Thiophene compounds, liquid crystal media, and liquid crystal displays comprising the same

Abstract

The present application relates to a liquid-crystalline medium, which preferably has a nematic phase and a dielectric anisotropy of 0.5 or more, comprising one or more compounds of formula T in which the symbols and the other parameters have the meanings given herein, to its use in electro-optical displays, in particular in active matrix displays based on the IPS or FFS effect, to such displays comprising such a liquid-crystalline medium and to the use of compounds of formula T for improving the transmission and / or the response time of a liquid-crystalline medium comprising one or more further mesogenic compounds.

Description

[0001] The present application relates to novel compounds, to novel liquid-crystalline media, in particular for liquid-crystalline displays, and to these liquid-crystalline displays, in particular to liquid-crystalline displays using the IPS (in-plane switching) or, preferably, the FFS (fringe field switching) effect, both using dielectrically positive liquid crystals. The latter is occasionally also called SB-FFS (super brightness FFS) effect. For this effect, dielectrically positive liquid crystals are used which comprise one or more compounds having a high dielectric constant both parallel and perpendicular to the molecular director, which leads to a large average dielectric constant and a high dielectric ratio and, at the same time, preferably a relatively small dielectric anisotropy. The liquid-crystalline media optionally additionally comprise dielectrically negative, dielectrically neutral compounds or both. The liquid-crystalline media are used for homeotropic (i.e. planar) initial alignment. The liquid-crystalline media of the present application have a positive dielectric anisotropy and comprise compounds having a large dielectric constant both parallel and perpendicular to the molecular director.

[0002] The media are characterized by a particularly high transmission and a reduced response time in the respective displays, which is brought about by their unique combination of physical properties, in particular by their dielectric properties and, in particular, by their high (ε ⊥ / ε av. ) ratio or their high dielectric ratio (ε ⊥ / Δε). This also leads to their excellent performance in displays according to the present application.

[0003] IPS and FFS displays using dielectrically positive liquid crystals are well known in the art and have been widely adopted for various types of displays, such as desktop monitors and televisions, but also for mobile applications.

[0004] However, at present, IPS and, in particular, FFS displays using dielectrically negative liquid crystals are widely adopted. The latter is sometimes also called UB-FFS (ultra bright FFS). Such displays are disclosed, for example, in US 2013 / 0207038 A1. These displays are characterized by a significantly increased transmission compared to the previously used IPS- and FFS displays, which were already dielectrically positive liquid crystals. However, these displays using dielectrically negative liquid crystals have the serious disadvantage that higher operating voltages are required compared to the respective displays using dielectrically positive liquid crystals. Liquid-crystalline media for UB-FFS have a dielectric anisotropy of -0.5 or less and, preferably, -1.5 or less.

[0005] Liquid-crystalline media for HB-FFS (high brightness FFS) have a dielectric anisotropy of 0.5 or more and, preferably, 1.5 or more. Liquid-crystalline media comprising both dielectrically negative and dielectrically positive liquid-crystalline compounds, or mesogenic compounds, are disclosed, for example, in US 2013 / 0207038 A1. These media are characterized by already quite large ε⊥ and ε av . values, but their ratio (ε ⊥ / Δε) is relatively small.

[0006] However, according to the present application, it is preferred to have an IPS or FFS effect with a dielectrically positive liquid-crystalline medium in planar alignment.

[0007] The industrial use of this effect in electro-optical display elements requires liquid-crystalline phases which must satisfy a number of requirements. Of particular importance here are the chemical resistance and the physical influences such as moisture, air, heat, radiation in the infrared, visible and ultraviolet regions, and direct current (DC) and alternating current (AC) electric fields.

[0008] Furthermore, an industrially useful liquid-crystalline phase requires a mesophase in the liquid-crystalline state in a suitable temperature range and at low viscosity.

[0009] None of the series of compounds having a mesophase in the liquid-crystalline state which have been disclosed to date comprises a single compound which meets all these requirements. Therefore, mixtures of 2 to 25, preferably 3 to 18, compounds are usually prepared to obtain a material which can be used as a liquid-crystalline phase.

[0010] Matrix liquid-crystalline displays (MLC displays) are known. Nonlinear elements which can be used for the individual switching of the pixels are, for example, active elements (i.e. transistors). The term "active matrix" is then used, in which thin-film transistors (TFTs) are usually used, which are usually arranged on a glass plate as substrate.

[0011] The distinction between the two technologies lies in the TFTs which comprise compound semiconductors such as CdSe or metal oxides such as ZnO, or in TFTs which are based on polycrystalline and especially amorphous silicon. The latter technology has currently the greatest commercial importance worldwide.

[0012] The TFT matrix is applied to the inner side of one glass plate of the display, while the other glass plate carries a transparent counter electrode on its inner side. The TFTs are very small compared to the size of the pixel electrodes and have virtually no adverse effect on the image. The technology can also be extended to full-color displays, in which a mosaic of red, green and blue filters is arranged in such a way that the filter elements are arranged opposite each switchable pixel.

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

[0014] The term MLC display here includes any matrix display with integrated non-linear elements, i.e. in addition to active matrices also displays with passive elements, such as varistors or diodes (MIM = metal-insulator-metal).

[0015] This type of MLC display is particularly suitable for TV applications, monitors and notebooks or for displays with high information density, for example in automobile construction or aircraft construction. In addition to problems with the angle dependence of the contrast and the response time, some problems also arise in MLC displays due to the insufficiently high specific resistance of the liquid-crystalline mixture [TOGASHI, S., SEKI-GUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, pp. 141 ff., Paris; STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, pp. 145 ff., Paris]. With decreasing resistance, the contrast of the MLC display deteriorates. Since the specific resistance of the liquid-crystalline mixture generally decreases with the lifetime of the MLC display as a result of interactions with the inner surfaces of the display, a high (initial) resistance is very important for the display in order to have an acceptable resistance value over a long operating period.

[0016] In addition to IPS displays (for example: 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) and the long-known TN displays, displays using the ECB effect have established themselves as so-called VAN (vertically aligned nematic) displays as one of the three most important newer types of liquid-crystalline displays, particularly for television applications.

[0017] Among the most important designs that can be mentioned here are MVA (multi-domain vertical alignment, e.g. Yoshide, H. et al., Paper 3.1 : "MVA LCD for Notebook or Mobile PCs... ", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6 to 9, and Liu, C. T. et al., Paper 15.1 : "A 46-inch TFT-LCD HDTV Technology... ", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 750 to 753), PVA (patterned vertical alignment, e.g. Kim, Sang Soo, Paper 15.4: "Super PVA Sets New State-of-the-Art for LCD-TV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 760 to 763) and ASV (advanced super view, e.g. Shigeta, Mitzuhiro and Fukuoka, Hirofumi, Paper 15.2: "Development of High Quality LCD TV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 754 to 757). More modern versions of the VA effect are the so-called PAVA (photo-alignment VA) and PSVA (polymer stabilized VA).

[0018] In general terms, 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, and Miller, Ian, SID Seminar 2004, Seminar M-7: "LCD-Television", Seminar Lecture Notes, M-7 / 1 to M-7 / 32. While the response time of modern ECB displays has been improved significantly by addressing methods with overdrive, for example, Kim, Hyeon Kyeong et al., Paper 9.1 : "A 57-in. Wide UXGA TFT-LCD for HDTV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 106 to 109, achieving video-compatible response times, in particular in the switching of gray levels, remains an unsatisfactory problem.

[0019] ECB displays, like ASV displays, use liquid-crystalline media with negative dielectric anisotropy (Δε), while TN and hitherto all conventional IPS displays use liquid-crystalline media with positive dielectric anisotropy. However, there is an increasing demand for IPS and FFS displays which make use of liquid-crystalline media with negative dielectric anisotropy.

[0020] In this type of liquid-crystalline display, the liquid crystal is used as an electric medium, the optical properties of which change reversibly when a voltage is applied.

[0021] Since, generally in displays, i.e. also in displays according to these mentioned effects, the operating voltage should be as low as possible, liquid-crystalline media which generally consist predominantly of liquid-crystalline compounds having the same sign of dielectric anisotropy and having the highest possible value of dielectric anisotropy are used. Generally, at most a relatively small proportion of neutral compounds and, if possible, no compounds having a dielectric anisotropy of opposite sign to the dielectric anisotropy of the medium are employed. In the case of liquid-crystalline media having a negative dielectric anisotropy, for example for ECB or UB-FFS displays, therefore predominantly compounds having a negative dielectric anisotropy are employed. The liquid-crystalline media employed generally consist predominantly and often even essentially of liquid-crystalline compounds having a negative dielectric anisotropy.

[0022] In media used according to the present application, usually a significant amount of dielectrically positive liquid crystalline compounds and usually only very small amounts of dielectric compounds or even no dielectric compounds at all are employed, since usually liquid crystal displays are intended to have the lowest possible addressing voltage. At the same time, in some cases it can be advantageous to use small amounts of dielectrically neutral compounds.

[0023] US 2013 / 0207038 A1 discloses liquid crystal media for HB-FFS displays, proposing to improve the performance of FFS displays using liquid crystals with positive dielectric anisotropy by additional incorporation of dielectrically negative liquid crystals. However, this leads to the need to compensate the negative contribution of these compounds to the overall dielectric anisotropy of the resulting media. For this, the concentration of dielectrically positive materials has to be increased, which in turn makes less space for using dielectrically neutral compounds as diluents in the mixture, or, alternatively, compounds with a stronger positive dielectric anisotropy have to be used. Both alternatives have the strong disadvantage of increasing the response time of the liquid crystals in the display.

[0024] Liquid crystal media with positive dielectric anisotropy for IPS and FFS displays have been disclosed. Some examples will be given in the following.

[0025] CN 104232105 A discloses liquid crystal media with positive dielectric anisotropy, which have a dielectric ratio (ε ⊥ / Δε) of at most 0.7.

[0026] WO 2014 / 192390 also discloses liquid crystal media with positive dielectric anisotropy, which have a rather high ε || value, but only a dielectric ratio (ε⊥ / Δε) of about 0.5.

[0027] WO 2015 / 007173 discloses liquid crystal media with positive dielectric anisotropy, some of which have a dielectric ratio (ε⊥ / Δε) of about 0.7 and slightly higher up to 0.88.

[0028] The publications DE 10 2016 003 902.3, EP 3 081 620 and EP 3 095 834 relate to liquid crystal compounds or liquid crystal media for use in corresponding displays.

[0029] The applicants of the present application’s pending, not yet published EP 17164891.8, EP 16190393.5, EP 16194162.0, EP 16197206.2 and EP 16199580.8 also relate to liquid crystal compounds or liquid crystal media for use in corresponding displays.

[0030]

[0031] The compounds of the above formula are disclosed in DE 10 2010 027 099 A1. The compounds of the following formula are also disclosed in this document

[0032]

[0033] The compounds of the following formula are disclosed in EP 2 265 692

[0034]

[0035] It is apparent that the nematic phase range of the liquid-crystalline mixture must be sufficiently broad for the intended display application.

[0036] The response time of the liquid-crystalline medium in the display must also be improved, i.e. reduced. This is particularly important for displays of television or 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 obtain a medium having the lowest possible rotational viscosity. However, the results achieved here are insufficient for many applications and it therefore appears desirable to find a further optimization.

[0037] The sufficient stability of the medium to extreme loads, in particular to UV exposure and heating, is of very particular importance. This can be critical, in particular in the case of applications in displays of mobile devices, such as mobile telephones.

[0038] In addition to their relatively poor transmittance and their relatively long response time, the MLC displays disclosed to date have further disadvantages. These are, for example, their relatively low contrast, their relatively high viewing-angle dependence and the difficult reproduction of grey levels in these displays, especially when viewed from an inclined viewing angle, and their insufficient VHR and their insufficient service life. A desired improvement in the transmittance of the displays and their response time is required in order to improve their energy efficiency or their ability to render rapidly moving pictures, respectively.

[0039] There is therefore a great demand for MLC displays having a very high specific resistance while at the same time a large operating temperature range, a short response time and a low threshold voltage, with the aid of which a large number of grey levels can be produced and which in particular have a good and stable VHR.

[0040] It is an object of the present application to provide MLC displays, not only for monitor and TV applications, but also for mobile applications, such as telephones and navigation systems, which are based on the ECB, IPS or FFS effect, without the above-mentioned disadvantages or with the above-mentioned disadvantages to a reduced extent, and at the same time have a very high specific resistance value. In particular, it must be ensured for mobile telephones and navigation systems that they also operate at extremely high and extremely low temperatures.

[0041] Surprisingly, it has been found that if a nematic liquid crystal mixture comprising components as described below is used in these display elements, liquid crystal displays can be obtained which, in particular in IPS and FFS displays, have a low threshold voltage and a short response time, a sufficiently wide nematic phase, a favorably, relatively low birefringence (Δn) and at the same time a high transmission, a good stability against decomposition by heating and UV exposure, and a stable high VHR, which nematic liquid crystal mixture comprises at least one, preferably two or more compounds of formula T, preferably selected from the group of compounds of the subformulae T-1 to T-4 and optionally compounds of formula I, preferably selected from I-1, I-2, I-3, I-4 and compounds of formula I comprising a diphenylthiophene moiety S, particularly preferred these subformulae I-2 and / or I-3 and / or I-4 and / or I-S-1 and / or I-S-2, more preferred I-2 and / or I-4 and / or I-S-2, and preferably additionally at least one compound, preferably two or more compounds, selected from the group of compounds of formula II and III, whereas the former preferably formula II-1 and / or II-2, and / or at least one, preferably two or more compounds selected from formula IV and / or V, and preferably one or more compounds selected from formulae VII to IX (all formulae are defined herein below).

[0042] This type of medium can be used in particular for electro-optical displays with active matrix addressing, such as IPS- or FFS displays.

[0043] The inventive medium preferably additionally comprises one or more compounds selected from the group of compounds of formula II and III, preferably one or more compounds of formula II, more preferably additionally one or more compounds of formula III, and most preferably, additionally one or more compounds selected from the group of compounds of formula IV and V and again preferably one or more compounds selected from the group of compounds of formulae VI to IX (all formulae are defined below).

[0044] The mixtures according to the application exhibit a very wide nematic phase range (clearing point > 70°C), a very favorable threshold of capacitance, a relatively high retention value and at the same time a good low-temperature stability at -20°C and -30°C, and a very low rotational viscosity. The mixtures according to the application are further characterized by a good ratio of clearing point to rotational viscosity and a relatively high positive dielectric anisotropy.

[0045] It has now surprisingly been found that FFS type liquid crystals using liquid crystals with a positive dielectric anisotropy can be realized by using specially selected liquid crystal media. These media are characterized by a specific combination of physical properties. Most decisive among these are their dielectric properties and here the high average dielectric constant (ε av. ), the high dielectric constant perpendicular to the director of the liquid crystal molecules (ε ⊥), a high dielectric anisotropy value (Δε), and in particular, a relatively high ratio of these latter two values: (ε ⊥ / Δε).

[0046] The liquid-crystalline medium according to the present application preferably has a positive dielectric anisotropy, preferably 1.5 or more to 20.0 or less, more preferably 3.0 or more to 8.0 or less and most preferably 4.0 or more to 7.0 or less.

[0047] The liquid-crystalline medium according to the present application preferably has a dielectric constant perpendicular to the director of the liquid-crystalline molecules (ε ⊥ ), more preferably 6.0 or more, more preferably 7.0 or more, more preferably 8.0 or more, more preferably 9 or more, and most preferably 10.0 or more.

[0048] The liquid-crystalline medium according to the present application preferably has a dielectric ratio (ε ⊥ / Δε), more preferably 0.75 or more and most preferably 1.0 or more.

