Liquid crystal medium, liquid crystal display containing liquid crystal medium and compound containing liquid crystal medium

Abstract

The invention relates to a liquid-crystalline medium having a nematic phase, comprising one or more compounds of formula X, # imgabs0, in which the parameters have the meanings given in the text, to the use thereof in electro-optic displays, in particular in active matrix displays based on the IPS or FFS effect, to displays of this type containing such a liquid-crystalline medium, and to the use thereof in electro-optic displays, in particular in active matrix displays based on the IPS or FFS effect. And to the use of a compound of formula X to improve the transmittance and / or response time of a liquid crystalline medium comprising one or more additional mesogenic compounds, and to a compound of formula X.

Description

[0001] This application is a divisional application of a Chinese patent application filed on July 2, 2020, with application number 202080048869.7, and invention name “Liquid crystal medium and liquid crystal display containing the same”. Technical Field

[0002] The present invention relates to novel liquid-crystal media, in particular for liquid-crystal displays, and to these liquid-crystal displays, in particular liquid-crystal displays using the IPS (in-plane switching) or preferably FFS (fringe field switching) effect with dielectrically positive liquid crystals. The last one is occasionally also referred to as SG-FFS (super-clamped ( s Uper g The invention relates to a liquid crystal medium which has a positive dielectric anisotropy and a dielectric constant parallel to and perpendicular to the molecular director. The liquid crystal medium is ...

[0003] The media are characterized by particularly high transmittance and reduced response times in the respective display, which is due to their unique combination of physical properties, especially through their dielectric properties and in particular through their high (ε ⊥ / ε av. ) ratio or their higher dielectric ratio (ε ⊥ This also leads to their excellent performance in the displays according to the invention. Background Art

[0004] IPS and FFS displays using dielectric positive liquid crystals are well known in the art and have been widely adopted for many types of displays, such as desktop monitors and televisions, but also for mobile applications.

[0005] However, IPS and in particular FFS displays using dielectric negative liquid crystals have recently been widely adopted. The latter is sometimes referred to as UB-FFS (Ultra Bright FFS). Such a display is disclosed, for example, in US2013 / 0207038A1. These displays are characterized by a significantly increased transmittance compared to previously used IPS and FFS displays, which are already dielectrically positive liquid crystals. However, these displays using conventional dielectric negative liquid crystals have a serious disadvantage: a higher operating voltage is required compared to individual displays using dielectrically positive liquid crystals. The liquid crystal medium for UB-FFS has a dielectric anisotropy of -0.5 or less and preferably -1.5 or less.

[0006] Liquid crystal media for HB-FFS (high brightness FFS) have a dielectric anisotropy of 0.5 or more and preferably 1.5 or more. Liquid crystal media for HB-FFS comprising both dielectrically negative and dielectrically positive liquid crystal compounds or mesogenic compounds are disclosed, for example, in US 2013 / 0207038 A1. These media are characterized by a relatively large ε ⊥ and ε av . value, however, its (ε ⊥ / Δε) ratio is relatively small.

[0007] However, according to the present application, the IPS or FFS effect in which the dielectrically positive liquid-crystalline medium exhibits a planar alignment is preferred.

[0008] Industrial use of this effect in electro-optical display elements requires liquid-crystal phases that must meet a variety of requirements. Of particular importance here is the chemical resistance to moisture, air and physical influences such as heat, radiation in the infrared, visible and ultraviolet regions as well as direct current (DC) and alternating current (AC) electric fields.

[0009] Furthermore, industrially usable liquid crystal phases need to have a liquid crystal mesophase in a suitable temperature range and with low viscosity.

[0010] The series of compounds having a liquid crystal mesophase which have been disclosed so far do not include a single compound which meets all of these requirements. Therefore, mixtures of 2 to 25, preferably 3 to 18 compounds are usually prepared to obtain substances which can be used as liquid crystal phases.

[0011] Matrix liquid crystal displays (MLC displays) are known. Non-linear elements that can be used for individual switching of individual pixels are, for example, active elements (ie transistors). The term "active matrix" is subsequently used, wherein thin-film transistors (TFTs) are usually used, which are usually arranged on a glass plate as substrate.

[0012] A distinction is made between two technologies: TFTs comprising compound semiconductors, for example CdSe or metal oxides such as ZnO, or TFTs based on polycrystalline and especially amorphous silicon. The latter technology is currently of greatest commercial importance worldwide.

[0013] The TFT matrix is ​​applied to the inside of one glass plate of the display, while the other glass plate carries a transparent counter electrode on its inside. The TFTs are very small compared to the size of the pixel electrodes and have almost no adverse effect on the image. The technology can also be extended to full-color capable displays, where a mosaic of red, green and blue filters is arranged in such a way that a filter element is arranged opposite each switchable pixel.

[0014] The TFT displays most commonly used to date are usually operated with transmissive crossed polarizers 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 notebook, laptop and mobile applications usually use TN, VA or FFS cells.

[0015] The term "MLC display" comprises here any matrix display with integrated non-linear elements, ie displays which, in addition to the active matrix, also have passive elements, such as varistors or diodes (MIM=metal-insulator-metal).

[0016] MLC displays of this type are particularly suitable for TV applications, monitors and notebooks or for displays with a high information density, for example in automobile construction or aircraft construction. In addition to the problems with the angular dependence of the contrast and the response time, problems also arise in MLC displays due to the insufficiently high specific resistance of the liquid crystal mixtures [TOGASHI, S., SEKI-GUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, September 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, pp. 141 ff., Paris; STROMER, M., Proc. Eurodisplay 84, September 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, pp. 145 ff., Paris]. As the resistance decreases, the contrast of the MLC display deteriorates. Since the specific resistance of the liquid crystal mixture generally decreases over the lifetime of the MLC display due to interactions with the inner surfaces of the display, a high (initial) resistance is very important for displays that must have acceptable resistance values ​​during long operation.

[0017] In addition to IPS displays (e.g. Yeo, SD, 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 crystal displays today, especially for television applications.

[0018] The most important designs can be mentioned here: MVA (multi-domain vertical alignment, for example: 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, CT 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, for example: Kim, SangSoo, 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 Vision, for example: 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 (photoaligned VA) and PSVA (polymer-stabilized VA).

[0019] In general form, 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. Although the response time of modern ECB displays has been significantly improved by using an overdrive addressing method, 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, particularly in grayscale switching, there are still unsatisfactory problems.

[0020] ECB displays, such as ASV displays, use liquid crystal media with negative dielectric anisotropy (Δε), whereas TN and all conventional IPS displays to date use liquid crystal media with positive dielectric anisotropy. However, there is currently an increasing demand for IPS and FFS displays which utilize dielectrically negative liquid crystal media.

[0021] In this type of liquid crystal display, liquid crystal is used as a dielectric material whose optical properties change reversibly when a voltage is applied.

[0022] Since the operating voltage should be as low as possible in displays, i.e. also in displays according to these mentioned effects, all liquid-crystalline media are used which usually consist predominantly of liquid-crystalline compounds which all have a dielectric anisotropy of the same sign and have the highest possible dielectric anisotropy value. Usually, relatively small proportions of neutral compounds are used at most and if possible no compounds with a dielectric anisotropy of the opposite sign to the dielectric anisotropy of the medium are used. In the case of liquid-crystalline media with negative dielectric anisotropy, for example for ECB or UB-FFS displays, therefore predominantly compounds with negative dielectric anisotropy are used. The respective liquid-crystalline medium used usually consists predominantly and often even substantially of liquid-crystalline compounds with negative dielectric anisotropy.

[0023] In the media used according to the present application, a significant amount of dielectrically positive liquid crystal compounds and usually only very small amounts of dielectric compounds or even no dielectric compounds at all are usually employed, since liquid crystal displays are usually intended to have the lowest possible addressing voltage. At the same time, small amounts of dielectrically neutral compounds can be used advantageously in certain cases.

[0024] US2013 / 0207038A1 discloses liquid crystal media for HB-FFS displays, proposing to improve the performance of FFS displays using liquid crystals with positive dielectric anisotropy by additionally incorporating 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 medium. To this end, the concentration of dielectrically positive materials must be increased, which in turn leaves less room for using dielectrically neutral compounds as diluents in the mixture, or alternatively compounds with stronger positive dielectric anisotropy must be used. These alternatives all have the strong disadvantage of increasing the response time of the liquid crystal in the display.

[0025] Liquid crystal media with positive dielectric anisotropy for use in IPS and FFS displays have been disclosed. Some examples are given below.

[0026] CN 104232105A, WO 2014 / 192390 and WO 2015 / 007131 disclose liquid crystal media having positive dielectric anisotropy, some of which have a relatively high dielectric constant perpendicular to the director.

[0027] Obviously, the phase range of the liquid crystal mixture must be broad enough to be useful for the intended application of the display.

[0028] The response time of liquid-crystalline media in displays must be improved, i.e. reduced. This is particularly important for displays for 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 with the lowest possible rotational viscosity. However, the results obtained here are insufficient for many applications and therefore it seems desirable to find methods for further optimization.

[0029] Adequate stability of the medium to extreme loads, in particular to UV exposure and heating, is very important. This can be critical, especially in the case of displays of mobile devices (eg mobile phones).

[0030] The MLC displays disclosed so far, besides their relatively poor transmittance and their relatively long response time, have other disadvantages. These are for example their relatively low contrast, their relatively high viewing angle dependence and the difficulty of grayscale regeneration in these displays, especially when viewed from oblique viewing angles, as well as their insufficient VHR and their insufficient lifetime. The desired improvement of the transmittance of displays and their response time is needed to improve their energy efficiency or their ability to render rapidly moving pictures.

[0031] There is therefore a continuing great demand for MLC displays which have a very high specific resistance and at the same time a large operating temperature range, a short response time and a relatively low threshold voltage, with which a large number of gray scales can be produced and which in particular have a good and stable VHR. Summary of the invention

[0032] The object of the present invention is 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, do not have the disadvantages indicated above, or have them only to a reduced extent, and at the same time have very high specific resistance values. In particular, it must be ensured that for mobile phones and navigation systems they also operate at extremely high and extremely low temperatures.

[0033] Surprisingly, it has been found that liquid crystal displays having low threshold voltages and short response times, sufficiently broad nematic phases, favorable birefringence (Δn) and at the same time high transmittance, good stability to decomposition by heating and UV exposure, and a stably high VHR can be obtained if a nematic liquid crystal mixture is used in these display elements, the nematic liquid crystal mixture comprising at least one compound, preferably two or more compounds of the formula X, preferably selected from the group of compounds of the subformulae X-1 and X-2, particularly preferably from the group of compounds of the subformulae X-1-1 and / or X-2-2 and / or X-2-3 and / or X-2-4 and / or X-2-5, more preferably comprising both compounds of the formulae X-1 and X-2, and preferably, furthermore one or more compounds selected from the group of compounds of the formulae I, B and S. Compounds, preferably compounds selected from the groups of compounds of sub-formulae I-1, I-2, I-3 and I-4 and B-1 and B-2 and S-1 and S-2, respectively, particularly preferably selected from sub-formulae I-1 and / or I-2 and / or I-3 and / or I-4 and / or B-1 and / or B-2 and / or S-1 and / or S-2, most preferably formulae I-2, I-4, B-1, B-2 and S-2, and most preferably both formulae I-1 and I-2 and said formula B-1 and / or formula B-2, and preferably at least one additional compound, preferably two or more compounds, selected from the group of compounds of formulae II and III, the former preferably being formulae II-1 and / or II-2, and / or at least one compound, preferably two or more compounds, selected from the group of formulae IV and / or V, and preferably one or more compounds selected from the group of formulae VII to IX (all formulae as defined herein below).

[0034] This type of media is particularly useful in electro-optical displays with active matrix addressing for IPS or FFS displays.

[0035] The present invention therefore relates to a liquid crystal medium comprising a mixture of polar compounds of one or more compounds having a dielectric ratio (ε 2.0 or less) of the dielectric constant perpendicular to the director to the dielectric anisotropy. ⊥ / Δε) and a high dielectric constant perpendicular to the director (ε) of preferably 3.8 or more, preferably 4.5 or more, and most preferably 6.0 or more ⊥ ).

[0036] The dielectric constant perpendicular to the director and the dielectric anisotropy (ε ⊥ / Δε) corresponds to the dielectric constant (ε) parallel to the director. || ) and the dielectric constant perpendicular to the director (ε ⊥ ) ratio, corresponding to 2.0 or less (ε || / ε ⊥)ratio.

[0037] The medium according to the invention preferably additionally comprises one or more compounds selected from the compounds of formulae II and III, preferably one or more compounds of formula II, more preferably additionally comprises one or more compounds of formula III, and most preferably additionally comprises one or more compounds selected from the compounds of formulae IV and V, and again preferably one or more compounds selected from the compounds of formulae VI to IX (all formulae are defined below).

[0038] The mixtures according to the invention exhibit a very broad nematic phase range (clearing point ≥ 70° C.), very favorable capacitance thresholds, relatively high retention values ​​and simultaneously good low temperature stability at -20° C. and -30° C., and very low rotational viscosities. The mixtures according to the invention are further characterized by a good ratio of clearing point to rotational viscosity and a relatively high positive dielectric anisotropy.

