Liquid crystal medium

Abstract

The present invention relates to a liquid crystal (LC) medium based on a mixture of polar compounds, to the use thereof for optical, electro-optical and electrical purposes, in particular in LC displays, in particular in vertical alignment mode LC displays, to vertical alignment mode LC displays, in particular energy-saving LC displays, comprising such an LC medium, and to the use thereof for optical, electro-optical and electrical purposes, in particular in LC displays, in particular in vertical alignment mode LC displays. The invention also relates to a method for manufacturing the LC display.

Description

[0001] The present invention relates to liquid crystal (LC) media based on mixtures of polar compounds, to their use for optical, electro-optical and electronic purposes, in particular in LC displays, in particular in LC displays in homeotropic mode, to LC displays in homeotropic mode comprising such LC media, in particular energy-saving LC displays, and to methods for producing such LC displays.

[0002] The popularity of 8K and gaming monitors has led to an increase in demand for LC display (LCD) panels with higher refresh rates, and therefore an increase in demand for LC media with faster response times. Many of these LCD panels use a display mode in which the LC molecules are aligned substantially perpendicularly or slightly tilted relative to the electrode surface in the off state.

[0003] Thus, so-called VA ("vertically aligned") displays are known, which have wide viewing angles and fast response times. The LC cell of a VA display contains an LC medium layer between two transparent electrodes, wherein the LC medium generally has a negative value for the dielectric anisotropy (Δε). In the switched-off state, the molecules of the LC layer are aligned perpendicularly to the electrode surfaces (homeotropic) or have a tilted homeotropic alignment. When a voltage is applied to the two electrodes, a realignment of the LC molecules parallel to the electrode surfaces occurs.

[0004] Furthermore, so-called FFS (“fringe field switching”) displays have been reported (see in particular SH Jung et al., Jpn. J. Appl. Phys., Vol. 43, No. 3, 2004, 1028), which contain two electrodes on the same substrate, one of which is structured in a comb-like manner and the other is not structured. Strong so-called “fringe fields” are thereby generated, i.e. strong electric fields close to the edges of the electrodes and electric fields with both strong vertical and strong horizontal components throughout the cell. FFS displays have a low viewing angle dependence of the contrast. FFS displays usually contain an LC medium with positive dielectric anisotropy and an alignment layer, usually a polyimide, which provides a planar alignment for the molecules of the LC medium.

[0005] FFS displays can operate as active matrix or passive matrix displays. In the case of active matrix displays, the individual pixels are typically addressed by integrated non-linear active elements such as transistors (e.g., thin film transistors ("TFTs")), while in the case of passive matrix displays, the individual pixels are typically addressed by multiplexing methods, as is known in the art.

[0006] Also known are so-called IPS ("in-plane switching") displays, which contain an LC layer with a planar orientation between two substrates, wherein two electrodes are arranged on only one of the two substrates and preferably have a crossed comb structure. When a voltage is applied to the electrodes, an electric field with a significant component parallel to the LC layer is generated between them. This leads to a realignment of the LC molecules in the layer plane.

[0007] Furthermore, FFS displays have been disclosed (see SH Lee et al., Appl. Phys. Lett. 73 (20), 1998, 2882-2883 and SH Lee et al., Liquid Crystals 39 (9), 2012, 1141-1148) which have similar electrode designs and layer thicknesses as FFS displays, but contain layers of LC media with negative dielectric anisotropy instead of LC media with positive dielectric anisotropy. LC media with negative dielectric anisotropy show more favorable director orientations with less tilted and more twisted orientations than LC media with positive dielectric anisotropy, as a result of which these displays have higher transmittance.

[0008] Furthermore, VA displays using alignment layers prepared by photoalignment, also known as UV 2 A mode (see, e.g., Q. Tang et al., SID Symposium Digest of Technical Papers 2018, 414-417). These displays utilize an alignment layer prepared from crosslinkable and photo-orientable monomers or prepolymers such as cinnamate chromophores, irradiated obliquely with linearly polarized UV light. Thus, a crosslinked alignment layer is formed, which induces a uniaxial alignment with a pretilt angle in the LC molecules near its surface. By changing the irradiation direction, a multi-domain structure with different pretilt directions can be obtained.

[0009] However, the use of LC media with negative dielectric anisotropy in VA or FFS displays also has several disadvantages. For example, they have significantly lower reliability compared to LC media with positive dielectric anisotropy.

[0010] The term "reliability" as used hereinafter refers to the performance quality of a display over a period of time and under different stress loads (e.g. light load, temperature, humidity or voltage) which lead to display defects (e.g. image sticking (areal and line image sticking), mura, smearing, etc.) and are known to those skilled in the art in the field of LC displays. As a standard parameter for classifying reliability, the voltage holding ratio (VHR) value is usually used, which is a measure of the maintenance of a constant voltage in a tested display. The higher the VHR value, the better the reliability of the LC medium.

[0011] The reduced reliability of LC media with negative dielectric anisotropy in VA or FFS displays can be explained by the interaction of the LC molecules with the polyimide of the alignment layer, as a result of which ions are extracted from the polyimide alignment layer and whereby LC molecules with negative dielectric anisotropy indeed extract such ions more efficiently.

[0012] This leads to new requirements for the LC media used in VA or FFS displays. In particular, the LC media must show high reliability and high VHR values ​​after UV exposure. Further requirements are high specific resistance, a large operating temperature range, short response times even at low temperatures, low threshold voltage, multiple grayscales, high contrast and wide viewing angles and reduced image sticking.

[0013] Therefore, in displays known from the prior art, undesirable effects so-called "image sticking" or "image burn-in" are often observed, in which the image produced in the LC display by temporary addressing of individual pixels remains visible even after the electric field in these pixels has been switched off, or after other pixels have been addressed.

[0014] On the one hand, such "image sticking" can occur if LC media with a low VHR are used. The UV component of sunlight or backlighting can lead to undesired decomposition reactions of the LC molecules therein and thus initiate the generation of ionic or radical impurities. These can accumulate in particular at the electrodes or alignment layers, where they can reduce the effectively applied voltage.

[0015] Another problem observed in the prior art is that LC media used for displays (including but not limited to VA and FFS displays) do often exhibit high viscosities and, therefore, high switching times. In order to reduce the viscosity and switching times of the LC media, it has been suggested in the prior art to add LC compounds having alkenyl groups. However, it has been observed that LC media containing alkenyl compounds often exhibit a reduction in reliability and stability, as well as a reduction in VHR, especially after exposure to UV radiation and visible light from a display backlight that does not normally emit UV light.

[0016] It was therefore an object of the present invention to provide a method for providing an improved LC medium in a VA-, IPS- or FFS-display which does not exhibit the abovementioned disadvantages or exhibits them only to a small extent and has improved properties. It was a further object of the present invention to provide FFS-displays having good transmittance, high reliability, in particular VHR values ​​after backlight exposure, high specific resistance, a large operating temperature range, short response times even at low temperatures, low threshold voltages, multiple grayscales, high contrast and wide viewing angles and reduced image sticking.

[0017] It has been found that one or more of these objects can be achieved by providing an LC medium as disclosed and claimed below.

[0018] The present invention therefore relates to a liquid-crystalline medium comprising one or more compounds of the formula IA, one or more compounds of the formula IB and one or more compounds of the formula IC,

[0019]

[0020] where the individual radicals, identical or different on each occurrence and independently of one another, have the following meanings:

[0021] R 1A , R 2A is a straight-chain, branched or cyclic alkyl radical having 1 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, CR- 0 =CR 00 -、-C≡C-、

[0022]

[0023] substituted, and wherein one or more H atoms are each optionally replaced by F or Cl, preferably alkyl or alkoxy having 1 to 6 C atoms,

[0024] R 0 ,R 00 is H or an alkyl radical having 1 to 12 C atoms,

[0025] L 1A ,L 2A is F or Cl, preferably F,

[0026] W is O or S,

[0027] Y 1 ,Y 2 is H, F, Cl, CF3, CHF2, CH3 or OCH3, preferably H, CH3 or OCH3, very preferably H,

[0028] A 3 a) 1,4-cyclohexenyl or 1,4-cyclohexylene, in which one or two non-adjacent CH2 groups may be replaced by -O- or -S-,

[0029] b) 1,4-phenylene, in which one or both CH groups may be replaced by N, or

[0030] c) a radical selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octane-2,6-diyl, 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,

[0031] wherein the groups a), b) and c) may be substituted singly or polysubstituted by halogen atoms,

[0032] n is 0, 1 or 2, preferably 0 or 1,

[0033] Z 1 is -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond,

[0034] R 1B , R 2B is an alkenyl group having 2 to 7 C atoms,

[0035] R 1C , R 2C With respect to R 1A One of the meanings given,

[0036] L 1C , L 2C With respect to L 1A One of the meanings given.

[0037] The invention further relates to the use of an LC medium as described above and below in an LC display, preferably in VA, IPS, FFS, UB-FFS or UV 2 Use in A-mode LC displays.

[0038] The liquid-crystalline medium preferably has a negative dielectric anisotropy.

[0039] The present invention also relates to a process for the preparation of an LC medium as described above and below, comprising the step of mixing one or more compounds of formula IA, IB and IC with one or more compounds of formula II or other compounds as described below and optionally with other LC compounds and / or additives.

[0040] The present invention further relates to an LC display comprising an LC medium according to the invention as described above and below, preferably a VA, IPS, FFS, UB-FFS or UV 2 A-mode LC display.

[0041] The invention also relates to a method of manufacturing an LC display as described above and below, comprising the step of filling or otherwise providing an LC medium as described above and below between substrates of the display.

[0042] When used in LC displays, the LC media according to the invention exhibit one or more of the following advantageous properties:

[0043] -High transmittance,

[0044] - High contrast,

[0045] - Reduced image retention,

[0046] - Reduced ODF non-uniformity,

[0047] - reduced rotational viscosity,

[0048] - High reliability and high VHR values ​​after UV exposure and / or heat treatment,

[0049] -Fast response time,

[0050] - A favorable low ratio of rotational viscosity to splay elastic constant γ1 / K1, which contributes to improved switching behavior, especially at low drive voltages, and is useful for realizing energy-efficient displays

[0051] - Low threshold voltage, which is useful for realizing energy-efficient displays.

[0052] Alkenyl groups in compounds of formula IA, IB, IC, or other components of the LC media disclosed below are not considered to be comprised within the meaning of the term "polymerizable group" as used herein. The conditions for polymerizing the polymerizable compounds of the LC media are preferably selected such that the alkenyl substituent does not participate in the polymerization reaction. Preferably, the LC media disclosed and claimed in the present application do not contain additives that initiate or enhance the participation of alkenyl groups in polymerization reactions.

[0053] Unless otherwise stated, the compounds disclosed above and below are preferably selected from achiral compounds, with the exception of chiral dopants.

[0054] As used herein, the expression "UV light having a wavelength of..." followed by a given wavelength range (in nm) or a given lower or upper wavelength limit (in nm) means that the UV emission spectrum of the corresponding radiation source has an emission peak, which is preferably the highest peak in the corresponding spectrum, within the given wavelength range or above the given lower wavelength limit or below the given upper wavelength limit, and / or means that the UV absorption spectrum of the corresponding compound has a long or short wavelength tail, which extends into the given wavelength range or above the given lower wavelength limit or below the given upper wavelength limit.

[0055] As used herein, the term "substantially transmissive" means that the filter transmits a majority of incident light of one or more desired wavelengths, preferably at least 50% of the intensity. As used herein, the term "substantially blocking" means that the filter does not transmit a majority of incident light of undesired wavelengths, preferably at least 50% of the intensity. As used herein, the term "desired (undesired) wavelengths" means, for example, wavelengths within (outside) a given range of λ in the case of a bandpass filter, and wavelengths above (below) a given value of λ in the case of a cutoff filter.

[0056] As used herein, the terms "active layer" and "switchable layer" are meant to refer to a layer in an electro-optical display (e.g. an LC display) that comprises one or more molecules, such as LC molecules, having structural and optical anisotropy, which change their orientation when subjected to an external stimulus such as an electric or magnetic field, resulting in a change in the transmittance of the layer to polarized or unpolarized light.

[0057] As used herein, the terms "tilt" and "tilt angle" are to be understood as meaning the tilted alignment of the LC molecules of an LC medium relative to the cell surface in an LC display, preferably a PSA display here, and are to be understood as comprising "pretilt" and "pretilt angle". Here, the tilt angle denotes the average angle (<90°) between the longitudinal molecular axes of the LC molecules (LC director) and the surfaces of the plane-parallel outer plates forming the LC cell. Here, low absolute values ​​of the tilt angle (i.e. large deviations from an angle of 90°) correspond to large tilts. Suitable methods for measuring the tilt angle are given in the examples. Unless otherwise indicated, the tilt angle values ​​disclosed above and below relate to this measurement method.

[0058] As used herein, the terms "reactive mesogen" and "RM" will be understood to mean a compound containing a mesogenic or liquid crystal backbone and attached thereto one or more functional groups suitable for polymerization and also referred to as "polymerizable groups" or "P".

[0059] Unless otherwise stated, the term "polymerizable compound" as used herein will be understood to mean a polymerizable monomeric compound.

[0060] A SA-VA display according to the invention will be of polymer-stabilized mode, since it comprises or is manufactured by using an LC medium comprising RMs (such as those described below). Thus, as used herein, the term "SA-VA display", when referring to a display according to the invention, will be understood to refer to a polymer-stabilized SA-VA display, even if this is not explicitly mentioned.

[0061] As used herein, the term "low molecular weight compound" will be understood to mean a monomeric compound as opposed to a "polymeric compound" or "polymer" and / or a compound that is not prepared by polymerization.

[0062] As used herein, the term "non-polymerizable compound" will be understood to mean a compound that does not contain a functional group that is suitable for polymerizing under the conditions normally applied to polymerize RMs.

[0063] The term "mesogenic group" as used herein is known to those skilled in the art and is described in the literature and means a group which, due to the anisotropy of its attraction and repulsion interactions, contributes substantially to the formation of a liquid crystal (LC) phase in a low molecular weight or polymeric substance. A compound containing a mesogenic group (mesogenic compound) does not necessarily have to have an LC phase itself. A mesogenic compound may also exhibit LC phase characteristics only after mixing with other compounds and / or after polymerization. Typical mesogenic groups are, for example, rigid rods or disc-shaped units. An overview of the terms and definitions used in connection with mesogenic or LC compounds is given in the following literature: Pure Appl. Chem. 2001, 73 (5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368.

[0064] As used herein, the term "spacer group", hereinafter also referred to as "Sp", is known to the person skilled in the art and is described in the literature, see for example Pure Appl. Chem. 2001, 73 (5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. As used herein, the term "spacer group" or "spacer" means a flexible group, such as an alkylene group, which connects the mesogenic group and one or more polymerizable groups in a polymerizable mesogenic compound.

[0065] Above and below, represents a trans-1,4-cyclohexylene ring,

[0066] and It represents a 1,4-phenylene ring.

[0067] In the group In the present invention, a single bond shown between two ring atoms may be attached to any free position of the benzene ring.

[0068] If in the formulae shown above and below, such as R 1A,2A , R 1B,2B , R 1C,2C , R1 , R 2 , R 11,12,13 , R 31,32 , R 41 ,42 , R 51,52 , R 61,62 , R 71,72 , R 81,82,83 , R Q , R 0 , R, R M , R S , R S1,S2,S3,S4 If the terminal group of L represents an alkyl group and / or an alkoxy group, it may be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms, and therefore preferably represents ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy or heptyloxy, and also methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.