[0049] In a preferred embodiment of the present application, the liquid-crystalline medium, preferably having a dielectric anisotropy (Δε) of 0.5 or more, preferably comprises

[0050] a) one or more compounds of formula T having a high dielectric constant both perpendicular to the director and parallel to the director, preferably in a concentration of 1% to 60%, more preferably 5% to 40%, particularly preferably 8% to 35%,

[0051]

[0052] wherein

[0053] denotes

[0054] one of denotes

[0055]

[0056] preferably

[0057]

[0058] more preferably

[0059] and one of

[0060]

[0061] preferably

[0062]

[0063] most preferably

[0064]

[0065] wherein each ring, and preferably the phenylene ring, is optionally, independently of one another, substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group,

[0066] n denotes 1 or 2, preferably 2,

[0067] R S denotes alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, and preferably alkyl or alkenyl, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene,

[0068] 1,3-cyclopentenylene is a moiety selected from the group consisting of

[0069]

[0070] preferably

[0071]

[0072] most preferably

[0073] and

[0074] X S denotes F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the last four radicals preferably having 1 to 4 C atoms, preferably 1 or 2 C atoms, preferably F, CI, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably CF3 or OCF3, and

[0075] b) one or more compounds selected from the group of compounds of the formulae II and III, which are preferably dielectrically positive, preferably each having a dielectric anisotropy of 3 or more:

[0076]

[0077] wherein

[0078] R 2alkyl, alkoxy, fluoroalkyl or fluoroalkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms and preferably alkyl or alkenyl,

[0079] independently of one another in each occurrence represent

[0080]

[0081]

[0082] preferably

[0083]

[0084] L 21 and L 22 independently of one another represent H or F, preferably L 21 represents F,

[0085] X 2 represents halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, preferably F, CI, -OCF3, -O-CH2CF3, -O-CH=CH2, -O-CH=CF2or -CF3, very preferably F, CI, -O-CH=CF2or -OCF3,

[0086] m represents 0, 1, 2 or 3, preferably 1 or 2 and particularly preferably 1,

[0087] R 3 represents alkyl, alkoxy, fluoroalkyl or fluoroalkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms and preferably alkyl or alkenyl,

[0088] independently of one another in each occurrence represent

[0089]

[0090] preferably

[0091]

[0092] L 31 and L 32 independently of one another represent H or F, preferably L 31 represents F,

[0093] X 3represents halogen, halogenated alkyl or alkoxy with 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy with 2 or 3 C atoms, F, CI, -OCF3, -OCHF2, -O-CH2CF3, -O-CH=CF2, -O-CH=CH2or -CF3, very preferably F, CI, -O-CH=CF2, -OCHF2or -OCF3,

[0094] Z 3 represents -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O- or a single bond, preferably -CH2CH2-, -COO-, trans-CH=CH- or a single bond and very preferably -COO-, trans-CH=CH- or a single bond, and

[0095] n represents 0, 1, 2 or 3, preferably 1, 2 or 3 and particularly preferably 1, and

[0096] c) optionally one or more compounds selected from the group of compounds of the formulae IV and V, which are preferably dielectrically neutral:

[0097]

[0098] wherein

[0099] R 41 and R 42 independently of one another have the meanings as given above for R 2 in formula II, preferably R 41 represents alkyl and R 42 represents alkyl or alkoxy or R 41 represents alkenyl and R 42 represents alkyl,

[0100] independently of one another and, if occur twice, these also independently of one another represent

[0101]

[0102]

[0103] preferably and one or more of the groups

[0104] Z 41 and Z 42 independently of one another and, if Z 41occur twice, these also independently of one another denote -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, -CF2O-, -C≡C- or a single bond, preferably one or more of them denote a single bond, and

[0105] p denotes 0, 1 or 2, preferably 0 or 1, and

[0106] R 51 and R 52 independently of one another have one of the meanings indicated for R 41 and R 42 one of the meanings indicated for R

[0107] each, if present, independently of one another denotes

[0108]

[0109] preferably

[0110]

[0111] preferably

[0112] denotes

[0113] and, if present,

[0114] preferably denotes

[0115] Z 51 to Z 53 each, independently of one another, denotes -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO- or a single bond, preferably -CH2-CH2-, -CH2-O- or a single bond and particularly preferably a single bond,

[0116] i and j each, independently of one another, denote 0 or 1,

[0117] (i + j) preferably denotes 0, 1 or 2, more preferably 0 or 1, and most preferably 1,

[0118] d) optionally, or alternatively or additionally, one or more compounds selected from the group consisting of formulae VI to IX, which are preferably dielectrically negative:

[0119]

[0120]

[0121] wherein

[0122] R 61 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a straight-chain alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, an unsubstituted alkenyl group having 2 to 7 C atoms, preferably a straight-chain alkenyl group, particularly preferably having 2 to 5 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms,

[0123] R 62 represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms, and

[0124] l represents 0 or 1,

[0125] R 71 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a straight-chain 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 straight-chain alkenyl group, particularly preferably having 2 to 5 C atoms,

[0126] 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, and

[0127] represents

[0128] R 81 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a straight-chain 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 straight-chain alkenyl group, particularly preferably having 2 to 5 C atoms,

[0129] R 82represents 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,

[0130] represents

[0131]

[0132] preferably

[0133] more preferably

[0134] Z 8 represents -(C=0)-0-, -CH2-0-, -CF2-0- or -CH2-CH2-, preferably

[0135] -(C=0)-0- or -CH2-0-, and

[0136] o represents 0 or 1,

[0137] R 91 and R 92 independently of one another have the meanings given above for R 72 ,

[0138] R 91 preferably represents an alkyl group having 2 to 5 C atoms, preferably having 3 to 5 C atoms,

[0139] 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.

[0140] represents

[0141] p and q independently of one another represent 0 or 1, and

[0142] (p+q) preferably represents 0 or 1, and if

[0143] represents

[0144] then, alternatively, preferably p=q=1,

[0145] e) optionally, one or more compounds of formula I having a high dielectric constant both perpendicular to the director and parallel to the director, preferably in a concentration of 1 % to 60 %, more preferably 5 % to 40 %, particularly preferably 8 % to 35 %, and

[0146]

[0147] wherein

[0148] denotes

[0149]

[0150] denotes

[0151]

[0152] n denotes 0 or 1,

[0153] R 11 and R 12 independently of one another denote alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkyl, alkoxy or alkenyloxy, and R 11 alternatively denotes R 1 and R 12 alternatively denotes X 1 ,

[0154] R 1 denotes alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, in which one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably cyclopropylene or 1,3-cyclopentylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, in which one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably cyclopropylene or 1,3-cyclopentylene, and preferably alkyl or alkenyl,

[0155] 1,3-cyclopentenylene is a moiety selected from the group consisting of

[0156]

[0157] preferably

[0158]

[0159] most preferably

[0160] and

[0161] X 1 denotes F, CI, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the last four radicals preferably having 1 to 4 C atoms, preferably F, CI, CF3or OCF3, in particular F for formulae I-1 and I-2 and OCF3for formula I-4, and

[0162] f) optionally again one or more compounds of formula S0 having a high dielectric constant both perpendicular to the director and parallel to the director, preferably in a concentration range of 1 to 60 %, more preferably in a range of 5 to 40 %, particularly preferably in a range of 8 to 35 %,

[0163]

[0164] wherein

[0165] denotes

[0166]

[0167] denotes

[0168]

[0169] R S1 and R S2 independently of one another denote alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one -CH2- group can be replaced by cyclopropylidene, 1,3-cyclobutylidene, 1,3-cyclopentylidene, 1,3-cyclopentenylidene, preferably by cyclopropylidene or 1,3-cyclopentylidene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, wherein one -CH2- group can be replaced by cyclopropylidene, 1,3-cyclobutylidene, 1,3-cyclopentylidene, 1,3-cyclopentenylidene, preferably by cyclopropylidene or 1,3-cyclopentylidene, and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkyl, alkoxy or alkenyloxy, and R S1 alternatively denotes R S and R S2 alternatively denotes X S ,

[0170] R S and X S have the meanings given above for R 1 and X 1 under formula I,

[0171] n denotes 0, and in R S2represents X S in the case of X = N, alternatively 1 is indicated.

[0172] The liquid-crystalline medium according to the application preferably has a nematic phase.

[0173] The application also relates to a compound of formula T.

[0174] Preferably, the compound of formula T is a compound selected from the following formulae T-1, T-2, T-3 and T-4:

[0175]

[0176]

[0177] wherein

[0178] R S represents alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,

[0179] X S represents F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the last four radicals preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, more preferably CF3 or OCF3, and

[0180] has the meaning given above, and

[0181] The compounds of formulae T-1 and T-2 are not included in formulae T-3 and T-4.

[0182] Particularly preferred are compounds of formulae T-1, T-2, T-3 and T-4 selected from the following formulae T-1 -1, T-2-1, T-3-1 to T-3-4 and T-4-1 to T4-4:

[0183]

[0184]

[0185]

[0186] The compounds of formula T-1-2 (CLS-n-X) and T-1-1 (CCS-n-X) are prepared in turn according to the following synthesis route as shown in Scheme 1. The key reaction step is the metallation of the bromothiophene, wherein the halogen is replaced by a metal group, which is then added to a derivative of cyclohexanone. After dehydration, the corresponding CLS compound can be isolated, which can be converted into the corresponding CCS compound by hydration.

[0187]

[0188] Scheme 1: General synthesis scheme for CCS and CLS type compounds.

[0189] Herein, R 1 and X have the respective meanings given under R S and X S above for formula T, and are preferably alkyl and F or CF3, respectively.

[0190] Accordingly, the present application also encompasses a method for preparing a compound of formula T as shown in Scheme 1, characterized in that it comprises the method step of metallation of the bromothiophene, wherein the halogen is replaced by a metal group, which is then added to a derivative of cyclohexanone.

[0191] The compounds of formula T-3 and T-4 are prepared according to the following synthesis route as shown in Scheme 2, wherein the ring A T2 is an optionally fluorinated aryl ring. In this case, a cyclohexenyl-aryl bromide is first prepared, which is subsequently coupled in the key step of the synthesis route by Suzuki coupling with a thiophene boronic acid to give a cyclohexenyl aryl thiophene compound. This can in turn be converted by hydrogenation to the corresponding cyclohexyl derivative.

[0192]

[0193] Scheme 2: General synthesis scheme for compounds of formula T-3 and T-4, wherein the ring A T2 is an optionally fluorinated benzene ring.

[0194] Herein, R 1 and X have the respective meanings given under R S and X S above for formula T, and are preferably alkyl and F or CF3, respectively, and R is independently of each other H or F, preferably one or two of R 2 are F and the other is H.

[0195] Preferably, the compounds of formula I comprising a dibenzothiophene moiety are selected from the group consisting of compounds of formula I-S-1 and I-S-2:

[0196]

[0197] wherein

[0198] R S represents alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,

[0199] X s represents F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the last four radicals preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, more preferably CF3 or OCF3.

[0200] Compounds of the formula I containing a dibenzothiophene moiety, in particular compounds of the formulae I-S-1 and I-S-2, can be prepared by various synthetic routes. In all cases, the essential steps are the successive Migita coupling and base-induced closure of the ring to form the S-heterocyclic ring system. These reactions can optionally, and in many cases advantageously, be carried out as "one-pot" (or "single-pot") reactions.

[0201] Compounds of the formula I-S-1 are prepared analogously to the synthesis of compounds of the formula I-3 according to WO 02 / 055463 and comprise two alkoxy groups: (Scheme C1).

[0202]

[0203] Scheme C1 : General synthesis scheme

[0204] Remark:

[0205] X 1 = F, CF3 or OCF3; R = ethyl or 2-ethylhexyl, R 1 = alkyl, or in the case of 1,4-cyclohexenylene compounds, alternatively also alkenyl.

[0206] It is apparent that corresponding cyclohexyl cyclohexanone derivatives can also be used instead of the cyclohexanone compounds.

[0207] For the following propyl homologs of the formula I-S-1, an alternative synthesis path is exemplified.

[0208]

[0209] Scheme C2: Alternative general synthesis scheme

[0210] Remark:

[0211] X 1 = F, CF3or OCF3; R = ethyl or 2-ethylhexyl, R 1 = alkyl or alkenyl.

[0212] (Tf = trifluoromethylsulfonyl = -SO2-CF3

[0213] The product can also be hydrogenated here to give the corresponding 1,4- cyclohexylidene compound. Instead of the cyclohexanone compound, the corresponding cyclohexyl cyclohexanone derivative can also be used.

[0214] A particularly suitable synthesis route for the compounds of the formulae I-S-1 and I-S-2 used according to the application is explained below with reference to Scheme C3.

[0215]

[0216] Scheme C3: Synthesis of compounds of the formula I-S. The radicals R, A, Z, X 1 , X 2 , Y and the subscript m have the corresponding meanings indicated for the ring A S1 , R S , X S in the formula I-S.

[0217] Scheme 3 should only be regarded as exemplary. The person skilled in the art will be able to carry out corresponding modifications of the synthesis shown and also to follow other suitable synthesis routes in order to obtain the compounds of the formulae I-S-1 and I-S-2.

[0218] According to the synthesis as described above and below, the application also comprises in one embodiment a process for the preparation of one or more compounds of the formulae I-S-1 and I-S-2.

[0219] The application thus encompasses a process for the preparation of a compound of the formula I which comprises a dibenzothiophene moiety, characterised in that it comprises the conversion of a compound of the formula II into a compound of the formulae I-S-1 and I-S-2 in the presence of a base, as shown in Scheme C3, in which R, A, Z, X 1 , X 2, W and m have the meanings described above and G represents -OH, -SH or SG' and G' represent a base-labile thiol protecting group. Preferred protecting groups are acetyl, dimethylaminocarbonyl, 2-tetrahydropyranyl, ethoxycarbonyl ethyl, tert-butyl, methyl and 2-ethylhexyloxycarbonyl ethyl, particularly preferred are ethoxycarbonyl ethyl or 2-ethylhexyloxycarbonyl ethyl.

[0220]

[0221] Scheme C4. Process for the preparation of compounds of formula I-S-1 and I-S-2.

[0222] The process and the subsequent work-up of the reaction mixture can be carried out essentially as a batch reaction or as a continuous reaction. Continuous reaction processes include, for example, reactions in a continuously stirred tank reactor, a cascade of stirred reactors, a loop or cross-flow reactor, a flow tube or a microreactor. The reaction mixture is optionally worked up, if necessary by solid-phase filtration, chromatography, separation between immiscible phases (for example extraction), adsorption on a solid support, removal of solvent and / or azeotrope by distillation, selective distillation, sublimation, crystallization, co-crystallization or by nanofiltration through a membrane.

[0223] The present application further relates to the use of the liquid-crystalline mixture and the liquid-crystalline medium according to the present application in IPS and FFS displays, in particular in SG-FFS displays containing the liquid-crystalline medium, for improving the response time and / or the transmittance.

[0224] The present application further relates to a liquid-crystalline display, in particular an IPS or FFS display, particularly preferably an FFS or SG-FFS display, containing the liquid-crystalline medium according to the present application.

[0225] The present application further relates to an IPS or FFS type liquid-crystalline display comprising a liquid-crystalline cell which consists of two substrates, at least one of which is transparent to light and at least one of which has an electrode layer, and a layer of a liquid-crystalline medium located between the substrates, which liquid-crystalline medium comprises a polymeric component and a low-molecular-weight component, wherein the polymeric component is obtainable by polymerization of one or more polymerizable compounds in the liquid-crystalline medium between the substrates of the liquid-crystalline cell, preferably with the application of a voltage, and wherein the low-molecular-weight component is a liquid-crystalline mixture according to the present application as described above and below.

[0226] The displays according to the present application are preferably addressed by an active matrix (active matrix LCD, for short AMD), preferably by a matrix of thin-film transistors (TFT). However, the liquid crystals according to the present application can also be used in a display having other known addressing modes in an advantageous manner.

