Liquid crystal medium comprising a polymerisable compound

Abstract

The present invention relates to a liquid-crystalline (LC) medium comprising polymerisable compounds containing a thioalkyl group for optical, electro-optical and electronic purposes, in particular for use in LC displays, especially in PSA (polymer sustained alignment) or SA (self-alignment) type LC displays, to a PSA or SA mode LC display comprising the LC medium and to a process for the production of the LC display.

Description

[0001] This application is a divisional application of Chinese patent application No. 202110380475.8, filed on April 9, 2021, entitled "Liquid Crystal Medium Containing a Polymerizable Compound". Technical Field

[0002] This invention relates to a liquid crystal (LC) medium comprising a polymerizable compound containing a thioalkyl group, for optical, electro-optical and electronic purposes, particularly for use in LC displays, especially in PSA (polymer-stabilized alignment) or SA (self-alignment) type LC displays, a PSA or SA mode LC display comprising the LC medium, and a method for manufacturing the LC display. Background Technology

[0003] The proliferation of 8K and gaming monitors has led to increased demand for LC display (LCD) panels with higher refresh rates, and consequently, for LC media with faster response times. Many of these LCD panels use polymer-stabilized (PS) or polymer-stabilized alignment (PSA) modes, such as PS-VA (vertically aligned), PS-IPS (in-plane switching), or PS-FFS (edge ​​field switching) modes or their derivatives, or self-aligned (SA) modes such as SA-VA, which are polymer-stabilized.

[0004] In PS or PSA mode, a small amount, typically 0.1-1%, of one or more polymerizable mesocrystalline compounds (also known as RM (reactive mesocrystalline)) is added to the LC medium. After the LC medium is filled into the display, the RM is then polymerized in situ via UV photopolymerization while a voltage is applied to the electrodes of the display. This creates a small tilt angle in the LC molecules of the LC medium, which is stabilized by the polymerized RM. The UV polymerization method (also known as the "PSA method") is typically carried out in two steps: a first UV exposure step ("UV1 step"), in which a voltage is applied to create the tilt angle, and a second UV exposure step ("UV2 step"), in which no voltage is applied, to complete the RM polymerization.

[0005] In SA-VA mode, the alignment layer is omitted from the display. Instead, a small amount, typically 0.1–2.5%, of self-aligning (SA) additive is added to the LC medium. This initiates the desired alignment, such as vertical or planar alignment, in situ via a self-assembly mechanism. SA additives typically contain an organic mesocrystalline core group with one or more polar anchoring groups, such as hydroxyl, carboxyl, amino, or thiol groups, attached thereto. These groups interact with the substrate surface, causing the additive to align on the substrate surface and inducing the desired alignment within the LC molecules. SA additives may also contain one or more polymerizable groups, which can be polymerized under conditions similar to the RM used in the PSA method. In addition to the SA additive, the LC medium also contains one or more RMs.

[0006] One approach to reducing the response time of LC media to PSA mode is, for example, by using alkenyl compounds as components of the LC host mixture. However, this can lead to reduced reliability of the mixture when exposed to the UV light required for polymerizing RM additives, which is believed to be due to the reaction of the alkenyl compound with the polyimide in the alignment layer, particularly problematic when using shorter UV wavelengths less than 320 nm. Therefore, there is a trend towards using longer UV wavelengths for PSA methods.

[0007] The use of UV-LED lamps in the PSA process is also recommended because they exhibit lower energy consumption, longer lifetime, and more efficient light energy transfer to the LC medium due to their narrower emission peaks, which allows for reduced UV intensity and / or UV irradiation time. This can shorten cycle time and save energy and production costs. Currently available UV lamps have higher wavelength emission, for example, at 365 nm.

[0008] Therefore, polymerizable LC media containing RM that can be effectively polymerized at longer UV wavelengths are needed.

