Liquid-crystal medium

Abstract

To provide a liquid-crystal medium.SOLUTION: The present invention relates to a liquid-crystal (LC) material as defined in claim 1, having negative dielectric anisotropy and to the use thereof for optical, electro-optical and electronic purposes, such as for example in LC displays, in particular energy saving displays based on the ECB, IPS or FFS effect.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to liquid crystal (LC) media having negative dielectric anisotropy and their use for optical, electro-optical and electronic purposes, in particular in LC displays.

Background Art

[0002] One of the currently used liquid-crystal display (LCD) modes is the TN ("twisted nematic") mode. However, TN LCDs have the disadvantage that the contrast strongly depends on the viewing angle.

[0003] In addition, so-called VA ("vertically aligned") displays with a wider viewing angle are known. The LC cell of a VA display has an LC media layer between two transparent electrodes, where the LC media usually has negative dielectric anisotropy. In the switched-off state, the molecules of the LC layer are oriented perpendicular to the electrode surface (homeotropic) or have a tilted homeotropic orientation. When a voltage is applied to the two electrodes, reorientation of the LC molecules occurs parallel to the electrode surface.

[0004] Also known are so-called IPS ("in-plane switching") displays having an LC layer between two substrates, where the two electrodes are arranged on only one of the two substrates and preferably have an intermeshed comb-shaped structure. When a voltage is applied to the electrodes, this creates an electric field having a significant component parallel to the LC layer between the electrodes. This causes reorientation of the LC molecules in the layer plane.

[0005] Furthermore, so-called FFS ("fringe-field switching") displays have been reported (see, in particular, S.H. Jung et al., Jpn. J. Appl. Phys., Vol. 43, No. 3, 2004, p. 1028 (Non-Patent Document 1)). This display has two electrodes on the same substrate, one of which is structured in a comb shape and the other is unstructured. This results in a strong so-called "fringe field", i.e., a strong electric field near the electrode ends, and an electric field having both a strong vertical component and a strong horizontal component is generated across the cell. The FFS display has a low viewing-angle dependence of contrast. The FFS display usually contains an LC medium having a positive dielectric anisotropy and an alignment layer, usually a polyimide alignment layer, thereby providing a planar alignment for the molecules of the LC medium.

[0006] The FFS display can be operated as an active matrix display or a passive matrix display. In the case of an active matrix display, individual pixels are usually addressed by integrated non-linear active elements, such as transistors (e.g., thin-film transistors ("TFTs")), while in the case of a passive matrix display, individual pixels are usually addressed by multiplexing methods known from the prior art.

[0007] An FFS display is disclosed that has an electrode design and layer thickness similar to that of an FFS display, but includes an LC medium layer having negative dielectric anisotropy instead of an LC medium layer having positive dielectric anisotropy (see, for example, S.H. Lee et al., Appl. Phys. Lett., Vol. 73, No. 20, 1998, pp. 2882 - 2883 (Non-Patent Document 2), and S.H. Lee et al., Liquid Crystals, Vol. 39, No. 9, 2012, pp. 1141 - 1148 (Non-Patent Document 3)). The LC medium having negative dielectric anisotropy exhibits a more preferable director orientation with a smaller tilt and a higher twist orientation compared to the LC medium having positive dielectric anisotropy. As a result, these displays have higher transmittance. This display further has an alignment layer, preferably a polyimide alignment layer provided on at least one of the substrates, which is in contact with the LC medium and causes planar alignment of the LC molecules of the LC medium. These displays are also known as "Ultra Brightness FFS (UB-FFS)" mode displays. These displays require an LC medium with high reliability.

[0008] In a more recent type of VA display, the uniform alignment of LC molecules is limited to a plurality of relatively small domains within the LC cell. There may be disclinations between these domains, which are also known as tilt domains. A VA display having tilt domains has a larger viewing angle independent of contrast and intermediate gradations compared to a conventional VA display. In addition, this type of display is easy to manufacture, and further processing of the electrode surface, such as rubbing, for uniformly aligning molecules in the switched-on state is no longer necessary. Instead, the preferential direction of the tilt angle or pretilt angle is controlled by a special design of the electrodes.

[0009] In a so-called MVA ("multidomain vertical alignment") display, this is usually achieved by electrodes having protrusions, which causes local pretilt. As a result, when a voltage is applied, LC molecules are oriented parallel to the electrode surface in various directions and in various defined regions of the cell. This achieves a "controlled" switch and prevents the formation of interfering disclination lines. Although this arrangement improves the viewing angle of the display, however, it results in a reduction in light transmittance. Further development of MVA uses protrusions only on one electrode side, while the opposite electrode has slits, thereby improving light transmittance. The electrode with slits generates a non-uniform electric field in the LC cell when a voltage is applied, which means that controlled switching is still achieved. The distance between the slits and the protrusions can be increased to further improve light transmittance, but this results in an increase in response time on the one hand. In a so-called PVA ("patterned VA") display, the protrusions are completely redundant in that both electrodes are structured by slits on the opposite side, which results in an increase in contrast and an improvement in light transmittance, but is technically difficult and makes the display more sensitive to mechanical effects ("tapping", etc.). However, for many applications, such as monitors, especially TV screens, a reduction in response time and an improvement in the contrast and brightness (transmittance) of the display are required.

[0010] Further developments are so-called PS ("polymer sustained") or PSA ("polymer sustained alignment") type displays, for which the term "polymer stabilised" is sometimes also used. In these displays, a small amount (e.g., 0.3 wt%, typically less than 1 wt%) of one or more polymerizable compounds (one or more), preferably polymerizable monomer compounds (one or more), is added to the LC medium. After filling the LC medium into the display, it is polymerized or crosslinked in situ, usually by ultraviolet photopolymerization, optionally while applying a voltage to the electrodes of the display. This polymerization is carried out at a temperature at which the LC medium exhibits a liquid crystal phase, usually at room temperature. It has been demonstrated that it is particularly appropriate to add a polymerizable mesogen or liquid crystal compound, also known as a reactive mesogen or "RM" to the LC mixture.

[0011] On the other hand, the PS(A) principle is used in various conventional LC display modes. Thus, for example, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS and PS-TN displays are known. The polymerization of RM is preferably carried out while applying a voltage in the case of PS-VA and PS-OCB displays, and in the case of PS-IPS displays, with or without applying a voltage, preferably without applying a charge. As can be demonstrated in a test cell, the PS(A) method results in a pretilt in the cell. In the case of a PS-VA display, the pretilt has a positive effect on the response time. For a PS-VA display, standard MVA or PVA pixels and electrode layouts can be used. However, in addition, for example, on the side of the electrode where only one is structured, it is also possible to make do without protrusions, which significantly simplifies the manufacturing and, as a result, provides a very good contrast and at the same time a very good light transmittance.

[0012] PS-VA displays are described, for example, in European Patent Application Publication No. 1170626 (Patent Document 1), U.S. Patent No. 6,861,107 (Patent Document 2), U.S. Patent No. 7,169,449 (Patent Document 3), U.S. Patent Application Publication No. 2004 / 0191428 (Patent Document 4), U.S. Patent Application Publication No. 2006 / 0066793 (Patent Document 5), and U.S. Patent Application Publication No. 2006 / 0103804 (Patent Document 6).

[0013] Especially for monitors, especially for TV applications, the response time of LC displays, however, the optimization of contrast and brightness (and thus also transmittance) continues to be required. Here, the PSA method can offer significant advantages. Especially in the case of PS-VA, PS-IPS, and PS-FFS displays, a shortening of the response time, which is correlated with the pretilt measurable in the test cell, can be achieved without a significant adverse effect on other parameters.

[0014] Another problem observed in the prior art is that when using a conventional LC medium in an LC display including but not limited to PSA type displays, especially when the LC medium is filled in a display cell manufactured using the one drop filling (ODF) method, unevenness often occurs in the display. This phenomenon is also known as "ODF unevenness". Therefore, it is desirable to provide an LC medium that leads to a reduction in ODF unevenness.

[0015] Another problem observed in the prior art is that LC media for use in PSA displays, including but not limited to PSA type displays, often exhibit high viscosities, and as a result, exhibit high switching times. To reduce the viscosity and switching time 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 decrease in reliability and stability and, in particular, a decrease in VHR after exposure to UV radiation. In particular, since the photopolymerization of RM in PSA displays is usually carried out by exposure to UV radiation, this can cause a decrease in VHR in the LC media, which is quite disadvantageous for use in PSA displays.

[0016] In addition, there is a great demand for PSA displays, and LC media and polymerizable compounds for use in such PSA displays, which enable a large operating temperature range together with high resistivity, short response times even at low temperatures, and low threshold voltages, low pretilt angles, a large number of intermediate gray levels, high contrast and wide viewing angles, high reliability and high values of VHR after UV exposure, and in the case of polymerizable compounds, low melting points and high solubility in LC host mixtures. For PSA displays for mobile applications, it is particularly desirable to be able to utilize LC media exhibiting low threshold voltages and high birefringence.

[0017] One trend in displays is to achieve the fastest possible response time to obtain the best video quality. In this regard, media with negative dielectric anisotropy are inherently disadvantaged compared to LC media with positive dielectric anisotropy. On the other hand, mixtures with negative dielectric anisotropy enable high transmittance in a standard FFS cell layout, and their use has a positive impact on power consumption and the environment. In the art, it is necessary to achieve both fast response times and higher transmittance. Especially in the use in portable devices, there is a great demand for displays with high transmittance, which enables the use of lower-intensity backlights, thus leading to longer battery life and, thus, more sustainable products. Alternatively, displays with improved contrast, especially under ambient light, and higher brightness can be realized. Also, due to the popularity of 8K and gaming monitors, there is an increasing demand for LC display panels with higher refresh rates, and thus, for LC media with faster response times.

[0018] Therefore, there is still a great demand for LC media that may contain polymerizable compounds for use in VA, FFS, or PSA displays that do not exhibit the above-mentioned drawbacks, or exhibit only minor drawbacks and have improved properties.

Prior Art Documents

Patent Documents

[0019]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

[0020] [Non-Patent Document 1] S.H. Jung et al., Jpn. J. Appl. Phys., Vol. 43, No. 3, 2004, p. 1028 [Non-Patent Document 2] S.H. Lee et al., Appl. Phys. Lett., Vol. 73 (No. 20), 1998, pp. 2882 - 2883 [Non-Patent Document 3] S.H. Lee et al., Liquid Crystals, Vol. 39 (No. 9), 2012, pp. 1141 - 1148 [Summary of the Invention] [Problems to be Solved by the Invention]

[0021] The present invention is based on the object of providing a novel and suitable LC medium that does not have the drawbacks shown above or has them to a reduced extent. [Means for Solving the Problems]

[0022] Surprisingly, by using a liquid crystal medium containing a compound of formula I and a compound of formula CPY defined below, a liquid crystal medium that does not exhibit the drawbacks of the prior art materials or exhibits them at least to a significantly reduced extent and has an appropriately high negative Δε, an appropriate phase range and Δn, and a high LTS can be realized.

[0023] The present invention relates to a liquid crystal medium containing a compound of formula I, a compound of formula CPY, and one or more compounds selected from the group of compounds of formulae IIA, IIB, IIC, and IID.

[0024] [Chemical Formula]

[0025]

Chem.

[0026]

Chem.

[0027] In the formula, R 2A , R 2B , R 2C and R 2D are the same or different and each represents H, a linear alkyl or alkoxy having 1 to 15 C atoms, a linear alkenyl or alkenyloxy having 2 to 15 C atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy each having 3 to 15 C atoms, provided that in these groups one or more CH2 groups are such that O atoms are not directly linked to each other, and each is independent of the others,

Chem.

[0028] The present invention further relates to an LC display comprising an LC medium according to the present invention, in particular a VA, IPS, FFS or UB-FFS or PSA display, particularly preferably an FFS, UB-FFS, VA or PS-VA display.

[0029] The present invention further relates to the use of an LC medium according to the present invention in a PSA display, in particular, preferably for generating a tilt angle in the LC medium by in-situ polymerization of a polymerizable reactive mesogen (RM) in the PSA display in an electric or magnetic field, in a PSA display comprising an LC medium.

[0030] The present invention further relates to a method for preparing an LC medium as described above and below, comprising the step of mixing one or more compounds of formula I with one or more compounds of formula CPY, with one or more compounds of formula IIA, IIB, IIC and / or IID, optionally with one or more chiral dopants, optionally with one or more polymerizable compounds, and optionally with further LC compounds and / or additives.

[0031] The present invention further relates to the use of an LC medium according to the present invention in a polymer-stabilized SA-VA display and to a polymer-stabilized SA-VA display comprising an LC medium according to the present invention.

[0032] According to another aspect of the present invention, an energy-saving display for games is provided, preferably comprising the liquid crystal medium defined above and below. In a preferred embodiment, the medium for an energy-saving display for games has a birefringence in the range of 0.125 to 0.155. The display according to the present invention preferably has a cell gap of 3.3 μm or less, more preferably 2.2 μm or less.

[0033] The present invention further relates to a method for manufacturing an LC display as described above and below, comprising the step of filling an LC medium as described above and below, which may contain one or more polymerizable compounds, between the substrates of the display or providing it by another method, and optionally the step of polymerizing the polymerizable compound.

[0034] The LC medium according to the present invention exhibits the following advantageous properties, particularly when used in an FFS display: · Excellent low-temperature stability (LTS), · Improved contrast ratio of the display, · High transmittance of the display, · High clearing temperature, · High voltage holding ratio, · Low rotational viscosity, · Fast switching, · Fast response time enabling a low power consumption LCD to extend the battery life for portable devices, · Sufficient stability against heat and / or UV, particularly when used outdoors, · A combination of fast response time suitable for use in gaming applications and appropriately high birefringence, particularly in displays having a cell gap of 3.3 μm or less.

Best Mode for Carrying Out the Invention

[0035] Preferred compounds of formulas IIA, IIB, IIC, and IID are shown below.

[0036]

Chemical Formula

[0037]

Chemical Formula

[0038]

Chemical Formula

[0039]

Chem.

[0040]

Chem.

[0041]

Chem.

[0042]

Chem.

[0043]

Chem.

[0044]

Chem.

[0045]

Chem.

[0046]

Chem.

[0047]

Chem.

[0048]

Chem.

[0049] [Chemical formula]

[0050] In the formula, the parameter a represents 1 or 2, alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 carbon atoms, alkenyl represents a linear alkenyl group having 2 to 6 carbon atoms, and (O) represents an oxygen atom or a single bond. Alkenyl preferably represents CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH- or CH3-CH=CH-(CH2)2-.

[0051] Highly preferred compounds of formula IID are selected from the following sub-formulas.

[0052] [Chemical formula]

[0053] [Chemical formula]

[0054] [Chemical formula]

[0055] [Chemical formula]

[0056] [Chemical formula]

[0057] In a preferred embodiment, the medium comprises one or more compounds of formula IID-10a.

[0058] [Chemical formula]

[0059] In the formula, the groups and parameters that appear have the meanings given above under formula IID, and R 2 represents [Chemical formula] wherein r is 0, 1, 2, 3, 4, 5 or 6, and s is 1, 2 or 3.