[0227] The present application further relates to a process for the preparation of a liquid-crystalline medium according to the present application by mixing one or more compounds of formula I comprising a dibenzothiophene moiety, preferably selected from compounds of formula I-S-1 and I-S-2, with one or more low-molecular-weight liquid-crystalline compounds or liquid-crystalline mixtures and, optionally, with further liquid-crystalline compounds and / or additives.

[0228] The following meanings apply mutatis mutandis:

[0229] The term "FFS" is used to denote FFS and SG-FFS displays, unless otherwise specified.

[0230] The term "mesogenic group" is known to the person skilled in the art and is described in the literature and denotes a group which, due to its anisotropy of attraction and repulsion interactions, contributes essentially to the induction of a liquid-crystalline (LC) phase in low-molecular-weight or polymeric substances. A compound containing mesogenic groups (mesogenic compound) does not necessarily have a liquid-crystalline phase itself. A mesogenic compound can also only exhibit liquid-crystalline behaviour when mixed with other compounds and / or after polymerisation. Typical mesogenic groups are, for example, rigid rod-like or disc-like units. A review of the terms and definitions used in connection with mesogenic or liquid-crystalline compounds is given in Pure Appl. Chem. 73(5), 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368.

[0231] The term "spacer group" or simply "spacer" (also referred to as "Sp" in the context) is known to the person skilled in the art and is described in the literature, see for example Pure Appl. Chem. 73(5), 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. Unless otherwise specified, the term "spacer group" or "spacer" in the context denotes a flexible group which links the mesogenic group and the polymerisable group to each other in a polymerisable mesogenic compound.

[0232] For the purposes of the present application, the term "liquid-crystalline medium" is intended to mean a medium comprising a liquid-crystalline mixture and one or more polymerisable compounds (e.g. reactive mesogens). The term "liquid-crystalline mixture" (or "host mixture") is intended to mean a liquid-crystalline mixture consisting only of non-polymerisable low-molecular-weight compounds, preferably two or more liquid-crystalline compounds and optionally further additives, such as chiral dopants or stabilisers.

[0233] Particularly preferred are liquid-crystalline mixtures and liquid-crystalline media which have a nematic phase, in particular at room temperature.

[0234] In a preferred embodiment of the present application, the liquid-crystalline medium comprises one or more compounds of formula I, preferably selected from the group consisting of compounds of formulae 1-1 to 1-4 and 1-S-1 and 1-S-2.

[0235]

[0236] wherein the parameters have the meanings given above and preferably

[0237] R 11 and R 12 independently of one another, alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, where one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, where one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,

[0238] R 1 and R S independently of one another, alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, where one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, where one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,

[0239] X 1 and X S F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the four last-mentioned radicals preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, in particular F for formulae 1-1 and 1-2, and OCF3 for formula 1-4.

[0240] In a preferred embodiment of the present application, the liquid-crystalline medium comprises one or more compounds of formula I-S0, preferably selected from the group consisting of compounds of formulae 1-S0-1 and 1-S0-2.

[0241]

[0242] wherein the parameters have the meanings given above and preferably

[0243] R S1 and R S2 independently of one another, alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, where one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, where one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentylene, and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,

[0244] X S denotes F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the latter four radicals preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, more preferably CF3 or OCF3.

[0245] In a preferred embodiment of the present application, the liquid-crystalline medium comprises one or more preferably dielectrically positive compounds, preferably having a dielectric anisotropy of 3 or more, selected from the group consisting of compounds of formulae II-1 and II-2:

[0246]

[0247] where the parameters have the respective meanings indicated above under formula II, and L 23 and L 24 independently of one another, H or F, preferably L 23 denotes F, and

[0248] have one of the meanings given for

[0249] and in the case of formulae II-1 and II-2, X 2 preferably denotes F or OCF3, particularly preferably F, and in the case of formula II-2,

[0250]

[0251] independently of one another, preferably denote

[0252]

[0253] and / or are selected from the group consisting of compounds of formulae III-1 and III-2: ​

[0254]

[0255] wherein the parameters have the meanings given in formula III,

[0256] and the medium according to the application can comprise one or more compounds of formula III-3 instead of and / or in addition to compounds of formula III-1 and / or III-2

[0257]

[0258] wherein the parameters have the respective meanings described above, and the parameter L 31 and L 32 independently of one another and of the other parameters, denote H or F.

[0259] The liquid-crystalline medium preferably comprises one or more compounds selected from compounds of formulae II-1 and II-2, wherein L 21 and L 22 and / or L 23 and L 24 all denote F.

[0260] In a preferred embodiment, the liquid-crystalline medium comprises one or more compounds selected from compounds of formulae II-1 and II-2, wherein L 21 , L 22 , L 23 and L 24 all denote F.

[0261] The liquid-crystalline medium preferably comprises one or more compounds of formula II-1. The compounds of formula II-1 are preferably selected from compounds of formulae II-1 a to II-1 e, preferably one or more compounds of formulae II-1 a and / or II-1 b and / or II-1 d, preferably compounds of formulae II-1 a and / or II-1 d or II-1 b and / or II-1 d, most preferably compounds of formula II-1 d:

[0262]

[0263] wherein the parameters have the respective meanings described above, and the parameter L 25 and L 26 independently of one another and of the other parameters, denote H or F, and preferably

[0264] In formulae II-1 a and II-1 b,

[0265] L 21 and L 22 all denote F,

[0266] In formulae II-1 c and II-1 d,

[0267] L 21 and L 22 each, independently of one another, denote F and / or L 23 and L 24 each, independently of one another, denote F, and

[0268] in formula II-1e,

[0269] L 21 , L 22 and L 23 denote F.

[0270] The liquid-crystalline medium preferably comprises one or more compounds of formula II-2, which are preferably selected from compounds of formulae II-2a to II-2k, preferably one or more compounds of each of formulae II-2a and / or II-2h and / or II-2j:

[0271]

[0272]

[0273] where the parameters have the respective meanings indicated above, and L 25 to L 28 each, independently of one another, denote H or F, preferably L 27 and L 28 each, independently of one another, denote H, particularly preferably L 26 denotes H.

[0274] The liquid-crystalline medium preferably comprises a compound selected from compounds of formulae II-1a to II-1e, wherein L 21 and L 22 each, independently of one another, denote F and / or L 23 and L 24 each, independently of one another, denote F.

[0275] In a preferred embodiment, the liquid-crystalline medium comprises a compound selected from compounds of formulae II-2a to II-2k, wherein L 21 , L 22 , L 23 and L 24 each, independently of one another, denote F.

[0276] Especially preferred compounds of formula II-2 are compounds of the following formulae, particularly preferably formulae II-2a-1 and / or II-2h-1 and / or II-2k-2:

[0277]

[0278]

[0279]

[0280] wherein R2 and X 2 have the above-mentioned meanings, and X 2 preferably denotes F.

[0281] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1. The compounds of formula III-1 are preferably selected from compounds of formulae III-1 a to III-1 j, preferably from formulae III-1 c, III-1 f, III-1 g and III-1 j:

[0282]

[0283]

[0284] where the parameters have the above-given meanings and preferably where the parameters have the above-mentioned respective meanings, the parameter L 35 and L 36 independently of one another and of the other parameters, denote H or F, and the parameter L 35 and L 36 independently of one another and of the other parameters, denote H or F.

[0285] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 c, which are preferably selected from compounds of formulae III-1 c-1 to III-1 c-5, preferably from formulae III-1 c-1 and / or III-1 c-2, most preferably from formula III-1 c-1 :

[0286]

[0287] where R 3 have the above-mentioned meanings.

[0288] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 f, which are preferably selected from compounds of formulae III-1 f-1 to III-1 f-6, preferably from formulae III-1 f-1 and / or III-1 f-2 and / or III-1 f-3 and / or III-1 f-6, more preferably from formulae III-1 f-3 and / or III-1 f-6, more preferably from formula III-1 f-6:

[0289]

[0290]

[0291] where R 3 have the above-mentioned meanings.

[0292] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 g, which are preferably selected from compounds of formulae III-1 g-1 to III-1 g-5, preferably from formula III-1 g-3:

[0293]

[0294] wherein R 3 have the above-mentioned meanings.

[0295] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 h, which are preferably selected from compounds of formulae III-1 h-1 to III-1 h-3, preferably of formula III-1 h-3:

[0296]

[0297] wherein the parameters have the meanings given above, and X 3 preferably denotes F.

[0298] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 i, which are preferably selected from compounds of formulae III-1 i-1 and III-1 i-2, preferably of formula III-1 i-2:

[0299]

[0300] wherein the parameters have the meanings given above, and X 3 preferably denotes F.

[0301] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 j, which are preferably selected from compounds of formulae III-1 j-1 and III-1 j-2, preferably of formula III-1 j-1:

[0302]

[0303] wherein the parameters have the meanings given above.

[0304] The liquid-crystalline medium preferably comprises one or more compounds of formula III-2. The compounds of formula III-2 are preferably selected from compounds of formulae III-2a and III-2b, preferably of formula III-2b:

[0305]

[0306] wherein the parameters have the above-mentioned meanings, and the parameter L 33 and L 34 independently of one another and of the other parameters, denote H or F.

[0307] The liquid-crystalline medium preferably comprises one or more compounds of formula III-2a, which are preferably selected from compounds of formulae III-2a-1 to III-2a-6:

[0308]

[0309] wherein R 3 have the above-mentioned meanings.

[0310] The liquid-crystalline medium preferably comprises one or more compounds of formula III-2b, which are preferably selected from compounds of formulae III-2b-1 to III-2b-4, preferably III-2b-4:

[0311]

[0312] wherein R 3 have the above-mentioned meanings.

[0313] Instead of or in addition to compounds of formulae III-1 and / or III-2, the medium according to the application can comprise one or more compounds of formula III-3

[0314]

[0315] wherein the parameters have the respective meanings indicated above in formula III.

[0316] These compounds are preferably selected from formulae III-3a and III-3b:

[0317]

[0318] wherein R 3 have the above-mentioned meanings.

[0319] The liquid-crystalline medium according to the application preferably comprises one or more dielectrically neutral compounds, preferably having a dielectric anisotropy of -1.5 to 3, preferably selected from compounds of formulae VI, VII, VIII and IX.

[0320] In the present application, the elements include all isotopes of the respective elements. In particular, one or more H in the compounds can be replaced by D, and this is particularly preferred in certain embodiments. The corresponding highly deuterated compounds can be detected and identified, for example, in the case of compounds of formula I. This is very useful in certain cases, in particular in the case of compounds of formula I.

[0321] In the present application,

[0322] alkyl preferably denotes straight-chain alkyl, in particular CH3-, C2H5-, n-C3H7-, n-C4H9- or n-C5H 11 - and

[0323] alkenyl preferably denotes CH2=CH-, E-CH3-CH=CH-, CH2=CH-CH2-CH2-, E-CH3-CH=CH-CH2-CH2- or E-(n-C3H7)-CH=CH-.

[0324] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VI, which are selected from the group consisting of the compounds of the formulae VI-1 and VI-2, preferably one or more compounds each of the formula VI-1 and one or more compounds of the formula VI-2,

[0325]

[0326] where the parameters have the respective meanings given in formula VI above, and preferably R 61 and R 62 independently of one another denote methoxy, ethoxy, propoxy, butoxy (alternatively also pentoxy), preferably ethoxy, butoxy or pentoxy, more preferably ethoxy or butoxy and most preferably butoxy;

[0327] in the formula VI-2

[0328] R 61 preferably denote 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, and

[0329] R 62 denote an unsubstituted alkyl radical having 1 to 7 C atoms, preferably having 2 to 5 C atoms, or preferably an unsubstituted alkoxy radical having 1 to 6 C atoms, particularly preferably having 2 or 4 C atoms, and most preferably ethoxy, and

[0330] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VII, which are selected from the group consisting of the compounds of the formulae VII-1 to VII-3, preferably one or more compounds each of the formula VII-1 and one or more compounds of the formula VII-2,

[0331]

[0332] where the parameters have the respective meanings given in formula VII above, and preferably

[0333] R 71 denote 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, and

[0334] R 72 denote an unsubstituted alkyl radical having 1 to 7 C atoms, preferably having 2 to 5 C atoms, or preferably an unsubstituted alkoxy radical having 1 to 6 C atoms, particularly preferably having 2 or 4 C atoms, and most preferably ethoxy.

[0335] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VI-1, selected from the following compounds:

[0336]

[0337] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VI-2, selected from the following compounds:

[0338]

[0339] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VII-1, selected from the following compounds:

[0340]

[0341] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VII-2, selected from the following compounds:

[0342]

[0343] In addition to the compounds of the formula I or of its preferred subformulae, the medium according to the application preferably also comprises one or more preferably dielectrically neutral compounds selected from the group of the compounds of the formulae VI and VII, preferably in a total concentration of 5% or more to 90% or less, preferably 10% or more to 80% or less, particularly preferably 20% or more to 70% or less.

[0344] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VIII, selected from the group of the compounds of the formulae VIII-1 to VIII-3, preferably one or more compounds each of the formula VIII-1 and / or one or more compounds of the formula VIII-3,

[0345]

[0346] in which the parameters have the respective meanings given in the above formula VIII, and preferably

[0347] R 81 denotes vinyl, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, ethyl, n-propyl or n-pentyl, alkyl, preferably ethyl, n-propyl or n-pentyl and

[0348] R 82represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably having 1 to 5 C atoms, or an unsubstituted alkoxy group having 1 to 6 C atoms.

[0349] in the formulae VIII-1 and VIII-2, R 82 represents an alkyl group, preferably methyl, ethyl or n-propyl, most preferably methyl, and in the formula VIII-3 it preferably represents an alkoxy group, preferably ethoxy, and most preferably ethoxy.

[0350] In a further preferred embodiment, the medium comprises one or more compounds of the formula IV one or more compounds of the formula IV

[0351]

[0352] wherein

[0353] R 41 represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, preferably an n-alkyl group, particularly preferably having 2, 3, 4 or 5 C atoms, and

[0354] 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, all preferably having 2 to 5 C atoms, an unsubstituted alkenyl group having 2 to 7 C atoms, preferably having 2, 3 or 4 C atoms, more preferably a vinyl group or a 1-propenyl group and particularly a vinyl group.

[0355] In a particularly preferred embodiment, the medium comprises one or more compounds of the formula IV one or more compounds of the formula IV-1 to IV-4, preferably of the formula IV-1,

[0356]

[0357] wherein

[0358] alkyl and alkyl' independently of one another represent an alkyl group having 1 to 7 C atoms, preferably having 2 to 5 C atoms,

[0359] alkenyl and alkenyl' independently of one another represent an alkenyl group having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably 2 C atoms,

[0360] alkenyl' represents an alkenyl group having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably having 2 to 3 C atoms, and

[0361] Alkoxy denotes an alkoxy group having 1 to 5 C atoms, preferably having 2 to 4 C atoms.

[0362] In a particularly preferred embodiment, the medium according to the application comprises one or more compounds of the formula IV-1 and / or one or more compounds of the formula IV-2.

[0363] In a further preferred embodiment, the medium comprises one or more compounds of the formula V.

[0364] The medium according to the application preferably comprises the following compounds in the total concentration stated:

[0365] 0 to 60 % by weight of one or more compounds selected from the group of the compounds of the formula T and

[0366] 0 to 60 % by weight, preferably 1 to 60 % by weight, of one or more compounds selected from the group of the compounds of the formulae I and I-S-1, I-S-2, I-S0-1 and I-S0-2 and / or

[0367] 5 to 60 % by weight of one or more compounds of the formula II, preferably selected from the group of the compounds of the formulae II-1 and II-2 and / or

[0368] 5 to 25 % by weight of one or more compounds of the formula III and / or

[0369] 5 to 45 % by weight of one or more compounds of the formula IV and / or

[0370] 5 to 25 % by weight of one or more compounds of the formula V and / or

[0371] 5 to 25 % by weight of one or more compounds of the formula VI and / or

[0372] 5 to 20 % by weight of one or more compounds of the formula VII and / or

[0373] 5 to 30 % by weight of one or more compounds of the formula VIII, preferably selected from the group of the compounds of the formulae VIII-1 and VIII-2 and / or

[0374] 0 to 60 % by weight of one or more compounds of the formula IX,

[0375] The total content of all compounds of the formulae T and I to IX present in the medium is preferably 95 % or more and more preferably 100 %.