[0039] Now, it has been surprisingly found that LCDs of the FFS type using liquid crystals with positive dielectric anisotropy can be realized by using specially selected liquid crystal media. These media are characterized by a specific combination of physical properties. The most decisive of these is their dielectric properties and here a high average dielectric constant (ε av .), a high dielectric constant perpendicular to the director of the liquid crystal molecules (ε⊥), and in particular, a relatively high ratio of these last two values: (ε⊥ / △ε).

[0040] On the one hand, the liquid crystal medium according to the invention preferably has a dielectric anisotropy value of 1.5 or more, preferably 3.5, or more preferably 4.5 or more. On the other hand, its dielectric anisotropy is preferably 26 or less.

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

[0042] Preferably, the dielectric ratio (ε ⊥ / Δε) is preferably 2.0 or less, more preferably 1.5 or less, most preferably 1.0 or less.

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

[0044] In a preferred embodiment which may be identical to the preferred embodiments mentioned above, the dielectric constant (ε) of the liquid-crystal medium according to the invention perpendicular to the director of the liquid-crystal molecules is⊥ ) is 5.0 or greater, more preferably 6.0 or greater, more preferably 7.0 or greater, more preferably 8.0 or greater, more preferably 9.0 or greater and most preferably 10.0 or greater.

[0045] The liquid crystal medium of the present invention has a dielectric anisotropy of 0.5 or more, preferably 1.5 or more, and a dielectric ratio (ε ⊥ / Δε) is 2.0 or less, and contains

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

[0047]

[0048] in

[0049] R 1X and R 2X independently of one another represent H, an alkyl radical having 1 to 15 C atoms, wherein one or more CH2 groups in these radicals may each independently of one another be linked via -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO-, wherein one or more H atoms may be replaced by halogen, and

[0050] R 1X Preferably represents preferably an alkyl or alkoxy group having 1 to 7 C atoms, an alkenyl group having 2 to 7 C atoms, more preferably an alkyl or alkoxy group having 2 to 5 C atoms or an alkenyl group having 2 to 5 C atoms,

[0051] R 2X Or and preferably represents X X ,

[0052] and

[0053] represents, identically or differently on each occurrence, a radical selected from the group consisting of,

[0054] a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and decahydronaphthalene-2,6-diyl, wherein one or more non-adjacent CH2 groups may be replaced by -O- and / or -S-, and wherein one or more H atoms may be replaced by F,

[0055] b) the group consisting of 1,4-phenylene and 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which, in addition, one or more H atoms may be replaced by L,

[0056] c) the group consisting of 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, thiophene-2,5-diyl, selenophene-2,5-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, each of which may be mono- or polysubstituted by L,

[0057] d) the group consisting of bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl and spiro[3.3]heptane-2,6-diyl, wherein one or more H atoms may be replaced by F,

[0058] L each, identically or differently, denotes halogen, cyano, alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl having 1 to 7 C atoms, wherein one or more H atoms may be substituted by F or Cl,

[0059] Z X represents, identically or differently on each occurrence, a single bond, -CF2O-, -OCF2-, -CH2CH2-, -CF2CF2-, -C(O)O-, -OC(O)-, -CH2O-, -OCH2-, -CF=CH-, -CH=CF-, -CF=CF-, -CH=CH- or -C≡C-,

[0060] Y 1 represents Cl, CF3, CHF2, OCF3, CN or NCS, preferably Cl, CF3 or OCF3, more preferably CF3 or OCF3,

[0061] Y 2 represents H, F, Cl, CF3, or CHF2, preferably F,

[0062] Preferred Y 1 and Y 2 One, preferably Y 1 is CF3 or OCF3 and the other is H, F, Cl, CF3, OCF3 or CHF2, and

[0063] X X represents F; Cl; CN:NCS; SF5; a fluorinated alkyl, alkoxy, alkenyl or alkenyloxy group each having up to 5 C atoms, preferably F, CF3, OCF3 or NCS, and

[0064] n represents 0, 1 or 2, preferably 0 or 1, most preferably 1, and

[0065] One or more additional compounds, preferably selected from the group of compounds according to conditions b) to f) below

[0066] b) one or more dielectrically positive compounds selected from the group of compounds of formula II and III, preferably compounds each having a dielectric anisotropy greater than 3, preferably one or more compounds of formula II:

[0067]

[0068] in

[0069] R 2 represents an alkyl group, an alkoxy group, a fluorinated alkyl group or a fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl group, an alkenyloxy group, an alkoxyalkyl group or a fluorinated alkenyl group having 2 to 7 C atoms, and is preferably an alkyl group or an alkenyl group,

[0070] and

[0071] In each occurrence, they are expressed independently of each other

[0072]

[0073] Best

[0074]

[0075] L 21 and L 22 Indicates H or F, preferably L 21 Indicates F,

[0076] X 2 denotes halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, preferably denotes F, Cl, -OCF3, -O-CH2CF3, -O-CH=CH2, -O-CH=CF2 or -CF3, very preferably denotes F, Cl, -O-CH=CF2 or -OCF3, m denotes 0, 1, 2 or 3, preferably 1 or 2 and particularly preferably 2,

[0077] R 3 represents an alkyl group, an alkoxy group, a fluorinated alkyl group or a fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl group, an alkenyloxy group, an alkoxyalkyl group or a fluorinated alkenyl group having 2 to 7 C atoms, and is preferably an alkyl group or an alkenyl group,

[0078] and

[0079] In each occurrence, independently

[0080]

[0081] Best

[0082]

[0083] L 31 and L 32 independently represent H or F, preferably L 31 Indicates F,

[0084] X 3 represents halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, F, Cl, -OCF3, -OCHF2, -O-CH2CF3, -O-CH=CF2, -O-CH=CH2 or -CF3, very preferably F, Cl, -O-CH=CF2, -OCHF2 or -OCF3,

[0085] Z 3 represents -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, or a single bond, preferably represents -CH2CH2-, -COO-, trans-CH=CH-, or a single bond, and very preferably represents -COO-, trans-CH=CH-, or a single bond, and

[0086] n is 0, 1, 2 or 3, preferably 1, 2 or 3 and particularly preferably 1, and

[0087] c) optionally, preferably necessarily, one or more dielectrically neutral compounds selected from the group consisting of formulae IV and V:

[0088]

[0089] in

[0090] R 41 and R 42 Independently of each other, the above formula II with respect to R 2 The meaning shown is preferably R 41 represents an alkyl group and R 42 represents an alkyl group or an alkoxy group, or R 41 represents an alkenyl group and R 42 represents an alkyl group,

[0091] and

[0092] Independent of each other and if

[0093] Appears twice,

[0094] These also represent independently of each other

[0095]

[0096] Preferably

[0097] and One or more of

[0098]

[0099] Z 41 and Z 42 Independently of each other and if Z 41 appears twice, these groups also independently represent -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, -CF2O-, -C≡C- or a single bond, preferably one or more of which represent a single bond, and

[0100] p represents 0, 1 or 2, preferably 0 or 1, and

[0101] R 51 and R 52 Independently of each other, they have 41 and R 42 one of the meanings given above and preferably denotes alkyl having 1 to 7 C atoms, preferably n-alkyl, particularly preferably n-alkyl having 1 to 5 C atoms; alkoxy having 1 to 7 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy having 2 to 5 C atoms; alkoxyalkyl, alkenyl or alkenyloxy, preferably alkenyloxy, having 2 to 7 C atoms, preferably 2 to 4 C atoms,

[0102] to

[0103] If present, they represent each independently of the other

[0104]

[0105] Best

[0106]

[0107] Best

[0108] express and, if present,

[0109] Preferred representation

[0110] Z 51 To Z 53 each independently represents -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,

[0111] i and j each independently represent 0 or 1,

[0112] (i+j) preferably represents 0, 1 or 2, more preferably represents 0 or 1 and most preferably represents 1.

[0113] d) optionally again, preferably necessarily, alternatively or additionally, one or more dielectrically negative compounds selected from the group of formulae VI to IX:

[0114]

[0115] in

[0116] R 61 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a straight-chain alkyl group, more preferably a n-alkyl group, most preferably a propyl group or a pentyl group; an unsubstituted alkenyl group having 2 to 7 C atoms, preferably a straight-chain alkenyl group, particularly preferably a group 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,

[0117] 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

[0118] l means 0 or 1,

[0119] 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 a propyl group or a pentyl group; or an unsubstituted alkenyl group having 2 to 7 C atoms, preferably a straight-chain alkenyl group, particularly preferably a group having 2 to 5 C atoms,

[0120] 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

[0121] express

[0122]

[0123] R 81 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a straight-chain alkyl group, more preferably a n-alkyl group, most preferably a propyl group or a pentyl group; or an unsubstituted alkenyl group having 2 to 7 C atoms, preferably a straight-chain alkenyl group, particularly preferably a group having 2 to 5 C atoms,

[0124] R 82 represents an unsubstituted alkyl radical having 1 to 7 C atoms, preferably having 2 to 5 C atoms; an unsubstituted alkoxy radical having 1 to 6 C atoms, preferably having 1, 2, 3 or 4 C atoms; or an unsubstituted alkenyloxy radical having 2 to 6 C atoms, preferably having 2, 3 or 4 C atoms,

[0125] express

[0126]

[0127] Best

[0128]

[0129] More preferred

[0130]

[0131] Z 8 represents -(C=O)-O-, -CH2-O-, -CF2-O- or -CH2-CH2-, preferably -(C=O)-O- or -CH2-O-, and

[0132] o means 0 or 1,

[0133] R 91 and R 92 Independently of each other, they have the above 72 The meaning given,

[0134] R 91 preferably denotes an alkyl radical having 2 to 5 C atoms, preferably having 3 to 5 C atoms,

[0135] R 92 Preferably it 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.

[0136] express

[0137] p and q are independently 0 or 1, and

[0138] (p+q) preferably represents 0 or 1, provided that

[0139] express

[0140] Alternatively, p=q=1 is preferred.

[0141] e) optionally, preferably necessarily, one or more compounds of the formula B and / or formula S, preferably selected from the group of compounds of the formulae B-1 and B-2, S-1 and S-2, preferably in a concentration in the range of 1% to 60%, more preferably in the range of 5% to 40%, particularly preferably in the range of 8% to 35%,

[0142]

[0143] in

[0144] express

[0145]

[0146] In each occurrence, they are expressed independently of each other

[0147]

[0148] Best

[0149] n represents 1 or 2, preferably 1,

[0150] R 1 represents preferably alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms; alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, and is preferably alkyl, alkoxy, alkenyl or alkenyloxy, more preferably alkyl, alkenyl, alkoxy or alkenyloxy, and most preferably alkyl, and

[0151] X 1 represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms, more preferably F, Cl, CF3 or OCF3, and

[0152]

[0153] in

[0154] express

[0155]

[0156] In each occurrence, they are expressed independently of each other

[0157]

[0158] Best

[0159] n represents 1 or 2, preferably 1,

[0160] R 1 represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy group, preferably having 1 to 7 C atoms; an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl group, preferably an alkyl, alkoxy, alkenyl or alkenyloxy group, more preferably an alkyl, alkenyl, alkoxy or alkenyloxy group, and most preferably an alkyl group, and

[0161] X 1 represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms, more preferably F, Cl, CF3 or OCF3, and

[0162] f) likewise optionally, preferably necessarily, alternatively or additionally, one or more compounds of the formula I:

[0163]

[0164] in

[0165] express

[0166]

[0167]

[0168] express

[0169]

[0170] Best

[0171]

[0172] n represents 0 or 1,

[0173] R 11 and R 12 independently of one another represent preferably alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms; alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, and are preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkyl, alkoxy or alkenyloxy, and R 11 Alternatively, R 1 And R 12 Alternatively, X 1 ,

[0174] R 1 represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy group preferably having 1 to 7 C atoms; an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl group having 2 to 7 C atoms, and is preferably an alkyl or alkenyl group, and

[0175] X 1 represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably having 1 to 4 C atoms, more preferably F, Cl, CF3 or OCF3,

[0176] Compounds of formula B and formula S are excluded therefrom.

[0177] The present invention also relates to compounds of formula X.

[0178] Preferably, the medium according to the present application comprises one or more compounds of formula X selected from the group of preferred compounds of subformulae X-1 and X-2 thereof,

[0179]

[0180] wherein the parameters have the respective meanings given above under formula X and are preferably

[0181] and

[0182] Independently express

[0183]

[0184] Best

[0185]

[0186] In a more preferred embodiment, the medium according to the present application comprises one or more compounds of the formula X-1 selected from the group of preferred compounds of the subformulae X-1-1 to X-1-4 thereof,

[0187]

[0188] The parameters have the meanings given above.

[0189] In a more preferred embodiment, the medium according to the present application comprises one or more compounds of the formula X-1 selected from the group of preferred compounds of its subformulae X-2-1 to X-2-6,

[0190]

[0191]

[0192] The parameters have the meanings given above.

[0193] The liquid-crystalline media according to the present application preferably have a nematic phase.