[0060] Preferred compounds of formula IID-10a are compounds IID-10a-1 to IID-10a-14.

[0061] [Chemical formula]

[0062] [Chemical formula]

[0063] [Chemical formula]

[0064] Particularly preferred mixtures according to the invention comprise one or more compounds of formulae IIA-2, IIA-8, IIA-10, IIA-16, IIA-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, IID-4 and IID-10.

[0065] Preferred media according to the invention comprise at least one compound of formula IIC-1.

[0066] [Chemical formula]

[0067] In the formula, alkyl and alkyl * have the meanings shown above.

[0068] In particular, the medium contains one or more compounds of formula IIA-2 selected from the following sub-formulas.

[0069]

Chemical formula

[0070] Alternatively or preferably, in addition to the compounds of formulas IIA-2-1 to IIA-2-5, the medium contains one or more compounds of formulas IIA-2a-1 to IIA-2a-5.

[0071]

Chemical formula

[0072] In particular, the medium contains one or more compounds of formula IIA-10 selected from the following sub-formulas.

[0073]

Chemical formula

[0074] Alternatively or preferably, in addition to the compounds of formulas IIA-10-1 to IIA-10-5, the medium contains one or more compounds of formulas IIA-10a-1 to IIA-10a-5.

[0075]

Chemical formula

[0076] In particular, the medium contains one or more compounds of formula IIB-10 selected from the following sub-formulas.

[0077]

Chemical formula

[0078] Alternatively, preferably in addition to the compounds of formulas IIB-10-1 to IIB-10-5, the medium comprises one or more compounds of formulas IIB-10a-1 to IIB-10a-5.

[0079]

Chemical formula

[0080] Alternatively, preferably in addition to the compound of formula IIC-1, the medium comprises one or more compounds of formulas IIC-1a-1 and IIC-1a-2.

[0081]

Chemical formula

[0082] In the formula, alkyl represents a linear alkyl having 1 to 7 C atoms, preferably 2 to 5 C atoms, and very preferably represents ethyl.

[0083] The medium according to the present invention preferably comprises one or more compounds of formula III.

[0084]

Chemical formula

[0085] In the formula, R 31 and R 32 each independently represents H, an alkyl or alkoxy group having 1 to 15 C atoms, provided that one or more CH2 groups in these groups are arranged such that O atoms are not directly linked to each other.

Chemical formula

[0086] The compound of formula III is preferably selected from the compounds of formula III-1 and / or III-2.

[0087] [Chemistry]

[0088] In the formula, the groups that appear have the same meanings as those given above in formula III, preferably R 31 and R 32 are each, independently of one another, an alkyl, alkenyl or alkoxy group having up to 15 carbon atoms, more preferably, one or both of them represent an alkoxy group, L 11 and L 12 each preferably represent F.

[0089] Preferably, the compound of formula III-1 is selected from the group of compounds of formulae III-1-1 to III-1-11, preferably formula III-1-6.

[0090] [Chemistry]

[0091] [Chemistry]

[0092] In the formula, alkyl and alkyl * each represent a linear alkyl group having 1 to 6 carbon atoms, independently of one another, alkenyl and alkenyl * each represent a linear alkenyl group having 2 to 6 carbon atoms, independently of one another, alkoxy and alkoxy * each represent a linear alkoxyl group having 1 to 6 carbon atoms, independently of one another, L 31 and L 32 each represent F or Cl, independently of one another, preferably both represent F.

[0093] Preferably, the compound of formula III-2 is selected from the group of compounds of formula III-2-1 to III-2-10, preferably the compound of formula III-2-6.

[0094]

Chemical formula

[0095]

Chemical formula

[0096] Wherein, alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 C atoms, alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 C atoms, alkoxy and alkoxy * each independently represents a linear alkoxyl group having 1 to 6 C atoms, L 31 and L 32 each independently represents F or Cl, preferably both F.

[0097] The medium may contain one or more compounds of formula IIIA-1 and / or IIIA-2.

[0098]

Chemical formula

[0099] Wherein, L 31 and L 32 have the same meaning as given above in formula III, (O) represents O or a single bond, R IIIA represents alkyl or alkenyl having up to 7 C atoms or the group Cy-C m H 2m+1 - represents, m and n are the same or different and are 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, Cy represents an alicyclic group having 3, 4 or 5 ring atoms, which may be substituted by alkyl or alkenyl or halogen or CN each having up to 3 C atoms, preferably represents cyclopropyl, cyclobutyl, cyclopentyl, cyclopent-1-enyl, cyclopent-2-enyl and cyclopent-3-enyl.

[0100] The compounds of formula IIIA-1 and / or IIIA-2 are either alternative or additional to the compounds of formula III and are preferably additionally contained in the medium.

[0101] Very preferred compounds of formula IIIA-1 and IIIA-2 are as follows.

[0102]

Chemical formula

[0103]

Chemical formula

[0104] wherein alkoxy is a linear alkoxy group having 1 to 6 C atoms, or -(CH2) n F (wherein n is 2, 3, 4 or 5), preferably represents C2H4F.

[0105] In a preferred embodiment of the present invention, the medium contains one or more compounds of formula III-3.

[0106]

Chemical formula

[0107] wherein R 31 、R 32represents an alkyl or alkoxy group having the same or different H, 1 to 15 C atoms, provided that in these groups, one or more CH2 groups are arranged so that O atoms are not directly linked to each other, and -C≡C-, -CF2O-, -OCF2-, -CH=CH-,

Chemical formula

[0108] The compound of formula III-3 is preferably selected from the group of compounds of formula III-3-1 to III-3-10.

[0109]

Chemical formula

[0110]

Chemical formula

[0111] In the formula, R 32 is alkyl having 1 to 7 C atoms, preferably ethyl, n-propyl or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl or alternatively -(CH2) n F (where n is 2, 3, 4 or 5), preferably represents C2H4F.

[0112] In a preferred embodiment of the present invention, the medium contains one or more compounds of formula III-4 to III-6, preferably compounds of formula III-5.

[0113]

Chemical formula

[0114] In the formula, the parameters have the meanings given above, and R 31represents preferably a linear alkyl, R 32 represents preferably an alkoxy, each having 1 to 7 C atoms.

[0115] In a preferred embodiment, the medium comprises one or more compounds of formula III selected from the group of compounds of formula III-7 to III-9, preferably of formula III-8.

[0116]

Chemical formula

[0117] In the formula, the parameters have the meanings given above, R 31 represents preferably a linear alkyl, R 32 represents preferably an alkoxy, each having 1 to 7 C atoms.

[0118] In a preferred embodiment, the medium comprises one or more compounds of formula IV.

[0119]

Chemical formula

[0120] In the formula, R 41 represents an alkyl group having 1 to 7 C atoms or an alkenyl group having 2 to 7 C atoms, preferably an n-alkyl group, particularly preferably having 2, 3, 4 or 5 C atoms, and R 42 represents an alkyl group having 1 to 7 C atoms or an alkoxy group having 1 to 6 C atoms (both preferably having 2 to 5 C atoms), an alkenyl group having 2 to 7 C atoms, preferably having 2, 3 or 4 C atoms, more preferably a vinyl group or a 1-propenyl group, particularly a vinyl group.

[0121] The compounds of formula IV are preferably selected from the group of compounds of formula IV-1 to IV-4.

[0122] [Chemical formula]

[0123] In the formula, alkyl and alkyl’ each independently represent an alkyl having 1 to 7 C atoms, preferably 1 to 5 C atoms. alkenyl represents an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 C atoms. alkenyl’ represents an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 to 3 C atoms. alkoxy represents an alkoxy having 1 to 5 C atoms, preferably 2 to 4 C atoms.

[0124] The compound of formula IV-1 is preferably selected from the group of compounds of formulae IV-1-1 to IV-1-6.

[0125] [Chemical formula]

[0126] The compound of formula IV-2 is preferably selected from the compounds of formulae IV-2-1 and IV-2-2.

[0127] [Chemical formula]

[0128] The compound of formula IV-3 is preferably selected from the group of compounds of formulae IV-3-1, IV-3-2 and IV-3-3.

[0129] [Chemical formula]

[0130] In the formula, alkyl has the meaning defined above, provided that the compounds of formula I are excluded from formula IV-3-2.

[0131] The compounds of formulae IV-3-1, IV-3-2 and IV-3-3 are preferably selected from the following compounds.

[0132]

Chemical formula

[0133] Very preferably, the medium according to the invention comprises a compound selected from the compounds of formula IV-4, in particular of formulae IV-4-1 to IV-4-3.

[0134]

Chemical formula

[0135] The liquid crystal medium preferably additionally comprises one or more compounds of formula IVa.

[0136]

Chemical formula

[0137] In the formula, R 41 and R 42 each independently represent a linear alkyl, alkoxy, alkenyl, alkoxyalkyl or alkoxy group having up to 12 carbon atoms, and

Chemical formula

[0138] Preferred compounds of formula IVa are shown below.

[0139] [Chemical formula]

[0140] In the formula, alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms.

[0141] The medium according to the present invention preferably contains at least one compound of formula IVa-1 and / or formula IVa-2.

[0142] The proportion of the compound of formula IVa in the whole mixture is preferably less than 5% by weight, very preferably less than 2% by weight.

[0143] Preferably, the medium contains one or more compounds of formula IVb-1 to IVb-4, more preferably compounds of formula IVb-1 to IVb-3.

[0144] [Chemical formula]

[0145] In the formula, alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms, and alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 carbon atoms.

[0146] Among the compounds of formula IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0147] Particularly preferred biphenyls.

[0148] [Chemical formula]

[0149] wherein alkyl * represents an alkyl group having 1 to 6 C atoms, preferably represents n-propyl. The medium according to the present invention particularly preferably contains one or more compounds of formula IVb-1-1 and / or IVb-2-3.

[0150] In a particularly preferred embodiment, the medium according to the present invention contains one or more compounds of formula V.

[0151]

Chemical formula

[0152] wherein R 51 , R 52 represents alkyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms,

Chemical formula

[0153] Compounds of formula V are preferably selected from compounds of formula V-1, V-2 and V-3.

[0154]

Chemical formula

[0155] wherein the groups occurring have the meanings given above for formula V.

[0156] The compound of formula V-1 is preferably selected from the compounds of formulas V-1-1 to V-1-8; The compound of formula V-2 is preferably selected from the compounds of formulas V-2-1 to V-2-4; and The compound of formula V-3 is preferably selected from the compounds of formulas V-3-1 to V-3-4.

[0157]

Chemical formula

[0158]

Chemical formula

[0159] In the formula, R 51 and R 52 have the meanings shown above in formula V. R 51 and R 52 preferably each independently represents a straight-chain alkyl having 1 to 7 carbon atoms or an alkenyl having 2 to 7 carbon atoms.

[0160] A highly preferred compound of formula V-2-1 is selected from the compounds of formulas V-2-1a to V-2-1g.

[0161]

Chemical formula

[0162] A highly preferred compound of formula V-2-2 is selected from the compounds of formulas V-2-2a to V-2-2i.

[0163]

Chemical formula

[0164] Preferably, the medium according to the present invention contains one or more compounds of formula CL.

[0165]

Chemical formula

[0166] In the formula R L represents H, a linear or branched alkyl or alkoxy group having 1 to 15 C atoms, or a linear or branched alkenyl group having 2 to 15 C atoms, provided that in these groups, one or more CH2 groups are arranged such that O atoms are not directly linked to each other,

Chemical formula

[0167] The compound of formula CL is preferably selected from the group consisting of compounds of formula CL-1, CL-2 and CL-3.

[0168]

Chemical formula

[0169] In the formula, R L1 and R L2 are the same or different and have the meanings given for formula I above, preferably representing alkyl or alkenyl having 1 to 7 or 2 to 7 C atoms respectively, and in the group, a CH2 group may be replaced with cyclopropane-1,2-diyl, or R L2 represents alkoxy having 1 to 5 C atoms.

[0170] The highly preferred compounds of formula CL are selected from the compounds of formulae CL-3-1 to CL-3-12.

[0171]

Chem.

[0172]

Chem.

[0173] In a particularly preferred embodiment, the medium according to the invention comprises the compound CL-3-1 or CLP-3-3.

[0174] In a preferred embodiment of the invention, the medium additionally comprises one or more compounds of formula VI.

[0175]

Chem.

[0176] wherein R 61 and R 62 represent H, F, a linear alkyl or alkoxy having 1 to 15 C atoms, a linear alkenyl or alkenyloxy having 2 to 15 C atoms or a branched alkyl, alkoxy, alkenyl or alkenyloxy each having 3 to 15 C atoms, provided that in these groups one or more CH2 groups are such that O atoms are not directly linked to each other, and each independently of one another

Chem.

[0177] The compound of formula VI is preferably selected from formula VI-1 and VI-2.

[0178]

Chemical formula

[0179] In the formula, the groups that appear have the meanings given in formula VI.

[0180] The compound of formula VI-1 is preferably selected from formula VI-1-1 to VI-1-21, very preferably from formula VI-1-4.

[0181]

Chemical formula

[0182]

Chemical formula

[0183]

Chemical formula

[0184] In the formula, R 6represents a linear alkyl or alkoxy group having 1 to 6 carbon atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5 or 6, and n is 0, 1, 2, 3 or 4. R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.

[0185] In the compound of formula IV-1-4, (O) preferably represents -O-.

[0186] The compound of formula VI-2 is preferably selected from formulae VI-2-1 to VI-1-15, and very preferably from formula VI-2-1.

[0187]

Chemical formula

[0188]

Chemical formula

[0189]

Chemical formula

[0190] In the formula, R 6 represents a linear alkyl or alkoxy group having 1 to 6 carbon atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5 or 6, and n is 0, 1, 2, 3 or 4. R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.

[0191] In a preferred embodiment of the present invention, the medium further contains one or more compounds of formulae VII-1 to VII-9.

[0192]

Chemical formula

[0193]

Chem.

[0194] In the formula, R 7 represents a linear alkyl or alkoxy group having 1 to 6 C atoms or a linear alkenyl group having 2 to 6 C atoms, and w is an integer from 1 to 6.

[0195] Preferably, the medium according to the invention comprises one or more compounds of formula VIII.

[0196]

Chem.

[0197] In the formula, R 81 and R 82 are the same or different and represent H, halogen, CN, SCN, a linear alkyl or alkoxy having 1 to 15 C atoms, a linear alkenyl or alkenyloxy having 2 to 15 C atoms or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 C atoms, provided that one or more CH2 groups in these groups are such that O atoms are not directly linked to each other,

Chem.

[0198] A in formula I 81 and A 81 are preferably phenylene-1,4-diyl (and the group may be mono- or polysubstituted by F), furthermore cyclohexane-1,4-diyl, cyclohexenylene-1,4-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, very preferably phenylene-1,4-diyl (and the group may be mono- or polysubstituted by F) or cyclohexane-1,4-diyl.

[0199] Z in formula VIII81 and Z 81 preferably represents -CF2O-, -OCF2- or a single bond, very preferably a single bond.