[0069] If one of the abovementioned terminal groups represents an alkyl group in which one or more CH2 groups are replaced by S, it may be straight-chain or branched. It is preferably straight-chain, has 1, 2, 3, 4, 5, 6 or 7 C atoms, and therefore preferably represents thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl or thioheptyl.

[0070] Oxaalkyl preferably denotes straight-chain 2-oxapropyl (=methoxymethyl), 2-oxabutyl (=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-oxanononyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.

[0071] If one of the abovementioned terminal groups represents an alkoxy or oxaalkyl group, it may also contain one or more additional oxygen atoms, provided that the oxygen atoms are not directly bonded to one another.

[0072] If one of the abovementioned terminal groups represents an alkyl group in which one CH2 group has been replaced by -CH=CH-, it may be straight-chain or branched. It is preferably straight-chain and has 2 to 10 C atoms. Thus, it particularly denotes 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.

[0073] If one of the abovementioned terminal groups represents an alkyl or alkenyl group which is at least monosubstituted by halogen, the group is preferably straight-chain and the halogen is preferably F or Cl. In the case of polysubstitution, the halogen is preferably F. The resulting groups also include perfluorinated groups. In the case of monosubstitution, the fluorine or chlorine substituent can be in any desired position, but is preferably in the ω position.

[0074] In another preferred embodiment, one or more of the above terminal groups, such as R 1A,2A , R 1B,2B , R 1C,2C , R 1 , R 2 , R 11,12,13 , R 31,32 , R 41,42 , R 51,52 , R 61,62 , R 71,72 , R 81,82,83 , R Q , R 0 , R, R M , R S , R S1,S2,S3,S4 or L, selected from the following: -S 1 -F, -OS 1 -F, -O-S1-O-S2, where S 1 C 1-12 -alkylene or C 2-12 -Alkenylene and S 2 H, C 1-12 -alkyl or C 2-12 -alkenyl, and very preferably selected from the following:

[0075] -OCH2OCH3, -O(CH2)2OCH3, -O(CH2)3OCH3, -O(CH2)4OCH3, -O(CH2)2F, -O(CH2)3F, -O(CH2)4F.

[0076] Halogen is preferably F or Cl, very preferably F.

[0077] Group-CR 0 =CR 00 -Preferably -CH=CH-.

[0078] -CO-, -C(=O)- and -C(O)- represent carbonyl groups, i.e.

[0079] Preferred substituents L are, for example, 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, straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, each having 1 to 25 C atoms, wherein one or more H atoms may be optionally replaced by F or Cl, optionally substituted silyl having 1 to 20 Si atoms, or optionally substituted aryl having 6 to 25, preferably 6 to 15 C atoms,

[0080] Where R x represents H, F, Cl, CN, or a straight-chain, branched or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that the O- and / or S-atoms are not directly connected to one another, and wherein one or more H atoms are each optionally replaced by F, Cl, P- or P-Sp-, and

[0081] Y 1 Represents halogen.

[0082] Particularly preferred substituents L are, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and phenyl.

[0083] Preferably

[0084] wherein L has one of the meanings indicated above.

[0085] Preferred compounds of formula IA are those wherein W is S, and / or wherein n is 0, and / or wherein L 1A and L 2A Indicates F.

[0086] Further preferred compounds of formula IA are selected from the following sub-formulae,

[0087]

[0088]

[0089] Where L 11 and L 12 Independently of each other, in Formula IA for L 1A one of the meanings given, and preferably denotes F,

[0090] Alkyl and alkyl* each independently represent a straight-chain alkyl radical having 1 to 6 C atoms,

[0091] alkenyl and alkenyl* each independently of one another represent straight-chain alkenyl having 2 to 6 C atoms,

[0092] alkoxy and alkoxy* each independently represent a straight-chain alkoxy radical having 1 to 6 C atoms, and

[0093] L 11 and L 12 Each independently represents F or Cl, preferably both are F.

[0094] Very preferred are compounds of formula IA1, especially L 11 and L 12 Those representing F. Very preferred IA compounds and IA1 compounds are selected from the following formulas,

[0095]

[0096]

[0097] Here, alkoxy represents a straight-chain group having 1 to 6 C atoms, preferably ethoxy, propoxy, butoxy or pentoxy, most preferably ethoxy or propoxy.

[0098] Particularly preferred are formulae IA1-1 to IA1-5, and most preferred are formulae IA1-3, IA-4 and IA-5.

[0099] Preferably, the LC medium comprises formula 1, 2 or 3 compounds of formula IA or subformulae thereof.

[0100] Preferably, the total proportion of compounds of the formula IA or its subformulae in the LC medium is from 1 to 30% by weight, very preferably from 2 to 20% and most preferably from 2 to 15% by weight.

[0101] Preferred compounds of formula IB are selected from the following sub-formulae:

[0102]

[0103] Very preferably, the compound of formula IB and its subformulae, wherein

[0104] R 1B and R 2B One or both of in

[0105] m is 0, 1 or 2 and n is 0, 1 or 2, very preferably selected from compounds of the formulae IB1 to IB3.

[0106] Preferably, the LC medium comprises formula 1, 2 or 3 compounds of formula IB or subformulae thereof.

[0107] Preferably, the total proportion of compounds of the formula IB or its subformulae in the LC medium is from 1 to 30% by weight, very preferably from 2 to 20% and most preferably from 3 to 15% by weight.

[0108] Preferred compounds of formula IC are those wherein L 1C and L 2C Indicates F.

[0109] Further preferred compounds of formula IC are selected from

[0110]

[0111]

[0112] Where L 1 and L 2 Independently of each other, in formula IC, for L 1C and preferably represents F, Alkyl and Alkyl* each independently represent a straight-chain alkyl group having 1 to 6 C atoms, Alkoxy represents a straight-chain alkoxy group having 1 to 6 C atoms, Alkenyl and Alkenyl* each independently represent a straight-chain alkenyl group having 2 to 6 C atoms, and O represents an oxygen atom or a single bond. Alkenyl and Alkenyl* preferably represent 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-.

[0113] Particularly preferred compounds of formula IC are selected from the following formulae:

[0114]

[0115] Therein, Alkoxy and Alkoxy* have the meanings indicated above and preferably denote methoxy, ethoxy, n-propoxy, n-butoxy or n-pentoxy.

[0116] Very preferred are compounds of the formula IC6a, in particular in which Alkoxy and Alkxoy* represent n-butoxy.

[0117] Preferably, the LC medium comprises formula 1, 2 or 3 compounds of formula IC or subformulae thereof.

[0118] Preferably, the total proportion of compounds of the formula IC or its subformulae in the LC medium is from 1 to 30% by weight, very preferably from 2 to 20% and most preferably from 2 to 15% by weight.

[0119] Preferably, the total proportion of compounds of the formulae IA, IB and IC or subformulae thereof in the LC medium is from 20 to 80% by weight, very preferably from 30 to 70% and most preferably from 30 to 50% by weight.

[0120] Further preferred embodiments of the LC media according to the invention are listed below, including any combinations thereof:

[0121] Preferably, the LC medium further comprises one or more compounds of formula II,

[0122]

[0123] where the individual radicals, independently of one another and identically or differently on each occurrence, have the following meanings:

[0124] R 21 and R 22 is H, a straight-chain, branched or cyclic alkyl or alkoxy group having 1 to 20 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, CR 0 =CR 00 -、-C≡C-、

[0125]

[0126] substituted, and wherein one or more H atoms are each optionally replaced by F, Cl, CN or CF3, preferably an alkyl or alkoxy group having 1 to 6 C atoms,

[0127] R0 ,R 00 is H or an alkyl group having 1 to 12 C atoms,

[0128] A 1 and A 2 is a group selected from the following formula

[0129]

[0130]

[0131] Preferably selected from the formulae A1, A2, A3, A4, A5, A6, A9 and A10, very preferably selected from the formulae A1, A2, A3, A4, A5, A9 and A10,

[0132] Z 1 and Z 2 is -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2F4-, -CF=CF-, -CH=CH-CH2O- or a single bond, preferably a single bond,

[0133] L 1 ,L 2 ,L 3 and L 4 is F, Cl, OCF3, CF3, CH3, CH2F or CHF2, preferably F or Cl, very preferably F,

[0134] Y is H, F, Cl, CF3, CHF2 or CH3, preferably H or CH3, very preferably H,

[0135] L C is CH3 or OCH3, preferably CH3,

[0136] a1 is 0, 1, or 2,

[0137] a2 is 0 or 1.

[0138] Preferably, the LC medium comprises one or more compounds of formula II selected from compounds of formulae IIA, IIB, IIC and IID,

[0139]

[0140] where the individual radicals are identical or different on each occurrence and each independently of one another have the following meanings:

[0141] R 21 , R 22is H, alkyl, alkoxy or alkenyl with up to 15 C atoms, which is unsubstituted or monosubstituted by F, Cl, CN or CF3, and wherein in addition, one or more CH2 groups in these groups may be replaced by -O-, -S-, -C≡C-, -CF2O-, -OCF2-, -OC-O-, -O-CO- in such a way that the O- and / or S-atoms are not directly connected to each other. Instead,

[0142] L 1 To L 4 is F, Cl, CF3 or CHF2,

[0143] Y is H, F, Cl, CF3, CHF2 or CH3, preferably H or CH3, particularly preferably H,

[0144] Z 1 ,Z 2 is a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CH=CHCH2O,

[0145] p is 0, 1, or 2, or

[0146] q is 0 or 1.

[0147] Preferred compounds of formula IIA, IIB, IIC and IID are those wherein R 22 represents an alkyl or alkoxy radical having up to 15 C atoms and very preferably represents (O)C v H 2v+1 wherein (O) is an oxygen atom or a single bond, and v is 1, 2, 3, 4, 5 or 6.

[0148] Further preferred compounds of formula IIA, IIB, IIC and IID are those wherein R 21 or R 22 Those representing or containing cycloalkyl or cycloalkoxy groups, preferably selected from

[0149]

[0150] Where S 1 C 1-12 -alkylene or C 2-12 -alkenylene, and S 2 H, C 1-12 -alkyl or C 2-12 -alkenyl, and very preferably selected from

[0151]

[0152] Further preferred compounds of the formulae IIA, IIB, IIC and IID are indicated below.

[0153] In a preferred embodiment, the LC medium comprises one or more compounds of formula IIA selected from the group consisting of:

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] Where the index a represents 1 or 2, alkyl and alkyl * Each independently of one another represents a straight-chain alkyl group having 1 to 6 C atoms, alkenyl represents a straight-chain alkenyl group having 2 to 6 C atoms, and (O) represents an oxygen atom or a single bond, and 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-.

[0166] Particularly preferred LC media according to the invention comprise one or more compounds selected from the group consisting of formulae IIA-2, IIA-8, IIA-10, IIA-16, IIA-18, IIA-40, IIA-41, IIA-42 and IIA-43.

[0167] In another preferred embodiment, the LC medium comprises one or more compounds of the formulae IIB-1 to IIB-26 selected from the group consisting of

[0168]

[0169]

[0170]

[0171]

[0172] wherein alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 C atoms, alkenyl represents a straight-chain alkenyl group having 2 to 6 C atoms, and (O) represents an oxygen atom or a single bond, and 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-.

[0173] Particularly preferred LC media according to the invention comprise one or more compounds selected from the group consisting of formulae IIB-2, IIB-10 and IIB-16.

[0174] In another preferred embodiment, the LC medium comprises one or more compounds of the formula IIC selected from the group consisting of formula IIC-1,

[0175]

[0176] wherein alkyl and alkyl* each independently of one another denote a straight-chain alkyl radical having 1 to 6 C atoms, preferably in an amount of 0.5 to 5 wt %, in particular 1 to 3 wt %.

[0177] In another preferred embodiment, the LC medium comprises one or more compounds of formula IID selected from the group consisting of

[0178]

[0179]

[0180]

[0181] wherein alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 C atoms, alkenyl represents a straight-chain alkenyl group having 2 to 6 C atoms, and (O) represents an oxygen atom or a single bond, and 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-.

[0182] Particularly preferred LC media according to the invention comprise one or more compounds of the formula IID-4.

[0183] Very preferred compounds of formula IID are those selected from the following sub-formulae,

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] where v is 1, 2, 3, 4, 5, or 6.

[0190] In a preferred embodiment, the LC medium comprises one or more compounds of formula IID-10a

[0191]

[0192] Where R 21 , Y and q have the meanings given in formula IID, and R 23 yes wherein r is 0, 1, 2, 3, 4, 5 or 6, and s is 1, 2 or 3.

[0193] Preferred compounds of formula IID-10a are selected from formula IID-10a-1 to IID-10a-14:

[0194]

[0195]

[0196]

[0197] Particularly preferred LC media according to the invention comprise one or more compounds selected from the group consisting of formulae IIA-2, IIA-8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1 and IID-4 and IID-10 or subformulae thereof.

[0198] The proportion of compounds of the formula IIA and / or IIB in the mixture as a whole is preferably at least 20% by weight.

[0199] Preferably, the LC medium comprises one or more compounds of formula IIA-2 selected from the following subformulae:

[0200]

[0201] Alternatively, it is preferred that the LC medium comprises, in addition to the compounds of the formulae IIA-2-1 to IIA-2-5, one or more compounds of the following formulae:

[0202]

[0203]

[0204] Further preferably, the LC medium comprises one or more compounds of formula IIA-10 selected from the following subformulae:

[0205]

[0206] Alternatively, it is preferred that the LC medium comprises, in addition to the compounds of the formulae IIA-10-1 to IIA-10-5, one or more compounds of the following formulae:

[0207]

[0208] Preferably, the LC medium comprises one or more compounds of formula IIB-10 selected from the following subformulae:

[0209]

[0210]

[0211] Alternatively, it is preferred that the LC medium comprises, in addition to the compounds of the formulae IIB-10-1 to IIB-10-5, one or more compounds of the formulae IIB-10a-1 to IIB-10a-5:

[0212]

[0213] In another preferred embodiment, the LC medium comprises one or more compounds of the formula III which are different from the formula IA,

[0214]

[0215] in

[0216] R 31 and R 32 each independently of one another represents H, alkyl, alkoxy or alkenyl having up to 15 C atoms, which is unsubstituted, monosubstituted by F, Cl, CN or CF3 or at least monosubstituted by halogen, wherein in addition one or more CH2 groups in these radicals may be replaced by -O-, -S-, -S-, -S- or -S- in such a way that the O atoms are not directly connected to one another. -C≡C-, -CF2O-, -OCF2-, -OC-O- or -O-CO-,

[0217] Y 1 ,Y 2 is H, F, Cl, CF3, CHF2, CH3 or OCH3, preferably H, CH3 or OCH3, very preferably H,

[0218] A 3 Each occurrence represents independently of each other

[0219] a) 1,4-cyclohexenyl or 1,4-cyclohexylene, in which one or two non-adjacent CH2 groups may be replaced by -O- or -S-,

[0220] b) 1,4-phenylene, in which one or both CH groups may be replaced by N, or

[0221] c) a radical selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octane-2,6-diyl, 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,

[0222] wherein the groups a), b) and c) may be substituted singly or polysubstituted by halogen atoms,

[0223] n represents 0, 1 or 2, preferably 0 or 1,

[0224] Z 1Each occurrence independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, and

[0225] L 11 and L 12 each independently of one another represents F, Cl, CF3 or CHF2, preferably H or F, most preferably F, and

[0226] W represents O or S.