[0009] Furthermore, there is a significant demand for PSA or SA displays, and for LC media and polymerizable compounds used in such displays, that possess high specific resistivity, a wide operating temperature range, short response time (even at low temperatures), low threshold voltage, low tilt angle, high tilt stability, multiple grayscale levels, high contrast and wide viewing angle, high reliability and high VHR value after UV exposure, and, in the case of polymerizable compounds, low melting point and high solubility in the LC bulk mixture. In displays for mobile applications, there is a particular desire for available LC media that exhibit low threshold voltage and high birefringence. Summary of the Invention

[0010] The present invention aims to provide novel suitable materials, particularly RM and LC media containing RM, for use in PSA or SA displays, which do not have the aforementioned disadvantages or have the aforementioned disadvantages to a reduced extent.

[0011] Specifically, the present invention is based on the following objectives: to include an LC medium containing RM for use in PSA or SA displays, which can have very high resistivity, high VHR, high reliability, low threshold voltage, short response time, high birefringence, good UV absorption, especially at longer UV wavelengths, preferably 340-380 nm, enabling rapid and complete polymerization of RM, producing low tilt angles, preferably produced as quickly as possible, and high tilt stability, even after longer times and / or after UV exposure, reducing or preventing “image stickiness” and “ODF inhomogeneity (mura)” in the display, and exhibiting high solubility in the LC medium when RM is polymerized as quickly and completely as possible, said LC medium being commonly used as the main mixture for PSA or SA displays.

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

[0013] Another object of the present invention is to provide novel LC media containing RM, particularly for optical, electro-optical and electronic applications, as well as suitable methods and intermediates for their preparation.

[0014] Another object of the present invention is to provide an LC medium containing RM, which exhibits one or more of the following advantageous effects:

[0015] - After exposure to UV light, they produce the desired tilt angle.

[0016] - They result in high tilt stability.

[0017] They exhibit good UV absorption, especially at higher UV wavelengths, particularly in the 340-400 nm range, and RM is able to polymerize rapidly and completely at these wavelengths.

[0018] - These are suitable for PSA displays manufactured using UV-LED lamps and polymerization methods.

[0019] - They are able to control the time range of the first UV step very well, where a tilt angle is generated during the UV process.

[0020] - They are able to maintain the timeframe of the second UV step, where any residual RM is polymerized and the tilt angle is stabilized, minimizing production costs as much as possible.

[0021] - After the first and second UV exposure steps, the residual RM has less or no negative impact on the performance parameters of the LC mixture, such as VHR, tilt stability, etc.

[0022] They exhibit good solubility and stability in LC mixtures over a wide temperature range, preferably -40 to 140°C.

[0023] It has been found that one or more of these purposes can be achieved by providing LC media as described herein and for which protection is sought. Detailed Implementation

[0024] Therefore, the present invention relates to an LC medium, characterized in that it comprises one or more polymerizable compounds of formula I.

[0025] P-Sp-A a -(Z a -A b ) z -R b I

[0026] Each group is independent of the others and, each time it appears, has the same or different meanings as follows:

[0027] R b For P-Sp- or R,

[0028] R is F, Cl, -CN, or a straight-chain, branched, or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups are optionally represented by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, or CR such that the O- and / or S- atoms are not directly connected to each other. 0 =CR 00 -、-C≡C-、

[0029]

[0030] Furthermore, one or more H atoms are each optionally replaced by F, Cl, or P-Sp-.

[0031] P is a polymerizable group.

[0032] Sp is an optional spacer group substituted with P, or a single bond.

[0033] A a A b It is an alicyclic, heterocyclic, aromatic, or heteroaromatic ring group having 4-20 ring atoms, which is monocyclic or polycyclic and optionally substituted by one or more A, L, or P-Sp- groups.

[0034] Z ais -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH2-CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 - or a single key,

[0035] R 0 , R 00 It is H or an alkyl group having 1-12 carbon atoms.

[0036] A is an alkyl group having 2-12, preferably 2-8, carbon atoms, wherein one or more, preferably non-terminal CH2 groups are replaced by S such that the S atoms are not directly connected to each other; preferably a thioalkyl group having 1-7 carbon atoms; very preferably SCH3.

