Liquid-crystal medium comprising polymerizable compounds

Abstract

To provide a liquid-crystal medium comprising polymerizable compounds.SOLUTION: The present invention relates to an LC medium comprising two or more polymerizable compounds, at least one of which contains a substituent comprising a tertiary OH group, to use of the LC medium for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the PSA (polymer sustained alignment) or SA (self-aligning) mode, to an LC display of the PSA or SA mode comprising the LC medium, and to a process of manufacturing the LC display using the LC medium, especially an energy-saving LC display and energy-saving LC display production process.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an LC medium comprising two or more polymerizable compounds, at least one of which comprises a substituent containing a tertiary OH group; the use of the LC medium for optical, electro-optical and electronic purposes, particularly in LC displays, especially in PSA (polymer sustained alignment) or SA (self-aligning) mode LC displays; a PSA or SA mode LC display comprising the LC medium; a method for manufacturing the LC display using the LC medium; and in particular, an energy-saving LC display and a method for manufacturing an energy-saving LC display. [Background technology]

[0002] The proliferation of 8K monitors and gaming monitors has led to increased demand for liquid crystal display (LCD) panels with higher refresh rates, and therefore for LC media with faster response times. Many of these LCD panels use polymer-stabilized (PS) or polymer-sustained alignment (PSA) modes, such as PS-VA (vertically aligned), PS-IPS (in-plane switching), or PS-FFS (fringe-field switching), or modes derived therefrom, or self-aligned (SA) modes such as polymer-stabilized SA-VA.

[0003] In PS or PSA modes, a small amount, typically 0.1–1%, of one or more polymerizable mesogen compounds, also known as reactive mesogens (RMs), is added to the LC medium. After filling the display with the LC medium, the RMs are polymerized in situ by UV photopolymerization while applying a voltage to the display electrodes. This generates a small tilt angle in the LC molecules of the LC medium, which is then stabilized by the polymerized RMs. The UV polymerization process, also called the "PSA process," is usually a two-step process, consisting of a first UV exposure step ("UV1 step") in which a voltage is applied to generate the tilt angle, and a second UV exposure step ("UV2 step") in which no voltage is applied to complete the polymerization of the RMs.

[0004] In SA-VA mode, the alignment layer in the display is omitted. Instead, a small amount, typically 0.1–2.5%, of self-alignment (SA) additives is added to the LC medium, which induces the desired orientation, such as homeotropic or planar orientation, through a self-assembly mechanism in situ.

[0005] SA additives typically contain an organic mesogenic core group to which one or more polar anchor groups, such as a hydroxyl group, carboxyl group, amino group, or thiol group, are linked. These anchor groups can interact with the substrate surface, orienting the additive on the substrate surface and inducing a desired orientation in the LC molecules. SA additives may also contain one or more polymerizable groups that can be polymerized under similar conditions to RM used in PSA processes. In addition to SA additives, the LC medium may also contain one or more types of RM.

[0006] One method to shorten the response time of the LC medium for PSA mode is to use compounds containing alkenyl groups as components of the LC host mixture, for example. However, this can lead to a decrease in the reliability of the mixture when exposed to the UV light required for polymerization of RM additives, which is thought to be due to the reaction of the alkenyl compound with the polyimide in the orientation layer, and this is particularly problematic when using UV wavelengths shorter than 320 nm. Therefore, PSA processes tend to use longer UV wavelengths.

[0007] UV-LED lamps have been proposed for use in PSA processes due to their low power consumption, long lifespan, and narrow emission peak, which allows for efficient transfer of light energy to liquid crystal media, thus reducing UV intensity and UV exposure time. This shortens cycle time and enables reductions in energy and manufacturing costs. UV lamps currently on the market have higher wavelength emission, for example, 365 nm.

[0008] Therefore, there is a demand for polymerizable LC media containing RM that can polymerize efficiently at longer UV wavelengths.

[0009] In addition, there is a great demand for PSA or SA displays, as well as LC media and polymerizable compounds, that enable high resistivity, a wide operating temperature range, short response time even at low temperatures, low threshold voltage, low tilt angle, high tilt stability, numerous intermediate tones, high contrast, and a wide viewing angle, while also possessing high reliability after UV exposure and a high VHR value, and, in the case of polymerizable compounds, a low melting point and high solubility in LC host mixtures. For displays intended for portable applications, the availability of LC media exhibiting low threshold voltage and high birefringence is particularly desirable. [Overview of the project] [Problems that the invention aims to solve]

[0010] The present invention is intended to provide novel and suitable materials, particularly RM and LC media containing the same, that do not have, or have to a reduced degree, the aforementioned defects for use in PSA or SA displays.

[0011] In particular, the present invention includes RM for use in PSA or SA displays, enabling very high resistivity, high VHR value, high reliability, low threshold voltage, short response time, and high birefringence, and in particular exhibiting good UV absorption in longer UV wavelengths, preferably in the range of 340-380 nm, enabling rapid and complete polymerization of RM, preferably generating the lowest possible tilt angle, enabling high stability of the tilt angle even after long periods and / or UV exposure, reducing or preventing the occurrence of "image fixation" and "ODF unevenness" in displays, polymerizing as rapidly and completely as possible in the case of RM, and is based on the purpose of an LC medium that exhibits high solubility in LC media typically used as host mixtures in PSA or SA displays.

[0012] A further object of the present invention is to provide an LC medium for use in PSA displays, in which RM exhibits both a fast polymerization rate and good reliability parameters such as high VHR or good tilt stability.

[0013] A further object of the present invention is to provide novel LC media containing RM, particularly for optical, electro-optical, and electronic applications, and suitable processes and intermediates for preparing them.

[0014] A further object of the present invention is to provide an LC medium containing RM that exhibits one or more of the following advantageous effects: They generate a tilt angle to the desired degree after exposure to UV light. • These provide good tilt stability. • These result in a high VHR. They exhibit good UV absorption, particularly in the longer UV wavelength range, especially in the 340-400 nm range, enabling rapid and complete polymerization of RM at these wavelengths. They are suitable for use in PSA displays prepared by polymerization processes using UV-LED lamps. These enable good control over the time range of the first UV process in which the tilt angle is generated during UV treatment. These allow for minimizing energy consumption and production costs by keeping the time range of the second UV process, which polymerizes all remaining RM to stabilize the tilt angle, as short as possible. After the first and second UV exposure steps, residual RM has little to no adverse effect on the performance parameters of the LC mixture, such as VHR and tilt stability. [Means for solving the problem]

[0015] It has been found that one or more of these objectives can be achieved by providing an LC medium containing a polymerizable compound as disclosed and claimed hereafter.

[0016] The present invention relates to an LC medium comprising one or more polymerizable compounds selected from formula IA and one or more polymerizable compounds selected from formulas IB and IC.

[0017] [ka]

[0018] In the formula, each base is independent of the others and, in each instance, identical or different in meaning as follows: P is a polymerizable group, Sp is a spacer group or a single bond. M 1 M 2 M 3 These are each bases individually selected from the following formulas, [ka] However, the benzene ring may be substituted with one or more groups L or P-Sp-, L is F, Cl, -CN, P-Sp- or a linear, branched or cyclic alkyl having 1 to 25 C atoms, provided that one or more non-adjacent CH2 groups may be replaced by O atoms and / or S atoms, respectively, such that they are not directly linked to each other by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and provided that one or more H atoms may be replaced by P, F or Cl, respectively, However, in the compound of formula IA, the group M 1 and / or at least one spacer group Sp is L a and is at least monosubstituted with L a is -C(R aa )(R bb )OH, R aa and R bb are linear alkyls having 1 to 6 C atoms, and in the compound of formula IC, the group M 3 is at least monosubstituted with L b and L b is a linear or branched alkenyl having 2 to 7 C atoms, preferably 3 or 4 C atoms.

[0019] The present invention further relates to a liquid crystal medium having negative dielectric anisotropy and containing one or more polymerizable compounds selected from formula IA, one or more polymerizable compounds selected from formula IB and IC, and further containing one or more compounds of formula II.

[0020]

Chemical formula

[0021] In the formula, each group, independently of one another, has the same or different meaning in each occurrence as follows R 1 and R2 These are linear, branched, or cyclic alkyl groups having 1 to 25 carbon atoms (where one or more non-adjacent CH2 groups have oxygen and / or sulfur atoms that are not directly linked to each other, resulting in -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, CR 0 =CR 00 -, -C≡C-, [ka] It may be replaced by, however, one or more H atoms may be replaced by F or Cl. ), preferably an alkyl or alkoxy having 1 to 6 C atoms. R 0 , R 00 This is an alkyl group having H or 1 to 12 C atoms, preferably H. A 1 and A 2 The following formula [ka] Preferably, the group is selected from formulas A1, A2, A3, A4, A5, A6, A9 and A10, and very preferably from formulas A1, A2, A3, A4, A5, A9 and A10. Z 1 and Z 2 These are -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2F4-, -CF=CF-, -CH=CH-CH2O- or single bonds, preferably single bonds. L 1 , L 2 , L 3 and L 4 is F, Cl, OCF3, CF3, CH3, CH2F or CHF2, preferably F or Cl, very preferably F. Y is H, F, Cl, CF3, CHF2, or CH3, preferably H or CH3, very preferably H. L C is CH3 or OCH3, preferably CH3. a1 is either 1 or 2. a2 is either 0 or 1.

[0022] The present invention further relates to the use of LC media in PSA or SA mode LC displays as described above and below.

[0023] 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 polymerizable compounds of formula I with one or more compounds of formula II and optionally with further LC compounds and / or additives.

[0024] The present invention further relates to an LC display comprising an LC medium according to the present invention as described above and below, wherein it is a PSA or SA display, preferably a PS-VA, PS-IPS, PS-FFS or SA-VA display.

[0025] The present invention further relates to an LC display comprising an LC medium as described above and below, wherein the polymerizable compound exists in a polymerized form, preferably a PSA or SA display, and more preferably a PS-VA, PS-IPS, PS-FFS or SA-VA display.

[0026] The present invention further relates to a PSA-type LC display comprising two substrates, at least one of which is transparent to light; electrodes provided on each substrate or two electrodes provided on only one of the substrates; and layers of LC medium as described above and below, disposed between the substrates, wherein a polymerizable compound is polymerized between the substrates of the display by UV photopolymerization.

[0027] The present invention further relates to a method for manufacturing an LC display as described above and below, comprising filling or otherwise providing an LC medium between substrates of a display as described above and below, preferably irradiating with UV light having a wavelength preferably greater than 340 nm, preferably greater than 360 nm, preferably in the range of 340 to 400 nm, more preferably in the range of 350 to 390 nm, very preferably in the range of 360 to 380 nm, and most preferably in the range of 360 to 368 nm, and preferably polymerizing a polymerizable compound while applying a voltage to the electrodes of the display.

[0028] The present invention further relates to a method for manufacturing an LC display as described above and below, wherein the irradiation of a polymerizable compound is performed using a UV-LED lamp.

[0029] When used in a PSA display, the LC medium according to the present invention exhibits the following advantageous characteristics: • Proper tilt generation within a specific process window. • Rapid polymerization to minimize RM residue after UV treatment. • High voltage retention rate of RM after UV treatment, • Good tilt stability, • Good VHR, • Sufficient thermal stability, • Sufficient solubility in organic solvents typically used in display manufacturing.

[0030] In addition, the LC medium according to the present invention exhibits one or more of the following advantageous properties: They generate a tilt angle to the desired degree after exposure to UV light. • They offer high tilt stability. They exhibit good UV absorption, particularly in the longer UV wavelength range, preferably in the range of 340-400 nm, more preferably in the range of 350-390 nm, very preferably in the range of 360-380 nm, and most preferably in the range of 360-368 nm, enabling rapid and complete polymerization of RM at these wavelengths. They are suitable for use in PSA displays prepared by polymerization processes using UV-LED lamps. These enable good control over the time range of the first UV process in which the tilt angle is generated during UV treatment. • They aim to minimize production costs by keeping the time range of the second UV process as short as possible. After the first and second UV exposure processes, they reduce or avoid the adverse effects of residual RM on all performance parameters of the LC mixture, such as VHR and tilt stability. [Modes for carrying out the invention]

[0031] Alkenyl groups in the compounds of formula II as disclosed below or in other components of the LC medium are not considered to be within the meaning of the term “polymerizable group” as used herein. The polymerization conditions of the polymerizable compounds in the LC medium are preferably selected so that the alkenyl substituent does not participate in the polymerization reaction. Preferably, the LC mediums disclosed and claimed in this application do not contain additives that initiate or promote the participation of alkenyl groups in the polymerization reaction.

[0032] Unless otherwise specified, polymerizable compounds and compounds of formula II are preferably selected from achiral compounds.

[0033] As used herein, the expression “UV light having wavelengths of” following a given wavelength range (in nm) or a given lower or upper limit of wavelength (in nm) means that the UV emission spectrum of each radiation source has an emission peak which is the highest peak within the given wavelength range or above the given lower limit of wavelength or below the given upper limit of wavelength, and / or the UV absorption spectrum of each chemical has a long or short wavelength tail that extends within the given wavelength range or above the given lower limit of wavelength or below the given upper limit of wavelength.

[0034] As used herein, the term “full width at half maximum” or “FWHM” means the width of the spectral curve measured between points on the y-axis that are half of the maximum amplitude.

[0035] As used herein, the term "substantially transmit" means that the filter transmits most, preferably at least 50%, of the incident light of the desired wavelength. As used herein, the term "substantially block" means that the filter does not transmit most, preferably at least 50%, of the incident light of the undesired wavelength. As used herein, the term "desired (undesired) wavelength" means, for example, wavelengths within (outside) a given range of λ in the case of a bandpass filter, and wavelengths above (below) a given value of λ in the case of a cutoff filter.

[0036] As used herein, the terms “active layer” and “switchable layer” refer to layers in electro-optical displays, such as LC displays, that contain one or more molecules having structural and optical anisotropy, such as LC molecules, whose orientation changes in response to external stimuli, such as electric or magnetic fields, resulting in a change in the transparency of the layer to polarized or unpolarized light.

[0037] As used herein, the terms “tilt” and “tilt angle” mean the tilted orientation of LC molecules in an LC medium relative to the cell surface in an LC display (preferably a PSA display). In this specification, the tilt angle means the average angle (less than 90°) between the molecular long axis (LC director) of the LC molecule and the surface of the flat, parallel outer plate forming the LC cell. In this specification, a low tilt angle (i.e., far from 90°) corresponds to a large tilt. Appropriate methods for measuring the tilt angle are given in the examples. Unless otherwise indicated, the tilt angle values ​​disclosed above and below refer to this measurement method.

[0038] As used herein, the terms “reactive mesogen” and “RM (reactive mesogen)” are understood to mean a compound containing a mesogen or liquid crystal skeleton and one or more functional groups linked to that skeleton and suitable for polymerization, and the functional group is also referred to as a “polymerizable group” or “P”.

[0039] Unless otherwise specified, the term "polymerizable compound" in this specification shall be understood to mean a polymerizable monomer compound.

[0040] The SA-VA display according to the present invention is a polymer-stabilized mode comprising or manufactured using an LC medium containing RM of formulas I and II. Consequently, as used herein, the term "SA-VA display" when referring to the display according to the present invention shall be understood to refer to the polymer-stabilized SA-VA display, even if not explicitly mentioned otherwise.

[0041] As used herein, the term "low molecular weight compound" is understood to mean a monomer and / or a compound not prepared by polymerization, as opposed to "polymer compound" or "polymer."

[0042] As used herein, the term "non-polymerizable compound" is understood to mean a compound that does not contain functional groups suitable for polymerization under the conditions normally applied for the polymerization of RM.

[0043] As used herein, the term “mesogenic group” refers to a group known to those skilled in the art and documented in the literature, which, due to the anisotropy of its attractive and repulsive interactions, essentially contributes to the formation of a liquid-crystalline (LC) phase in low-molecular-weight or high-molecular-weight materials. Compounds containing mesogenic groups (mesogenic compounds) do not necessarily have an LC phase themselves. It is also possible for mesogenic compounds to exhibit LC phase behavior only after mixing with other compounds and / or polymerization. Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units. An overview of the terms and definitions used with respect to mesogenic 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.

[0044] As used herein, the term “spacer group” is also hereafter referred to as “Sp,” and 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.

[0045] Above and below, [ka] This represents a trans-1,4-cyclohexylene ring, [ka] This represents a 1,4-phenylene ring.

[0046] base [ka] In this example, the single bond between the two ring atoms can be linked to any unbonded position on the benzene ring.

[0047] In the formulas shown above and below, the base R 1~13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 If R or L represents an alkyl and / or alkoxy group, it may be linear or branched. It is preferably linear and has 2, 3, 4, 5, 6 or 7 C atoms, and therefore preferably represents ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, and furthermore, methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.

[0048] In the formulas shown above and below, the base R 1~13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2If R or L represents an alkyl group in which one or more CH2 groups are replaced by S, it may be linear or branched. It is preferably linear and has 2, 3, 4, 5, 6 or 7 C atoms, and therefore preferably represents thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl or thioheptyl.

[0049] Oxaalkyl preferably represents linear 2-oxapropyl (=methoxymethyl), 2-(=ethoxymethyl) or 3-oxabutyl (=2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, or 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.

[0050] In the formulas shown above and below, the base R 1~13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 If R or L represents an alkoxy or oxaalkyl group, it may also include one or more additional oxygen atoms, provided that the oxygen atoms are not directly bonded to each other.

[0051] In another preferred embodiment, one or more R 1~13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2, R or L is,

Chem.

Chem.