[0227] In the compound of formula III, R 31 and R 32 It is preferably selected from straight-chain alkyl or alkoxy having 1 to 12, preferably 1 to 7, C atoms, straight-chain alkenyl having 2 to 12, preferably 2 to 7, C atoms and cyclic alkyl or alkoxy having 3 to 12, preferably 3 to 8, C atoms.

[0228] In a preferred embodiment of the present invention, the LC medium comprises one or more compounds of the formula III-1,

[0229]

[0230] The radicals occurring therein have the same meanings as given above under formula III and are preferably

[0231] R 31 and R 32 each independently of one another is alkyl, alkenyl or alkoxy having up to 15 C atoms, more preferably one or two of them represent alkoxy, and

[0232] L 11 and L 12 Each preferably represents F.

[0233] In another preferred embodiment, the LC medium comprises one or more compounds of the formula III-1 selected from the compounds of the formulae III-1-1 to III-1-10, preferably the compounds of the formula III-1-6,

[0234]

[0235]

[0236] Among them, alkyl and alkyl *each independently of one another represents a straight-chain alkyl radical having 1 to 6 C atoms, alkenyl and alkenyl * each independently of one another represents a straight-chain alkenyl group having 2 to 6 C atoms, alkoxy and alkoxy * each independently represents a straight-chain alkoxy group having 1 to 6 C atoms, and L 11 and L 12 Each independently represents F or Cl, preferably both are F.

[0237] In another preferred embodiment of the present invention, the LC medium comprises one or more compounds of the formula III-3-1

[0238]

[0239] Where L 11 and L 12 have the same meanings as given under formula III, (O) represents O or a single bond,

[0240] R 33 represents an alkyl or alkenyl group having up to 7 C atoms, or a group Cy-C m H 2m+1 -,

[0241] m and n, identically or differently, are 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, and

[0242] Cy denotes a cycloaliphatic radical having 3, 4 or 5 ring atoms, which is optionally substituted with alkyl or alkenyl having up to 3 C atoms each, or with halogen or CN, and preferably denotes cyclopropyl, cyclobutyl or cyclopentyl.

[0243] The compound of formula III3-1 can be contained in the LC medium instead of the compound of formula III or in addition, preferably in addition.

[0244] A very preferred compound of formula III3-1 is as follows,

[0245]

[0246] Here, alkoxy represents a straight-chain alkoxy group having 1 to 6 C atoms.

[0247] In another preferred embodiment of the present invention, the LC medium comprises one or more compounds of the formulae III-4 to III-6, preferably a compound of the formula III-5,

[0248]

[0249]

[0250] where the parameters have the meanings given above, R 11 Preferably represents a straight chain alkyl group and R 12 Preferably it denotes alkoxy, each having 1 to 7 C atoms.

[0251] In another preferred embodiment, the LC medium comprises one or more compounds of formula III selected from compounds of formulae III-7 to III-9, preferably compounds of subformula III-8,

[0252]

[0253] where the parameters have the meanings given above, R 11 Preferably represents a straight chain alkyl group and R 12 Preferably it denotes alkoxy, each having 1 to 7 C atoms.

[0254] In a preferred embodiment, the LC medium comprises one or more compounds of formula IV which are different from formula IB,

[0255]

[0256] in

[0257] R 41 represents an unsubstituted alkyl radical having 1 to 7 C atoms, wherein in addition one or more CH2 groups may be substituted, or unsubstituted alkenyl having 2 to 7 C atoms, preferably n-alkyl, particularly preferably having 2, 3, 4 or 5 C atoms, and

[0258] R 42 denotes unsubstituted alkyl having 1-7 C atoms, or unsubstituted alkoxy having 1-6 C atoms, both preferably having 2-5 C atoms, unsubstituted alkenyl having 2-7 C atoms, preferably having 2, 3 or 4 C atoms, more preferably vinyl or 1-propenyl and in particular vinyl.

[0259] The compound of formula IV is preferably selected from the compounds of formulae IV-1 to IV-3,

[0260]

[0261] in

[0262] Alkyl and alkyl' independently of one another denote an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms,

[0263] Alkenyl is an alkenyl radical having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 C atoms,

[0264] Alkoxy is an alkoxy group having 1 to 5 C atoms, preferably having 2 to 4 C atoms.

[0265] Preferably, the LC medium comprises one or more compounds selected from the compounds of formulae IV-1-1 to IV-1-6

[0266]

[0267]

[0268] Very preferably, the LC media according to the invention comprise one or more compounds of the formula IV-2-1 and / or IV-2-2

[0269]

[0270] Very preferably, the LC media according to the invention comprise a compound of the formula IV-3, in particular a compound selected from the group consisting of the formulae IV-3-1 to IV-3-9:

[0271]

[0272]

[0273] Very preferably, the LC media according to the invention comprise one or more compounds of the formula IV-3 and / or one or more compounds of the formula IV-1, wherein the total concentration of the compounds of the formula IV-1 is in the range from 1% to 30%.

[0274] In another preferred embodiment, the LC media according to the invention comprise one or more compounds of the formula IV-3 selected from the following compounds of the formulae IV-3-10 to IV-3-27:

[0275]

[0276]

[0277]

[0278] wherein alkyl represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or n-pentyl.

[0279] The LC media according to the invention preferably additionally comprise one or more compounds of the formula IVa,

[0280]

[0281] in

[0282] R 41 and R 42each independently of one another represents a straight-chain alkyl, alkoxy, alkenyl, alkoxyalkyl or alkoxy radical having up to 12 C atoms, and

[0283] express

[0284]

[0285] Z 4 Represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8- or -CF=CF-.

[0286] Preferred compounds of formula IVa are indicated below:

[0287]

[0288]

[0289] Here, alkyl and alkyl* each independently represent a straight-chain alkyl radical having 1 to 6 C atoms.

[0290] The LC media according to the invention preferably comprise at least one compound of the formula IVa-1 and / or formula IVa-2.

[0291] The proportion of the compound of the formula IVa in the mixture as a whole is preferably at least 5% by weight.

[0292] Preferably, the LC medium comprises one or more compounds of the formulae IVb-1 to IVb-3

[0293]

[0294] in

[0295] Alkyl and alkyl* each independently represent a straight-chain alkyl radical having 1 to 6 C atoms, and

[0296] Alkenyl and alkenyl* each independently of one another represent straight-chain alkenyl having 2 to 6 C atoms.

[0297] The proportion of compounds of the formulae IV-1 to IV-3 in the mixture as a whole is preferably at least 3% by weight, in particular ≥5% by weight.

[0298] Among the compounds of the formulae IVb-1 to IVb-3, the compounds of the formula IVb-2 are particularly preferred.

[0299] Particularly preferred compounds of formulae IV-1 to IV-3 are selected from the following

[0300]

[0301] Therein, alkyl* denotes an alkyl group having 1 to 6 C atoms, preferably an n-propyl group.

[0302] The LC media according to the invention particularly preferably comprise one or more compounds of the formula IVb-1-1 and / or IVb-2-3.

[0303] In another preferred embodiment, the LC media according to the invention comprise one or more compounds of the formula V

[0304]

[0305] in

[0306] R 51 and R 52 independently of one another denotes H, alkyl, alkoxy or alkenyl having up to 15 C atoms, which is unsubstituted, monosubstituted by F, Cl, CN or CF3 or at least monosubstituted by halogen, wherein in addition one or more CH2 groups in these radicals may be replaced by -O-, -S-, -C≡C-, -CF2O-, -OCF2-, -OC-O-, -O-CO ...

[0307] , preferably alkyl with 1 to 7 C atoms, preferably n-alkyl, particularly preferably n-alkyl with 1 to 5 C atoms, alkoxy with 1 to 6 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy with 2 to 5 C atoms, alkoxyalkyl with 2 to 7 C atoms, preferably with 2 to 4 C atoms, alkenyl or alkenyloxy, preferably alkenyloxy,

[0308] Same or different

[0309]

[0310] in

[0311] Preferred representation

[0312] Z 51 ,Z 52 each independently represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO- or a single bond, preferably -CH2-CH2-, -CH2-O- or a single bond, and particularly preferably a single bond, and

[0313] n is 1 or 2.

[0314] The compound of formula V is preferably selected from the compounds of formulae V-1 to V-17:

[0315]

[0316]

[0317] Where R 1 and R 2 With the above R 51 and R 52 Meaning of the instructions.

[0318] R 1 and R 2 Preferably each independently of one another represents a straight-chain alkyl or alkenyl group.

[0319] Preferred LC media comprise one or more compounds of the formula V-1, V-3, V-4, V-6, V-7, V-10, V-11, V-12, V-14, V-15 and / or V-16.

[0320] The LC media according to the invention very particularly preferably comprise compounds of the formula V-10 and / or IV-1, in particular in an amount of 5 to 30%.

[0321] Preferred compounds of formula V-10 are indicated below:

[0322]

[0323] The LC medium according to the invention particularly preferably comprises a combination of a tricyclic compound of the formula V-10a and / or V-10b with one or more bicyclic compounds of the formula IV-1. The total proportion of the combination of the compounds of the formula V-10a and / or V-10b with one or more bicyclohexyl compounds selected from the group consisting of the compounds of the formula IV-1 is 5 to 40%, very particularly preferably 15 to 35%.

[0324] Particularly preferred LC media comprise compounds V-10a and / or IV-1-1

[0325]

[0326] The compounds V-10a and IV-1-1 are preferably present in the mixture in a concentration of 5 to 30%, very preferably 10 to 25%, based on the mixture as a whole.

[0327] Preferred LC media comprise at least one compound selected from the group consisting of

[0328]

[0329] Where R1 ,R 2 ,R 41 and R 42 has the meaning indicated above. Preferably, in compounds V-6, V-7 and IV, R 1 and R 41 represents an alkyl or alkenyl group having 1 to 6 or 2 to 6 C atoms, R 2 and R 42 represents an alkenyl group having 2 to 6 C atoms. Preferably, in compound V-14, R 1 represents an alkyl or alkenyl group having 1-6 or 2-6 C atoms, and R 2 represents an alkyl group having 1 to 6 C atoms.

[0330] In another preferred embodiment, the LC media according to the invention comprise one or more compounds of the formula V-7, preferably selected from the group consisting of the compounds of the formulae V-7a to V-7e:

[0331]

[0332]

[0333] Wherein alkyl represents an alkyl group having 1-7 C atoms, alkenyl represents an alkenyl group having 2-7 C atoms, and cycloalkyl represents a cyclic alkyl group having 3-12 C atoms, preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylalkyl, cyclobutylalkyl or cyclopentylalkyl.

[0334] Very preferred compounds of formula V-7a to V-7e are selected from the following compounds of formula V7-b1 to V7-b3, V-7d-1 to V-7d-8 and V-7e-1 to V-7e-12:

[0335]

[0336]

[0337]

[0338] wherein alkyl represents ethyl, n-propyl, n-butyl or n-pentyl, preferably n-propyl.

[0339] Further preferred are compounds of formula V, wherein R 51 and R 52 Independently of one another represent straight-chain alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms.

[0340] In a preferred embodiment of the present invention, the LC medium additionally comprises one or more compounds of the formulae VI-1 to VI-25,

[0341]

[0342]

[0343]

[0344] in

[0345] R represents a straight chain alkyl or alkoxy group having 1 to 6 carbon atoms, (O) represents -O- or a single bond, X represents F, Cl, OCF3 or OCHF2, L x represents H or F, m is 0, 1, 2, 3, 4, 5 or 6 and n is 0, 1, 2, 3 or 4.

[0346] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentyloxy.

[0347] X preferably represents F or OCH3, very preferably F.

[0348] The LC media according to the invention preferably comprise the terphenyls of the formulae VI-1 to VI-25 in an amount of 2 to 30% by weight, in particular 5 to 20% by weight.

[0349] Particularly preferred are compounds of formulae VI-1, VI-2, VI-4, VI-20, VI-21 and VI-22, in which X represents F. In these compounds, R preferably represents alkyl and alkoxy, each having 1 to 5 C atoms. In the compound of formula VI-20, R preferably represents alkyl or alkenyl, in particular alkyl. In the compound of formula VI-21, R preferably represents alkyl. In the compounds of formulae VI-22 to VI-25, X preferably represents F.

[0350] Terphenyls of the formulae VI-1 to VI-25 are preferably used in the LC media according to the invention if the Δn value of the mixture is ≥ 0.1. Preferred LC media comprise 2 to 20 wt % of one or more terphenyl compounds selected from the compounds of the formulae VI-1 to VI-25.

[0351] In another preferred embodiment of the present invention, the LC medium additionally comprises one or more compounds of the formulae VII-1 to VII-9

[0352]

[0353]

[0354] in

[0355] R 1 Each independently has the formula IIA for R21 One of the meanings of the indication, and

[0356] w and x each independently represent 1 to 6.

[0357] Particular preference is given to LC media which comprise at least one compound of the formula VII-9.

[0358] Further embodiments of the present invention are as follows:

[0359] a) an LC medium comprising at least one compound of the formulae Z-1 to Z-7,

[0360]

[0361]

[0362] wherein R, (O) and alkyl have the meanings indicated for formula III.

[0363] b) LC media comprising one or more substances containing tetrahydronaphthyl or naphthyl units, for example compounds of the formulae N-1 to N-5,

[0364]

[0365] Where R 61 and R 62 Each independently has a 21 The indicated meanings preferably represent straight-chain alkyl, straight-chain alkoxy or straight-chain alkenyl, and

[0366] Z 61 and Z 62 Each independently represents -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CH2- or a single bond.

[0367] c) an LC medium comprising one or more compounds selected from the group consisting of difluorodibenzochroman compounds of formula BC, chroman compounds of formula CR and fluorinated phenanthrene compounds of formulae PH-1 and PH-2,

[0368]

[0369] in

[0370] R 71 and R 72 Each independently has R21 and c is 0, 1 or 2. 71 and R 72 Preferably, independently of one another, they are alkyl or alkoxy radicals having 1 to 6 C atoms.

[0371] The LC media according to the invention preferably comprise the compound of the formula BC, CR, PH-1, PH-2 in an amount of 3 to 20 wt.-%, in particular in an amount of 3 to 15 wt.-%.

[0372] Particularly preferred compounds of formula BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5,

[0373]

[0374]

[0375]

[0376] in

[0377] Alkyl and alkyl* each independently represent a straight-chain alkyl radical having 1 to 6 C atoms, and

[0378] Alkenyl and alkenyl* each independently of one another represent straight-chain alkenyl having 2 to 6 C atoms.

[0379] Very particular preference is given to LC media which comprise one, two or three compounds of the formula BC-2, BF-1 and / or BF-2.

[0380] d) an LC medium comprising one or more indane compounds of the formula In,

[0381]

[0382] in

[0383] R 81 ,R 82 ,R 83 Each independently of one another represents straight-chain alkyl, alkoxy, alkoxyalkyl or alkenyl having 1 to 6 C atoms.

[0384] R 82 and R 83 It can also represent halogen, preferably F,

[0385] express

[0386]

[0387] i represents 0, 1 or 2.

[0388] Preferred compounds of formula In are compounds of formula In-1 to In-16 indicated below:

[0389]

[0390]

[0391] Compounds of the formulae In-1, In-2, In-3 and In-4 are particularly preferred.

[0392] The compounds of the formula In and subformulae In-1 to In-16 are preferably used in the LC media according to the invention in a concentration of ≥5% by weight, in particular 5 to 30% by weight and very particularly preferably 5 to 25% by weight.

[0393] e) an LC medium comprising one or more compounds of the formulae L-1 to L-8,

[0394]

[0395] in

[0396] R to R 1 Each independently has the above R 21 The parameter s represents 1 or 2.

