Liquid crystal medium

Abstract

To provide a liquid crystal medium.SOLUTION: The present invention relates to liquid-crystalline (LC) media having positive dielectric anisotropy and liquid-crystal displays (LCDs) containing these media, in particular to displays addressed by an active matrix, and in particular to LCDs of the TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, SA-HB-FFS, SA-XB-FFS, polymer-stabilized SA-HB-FFS, polymer-stabilized SA-XB-FFS, positive VA, or positive PS-VA type.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to liquid-crystalline (LC) media with positive dielectric anisotropy and to liquid-crystal displays (LCDs) containing these media, in particular displays addressed by active matrix, and in particular liquid-crystal displays of the TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, PS-HB-FFS, SA-HB-FFS, polymer-stabilized SA-HB-FFS, positive VA or positive PS-VA type. [Background technology]

[0002] Liquid crystal displays (LCDs) are used in many fields to display information. LCDs are used in both direct-view and projection displays. Electro-optical modes used include, for example, twisted nematic (TN), super twisted nematic (STN), optically compensated bend (OCB), and electrically controlled birefringence (ECB) modes, along with their various modifications. All of these modes utilize an electric field generated substantially perpendicular to the substrates and liquid crystal layer.

[0003] In addition to these modes, there is also an electro-optical mode that utilizes an electric field substantially parallel to the substrates and the liquid crystal layer. For example, International Publication No. 91 / 10936 (Patent Document 1) discloses a liquid crystal display in which the electric signal is generated so that the electric field has a component parallel to the liquid crystal layer, which has since become known as an in-plane switching (IPS) display. The operating principle of such a display is described, for example, in RA Soref, Journal of Applied Physics, Vol. 45, No. 12, pp. 5466-5468 (1974) (Non-Patent Document 1).

[0004] IPS displays contain an LC layer between two planarly arranged substrates, with two electrodes located on only one of the substrates, preferably in an interdigitated configuration. When a voltage is applied to the electrodes, an electric field is generated between the electrodes with a significant component parallel to the LC layer, which causes a reorientation of the LC molecules in the plane of the layer.

[0005] EP 0 588 568 A1 discloses, for example, various possibilities for designing electrodes and addressing IPS displays. DE 198 24 137 A1 likewise describes various embodiments of such IPS displays.

[0006] Liquid crystal materials for this type of IPS display are described, for example, in DE 195 28 104 A1.

[0007] Furthermore, so-called "fringe-field switching" (FFS) displays have been reported (see, in particular, SH Jung et al., Jpn. J. Appl. Phys., Vol. 43, No. 3, 2004, p. 1028 (Non-Patent Document 2)), which comprise two electrodes on the same substrate, one of which is structured like a comb and the other unstructured. This generates strong so-called "fringe fields", i.e., a strong electric field near the edge of the electrode and an electric field with both a strong vertical component and a strong horizontal component throughout the cell. FFS displays have a small viewing angle dependence of their contrast. FFS displays typically comprise an LC medium with positive dielectric anisotropy and an alignment layer, usually a polyimide, which provides a planar alignment to the molecules of the LC medium.

[0008] Liquid crystal displays in IPS and FFS electro-optical modes are particularly suitable for use in modern desktop monitors, television sets and multimedia applications, as well as in mobile phones and tablet PCs. The liquid crystal media according to the invention are preferably used in displays of this type. Generally, in FFS displays, dielectrically positive liquid crystal media with rather low values ​​of dielectric anisotropy are used, but in some cases, liquid crystal media with a dielectric anisotropy of only about 3 or less are also used in IPS displays.

[0009] Further improvements have been achieved with the so-called HB-FFS mode, which, in contrast to conventional FFS technology, allows for higher transmission and allows the panel to operate with less energy consumption.

[0010] Liquid crystal compositions suitable for LCDs, particularly FFS and IPS displays, are known, for example, from JP 07-181439 A (Patent Document 5), EP 0 667 555 B (Patent Document 6), EP 0 673 986 B (Patent Document 7), DE 195 09 410 B (Patent Document 8), DE 195 28 106 B (Patent Document 9), DE 195 28 107 B (Patent Document 10), WO 96 / 23 851 B (Patent Document 11), and WO 96 / 28 521 B (Patent Document 12). However, these compositions have certain drawbacks. Among other defects, most of them result in undesirably long address times, have inadequate values ​​of resistivity, and / or require excessively high operating voltages. Improvements are needed in both operating characteristics and shelf life.

[0011] FFS and IPS displays can be operated as active-matrix displays (AMD) or passive-matrix displays (PMD). In the case of active-matrix displays, individual pixels are typically addressed by integrated non-linear active elements such as thin-film transistors (TFT), while in the case of passive-matrix displays, individual pixels are typically addressed by multiplexing methods as known from the prior art.

[0012] Displays according to the invention are preferably addressed with an active matrix, preferably a TFT matrix, but the liquid crystals according to the invention can also be used to advantage in displays with other known addressing means.

[0013] Both IPS and FFS technologies have certain advantages over other LCD technologies, such as vertical alignment (VA) technologies, such as a wide viewing angle dependence of contrast.

[0014] The provision of further liquid crystal media and their use in displays with high transmittance, good black state and high contrast ratio is a central issue for modern FFS and IPS applications. In addition, modern applications also require good low temperature stability and fast addressing times. Contrast can be improved by increasing the transmittance in the bright state and improving the dark state. One solution to improve the dark state is to use K Avg. The solution is to develop liquid crystal mixtures with high scattering parameters to lower the scattering parameters, but this usually comes at the expense of slower response times.

[0015] In displays such as those in the HB-FFS mode, the liquid crystal molecules have a positive dielectric anisotropy, and the dielectric constant ε ⊥ It was observed that high brightness can be achieved by using a liquid crystal medium with an increased ε ⊥ This can be achieved by adding a limited amount of a liquid crystal compound with negative dielectric anisotropy to the liquid crystal medium, while maintaining the positive dielectric anisotropy of the entire medium. ⊥ The addition of a compound having the formula (I) has some drawbacks. For example, this can increase the value of the rotational viscosity γ1, which can result in a higher value of the ratio γ1 / K2 of the rotational viscosity γ1 and the elastic constant K2 of the torsional deformation, resulting in a longer response time. 22 Since is approximately proportional to the elastic constant K1 of the splay deformation (the value of K2 is typically about half the value of K1), it can be easily determined by measuring γ1 and K1.

[0016] Another drawback is that the reliability (VHR) of HB-FFS mixtures is inferior to that of conventional FFS mixtures.

[0017] It is also important to maintain good low-temperature stability (LTS) of the media. In particular, car navigation systems require good LTS even at -40°C. This requirement makes it difficult to further improve optical performance. [Prior art documents] [Patent documents]

[0018] [Patent Document 1] International Publication No. 91 / 10936 [Patent Document 2] European Patent No. 0 588 568 [Patent Document 3] DE 198 24 137 A1 [Patent Document 4] DE 195 28 104 A1 [Patent Document 5] Japanese Patent Application Publication No. 07-181439 [Patent Document 6] European Patent No. 0 667 555 [Patent Document 7] European Patent No. 0 673 986 [Patent Document 8] German Patent No. 195 09 410 [Patent Document 9] German Patent No. 195 28 106 [Patent Document 10] German Patent No. 195 28 107 [Patent Document 11] WO 96 / 23 851 [Patent Document 12] WO 96 / 28 521 [Non-patent literature]

[0019] [Non-Patent Document 1] RA Soref, Journal of Applied Physics, Vol. 45, No. 12, pp. 5466-5468 (1974) [Non-patent document 2] SHJung et al., Jpn.J.Appl.Phys., Volume 43, No. 3, 2004, Page 1028 Summary of the Invention [Problem to be solved by the invention]

[0020] The present invention has the object of providing new compounds and liquid-crystalline media, preferably for FFS and IPS displays, in particular for HB-FFS displays, but also for TN, positive VA or STN displays, in particular for active matrix displays such as those addressed by TFT, which do not exhibit the disadvantages indicated above or exhibit them only to a lesser extent, and in particular enable displays with improved contrast without degrading other display parameters. [Means for solving the problem]

[0021] To achieve the above object, the present invention provides a compound of formula I and a liquid-crystalline medium comprising a compound of formula I.

[0022] Advantageous embodiments of the invention are the subject matter of the dependent claims and can also be seen from the description. DETAILED DESCRIPTION OF THE INVENTION

[0023] The present invention relates to compounds of formula I:

[0024] [ka]

[0025] During the ceremony, R 11 and R 12 are the same or different and represent H, linear alkyl or alkoxy having 1 to 15 C atoms, linear alkenyl or alkenyloxy having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl, alkenyloxy, respectively, having 3 to 15 C atoms, provided that one or more CH groups in these groups are not directly linked to O atoms, [ka] -CH=CH-, -C≡C-, -CF2O-, -OCF2-, -O-, -CO-O- or -O-CO-, each of which may be replaced independently of the other, provided that one or more H atoms may be replaced by halogen; L 11 , L 12 , L 13 , L 14 are the same or different and represent H, F, Cl, CH3, CF3 or CHF2, provided that L 11 , L 12 , L 13 , L 14 At least one of represents F, Cl, CH3, CF3 or CHF2.

[0026] The present invention further provides a) one or more compounds of formula I and preferably b) relates to a liquid-crystalline medium with positive dielectric anisotropy which comprises one or more compounds selected from the group of compounds of the formulae II and III

[0027] [ka]

[0028] During the ceremony, R 2 and R 3 is R 11 has the meaning given above and preferably denotes alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms, [ka] are, independently of each other, [ka] represents L 21 , L 22 , L 31 and L 32 each independently represents H or F, Y 2 and Y 3are the same or different and represent H or CH, preferably H; X 2 and X 3 each independently represent a halogen, a halogenated alkyl or alkoxy having 1 to 3 C atoms or a halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, preferably F, Cl, CF3, OCF3 or OCHF2, more preferably F or OCF3, Z 3 represents -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CHO- or a single bond, preferably a single bond, and l, m, n and o are each independently 0 or 1.

[0029] The compounds of formula I, preferably in combination with compounds of formula II and / or formula III, enable liquid crystal media exhibiting low rotational viscosity and low values ​​of the ratios γ1 / K2 and γ1 / K1. This enables liquid crystal displays, particularly in IPS and FFS modes, to have high brightness and transmittance and fast response times. In addition, higher mean elastic constants (K) are achieved while maintaining other relevant physical properties. av ) can be achieved, leading to a lower scattering parameter and improving the dark state of the display and thus the contrast.

[0030] In particular, the low-temperature stability (LTS) of the medium according to the present invention is remarkably high. The medium is sufficiently stable even at temperatures as low as -40°C, making it particularly suitable for mobile applications such as automobile applications.

[0031] The liquid-crystalline media according to the invention are suitable for mobile applications and TFT applications, such as, for example, mobile phones and PDAs. Furthermore, the liquid-crystalline media according to the invention are particularly suitable for FSSHB-FFS and IPS displays based on dielectrically positive liquid crystals.

[0032] The liquid-crystalline media according to the invention are likewise intended for large-screen television applications and are suitable for use in liquid-crystal displays of the FFS, HB-FFS and IPS mode based on dielectrically positive liquid crystals and their polymer-stabilized modifications.

[0033] The present invention further relates to the use of liquid-crystalline media as described above and below for electro-optical purposes, in particular in liquid crystal displays, shutter glasses, LC windows, 3D applications, preferably in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, PS-HB-FFS, SA-HB-FFS, polymer-stabilized SA-HB-FFS, positive VA and positive PS-VA displays, very preferably FFS, HB-FFS, IPS, PS-HB-FFS and PS-IPS displays.

[0034] The present invention further relates to electro-optical liquid crystal displays comprising a liquid crystal medium as described above and below, in particular TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, PS-HB-FFS, SA-HB-FFS, polymer-stabilized SA-HB-FFS, positive VA or positive PS-VA displays, preferably FFS, HB-FFS, IPS, PS-HB-FFS or PS-IPS displays.

[0035] According to another aspect of the present invention, there is provided a compound of formula (3), as defined below in Scheme 1. A preferred synthetic route to compounds of formula I is shown in Scheme 1.