[0052] In the formulas shown above and below, the group R 1~13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R [[ID=At 47]] IIIA , R <000't 096>, R 2N , R <000009'8>, R B2 , R CR1 , R CR2If R or L represents an alkyl group in which one or more CH2 groups are replaced with -CH=CH-, it may be linear or branched. It is preferably linear and has 2 to 10 C atoms. Therefore, it represents vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, penta-1-, -2-, -3- or -4-enyl, hexa-1-, -2-, -3-, -4- or -5-enyl, hepta-1-, -2-, -3-, -4-, -5- or -6-enyl, octa-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, nona-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, deca-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or -9-enyl.

[0053] In the formulas shown above and below, the base R 1~13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 When R or L represents an alkyl or alkenyl group that is at least one-substituted with a halogen, the group is preferably linear, and the halogen is preferably F or Cl. In the case of polysubstituted groups, the halogen is preferably F. Perfluoro groups are also included in the resulting groups. In the case of monosubstituted groups, the fluorine or chlorine substituent may be at any desired position, but is preferably at the ω position.

[0054] The halogen is preferably F or Cl, and very preferably F.

[0055] Group-CR 0 =CR 00 - is preferably -CH=CH-.

[0056] -CO-, -C(=O)-, and -C(O)- are carbonyl groups, i.e., [ka] It represents.

[0057] Preferred substituents L are, for example, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x )2, -C(=O)Y 1 -C(=O)R x , -N(R x )2, linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms each (wherein one or more H atoms may be replaced with F or Cl), silyl having 1 to 20 Si atoms which may be substituted, or aryl having 6 to 25, preferably 6 to 15 C atoms which may be substituted.

[0058] In the formula, R x represents an alkyl chain having 1 to 25 carbon atoms, wherein one or more non-adjacent CH2 groups may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, such that the O- and / S- atoms are not directly linked to each other, wherein one or more H atoms may be replaced with F, Cl, P- or P-Sp-, and

[0059] Y 1 This represents halogen.

[0060] Particularly preferred substituents L include, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and phenyl.

[0061] [ka] In the formula, L has one of the meanings shown above.

[0062] The polymerizable group P is suitable for polymerization reactions such as free radical or ionic chain polymerization, polyaddition or polycondensation, or for polymer-like reactions such as addition or condensation onto a polymer backbone. 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 oxetane or epoxide groups, are especially preferred.

[0063] The preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -(O) k3 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -, HS-CW 2 W 3 -, HW 2 N-, HO-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-, in the formula, W 1This 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 of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 k1, k2, and k3 each independently represent H, Cl, or an alkyl group having 1 to 5 C atoms; Phe represents 1,4-phenylene which may be substituted with one or more groups L as defined above, other than P-Sp-; k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0064] A very preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -O-, CH2=CW 2 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH- and W 4 W 5 W6 Selected from the group consisting of Si-, in the formula, W 1 This 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 of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 k1, k2, and k3 each independently represent H, Cl, or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene, k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0065] A particularly preferred group P is CH2=CW 1 -CO-O-, in particular CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, furthermore CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, [ka] Selected from the group consisting of

[0066] A more preferred polymerizable group P is selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide groups, most preferably from acrylate and methacrylate.

[0067] Preferably, all polymerizable groups in the polymerizable compound have the same meaning.

[0068] If the spacer group Sp is different from the single bond, it is preferably Sp"-X" such that each group P-Sp- corresponds to formula R-Sp"-X"-, however,

[0069] Sp'' represents a linear or branched alkylene having 1 to 20, preferably 1 to 12, carbon atoms, the group may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, except that one or more non-adjacent CH2 groups are independently -O-, -S-, -NH-, -N(R) such that the O and / or S atoms are not directly linked to each other. 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 also be used as substitutes. “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 single bond are represented. R 0 and R 00 Each of these independently represents an alkyl group having either H or 1 to 20 C atoms. Y 2 and Y 3 Each of these elements independently represents either H, F, Cl, or CN.

[0070] X" is sometimes -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 -or it is a single bond.

[0071] Typical spacer bases 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 -In the formula, p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, R 0 and R 00 The above has the meanings shown.

[0072] Particularly preferred spacer bases Sp and -Sp”-X”- are -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, where p1 and q1 have the meanings shown above.

[0073] Particularly preferred groups Sp'' are linear in each case and are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, etenylene, propenylene, and butenylene.

[0074] In preferred embodiments of the present invention, compounds of formula IA and / or IB and / or IC and their sub-formulas are such that the group Sp-P is Sp(P) s It contains a spacer group Sp (branched polymerizable group) substituted with one or more polymerizable groups P to correspond to (where s is 2 or greater).

[0075] The preferred compounds of formulas IA, IB, and IC according to this preferred embodiment are those with s = 2, i.e., compounds containing the group Sp(P)2. The very preferred compounds of formulas IA and IB according to this preferred embodiment contain a group selected from the following formulas.

[0076] [ka]

[0077] In the formula, P is defined as in formula I, Alkyl groups represent linear or branched alkylenes having single bonds or 1 to 12 carbon atoms, and the group is either unsubstituted or monosubstituted or polysubstituted with F, Cl, or CN, provided that one or more non-adjacent CH2 groups are each independently bonded to each other such that the O and / or S atoms are not directly bonded to each other, and -C(R 0 )=C(R 0 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- may be substituted, however R 0 It 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 in "X", and is preferably O, CO, SO2, O-CO-, CO-O, or a single bond.

[0078] A preferred spacer base Sp(P)2 is selected from formulas S1, S2, and S3.

[0079] A highly preferred spacer base Sp(P)2 is selected from the following sub-formulas.

[0080] [ka]

[0081] In the compounds of formula P and its subformulas as described above and below, P is preferably selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide, most preferably from acrylate and methacrylate.

[0082] More preferably, all polymerizable groups P present in the compound have the same meaning and represent either acrylate or methacrylate, most preferably methacrylate.

[0083] Sp is a single bond or -(CH2) p1 -, -O-(CH2) p1 -, -O-CO-(CH2) p1 Or -CO-O-(CH2) p1 This represents a function where p1 is 2, 3, 4, 5, or 6, preferably 2 or 3, and p2 and p3 are each independently 0, 1, 2, or 3, and Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 In this case, either an O atom or a CO group is linked to the benzene ring.

[0084] In preferred embodiments of compounds of formula IA and / or IB and / or IC, at least one group Sp is a single bond.

[0085] In a very preferred embodiment of the compound of formula IB, all Sp groups are single bonds.

[0086] In another preferred embodiment of the compound of formula IA and / or IB and / or IC, at least one group Sp is a single bond and at least one group Sp is not a single bond.

[0087] If the group Sp is different from a single bond, it is preferably -(CH2) p1 -,-(CH2) p2 -CH=CH-(CH2) p3 -, -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 Selected from the formula, where p1 is 2, 3, 4, 5, or 6, preferably 2 or 3, p2 and p3 are each independently 0, 1, 2, or 3, and Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 In each case, an O atom or a CO group is linked to the benzene ring. Very preferably, if Sp is different from a single bond, it is selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2 and -CO-O-(CH)2-, in which an O atom or a CO group is linked to the benzene ring.

[0088] In preferred embodiments of the present invention, compounds of formula IA and its sub-formulas contain one or more, preferably one, group L a Includes a spacer group Sp which is replaced by

[0089] In compounds of formula IA and its subformulas, R aa and R bb Preferably, R represents a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms. More preferably, R aa and R bb Each of these independently represents methyl, ethyl, propyl, and butyl, very preferably methyl or ethyl, and most preferably methyl.

[0090] R aa and R bb More preferably are compounds of formula IA and its subformulas as described above and below, which, together with the C atoms to which they are bonded, form a cyclic alkyl group having 3 to 12 C atoms, very preferably a cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl group.

[0091] More preferably, the compound of formula IA is a group L selected from the following formulas. a Includes.

[0092] [ka]

[0093] In the formula, the asterisk represents linkage to an adjacent group in the compound of formula I.

[0094] In another preferred embodiment of the present invention, compounds of formula IA and its subformulas include one or more groups L a It contains a spacer group Sp, which is a linear or branched alkylene having 1 to 12, preferably 1 to 7, carbon atoms substituted by. A preferred compound of formula IA according to this preferred embodiment contains a group P-Sp- selected from the following formulas.

[0095] [ka]

[0096] In the formula, P and L a cc is as defined in Formula I, or has one of the meanings given above and below, where cc is 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3.

[0097] Preferred compounds of formula I contain one or more P-Sp- groups selected from formulas SL1, SL2, and SL3, very preferably from formula SL1.

[0098] Preferably, in a compound of formula IA, M1 is selected from Formula 1 or 2.

[0099] Preferred compounds of Formula IA are selected from the following sub-formulas.

[0100]

Chemical formula

[0101]

Chemical formula

[0102]

Chemical formula

[0103] Wherein, P, Sp and L have one of the meanings given in Formula IA or the preferred meanings given above and below, r1, r2, r3 are each independently 0, 1, 2, 3 or 4, r4 is 0, 1, 2 or 3, provided that the compound has at least one group Sp and / or at least one group L represented by L a which is at least monosubstituted by a and includes at least one group L.

[0104] Very preferred compounds of Formula I are selected from the following sub-formulas.

[0105]

Chemical formula

[0106]

Chemical formula

[0108]

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[0109]

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[0110]

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[0111]

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[0112]

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[0113]

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[0114]

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[0115]

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[0116]

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[0117]

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[0118]

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[0119] In the formula, P, Sp and L a Sp has the meaning given by formula IC or one of the preferred meanings given above or below, Sp is preferably different from a single bond, and Sp' is the base L a A spacer group that is replaced by, preferably selected from formulas SL1 to SL4, where L' has one of the meanings given to L as above or below, preferably L a It is different.

[0120] The highly preferred compounds of subformulas IA-1-1 to IA-10-5 are those in which all groups P are identical, representing acrylate or methacrylate, preferably methacrylate, and furthermore, Sp is -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO- or -(CH2) p1 The formula is -CO-O-, where p1 is an integer from 1 to 12, preferably from 1 to 6, the O- or CO- group is attached to a benzene ring, Sp' is selected from formula SL1, and L' is F.

[0121] More preferred compounds of formula IA and its subformulas are selected from the following preferred embodiments, including any combination thereof: • All groups P in a compound have the same meaning. Ma is either formula 1 or 2, and very preferably formula 1. The compound contains only two polymerizable groups (represented by group P). The compound contains only three polymerizable groups (represented by group P). P is selected from the group consisting of acrylates, methacrylates, and oxetanes, very preferably acrylates or methacrylates. • Compounds are L aSubstituted by, preferably comprising at least one, preferably only one, base Sp selected from formulas SL1 to SL4, and very preferably from formulas SL1, SL2 and SL3. • If Sp is different from a single bond, it is -(CH2) p2 -,-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 The formula is -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O atom or CO group is each connected to a benzene ring. ·Sp' is selected from formula SL1, L represents F, Cl, CH3, C2H5, OCH3, or OC2H5, very preferably F. ·L' represents F, Cl, CH3, C2H5, OCH3 or OC2H5, very preferably F. ·L a This represents -C(CH3)2-OH, -C(C2H5)2-OH, or -C(CH3)(C2H5)OH, very preferably -C(CH3)2-OH. r1, r2, r3, and r4 represent 0 or 1. r1+r2 is 0, r1 + r2 is 1, ·r3 is 0, r4 is 0.

[0122] Highly preferred compounds of formula IA and its subformulas are selected from the following list.

[0123] [ka]

[0124] [ka]

[0125] [ka]

[0126] In the formula, "Me" represents methyl and "Et" represents ethyl.

[0127] In preferred embodiments, the LC medium comprises one or more compounds of formula IB having two polymerizable groups, preferably selected from formulas IB-D.

[0128] [ka]

[0129] In the formula, P and Sp have the meanings given in formula IB, L is different from P-Sp- and has one of the meanings given in formula IB, r1, r2 and r3 are each independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1, and k is 0 or 1.

[0130] The preferred compound of formula IB-D is selected from the following sub-formulas.

[0131] [ka]

[0132] In the formula, P and Sp, L, r1, r2 and r3 each independently have one of the meanings given in formula IB-D or one of the preferred meanings given above and below.

[0133] In the compound of formula IB-D, preferably at least one of r1, r2, and r3 is not 0. P is preferably an acrylate or methacrylate, very preferably methacrylate. Preferably all groups P in formulas IB-D, IB-D-1, and IB-D-2 have the same meaning and very preferably represent methacrylate. Sp'' is preferably selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2, and -CO-O-(CH)2-, in which an O atom or CO group is linked to a benzene ring. L is preferably selected from F, CH3, OCH3, OC2H5, and C2H5, very preferably F.

[0134] Compounds of formula IB-D-1 are highly preferred.

[0135] A more preferred compound of formula IB-D is selected from the following sub-formulas.

[0136] [ka]

[0137] [ka]

[0138] [ka]

[0139] [ka]

[0140] [ka]

[0141] [ka]

[0142] [ka]

[0143] In the formulas, P and L have one of the meanings given in formulas IB-D, and Sp' has one of the meanings given for Sp different from a single bond. P is preferably an acrylate or methacrylate, very preferably methacrylate. Preferably, all groups P in formulas IB-D-1-1 to IB-D-2-30 have the same meaning and very preferably represent methacrylate. Sp' is preferably selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2 and -CO-O-(CH)2-, where the O atom or CO group is linked to the benzene ring. L is preferably selected from F, CH3, OCH3, OC2H5 and C2H5, very preferably F and OCH3.

[0144] Compounds of formulas IB-D-1-1, IB-D-1-2, IB-D-1-3, IB-D-1-4, IB-D-1-5, IB-D-1-6, IB-D-2-1, IB-D-2-2, IB-D-2-12, IB-D-2-13, and IB-D-2-14 and their subformulas are highly preferred. Compounds of formula IB-D-1-1 are most preferred.

[0145] A highly preferred compound of formula IB-D is selected from the following sub-formulas.

[0146] [ka]

[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] Compounds of formulas IBD1, IBD2, IBD4, IBD17, IBD21, and IBD22 are very preferred. Compounds of formula IBD1 are most preferred.

[0152] Compounds of formula IBD1 to IBD16 in which one or two methacrylate groups are replaced by acrylate groups are even more preferred.

[0153] A more preferred compound of formula IB-D is selected from Table D below, most preferably from the group consisting of RM-1, RM-2, RM-3, RM-7 to RM-49 and RM-58 to RM-77, and most preferably from the group consisting of RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-58, RM-64, RM-72 and RM-74.

[0154] In another preferred embodiment, the LC medium comprises one or more polymerizable compounds of formula IB having three polymerizable groups, preferably selected from formula IB-T.

[0155] [ka]

[0156] In the formula, P, Sp, L, r1, r2, and k each independently have the meaning given in formula IB-D or one of their preferred meanings given above and below, and r4 is 0, 1, 2, or 3, preferably 0, 1, or 2, very preferably 0 or 1.

[0157] The preferred compound of formula IB-T is selected from the following sub-formulas.

[0158] [ka]

[0159] [ka]

[0160] In the formula, P, Sp, L, r1, r2, and r4 each independently have one of the meanings given in formula IB-T or one of their preferred meanings given above and below. Preferably, at least one of r1, r2, and r4 is not 0. P is preferably an acrylate or methacrylate, very preferably methacrylate. L is preferably selected from F, CH3, OCH3, OC2H5, and C2H5, very preferably OCH3 or F. Preferably, all groups P in formulas IB-T and IB-T-1 to IB-T-6 have the same meaning and very preferably represent methacrylate.

[0161] Compounds of formulas IB-T-1, IB-T-4, and IB-T-5 are highly preferred.

[0162] The most preferred compound of formula IB-T is selected from the following sub-formulas.

[0163] [ka]

[0164] [ka]

[0165]

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[0166]

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[0167]

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[0168]

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[0169]

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[0170]

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[0171]

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[0172]

change

[0173] In the formulas, P, Sp, and L have one of the meanings given in formula IB-T, and Sp' has one of the meanings given for Sp that is different from a single bond. P is preferably an acrylate or methacrylate, very preferably methacrylate. Preferably, in formulas IB-T-1-1 to IB-T-6-12, all groups P have the same meaning and very preferably represent methacrylate. Sp' is preferably selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2 and -CO-O-(CH)2-, in which an O atom or CO group is linked to a benzene ring. L is preferably selected from F, CH3, OCH3, OC2H5 and C2H5, very preferably F and OCH3.

[0174] Compounds of formulas IB-T-1-1, IB-T-1-6, IB-T-4-1, IB-T-5-1, and their sub-formulas are highly preferred.

[0175] A highly preferred compound of formula IB-T is selected from the following sub-formulas.

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] [ka]

[0181]

change

[0182]

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[0183]

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[0184]

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[0185]

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[0186]

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[0187]

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[0188]

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[0189]

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[0190]

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[0191]

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[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] Among the compounds of formula IBT1 to IB-T21 having two benzene rings, compounds of formula IBT1, IBT2, IBT3, IBT8, IBT9, IBT10, IBT15, IBT16, and IBT17 are very preferred. Compounds of formula IBT1, IBT2, IBT3, IBT8, IBT9, and IB10 are most preferred.

[0197] Among the compounds of formula IBT22 to IBT53 having three benzene rings, compounds of formula IBT22 to IBT46 are very preferred. Compounds of formula IBT22, IBT28, IBT29, IBT35 and IBT36 are most preferred.

[0198] Compounds of formula IBT1 to IBT53 in which one or two methacrylate groups are replaced by acrylate groups are even more preferred.

[0199] Compounds of formula IBT1 to IBT53, in which all methacrylate groups are replaced with acrylate groups, are even more preferred.