[0397] The compounds of the formulae L-1 to L-8 are preferably used in a concentration of 5 to 15% by weight, in particular 5 to 12% by weight, very particularly preferably 8 to 10% by weight.

[0398] f) LC medium comprising one or more quaternary compounds selected from the group consisting of:

[0399]

[0400] in

[0401] R Q is alkyl, alkoxy, oxaalkyl or alkoxyalkyl having 1 to 9 C atoms, or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated,

[0402] X Q is F, Cl, a haloalkyl or alkoxy group having 1 to 6 C atoms, or a haloalkenyl or alkenyloxy group having 2 to 6 C atoms,

[0403] L Q1 -L Q6 are independently H or F, where L Q1 -L Q6 At least one of them is F.

[0404] Preferred compounds of formula Q are those wherein R Q denotes straight-chain alkyl radicals having 2 to 6 C atoms, very preferably those which are ethyl, n-propyl or n-butyl.

[0405] Preferred compounds of formula Q are those wherein L Q3 and L Q4 Those wherein L is F. Further preferred compounds of formula Q are those wherein L Q1 and L Q2 One or both of L Q3 , L Q4 Those for F.

[0406] Preferred compounds of formula Q are those wherein X Q represents F or OCF3, those of F being very preferred.

[0407] The compound of formula Q is preferably selected from the following sub-formula

[0408]

[0409] Where R Q has one of the meanings of the formula Q or one of the preferred meanings given above and below, and is preferably ethyl, n-propyl or n-butyl.

[0410] Particularly preferred are compounds of formula Q1, especially wherein R Q Those compounds which are n-propyl.

[0411] Preferably, the proportion of the compound of the formula Q in the LC medium is >0 to ≤5% by weight, very preferably 0.05 to 2% by weight, more preferably 0.1 to 1% by weight, most preferably 0.1 to 0.8% by weight.

[0412] Preferably, the LC medium contains 1 to 5, preferably 1 or 2, compounds of formula Q.

[0413] Adding quaterphenyl compounds of formula Q to the LC mixture of a polymerizable LC medium enables reduction of ODF inhomogeneities while maintaining high UV absorption, which enables fast and complete polymerisation, enables strong and fast tilt angle generation and improves the UV stability of the LC medium.

[0414] Furthermore, the addition of compounds of formula Q with positive dielectric anisotropy to LC media with negative dielectric anisotropy allows for better control of the dielectric constant ε || and ε ⊥ and in particular enables a high dielectric constant ε to be achieved while keeping the dielectric anisotropy Δε constant. ||value, thereby reducing the kick-back voltage and reducing image retention.

[0415] In another preferred embodiment, the LC liquid crystals contain small amounts, preferably 0.05 to 3%, very preferably 0.1 to 2%, of one or more compounds having positive dielectric anisotropy and preferably selected from the group consisting of formulae P1 and P2

[0416]

[0417] Therein, the individual radicals, independently of one another and identically or differently on each occurrence, have the following meanings:

[0418] R 0 A straight-chain, branched or cyclic alkyl radical having 1 to 25 C atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, CR 0 =CR 00 -,-C≡C-,

[0419]

[0420] substituted in such a way that O- and / or S-atoms are not adjacent to one another, and wherein one or more H atoms are each optionally replaced by F or Cl, preferably an alkyl or alkoxy radical having 1 to 6 C atoms,

[0421] R 0 ,R 00 H or alkyl having 1 to 12 C atoms,

[0422]

[0423] X 0 F, Cl, CN, SF5, SCN, NCS, haloalkyl, haloalkenyl, haloalkoxy or haloalkenyloxy with up to 6 C atoms,

[0424] Y 0 H, F, Cl, CF3, CHF2, CH3 or OCH3, preferably H, CH3 or OCH3, very preferably H,

[0425] Y 1-6 H or F.

[0426] Preferably, the LC medium comprises one or more compounds of formula II, wherein Y 0 is H, preferably selected from the following sub-formulae:

[0427]

[0428] Where R 0 and X 0 has the meaning given above:

[0429] Preferred compounds are compounds of formula P1-1, P1-2 and P1-3, with formula P1-1 and P1-2 being very preferred.

[0430] In the compounds of formula P1-1 and P1-7, R 0 preferably represents alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, and X 0 Preferably it represents F or OCF3, very preferably F.

[0431] In another preferred embodiment, the LC medium comprises one or more compounds of the formula P1, wherein Y 0 is CH3, preferably selected from the following subformulae:

[0432]

[0433]

[0434] Where R 0 and X 0 has the meaning given above.

[0435] Preferred compounds are those of formulae P1A-1, P1A-2 and P1A-3, with formulae P1A-1 and P1A-2 being very preferred.

[0436] In Formulas P1A-1 to P1A-7, R 0 preferably represents alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, and X 0 Preferably it represents F or OCF3, very preferably F.

[0437] Further preferably, the LC medium comprises one or more compounds of formula P2, wherein Y 0 is H, preferably selected from the following sub-formulae:

[0438]

[0439]

[0440]

[0441]

[0442] Where R 0 and X 0 has the meaning given above.

[0443] Preferred compounds are those of formula P2-1, P2-4, P2-6, P2-16, P2-19 and P2-20.

[0444] In the compounds of formulae P2-1 to P2-21, R 0 Preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, X 0 Preferably it represents F or OCF3, very preferably F and Y 2 Preferably it represents F.

[0445] In another preferred embodiment, the LC medium comprises one or more compounds of formula P2, wherein Y 0 is CH3, preferably selected from the following sub-formula:

[0446]

[0447]

[0448]

[0449]

[0450] Where R 0 and X 0 has the meaning given above.

[0451] Preferred compounds are those of formula P2A-1, P2A-4, P2A-6, P2A-16, P2A-19 and P2A-20.

[0452] In the compounds of formulae P2A-1 to P2A-21, R 0 Preferably denotes alkyl having 1 to 6 C atoms, very preferably ethyl or propyl, X 0 Preferably represents F or OCF3, very preferably F, and Y 2 Preferably it represents F.

[0453] The concentration of the individual compounds of the formula P1 or subformulae thereof in the LC medium is preferably from 0.1 to 3% by weight. The total concentration of the compounds of the formula II in the LC medium is preferably from 0.2 to 0.9% by weight.

[0454] The concentration of the individual compounds of the formula P2 or subformulae thereof in the LC medium is preferably from 0.1 to 3% by weight. The total concentration of the compounds of the formula III in the LC medium is preferably from 0.2 to 0.9% by weight.

[0455] Preferably, the LC medium comprises 1, 2 or 3 compounds of formula P1 and / or formula P2 or subformulae thereof.

[0456] The LC media according to the invention preferably comprise

[0457] one or more compounds of the formula IA or its subformulae, preferably selected from the compounds of the formulae IA1-1 to IA1-5, preferably in a proportion of 1 to 30% by weight, very preferably 2 to 20% by weight, most preferably 2 to 15% by weight;

[0458] one or more compounds of the formula IB or its subformulae, preferably selected from the compounds of the formulae IB1 to IB6, preferably in a proportion of 1 to 30% by weight, very preferably 2 to 20% by weight, most preferably 3 to 15% by weight;

[0459] one or more compounds of the formula IC or its subformulae, preferably selected from the compounds of the formula IC6a, preferably in a proportion of 1 to 30% by weight, very preferably 2 to 20% by weight, most preferably 2 to 15% by weight;

[0460] and / or

[0461] - one or more compounds of the formula IA, one or more compounds of the formula IB and one or more compounds of the formula IC or subformulae thereof in a total concentration of 20 to 80% by weight, very preferably 30 to 70% by weight, most preferably 30 to 50% by weight;

[0462] and / or

[0463] - one or more compounds of the formula IV, preferably in a total concentration ranging from 35% to 60%, more preferably from 40% to 55%, particularly preferably from 45% to 50%;

[0464] and / or

[0465] - one or more compounds of the formula IIA and / or IIB, preferably in a total concentration in the range of 30% to 65%, more preferably 35% to 60%, particularly preferably 40 to 55%.

[0466] In particular, the LC medium comprises

[0467] - one or more compounds CY-n-Om, in particular CY-3-O4, CY-5-O4 and / or CY-3-O2, preferably in a total concentration in the range of 5% to 30%, preferably 10% to 20%, based on the mixture as a whole;

[0468] and / or

[0469] - one or more compounds PY-n-Om, in particular PY-1-O2, PY-2-O2 and / or PY-3-O2, preferably in a total concentration in the range of 5% to 40%, preferably 10% to 30%, based on the mixture as a whole;

[0470] and / or

[0471] - one or more compounds PY-n-Om, in particular CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably in a concentration of >5%, in particular 7 to 20%, based on the mixture as a whole;

[0472] and / or

[0473] - one or more compounds CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, preferably in a concentration of >3%, in particular 5 to 15%, based on the mixture as a whole;

[0474] and / or

[0475] - one or more compounds CPY-n-Om and CY-n-Om, preferably in a concentration of 10 to 80%, based on the mixture as a whole,

[0476] and / or

[0477] one or more compounds CPY-n-Om and PY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2 and PY-3-O2 or PY-1-O2, preferably in a concentration of 5 to 20%, more preferably 10 to 15%, based on the mixture as a whole,

[0478] and / or

[0479] - one or more compounds selected from CCH-13, CCH-23, CCH-34, CCH-35, CCH-301 and CCH-303, preferably in a total concentration of 3 to 40%, preferably 3 to 25%, based on the mixture as a whole,

[0480] and / or

[0481] - one or more compounds selected from CC-2-V1, CC-3-V1, CC-3-V2, CC-4-V1, CC-3-V, CC-4-V and CC-5-V, preferably in a total concentration of 3 to 40%, more preferably 5 to 30%, based on the mixture as a whole,

[0482] and / or

[0483] one or more compounds CCP-nm and / or CCP-Vn-m and / or CPP-nm, preferably selected from CCP-3-1, CCP-V-1, CCP-V2-1 and CPP-3-2, preferably in a total concentration of 4 to 35%, preferably 5 to 25%, based on the mixture as a whole,

[0484] and / or

[0485] one or more compounds CLP-nm and / or CLP-Vn-m, preferably selected from CLP-3-1, CLP-3-2 and CLP-V-1, preferably in a total concentration of 1 to 25%, preferably 2 to 15%, based on the mixture as a whole,

[0486] and / or

[0487] - one or more selected from PY-Vn-Om, CCY-V-Om and CPY-V-Om, preferably selected from PY-V2-O2, CCY-V-O2, CPY-V-O2 and CPY-V-O4, preferably with a total concentration of 4 to 30%, preferably 5 to 25%, based on the entire mixture,

[0488] and / or

[0489] - one or more compounds selected from PYP-nm, PGIY-n-Om and PGP-n-2V, preferably in a total concentration of 2 to 20%, more preferably 2 to 15%, most preferably 2 to 10%, based on the entire mixture,

[0490] and / or

[0491] one or more compounds COY-n-Om and / or CCOY-n-Om, preferably selected from COY-3-O2, CCOY-2-O2 and CCOY-3-O2, preferably in a total concentration of 2 to 25%, preferably 3 to 20%, based on the mixture as a whole,

[0492] and / or

[0493] - the compound CCQU-3-F, preferably in a concentration of 0.1 to 3%, very preferably 0.1 to 0.9%, based on the mixture as a whole,

[0494] and / or

[0495] - the compound PPGU-3-F, preferably in a concentration of 0.1% to 3%, based on the mixture as a whole.

[0496] Advantageously, the liquid-crystalline media according to the invention preferably have a nematic phase from ≤-20°C to ≥70°C, particularly preferably from ≤-30°C to ≥80°C, very particularly preferably from ≤-40°C to ≥90°C.

[0497] The LC media according to the invention have a clearing temperature of 70° C. or higher, preferably 74° C. or higher.

[0498] Here, the expression "has a nematic phase" means on the one hand that no smectic phase and no crystallization is observed at low temperatures at the corresponding temperature and on the other hand that no clearing occurs even when heating from the nematic phase. The investigations at low temperatures are carried out in a flow viscometer at the corresponding temperature and checked by storage for at least 100 hours in test cells with a layer thickness corresponding to the electro-optical application. If the storage stability at a temperature of -20°C in a corresponding test cell is 1000 hours or more, the LC medium is said to be stable at this temperature. At temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the clearing point is measured in a capillary by conventional methods.

[0499] The liquid crystal mixture preferably has a nematic phase range of at least 60 K and a nematic phase range of at most 30 mm at 20° C. 2 ·s -1 The flow viscosity ν 20 .

[0500] The mixture is nematic at a temperature of -20°C or below, preferably at a temperature of -30°C or below, very preferably at a temperature of -40°C or below.

[0501] The value of the birefringence Δn in the liquid-crystal mixture is generally between 0.07 and 0.16, preferably between 0.08 and 0.15, very preferably between 0.09 and 0.14. In a preferred embodiment of the invention, the LC medium has a birefringence in the range of 0.090 to 0.110, preferably 0.095 to 0.108, in particular 0.102 to 0.107.

[0502] The liquid-crystal mixtures according to the invention have a dielectric anisotropy Δε of -1.5 to -8.0, in particular -2.0 to -4.0, in particular -2.5 to -3.6.

[0503] The rotational viscosity γ1 at 20° C. is preferably ≤120 mPa·s, in particular ≤105 mPa·s. In a preferred embodiment, the rotational viscosity γ1 at 20° C. is ≤100 mPa·s, in particular ≤95 mPa·s.

[0504] The liquid-crystal media according to the invention have relatively low threshold voltage (V0) values, which are preferably in the range from 1.7 V to 3.0 V, particularly preferably ≤2.7 V and very particularly preferably ≤2.5 V.

[0505] For the present invention, unless explicitly stated otherwise, the term "threshold voltage" relates to the capacitance threshold (V0) also known as the Freedericks threshold.

[0506] Furthermore, the liquid-crystalline media according to the invention have high voltage holding ratio values ​​in liquid-crystal cells.

[0507] Typically, liquid crystal media having a low addressing voltage or threshold voltage exhibit a lower voltage holding ratio than those having a higher addressing voltage or threshold voltage, and vice versa.

[0508] For the purposes of the present invention, the term "dielectrically positive compounds" refers to compounds with Δε>1.5, the term "dielectrically neutral compounds" refers to those compounds with -1.5≤Δε≤1.5, and the term "dielectrically negative compounds" refers to those compounds with Δε<-1.5. The dielectric anisotropy of the compounds is determined here by dissolving 10% of the compounds in a liquid-crystal host and determining the capacitance of the resulting mixture at 1 kHz with homeotropic surface alignment and with planar surface alignment in at least one test cell, the cell having a layer thickness of 20 μm in each case. The measuring voltage is typically 0.5 V to 1.0 V, but is always below the capacitance threshold of the respective liquid-crystal mixture under investigation.

[0509] All temperature values ​​indicated in the present invention are in ° C.

[0510] The LC media according to the invention are suitable for all VA-TFT (vertically aligned thin film transistor) applications, such as VAN (vertically aligned nematic), MVA (multidomain VA), (S)-PVA (super patterned VA), ASV (advanced super view, or axisymmetric VA), PSA (polymer sustained VA) and PS-VA (polymer stabilized VA). They are also suitable for IPS (in-plane switching) and FFS (fringe field switching) applications with negative Δε.

[0511] The nematic LC media in the displays according to the invention generally comprise two components A and B, which themselves consist of one or more individual compounds.

[0512] Component A has a significantly negative dielectric anisotropy and provides a dielectric anisotropy of ≤-0.5 for the nematic phase. In addition to one or more compounds of the formulae IA and IB, it preferably comprises compounds of the formulae IIA, IIB and / or IIC and furthermore one or more compounds of the formula IV-1.