[0194] Throughout this application and in particular with respect to R 1 The definition of alkyl is taken to mean an alkyl group which may be straight-chain or branched. Each of these groups is preferably straight-chain and preferably has 1, 2, 3, 4, 5, 6, 7 or 8 C atoms and is therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0195] In case alkyl means a branched alkyl group, it preferably means 2-alkyl, 2-methylalkyl or 2-(2-ethyl)-alkyl, preferably 2-butyl (=1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular 2-methylbutyl, 2-methylbutoxy-4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl and 2-dodecyl. These groups are most preferably 2-hexyl and 2-octyl.

[0196] Each branched group, especially for R 1 (which produces chiral compounds) are also referred to as chiral groups in the present application. Particularly preferred chiral groups are 2-alkyl, 2-alkoxy, 2-methylalkyl, 2-methylalkoxy, 2-fluoroalkyl, 2-fluoroalkoxy, 2-(2-ethin)-alkyl, 2-(2-ethin)-alkoxy, 1,1,1-trifluoro-2-alkyl and 1,1,1-trifluoro-2-alkoxy.

[0197] By way of example, particularly preferred chiral groups are 2-butyl (=1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular 2-methylbutyl, 2-methylbutoxy, 2-methylpentyloxy, 3-methylpentyloxy, 2-ethylhexyl, 1-methylhexyloxy, 2-octyloxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpentyl, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl, 2-dodecyl, 6-methoxyoctyloxy, 6-methyloctyloxy, 6-methyloctanoyloxy, 5-methyl Heptyloxycarbonyl, 2-methylbutyryloxy, 3-methylvaleryloxy, 4-methylhexanoyloxy, 2-chloropropionyloxy, 2-chloro-3-methylbutyryloxy, 2-chloro-4-methylvaleryloxy, 2-chloro-3-methylvaleryloxy, 2-methyl-3-oxapentyl, 2-methyl-3-oxahexyl, 1-methoxypropyl-2-oxy, 1-ethoxypropyl-2-oxy, 1-propoxypropyl-2-oxy, 1-butoxypropyl-2-oxy, 2-fluorooctyloxy, 2-fluorodecyloxy, 1,1,1-trifluoro-2-octyloxy, 1,1,1-trifluoro-2-octyl, 2-fluoromethyloctyloxy. Very preferred are 2-hexyl, 2-octyl, 2-octyl, 1,1,1-trifluoro-2-hexyl, 1,1,1-trifluoro-2-octyl and 1,1,1-trifluoro-2-octyl.

[0198] Preferably, the compound of formula B is selected from the group of compounds of formula B-1 and B-2:

[0199]

[0200] in

[0201] R 1 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, preferably having 1 to 7 C atoms; alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, preferably alkyl or alkenyl, and

[0202] X 1 represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably have 1 to 4 C atoms, preferably F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, and most preferably OCF3 or CF3.

[0203] Preferably, the compound of formula S is selected from the group of compounds of formula S-1 and S-2:

[0204]

[0205] in

[0206] R1 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, preferably having 1 to 7 C atoms; alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, preferably alkyl or alkenyl, and

[0207] X 1 represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably have 1 to 4 C atoms, preferably F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, and most preferably OCF3 or CF3.

[0208] Preferably, the compound of formula I is selected from the group of compounds of formula I-1, I-2, I-3 and I-4:

[0209]

[0210]

[0211] in

[0212] R 11 and R 12 independently of one another represent alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, preferably having 1 to 7 C atoms; alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,

[0213] R 1 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, preferably having 1 to 7 C atoms; alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl, preferably alkyl or alkenyl, and

[0214] X 1 represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, the latter four groups preferably have 1 to 4 C atoms, preferably F, Cl, CF3 or OCF3, more preferably F, CF3 or OCF3, and most preferably OCF3 or CF3.

[0215] As described in the literature (for example in standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), the compounds of the general formula X are prepared by methods known per se, specifically under reaction conditions known and suitable for the reaction. Variants known per se but not mentioned in greater detail here may be used.

[0216] If desired, the starting materials can also be formed in situ by not isolating them from the reaction mixture, but instead converting them further into the compounds of the general formula X immediately afterwards.

[0217] Preferred synthetic routes to the compounds according to the invention are shown in the following schemes and further illustrated by means of working examples. The synthesis can be adapted to the specific desired compound of general formula X by selecting appropriate starting materials.

[0218] Solution 1

[0219]

[0220] The parameters R, Y1, Y2 and X have the following formula X for R 1X , Y, Y and X X The respective meanings given, and Hal is halogen, preferably Br or I, and wherein the 1,4-phenylene part of the halide, such as bromide, may optionally be substituted by one or two F atoms.

[0221] Solution 2

[0222]

[0223] The parameters R, Y1, Y2 and X have the following formula X for R 1X , Y 1 , Y 2 and X X The various meanings given.

[0224] Solution 3

[0225]

[0226] The parameters R, Y1, Y2 and X have the following formula X for R 1X , Y 1 , Y 2 and X X The respective meanings given, and Hal is halogen, preferably Br or I, wherein the 1,4-phenylene part of the bromide may optionally be substituted by one or two F atoms.

[0227] Solution 4

[0228]

[0229] The parameters R, Y1, Y2 and X have the following formula X for R 1X , Y1, Y2 and X X The respective meanings given, and Hal is halogen, preferably Br or I, wherein each of the 4,4'-phenylene parts of the bromide may be optionally substituted by one, two or more F atoms.

[0230] Another object of the present invention is to prepare a 1-halo-2-Y 2 -3-Y 1 -4-X-phenyl compound to synthesize the compound of formula X. In the key step of the synthesis, the block 1-halogen-2-Y 2 -3-Y 1 -4-X-phenyl reacts with ketones via metal-mediated coupling reactions to give the corresponding tertiary alcohols, which are subsequently dehydrated to the corresponding styrene derivatives which can undergo hydrogenation in the following step. 2 -3-Y 1 -4-X-phenyl groups are preferably reacted in a Suzuki coupling reaction with aromatic boronic acid derivatives to give the corresponding biphenyl derivatives which can also undergo hydrogenation.

[0231] The reactions described should be regarded as illustrative only. A person skilled in the art can carry out corresponding modifications of the syntheses described and also follow other suitable synthetic routes in order to obtain compounds of formula X.

[0232] The compounds of the general formula X can be used in liquid-crystalline media. The present invention therefore also relates to a liquid-crystalline medium comprising two or more liquid-crystalline compounds, which comprises one or more compounds of the general formula X.

[0233] The present invention further relates to a liquid-crystal display, in particular an IPS or FFS display, particularly preferably an FFS or SG-FFS display, which contains the liquid-crystal medium according to the invention.

[0234] The invention further relates to an IPS or FFS type liquid crystal display comprising a liquid crystal cell consisting of two substrates, at least one of which is transparent to light and at least one of which has an electrode layer, and a layer of a liquid crystal medium located between the substrates, the liquid crystal medium comprising a polymerized component and a low molecular weight component, wherein the polymerized component is obtainable by polymerization of one or more polymerizable compounds in the liquid crystal medium between the substrates of the liquid crystal cell, preferably by applying an electric voltage and wherein the low molecular weight component is a liquid crystal mixture according to the invention as described above and below.

[0235] The display according to the invention is preferably addressed by an active matrix (active matrix LCD, AMD for short), preferably by a matrix of thin film transistors (TFTs). However, the liquid crystals according to the invention can also be used in an advantageous manner in displays with other known addressing mechanisms.

[0236] The invention further relates to a process for preparing the liquid-crystalline media according to the invention by mixing one or more compounds of the formula X, preferably selected from the group of compounds of the formulae XA and XB, with one or more low molecular weight liquid-crystalline compounds or liquid-crystalline mixtures and optionally further liquid-crystalline compounds and / or additives.

[0237] The following meanings apply in this context:

[0238] Unless otherwise stated, the term "FFS" is used to refer to both FFS and SG-FFS displays.

[0239] The term "mesogenic group" is known to those skilled in the art and is described in the literature and denotes a group which, due to the anisotropy of its attraction and repulsion interactions, substantially contributes to the induction of a liquid crystal (LC) phase in a low molecular weight or polymeric substance. A compound containing a mesogenic group (mesogenic compound) does not necessarily have a liquid crystal phase itself. A mesogenic compound may also exhibit liquid crystal phase behavior only after mixing with other compounds and / or after polymerization. Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units. An overview of the terms and definitions used in connection with mesogenic or liquid crystal compounds is given in Pure Appl. Chem. 73 (5), 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368.

[0240] The term "spacer" or "spacer" for short (also referred to above and below as "Sp") 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 indicated, the term "spacer" or "spacer" above and below denotes a flexible group which connects the mesogenic group and the polymerizable group to each other in a polymerizable mesogenic compound.

[0241] For the purposes of the present invention, the term "liquid-crystal medium" is intended to mean a medium comprising a liquid-crystal mixture and one or more polymerizable compounds, such as reactive mesogens. The term "liquid-crystal mixture" (or "host mixture") is intended to mean a liquid-crystal mixture consisting only of non-polymerizable low molecular weight compounds, preferably two or more liquid-crystal compounds, and optionally other additives, such as chiral dopants or stabilizers.

[0242] Particular preference is given to liquid-crystalline mixtures and liquid-crystalline media which have a nematic phase, in particular at room temperature.

[0243] In a preferred embodiment of the present invention, the liquid crystal medium comprises one or more positive dielectric compounds having a dielectric anisotropy greater than 3, which are selected from the group of compounds of the formulae II-1 and II-2:

[0244]

[0245] wherein the parameters have the respective meanings indicated above under formula II, and L 23 and L 24 independently represent H or F, preferably L 23 represents F, and

[0246] With

[0247] One of the meanings given

[0248] In the case of formula II-1 and II-2, X 2 Preferably represents F or OCF3, particularly preferably F, and in the case of formula II-2,

[0249] and

[0250] Independently of each other, preferred representation

[0251]

[0252] And / or a compound selected from formula III-1 and III-2:

[0253]

[0254] wherein the parameters have the meanings given in formula III,

[0255] The media according to the invention may comprise, instead of or in addition to the compounds of formula III-1 and / or III-2, one or more compounds of formula III-3

[0256]

[0257] The parameters have the meanings given above, and the parameter L 31 and L 32 , independently of each other and of the other parameters, represent H or F.

[0258] The liquid-crystalline medium preferably comprises a compound selected from the group consisting of compounds of the formulae II-1 and II-2, in which L 21 and L 22 and / or L 23 and L 24 Both represent F.

[0259] In a preferred embodiment, the liquid-crystalline medium comprises a compound selected from the group consisting of compounds of the formulae II-1 and II-2, in which L 21 , L 22 , L 23 and L 24 All represent F.

[0260] The liquid crystal medium preferably comprises one or more compounds of formula II-1. The compound of formula II-1 is preferably selected from the compounds of formula II-1a to II-1e, preferably one or more compounds of formula II-1a and / or II-1b and / or II-1d, preferably compounds of formula II-1a and / or II-1d or II-1b and / or II-1d, most preferably compounds of formula II-1d:

[0261]

[0262] Wherein the parameters have the respective meanings as stated above, and L 25 and L 26 , independently of each other and of the other parameters, represents H or F, and preferably

[0263] In Formula II-1a and II-1b,

[0264] L 21 and L 22 All represent F,

[0265] In Formula II-1c and II-1d,

[0266] L 21 and L 22 All represent F and / or L 23 and L 24 Both represent F, and

[0267] In formula II-1e,

[0268] L 21 , L 22 and L 23 Indicates F.

[0269] The liquid crystal medium preferably comprises one or more compounds of the formula II-2, which are preferably selected from the compounds of the formulae II-2a to II-2k, preferably one or more compounds each of the formulae II-2a and / or II-2h and / or II-2j:

[0270]

[0271]

[0272] Wherein the parameters have the respective meanings as described above, and L 25 To L 28 , independently of each other, represent H or F, preferably L 27 and L 28 All represent H, and L is particularly preferred 26 Indicates H.

[0273] The liquid-crystalline medium preferably comprises a compound selected from the group consisting of compounds of the formulae II-2a to II-2k, in which L 21 and L 22 All represent F and / or L 23 and L 24 Both represent F.

[0274] In a preferred embodiment, the liquid-crystalline medium comprises a compound selected from the group consisting of compounds of the formulae II-2a to II-2k, in which L 21 , L 22 , L 23 and L 24 All represent F.

[0275] Particularly preferred compounds of formula II-2 are compounds of the following formula, particularly preferably formula II-2a-1 and / or II-2h-1 and / or II-2k-2:

[0276]

[0277]

[0278]

[0279] Where R 2 and X 2 has the meanings given above, and X 2 Preferably it represents F.

[0280] The liquid crystal medium preferably comprises one or more compounds of the formula III-1. The compound of the formula III-1 is preferably selected from the compounds of the formulae III-1a to III-1j, preferably from the compounds of the formulae III-1c, III-1f, III-1g and III-1j:

[0281]

[0282]

[0283] wherein the parameters have the meanings given above and preferably wherein the parameters have the respective meanings given above, the parameter L 33 and L 34 , independently of each other and of the other parameters, represents H or F, and the parameter L 35 and L 36 , independently of each other and of the other parameters, represent H or F.