[0200] A in formula VIII 81 and A 81 are particularly preferably

Chemical formula

[0201] R 81 and R 82 each independently represents H, F or alkyl, alkoxy, alkenyl or alkynyl having 1 to 8, preferably 1 to 5 C atoms, and each of said groups may be replaced by halogen, especially F, and compounds of formula VIII are more preferred.

[0202] R 81 and R 82 preferably represents H, fluorinated alkyl or alkoxy having 1 to 7 C atoms, fluorinated alkenyl or alkynyl having 2 to 7 C atoms, fluorinated cycloalkyl having 3 to 12 C atoms.

[0203] Preferably R 81 and R 82 at least one of them is not H, particularly preferably neither R 81 and R 82 is H. R 81 is very particularly preferably alkyl. R 82 is more preferably H, alkyl or F. Very particularly preferably R 81 is alkyl and R 82 is H or alkyl. R 81 R 82 each independently very particularly preferably represents unbranched alkyl having 1 to 5 C atoms. R 81 and R 82When representing alkyl, alkoxy, alkenyl or alkynyl which is substituted, the total number of C atoms in two groups R 81 and R 82 is preferably less than 10.

[0204] Preferred compounds of formula VIII are selected from the compounds of formula VIIIa.

[0205]

Chemical formula

[0206] In the formula, R 1 and R 2 are the same or different and represent linear alkyl having 1 to 15 C atoms, linear alkenyl having 2 to 15 C atoms or branched alkyl or alkenyl having 3 to 15 C atoms, provided that one or more CH2 groups in these groups are

Chemical formula

[0207] Highly preferred compounds of formula VIIIa are selected from the compounds of formula VIIIa-1 to VIIIa-35.

[0208]

Chemical formula

[0209]

Chemical formula

[0210]

Chemical formula

[0211]

Chem.

[0212]

Chem.

[0213]

Chem.

[0214] In the formula, v is an integer from 1 to 6.

[0215] More preferred compounds of formula VIII are selected from the following sub-formulas.

[0216]

Chem.

[0217] In the formula, R 81 , R 82 and L have the meanings shown above, L preferably represents F, and r, s and t are independently 0, 1, 2, 3 or 4. r is preferably 1 or 2, very preferably 2, and s and t are independently preferably 0 or 1, very preferably 0. R 81 and R 82 each independently represent n-alkyl having 1 to 5 carbon atoms.

[0218] In the first very preferred embodiment, the compounds of formulas VIII-1 to VIII-6 are selected from the compounds of formulas VIII-1a to VIII-6a, particularly the compound of formula VIII-3a.

[0219]

Chem.

[0220] In the formula, R81 and R 82 , r and s have the meanings defined above.

[0221] In a second highly preferred embodiment, the compounds of formulas VIII-1 to VIII-6 are selected from the compounds of formulas VIII-1b to VIII-6b, in particular the compound of formula I3-b.

[0222]

Chemical formula

[0223] wherein R 81 and R 82 , L, r and s have the meanings defined above.

[0224] In a third highly preferred embodiment, the compounds of formulas VIII-1 to III-6 are selected from the compounds of formulas III-1c to III-6c, in particular the compound of formula I3-c.

[0225]

Chemical formula

[0226] wherein R 81 and R 82 , L, r and s have the meanings defined above.

[0227] In a fourth highly preferred embodiment, the compounds of formulas VIII-1 to VIII-6 are selected from the compounds of formulas VIII-1d to VIII-6d, in particular the compound of formula VIII-3d.

[0228]

Chemical formula

[0229] wherein R 81 and R 82 , L, r and s have the meanings defined above.

[0230] In a particularly preferred embodiment, the medium according to the invention comprises one or more compounds selected from the group of formulas VIII-1a to VIII-6a and one or more compounds selected from the group of formulas VIII-1b to VIII-6b.

[0231] Very particularly preferably, the medium comprises one or more compounds selected from the group of the compounds of formulas VIII-3a, VIII-3b, VIII-3c and VIII-3d.

[0232]

Chem.

[0233] wherein R 81 , R 82 , L and r have the meanings defined above, and preferably r is 0.

[0234] The most preferred compounds of formula I include, in particular, one or more of the following.

[0235]

Chem.

[0236]

Chem.

[0237]

Chem.

[0238] Alternatively or in addition, the following compounds of formula I may be used.

[0239]

Chem.

[0240]

Chem.

[0241]

Chem.

[0242]

Chem.

[0243] In a preferred embodiment, the medium comprises one or more compounds of formula IX.

[0244]

Chem.

[0245] wherein R 1 and R 2 are the same or different and each represents H, halogen, a linear alkyl or alkoxy having 1 to 15 C atoms, a linear alkenyl or alkenyloxy having 2 to 15 C atoms or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 C atoms, provided that one or more CH2 groups in these groups are such that O atoms are not directly linked to each other,

Chem.

[0246] When n is 0 and Y represents H or CH3, more preferably H, L 11 and L 12 represents F, and an LC medium containing a compound of Formula IX is preferred.

[0247] Highly preferred compounds of Formula IX are selected from the compounds of Formulas IX-1 to IX-35.

[0248] [Chemical formula]

[0249] [Chemical formula]

[0250] [Chemical formula]

[0251] [Chemical formula]

[0252] [Chemical formula]

[0253] [Chemical formula]

[0254] In a preferred embodiment of the present invention, the medium contains one or more compounds of Formula X.

[0255] [Chemical formula]

[0256] In the formula, [Chemical formula] represents [Chemical formula] represents R X represents a linear or branched alkyl or alkoxy group having 1 to 15 C atoms, provided that in these groups, one or more CH2 groups are arranged such that O atoms are not directly connected to each other. [Chemical formula] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO-, and may each be independently replaced with each other. In addition, one or more H atoms in the group may be replaced with a halogen, preferably F. X X represents F, Cl, CN, SF5, SCN, NCS, a halogenated alkyl group or halogenated alkoxy group each having 1 to 6 C atoms, or a halogenated alkenyl group or halogenated alkenyloxy group each having 2 to 6 C atoms. Z X represents -C2H4-, -CH2O-, CF2O, -CH=CH- or a single bond.

[0257] In the compound of formula X, R X preferably represents alkyl having 1 to 6 C atoms or alkenyl having 2 to 6 C atoms, and the group is preferably linear.

[0258] In the compound of formula X, X X is preferably F, Cl, or a monofluorinated or polyfluorinated alkyl or alkoxy group having 1, 2 or 3 C atoms, or a monofluorinated or polyfluorinated alkenyl group having 2 or 3 C atoms. XX is more preferably F, Cl, CF3, CHF2, OCF3, OCHF2, OCFHCF3, OCFHCHF2, OCFHCHF2, OCF2CH3, OCF2CHF2, OCF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCFHCF2CF3, OCFHCF2CHF2, OCF2CF2CF3, OCF2CF2CClF2, OCClFCF2CF3, OCH=CF2 or CH=CF2, very preferably F or OCF3, further CF3, OCF=CF2, OCHF2 or OCH=CF2, very particularly preferably F, OCF3 or CF3, and most preferably F.

[0259] Preferred compounds of formula X are selected from the following sub-formulas.

[0260]

Chemical formula

[0261] In the formula, R X has one of the meanings given by formula X, preferably a linear alkyl having 1 to 6 C atoms, very preferably ethyl, propyl or butyl, or a linear alkenyl having 2 to 6 C atoms, very preferably vinyl or 1-propenyl, and most preferably vinyl, and X X has one of the meanings given by formula X, preferably represents F, CF3 or OCF3, and very preferably represents F.

[0262] Very preferred compounds of formula X are selected from the following sub-formulas.

[0263]

Chemical formula

[0264]

Chemical formula

[0265]

Chemical formula

[0266] [Chemical]

[0267] [Chemical]

[0268] Preferably, the LC medium contains one or more compounds selected from the group consisting of formulas X1-1, X1-3, X2-1, and X2-3.

[0269] Even more preferred embodiments are listed below.

[0270] a) A liquid crystal medium containing at least one compound of formulas Z-1 to Z-8, preferably formulas Z-2, Z-4, and Z-6, and very preferably Z-4.

[0271] [Chemical]

[0272] In the formula, R Z has the meaning of R shown above 2A and preferably represents alkyl having 1 to 7 carbon atoms or alkenyl having 2 to 7 carbon atoms, (O) represents O or a single bond, and alkyl represents alkyl having 1 to 7 carbon atoms.

[0273] b) Preferred liquid crystal media according to the invention contain one or more substances containing tetrahydronaphthyl or naphthyl units, such as compounds of formulas N-1 to N-5.

[0274] [Chemical]

[0275] wherein R 1N and R 2N each independently has the meaning shown for R 2A and preferably represents a linear alkyl, linear alkoxy or linear alkenyl, Z 1 and Z 2 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.

[0276] c) Preferred mixtures comprise one or more compounds selected from the group consisting of difluorodibenzochroman compounds of formula BC, chromans of formula CR and fluorinated phenanthrenes of formulae PH-1 and PH-2.

[0277]

Chemical formula

[0278] wherein R B1 , R B2 , R CR1 , R CR2 , R P1 , R P2 each independently has the meaning of R of formula III 31 and c is 0, 1 or 2. R 1 and R 2 preferably each independently represents an alkyl or alkoxy having 1 to 6 C atoms.

[0279] Particularly preferred compounds of formulae BC, CR and PH-1 are compounds BC-1 to BC-7, CR-1 to CR-5 and BC-1 to BC-7.

[0280]

Chemical formula

[0281]

Chem.

[0282]

Chem.

[0283] In the formula, alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 carbon atoms.

[0284] A mixture containing one, two or three compounds of formula BC-2, BC-3, BP-2 and / or BP-3, very preferably BP-2 and / or BP-3, is highly particularly preferred.

[0285] d) Preferred mixtures contain one or more indane compounds of formula In.

[0286]

Chem.

[0287] In the formula, R 11 , R 12 and R 13 each independently represents a linear alkyl, alkoxy, alkoxyalkyl or alkenyl group having 1 to 6 carbon atoms, R 12 and R 13 represent halogen, preferably F,

Chem.

[0288] Preferred compounds of formula In are compounds of formulae In-1 to In-16 shown below.

[0289]

Chem.

[0290]

Chem.

[0291]

Chem.

[0292] Compounds of formulae In-1, In-2, In-3 and In-4 are particularly preferred.

[0293] e) Preferred mixtures additionally contain one or more compounds of formulae L-1 to L-5.

[0294]

Chem.

[0295]

Chem.

[0296]

Chem.

[0297] wherein R, R 1 and R 2 each independently have the meanings shown for R 2A in formula IIA above, and alkyl represents an alkyl group having 1 to 6 C atoms. The parameter s represents 1 or 2.

[0298] The compounds of formulas L1 to L9 are preferably used at a concentration of 5 to 15% by weight, particularly 5 to 12% by weight, and very particularly preferably 8 to 10% by weight.

[0299] f) Preferred mixtures additionally contain one or more compounds of formula IIA-Y.

[0300]

Chemical formula

[0301] wherein R 11 and R 12 have one of the meanings given for R 2A in formula IIA above, and L 1 and L 2 represent F or Cl, which may be the same or different.

[0302] Preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0303]

Chemical formula

[0304]

Chemical formula

[0305] wherein Alkyl and Alkyl * each independently represent a linear alkyl group having 1 to 6 carbon atoms, Alkoxy represents a linear alkoxy group having 1 to 6 carbon atoms, Alkenyl and Alkenyl * each independently represent a linear alkenyl group having 2 to 6 carbon atoms, and O represents an oxygen atom or a single bond. Alkenyl 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-.

[0306] Particularly preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0307]

Chemical formula

[0308] wherein Alkoxy and Alkoxy * have the meanings defined above and preferably represent methoxy, ethoxy, n-propyloxy, n-butyloxy or n-pentyloxy.

[0309] Preferably, the medium according to the present invention is of formula ST-1 to formula ST-18,

[0310] Very preferably, it contains compounds selected from the group of compounds of formula ST-3.

[0311]

Chemical formula

[0312]

Chemical formula

[0313]

Chemical formula

[0314]

Chemical formula

[0315] wherein R STrepresents an alkyl or alkoxy group having H and 1 to 15 C atoms, provided that in addition, one or more CH2 groups in these groups are arranged such that O atoms are not directly connected to each other, and -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [Chemical formula] -O-, -CO-O-, -O-CO- may each be independently replaced with each other, and in addition, one or more H atoms in the group may be replaced with halogen, [Chemical formula] is the same or different at each occurrence, [Chemical formula] represents, Z ST 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, independently of each other, L 1 and L 2 each represents F, Cl, CH3, CF3 or CHF2, independently of each other, p represents 0, 1 or 2, q represents 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0316] Among the compounds of formula ST, the compounds of the following formula are particularly preferred.

[0317] [Chemical formula]

[0318] [Chemical formula]

[0319]

Chem.

[0320] In the compounds of formulae ST-3a and ST-3b, n preferably represents 3. In the compound of formula ST-2a, n preferably represents 7.

[0321] A very particularly preferred mixture according to the invention comprises one or more stabilizers from the group of compounds of formulae ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1, ST-12.

[0322]

Chem.

[0323]

Chem.

[0324] Preferably, the medium comprises one or more compounds of formula S.

[0325]

Chem.

[0326] wherein Ar represents a methylene group, an aromatic hydrocarbon group having 6 to 40 carbon atoms or a heteroaromatic hydrocarbon group having 4 to 40 carbon atoms; preferably represents an aromatic hydrocarbon group having 6 to 40 carbon atoms; Sp represents a spacer group; R S represents H, alkyl having 1 to 12 carbon atoms or alkenyl having 2 to 12 carbon atoms; Z S is -O-, -C(O)O-, -(CH2) z - or -(CH2) zrepresents O- or a single bond; HA is [Chemical formula] represents; R H is H, O · , CH3, OH or OR S represents; R S1 , R S2 , R S3 and R S4 are the same or different and represent alkyl having 1 to 6 C atoms, preferably 1 to 3 C atoms, very preferably CH3; G is H or R S or group Z S -HA; z is an integer from 1 to 6; and q is 2, 3 or 4, preferably 3 or 4.

[0327] In formula S, aryl represents an aromatic or heteroaromatic hydrocarbon group having 4 to 40 C atoms, and may contain 1, 2, 3 or 4 aromatic rings including a condensed ring which may be bonded directly or via an alkylene linking group having 1 to 12 C atoms. In the group, one or more H atoms may be replaced by alkyl or alkoxy having 1 to 6 C atoms or alkenyl having 2 to 6 C atoms, or by CN, CF3 or halogen. In the group, one or more CH2 groups may each be independently replaced by -O-, -S-, -NH-, -N(C1-C4-alkyl)-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH- or -C≡C- so that O or S atoms do not bond directly to each other.

[0328] Preferred aryl groups are benzene, naphthalene, anthracene, biphenyl, m-terphenyl, p-terphenyl and (phenylalkyl)benzene, and in the group, alkyl is linear alkyl having 1 to 12 C atoms.