[0513] The proportion of component A is preferably between 45 and 100%, in particular between 60 and 85%.

[0514] For component A, preference is given to selecting one (or more) individual compounds having a Δε value of ≤−0.8. The smaller the proportion A in the mixture as a whole, the more negative this value must be.

[0515] Component B has significant nematogeneity and a particle size of no more than 30 mm at 20°C. 2 ·s -1 , preferably no more than 25mm 2 ·s -1 The flow viscosity.

[0516] A large number of suitable materials are known to the person skilled in the art from the literature. Compounds of the formula O-17 are particularly preferred.

[0517] Particularly preferred individual compounds in component B are those having a molecular weight of not more than 18 mm at 20°C. 2 ·s -1 , preferably no more than 12mm 2 ·s -1 Very low viscosity nematic liquid crystal with a flow viscosity of .

[0518] Component B is monotropically or enantiotropically nematic, has no smectic phase, and is capable of preventing the appearance of a smectic phase in the LC medium at low to very low temperatures. For example, if various highly nematic materials are added to a smectic liquid crystal mixture, the nematicity of these materials can be compared by the degree of suppression of the smectic phase achieved.

[0519] The mixture may optionally further comprise a component C comprising compounds having a dielectric anisotropy of Δε≥1.5. These so-called positive compounds are generally present in mixtures of negative dielectric anisotropy in an amount of ≤20% by weight, based on the mixture as a whole.

[0520] In addition to one or more compounds of the formulae IA and IB, the LC medium preferably comprises 4 to 15, in particular 5 to 12 and particularly preferably <10 compounds of the formulae IIA, IIB and / or IIC and optionally one or more compounds of the formula IV-1.

[0521] Besides the compounds of the formulae IA and IB and the compounds of the formulae IIA, IIB and / or IIC and optionally IV-1, further constituents may be present, for example in amounts of up to 45%, but preferably up to 35%, in particular up to 10%, of the mixture as a whole.

[0522] The further components are preferably selected from nematic or nematic substances, in particular from the known substances of the class of azobenzene, benzylideneaniline, biphenyl, terphenyl, phenyl or cyclohexyl benzoate, phenyl or cyclohexyl cyclohexanecarboxylate, phenylcyclohexane, cyclohexylbiphenyl, cyclohexylcyclohexane, cyclohexylnaphthalene, 1,4-dicyclohexylbiphenyl or cyclohexylpyrimidine, phenyldioxane or cyclohexyldioxane, optionally halogenated stilbenes, benzylphenyl ethers, tolans and substituted cinnamic esters.

[0523] The most important compounds suitable as constituents of this type of liquid-crystalline phase can be characterized by the formula IV

[0524] R 20 -LGER 21 IV

[0525] wherein L and E each represent a carbocyclic or heterocyclic ring system, the system being derived from a radical formed from 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyls, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidines and 1,3-disubstituted Alkanes, 2,6-disubstituted naphthalenes, dihydronaphthalenes and tetrahydronaphthalenes, quinazolines and tetrahydroquinazolines,

[0526] G represents -CH=CH- -N(O)=N-

[0527] -CH=CQ- -CH=N(O)-

[0528] -C≡C- -CH2-CH2-

[0529] -CO-O- -CH2-O-

[0530] -CO-S- -CH2-S-

[0531] -CH=N- -COO-Phe-COO-

[0532] -CF2O- -CF=CF-

[0533] -OCF2- -OCH2-

[0534] -(CH2)4- -(CH2)3O-

[0535] or CC single key,

[0536] Q represents halogen, preferably chlorine, or -CN, and

[0537] R 20 and R 21Each represents an alkyl, alkenyl, alkoxy, alkoxyalkyl or alkoxycarbonyloxy group having up to 18, preferably up to 8, carbon atoms, or one of these groups alternatively represents CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl or Br.

[0538] In most of these compounds, R 20 and R 21 are different from one another, one of these groups being generally an alkyl or alkoxy group. Other variants of the proposed substituents are also common. Many such substances or also mixtures thereof are commercially available. All these substances can be prepared by methods known from the literature.

[0539] It is self-evident to the person skilled in the art that the VA, IPS or FFS mixtures according to the invention may also comprise compounds in which, for example, H, N, O, Cl and F have been replaced by the corresponding isotopes.

[0540] The LC medium preferably has a nematic LC phase.

[0541] Preferably, the LC medium comprises one or more polymerizable compounds, which are preferably selected from polymerizable mesogenic compounds, which are also called "reactive mesogens" or RMs, very preferably selected from the formula M

[0542] R a -B 1 -(Z m -B 2 ) m -R b M

[0543] where the individual radicals, identically or differently on each occurrence and independently of one another, have the following meanings:

[0544] R a and R b represents P, P-Sp-, H, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, SF5 or a straight-chain or branched alkyl radical having 1 to 25 C atoms, wherein in addition one or more non-adjacent CH2 groups may also be each independently replaced by -C(R 0 )=C(R 00 )-、-C≡C-、-N(R 00 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, in such a way that O and / or S atoms are not directly connected to one another, and wherein in addition one or more H atoms may also be replaced by F, Cl, Br, I, CN, P or P-Sp-, wherein if B 1 and / or B2 Contains saturated C atoms, then R a and / or R b It can also represent a group connected to this saturated C atom spiro ring,

[0545] The group R a and R b At least one of them represents or contains a group P or P-Sp-,

[0546] P represents a polymerizable group,

[0547] Sp represents a spacer group or a single bond,

[0548] B 1 and B 2 denotes an aromatic, heteroaromatic, alicyclic or heterocyclic radical, which preferably has 4 to 25 ring atoms, which may also contain fused rings, and which is unsubstituted or mono- or polysubstituted by L,

[0549] Z m Represents -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-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-COO-, -OCO-CH=CH-, -CH2CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 - or single key,

[0550] R 0 and R 00 represents H or an alkyl group having 1 to 12 C atoms,

[0551] m represents 0, 1, 2, 3 or 4,

[0552] n1 means 1, 2, 3 or 4,

[0553] L represents 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 straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which one or more H atoms may also be replaced by F, Cl, P or P-Sp-,

[0554] Y 1 represents halogen,

[0555] R x represents P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein in addition one or more non-adjacent CH2 groups can also be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that the O and / or S atoms are not directly connected to one another, and in which in addition one or more H atoms can also be replaced by F, Cl, P or P-Sp-, optionally substituted aryl or aryloxy groups having 6 to 40 C atoms, or optionally substituted heteroaryl or heteroaryloxy groups having 2 to 40 C atoms.

[0556] The polymerizable group P is a group suitable for polymerization reactions (e.g. free radical or ionic chain polymerization, addition polymerization or condensation polymerization) or for polymer-analogous transformation reactions (e.g. addition or condensation to the polymer backbone). Particularly preferred are groups for chain polymerization, in particular those containing a C=C double bond or a -C≡C- triple bond, and groups suitable for polymerization under ring opening, such as oxetane or epoxy groups.

[0557] Preferred groups P are selected from CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, 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-CW 2 W3 -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-, where W 1 represents H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, W 2 and W 3 each independently of one another represents 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 C atoms, W 7 and W 8 Each independently represents H, Cl or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene which is optionally substituted by one or more groups L other than P-Sp- as defined above, k1, k2 and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0558] Very preferably the group P is selected from CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, 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-, where W 1 represents H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, W 2 and W 3 each independently of one another represents 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 C atoms, W 7 and W 8 Each independently represents H, Cl or an alkyl group 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.

[0559] Very particularly preferred groups P are selected from the group consisting of CH2=CW 1 -CO-O-, especially CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, in addition CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-,

[0560] Further preferred polymerizable groups P are selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetanyl and epoxy, most preferably from acrylate and methacrylate.

[0561] Very preferably, all polymerizable groups in the polymerizable compounds have the same meaning.

[0562] If the spacer group Sp is not a single bond, it is preferably a spacer group of the formula Sp"-X", so that the corresponding group P-Sp- conforms to the formula P-Sp"-X"-, where

[0563] Sp" denotes a straight-chain or branched alkylene radical having 1 to 20, preferably 1 to 12 C atoms, which is optionally mono- or polysubstituted by F, Cl, Br, I or CN, and in which one or more non-adjacent CH2 groups may also each independently of one another be substituted by -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- in such a way that the O and / or S atoms are not directly connected to each other,

[0564] X" means -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 -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or a single bond,

[0565] R 0 and R 00 each independently of one another represents H or an alkyl group having 1 to 20 C atoms, and

[0566] Y 2 and Y 3 Each independently of one another represents H, F, Cl or CN.

[0567] X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -、-NR 0 -CO-、-NR 0 -CO-NR 00 - or single key.

[0568] Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH2) p1 -、-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, -(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 indicated above.

[0569] 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-, wherein p1 and q1 have the meanings indicated above.

[0570] 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, vinylene, propenylene and butenylene.

[0571] In a preferred embodiment of the present invention, the polymerizable compound contains a spacer group Sp which is substituted by one or more polymerizable groups P such that the group Sp-P corresponds to Sp(P) s , wherein s is ≥ 2 (branched polymerizable group).

[0572] Preferred polymerizable compounds according to this preferred embodiment are those compounds wherein s is 2, ie compounds containing the group Sp(P)2. Very preferred polymerizable compounds according to this preferred embodiment contain a group selected from the formula:

[0573]

[0574]

[0575] wherein P is as defined in Formula M,

[0576] Alkyl represents a single bond or a straight-chain or branched alkylene radical having 1 to 12 C atoms, which is unsubstituted or mono- or polysubstituted by F, Cl or CN, and in which one or more non-adjacent CH2 groups may each be replaced independently of one another by -C(R 0)=C(R 0 )-、-C≡C-、-N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, wherein O and / or S atoms are not directly connected to each other, wherein R 0 has the meaning given above,

[0577] aa and bb each independently represent 0, 1, 2, 3, 4, 5 or 6,

[0578] X has one of the meanings indicated for X" and is preferably O, CO, SO2, O-CO-, CO-O or a single bond.

[0579] Preferred spacer groups Sp(P)2 are selected from the group consisting of formulae S1, S2 and S3.

[0580] Very preferred spacer groups Sp(P)2 are selected from the following sub-formulae:

[0581]

[0582] P is preferably selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetanyl and epoxy, very preferably from acrylate and methacrylate, most preferably from methacrylate.

[0583] It is further preferred that all polymerizable groups P present in the same compound have the same meaning and very preferably denote acrylate or methacrylate groups, most preferably methacrylate groups.

[0584] Sp preferably represents a single bond or -(CH2) p1 -、-(CH2) p2 -CH=CH-(CH2) p3 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 , wherein p1 is 2, 3, 4, 5 or 6, preferably 2 or 3, p2 and p3 are independently 0, 1, 2 or 3, and if Sp is -O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 , then the O atom or CO group is connected to the benzene ring respectively.

[0585] Further preferably, at least one group Sp is a single bond.

[0586] Further preferably, at least one group Sp is not a single bond and is preferably selected from -(CH2) p1 -、-(CH2) p2 -CH=CH-(CH2) p3 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 , wherein p1 is 2, 3, 4, 5 or 6, preferably 2 or 3, p2 and p3 are independently 0, 1, 2 or 3, and if Sp is -O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 , then the O atom or CO group is connected to the benzene ring respectively.

[0587] Very preferably, Sp is not a single bond and is selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2 and -CO-O-(CH)2-, wherein the O atom or the CO group is attached to the benzene ring.

[0588] Particularly preferred compounds of formula M are those wherein B 1 and B 2 each independently represents 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, flavonoids, wherein in addition one or more CH groups in these radicals can also be replaced by N, cyclohexane-1,4-diyl, wherein one or more non-adjacent CH2 groups can also 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, indane-2,5-diyl or octahydro-4,7-methanoindane-2,5-diyl, all of which may be unsubstituted or mono- or polysubstituted by L as defined above.

[0589] Particularly preferred compounds of formula M are those wherein B 1 and B 2 Each independently represents 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl.

[0590] Further preferred compounds of formula M are those wherein the group -B in formula M 1 -(Z m -B 2 ) m -Selected from the following formula

[0591]

[0592] wherein at least one phenyl ring is substituted by at least one group L, and the phenyl ring is optionally further substituted by one or more groups L or P-Sp-.

[0593] Preferred compounds of formula M and its subformulae are selected from the following preferred embodiments, including any combination thereof:

[0594] - all the groups P in the compounds have the same meaning,

[0595] —-B 1 -(Z m -B 2 ) m - is selected from the group consisting of formulae A1, A2 and A5,

[0596] - said compound contains exactly two polymerizable groups (represented by the group P),

[0597] - said compound contains exactly three polymerizable groups (represented by the group P),

[0598] - P is selected from acrylate, methacrylate and oxetanyl, very preferably acrylate or methacrylate,

[0599] - P is a methacrylate group,

[0600] - all groups Sp are single bonds,

[0601] - at least one of the groups Sp is a single bond and at least one of the groups Sp is not a single bond,

[0602] —Sp, when not a single bond, is -(CH2) p2 -、-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 -O-CO-, wherein p2 is 2, 3, 4, 5 or 6, and the O atom or the CO group is respectively attached to a benzene ring,

[0603] —Sp is a single bond or represents -(CH2) p2 -、-(CH2) p2 -O-, -(CH2) p2-CO-O-, -(CH2) p2 -O-CO-, wherein p2 is 2, 3, 4, 5 or 6, and the O atom or the CO group is respectively attached to a benzene ring,

[0604] —R stands for P-Sp-,

[0605] - R does not represent or contain a polymerizable group,

[0606] —R does not represent or contain a polymerizable group, and represents a linear, branched or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2 groups are optionally 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 connected to each other, and wherein one or more H atoms are each optionally replaced by F, Cl or L a Instead,

[0607] - L or L' represents F, Cl or CN,

[0608] —L is F.

[0609] Very preferred compounds of formula M are selected from the following formulae:

[0610]

[0611]

[0612]

[0613]

[0614]

[0615]

[0616] where the individual radicals, identically or differently on each occurrence and independently of one another, have the following meanings:

[0617] P 1 , P 2 , P 3 denotes a polymerizable group which is preferably selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetanyl and epoxy, very preferably acrylate or methacrylate,

[0618] Sp 1 、Sp 2 、Sp 3 represents a single bond or a spacer group, wherein in addition one or more groups P 1 -Sp1 -、P 2 -Sp 2 - and P 3 -Sp 3 - can also represent R M , with the additional condition that the group P 1 -Sp 1 -、P 2 -Sp 2 and P 3 -Sp 3 -At least one of them is not R M , which preferably has one of the preferred meanings of Sp as given above, very preferably -(CH2) p1 -、-(CH2) p1 -O-, -(CH2) p1 -CO-O- or -(CH2) p1 -O-CO-O-, wherein p1 is an integer from 1 to 12,

[0619] R M represents H, F, Cl, CN or a straight-chain or branched alkyl radical having 1 to 25 C atoms, wherein in addition one or more non-adjacent CH2 groups may also each independently of one another be replaced by -C(R 0 )=C(R 00 )-、-C≡C-、-N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, with O and / or S atoms not being directly connected to one another, and wherein one or more H atoms may also be replaced by F, Cl, CN or P 1 -Sp 1 - is substituted, particularly preferably, by a linear or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy radical having 1 to 12 C atoms, wherein the alkenyl and alkynyl radicals have at least two C atoms and the branched radicals have at least three C atoms, and wherein R aa Does not represent or contain group P 1 , P 2 or P 3 ,

[0620] R 0 , R 00 represents H or an alkyl group having 1 to 12 C atoms,

[0621] R y and R z represents H, F, CH3 or CF3,

[0622] X 1, X 2 , X 3 represents -CO-O-, -O-CO- or a single bond,

[0623] Z M1 Indicates -O-, -CO-, -C(R y R z )- or -CF2CF2-,

[0624] Z M2 , Z M3 Represents -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2- or -(CH2) n -, where n is 2, 3, or 4,

[0625] L represents F, Cl, CN or linear or branched, optionally mono- or polyfluorinated, alkyl, alkoxy, thioalkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy radicals having 1 to 12 C atoms,

[0626] L', L" represent H, F or Cl,

[0627] k represents 0 or 1,

[0628] r represents 0, 1, 2, 3 or 4,

[0629] s represents 0, 1, 2, or 3,

[0630] t represents 0, 1 or 2,

[0631] x represents 0 or 1.