[0200] In another preferred embodiment, the LC medium is an alkenyl group L bIt includes at least one compound of formula IC that is at least one-substituted by . The preferred compound of formula IC in this preferred embodiment is selected from the following sub-formulas.

[0201] [ka]

[0202] [ka]

[0203] [ka]

[0204] In the formula, P, Sp, L, r1, r2, r3, and r4 have the meanings given in formulas IB-D and IB-T or one of the preferred meanings given above and below, r1+r2+r3+r4≧1, and the compound is L b It contains at least one base L representing [the specified value].

[0205] In compounds of formula IC-1 to IC-9, preferably L b -CH=CH2, -CH2-CH=CH2, -CH=CH-CH3, -CH=CH-CH=CH2, or -C(CH3)=CH2, very preferably -CH=CH2 or C(CH3)=CH2.

[0206] In the compounds of formulas IC-1 to IC-9, P is preferably an acrylate or methacrylate, and very preferably a methacrylate. When Sp is different from a single bond, it is preferably selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2 and -CO-O-(CH)2-, where an O atom or CO group is linked to a benzene ring. L is preferably selected from F, CH3, OCH3, OC2H5 or C2H5, and very preferably OCH3 or F. Preferably, all groups P in formulas IC-1 to IC-9 have the same meaning and very preferably represent methacrylate.

[0207] Preferred compounds of formulas IC-1 to IC-9 are selected from the following sub-formulas.

[0208] [ka]

[0209] [ka]

[0210] [ka]

[0211] [ka]

[0212] [ka]

[0213] [ka]

[0214] [ka]

[0215]

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[0216]

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[0217]

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[0218]

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[0219]

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[0220]

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[0221]

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[0222]

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[0223]

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[0224]

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[0225] [ka]

[0226] [ka]

[0227] [ka]

[0228] [ka]

[0229] [ka]

[0230] [ka]

[0231] [ka]

[0232] In the formula, A is L b This represents P, Sp, and L having the meanings given in formula I or one of the preferred meanings given above and below, and L may also have one of the meanings given for A.

[0233] Preferably, in these compounds, A is -CH=CH2, -CH2-CH=CH2, -CH=CH-CH3, -CH=CH-CH=CH2, or -C(CH3)=CH2, very preferably -CH=CH2 or C(CH3)=CH2. Even more preferably, in these compounds, L represents F, Cl, CH3, C2H5, OCH3, or OC2H5, very preferably F. Even more preferably, in these compounds, L has one of the meanings given for A, preferably -CH=CH2 or C(CH3)=CH2. Even more preferably, in these compounds, at least one group Sp represents a single bond. Even more preferably, in these compounds, P represents an acrylate or methacrylate, very preferably methacrylate.

[0234] The most preferred compounds of formulas IC-1 to IC-9 are selected from the following sub-formulas.

[0235] [ka]

[0236] [ka]

[0237] [ka]

[0238] [ka]

[0239] [ka]

[0240] [ka]

[0241] [ka]

[0242] [ka]

[0243] Compounds of formula IC1 to IC46 in which one, two, or all methacrylate groups are replaced by acrylate groups are even more preferred.

[0244] In preferred embodiments, the LC medium comprises at least one polymerizable compound of formula IA and / or formula IB and / or formula IC having absorption in the range of 330–390 nm. Very preferably, these compounds have an extinction coefficient of at least 0.5 at wavelengths in the range of 330–390 nm, more preferably 340–380 nm, very preferably 350–370 nm, and most preferably 355–365 nm. The extinction coefficient and absorption wavelength are measured in a solution of the compound at a concentration of 3 g / L in the DCM unless otherwise specified.

[0245] The total proportion of polymerizable compounds of formulas IA, IB, IC and their sub-formulas in the LC medium according to the present invention is preferably 0.05 to 3.0%, more preferably 0.1 to 1.5%, and very preferably 0.1 to 0.9%.

[0246] In a first preferred embodiment of the present invention, the LC medium comprises one or more compounds of formula IA or its sub-formula (one or more) and one or more compounds of formula IB or IC their sub-formulas, preferably without further polymerizable compounds.

[0247] Preferably, in the LC medium of this first preferred embodiment, the proportion of one or more compounds of formula IA or its sub-formulas is 0.01 to 1.0%, more preferably 0.05 to 0.8%, and very preferably 0.1 to 0.6%, and the proportion of one or more compounds of formula IB or IC or its sub-formulas is 0.01 to 1.0%, more preferably 0.02 to 0.8%, and very preferably 0.05 to 0.5%.

[0248] In a second preferred embodiment of the present invention, the LC medium comprises one or more compounds of formula IA or its sub-formula (one or more), preferably one or more compounds of formula IB or its sub-formula (one or more), and one or more compounds of formula IC or its sub-formula (one or more), preferably without any further polymerizable compounds.

[0249] More preferably, the LC medium of this second preferred embodiment comprises one or more compounds of formula IA or its sub-formula (one or more), one or more compounds of formula IB-D or IB-T or their sub-formulas (one or more), and one or more compounds selected from formulas IC-1 to IC-9 or their sub-formulas (one or more), and preferably no further polymerizable compounds.

[0250] Preferably, in the LC medium of this second preferred embodiment, the proportion of one or more compounds of formula IA or its sub-formulas is 0.01 to 1.0%, more preferably 0.05 to 0.8%, and very preferably 0.1 to 0.6%, the total proportion of one or more compounds of formulas IB-D and IB-T or their sub-formulas is 0.01 to 1.0%, more preferably 0.05 to 0.8%, and very preferably 0.1 to 0.6%, and the total proportion of one or more compounds of formulas IC-1 to IC-9 or their sub-formulas is 0.01 to 1.0%, more preferably 0.02 to 0.8%, and very preferably 0.05 to 0.5%.

[0251] In another preferred embodiment, the LC medium comprises polymerizable compounds of formulas IA, IB, IC and their subformulas, in addition to at least one further polymerizable compound.

[0252] Preferred further polymerizable compounds are selected from the group consisting of formulas 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-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121, RM-122, RM-139, RM-142, RM-143, RM-148 to RM-158, RM-164, RM-165, and RM-166 to RM-178.

[0253] The proportion of these further polymerizable compounds in the LC medium is preferably 0.01 to 1.0%, more preferably 0.05 to 0.6%.

[0254] Polymerizable compounds are known to those skilled in the art and can be prepared by processes similar to those described in standard organic chemistry textbooks such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Thieme-Verlag, and Stuttgart.

[0255] For example, acrylic acid esters or methacrylic acid esters can be prepared by esterifying the corresponding alcohol with an acid derivative such as (meth)acryloyl chloride or (meth)acrylic anhydride in the presence of a base such as pyridine or triethylamine or 4-(N,N-dimethylamino)pyridine (DMAP). Alternatively, esters can also be prepared by esterifying alcohols with (meth)acrylic acid using dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC), or N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and DMAP in the presence of a dehydrating agent, for example, according to Steglich.

[0256] The present invention further relates to an LC medium or LC display as described above, wherein the polymerizable compound exists in a polymerized form.

[0257] The LC display is preferably a PS-VA, PS-IPS, PS-FFS, or SA-VA display.

[0258] For the production of PSA or polymer-stabilized SA displays, polymerizable compounds contained in the LC medium are preferably polymerized by in-situ polymerization in the LC medium between the substrates of the LC display while applying a voltage to the electrodes.

[0259] The display structure according to the present invention corresponds to the usual geometric shape of a PSA display, as described in the prior art cited at the beginning. A geometry without protrusions is preferred, and in particular, a geometry in which the electrodes on the color filter side are unstructured and only the electrodes on the TFT side have slots is preferred. A particularly suitable and preferred electrode structure for a PS-VA display is described, for example, in U.S. Patent Application Publication No. 2006 / 0066793.

[0260] A preferred PSA-type LC display of the present invention is: A first substrate including a pixel electrode that defines a pixel region, the pixel electrode being connected to a switch element placed in each pixel region, and optionally including a microslit pattern, and a first orientation layer optionally placed on the pixel electrode, A second substrate comprising a common electrode layer which may be arranged over the entire portion of the second substrate facing the first substrate, and optionally a second orientation layer, • An LC layer disposed between a first substrate and a second substrate, comprising an LC medium as described above and below, wherein the polymerizable compound may be present in a polymerized form. Includes.

[0261] The first and / or second orientation layers control the orientation direction of the LC molecules in the LC layer. For example, in a PS-VA display, the orientation layer is selected to impart homeotropic (or perpendicular) orientation (i.e., perpendicular to the surface) or tilt orientation to the LC molecules. Such an orientation layer may, for example, contain polyimide, and may be rubbed or prepared by a photo-alignment method.

[0262] An LC layer containing an LC medium can be deposited between display substrates using a method conventionally employed by display manufacturers, such as the so-called one-drop-filling (ODF) method. Next, the polymerizable components of the LC medium are polymerized, for example, by UV photopolymerization. Polymerization can be carried out in one step or in two or more steps.

[0263] A PSA display may include further elements such as a color filter, a black matrix, a passivation layer, an optical delay layer, and transistor elements for addressing individual pixels, all of which are well known to those skilled in the art and can be employed without inventive skill.

[0264] The electrode structure can be designed by those skilled in the art according to the type of display. For example, in the case of PS-VA displays, multi-domain orientation of LC molecules can be induced by providing electrodes having slits and / or bumps or protrusions to create two or four or more different tilt orientation directions.

[0265] During polymerization, polymerizable compounds form copolymers, which cause LC molecules in the LC medium to have a certain tilt angle. While we do not wish to be bound by any particular theory, it is thought that at least a portion of the crosslinked polymers formed by polymerizable compounds undergo phase separation or precipitation from the LC medium, forming a polymer layer on the substrate or electrode, or on an orientation layer provided thereon. Microscopic measurements (SEM and AFM, etc.) have confirmed that at least a portion of the formed polymer accumulates at the LC / substrate interface.

[0266] Polymerization can be carried out in a single step. In addition, in the first step, polymerization can be carried out while applying an arbitrary voltage to create a tilt angle, and then in the second polymerization step, without applying a voltage, the compounds that did not react in the first step can be polymerized or crosslinked ("final curing").

[0267] A preferred polymerization method is, for example, thermal polymerization or photopolymerization, preferably photopolymerization, particularly UV-induced photopolymerization, which can be achieved by exposing the polymerizable compound to UV radiation.

[0268] A preferred method for preparing a PSA display includes one or more of the following features:

[0269] The polymerizable medium is exposed to UV light within the display, and the process includes a two-step procedure in which a tilt angle is generated in a first UV exposure step ("UV1 step") by applying a voltage, and complete polymerization is carried out in a second UV exposure step ("UV2 step") without applying a voltage.

[0270] The polymerizable medium is exposed to UV light in a display generated by a UV-LED lamp, preferably in at least two UV steps, and more preferably in both UV1 and UV2 steps.

[0271] The polymerizable medium is exposed to UV light in the display generated by a UV lamp having an emission spectrum shifted to longer wavelengths, preferably 340 nm or longer, more preferably 350-370 nm, and very preferably 355-368 nm, in order to avoid short UV light exposure in the PS-VA process.

[0272] Using both lower intensity and longer wavelength UV shifts, organic layers are protected from damage that can occur with UV light.

[0273] A preferred embodiment of the present invention is for preparing a PSA display as described above and below, and is a method comprising one or more of the following features: The polymerizable LC medium is irradiated with UV light in two steps, including a first UV exposure step ("UV-1 step") in which a voltage is applied to generate a tilt angle, and a second UV exposure step ("UV-2 step") in which no voltage is applied to complete polymerization. • The polymerizable LC medium is preferably exposed to UV2 in the UV2 step, and optionally in the UV1 step, at a wavelength range of 300-380 nm at 0.5 mW / cm². 2 ~10mW / cm 2 Irradiated with UV light generated by a UV lamp having the following intensity, The polymerizable LC medium is irradiated with UV light having a wavelength of 340 nm or more, preferably 420 nm or less, preferably more than 350 nm, preferably in the range of 340 to 400 nm, more preferably in the range of 350 to 390 nm, very preferably in the range of 360 to 380 nm, and most preferably in the range of 360 to 368 nm. • While applying voltage to the electrodes of the display, the polymerizable LC medium is irradiated with UV light. • Use a UV-LED lamp to irradiate with UV light.

[0274] This preferred method can be implemented, for example, by using a desired UV lamp or by using bandpass filters and / or cutoff filters that substantially transmit UV light having the desired wavelength and substantially block light having the undesired wavelength. For example, if irradiation with UV light with a wavelength λ of 300-400 nm is desired, UV irradiation can be performed using a widebandpass filter that substantially transmits wavelengths λ greater than 300 nm and less than 400 nm. If irradiation with UV light with a wavelength λ greater than 340 nm is desired, UV irradiation can be performed using a cutoff filter that substantially transmits wavelengths λ greater than 340 nm.

[0275] Preferably, UV irradiation is performed using a UV-LED lamp.

[0276] Using a UV-LED lamp with only one narrow emission peak in the PSA process offers several advantages, such as more effective light energy transfer to the polymerizable compound in the LC medium, depending on the selection of a suitable polymerizable compound that absorbs the LED lamp's emission wavelength. This allows for a reduction in UV intensity and / or UV irradiation time, thus enabling shorter cycle times and savings in energy and manufacturing costs. Another advantage is that the narrow emission spectrum of the lamp makes it easier to select a wavelength suitable for photopolymerization.

[0277] Very preferably, the UV light source is a UV-LED lamp that emits wavelengths in the range of 340 to 400 nm, more preferably in the range of 350 to 390 nm, very preferably in the range of 360 to 380 nm, and most preferably in the range of 360 to 368 nm. A UV-LED lamp that emits UV light with a wavelength of 365 nm is particularly preferred.

[0278] Preferably, the UV-LED lamp emits light having an emission peak with a full width at half maximum (FWHM) of 30 nm or less.

[0279] UV-LED lamps are commercially available, for example, from Dr. Hoenle GmbH, Germany, or Primelite GmbH, Germany, or IST Metz GmbH, Germany, with emission wavelengths such as 365, 385, 395, and 405 nm.

[0280] This preferred process allows for the manufacture of displays by using longer ultraviolet wavelengths, thereby reducing or even avoiding the hazardous and harmful effects of shorter UV light components.

[0281] UV radiation energy is generally between 6 and 100 J, depending on the manufacturing process conditions.

[0282] The LC medium according to the present invention may preferably contain one or more additional components or additives selected from the list including, but not limited to, comonomers, chiral dopants, polymerization initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricants, dispersants, hydrophobic agents, adhesives, flow improvers, defoamers, deaeration agents, diluents, reaction diluents, auxiliary agents, colorants, dyes, pigments, and nanoparticles.

[0283] The LC medium preferably has a nematic LC phase.

[0284] One or more initiators may be added to the LC medium. Suitable conditions for polymerization, as well as suitable types and amounts of initiators, are known to those skilled in the art and described in the literature. For example, commercially available photoinitiators Irgacure 651®, Irgacure 184®, Irgacure 907®, Irgacure 369®, or Darocure 1173® (Ciba Corporation) are suitable for free radical polymerization. When initiators are used, their proportion in the total mixture is preferably 0.001 to 5% by weight, and particularly preferably 0.001 to 1% by weight.

[0285] Furthermore, the polymerizable compounds according to the present invention are also suitable for polymerization without an initiator, and such polymerization offers considerable advantages, such as lower material costs and, in particular, reduced contamination of the LC medium due to the expected residual amount of initiator or its degradation products.

[0286] Therefore, polymerization can be carried out without adding an initiator. Thus, in another preferred embodiment, the LC medium does not contain a polymerization initiator.

[0287] Furthermore, for example, to prevent undesirable spontaneous polymerization of RM during storage or transport, the polymerizable component of the cholesteric liquid crystal medium may also 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 stabilizers are used, the proportion of stabilizers based on RM or the polymerizable component (component A) is preferably 10 to 50,000 ppm, and particularly preferably 50 to 5,000 ppm.

[0288] In a preferred embodiment, the LC medium contains one or more chiral dopants at a concentration of preferably 0.01 to 1% by weight, and very preferably 0.05 to 0.5% by weight. The chiral dopant is preferably selected from the group consisting of compounds from Table B below, and very preferably from the group consisting of R- or S-1011, R- or S-2011, R- or S-3011, R- or S-4011, and R- or S-5011.

[0289] In another preferred embodiment, the LC medium comprises a racemate of one or more chiral dopants, which are preferably selected from the chiral dopants described in the preceding paragraph.

[0290] In another preferred embodiment of the present invention, the LC medium comprises one or more further stabilizers, preferably selected from the group consisting of the following formulas.

[0291] [ka]

[0292] In the formula, each base, independently of the others, has the following meanings, whether identical or different in each instance: R a~d This is a linear or branched alkyl group having 1 to 10, preferably 1 to 6, and very preferably 1 to 4 carbon atoms, most preferably methyl. X S is H, CH3, OH or O ● And, A S This is a linear, branched, or cyclic alkylene having 1 to 20 C atoms, which may be substituted. n is an integer between 1 and 6, preferably 3.

[0293] The preferred stabilizer for formula S3 is selected from formula S3A.

[0294] [ka]

[0295] In the formula, n² is an integer between 1 and 12, provided that the base (CH²) n2 One or more H atoms in may be optionally replaced with methyl, ethyl, propyl, butyl, pentyl, or hexyl atoms.

[0296] A highly preferred stabilizer is selected from the group consisting of the following formulas.

[0297] [ka]

[0298] [ka]

[0299] [ka]

[0300] In a preferred embodiment, the liquid crystal medium includes one or more stabilizers selected from the group consisting of formulas S1-1, S2-1, S3-1, S3-1, and S3-3.