[0329] In a preferred embodiment, the medium according to the invention has a parameter q of 3 and G is a group Z S and comprises a compound of formula S representing -HA.

[0330] In another preferred embodiment, the medium according to the invention has a parameter q of 4 and G is H or R S and comprises a compound of formula S.

[0331] The compound of formula S is preferably selected from the compounds of formulae S-1, S-2 and S-3.

[0332]

Chemical formula

[0333]

Chemical formula

[0334] wherein R H has the meaning given above and is preferably H or O · and represents; Sp represents a spacer group, which is the same or different at each occurrence, W represents an alkylene which is linear or branched and optionally unsubstituted and has 1 to 12 C atoms, and in which one or more non-adjacent -CH2- groups may be replaced by -O-.

[0335] Preferred compounds of formula S-1 are selected from the compounds of formula S-1-1.

[0336]

Chemical formula

[0337] wherein R H has the meaning given above and is preferably H or O · and represents, and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7.

[0338] The preferred compounds of formula S-2 are selected from the compounds of formula S-2-1.

[0339]

Chemical formula

[0340] wherein R H has the meaning given above, preferably H or O · represents, and n2 is, in each occurrence, the same or different, preferably the same and an integer from 0 to 12, preferably 2, 3, 4, 5 or 6, very preferably 3, and R S is, in each occurrence, the same or different, preferably the same and alkyl having 1 to 6 C atoms, preferably n-butyl.

[0341] The preferred compounds of formula S-3 are selected from the compounds of formula S-3-1.

[0342]

Chemical formula

[0343] wherein R H has the meaning given above, preferably H or O · represents, and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7.

[0344] The compounds of formula S and ST-1 to ST-18 are preferably present in the liquid crystal mixture according to the invention in an amount of 0.005 to 0.5% based on the respective mixture.

[0345] When the mixture according to the invention contains two or more compounds from the group of compounds of formula S and ST-1 to ST-18, the concentration increases correspondingly to 0.01 to 1% for two compounds based on the mixture.

[0346] However, the total proportion of the compounds of formulas S and ST-1 to ST-18 based on the mixture according to the invention preferably does not exceed 2%.

[0347] The liquid crystal medium according to the invention, also referred to herein as a liquid crystal host mixture, is suitable for use in polymer stabilized displays. For this purpose, the medium according to the invention may contain one or more polymerizable compounds of formula P.

[0348]

Chemical formula

[0349] In the formula, each independently of one another, the same or different in each occurrence, P represents a polymerizable group, Sp represents a spacer group or a single bond, A 1 、A 2 is an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably having 4 to 25 ring atoms, the group may include a fused ring, the group is unsubstituted or mono- or polysubstituted by L, Z 1 is -O-, -S-, -CO-, -CO-O-, -O-CO-, -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-CO-O-, -O-CO-CH=CH-, -CH2-CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 - or represents a single bond, R 0 、R 00 represents H or alkyl having 1 to 12 carbon atoms, R represents H, L or P-Sp-, L represents a straight-chain, branched or cyclic alkyl having F, Cl, -CN, P-Sp- or 1 to 25 C atoms, provided that one or more non-adjacent CH2 groups may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that O and / or S atoms are not directly linked to each other independently, provided that one or more H atoms may each be replaced by P-Sp-, F or Cl, z is 0, 1, 2 or 3, and n1 is 1, 2, 3 or 4.

[0350] As used herein, the term "reliability" means the quality of the performance of a display consisting of different stress loads such as optical load, temperature, humidity, voltage, etc. over time, and display effects such as image sticking (area and line image sticking), unevenness, and stain known to those skilled in the art in the field of liquid crystal displays. As a standard parameter for classifying reliability, a voltage holding ratio (VHR) value is usually used, which is a measure for maintaining a constant electric voltage in a test display. A high VHR is a prerequisite for high reliability of the LC medium.

[0351] Hereinafter, unless otherwise specified, the term "PSA" is used when referring to polymer-maintained alignment type displays in general, and the term "PS" is used when referring to specific display modes such as PS-VA and PS-TN.

[0352] As used herein, the terms "active layer" and "switchable layer" mean layers in an electro-optical display, such as an LC display, containing one or more types of molecules having structural and optical anisotropy, such as LC molecules, whose molecular orientation changes upon external stimuli such as an electric field or a magnetic field, and as a result, the permeability of the layer to polarized or non-polarized light changes.

[0353] As used herein, the terms "tilt" and "tilt angle" are to be understood to mean an orientation in which the LC molecules of the LC medium are tilted with respect to the cell surface in an LC display (preferably, a PSA display in this specification). In this specification, the tilt angle means the average angle (less than 90°) between the molecular long axis (LC director) of the LC molecules and the surface of the flat and parallel outer plates forming the LC cell. In this specification, a low value of the tilt angle (i.e., significantly deviating from the angle of 90°) corresponds to a large tilt. An appropriate method for measuring the tilt angle is given in the examples. Unless otherwise indicated, the values of the tilt angles disclosed above and below relate to this measurement method.

[0354] As used herein, the terms "reactive mesogen" and "RM (reactive mesogen)" are to be understood to mean a compound containing a mesogen or liquid crystal backbone and one or more functional groups suitable for polymerization linked to the backbone, and the functional groups are also referred to as "polymerizable groups" or "P".

[0355] Unless otherwise stated, as used herein, the term "polymerizable compound" is to be understood to mean a polymerizable monomer compound.

[0356] As used herein, the term "low molecular weight compound" is a term relative to "polymer compound" or "polymer", and is to be understood to mean a monomer and / or a compound not prepared by a polymerization reaction.

[0357] As used herein, the term "non-polymerizable compound" is to be understood to mean a compound that does not contain functional groups suitable for polymerization under the conditions normally applied for the polymerization of RM.

[0358] As used herein, the term "mesogenic group" is known to those skilled in the art and described in the literature, and means a group that essentially contributes to the generation of a liquid-crystalline (LC) phase in low-molecular-weight or high-molecular-weight substances due to the anisotropy of its attractive and repulsive interactions. A compound containing a mesogenic group (mesogenic compound) does not necessarily have an LC phase by itself. Also, it is possible for the mesogenic compound to exhibit LC phase behavior only after mixing with other compounds and / or polymerization. Typical mesogenic groups are, for example, units having a rigid rod-like or disc-like shape. An overview of the terms and definitions used with respect to mesogens or LC compounds is given in Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340 - 6368.

[0359] As used herein, the terms "optically active" and "chiral" are synonyms for a material that can induce a helical pitch in a nematic host material, and are also referred to as "chiral dopants".

[0360] As used herein, the term "spacer group", also referred to as "Sp" above and below, is known to those skilled in the art and described in the literature. See, for example, Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340 - 6368. As used herein, the term "spacer group" or "spacer" means a flexible group, such as an alkylene group, that links a mesogenic group and one or more polymerizable groups in a polymerizable mesogenic compound.

[0361] Similarly, in the compound of formula I, the spacer group is linked to a central hydrocarbon group having optical activity to stabilize the hindered amine functional group.

[0362] Above and below, [Chemistry] represents a trans-1,4-cyclohexylene ring.

[0363] group [Chemistry] In [chemical formula], the single bond shown between two ring atoms can be linked to any unbonded position of the benzene ring.

[0364] Above and below, "organic group" represents a carbon or hydrocarbon group.

[0365] "Carbon group" represents a monovalent or polyvalent organic group containing at least one carbon atom, provided that this either does not contain any further types of atoms (e.g., -C≡C-), or may contain one or more further atoms such as N, O, S, B, P, Si, Se, As, Te, or Ge (e.g., carbonyl, etc.). The term "hydrocarbon group" additionally contains one or more H atoms and represents a carbon group that may contain one or more heteroatoms such as N, O, S, B, P, Si, Se, As, Te, or Ge.

[0366] "Halogen" represents F, Cl, Br, or I, preferably F or Cl.

[0367] -CO-, -C(=O)-, and -C(O)- represent a carbonyl group, i.e., [Chemistry] represents.

[0368] The carbon or hydrocarbon group may be either a saturated or unsaturated group. Unsaturated groups are, for example, aryl, alkenyl, or alkynyl groups. Carbon or hydrocarbon groups having more than three C atoms may be linear, branched, and / or cyclic, and may also contain spiro linkages or fused rings.

[0369] Also, terms such as "alkyl", "aryl", "heteroaryl", etc. also include polyvalent groups, for example, alkylene, arylene, heteroarylene, etc.

[0370] The term "aryl" represents an aromatic carbon group or a group derived therefrom. The term "heteroaryl" contains one or more heteroatoms (preferably selected from N, O, S, Se, Te, Si, and Ge) and represents "aryl" as defined above.

[0371] Preferred carbon and hydrocarbon groups may be substituted and have 1 to 40, preferably 1 to 20, particularly preferably 1 to 12 C atoms, and are linear, branched, or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, and alkoxycarbonyloxy, may be substituted and have 5 to 30, preferably 6 to 25 C atoms, aryl or aryloxy, or may be substituted and have 5 to 30, preferably 6 to 25 C atoms, alkylaryl, arylalkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy, and aryloxycarbonyloxy, provided that one or more C atoms may preferably be replaced by a heteroatom selected from N, O, S, Se, Te, Si, and Ge.

[0372] Even more preferred carbon and hydrocarbon groups are C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C2-C 20 allyl, C4-C 20 alkyldienyl, C4-C 20 polyenyl, C6-C 20 cycloalkyl, C4-C 15 cycloalkenyl, C6-C 30 aryl, C6-C 30 alkylaryl, C6-C 30 arylalkyl, C6-C30 Alkylaryl oxy, C6 - C 30 Arylalkyl oxy, C2 - C 30 Heteroaryl, C2 - C 30 It is heteroaryl oxy.

[0373] C1 - C 12 Alkyl, C2 - C 12 Alkenyl, C2 - C 12 Alkynyl, C6 - C 25 Aryl and C2 - C 25 Heteroaryl is particularly preferred.

[0374] More preferred carbon and hydrocarbon groups are linear, branched or cyclic alkyl having 1 - 20, preferably 1 - 12 C atoms, and the group is unsubstituted or mono - or polysubstituted with F, Cl, Br, I or CN, provided that one or more non - adjacent CH2 groups are each independently replaced by -C(R x )=C(R x ) -, -C≡C -, -N(R x ) -, -O -, -S -, -CO -, -CO - O -, -O - CO -, -O - CO - O - so that O and / or S atoms are not directly linked to each other.

[0375] R x preferably represents H, F, Cl, CN, a linear, branched or cyclic alkyl chain having 1 - 25 C atoms (provided that in addition, one or more non - adjacent C atoms may be replaced by -O -, -S -, -CO -, -CO - O -, -O - CO -, -O - CO - O -, provided that one or more H atoms may be replaced by F or Cl), or an optionally substituted aryl or aryloxy group having 6 - 30 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 - 30 C atoms.

[0376] Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecanyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, perfluorohexyl, and the like.

[0377] Preferred alkenyl groups include, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, and the like.

[0378] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl, and the like.

[0379] Preferred alkoxy groups include, for example, methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, and the like.

[0380] Preferred amino groups include, for example, dimethylamino, methylamino, methylphenylamino, phenylamino, and the like.

[0381] Aryl and heteroaryl groups may be monocyclic or polycyclic, i.e., they may contain one ring (e.g., phenyl, etc.) or two or more rings, and the group may be fused (e.g., naphthyl, etc.) or linked by a covalent bond (e.g., biphenyl, etc.), or may contain a combination of fused and linked rings. The heteroaryl group preferably contains one or more heteroatoms selected from O, N, S, and Se.

[0382] Monocyclic, bicyclic or tricyclic aryl groups having 6 to 25 C atoms and monocyclic, bicyclic or tricyclic heteroaryl groups having 5 to 25 ring atoms are particularly preferred, and these groups may contain fused rings and may be substituted. Further, 5-membered, 6-membered or 7-membered aryl and heteroaryl groups are preferred, provided that in addition, one or more CH groups may be replaced by N, S or O such that O atoms and / or S atoms are not directly linked to each other.

[0383] Preferred aryl groups are, for example, phenyl, biphenyl, terphenyl, [1,1’:3’,1”]terphenyl-2’-yl, naphthyl, anthracene, binaphthyl, phenanthrene, 9,10-dihydrophenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene, spirobifluorene, etc.

[0384] Preferred heteroaryl groups include, for example, 5-membered rings such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole; 6-membered rings such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine; or fused groups such as indole, isoindole, indolizine, indazole, benzimidazole, benzotriazole, purine, naphthimidazole, phenanthroimidazole, pyridimidazole, pyrazineimidazole, quinoxalineimidazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, benzoisoquinoline, acridine, phenothiazine, phenoxazine, benzopyridazine, benzopyrimidine, quinoxaline, phenazine, naphthyridine, azacarbazole, benzocarbazole, phenanthridine, phenanthroline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, isobenzothiophene, dibenzothiophene, benzothiadiazothiophene; or combinations of these groups.

[0385] Also, the aryl and heteroaryl groups described above and below may be substituted with alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl or a further aryl or heteroaryl group.

[0386] (Non-aromatic) Alicyclic and heterocyclic groups include both saturated rings, i.e., those containing exclusively single bonds, and also partially unsaturated rings, i.e., those that may also contain multiple bonds. Heterocyclic rings preferably contain one or more heteroatoms selected from Si, O, N, S, and Se.

[0387] (Non-aromatic) Alicyclic and heterocyclic groups may be monocyclic, i.e., contain only one ring (e.g., cyclohexane, etc.), or polycyclic, i.e., contain multiple rings (e.g., decahydronaphthalene or bicyclooctane, etc.). Saturated groups are particularly preferred. Further, groups that are monocyclic, bicyclic, or tricyclic and have 5 to 25 ring atoms are preferred, and the group may contain fused rings and may be substituted. Further, 5-membered, 6-membered, 7-membered, or 8-membered carbocyclic groups are preferred, provided that in addition, one or more C atoms may be replaced by Si, and / or one or more CH groups may be replaced by N, and / or one or more non-adjacent CH2 groups may be replaced by -O- and / or -S-.

[0388] Preferred alicyclic and heterocyclic groups are, for example, 5-membered groups such as cyclopentane, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, etc., 6-membered groups such as cyclohexane, silinane, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, piperidine, etc., 7-membered groups such as cycloheptane, etc., and fused groups such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, octahydro-4,7-methanoindane-2,5-diyl, etc.

[0389] Preferred substituents are, for example, dissolution promoting groups such as alkyl or alkoxy, electron-withdrawing groups such as fluorine, nitro or nitrile, or substituents for raising the glass transition temperature (Tg) in the polymer, particularly, for example, bulky groups such as t-butyl or optionally substituted aryl groups.

[0390] Preferred substituents will hereinafter also be referred to as "L" S ", and include, 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, linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy each having 1 to 25 C atoms (provided that one or more H atoms may be replaced by F or Cl), silyl which may be substituted and has 1 to 20 Si atoms, or aryl which may be substituted and has 6 to 25 C atoms, preferably 6 to 15 C atoms.