[0632] Very preferred are compounds of the formulae M2, M13 and M32, especially those containing exactly two polymerizable groups P 1 and P 2 of direactive compounds.

[0633] Further preferred are compounds selected from the formulae M17 to M31, in particular compounds selected from the formulae M20, M22, M26, M29 and M31, especially compounds containing exactly three polymerizable groups P 1 , P 2 and P 3 of tri-reactive compounds.

[0634] In the compounds of formulae M1 to M32, the group Preferably

[0635] in which L has, identically or differently on each occurrence, one of the meanings given above and below and is preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, -CH═CH2, C(CH3)═CH2, SCH3, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, -CH═CH2, C(CH3)═CH2, SCH3, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, -CH═CH2, C(CH3)═CH2, SCH3, OCH3, COCH3 or OCF3 and most preferably F, SCH3 or OCH3.

[0636] Preferred compounds of formulae M1 to M32 are those wherein P 1 , P 2 and P 3 represents an acrylate group, a methacrylate group, an oxetanyl group or an epoxy group, very preferably an acrylate group or a methacrylate group, most preferably a methacrylate group.

[0637] Further preferred compounds of formulae M1 to M32 are those wherein Sp 1 、Sp 2 and Sp 3 It is a single bond.

[0638] Further preferred compounds of formulae M1 to M32 are those wherein Sp 1 、Sp 2 and Sp 3 One of them is a single bond, and Sp 1 、Sp 2 and Sp 3 The other one in is not a single bond.

[0639] Further preferred compounds of the formulae M1 to M32 are those in which those radicals Sp which are not single bonds 1 、Sp 2 and Sp 3 Represents -(CH2) s1 -X"-, wherein s1 is an integer from 1 to 6, preferably 2, 3, 4 or 5, and X" is a bond to the benzene ring, and is -O-, -O-CO-, -CO-O-, -O-CO-O- or a single bond.

[0640] Further preferred polymerizable compounds are selected from Table E below, in particular from formulae 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-109, 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.

[0641] Particular preference is given to LC media which comprise one, two or three polymerisable compounds of the formula M.

[0642] Further preferred are LC media comprising two or more direactive polymerizable compounds of the formula M, preferably selected from the formulae M1 to M16 and M32, very preferably from the formulae M2, M13 and M32.

[0643] Further preferred are LC media comprising one or more direactive polymerizable compounds of formula M, preferably selected from the group consisting of formulae M1 to M16 and M32, very preferably selected from the group consisting of formulae M2, M13 and M32, and one or more trireactive polymerizable compounds of formula M, preferably selected from the group consisting of formulae M17 to M32, very preferably selected from the group consisting of formulae M20, M22, M26, M29 and M31.

[0644] Further preferred are LC media comprising one or more polymerizable compounds of formula M, wherein at least one r is not 0, or at least one of s and t is not 0, said formula M being very preferably selected from the group consisting of formulae M2, M13, M22, M24, M27, M29, M31 and M32, and wherein L is selected from the preferred groups indicated above, most preferably from F, OCH3 and SCH3.

[0645] Further preferred are LC media comprising one or more polymerisable compounds which show absorption in the wavelength range from 320 to 380 nm, preferably selected from the formula M, very preferably from the formulae M1 to M32.

[0646] Particular preference is given to LC media which comprise one, two or three polymerisable compounds selected from the formula M or the formulae M1 to M32.

[0647] The combination of the compounds of the preferred embodiments mentioned above with the polymeric compounds described above and below leads in the LC media according to the invention to low threshold voltages, low rotational viscosities and very good low temperature stability, while at the same time leading to constant high bright spots and high HR values ​​and allowing particularly low tilt angles (i.e. large tilts) to be established quickly in PSA displays. In particular, the LC media, compared with the LC media of the prior art, exhibit significantly shortened response times, in particular also grayscale response times, in PSA displays.

[0648] For use in PSA displays, the total proportion of the polymerizable compounds (such as those of the formula M or M1 to M32) in the LC medium is preferably from 0.01 to 2.0%, very preferably from 0.1 to 1.0%, most preferably from 0.2 to 0.8%.

[0649] For use in SA-VA displays, the total proportion of the polymerizable compounds (such as those of the formula M or M1 to M32) in the LC medium is preferably >0 to <3%, very preferably >0 to <2%, more preferably 0.05 to 2.0, most preferably 0.05 to 1.0%.

[0650] The compounds of the formula M and its subformulae can be prepared analogously to the methods known to the person skilled in the art and described in standard texts of organic chemistry, for example in Houben-Weyl, Methoden der organischen Chemie (Methods in Organic Chemistry), Thieme-Verlag, Stuttgart.

[0651] For example, acrylates or methacrylates can be prepared by esterification of the corresponding alcohol with an acid derivative, such as (meth)acryloyl chloride or (meth)acrylic anhydride, in the presence of, for example, pyridine or triethylamine and 4-(N,N-dimethylamino)pyridine (DMAP). Alternatively, the esters can be prepared by esterification of the alcohol with (meth)acrylic acid in the presence of a dehydrating agent, such as, for example, Steglich with dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC) or N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and DMAP.

[0652] The invention also relates to an LC medium or an LC display as described above, wherein the polymerisable compounds, such as those of formula M and subformulae thereof, are present in polymerised form.

[0653] Optionally, one or more polymerization initiators are added to the LC medium. Suitable polymerization conditions and suitable types and amounts of initiators are known to the person skilled in the art and described in the literature. Suitable free-radical polymerizations are commercially available, for example, as photoinitiators or (Ciba AG). If a polymerization initiator is used, its proportion is preferably from 0.001 to 5% by weight, particularly preferably from 0.001 to 1% by weight.

[0654] The polymerizable compounds according to the invention are also suitable for polymerization without initiators, which is accompanied by considerable advantages, such as lower material costs and, in particular, less contamination of the LC medium by possible residual amounts of initiators or their degradation products. The polymerization can therefore also be carried out without the addition of initiators. In a preferred embodiment, the LC medium therefore contains no polymerization initiator.

[0655] The LC medium may further comprise one or more stabilizers to prevent the RM from undesired spontaneous polymerization, for example during storage or transport. Suitable types and amounts of stabilizers are known to the person skilled in the art and are described in the literature. Particularly suitable are, for example, Commercially available stabilizers of the TUNA series (Ciba AG), for example 1076. If stabilizers are used, their proportion, based on the total amount of RM or polymerizable component (component A), is preferably 10 to 50,000 ppm, particularly preferably 50 to 5,000 ppm.

[0656] In a preferred embodiment, the LC medium contains one or more chiral dopants, preferably in a concentration of 0.01 to 1% by weight, very preferably 0.05 to 0.5% by weight. The chiral dopants are preferably selected from the compounds of Table C below, very preferably selected from R- or S-1011, R- or S-2011, R- or S-3011, R- or S-4011 and R- or S-5011.

[0657] In another preferred embodiment, the LC medium contains the racemate of one or more chiral dopants, preferably selected from the chiral dopants mentioned in the previous paragraph.

[0658] In another preferred embodiment of the present invention, the LC medium contains one or more additional stabilizers.

[0659] Preferred stabilizers are selected from compounds of formula H

[0660]

[0661] in

[0662] Ar represents an aromatic or heteroaromatic hydrocarbon radical having 4 to 40 C atoms, preferably 6 to 30 C atoms;

[0663] Sp represents a spacer group;

[0664] R S represents H, alkyl having 1 to 12 C atoms or alkenyl having 2 to 12 C atoms;

[0665] Z S Indicates -O-, -C(O)O-, -(CH2) z -or-(CH2) z O-, or single bond,

[0666] HA means

[0667] R H Indicates H, O, CH3, OH or OR S , preferably H or O;

[0668] R S1 , R S2 , R S3 and R S4 represent, identically or differently, alkyl having 1 to 6 C atoms, preferably having 1 to 3 C atoms, very preferably CH3;

[0669] G stands for H or R S or group Z S -HA;

[0670] z is an integer from 1 to 6; and

[0671] q is 3 or 4.

[0672] Compounds of formula H are described in EP3354710 A1 and EP3354709 A1.

[0673] Preferred compounds of formula H are selected from formula H-1, H-2 and H-3:

[0674]

[0675]

[0676] Where R H has the meanings given above and preferably denotes H or O, and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7, and Sp denotes a spacer group, preferably an alkylene group having 1 to 12 C atoms, in which one or more non-adjacent -CH2- groups can be replaced by -O-.

[0677] Preferred compounds of formula H-1 are selected from compounds of formula H-1-1:

[0678]

[0679] Where R H has the meanings given above and preferably denotes H or O, and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7.

[0680] Very preferred compounds of formula H-1-1 are those of formula H-1-1-1:

[0681]

[0682] Preferred compounds of formula H-2 are selected from compounds of formula H-2-1:

[0683]

[0684] Where R H has the meanings given above and preferably denotes H or O, and n2 is, identically or differently, preferably identically, an integer from 1 to 12 on each occurrence, preferably 2, 3, 4, 5 or 6, very preferably 3, and R S Identically or differently, preferably identically, on each occurrence represents alkyl having 1 to 6 C atoms, preferably n-butyl.

[0685] Very preferred compounds of formula H-2-1 are those of formula H-2-1-1:

[0686]

[0687] Preferred compounds of formula H-3 are selected from formula H-3-1:

[0688]

[0689] Where Sp and R H has the meaning given above, and R H Preferably it represents H or O, and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7.

[0690] Further preferred stabilizers are selected from the group consisting of formulae ST-1 to ST-18:

[0691]

[0692]

[0693]

[0694]

[0695] in

[0696] R STrepresents H, an alkyl or alkoxy group having 1 to 15 C atoms, wherein one or more CH2 groups can also be each independently of one another replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO- are replaced in such a way that the O atoms are not directly connected to one another, and one or more H atoms may also be replaced by halogen,

[0697] To express the same or different meaning on each occurrence

[0698] Z ST each independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-, -CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond,

[0699] L 1 and L 2 each independently represents F, Cl, CH3, CF3 or CHF2,

[0700] p represents 0, 1 or 2,

[0701] q represents 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0702] Preferred compounds of formula ST are those selected from formula ST-3, and in particular:

[0703] wherein n=1, 2, 3, 4, 5, 6 or 7, preferably n=3

[0704]

[0705] wherein n=1, 2, 3, 4, 5, 6 or 7, preferably n=3

[0706]

[0707] wherein n=1, 2, 3, 4, 5, 6 or 7, preferably n=1 or 7

[0708]

[0709]

[0710] 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.

[0711] Very preferred stabilizers are selected from the group consisting of compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1 and ST-12:

[0712]

[0713]

[0714] In another preferred embodiment, the LC medium comprises one or more stabilizers selected from Table D below.

[0715] Preferably, the proportion of stabilizer in the LC medium is from 10 to 500 ppm, very preferably from 20 to 100 ppm.

[0716] In another preferred embodiment, the LC media according to the invention contain a self-aligning (SA) additive, preferably in a concentration of 0.1 to 2.5%.

[0717] In a preferred embodiment, the SA-VA display according to the invention does not contain a polyimide alignment layer. In another preferred embodiment, the SA-VA display according to the preferred embodiment contains a polyimide alignment layer.

[0718] Preferred SA additives for use in this preferred embodiment are selected from compounds comprising a mesogenic group and a linear or branched alkyl side chain terminated by one or more polar anchoring groups selected from hydroxyl, carboxyl, amino or thiol groups.

[0719] Further preferred SA additives contain one or more polymerizable groups, which are optionally attached to the mesogenic group via a spacer group.These polymerizable SA additives can be polymerized in the LC medium under conditions similar to those applied for RMs in the PSA process.

[0720] Suitable SA additives for inducing homeotropic alignment, especially SA additives used in SA-VA mode displays, are disclosed in, for example, US 2013 / 0182202 A1, US 2014 / 0838581 A1, US 2015 / 0166890 A1, and US 2015 / 0252265 A1.

[0721] In a further preferred embodiment, the LC media or polymer-stabilized SA-VA displays according to the invention contain one or more self-aligning additives selected from Table F below.

[0722] In another preferred embodiment, the LC media according to the invention contain one or more SA additives, preferably selected from formula II or its subformulae or from Table F below, in a concentration of 0.1 to 5%, very preferably 0.2 to 3%, most preferably 0.2 to 1.5%.

[0723] The invention furthermore relates to an LC display comprising an LC medium according to the invention as described above and below, which is preferably a PSA or SA display, very preferably a PS-VA, PS-IPS, PS-FFS or SA-VA display.

[0724] The invention furthermore relates to an LC display comprising an LC medium as described above and below, wherein the polymerisable compound is present in polymerised form, the LC display preferably being a PSA or SA display, very preferably a PS-VA, PS-IPS, PS-FFS or SA-VA display.

[0725] To prepare a PSA or polymer-stabilized SA display, the polymerizable compounds comprised in the LC medium are polymerized in the LC medium between the substrates of the LC display by in situ polymerization, preferably while applying a voltage to the electrodes.

[0726] The structure of the display according to the invention corresponds to the usual geometry of PSA displays, as described in the prior art cited at the outset. Geometries without protrusions are preferred, in particular those in which the electrode on the color filter side is unstructured and only the electrode on the TFT side has grooves. Particularly suitable and preferred electrode structures for PS-VA displays are described, for example, in US 2006 / 0066793 A1.

[0727] Preferred PSA-type LC displays according to the invention comprise:

[0728] a first substrate comprising a pixel electrode defining a pixel area, the pixel electrode being connected to a switching element disposed in each pixel area and optionally comprising a micro-slit pattern, and optionally a first alignment layer disposed on the pixel electrode,

[0729] a second substrate comprising a common electrode layer and an optional second alignment layer which may be arranged on the entire portion of the second substrate facing the first substrate,

[0730] - an LC layer, which is arranged between said first and second substrates and comprises an LC medium as described above and below, wherein said polymerisable compound may also be present in polymerised form.

[0731] The first and / or second alignment layer controls the alignment direction of the LC molecules of the LC layer. For example, in a PS-VA display, the alignment layer is selected such that it imparts a homeotropic (or vertical) alignment (i.e. perpendicular to the surface) or a tilted alignment to the LC molecules. Such an alignment layer may, for example, comprise polyimide, which may also be rubbed, or may be prepared by a photoalignment method.

[0732] The LC layer with the LC medium can be deposited between the substrates of the display by methods commonly used by display manufacturers, such as the so-called drop-on-die (ODF) method. The polymerizable components of the LC medium are then polymerized, for example by UV photopolymerization. The polymerization can be performed in one step or in two or more steps.