[0037] L is F, Cl, -CN, P-Sp- or a straight-chain, branched or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups are optionally arranged such that the O- and / or S- atoms are not directly connected to each other by O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, CR 0 =CR 00 -、-C≡C-、

[0038]

[0039] Furthermore, one or more H atoms are each optionally replaced by P-Sp-, F, or Cl.

[0040] z is 0, 1, 2, 3 or 4.

[0041] n1 is 1, 2, 3, or 4.

[0042] The compound of formula I contains at least one group A substituted by at least one group A. a Or A b ,

[0043] It also contains one or more compounds of formula II.

[0044]

[0045] Each group is independent of the others and, each time it appears, has the same or different meanings as follows:

[0046] R 1 , R 2 It is a straight-chain, branched, or cyclic alkyl group having 1-25 carbon atoms, wherein one or more non-adjacent CH2 groups are optionally configured such that the O- and / or S- atoms are not directly connected to each other by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O-, CR 0 =CR 00 -、-C≡C-、

[0047]

[0048] Furthermore, one or more H atoms are optionally replaced by F or Cl, preferably alkyl or alkoxy groups having 1-6 C atoms.

[0049] A 1 A 2 Groups selected from the following formulas

[0050]

[0051] Preferred formulas A1, A2, A3, A4, A5, A6, A9, and A10; Very preferred formulas A1, A2, A3, A4, A5, A9, and A10.

[0052] Z 1 Z 2 The bond type can be -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2F4-, -CF=CF-, -CH=CH-CH2O-, or a single bond, preferably a single bond.

[0053] L 1 , L 2 , L 3 , L 4 The solvent is F, Cl, OCF3, CF3, CH3, CH2F, or CHF2, with F or Cl being preferred, and F being very preferred.

[0054] Y is H, F, Cl, CF3, CHF2, or CH3, preferably H or CH3, and very preferably H.

[0055] L C It is CH3 or OCH3, preferably CH3.

[0056] a1 is 1 or 2.

[0057] a2 is 0 or 1.

[0058] The present invention also relates to the use of LC media in PSA or SA mode LC displays as described in the context.

[0059] LC dielectrics preferably have negative dielectric anisotropy.

[0060] Preferred polymerizable compounds of formula I are selected such that they exhibit absorption in the range of 340-400 nm, preferably 350-370 nm.

[0061] The present invention also relates to an LC medium, comprising

[0062] - Polymerizable component A) comprises, preferably, one or more polymerizable compounds, at least one of which is a compound of formula I.

[0063] - Liquid crystal component B), hereinafter also referred to as "LC host mixture", contains one or more liquid crystal compounds, at least one of which is a compound of formula II.

[0064] as well as

[0065] - Optional one or more additives, selected from self-orienting additives and stabilizers.

[0066] The present invention further relates to a method for preparing LC media as described in the context, comprising the steps of: mixing one or more polymerizable compounds of formula I with one or more compounds of formula II, and optionally mixing with further LC compounds and / or additives.

[0067] The present invention further relates to an LC display comprising the LC medium of the present invention as described in the context, which is a PSA or SA display, preferably a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS or SA-VA display.

[0068] The present invention further relates to an LC display comprising an LC medium as described in the context, wherein the polymerizable compound is present in a polymeric form, preferably a PSA or SA display, and very preferably a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS, or SA-VA display.

[0069] The present invention further relates to a PSA-type LC display comprising two substrates, at least one of which is transparent to light, an electrode disposed on each substrate, or two electrodes disposed on only one substrate, and a layer of LC dielectric as described in the context located between the substrates, wherein a polymerizable compound is polymerized between the substrates of the display by UV light polymerization.