[0036] [ka]

[0037] wherein X represents Br or I, and the other radicals occurring have the meanings given above.

[0038] In this specification, alkyl and / or alkoxy groups are understood to mean linear, branched or cyclic alkyl, which is preferably linear and has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.

[0039] In this specification, branched alkyl is preferably isopropyl, s-butyl, isobutyl, isopentyl, 2-methylbutyl, 2-methylhexyl or 2-ethylhexyl.

[0040] As used herein, cyclic alkyl is understood to mean a linear or branched alkyl or alkenyl having up to 12 C atoms, preferably an alkyl having 1 to 7 C atoms, in which the group CH2 is replaced by a carbocyclic ring having 3 to 5 C atoms, very preferably selected from the group consisting of cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl and cyclopentenylalkyl, in which alkyl is a linear alkyl having 1 to 5 C atoms.

[0041] In this context, oxaalkyl preferably denotes straight-chain 2-oxapropyl (= methoxymethyl), 2- (= ethoxymethyl) or 3-oxabutyl (= 2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.

[0042] In this specification, alkenyl, i.e. an alkyl group in which one CH2 group is replaced by -CH=CH-, may be linear or branched. It is preferably linear and has 2 to 10 C atoms. It therefore stands in particular for vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, oct-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, non-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, dec-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or -9-enyl.

[0043] As used herein, alkyl or alkenyl groups that are at least monosubstituted with a halogen are preferably linear, and the halogen is preferably F or Cl. In the case of polysubstitution, the halogen is preferably F. The resulting group also includes perfluoro groups. In the case of monosubstitution, the fluorine or chlorine substituent may be in any desired position, but is preferably in the ω-position.

[0044] In this context, a monofluorinated or polyfluorinated alkyl or alkoxy group having 1, 2 or 3 C atoms or a monofluorinated or polyfluorinated alkenyl group having 2 or 3 C atoms is particularly preferably F, Cl, CF3, CHF2, OCF3, OCHF2, OCFHCF3, OCFHCHF2, OCFHCHF2, OCF2CH3, OCF2CHF2, OCF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCF2CF2CF2CHF2, OCFHCF2CF3, OCFHCF2CHF2, OCF2CF2CF3, OCF2CF2CClF2, OCClFCF2CF3, OCH=CF2 or CH=CF2, very particularly preferably F or OCF3, also CF3, OCF=CF2, OCHF2 or OCH=CF2.

[0045] In compounds of formula I, the group L 11 , L12 , L 13 and L 14 Preferably one or two, more preferably one of the groups represents F, and the remaining groups L 11 , L 12 , L 13 , L 14 represents H.

[0046] The compound of formula I is preferably selected from the compounds of formulae I-1 to I-6, more preferably from the compounds of formulae I-1 to I-4, and very preferably from the compounds of formulae I-1 and I-2, in particular from the compounds of formula I-1.

[0047] [ka]

[0048] In the formula, R 11 and R 12 has the meaning defined above in formula I, preferably a straight-chain alkyl or alkoxy having 1 to 9 C atoms or a straight-chain alkenyl having 2 to 9 C atoms, respectively, with the proviso that one or more CH groups in these groups [ka] which may each be replaced independently of one another.) and very preferably represents straight-chain alkyl having 1 to 7 C atoms or straight-chain alkenyl having 1 to 7 C atoms.

[0049] The medium according to the invention particularly preferably comprises one or more compounds of the formula I-1, preferably selected from the compounds of the formulae I-1-1 to I-1-23.

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] In the formula, R 12 has the meaning given above for formula I and its sub-formulas and preferably denotes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octyloxy, n-nonyloxy, but-3-en-1-yl, trans-pent-3-en-1-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclopropylmethoxy, cyclopentyloxy or cyclopentylmethoxy.

[0055] Preferably, the medium comprises one or more compounds of formula II, preferably selected from the group of compounds of formulae II-1 to II-3, very preferably selected from the group of compounds of formulae II-1 and II-3.

[0056] [ka]

[0057] In the formula, the occurring groups have the respective meanings given in formula II above, and in formula II-1, the group L 23 and L 24 are each independently H or F, and in formula II-1, preferably [ka] Represents.

[0058] In formulas II-1, II-2 and II-3, L 21 and L 22 or L 23 and L 24 Preferably, both represent F.

[0059] In another preferred embodiment of formula II-1 and II-2, L 21 , L 22 , L 23 and L 24 All represent F.

[0060] The compound of formula II-1 is preferably selected from the group of compounds of formulae II-1a to II-1h:

[0061] [ka]

[0062] [ka]

[0063] In the formulae, the occurring radicals have the respective meanings given above.

[0064] In a preferred embodiment of the present invention, the medium is L 21 and L 22 and / or L 23 and L 24 and R are each independently one or more compounds selected from the group of compounds of formulae II-1a to II-1h, wherein R and R are both F.

[0065] In another preferred embodiment, the medium is L 21 , L 22 , L 23 and L 24 and n is 0 or 1. The present invention also includes compounds selected from the group of compounds of formulae II-1a to II-1h, wherein all are F.

[0066] Particularly preferred are compounds of formula II-1.

[0067] [ka]

[0068] In the formula, R 2 has the meaning given above.

[0069] Preferably, the compound of formula II-2 is selected from the group of compounds of formulae II-2a to II-2c:

[0070] [ka]

[0071] In the formula, the occurring radicals have the respective meanings given above, preferably L 21 and L 22 are both F.

[0072] Preferably, the compound of formula II-3 is selected from the group of compounds of formulae II-3a to II-3e:

[0073] [ka]

[0074] In the formula, the occurring radicals have the respective meanings given above, preferably L 21 and L 22 are both F and L 23 and L 24 are both H, or L 21 , L 22 , L 23 and L 24 are all F.

[0075] Particularly preferred are compounds of formula II-3.

[0076] [ka]

[0077] In the formula, R 2 has the meaning given above.

[0078] In addition to the preferred compounds of formula II above, the medium may contain one or more compounds of formula II selected from the compounds of formulae IIA1 to IIA7.

[0079] [ka]

[0080] In the formula, R 2 and X 2 has the meaning given in formula II or one of the preferred meanings given above and below.

[0081] Preferred compounds are of formula IIA1, IIA2 and IIA3, very preferably of formula IIA1 and IIA2.

[0082] In the compounds of formula IIA1 to IIA7, R 2 preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or n-propyl, and X 2 preferably represents F or OCF3, very preferably F.

[0083] In another preferred embodiment of the present invention, the medium comprises one or more compounds of formula III, preferably selected from the group of formulae III-1 and III-2, preferably formula III-2.

[0084] [ka]

[0085] wherein the occurring groups and parameters have the respective meanings given in Formula III above.

[0086] R 3preferably represents alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms.

[0087] Preferably, the compound of formula III-1 is selected from the group of compounds of formula III-1a and III-1b:

[0088] [ka]

[0089] wherein the occurring groups have the respective meanings given above, and L 33 and L 34 each independently represents H or F.

[0090] The compound of formula III-1a is preferably selected from the group of compounds of formulae III-1a-1 to III-1a-6:

[0091] [ka]

[0092] In the formula, R 3 has the meaning given above.

[0093] Preferably, the compound of formula III-2 is selected from the group of compounds of formulae III-2a to III-2n:

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] wherein the occurring groups have the respective meanings given above, and L 35 and L 36 are each independently H or F.

[0098] Preferably, the compound of formula II-2a is selected from the group of compounds of formulae III-2a-1 to III-2a-4:

[0099] [ka]

[0100] In the formula, R 3 has the meaning given above.

[0101] The compounds of formula III-2b are preferably selected from the group of compounds of formula III-2b-1 and III-2b-2, preferably III-2b-2.

[0102] [ka]

[0103] In the formula, R 3 has the meaning given above.

[0104] The compound of formula II-2c is preferably selected from the group of compounds of formulae III-2c-1 to III-2c-5:

[0105] [ka]

[0106] In the formula, R 3 has the meaning given above.

[0107] The compounds of the formulae III-2d and III-2e are preferably selected from the group of the compounds of the formulae III-2d-1 and III-2e-1:

[0108] [ka]

[0109] In the formula, R 3 has the meaning given above.

[0110] The compound of formula III-2f is preferably selected from the group of compounds of formulae III-2f-1 to III-2f-7:

[0111] [ka]

[0112] In the formula, R 3 has the meaning given above.

[0113] The compound of formula III-2g is preferably selected from the group of compounds of formulae III-2g-1 to III-2g-7:

[0114] [ka]

[0115] In the formula, R 3 has the meaning given above.

[0116] The compound of formula III-2h is preferably selected from the group of compounds of formulae III-2h-1 to III-2h-5:

[0117] [ka]

[0118] In the formula, R 3 has the meaning given above.

[0119] The compound of formula III-2i is preferably selected from the group of compounds of formulae III-2i-1 to III-2i-3:

[0120] [ka]

[0121] In the formula, R 3 has the meaning given above.

[0122] The compound of formula III-2j is preferably selected from the group of compounds of formulae III-2j-1 to III-2j-3:

[0123] [ka]

[0124] In the formula, R 3 has the meaning given above.

[0125] The compound of formula III-2k is preferably selected from the group of compounds of formulae III-2k-1 to III-2k-6:

[0126] [ka]

[0127] In the formula, R 3 has the meaning given above.

[0128] The compound of formula III-2l is preferably selected from the group of compounds of formulae III-2l-1 to III-2l-6:

[0129] [ka]

[0130] In the formula, R 3 has the meaning given above.

[0131] The compounds of formula III-2m are preferably selected from the compounds of formula III-2m-1:

[0132] [ka]

[0133] In the formula, R 3 has the meaning given above.

[0134] The compounds of formula III-2n are preferably selected from the compounds of formula III-2n-1.

[0135] [ka]

[0136] In the formula, R 3 has the meaning given above.

[0137] Alternatively, 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, preferably III-3a.

[0138] [ka]

[0139] wherein the groups and parameters have the respective meanings given in Formula III above.

[0140] [ka]

[0141] In the formula, R 3 has the meaning given above.

[0142] In addition to the preferred compounds of formula III above, the medium may comprise one or more compounds selected from the group consisting of formulae IIIA-1 to IIIA-21.

[0143] [ka]

[0144] [ka]

[0145] [ka]

[0146] [ka]

[0147] In the formula, R 3 and X 3 has the meaning given in formula III or one of the preferred meanings given above and below. Preferred compounds are those of formulae IIIA1, IIIA4, IIIA6, IIIA16, IIIA19 and IIIA20

[0148] In the compounds of formula IIIA1 to IIIA21, R 3 preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, and X 3 preferably represents F or OCF3, very preferably F.

[0149] Preferably, the medium according to the invention comprises one or more compounds of formula IV.

[0150] [ka]

[0151] During the ceremony, R 11represents a linear alkyl or alkoxy group having 1 to 12 C atoms, or a branched or cyclic alkyl group having 3 to 12 C atoms, or a linear alkenyl group having 2 to 12 C atoms, or a branched alkenyl group having 3 to 12 C atoms, or a cyclic alkenyl group having 5 to 12 C atoms, whereby one or more H atoms may be replaced by fluorine, preferably a linear alkyl group having 1 to 12 C atoms, very preferably having 1 to 7 C atoms, R 12 represents a linear alkyl or alkoxy group having 1 to 12 C atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 12 C atoms, or a linear alkenyl group having 2 to 12 C atoms, or a branched alkenyl group having 3 to 12 C atoms, or a cyclic alkenyl group having 5 to 12 C atoms (wherein one or more H atoms may be replaced by fluorine), preferably a linear alkenyl group having 2 to 12 C atoms, very preferably having 2 to 7 C atoms.

[0152] The compounds of formula IV are preferably selected from the group of compounds of formulae IV-1 to IV-4, very preferably of formula IV-3.

[0153] [ka]

[0154] During the ceremony, alkyl and alkyl' independently denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, alkoxy represents alkoxy having 1 to 5 C atoms, preferably 2 to 4 C atoms, alkenyl represents an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 C atoms, Alkenyl' denotes an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 to 3 C atoms.