[0301] In a preferred embodiment, the liquid crystal medium includes one or more stabilizers selected from Table C below.

[0302] The proportion of stabilizers such as those in formulas S1 to S3 in the liquid crystal medium is preferably 10 to 500 ppm, and very preferably 20 to 100 ppm.

[0303] In another preferred embodiment, the LC medium according to the present invention contains a self-alignment (SA) additive, preferably at a concentration of 0.1 to 2.5%.

[0304] In a preferred embodiment, the SA-VA display according to the present invention does not include a polyimide orientation layer. In another preferred embodiment, the SA-VA display according to a preferred embodiment includes a polyimide orientation layer.

[0305] Preferred SA additives for use in this preferred embodiment are selected from compounds comprising a mesogenic group and a linear or branched alkyl side chain terminated by one or more polar anchor groups selected from hydroxy, carboxy, amino, or thiol groups.

[0306] A more preferred SA additive comprises one or more polymerizable groups optionally linked to a mesogenic group via spacer groups. These polymerizable SA additives can be polymerized in an LC medium under conditions similar to those applied to RM in the PSA process.

[0307] Suitable SA additives for inducing homeotropic orientation, particularly for use in SA-VA mode displays, are disclosed, for example, in U.S. Patent Application Publication No. 2013 / 0182202, U.S. Patent Application Publication No. 2014 / 0838581, U.S. Patent Application Publication No. 2015 / 0166890, and U.S. Patent Application Publication No. 2015 / 0252265.

[0308] In another preferred embodiment, the LC medium or polymer-stabilized SA-VA display according to the present invention comprises one or more self-orienting additives selected from Table E below.

[0309] In another preferred embodiment, the LC medium according to the present invention preferably contains one or more SA additives selected from Table E at a concentration of 0.1 to 5%, very preferably 0.2 to 3%, and most preferably 0.2 to 1.5%.

[0310] In addition to the polymerizable compounds and additives described above, the LC medium for use in the LC display according to the present invention comprises an LC mixture ("host mixture") containing one or more, preferably two or more, LC compounds selected from non-polymerizable low molecular weight compounds, at least one of which is a compound of formula II. These LC compounds are selected to be stable and / or non-reactive to polymerization reactions under the conditions applicable to the polymerization of polymerizable compounds.

[0311] A particularly preferred embodiment of such an LC medium is shown below.

[0312] Preferably, the LC medium contains one or more compounds of formula II selected from the group consisting of compounds of formulas IIA, IIB, IIC, and IID.

[0313] [ka]

[0314] During the ceremony R 2A and R 2BEach of these groups is an alkyl or alkenyl group having H and up to 15 C atoms independently of each other, and the group is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, provided that one or more CH2 groups in these groups are -O-, -S-, such that the O atoms are not directly bonded to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CO-O-, or -O-CO- can be substituted, L 1 ~L 4 Each of these independently represents F, Cl, CF3, or CHF2. Y represents H, F, Cl, CF3, CHF2, or CH3, preferably H or CH3, and particularly preferably H. Z 2 , Z 2B and Z 2D These each represent a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-, independently of each other. p represents 0, 1 or 2, and q represents either 0 or 1, whether identical or different in each occurrence.

[0315] Preferred compounds of formulas IIA, IIB, IIC, and IID are R 2B represents an alkyl or alkoxy group having 1 to 15 C atoms, very preferably (O)C v H 2v+1 This represents a θ such that (O) is an oxygen atom or a single bond, and v is 1, 2, 3, 4, 5, or 6.

[0316] More preferred compounds of formulas IIA, IIB, IIC, and IID are R 2A or R 2B Preferably [ka] (S in the formula 1 is C 1~5 - Alkylene or C 2~5 -It is an alkenylene, S 2 H, C 1~7 -alkyl or C 2~7 - is an alkenil.) Selected from the group consisting of, very preferably [ka] This represents or contains a cycloalkyl or cycloalkoxy group selected from the group consisting of the following:

[0317] More preferred compounds of formulas IIA, IIB, IIC, and IID are shown below.

[0318] [ka]

[0319] [ka]

[0320] [ka]

[0321] [ka]

[0322] [ka]

[0323] [ka]

[0324] [ka]

[0325] [ka]

[0326] [ka]

[0327] [ka]

[0328] In the formula, parameter a represents 1 or 2, and alkyl and alkyl * Each of the following independently represents 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-.

[0329] Particularly preferred LC media according to the present invention include one or more compounds of the formulas IIA-2, IIA-8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, and IID-4.

[0330] The proportion of the compound of formula IIA and / or IIB in the overall mixture is preferably at least 20% by weight. In another preferred embodiment, the LC medium comprises one or more compounds of formula III.

[0331] [ka]

[0332] During the ceremony R 11 and R 12 Each of these represents an alkyl or alkoxy group having H and 1 to 15 C atoms independently of each other, provided that one or more CH2 groups in these groups are arranged so that the O atoms are not directly bonded to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO- may be substituted for each other independently, and in the group, one or more H atoms may be replaced by halogens. A 3 Each of them appeared independently of the others. a) A 1,4-cyclohexenylene or 1,4-cyclohexylene group, wherein one or two non-adjacent CH2 groups in the group may be replaced by -O- or -S-, b) A 1,4-phenylene group, in which one or two CH groups may be replaced by N, or c) A group 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 This represents, However, groups a), b), and c) may be monosubstituted or polysubstituted with halogen atoms. n represents 0, 1, or 2, preferably 0 or 1. Z 1 Each of these independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, and L11 and L 12 Each of these independently represents F, Cl, CF3 or CHF2, preferably H or F, most preferably F, and W represents either O or S.

[0333] In a preferred embodiment of the present invention, the LC medium comprises one or more compounds of formula III-1 and / or III-2.

[0334] [ka]

[0335] The bases appearing in the formula have the same meaning as those given in formula III above, and this means, R 11 and R 12 Each of these is an alkyl, alkenyl, or alkoxy group having up to 15 C atoms independently of each other, more preferably one or both of which represent an alkoxy group. L 11 and L 12 These preferably represent F.

[0336] In another preferred embodiment, the LC medium comprises one or more compounds of formula III-1 selected from the group of compounds of formula III-1-1 to III-1-10, preferably formula III-1-6.

[0337] [ka]

[0338] [ka]

[0339] In the formula, alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other, and alkenyl and alkenyl *Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other, and alkoxy and alkoxy * Each represents a linear alkoxyl group having 1 to 6 C atoms independently of each other, and L 11 and L 12 Each of these independently represents either F or Cl, preferably both representing F.

[0340] In another preferred embodiment, the LC medium comprises one or more compounds of formula III-2 selected from the group of compounds of formula III-2-1 to III-2-10, preferably formula III-2-6.

[0341] [ka]

[0342] [ka]

[0343] In the formula, alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other, and alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other, and alkoxy and alkoxy * Each represents a linear alkoxyl group having 1 to 6 C atoms independently of each other, and L 11 and L 12 Each of these independently represents either F or Cl, preferably both representing F.

[0344] In another preferred embodiment of the present invention, the LC medium comprises one or more compounds of formula IIIA-1 and / or IIIA-2.

[0345] [ka]

[0346] In the formula, L 11 and L 12 (O) has the same meaning as given in equation III, where (O) represents O or a single bond. R IIIA This refers to an alkyl or alkenyl group having up to 7 C atoms or a Cy-C group. 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, and very preferably 1. Cy represents an alicyclic group having 3, 4, or 5 ring atoms, which may be substituted with an alkyl or alkenyl group or halogen or CN, each having up to 3 C atoms, preferably representing cyclopropyl, cyclobutyl, or cyclopentyl.

[0347] The compounds of formula IIIA-1 and / or IIIA-2 are included in the LC medium as an alternative or additional, preferably additional, to the compounds of formula III.

[0348] The following are highly preferred compounds of formulas IIIA-1 and IIIA-2.

[0349] [ka]

[0350] In the formula, alkoxy is a linear alkoxy group having 1 to 6 carbon atoms.

[0351] In a preferred embodiment of the present invention, the LC medium comprises one or more compounds of formula III-3.

[0352] [ka]

[0353] During the ceremony R 11 , R 12-CH=CH-, -CF2O-, -OCF2-, -CH=CH [ka] -O-, -CO-O-, or -O-CO- may be substituted for each other independently, and one or more H atoms in the group may be replaced by halogens.

[0354] The compound of formula III-3 is preferably selected from the group of compounds of formula III-3-1 to III-3-10.

[0355] [ka]

[0356] [ka]

[0357] In the formula, R 12 represents an alkyl group having 1 to 7 carbon atoms, preferably ethyl, n-propyl, or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl, or cyclopentylmethyl.

[0358] In another preferred embodiment of the present invention, the LC medium comprises one or more compounds of formulas III-4 to III-6, preferably III-5.

[0359] [ka]

[0360] The parameters in the formula have the meaning given above, R 11 R preferably represents a linear alkyl group, 12Preferably, represents an alkoxy, each having 1 to 7 C atoms.

[0361] In another preferred embodiment, the LC medium comprises one or more compounds of formula I, preferably formula III-8, selected from the group of compounds of formula III-7 to III-9.

[0362] [ka]

[0363] The parameters in the formula have the meaning given above, R 11 R preferably represents a linear alkyl group, 12 Preferably, represents an alkoxy, each having 1 to 7 C atoms.

[0364] In preferred embodiments, the medium comprises one or more compounds of formula IV.

[0365] [ka]

[0366] During the ceremony, R 41 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably an n-alkyl group, and particularly preferably having 2, 3, 4 or 5 carbon atoms. R 42 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkoxy group having 1 to 6 carbon atoms (both preferably having 2 to 5 carbon atoms), an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably having 2, 3, or 4 carbon atoms, more preferably a vinyl group or a 1-propenyl group, particularly a vinyl group.

[0367] The compound of formula IV is preferably selected from the group of compounds of formula IV-1 to IV-4.

[0368] [ka]

[0369] During the ceremony, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. Alkenyl represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms. 'alkenyl' represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms. The term "alkoxy" represents an alkoxy having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0370] Preferably, the LC medium contains one or more compounds selected from the compounds of formulas IV-1-1 to IV-1-4.

[0371] [ka]

[0372] More preferably, the LC medium according to the present invention comprises one or more compounds of formula IV-2-1 and / or IV-2-2.

[0373] [ka]

[0374] More preferably, the LC medium according to the present invention comprises a compound of formula IV-3 selected from compounds of formula IV-3-1 to IV-3-4.

[0375] [ka]

[0376] More preferably, the LC medium according to the present invention comprises a compound of formula IV-4, selected particularly from compounds of formula IV-4-1 and IV-4-2.

[0377] [ka]

[0378] The LC medium preferably includes one or more compounds of formula IVa.

[0379] [ka]

[0380] During the ceremony, R 41 and R 42 Each represents a linear alkyl, alkoxy, alkenyl, alkoxyalkyl, or alkoxy group having up to 12 C atoms independently of each other, and [ka] Z 4 These represent single bonds, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, and -CF=CF-.

[0381] Preferred compounds of formula IVa are shown below.

[0382] [ka]

[0383] In the formula, alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other.

[0384] The LC medium according to the present invention preferably comprises at least one compound of formula IVa-1 and / or formula IVa-2.

[0385] The proportion of the compound of formula IVa in the whole mixture is preferably at least 5% by weight.

[0386] Preferably, the LC medium contains one or more compounds of formulas IVb-1 to IVb-3.

[0387] [ka]

[0388] During the ceremony, Alkyl and alkyl * Each represents a linear alkyl group having 1 to 6 C atoms independently of each other, and alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other.

[0389] The proportion of biphenyls of formulas IV-1 to IV-3 in the overall mixture is preferably at least 3% by weight, and more preferably 5% by weight or more.

[0390] Of the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0391] These are particularly preferred biphenyls.

[0392] [ka]

[0393] In the formula, alkyl * represents an alkyl group having 1 to 6 carbon atoms, preferably representing n-propyl.

[0394] The LC medium according to the present invention is particularly preferably composed of one or more compounds of formula IVb-1-1 and / or IVb-2-3.

[0395] In a particularly preferred embodiment, the LC medium comprises one or more compounds of formula V.

[0396] [ka]

[0397] During the ceremony, R 51 and R 52 R is independent of each other 41 and R 42 It has one of the meanings given to it and preferably represents an alkyl having 1 to 7 carbon atoms, preferably an n-alkyl, particularly preferably an n-alkyl having 1 to 5 carbon atoms, an alkoxy having 1 to 7 carbon atoms, preferably an n-alkoxy, particularly preferably an n-alkoxy having 2 to 5 carbon atoms, an alkoxyalkyl having 2 to 7 carbon atoms, preferably an alkoxyalkyl having 2 to 4 carbon atoms, an alkenyl or alkenyloxy, preferably an alkenyloxy. [ka] During the ceremony, [ka] Z 51 , Z 52 Each of these independently represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond, preferably -CH2-CH2-, -CH2-O-, or a single bond, particularly preferably a single bond. n is either 1 or 2.

[0398] The compound of formula V is preferably selected from the compounds of formulas V1 to V16.

[0399] [ka]

[0400] [ka]

[0401] In the formula, R 1 and R 2 R is above 2A It has the meaning shown in R. 1 and R 2 Preferably, each represents a linear alkyl or alkenyl molecule independently of the others.

[0402] A preferred LC medium comprises one or more compounds of formulas V-1, V-3, V-4, V-6, V-7, V-10, V-11, V-12, V-14, V-15 and / or V-16.

[0403] The LC medium according to the present invention is very preferably composed of compounds of formula V-10, V-12, V-16 and / or IV-1 in an amount particularly of 5 to 30%.

[0404] Preferred compounds for formula V-10 are shown below.

[0405] [ka]

[0406] The LC medium according to the present invention particularly preferably contains a tricyclic compound of formula V-10a and / or formula V-10b in combination with one or more bicyclohexyl compounds of formula IV-1. The total proportion of the compounds of formula V-10a and / or V-10b in combination with one or more compounds selected from the bicyclohexyl compounds of formula IV-1 is 5 to 40%, and very particularly preferably 15 to 35%.

[0407] A particularly preferred LC medium is one comprising compounds V-10a and IV-1-1.

[0408] [ka]

[0409] Compounds V-10a and IV-1-1 are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22%, relative to the whole mixture.

[0410] A particularly preferred LC medium is one comprising compounds V-10b and IV-1-1.

[0411] [ka]

[0412] Compounds V-10b and IV-1-1 are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22%, relative to the whole mixture.

[0413] The most particularly preferred LC media include the following three compounds.

[0414] [ka]

[0415] Compounds V-10a, V-10b, and IV-1-1 are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22%, relative to the whole mixture.

[0416] A preferred LC medium comprises at least one compound selected from the group of compounds listed below.

[0417] [ka]

[0418] In the formula, R 41 and R 42 Furthermore, R 51 and R 52 This has the meaning shown above. Preferably, in compounds V-6, V-7 and IV-1, R 41 and R51 Each represents an alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms, and R 42 and R 52 This represents an alkenyl having 2 to 6 carbon atoms.

[0419] A preferred LC medium includes at least one compound of formulas V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a, and IV-3b.

[0420] [ka]

[0421] In the formula, alkyl represents an alkyl group having 1 to 6 carbon atoms, and alkenyl represents an alkenyl group having 2 to 6 carbon atoms.

[0422] The compounds of formulas V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a, and IV-3b are preferably present in the mixture according to the present invention in an amount of 1 to 40% by weight, preferably 5 to 35% by weight, and very preferably 10 to 30% by weight.

[0423] In a preferred embodiment of the present invention, the LC medium further comprises one or more compounds of formulas VI-1 to VI-9.

[0424] [ka]

[0425] [ka]

[0426] During the ceremony, R 7 These are R, which is independent of each other in equation IIA. 2A It has one of the meanings shown, w and x each represent 1 through 6 independently of each other.

[0427] An LC medium containing at least one compound of formula V-9 is particularly preferred.

[0428] In a preferred embodiment of the present invention, the LC medium further comprises one or more compounds of formulas VII-1 to VII-25.

[0429] [ka]

[0430] [ka]

[0431] [ka]

[0432] [ka]

[0433] During the ceremony, R represents a linear alkyl or alkoxy group having 1 to 6 C atoms, (O) represents -O- or a single bond, X represents F, Cl, OCF3 or OCHF2, L x represents H or F, m is 0, 1, 2, 3, 4, 5, or 6, and n is 1, 2, 3, or 4.

[0434] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0435] X preferably represents F or OCH3, and very preferably F.

[0436] The LC medium according to the present invention preferably contains 2 to 30% by weight, particularly 5 to 20% by weight, of terphenyls of formulas VII-1 to VII-25.

[0437] Compounds of formulas VII-1, VII-2, VII-4, VII-20, VII-21, and VII-22, where X is F, are particularly preferred. In these compounds, R preferably represents an alkyl group having 1 to 5 carbon atoms, and more preferably an alkoxy group. In compound VII-20, R preferably represents an alkyl or alkenyl group, particularly an alkyl group. In compound VII-21, R preferably represents an alkyl group. In compounds VII-22 to VII-25, X preferably represents F.

[0438] When the Δn value of the mixture is 0.1 or greater, terphenyls are preferably used in the LC medium according to the present invention. The preferred LC medium contains 2 to 20% by weight of one or more terphenyl compounds selected from the group of compounds VII-1 to VII-25.

[0439] Further preferred embodiments are listed below.

[0440] a) An LC medium containing at least one compound of formulas Z-1 to Z-7.