[0376] The latter condition is preferred for all media according to the present application.

[0377] In a further preferred embodiment, the medium according to the application, in addition to the compound of the formula T or a preferred subformulae thereof and / or the compound of the formula I or a preferred subformulae thereof and the compound of the formulae VI and / or VII and / or VIII and / or IX, preferably comprises one or more preferred dielectrically neutral compounds selected from the group of the compounds of the formulae IV and V, preferably in a total concentration of 5% or more to 90% or less, preferably 10% or more to 80% or less, particularly preferably 20% or more to 70% or less.

[0378] In a particularly preferred embodiment, the medium according to the application comprises

[0379] one or more compounds of the formula II in a total concentration of 5% or more to 50% or less, preferably 10% or more to 40% or less, and / or

[0380] one or more compounds of the formula VII-1 in a total concentration of 5% or more to 30% or less, and / or

[0381] one or more compounds of the formula VII-2 in a total concentration of 3% or more to 30% or less.

[0382] Preferably, the concentration of the compound of the formula T in the medium according to the application is 1% or more to 60% or less, more preferably 5% or more to 40% or less, most preferably 8% or more to 35% or less.

[0383] Preferably, the concentration of the compound of the formula I, preferably selected from the group of the formulae I-1 to I-4, preferably I-3 and / or I-4 and / or I-S-1 and / or I-S-2, if present, in the medium according to the application is 1% or more to 60% or less, more preferably 5% or more to 40% or less, most preferably 8% or more to 35% or less.

[0384] In a preferred embodiment of the present application, the medium comprises one or more compounds of the formula I comprising a dibenzothiophene moiety, preferably selected from the group of the formulae I-S-1 and I-S-2 and one or more compounds of the formula I, preferably selected from the group of the formulae I-1 to I-4, preferably I-3 and / or I-4.

[0385] Preferably, the concentration of the compounds of the formulae I-S-1 and I-S-2 in the medium according to the application is 1% or more to 60% or less, more preferably 5% or more to 40% or less, most preferably 8% or more to 35% or less.

[0386] In a preferred embodiment of the present application, the concentration of the compound of the formula II in the medium is 3% or more to 60% or less, more preferably 5% or more to 55% or less, more preferably 10% or more to 50% or less and most preferably 15% or more to 45% or less.

[0387] In a preferred embodiment of the present application, the concentration of the compound of formula VII in the medium is 2 % or more to 50 % or less, more preferably 5 % or more to 40 % or less, more preferably 10 % or more to 35 % or less and most preferably 15 % or more to 30 % or less.

[0388] In a preferred embodiment of the present application, the concentration of the compound of formula VII-1 in the medium is 1 % or more to 40 % or less, more preferably 2 % or more to 35 % or less or, alternatively, 15 % or more to 25 % or less.

[0389] In a preferred embodiment of the present application, the concentration of the compound of formula VII-2, if present, in the medium is 1 % or more to 40 % or less, more preferably 5 % or more to 35 % or less and most preferably 10 % or more to 30 % or less.

[0390] The present application also relates to an electro-optical display or electro-optical component comprising the liquid-crystalline medium according to the present application. Preferred are electro-optical displays based on the VA, ECB, IPS or FFS effect, preferably based on the VA; IPS or FFS effect, and in particular those which are addressed by active matrix addressing devices.

[0391] Accordingly, the present application also relates to the use of a liquid-crystalline medium according to the present application in an electro-optical display or electro-optical component, and to a process for the preparation of a liquid-crystalline medium according to the present application, characterized in that one or more compounds of formula I are mixed with one or more compounds of formula II, preferably with one or more compounds of the subformulae II-1 and / or II-2 and / or with one or more compounds of formula VII, preferably with one or more compounds of the subformulae VII-1 and / or VII-2, particularly preferably with two or more, preferably three or more and very particularly preferably with all four compounds selected from these formulae II-1, II-2, VII-1 and VII-2 and one or more further compounds, preferably compounds selected from formulae IV and V, more preferably with one or more compounds of formula IV and formula V.

[0392] In a further preferred embodiment, the medium comprises one or more compounds of formula IV selected from the group consisting of the compounds of formulae IV-2 and IV-3,

[0393]

[0394] wherein

[0395] alkyl and alkyl' independently of each other denote alkyl having 1 -7 C atoms, preferably having 2-5 C atoms,

[0396] alkoxy denotes an alkoxy group having 1 to 5 C atoms, preferably having 2 to 4 C atoms.

[0397] In a further preferred embodiment, the medium comprises one or more compounds of formula V selected from the group consisting of compounds of formulae V-1 and V-2, preferably of formula V-1,

[0398]

[0399]

[0400] wherein the parameters have the meanings given above in formula V, and preferably

[0401] R 51 denotes alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms, and

[0402] R 52 denotes 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.

[0403] In a further preferred embodiment, the medium comprises one or more compounds of formula V-1 selected from the group consisting of compounds of formulae V-1 a and V-1 b,

[0404]

[0405] wherein

[0406] alkyl and alkyl' independently of each other denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, and

[0407] alkenyl denotes alkenyl having 2 to 7 C atoms, preferably having 2 to 5 C atoms.

[0408] Furthermore, the present application relates to a method for reducing the wavelength dispersion of the birefringence of a liquid-crystalline medium comprising one or more compounds of formula II, optionally one or more compounds selected from the group consisting of compounds of formulae VII-1 and VII-2 and / or one or more compounds of formula IV and / or one or more compounds of formula V, characterised in that one or more compounds of formula I are used in this medium.

[0409] In addition to the compounds of formulae I to V, other constituents can also be present, for example in an amount of up to 45 %, but preferably up to 35 %, in particular up to 10 %, based on the entire mixture.

[0410] The medium according to the present application can also optionally comprise a dielectrically positive component, the total concentration of which is preferably 20 % or less, more preferably 10 % or less, based on the entire medium.

[0411] In a preferred embodiment, the liquid-crystalline medium according to the application comprises in total, based on the entire mixture:

[0412] 1 % or more to 50 % or less, preferably 2 % or more to 35 % or less, particularly preferably 3 % or more to 25 % or less, of compounds of formula T,

[0413] 1 % or more to 50 % or less, preferably 2 % or more to 35 % or less, particularly preferably 3 % or more to 25 % or less, of compounds of formula I containing a dibenzothiophene moiety,

[0414] 1 % or more to 20 % or less, preferably 2 % or more to 15 % or less, particularly preferably 3 % or more to 12 % or less, of compounds of formula I,

[0415] 20 % or more to 50 % or less, preferably 25 % or more to 45 % or less, particularly preferably 30 % or more to 40 % or less, of compounds of formula II and / or III, and

[0416] 0 % or more to 35 % or less, preferably 2 % or more to 30 % or less, particularly preferably 3 % or more to 25 % or less, of compounds of formula IV and / or V, and

[0417] 5 % or more to 50 % or less, 10 % or more to 45 % or less, preferably 15 % or more to 40 % or less, of compounds of formula VI and / or VII and / or VIII and / or IX.

[0418] The liquid-crystalline medium according to the application can comprise one or more chiral compounds.

[0419] Particularly preferred embodiments of the application meet one or more of the following conditions:

[0420] wherein the abbreviations (short forms) are explained in Tables A to C and illustrated by examples in Table D.

[0421] In a preferred embodiment of the present application, the compounds of formula T, which are preferred per se and preferably used in the liquid-crystalline medium, comprise one or more rings, preferably one ring

[0422] are selected from

[0423]

[0424] are preferably selected from

[0425]

[0426] are most preferably

[0427] Preferably the medium according to the present application fulfils one or more of the following conditions:

[0428] i. the liquid crystalline medium has a birefringence of 0.060 or more, particularly preferably 0.070 or more.

[0429] ii. the liquid crystalline medium has a birefringence of 0.200 or less, particularly preferably 0.180 or less.

[0430] iii. the liquid crystalline medium has a birefringence of 0.090 or more to 0.120 or less.

[0431] iv. the liquid crystalline medium comprises one or more compounds of formula T, preferably selected from the group consisting of compounds of formulae CCS-n-F, CCS-n-Cl, CCS-n-T, CLS-n-F, CLS-n-Cl, CLS-n-T, CPS-n-F, CPS-n-T, CGS-n-T, CUS-n-T, CYS-n-T and LGS-n-T, preferably selected from the group consisting of compounds of formulae CCS-n-T, CLS-n-T, CGS-n-T, CUS-n-T, CYS-n-T and LGS-n-T,

[0432] v. the liquid crystalline medium comprises one or more compounds of formula I-4, particularly preferably.

[0433] vi. the total concentration of compounds of formula IV in the mixture as a whole is 25% or more, preferably 30% or more, and preferably 25% or more to 49% or less, particularly preferably 29% or more to 47% or less, and very particularly preferably 37% or more to 44% or less.

[0434] vii. the liquid crystalline medium comprises one or more compounds of formula IV selected from the group consisting of compounds of formulae CC-n-V and / or CC-n-Vm and / or CC-V-V and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably CC-3-V, preferably in a concentration of at most 60% or less, particularly preferably at most 50% or less, and optionally additional CC-3-V1, preferably in a concentration of at most 15% or less, and / or CC-4-V, preferably in a concentration of at most 24% or less, particularly preferably at most 30% or less.

[0435] viii. the medium comprises a compound of formula CC-n-V, preferably CC-3-V, preferably in a concentration of 1% or more to 60% or less, more preferably in a concentration of 3% or more to 35% or less.

[0436] The total concentration of compounds of formula CC-3-V in the mixture as a whole is preferably 15% or less, preferably 10% or less or 20% or more, preferably 25% or more.

[0437] ix. the total concentration of compounds of formula Y-nO-Om in the mixture as a whole is 2% or more to 30% or less, preferably 5% or more to 15% or less.

[0438] x. the total concentration of compounds of formula CY-n-Om in the mixture as a whole is 5% or more to 60% or less, preferably 15% or more to 45% or less.

[0439] xi. the total concentration of compounds of formulae CCY-n-Om and / or CCY-n-m, preferably CCY-n-Om, in the mixture as a whole is 5% or more to 40% or less, preferably 1% or more to 25% or less.

[0440] xii. the total concentration of compounds of formula CLY-n-Om in the mixture as a whole is 5% or more to 40% or less, preferably 10% or more to 30% or less.

[0441] xiii. the liquid-crystalline medium comprises one or more compounds of formula IV, preferably of formulae IV-1 and / or IV-2, preferably in a total concentration of 1% or more, in particular 2% or more, and very particularly preferably 3% or more to 50% or less, preferably 35% or less.

[0442] xiv. the liquid-crystalline medium comprises one or more compounds of formula V, preferably of formulae V-1 and / or V-2, preferably in a total concentration of 1% or more, in particular 2% or more, and very particularly preferably 15% or more to 35% or less, preferably to 30% or less.

[0443] xv. the total concentration of compounds of formulae CCP-V-n, preferably CCP-V-1, in the mixture as a whole, preferably is 5% or more to 30% or less, preferably 15% or more to 25% or less.

[0444] xvi. the total concentration of compounds of formulae CCP-V2-n, preferably CCP-V2-1, in the mixture as a whole, preferably is 1% or more to 15% or less, preferably 2% or more to 10% or less.

[0445] The application further relates to an electro-optical display having an active matrix addressing on the basis of the VA, ECB, IPS, FFS or UB-FFS effect, characterized in that it contains, as dielectric, a liquid-crystalline medium according to the application.

[0446] The liquid-crystalline mixture preferably has a nematic phase range of at least 70 degrees in width.

[0447] The rotational viscosity γ1 is preferably 200 mPa-s or less, preferably 150 mPa-s or less and in particular 120 mPa-s or less.

[0448] The mixtures according to the application are suitable for all IPS and FFS-TFT applications using dielectrically positive liquid-crystalline media, for example SG-FFS (super- controlled FFS).

[0449] The liquid-crystalline medium according to the application preferably consists essentially of 4 to 18, in particular 5 to 15, and particularly preferably 12 or fewer compounds. These are preferably selected from the group of the compounds of the formulae S, I, II, III, IV, V, VI, VII, VIII and IX.

[0450] The liquid-crystalline medium according to the application can also optionally comprise more than 18 compounds. In this case, they preferably comprise 18 to 25 compounds.

[0451] In a preferred embodiment, the liquid-crystalline medium according to the application consists essentially of, preferably consists essentially of and most preferably consists essentially of compounds which do not comprise a cyano group.

[0452] In a preferred embodiment, the liquid-crystalline medium according to the application comprises compounds selected from the group of the compounds of the formulae T, I, II and III, IV and V and VI to IX, preferably from the group of the compounds of the formula T, preferably from the group consisting of T-1 to T-4, I, preferably from the group consisting of I-1, I-2, I-3 and I-4, I, which comprise a dibenzothiophene moiety, the latter being preferably selected from the group consisting of I-S-1, I-S-2, I-S-0, preferably from the group consisting of I-S-0-1 and I-S-0-2, II, preferably from the group consisting of II-1 and II-2, III, preferably from the group consisting of III-1 and III-2, IV, V, VII, preferably from the group consisting of VII-1 and VII-2, VIII and IX; they preferably consist essentially of, particularly preferably essentially of and very particularly preferably essentially of the compounds of the said formulae.

[0453] The liquid-crystalline medium according to the application preferably has a nematic phase in each case of at least -10°C or less to 70°C or more, particularly preferably -20°C or less to 80°C or more, very particularly preferably -30°C or less to 85°C or more and most preferably -40°C or less to 90°C or more.

[0454] The expression "has a nematic phase" here means on the one hand that no smectic phase and no crystallization is observed at the respective temperature at low temperature and on the other hand that no clearing occurs on heating from the nematic phase. The investigations at low temperature are carried out in a flow viscosimeter at the respective temperature and checked by storage in test cells having a cell thickness corresponding to the electrical-optical applications of at least 100 hours. If the storage stability at a temperature of -20°C is 1000 h or more in the respective test cell, the medium is regarded as stable at this temperature. At temperatures of -30°C and -40°C, the respective times are 500 h and 250 h, respectively. At high temperature, the clearing point is measured in a capillary by conventional methods.

[0455] In a preferred embodiment, the liquid-crystalline medium according to the present application is characterized by an optical anisotropy value in the moderate to low range. The birefringence value is preferably 0.075 or more to 0.130 or less, particularly preferably 0.085 or more to 0.120 or less and very particularly preferably 0.090 or more to 0.115 or less.

[0456] In this embodiment, the liquid-crystalline medium according to the present application has a positive dielectric anisotropy and a relatively high absolute value of the dielectric anisotropy Δε, which is preferably 0.5 or more, preferably 1.0 or more, more preferably 2.0 or more to 20 or less, more preferably to 15 or less, more preferably 3.0 or more to 10 or less, particularly preferably 4.0 or more to 9.0 or less and very particularly preferably 4.5 or more to 8.0 or less.

[0457] The liquid-crystalline medium according to the present application preferably has a relatively low threshold voltage (Vo) value in the range of 1.0 V or more to 2.7 V or less, preferably 1.2 V or more to 2.5 V or less, particularly preferably 1.3 V or more to 2.2 V or less.

[0458] In a further preferred embodiment, the liquid-crystalline medium according to the present application preferably has a relatively high average dielectric constant value (ε av. ≡ (ε || + 2ε ⊥ ) / 3), which is preferably 4.0 or more to 25.0 or less, preferably 5.0 or more to 20.0 or less, still more preferably 6.0 or more to 19.0 or less, particularly preferably 10.0 or more to 18.0 or less and very particularly preferably 9.0 or more to 16.5 or less.

