a solution of 2-propylpropane-1,3-diol 1 (23.9 g, 193 mmol) and 4-oxocyclohexanecarbaldehyde 2 (CAS 96184-81-5, 30.0 g, 170 mmol) in dichloromethane (270 ml). The mixture is heated under reflux in a Dean-Stark apparatus. After 90 min, the reaction mixture is allowed to cool to ambient temperature and purified on silica gel (dichloromethane / ethyl acetate 9:1). 4-(5-propyl-1,3-dioxan-2-yl)cyclohexanone 3 is isolated as a yellow clear oil that solidifies on standing at ambient temperature. Ambient temperature herein means about 20°C, preferably (20±2)°C.

[0382] <Step 1.2>: 1-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-4-(5-propyl-1,3-dioxan-2-yl)cyclohexanol

[0383] [ka]

[0384] At a temperature of 30° C., a solution of 5-(4-bromo-2-fluoro-phenyl)-1,2,3-trifluorobenzene 4 (CAS 187804-77-9, 25.0 g, 80 mmol) in THF (150 ml) is added dropwise to a solution of isopropylmagnesium chloride-lithium chloride (116 ml, 150 mmol, 1.3 mol / l in THF). After 60 min, a solution of 4-(5-propyl-1,3-dioxan-2-yl)cyclohexanone 3 (25.0 g, 80 mmol) in THF (150 ml) is added dropwise at a temperature of at most 30° C. After another 60 min, distilled water is added to the reaction mixture and it is acidified to pH=5 with hydrochloric acid. The aqueous phase is separated and extracted with MTB-ether. The combined organic phases are washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate, filtered and reduced in volume under vacuum. From the residue, 1-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-4-(5-propyl-1,3-dioxan-2-yl)cyclohexanol 5 is obtained as slightly yellow crystals.

[0385] <Step 1.3>: 2-[4-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane

[0386] [ka]

[0387] To a solution of 1-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-4-(5-propyl-1,3-dioxano-2-yl)cyclohexanol 5 (15.8 g, 15 mmol) in toluene (80 ml), toluene-4-sulfonic acid monohydrate (0.5 g, 3 mmol) is added and the mixture is heated under reflux in a Dean-Stark apparatus for 3 h. The reaction mixture is cooled to ambient temperature, heptane is added, and the diluted solution is then purified on silica gel (heptane / MTB-ether 95:5). After crystallization from 2-propanol and heptane, 2-[4-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane 6 is obtained as a colorless solid. Compound 6 (DLGU-3-F) exhibits the following phase behavior and physical properties: [Table 45]

[0388] The following compounds are prepared analogously:

[0389] <Synthesis Example 2>: Synthesis of 2-[4-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]cyclohexen-3-en-1-yl]-5-butyl-1,3-dioxane

[0390] [ka]

[0391] Compound 7 (abbreviated as DLGU-4-F) exhibits the following phase and physical properties: [Table 46]

[0392] <Synthesis Example 3>: Synthesis of 2-[4-[4-[3,5-difluoro-4-(trifluoromethyl)phenyl]-3-fluorophenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane

[0393] [ka]

[0394] <Step 3.1>: [3,5-difluoro-4-(trifluoromethyl)phenyl]boronic acid

[0395] [ka]

[0396] [3,5-Difluoro-4-(trifluoromethyl)phenyl]boronic acid 9 is obtained as a beige solid.

[0397] <Step 3.2>: 5-(4-bromo-2-fluorophenyl)-1,3-difluoro-2-(trifluoromethyl)benzene

[0398] [ka]

[0399] This gives 5-(4-bromo-2-fluorophenyl)-1,3-difluoro-2-(trifluoromethyl)benzene 11 as a clear, colorless oil.

[0400] <Step 3.3>: 1-[4-[3,5-difluoro-4-(trifluoromethyl)phenyl]-3-fluoro-phenyl]-4-(5-propyl-1,3-dioxan-2-yl)cyclohexanol

[0401] [ka]

[0402] 1-[4-[3,5-Difluoro-4-(trifluoromethyl)phenyl]-3-fluoro-phenyl]-4-(5-propyl-1,3-dioxan-2-yl)cyclohexanol 12 is produced as slightly brown crystals.