[0284] The liquid crystal medium preferably comprises one or more compounds of the formula III-1c, which are preferably selected from the compounds of the formulae III-1c-1 to III-1c-5, preferably the formula III-1c-1 and / or III-1c-2, most preferably the formula III-1c-1:

[0285]

[0286] Where R 3 Has the meaning stated above.

[0287] The liquid crystal medium preferably comprises one or more compounds of the formula III-1f, which are preferably selected from the compounds of the formulae III-1f-1 to III-1f-6, preferably formula III-1f-1 and / or III-1f-2 and / or III-1f-3 and / or III-1f-6, more preferably formula III-1f-3 and / or III-1f-6, more preferably formula III-1f-6:

[0288]

[0289] Where R 3 Has the meaning stated above.

[0290] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1g, which are preferably selected from the compounds of the formulae III-1g-1 to III-1g-5, preferably the formula III-1g-3:

[0291]

[0292] Where R 3 Has the meaning stated above.

[0293] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1h, which are preferably selected from the compounds of the formulae III-1h-1 to III-1h-3, preferably the formula III-1h-3:

[0294]

[0295]

[0296] where the parameters have the meanings given above, and X 3 Preferably it represents F.

[0297] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1i, which are preferably selected from the compounds of the formulae III-1i-1 and III-1i-2, preferably the formula III-1i-2:

[0298]

[0299] where the parameters have the meanings given above, and X 3 Preferably it represents F.

[0300] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-1j, which are preferably selected from the compounds of the formulae III-1j-1 and III-1j-2, preferably the formula III-1j-1:

[0301]

[0302] where the parameters have the meanings given above.

[0303] The liquid crystal medium preferably comprises one or more compounds of formula III-2. The compound of formula III-2 is preferably selected from the compounds of formula III-2a and III-2b, preferably formula III-2b:

[0304]

[0305] The parameters have the meanings given above, and the parameter L 33 and L 34 , independently of each other and of the other parameters, represent H or F.

[0306] The liquid-crystalline medium preferably comprises one or more compounds of the formula III-2a, which are preferably selected from the compounds of the formulae III-2a-1 to III-2a-6:

[0307]

[0308]

[0309] Where R 3 Has the meaning stated above.

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

[0311]

[0312] Where R 3 Has the meaning stated above.

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

[0314]

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

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

[0317]

[0318] Where R 3 Has the meaning stated above.

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

[0320] In the present application, elements all include their respective isotopes. In particular, one or more H in the compound can be replaced by D, and this is also particularly preferred in certain embodiments. The corresponding high degree of deuteration of the corresponding compound can, for example, detect and identify the compound. This is very useful in some cases, particularly in the case of formula I compound.

[0321] In this application,

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

[0323] Alkenyl particularly preferably represents 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 invention, the medium according to the invention comprises in each case one or more compounds of the formula VI selected from the group consisting of compounds of the formulae VI-1 and VI-2, preferably one or more compounds of each of the formula VI-1 and one or more compounds of the formula VI-2,

[0325]

[0326] wherein the parameters have the respective meanings given in the above formula VI, and preferably R in formula VI-1 61 and R 62 independently of one another represent methoxy, ethoxy, propoxy, butoxy (or also pentoxy), preferably ethoxy, butoxy or pentoxy, more preferably ethoxy or butoxy and most preferably butoxy;

[0327] In formula VI-2

[0328] R 61 Preferably, it represents 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 represents 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 invention, the medium according to the invention comprises in each case one or more compounds of the formula VII selected from the group consisting of compounds of the formulae VII-1 to VII-3, preferably one or more compounds of each of the formula VII-1 and one or more compounds of the formula VII-2,

[0331]

[0332]

[0333] wherein the parameters have the respective meanings given in formula VII above, and preferably

[0334] R 71 represents vinyl, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, n-propyl or n-pentyl, and

[0335] R 72 represents 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.

[0336] In a preferred embodiment of the present invention, the medium according to the invention comprises in each case one or more compounds of the formula VI-1 selected from the following compounds:

[0337]

[0338] In a preferred embodiment of the present invention, the medium according to the invention comprises in each case one or more compounds of the formula VI-2 selected from the following compounds:

[0339]

[0340] In a preferred embodiment of the invention, the media according to the invention comprise in each case one or more compounds of the formula VII-1 selected from the following compounds:

[0341]

[0342] In a preferred embodiment of the present invention, the media according to the invention comprise in each case one or more compounds of the formula VII-2 selected from the following compounds:

[0343]

[0344]

[0345] In addition to the compound of formula B or its preferred subformulae, the medium according to the invention preferably contains one or more dielectrically negative compounds selected from the compounds of 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.

[0346] In a preferred embodiment of the present invention, the medium according to the invention comprises in each case one or more compounds of the formula VIII selected from the compounds of the formulae VIII-1 to VIII-3, preferably one or more compounds of each of the formula VIII-1 and / or one or more compounds of the formula VIII-3,

[0347]

[0348] wherein the parameters have the respective meanings given above in formula VIII, and preferably

[0349] R 81 represents 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

[0350] R 82 represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably an unsubstituted alkoxy group having 1 to 5 C atoms or an unsubstituted alkoxy group having 1 to 6 C atoms.

[0351] In Formula VIII-1 and VIII-2, R 82 Preferably it represents an alkoxy group having 2 or 4 C atoms and, most preferably, an ethoxy group and in the formula VIII-3 it preferably represents an alkyl group, preferably a methyl group, an ethyl group or an n-propyl group, most preferably a methyl group.

[0352] In a further preferred embodiment, the medium comprises one or more compounds of formula IV, preferably compounds of formula IVa

[0353]

[0354] in

[0355] R 41 represents an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms, preferably an n-alkyl radical, particularly preferably having 2, 3, 4 or 5 C atoms, and

[0356] R 42 represents an unsubstituted alkyl group having 1-7 C atoms, an unsubstituted alkenyl group having 2-7 C atoms or an unsubstituted alkoxy group having 1-6 C atoms (each preferably having 2-5 C atoms), preferably an unsubstituted alkenyl group having 2, 3 or 4 C atoms, more preferably a vinyl group or a 1-propenyl group and in particular a vinyl group.

[0357] In a particularly preferred embodiment, the medium comprises one or more compounds of the formula IV from the compounds of the formulae IV-1 to IV-4, preferably of the formula IV-1,

[0358]

[0359] in

[0360] Alkyl and alkyl' independently represent an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms,

[0361] alkenyl and alkenyl' independently of one another represent an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 C atoms,

[0362] alkenyl′ preferably denotes 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

[0363] Alkoxy represents an alkoxy group having 1 to 5 C atoms, preferably 2 to 4 C atoms.

[0364] In a particularly preferred embodiment, the medium according to the invention comprises one or more compounds of the formula IV-1 and / or one or more compounds of the formula IV-2.

[0365] In a further preferred embodiment, the medium comprises one or more compounds of the formula V.

[0366] The medium according to the invention preferably comprises the following compounds in the stated total concentration:

[0367] 1-60% by weight of one or more compounds selected from the group of compounds of formula X, and

[0368] 1-60% by weight of one or more compounds selected from the group of compounds of formula B, and

[0369] 0-60% by weight of one or more compounds of formula I, which are preferably selected from the group of compounds of formula I-1 and I-2, most preferably compounds of formula I-2, and / or

[0370] 5-60% by weight of one or more compounds of formula II, preferably selected from the group of compounds of formula II-1 and II-2, and / or

[0371] 5-25% by weight of one or more compounds of formula III, and / or

[0372] 5-45% by weight of one or more compounds of formula IV, and / or

[0373] 5-25% by weight of one or more compounds of formula V, and / or

[0374] 5-25% by weight of one or more compounds of formula VI, and / or

[0375] 5-20% by weight of one or more compounds of formula VII, and / or

[0376] 5-30% by weight of one or more compounds of formula VIII, preferably selected from the group of compounds of formula VIII-1 and VIII-2, and / or

[0377] 0-60% by weight of one or more compounds of formula IX

[0378] The proportion of all compounds of formula X, compounds of formula B and compounds of formulae I to IX present in the medium is preferably 95% or greater, more preferably 97% or greater, and most preferably 100%.

[0379] The latter applies to all media according to the present application.

[0380] In another preferred embodiment, the medium according to the invention preferably contains, in addition to the compound of formula X or its preferred subformulae and compounds of formula II and / or III and / or VI and / or VII and / or VIII and / or IX and / or I and / or B, one or more dielectrically neutral compounds selected from the group of compounds of formulae IV and V, preferably in a total concentration in the range 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.

[0381] In a particularly preferred embodiment, the medium according to the invention comprises

[0382] one or more compounds of formula X, the total concentration of which is in the range of 3% or more to 50% or less, preferably in the range of 5% or more to 30% or less, and

[0383] one or more compounds of formula B, the total concentration of which is in the range of 3% or more to 50% or less, preferably in the range of 5% or more to 30% or less, and

[0384] one or more compounds of formula I in a total concentration ranging from 3% or more to 50% or less, preferably ranging from 5% or more to 30% or less, and / or

[0385] One or more compounds of formula II, in a total concentration ranging from 5% or more to 50% or less, preferably ranging from 10% or more to 40% or less, and / or

[0386] One or more compounds of formula VII-1, in a total concentration ranging from 5% or more to 30% or less, and / or

[0387] One or more compounds of formula VII-2, with a total concentration ranging from 3% or more to 30% or less.

[0388] Preferably, the concentration of the compound of formula X in the medium according to the present invention is in the range of 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.

[0389] Preferably, the concentration of the compound of formula B in the medium according to the present invention is in the range of 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.

[0390] Preferably, the concentration of the compound of formula S in the medium according to the present invention is in the range of 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.

[0391] In a preferred embodiment of the present invention, the concentration of the compound of formula I in the medium according to the present invention is in the range of 1% or more to 60% or less, more preferably 5% or more to 40% or less, most preferably 8% or more to 35% or less.

[0392] In a preferred embodiment of the present invention, the concentration of the compound of formula II in the medium is in the range of 3% or more 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.

[0393] In a preferred embodiment of the present invention, the concentration of the compound of formula VII in the medium is in the range of 2% or more 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.

[0394] In a preferred embodiment of the present invention, the concentration of the compound of formula VII-1 in the medium is in the range of 1% or more to 40% or less, more preferably 2% or more to 35% or less, or alternatively 15% or more to 25% or less.

[0395] In a preferred embodiment of the present invention, if present, the concentration of the compound of formula VII-2 in the medium is in the range of 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.

[0396] The invention also relates to an electro-optical display or electro-optical component containing a liquid crystal medium according to the invention, preferably based on the VA, ECB, IPS or FFS effect, preferably an electro-optical display based on the VA, IPS or FFS effect, and in particular those addressed by means of an active matrix addressing device.

[0397] The present invention therefore likewise relates to the use of a liquid-crystalline medium according to the invention in an electro-optical display or in an electro-optical component and to a process for preparing a liquid-crystalline medium according to the invention, characterized in that one or more compounds of the formula B are mixed with one or more compounds of the formula I, preferably with one or more compounds of the sub-formulae I-1 and / or I-2, preferably compounds of the formula I-2 and / or one or more compounds of the formula II, preferably with one or more compounds of the sub-formulae II-1 and / or II-2 and one or more compounds of the formula VII, preferably with one or more compounds of the sub-formulae VII-1 and / or VII-2, particularly preferably with compounds from two or more, preferably from three or more of their different formulae and very preferably from all four of these formulae II-1, II-2, VII-1 and VII-2 and one or more further compounds, preferably selected from the group of compounds of the formulae IV and V, more preferably with one or more compounds of both the formulae IV and V.

[0398] In another preferred embodiment, the medium comprises one or more compounds of the formula IV selected from the group of compounds of the formulae IV-2 and IV-3,

[0399]

[0400] in

[0401] Alkyl and alkyl', independently of one another, represent an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms,

[0402] Alkoxy represents an alkoxy group having 1 to 5 C atoms, preferably 2 to 4 C atoms.

[0403] In a further preferred embodiment, the medium comprises one or more compounds of the formula V selected from the group consisting of the compounds of the formula V-1 and V-2, preferably the compounds of the formula V-1,

[0404]

[0405] wherein the parameters have the meanings given above in formula V, and preferably

[0406] R 51 represents an alkyl group having 1 to 7 C atoms or an alkenyl group having 2 to 7 C atoms, and

[0407] R 52 It represents an alkyl group having 1 to 7 C atoms, an alkenyl group having 2 to 7 C atoms or an alkoxy group having 1 to 6 C atoms, preferably an alkyl group or an alkenyl group, particularly preferably an alkyl group.

[0408] In a further preferred embodiment, the medium comprises one or more compounds of the formula V-1 selected from the group consisting of compounds of the formula V-1a and V-1b,

[0409]

[0410] in

[0411] Alkyl and alkyl', independently of one another, represent an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, and

[0412] Alkenyl is an alkenyl radical having 2 to 7 C atoms, preferably 2 to 5 C atoms.