[0070] The present invention also relates to a method of manufacturing an LC display as described in the context, comprising the steps of: filling or otherwise providing an LC medium as described in the context between substrates of the display, and polymerizing a polymerizable compound, preferably by UV light irradiation, wherein the UV light preferably has a wavelength > 340 nm, preferably in the range of 340-400 nm, more preferably in the range of 340-380 nm, very preferably in the range of 350 to < 370 nm, most preferably in the range of 355-368 nm, and preferably simultaneously applying a voltage to electrodes of the display.

[0071] The present invention further relates to a method for manufacturing an LC display as described in the context, wherein the irradiation of the polymerizable compound is performed using a UV-LED lamp.

[0072] When used in a PSA display, the LC medium of the present invention exhibits the following advantageous characteristics:

[0073] - Appropriate tilting is generated within a certain process window.

[0074] - Rapid polymerization minimizes residual RM levels after UV treatment.

[0075] - High voltage retention rate after UV treatment

[0076] - Good tilt stability,

[0077] - Excellent thermal stability,

[0078] - It has sufficient solubility in organic solvents typically used in display manufacturing.

[0079] In addition, the LC medium of the present invention helps to solve one or more of the following problems:

[0080] - To create the desired tilt angle after exposure to UV.

[0081] - Provides high tilt stability,

[0082] - It exhibits good UV absorption, especially at longer UV wavelengths, preferably in the range of 340-400 nm, more preferably in the range of 340-380 nm, very preferably in the range of 350 to <370 nm, and most preferably in the range of 355-368 nm, and can rapidly and completely polymerize RM at these wavelengths.

[0083] - Suitable for PSA displays manufactured using a polymerization process employing UV-LED lamps.

[0084] - During UV processing, control the time range of the first UV step that generates the tilt angle.

[0085] - Minimize the time frame of the second UV step as much as possible to minimize production costs.

[0086] - After the first and second UV exposure steps, reduce or avoid any negative impact of residual RM on the performance parameters of the LC mixture, such as VHR, tilt stability, etc.

[0087] - It provides good solubility and stability in LC bulk mixtures over a wide temperature range, preferably -40°C to about 140°C.

[0088] As described below, alkenyl groups in the compound of Formula II or other components of the LC medium are not considered within the meaning of the term "polymerizable group" as used herein. Preferably, the polymerization conditions of the polymerizable compound in the LC medium are selected such that the alkenyl substituents do not participate in the polymerization reaction. Preferably, the LC media disclosed and claimed in this application do not contain additives that initiate or enhance the participation of alkenyl groups in the polymerization reaction.

[0089] Unless otherwise stated, polymerizable compounds and compounds of formula II are preferably selected from achiral compounds.

[0090] As used herein, the expression “UV light with wavelength of…” followed by a wavelength range (in nm), or a given lower or upper wavelength limit (in nm), indicates that the UV emission spectrum of the corresponding irradiation source has an emission peak, which is preferably the highest peak in the corresponding spectrum within the given wavelength range or above the given lower wavelength limit or below the given upper wavelength limit, and / or the UV absorption spectrum of the corresponding chemical compound has a long wavelength tail or a short wavelength tail extending into the given wavelength range or above the given lower wavelength limit or below the given upper wavelength limit.

[0091] As used in this article, the term "full width at half maximum" or "FWHM" refers to the width of the spectral curve measured between those points on the y-axis that are half the maximum amplitude.

[0092] As used herein, the term "substantially transmittant" means that the filter transmits a substantial portion, preferably at least 50% of the intensity, of incident light at the desired wavelength. As used herein, the term "substantially blocking" means that the filter does not transmit a substantial portion, preferably at least 50% of the intensity, of incident light at the undesired wavelength. As used herein, the term "desired (undesired) wavelength" refers, for example, to wavelengths within (outside) a given range λ for a bandpass filter, and to wavelengths above (below) a given value λ for a cutoff filter.

[0093] As used herein, the terms “active layer” and “switchable layer” refer to layers in electro-optic displays, such as LC displays, which contain one or more molecules with structural and optical anisotropy, such as LC molecules, that change their orientation when subjected to external stimuli such as an electric or magnetic field, resulting in a change in the layer’s transmittance to polarized or unpolarized light.