[0403] <Step 3.4>: 2-[4-[4-[3,5-difluoro-4-(trifluoromethyl)phenyl]-3-fluorophenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane

[0404] [ka]

[0405] This gives 2-[4-[4-[3,5-difluoro-4-(trifluoromethyl)phenyl]-3-fluorophenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane 13 as a colorless solid. Compound 13 (abbreviated DLGU-3-T) exhibits the following phase sequence and physical properties: [Table 47]

[0406] <Synthesis Example 4>: Synthesis of 2-[4-[4-[3,5-difluoro-4-(trifluoromethoxy)-phenyl]-3-fluorophenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane

[0407] [ka]

[0408] <Step 4.1>: 2-[3,5-difluoro-4-(trifluoromethoxy)phenyl]-4,4,5,5-tetramethyl-1,3-dioxa-2-boronane

[0409] [ka]

[0410] This produces 2-[3,5-difluoro-4-(trifluoromethoxy)phenyl]-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane 15 as a colorless solid.

[0411] <Step 4.2>: 5-(4-bromo-2-fluoro-phenyl)-1,3-difluoro-2-(trifluoromethoxy)benzene

[0412] [ka]

[0413] This produces 5-(4-bromo-2-fluoro-phenyl)-1,3-difluoro-2-(trifluoromethoxy)benzene 16 as a colorless solid.

[0414] <Step 4.3>: 1-[4-[3,5-difluoro-4-(trifluoromethoxy)phenyl]-3-fluorophenyl]-4-(5-propyl-1,3-dioxan-2-yl)cyclohexanol

[0415] [ka]

[0416] 1-[4-[3,5-Difluoro-4-(trifluoromethoxy)phenyl]-3-fluorophenyl]-4-(5-propyl-1,3-dioxan-2-yl)cyclohexanol 17 is produced as yellow crystals.

[0417] <Step 4.4>: 2-[4-[4-[3,5-difluoro-4-(trifluoromethoxy)phenyl]-3-fluorophenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane

[0418] [ka]

[0419] This gives 2-[4-[4-[3,5-difluoro-4-(trifluoromethoxy)phenyl]-3-fluorophenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane 18 as a colorless solid. Compound 18 (abbreviated DLGU-3-OT) exhibits the following phase sequence and physical properties: [Table 48]

[0420] <Synthesis Example 5>: Synthesis of 2-[4-[3-fluoro-4-(2-methyl-3,4,5-trifluorophenyl)phenyl]cyclohex-3-en-1-yl]-5-propyl-1,3-dioxane

[0421] [ka]

[0422] The following abbreviations are used for the end groups in the table below:

[0423] [Table 49]

[0424] Physical properties are given at a temperature of 20°C, and γ1 is given in mPa·sec.

[0425] [ka]

[0426] [Table 50]

[0427] [Table 51]

[0428] <Mixture example> Exemplary mixtures are disclosed below.

[0429] <Comparative Example 1.1> The following mixture (CM-1.1) is prepared and examined:

[0430] [Table 52]

[0431] <Comparative Example 1.2> The following mixture (CM-1.2) is prepared and examined:

[0432] [Table 53]

[0433] <Example 1.0~1.2>

[0434] <Example 1.0> The following mixture (M-1) is prepared and examined:

[0435] [Table 54]

[0436] This mixture, mixture M-1, has an average elastic constant (k av. =(k 11 +1 / 2·k 11 +k 33 ) / 3) and a response time parameter (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good contrast.

[0437] <Examples 1.1~1.3> Alternatively, 0.05% of each of the compounds of the following formula is added to mixture M-1. The resulting mixtures M-1.1, M-1.2 and M-1.3 are characterized by improved stability to harsh conditions, especially to exposure to light.