[0155] Preferably, the medium comprises one or more compounds of formula IV-1, preferably selected from the compounds of formulae IV-1-1 to IV-1-6.

[0156] [ka]

[0157] Preferably, the medium according to the invention comprises one or more compounds of formula IV-2-1 and / or IV-2-2.

[0158] [ka]

[0159] Preferably, the medium according to the invention comprises a compound of the formula IV-3, very preferably selected from the compounds of the formulae IV-3-1 to IV-3-6, in particular the compounds of the formulae IV-3-2 and / or IV-3-6.

[0160] [ka]

[0161] Preferably, the medium according to the invention comprises a compound of formula IV-4, in particular selected from the compounds of formulae IV-4-1 and IV-4-2:

[0162] [ka]

[0163] Preferably, the medium according to the invention comprises one or more compounds of formula IVa and / or IVb, very preferably IVb.

[0164] [ka]

[0165] During the ceremony R 41 and R 42 each independently represent a straight-chain alkyl, alkoxy, alkenyl, alkoxyalkyl or alkenyloxy group having up to 12 C atoms, and [ka] represents Z 4 represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8- or -CF=CF-.

[0166] Preferred compounds of formula IVa are selected from compounds of formulae IVa-1 to IVa-4:

[0167] [ka]

[0168] During the ceremony Alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms.

[0169] The medium according to the invention preferably comprises at least one compound of formula IVa-2.

[0170] Preferred compounds of formula IVb are selected from compounds of formulae IVb-1 to IVb-3:

[0171] [ka]

[0172] During the ceremony Alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl *each independently represents a linear alkenyl group having 2 to 6 carbon atoms.

[0173] Among the compounds of formulae IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0174] Very particularly preferred compounds of formula IVb are selected from the following compounds:

[0175] [ka]

[0176] The medium according to the invention particularly preferably comprises the compound IVb-2-3.

[0177] In a preferred embodiment, the medium according to the invention comprises one or more compounds of formula V:

[0178] [ka]

[0179] During the ceremony, R 51 , R 52 represents alkyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms or alkoxyalkyl having 2 to 7 C atoms, alkenyl or alkenyloxy, [ka] represents Z 51 , Z 52 each independently represent -CH-CH-, -CH-O-, -CH=CH-, -C≡C-, -COO- or a single bond, and n is 1 or 2, However, compounds of formula I and CL are excluded from formula V.

[0180] The compound of formula V is preferably selected from the compounds of formula V-1, V-2, V-3 and V-4.

[0181] [ka]

[0182] wherein the occurring radicals have the meanings given above in formula V.

[0183] The compound of formula V-1 is preferably selected from the compounds of formulae V1-1 to V1-8.

[0184] The compound of formula V-2 is preferably selected from the compounds of formulae V2-1 to V2-4.

[0185] The compound of formula V-3 is preferably selected from the compounds of formulae V3-1 to V3-5.

[0186] [ka]

[0187] [ka]

[0188] [ka]

[0189] In the formula, R 51 and R 52 has the meaning given above in formula V. 51 and R 52 preferably each independently represent straight-chain alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms.

[0190] Highly preferred compounds of formula V-2-1 are selected from the compounds of formulae V-2-1a to V-2-1g:

[0191] [ka]

[0192] [ka]

[0193] Highly preferred compounds of formula V-2-2 are selected from the compounds of formulae V-2-2a to V-2-2i:

[0194] [ka]

[0195] [ka]

[0196] A preferred medium according to the invention comprises one or more compounds of formula CL.

[0197] [ka]

[0198] During the ceremony R L represents H, a linear or branched alkyl or alkoxy group having 1 to 15 C atoms, or a linear or branched alkenyl group having 2 to 15 C atoms, provided that one or more CH groups in these groups are not directly linked to O atoms, [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO-, each of which may be replaced independently of the other, in which additionally one or more H atoms may be replaced by halogen; X Lrepresents F, Cl, CN, CHF2, CF3, OCF3, or the same or different R L has one of the meanings of Y L represents H, F, Cl or CH3.

[0199] The compound of formula CL is preferably selected from the group of compounds of formula CL-1, CL-2 and CL-3.

[0200] [ka]

[0201] During the ceremony, R L1 and R L2 are identical or different and have the meaning given above in formula I, preferably denote alkyl or alkenyl having 1 to 7 or 2 to 7 C atoms, respectively, in which the CH groups may be replaced by cyclopropane-1,2-diyl, or R L2 represents alkoxy having 1 to 5 C atoms.

[0202] Highly preferred compounds of formula CL are selected from compounds of formulae CL-3-1 to CL-3-12:

[0203] [ka]

[0204] [ka]

[0205] In a particularly preferred embodiment, the medium according to the invention comprises the compound CL-3-1 or CLP-3-3.

[0206] In a preferred embodiment of the invention, the medium additionally comprises one or more compounds of formulae VI-1 to VI-9.

[0207] [ka]

[0208] [ka]

[0209] During the ceremony, R 6 are each independently of one another in claim 1. 1 and Each w independently represents an integer of 1 to 6.

[0210] In a preferred embodiment of the invention, the medium additionally comprises one or more compounds of formula VII.

[0211] [ka]

[0212] During the ceremony, R 71 and R 72 represents H, F, linear alkyl or alkoxy having 1 to 15 C atoms, linear alkenyl or alkenyloxy having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy, respectively, having 3 to 15 C atoms, provided that in these groups one or more CH2 groups are each independently of one another such that O atoms are not directly linked to one another [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO-, provided that one or more H atoms may be replaced by halogen; X 71 ~X 76 are the same or different and represent H or F, preferably X 71 ~X 76At least one of X represents F, more preferably X 71 ~X 76 at least two of which represent F; Z 71 and Z 72 are the same or different and represent CH2CH2 or a single bond.

[0213] The compound of formula VII is preferably selected from formulae VII-1 and VII-2.

[0214] [ka]

[0215] wherein the occurring radicals have the meanings given in formula VII.

[0216] The compounds of formula VII-1 are preferably selected from formulae VII-1-1 to VII-1-21, very preferably from formula VII-1-4.

[0217] [ka]

[0218] [ka]

[0219] [ka]

[0220] [ka]

[0221] In the formula, R 7 represents a linear alkyl or alkoxy group having 1 to 6 C atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5 or 6, and n is 0, 1, 2, 3 or 4. R7 preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.

[0222] In the compounds of formula VII-1-4, (O) preferably represents —O—.

[0223] In Formula VII-1-22, R 7 preferably represents n-propyl.

[0224] The compounds of formula VII-2 are preferably selected from formulae VII-2-1 to VII-1-15, very preferably from formula VII-2-1.

[0225] [ka]

[0226] [ka]

[0227] [ka]

[0228] During the ceremony, R 7 represents a linear alkyl or alkoxy group having 1 to 6 C atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5 or 6, and n is 0, 1, 2, 3 or 4. R 7 preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.

[0229] Preferably, the medium according to the invention comprises one or more compounds of formula VIII.

[0230] [ka]

[0231] During the ceremony, R 81 and R 82 are the same or different and represent H, halogen, CN, SCN, linear alkyl or alkoxy having 1 to 15 C atoms, linear alkenyl or alkenyloxy having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 C atoms, provided that one or more CH2 groups in these groups are not directly linked to O atoms, [ka] each independently being replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO-, in which one or more H atoms may be replaced by halogen; A 0 , A 81 and A 82 are each independently phenylene-1,4-diyl (in which one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2 or OCF3), cyclohexane-1,4-diyl (in which one or two non-adjacent CH2 groups may be replaced independently by O and / or S and one or more H atoms may be replaced by F), cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl; Z 81 and Z 82represent, independently of one another, -CF2O-, -OCF2-, -C2O-, -OCH2-, -CO-O-, -O-CO-, -C2H4-, -C2F4-, -CF2CH2-, -CH2CF2-, -CFHCFH-, -CFHCH2-, -CH2CFH-, -CF2CFH-, -CFHCF2-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C- or a single bond; n represents 0, 1, 2 or 3, preferably 0, 1 or 2, very preferably 0 or 1, particularly preferably 0; and m represents 0, 1, 2 or 3, preferably 0, 1 or 2, very preferably 1 or 2, in particular 1, However, compounds of formula I are excluded from formula VIII.

[0232] A in Formula I 81 and A 81 preferably denotes phenylene-1,4-diyl (which may also be mono- or polysubstituted by F), furthermore cyclohexane-1,4-diyl, cyclohexenylene-1,4-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, very preferably phenylene-1,4-diyl (which may also be mono- or polysubstituted by F) or cyclohexane-1,4-diyl.

[0233] Z in Formula I 81 and Z 81 preferably represents -CF2O-, -OCF2- or a single bond, very preferably a single bond.

[0234] A in Formula I 81 and A 81 is particularly preferably [ka] wherein L represents halogen, CF3 or CN, preferably F.

[0235] R 81 and R 82Further preferred are compounds of formula VIII, in which each independently of one another denotes H, F or alkyl, alkoxy, alkenyl or alkynyl having 1 to 8, preferably 1 to 5, C atoms, each of which may be replaced by halogen, in particular F.

[0236] R 81 and R 82 preferably represents H, optionally fluorinated alkyl or alkoxy having 1 to 7 C atoms, optionally fluorinated alkenyl or alkynyl having 2 to 7 C atoms, optionally fluorinated cycloalkyl having 3 to 12 C atoms.

[0237] Preferably R 81 and R 82 At least one of these is not H, and particularly preferably R 81 and R 82 Both of these are not H. 81 is very particularly preferably alkyl. 82 is more preferably H, alkyl or fluorine. Very particularly preferably R 81 is alkyl, and R 82 is H or alkyl. R 81 , R 82 R each independently very particularly preferably denotes unbranched alkyl having 1 to 5 C atoms. 81 and R 82 represents a substituted alkyl, alkoxy, alkenyl or alkynyl, two groups R 81 and R 82 The total number of C atoms in is preferably less than 10.

[0238] Preferred compounds of formula VIII are selected from the following sub-formulae, more preferably from compounds of formula VIII-3:

[0239] [ka]

[0240] In the formula, R81 and R 82 has the meaning given above, L represents F, and r, s and t are independently 0, 1, 2, 3 or 4. r is preferably 1 or 2, very preferably 2, and s and t are independently preferably 0 or 1, very preferably 0. R 81 and R 82 particularly independently denotes n-alkyl having 1 to 5 C atoms.

[0241] In a first very preferred embodiment, the compounds of the formulae VIII-1 to VIII-6 are selected from the compounds of the formulae VIII-1a to VIII-6a, in particular from the compounds of the formula VIII-3a.

[0242] [ka]

[0243] In the formula, R 81 , R 82 , L, r and s have the meanings defined above.

[0244] In a second very preferred embodiment, the compounds of the formulae VIII-1 to VIII-6 are selected from the compounds of the formulae VIII-1b to VIII-5b, in particular of the formula VIII-2b.

[0245] [ka]

[0246] In the formula, R 81 , R 82 , L, r and s have the meanings defined above.

[0247] In a third very preferred embodiment, the compounds of formulae VIII-1 to III-6 are selected from the compounds of formulae III-1c to III-6c, in particular from the compounds of formula I3-c.

[0248] [ka]

[0249] In the formula, R 81 , R 82 , L, r and s have the meanings defined above.

[0250] In a fourth very preferred embodiment, the compounds of the formulae VIII-1 to VIII-6 are selected from the compounds of the formulae VIII-1d to VIII-6d, in particular the compounds of the formula VIII-3d.

[0251] [ka]

[0252] In the formula, R 81 , R 82 , L, r and s have the meanings defined above.

[0253] In a particularly preferred embodiment, the medium according to the invention comprises one or more compounds selected from the group of formulae VIII-1a to VIII-6a and one or more compounds selected from the group of formulae VIII-1b to VIII-6b.

[0254] Very particularly preferably, the medium comprises one or more compounds selected from the group of the compounds of the formulae VIII-3a, VIII-2b, VIII-3c and VIII-3d.

[0255] [ka]

[0256] In the formula, R 81 , R 82 , L and r have the meanings defined above, and preferably r is 0.