[0733] The PSA display may comprise further elements such as colour filters, a black matrix, a passivation layer, an optical retardation layer, transistor elements for addressing the individual pixels etc., all of which are well known to those skilled in the art and can be used without inventive skill.

[0734] The electrode structure can be designed by a person skilled in the art according to the individual display type. For example, for a PS-VA display, a multi-domain orientation of the LC molecules can be induced by providing electrodes having slits and / or bumps or protrusions to produce two, four or more different tilted alignment directions.

[0735] When polymerized, the polymerizable compounds form copolymers which result in specific tilt angles of the LC molecules in the LC medium. Without wishing to be bound by a particular theory, it is believed that at least a portion of the cross-linked polymers formed from the polymerizable compounds will phase separate or precipitate from the LC medium and form a polymer layer on the substrate or electrode, or an alignment layer provided thereon. Microscopic measurement data (such as SEM and AFM) have demonstrated that at least a portion of the formed polymers accumulate at the LC / substrate interface.

[0736] The polymerization can be carried out in one step. It is also possible to first carry out the polymerization in a first step, optionally while applying a voltage, to produce the tilt angle, and then, in a second polymerization step, polymerize or crosslink the compounds that have not yet reacted in the first step without applying a voltage ("final curing").

[0737] Suitable and preferred polymerisation methods are, for example, thermal polymerisation or photopolymerisation, preferably photopolymerisation, in particular UV-induced photopolymerisation, which can be achieved by exposing the polymerisable compound to UV radiation.

[0738] The polymerizable compounds of formula M and its subformulae do show particularly good UV absorption in the process for producing a PSA display and are therefore particularly suitable for use in a process for producing a PSA display comprising one or more of the following features or any combination thereof:

[0739] the polymerizable medium is exposed to UV light in a display in a two-step process, the two-step process comprising a first UV exposure step ("UV1 step") with a voltage applied to electrodes of the display to produce a tilt angle, and a second UV exposure step ("UV2 step") without a voltage applied to electrodes of the display to complete polymerization of the polymerizable compound,

[0740] - exposing the polymerizable medium to UV light generated by a UV-LED lamp in a display, preferably at least in the UV2 step, more preferably in both the UV1 and UV2 steps,

[0741] - exposing the polymerizable medium to UV light generated by energy-saving UV lamps (also called "green UV lamps") in a display. These lamps are characterized by relatively low intensities (1 / 100-1 / 10 of conventional UV1 lamps) in their absorption spectrum of 300-380 nm and are preferably used in the UV2 step, but are also optionally used in the UV1 step when the process needs to avoid high intensities,

[0742] - exposing the polymerizable medium in a display to UV light generated by a UV lamp having a radiation spectrum shifted to longer wavelengths, preferably ≥340 nm, more preferably 350 to <370 nm, very preferably 355 to 368 nm, in order to avoid short-term UV light exposure in the PS-VA process.

[0743] Both the use of lower intensity and the shift to longer wavelengths of UV can protect the organic layers from damage that can be caused by UV light.

[0744] A preferred embodiment of the present invention relates to a method for producing a PSA display as described above and below, which method comprises one or more of the following features or any combination thereof:

[0745] - irradiating the polymerisable LC medium by UV light in a two-step process comprising a first UV exposure step with applied voltage ("UV1 step") to produce the tilt angle, and a second UV exposure step without applied voltage ("UV2 step") to complete the polymerisation of the polymerisable compound,

[0746] - irradiating the polymerizable LC medium with UV light generated by a UV lamp, the intensity of which is 0.5 mW / cm 2 Up to 10mW / cm 2 , with a wavelength in the range of 300-380 nm, preferably in the UV2 step, and optionally also in the UV1 step,

[0747] - irradiating the polymerisable LC medium with UV light having a wavelength of ≥340 nm and preferably ≤420 nm, very preferably in the range of 340 to 380 nm, more preferably in the range of 350 to <370 nm, most preferably in the range of 355 to 368 nm,

[0748] - subjecting the polymerisable LC medium to irradiation with UV light while applying a voltage to the electrodes of the display,

[0749] ——Use UV-LED lamp for UV light irradiation.

[0750] For example, this preferred method can be implemented by using a desired UV lamp or by using a bandpass filter and / or a cutoff filter that is substantially transmissive to UV light having one or more corresponding desired wavelengths and substantially blocks light having corresponding undesired wavelengths. For example, when irradiation with UV light having a wavelength λ of 300-400 nm is desired, UV exposure can be implemented using a wide bandpass filter that is substantially transmissive to wavelengths of 300 nm <λ <400 nm. When irradiation with UV light having a wavelength λ of more than 340 nm is desired, UV irradiation can be implemented using a cutoff filter that is substantially transmissive to wavelengths λ >340 nm.

[0751] In a preferred embodiment of the present invention, UV irradiation is performed using a UV-LED lamp.

[0752] In the PSA process, the use of a UV-LED lamp with only one narrow emission peak provides several advantages, such as more efficient transfer of light energy to the polymerizable compounds in the LC medium, depending on the selection of appropriate polymerizable compounds that show absorption at the emission wavelength of the LC lamp. This allows a reduction in UV intensity and / or UV irradiation time, thus enabling reduced operating times and saving energy and production costs. Another advantage is that the narrow emission spectrum of the lamp allows an easier selection of a suitable wavelength for photopolymerization.

[0753] Very preferably, the UV light source is a UV-LED lamp emitting a wavelength in the range of 340 to 400 nm, more preferably in the range of 340 to 380 nm. A UV-LED lamp emitting UV light with a wavelength of 365 nm is particularly preferred.

[0754] This preferred method allows the manufacture of displays by using longer UV wavelengths, thereby reducing or even avoiding the harmful and damaging effects of the short UV light component.

[0755] The UV radiation energy is generally 6 to 100 J, depending on the preparation process conditions.

[0756] The LC medium according to the present invention may additionally comprise one or more further components or additives, which are preferably selected from the group consisting of, but not limited to, comonomers, chiral dopants, polymerization initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricants, dispersants, hydrophobic agents, binders, flow improvers, defoamers, deaerators, diluents, reactive diluents, auxiliaries, colorants, dyes, pigments and nanoparticles.

[0757] Furthermore, it is possible to add, for example, 0 to 15% by weight of pleochroic dyes to the LC medium, in addition to nanoparticles, conductive salts, preferably ethyldimethyldodecyl 4-hexyloxyammonium benzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (see, for example, Haller et al., Mol. Cryst. Liq. Cryst. 24 , 249-258 (1973)) for improving the electrical conductivity, or adding substances for modifying the dielectric anisotropy, viscosity and / or orientation of the nematic phase. For example, DE-A 2209 127, 2240 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430 and 28 53 728 describe substances of this type.

[0758] The individual components of the preferred embodiments of the LC media according to the invention listed above are known or the processes for preparing them are available from the prior art to the person skilled in the relevant art, since they are based on standard processes described in the literature. The corresponding compounds of the formula CY are described, for example, in EP-A-0 364 538. The corresponding compounds of the formula ZK are described, for example, in DE-A-26 36 684 and DE-A-33 21 373.

[0759] The LC media which can be used according to the invention are prepared in a manner conventional per se, for example by mixing one or more of the above-mentioned compounds with one or more polymerizable compounds as defined above, and optionally with further liquid-crystalline compounds and / or additives. Usually, the desired amount of the components used in smaller amounts is dissolved in the components making up the main constituents, this being advantageously done at elevated temperature. It is also possible to mix the solutions of the components in an organic solvent, for example acetone, chloroform or methanol, and to remove the solvent again, for example by distillation after thorough mixing. The invention also relates to a process for the preparation of the LC media according to the invention.

[0760] It goes without saying to the person skilled in the art that the LC media according to the invention can also comprise compounds in which H, N, O, Cl, F are replaced by corresponding isotopes, for example deuterium.

[0761] The following examples illustrate the present invention but do not limit the present invention. However, they show preferred mixture concepts to those skilled in the art, as well as the compounds preferably used and their respective concentrations, and their combinations with each other. In addition, the examples illustrate which properties and combinations of properties are obtainable.

[0762] For the present invention and in the following examples, the structures of the liquid-crystal compounds are indicated with the aid of acronyms. Unless otherwise indicated, the conversion into chemical formulae is carried out according to the following Tables A.1 to A.3. All radicals C n H 2n+1 , C m H 2m+1 and C l H 2l+1 or C n H 2n , C m H 2m and C l H 2l is a straight-chain alkyl group or alkylene group having n, m and 1 C atoms, respectively, in each case. Preferably, n, m and 1 are independently 1, 2, 3, 4, 5, 6 or 7. Table A.1 shows the ring element codes of the core structure of the compounds, Table A.2 lists the bridging units, and Table A.3 lists the meanings of the symbols of the left-hand and right-hand end groups of the molecules. The acronyms consist of the code for the ring element with the optional linking group, followed by a first hyphen, and the code for the left-hand end group, and a second hyphen and the code for the right-hand end group.

[0763] Table A.1: Ring elements

[0764]

[0765]

[0766]

[0767]

[0768] Table A.2: Bridge unit

[0769]

[0770] Table A.3: End groups

[0771]

[0772]

[0773]

[0774] Where n and m are each integers and the three dots "..." are placeholders for other abbreviations from the table.

[0775] Table B shows the schematic structures of the compounds and their corresponding abbreviations.

[0776] Table B

[0777] In Table B, n, m, k and l are each independently an integer, preferably 1 to 9, preferably 1 to 7, k and l may also be 0, preferably 0 to 4, more preferably 0 or 2, most preferably 2, n is preferably 1, 2, 3, 4 or 5, in the combination "-nO-", n is preferably 1, 2, 3 or 4, very preferably 2 or 4, m is preferably 1, 2, 3, 4 or 5, in the combination "-Om", m is preferably 1, 2, 3 or 4, more preferably 2 or 4. The combination "-nVm" is preferably "2V1". (O)C m H 2m+1 Meaning C m H 2m+1 or OC m H 2m+1 .

[0778]

[0779]

[0780]

[0781]

[0782]

[0783]

[0784]

[0785]

[0786]

[0787]

[0788]

[0789]

[0790]

[0791]

[0792]

[0793]

[0794]

[0795]

[0796]

[0797]

[0798]

[0799] In a preferred embodiment of the present invention, the LC media according to the invention comprise one or more compounds selected from the compounds of Table B.

[0800] Table C

[0801] Table C shows possible chiral dopants which can be added to the LC media according to the invention.

[0802]

[0803]

[0804] The LC medium preferably comprises 0 to 10 wt %, in particular 0.01 to 5 wt %, particularly preferably 0.1 to 3 wt % of dopant. The LC medium preferably comprises one or more dopants selected from the compounds of Table C.

[0805] Table D

[0806] Table D shows possible stabilizers which can be added to the LC media according to the invention. wherein n represents an integer from 1 to 12, preferably 1, 2, 3, 4, 5, 6, 7 or 8, the terminal methyl groups are not shown.

[0807]

[0808]

[0809]

[0810]

[0811]

[0812]

[0813]

[0814] The LC medium preferably comprises 0 to 10 wt %, in particular 1 ppm to 5 wt %, particularly preferably 1 ppm to 1 wt % of stabilizer. The LC medium preferably comprises one or more stabilizers selected from the compounds from Table D.

[0815] Table E

[0816] Table E shows exemplary reactive mesogenic compounds which can be used in the LC media according to the present invention.

[0817]

[0818]

[0819]

[0820]

[0821]

[0822]

[0823]

[0824]

[0825]

[0826]

[0827]

[0828]

[0829]

[0830]

[0831]

[0832]

[0833]

[0834]

[0835]

[0836] In a preferred embodiment, the mixture according to the invention comprises one or more polymerizable compounds, preferably selected from the group consisting of 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-10 are particularly preferred. 3. RM-109, 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.

[0837] Table F

[0838] Table F shows self-aligning compounds for homeotropic alignment which can be used together with polymerisable compounds in LC media for SA-VA and SA-FFS displays according to the invention:

[0839]

[0840]

[0841]

[0842]

[0843]

[0844]

[0845]

[0846]

[0847]

[0848]

[0849]

[0850] In a preferred embodiment, the LC media, SA-VA and SA-FFS displays according to the invention comprise one or more SA additives selected from the formulae SA-1 to SA-48, preferably from the formulae SA-14 to SA-48, very preferably from the formulae SA-20 to SA-34 and SA-44 in combination with one or more RMs. Example

[0851] The following examples explain the present invention without limiting it. However, they show preferred mixture concepts and preferably used compounds and their corresponding concentrations and their combinations with each other to those skilled in the art. In addition, the examples illustrate obtainable properties and property combinations.

[0852] In addition, the following abbreviations and symbols are used:

[0853] V0 represents the threshold voltage at 20°C, capacitive [V],

[0854] n e represents the extraordinary refractive index at 20°C and 589nm,

[0855] n o represents the ordinary refractive index at 20°C and 589nm,

[0856] Δn represents the optical anisotropy at 20°C and 589 nm,

[0857] ε ⊥ represents the dielectric constant perpendicular to the director at 20°C and 1kHz,

[0858] ε || represents the dielectric constant parallel to the director at 20°C and 1kHz,

[0859] Δε represents the dielectric anisotropy at 20°C and 1kHz,

[0860] cl.p., T(N,I) represents the clearing point [℃],

[0861] γ1 represents the rotational viscosity at 20°C [mPa·s],

[0862] K1 is the elastic constant at 20°C, the “bending” deformation [pN],

[0863] K2 represents the elastic constant at 20°C, "torsion" deformation [pN],

[0864] K3 represents the elastic constant at 20°C, "bending" deformation [pN],

[0865] K 平均represents the average elastic constant [pN] at 20°C and is defined in this paper as K 平均 ≡( 3 / 2K1+K3) / 3≈(K1+K2+K3) / 3,

[0866] LTS stands for the low temperature stability of the phase, which is determined in a test cell.

[0867] VHR stands for voltage holding ratio

[0868] Unless expressly stated otherwise, all concentrations in the present application are given as percentages by weight and relate to the respective entire mixture, which comprises all solid or liquid-crystalline components (without solvent).

[0869] Unless otherwise stated, all temperature values ​​indicated in this application, such as melting point T(C,N), transition from smectic phase (S) to nematic phase (N) T(S,N) and clearing point T(N,I) are expressed in degrees Celsius (°C). Mp stands for melting point, cl.p. = clearing point. In addition, C = liquid crystal phase, N = nematic phase, S = smectic phase and I = isotropic phase. The data between these symbols represent transition temperatures.

[0870] All physical properties are and have been determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals" Status November 1997, Merck KGaA, Germany, and are valid for a temperature of 20°C, with Δn measured at 589 nm and Δε measured at 1 kHz, unless expressly stated otherwise in each case.

[0871] The term "threshold voltage" as used in the present invention relates to the capacitive threshold (V0), which is also referred to as the Freedericks threshold unless otherwise stated. In the embodiments, the optical threshold is also generally for a relative contrast ratio of 10% (V 10 ) given.

[0872] Unless otherwise stated, the process for polymerising the polymerisable compounds in a PSA display as described above and below is carried out at a temperature at which the LC medium exhibits a liquid crystal phase, preferably a nematic phase, and most preferably at room temperature.

[0873] Unless otherwise stated, the methods for preparing the test cells and measuring their electro-optical and other properties were performed by the methods described below or methods analogous thereto.

[0874] Unless otherwise stated, the PSVA display or PSVA test cell used for photopolymerization and measuring tilt angles, etc., consists of two plane-parallel glass outer plates separated by 3-4 μm, each having an electrode layer on the inside and a polyimide alignment layer on top, wherein the two polyimide layers are rubbed antiparallel to each other and result in homeotropic edge alignment of the liquid crystal molecules. The SAVA display or test cell has the same structure, but in which one or both polyimide layers are omitted.