[0441] [ka]

[0442] In the formula, R, (O), and alkyl have the meanings shown in Formula III above.

[0443] b) A preferred LC medium according to the present invention comprises, for example, one or more substances containing tetrahydronaphthyl or naphthyl units, such as compounds of formula N-1 to N-5.

[0444] [ka]

[0445] R in the formula 1N and R 2N Each of them is R independently of the others.2A It has the meaning shown, and preferably represents a linear alkyl, linear alkoxy, or linear alkenyl. Z 1 and Z 2 These each independently represent -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.

[0446] c) A preferred LC medium comprises one or more compounds selected from the group consisting of difluorodibenzochromane compounds of formula BC, chromanes of formula CR, and fluorinated phenanthrenes of formulas PH-1 and PH-2.

[0447] [ka]

[0448] During the ceremony, R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 Each of them is R independently of the others. 2A It has the meaning of c being 0, 1, or 2. 1 and R 2 Preferably, each element represents an alkyl or alkoxy having 1 to 6 C atoms independently of each other.

[0449] The LC medium according to the present invention preferably contains a compound of formula BC, CR, PH-1, or PH-2 in an amount of 3 to 20% by weight, and more particularly in an amount of 3 to 15% by weight.

[0450] Particularly preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5.

[0451] [ka]

[0452] [ka]

[0453] During the ceremony, Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other. alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other.

[0454] An LC medium containing one, two, or three compounds of formula BC-2, BF-1, and / or BF-2 is very preferably preferred.

[0455] d) A preferred LC medium comprises one or more indane compounds of the formula In.

[0456] [ka]

[0457] During the ceremony, R 11 , R 12 , R 13 Each of these represents a linear alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1 to 6 carbon atoms independently of each other. R 12 and R 13 This is represented by adding a halogen, preferably F, [ka] This represents, i represents 0, 1, or 2.

[0458] Preferred compounds of formula In are the compounds of formula In-1 to In-16 shown below.

[0459] [ka]

[0460] [ka]

[0461] [ka]

[0462] Compounds of formulas In-1, In-2, In-3, and In-4 are particularly preferred.

[0463] Compounds of formula In and sub-formulas In-1 to In-16 are preferably used in the LC medium according to the present invention at a concentration of 5% by weight or more, particularly 5 to 30% by weight, and very preferably 5 to 25% by weight.

[0464] e) A preferred LC medium is to include one or more compounds of formulas L-1 to L-5.

[0465] [ka]

[0466] [ka]

[0467] During the ceremony, R and R 1 Each of these independently of the other in equation IIA is R 2A The meaning shown is as follows: alkyl represents an alkyl group having 1 to 6 carbon atoms. The parameter s represents 1 or 2.

[0468] The compounds of formulas L1 to L5 are preferably used at a concentration of 5 to 50% by weight, particularly 5 to 40% by weight, and very preferably 10 to 40% by weight.

[0469] f) A preferred LC medium is one or more compounds of formula IIA-Y in addition.

[0470] [ka]

[0471] R in the formula 11 and R 12 In equation IIA above, R 2A It has one of the meanings that can be given to L 1 and L 2 These represent F or Cl, either identical or different.

[0472] The preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0473] [ka]

[0474] [ka]

[0475] Alkyl and Alkyl * Each of these independently represents a linear alkyl group having 1 to 6 carbon atoms, Alkoxy represents a linear alkoxy group having 1 to 6 carbon atoms, and Alkenyl and Alkenyl * Each represents a linear alkenyl group having 2 to 6 C atoms independently of each other, and O represents an oxygen atom or a single bond. *Preferably, 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-.

[0476] Particularly preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0477] [ka]

[0478] In the formula, Alkoxy and Alkoxy * The terms have the meanings defined above, and preferably represent methoxy, ethoxy, n-propyloxy, n-butyloxy, or n-pentyloxy.

[0479] g) An LC medium containing one or more quarter-phenyl compounds selected from the following formulas.

[0480] [ka]

[0481] During the ceremony, R Q This is an alkyl, alkoxy, oxaalkyl or alkoxyalkyl group having 1 to 9 carbon atoms, or an alkenyl or alkenyloxy group having 2 to 9 carbon atoms, wherein all of the group may be fluorinated. X Q This is an alkyl or alkoxy halogen having F, Cl, 1 to 6 C atoms, or an alkenyl or alkenyloxy halogen having 2 to 6 C atoms, L Q1 ~L Q6 Each is either H or F independently of the other, except L Q1 ~L Q6 At least one of them is F.

[0482] The preferred compound of formula Q is R Q The C atom is a linear alkyl group having 2 to 6 C atoms, and is very preferably ethyl, n-propyl, or n-butyl.

[0483] The preferred compound of formula Q is L Q3 and L Q4 This is the one where F is.

[0484] A more preferred compound of formula Q is L Q3 , L Q4 Furthermore, L Q1 and L Q2 One or two of them are F.

[0485] The preferred compound of formula Q is X Q This represents F or OCF3, very preferably F.

[0486] The compound of formula Q is preferably selected from the following sub-formulas.

[0487] [ka]

[0488] In the formula, R Q is having one of the meanings of formula Q or one of its preferred meanings given above and below, and is preferably ethyl, n-propyl, or n-butyl.

[0489] Especially R Q Compounds of formula Q1 in which n-propyl is particularly preferred.

[0490] Preferably, the proportion of the compound of formula Q in the LC host mixture is more than 0 and up to 5% by weight, very preferably 0.05 to 2% by weight, more preferably 0.1 to 1% by weight, and most preferably 0.1 to 0.8% by weight.

[0491] Preferably, the LC medium contains 1 to 5 types, preferably 1 or 2 types of compounds of formula Q.

[0492] Adding a quarter-phenyl compound of formula Q to an LC host mixture can reduce ODF unevenness while maintaining high UV absorption, enabling rapid and complete polymerization, allowing for strong and rapid tilt angle generation, and improving the UV stability of the LC medium.

[0493] In addition, by adding a compound of formula Q having positive dielectric anisotropy to an LC medium having negative dielectric anisotropy, the dielectric constant ε ∥ and ε ⊥ The value of can be controlled more effectively, and in particular, the dielectric constant ε can be controlled while keeping the dielectric anisotropy Δε constant. ∥ This makes it possible to achieve high values, thereby reducing kickback voltage and reducing image fixation.

[0494] The LC medium according to the present invention is preferably,

[0495] One or more compounds of formula IA and one or more compounds of formula IB or IC, preferably selected from the sub-formulas as defined above, in a total concentration preferably in the range of 0.01% to 2.0%, more preferably 0.1% to 1.0%, and most preferably 0.2% to 0.8%;

[0496] One or more compounds of formula IA, one or more compounds of formula IB, and one or more compounds of formula IC are preferably selected from the sub-formulas as defined above, in a total concentration preferably in the range of 0.01% to 2.0%, more preferably 0.1% to 1.0%, and most preferably 0.2% to 0.8%;

[0497] and / or One or more compounds of formula IIA, preferably in a total concentration of 5% to 30%, more preferably 7% to 25%, and particularly preferably 10% to 20%;

[0498] and / or One or more compounds of formulas IIA and IIB, preferably in a total concentration ranging from 30% to 45%;

[0499] and / or One or more compounds of formula IV, preferably in a total concentration of 35% to 70%, more preferably 40% to 65%, and particularly preferably 45% to 60%;

[0500] and / or One or more compounds of formula IV-3, preferably in a total concentration within the range of 35% to 60%, more preferably 40% to 55%, and particularly preferably 45% to 50%;

[0501] and / or • One or more compounds of formula III-2, preferably formula III-2-6, in a total concentration preferably in the range of 2% to 25%, more preferably 5% to 15%, and particularly preferably 5% to 12%. Includes.

[0502] In particular, the media

[0503] One or more compounds CY-n-Om, particularly CY-3-O4, CY-5-O4, and / or CY-3-O2, in a total concentration preferably in the range of 5% to 30%, preferably 10% to 20%;

[0504] and / or One or more compounds PY-n-Om, particularly PY-3-O2 and / or PY-1-O2, in a total concentration preferably in the range of 5% to 30%, preferably 5% to 20%;

[0505] and / or CPY-n-Om, particularly CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably more than 5% and especially 7% to 20% of the whole mixture;

[0506] and / or One or more compounds CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, in a concentration of preferably more than 3%, and particularly 5-15%, based on the whole mixture;

[0507] and / or One or more compounds CPY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2, in a concentration of more than 3%, particularly 5-15%, based on the whole mixture;

[0508] and / or CLY-n-Om, preferably CLY-2-O4, CLY-3-O2 and / or CLY-3-O3, at a concentration of preferably more than 5%, particularly 10-30%, and very preferably 15-20%, based on the whole mixture;

[0509] and / or CPY-n-Om and CY-n-Om are added to the mixture, preferably at a concentration of 10-80% of the total mixture;

[0510] and / or CPY-n-Om and PY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2 and PY-3-O2 or PY-1-O2, are used in the mixture at a concentration of preferably 5-20%, more preferably 10-15%, based on the whole mixture.

[0511] and / or • Add CC-3-V to the mixture, preferably at a concentration of 5-50% of the total mixture.

[0512] and / or • The compound of formula CC-3-V1 is used in a total concentration ranging from 5% to 40%, more preferably 15% to 35%, and particularly preferably 20% to 30%.

[0513] and / or One or more compounds of the formula B-nO-Om and / or B(S)-nO-Om, particularly compounds B(S)-2O-O4 and / or B(S)-2O-O5, preferably in a concentration of 2 to 12%,

[0514] and / or • 0.1% to 3% of the compound PPGU-3-F Includes.

[0515] The present invention further relates to an electro-optical display having an active matrix address, wherein the dielectric is the LC medium described in claim 1, wherein the display is a VA, SA-VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-positive-VA, PS-TN, polymer-retaining SA-VA, or polymer-stabilized SA-FFS display.

[0516] The LC medium according to the present invention is advantageous in that it preferably has a nematic phase at temperatures of -20°C or lower to 70°C or higher, particularly preferably -30°C or lower to 80°C or higher, and very particularly preferably -40°C or lower to 90°C or higher.

[0517] The medium according to the present invention has a transparency temperature of 70°C or higher, preferably 74°C or higher.

[0518] In this specification, the expression "having a nematic phase" means, on the one hand, that neither the smectic phase nor crystallization is observed at the corresponding low temperature, and on the other hand, that heating from the nematic phase does not yet result in transparency. Low-temperature studies are performed using a fluid viscometer at the corresponding temperature and confirmed by storage for at least 100 hours in a test cell with a layer thickness corresponding to electro-optical applications. If the storage stability of the corresponding test cell at -20°C is 1000 hours or more, the medium is considered stable at this temperature. At temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the transparency point is measured in a capillary by conventional methods.

[0519] The liquid crystal mixture preferably has a nematic phase range of at least 60K and a maximum of 30mm at 20°C. 2 ·s -1 The fluid viscosity ν 20 It holds.

[0520] The mixture is nematic at temperatures below -20°C, preferably below -30°C, and very preferably below -40°C.

[0521] The birefringence value Δn of a liquid crystal mixture is generally between 0.07 and 0.16, preferably between 0.08 and 0.15, and very preferably between 0.09 and 0.14.

[0522] In a preferred embodiment of the present invention, the medium has a birefringence in the range of 0.090 to 0.110, preferably 0.095 to 0.105, and particularly 0.100 to 0.105.

[0523] In another preferred embodiment, the medium according to the present invention has a birefringence of 0.120 or higher, preferably in the range of 0.125 to 0.145, and more preferably in the range of 0.130 to 0.140.

[0524] The liquid crystal mixture according to the present invention has a dielectric anisotropy Δε of -1.5 to -8.0, preferably -2.0 to -4.0, and particularly -2.5 to -3.5.

[0525] The rotational viscosity γ1 at 20°C is preferably 120 mPa·s or less, and particularly 100 mPa·s or less.

[0526] In a preferred embodiment, the rotational viscosity γ1 at 20°C is 100 mPa·s or less, and particularly 95 mPa·s or less.

[0527] The liquid crystal medium according to the present invention has a relatively low threshold voltage (V0) value. These are preferably in the range of 1.7V to 3.0V, particularly preferably 2.7V or less, and very particularly preferably 2.5V or less.

[0528] In the present invention, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Fredericks threshold, unless otherwise specified.

[0529] In addition, the liquid crystal medium according to the present invention has a high voltage retention rate in liquid crystal cells.

[0530] Generally, liquid crystal media with a low address voltage or threshold voltage exhibit a lower voltage retention rate than those with a high address voltage or threshold voltage, and vice versa.

[0531] In this invention, the term "dielectrically positive compound" refers to a compound with Δε > 1.5, the term "dielectrically neutral compound" refers to one with -1.5 ≤ Δε ≤ 1.5, and the term "dielectrically negative compound" refers to one with Δε < -1.5. The dielectric anisotropy of the compound is determined herein by dissolving 10% of the compound in an LC host and measuring the capacitance of the resulting mixture in at least one test cell having a layer thickness of 20 μm and homeotropic and homogeneous surface orientation at 1 kHz in each case. The measurement voltage is typically 0.5 V to 1.0 V, but is always lower than the capacitance threshold of each liquid crystal mixture under consideration.

[0532] All temperature values ​​shown in this invention are in °C.

[0533] The LC media according to the present invention are suitable for all VA-TFT (vertical alignment-thin film transistor) applications, such as VAN (vertically aligned nematic), MVA (multidomain VA), (S)-PVA (super patterned VA), ASV (advanced super view or axially symmetric VA), PSA (polymer sustained VA), and PS-VA (polymer stabilized VA). They are also suitable for IPS (in-plane switching) and FFS (fringe field switching) applications with negative Δε.

[0534] The nematic LC medium in the display according to the present invention generally comprises two components A and B, each consisting of one or more individual compounds.

[0535] Component A has significantly negative dielectric anisotropy, giving the nematic phase a dielectric anisotropy of -0.5 or less. It preferably comprises one or more compounds of formula I, as well as compounds of formulas IIA, IIB and / or IIC, and one or more compounds of formula IV-1.

[0536] The proportion of component A is preferably between 45% and 100%, and particularly between 60% and 85%.

[0537] For component A, one (or more) individual compounds having a Δε value of -0.8 or less are preferably selected. This value must be more negative as the proportion of component A in the whole mixture decreases.

[0538] Component B exhibits significant nematogenic properties, and at 20°C, 30 mm 2 ·s -1The following is preferably 25 mm 2 ·s -1 It has the following flow viscosity.

[0539] Numerous suitable materials are known to those skilled in the art from the literature. Compounds of formula O-17 are particularly preferred.

[0540] Particularly preferred individual compounds in component B are 18 mm at 20°C. 2 ·s -1 The following is preferably 12 mm 2 ·s -1 This is an extremely low viscosity nematic liquid crystal having the following fluid viscosity.

[0541] Component B is unidirectional or enantiomerically nematic, does not have a smectic phase, and can prevent the formation of a smectic phase in LC media down to very low temperatures. For example, when various highly nematogenic materials are added to a smectic liquid crystal mixture, the nematogenicity of these materials can be compared through the degree of smectic phase suppression achieved.

[0542] The mixture may also contain component C, which includes a compound having dielectric anisotropy Δε≧1.5. These so-called positive compounds are generally present in the mixture with negative dielectric anisotropy in amounts of 20% by weight or less, based on the whole mixture.

[0543] In addition to compounds of formulas I1, I2, and optionally I3, the medium preferably comprises 4 to 15 types, particularly 5 to 12 types, and especially preferably fewer than 10 types of compounds of formulas IIA, IIB, and / or IIC, and optionally one or more compounds of formula IV-1.

[0544] In addition to compounds of formulas I1, I2 and optionally I3, and compounds of formulas IIA, IIB and / or IIC and optionally IV-1, other components may also be present in amounts up to 45%, preferably up to 35%, and particularly up to 10% of the total mixture.

[0545] Other components are preferably selected from azoxybenzene, benzylideneaniline, biphenyl, terphenyl, phenyl or cyclohexyl benzoate, phenyl or cyclohexylcyclohexane carboxylate, phenylcyclohexane, cyclohexyl biphenyl, cyclohexyl cyclohexane, cyclohexyl naphthalene, 1,4-biscyclohexyl biphenyl or cyclohexylpyrimidine, phenyl or cyclohexyl dioxane, optionally halogenated stilbene, benzylphenyl ether, tran and substituted cinnamic acid esters, particularly known substances.

[0546] The most important compound suitable as a component of this type of liquid crystal phase can be characterized by formula OC.

[0547] [ka]

[0548] In the formula, L and E represent carbocyclic or heterocyclic systems from the group formed by 1,4-disubstituted benzenes and cyclohexane rings, 4,4'-disubstituted biphenyls, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidines and 1,3-dioxane rings, 2,6-disubstituted naphthalenes, di and tetrahydronaphthalenes, quinazolines and tetrahydroquinazolines, respectively. G is -CH=CH-, -N(O)=N-, -CH=CQ-, -CH=N(O)-, -C≡C-, -CH2-CH2-, -CO-O-, -CH2-O-, -CO-S-, -C Represents H2-S-, -CH=N-, -COO-Phe-COO-, -CF2O-, -CF=CF-, -OCF2-, -OCH2-, -(CH2)4-, -(CH2)3O-, Alternatively, CC represents a single bond, Q represents a halogen, preferably chlorine, or -CN, and R 20 and R 21Each of these groups represents an alkyl, alkenyl, alkoxy, alkoxyalkyl, or alkoxycarbonyloxy group having up to 18, preferably up to 8, carbon atoms, or one of these groups represents CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl, or Br.