[0094] As used herein, the terms “tilt” and “tilt angle” should be understood to refer to the tilted orientation of LC molecules of the LC medium relative to the cell surface in an LC display (preferably a PSA display), and should be understood to include “pre-tilt” and “pre-tilt angle”. The tilt angle described herein represents the average angle (<90°) between the longitudinal molecular axis (LC director) of the LC molecules and the planar parallel outer surface forming the LC cell. Low absolute tilt angles (i.e., significantly deviating from 90°) correspond to large tilts. Suitable methods for measuring tilt angles are given in the embodiments. Unless otherwise stated, tilt angle values ​​disclosed in the context are related to this measurement method.

[0095] As used herein, the terms “reactive mesocrystalline” and “RM” should be understood to refer to a compound containing a mesocrystalline or liquid crystal framework and one or more polymerizable functional groups attached thereto, and said functional groups are also referred to as “polymerizable groups” or “P”.

[0096] Unless otherwise stated, the term “polymerizable compound” as used herein should be understood to mean polymerizable monomeric compound.

[0097] The SA-VA display of this invention will be of polymer-stabilized mode because it comprises an LC medium containing RMs of formulas I and II or is manufactured using an LC medium containing RMs of formulas I and II. Therefore, as used herein, unless explicitly mentioned, the term "SA-VA display" should be understood to refer to a polymer-stabilized SA-VA display when referring to the display of this invention.

[0098] As used herein, the term “low molecular weight compound” should be understood to mean a monomer and / or a compound not prepared by polymerization, as opposed to “polymeric compound” or “polymer”.

[0099] As used herein, the term "non-polymerizable compound" will be understood to mean a compound that does not contain functional groups suitable for polymerization under the conditions typically applied to RM polymerization.

[0100] As used herein, the term "mesocrystalline group" is known to those skilled in the art and described in the literature, and it refers to a group that substantially contributes to the formation of a liquid crystal (LC) phase in low molecular weight or polymeric substances due to the anisotropy of its attractive and repulsive interactions. A compound containing a mesocrystalline group (mesocrystalline compound) does not necessarily have an LC phase by itself. Mesocrystalline compounds can exhibit LC phase behavior only after being mixed with other compounds and / or after polymerization. Typical mesocrystalline groups are, for example, rigid rod-shaped or disk-shaped units. Pure Appl. Chem. 2001, 73(5), 888 and C.Tschierske, G. Pelzl, S. Diele, Angew. Chem. The terms and definitions used in relation to mesocrystalline or LC compounds are given in 2004, 116, 6340-6368.

[0101] As used herein, the term "spacer group" (hereinafter also referred to as "Sp") is known to those skilled in the art and described in the literature, see, for example... Pure Appl. Chem. 2001, 73(5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. As used herein, the term "spacer group" or "spacer base" refers to a flexible group, such as an alkylene group, attached to a mesocrystalline or polymerizable group in a polymerizable mesocrystalline compound. In the context,

[0102] Represents the trans-1,4-cyclohexyl ring, and

[0103] It represents a 1,4-phenylene ring.

[0104] In groups

[0105] In this system, the single bond between the two ring atoms can be attached to any free position on the benzene ring.

[0106] If the group R in the formula is shown in the context 1-12 , R Q R or L represents alkyl and / or alkoxy, which can be straight-chain or branched. It is preferably straight-chain, having 2, 3, 4, 5, 6 or 7 C atoms and correspondingly preferably representing ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, as well as methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonoxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.

[0107] If the group R in the formula is shown in the context 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 represents alkyl and / or alkoxy, and it can be straight-chain or branched. It is preferably straight-chain, having 2, 3, 4, 5, 6 or 7 C atoms and correspondingly preferably representing ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, as well as methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonoxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.