[0438] [ka]

[0439] <Comparative Example 2> The following mixture (CM-2) is prepared and examined:

[0440] [Table 55]

[0441] <Example 2> The following mixture (M-2) is prepared and examined:

[0442] [Table 56]

[0443] This mixture, mixture M-2, has a k av. and a response time parameter (γ1 / k 11 ) and is characterized by very good transmission in FFS displays and has very good contrast.

[0444] <Example 3> The following mixture (M-3) is prepared and examined:

[0445] [Table 57]

[0446] This mixture, Mixture M-3, has:

[0447] <Example 4> The following mixture (M-4) is prepared and examined:

[0448] [Table 58]

[0449] This mixture, mixture M-4, has a very high elastic constant.

[0450] <Example 5> The following mixture (M-5) is prepared and examined:

[0451] [Table 59]

[0452] This mixture, Mixture M-5, has a fast response time.

[0453] <Example 6> The following mixture (M-6) is prepared and examined:

[0454] [Table 60]

[0455] This mixture, mixture M-6, has a high ε ⊥ and exhibits very good transmission in the FFS cell.

[0456] <Example 7> The following mixture (M-7) is prepared and examined:

[0457] [Table 61]

[0458] This mixture, mixture M-7, has a high ε⊥ and exhibits very good transmission in the FFS cell.

[0459] <Example 8> The following mixture (M-8) is prepared and examined:

[0460] [Table 62]

[0461] This mixture, mixture M-8, has a high ε ⊥ and exhibits very good transmission in the FFS cell.

[0462] <Example 9> The following mixture (M-9) is prepared and examined:

[0463] [Table 63]

[0464] This mixture, mixture M-9, has a high ε ⊥ and exhibits very good transmission in the FFS cell.

[0465] <Example 10> The following mixture (M-10) is prepared and examined:

[0466] [Table 64]

[0467] This mixture, mixture M-10, has high contrast and fast response in FFS cells.

[0468] <Example 11> The following mixture (M-11) is prepared and examined:

[0469] [Table 65]

[0470] This mixture, mixture M-11, has high contrast and fast response in FFS cells.

[0471] <Example 12> The following mixture (M-12) is prepared and examined:

[0472] [Table 66]

[0473] This mixture, Mixture M-12, has a relatively high ε ⊥ has.

[0474] <Example 13> The following mixture (M-13) is prepared and examined:

[0475] [Table 67]

[0476] This mixture, mixture M-13, has a fairly high ε ⊥ has.

[0477] <Example 14> The following mixture (M-14) is prepared and examined:

[0478] [Table 68]

[0479] This mixture, Mixture M-14, has a relatively high ε ⊥ has.

[0480] <Example 15> The following mixture (M-15) is prepared and examined:

[0481] [Table 69]

[0482] This mixture, Mixture M-15, has a relatively high ε ⊥ has.

[0483] <Example 16> The following mixture (M-16) is prepared and examined:

[0484] [Table 70]

[0485] This mixture, Mixture M-16, has a relatively high ε ⊥ has.

[0486] <Example 17> The following mixture (M-17) is prepared and examined:

[0487] [Table 71]

[0488] This mixture, mixture M-17, has a fairly high ε ⊥ has.

[0489] <Example 18> The following mixture (M-18) is prepared and examined:

[0490] [Table 72]

[0491] This mixture, mixture M-18, has high contrast in FFS displays.

[0492] <Example 19> The following mixture (M-19) is prepared and examined:

[0493] [Table 73]

[0494] This mixture, mixture M-19, has a fast response time and good contrast in FFS displays.

[0495] <Example 20> The following mixture (M-20) is prepared and examined:

[0496] [Table 74]

[0497] This mixture, mixture M-20, has a very fast response.

[0498] <Example 21> The following mixture (M-21) is prepared and examined:

[0499] [Table 75]

[0500] This mixture, mixture M-21, has good contrast on FFS displays.

[0501] <Example 22> The following mixture (M-22) is prepared and examined:

[0502] [Table 76]

[0503] This mixture, Mixture M-22, has a high clearing point and good contrast in FFS displays.