[0459] Furthermore, the liquid-crystalline medium according to the present application has a high VHR value in the liquid-crystalline cell.

[0460] In a freshly filled cell at 20 °C, these VHR values are greater than or equal to 95 %, preferably greater than or equal to 97 %, particularly preferably greater than or equal to 98 % and very particularly preferably greater than or equal to 99 % in the cell, and after 5 minutes in the oven at 100 °C, these values are greater than or equal to 90 %, preferably greater than or equal to 93 %, particularly preferably greater than or equal to 96 % and very particularly preferably greater than or equal to 98 % in the cell.

[0461] Generally, the liquid-crystalline media having a low addressing voltage or threshold voltage here have a lower VHR than those having a higher addressing voltage or threshold voltage, and vice versa.

[0462] These preferred values of the individual physical properties are also preferably maintained in each case in combination with one another by the medium according to the present application.

[0463] In the present application, the term "compound", also written as "compound(s)", refers to one or more compounds, unless explicitly stated otherwise.

[0464] In a preferred embodiment, the liquid-crystalline medium according to the present application comprises

[0465] one or more compounds of formula S and

[0466] one or more compounds of formula I and / or

[0467] one or more compounds of formula II, preferably compounds of formulae PUQU-n-F, CDUQU-n-F, APUQU-n-F and PGUQU-n-F, and / or

[0468] one or more compounds of formula III, preferably compounds of formulae CCP-n-OT, CLP-n-T, CGG-n-F and CGG-n-OD, and / or

[0469] one or more compounds of formula IV, preferably compounds of formulae CC-n-V, CC-n-Vm, CC-n-m, and CC-V-V, and / or

[0470] one or more compounds of formula V, preferably compounds of formulae CCP-n-m, CCP-V-n, CCP-V2-n, CLP-V-n, CCVC-n-V, and CGP-n-m, and / or

[0471] one or more compounds of formula VI, preferably compounds of formulae Y-n-Om, Y-nO-Om and / or CY-n-Om, selected from the group consisting of compounds of formulae Y-3-O1, Y-4O-O4, CY-3-O2, CY-3-O4, CY-5-O2 and CY-5-O4, and / or

[0472] optionally, preferably mandatorily, one or more compounds of formula VII-1, preferably selected from the group consisting of compounds of formulae CCY-n-m and CCY-n-Om, preferably of formula CCY-n-Om, preferably selected from the group consisting of compounds of 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

[0473] optionally, preferably mandatorily, one or more compounds of formula VII-2, preferably of formula CLY-n-Om, preferably selected from the group consisting of compounds of formulae CLY-2-O4, CLY-3-O2, CLY-3-O3, and / or

[0474] one or more compounds of formula VIII, preferably of formulae CZY-n-On and CCOY-n-m and / or

[0475] one or more compounds of formula IX, preferably of formulae PYP-n-m and / or

[0476] optionally, preferably mandatorily, one or more compounds of formula IV, preferably selected from the group consisting of compounds of formulae CC-n-V, CC-n-Vm and CC-nV-Vm, preferably CC-3-V, CC-3-V1, CC-4-V, CC-5-V and CC-V-V, particularly preferably selected from the group consisting of compounds CC-3-V, CC-3-V1, CC-4-V and CC-V-V, very particularly preferably compound CC-3-V, and optionally additional compounds CC-4-V and / or CC-3-V1 and / or CC-V-V, and / or

[0477] optionally, preferably mandatorily, one or more compounds of formula V, preferably of formulae CCP-V-1 and / or CCP-V2-1.

[0478] In a particularly preferred embodiment of the present application, the medium according to the present application comprises one or more compounds of formula IX,

[0479] Compounds of formula IX are also highly suitable as stabilizers in liquid-crystalline mixtures, especially in the case where p = q = 1 and ring A 9 = 1,4-phenylene. In particular, they stabilize the mixtures against VHR upon UV exposure.

[0480] In a preferred embodiment, the medium according to the present application comprises one or more compounds of formula IX selected from one or more compounds of formulae IX-1 to IX-4, very particularly preferably of formulae IX-1 to IX-3,

[0481]

[0482] wherein the parameters have the meanings given in formula IX.

[0483] In a further preferred embodiment, the medium comprises one or more compounds of formula IX-3, preferably of formula IX-3-a,

[0484]

[0485] wherein

[0486] alkyl and alkyl', independently of each other, denote alkyl having 1 -7 C atoms, preferably having 2-5 C atoms.

[0487] In case the compounds of formula IX are used in a liquid crystalline medium according to the present application, they are preferably present in a concentration of 20% or less, more preferably 10% or less and most preferably 5% or less and for the individual, i.e. homologous, compounds preferably in a concentration of 10% or less and more preferably 5% or less.

[0488] For the present application the following definitions apply to describe the composition of the compositions, unless indicated otherwise in each case:

[0489] "comprises": the concentration of the ingredient in question in the composition is preferably 5% or more, particularly preferably 10% or more and very particularly preferably 20% or more,

[0490] "consists essentially of": the concentration of the ingredient in question in the composition is preferably 80% or more, particularly preferably 90% or more and very particularly preferably 95% or more, and

[0491] "consists essentially of": the concentration of the ingredient in question in the composition is preferably 80% or more, particularly preferably 90% or more and very particularly preferably 95% or more, and

[0492] "consists essentially of": the concentration of the ingredient in question in the composition is preferably 80% or more, particularly preferably 90% or more and very particularly preferably 95% or more, and

[0493] This applies both to the medium as a composition with its ingredients, which can be components and compounds, and also to the components with their ingredients, the compounds. Only when referring to the concentration of individual compounds relative to the medium as a whole does the term "comprises" mean that the concentration of the compound in question is preferably 1% or more, particularly preferably 2% or more and very particularly preferably 4% or more.

[0494] For the present application "<=" means less than or equal to, preferably less than, and ">=" means greater than or equal to, preferably greater than.

[0495] For the present application,

[0496]

[0497] denotes trans-1,4-cyclohexylene,

[0498]

[0499] denotes 1,4-cyclohexylene, preferably trans-1,4-cyclohexylene, and

[0500]

[0501] denotes 1,4-phenylene.

[0502] For the present application, the expression "dielectrically positive compound" means a compound having Δε > 1.5, the expression "dielectrically neutral compound" generally means those with -1.5 < Δε < 1.5 and the expression "dielectrically negative compound" means those with Δε < -1.5. The dielectric anisotropy of a compound here is determined by dissolving 10% of the compound in a liquid crystal host and measuring the capacitance of the resulting mixture in each case in at least one test cell with a homeotropic surface alignment and with a planar surface alignment having a cell thickness of 20 μιη at a temperature of 20 °C and a frequency of 1 kHz. The measurement voltage is generally 1.0 V, but is always below the threshold of the capacitance of the respective liquid crystal mixture investigated.

[0503] The host mixture for the dielectrically positive and dielectrically neutral compounds is ZLI-4792 and for the dielectrically negative compounds is ZLI-2857, both from Merck KGaA, Germany. The values of the respective compounds to be investigated are obtained from the change in the dielectric constant of the host mixture after addition of the compound to be investigated and extrapolated to 100% of the compound employed. The compound to be investigated is dissolved in the host mixture in an amount of 10%. If the solubility of the substance is too low for this purpose, the concentration is halved stepwise until the investigation can be carried out at the desired temperature.

[0504] If necessary, the liquid-crystalline media according to the application can also comprise further additives, such as stabilizers and / or pleochroic dyes, such as dichroic dyes and / or chiral dopants, in usual amounts. The amounts of these additives employed preferably add up to 0% or more to 10% or less, based on the amount of the entire mixture, particularly preferably 0.1% or more to 6% or less. The concentration of each compound employed is preferably 0.1% or more to 3% or less. When specifying the concentration and concentration range of the liquid-crystalline compounds in a liquid-crystalline medium, the concentration of these and similar additives is generally not taken into account.

[0505] In a preferred embodiment, the liquid-crystalline media according to the application comprise a polymer precursor, which comprises one or more reactive compounds, preferably reactive mesogens, and if desired further additives, such as polymerization initiators and / or polymerization moderators, in usual amounts. The amounts of these additives employed add up to 0% or more to 10% or less, preferably 0.1% or more to 2% or less, based on the amount of the entire mixture. When specifying the concentration and concentration range of the liquid-crystalline compounds in a liquid-crystalline medium, the concentration of these and similar additives is not taken into account.

[0506] The composition consists of a plurality of compounds, preferably 3 or more to 30 or less, particularly preferably 6 or more to 20 or less and very particularly preferably 10 or more to 16 or less compounds, which are mixed in the usual manner. Usually, the desired amount of the components used in smaller amounts is dissolved in the components which make up the main constituents of the mixture. This is advantageously carried out at elevated temperature. If the temperature chosen is above the clearing point of the main constituents, the completion of the dissolution operation is particularly easily observed. However, the liquid-crystalline mixtures can also be prepared in other usual ways, for example using premixes or from so-called "multi-bottle systems".

[0507] The mixtures according to the application exhibit a very broad nematic phase range with a clearing point of 65°C or more, a very advantageous capacitance threshold, a relatively high voltage holding ratio (VHR) value and at the same time very good low-temperature stability at -30°C and -40°C. Furthermore, the mixtures according to the application are characterized by a low rotational viscosity γ1.

[0508] It is self-evident to the person skilled in the art that the media according to the application for VA, IPS, FFS or PALC displays can also comprise compounds in which, for example, H, N, O, CI, F have been replaced by the corresponding isotopes.

[0509] The structure of the liquid-crystalline display according to the application corresponds to the general geometry as described, for example, in EP-A 0 240 379.

[0510] The liquid-crystalline phases according to the application can be varied by suitable additives in such a way that they can be used in any type of the hitherto disclosed displays, for example IPS and FFS LCD displays.

[0511] The following table E indicates possible dopants which can be added to the mixtures according to the application. If the mixture comprises one or more dopants, this / these is / are employed in an amount of 0.01 % to 4 %, preferably 0.1 % to 1.0 %.

[0512] The stabilizers which can be added to the mixtures according to the application, for example, in an amount of 0.01 % to 6 %, in particular 0.1 % to 3 %, are indicated in the following table F.

[0513] For the purposes of the present application, all concentrations are indicated in percent by weight, unless explicitly stated otherwise, and all concentrations are relative to the respective mixture as a whole or relative to the individual mixture components, too, as a whole, unless explicitly stated otherwise. In this context, the term "mixture" describes a liquid-crystalline medium.

[0514] All temperature values stated in the present application, such as melting point T(C,N), transition from smectic (S) to nematic (N) phase T(S,N) and clearing point T(N,I), are expressed in degrees Celsius (°C) and all temperature differences accordingly in differential degrees (° or degree) unless explicitly stated otherwise.

[0515] For the present application, the term "threshold voltage" refers to the capacitive threshold (V0), also called Freedericks- threshold, unless explicitly stated otherwise.

[0516] All physical properties are and have been determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals", Status November 1997, Merck KGaA (Germany) and apply for a temperature of 20°C, and Δn is determined at 436 nm, 589 nm and 633 nm and Δε is determined at 1 kHz, unless explicitly stated otherwise in each case.

[0517] Electro-optical properties, such as threshold voltage (V0) (capacitive measurement) (which is the switching behavior), are measured in a test cell produced by Merck Japan. The measurement cell has a soda lime glass substrate and is constructed in an ECB or VA configuration (with diluent ＊＊ The SE-1211 of 26 (mixed ratio 1 : 1), both from Nissan Chemicals, Japan), which have been rubbed perpendicular to each other and influence the homeotropic alignment of the liquid crystal. The surface area of the transparent, almost square ITO electrodes is 1 cm 2 .

[0518] Unless otherwise stated, no chiral dopant is added to the liquid crystal mixture used, but the latter is also particularly suitable for applications in which this type of doping is necessary.

[0519] The rotational viscosity is measured using the rotating permanent magnet method and the flow viscosity in a modified Ubbelohde viscometer. For the liquid crystal mixtures ZLI-2293, ZLI-4792 and MLC-6608 (all products from Merck KGaA, Darmstadt, Germany), the rotational viscosity values determined at 20°C are 161 mPa-s, 133 mPa-s and 186 mPa-s, respectively, and the flow viscosity values (v) are 21 mm 2 ·s -1 , 14 mm 2 ·s -1 and 27 mm 2 ·s -1 .

[0520] For practical purposes, the refractive index dispersion of a material can be conveniently characterized in the following manner, which is used throughout this application unless explicitly stated otherwise. Birefringence values are determined at a temperature of 20°C at several fixed wavelengths using a modified Abbe refractometer, in which a homeotropically aligned surface is in contact with the material on the side of the prism. Birefringence values are determined at specific wavelength values of 436 nm (a selected spectral line of a low-pressure mercury lamp), 589 nm (the sodium "D" line), and 633 nm (the wavelength of a He-Ne laser, which is used in combination with an attenuator / diffuser to prevent eye damage to the observer). In the following table, Δn is given at 589 nm and Δ(Δn) is given as Δ(Δn) = Δn(436 nm) - Δn(633 nm).

[0521] The following symbols are used unless explicitly stated otherwise:

[0522] V0 threshold voltage, capacitive [V], at 20°C,

[0523] n e extraordinary refractive index measured at 20°C and 589 nm,

[0524] n o ordinary refractive index measured at 20°C and 589 nm,

[0525] Δn optical anisotropy measured at 20°C and 589 nm,

[0526] λ wavelength λ [nm],

[0527] Δn(λ) optical anisotropy measured at 20°C and wavelength λ,

[0528] Δ(Δn) change in optical anisotropy, defined as: Δn(20°C, 436 nm) - Δn(20°C, 633 nm),

[0529] Δ(Δn*) "relative change in optical anisotropy", defined as: Δ(Δn) / Δn(20°C, 589 nm),

[0530] ε ⊥ dielectric permittivity perpendicular to the director at 20°C and 1 kHz,

[0531] ε || dielectric permittivity parallel to the director at 20°C and 1 kHz,

[0532] Δε dielectric anisotropy at 20°C and 1 kHz,

[0533] T(N, I) or cl.p. clearing point [°C],

[0534] Flow viscosity [mPa-s] measured at 20°C 2 -1 ],

[0535] Rotational viscosity [mPa-s] measured at 20°C

[0536] k 11 Elastic constant, "splay" deformation at 20°C [pN]

[0537] k 22 Elastic constant, "twist" deformation at 20°C [pN]

[0538] k 33 Elastic constant, "bend" deformation at 20°C [pN]

[0539] LTS Low temperature stability of the phase measured in a test cell

[0540] VHR Voltage holding ratio

[0541] AVHR Reduction of the voltage holding ratio, and

[0542] S rel Relative stability of the VHR

[0543] The following examples illustrate the present application without limiting it. They show, however, to the person skilled in the art the concept of using preferred compounds to be employed and their respective concentrations as well as preferred mixtures of their combinations with each other. Furthermore, the examples elucidate the properties and property combinations which can be obtained.

[0544] For the present application and in the following examples, the structure of the liquid crystalline compounds is indicated by the abbreviations which are translated into chemical formula according to the following Tables A to C. All groups C 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 ​R1is a straight-chain alkyl group or alkylene group, each having n, m and l C atoms in each case. Preferably, n, m and l are independently of each other 1, 2, 3, 4, 5, 6 or 7. Table A shows the codes for the ring elements of the compound nucleus, Table B lists the bridging units, and Table C lists the symbolic meanings of the left-hand and right-hand end groups. The abbreviations consist of the code of the ring element with optional linking group, followed by a first hyphen and the code of the left-hand end group, and a second hyphen and the code of the right-hand end group. Table D shows exemplary structures of the compounds and their respective abbreviations.

[0545] Table A: Ring Elements

[0546]

[0547]

[0548]

[0549] Table B: Bridging Units

[0550]

[0551] Table C: End Groups

[0552]

[0553]

[0554] wherein n and m are each an integer, and the three dots "..." are a placeholder for further abbreviations from the table.