[0391] In the formula, R x represents H, F, Cl, CN, a linear, branched or cyclic alkyl chain having 1 to 25 C atoms, provided that one or more non-adjacent CH2 groups may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that O- and / S-atoms are not directly linked to each other, provided that one or more H atoms may each be replaced by F, Cl, P- or P-Sp-, and Y 1 represents halogen.

[0392] "Substituted silyl or aryl" is preferably halogen, -CN, R 0 , -OR 0 , -CO-R 0 , -CO-O-R 0 , -O-CO-R 0 or -O-CO-O-R 0means substitution by, provided that R 0 represents H or an alkyl having 1 to 20 C atoms.

[0393] Particularly preferred substituents L are, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and further, phenyl.

[0394] A 1 and A 2 are very preferably [Chemical formula] represents, where L has one of the meanings shown above, r represents 0, 1, 2, 3 or 4, particularly [Chemical formula] represents.

[0395] The polymerizable group P is a group suitable for polymerization reactions such as free radical or ionic chain polymerization, polyaddition or polycondensation, or for polymer-analogous reactions such as addition or condensation onto the polymer main chain. Groups for chain polymerization, particularly those containing a C=C double bond or a C≡C triple bond, and groups suitable for ring-opening polymerization such as, for example, an oxetane or epoxide group are particularly preferred.

[0396] Preferred groups P are CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [Chemical formula] 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 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 selected from the group consisting of Si-, wherein W 1 represents H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, and W 2 and W 3 each independently of one another represents H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, and W 4 , W 5 and W 6 each independently of one another represents Cl, oxaalkyl or oxocarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 each independently of one another represents H, Cl or alkyl having 1 to 5 C atoms, Phe represents 1,4-phenylene which may be substituted by one or more groups L as defined above other than P-Sp-, k1, k2 and k3 each independently of one another represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0397] A very preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [Chemical] 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 selected from the group consisting of Si-, wherein W 1 represents H, F, Cl, CN, CF3, phenyl or alkyl having 1 to 5 C atoms, in particular, H, F, Cl or CH3, and W 2 and W 3 each independently of one another represents H or alkyl having 1 to 5 C atoms, in particular, H, methyl, ethyl or n-propyl, and W 4 W 5 and W 6 each independently of one another represents Cl, oxaalkyl or oxocarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 each independently of one another represents H, Cl or alkyl having 1 to 5 C atoms, Phe represents 1,4-phenylene, k1, k2 and k3 each independently of one another represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0398] A very particularly preferred group P is CH2=CW 1-CO-O-, especially, CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, further, CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, [Chemical formula] is selected from the group consisting of.

[0399] A more preferable polymerizable group P is selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide groups, and most preferably is selected from acrylate and methacrylate.

[0400] When the spacer group Sp is different from a single bond, Sp is preferably of the formula Sp”-X” such that each group P-Sp- corresponds to the formula R-Sp”-X”-, where Sp” and X” have the following meanings.

[0401] Sp” represents a linear or branched alkylene having 1 to 20, preferably 1 to 12 C atoms, which group may be mono- or polysubstituted with F, Cl, Br, I or CN, provided that in addition, one or more non-adjacent CH2 groups are each independently of one another, so that O and / or S atoms are not directly linked to each other, -O-, -S-, -NH-, -N(R 0 )-, -Si(R 0 R 00 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 )-CO-O-, -O-CO-N(R 0 )-, -N(R 0 )-CO-N(R 00 )-, -CH=CH- or -C≡C- may be replaced, X” is -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-, -N(R 0 )-CO-, -N(R 0)-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -, -CY 2 =CY 3 -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or a single bond, R 0 and R 00 each independently represents H or alkyl having 1 to 20 C atoms, Y 2 and Y 3 each independently represents H, F, Cl or CN.

[0402] X” is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 - or a single bond.

[0403] 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 -, where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 have the meanings shown above.

[0404] Particularly preferred spacer groups Sp and -Sp”-X”- are -(CH2) p1 -, -(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, provided that p1 and q1 have the meanings given above.

[0405] Particularly preferred groups Sp” are each linear and are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methylenoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.

[0406] In a preferred embodiment of the present invention, the compounds of formula P and its sub-formulas contain a spacer group Sp (branched polymerizable group) substituted with one or more polymerizable groups P such that the group Sp-P corresponds to Sp(P) s (where s is 2 or more).

[0407] Preferred compounds of formula P according to this preferred embodiment are those in which s is 2, i.e., compounds containing the group Sp(P)2. Very preferred compounds of formula P according to this preferred embodiment contain a group selected from the following formulas.

[0408]

Chemical formula

[0409] wherein P is as defined by formula P, Alkyl represents a single bond or a straight-chain or branched alkylene having 1 to 12 carbon atoms, and the group is unsubstituted or mono- or polysubstituted with F, Cl or CN, provided that one or more non-adjacent CH2 groups are each independently of one another such that O and / or S atoms are not directly linked to each other, -C(R 0 )=C(R 0 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- may be replaced, provided that R 0 has the meaning shown above, aa and bb each independently represent 0, 1, 2, 3, 4, 5 or 6, X has one of the meanings shown for X”, and preferably is O, CO, SO2, O-CO-, CO-O or a single bond.

[0410] Preferred spacer group Sp(P)2 is selected from formulas S1, S2 and S3.

[0411] Highly preferred spacer group Sp(P)2 is selected from the following sub-formulas.

[0412]

Chemical formula

[0413] In the compounds of formula P and its sub-formulas as above and below, P is preferably selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide, most preferably acrylate and methacrylate.

[0414] All polymerizable groups P present in the compound have the same meaning, and the compounds of formula P and its sub-formulas as above and below, which very preferably represent acrylate or methacrylate, most preferably methacrylate, are even more preferred.

[0415] In the compounds of formula P and its sub-formulas as described above and below, R preferably represents P-Sp.

[0416] Sp is a single bond or -(CH2) p1 -, -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 where p1 is 2, 3, 4, 5 or 6, and when Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 the compounds of formula P and its sub-formulas as described above and below in which the O atom or CO group is respectively linked to the benzene ring are more preferred.

[0417] The compounds of formula P and its sub-formulas as described above and below in which at least one group Sp is a single bond are more preferred.

[0418] At least one group Sp is different from a single bond and is preferably -(CH2) p1 -, -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 where p1 is 2, 3, 4, 5 or 6, and when Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 the compounds of formula P and its sub-formulas as described above and below in which the O atom or CO group is respectively linked to the benzene ring are more preferred.

[0419] The very preferred group -A 1 -(Z-A 2 ) z - in formula P is selected from the following formulas.

[0420]

Chemical formula

[0421] In the formula, at least one benzene ring is substituted with at least one group L, and the benzene ring may be further substituted with one or more groups L or P-Sp-.

[0422] Preferred compounds of formula P and their sub-formulas are selected from the following preferred embodiments (including any combination thereof): · All groups P in the compound have the same meaning. · -A 1 -(Z-A 2 ) z - is selected from A1, A2 and A5. · The compound has exactly two polymerizable groups (represented by group P). · The compound has exactly three polymerizable groups (represented by group P). · P is selected from the group consisting of acrylate, methacrylate, and oxetane, and very preferably acrylate or methacrylate. · P is methacrylate. · All groups Sp are single bonds. · At least one of the groups Sp is a single bond, and at least one of the groups Sp is different from a single bond. · When Sp is different from a single bond, -(CH2) p2 -, -(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 -O-CO-, where p2 is 2, 3, 4, 5 or 6, and the O atom or the CO group is each connected to the benzene ring. · Sp is a single bond or -(CH2) p2 -, -(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 -O-CO-, where p2 is 2, 3, 4, 5 or 6, and the O atom or the CO group is each connected to the benzene ring. · R represents P-Sp-. ·R does not represent or contain a polymerizable group. ·R does not represent or contain a polymerizable group and represents an alkyl having 1 to 25 C atoms in a linear, branched or cyclic form, provided that one or more non-adjacent CH2 groups are not directly linked to each other by O and / or S atoms and may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, provided that one or more H atoms may each be replaced by F, Cl or L a and may be replaced by. ·L or L‘ represents F, Cl or CN. ·L is F.

[0423] Suitable and preferred compounds of formula P are selected from the following formulas.

[0424]

Chemical formula

[0425]

Chemical formula

[0426]

Chemical formula

[0427]

Chemical formula

[0428]

Chemical formula

[0429]

Chemical formula

[0430] In the formula, each group has the following meaning: P 1 、P2 , P 3 each independently represents an acrylate or methacrylate group, Sp 1 Sp 2 Sp 3 each independently represents a single bond or a spacer group having one of the meanings shown for Sp above and below, particularly preferably -(CH2) p1 -, -(CH2) p1 -O-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO- or -(CH2) p1 -O-CO-O-, where p1 is an integer from 1 to 12, provided that any additional group P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - of at least one is different from R aa provided that one or more groups P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - may represent R aa provided that, R aa is H, F, Cl, CN or a linear or branched alkyl having 1 to 25 C atoms (provided that one or more non-adjacent CH2 groups are each independently replaced by -C(R 0 )=C(R 00 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- so that O and / or S atoms are not directly linked to each other, provided that one or more H atoms are replaced by F, Cl, CN or P 1 -Sp 1- may be replaced by), particularly preferably alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl or alkylcarbonyloxy having 1 to 12 C atoms, which may be linear or branched and may be mono-fluorinated or poly-fluorinated (provided that alkenyl and alkynyl groups have at least 2 C atoms and branched groups have at least 3 C atoms). R 0 , R 00 each independently of one another, in each occurrence, represents the same or different, H or alkyl having 1 to 12 C atoms. R y and R z each independently of one another represents H, F, CH3 or CF3. X 1 , X 2 and X 3 each independently of one another represents -CO-O-, -O-CO- or a single bond. Z 1 is -O-, -CO-, -C(R y R z )- or -CF2CF2-. Z 2 and Z 3 each independently of one another represents -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2- or -(CH2) n -, provided that n is 2, 3 or 4. L, in each occurrence, represents the same or different, F, Cl, CN or alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, which may be linear or branched and may be mono-fluorinated or poly-fluorinated, preferably F. L’ and L” each independently of one another represent H, F or Cl. k represents 0 or 1. r represents 0, 1, 2, 3 or 4. s represents 0, 1, 2 or 3. t represents 0, 1 or 2, x represents 0 or 1.

[0431] Compounds of formulas P2, P13, P17, P22, P23, P24, P30, P31 and P32 are particularly preferred.

[0432] Trifunctional compounds selected from formulas P15 - P30, particularly formulas P17, P18, P19, P22, P23, P24, P25, P26, P30, P31 and P32 are even more preferred.

[0433] In the compounds of formulas P1 - P32, [Chemical formula]

[0434] wherein L has, in each occurrence, the same or different one of the meanings shown above and below, preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, OCH3, COCH3 or OCF 3、 especially F or CH3.

[0435] Very particularly preferred compounds of formula P are selected from Table E below.

[0436] To produce a PSA display, while optionally applying a voltage to the electrodes, in the LC medium between the substrates of the LC display, the polymerizable compounds contained in the LC medium are polymerized or crosslinked (when one compound contains two or more polymerizable groups) by in-situ polymerization.

[0437] The structure of the PSA display according to the present invention corresponds to the normal configuration of the PSA display as described in the prior art cited at the beginning. A configuration without protrusions is preferred. In particular, it is preferred that the electrodes on the color filter side are not structured and only the electrodes on the TFT side have slits. An electrode structure particularly suitable and preferred for a PS-VA display is described, for example, in U.S. Patent Application Publication No. 2006 / 0066793.

[0438] A preferred PSA type LC display of the present invention is · a first substrate including pixel electrodes defining pixel regions, the pixel electrodes being connected to switching elements arranged in respective pixel regions and optionally having a micro-slit pattern, and a first alignment layer optionally arranged on the pixel electrodes; · a second substrate including a common electrode layer that may be arranged on the entire portion of the second substrate facing the first substrate, and an optional second alignment layer; · an LC layer including an LC medium layer arranged between the first substrate and the second substrate, the LC medium layer including a polymerizable component including one or more compounds of formula R and a liquid crystal host including those described above and below (however, the polymerizable component may be polymerized). including.

[0439] The first and / or second alignment layer controls the alignment direction of the LC molecules in the LC layer. For example, in a PS-VA display, the alignment layer is selected so that the LC molecules are in a homeotropic (or perpendicular) alignment (i.e., perpendicular to the surface) or a tilted alignment. Such an alignment layer includes, for example, polyimide, and the polyimide may be rubbed or prepared by an optical alignment method.

[0440] The LC layer having the LC medium can be arranged between the substrates of the display by a method commonly used in the manufacture of displays, for example, the so-called one-drop-filling (ODF) method. Then, the polymerizable component of the LC medium is polymerized, for example, by UV photopolymerization. The polymerization can be carried out in one step or two or more steps.

[0441] The PSA display may include further elements such as color filters, black matrices, passivation layers, optical retardation layers, transistor elements for addressing individual pixels, etc., all of which are known to those skilled in the art and can be used without exercising patentable skills.

[0442] The electrode structure can be designed by those skilled in the art according to the type of individual display. For example, for a PS-VA display, by providing electrodes having slits and / or ridges or protrusions to generate two, four or more different tilt alignment directions, the multi-domain alignment of LC molecules can be induced.

[0443] Upon polymerization, the polymerizable compound forms a cross-linked polymer, and a certain pretilt of LC molecules occurs in the LC medium. Although not wishing to be bound by a particular theory, it is considered that at least a part of the cross-linked polymer formed by the polymerizable compound phase-separates or precipitates from the LC medium and forms a polymer layer on the substrate or electrode or the alignment layer provided thereon. Microscopic measurement data (such as SEM and AFM) confirmed that at least a part of the formed polymer accumulates at the LC / substrate interface.

[0444] The polymerization can be carried out in a single step. Also, first, polymerization can be carried out while optionally applying a voltage in the first step to generate a pretilt angle, and subsequently, in the second polymerization step, without applying a voltage, polymerize or cross-link the compounds that did not react in the first step ("final curing").

[0445] Suitable and preferred polymerization methods can be achieved, for example, by thermal or photopolymerization, preferably by photopolymerization, particularly by UV-induced photopolymerization, by exposing the polymerizable compound to UV irradiation.

[0446] One or more types of polymerization initiators can be added to the LC medium. Appropriate conditions for polymerization and the appropriate type and amount of initiator are known to those skilled in the art and are described in the literature. For example, commercially available photoinitiators such as Irgacure651®, Irgacure184®, Irgacure907®, Irgacure369® or Darocure1173® (Ciba) are suitable for free radical polymerization. When using a polymerization initiator, the proportion of the initiator is preferably 0.001 to 5% by weight, particularly preferably 0.001 to 1% by weight.

[0447] Also, the polymerizable compound according to the present invention is also suitable for polymerization without an initiator, which has remarkable advantages such as, for example, lower material costs, and particularly less contamination of the LC medium by the amount of the initiator or its degradation products that can remain. Thus, polymerization can also be carried out without adding an initiator. Therefore, in a preferred embodiment, the LC medium does not contain a polymerization initiator.