[0504] <Example 23> The following mixture (M-23) is prepared and examined:

[0505] [Table 77]

[0506] This mixture, Mixture M-23, has a high clearing point and good contrast in FFS displays.

[0507] <Example 24> The following mixture (M-24) is prepared and examined:

[0508] [Table 78]

[0509] This mixture, mixture M-24, has good contrast on FFS displays.

[0510] <Example 25> The following mixture (M-25) is prepared and examined:

[0511] [Table 79]

[0512] This mixture, mixture M-25, has good contrast on FFS displays.

[0513] <Example 26> The following mixture (M-26) is prepared and examined:

[0514] [Table 80]

[0515] This mixture, mixture M-26, has good contrast on FFS displays.

[0516] <Example 27> The following mixture (M-27) is prepared and examined:

[0517] [Table 81]

[0518] This mixture, Mixture M-27, has negative dielectric anisotropy and has a high clearing point and good contrast in VA displays.

[0519] <Example 28> The following mixture (M-28) is prepared and examined:

[0520] [Table 82]

[0521] This mixture, mixture M-28, has a fairly high ε ⊥ has.

Claims

1. comprising one or more compounds of formula D and one or more additional compounds, However, the total concentration of the one or more compounds of formula D is in the range of 1% to 50% by weight. A liquid crystal medium having a nematic phase, characterized in that: 【Chemistry 1】 (In the formula, R Ｄ is H, an alkyl group having 1 to 15 C atoms (one or more CH ２ The groups are each independently -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -(CO)-O-, -O-(C=O)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene), alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms (one -CH ２ The - group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, such that the O atoms are not directly linked to each other, and one or more H atoms may be replaced by halogen. Y Ｄ１ , Y Ｄ２ , Y Ｄ３ and Y Ｄ４ are the same or different and represent H, F or Cl, with the proviso that Y Ｄ１ and Y Ｄ２ is not H, and X Ｄ is F, Cl, CN, NCS, SF ５ , each of which represents a fluorinated alkyl, alkoxy, alkenyl or alkenyloxy having up to 5 C atoms, However, each ring may be substituted with one or two alkyl groups.

2. 2. The medium according to claim 1, characterized in that the compound of formula D is selected from the group of compounds of formula D-2, D-3, D-5, D-6, D-8 or D-9: 【Chemistry 2】 【Chemistry 3】 in which the parameters have the respective meanings given in claim 1, and However, each ring may be substituted with one or two alkyl groups.

3. 3. The medium according to claim 2, characterized in that the total concentration of one or more compounds of the formulae D-2, D-3, D-5, D-6, D-8 or D-9 is in the range of ≧1% to ≦50% by weight.

4. The medium according to claim 2 or 3, characterized in that it contains one or more compounds of the formula D-6.

5. A medium according to any one of claims 1 to 4, characterized in that it contains one or more compounds of formula D-6 selected from the group consisting of the compounds with the following initials: 【Chemistry 4】 (In the formula, n is 1 to 7.)

6. A medium according to any one of claims 1 to 5, characterized in that it comprises one or more compounds selected from the group of compounds of formulae II and III: 【Chemistry 5】 【Chemistry 6】 (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 7】 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 8】 L ３１ and L ３２ represent, independently of one another, 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, n represents 0, 1, 2 or 3; provided that each ring may be substituted with one or two alkyl groups; With the proviso that compounds of formula D are excluded from compounds of formula III.

7. 7. Liquid-crystalline medium according to claim 1, characterized in that it comprises one or more dielectrically neutral compounds selected from the group of the formulae IV and V 【Chemistry 9】 (In the formula, R ４１ and R ４２ are independently R in formula II ２ has the meaning given in claim 6, 【Chemistry 10】 Z ４１ and Z ４２ are independent of each other, and Z ４１ occurs twice, each of which independently represents -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 each independently R ４１ and R ４２ has one of the meanings given to 【Chemistry 11】 Z ５１ ~Z ５３ are each independently -CH ２ -CH ２ --, --CH ２ represents —O—, —CH═CH—, —C≡C—, —COO— or a single bond; i and j each independently represent 0 or 1; However, each ring may be substituted with one or two alkyl groups.