[0549] In most of these compounds, R 20 and R 21 These groups are distinct from one another, and one of these groups is usually an alkyl or alkoxy group. Other variants of the proposed substituents are also common. Many such substances or mixtures thereof are commercially available. All of these substances can be prepared by methods known from the literature.

[0550] It goes without saying to those skilled in the art that the VA, IPS, or FFS mixture according to the present invention may also include compounds in which, for example, H, N, O, Cl, and F are replaced with corresponding isotopes.

[0551] By combining the compounds of the preferred embodiments described above with the polymerization compounds described above, a consistently high transparency point and high HR value are obtained, along with a low threshold voltage, low rotational viscosity, and excellent low-temperature stability in the LC medium according to the present invention, making it possible to quickly establish particularly low tilt angles (i.e., large tilts) in PSA displays. In particular, the LC medium also exhibits significantly shorter response times in PSA displays compared to LC media of the prior art, especially intermediate grayscale response times.

[0552] The LC medium according to the present invention may also include further additives known to those skilled in the art and described in the literature, such as polymerization initiators, inhibitors, stabilizers, surfactants, or chiral dopants. These may be polymerizable or nonpolymerizable. Polymerizable additives are accordingly assigned to polymerizable components or component A). Nonpolymerizable additives are accordingly assigned to nonpolymerizable components or component B).

[0553] Furthermore, the LC medium may be supplemented with substances that improve the conductivity of the LC medium, such as 0-15% by weight of a polychromatic dye, nanoparticles, conductive salts, preferably complex salts of ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphenylborate, or crown ether (e.g., Haller et al., Mol. Cryst. Liq. Cryst. Vol. 24, pp. 249-258 (1973)), or substances that alter the dielectric anisotropy, viscosity, or orientation of the nematic phase. This type of substance is described, for example, in German Patent Application Publications No. 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430, and 28 53 728.

[0554] The individual components of the preferred embodiments listed above for the LC media according to the present invention are either known, or the methods for preparing them are based on standard methods described in the literature, so the methods for preparing them can be easily derived from the prior art by those skilled in the art. The corresponding compound of formula CY is described, for example, in European Patent Application Publication No. 0 364 538. The corresponding compound of formula ZK is described, for example, in German Patent Application Publication No. 26 36 684 and German Patent Application Publication No. 33 21 373.

[0555] LC media usable according to the present invention are themselves prepared in a conventional manner by mixing, for example, one or more of the above-mentioned compounds with one or more polymerizable compounds as defined above, and, optionally, with further liquid crystal compounds and / or additives. Generally, a desired amount of a component used in smaller quantities is dissolved in the components constituting the main components, preferably by raising the temperature. Alternatively, solutions of the components in an organic solvent, for example, acetone, chloroform, or methanol, can be mixed, and after complete mixing, the solvent can be removed again, for example, by distillation. The present invention further relates to a method for preparing LC media according to the present invention.

[0556] Furthermore, it goes without saying to those skilled in the art that the LC medium according to the present invention may also include compounds in which, for example, H, N, O, Cl, and F are replaced with corresponding isotopes such as deuterium.

[0557] The following examples illustrate the present invention without limiting it. However, they will be helpful to those skilled in the art to understand preferred mixing concepts, along with preferred compounds, their respective concentrations, and combinations thereof. In addition, the examples illustrate the available properties and combinations of properties.

[0558] The preferred mixture components are shown in Table A below.

[0559] In Table A, m and n are each an integer from 1 to 12, preferably 1, 2, 3, 4, 5, or 6, and k is 0, 1, 2, 3, 4, 5, or 6, (O)C m H 2m+1 is C m H 2m+1 or OC m H 2m+1 It means...

[0560] [Table 1]

[0561] [Table 2]

[0562] [Table 3]

[0563] [Table 4]

[0564] [Table 5]

[0565] Table 6

[0566] Table 7

[0567] Table 8

[0568] Table 9

[0569] Table 10

[0570] Table 11

[0571] Table 12

[0572] Table 13

[0573] Table 14

[0574] Table 15

[0575] [Table 16]

[0576] [Table 17]

[0577] [Table 18]

[0578] [Table 19]

[0579] [Table 20]

[0580] In a preferred embodiment of the present invention, the LC medium according to the present invention comprises one or more compounds selected from the group consisting of compounds from Table A.

[0581] Table B shows the chiral dopants that can be added to the LC medium according to the present invention.

[0582] [Table 21]

[0583] [Table 22]

[0584] The LC medium preferably contains 0 to 10% by weight, particularly 0.01 to 5% by weight, and most preferably 0.1 to 3% by weight of a dopant. The LC medium preferably contains one or more dopants selected from the group consisting of compounds from Table B.

[0585] Table C shows possible stabilizers that can be added to the LC medium according to the present invention, where n is an integer from 1 to 12, preferably 1, 2, 3, 4, 5, 6, 7, or 8, and terminal methyl groups are not shown.

[0586] [Table 23]

[0587] [Table 24]

[0588] [Table 25]

[0589] [Table 26]

[0590] [Table 27]

[0591] [Table 28]

[0592] [Table 29]

[0593] The LC medium preferably contains 0 to 10% by weight of a stabilizer, particularly 1 ppm to 5% by weight, and most preferably 1 ppm to 1% by weight. The LC medium preferably contains one or more stabilizers selected from the group consisting of compounds from Table C.

[0594] Table D shows exemplary reactive mesogenic compounds that can be used with the LC medium according to the present invention.

[0595] [Table 30]

[0596] [Table 31]

[0597] [Table 32]

[0598] [Table 33]

[0599] [Table 34]

[0600] [Table 35]

[0601] [Table 36]

[0602] [Table 37]

[0603] [Table 38]

[0604] [Table 39]

[0605] Table 40

[0606] Table 41

[0607] Table 42

[0608] Table 43

[0609] Table 44

[0610] Table 45

[0611] Table 46

[0612] Table 47

[0613] Table 48

[0614] Table 49

[0615] [Table 50]

[0616] In a preferred embodiment, the mixture according to the present invention preferably comprises one or more polymerizable compounds selected from polymerizable compounds of formulas RM-1 to RM-178. Of these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121, RM-122, RM-139, RM-142, RM-143, RM-148 to RM-158, RM-164, RM-165, and RM-166 to RM-178 are particularly preferred.

[0617] Table E shows self-aligning additives for vertical orientation that can be used in LC media for SA-VA and SA-FFS displays according to the present invention, together with polymerizable compounds of formula M.

[0618] [Table 51]

[0619] [Table 52]

[0620] [Table 53]

[0621] [Table 54]

[0622] [Table 55]

[0623] Table 56

[0624] Table 57

[0625] Table 58

[0626] Table 59

[0627] Table 60

[0628] Table 61

[0629] Table 62

[0630] Table 63

[0631] Table 64

[0632] In a preferred embodiment, the LC medium, SA-VA, and SA-FFS display according to the present invention is combined with one or more RMs of formula M and includes one or more SA additives selected from formulas SA-1 to SA-48, preferably from formulas SA-14 to SA-48, and very preferably from formulas SA-20 to SA-34 and SA-44. [Examples]

[0633] The following examples illustrate the present invention without limiting it. However, they will be helpful to those skilled in the art to understand preferred mixing concepts, along with preferred compounds, their respective concentrations, and combinations thereof. In addition, the examples illustrate the available properties and combinations of properties.

[0634] In addition, the following abbreviations and symbols will be used: V0 is the capacitance threshold voltage [V] at 20°C. n e This is an anomalous refractive index at 20°C and 589nm. n0 is the typical refractive index at 20°C and 589nm. Δn is the optical anisotropy at 20°C and 589 nm. ε ⊥ This is the dielectric constant perpendicular to the director at 20°C and 1kHz. ε ∥ This is the dielectric constant parallel to the director at 20°C and 1kHz. Δε is the dielectric anisotropy at 20°C and 1kHz. cl.p., T(N,I) is the point of transparency [°C], γ1 is the rotational viscosity [mPa·s] at 20°C, K1 is the elastic constant [pN] for "splay" deformation at 20°C. K2 is the elastic constant [pN] for "twist" deformation at 20°C. K3 is the elastic constant [pN] for "bend" deformation at 20°C.

[0635] Unless otherwise specified, all concentrations in this application are expressed in weight percent and, with respect to the entire corresponding mixture, include all solid or liquid crystal components but not solvents.

[0636] Unless otherwise specified, all temperature values ​​expressed 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 transparency point T(N,I), are expressed in degrees Celsius (°C). mp represents the melting point, and cl.p. represents the transparency point. Furthermore, C represents the crystalline state, N represents the nematic phase, S represents the smectic phase, and I represents the isotropic phase. The data between these symbols represents the transition temperature.

[0637] All physical properties are determined or have been determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals," November 1997, Merck AG, Germany. Unless otherwise specified, a temperature of 20°C is applied, Δn is determined at 589 nm, and Δε is determined at 1 kHz.

[0638] In this invention, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Frederick's threshold, unless otherwise specified. Furthermore, in the example, although generally typical, 10% relative contrast (V0) is used. 10 The optical threshold for ) may also be indicated.

[0639] Unless otherwise specified, the process of polymerizing polymerizable compounds in a PSA display is carried out at a temperature in which the LC medium exhibits a liquid crystal phase, preferably a nematic phase, and most preferably at room temperature, as described above and below.

[0640] Unless otherwise specified, the method for preparing test cells and measuring their electro-optical and other properties shall be as described below or similarly.

[0641] Displays used for measuring capacitance threshold voltage typically consist of two flat, parallel glass outer plates separated by a 25 μm gap, each having an electrode layer on the inside and an unrubbed polyimide orientation layer on top, which induces homeotropic edge orientation of liquid crystal molecules.

[0642] Unless otherwise specified, PSVA displays or PSVA test cells used for measuring tilt angle typically consist of two flat, parallel glass outer plates separated by approximately 4 μm, each having an electrode layer on the inside and a polyimide orientation layer on top, however, the two polyimide layers are rubbed antiparallel to each other, resulting in homeotropic edge orientation of liquid crystal molecules. PSVA displays or test cells have the same structure, but one or both polyimide layers are omitted.

[0643] Polymerizable compounds typically polymerize within a display or test cell by simultaneously applying a voltage to the display (usually 10V to 30V AC, 1kHz) and irradiating it with UV light of a specified intensity for a predetermined time.

[0644] The intensity is measured using a standard meter (a high-frequency Hoenle UV meter equipped with a UV sensor).

[0645] The tilt angle is typically determined using an Axometrics Mueller matrix polarimeter, "AxoScan." In this specification, a low value (i.e., a large deviation from 90°) corresponds to a large tilt.

[0646] Unless otherwise specified, the term “tilt angle” refers to the angle between the LC director and the substrate, and “LC director” refers to the preferred orientation direction of the optical principal axes of LC molecules in a uniformly oriented layer of LC molecules. In the case of calamitic, i.e., uniaxial and positively birefringent LC molecules, “LC director” corresponds to the molecular long axis of the LC molecule.

[0647] <Example 1> The nematic LC host mixture N1 is formulated as follows:

[0648] [Table 65]

[0649] The polymerizable mixtures P11 to P13 according to the present invention are prepared by adding polymerizable compound MA1 of formula IA1 and polymerizable compound MB1 of formula IBD1 to a nematic LC host mixture N1 at varying concentrations.

[0650] For comparative purposes, polymerizable mixture C11 is prepared by adding only 0.3% of the polymerizable compound MA1 of formula IA6 to the nematic LC host mixture N1.

[0651] [ka]

[0652] Polymerizable mixed compositions are shown in Table 1.1.

[0653] <Table 1.1-Polymerizable mixed composition>

[0654] [Table 66]

[0655] Each polymerizable mixture further contains 150 ppm of stabilizer S1-1 and 10 ppm of Irganox® 1076.

[0656] [ka]

[0657] <Tilt angle generation> An electro-optical VA test cell containing a polymerizable mixture and having an AF glass substrate is exposed to UV light in two steps: a first step (UV1) to generate a tilt angle, and a second step (UV2) to polymerize all residual monomers that did not polymerize in the first step. Voltage (cured in 0.1V steps and at DC15V) is applied in the UV1 step. No voltage is applied in the UV2 step. A C-type fluorescent UV lamp with a 313nm cutoff filter was used as the irradiation source. UV intensity was confirmed with a 313nm UV detector. Other conditions are as follows unless otherwise specified.

[0658] UV1 (Type C lamp): 0.22 mW / cm² 2 Room temperature, 30-200 seconds UV2 (Type C lamp): 0.32 mW / cm² 2 Room temperature, 120 minutes

[0659] After varying the irradiation time and completing one UV treatment step, the tilt angle generated in the test cell was measured using the T RETS-10 system manufactured by Otsuka Corporation. The results are shown in Table 1.2.

[0660] <Table 1.2 - Tilt Angle>

[0661] [Table 67]

[0662] It can be seen that polymerizable mixtures P11 to P13 according to the present invention exhibit significantly faster tilt angle generation than reference mixture C11.

[0663] <Tilt Stability> Tilt stability, i.e., the change in tilt angle after repeated electrical stress, is a criterion for evaluating the risk of image fixation. Low values ​​for tilt angle change indicate good tilt and a low potential risk of image fixation.

[0664] To measure tilt stability, after the above polymerization for tilt angle generation, the test cell is subjected to 40V at 60Hz in the backlight unit. PPElectrical stress is applied for 168 hours using a square wave. After a relaxation period of 5-10 minutes, the tilt angle is measured using the Otsuka T RETS-10 system.

[0665] The change in tilt angle, Δtilt, is determined by equation (1).

[0666]

number

[0667] The lower the value of Δtilt, the higher the tilt stability.

[0668] The results are shown in Table 1.3.

[0669] <Table 1.3 - Tilt Stability>

[0670] [Table 68]

[0671] It can be seen that the polymerizable mixtures P11 to P13 according to the present invention exhibit better tilt stability than the reference mixture C11.

[0672] <Residual RM> The amount of unpolymerized monomers remaining in the mixture after UV photopolymerization (in ppm) was determined. A lower residual monomer content after a given time interval indicates faster polymerization. For this purpose, a polymerizable mixture was packed into a test cell and measured at 0.32 mW / cm². 2 Polymerization was carried out at room temperature by UV exposure at varying time intervals using a C-type fluorescent UV lamp with a specific intensity. UV intensity was confirmed with a 313 nm UV detector. After a certain period of photopolymerization, the test cell was opened, the mixture was dissolved with methyl ethyl ketone, washed out of the test cell, and analyzed by ultra-high-performance liquid chromatography (UPLC).

[0673] The results are shown in Table 1.4.

[0674] <Table 1.4-Residual RM>

[0675] [Table 69] nd: Not detected

[0676] It can be seen that the total residual amount of all monomers after polymerization in the polymerizable mixtures P11 to P13 according to the present invention is smaller than that of the polymerizable reference mixture C11. This is particularly surprising considering that the initial amount of monomers in mixtures P11 to P13 was twice that of the reference mixture C11.

[0677] <Voltage Holding Ratio (VHR)> For VHR measurement, a polymerizable LC medium was packed into a test cell having a fishbone-shaped patterned ITO electrode, and monomers were polymerized under the same conditions as above for tilt angle generation. VHR was measured before and after UV exposure while applying a voltage of 1V / 0.6Hz at 60°C.

[0678] Typically, light stress causes a decrease in the VHR of LC mixtures; therefore, the smaller the decrease in the absolute value of VHR after stress, the better the performance for display applications.

[0679] The results are shown in Table 1.5.

[0680] <Table 1.5-VHR>

[0681] [Table 70]

[0682] In particular, considering that the total amount of monomers in mixtures P11 to P13 is twice that of reference mixture C11, it can be seen that the VHR of polymerizable mixtures P11 to P13 according to the present invention after UV stress is at a similar level to that of polymerizable mixture C11.

[0683] Overall, the results above indicate that polymerizable mixtures containing both polymerizable compounds of formula IA and formula IB show significant improvements, including better tilt stability and lower residual monomer content.

[0684] <Example 2> The nematic LC host mixture N2 is formulated as follows:

[0685] [Table 71]

[0686] The polymerizable mixtures P21 to P23 according to the present invention are prepared by adding the polymerizable compound MA1 of formula IA6 and the polymerizable compound MB1 of formula IB-D-1-1a to the nematic LC host mixture N2 at varying concentrations.

[0687] Polymerizable mixed compositions are shown in Table 2.1.

[0688] <Table 2.1-Polymerizable mixed composition>

[0689] [Table 72]

[0690] Each polymerizable mixture further contains 150 ppm of stabilizer S1-1 and 10 ppm of Irganox® 1076.

[0691] <Tilt Stability> Tilt stability is determined as described in Example 1. The results are shown in Table 2.2.

[0692] <Table 2.2 - Tilt Stability>

[0693] [Table 73]

[0694] The polymerizable mixtures P21 to P23 according to the present invention exhibit good tilt stability.

[0695] <Residual RM> The amount of unpolymerized monomer remaining is measured as described in Example 1. The results are shown in Table 2.3.

[0696] <Table 2.3-Residual RM>

[0697] [Table 74] nd: Not detected

[0698] The polymerizable mixtures P21 to P23 according to the present invention exhibit rapid and complete polymerization with a low residual amount of unreacted monomers under appropriate UV exposure time.

[0699] <Voltage Holding Ratio (VHR)> The VHR of the polymerizable LC medium is measured as described in Example 1. The results are shown in Table 2.4.

[0700] <Table 2.4-VHR>

[0701] [Table 75]

[0702] The VHR of polymerizable mixtures P21-P23 according to the present invention remains high after UV stress, and in particular, there is only a small decrease in VHR in mixtures P21 and P23 with higher monomer content M1.