[0555] In addition to the compounds of the formula I, the mixtures according to the application preferably also comprise one or more compounds of the following-mentioned compounds.

[0556] The following abbreviations are used:

[0557] (n, m and l are each independently of one another an integer, preferably 1 to 6, l can also be 0 and is preferably 0 or 2)

[0558] Table D

[0559] Exemplary preferred compounds of the formula T having a high ε⊥:

[0560]

[0561]

[0562] Exemplary preferred compounds of the formula I containing a dibenzothiophene moiety having a high ε⊥:

[0563]

[0564]

[0565] Exemplary preferred compounds of formula I-S-01 having high ε

[0566]

[0567] Exemplary preferred compounds of formula I-S-02 having high ε

[0568]

[0569]

[0570] Exemplary preferred compounds of formula I having high ε ⊥

[0571]

[0572]

[0573] Also

[0574]

[0575]

[0576] Exemplary preferred dielectric positive compounds:

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

[0584]

[0585] Exemplary preferred dielectric neutral compounds:

[0586]

[0587] ​

[0588]

[0589]

[0590]

[0591]

[0592] Exemplary preferred dielectrically negative compounds:

[0593]

[0594]

[0595]

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602] Table E shows chiral dopants which can preferably be employed in the mixtures according to the application.

[0603] Table E

[0604]

[0605]

[0606]

[0607] In a preferred embodiment of the application, the medium according to the application comprises one or more compounds selected from the group of the compounds of Table E.

[0608] Table F shows stabilizers which can preferably be employed in the mixtures according to the application in addition to the compounds of the formula I. Here, the parameter n denotes an integer from 1 to 12. In particular, the shown phenolic derivatives can be employed as additional stabilizers since they act as antioxidants.

[0609] Table F

[0610]

[0611]

[0612]

[0613]

[0614]

[0615] In a preferred embodiment of the application, the medium according to the application 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

[0616] Examples

[0617] The following examples illustrate the application without limiting it in any way. The physical properties, however, make it clear to the person skilled in the art which properties can be achieved and in which ranges they can be adjusted. In particular, the combination of a plurality of properties which can thus be achieved with preference is well defined for the person skilled in the art.

[0618] The following abbreviations are used in the synthetic examples of the present application:

[0619] BuLi n-butyllithium,

[0620] MTB ether tert-butyl methyl ether,

[0621] THF tetrahydrofuran,

[0622] dist. distilled Synthesis Example 1

[0623] Synthesis of 2-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene (CLS-3-T)

[0624]

[0625] Step 1.1: 4-(4-Propylcyclohexyl)-1-[5-(trifluoromethyl)-2-thienyl]cyclohexanol

[0626]

[0627] Under a nitrogen atmosphere, BuLi (59.0 ml, 15% in n-hexane, 93 mmol) was slowly added to a solution of 2-bromo-5-(trifluoromethyl)thiophene (1, CAS 143469-22-1) (20.0 g, 86 mmol) in diethyl ether (250 mL) at -70°C. After 1 hour the mixture was allowed to warm to -50°C. It was then cooled again to -70°C and a solution of 4-(4-propylcyclohexyl)-cyclohexanone (2, CAS 82832-73-3) (22.0 g, 98 mmol) in diethyl ether (100 mL) was added dropwise. The reaction mixture was stirred for 1 hour, then it was allowed to warm to room temperature and quenched with distilled water and hydrochloric acid (2 M). The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with brine, dried (sodium sulfate) and concentrated in vacuo to give 4-(4-propylcyclohexyl)-1-[5-(trifluoromethyl)-2- thiophenyl]cyclohexanol (3) as a brown solid.

[0628] Step 1.2: 2-[4-(4-Propylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene (CLS-3-T)

[0629]

[0630] A mixture of 4-(4-propylcyclohexyl)-1-[5-(trifluoromethyl)-2-thiophenyl]cyclohexanol (3) (37.8 g, 86 mmol) and toluene-4-sulfonic acid monohydrate (1.5 g, 7.9 mmol) in toluene (400 mL) was heated at reflux temperature in a Dean Stark trap for 2 hours. It was then cooled to room temperature and the mixture was quenched with an aqueous sodium hydroxide solution. The aqueous phase was separated and extracted with toluene. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent n-heptane). The crude product was subsequently recrystallized from isopropanol to give 2-[4-(4- butylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene as colorless crystals (4).

[0631] Compound (4) has the following phase characteristics:

[0632] K 76N 104I.

[0633] Synthesis Example 2

[0634] Synthesis of 2-[4-(4-Propylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene (CLS-3-T)

[0635]

[0636] Step 2.1:2-[4-(4-Propylcyclohexyl)cyclohexyl]-5-(trifluoromethyl)thiophene

[0637]

[0638] A solution of 2-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-5- (trifluoromethyl)thiophene (1) (23.5 g, 65 mmol) in toluene (300 mL) was reacted with hydrogen gas in the presence of a catalytic amount of palladium on activated carbon for 24 hours. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (solvent n-heptane) to give the trans isomer of the desired product. The crude product was then recrystallized from a mixture of isopropanol and methylcyclohexane to give 2-[4-(4-propylcyclohexyl)cyclohexyl]-5- (trifluoromethyl)thiophene as colorless crystals (2).

[0639] Compound (2) has the following phase characteristics:

[0640] K 41 S X 45 S B 52 N 95 I.

[0641] Synthesis Example 3

[0642] Synthesis of 2-[2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-5- (trifluoromethyl)thiophene (LGS-3-T)

[0643]

[0644] Step 3.1: 1-(4-Bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol

[0645]

[0646] A solution of isopropylmagnesium chloride (2.0 M) in THF (260 mL, 0.52 mol, diluted in 200 mL THF) was slowly added to a solution of 1-bromo-2-fluoro-4- iodobenzene (1, CAS 136434-77-0) (150 g, 0.50 mol) in THF (1 L) at -10 °C under a nitrogen atmosphere. The reaction mixture was stirred at this temperature for 3 hours. A solution of 4-propylcyclohexanone (2, CAS 40649-36-3) (73.0 g, 0.52 mol) in THF (200 mL) was then added at -10 °C. The mixture was allowed to warm to room temperature and stirred overnight.

[0647] The mixture was then quenched with distilled water and hydrochloric acid (10%) at 0°C, then diluted with MTB ether. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated under vacuum to give 1-(4-bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol (3) as a brown oil.

[0648] Step 3.2: 1 -Bromo-2-fluoro-4-(4-propylcyclohex- 1 -en- 1 -yl)benzene

[0649]

[0650] A mixture of 1-(4-bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol (3) (194.0 g, 0.44 mol) and toluene-4-sulfonic acid monohydrate (5.0 g, 26.3 mmol) in toluene (1.3 L) was heated in a Dean Stark trap at reflux temperature for 3 hours. It was then cooled to room temperature and concentrated under vacuum. The residue was purified by silica gel chromatography (solvent n-heptane) to give 1-bromo-2-fluoro-4-(4-propylcyclohex-1-en-1-yl)benzene (4) as a light yellow oil.

[0651] Step 3.3: 2-[2-Fluoro-4-(4-propylcyclohex-1-en-1-yl)phenyl]-5-(trifluoromethyl)thiophene

[0652]

[0653] A mixture of 1-bromo-2-fluoro-4-(4-propylcyclohex-1-en-1-yl)benzene (4) (7.2 g, 24.2 mmol), potassium carbonate (5.5 g, 39.8 mmol), a mixture of tris(dibenzylideneacetone)-dipalladium (0) (100 mg, 0.11 mmol) and CataCXium A (70 mg, 0.19 mmol) in THF (100 mL) and distilled water (25 mL) was heated to reflux under nitrogen atmosphere, then a solution of [5-(trifluoromethyl)-2-thienyl]boronic acid (5, CAS 958451-91-7) (5.0 g, 25.5 mmol) in THF (30 mL) was added dropwise. The reaction mixture was heated at reflux temperature for 3 hours. It was then cooled to room temperature and diluted with MTB ether and distilled water. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated under vacuum. The residue was purified by silica gel chromatography (solvent heptane). The crude product was then recrystallized from isopropanol and heptane to give 2-[2-fluoro-4-(4-propylcyclohex-1-en-1-yl)phenyl]-5-(trifluoromethyl)thiophene (6) as colorless crystals.

[0654] Compound (6) has the following phase characteristics:

[0655] K 72SmA 123I.

[0656] Synthesis Example 4

[0657] Synthesis of 2-[2-fluoro-4-(4-propylcyclohexyl)phenyl]-5- (trifluoromethyl)thiophene

[0658]

[0659] Step 4.1: 2-[2-fluoro-4-(4-propylcyclohexyl)phenyl]-5-(trifluoromethyl)thiophene

[0660]

[0661] In the presence of catalytic amounts of palladium on activated carbon, 2-[2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-5-(trifluoromethyl)thiophene (3.5 g, 9.5 mmol) in toluene (30 mL) was reacted with hydrogen for 24 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (solvent n-heptane) to give the trans isomer of the desired product. Subsequent recrystallization of the crude product from a mixture of isopropanol and methylcyclohexane gave 2-[2-fluoro-4-(4-propylcyclohexyl)phenyl]-5-(trifluoromethyl)thiophene (2) as colorless crystals.

[0662] Compound (2) has the following phase characteristics:

[0663] K 70N 77I.

[0664] Synthesis Example C-1 (LB(S)-3-OT)

[0665] Synthesis of 4,6-difluoro-3-(4-propyl-cyclohex-1-enyl)-7- trifluoromethoxy-dibenzo-thiophene:

[0666]

[0667] Step C-1.1: 3,2',3'-trifluoro-4'-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy- biphenyl-2-ol

[0668]

[0669] A mixture of 6-bromo-2-fluoro-3-trifluoromethoxyphenol (2, CAS 1805580-01-1) (68.0 g, 0.25 mol), potassium carbonate (50.0 g, 0.36 mol), tris(dibenzylideneacetone)-dipalladium(0) (1.2 g, 1.25 mmol) and CataCXium A (1.4 g, 3.71 mmol) in THF (500 mL) and distilled water (100 mL) was heated to reflux under a nitrogen atmosphere, then a solution of 2,3-difluoro-4-(4-propyl-cyclohex-1-enyl)-phenylboronic acid (1, CAS 947607-78-5) (70.6 g, 0.25 mol) in THF (200 mL) was added dropwise. The reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature and diluted with MTB ether and distilled water. Throughout the application, room temperature and ambient temperature are used synonymously and represent a temperature of about 20 °C, typically (20 ± 1) °C, unless explicitly stated otherwise. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent 1-chlorobutane / heptane 1 :1). 3,2',3'-Trifluoro-4'-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol (3) was isolated as a brown solid.

[0670] Step C-1.2: 3,2',3'-Trifluoro-4'-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl trifluoromethanesulfonate

[0671]

[0672] Trifluoromethanesulfonic anhydride (31 mL, 0.19 mol) was slowly added to a solution of 3,2',3'-trifluoro-4'-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol (3) (66 g, 0.15 mol), TEA (32 mL, 0.23 mol) and DMAP (560 mg, 4.58 mmol) in dichloromethane (500 mL) at 5 °C under a nitrogen atmosphere. The solution was stirred at room temperature overnight. The reaction mixture was purified by silica gel chromatography (solvent dichloromethane) to give 3,2',3'-trifluoro-4'-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl trifluoromethanesulfonate (4) as a brown oil.

[0673] Step C-1.3: 4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethoxy-dibenzo-thiophene

[0674]

[0675] The reaction was carried out as a one pot reaction. In the first step, a solution of 3,2',3'-trifluoro-4'-(4-propyl-cyclohex-1 -enyl)-4-trifluoromethoxy-biphenyl-2-yl triflate (4) (87 g, 0.15 mol), 3-mercapto-propionic acid 2-ethylhexyl ester (45 mL, 0.19 mol), N- ethyldiisopropylamine (40 mL, 0.24 mol) and toluene (350 mL) was degassed with argon for 1 h. Tris(dibenzylideneacetone)dipalladium(0) (1.5 g, 1.56 mmol) and (oxydi-2,1 -phenylene)bis(diphenylphosphane) (1.6 g, 2.91 mmol) were quickly added to the solution and the reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature. In the second step, a solution of potassium tert-butoxide (22 g, 0.20 mol) in THF (200 mL) was added in situ to the reaction mixture containing intermediate (5). The reaction mixture was heated at reflux temperature overnight, then a second portion of potassium tert-butoxide (1 1 g, 0.1 mol) in THF (100 mL) was added. The reaction mixture was heated at reflux temperature overnight again. It was then cooled to room temperature, quenched at 0°C with distilled water and hydrochloric acid (25%) and diluted with MTB ether. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent heptane) to give 4,6-difluoro-3-(4-propyl-cyclohex-1 -enyl)-7-trifluoromethoxy-dibenzothiophene (6) as white crystals.

[0676] Compound (6) has the following phase characteristics:

[0677] K 66°C SmA 181 °C I.

[0678] Synthesis Example C-2 (LB(S)-3-T)

[0679] Synthesis of 4,6-difluoro-3-(4-propyl-cyclohex-1 -enyl)-7-trifluoromethyl- dibenzothiophene:

[0680]

[0681] Step C-2.1: 3,2',3'-trifluoro-4-trifluoromethyl-biphenyl-2-ol

[0682]

[0683] A mixture of 6-bromo-2-fluoro-3-trifluoromethylphenol (2, CAS 1804908-52-8) (100 g, 0.38 mol), potassium carbonate (80 g, 0.58 mol), tris(dibenzylideneacetone)-dipalladium(0) (1.9 g, 2.0 mmol) and CataCXium A (2.2 g, 5.8 mmol) in THF (500 mL) and distilled water (200 mL) was heated to reflux under a nitrogen atmosphere, then a solution of 2,3-difluoro-4-phenylboronic acid (1, CAS 121219-16-7) (70 g, 0.43 mol) in THF (300 mL) was added dropwise. The reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature and diluted with MTB ether and distilled water. Throughout the application, room temperature and ambient temperature are used synonymously and represent a temperature of about 20 °C, typically (20 ± 1) °C, unless explicitly stated otherwise. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent dichloromethane). 3,2',3'-Trifluoro-4-trifluoromethyl-biphenyl-2-ol (3) was isolated as a brown solid.

[0684] Step C-2.2: 3,2',3'-Trifluoro-4-trifluoromethyl-biphenyl-2-yl trifluoromethanesulfonate

[0685]

[0686] Trifluoromethanesulfonic anhydride (30.0 mL, 0.18 mol) was slowly added to a solution of 3,2',3'-trifluoro-4-trifluoromethyl-biphenyl-2-ol (3) (46.8 g, 0.15 mol), TEA (32 mL, 0.23 mol) and DMAP (600 mg, 4.9 mmol) in dichloromethane (300 mL) at 5 °C under a nitrogen atmosphere. The solution was stirred at room temperature overnight. The reaction mixture was purified by chromatography on silica gel (solvent dichloromethane) to give 3,2',3'-trifluoro-4-trifluoromethyl-biphenyl-2-yl trifluoromethanesulfonate (4) as a yellow oil.

[0687] Step C-2.3: 4,6-Difluoro-3-trifluoromethyl-dibenzothiophene

[0688]

[0689] The reaction was carried out as a one-pot reaction. In the first step, a solution of triflic acid 3,2',3'-trifluoro-4-trifluoromethyl-biphenyl-2-yl ester (4) (66 g, 0.15 mol) and ethyl 3-mercaptopropionate (24 mL, 0.18 mol) in toluene (500 mL) was heated to 80 °C under a nitrogen atmosphere. Potassium carbonate (50 grams, 0.36 moles), tris(dibenzylideneacetone)dipalladium(0) (7.0 grams, 7.3 mmoles) and (oxydi-2,1-phenylene)bis(diphenylphosphane) (8.0 grams, 14.6 mmoles) were quickly added to the solution and the reaction mixture was heated at reflux overnight. It was then cooled to room temperature. In the second step, a solution of potassium tert-butoxide (18 g, 0.16 mol) in THF (150 mL) was added in situ to the reaction mixture containing intermediate (5). The reaction mixture was heated at reflux overnight. It was then cooled to room temperature, quenched with distilled water and hydrochloric acid (25%) at 0 °C and diluted with MTB ether. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent heptane) to give 4,6-difluoro-3-trifluoromethyl-dibenzo-thiophene (6) as yellow crystals.