[0448] Also, for example, in order to prevent undesirable spontaneous polymerization of the RM during storage or transportation, the LC medium may contain one or more stabilizers. Appropriate types and amounts of stabilizers are known to those skilled in the art and are described in the literature. For example, commercially available stabilizers from the Irganox® series (Ciba), such as Irganox® 1076, are particularly suitable. When using a stabilizer, the proportion of the stabilizer is preferably 10 to 500,000 ppm, particularly preferably 50 to 50,000 ppm, based on the total amount of the RM or the polymerizable component (component P).

[0449] The polymerizable compound of formula P exhibits particularly good UV absorption in a method comprising one or more of the following features for preparing a PSA display, and is thus particularly suitable for that method: · Exposing the polymerizable medium to UV light in a display in a two-step process comprising a first UV exposure step (the "UV-1 step") for generating a tilt angle and a second UV exposure step (the "UV-2 step") for completing the polymerization; · Expose the polymerizable medium to UV light generated by an energy-saving UV lamp (also known as a "green UV lamp") within the display. These lamps are characterized by a relatively low intensity (1 / 100 to 1 / 10 of that of conventional UV lamps) in the absorption spectrum of 300 - 380 nm, and are preferably used in the UV2 process, but can be used in the UV1 process if it is necessary to avoid high intensity; · To avoid exposing the polymerizable medium to short-wavelength UV light in the PS-VA process, expose the polymerizable medium to UV light generated by a UV lamp having an emission spectrum shifted to a longer wavelength (preferably 340 nm or more) within the display.

[0450] Protect the organic layer from damage that can be caused by UV light, either by using a lower intensity or shifting to UV with a longer wavelength.

[0451] Preferred embodiments of the present invention relate to a method for preparing the PSA display described above and below, and include one or more of the following features: · Expose the polymerizable LC medium to UV light in a two-step process that includes a first UV exposure step ("UV-1 step") for generating a tilt angle and a second UV exposure step ("UV-2 step") for completing polymerization; · Expose the polymerizable LC medium to UV light generated by a UV lamp having an intensity in the wavelength range of 300 - 380 nm of 0.5 mW / cm 2 ~10 mW / cm 2 (preferably, use this UV lamp in the UV2 process and optionally also in the UV1 process); · Expose the polymerizable LC medium to UV light having a wavelength of 340 nm or more, preferably 400 nm or less.

[0452] This preferred method can be implemented, for example, by using a desired UV lamp or by using a band-pass filter and / or a cut-off filter that substantially transmits UV light having a respective desired wavelength and substantially blocks light having a respective undesired wavelength. For example, when irradiation with UV light having a wavelength λ of 300 to 400 nm is desired, UV exposure can be carried out using a wide-band pass filter that substantially transmits wavelengths where λ is greater than 300 nm and less than 400 nm. When it is desired to irradiate with UV light having a wavelength λ greater than 340 nm, UV exposure can be carried out using a cut-off filter that substantially transmits wavelengths λ greater than 340 nm.

[0453] "Substantially transmits" means that the filter transmits most, preferably at least 50% of the intensity of the incident light of the desired wavelength. "Substantially blocks" means that the filter does not transmit most, preferably at least 50% of the intensity of the incident light of the undesired wavelength. "Desired (undesired) wavelength" means, for example, in the case of a band-pass filter, a wavelength within (outside) the given range of λ, and in the case of a cut-off filter, a wavelength above (below) the given value of λ.

[0454] This preferred method enables the manufacture of displays using longer wavelength UV, thereby reducing or avoiding the harmful and damaging effects of the short wavelength components of UV light.

[0455] The UV irradiation energy is generally 6 to 100 J, depending on the conditions of the manufacturing process.

[0456] Preferably, the LC medium according to the present invention consists essentially of a polymerizable component (P) containing a polymerizable compound of formula R as described above and below, or one or more polymerizable compounds of formula P, an LC host mixture, and an optically active component containing one or more chiral dopants. However, the LC medium preferably further contains one or more additional components or additives selected without limitation from the list including comonomers, chiral dopants, polymerization initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricants, dispersants, hydrophobizing agents, adhesives, fluidity improvers, defoamers, degassing agents, diluents, reactive diluents, auxiliaries, colorants, dyes, pigments, and nanoparticles.

[0457] Particularly preferred are LC media containing one, two, or three polymerizable compounds of formula P.

[0458] Preferably, the proportion of the compound of formula P in the LC medium is more than 0% to less than 5%, very preferably more than 0% to less than 1%, and most preferably 0.01 to 0.5%.

[0459] In a preferred embodiment, the medium according to the present invention contains one or more compounds of formula S, preferably in a total concentration in the range of 10 ppm to 2000 ppm, more preferably 100 ppm to 1000 ppm, even more preferably 150 ppm to 500 ppm, very preferably 200 ppm to 400 ppm, particularly 250 to 300 ppm.

[0460] In another preferred embodiment, the medium according to the present invention contains one or more compounds of formula S, preferably in a total concentration in the range of 1000 ppm to 5000 ppm, more preferably more than 1000 ppm to 5000 ppm, even more preferably 1200 ppm to 4500 ppm, very preferably 2000 ppm to 4000 ppm, particularly 2500 to 3500 ppm.

[0461] The medium according to the present invention preferably has a negative dielectric anisotropy.

[0462] The medium according to the present invention contains a compound of formula I at a concentration in the range of 1% to 35%, preferably 5% to 30%, more preferably 6% to 26%, and very preferably 8% to 25%, and contains a compound of formula CPY at a concentration in the range of 1% to 15%, preferably 2% to 14%, more preferably 3% to 13%, and very preferably 4% to 12%.

[0463] Preferred embodiments are as follows, either alone or in combination with each other.

[0464] According to a first preferred embodiment of the present invention, the medium has birefringence in the range of 0.120 to 0.150, more preferably 0.125 to 0.145, and particularly 0.128 to 0.138.

[0465] The medium according to the first preferred embodiment preferably has:

[0466] · one or more compounds of formula IIA in a total amount of less than 3%, more preferably less than 2%, and very preferably less than 1%; or

[0467] · one or more compounds of formula IIA in the range of 0% to 1%, very preferably 0%; and / or

[0468] · one or more compounds of formula IIB and CPY, preferably formula IIB-2 and / or IIB-10 and CPY, more preferably formula IIB-2 and IIB-10 and CPY, in a total concentration in the range of 10% to 50%, more preferably 15% to 45%, even more preferably 20% to 40%, and particularly 26% to 37%; and / or

[0469] · one or more compounds of formula IIC, preferably in a total concentration in the range of 1% to 15%, more preferably 1.5% to 12%, and very preferably 3% to 10%; and / or

[0470] · one or more compounds of formula IID in a total amount of less than 2%, very preferably 0%. and / or

[0471] ·One or more compounds of formula III, preferably formula III-2 and / or III-3, more preferably formula III-2-6 and / or III-3, especially one or more compounds B(S)-nO-Om and / or COB(S)-n-Om, very preferably B(S)-2O-O4, B(S)-2O-O5, B(S)-2O-O6 and / or COB(S)-2-O4, preferably at a total concentration in the range of 3% to 20%, more preferably 3% to 17%, very preferably 4% to 15%; and / or

[0472] ·One or more compounds of formula VI-1-4, preferably at a total concentration in the range of 1% to 15%, more preferably 2% to 12%, very preferably 3% to 10%; and / or

[0473] ·One or more compounds of formula IIC and VI-1-4, preferably at a total concentration in the range of 1% to 18%, more preferably 3% to 15%, very preferably 4% to 13%;

[0474] ·One or more compounds selected from the group of compounds of formula CPY, IIA, IIB, IIC, IID, III and VI-1-4, preferably compounds of formula CPY, IIB, IIC and optionally VI-1-4, at a total concentration in the range of 32% to 70%, more preferably 38% to 65%, very preferably 45% to 60%; and / or

[0475] ·A compound of formula I and one or more compounds of formula IV, preferably formula I and IV-3, at a total concentration in the range of 20% to 65%, more preferably 23% to 58%, even more preferably 26% to 50%, very preferably 28% to 45%, especially 30% to 42%; and / or

[0476] ·A compound of formula I and a compound of formula IV-3-2b, preferably at a total concentration in the range of 20% to 40%, more preferably 22% to 38%, particularly 24% to 32%; and / or

[0477] ·One or more compounds of formula IVb, more preferably formula IVb-2, at a total concentration in the range of 1% to 15%, more preferably 2% to 12%, very preferably 4% to 10%; and / or

[0478] ·One or more compounds of formula V, more preferably V-2-1 and / or V-2-2, preferably at a total concentration in the range of 1% to 18%, more preferably 2% to 15%, very preferably 3% to 10%; and / or

[0479] One or more compounds of formula IIA-Y, preferably formula IIA-Y6, at a total concentration in the range of 0.5% to 10%, more preferably 1% to 8%, very preferably 2% to 5%; and / or

[0480] One or more compounds of formula CL, more preferably formula CL-3, very preferably selected from formula CLP-V-m, CLP-V-Om, CLP-n-m and CLP-n-Om (wherein n and m are independently 1, 2, 3, 4 or 5), preferably at a total concentration in the range of 1% to 12%, more preferably 2% to 10%, very preferably 3% to 7% contained therein.

[0481] The liquid crystal medium according to the invention preferably advantageously has a nematic phase from -20 °C or below to 70 °C or above, particularly preferably from -30 °C or below to 72 °C or above, very particularly preferably from -40 °C or below to 74 °C or above.

[0482] In a first preferred embodiment, the medium according to the invention has a clearing temperature of 70 °C or above, preferably 72 °C or above, more preferably 73 °C or above, particularly 74 °C or above.

[0483] The expression "having a nematic phase" means that on the one hand, no smectic phase and crystallization are observed at a lower temperature corresponding to the temperature, and on the other hand, no transparency (transition to an isotropic phase) occurs during heating of the nematic phase at a given temperature. The examination at low temperature is carried out using a rheometer at the corresponding temperature and confirmed by storing in a test cell having a layer thickness corresponding to electro-optical applications for at least 100 hours. If the storage stability in the test cell at a temperature of -20 °C is 1000 hours or more, the medium is called stable at this temperature. In the case of temperatures of -30 °C and -40 °C, the corresponding times are 500 hours and 250 hours respectively. At high temperature, the clearing point is measured by a conventional method in a capillary tube.

[0484] The liquid crystal mixture according to the invention is preferably nematic at a temperature of -20 °C or lower, preferably -30 °C or lower, very preferably -40 °C or lower.

[0485] In a preferred embodiment, the liquid crystal mixture according to the invention has a dielectric anisotropy Δη of -2.0 to -5.0, preferably -2.5 to -4.0, particularly -2.8 to -3.3.

[0486] In a preferred embodiment, the liquid crystal mixture according to the invention has a dielectric anisotropy Δη of -2.5 to -6.0, preferably -2.8 to -5.0, particularly -3.0 to -4.3.

[0487] The rotational viscosity γ1 at 20 °C is preferably in the range of 60 to 120 mPas, more preferably 80 to 110 mPa·s.

[0488] In another embodiment, the rotational viscosity γ1 at 20 °C is preferably in the range of 60 to 200 mPas, more preferably 80 to 180 mPa·s.

[0489] The elastic constant K1 is preferably in the range of 13.0 to 17.0, more preferably 14.0 to 16.8, particularly 15.0 to 16.5.

[0490] The elastic constant K3 is preferably in the range of 13.0 to 17.0, more preferably in the range of 14.0 to 16.8, and particularly in the range of 15.0 to 16.5.

[0491] According to a second preferred embodiment of the present invention, the medium has a birefringence in the range of 0.105 to 0.125, more preferably in the range of 0.107 to 0.117, and particularly in the range of 0.110 to 0.119.

[0492] The medium according to the second preferred embodiment preferably comprises:

[0493] ·One or more compounds of formula IIA, preferably selected from formula IIA-2 and IIA-10, preferably at a total concentration in the range of 5% to 40%, more preferably in the range of 7% to 35%, and particularly in the range of 10% to 40%; and / or

[0494] ·One or more compounds of formula IIB and CPY, preferably formula IIB-2 and / or IIB-10 and CPY, more preferably formula IIB-2 and IIB-10 and CPY, at a total concentration in the range of 5% to 45%, more preferably in the range of 6% to 42%, and particularly in the range of 8% to 40%; and / or

[0495] ·One or more compounds of formula IIC, preferably at a total concentration in the range of 1% to 10%, more preferably in the range of 1% to 9%, and very preferably in the range of 1% to 8%; and / or

[0496] ·One or more compounds of formula IID, preferably at a total concentration in the range of 1% to 10%, more preferably in the range of 1.5% to 8%, and very preferably in the range of 2% to 6%; and / or

[0497] ·One or more compounds of formula III, preferably formula III-2, more preferably formula III-2-6, particularly selected from B(S)-2O-O4, B(S)-2O-O5 and B(S)-2O-O6, preferably at a total concentration in the range of 1% to 12%, more preferably in the range of 2% to 11%, and very preferably in the range of 3% to 10%. and / or

[0498] ·One or more compounds of formula III, preferably formula III-2 and / or III-3, more preferably formula III-2-6 and / or III-3, particularly one or more compounds B(S)-nO-Om and / or COB(S)-n-Om, very preferably B(S)-2O-O4, B(S)-2O-O5, B(S)-2O-O6 and / or COB(S)-2-O4, preferably at a total concentration in the range of 5% to 25%, more preferably 7% to 20%, very preferably 10% to 18%; and / or

[0499] ·One or more compounds of formula VI-1-4, preferably at a total concentration in the range of 1% to 12%, more preferably 2% to 9%, very preferably 3% to 8%; and / or

[0500] ·One or more compounds of formula IIC and VI-1-4, preferably at a total concentration in the range of 1% to 18%, more preferably 3% to 15%, very preferably 6% to 12%;

[0501] ·One or more compounds selected from the group of compounds of formula CPY, IIA, IIB, IIC, IID, III and VI-1-4, preferably at a total concentration in the range of 32% to 70%, more preferably 38% to 65%, very preferably 45% to 60%; and / or

[0502] ·A compound of formula I and one or more compounds of formula IV, more preferably formula I and IV-1 and IV-3, at a total concentration in the range of 20% to 65%, more preferably 23% to 58%, even more preferably 26% to 50%, very preferably 28% to 45%, particularly 30% to 42%; and / or

[0503] ·A compound of formula I and a compound of formula IV-3-2b, preferably at a total concentration in the range of 5% to 40%, more preferably 8% to 35%, particularly 10% to 30%; and / or

[0504] ·One or more compounds of formula IVa, more preferably formula IVa-2, especially CP-3-O2, at a total concentration in the range of 1% to 14%, more preferably 2% to 12%, very preferably 4% to 10%; and / or

[0505] ·One or more compounds of formula IVb, very preferably selected from the group consisting of PP-n-m and / or PP-n-nVm, especially PP-1-3, PP-1-4, PP-1-5, PP-1-2V and PP-1-2V1, at a total concentration in the range of 1% to 15%, more preferably 2% to 13%, very preferably 4% to 12%; and / or

[0506] ·One or more compounds of formula V, more preferably selected from the compounds of formula V-1-1 and V-1-6, especially CCC-n-m and / or CCC-n-V, very especially CCC-3-V and / or CCC-V-V, preferably at a total concentration in the range of 1% to 20%, more preferably 2% to 17%, very preferably 3% to 14%; and / or

[0507] ·One or more compounds of formula V, more preferably selected from the compounds of formula V-2-1 and V-2-2, especially selected from the group consisting of CCP-n-m and / or CCP-Vn-m and / or CPP-n-m, very especially CCP-3-1, CCP-V-1, CCP-V2-1 and CPP-3-2, preferably at a total concentration in the range of 1% to 20%, more preferably 2% to 17%, very preferably 3% to 14%; and / or

[0508] One or more compounds of formula IIA-Y, preferably formula IIA-Y6, especially Y-nO-Om, very especially Y-4O-O4, at a total concentration in the range of 0.5% to 10%, more preferably 1% to 8%, very preferably 2% to 5%; and / or

[0509] One or more compounds of formula CL, more preferably formula CL-3, and very preferably compounds CLP-V-m, CLP-V-Om, CLP-n-m and CLP-n-Om (wherein n and m are independently 1, 2, 3, 4 or 5), preferably in a total concentration in the range of 1% to 12%, more preferably 2% to 10%, and very preferably 3% to 7%; and / or

[0510] Compounds of formula COYOIC-n-m and compounds of formula GIY-n-Om are included.