[0703] Overall, the results above indicate that polymerizable mixtures containing both polymerizable compounds of formulas IA and IB exhibit significant improvements, including better tilt angle generation, higher tilt stability, and lower amounts of residual monomers.

[0704] <Example 3> The polymerizable mixtures P31 and P32 according to the present invention are prepared by adding polymerizable compound MA1 of formula IA6, polymerizable compound MB1 of formula IB-D-1-1a, and polymerizable compound MC1 of formula IC45 to a nematic LC host mixture N2 at varying concentrations.

[0705] [ka]

[0706] Polymerizable mixed compositions are shown in Table 3.1.

[0707] <Table 3.1-Polymerizable mixed composition>

[0708] [Table 76]

[0709] Each polymerizable mixture further contains 150 ppm of stabilizer S1-1 and 10 ppm of Irganox® 1076.

[0710] <Tilt Stability> Tilt stability is determined as described in Example 1. The results are shown in Table 3.2.

[0711] <Table 3.2 - Tilt Stability>

[0712] [Table 77]

[0713] The polymerizable mixtures P31 and P32 according to the present invention exhibit good tilt stability.

[0714] <Residual RM> The amount of unpolymerized monomer remaining is measured as described in Example 1. The results are shown in Table 3.3.

[0715] <Table 3.3-Residual RM>

[0716] [Table 78] nd: Not detected

[0717] The polymerizable mixtures P31 and P32 according to the present invention exhibit rapid and complete polymerization with a low residual amount of unreacted monomers when exposed to UV light for an appropriate duration.

[0718] <Voltage Holding Ratio (VHR)> The VHR of the polymerizable LC medium is measured as described in Example 1. The results are shown in Table 3.4.

[0719] <Table 3.4-VHR>

[0720] [Table 79]

[0721] The VHR of polymerizable mixtures P31 and P32 according to the present invention remains high after UV stress, and in particular, there is only a small decrease in VHR in mixtures P21 and P23 with a higher content of monomer M1.

[0722] Overall, the results above indicate that polymerizable mixtures containing both polymerizable compounds of formulas IA and IB exhibit significant improvements, such as better tilt stability and lower amounts of residual monomers.

[0723] <Example 4> The nematic LC host mixture N3 is formulated as follows:

[0724] [Table 80]

[0725] Polymerizable mixture P4 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm Irganox® 1076 to 99.434% nematic LC host mixture N3.

[0726] <Example 5> Polymerizable mixture P5 is prepared by adding 0.3% compound MA1, 0.2% compound MB1, and 100 ppm stabilizer S1-1 to 99.49% nematic LC host mixture N3.

[0727] <Example 6> The nematic LC host mixture N4 is formulated as follows:

[0728] [Table 81]

[0729] Polymerizable mixture P6 is prepared by adding 0.2% compound MA1 and 0.2% compound MB1 to 99.6% nematic LC host mixture N4.

[0730] <Example 7> Polymerizable mixture P7 is prepared by adding 0.2% compound MA1, 0.25% compound MB1, 0.05% compound MC1, 100 ppm stabilizer S1-1, and 10 ppm Irganox® 1076 to 99.539% nematic LC host mixture N4.

[0731] <Example 8> The nematic LC host mixture N5 is formulated as follows:

[0732] [Table 82]

[0733] Polymerizable mixture P8 is prepared by adding 0.2% of compound MA1 and 0.1% of compound MC1 to nematic LC host mixture N5.

[0734] Polymerizable mixture P8 is prepared by adding 0.2% of compound MA1 and 0.1% of compound MC1 to nematic LC host mixture N5.

[0735] <Example 9> Polymerizable mixture P9 is prepared by adding 0.2% compound MA1, 0.2% compound MB1, and 50 ppm stabilizer S1-1 to nematic LC host mixture N8.

[0736] <Example 10> The nematic LC host mixture N6 is formulated as follows:

[0737] [Table 83]

[0738] Polymerizable mixture P10 is prepared by adding 0.1% of compound MA1 and 0.3% of compound MB1 to nematic LC host mixture N6.

[0739] <Example 11> Polymerizable mixture P11 is prepared by adding 0.1% of compound MA1, 0.3% of compound MB1, 0.1% of compound MC1, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N6.

[0740] <Example 12> Polymerizable mixture P12 is prepared by adding 0.2% of compound MA1 and 0.2% of compound MC1 to nematic LC host mixture N1.

[0741] <Example 13> Polymerizable mixture P13 is prepared by adding 0.2% compound MA1, 0.2% compound MB1, 0.1% compound MC1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N3.

[0742] <Example 14> Polymerizable mixture P14 is prepared by adding 0.1% of compound MA2 and 0.3% of compound MB1 of formula IA1 to nematic LC host mixture N1.

[0743] [ka]

[0744] <Example 15> Polymerizable mixture P15 is prepared by adding 0.1% of compound MA2, 0.3% of compound MB1, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N2.

[0745] <Example 16> Polymerizable mixture P16 is prepared by adding 0.2% compound MA2, 0.1% compound MC1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N1.

[0746] <Example 17> Polymerizable mixture P17 is prepared by adding 0.2% compound MA2, 0.1% compound MB1, 0.05% compound MC1, and 100 ppm stabilizer S1-1 to nematic LC host mixture N3.

[0747] <Example 18> Polymerizable mixture P18 is prepared by adding 0.1% of compound MA1, 0.3% of compound IBD4, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N1.

[0748] [ka]

[0749] <Example 19> Polymerizable mixture P19 is prepared by adding 0.1% of compound MA2, 0.3% of compound MB2, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N2.

[0750] <Example 20> Polymerizable mixture P20 is prepared by adding 0.2% compound MA1, 0.3% compound MB2, 0.2% compound MC1, and 100 ppm stabilizer S1-1 to nematic LC host mixture N3.

[0751] <Example 21> Polymerizable mixture P21 is prepared by adding 0.1% of compound MA1, 0.3% of compound MB3 of formula IBT1, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N1.

[0752] [ka]

[0753] <Example 22> Polymerizable mixture P22 is prepared by adding 0.2% compound MA1, 0.1% compound MC1, and 100 ppm stabilizer S1-1 to nematic LC host mixture N3.

[0754] <Example 23> Polymerizable mixture P23 is prepared by adding 0.1% of compound MA2, 0.3% of compound MB3, and 100 ppm of stabilizer S1-1 to the nematic LC host mixture N2.

[0755] <Example 24> Polymerizable mixture P24 is prepared by adding 0.1% of compound MA1, 0.3% of compound MB4 of formula IBT22, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N1.

[0756] [ka]

[0757] <Example 25> Polymerizable mixture P25 is prepared by adding 0.2% compound MA2, 0.2% compound MB4, and 100 ppm stabilizer S1-1 to nematic LC host mixture N1.

[0758] <Example 26> Polymerizable mixture P26 is prepared by adding 0.2% compound MA1, 0.3% compound MB4, 0.05% compound MC1, and 100 ppm stabilizer S1-1 to nematic LC host mixture N3.

[0759] <Example 27> Polymerizable mixture P27 is prepared by adding 0.1% of compound MA1, 0.3% of compound MB5 of formula IBT35, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N1.

[0760] [ka]

[0761] <Example 28> Polymerizable mixture P28 is prepared by adding 0.2% of compound MA1, 0.2% of compound MB5, 0.05% of compound MC1, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N3.

[0762] <Example 29> Polymerizable mixture P29 is prepared by adding 0.1% of compound MA2, 0.3% of compound MB5, and 100 ppm of stabilizer S1-1 to the nematic LC host mixture N2.

[0763] <Example 30> The nematic LC host mixture N7 is formulated as follows:

[0764] [Table 84]

[0765] Polymerizable mixture P30 is prepared by adding 0.35% compound MA1, 0.15% compound MB1, and 50 ppm stabilizer S1-1 to nematic LC host mixture N6.

[0766] <Example 31> The nematic LC host mixture N8 is formulated as follows:

[0767] [Table 85]

[0768] Polymerizable mixture P31 is prepared by adding 0.2% compound MA1, 0.2% compound MB1, and 50 ppm stabilizer S2-1 to nematic LC host mixture N8.

[0769] [ka]

[0770] <Example 32> The nematic LC host mixture N9 is formulated as follows:

[0771] [Table 86]

[0772] Polymerizable mixture P32 is prepared by adding 0.3% compound MA1, 0.2% compound MB1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N9.

[0773] <Example 33> The nematic LC host mixture N10 is formulated as follows:

[0774] [Table 87]

[0775] Polymerizable mixture P33 is prepared by adding 0.3% compound MA1, 0.2% compound MB1, and 0.6% SA additive SA23 to nematic LC host mixture N10.

[0776] [ka]

[0777] <Example 34> The nematic LC host mixture N11 is formulated as follows:

[0778] [Table 88]

[0779] Polymerizable mixture P34 is prepared by adding 0.1% of compound MA2, 0.2% of compound MB1, 0.05% of compound MC1, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N11.

[0780] <Example 35> The nematic LC host mixture N12 is formulated as follows:

[0781] [Table 89]

[0782] Polymerizable mixture P35 is prepared by adding 0.2% of compound MA1, 0.2% of compound MB1, and 150 ppm of stabilizer S2-1 to the nematic LC host mixture N12.

[0783] <Example 36> The nematic LC host mixture N13 is formulated as follows:

[0784] [Table 90]

[0785] Polymerizable mixture P36 is prepared by adding 0.1% of compound MA1, 0.3% of compound MB1, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N13.

[0786] <Example 37> The nematic LC host mixture N14 is formulated as follows:

[0787] [Table 91]

[0788] Polymerizable mixture P37 is prepared by adding 0.3% compound MA1, 0.1% compound MB1, and 50 ppm stabilizer S1-1 to nematic LC host mixture N14.

[0789] <Example 38> The nematic LC host mixture N15 is formulated as follows:

[0790] [Table 92]

[0791] Polymerizable mixture P38 is prepared by adding 0.4% compound MA1, 0.1% compound MB1, and 50 ppm stabilizer S2-1 to nematic LC host mixture N15.

[0792] <Example 39> The nematic LC host mixture N16 is formulated as follows:

[0793] [Table 93]

[0794] Polymerizable mixture P39 is prepared by adding 0.3% compound MA2, 0.2% compound MB1, and 150 ppm stabilizer S3-1 to nematic LC host mixture N16.

[0795] [ka]

[0796] <Example 40> The nematic LC host mixture N17 is formulated as follows:

[0797] [Table 94]

[0798] Polymerizable mixture P40 is prepared by adding 0.25% of compound MA1, 0.1% of compound MB1, and 150 ppm of stabilizer S1-1 to nematic LC host mixture N17.

[0799] <Example 41> The nematic LC host mixture N18 is formulated as follows:

[0800] [Table 95]

[0801] Polymerizable mixture P41 is prepared by adding 0.15% of compound MA2, 0.2% of compound MB3, and 100 ppm of stabilizer S3-2 to nematic LC host mixture N18.

[0802] [ka]

[0803] <Example 42> The nematic LC host mixture N19 is formulated as follows:

[0804] [Table 96]

[0805] Polymerizable mixture P42 is prepared by adding 0.3% compound MA1, 0.2% compound MB3, and 100 ppm stabilizer S1-1 to nematic LC host mixture N19.

[0806] <Example 43> The nematic LC host mixture N20 is formulated as follows:

[0807] [Table 97]

[0808] Polymerizable mixture P43 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, and 100 ppm stabilizer S1-1 to nematic LC host mixture N20.

[0809] <Example 44> The nematic LC host mixture N21 is formulated as follows:

[0810] [Table 98]

[0811] Polymerizable mixture P44 is prepared by adding 0.15% of compound MA1, 0.2% of compound MB1, 0.05% of compound MC1, and 150 ppm of stabilizer S1-1 to the nematic LC host mixture N21.

[0812] [ka]

[0813] <Example 45> The nematic LC host mixture N22 is formulated as follows:

[0814] [Table 99]

[0815] Polymerizable mixture P45 is prepared by adding 0.2% compound 1, 0.25% compound MB1, 0.05% compound MC1, and 50 ppm stabilizer S1-1 to the nematic LC host mixture N22.

[0816] <Example 46> The nematic LC host mixture N23 is formulated as follows:

[0817] [Table 100]

[0818] Polymerizable mixture P46 is prepared by adding 0.3% compound MA1, 0.3% compound MB1, and 0.6% SA additive SA32 to the nematic LC host mixture N23.

[0819] [ka]

[0820] <Example 47> The nematic LC host mixture N24 is formulated as follows:

[0821] [Table 101]

[0822] Polymerizable mixture P47 is prepared by adding 0.25% of compound MA1, 0.15% of compound MB1, and 150 ppm of stabilizer S1-1 to the nematic LC host mixture N24.

[0823] <Example 48> The nematic LC host mixture N25 is formulated as follows:

[0824] [Table 102]

[0825] Polymerizable mixture P48 is prepared by adding 0.1% of compound MA1, 0.3% of compound MB1, and 100 ppm of stabilizer S2-1 to nematic LC host mixture N25.

[0826] <Example 49> The nematic LC host mixture N26 is formulated as follows:

[0827] [Table 103]

[0828] Polymerizable mixture P49 is prepared by adding 0.2% compound MA1, 0.05% compound MC1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N26.

[0829] <Example 50> The nematic LC host mixture N27 is formulated as follows:

[0830] [Table 104]

[0831] Polymerizable mixture P50 is prepared by adding 0.3% compound MA2, 0.2% compound MB1, and 50 ppm stabilizer S3-1 to the nematic LC host mixture N27.

[0832] <Example 51> The nematic LC host mixture N28 is formulated as follows:

[0833] [Table 105]

[0834] Polymerizable mixture P51 is prepared by adding 0.3% compound MA1, 0.2% compound MB2, and 50 ppm stabilizer S3-3 to nematic LC host mixture N28.

[0835] <Example 52> The nematic LC host mixture N29 is formulated as follows:

[0836] [Table 106]

[0837] Polymerizable mixture P52 is prepared by adding 0.3% compound MA1, 0.2% compound MB4, and 150 ppm stabilizer S2-1 to nematic LC host mixture N29.

[0838] <Example 53> The nematic LC host mixture N30 is formulated as follows:

[0839] [Table 107]

[0840] Polymerizable mixture P53 is prepared by adding 0.2% compound MA2, 0.1% compound MB1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N30.

[0841] <Example 54> The nematic LC host mixture N31 is formulated as follows:

[0842] [Table 108]

[0843] Polymerizable mixture P54 is prepared by adding 0.3% compound MA1, 0.2% compound MB5, and 150 ppm stabilizer S1-1 to nematic LC host mixture N31.

[0844] <Example 55> The nematic LC host mixture N32 is formulated as follows:

[0845] [Table 109]

[0846] Polymerizable mixture P55 is prepared by adding 0.3% compound MA2, 0.4% compound MB4, and 0.6% SA additive SA23 to the nematic LC host mixture N32.

[0847] <Example 56> The nematic LC host mixture N33 is formulated as follows:

[0848] [Table 110]

[0849] Polymerizable mixture P56 is prepared by adding 0.4% compound MA1, 0.2% compound MB1, 0.6% SA additive SA23, and 50 ppm stabilizer S3-3 to nematic LC host mixture N33.

[0850] <Example 57> The nematic LC host mixture N34 is formulated as follows:

[0851] [Table 111]

[0852] Polymerizable mixture P57 is prepared by adding 0.4% compound MA2, 0.2% compound MB1, 0.6% SA additive SA32, and 50 ppm stabilizer S3-1 to nematic LC host mixture N34.

[0853] <Example 58> The nematic LC host mixture N35 is formulated as follows:

[0854] [Table 112]

[0855] Polymerizable mixture P58 is prepared by adding 0.3% compound MA1, 0.2% compound MB5, 0.1% compound MC1, and 150 ppm stabilizer S3-2 to nematic LC host mixture N35.

[0856] <Example 59> The nematic LC host mixture N36 is formulated as follows:

[0857] [Table 113]

[0858] Polymerizable mixture P59 is prepared by adding 0.2% compound MA2, 0.3% compound MB2, 0.05% compound MC1, and 150 ppm stabilizer S3-3 to nematic LC host mixture N36.

[0859] <Example 60> The nematic LC host mixture N37 is formulated as follows:

[0860] [Table 114]

[0861] Polymerizable mixture P60 is prepared by adding 0.3% compound MA1, 0.3% compound MB1, 0.6% SA additive SA23, and 50 ppm stabilizer S1-1 to nematic LC host mixture N37.

[0862] <Example 61> The nematic LC host mixture N38 is formulated as follows:

[0863] [Table 115]

[0864] Polymerizable mixture P61 is prepared by adding 0.2% compound MA2, 0.3% compound MB3, 0.1% compound MC1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N38.

[0865] <Example 62> The nematic LC host mixture N39 is formulated as follows:

[0866] [Table 116]

[0867] Polymerizable mixture P62 is prepared by adding 0.2% compound MA1, 0.2% compound MB4, 0.1% compound MC1, and 150 ppm stabilizer S3-3 to nematic LC host mixture N39.

[0868] <Example 63> The nematic LC host mixture N40 is formulated as follows:

[0869] [Table 117]

[0870] Polymerizable mixture P63 is prepared by adding 0.2% compound MA1, 0.1% compound MC1, and 150 ppm stabilizer S3-2 to nematic LC host mixture N40.

[0871] <Example 64> The nematic LC host mixture N41 is formulated as follows:

[0872] [Table 118]

[0873] Polymerizable mixture P64 is prepared by adding 0.3% compound MA1, 0.2% compound MB1, 0.1% compound MC1, and 100 ppm stabilizer S3-3 to nematic LC host mixture N41.