[0690] Step C-2.4: 1-(4,6-Difluoro-7-trifluoromethyl-dibenzo-thiophen-3-yl)-4-propyl-cyclohexanol

[0691]

[0692] Lithium diisopropyl amide (6 mL, 2M in cyclohexane / ethylbenzene / THF, 12 mmol) was added to a solution of 4,6-difluoro-3-trifluoromethyl-dibenzo-thiophene (6) (3.2 g, 10 mmol) in THF (100 mL) at -70 °C under a nitrogen atmosphere. After 1 hour, a solution of 4-propylcyclohexanone (1.7 g, 12 mmol) in THF (10 mL) was added and the reaction mixture was stirred at -70 °C for 2 hours. It was then allowed to warm to room temperature and stirred overnight. The reaction was quenched with distilled water and hydrochloric acid (25%) at 0 °C and diluted with MTB ether. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent dichloromethane) to give 1-(4,6-difluoro-7-trifluoromethyl-dibenzo-thiophen-3-yl)-4-propyl-cyclohexanol (7) as yellow crystals.

[0693] Step C-2.5: 4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzo-thiophene

[0694]

[0695] A mixture of 1-(4,6-difluoro-7-trifluoromethyl-dibenzo-thiophen-3-yl)-4- propyl-cyclohexanol (7) (1.2 g, 2.5 mmol) and toluene-4-sulfonic acid monohydrate (50 mg, 0.3 mmol) in toluene (50 mL) was heated in a Dean Stark trap at reflux temperature overnight. It was then cooled to room temperature and diluted with MTB ether and distilled water. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent 1-chlorobutane). The crude product was subsequently recrystallized from heptane to give 4,6-difluoro-3-(4-propyl-cyclohex-1-enyl)-7- trifluoromethyl-dibenzo-thiophene as colorless crystals.

[0696] Compound (7) has the following phase characteristics:

[0697] K 121 °C SmA 162 °C I.

[0698] Synthesis Example C-3 (CB(S)-3-T)

[0699] Synthesis of 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl- dibenzo-thiophene:

[0700]

[0701] Step 3.1: 3,2',3'-trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-ol

[0702]

[0703] A mixture of 6-bromo-2-fluoro-3-trifluoromethylphenol (2, CAS 1804908-52-8) (7.1 g, 26.9 mmol), potassium carbonate (5.6 g, 40.5 mmol), tris(dibenzylideneacetone)-dipalladium(0) (130 mg, 0.14 mmol) and CataCXium A (150 mg, 0.40 mmol) in THF (50 mL) and distilled water (15 mL) was heated to reflux under a nitrogen atmosphere, then a solution of 2,3-difluoro-4-(4-propyl-cyclohexyl)-phenylboronic acid (1, CAS 183438-45-1) (7.8 g, 27.2 mmol) in THF (25 mL) was added dropwise. The reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature and diluted with MTB ether and distilled water. Throughout the application, room temperature and ambient temperature are used synonymously and represent a temperature of about 20 °C, typically (20 ± 1) °C, unless explicitly stated otherwise. The aqueous phase was separated and the organic phases were extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent 1-chlorobutane / heptane 1 :1). 3,2',3'-Trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-ol (3) was isolated as a yellow solid.

[0704] Step C-3.2: 3,2',3'-Trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-yl trifluoromethanesulfonate

[0705]

[0706] Trifluoromethanesulfonic acid 3,2',3'-trifluoro-4'-(4-propyl-cyclohexyl)-4- trifluoromethyl-biphenyl-2-yl ester (4) was obtained by purifying the reaction mixture by chromatography on silica gel (solvent dichloromethane) to give a yellow oil.

[0707] Step C-3.3 4,6-Difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl-dibenzothiophene

[0708]

[0709] The reaction was carried out as a one-pot reaction. In the first step, a solution of trifluoromethanesulfonic acid 3,2',3'-trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethyl- biphenyl-2-yl ester (4) (7.3 g, 13.1 mmol) and ethyl 3-mercapto propionate (2.2 mL, 16.7 mmol) in toluene (70 mL) was rapidly heated to 80 °C under a nitrogen atmosphere. Potassium carbonate (5.0 g, 36.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.7 g, 0.73 mmol) and (oxydi-2,1-phenylene)bis(diphenylphosphane) (0.8 g, 1.46 mmol) were rapidly added to the solution and the reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature. In the second step, a solution of potassium tert-butoxide (1.8 g, 16.0 mmol) in THF (20 mL) was added in situ to the reaction mixture containing intermediate (5). The reaction mixture was heated at reflux temperature overnight, then a second portion of potassium tert-butoxide (1.8 g, 16.0 mmol) in THF (20 mL) was added. The reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature, quenched at 0 °C with distilled water and hydrochloric acid (25%) and diluted with MTB ether. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent heptane) to give 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl-dibenzo-thiophene (6) as light yellow crystals.

[0710] Compound (6) has the following phase characteristics:

[0711] K 150 °C N (139 °C) I

[0712] Synthesis Example C-3a (CB(S)-3-T)

[0713] Alternatively, 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl- dibenzo-thiophene is obtained by hydrogenation of 4,6-difluoro-3-(4-propyl- cyclohex-1-enyl)-7-trifluoromethyl-dibenzo-thiophene:

[0714]

[0715] Synthesis Example C-4 (CB(S)-3-OT)

[0716] Synthesis of 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethoxy- dibenzo-thiophene:

[0717]

[0718] Step C-4.1 : 3,2',3'-Trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-ol

[0719]

[0720] A mixture of 6-bromo-2-fluoro-3-trifluoromethoxyphenol (2, CAS 1805580-01-1) (33.0 g, 0.12 mol), potassium carbonate (25.0 g, 0.18 mol), tris(dibenzylideneacetone)-dipalladium(0) (600 mg, 0.6 mmol) and CataCXium A (700 mg, 1.9 mmol) in THF (250 mL) and distilled water (75 mL) was heated to reflux under a nitrogen atmosphere, then a solution of 2,3-difluoro-4-(4-propyl-cyclohexyl)-phenylboronic acid (1, CAS 183438-45-1) (34.4 g, 0.12 mol) in THF (100 mL) was added dropwise. The reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature and diluted with MTB ether and distilled water. Throughout the application, room temperature and ambient temperature are used synonymously and represent a temperature of about 20 °C, typically (20 ± 1) °C, unless explicitly stated otherwise. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent 1-chlorobutane / heptane 1 :1). 3,2',3'-Trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-ol (3) was isolated as a yellow solid.

[0721] Step C-4.2: Trifluoromethanesulfonic acid 3,2',3'-trifluoro-4'-(4-propyl-cyclohexyl)-4- trifluoromethoxy-biphenyl-2-yl ester

[0722]

[0723] Trifluoromethanesulfonic anhydride (6.0 mL, 36.4 mmol) was slowly added to a solution of 3,2',3'-trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-ol (3) (12.6 g, 29.0 mmol), TEA (6.3 mL, 45.4 mmol) and DMAP (110 mg, 0.9 mmol) in dichloromethane (100 mL) at 5 °C under a nitrogen atmosphere. The solution was stirred at room temperature overnight. The reaction mixture was purified by silica gel chromatography (solvent dichloromethane) to give trifluoromethanesulfonic acid 3,2',3'-trifluoro-4'-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-yl ester (4) as a yellow oil.

[0724] Step C-4.3: 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethoxy-dibenzo- thiophene

[0725]

[0726] The reaction was performed as a one-pot reaction. In the first step, a solution of trifluoromethanesulfonic acid 3,2',3'-trifluoro-4'-(4-propyl-cyclohexyl)-4- trifluoromethoxy-biphenyl-2-yl ester (4) (16.3 g, 28.1 mmol) and ethyl 3- mercaptopropionate (5.0 mL, 37.9 mmol) in toluene (150 mL) was rapidly heated to 80 °C under a nitrogen atmosphere. Potassium carbonate (10 g, 72.4 mmol), tris(dibenzylidene-acetone)dipalladium(0) (1.4 g, 1.5 mmol) and (oxybis-2,1-phenylene)bis(diphenylphosphane) (1.6 g, 2.9 mmol) were rapidly added to the solution and the reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature. In the second step, a solution of potassium tert-butoxide (3.5 g, 31.2 mmol) in THF (50 mL) was added in situ to the reaction mixture containing intermediate (5). The reaction mixture was heated at reflux temperature overnight, then a second portion of potassium tert-butoxide (3.5 g, 31.2 mmol) in THF (50 mL) was added. The reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature, quenched at 0 °C with distilled water and hydrochloric acid (25%) and diluted with MTB ether. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by chromatography on silica gel (solvent heptane) to give 4,6-difluoro-3-(4-propyl-cyclohexyl)-7- trifluoromethoxy-dibenzo-thiophene (6) as colorless crystals.

[0727] Compound (6) has the following phase characteristics:

[0728] K 108 °C SmA 141 °C N 169 °C I

[0729] Synthesis Example C-4a (CB(S)-3-OT)

[0730] Alternatively, 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethoxy- dibenzo-thiophene is obtained by hydrogenation of 4,6-difluoro-3-(4-propyl- cyclohex-1-enyl)-7-trifluoromethoxy-dibenzo-thiophene:

[0731]

[0732] Compound Examples

[0733] with a high dielectric constant perpendicular to the director (ε⊥ ) and high average dielectric constant (ε av. ) are exemplified in the following compound examples.

[0734] Compound Examples 1 to 10

[0735] Compounds of formula T are for example

[0736]

[0737] This compound (CCS-3-T) has a melting point of 41 °C, a clearing point of 95 °C, a phase range of K 41 °C S X 45 °C S A 52 °C N 95 °C I and a Δε of +7.4.

[0738]

[0739] This compound (CLS-3-T) has a melting point of 76 °C, a clearing point of 104 °C, a phase range of K 76 °C N 104 °C I and a Δε of +8.4.

[0740]

[0741]

[0742] This compound (CGS-3-T) has a melting point of 70 °C, a clearing point of 77 °C, a phase range of K 70 °C N 77 °C I and a Δε of +11.1.

[0743]

[0744] This compound (CYS-3-T) has a melting point of 68 °C, a single clearing point of 66 °C, a phase range of K 68 °C S A (40 °C) N (66 °C) I and a Δε of +5.7.

[0745]

[0746] This compound (CUS-3-T) has a melting point of 61 °C, a clearing point of 172 °C, a phase range of K 61 °C S B 98 °C S A 172 °C I and a Δε of +14.4.

[0747]

[0748] This compound (LGS-3-T) has a melting point of 72 °C, a clearing point of 123 °C, a phase range of K 72 °C S A123 °C I and Δε are +13.3.

[0749]

[0750] The melting point (T(K->I)) of this compound (PS-3-T) is 69 °C and Δε is +9.1.

[0751]

[0752] The melting point (T(K->I)) of this compound (YS-2O-T) is 68 °C and Δε is +5.5.

[0753] Similarly, the following compound of formula T-1-1 is prepared

[0754]

[0755]

[0756]

[0757]

[0758] Similarly, the following compound of formula T-2-1 is prepared

[0759]

[0760]

[0761]

[0762] Similarly, the following compound of formula T-3-1 is prepared

[0763]

[0764]

[0765]

[0766]

[0767] Similarly, the following compound of formula T-3-2 is prepared

[0768]

[0769]

[0770]

[0771] Similarly, the following compound of formula T-3-3 is prepared

[0772]

[0773]

[0774]

[0775]

[0776] Similarly, the following compounds of Formula T-3-4 were prepared

[0777]

[0778]

[0779]

[0780] Similarly, the following compounds of Formula T-4-1 were prepared

[0781]

[0782]

[0783]

[0784] Similarly, the following compounds of Formula T-4-2 were prepared

[0785]

[0786]

[0787]

[0788] Similarly, the following compounds of Formula T-4-3 were prepared

[0789]

[0790]

[0791]

[0792] Similarly, the following compounds of Formula T-4-4 were prepared

[0793]

[0794]

[0795]

[0796]

[0797] Other compound examples

[0798]

[0799]

[0800]

[0801] Additional comparative compounds 1 to 6

[0802] The compound of formula I-S-1 is, for example,

[0803]

[0804] The compound (LB(S)-3-F) has a melting point of 133°C, a clearing point of 155.3°C, a phase range of K 133°C N 155.3°C I and a delta epsilon of +1.3.

[0805]

[0806] The compound (LB(S)-3-OT), the compound of synthesis example 2, has a melting point of 66°C, a clearing point of 181°C, a phase range of K 66°C S A 181°C I and a delta epsilon of +4.7.

[0807]

[0808] The compound of formula I-S-2 is, for example,

[0809] The compound (LB(S)-3-T) has a melting point of 121°C, a clearing point of 162°C, a phase range of 121°C S A 162°C I and a delta epsilon of +7.8.

[0810]

[0811] The compound (CB(S)-3-F) has a melting point of 157°C, a clearing point of 170.3°C, a phase range of K 157°C N 170.3 I.

[0812]

[0813] The compound (CB(S)-3-OT), the compound of synthesis example 2, has a melting point of 108°C, a clearing point of 168.5°C, a phase range of K 108°C S A 141°C N 168.5°C I and a delta epsilon of +4.5.

[0814]

[0815] The melting point of this compound (CB(S)-3-T) is 150°C, the clearing point (monotropic) is 138.8°C, the phase range is K 150°C N (138.8°C) I and the Δε is +8.1.

[0816] Similarly, the following compounds of formula I containing a dibenzothiophene moiety were prepared

[0817]

[0818] The melting point of this compound (DB(S)-3-OT) is 153°C, the clearing point is 174.1°C and the phase range is K 153°C S A 165°C N 174.1°C I.

[0819]

[0820] The melting point of this compound (DB(S)-3-OT) is 153°C, the clearing point is 174.1°C and the phase range is K 153°C S A 168°C I.

[0821] Other comparative, additional compound examples

[0822]

[0823]

[0824]

[0825] Mixture Examples

[0826] The following exemplary mixtures are disclosed.

[0827] Example 1

[0828] The following mixture (M-1) was prepared and investigated.

[0829]

[0830]

[0831] Note: *: [mPa-s / pN].

[0832] This mixture, mixture M-1, is characterized by a good transmittance in FFS displays and shows a short response time.

[0833] Example 2

[0834] The following mixture (M-2) was prepared and investigated.

[0835]

[0836]

[0837] Note: *: [mPa s / pN].

[0838] This mixture, mixture M-2, is characterized by a good transmittance in FFS displays and shows a short response time.

[0839] Example 3

[0840] The following mixture (M-3) was prepared and investigated.

[0841]

[0842]

[0843] Note: *: [mPa s / pN].

[0844] This mixture, mixture M-3, is characterized by a good transmittance in FFS displays and shows a short response time.

[0845] Example 4

[0846] The following mixture (M-4) was prepared and investigated.

[0847]

[0848]

[0849] Note: *: [mPa s / pN].

[0850] This mixture, mixture M-4, is characterized by a good transmittance in FFS displays and shows a short response time.

[0851] Example 5

[0852] The following mixture (M-5) was prepared and investigated.

[0853]

[0854]

[0855] Note: *: [mPa s / pN].

[0856] This mixture, mixture M-5, is characterized by a good transmittance in FFS displays and shows a short response time.

[0857] Example 6

[0858] The following mixture (M-6) was prepared and investigated.