[0413] Furthermore, the present invention relates to a method for reducing the birefringence wavelength dispersion of a liquid-crystalline medium, said 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 B are used for the medium.

[0414] Besides the compounds of the formulae X, B and I to IX, further constituents may also be present, for example in an amount of up to 45%, but preferably up to 35%, in particular up to 10%, of the mixture as a whole.

[0415] The medium according to the invention may optionally further comprise dielectrically positive components, the total concentration of which is preferably 20% or less, more preferably 10% or less, based on the entire medium.

[0416] In a preferred embodiment, the liquid-crystalline medium according to the invention comprises in total, based on the mixture as a whole:

[0417] 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 the compound of formula X, and / or

[0418] 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 the compound of formula B, and / or

[0419] 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 a compound of formula S, and / or

[0420] 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 the compound of formula I, and / or

[0421] 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 the compound of formula II and / or III, and / or

[0422] 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 the compound of formula IV and / or V, and / or

[0423] 5% or more to 50% or less, 10% or more to 45% or less, preferably 15% or more to 40% or less of the compounds of formula VI and / or VII and / or VIII and / or IX.

[0424] The liquid-crystalline media according to the invention may comprise one or more chiral compounds.

[0425] Particularly preferred embodiments of the present invention satisfy one or more of the following conditions,

[0426] The acronyms (abbreviations) are explained in Tables A to C and illustrated with examples in Table D.

[0427] Preferably, the medium according to the invention satisfies one or more of the following conditions.

[0428] i. The birefringence of the liquid crystal medium is 0.060 or more, particularly preferably 0.070 or more.

[0429] ii. The birefringence of the liquid crystal medium is 0.200 or less, particularly preferably 0.180 or less.

[0430] iii. The birefringence of the liquid crystal medium is in the range of 0.090 or more and 0.160 or less.

[0431] iv. The liquid crystal medium comprises one or more particularly preferred compounds of formula X, preferably selected from (sub)formulae X-1 and X-2, most preferably compounds of (sub)formulae X-1-1 and / or X-2-2 and / or X-2-3 and / or X-2-4 and / or X-2-5.

[0432] v. The liquid-crystalline medium comprises one or more particularly preferred compounds of the formula B, preferably selected from the group consisting of (sub)formulae B-1 and B-2, most preferably compounds of (sub)formula B-2.

[0433] vi. The liquid crystal medium comprises one or more particularly preferred compounds of the formula S, preferably selected from (sub)formula S-1 and formula S-2, most preferably (sub)formula S-2.

[0434] vii. The liquid-crystalline medium comprises one or more particularly preferred compounds of the formula I, preferably selected from (sub)formulae I-1 and I-2, most preferably compounds of (sub)formulae I-2.

[0435] viii. The total concentration of the compounds of formula II in the overall mixture is 25% or more, preferably 30% or more, and preferably in the range of 25% or more to 49% or less, particularly preferably in the range of 29% or more to 47% or less, and very particularly preferably in the range of 37% or more to 44% or less.

[0436] ix. The liquid crystal medium comprises one or more compounds of the formula IV selected from the group of compounds of the following formulae: CC-nV and / or CC-n-Vm and / or CC-VV and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably CC-3-V, preferably in a concentration of up to 60% or less, particularly preferably up to 50% or less; and optionally further CC-3-V1, preferably in a concentration of up to 15% or less; and / or CC-4-V, preferably in a concentration of up to 40% or less, particularly preferably up to 30% or less.

[0437] x. The medium comprises a compound of formula CC-nV, preferably formula CC-3-V, in a concentration of preferably 1% or more to 60% or less, more preferably in a concentration of 3% or more to 35% or less.

[0438] xi. The total concentration of the compound of formula CC-3-V in the overall mixture is preferably 15% or less, preferably 10% or less or 20% or more, preferably 25% or more.

[0439] xii. The total concentration of the compounds of formula Y-nO-Om in the overall mixture is 2% or more to 30% or less, preferably 5% or more to 15% or less.

[0440] xiii. The total concentration of the compound of formula CY-n-Om in the overall mixture is 5% or more to 60% or less, preferably 15% or more to 45% or less.

[0441] xiv. The total concentration of compounds of formula CCY-n-Om and / or CCY-nm, preferably compounds of formula CCY-n-Om in the overall mixture is 5% or more to 40% or less, preferably 1% or more to 25% or less.

[0442] xv. The total concentration of the compound of formula CLY-n-Om in the overall mixture is 5% or more to 40% or less, preferably 10% or more to 30% or less.

[0443] xvi. The liquid crystal medium comprises one or more compounds of the formula IV, preferably of the formula IV-1 and / or IV-2, in a total concentration of preferably 1% or more, in particular 2% or more and very particularly preferably 3% or more to 50% or less, preferably 35% or less.

[0444] xvii. The liquid crystal medium comprises one or more compounds of formula V, preferably formula V-1 and / or V-2, in a total concentration of preferably 1% or more, in particular 2% or more and very particularly preferably 15% or more to 35% or less, preferably to 30% or less.

[0445] xviii. The total concentration of the compound of formula CCP-Vn, preferably CCP-V-1, in the overall mixture is preferably 5% or more to 30% or less, preferably 15% or more to 25% or less.

[0446] xix. The total concentration of the compounds of formula CCP-V2-n, preferably CCP-V2-1, in the overall mixture is preferably 1% or more to 15% or less, preferably 2% or more to 10% or less.

[0447] The invention furthermore relates to an electro-optical display with active-matrix addressing based on the VA, ECB, IPS, FFS or UB-FFS effect, characterised in that it contains a liquid-crystalline medium according to the invention as dielectric.

[0448] The nematic phase range of the liquid-crystal mixture preferably has a width of at least 70 degrees.

[0449] The rotational viscosity γ1 is preferably 350 mPa·s or less, preferably 250 mPa·s or less, and particularly 150 mPa·s or less.

[0450] The mixtures according to the invention are suitable for all IPS and FFS-TFT applications using dielectrically positive liquid-crystalline media, such as SG-FFS.

[0451] The liquid-crystalline media according to the invention preferably consist almost entirely of 4 to 15, in particular 5 to 12 and particularly preferably 10 or fewer compounds. These compounds are preferably selected from the group of compounds of the formulae X, B, I, II, III, IV, V, VI, VII, VIII and IX.

[0452] The liquid-crystalline media according to the invention may optionally also comprise more than 18 compounds. In this case, they preferably comprise from 18 to 25 compounds.

[0453] In a preferred embodiment, the liquid-crystalline media according to the invention predominantly comprise, preferably consist essentially of and most preferably consist almost completely of compounds which do not contain cyano groups.

[0454] In a preferred embodiment, the liquid-crystalline media according to the invention comprise compounds selected from the group of compounds of the formulae X, B, I, II and II, IV and V and VI to IX, preferably selected from the group of compounds of the formulae XA, XB, B-1, B-2, I-1, I-2, II-1, II-2, III-1, III-2, IV, V, VII-1, VII-2, VIII and IX; it preferably consists predominantly of compounds of the said formulae, particularly preferably consists essentially of them and very particularly preferably consists almost entirely of them.

[0455] The liquid-crystalline media according to the invention preferably have a nematic phase in each case at least at -10°C or lower to 70°C or higher, particularly preferably at -20°C or lower to 80°C or higher, very particularly preferably at -30°C or lower to 85°C or higher and most preferably at -40°C or lower to 90°C or higher.

[0456] The expression "having a nematic phase" here means on the one hand that at low temperatures no smectic phase and no crystallization are observed at the corresponding temperature, and on the other hand no clearing occurs on heating from the nematic phase. The investigations at low temperatures are carried out in a flow viscometer at the corresponding temperature and are checked by storage for at least 100 hours in a test cell with a cell thickness corresponding to the electro-optical application. If the storage stability at a temperature of -20°C in a corresponding test cell is 1000 h or more, the medium is considered to be stable at this temperature. At temperatures of -30°C and -40°C, the corresponding times are 500 h and 250 h, respectively. At high temperatures, the clearing point is measured in a capillary by conventional methods.

[0457] In a preferred embodiment, the liquid crystal media according to the invention are characterized by optical anisotropy values ​​in the moderate to low range. The birefringence values ​​are preferably from 0.075 or more to 0.130 or less, particularly preferably from 0.085 or more to 0.120 or less and very particularly preferably from 0.090 or more to 0.115 or less.

[0458] In this embodiment, the liquid-crystalline medium according to the invention has a positive dielectric anisotropy and a relatively high absolute value of the dielectric anisotropy Δε, which is preferably in the range of 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.

[0459] The liquid crystal media according to the invention preferably have relatively low threshold voltage (V0) values ​​in the range from 1.0 V or more to 5.0 V or less, preferably to 2.5 V or less, preferably 1.2 V or more to 2.2 V or less, particularly preferably 1.3 V or more to 2.0 V or less.

[0460] In a further preferred embodiment, the liquid-crystalline media according to the invention preferably have a relatively high average dielectric constant (ε av. ≡(ε ║ +2ε ⊥ ) / 3) value, which is preferably in the range of 8.0 or more to 25.0 or less, preferably 8.5 or more to 20.0 or less, still more preferably 9.0 or more to 19.0 or less, particularly preferably 10.0 or more to 18.0 or less and very particularly preferably 11.0 or more to 16.5 or less.

[0461] Furthermore, the liquid-crystalline media according to the invention have high VHR values ​​in liquid-crystal cells.

[0462] In freshly filled boxes at 20° C., the VHR values ​​of these media in the boxes 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%, and after 5 minutes in an oven at 100° C., in the boxes, 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%.

[0463] In general, liquid-crystal 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.

[0464] These preferred values ​​for the individual physical properties are preferably also maintained in each case by combining the media according to the invention with one another.

[0465] In the present application, the term "compound", also written as "compound(s)", refers to both a single compound and a plurality of compounds, unless otherwise expressly stated.

[0466] In a preferred embodiment, the liquid-crystalline medium according to the invention comprises

[0467] one or more compounds of formula X, and

[0468] one or more compounds of formula B, preferably selected from the group consisting of formulae CB-nF, CB-n-OT, CB-nT, LB-nF, LB-n-OT and LB-nT, more preferably selected from the group consisting of formulae CB-n-OT, CB-nT, LB-n-OT and LB-nT, preferably selected from the group consisting of formulae CB-n-OT, CB-nT, and / or

[0469] one or more compounds of formula I, preferably selected from the group consisting of formula B-nO-Om, B(S)-nO-Om, B-nO-OT, B-nO-T, Bn-OT and BnF, more preferably selected from the group consisting of formula B-nO-OT, B-nO-T, Bn-OT and BnF, and / or

[0470] One or more compounds of formula II, preferably selected from the group consisting of formula PUQU-nF, CDUQU-nF, APUQU-nF and PGUQU-nF, and / or

[0471] One or more compounds of formula III, preferably selected from the group consisting of CCP-n-OT, CGG-nF and CGG-n-OD, and / or

[0472] One or more compounds of formula IV and / or V, preferably selected from the group consisting of formula CC-nV, CCP-nm, CCP-Vn, CCP-V2-n and CGP-nn, and / or

[0473] one or more compounds of formula VI, preferably selected from the group of formulae Yn-Om, Y-nO-Om and / or CY-n-Om, preferably selected from the group of compounds of formulae Y-3-O1, Y-4O-O4, CY-3-O2, CY-3-O4, CY-5-O2 and CY-5-O4, and / or

[0474] Optionally, preferably compulsorily, one or more compounds of the formula VII-1, which are preferably selected from the group of compounds of the formula CCY-nm and CCY-n-Om, preferably of the formula CCY-n-Om, preferably from the group of compounds of the formula CCY-3-O2, CCY-2-O2, CCY-3-O1, CCY-3-O3, CCY-4-O2, CCY-3-O2 and CCY-5-O2, and / or

[0475] Optionally, preferably compulsorily, one or more compounds of formula VII-2, preferably of formula CLY-n-Om, preferably selected from the group of compounds of formula CLY-2-O4, CLY-3-O2, CLY-3-O3, and / or

[0476] One or more compounds of formula VIII, preferably selected from the group consisting of formula CZY-n-On and CCOY-nm, and / or

[0477] one or more compounds of formula IX, preferably selected from the group of formulae PYP-nm, PYP-n-mV1 and PYP-n-mV1, preferably selected from the group of formulae PYP-2-3, PYP-2-4, PYP-2-5, PYP-2-V and PYP-2-2V1, and / or

[0478] One or more compounds selected from the group consisting of formula PGP-nm, PGP-nV, PGP-n-Vm, PGP-n-mV and PGP-n-mVl, preferably selected from the group consisting of formula PGP-2-3, PGP-2-4, PGP-2-5, PGP-1-V, PGP-2-V and PGP-2-2V1, and / or

[0479] Optionally, preferably compulsorily, one or more compounds of the formula IV, preferably selected from the group of compounds of the formulae CC-nV, CC-n-Vm, CC-n-mV1 and CC-nV-Vm, preferably CC-3-V, CC-3-V1, CC-4-V, CC-5-V, CC-3-2V1 and CC-VV, particularly preferably selected from the group of compounds CC-3-V, CC-3-V1, CC-4-V, CC-3-2V1 and CC-VV, very particularly preferably compound CC-3-V, and optionally additionally compounds CC-4-V and / or CC-3-V1 and / or CC-3-2V1 and / or CC-VV, and / or

[0480] Optionally, preferably compulsorily, are one or more compounds of the formula V, preferably selected from the group of formula CCP-V-1 and / or CCP-V2-1.