[0511] The liquid crystal medium according to the present invention has a high value of voltage holding ratio in a liquid crystal cell.

[0512] Generally, a liquid crystal medium having a low addressing voltage or threshold voltage exhibits a lower voltage holding ratio than one having a high addressing voltage or threshold voltage, and vice versa.

[0513] As used herein, the term "dielectrically positive compound" refers to a compound having a Δε greater than 1.5, the term "dielectrically neutral compound" refers to one having a Δε between -1.5 and 1.5, and the term "dielectrically negative compound" refers to one having a Δε less than -1.5. The dielectric anisotropy of a compound is determined by measuring the capacitance of a mixture obtained by dissolving 10% of the compound in a liquid crystal host in at least one test cell having a layer thickness of 20 μm each of homeotropic and homogeneous surface orientations at 1 kHz. The measurement voltage is typically 0.5 V to 1.0 V, but always lower than the capacitance threshold of the liquid crystal mixture being considered.

[0514] All values of temperature shown in the present invention are in °C.

[0515] The mixtures according to the invention are suitable for all VA-TFT applications such as, for example, VAN, MVA, (S)-PVA, ASV, PSA (polymer sustained VA), and PS-VA (polymer stabilized VA). They are furthermore suitable for IPS (in-plane-switching) and FFS (fringe field switching) applications having a negative Δε, in particular UB-FFS.

[0516] It goes without saying for a person skilled in the art that the VA, IPS or FFS mixtures according to the invention may also include compounds in which, for example, H, N, O, Cl and F are replaced by the corresponding isotopes.

[0517] The compounds according to the invention can be synthesized by known methods described in the literature (for example, standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart) or by methods analogous thereto under known reaction conditions suitable for said reactions. Although not mentioned herein, variations known per se can be used herein. In particular, they can be prepared by methods described in or analogous to the following reaction schemes. Further methods for preparing the compounds of the invention can be obtained from the examples.

[0518] Other mesogenic compounds not explicitly mentioned above can also advantageously be used in the media according to the invention. Such compounds are known to a person skilled in the art.

[0519] In the present invention and in the following examples, the structures of the liquid crystal compounds are indicated by acronyms and the conversion to chemical formulas is carried out according to Tables A to C below. All groups C m H 2m+1 、C n H 2n+1 、およびC l H2l+1 or C m H 2m-1 、C n H 2n-1 and C l H 2l-1 is a linear alkyl group or alkylene group having n, m, and l carbon atoms, respectively, in each case. Preferably, n, m, and l are each independently 1, 2, 3, 4, 5, 6, or 7. Table A shows the codes of the ring elements of the nucleus of the compound, Table B lists the cross-linking units, and Table C lists the meanings of the symbols of the left and right end groups of the molecule. The acronym is composed of the code of the ring element having any linking group followed by the first hyphen and the code of the left end group, and the second hyphen and the code of the right end group. Table D shows examples of the structures of the compounds together with their respective abbreviations.

[0520] <Table A: Ring Elements>

[0521]

Table 1

[0522]

Table 2

[0523]

Table 3

[0524] <Table B: Cross-Linking Units>

[0525]

Table 4

[0526] <Table C: End Groups>

[0527]

Table 5

[0528]

Table 6

[0529] In the table, n and m are each integers, and the three dots "..." are places for other abbreviations from this table.

[0530] Apart from the compounds of Formula I, IIA, IIB, IIC and / or IID, IVa, IVb and V, the mixtures according to the invention may contain one or more of the compounds described below.

[0531] The following abbreviations are used: (n, m, k and l are each independently integers, preferably from 1 to 9, preferably from 1 to 7, and k and l may also be 0, preferably from 0 to 4, more preferably 0 or 2, most preferably 2, n is preferably 1, 2, 3, 4 or 5, and in the combination "-nO-", it is preferably 1, 2, 3 or 4, more preferably 2 or 4, m is preferably 1, 2, 3, 4 or 5, and in the combination "-Om", it is preferably 1, 2, 3 or 4, more preferably 2 or 4. The combination "-lVm" is preferably "2V1".)

[0532]

[0533]

Table 7

[0534]

Table 8

[0535]

Table 9

[0536]

Table 10

[0537]

Table 11

[0538]

Table 12

[0539]

Table 13

[0540]

Table 14

[0541]

Table 15

[0542]

Table 16

[0543]

Table 17

[0544]

Table 18

[0545]

Table 19

[0546]

Table 20

[0547]

Table 21

[0548]

Table 22

[0549]

Table 23

[0550]

Table 24

[0551]

Table 25

[0552]

Table 26

[0553]

Table 27

[0554]

Table 28

[0555]

Table 29

[0556]

Table 30

[0557] Table E shows exemplary reactive mesogenic compounds that can be used in the LC medium according to the present invention.

[0558] [Table 31]

[0559] [Table 32]

[0560] [Table 33]

[0561] [Table 34]

[0562] [Table 35]

[0563] [Table 36]

[0564] [Table 37]

[0565] [Table 38]

[0566] [Table 39]

[0567] [Table 40]

[0568]

Table 41

[0569]

Table 42

[0570]

Table 43

[0571]

Table 44

[0572]

Table 45

[0573]

Table 46

[0574]

Table 47

[0575]

Table 48

[0576]

Table 49

[0577]

Table 50

[0578]

Table 51

[0579]

Table 52

[0580]

Table 53

[0581] In a preferred embodiment, the mixture according to the invention preferably comprises one or more polymerizable compounds selected from the polymerizable compounds of formulas RM-1 to RM-182. Among these, the compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-58, RM-64, RM-74, RM-76, RM-88, RM-91, RM-102, RM-103, RM-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 are particularly preferred.

Examples

[0582] The present invention will be described in detail by the following non-limiting examples.

[0583] The following abbreviations and symbols are used: V0 is the capacitance threshold voltage [V] at 20 °C, n e is the abnormal refractive index at 20 °C and 589 nm, n0 is the normal refractive index at 20 °C and 589 nm, Δn is the optical anisotropy at 20 °C and 589 nm, ε ⊥is the dielectric constant perpendicular to the director at 20 °C and 1 kHz, ε ∥ is the dielectric constant parallel to the director at 20 °C and 1 kHz, Δε is the dielectric anisotropy at 20 °C and 1 kHz, cl.p., T(N,I) is the clearing point [°C], γ1 is the rotational viscosity [mPa·s] at 20 °C, K1 is the elastic constant [pN] for the "splay" deformation at 20 °C, K2 is the elastic constant [pN] for the "twist" deformation at 20 °C, K3 is the elastic constant [pN] for the "bend" deformation at 20 °C.

[0584] Unless otherwise explicitly stated, all concentrations in this application are cited in weight percent and relate to the corresponding mixture consisting of all solid or liquid crystal components without solvent.

[0585] Unless otherwise explicitly stated, all temperature values shown in this application, such as the melting point T(C,N), the transition T(S,N) from the smectic (S) phase to the nematic (N) phase, and the clearing point T(N,I), are cited in degrees Celsius (°C). M.p. is the melting point and cl.p. is the clearing point. Further, C is the crystalline state, N is the nematic phase, S is the smectic phase, and I is the isotropic phase. The data between these symbols represent the transition temperatures.

[0586] All physical properties are determined or have been determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", November 1997 issue, Merck & Co., Inc., Germany, applied at a temperature of 20 °C, and Δn is determined at 589 nm and Δε is determined at 1 kHz unless otherwise explicitly indicated in each case.

[0587] For the present invention, unless otherwise specified, the term "threshold voltage" relates to the capacitance threshold (V0), also known as the Frederiks threshold. Also, in the examples, although generally normal, the optical threshold for 10% relative contrast (V 10 ) may also be shown.

[0588] Unless otherwise stated, the polymerization process of the polymerizable compound in the 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.

[0589] Unless otherwise stated, the method for preparing the test cells and the method for measuring their electro-optical and other properties are carried out in a manner as described hereinafter or similar thereto.

[0590] The display used for measuring the capacitance threshold voltage consists of two planar parallel glass outer plates with a 25 μm spacing, each having an electrode layer on the inner side and an unrubbed polyimide alignment layer on the upper side that provides a homeotropic alignment of the liquid crystal molecules.

[0591] The display or test cell used for measuring the tilt angle consists of two planar parallel glass outer plates with a 4 μm spacing, each having an electrode layer on the inner side and a polyimide alignment layer on the upper side, provided that the two polyimide layers are rubbed antiparallel to each other, resulting in a homeotropic edge alignment of the liquid crystal molecules.

[0592] The polymerizable compound is polymerized by irradiating it with UV light of a specified intensity in the display or test cell for a predetermined time while a voltage is applied to the display (usually 10V - 30V AC, 1kHz). Unless otherwise indicated in the examples, a fluorescent lamp and an intensity of 0 - 20 mW / cm 2 are used for polymerization. The intensity is measured using a standard meter (Ushio Accumulate UV meter with a center wavelength of 313 nm).

[0593] The transmittance measurement is carried out in a test cell having a fishbone electrode layout (manufactured by Merck KGaA, Japan; 1-pixel fishbone electrode (ITO, 10×10 mm, fishbone angle 47.7° having 3-μm lines / 3-μm spaces), 3.2-μm cell gap, AF glass, tilt angle 1°).

[0594] The storage stability (LTS bulk ) in the bulk of the medium according to the present invention at a predetermined temperature T is determined by visual inspection. 2 g of the target medium is filled into a sealed glass container (bottle) of appropriate size and placed in a refrigerator at a predetermined temperature. The bottle is checked at defined time intervals for the occurrence of a smectic phase or crystallization. For all materials and for each temperature, two bottles are stored. If crystallization or the appearance of a smectic phase is observed in at least one of the two corresponding bottles, the test is terminated and the time of the last inspection before the occurrence of the higher-order phase is observed is recorded as the respective storage stability.

[0595] <Example of mixture> Mixtures M1 to M102 and P1 to P10 have the compositions and physical properties shown in the following table.

[0596] <Mixture example M1>

[0597] [Table 54]

[0598] Medium M1 contains compound CCG-V-F. This mixture is distinguished by improved “flicker” in the FFS panel, and thus the addressing frequency can be reduced, enabling a more energy-efficient panel to be realized.

[0599] <Mixture example M2>

[0600] [Table 55]

[0601] <Mixture Example M3>

[0602]

Table 56

[0603] <Mixture Example M4>

[0604]

Table 57

[0605] <Mixture Example M5>

[0606]

Table 58

[0607] <Mixture Example M6>

[0608]

Table 59

[0609] <Mixture Example M7>

[0610]

Table 60

[0611] <Mixture Example M8>

[0612]

Table 61

[0613] <Mixture Example M9>

[0614]

Table 62

[0615] <Mixture Example M10>

[0616]

Table 63

[0617] <Mixture Example M11>

[0618]

Table 64

[0619] <Mixture Example M12>

[0620]

Table 65

[0621] <Mixture Example M13>

[0622]

Table 66

[0623] <Mixture Example M14>

[0624]

Table 67

[0625] <Mixture Example M15>

[0626]

Table 68

[0627] <Mixture Example M16>

[0628]

Table 69

[0629] <Mixture Example M17>

[0630]

Table 70

[0631] <Mixture Example M18>

[0632]

Table 71

[0633] <Mixture Example M19>

[0634]

Table 72

[0635] <Mixture Example M20>

[0636]

Table 73

[0637] <Mixture Example M21>

[0638]

Table 74

[0639] <Mixture Example M22>

[0640]

Table 75

[0641] <Mixture Example M23>

[0642]

Table 76

[0643] <Mixture Example M24>

[0644]

Table 77

[0645] <Mixture Example M25>

[0646]

Table 78

[0647] <Mixture Example M26>

[0648]

Table 79

[0649] <Mixture Example M27>

[0650]

Table 80

[0651] <Mixture Example M28>

[0652]

Table 81

[0653] <Mixture Example M29>

[0654]

Table 82

[0655] <Mixture Example M30>

[0656]

Table 83

[0657] <Mixture Example M31>

[0658]

Table 84

[0659] <Mixture Example M32>

[0660]

Table 85

[0661] <Mixture Example M33>

[0662]

Table 86

[0663] <Mixture Example M34>

[0664]

Table 87

[0665] <Mixture Example M35>

[0666]

Table 88

[0667] <Mixture Example M36>

[0668]

Table 89

[0669] <Mixture Example M37>

[0670]

Table 90

[0671] <Mixture Example M38>

[0672]

Table 91

[0673] <Mixture Example M39>

[0674]

Table 92

[0675] <Mixture Example M40>

[0676]

Table 93

[0677] <Mixture Example M41>

[0678]

Table 94

[0679] <Mixture Example M42>

[0680]

Table 95

[0681] <Mixture Example M43>

[0682]

Table 96

[0683] <Mixture Example M44>

[0684]

Table 97

[0685] <Mixture Example M45>

[0686]

Table 98

[0687] <Mixture Example M46>

[0688]

Table 99

[0689] <Mixture Example M47>

[0690]

Table 100

[0691] <Mixture Example M48>

[0692]

Table 101

[0693] <Mixture Example M49>

[0694]

Table 102

[0695] <Mixture Example M49>

[0696]

Table 103

[0697] <Mixture Example M50>

[0698]

Table 104

[0699] <Mixture Example M51>

[0700]

Table 105

[0701] <Mixture Example M52>

[0702] Mixture Example M52 consists of 99.985% of Mixture Example M1 and 0.015% of the compound of formula S1-1a.