[0257] The most preferred compounds of formula VIII include, in particular, one or more of the following:

[0258] [ka]

[0259] [ka]

[0260] [ka]

[0261] Alternatively or additionally, a compound of formula VIII below may be used:

[0262] [ka]

[0263] [ka]

[0264] [ka]

[0265] [ka]

[0266] The medium according to the invention may comprise one or more compounds with negative dielectric anisotropy, preferably selected from the group consisting of the formulae Y, B, BC, CR, PH-1 and PH-2.

[0267] [ka]

[0268] In the formula, R Y1 , R Y2 , R B1 , R B2 , R CR1 , R CR2 , RP1 and R P2 each independently represent H, a linear alkyl or alkoxy, each having 1 to 15 C atoms, a linear alkenyl or alkenyloxy, each having 2 to 15 C atoms, or a branched alkyl, alkoxy, alkenyl, alkenyloxy, each having 3 to 15 C atoms, provided that in these groups one or more CH2 groups are each independently of one another such that O atoms are not directly linked to one another, [ka] -CH=CH-, -C≡C-, -CF2O-, -OCF2-, -O-, -CO-O- or -O-CO-, provided that one or more H atoms may be replaced by halogen; [ka] occur independently of each other, a) a 1,4-cyclohexenylene group or a 1,4-cyclohexylene group, in which one or two non-adjacent CH groups may be replaced by —O— or —S—; b) a 1,4-phenylene group, in which one or two CH groups may be replaced by N, or c) a radical selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]-octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl, provided that groups a), b) and c) may be mono- or polysubstituted with halogen atoms; Preferably [ka] represents Z x , Z yare the same or different and represent -CH2CH2-, -CH=CH-, -CF2O-, -OCF-, -CHO-, -OCH2-, -CO-O-, -O-CO-, -C2F4-, -CF=CF-, -CH=CH-CHO- or a single bond, preferably a single bond; Z 1 represent, in each occurrence independently of one another, -CO-O-, -O-CO-, -CF2O-, -OCF2-, -C2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-C2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, preferably -C2O or - a single bond, L 11 and L 12 each independently represent F, Cl, CF or CHF, preferably H or F, most preferably F, and W represents O or S; n is 0, 1 or 2, preferably 0 or 1; c is 0, 1 or 2, preferably 1 or 2; x and y are independently 0, 1 or 2, with the proviso that x+y≦3.

[0269] The compound of formula Y is preferably selected from the group of compounds of formula YA, YB, YC and YD.

[0270] [ka]

[0271] During the ceremony, R 2A , R 2B , R 2C and R 2Deach independently represent H, an alkyl or alkenyl group having up to 15 C atoms, which is unsubstituted, monosubstituted with CN or CF3 or at least monosubstituted with a halogen, provided that in addition one or more CH2 groups in these groups are not joined together by -O-, -S-, ... [ka] may be replaced by -C≡C-, -CF2O-, -OCF2-, -OC-O- or -O-CO-; L 1 ~L 4 each independently represent F, Cl, CF3 or CHF2, Y represents H, F, Cl, CF3, CHF2 or CH3, preferably H or CH3, very preferably H, Z 2 , Z 2B and Z 2D each independently represents a single bond, -CHCH-, -CH=CH-, -CFO-, -OCF-, -CHO-, -OCH-, -COO-, -OCO-, -CF-, -CF=CF- or -CH=CHCHO-; (O) represents O or a single bond; p represents 0, 1 or 2; q represents 0 or 1, and v represents 1, 2, 3, 4, 5 or 6.

[0272] Preferred compounds of formula YA, YB, YC and YD are shown below.

[0273] [ka]

[0274] [ka]

[0275] [ka]

[0276]

change

[0277]

change

[0278]

change

[0279]

change

[0280]

change

[0281]

change

[0282]

change

[0283]

change

[0284]

change

[0285]

change

[0286] In the formula, the parameter a represents 1 or 2, and alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, alkenyl represents a linear alkenyl group having 2 to 6 C atoms, and (O) represents an oxygen atom or a single bond. Alkenyl preferably represents CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH- or CH3-CH=CH-(CH2)2-.

[0287] Particularly preferred mixtures according to the invention comprise one or more compounds of the formulae YA-2, YA-8, YA-10, YA-16, YA-18, YA-40, YA-41, YA-42, YA-43, YB-2, YB-10, YB-16, YC-1, YD-4 and YD-10.

[0288] The proportion of compounds of formula YA and / or YB in the mixture as a whole is preferably at least 20% by weight.

[0289] Preferred media according to the invention comprise at least one compound of formula YC-1.

[0290] [ka]

[0291] In the formula, alkyl and alkyl * has the meaning given above and is preferably in an amount of less than 5% by weight, in particular more than 3% by weight.

[0292] The compound of formula B is preferably selected from the compounds of formula B-1 and / or B-2.

[0293] [ka]

[0294] During the ceremony, R 11 and R 12 each independently of one another represents an alkyl, alkenyl or alkoxy group having up to 15 C atoms, more preferably one or both of them represents an alkoxy group, and L 11 and L 12 represents F, respectively.

[0295] Preferably, the compound of formula B-1 is selected from the group of compounds of formula B-1-1 to B-1-11, preferably of formula B-1-6.

[0296] [ka]

[0297] [ka]

[0298] During the ceremony, Alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms, and alkenyl and alkenyl * each independently represent a linear alkenyl group having 2 to 6 carbon atoms, alkoxy and alkoxy * each independently represents a linear alkoxy group having 1 to 6 carbon atoms, and L 11 and L 12 each independently represents F or Cl, preferably both represent F.

[0299] Preferably, the compound of formula B-2 is selected from the group of compounds of formula B-2-1 to B-1-10, preferably of formula B-2-6.

[0300] [ka]

[0301] [ka]

[0302] During the ceremony, Alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms, and alkenyl and alkenyl * each independently represent a linear alkenyl group having 2 to 6 carbon atoms, alkoxy and alkoxy * each independently represents a linear alkoxy group having 1 to 6 carbon atoms, and L 1 and L 2 each independently represents F or Cl, preferably both represent F.

[0303] The medium may comprise one or more compounds of formula BA-1 and / or BA-2.

[0304] [ka]

[0305] In the formula, L 11 and L 12 has the same meaning as given in formula B, (O) represents O or a single bond, R IIIA is an alkyl or alkenyl group having up to 7 C atoms or a group Cy-C m H 2m+1 - represents m and n are the same or different and are 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, Cy represents alkyl or alkenyl, each having up to 3 C atoms, or an alicyclic group having 3, 4 or 5 ring atoms, optionally substituted by halogen or CN, and preferably represents cyclopropyl, cyclobutyl or cyclopentyl.

[0306] The compounds of formula BA-1 and / or BA-2 are contained in the medium alternatively or additionally, preferably additionally, to the compounds of formula B.

[0307] Highly preferred compounds of formula BA-1 and BA-2 are:

[0308] [ka]

[0309] where alkoxy is a linear alkoxy group having 1 to 6 C atoms or alternatively -(CH2) n F (where n is 2, 3, 4 or 5), preferably C2H4F.

[0310] Alternatively, the medium comprises one or more compounds of formula BAa-1-3.

[0311] [ka] In the formula, alkenyl denotes a straight-chain alkenyl having 2 to 6 C atoms, preferably 4 C atoms, very preferably CH3-CH=CH-CH2-.

[0312] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula B-3.

[0313] [ka]

[0314] During the ceremony R 1 , R 3 are the same or different and represent H, an alkyl or alkoxy group having 1 to 15 C atoms, provided that one or more CH groups in these groups are not directly linked to O atoms, and are -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] Each may be replaced independently by -O-, -CO-O- or -O-CO-, provided that in addition one or more H atoms may be replaced by a halogen.

[0315] The compound of formula B-3 is preferably selected from the group of compounds of formulae B3-1 to B3-10:

[0316] [ka]

[0317] [ka]

[0318] In the formula, R 12 is alkyl having 1 to 7 C atoms, preferably ethyl, n-propyl or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl, or alternatively -(CH2) n F (where n is 2, 3, 4 or 5), preferably C2H4F.

[0319] In a preferred embodiment of the invention, the medium comprises one or more compounds of formulae B-4 to B-6, preferably of formula B-5.

[0320] [ka]

[0321] in which the occurring groups have the meanings given above and R 11 preferably represents a linear alkyl having 1 to 7 C atoms, R 12 preferably represents optionally fluorinated alkoxy having 1 to 7 C atoms.

[0322] In a highly preferred embodiment, the medium comprises one or more compounds of formula B-5-1.

[0323] [ka]

[0324] In the formula, R 11 represents a straight-chain alkyl having 1 to 7 C atoms.

[0325] In a preferred embodiment, the medium comprises one or more compounds of formula I selected from the group of compounds of formulae B-7 to B-9, preferably of formula B-8.

[0326] [ka]

[0327] where the parameters have the meanings given above and R 11 preferably represents a linear alkyl, and R 12 preferably represents F or optionally fluorinated alkoxy, each having 1 to 7 C atoms.

[0328] Particularly preferred compounds of formulae BC, CR and PH-1 are compounds BC-1 to BC-7, CR-1 to CR-5 and BP-1 to BP-7.

[0329] [ka]

[0330] [ka]

[0331] During the ceremony, Alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, and alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 carbon atoms.

[0332] More preferred are mixtures comprising one, two or three compounds of formula BC-2, BC-3, BP-2 and / or BP-3, very preferably BP-2 and / or BP-3, especially BP-3 compounds.

[0333] In a preferred embodiment, the medium according to the invention comprises one or more HALS stabilizers of formula H.

[0334] [ka]

[0335] During the ceremony, Ar represents a methylene group, or an aromatic hydrocarbon group having 6 to 40 C atoms, or a heteroaromatic hydrocarbon group having 4 to 40 C atoms, preferably an aromatic hydrocarbon group having 6 to 40 C atoms; Sp represents a spacer group; R S represents H, alkyl having 1 to 12 C atoms or alkenyl having 2 to 12 C atoms; Z S are -O-, -C(O)O-, and -(CH2) z -or-(CH2) z O-, or a single bond; HA is [ka] represents; R H H, O · , CH3, OH or OR S represents; R S1 , R S2 , R S3 and R S4 are identical or different and represent alkyl having 1 to 6 C atoms, preferably having 1 to 3 C atoms, very preferably CH3; G is H or R S or group Z S - represents HA; z is an integer from 1 to 6, and q is 2, 3 or 4, preferably 3 or 4.

[0336] The compounds of formula I are preferably selected from the compounds of formulae H-1, H-2 and H-3.

[0337] [ka]

[0338] In the formula, R H has the meaning given above, preferably H or O · represents Sp, which may be the same or different in each occurrence, represents a spacer group; W represents an alkylene group which may be linear or branched and unsaturated having 1 to 12 C atoms, provided that one or more non-adjacent -CH2- groups may be replaced by -O-.

[0339] Preferred compounds of formula H-1 are selected from compounds of formula H-1-1:

[0340] [ka]

[0341] In the formula, R H has the meaning given above, preferably H or O · and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, and very preferably 7.

[0342] Preferred compounds of formula H-2 are selected from compounds of formula H-2-1:

[0343] [ka]

[0344] In the formula, R Hhas the meaning given above, preferably H or O · and n2 is the same or different in each occurrence, preferably the same and an integer from 0 to 12, preferably 2, 3, 4, 5 or 6, very preferably 3, and R S are identical or different at each occurrence, preferably identical and denote alkyl having 1 to 6 C atoms, preferably n-butyl.

[0345] Preferred compounds of formula H-3 are selected from compounds of formula H-3-1:

[0346] [ka]

[0347] In the formula, R H has the meaning given above, preferably H or O · and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, and very preferably 7.

[0348] Preferably, the medium according to the invention comprises a stabilizer selected from the group of compounds of the formulae ST-1 to ST-19.