[0875] The polymerizable compound is polymerized in the display or test cell by irradiation with UV light of defined intensity for a pre-specified time while applying a voltage (typically 10 V to 30 V AC, 1 kHz) to the display.

[0876] The tilt angle is determined using a Mueller Matrix Polarimeter "AxoScan" from Axometrics. Here, low values ​​(ie large deviations from an angle of 90°) correspond to large tilts.

[0877] Unless otherwise stated, the term "tilt angle" means the angle between the LC director and the substrate, and "LC director" means the preferred orientation direction of the optical principal axes of the LC molecules in a layer with uniformly oriented LC molecules, which in the case of calamitic uniaxial positively birefringent LC molecules corresponds to their molecular long axes.

[0878] Example 1

[0879] Nematic LC mixture N1 was prepared as follows:

[0880]

[0881] To mixture N1 was added 150 ppm of stabilizer H-1-1-1.

[0882]

[0883] Example 2

[0884] The nematic LC mixture N2 was prepared as follows:

[0885]

[0886] To the mixture N2 was added 150 ppm of stabilizer H-2-1-1.

[0887]

[0888] Example 3

[0889] Nematic LC mixture N3 was prepared as follows:

[0890]

[0891] To mixture N3 was added 100 ppm of stabilizer ST-3a-1.

[0892]

[0893] Example 4

[0894] Nematic LC mixture N4 was prepared as follows:

[0895]

[0896] To mixture N4 was added 150 ppm of stabilizer ST-3b-1.

[0897]

[0898] Example 5

[0899] Nematic LC mixture N5 was prepared as follows:

[0900]

[0901] To mixture N5 was added 100 ppm of stabilizer ST-8-1.

[0902]

[0903] Example 6

[0904] Nematic LC mixture N6 was prepared as follows:

[0905]

[0906]

[0907] To mixture N6 was added 100 ppm of stabilizer ST-9-1.

[0908]

[0909] Example 7

[0910] Nematic LC mixture N7 was prepared as follows:

[0911]

[0912]

[0913] To mixture N7 was added 50 ppm of stabilizer ST-12.

[0914]

[0915] Example 8

[0916] Nematic LC mixture N8 was prepared as follows:

[0917]

[0918]

[0919] To mixture N8 was added 100 ppm of stabilizer ST-12.

[0920] Example 9

[0921] Nematic LC mixture N9 was prepared as follows:

[0922]

[0923] To mixture N9 was added 100 ppm of stabilizer ST-3a-1.

[0924] Example 10

[0925] Nematic LC mixture N10 was prepared as follows:

[0926]

[0927] To mixture N10 was added 50 ppm of stabilizer ST-3b-1.

[0928] Embodiment 11

[0929] Nematic LC mixture N11 was prepared as follows:

[0930]

[0931]

[0932] To mixture N11 were added 150 ppm of stabilizer H-1-1-1.

[0933] Example 12

[0934] Nematic LC mixture N12 was prepared as follows:

[0935]

[0936]

[0937] To mixture N12 was added 100 ppm of stabilizer H-2-1-1.

[0938] Embodiment 13

[0939] Nematic LC mixture N13 was prepared as follows:

[0940]

[0941] To mixture N13 was added 100 ppm of stabilizer ST-8-1.

[0942] Embodiment 14

[0943] Nematic LC mixture N14 was prepared as follows:

[0944]

[0945] To mixture N14 was added 100 ppm of stabilizer H-2-1-1.

[0946] Embodiment 15

[0947] Nematic LC mixture N15 was prepared as follows:

[0948]

[0949]

[0950] To mixture N15, 150 ppm of stabilizer ST-12 was added.

[0951] Example 16

[0952] Nematic LC mixture N16 was prepared as follows:

[0953]

[0954]

[0955] To mixture N16 was added 50 ppm of stabilizer H-2-1-1.

[0956] Embodiment 17

[0957] Nematic LC mixture N17 was prepared as follows:

[0958]

[0959] To mixture N17 was added 150 ppm of stabilizer H-1-1-1.

[0960] Embodiment 18

[0961] Nematic LC mixture N18 was prepared as follows:

[0962]

[0963] To mixture N18 was added 100 ppm of stabilizer ST-9-1.

[0964] Embodiment 19

[0965] Nematic LC mixture N19 was prepared as follows:

[0966]

[0967]

[0968] To mixture N19 was added 150 ppm of stabilizer ST-9-1.

[0969] Embodiment 20

[0970] Nematic LC mixture N20 was prepared as follows:

[0971]

[0972]

[0973] To mixture N20 was added 100 ppm of stabilizer ST-3a-1.

[0974] Embodiment 21

[0975] Nematic LC mixture N21 was prepared as follows:

[0976]

[0977] To mixture N21 were added 150 ppm of stabilizer ST-3b-1.

[0978] Embodiment 22

[0979] Nematic LC mixture N22 was prepared as follows:

[0980]

[0981] To mixture N22 was added 100 ppm of stabilizer ST-8-1.

[0982] Embodiment 23

[0983] Nematic LC mixture N23 was prepared as follows:

[0984]

[0985]

[0986] To mixture N23 was added 100 ppm of stabilizer ST-3b-1.

[0987] Embodiment 24

[0988] Nematic LC mixture N24 was prepared as follows:

[0989]

[0990]

[0991] To mixture N24 was added 100 ppm of stabilizer ST-9-1.

[0992] Embodiment 25

[0993] Nematic LC mixture N25 was prepared as follows:

[0994]

[0995] To mixture N25 was added 50 ppm of stabilizer H-1-1-1.

[0996] Embodiment 26

[0997] Nematic LC mixture N26 was prepared as follows:

[0998]

[0999] To mixture N26 was added 100 ppm of stabilizer ST-12.

[1000] Embodiment 27

[1001] Nematic LC mixture N27 was prepared as follows:

[1002]

[1003]

[1004] To mixture N27 was added 100 ppm of stabilizer ST-8-1.

[1005] Embodiment 28

[1006] Nematic LC mixture N28 was prepared as follows:

[1007]

[1008]

[1009] To mixture N28 was added 150 ppm of stabilizer ST-3b-1.

[1010] Embodiment 29

[1011] Nematic LC mixture N29 was prepared as follows:

[1012]

[1013] To mixture N29 was added 100 ppm of stabilizer H-2-1-1.

[1014] Embodiment 30

[1015] Nematic LC mixture N30 was prepared as follows:

[1016]

[1017] To mixture N30 was added 100 ppm of stabilizer ST-3a-1.

[1018] Embodiment 31

[1019] Nematic LC mixture N31 was prepared as follows:

[1020]

[1021]

[1022] To mixture N31 was added 100 ppm of stabilizer ST-3a-1.

[1023] Embodiment 32

[1024] Nematic LC mixture N32 was prepared as follows:

[1025]

[1026] To mixture N32 was added 100 ppm of stabilizer ST-3a-1.

[1027] Embodiment 33

[1028] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-1 and 150 ppm of stabilizer ST-3a-1 to the mixture of Example 1.

[1029]

[1030] Embodiment 34

[1031] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-35 and 100 ppm of stabilizer ST-3b-1 to the mixture of Example 1.

[1032]

[1033] Embodiment 35

[1034] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-58 and 150 ppm of stabilizer ST-8-1 to the mixture of Example 2.

[1035]

[1036] Embodiment 36

[1037] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-64 and 100 ppm of stabilizer ST-9-1 to the mixture of Example 3.

[1038]

[1039] Embodiment 37

[1040] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-120 and 150 ppm of stabilizer ST-12 to the mixture of Example 4.

[1041]

[1042] Embodiment 38

[1043] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-142 and 150 ppm of stabilizer H-1-1-1 to the mixture of Example 1.

[1044]

[1045] Embodiment 39

[1046] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-143 and 50 ppm of stabilizer H-2-1-1 to the mixture of Example 6.

[1047]

[1048] Embodiment 40

[1049] A polymerizable mixture was prepared by adding 0.3% of the polymerizable compound RM-145 to the mixture of Example 8.

[1050]

[1051] Embodiment 41

[1052] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-156 and 150 ppm of stabilizer ST-8-1 to the mixture of Example 5.

[1053]

[1054] Embodiment 42

[1055] A polymerizable mixture was prepared by adding 0.35% of polymerizable compound RM-157 and 100 ppm of stabilizer H-1-1-1 to the mixture of Example 11.

[1056]

[1057] Embodiment 43

[1058] A polymerizable mixture was prepared by adding 0.4% of polymerizable compound RM-159 and 150 ppm of stabilizer ST-3a-1 to the mixture of Example 12.

[1059]

[1060] Embodiment 44

[1061] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-160 and 150 ppm of stabilizer ST-8-1 to the mixture of Example 15.

[1062]

[1063] Embodiment 45

[1064] A polymerizable mixture was prepared by adding 0.4% of polymerizable compound RM-162 and 100 ppm of stabilizer ST-9-1 to the mixture of Example 21.

[1065]

[1066] Embodiment 46

[1067] A polymerizable mixture was prepared by adding 0.4% of polymerizable compound RM-163 and 100 ppm of stabilizer ST-3b-1 to the mixture of Example 24.

[1068]

[1069] Embodiment 47

[1070] A polymerizable mixture was prepared by adding 0.4% of polymerizable compound RM-169 and 100 ppm of stabilizer ST-9-1 to the mixture of Example 27.

[1071]

[1072] Embodiment 48

[1073] A polymerizable mixture was prepared by adding 0.3% of polymerizable compound RM-171 and 100 ppm of stabilizer ST-3a-1 to the mixture of Example 1.

[1074]

[1075] Embodiment 49

[1076] A polymerizable mixture was prepared by adding 0.4% of polymerizable compound RM-172 and 150 ppm of stabilizer H-1-1-1 to the mixture of Example 16.

[1077]

[1078] Embodiment 50

[1079] A polymerizable mixture was prepared by adding 0.4% of polymerizable compound RM-171 and 100 ppm of stabilizer ST-12 to the mixture of Example 15.

[1080] Embodiment 51

[1081] A polymerizable mixture was prepared by adding 0.4% of polymerizable compound RM-171 and 100 ppm of stabilizer ST-12 to the mixture of Example 30.

Claims

1. LC medium comprising one or more compounds of formula IA, one or more compounds of formula IB and one or more compounds of formula IC, where the individual radicals have the following meanings on each occurrence, identically or differently and independently of one another: R 1A , R 2A is a straight-chain, branched or cyclic alkyl radical having 1 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, CR 0 =CR 00 -、-C≡C-、 and wherein one or more H atoms are each optionally replaced by F or Cl, R 0 , R 00 is H or an alkyl radical having 1 to 12 C atoms, L 1A , L 2A is F or Cl, preferably F, W is O or S, Y 1 , Y 2 is H, F, Cl, CF3, CHF2, CH3 or OCH3, preferably H, CH3 or OCH3, very preferably H, A 3 a) 1,4-cyclohexenylene or 1,4-cyclohexylene, in which one or two non-adjacent CH2 groups may be replaced by -O- or -S-, b) 1,4-phenylene, in which one or both 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]-octane-2,6-diyl, 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, wherein the groups a), b) and c) may be mono- or poly-substituted by halogen atoms, n is 0, 1, or 2, Z 1 is -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, R 1B , R 2B is an alkenyl group having 2 to 7 C atoms, R 1C , R 2C With respect to R 1A One of the meanings given, L 1C , L 2C With respect to L 1A One of the meanings given.

2. LC medium according to claim 1, characterized in that The compound of formula IA is selected from the following sub-formulae: Where L 11 and L 12 Independently of each other, claim 1 has the following aspects: 1A one of the meanings given, alkyl and alkyl* each independently represent a straight-chain alkyl radical having 1 to 6 C atoms, alkenyl and alkenyl* each independently represent a straight-chain alkenyl radical having 2 to 6 C atoms, alkoxy and alkoxy* each independently represent a straight-chain alkoxy radical having 1 to 6 C atoms, and L 11 and L 12 Each independently represents F or Cl.

3. LC medium according to claim 1 or 2, characterized in that The compound of formula IB is selected from the following sub-formulae:

4. LC medium according to any one of claims 1 to 3, characterized in that The compound of formula IC is selected from the following subformulae: Where L 1 and L 2 Independently of each other, claim 1 has the following aspects: 1C one of the meanings given, Alkyl and Alkyl* each independently of one another denote a straight-chain alkyl group having 1 to 6 C atoms, Alkoxy each independently of one another denotes a straight-chain alkoxy group having 1 to 6 C atoms, Alkenyl and Alkenyl* each independently of one another denote a straight-chain alkenyl group having 2 to 6 C atoms, and O denotes an oxygen atom or a single bond.

5. LC medium according to any one of claims 1 to 4, characterized in that It also comprises one or more compounds selected from the group consisting of compounds of formula IIA, IIB, IIC and IID where the individual radicals have the following meanings on each occurrence, identically or differently and independently of one another: R 21 , R 22 is H, an alkyl, alkoxy or alkenyl radical having up to 15 C atoms, which is unsubstituted or monosubstituted by F, Cl, CN or CF3, and wherein in addition, one or more CH2 groups in these radicals may be replaced by -O-, -S-, -C≡C-, -CF2O-, -OCF2-, -OC-O-, -O-CO ...C≡C-, -C≡C-, -C≡C-, -C≡C-, -C≡C-, -C≡C-, -C≡C Instead, L 1 To L 4 is F, Cl, CF3 or CHF2, Y is H, F, Cl, CF3, CHF2 or CH3, Z 1 , Z 2 is a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CH=CHCH2O-, p is 0, 1, or 2, and q is 0 or 1.

6. LC medium according to any one of claims 1 to 5, characterized in that It additionally comprises one or more compounds selected from the compounds of formulae IV-1 to IV-3 in Alkyl and alkyl' independently represent an alkyl radical having 1 to 7 C atoms, Alkenyl represents an alkenyl group having 2 to 5 C atoms, Alkoxy represents an alkoxy group having 1 to 5 C atoms.

7. LC medium according to one or more of claims 1 to 6, characterized in that The LC medium additionally comprises one or more compounds of the formula V, in R 51 and R 52 independently of one another denotes H, alkyl, alkoxy or alkenyl having up to 15 C atoms, which is unsubstituted, monosubstituted by F, Cl, CN or CF3 or at least monosubstituted by halogen, wherein in addition one or more CH2 groups in these radicals may be replaced by -O-, -S-, -C≡C-, -CF2O-, -OCF2-, -OC-O-, -O-CO-, -S-, -C≡C ... Instead, Same or different Z 51 , Z 52 each independently represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO- or a single bond, and n is 1 or 2.

8. LC medium according to one or more of claims 1 to 7, characterized in that It additionally comprises one or more additives selected from polymerizable compounds, stabilizers, chiral dopants, polymerization initiators and self-aligning additives.

9. Process for the preparation of an LC medium according to one or more of claims 1 to 8, comprising the following steps: One or more compounds of the formulae IA, IB and IC as defined in one or more of claims 1 to 4 are mixed with one or more further LC compounds and optionally with one or more additives.

10. LC display comprising an LC medium as defined in one or more of claims 1 to 8.

11. The LC display according to claim 10, characterized in that It is VA, IPS, FFS, UB-FFS or UV 2 A-mode LC display.

12. Use of an LC medium according to one or more of claims 1 to 8 or an LC display according to claim 10 or 11 for energy-saving LC displays.

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