8. A medium according to any one of claims 1 to 7, characterized in that it comprises one or more compounds of formula B: 【Chemistry 12】 (In the ceremony 【Chemistry 13】 【Chemistry 14】 n represents 1 or 2; R １ represents alkyl, alkoxy, fluorinated alkyl, fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl; X １ represents F, Cl, a fluorinated alkyl, a fluorinated alkenyl, a fluorinated alkoxy or a fluorinated alkenyloxy.

9. A medium according to any one of claims 1 to 8, characterized in that it additionally comprises one or more compounds of formula I. 【Chemistry 15】 (In the ceremony 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 n represents 0 or 1; R １１ and R １２ each independently represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, alkenyl having 2 to 7 C atoms, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, or R １１ is R １ or R １２ Is 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, X １ represents F, Cl, a fluorinated alkyl, a fluorinated alkenyl, a fluorinated alkoxy or a fluorinated alkenyloxy; Compounds of formula B are excluded, and However, each ring may be substituted with one or two alkyl groups.

10. 10. 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 19】 (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, 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 20】 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 21】 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 each independently R ７２ has the meaning given to 【Chemical 22】 p and q each independently represent 0 or 1; However, each ring may be substituted with one or two alkyl groups.

11. 9. The medium of claim 8, wherein the total concentration of the compound of formula B in the entire medium is from 1% to 60%.

12. The medium according to any one of claims 1 to 11, characterized in that it additionally comprises one or more chiral compounds and / or stabilizers.

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

14. Display according to claim 13, characterized in that it is based on the IPS or FFS mode.

15. 15. A display as claimed in claim 13 or 14, characterised in that it comprises an active matrix addressable device.

16. Use of a medium according to any one of claims 1 to 12 in an electro-optical display or electro-optical component.

17. A process for the preparation of a liquid-crystalline medium according to any one of claims 1 to 12, characterized in that one or more compounds of formula D are mixed with one or more further mesogenic compounds and optionally one or more additives.

18. A compound selected from the group of compounds of formula D-2, D-3, D-5, D-6, D-8 or D-9. 【Chemistry 23】 【Chemistry 24】 (In the formula, R D represents H, an alkyl group having 1 to 15 C atoms (in which one or more CH 2 groups may be replaced independently by -C≡C-, -CF 2 O-, -OCF 2 -, -CH═CH-, -O-, -(CO)-O-, -O-(C═O)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene), an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms (one -CH 2 - group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene in such a way that the O atoms are not directly linked to each other, and one or more H atoms may be replaced by halogen), XD represents F, Cl, CN, NCS, SF5, fluorinated alkyl, alkoxy, alkenyl or alkenyloxy, each having up to 5 C atoms; However, each ring may be substituted with one or two alkyl groups.

19. A method for preparing a compound selected from the group of compounds of formula D-2, D-3, D-5, D-6, D-8 or D-9, comprising the steps of: reacting an aryl halide compound of formula DI with a compound of formula D-II to give a compound of formula D-III; in a further step, said compound is converted to a compound of formula D-2, D-3, D-5, D-6, D-8 or D-9. 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 (In the formula, In formula D-I, Hal represents Br, I or Cl; R D represents H, an alkyl group having 1 to 15 C atoms (in which one or more CH 2 groups may be replaced independently by -C≡C-, -CF 2 O-, -OCF 2 -, -CH═CH-, -O-, -(CO)-O-, -O-(C═O)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene), an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms (one -CH 2 - group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene in such a way that the O atoms are not directly linked to each other, and one or more H atoms may be replaced by halogen), Y D1 , Y D2 , Y D3 and Y D4 are the same or different and represent H, F or Cl, provided that at least one of Y D1 and Y D2 is not H; and XD represents F, Cl, CN, NCS, SF5, fluorinated alkyl, alkoxy, alkenyl or alkenyloxy, each having up to 5 C atoms; However, each ring may be substituted with one or two alkyl groups.

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