[0349] [ka]

[0350] [ka]

[0351] [ka]

[0352] [ka]

[0353] [ka]

[0354] [ka]

[0355] [ka]

[0356] During the ceremony R ST represents H, an alkyl or alkoxy group having 1 to 15 C atoms, provided that in addition, one or more CH groups in these groups are not directly linked to O atoms, and are -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] -O-, -CO-O-, -O-CO-, each of which may be replaced independently of the other, provided that in addition one or more H atoms may be replaced by halogen; [ka] [ka] represents Z ST represent, independently of one another, -CO-O-, -O-CO-, -CF2O-, -OCF2-, -C2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-, -C2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond; L 1 and L 2 each independently represents F, Cl, CF3 or CHF2, n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, and very preferably 7; n2 is the same or different in each occurrence, preferably the same and an integer from 1 to 12, preferably 2, 3, 4, 5 or 6, very preferably 3; and R S are identical or different at each occurrence, preferably identical and denote alkyl having 1 to 6 C atoms, preferably n-butyl, p represents 1 or 2; q represents 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0357] Among the compounds of formula ST, the compounds of the following formula are particularly preferred:

[0358] [ka]

[0359] [ka]

[0360] [ka]

[0361] In the compounds of formulae ST-3a and ST-3b, n preferably represents 3. In the compounds of formula ST-2a, n preferably represents 7.

[0362] Very particularly preferred mixtures according to the invention comprise one or more stabilizers selected from the group of compounds of the formulae ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1 and ST-12.

[0363] [ka]

[0364] [ka]

[0365] The compounds of the formulae ST-1 to ST-19 are present in the liquid crystal mixture according to the invention in an amount of preferably 0.005 to 0.5% each, based on the mixture.

[0366] If the mixture according to the invention comprises two or more compounds from the group of compounds of formulae ST-1 to ST-19, the concentration increases accordingly in the case of two compounds to 0.01 to 1%, based on the mixture.

[0367] However, based on the mixture according to the invention, the total proportion of compounds of the formulae ST-1 to ST-19 must not exceed 2%.

[0368] In another preferred embodiment of the present invention the liquid crystal medium additionally comprises one or more polymerisable compounds, which are preferably selected from the group consisting of:

[0369] [ka]

[0370] In the formula, the individual substituents, identical or different at each occurrence, each have, independently of one another, the following meanings: R a and R b is P, P-Sp-, H, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, SF5 or a linear or branched alkyl having 1 to 25 C atoms, provided that in addition one or more non-adjacent CH2 groups are present in -C(R) such that O and / or S atoms are not directly linked to each other; 0 )=C(R 00 )-, -C≡C-, -N(R 00)-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, each independently of the other, provided that in addition one or more H atoms may be replaced by F, Cl, Br, I, CN, P or P-Sp-, provided that B 1 and / or B. 2 If contains saturated C atoms, R a and / or R b may also represent a group spiro-linked to this saturated C atom, However, the group R a and R b at least one of which represents or contains the group P or P-Sp-, P is a polymerizable group, Sp is a spacer group or a single bond; B 1 and B 2 is preferably an aromatic, heteroaromatic, alicyclic or heterocyclic group having 4 to 25 ring atoms, which may also contain fused rings, and which is unsubstituted or mono- or polysubstituted by L; Z b -O-, -S-, -CO-, -CO-O-, -OCO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, CR 0 R 00 or a single bond, R 0 and R 00 each independently represent H or alkyl having 1 to 12 C atoms, m represents 0, 1, 2, 3 or 4; n1 represents 1, 2, 3 or 4; L is P, P-Sp-, OH, CH2OH, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x)2, -C(=O)Y 1 , -C(=O)R x , -N(R x ) 2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms or linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, provided that in addition, one or more H atoms may be replaced by F, Cl, P or P-Sp-, P and Sp have the meanings indicated above, Y 1 represents a halogen, R x represents P, P-Sp-, H, halogen, linear, branched or cyclic alkyl having 1 to 25 C atoms (provided that in addition, one or more non-adjacent CH groups may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that O and / or S atoms are not directly linked to one another, and in addition, one or more H atoms may be replaced by F, Cl, P or P-Sp-), an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms.

[0371] Particularly preferred compounds of formula I are B 1 and B 2are each independently 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, 9,10-dihydrophenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarin, flavone (in addition, one or more CH groups in these groups may be replaced by N), cyclohexane-1,4-diyl (in addition, one or more non-adjacent CH groups may be replaced by O and / or S), 1, 4-cyclohexenylene, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, piperidine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indan-2,5-diyl or octahydro-4,7-methanoindan-2,5-diyl, all of which groups may be unsubstituted or mono- or polysubstituted by L as defined above.

[0372] Particularly preferred compounds of formula M are B 1 and B 2 are each independently 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl.

[0373] Highly preferred compounds of formula M are selected from the following formulae:

[0374] [ka]

[0375] [ka]

[0376] [ka]

[0377] [ka]

[0378] [ka]

[0379] [ka]

[0380] In the formula, the individual radicals, which are identical or different at each occurrence, each have the following meaning independently of one another: P 1 , P 2 , P 3 is a polymerizable group, preferably selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxy; Sp 1 , Sp 2 , Sp 3 is a single bond or a spacer group, provided that in addition there is one or more groups P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - is R aa may represent, provided that any group P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 -At least one R aa preferably -(CH2) p1 -, -(CH2) p1 -O-, -(CH2) p1 -CO-O- or -(CH2) p1 -O-CO-O-, wherein p1 is an integer of 1 to 12; R aais H, F, Cl, CN or a straight-chain or branched alkyl having 1 to 25 C atoms (provided that in addition one or more non-adjacent CH groups are present in the -C(R) group so that O and / or S atoms are not directly linked to each other); 0 )=C(R 00 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, each independently of the other, provided that in addition one or more H atoms are replaced by F, Cl, CN or P 1 -Sp 1 -), particularly preferably linear or branched, mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxybonyloxy having 1 to 12 C atoms, with the proviso that alkenyl and alkynyl groups have at least 2 C atoms and branched groups have at least 3 C atoms, R 0 , R 00 is H or alkyl having 1 to 12 C atoms, R y and R z is H, F, CH3 or CF3, X 1 , X 2 , X 3 is -CO-O-, -O-CO- or a single bond, Z M1 -O-, -CO-, -C(R y R z )- or -CF2CF2-, Z M2 , Z M3 is -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2- or -(CH2) n where n is 2, 3 or 4; L is F, Cl, CN or linear or branched, optionally monofluorinated or polyfluorinated, alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, L', L" are H, F or Cl; r is 0, 1, 2, 3 or 4; s is 0, 1, 2 or 3; t is 0, 1, or 2; x is 0 or 1.

[0381] Compounds of formulae M2 and M13 are particularly preferred.

[0382] More preferred are the trireactive compounds M15 to M31, in particular M17, M18, M19, M22, M23, M24, M25, M30 and M31.

[0383] In the compounds of formulae M1 to M31, the group [ka] in which L has one of the meanings given above and r represents 0, 1, 2, 3 or 4, are in particular [ka] Represents.

[0384] in which L, identically or differently, on each occurrence has one of the meanings given above or below, preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, OCH3, COCH3 or OCF3, in particular F or CH3.

[0385] Preferred compounds of formulae M1 to M31 are P 1 , P 2 and P 3 represents an acrylate, methacrylate, oxetane or epoxy group, very preferably an acrylate or methacrylate group.

[0386] Further preferred compounds of formulae M1 to M31 are Sp 1 , Sp 2 and Sp 3 is a single bond.

[0387] Further preferred compounds of formulae M1 to M31 are Sp 1 , Sp 2 and Sp 3 One of them represents a single bond, and Sp 1 , Sp 2 and Sp 3 The other one is different from a single bond.

[0388] Further preferred compounds of the formulae M1 to M31 are those which contain a group Sp different from a single bond 1 , Sp 2 and Sp 3 -(CH2) s1 represents -X"-, where s1 is an integer of 1 to 6, preferably 2, 3, 4, or 5, and X" is a bond to the adjacent benzene ring and is -O-, -O-CO-, -CO-O-, -O-CO-O-, or a single bond.

[0389] Particularly preferred are liquid crystal media comprising one, two or three polymerizable compounds of the formula M, preferably selected from the formulae M1 to M31.

[0390] More preferably, the liquid crystal medium according to the invention comprises one or more polymerizable compounds selected from Table E below.

[0391] The proportion of polymerizable compounds preferably selected from formula M and table E in the liquid-crystalline medium is between 0.01 and 5%, very preferably between 0.05 and 1%, most preferably between 0.1 and 0.5%.

[0392] It has been observed that the addition of one or more polymerizable compounds, such as those selected from Formula M and Table E, to a liquid crystal medium can result in advantageous properties such as fast response times. Such liquid crystal media are particularly suitable for use in PSA displays, exhibiting low image fixing, rapid and complete polymerization, rapid generation of a low pretilt angle that is stable after UV exposure, high reliability, high VHR values ​​after UV exposure, and high birefringence. By appropriately selecting the polymerizable compound, it is possible to increase the absorption of the liquid crystal medium at longer UV wavelengths, thereby enabling the use of such longer UV wavelengths for polymerization, which is advantageous for the display manufacturing process.

[0393] The polymerizable group P is a group suitable for polymerization reactions, such as, for example, free-radical or ionic chain polymerization, polyaddition or polycondensation, or polymer-analogous reactions, such as addition or condensation onto the main chain. Groups for chain polymerization, especially those containing a C=C double bond or a -C≡C- triple bond, and groups suitable for ring-opening polymerization, such as, for example, oxetane or epoxide groups, are particularly preferred.

[0394] The preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -(O) k3 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -, HS-CW 2 W 3 -, HW 2 N-, HO-CW2 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 Si—, wherein W 1 represents H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, and W 2 and W 3 each independently of one another denotes H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, W 4 , W 5 and W 6 each independently represents Cl, oxaalkyl or oxacarbonylalkyl having 1 to 5 carbon atoms, W 7 and W 8 each independently represent H, Cl or alkyl having 1 to 5 C atoms; Phe represents 1,4-phenylene optionally substituted with one or more groups L as defined in the above formula M other than P-Sp-; k1, k2 and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0395] A highly preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -O-, CH2=CW 2 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1-CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH- and W 4 W 5 W 6 Si—, wherein W 1 represents H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, and W 2 and W 3 each independently of one another denotes H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, W 4 , W 5 and W 6 each independently represents Cl, oxaalkyl or oxacarbonylalkyl having 1 to 5 carbon atoms, W 7 and W 8 each independently represent H, Cl, or alkyl having 1 to 5 C atoms; Phe represents 1,4-phenylene; k1, k2, and k3 each independently represent 0 or 1; k3 preferably represents 1; and k4 represents an integer of 1 to 10.

[0396] Very particularly preferred groups P are CH2=CW 1 -CO-O-, in particular CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, further CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, [ka] is selected from the group consisting of:

[0397] More preferably, the polymerizable group P is selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide, most preferably from the group consisting of acrylate and methacrylate.

[0398] Sp, when different from a single bond, is preferably of the formula Sp"-X", so that each group P-Sp- corresponds to the formula P-Sp"-X"-, in which: Sp" represents alkylene having 1 to 20, preferably 1 to 12, C atoms, which may optionally be mono- or polysubstituted by F, Cl, Br, I or CN, provided that in addition, one or more non-adjacent CH groups are each independently of one another -O-, -S-, -NH-, -N(R 0 )-, -Si(R 0 R 00 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 )-CO-O-, -O-CO-N(R 0 )-, -N(R 0 )-CO-N(R 00 -, -CH=CH- or -C≡C- may be substituted such that the O and / or S atoms are not directly linked to one another, “X” is -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-, -N(R 0 )-CO-, -N(R 0 )-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -, -CY 2 =CY 3 represents -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or a single bond; R 0 and R 00each independently represent H or alkyl having 1 to 20 C atoms, Y 2 and Y 3 each independently represents H, F, Cl or CN.

[0399] X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, or -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 - or a single bond.

[0400] Exemplary spacer groups Sp and -Sp"-X"- include, for example, -(CH2) p1 -, -(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR 0 R 00 -O) p1 wherein p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 has the meaning shown in the formula M above.

[0401] Particularly preferred groups Sp and -Sp"-X"- are -(CH2) p1 -, -(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, in which p1 and q1 have the meanings given above.

[0402] Particularly preferred radicals Sp" are in each case linear ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.