[0481] In a particularly preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of the formula IX,

[0482] The compounds of the formula IX are also highly suitable as stabilizers in liquid crystal mixtures, especially in the case where p=q=1 and ring A 9 =1,4-phenylene. In particular, they stabilize the VHR of the mixture against UV exposure.

[0483] In a preferred embodiment, the medium according to the invention comprises one or more compounds of the formula IX selected from one or more compounds of the formulae IX-1 to IX-4, very particularly preferably the formulae IX-1 to IX-3,

[0484]

[0485]

[0486] wherein the parameters have the meanings given in formula IX.

[0487] In a further preferred embodiment, the medium comprises one or more compounds of the formula IX-3, preferably the formula IX-3-a,

[0488]

[0489] in

[0490] Alkyl and alkyl', independently of one another, denote an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms.

[0491] In case compounds of formula IX are used in the liquid-crystalline media 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 each (homologous) compound the preferred concentration is 10% or less and more preferably 5% or less.

[0492] For the purposes of the present invention, the following definitions apply to describe the composition of the compositions, unless otherwise indicated in each individual case:

[0493] - "comprising": the concentration of the ingredient in question in the composition is preferably 5% or more, particularly preferably 10% or more, very particularly preferably 20% or more,

[0494] - "essentially consists of": the concentration of the ingredient in question in the composition is preferably 50% or more, particularly preferably 55% or more and very particularly preferably 60% or more,

[0495] - "essentially consists 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

[0496] - "consists essentially entirely of": the concentration of the ingredient in question in the composition is preferably 98% or more, particularly preferably 99% or more and very particularly preferably 100.0%.

[0497] This applies both to the medium as a composition with its constituents (which may be components and compounds) and to the components with its constituents (compounds). Only when it comes to the concentration of the individual compounds relative to the medium as a whole, the term "comprising" means that the concentration of the compound in question is preferably 1% or more, particularly preferably 2% or more, very particularly preferably 4% or more.

[0498] For the present invention, "≤" means less than or equal to, preferably less than, and "≥" means greater than or equal to, preferably greater than.

[0499] For the present invention,

[0500]

[0501] represents trans-1,4-cyclohexylene,

[0502]

[0503] represents a mixture of cis-1,4-cyclohexylene and trans-1,4-cyclohexylene,

[0504] and

[0505] and It represents 1,4-phenylene.

[0506] For the purposes of the present invention, the expression "dielectrically positive compounds" is understood to mean compounds having Δε>1.5, the expression "dielectrically neutral compounds" is understood to mean those for which -1.5≤Δε≤1.5 and the expression "dielectrically negative compounds" is understood to mean those for which Δε<-1.5. The dielectric anisotropy of the compounds is determined here by dissolving 10% of the compound in a liquid-crystalline host and measuring the capacitance of the resulting mixture in each case at 1 kHz in at least one test cell with a homeotropic surface alignment and with a planar surface alignment with a cell thickness of 20 μm. The measuring voltage is generally between 0.5 V and 1.0 V, but is always below the capacitance threshold of the respective liquid-crystalline mixture under investigation.

[0507] The host mixture for dielectrically positive and dielectrically neutral compounds was ZLI-4792 and the host mixture for dielectrically negative compounds was ZLI-2857, both from Merck KGaA, Germany. The value for each compound to be investigated was 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 was dissolved in the host mixture in an amount of 10%. If the solubility of the substance was too low for this purpose, the concentration was halved stepwise until the investigation could be carried out at the desired temperature.

[0508] If necessary, the liquid crystal medium according to the invention may also contain other additives in the usual amounts, such as stabilizers and / or pleochroic dyes, such as dichroic dyes and / or chiral dopants. The amount of these additives used is preferably 0% or more to 10% or less in total, based on the amount of the entire mixture, particularly preferably 0.1% or more to 6% or less. The concentration of each compound used is preferably 0.1% or more to 3% or less. When specifying the concentration and concentration range of the liquid crystal compound in the liquid crystal medium, the concentration of these and similar additives is generally not taken into account.

[0509] In a preferred embodiment, the liquid-crystalline medium according to the invention comprises a polymer precursor comprising one or more reactive compounds, preferably reactive mesogens, and if desired also further comprising other additives in the usual amounts, such as polymerization initiators and / or polymerization moderators. The amount of these additives employed is in the range of 0% or more to 10% or less, preferably 0.1% or more to 2% or less, based on the amount of the entire mixture. The concentrations of these and similar additives are not taken into account when specifying the concentrations and concentration ranges of the liquid-crystalline compounds in the liquid-crystalline medium.

[0510] The composition is composed of a variety 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 a conventional manner. Usually, the desired amount of components used in a smaller amount is dissolved in the components constituting the main component of the mixture. This is advantageously carried out at an elevated temperature. If the selected temperature is higher than the clearing point of the main component, it is particularly easy to observe that the dissolving operation is completed. However, the liquid crystal mixture can also be prepared in other conventional ways, for example using premixing or by a so-called "multi-bottle system".

[0511] The mixtures according to the invention exhibit a very broad nematic phase range with a clearing point of 65° C. or more, very favorable capacitance thresholds, relatively high retention values ​​and very good low-temperature stability at -30° C. and -40° C. Furthermore, the mixtures according to the invention are characterized by a low rotational viscosity γ1.

[0512] It is self-evident to the person skilled in the art that the media according to the invention for VA, IPS, FFS or PALC displays can also comprise compounds in which, for example, H, N, O, Cl, F have been replaced by the corresponding isotopes.

[0513] The structure of the liquid-crystal display according to the invention corresponds to a general geometry, as described, for example, in EP-A 0 240 379.

[0514] The liquid-crystalline phases according to the invention can be modified by means of suitable additives in such a way that they can be used in any type of LCD displays disclosed to date, for example IPS and FFS.

[0515] Table E below indicates possible dopants which can be added to the mixtures according to the invention. If the mixture comprises one or more dopants, it(s) are employed in an amount of 0.01% to 4%, preferably 0.1% to 1.0%.

[0516] For example, stabilizers that can be added to the mixture according to the invention in an amount of preferably 0.01% to 6%, in particular 0.1% to 3%, are shown in Table F below.

[0517] For the purposes of the present invention, unless expressly stated otherwise, all concentrations are expressed as percentages by weight and, unless expressly stated otherwise, all concentrations relate to the respective mixture as a whole or to the components of the mixture also as a whole. Above and below, the term "mixture" describes a liquid-crystalline medium.

[0518] Unless expressly stated otherwise, all temperature values ​​described in this application, such as melting point T(C,N), transition from smectic (S) phase to nematic (N) phase T(S,N) and clearing point T(N,I), are expressed in Celsius (°C) and all temperature differences are expressed in differential degrees (° or degrees), respectively.

[0519] For the purposes of the present invention, the term “threshold voltage” refers to the capacitive threshold ( V0 ), also called Freedericks-threshold, unless expressly stated otherwise.

[0520] 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 to a temperature of 20° C., with Δn measured at 436 nm, 589 nm and 633 nm, and Δε measured at 1 kHz, unless expressly stated otherwise in each case.

[0521] The electro-optical properties, such as the threshold voltage (V0) (capacitive measurement), which is the switching behavior, were measured in a test cell produced by Merck Japan. The cell had a soda-lime glass substrate and was constructed in an ECB or VA configuration with a polyimide alignment layer (with diluent ** 26 of SE-1211 (mixing 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 electrode is 1 cm 2 .

[0522] Unless otherwise stated, no chiral dopants are added to the liquid-crystal mixtures used, but the latter are also particularly suitable for applications in which doping of this type is necessary.

[0523] The rotational viscosity was measured using the rotating permanent magnet method and the flow viscosity was measured 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 ​​measured at 20° C. were 161 mPa·s, 133 mPa·s and 186 mPa·s, respectively, and the flow viscosity values ​​(ν) were 21 mm·s, respectively. 2 ·s -1 , 14mm 2 ·s -1 and 27mm 2 ·s -1 .

[0524] For practical purposes, the dispersion of a material may conveniently be characterized in the following manner, which is used throughout the application unless otherwise expressly stated. The birefringence values ​​are determined at a temperature of 20°C at several fixed wavelengths using a modified Abbe refractometer, with the homeotropically aligned surface in contact with the material on the side of the prism. The birefringence values ​​are determined at specific wavelength values ​​of 436 nm (selected spectral lines 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 damage to the observer's eyes). In the following table, Δn is given at 589 nm and Δ(Δn) is given as Δ(Δn)=Δn(436 nm)-Δn(633 nm).

[0525] Unless explicitly stated otherwise, the following symbols are used:

[0526] V0 threshold voltage, capacitive [V], at 20°C,

[0527] n e The extraordinary refractive index measured at 20°C and 589 nm,

[0528] n o Ordinary refractive index measured at 20°C and 589 nm,

[0529] △n Optical anisotropy measured at 20°C and 589nm,

[0530] λ wavelength λ [nm],

[0531] △n(λ) is the optical anisotropy measured at 20°C and wavelength λ,

[0532] The change in △(△n) optical anisotropy is defined as:

[0533] △n(20℃, 436nm)-△n(20℃, 633nm),

[0534] △(△n*) "Relative change in optical anisotropy", defined as:

[0535] △(△n) / △n(20℃,589nm),

[0536] ε⊥dielectric polarizability perpendicular to the director at 20°C and 1kHz,

[0537] ε || The dielectric polarizability parallel to the director at 20°C and 1kHz,

[0538] Dielectric anisotropy of △ε at 20℃ and 1kHz,

[0539] T(N,I) or clp. clearing point [℃],

[0540] ν Flow viscosity measured at 20°C [mm 2 ·s -1 ],

[0541] γ1 Rotational viscosity measured at 20°C [mPa·s],

[0542] k 11 Elastic constant, "slant" deformation at 20°C [pN],

[0543] k 22 Elastic constant, "twist" deformation at 20°C [pN],

[0544] k 33 Elastic constant, "bending" deformation at 20°C [pN],

[0545] LTS is the low temperature stability of the phase measured in a test cell.

[0546] VHR voltage holding rate,

[0547] The decrease of △VHR voltage holding ratio, and

[0548] S rel The relative stability of VHR, DETAILED DESCRIPTION

[0549] The following examples explain the present invention, but do not limit it. However, they show the preferred mixture concept of the compounds to be preferably adopted and their respective concentrations and their combinations with each other to those skilled in the art. In addition, the examples illustrate the properties and property combinations that can be obtained.

[0550] For the present invention and in the following examples, the structures of the liquid crystal compounds are indicated by abbreviations, which are converted into chemical formulae according to the following Tables A to 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 2lFor straight chain alkyl group or alkylene group, each has n, m and 1 C atom in each case. Preferably, n, m and 1 are 1,2,3,4,5,6 or 7 independently of each other. Table A shows the code of the ring element of the compound core, Table B lists the bridging unit, and Table C lists the symbolic meaning of the left-hand and right-hand end groups of the molecule. The abbreviations are composed of the code of the ring element with optional connecting group, followed by the first hyphen and the left-hand end group code, and the second hyphen and the right-hand end group code. Table D shows the exemplary structure of the compound and their respective abbreviations.

[0551] Table A: Ring elements

[0552]

[0553]

[0554]

[0555] Table B: Bridge Unit

[0556]

[0557] Table C: End Groups

[0558]

[0559]

[0560] Where n and m each represent an integer, and the triple dots "..." are placeholders for other abbreviations from this table.

[0561] In addition to the compound of the formula B, the mixtures according to the invention preferably comprise one or more of the compounds described below.

[0562] The following abbreviations are used:

[0563] (n, m, k and l are each independently an integer, preferably 1 to 9, preferably 1 to 7, k and l may also be 0, and preferably 0 to 4, more preferably 0 or 2, and most preferably 2, n is preferably 1, 2, 3, 4 or 5, in the combination "-nO-" it is preferably 1, 2, 3 or 4, preferably 2 or 4, m is preferably 1, 2, 3, 4 or 5, in the combination "-Om" it is preferably 1, 2, 3 or 4, more preferably 2 or 4. The combination "-lVm" is preferably "2V1".

[0564] Table D

[0565] Exemplary preferred compounds of formula X

[0566]

[0567]

[0568]

[0569] Exemplary preferred having high ε ⊥ Compound of formula B:

[0570]

[0571]

[0572] Exemplary preferred having high ε ⊥ Compounds of formula I:

[0573]

[0574]

[0575]

[0576]

[0577]

[0578] Exemplary Preferred Dielectric Positive Compounds

[0579]

[0580]

[0581]

[0582]

[0583]

[0584]

[0585]

[0586]

[0587]

[0588] Exemplary Preferred Dielectric Neutral Compounds

[0589]

[0590]

[0591]

[0592]

[0593]

[0594]

[0595] Exemplary Preferred Dielectric Negative Compounds

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602]

[0603]

[0604]

[0605] Table E shows chiral dopants which are preferably used in the mixtures according to the invention.