[0859]

[0860]

[0861] Note: *: [mPa s / pN].

[0862] This mixture, mixture M-6, is characterized by a good transmittance in FFS displays and shows a short response time.

[0863] Example 7

[0864] The following mixture (M-7) was prepared and investigated.

[0865]

[0866] Note: *: [mPa s / pN].

[0867] This mixture, mixture M-7, is characterized by a good transmittance in FFS displays and shows a short response time.

[0868] Example 8

[0869] The following mixture (M-8) was prepared and investigated.

[0870]

[0871] Note: *: [mPa s / pN].

[0872] This mixture, mixture M-8, is characterized by a good transmittance in FFS displays and shows a short response time.

[0873] Example 9

[0874] The following mixture (M-9) was prepared and investigated.

[0875]

[0876] Note: *: [mPa s / pN].

[0877] This mixture, mixture M-9, is characterized by a good transmittance in FFS displays and shows a short response time.

[0878] Example 10

[0879] The following mixture (M-10) was prepared and investigated.

[0880]

[0881]

[0882] Note: *: [mPa s / pN].

[0883] This mixture, mixture M-10, is characterized by a good transmittance in FFS displays and shows a short response time.

[0884] Example 11

[0885] The following mixture (M-11) was prepared and investigated.

[0886]

[0887]

[0888] Note: *: [mPa s / pN].

[0889] This mixture, mixture M-11, is characterized by a good transmittance in FFS displays and shows a short response time.

[0890] Example 12

[0891] The following mixture (M-12) was prepared and investigated.

[0892]

[0893]

[0894] Note: *: [mPa s / pN].

[0895] This mixture, mixture M-12, is characterized by a good transmittance in FFS displays and shows a short response time.

[0896] Example 13

[0897] The following mixture (M-13) was prepared and investigated.

[0898]

[0899]

[0900] Note: *: [mPa s / pN].

[0901] The mixture, mixture M-13, is characterized by good transmittance in FFS displays and shows a short response time.

[0902] Example 14

[0903] The following mixture (M-14) was prepared and investigated.

[0904]

[0905]

[0906] Remark: *: [mPa s / pN].

[0907] The mixture, mixture M-14, is characterized by good transmittance in FFS displays and shows a short response time.

[0908] Example 15

[0909] The following mixture (M-15) was prepared and investigated.

[0910]

[0911]

[0912] Remark: *: [mPa s / pN].

[0913] The mixture, mixture M-15, is characterized by good transmittance in FFS displays and shows a short response time.

[0914] Example 16

[0915] The following mixture (M-16) was prepared and investigated.

[0916]

[0917]

[0918] Remark: *: [mPa s / pN].

[0919] The mixture, mixture M-16, is characterized by good transmittance in FFS displays and shows a short response time.

[0920] Example 17

[0921] The following mixture (M-17) was prepared and investigated.

[0922]

[0923] Remark: *: [mPa s / pN].

[0924] This mixture, mixture M-17, is characterized by a good transmittance in FFS displays and shows a short response time.

[0925] Example 18

[0926] The following mixture (M-18) was prepared and investigated.

[0927]

[0928] Remark: *: [mPa s / pN].

[0929] This mixture, mixture M-18, is characterized by a good transmittance in FFS displays and shows a short response time.

[0930] Example 19

[0931] The following mixture (M-19) was prepared and investigated.

[0932]

[0933] Remark: t.b.d.: to be determined and *: [mPa s / pN].

[0934] This mixture, mixture M-19, is characterized by a good transmittance in FFS displays and shows a short response time.

[0935] Example 20

[0936] The following mixture (M-20) was prepared and investigated.

[0937]

[0938] Remark: t.b.d.: to be determined and *: [mPa s / pN].

[0939] This mixture, mixture M-20, is characterized by a good transmittance in FFS displays and shows a short response time.

[0940] Example 21

[0941] The following mixture (M-21) was prepared and investigated.

[0942]

[0943]

[0944] Remark: *: [mPa s / pN].

[0945] This mixture, mixture M-21, is characterized by a good transmittance in FFS displays and shows a short response time.

[0946] Example 22

[0947] The following mixture (M-22) was prepared and investigated.

[0948]

[0949]

[0950] Remark: t.b.d.: to be determined and *: [mPa s / pN].

[0951] This mixture, mixture M-22, is characterized by a good transmittance in FFS displays and shows a short response time.

[0952] Example 23

[0953] The following mixture (M-23) was prepared and investigated.

[0954]

[0955] Remark: *: [mPa s / pN].

[0956] This mixture, mixture M-23, is characterized by a good transmittance in FFS displays and shows a short response time.

[0957] Example 24

[0958] The following mixture (M-24) was prepared and investigated.

[0959]

[0960] Remark: *: [mPa s / pN].

[0961] This mixture, mixture M-24, is characterized by a good transmittance in FFS displays and shows a short response time.

[0962] Example 25

[0963] The following mixture (M-25) was prepared and investigated.

[0964]

[0965]

[0966] Note: t.b.d.: to be determined and *: [mPa-s / pN].

[0967] This mixture, mixture M-25, is characterized by a good transmittance in FFS displays and shows a short response time.

[0968] Example 26

[0969] The following mixture (M-26) was prepared and investigated.

[0970]

[0971]

[0972] Note: t.b.d.: to be determined and *: [mPa-s / pN].

[0973] This mixture, mixture M-26, is characterized by a good transmittance in FFS displays and shows a short response time.

[0974] Comparative Example A

[0975] The following mixture (CE-A) was prepared and investigated.

[0976]

[0977] Note: *): γ1 / k 11 in mPa-s / pN

[0978] This comparative mixture, mixture A, has a dielectric ratio (ε ⊥ / Δε) of 0.50, a (γ1 / k 11 ) ratio of 4.81 mPa-s / pN and is characterized by a moderately good transmittance in FFS displays and shows at best an acceptable short response time.

[0979] To this mixture, used as host mixture, several target compounds were added and the resulting mixtures were investigated.

[0980] Table 1

[0981]

[0982] Note: all values (except clearness point) at 20°C,

[0983] *: [mPa-s / pN] and

[0984] t.b.d.: to be determined.

[0985] Table 1 (continued)

[0986]

[0987] Note: All values (except clear point) at 20°C,

[0988] *: [mPa-s / pN] and

[0989] t.b.d.: to be determined.

[0990] Table 1 (continued)

[0991]

[0992]

[0993] Note: All values (except clear point) at 20°C,

[0994] *: [mPa-s / pN] and

[0995] t.b.d.: to be determined.

[0996] Table 1 (continued)

[0997]

[0998]

[0999] Note: All values (except clear point) at 20°C,

[1000] *: [mPa-s / pN] and

[1001] t.b.d.: to be determined.

[1002] Comparative Example B

[1003] The following mixture (CE-B) was prepared and studied.

[1004]

[1005] Note: * ) γ1 / k 11 in mPa-s / pN

[1006] This comparative mixture, Mixture B, has a dielectric ratio (ε ⊥ / Δε) of 0.59, a (γ1 / k 11 ) ratio of 9.04 mPa-s / pN and is characterized by a moderate good transmittance in FFS displays and shows at best an acceptable short response time.

[1007] To this mixture, which serves as another host mixture, are also added several target compounds, and the resulting mixture is investigated.

[1008] Table 2

[1009]

[1010] Table 2 (continued)

[1011]

[1012] Comparative Example C

[1013] The following mixture (CE-C) is prepared and investigated.

[1014]

[1015]

[1016] Note: *): γ1 / k 11 in mPa-s / pN

[1017] This comparative mixture, mixture C, has a dielectric ratio (ε⊥ / Δε) of 0.84, a (γ1 / k 11 ) ratio of 5.96 mPa-s / pN and is characterized by a moderately good transmission in FFS displays and shows at best acceptable short response times.

[1018] Table 3

[1019]

[1020]

[1021] Note: All values (except clearing point) at 20°C,

[1022] *: [mPa-s / pN] and

[1023] t.b.d.: to be determined.

[1024] Comparative Example D-0

[1025] The following mixture (CE-D-0) is prepared and investigated.

[1026]

[1027]

[1028] The comparative mixture, mixture D-0, has a high clearing point and is characterized by a moderate good transmittance in FFS displays and shows at best acceptable short response times.

[1029] To this mixture, Mixture D-0, was added 0.04% of a compound of the following formula where n is 3

[1030]

[1031] The resulting mixture is referred to as Mixture D. As with the base mixture D-0, it has a clear point of 105°C. Comparative Example D-1

[1032] Table 2

[1033]

Claims

1. A liquid crystal medium, characterized in that, It contains one or more compounds of formula T, in amounts of 3% by weight or more up to 25% by weight or less, selected from compounds of formula T-1 and T-2. express R S This refers to alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, alkenyl, alkenoxy, alkoxyalkyl or fluoroalkenyl groups having 2-7 carbon atoms. X S Indicates F,CF3 or OCF3, and One or more compounds of formula IV in amounts of 5-45% by weight in R 41 This indicates an unsubstituted alkyl group having 1-7 carbon atoms or an unsubstituted alkenyl group having 2-7 carbon atoms, and R 42 It indicates an unsubstituted alkyl group having 1-7 carbon atoms, an unsubstituted alkenyl group having 2-7 carbon atoms, or an unsubstituted alkoxy group having 1-6 carbon atoms; One or more compounds of formula II-2 in an amount of 5-25% by weight in R 2 This indicates alkyl, alkoxy, fluoroalkyl, or fluoroalkoxy groups having 1-7 carbon atoms, and alkenyl, alkenoxy, alkoxyalkyl, or fluoroalkenyl groups having 2-7 carbon atoms. Each occurrence represents an independent entity. L 21 and L 22 and L 23 and L 24 Indicates H or F, X 2 It represents a halogen, a haloalkyl or alkoxy group having 1-3 carbon atoms, or a haloalkenyl or alkenoxy group having 2 or 3 carbon atoms.

2. The medium according to claim 1, characterized in that, Compounds that contain one or more III compounds: in R 3 This indicates alkyl, alkoxy, fluoroalkyl, or fluoroalkoxy groups having 1-7 carbon atoms, and alkenyl, alkenoxy, alkoxyalkyl, or fluoroalkenyl groups having 2-7 carbon atoms. Each occurrence represents an independent entity. L 31 and L 32 H or F can be represented independently of each other. X 3 The term indicates a halogen, which is a haloalkyl or alkoxy group having 1-3 carbon atoms, or a haloalkenyl or alkenoxy group having 2 or 3 carbon atoms. Z 3 This represents -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O- or a single bond, and n represents 0, 1, 2, or 3.

3. The medium according to claim 1 or 2, characterized in that, It contains one or more compounds selected from formulas IV and V: in R 41 and R 42 Independently possessing, in claim 1, the form II-2 for R 2 The meaning indicated Independent of each other and, if These appear twice, and they also represent each other independently. Z 41 and Z 42 Independent of each other, and if Z 41 These appear twice and independently represent -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, -CF2O-, -C≡C-, or a single bond. p represents 1 or 2, R 51 and R 52 Independently possessing, in claim 1, the form II-2 for R 2 The meaning indicated to If they exist, they are represented independently of each other. Z 51 To Z 53 Each of these can be independently represented as -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond, and i and j each represent 0 or 1 independently.

4. The liquid crystal medium according to claim 1, characterized in that, It contains one or more compounds selected from formulas VI to IX: in R 61 This indicates an unsubstituted alkyl group having 1-7 carbon atoms, an unsubstituted alkenyl group having 2-7 carbon atoms, an unsubstituted alkoxy group having 1-6 carbon atoms, or an unsubstituted alkenoxy group having 2-6 carbon atoms. R 62 This indicates an unsubstituted alkyl group having 1-7 carbon atoms, an unsubstituted alkoxy group having 1-6 carbon atoms, or an unsubstituted olefinic group having 2-6 carbon atoms, and l represents 0 or 1. R 71 This indicates an unsubstituted alkyl group having 1-7 carbon atoms, or an unsubstituted alkenyl group having 2-7 carbon atoms. R 72 This indicates an unsubstituted alkyl group having 1-7 carbon atoms, an unsubstituted alkoxy group having 1-6 carbon atoms, or an unsubstituted olefinic group having 2-6 carbon atoms. express R 81 This indicates an unsubstituted alkyl group having 1-7 carbon atoms, or an unsubstituted alkenyl group having 2-7 carbon atoms. R 82 This indicates an unsubstituted alkyl group having 1-7 carbon atoms, an unsubstituted alkoxy group having 1-6 carbon atoms, or an unsubstituted olefinic group having 2-6 carbon atoms. express Z 8 This represents -(C=O)-O-, -CH2-O-, -CF2-O-, or -CH2-CH2-. o represents 0 or 1. R 91 and R 92 Each independently possesses the above for R 72 The meaning given, express p and q represent 0 or 1 independently of each other.

5. The medium according to claim 1 or 2, characterized in that, It contains one or more compounds of formula I. in express express n represents 0 or 1, R 11 and R 12 The groups, which are independently alkyl, alkoxy, fluoroalkyl, or fluoroalkoxy groups, have 1 to 7 carbon atoms, wherein one of the -CH2- groups can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, or 1,3-cyclopentenylene groups, and have 2 to 7 carbon atoms, are alkenyl, alkenoxy, alkoxyalkyl, or fluoroalkenyl groups, wherein one of the -CH2- groups can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, or 1,3-cyclopentenylene groups.

6. The medium according to claim 1 or 2, characterized in that, It contains one or more compounds of formula I. in express express n represents 0 or 1, R 11 R represents 1 And R 12 X represents 1 ,in R 1 The terms "alkyl", "alkoxy", "fluoroalkyl", or "fluoroalkoxy" having 1-7 carbon atoms, wherein one of the -CH2- groups can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, or 1,3-cyclopentenyl; and "alkenyl", "alkenoxy", "alkoxyalkyl", or "fluoroalkenyl" having 2-7 carbon atoms, wherein one of the -CH2- groups can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, or 1,3-cyclopentenyl. X 1 It represents F, Cl, fluoroalkyl, fluoroalkenyl, fluoroalkoxy, or fluoroalkenyloxy.

7. The medium according to claim 5 or 6, characterized in that, The total concentration of Formula I compounds in the entire medium is 1% or higher to 60% or lower.

8. The medium according to claim 5 or 6, characterized in that, The total concentration of Formula I compounds in the entire medium is 1% by weight or higher up to 30% by weight or lower.

9. The medium according to claim 1 or 2, characterized in that, It additionally contains one or more chiral compounds.

10. An electro-optic display, characterized in that, It comprises a liquid crystal medium according to any one of claims 1-9.

11. The display according to claim 10, characterized in that, It is based on IPS-, FFS, HB-FFS and XB-FFS modes.

12. The display according to claim 10 or 11, characterized in that... It includes active matrix addressing devices.

13. An electro-optical component, characterized in that, It comprises a liquid crystal medium according to any one of claims 1-9.

14. Use of the medium according to any one of claims 1-9 in an electro-optic display or electro-optic assembly.

15. The display according to claim 10, characterized in that, It is a mobile display.

16. The method for preparing a liquid crystal medium according to any one of claims 1-9, characterized in that, Mix one or more compounds of formula T with one or more other mesocrystalline compounds, wherein the compounds of formula T are selected from compounds of formula T-1 and T-2. The parameters have the corresponding meanings given in claim 1.

17. A compound of formula T, selected from compounds of formula T-1 and T-2. The parameters have the corresponding meanings given in claim 1.

18. A method for preparing compounds of formula T, selected from compounds of formula T-1 and T-2, characterized in that... A cyclohexenyl-aryl bromide is coupled with a thiophene boric acid substituted with a polar group to obtain a cyclohexenyl-arylthiophene compound, or characterized by coupling a cyclohexenyl-aryl bromide with a thiophene boric acid to obtain a cyclohexenyl-arylthiophene compound. The parameters have the corresponding meanings given in claim 1.

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