[0108] If the group R in the formula is shown in the context 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 represents an alkyl group in which one or more CH2 groups are replaced by S, and it can be straight-chain or branched. It is preferably straight-chain, having 1, 2, 3, 4, 5, 6 or 7 C atoms and correspondingly preferably representing thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl or thioheptyl.

[0109] The oxane group preferably represents straight-chain 2-oxapropyl (= methoxymethyl), 2-oxabutyl (= ethoxymethyl) or 3-oxabutyl (= 2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.

[0110] If the group R in the formula is shown in the context 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 represents alkoxy or oxalyl, and it may also contain one or more additional oxygen atoms, provided that the oxygen atoms are not directly connected to each other.

[0111] In another preferred embodiment, 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 One or more of R or L are selected from the following groups

[0112]

[0113] -S 1 -F, -OS 1 -F, -O-S1-O-S2, where S 1 C 1-12 -alkylene or C 2-12 - Idemenyl and S 2 For H, C 1-12 -alkyl or C 2-12 -Alkenyl, and very preferably selected from the following groups

[0114]

[0115] -OCH2OCH3, -O(CH2)2OCH3, -O(CH2)3OCH3, -O(CH2)4OCH3, -O(CH2)2F, -O(CH2)3F and -O(CH2)4F.

[0116] If the group R in the formula is shown in the context 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 indicates an alkyl group in which one of the CH2 groups has been replaced by -CH=CH-, and it can be straight-chain or branched. It is preferably straight-chain and has 2-10 C atoms. Accordingly, it represents, in particular, vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hep-1-, -2-, -3-, -4-, -5- or -6-enyl, oct-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, non-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, dec-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or -9-enyl.

[0117] If the group R in the formula is shown in the context 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 CR2R or L represents an alkyl or alkenyl group that is at least monosubstituted with a halogen, preferably a straight chain, and the halogen is preferably F or Cl. In the case of multiple substitution, the halogen is preferably F. The resulting group also includes perfluorinated groups. In the case of monosubstituted substitution, the fluorine or chlorine substituent can be at any desired position, but is preferably in the position of fluorine or chlorine. -Bit.

[0118] The halogen is preferably F or Cl, with F being the most preferred.

[0119] Group -CR 0 =CR 00 - Preferably -CH=CH-.

[0120] -OC-, -CO-, -C(=O)-, and -C(O)- represent carbonyl groups, i.e. .

[0121] Preferred substituents L are, for example, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R). x )2、-C(=O)Y 1 -C(=O)R x -N(R) x 2. Straight-chain or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy, or alkoxy carbonyloxy groups, each having 1-25 carbon atoms, wherein one or more H atoms may optionally be replaced by F or Cl, optionally substituted silyl groups having 1-20 Si atoms, or optionally substituted aryl groups having 6-25, preferably 6-15 carbon atoms.

[0122] Where R x Represents H, F, Cl, CN, or a straight-chain, branched, or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, or -O-CO-O- in such a manner that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are each optionally replaced by F, Cl, P-, or P-Sp-.

[0123] Y 1 It represents halogens.

[0124] Particularly preferred substituents L are, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and phenyl.

[0125]

[0126] L has one of the meanings described above.

[0127] The polymerizable group P is a group suitable for polymerization reactions, such as free radical or ionic chain polymerization, addition polymerization, or condensation polymerization, or a group suitable for polymer-like reactions, such as a group that adds to or condenses on the polymer backbone. Groups suitable for chain polymerization are particularly preferred, especially those containing C=C double bonds or -C≡C- triple bonds, and groups suitable for ring-opening polymerization, such as oxobutane or epoxy groups.