[0606] Table E

[0607]

[0608]

[0609]

[0610] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds selected from the group of compounds in Table E.

[0611] Table F shows stabilizers which can preferably be used in the mixtures according to the invention in addition to the compounds of the formula B. The parameter n here denotes an integer in the range from 1 to 12. In particular, the phenol derivatives shown can be used as additional stabilizers because they act as antioxidants.

[0612] Table F

[0613]

[0614]

[0615]

[0616]

[0617]

[0618]

[0619] In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds selected from the group of compounds of Table F, in particular one or more compounds selected from the group of compounds of the following two formulae

[0620]

[0621] Example

[0622] The following examples illustrate the present invention without limiting it in any way. However, the physical properties make it clear to a person skilled in the art which properties can be achieved and in what range they can be modified. In particular, the person skilled in the art therefore fully defines the combination of various properties that can preferably be achieved.

[0623] The following abbreviations are used in the Synthesis Examples.

[0624] BuLi n-butyllithium

[0625] conc. Concentration

[0626] dist. distillation

[0627] MTB ether tert-butyl methyl ether

[0628] THF Tetrahydrofuran

[0629] Synthesis Example 1

[0630] Synthesis of 1,3-difluoro-4-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-2-(trifluoromethyl)benzene

[0631]

[0632] Step 1.1: 1-[2,4-difluoro-3-(trifluoromethyl)phenyl]-4-(4-propylcyclohexyl)cyclohexanol

[0633]

[0634] BuLi (8.5 mL, 15% in n-hexane, 13.5 mmol) was slowly added to a solution of 1-bromo-2,4-difluoro-3-(trifluoromethyl)benzene (1, CAS 1263377-74-7) (3.4 g, 13.0 mmol) in diethyl ether (50 mL) at -50 °C under nitrogen atmosphere. The mixture was stirred for 1 hour, then a solution of 4-(4-propylcyclohexyl)cyclohexanone (2, CAS 82832-73-3) (3.0 g, 13.5 mmol) in 20 mL of diethyl ether was slowly added. The reaction mixture was stirred for 1 hour, then allowed to warm to room temperature. Throughout this application, unless otherwise explicitly stated, room temperature and ambient temperature are used synonymously and represent a temperature of about 20 °C, typically (20 ± 1 °C). The reaction mixture was quenched with distilled water and hydrochloric acid (2 M). The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with brine, dried (sodium sulfate) and concentrated in vacuo to give 1-[2,4-difluoro-(trifluoromethyl)phenyl]-4-(4-propylcyclohexyl)cyclohexanol (3) as a yellow oil.

[0635] Step 1.2: 1,3-Difluoro-4-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-2-(trifluoromethyl)benzene

[0636]

[0637] A mixture of 1-[2,4-difluoro-3-(trifluoromethyl)phenyl]-4-(4-propylcyclohexyl)cyclohexanol (3) (5.5 g, 11 mmol) and concentrated sulfuric acid (0.1 g, 1.0 mmol) in xylene (mixture of isomers) (40 mL) was heated at reflux temperature in a deanstark trap for 1 hour. It was then cooled to room temperature and the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (solvent: n-heptane). Subsequent recrystallization of the crude product from ethanol produced colorless crystals of 1,3-difluoro-4-[4-(4-propylcyclohexyl)cyclohexene-1-yl]-2-(trifluoromethyl)benzene (4).

[0638] Compound (4) has the following phase characteristics: Tg-68°C K 39°C I.

[0639] Synthesis Example 2

[0640] Synthesis of 1,3-difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethyl)benzene

[0641]

[0642] Step 2.1: 1-(4-Bromophenyl)-4-propyl-cyclohexanol

[0643]

[0644] BuLi (100 mL, 15% in hexanes, 159 mmol) was slowly added to a solution of 1,4-dibromobenzene (1, CAS 106-37-6) (35.0 g, 148 mmol) in diethyl ether (650 mL) under nitrogen at about -50 °C. The mixture was stirred for 1 hour, then a solution of 4-propylcyclohexanone (2, CAS 40649-36-3) (21.0 g, 150 mmol) in 50 mL of diethyl ether was slowly added. The reaction mixture was stirred for 1 hour, then allowed to warm to room temperature. The reaction mixture was 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 1-(4-bromophenyl)-4-propyl-cyclohexanol (3) as a yellow oil.

[0645] Step 2.2: 1-Bromo-4-(4-propylcyclohexen-1-yl)benzene

[0646]

[0647]

[0648] A mixture of 1-(4-bromophenyl)-4-propyl-cyclohexanol (3) (47.2 g, 259 mmol) and toluene-4-sulfonic acid monohydrate (1.5 g, 8.7 mmol) in toluene (500 mL) was heated at reflux temperature in a dean stark trap for 90 minutes. It was then cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent n-heptane / toluene) to give 1-bromo-4-(4-propylcyclohexen-1-yl)benzene (4) as a colorless solid.

[0649] Step 2.3: [4-(4-Propylcyclohexen-1-yl)phenyl]boronic acid

[0650]

[0651] BuLi (74 mL, 15% in n-hexane, 118 mmol) was slowly added to a solution of 1-bromo-4-(4-propylcyclohexene-1-yl)benzene (4) (30.0 g, 107 mmol) in THF (470 mL) at -65 °C under a nitrogen atmosphere. The mixture was stirred for 1 hour, and then a solution of trimethyl borate (5, CAS121-43-7) (12.5 g, 120 mmol) in THF (30 mL) was slowly added. The reaction mixture was stirred for 1 hour, and then it was warmed to 5 °C. The reaction mixture was quenched with distilled water and acidified with hydrochloric acid (2 M). The aqueous phase was separated and extracted with MTB ether. The combined organic phase was washed with brine, dried (sodium sulfate) and concentrated in vacuo.

[0652] The residue was suspended in n-heptane, heated to 50 °C, cooled to 5 °C and filtered in vacuo to give [4-(4-propylcyclohexen-1-yl)phenyl]boronic acid (6) as a colorless solid.

[0653] Step 2.4: 1,3-Difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethyl)benzene

[0654]

[0655] A mixture of [4-(4-propylcyclohexen-1-yl)phenyl]boronic acid (6) (6.4 g, 26 mmol), 1-bromo-2,4-difluoro-3-(trifluoromethyl)benzene (7) (CAS 1263377-74-17 (6.0 g, 23.0 mmol), bis(dibenzylideneacetone)-palladium (0) (15 mg, 26 μmol) and tri-(o-tolyl)phosphine (40 mg, 131 μmol) in acetone (100 mL) was heated to reflux under nitrogen atmosphere, and then sodium hydroxide solution was added dropwise. The mixture was stirred for 2 hours at 4 ℃ for 10 minutes at 4 ℃ for 30 minutes. The mixture was stirred for 2 hours ...

[0656] Compound (8) has the following phase characteristics: K 80℃I.

[0657] Synthesis Example 3

[0658] Synthesis of 1,3-difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethoxy)benzene

[0659]

[0660] Step 3.1: 1,3-Difluoro-4-iodo-2-(trifluoromethoxy)benzene

[0661]

[0662] BuLi (49.0 mL, 1.6 M in n-hexane, 78 mmol) was slowly added to a solution of 1,3-difluoro-2-(trifluoromethoxy)benzene (1) (15.0 g, 76 mmol) in THF (120 mL) at -70 °C under a nitrogen atmosphere. The reaction mixture was stirred at -70 °C for 1 hour. A solution of iodine (CAS 7553-56-2) (19.5 g, 77 mmol) in THF (80 mL) was then slowly added at -70 °C. The reaction mixture was allowed to warm to room temperature after 30 minutes. It was quenched with a diluted aqueous sodium bisulfite solution. 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 pentane) and vacuum distillation to give 1,3-difluoro-2-(trifluoromethoxy)benzene (2) as a colorless oil.

[0663] Step 3.2: 1,3-Difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethoxy)benzene

[0664]

[0665]

[0666] A mixture of [4-(4-propylcyclohexen-1-yl)phenyl]boronic acid (3) (5.9 g, 24 mmol), 1,3-difluoro-4-diiodo-2-(trifluoromethoxy)benzene (2) (8.5 g, 23 mmol), bis(dibenzylideneacetone)-palladium (0) (15 mg, 26 μmol) and tri-(o-tolyl)phosphine (40 mg, 131 μmol) in acetone (100 mL) was heated to reflux under a nitrogen atmosphere, followed by dropwise addition of sodium hydroxide solution (2N, 23 mL, 46 mmol). 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 in vacuo. The residue was purified by silica gel chromatography (solvent heptane). Subsequent recrystallization of the crude product from ethanol and heptane yielded colorless crystals of 1,3-difluoro-4-[4-(4-propylcyclohexen-1-yl)phenyl]-2-(trifluoromethyl)benzene.

[0667] Compound (4) has the following phase characteristics: K 75°C SmA 50°C I.

[0668] Compound Examples

[0669] Embodiment 1: (1)

[0670]

[0671] Phase sequence: T g -76°C K 4I; Δn=0.0220; Δε=3.3.

[0672] Compound Example 2: (2)

[0673]

[0674] Phase sequence: T g -81℃K 8℃I.

[0675] Compound Example 3: (3)

[0676]

[0677] Compound Example 4: (4)

[0678]

[0679] Compound Example 5: (5)

[0680]

[0681] Phase sequence: T g -68℃K 39℃I; Δn=0.0707; Δε=3.8; γ1=217mPa·s.

[0682] Compound Example 6: (6)

[0683]

[0684] Phase sequence: K 38℃N(-4℃)I; Δn=0.0701; Δε=3.9; γ1=251mPa·s.

[0685] Compound Example 7: (7)

[0686]

[0687] Phase sequence: K 59°CI; Δn=0.0951; Δε=4.4; γ1=215mPa·s.

[0688] Compound Example 8: (8)

[0689]

[0690] Phase sequence: K 92℃I; Δn=0.0971; Δε=4.0; γ1=210mPa·s.

[0691] Compound Example 9: (9)

[0692]

[0693] Phase sequence: K 80°CI; Δn=0.1383; Δε=6.0; γ1=275mPa·s.

[0694] Compound Example 10: (10)

[0695]

[0696] Phase sequence: K 75C S A (50°C)I; Δn=0.1363; Δε=5.9; γ1=273mPa·s.

[0697] Example 11: (11)

[0698]

[0699] Phase sequence: K 103C S A (83°C)I; Δn=0.1830; Δε=6.9; γ1=222mPa·s.

[0700] Example 12: (12)

[0701]

[0702] Phase sequence: K 96C S A 101℃I; Δn=0.1810; Δε=6.3; γ1=209mPa·s.

[0703] Example 13: (13)

[0704]

[0705] Phase sequence: K 155℃I.

[0706] Example 14: (14)

[0707]

[0708] Phase sequence: K 123℃I.

[0709] Analogously to the examples described above, the following exemplary compounds of formula X and their corresponding subformulae were obtained:

[0710] In the following tables, the following abbreviations for end groups are used.

[0711]

[0712]

[0713]

[0714]

[0715]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723]

[0724]

[0725]

[0726]

[0727]

[0728]

[0729]

[0730]

[0731]

[0732]

[0733]

[0734]

[0735]

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750]

[0751]

[0752]

[0753]

[0754] Mixture Examples Exemplary mixtures are disclosed below.

[0755] Comparative Example A

[0756] The following mixture (CE-A) was prepared and investigated.

[0757]

[0758]

[0759] Note: tbd: to be determined

[0760] Table 1

[0761]

[0762]

[0763] Note: All extrapolated values ​​at 20℃, *: [mPa·s / pN] and tbd: to be determined

[0764] Table 1 (continued)

[0765]

[0766]

[0767] Note: All extrapolated values ​​and *: [mPa·s / pN] at 20°C.

[0768] Table 1 (continued)

[0769]

[0770] Note: All extrapolated values ​​at 20°C, *: [mPa·s / pN] and

[0771] tbd: to be determined

[0772] Table 1 (continued)

[0773]

[0774] Note: All extrapolated values ​​at 20°C.

[0775] *:[mPa·s / pN] and

[0776] tbd: to be determined

[0777] These mixtures (mixtures A-1 to A-12) have good dielectric ratios (ε ⊥ / △ε), good (γ1 / k 11 ) ratio and is characterized by very good transmittance in FFS displays and exhibits very short response times. In addition, it exhibits excellent deep temperature stability at least up to a temperature of -20°C.

[0778] Example 1

[0779] The following mixture (M-1) was prepared and investigated.

[0780]

[0781] This mixture (Mixture M-1) has a dielectric ratio (ε ⊥ / △ε), 4.71mPa·s / pN (γ1 / k 11 ) ratio, characterized by very good transmittance and good response time in FFS displays and has very good low temperature stability.

[0782] Example 2

[0783] The following mixture (M-2) was prepared and investigated.

[0784]

[0785]

[0786] This mixture (Mixture M-2) has a dielectric ratio (ε ⊥ / △ε)、4.64mPa·s / pN(γ1 / k 11 ) ratio, characterized by very good transmittance in FFS displays and having very good low temperature stability.