[0403] For the production of PSA displays, the polymerizable compounds contained in the liquid crystal medium are polymerized or (if one compound contains more than one polymerizable group) crosslinked by in situ polymerization in the liquid crystal medium between the substrates of the LC display, optionally with application of a voltage to the electrodes.

[0404] The structure of the PSA display according to the present invention corresponds to the usual configuration of a PSA display as described in the prior art cited at the beginning. A configuration without protrusions is preferred, in particular one in which the electrode on the color filter side is unstructured and only the electrode on the TFT side has slots. A particularly suitable and preferred electrode structure for PS-VA displays is described, for example, in US Patent Application Publication No. 2006 / 0066793.

[0405] The combination of the compounds of the above-mentioned preferred embodiments with the above-mentioned polymerizable compounds in the liquid-crystalline media according to the invention always leads to high clearing points and high VHR values, as well as low threshold voltages, low rotational viscosities and very good low-temperature stability.

[0406] By using a liquid crystal medium containing a polymerizable compound, a particularly low pretilt angle can be rapidly established in a PSA display. In particular, the liquid crystal medium also shows a significantly reduced response time, especially the gray-scale response time, in a PSA display compared with media from the prior art.

[0407] In a further preferred embodiment, alone or in combination with one another, the medium according to the invention comprises the following compounds, where the acronyms are explained in Table D below:

[0408] one or more compounds of formula I in a total concentration in the range of 0.5% to 10%, preferably 1% to 8%, particularly preferably 2% to 7%;

[0409] and / or one or more compounds of the formula II, preferably of the formula II-1 and optionally II-3, more preferably of the sub-formulae II-1a and / or II-1f and / or II-1g and / or II-1h and / or II-3a and / or II-3d, in a total concentration in the range from 5% to 35%, preferably from 6% to 32%, particularly preferably from 8% to 28%;

[0410] and / or one or more compounds of the formula II-1, preferably of the sub-formulae II-1a and / or II-1f and / or II-1g and / or II-1h, in particular of the formulae II-1a-1 and II-1f-1, or of the formulae II-1a-1 and II-1f-1 and II-1h-1, or of the formulae II-1f-1 and II-1g-1 and II-1h-1, preferably in a total concentration in the range from 2% to 22%, preferably from 3% to 19%, particularly preferably from 4% to 17%;

[0411] and / or one or more compounds of formula II-1f-1 in a total concentration in the range of 0.3% to 8%, preferably 0.5% to 6%, particularly preferably 1% to 5%;

[0412] and / or one or more compounds of formula II-1g-1 in a total concentration in the range of 1% to 15%, preferably 2% to 12%, particularly preferably 3% to 10%;

[0413] and / or one or more compounds of formula II-1a-1 at a total concentration in the range of 0.5% to 15%, preferably 1% to 10%;

[0414] and / or one or more compounds of formula III, preferably selected from the group of compounds of formula III-2, more preferably of formulae III-2c and / or III-2d and / or III-2g and / or III-2i and / or III-2l and / or III-2m, very preferably of formulae III-2c-3 and / or III-2d-1 and / or III-2g-2 and / or III-2l-3 and / or III-2m-1, in a total concentration ranging from 0.1% to 30%, preferably from 0.2% to 28%, more preferably from 0.3% to 25%, with the proviso that the concentration of the compound(s) of formula III-2m-1 is very preferably between 0.1% and 1%;

[0415] and / or one or more compounds of the formula YA, preferably of the formulae YA-2 and / or YA-10, in a total concentration in the range from 1% to 10%, preferably from 2% to 8%, particularly preferably from 3% to 7%;

[0416] and / or one or more compounds of the formula YD, preferably of the formulae YD-7 and / or YD-10, in a total concentration in the range from 1% to 10%, preferably from 2% to 8%, particularly preferably from 3% to 7%;

[0417] and / or one or more compounds of the formula YB, preferably of the formulae YB-2 and / or YB-10, in a total concentration in the range from 0.5% to 10%, preferably from 1% to 7%, particularly preferably from 2% to 5%;

[0418] and / or one or more compounds of the formulae I and YD and optionally YA, preferably selected from the compounds of the formulae YA-2, YA-10, YD-7 and YD-10, in a total concentration in the range from 1% to 20%, preferably from 3% to 17%, particularly preferably from 4% to 14%;

[0419] and / or one or more compounds of the formula B, preferably B-2, very preferably B-2-6, in a total concentration in the range of 0.1% to 10%, preferably 0.5% to 8%, particularly preferably 1% to 6%;

[0420] and / or one or more compounds of the formula B, preferably B-5, very preferably B-5-1 or LB(S)-n-OT, in particular LB(S)-3-OT, in a total concentration in the range from 0.1% to 10%, preferably from 0.5% to 8%, particularly preferably from 1% to 6%;

[0421] and / or one or more compounds of the formula B-2 and one or more compounds of the formula B-5 in a total concentration in the range from 1% to 20%, preferably from 2% to 15%, particularly preferably from 5% to 11%;

[0422] and / or less than 5% of one or more compounds of formula IV-1, preferably less than 3%, very preferably less than 1%;

[0423] and / or one or more compounds of formula IV, preferably of formula IV-3, preferably selected from the compounds of the formulae IV-3-1 to IV-3-6, in particular selected from the compounds of the formulae IV-3-1, IV-3-2, IV-3-4 and IV-3-6, in a total concentration ranging from 15% to 60%, more preferably from 18% to 50%, very preferably from 20% to 45%;

[0424] and / or 0.5% to 8%, preferably 1% to 6%, of compound IV-3-6 (CC-3-2V1) or IV-3-4 (CC-4-V1);

[0425] and / or one or more compounds of formula IVa, preferably of formula IVa-2, in a total concentration ranging from 0.1% to 3%, more preferably from 0.2% to 2%;

[0426] and / or one or more compounds of the formula IVb, preferably of the formula IVb-2, very preferably of the formula IVb-2-3, preferably in a total concentration in the range of 0.2% to 8%, more preferably 0.5% to 7%, in particular 1% to 6%;

[0427] and / or one or more compounds of formula V, preferably selected from the group consisting of compounds V-1-1, V-1-6, V-2-1, V-2-2, V-2-3, V-2-4, V-3-5 and V-4-1, preferably in a total concentration ranging from 5% to 50%, preferably from 10% to 40%, in particular from 15% to 33%;

[0428] and / or one or more compounds of formula CL, preferably selected from formula CL-3, preferably in a total concentration in the range of 1% to 15%, preferably 2% to 12%, in particular 3% to 10%;

[0429] and / or one or more compounds of formula V-1-1 or V-1-6, preferably selected from compounds CCC-nV, CCC-VV and CVCC-nm, preferably in a total concentration ranging from 0.5% to 15%, preferably from 1% to 12%, in particular from 2% to 10%;

[0430] and / or one or more compounds of formula V-2-1 and / or V-2-2, preferably selected from the group consisting of CCP-nm and / or CCP-Vn-m and / or CPP-nm, very preferably CCP-3-1, CCP-V-1 and CCP-V2-1, preferably in a total concentration ranging from 8% to 35%, more preferably from 10% to 30%, very preferably from 12% to 28%;

[0431] and / or one or more compounds of formula VII, preferably of formula VII-1-20 and / or VII-1-21, preferably in a total concentration in the range of 1% to 15%, preferably 2% to 13%, in particular 3% to 11%;

[0432] and / or one or more compounds of formula VIII, preferably selected from compounds of formula VIII-3, more preferably VIII-3a, preferably in a total concentration ranging from 1% to 25%, preferably from 2% to 20%, in particular from 3% to 18% or from 5% to 18% or from 10% to 18%;

[0433] and / or one or more compounds of formula I and V-3-4, preferably in a total concentration in the range of 1% to 15%, preferably 2% to 13%, in particular 3% to 12%;

[0434] and / or compound CC-3-V, preferably at a concentration of 20% or more, more preferably 30% or more, very preferably 40% or more, in combination with CC-3-V1 and / or CC-4-V1 and / or CC-3-2V1, preferably at a concentration of 2% or more, more preferably 5% or more.

[0435] The liquid crystal media according to the present invention retain a nematic phase down to -20°C, preferably down to -30°C, particularly preferably down to -40°C, and a clearing point of 90°C or higher, preferably 100°C or higher, while at the same time achieving a rotational viscosity γ1 of 200 mPa·s or less, particularly preferably 150 mPa·s or less, thereby enabling excellent MLC displays with fast response times. The rotational viscosity is determined at 20°C.

[0436] The liquid crystal medium according to the present invention has a positive dielectric anisotropy Δε at 20° C. and 1 kHz, preferably +1.5 or more, preferably 1.5 to 12, more preferably 2.0 to 10.0, very preferably 2.5 to 9.0, particularly preferably 3.0 to 8.5.

[0437] In a preferred embodiment, the dielectric anisotropy Δε at 20° C. and 1 kHz of the liquid-crystalline media according to the invention is preferably in the range of 3.8 to 4.8.

[0438] The birefringence Δn of the liquid-crystalline media according to the invention is preferably 0.080 to 0.140, very preferably 0.090 to 0.135, in particular 0.091 to 0.132.

[0439] In a preferred embodiment of the invention the medium has a birefringence of 0.090 to 0.115, very preferably 0.095 to 0.110, in particular 0.100 to 0.113.

[0440] In a preferred embodiment of the invention the medium has a birefringence of 0.110 to 0.130, very preferably 0.119 to 0.128, in particular 0.120 to 0.123.

[0441] In a preferred embodiment of the invention the medium has a birefringence of 0.120 to 0.140, very preferably 0.125 to 0.135, in particular 0.129 to 0.132.

[0442] The rotational viscosity γ1 of the liquid-crystalline media according to the invention is preferably 180 mPa·s or less, more preferably 160 mPa·s or less, very preferably 150 mPa·s or less.

[0443] The ratio γ1 / K1 of the liquid-crystalline media according to the invention is preferably 5.5 mPa·s / pN or less, more preferably 5.3 mPa·s / pN or less, very preferably 5.0 mPa·s / pN or less.

[0444] In this specification, the structures of mesogenic compounds are represented by abbreviations, also called acronyms. These acronyms are used to abbreviate the chemical formulas as follows, using Tables A to C below: n H 2n+1 , C m H 2m+1 and C l H 2l+1 and C n H2 n-1 , C m H 2m-1 and C l H 2lrepresent straight-chain alkyl or alkenyl, respectively, having n, m and l C atoms, respectively, where n and m are independently 0, 1, 2, 3, 4, 5, 6 or 7, and l is 1, 2 or 3. Table A lists the codes used for the ring elements of the core structure of the compounds, while Tables B and C show the linking and terminal groups. Table D shows exemplary structures of compounds along with their respective abbreviations.

[0445] <Table A: Ring elements>

[0446] [Table 1]

[0447] [Table 2]

[0448] [Table 3]

[0449] <Table B: Crosslinking group>

[0450] [Table 4]

[0451] <Table C: Terminal group>

[0452] [Table 5]

[0453] [Table 6]

[0454] In the table, n and m each represent an integer, and the three dots "..." are places for other abbreviations from this table.

[0455]

[0456] Table 7

[0457] Table 8

[0458] Table 9

[0459] Table 10

[0460] Table 11

[0461] Table 12

[0462] Table 13

[0463] Table 14

[0464] Table 15

[0465] Table 16

[0466] Table 17

[0467] Table 18

[0468] Table 19

[0469] Table 20

[0470] Table 21

[0471] Table 22

[0472] Table 23

[0473] Table 24

[0474] Table 25

[0475] Table 26

[0476] Table 27

[0477] Table 28

[0478] Table 29

[0479] Table 30

[0480] Table 31

[0481] Table 32

[0482] Table 33

[0483] Table 34

[0484] Table 35

[0485] Table 36

[0486] Table 37

[0487] [Table 38]

[0488] [Table 39]

[0489] [Table 40]

[0490] [Table 41]

[0491] In a preferred embodiment of the invention, the medium comprises one or more compounds selected from the group of compounds in Table D.

[0492] Table E shows chiral dopants that are preferably used in the mixtures according to the invention.