[0874] <Example 65> The nematic LC host mixture N42 is formulated as follows:

[0875] [Table 119]

[0876] Polymerizable mixture P65 is prepared by adding 0.3% compound MA1, 0.2% compound MB1, 0.1% compound MC1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N42.

[0877] <Example 66> The nematic LC host mixture N43 is formulated as follows:

[0878] [Table 120]

[0879] Polymerizable mixture P66 is prepared by adding 0.4% of compound MA1, 0.2% of compound MB1, and 150 ppm of stabilizer S2-1 to nematic LC host mixture N43.

[0880] <Example 67> The nematic LC host mixture N44 is formulated as follows:

[0881] [Table 121]

[0882] Polymerizable mixture P67 is prepared by adding 0.2% compound MA2, 0.3% compound MB2, and 150 ppm stabilizer S3-2 to nematic LC host mixture N44.

[0883] <Example 68> The nematic LC host mixture N45 is formulated as follows:

[0884] [Table 122]

[0885] Polymerizable mixture P68 is prepared by adding 0.3% compound MA1, 0.2% compound MB3, 0.05% compound MC1, and 150 ppm stabilizer S3-3 to nematic LC host mixture N45.

[0886] <Example 69> The nematic LC host mixture N46 is formulated as follows:

[0887] [Table 123]

[0888] Polymerizable mixture P69 is prepared by adding 0.4% compound MA1, 0.2% compound MB1, 0.6% SA additive SA32, and 50 ppm stabilizer S3-1 to nematic LC host mixture N46.

[0889] <Example 70> The nematic LC host mixture N47 is formulated as follows:

[0890] [Table 124]

[0891] Polymerizable mixture P70 is prepared by adding 0.3% compound MA1, 0.2% compound MB1, 0.6% SA additive SA32, and 50 ppm stabilizer S2-1 to nematic LC host mixture N47.

[0892] <Example 71> The nematic LC host mixture N48 is formulated as follows:

[0893] [Table 125]

[0894] Polymerizable mixture P71 is prepared by adding 0.4% compound MA1, 0.3% compound MB1, 0.6% SA additive SA32, and 50 ppm stabilizer S3-3 to nematic LC host mixture N48.

[0895] <Example 72> The nematic LC host mixture N49 is formulated as follows:

[0896] [Table 126]

[0897] Polymerizable mixture P72 is prepared by adding 0.2% of compound MA1 and 0.2% of compound MB1 to nematic LC host mixture N49.

[0898] <Example 73> Polymerizable mixture P73 is prepared by adding 0.2% of compound MA1, 0.3% of compound MB1, 0.05% of compound MC2 of formula IC1, and 150 ppm of stabilizer S1-1 to nematic LC host mixture N1.

[0899] [ka]

[0900] <Example 74> Polymerizable mixture P74 is prepared by adding 0.1% of compound MA1, 0.3% of compound MB2, 0.05% of compound MC2, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N1.

[0901] <Example 75> Polymerizable mixture P75 is prepared by adding 0.2% compound MA2, 0.1% compound MC2, and 100 ppm stabilizer S1-1 to nematic LC host mixture N1.

[0902] <Example 76> Polymerizable mixture P76 is prepared by adding 0.2% of compound MA1, 0.3% of compound MB1, 0.05% of compound MC3 of formula IC13, and 150 ppm of stabilizer S1-1 to nematic LC host mixture N3.

[0903] [ka]

[0904] <Example 77> Polymerizable mixture P77 is prepared by adding 0.2% compound MA2, 0.2% compound MB2, 0.1% compound MC2, and 100 ppm stabilizer S1-1 to nematic LC host mixture N1.

[0905] <Example 78> Polymerizable mixture P76 is prepared by adding 0.2% of compound MA1, 0.3% of compound MB1, 0.05% of compound MC4 of formula IC22, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N3.

[0906] [ka]

[0907] <Example 79> Polymerizable mixture P79 is prepared by adding 0.2% compound MA1, 0.1% compound MC5 of formula IC23, and 150 ppm stabilizer S1-1 to nematic LC host mixture N1.

[0908] [ka]

[0909] <Example 80> Polymerizable mixture P80 is prepared by adding 0.1% of compound MA2, 0.3% of compound MB2, 0.05% of compound MC5, and 100 ppm of stabilizer S1-1 to nematic LC host mixture N1.

[0910] <Example 81> Polymerizable mixture P81 is prepared by adding 0.2% of compound MA1, 0.3% of compound MB1, 0.05% of compound MC6 of formula IC25, and 150 ppm of stabilizer S1-1 to nematic LC host mixture N3.

[0911] [ka]

[0912] <Example 82> Polymerizable mixture P82 is prepared by adding 0.2% compound MA2, 0.2% compound MB4, 0.05% compound MC6, and 150 ppm stabilizer S1-1 to nematic LC host mixture N1.

[0913] <Example 83> Polymerizable mixture P83 is prepared by adding 0.2% compound MA1, 0.1% compound MC6, and 150 ppm stabilizer S1-1 to nematic LC host mixture N3.

[0914] <Example 84> The nematic LC host mixture N50 is formulated as follows:

[0915] [Table 127]

[0916] Polymerizable mixture P84 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.484% nematic LC host mixture N50.

[0917] <Example 85> The nematic LC host mixture N51 is formulated as follows:

[0918] [Table 128]

[0919] Polymerizable mixture P85 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.484% nematic LC host mixture N51.

[0920] <Example 86> The nematic LC host mixture N52 is formulated as follows:

[0921] [Table 129]

[0922] Polymerizable mixture P86 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N52.

[0923] <Example 87> The nematic LC host mixture N53 is formulated as follows:

[0924] [Table 130]

[0925] Polymerizable mixture P87 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N53.

[0926] <Example 88> The nematic LC host mixture N54 is formulated as follows:

[0927] [Table 131]

[0928] Polymerizable mixture P88 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N54.

[0929] <Example 89> Polymerizable mixture P89 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.484% nematic LC host mixture N54.

[0930] <Example 90> The nematic LC host mixture N55 is formulated as follows:

[0931] [Table 132]

[0932] Polymerizable mixture P90 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.484% nematic LC host mixture N55.

[0933] <Example 91> Polymerizable mixture P91 is prepared by adding 0.94% chiral dopant S-4011 to 99.06% polymerizable mixture P90.

[0934] <Example 92> The nematic LC host mixture N56 is formulated as follows:

[0935] [Table 133]

[0936] Polymerizable mixture P92 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N56.

[0937] <Example 93> Polymerizable mixture P93 is prepared by adding 0.89% chiral dopant S-4011 to 99.11% polymerizable mixture P92.

[0938] <Example 94> The nematic LC host mixture N57 is formulated as follows:

[0939] [Table 134]

[0940] Polymerizable mixture P94 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N57.

[0941] <Example 95> Polymerizable mixture P95 is prepared by adding 0.91% chiral dopant S-4011 to 99.09% polymerizable mixture P94.

[0942] <Example 96> The nematic LC host mixture N58 is formulated as follows:

[0943] [Table 135]

[0944] Polymerizable mixture P96 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.484% nematic LC host mixture N58.

[0945] <Example 97> The nematic LC host mixture N59 is formulated as follows:

[0946] [Table 136]

[0947] Polymerizable mixture P97 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N59.

[0948] <Example 98> The nematic LC host mixture N60 is formulated as follows:

[0949] [Table 137]

[0950] Polymerizable mixture P98 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N60.

[0951] <Example 99> The nematic LC host mixture N61 is formulated as follows:

[0952] [Table 138]

[0953] Polymerizable mixture P99 is prepared by adding 0.2% compound MA1, 0.3% compound MB1, 0.05% compound MC1, 150 ppm stabilizer S1-1, and 10 ppm stabilizer Irganox® 1076 to 99.434% nematic LC host mixture N61.

[0954] <Example 100> Polymerizable mixture P100 is prepared by adding 0.92% chiral dopant S-4011 to 99.08% polymerizable mixture P99.

[0955] <Example 101> The nematic LC host mixture N62 is formulated as follows:

[0956] [Table 139]

[0957] Polymerizable mixture P101 is prepared by adding 0.2% compound MA1, 0.4% compound MB1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N62.

[0958] <Example 102> The nematic LC host mixture N63 is formulated as follows:

[0959] [Table 140]

[0960] Polymerizable mixture P102 is prepared by adding 0.2% compound MA1, 0.4% compound MB1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N63.

[0961] <Example 103> The nematic LC host mixture N64 is formulated as follows:

[0962] [Table 141]

[0963] Polymerizable mixture P103 is prepared by adding 0.2% compound MA1, 0.4% compound MB1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N64.

[0964] <Example 104> The nematic LC host mixture N65 is formulated as follows:

[0965] [Table 142]

[0966] Polymerizable mixture P104 is prepared by adding 0.2% compound MA1, 0.4% compound MB1, and 150 ppm stabilizer S1-1 to nematic LC host mixture N65.

Claims

1. LC medium comprising one or more polymerisable compounds selected from the formula IA and one or more polymerisable compounds selected from the formula IB and the formula IC. 【Chemistry 1】 wherein the individual radicals, each independently of one another, have the following meanings at each occurrence, which may be the same or different: P is a polymerizable group, Sp is a spacer group or a single bond; M １ , M ２ , M ３ are each independently a group selected from formulas 1 to 3, 【Chemistry 2】 provided that the benzene ring may be substituted by one or more groups L or P-Sp-; L is F, Cl, —CN, P-Sp- or linear, branched or cyclic alkyl having 1 to 25 C atoms, provided that there are one or more non-adjacent CH ２ In the group, O and / or S atoms may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that they are not directly linked to one another, and one or more H atoms may be replaced by P, F or Cl, respectively; provided that in the compound of formula IA, the group M １ and / or at least one spacer group Sp is L ａ is at least monosubstituted with L ａ is -C(R ａａ ) (R ｂｂ ) OH, R ａａ , R ｂｂ is a straight-chain alkyl having 1 to 6 C atoms, and in compounds of formula IC, the group M ３ Is L ｂ is at least monosubstituted with L ｂ is a straight-chain or branched alkenyl having 3 to 7 C atoms.

2. LC medium according to claim 1, characterized in that the compound of formula IA is selected from the following subformulae: 【Transformation 3】 【Chemistry 4】 【Transformation 5】 wherein P and Sp have the meanings given in claim 1, L has one of the meanings given in claim 1 different from P-Sp-, r1, r2, r3 are each independently 0, 1, 2, 3 or 4, and r4 is 0, 1, 2 or 3, However, the compound is L ａ at least one group Sp and / or L at least monosubstituted with ａ and at least one group L representing

3. LC medium according to claim 1, characterized in that it comprises one or more compounds of the formula IB selected from the formula IB-D and which have two polymerizable groups. 【Transformation 6】 (wherein P and Sp have the meanings given in claim 1, L has one of the meanings given in claim 1 different from P-Sp-, r1, r2, r3 are each independently 0, 1, 2, 3 or 4, and k is 0 or 1.)

4. LC medium according to claim 1, characterized in that it comprises one or more compounds of the formula IB selected from the formula IB-T and having three polymerizable groups. 【Transformation 7】 (wherein P and Sp have the meanings given in claim 1, L has one of the meanings given in claim 1 different from P-Sp-, r1 and r2 are each independently 0, 1, 2, 3 or 4, r4 is 0, 1, 2 or 3, and k is 0 or 1.)

5. LC medium according to claim 1, characterized in that it comprises one or more polymerizable compounds selected from the following subformulae: 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 wherein P and Sp have the meanings given in claim 1, L has one of the meanings given in claim 1 different from P-Sp-, r1, r2 and r3 are each independently 0, 1, 2, 3 or 4, and r4 is 0, 1, 2 or 3, with the proviso that r1 + r2 + r3 + r4 is 1 or more, provided that the compound does not contain L as defined in claim 1. ｂ and at least one group L representing

6. LC medium according to claim 1, characterized in that it comprises one or more compounds of the formula II 【Chemistry 11】 wherein the individual radicals, each independently of one another, have the following meanings at each occurrence, which may be the same or different: R １ and R ２ is a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms (provided that there are one or more non-adjacent CH ２ The groups are each formed by combining -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CR ０ =CR ００ -, -C≡C-, 【Chemistry 12】 wherein one or more H atoms may be replaced by F or Cl, R ０ and R ００ is H or alkyl having 1 to 12 C atoms, A １ and A ２ is a group selected from the following formulae: 【Chemistry 13】 in which the individual radicals, each independently of one another, have the following meanings at each occurrence, which may be the same or different: Z １ and Z ２ is -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -CO-O-, -O-CO-, -C ２ F ４ -, -CF=CF-, -CH=CH-CH ２ O— or a single bond, L １ , L ２ , L ３ and L ４ are F, Cl, OCF ３ , C.F. ３ , C.H. ３ , C.H. ２ F or CHF2, Y is H, F, Cl, CF ３ , CHF ２ or CH3, L Ｃ is CH ３ or OCH3, a1 is 1 or 2; a2 is 0 or 1.

7. LC medium according to claim 1, characterized in that it comprises one or more compounds of the formula II selected from the group consisting of the compounds of the formulae IIA, IIB, IIC and IID. 【Chemistry 14】 (In the formula, R ２Ａ and R ２Ｂ are each independently H, an alkyl or alkenyl group having up to 15 C atoms, which group is unsubstituted or is CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ The groups are formed by -O-, -S-, etc. so that the O atoms are not directly linked to each other. 【Chemistry 15】 -C≡C-, -CF ２ O-, -OCF ２ may be replaced by —, —CO—O— or —O—CO—, L １ ~L ４ are each independently F, Cl, CF ３ or CHF ２ represents Y is H, F, Cl, CF ３ , CHF ２ or CH3, Z ２ , Z ２Ｂ and Z ２Ｄ are each independently 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-, -CH=CHCH ２ represents O-, p represents 0, 1 or 2, and q is the same or different and represents 0 or 1 in each occurrence.

8. LC medium according to claim 1, characterized in that it comprises one or more compounds of the formula III 【Chemistry 16】 (In the formula, R １１ and R １２ each independently represent H, an alkyl or alkoxy group having 1 to 15 C atoms, provided that one or more CH ２ The group is formed so that the O atoms are not directly connected to each other. 【Chemistry 17】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO-, each of which may be replaced independently, in which one or more H atoms may additionally be replaced by halogen; A ３ occur independently of each other, a) a 1,4-cyclohexenylene or 1,4-cyclohexylene group, in which one or two non-adjacent CH ２ The group may be replaced by —O— or —S—; b) a 1,4-phenylene group, in which one or two CH groups may be replaced by N, or c) a group 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. represents provided that groups a), b) and c) may be mono- or polysubstituted with halogen atoms; n represents 0, 1 or 2; Z １ are each independently -CO-O-, -O-CO-, -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -CH ２ -, -CH ２ CH ２ -, -(CH ２ ) ４ -, -CH=CH-CH ２ O-, -C ２ F ４ -, -CH ２ CF ２ -, -CF ２ CH ２ represents -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, L １１ and L １２ are each independently F, Cl, CF ３ or CHF2, and W represents O or S.

9. LC medium according to claim 1, characterized in that it comprises one or more compounds of the formula IV [Chemistry 18] (In the formula, R ４１ represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, R ４２ represents an unsubstituted alkyl group having 1 to 7 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, or an unsubstituted alkenyl group having 2 to 7 carbon atoms.

10. LC medium according to claim 1, characterized in that it comprises one or more compounds of the formula V 【Chemistry 19】 (In the formula, R 51 represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms; R 52 represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or an unsubstituted alkenyl group having 2 to 7 C atoms; 【Chemistry 20】 During the ceremony, 【Chemistry 21】 Z ５１ , Z ５２ are each independently —CH ２ -CH ２ -, -CH ２ represents —O—, —CH═CH—, —C≡C—, —COO— or a single bond; n is 1 or 2.

11. LC medium according to claim 1, characterized in that it additionally comprises one or more chiral dopants.

12. LC medium according to claim 1, characterized in that it additionally comprises one or more additives selected from the group consisting of stabilizers, polymerization initiators and self-aligning additives.

13. 13. Process for preparing an LC medium according to any one of claims 1 to 12, comprising the steps of mixing one or more polymerizable compounds as defined in any one of claims 1 to 5 with one or more compounds of formula II, III, IV and / or V as defined in any one of claims 6 to 10, optionally with further liquid crystal compounds and / or additives, and optionally polymerizing the polymerizable compounds.

14. LC display comprising an LC medium as defined in claim 1.

15. 2. An LC display comprising an LC medium as defined in claim 1, which is a PS-VA, PS-IPS, PS-FFS or SA-VA display.

16. 10. An LC display comprising an LC medium as defined in claim 1, characterized in that it comprises two substrates, at least one of which is transparent to light, an electrode on each substrate or two electrodes on only one of the substrates, and a layer of an LC medium according to claim 1 arranged between the substrates, with the proviso that the polymerizable compound has been polymerized between the substrates of the display by UV photopolymerization.

17. A method for producing an LC display comprising two substrates, at least one of which is transparent to light, an electrode provided on each substrate or two electrodes provided on only one of the substrates, and a layer of the LC medium according to claim 1 disposed between the substrates, wherein the polymerizable compound is polymerized between the substrates of the display by UV photopolymerization, comprising:

10. A method comprising the steps of providing an LC medium according to claim 1 between the substrates of a display and polymerising the polymerisable compound by irradiating with UV light whilst applying a voltage to the electrodes of the display.

18. 10. Use of an LC medium according to claim 1 for an energy-saving LC display or for a method for producing an energy-saving LC display.

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