[0787] Example 3

[0788] The following mixture (M-3) was prepared and investigated.

[0789]

[0790]

[0791] This mixture (Mixture M-3) has a dielectric ratio (ε ⊥ / △ε), 4.68mPa·s / pN (γ1 / k 11 ) ratio, characterized by very good transmittance and good response time in FFS displays and has very good low temperature stability.

[0792] Example 4

[0793] The following mixture (M-4) was prepared and investigated.

[0794]

[0795]

[0796] Note: tbd: to be determined

[0797] This mixture (Mixture M-4) has a dielectric ratio (ε ⊥ / Δε), is characterized by very good transmittance in FFS displays and has very good low temperature stability.

[0798] Example 5

[0799] The following mixture (M-5) was prepared and investigated.

[0800]

[0801] This mixture (Mixture M-5) has a dielectric ratio (ε ⊥ / △ε), 4.51mPa·s / pN (γ1 / k 11 ) ratio, characterized by very good transmittance in FFS displays and having very good low temperature stability.

[0802] Example 6

[0803] The following mixture (M-6) was prepared and studied.

[0804]

[0805] Note: tbd: to be determined

[0806] The mixture (Mixture M-6) had a dielectric ratio (ε ⊥ / △ε), characterized by very good transmittance in FFS displays and very good low temperature stability.

[0807] Example 7

[0808] The following mixture (M-7) was prepared and studied.

[0809]

[0810] The mixture (Mixture M-7) had a dielectric ratio (ε ⊥ / △ε), 4.40mPa·s / pN ratio (γ1 / k 11 ), characterized by very good transmittance in FFS displays and very good low temperature stability.

[0811] Example 8

[0812] The following mixture (M-8) was prepared and studied.

[0813]

[0814] The mixture (Mixture M-8) had a dielectric ratio (ε⊥ / △ε), 5.21mPa·s / pN ratio (γ1 / k 11 ), characterized by very good transmittance in FFS displays and very good low temperature stability.

[0815] Example 9

[0816] The following mixture (M-9) was prepared and studied.

[0817]

[0818]

[0819] The mixture (Mixture M-9) had a dielectric ratio (ε ⊥ / △ε), 5.40mPa·s / pN ratio (γ1 / k 11 ), characterized by very good transmittance in FFS displays and very good low temperature stability.

[0820] Example 10

[0821] The following mixture (M-10) was prepared and studied.

[0822]

[0823]

[0824] The mixture (Mixture M-10) had a dielectric ratio (ε ⊥ / △ε), 4.44mPa·s / pN ratio (γ1 / k 11 ), characterized by very good transmittance in FFS displays and very good low temperature stability.

[0825] Embodiment 11

[0826] The following mixture (M-11) was prepared and studied.

[0827]

[0828]

[0829] This mixture (mixture M-11) is distinguished by very good transmittance in FFS displays and has very good low-temperature stability.

[0830] Example 12

[0831] The following mixture (M-12) was prepared and studied.

[0832]

[0833]

[0834] This mixture (mixture M-12) features very good transmittance in FFS displays and has very good low-temperature stability.

[0835] Embodiment 13

[0836] The following mixture (M-13) was prepared and studied.

[0837]

[0838]

[0839] This mixture (mixture M-13) is distinguished by very good transmittance in FFS displays and has very good low-temperature stability.

[0840] Embodiment 14

[0841] The following mixture (M-14) was prepared and studied.

[0842]

[0843]

[0844] This mixture (mixture M-14) features very good transmittance in FFS displays and has very good low-temperature stability.

[0845] Embodiment 15

[0846] The following mixture (M-15) was prepared and studied.

[0847]

[0848]

[0849] This mixture (mixture M-15) is distinguished by very good transmittance in FFS displays and has very good low-temperature stability.

[0850] Example 16

[0851] The following mixture (M-16) was prepared and studied.

[0852]

[0853]

[0854] This mixture (mixture M-16) is distinguished by very good transmittance in FFS displays and has very good low-temperature stability.

[0855] Embodiment 17

[0856] The following mixture (M-17) was prepared and studied.

[0857]

[0858]

[0859] This mixture (mixture M-17) is distinguished by very good transmittance in FFS displays and has very good low-temperature stability.

[0860] Embodiment 18

[0861] The following mixture (M-18) was prepared and studied.

[0862]

[0863]

[0864] This mixture (mixture M-18) features very good transmittance in FFS displays and has very good low-temperature stability.

[0865] Embodiment 19

[0866] The following mixture (M-19) was prepared and studied.

[0867]

[0868]

[0869] This mixture (mixture M-19) features very good transmittance in FFS displays and has very good low-temperature stability.

[0870] Embodiment 20

[0871] The following mixture (M-20) was prepared and studied.

[0872]

[0873] This mixture (mixture M-20) is characterized by good properties.

[0874] Embodiment 21

[0875] The following mixture (M-21) was prepared and studied.

[0876]

[0877] This mixture (mixture M-21) is characterized by good properties.

[0878] Embodiment 22

[0879] The following mixture (M-22) was prepared and studied.

[0880]

[0881]

[0882] This mixture (mixture M-22) is characterized by good properties.

[0883] Embodiment 23

[0884] The following mixture (M-23) was prepared and studied.

[0885]

[0886]

[0887] This mixture (mixture M-23) is characterized by good properties.

[0888] Embodiment 24

[0889] The following mixture (M-24) was prepared and studied.

[0890]

[0891] This mixture (mixture M-24) is characterized by good properties.

Claims

1. A liquid crystal medium having a nematic phase and a dielectric anisotropy (Δε) of 0.5 or more, Features It contains one or more compounds of formula X Where n is 0, 1 or 2, R 1X and R 2X independently of one another represent H, alkyl radicals having 1 to 15 C atoms, wherein one or more of these radicals CH 2 The groups can each be substituted independently of one another in such a way that the O atoms are not directly connected to one another by the following groups: -C≡C-, -CF 2 O-、-OCF 2 -、-CH=CH-、 -O-, -CO-O- or -O-CO-, wherein one or more H atoms may be replaced by halogen, and R 2X Alternatively, X X , and represents, identically or differently on each occurrence, a radical selected from the following group: a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and decahydronaphthalene-2,6-diyl, wherein one or more non-adjacent CH 2 The group may be substituted by -O- and / or -S-, and one or more H atoms may be substituted by F, b) the group consisting of 1,4-phenylene and 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which, in addition, one or more H atoms may be replaced by L, c) the group consisting of 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, thiophene-2,5-diyl, selenophene-2,5-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, each of which may be mono- or polysubstituted by L, d) the group consisting of bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl and spiro[3.3]heptane-2,6-diyl, wherein one or more H atoms may be replaced by F, L each, identically or differently, represents halogen, cyano, alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl having 1 to 7 C atoms, in which one or more H atoms may be substituted by F or Cl, Z X represents a single bond, -CF 2 O-、-OCF 2 -、-CH 2 CH 2 -、-CF 2 CF 2 -、-C(O)O-、-OC(O)-、-CH 2 O-、-OCH 2 -, -CF=CH-, -CH=CF-, -CF=CF-, -CH=CH- or -C≡C-, Y 1 Indicates Cl, CF 3 , CHF 2 、OCF 3 , CN or NCS, Y 2 Indicates H, F, Cl, CF 3 or CHF 2 ,and X X Indicates F, Cl, CN, NCS, SF 5 , fluorinated alkyl, alkoxy, alkenyl or alkenyloxy groups each having up to 5 C atoms, and One or more additional compounds.

2. A medium according to claim 1, Features X X Indicates F, CF 3 、OCF 3 or NCS.

3. A medium according to claim 1, Features It comprises one or more compounds of formula B and / or compounds of formula S, in express express n represents 1 or 2, R 1 represents an alkyl group, an alkoxy group, a fluorinated alkyl group, a fluorinated alkoxy group, an alkenyl group, an alkenyloxy group, an alkoxyalkyl group or a fluorinated alkenyl group, and X 1 represents F, Cl, a fluorinated alkyl group, a fluorinated alkenyl group, a fluorinated alkoxy group or a fluorinated alkenyloxy group, in express express n represents 1 or 2, R 1 represents an alkyl group, an alkoxy group, a fluorinated alkyl group, a fluorinated alkoxy group, an alkenyl group, an alkenyloxy group, an alkoxyalkyl group or a fluorinated alkenyl group, and X 1 represents F, Cl, a fluorinated alkyl group, a fluorinated alkenyl group, a fluorinated alkoxy group or a fluorinated alkenyloxy group.

4. A medium according to any one of claims 1 to 3, Features It further comprises one or more compounds of formula I: in express express n represents 0 or 1, R 11 and R 12 independently of one another represent alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, and R 11 Alternatively, R 1 , and R 12 Alternatively, X 1 , R 1 represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl group having 2 to 7 C atoms, and X 1 represents F, Cl, a fluorinated alkyl group, a fluorinated alkenyl group, a fluorinated alkoxy group or a fluorinated alkenyloxy group, The compound of formula B is excluded therefrom.

5. A medium according to any one of claims 1 to 3, Features It comprises one or more compounds selected from the group of compounds of formula II and III: in R 2 represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy group having 1 to 7 C atoms, an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl group having 2 to 7 C atoms, and In each occurrence, they are expressed independently of each other L 21 and L 22 Indicates H or F, X 2 represents halogen, a halogenated alkyl or alkoxy group having 1 to 3 C atoms, or a halogenated alkenyl or alkenyloxy group having 2 or 3 C atoms, m represents 0, 1, 2 or 3, R 3 represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl group having 2 to 7 C atoms, and In each occurrence, independently of each other L 31 and L 32 , independently of each other, represent H or F, X 3 represents halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, F, Cl, -OCF 3 、-OCHF 2 、-O-CH 2 CF 3 、-O-CH=CF 2 、-O-CH=CH 2 or -CF 3 , Z 3 Indicates -CH 2 CH 2 -、-CF 2 CF 2 -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH 2 O- or a single bond, and n represents 0, 1, 2 or 3.

6. A liquid-crystalline medium according to any one of claims 1 to 3, Features It comprises one or more dielectrically neutral compounds selected from the group consisting of formula IV and V: in R 41 and R 42 , independently of each other, have the following formula II with respect to R in claim 5 2 The meaning indicated, and Independent of each other and if Appears twice, These also represent independently of each other Z 41 and Z 42 , independently of each other and if Z 41 appears twice, these also represent independently of each other -CH 2 CH 2 -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH 2 O-、-CF 2 O-, -C≡C- or single bond, p represents 0, 1 or 2, R 51 and R 52 , independently of each other, have 41 and R 42 One of the meanings given to If present, they represent each independently of the other Z 51 To Z 53 Each independently represents -CH 2 -CH 2 -、-CH 2 -O-, -CH=CH-, -C≡C-, -COO- or a single bond, and i and j each independently represent 0 or 1.

7. A liquid-crystalline medium according to claim 6, Features It comprises one or more compounds selected from the group consisting of formulae VI to IX: in R 61 represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkenyl group having 2 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms, R 62 represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms, and l means 0 or 1, R 71 represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, R 72 represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms, express R 81 represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, R 82 represents an unsubstituted alkyl group having 1 to 7 C atoms; an unsubstituted alkoxy group having 1 to 6 C atoms; or an unsubstituted alkenyloxy group having 2 to 6 C atoms, express Z 8 Indicates -(C=O)-O-, -CH 2 -O-, -CF 2 -O- or -CH 2 -CH 2 -, o means 0 or 1, R 91 and R 92 Independently of each other, they have the above 72 The meaning given, express p and q represent 0 or 1 independently of each other.

8. A medium according to any one of claims 1 to 3, Features The total concentration of the compound of formula B in the medium as a whole is 1% or more to 60% or less.

9. A medium according to any one of claims 1 to 3, Features It additionally comprises one or more chiral compounds and / or stabilizers.

10. An electro-optical display or an electro-optical component, Features It comprises a liquid-crystalline medium according to any one of claims 1 to 9.

11. A display according to claim 10, Features It is based on IPS mode or FFS mode.

12. A display according to claim 10 or 11, Features It contains an active matrix addressing device.

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

14. A process for preparing a liquid-crystalline medium according to any one of claims 1 to 9, Features One or more compounds of formula X are mixed with one or more additional mesogenic compounds and optionally one or more additives.

15. A compound of formula X The parameters have the respective meanings given according to formula X in claim 1.

16. A process for preparing a compound of formula X according to claim 15, Features It includes: The block 1-halogen-2-Y 2 -3-Y 1 -4-X-phenyl is reacted with a ketone via a metal-mediated coupling reaction to give a corresponding tertiary alcohol, which is then dehydrated to the corresponding styrene derivative; or wherein a block 1-halogen-2-Y 2 -3-Y 1 -4-X-phenyl reacts with aromatic boronic acid to obtain the corresponding biphenyl derivative, wherein X represents F, Cl, CN, NCS, SF 5 , fluorinated alkyl, alkoxy, alkenyl or alkenyloxy groups each having up to 5 C atoms.

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