[0493]

[0494] [Table 42]

[0495] [Table 43]

[0496] [Table 44]

[0497] Preferably, the medium according to the invention comprises one or more compounds selected from the group of compounds of Table E.

[0498] Table F shows exemplary reactive mesogenic compounds (RM) that can be used in the LC media according to the present invention.

[0499] [Table 45]

[0500] [Table 46]

[0501] [Table 47]

[0502] [Table 48]

[0503] [Table 49]

[0504] [Table 50]

[0505] [Table 51]

[0506] [Table 52]

[0507] [Table 53]

[0508] Table 54

[0509] Table 55

[0510] Table 56

[0511] Table 57

[0512] Table 58

[0513] Table 59

[0514] Table 60

[0515] Table 61

[0516] Table 62

[0517] Table 63

[0518] Table 64

[0519] [Table 65]

[0520] In a preferred embodiment, the mixture according to the invention comprises one or more polymerizable compounds, preferably selected from the polymerizable compounds of the formulae RM-1 to RM-182. Among these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48 , RM-52, RM-54, RM-57, RM-58, RM-64, RM-74, RM-76, RM-88, RM-91, RM-102, RM-103, RM-1 09, RM-116, RM-117, RM-120, RM-121, RM-122, RM-139, RM-140, RM-142, RM-143, RM-145 , RM-146, RM-147, RM-149, RM-156 to RM-163, RM-169, RM-170 and RM-171 to RM-183 are particularly preferred. [Example]

[0521] The following examples are intended to illustrate but not limit the invention. In the examples, mp represents the melting point, T (N,I) denotes the clearing point of the liquid crystal material in degrees Celsius. Furthermore, C denotes the crystalline solid state, S denotes the smectic phase (the subscript indicates the type of phase), N denotes the nematic phase, Ch denotes the cholesteric phase, I denotes the isotropic phase, and T g represents the glass transition temperature. The number between the two symbols indicates the transition temperature in degrees Celsius.

[0522] The host mixture used to determine the optical anisotropy Δn of a single compound is the commercially available mixture ZLI-4792 (Merck). The dielectric anisotropy Δε is determined using the commercially available mixture ZLI-2857. The physical data of the compound under consideration are obtained from the change in the dielectric constant of the host mixture after adding the compound under consideration and are extrapolated to 100% of the compound used. Typically, 10% of the compound under consideration is dissolved in the host mixture, depending on the solubility.

[0523] Unless otherwise indicated, parts or percentage data refer to parts by weight or percentages by weight.

[0524] Above and below: V0 represents the capacitance threshold voltage [V] at 20°C, n e represents the extraordinary refractive index at 20°C and 589 nm, n0 represents the ordinary refractive index at 20°C and 589 nm; Δn represents the optical anisotropy (birefringence) at 20°C and 589 nm; ε ⊥ represents the dielectric constant perpendicular to the director at 20°C and 1 kHz, ε ∥ represents the dielectric constant parallel to the director at 20°C and 1 kHz, Δε represents the dielectric anisotropy at 20°C and 1 kHz; cl.p., T(N,I) represents the clearing point [℃], γ1 represents the rotational viscosity [mPa·s] measured at 20°C, K1 represents the elastic constant for "splay" deformation at 20°C [pN], K2 represents the elastic constant [pN] for "twist" deformation at 20°C, K3 represents the elastic constant [pN] for "bend" deformation at 20°C, K av is at 20°C

number

[0525] Unless explicitly stated otherwise, all temperature values ​​given in this application, such as the melting point T(C,N), the smectic (S) to nematic (N) phase transition T(S,N) and the clearing point T(N,I) or cl.p., are quoted in degrees Celsius (°C).

[0526] The term "threshold voltage" for the present invention relates to the capacitive threshold (V), also known as the Freederickss threshold, unless otherwise specified. Also, in the examples, and as is generally customary, the threshold voltage for 10% relative contrast (V 10 ) may also be given as the optical threshold.

[0527] The display used to measure the capacitive threshold voltage consists of two outer plane-parallel glass plates spaced 20 μm apart, each with an electrode layer on the inside and an unrubbed polyimide alignment layer on top that provides homeotropic alignment of the liquid crystal molecules.

[0528] The display used to measure the tilt angle consists of two outer plane-parallel glass plates spaced 4 μm apart, each with an electrode layer on the inside and a polyimide alignment layer on the top. The two polyimide layers are rubbed antiparallel to each other, causing homeotropic edge alignment of the liquid crystal molecules.

[0529] Polymerizable compounds are polymerized in the display or test cell by irradiating them with UV light of a specified intensity for a specified time while simultaneously applying a voltage to the display (typically 10 V to 30 V AC at 1 kHz). Unless otherwise indicated in the examples, polymerization is performed using a metal halide lamp and 100 mW / cm 2 The intensity is measured using a standard meter (Hoenle, UV Meter High End with UV Sensor).

[0530] The tilt angle is determined using a Mueller matrix polarimeter "AxoScan" manufactured by Axometrics, Inc. Herein, lower values ​​(i.e., larger deviations from 90°) correspond to larger tilts.

[0531] Unless otherwise stated, the term "tilt angle" refers to the angle between the LC director and the substrate, and "LC director" refers to the preferred orientation direction of the principal optical axes of the LC molecules in a layer of LC molecules with uniform orientation, which corresponds to the molecular long axis in the case of calamitic, i.e., uniaxially positively birefringent, LC molecules.

[0532] Unless otherwise indicated, VHR is measured at 20°C (VHR 20 ) and after 5 minutes in a 100°C oven (VHR 100 ) on an instrument model LCM-1 (O0004) commercially available from Toyo Corporation, Japan. Unless more precisely stated, the voltages used have frequencies in the range of 1 Hz to 60 Hz.

[0533] The stability to UV irradiation is investigated using a xenon lamp NXE1500B with a "Suntest CPS+" from Heraeus GmbH, Germany. The sealed test cells are irradiated for 2.0 hours without additional heating unless otherwise specified. The irradiation power in the wavelength range from 300 nm to 800 nm is 765 W / m 2 V. To simulate the so-called window pane mode, a UV "cut-off" filter with an edge wavelength of 310 nm is used. For each set of experiments, at least four test cells are considered for each condition, and each result is presented as the average of the corresponding individual measurements.

[0534] To study the low-temperature stability (LTS), i.e., the stability of LC mixtures in bulk against spontaneous crystallization of individual components or the development of smectic phases at low temperatures, several sealed bottles, each containing approximately 1 g of material, are stored at one or more predetermined temperatures, typically -10°C, -20°C, -30°C, and / or -40°C, and visually inspected at regular intervals to see if a phase transition is observed. The time is recorded when the first sample at a given temperature shows a change. The time until the final inspection, at which no change is observed, is recorded as the respective LTS. The test is conducted for 1000 hours. If no change is observed after 1000 hours, the result is "LTS>1000 hours."

[0535] The ion density for calculating the resistivity is measured using a commercially available LC Material Property Measurement System Model 6254 from Toyo Corporation, Japan, using a VHR test cell with AL16301 polyimide (JSR Corporation, Japan) and a cell gap of 3.2 μm. Measurements are performed after storing the sample in an oven at 60°C or 100°C for 5 minutes.

[0536] The so-called "HTP" refers to the helical twisting power (unit: μm) of an optically active or chiral substance in a liquid crystal medium. Unless otherwise indicated, HTP is measured at a temperature of 20° C. in the commercially available nematic liquid crystal host mixture MLD-6260 (Merck).

[0537] The clearing point is measured using a Mettler Thermosystem FP900. The optical anisotropy (n) is measured using an Abbe refractometer H005 (sodium spectral lamp Na10, 589 nm, 20°C). The dielectric anisotropy (Δε) is measured using an LCR meter E4980A / Agilent (G005) at 20°C (ε-parallel cell equipped with JALS2096-R1). The starting voltage (V0) is measured using an LCR meter E4980A / Agilent (G005) at 20°C (ε-parallel cell equipped with JALS2096-R1). The rotational viscosity (γ1) is measured using a Toyo Corporation LCM-2 (0002) at 20°C (gamma 1 negative cell equipped with JALS-2096-R1). The elastic constant (K1, splay) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell with JALS2096-R1). K3: The elastic constant (K3, bend) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell with JALS2096-R1).

[0538] Unless expressly stated otherwise, all concentrations in this application are given in weight percent and relate to the corresponding whole mixture containing all solid or liquid crystal components without solvent. All physical properties are measured according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", published November 1997, Merck GmbH, Germany, and apply to a temperature of 20°C, unless expressly stated otherwise.

[0539] The following examples of mixtures with positive dielectric anisotropy are particularly suitable for liquid crystal displays with at least one planar alignment layer, such as for example IPS and FFS displays, in particular UB-FFS (ultra-bright FFS) displays, as well as VA displays.

[0540] The dielectric anisotropy Δε, birefringence Δn and rotational viscosity γ1 of the single compounds are extrapolated from a 10% solution in the liquid crystal host mixture ZLI-4792 (Merck, Darmstadt).

[0541] <Synthesis example> <Synthesis Example 1: 4'-ethyl-3-fluoro-4-[4-(4-propylcyclohexyl)cyclohex-1-en-1-yl]-1,1'-biphenyl> Step 1: 4-{4'-ethyl-3-fluoro-[1,1'-biphenyl]-4-yl}-4'-propyl-[1,1'-bi(cyclohexane)]-4-ol

[0542] [ka]

[0543] 50 g (250 mmol) of 4'-ethyl-3-fluoro-1,1'-biphenyl is dissolved in 350 ml of THF and cooled to -70°C. 200 ml (1.1 equivalents) of sec-BuLi (1.4 M in cyclohexane) is added dropwise. The solution is stirred at -70°C for 1.5 hours before a solution of 60 g (270 mmol) of trans-4'-propyl[1,1'-bicyclohexyl]-4-one in 250 ml of THF is added dropwise at -70°C. The reaction mixture is stirred for 2 hours and then allowed to warm to room temperature. The reaction is quenched with water and 100 ml of 2N HCl. The organic phase is extracted with MTBE and evaporated. The crude product is crystallized in the cold from 400 ml of hot heptane to give 4-{4'-ethyl-3-fluoro-[1,1'-biphenyl]-4-yl}-4'-propyl-[1,1'-bicyclohexan]-4-ol as colorless crystals, which is used in the next step without further purification. GC-MS (+EI): 422 g / mol of two isomers.

[0544] Process 2

[0545] [ka]

[0546] 77 g (182 mmol) of 4-{4'-ethyl-3-fluoro-[1,1'-biphenyl]-4-yl}-4'-propyl-[1,1'-bi(cyclohexane)]-4-ol was dissolved in 1 L of toluene. 3.5 g (18 mmol) of 4-toluenesulfonic acid monohydrate was added, and the reaction mixture was refluxed in a Dean-Stark apparatus for 2 h. The solution was cooled to room temperature and extracted with MTBE. The crude product was dissolved in 200 mL of methylene chloride, filtered through silica, and evaporated to dryness. Crystallization from 1-chlorobutane gave 4'-ethyl-3-fluoro-4-[4-(4-propylcyclohexyl)cyclohex-1-en-1-yl]-1,1'-biphenyl as a colorless solid. Phase sequence: K64SmB165SmA176N290.3I.

[0547] GC-MS(+EI): 404.3g / mol

[0548] [Table 66]

[0549] <Synthesis Example 2>

[0550] [ka]

[0551] By analogy with Synthesis Example 1, 4'-(but-3-en-1-yl)-4-[4-(4-ethylcyclohexyl)cyclohex-1-en-1-yl]-3-fluoro-1,1'-biphenyl was obtained as colorless crystals with the phase sequence: K134SmA178N275.8I.

[0552] Δε=2.5

[0553] <Mixture example> The compositions and physical properties of nematic mixtures M-1 to M-41 are given in the table below. The compositions are given in weight percent.