[0703]

Chemical Formula

[0704] <Mixture Example M53>

[0705] Mixture Example M53 consists of 99.98% of Mixture Example M2 and 0.02% of the compound of formula S2-1a.

[0706]

Chemical Formula

[0707] <Mixture Example M54>

[0708]

Table 106

[0709] <Mixture Example M55>

[0710]

Table 107

[0711] <Mixture Example M56>

[0712]

Table 108

[0713] <Mixture Example M57>

[0714]

Table 109

[0715] <Mixture Example M58>

[0716]

Table 110

[0717] <Mixture Example M59>

[0718]

Table 111

[0719] <Mixture Example M60>

[0720]

Table 112

[0721] <Mixture Example M61>

[0722]

Table 113

[0723] <Mixture Example M62>

[0724]

Table 114

[0725] <Mixture Example M63>

[0726]

Table 115

[0727] <Mixture Example M64>

[0728]

Table 116

[0729] <Mixture Example M65>

[0730]

Table 117

[0731] <Mixture Example M66>

[0732]

Table 118

[0733] <Mixture Example M67>

[0734]

Table 119

[0735] <Mixture Example M68>

[0736]

Table 120

[0737] <Mixture Example M69>

[0738]

Table 121

[0739] <Mixture Example M70>

[0740]

Table 122

[0741] <Mixture Example M71>

[0742]

Table 123

[0743] <Mixture Example M72>

[0744]

Table 124

[0745] <Mixture Example M73>

[0746]

Table 125

[0747] <Mixture Example M74>

[0748] Mixture Example M74 consists of 99.98% of Mixture Example M1 and 0.02% of the compound of formula ST-12b-1.

[0749]

Chemical formula

[0750] <Mixture Example M75>

[0751]

Table 126

[0752] <Mixture Example M76>

[0753]

Table 127

[0754] <Mixture Example M77>

[0755]

Table 128

[0756] <Mixture Example M78>

[0757]

Table 129

[0758] <Mixture Example M79>

[0759]

Table 130

[0760] <Mixture Example M80>

[0761]

Table 131

[0762] <Mixture Example M81>

[0763] Mixture Example M81 consists of 99.975% of the medium of Mixture Example M79 and 0.025% of Compound ST-3c.

[0764]

Chemical Formula

[0765] <Mixture Example M82>

[0766] Mixture Example M82 consists of 99.980% of the medium of Mixture Example M78 and 0.020% of Compound ST-3d.

[0767]

Chemical

[0768] <Mixture Example M83>

[0769]

Table 132

[0770] <Mixture Example M84>

[0771]

Table 133

[0772] <Mixture Example M85>

[0773]

Table 134

[0774] <Mixture Example M86>

[0775]

Table 135

[0776] <Mixture Example M87>

[0777]

Table 136

[0778] <Mixture Example M88>

[0779]

Table 137

[0780] <Mixture Example M89>

[0781]

Table 138

[0782] <Mixture Example M90>

[0783]

Table 139

[0784] <Mixture Example M91>

[0785]

Table 140

[0786] <Mixture Example M92>

[0787]

Table 141

[0788] <Mixture Example M93>

[0789]

Table 142

[0790] <Mixture Example M94>

[0791]

Table 143

[0792] <Mixture Example M95>

[0793]

Table 144

[0794] <Mixture Example M96>

[0795]

Table 145

[0796] <Mixture Example M97>

[0797]

Table 146

[0798] <Mixture Example M98>

[0799]

Table 147

[0800] <Mixture Example M99>

[0801]

Table 148

[0802] <Mixture Example M100>

[0803]

Table 149

[0804] <Mixture Example M101>

[0805]

Table 150

[0806] <Mixture Example M102>

[0807]

Table 151

[0808] <Coincidence mixture> The polymerizable mixtures P1 to P9 are prepared from the nematic mixtures given in Table 1 by adding a reactive mesogen (RM) selected from the group of compounds of formulae RM-1, RM-17, RM-35, RM-64 and RM-171 in the amounts (%RM) given in Table 1.

[0809]

Table 152

[0810]

Table 153

[0811] <Table 1: Polymerizable mixture>

[0812]

Table 154

[0813] <Mixture Example P10> The polymerizable mixture P10 consists of 99.434% of mixture example M1, 0.300% of RM-1, 0.200% of RM-145, 0.050% of RM-163, 0.001% of Irganox® 1076 and 0.015% of compound ST-3a-1.

[0814]

Chemical formula

[0815]

Chemical formula

Claims

1. A liquid crystal medium comprising one or more compounds selected from the group consisting of compounds of formula I, compounds of formula CPY, and compounds of formulae IIA, IIB, IIC and IID. 【Chemical 1】 [Chemical 2] [Chemical Formula 3] (In the formula, R ２Ａ , R ２Ｂ , R ２Ｃ and R ２Ｄ are, independently of one another, H, a straight-chain alkyl or alkoxy having 1 to 15 C atoms, a straight-chain alkenyl or alkenyloxy having 2 to 15 C atoms or a branched alkyl, alkoxy, alkenyl or alkenyloxy each having 3 to 15 C atoms, with the proviso that in these groups one or more CH ２ groups are arranged such that O atoms are not directly linked to one another 【Chemical Formula 4】 -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ -, -O-, -CO-O- or -O-CO-, each of which may be independently replaced with one another, and one or more H atoms in the group may be replaced with halogen, L １ and L ２ each independently represents F, Cl, CF ３ or CHF ２ and Y represents H, F, Cl, CF ３ , CHF ２ or CH ３ and Z ２ 、Z ２Ｂ and Z ２Ｄ are each, independently of one another, a single bond, -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -COO-, -OCO-, -C ２ F ４ -, -CF=CF- or -CH=CHCH ２ O- and (O) represents O or a single bond, p represents 0, 1 or 2, q represents 0 or 1, and v represents an integer from 1 to 6, provided that the compound of formula CPY is excluded from formula IIB.)

2. The liquid crystal medium according to claim 1, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formula III, BC, CR, PH-1 and PH-2. [Chemical Formula 5] (In the formula, R ３１ 、R ３２ 、R Ｂ１ 、R Ｂ２ 、R ＣＲ１ 、R ＣＲ２ 、R Ｐ１ and R Ｐ２ each independently represents H, an alkyl or alkoxy group having 1 to 15 C atoms, provided that in these groups, one or more CH ２ groups are arranged such that O atoms are not directly linked to each other. [Chemical Formula 6] -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ -, -O-, -CO-O- or -O-CO-, may each be independently replaced with each other, and one or more H atoms in the group may be replaced with halogen, A ３ are, in each occurrence, independent of each other a) a 1,4-cyclohexenylene or 1,4-cyclohexylene group, in which one or two non-adjacent CH ２ groups may be replaced by -O- or -S-. b) a 1,4-phenylene group (in which one or two CH groups may be replaced by N), or c) a group selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl, provided that the groups a), b) and c) may be mono- or polysubstituted by halogen atoms, n represents 0, 1 or 2, Z ３１ is, independently of each other at each occurrence, -CO-O-, -O-CO-, -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -CH ２ -, -CH ２ CH ２ -, -(CH ２ ) ４ -, -CH=CH-CH ２ O-, -C ２ F ４ -, -CH ２ CF ２ -, -CF ２ CH ２ -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, L ３１ and L ３２ each independently represents F, Cl, CF ３ or CHF ２ and W represents O or S, and c is 0, 1 or 2.)

3. The liquid crystal medium according to claim 1 or 2, wherein the medium comprises one or more compounds of formula VI. 【Chemical Formula 7】 (In the formula, R ６１ and R ６２ represent H, F, a linear alkyl or alkoxy having 1 to 15 C atoms, a linear alkenyl or alkenyloxy having 2 to 15 C atoms, or a branched alkyl, alkoxy, alkenyl, alkenyloxy each having 3 to 15 C atoms, provided that in these groups one or more CH ２ groups are arranged such that O atoms are not directly linked to each other, 【Chemical 8】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO- and may each be independently replaced with each other, and one or more H atoms in the group may be replaced with halogen, X ６１ ~X ６６ represents H or F, either the same or different, and Z ６１ and Z ６２ are the same or different and represent CH ２ CH ２ or a single bond. )

4. The liquid crystal medium according to any one of claims 1 to 3, wherein the medium comprises one or more compounds of formula VIII. 【Chemical Formula 9】 (In the formula, R ８１ and R ８２ are the same or different and represent H, F, a linear alkyl or alkoxy having 1 to 15 C atoms, a linear alkenyl or alkenyloxy having 2 to 15 C atoms or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 C atoms, provided that one or more CH ２ groups in these groups are such that O atoms are not directly linked to each other. 【Chemical Formula 10】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO-, each of which may be independently replaced with one another, and one or more H atoms in the group may be replaced with halogen; A ０ 、 A ８１ and A ８２ are each, independently of one another, phenylene-1,4-diyl (in which one or two CH groups in the group may be replaced by N, and one or more H atoms are halogen, CN, CH ３ , CHF ２ , CH ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ and may be replaced by); cyclohexane-1,4-diyl (in which one or two non-adjacent CH ２ groups may each, independently of one another, be replaced by O and / or S, and one or more H atoms may be replaced by F); cyclohexene-1,4-diyl; bicyclo[1.1.1]pentane-1,3-diyl; bicyclo[2.2.2]octane-1,4-diyl; spiro[3.3]heptane-2,6-diyl; tetrahydropyran-2,5-diyl; or 1,3-dioxane-2,5-diyl; Z ８１ and Z ８２ are each independently of the other, -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -CO-O-, -O-CO-, -C ２ H ４ -, -C ２ F ４ -, -CF ２ CH ２ -, -CH ２ CF ２ -, -CFHCFH-, -CFHCH ２ -, -CH ２ CFH-, -CF ２ CFH-, -CFHCF ２ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C- or a single bond; n represents 0, 1, 2 or 3; and m represents 0, 1, 2 or 3.)

5. The liquid crystal medium according to any one of claims 1 to 4, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulae Z-1 to Z-8. 【Chemical 11】 (In the formula, R Ｚ has the meaning of R in claim 1 ２Ａ and (O) represents O or a single bond, and alkyl represents an alkyl having 1 to 7 C atoms.)

6. The liquid crystal medium according to any one of claims 1 to 5, wherein the medium comprises one or more compounds of formula IV. 【Chemical 12】 (In the formula, R ４１ represents alkyl having 1 to 7 carbon atoms or alkenyl having 2 to 7 carbon atoms, R ４２ represents alkyl having 1 to 7 C atoms, alkoxy having 1 to 6 C atoms, or alkenyl having 2 to 7 C atoms, provided that the compound of formula I according to claim 1 is excluded.)

7. The liquid crystal medium according to any one of claims 1 to 6, wherein the medium comprises one or more compounds of formulae IVb-1 to IVb-3. 【Chemical 13】 (In the formula, alkyl and alkyl ＊ each independently represents a linear alkyl group having 1 to 6 C atoms, and alkenyl and alkenyl ＊ each independently represents a linear alkenyl group having 2 to 6 C atoms.)

8. The liquid crystal medium according to any one of claims 1 to 7, wherein the medium comprises one or more compounds of formula V. 【Chemical 14】 (In the formula, R ５１ , R ５２ represents alkyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms, or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms, 【Chemical Formula 15】 represents, Z ５１ and Z ５２ are, the same or different, -CH ２ -CH ２ -, -CH ２ -O-, -CH=CH-, -C≡C-, -COO- or a single bond, and n is 1 or 2.)

9. The liquid crystal medium according to any one of claims 1 to 8, wherein the medium contains one or more compounds selected from the compounds of formulas V-1, V-2, and V-3. 【Chemical Formula 16】 (In the formula, the groups that appear have the meanings given in claim 8.)

10. The liquid crystal medium according to any one of claims 1 to 9, wherein the medium according to the invention contains one or more compounds of formula CL. 【Chemical 17】 (In the formula R Ｌ represents H, a linear or branched alkyl or alkoxy group having 1 to 15 C atoms, or a linear or branched alkenyl group having 2 to 15 C atoms, provided that in these groups, one or more CH ２ groups are arranged so that O atoms are not directly connected to each other. 【Chemical 18】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO-, each of which may be independently replaced with one another, and in addition, one or more H atoms in the group may be replaced with halogen, X Ｌ represents F, Cl, CN, CHF ２ , CF ３ , OCF ３ , or represents, identically or differently, one of the meanings of R Ｌ and has Y Ｌ represents H, F, Cl or CH ３ .)

11. The liquid crystal medium according to any one of claims 1 to 10, wherein the medium contains one or more compounds of formula X. 【Chemical 19】 (In the formula, R Ｘ represents a linear or branched alkyl or alkoxy group having 1 to 15 carbon atoms, provided that in these groups, one or more CH ２ groups are arranged so that O atoms are not directly connected to each other. 【Chemical 20】 -C≡C-, -CF ２ O-, -OCF ２ -,-CH=CH-,-O-,-CO-O- or -O-CO-, each of which may be independently replaced with one another, and in addition, one or more H atoms in the group may be replaced with halogen, 【Chemical 21】 represents 【Chemical 22】 represents X Ｘ represents F, Cl, CN, an alkyl halide group or an alkoxy halide group having 1 to 6 C atoms each, or an alkenyl halide group or an alkenyloxy halide group having 2 to 6 C atoms each, Z Ｘ represents -C ２ H ４ -, -CH ２ O-, CF ２ O, -CH=CH- or a single bond.

12. The liquid crystal medium according to any one of claims 1 to 11, wherein the medium contains one or more compounds of formula S. 【Chemical 23】 (In the formula, Ar represents a methylene group, an aromatic hydrocarbon group having 6 to 40 C atoms, or a heteroaromatic hydrocarbon group having 4 to 40 C atoms; Sp represents a spacer group; R Ｓ represents H, alkyl having 1 to 12 C atoms or alkenyl having 2 to 12 C atoms; Z Ｓ represents -O-, -C(O)O-, -(CH ２ ) ｚ - or -(CH ２ ) ｚ O- or a single bond; HA is 【Chemical Formula 24】 represents R Ｈ represents H, O ・ , CH ３ , OH or OR Ｓ ; R Ｓ１ 、 R Ｓ２ 、 R Ｓ３ and R Ｓ４ represent alkyl having 1 to 6 C atoms, which may be the same or different; G is H or R Ｓ or radical Z Ｓ -HA; z is an integer from 1 to 6; and q is 3 or 4.)

13. The liquid crystal medium according to any one of claims 1 to 12, wherein the medium contains a polymerizable compound.

14. A liquid crystal display comprising the liquid crystal medium according to any one of claims 1 to 13.

15. The liquid crystal display according to claim 14, wherein the display is a VA, IPS, FFS, PS-VA, PS-IPS, or PS-FFS type display.

16. Use of the liquid crystal medium according to any one of claims 1 to 13 in a VA, IPS, FFS, PS-VA, PS-IPS, or PS-FFS display.

17. An energy-saving display for games comprising the liquid crystal medium according to any one of claims 1 to 13.

Images