[0554] <Mixture Example M1>

[0555] Table 67

[0556] <Mixture Example M2>

[0557] Table 68

[0558] <Mixture Example M3>

[0559] Table 69

[0560] <Mixture Example M4>

[0561] Table 70

[0562] <Mixture Example M5>

[0563] Table 71

[0564] <Mixture Example M6>

[0565] Table 72

[0566] <Mixture Example M7>

[0567] Table 73

[0568] <Mixture Example M8>

[0569] Table 74

[0570] <Mixture Example M9>

[0571] Table 75

[0572] <Mixture Example M10>

[0573] Table 76

[0574] <Mixture Example M11>

[0575] Table 77

[0576] <Mixture Example M12>

[0577] Table 78

[0578] <Mixture Example M13>

[0579] Table 79

[0580] <Mixture Example M14>

[0581] Table 80

[0582] <Mixture Example M15>

[0583] Table 81

[0584] <Mixture Example M16>

[0585] Table 82

[0586] <Mixture Example M17>

[0587] Table 83

[0588] <Mixture Example M18>

[0589] Table 84

[0590] <Mixture Example M19>

[0591] Table 85

[0592] <Mixture Example M20>

[0593] Table 86

[0594] <Mixture Example M21>

[0595] Table 87

[0596] <Mixture Example M22>

[0597] Table 88

[0598] <Mixture Example M23>

[0599] Table 89

[0600] <Mixture Example M24>

[0601] Table 90

[0602] <Mixture Example M25>

[0603] Table 91

[0604] <Mixture Example M26>

[0605] Table 92

[0606] <Mixture Example M27>

[0607] Table 93

[0608] <Mixture Example M28>

[0609] Table 94

[0610] <Mixture example M29>

[0611] [Table 95]

[0612] <Mixture example M30>

[0613] [Table 96]

[0614] <Mixture example M31> Mixture Example M31 consists of 99.975% Mixture Example 1 and 0.025% Compound ST-3d.

[0615] [ka]

[0616] <Mixture example M32> Example Mixture M32 consists of 99.98% Example Mixture M1 and 0.02% of the compound of formula ST-12b-1.

[0617] [ka]

[0618] <Mixture example M33> Example Mixture M33 consists of 99.985% Example Mixture M1 and 0.015% of the compound of formula S1-1a.

[0619] [ka]

[0620] <Mixture example M34> Example Mixture M34 consists of 99.995% Example Mixture M2 and 0.005% of the compound of formula ST-9-1.

[0621] [ka]

[0622] <Mixture example M35> Blend Example M35 consists of 99.97% Blend Example 2 and 0.03% Compound ST-3d.

[0623] [ka]

[0624] <Mixture example M36> Blend Example M36 consists of 99.97% Blend Example 1 and 0.03% Compound ST-3b-1.

[0625] [ka]

[0626] <Mixture example M37>

[0627] [Table 97]

[0628] <Mixture example M38>

[0629] [Table 98]

[0630] <Mixture example M39>

[0631] [Table 99]

[0632] <Mixture Example M40>

[0633] Table 100

[0634] <Mixture Example M41>

[0635] Table 101

Claims

1. A compound of formula I. 【Chemistry 1】 (In the formula, R １１ and R １２ are the same or different and represent H, linear alkyl or alkoxy, each having 1 to 15 C atoms, linear alkenyl or alkenyloxy, each having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl, alkenyloxy, each having 3 to 15 C atoms, provided that one or more CH ２ The group is arranged such that the O atoms are not directly linked to each other. 【Chemistry 2】 -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ -, -O-, -CO-O- or -O-CO-, each independently replaced by one another, provided that one or more H atoms may be replaced by halogen; L １１ , L １２ , L １３ , L １４ are the same or different and are H, F, Cl, CH ３ , C.F. ３ or CHF ２ where L １１ , L １２ , L １３ , L １４ At least one of the following is F, Cl, or CH ３ , C.F. ３ or CHF ２ Represents.)

2. one or two groups L １１ , L １２ , L １３ and L １４ represents F, and the remaining groups L １１ , L １２ , L １３ , L １４ The compound of claim 1 , wherein represents H.

3. 3. Liquid-crystalline medium comprising one or more compounds according to claim 1 or 2.

4. 4. Liquid-crystalline medium according to claim 3, comprising one or more compounds selected from the group of compounds of the formulae II and III 【Transformation 3】 (In the formula, R ２ and R ３ are each independently H, a straight-chain alkyl or alkoxy having 1 to 15 C atoms, a straight-chain alkenyl or alkenyloxy having 2 to 15 C atoms, or a branched alkyl, alkoxy, alkenyl, alkenyloxy having 3 to 15 C atoms, provided that one or more CH ２ The group is arranged such that the O atoms are not directly linked to each other. 【Chemistry 4】 -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ -, -O-, -CO-O- or -O-CO-, each independently replaced by one another, provided that one or more H atoms may be replaced by halogen; 【Transformation 5】 are, independently of each other, 【Transformation 6】 represents L ２１ , L ２２ , L ３１ and L ３２ each independently represents H or F, Y ２ and Y ３ are the same or different and represent H or CH ３ represents X ２ and X ３ each independently represent a halogen, a halogenated alkyl or alkoxy having 1 to 3 C atoms or a halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, Z ３ is -CH ２ CH ２ -, -CF ２ CF ２ -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH ２ represents O— or a single bond, and l, m, n and o are each independently 0 or 1.

5. 5. Liquid-crystalline medium according to claim 3, which comprises one or more compounds of the formula II selected from compounds of the formulae II-1, II-2 and II-3 【Transformation 7】 (In the formula, L ２３ and L ２４ represents H or F, and L ２１ , L ２２ , R ２ , X ２ and ring element A ２２ and A ２３ has the meaning given in formula II in claim 4.

6. 6. Liquid-crystalline medium according to claim 3, comprising one or more compounds of the formula III selected from compounds of the formulae III-1 and III-2 【Transformation 8】 (In the formula, R ３ , X ３ , L ３１ , L ３２ , ring element A ３１ , A ３２ and A ３３ and n and o have the meanings given in formula III in claim 4.

7. 7. Liquid-crystalline medium according to claim 3, comprising one or more compounds selected from the group consisting of the formulae Y, B, BC, CR, PH-1 and PH-2. 【Chemistry 9】 (In the formula, R Ｙ１ , R Ｙ２ , R Ｂ１ , R Ｂ２ , R ＣＲ１ , R ＣＲ２ , R Ｐ１ and R Ｐ２ each independently represent H, a linear alkyl or alkoxy having 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl, alkenyloxy having 3 to 15 carbon atoms, provided that in these groups one or more CH ２ The groups are each independently: 【Chemistry 10】 -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ may be replaced by -, -O-, -CO-O- or -O-CO-, provided that one or more H atoms may be replaced by halogen; 【Chemistry 11】 occur independently of each other, a) a 1,4-cyclohexenylene or 1,4-cyclohexylene group, provided that one or two non-adjacent CH ２ The group may be replaced by —O— or —S—; b) a 1,4-phenylene group, in which one or two CH groups may be replaced by N, or c) a group from the group spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]-octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl represents provided that groups a), b) and c) may be mono- or polysubstituted with halogen atoms; Z ｘ , Z ｙ are the same or different and represent -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF-, -CH ２ O-, -OCH ２ -, -CO-O-, -O-CO-, -C ２ F ４ -, -CF=CF-, -CH=CH-CH ２ represents O— or a single bond, preferably a single bond, Z １ are each independently, at each occurrence, —CO—O—, —O—CO—, —CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -CH ２ -, -CH ２ CH ２ -, -(CH ２ ) ４ -, -CH=CH-CH ２ O-, -C ２ F ４ -, -CH ２ CF ２ -, -CF ２ CH ２ represents -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, L １１ and L １２ are each independently F, Cl, CF ３ or CHF ２ represents W represents O or S; n is 0, 1 or 2; c is 0, 1 or 2; x and y are independently 0, 1, or 2, provided that x + y ≦ 3.

8. Liquid-crystalline medium according to any one of claims 3 to 7, comprising one or more compounds of the formula VII 【Chemistry 12】 (In the formula, R ７１ and R ７２ represents H, F, linear alkyl or alkoxy having 1 to 15 C atoms, linear alkenyl or alkenyloxy having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy, respectively, having 3 to 15 C atoms, provided that in these groups one or more CH ２ The groups are each independently: 【Chemistry 13】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO-, provided that one or more H atoms may be replaced by halogen; X ７１ , X ７２ , X ７３ , X ７４ , X ７５ and X ７６ are the same or different and represent H or F; Z ７１ and Z ７２ are the same or different CH ２ CH ２ or a single bond.)

9. Liquid-crystalline medium according to any one of claims 3 to 8, comprising one or more compounds of the formula IV 【Chemistry 14】 (In the formula, R １１ represents a linear alkyl or alkoxy group having 1 to 12 C atoms or a branched or cyclic alkyl group having 3 to 12 C atoms or a linear alkenyl group having 2 to 12 C atoms or a branched alkenyl group having 3 to 12 C atoms or a cyclic alkenyl group having 5 to 12 C atoms, with the proviso that one or more H atoms may be replaced by fluorine, R １２ represents a linear alkyl or alkoxy group having 1 to 12 C atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 12 C atoms, or a linear alkenyl group having 2 to 12 C atoms, or a branched alkenyl group having 3 to 12 C atoms, or a cyclic alkenyl group having 5 to 12 C atoms, with the proviso that one or more H atoms may be replaced by fluorine.

10. Liquid-crystalline medium according to any one of claims 3 to 9, comprising one or more compounds of the formulae IVa and / or IVb 【Chemistry 15】 (In the formula, R ４１ and R ４２ each independently represent a straight-chain alkyl, alkoxy, alkenyl, alkoxyalkyl or alkenyloxy group having up to 12 C atoms, 【Chemistry 16】 represents Z ４ is a single bond, -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -COO-, -OCO-, -C ２ F ４ -, -C ４ H ８ - or -CF=CF-.)

11. 11. Liquid-crystalline medium according to claim 3, comprising one or more compounds of the formula V 【Chemistry 17】 (In the formula, R ５１ , R ５２ represents alkyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms, [Chemistry 18] represents Z ５１ , Z ５２ are each independently —CH ２ -CH ２ -, -CH ２ represents —O—, —CH═CH—, —C≡C—, —COO— or a single bond, and n is 1 or 2.

12. 12. Liquid-crystalline medium according to claim 3, comprising one or more compounds of the formula V-3 【Chemistry 19】 (In the formula, Z) ５１ Z ５２ , 【Chemistry 20】 and ５１ has the meaning defined in claim 11.

13. Liquid-crystalline medium according to any one of claims 3 to 12, comprising one or more compounds of the formula VIII 【Chemistry 21】 (In the formula, R ８１ and R ８２ are the same or different and represent H, halogen, CN, SCN, linear alkyl or alkoxy having 1 to 15 C atoms, linear alkenyl or alkenyloxy having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 C atoms, provided that one or more CH ２ The group is formed so that the O atoms are not directly connected to each other. 【Chemistry 22】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO-, each independently replaced by one another, provided that one or more H atoms may be replaced by halogen; A ０ , A ８１ and A ８２ are each independently phenylene-1,4-diyl (wherein one or two CH groups may be replaced by N, and one or more H atoms are halogen, CN, CH ３ , CHF ２ , C.H. ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ ), cyclohexane-1,4-diyl (wherein one or two non-adjacent CH ２ groups may be replaced independently of one another by O and / or S, and one or more H atoms may be replaced by F.), cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl; Z ８１ and Z ８２ are each independently -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -CO-O-, -O-CO-, -C ２ H ４ -, -C ２ F ４ -, -CF ２ CH ２ -, -CH ２ CF ２ -, -CFHCFH-, -CFHCH ２ -, -CH ２ CFH-, -CF ２ CFH-, -CFHCF ２ represents -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C- or a single bond; n represents 0, 1, 2 or 3, and m represents 0, 1, 2 or 3.

14. Liquid crystal display, characterized in that it comprises a liquid crystal medium according to any one of claims 3 to 13.

15. 15. The liquid crystal display of claim 14, configured to operate in IPS or FFS mode.

16. 10. A process for preparing a compound of formula I according to claim 1, comprising at least the step of removing water from a compound of formula (3). 【Chemistry 23】 (In the formula, R １１ , R １２ , L １１ , L １２ , L １３ and L １４ has the meaning given to formula I in claim 11.

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