[0128] Preferred group P is selected from the following groups

[0129] CH2=CW 1 -CO-O-、CH2=CW 1 -CO-、 , , , , CH2=CW 2 -(O) k3 -、CW 1 =CH-CO-(O) k3 -、CW 1 =CH-CO-NH-、CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -、HS-CW 2 W 3 -、HW 2 N-, HO-CW 2 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 - CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 Si-, where W 1 It represents H, F, Cl, CN, CF3, phenyl, or alkyl groups having 1-5 carbon atoms, especially H, F, Cl, or CH3, W 2 and W 3Each independently represents H or an alkyl group having 1-5 carbon atoms, especially H, methyl, ethyl, or n-propyl, W 4 W 5 and W 6 Each independently represents Cl, an oxaalkyl or oxacarbonylalkyl group having 1-5 carbon atoms, and W. 7 and W 8 Each of them independently represents H, Cl or an alkyl group having 1-5 C atoms, Phe represents 1,4-phenylene, which is optionally substituted with one or more groups L different from P-Sp- as defined above, k1, k2 and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0130] The highly preferred group P is selected from the following groups:

[0131] CH2=CW 1 -CO-O-、CH2=CW 1 -CO-、 , , , , CH2=CW 2 -O-、CH2=CW 2 -、CW 1 =CH-CO-(O) k3 -、CW 1 =CH-CO-NH-、CH2=CW 1 -CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 - CH2=CH-(CO) k1 -Phe-(O) k2 -、Phe-CH=CH- and W 4 W 5 W 6 Si-, where W 1 It represents H, F, Cl, CN, CF3, phenyl, or alkyl groups having 1-5 carbon atoms, especially H, F, Cl, or CH3, W 2 and W 3 Each independently represents H or an alkyl group having 1-5 carbon atoms, especially H, methyl, ethyl, or n-propyl, W 4 W5 and W 6 Each independently represents Cl, an oxaalkyl or oxacarbonylalkyl group having 1-5 carbon atoms, and W. 7 and W 8 Each of them independently represents H, Cl or an alkyl group having 1-5 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.

[0132] The highly preferred group P is selected from the group CH2=CW. 1 -CO-O-, especially CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, as well as CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O- and .

[0133] Further preferred polymerizable groups P are selected from ethylene oxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxy groups, with acrylate and methacrylate being the most preferred.

[0134] In a highly preferred polymerizable compound, all polymerizable groups have the same meaning.

[0135] If the spacer group Sp is different from a single bond, it is preferably of the formula Sp"-X, so that each group P-Sp- conforms to the formula P-Sp"-X"-, wherein

[0136] "Sp" indicates a linear or branched alkylene group having 1-20, preferably 1-12, carbon atoms, optionally mono- or polysubstituted with F, Cl, Br, I, or CN, wherein one or more non-adjacent CH2 groups may be independently replaced by -O-, -S-, -NH-, or -N(R) groups such that the O and / or S atoms are not directly connected 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 Substitute with -, -CH=CH- or -C≡C-.

[0137] X" means -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-、-N(R 0 )-CO-、-N(R 0 )-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -、-CY 2 =CY 3 -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or single bonds

[0138] R 0 and R 00 Each of these independently represents H or an alkyl group having 1-20 carbon atoms, and

[0139] Y 2 and Y 3 Each can be represented independently as H, F, Cl, or CN.

[0140] X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, or -CO-NR. 0 -、-NR 0 -CO-、-NR 0 -CO-NR 00 - or a single key.

[0141] Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -O-CO-、-(CH2) p1 -CO-O-、-(CH2) p1 -O-CO-O-、-(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR) 0 R 00 -O) p1 - where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 It has the meaning described above.

[0142] The particularly preferred groups Sp and -Sp"-X"- are -(CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -O-CO-、-(CH2) p1 -CO-O-、-(CH2) p1 -O-CO-O-, where p1 and q1 have the meanings described above.

[0143] The particularly preferred group Sp" is, in each case, a straight-chain ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, vinylene, propenylene, and butenylene.

[0144] In a preferred embodiment of the invention, Formula I and its sub-formulas contain a spacer group Sp substituted with one or more polymerizable groups P, such that the group Sp-P corresponds to Sp(P). s , where s is ≥2 (branched polymerizable groups).

[0145] The preferred formula I compound according to this preferred embodiment is one in which s is 2, i.e., a compound containing the group Sp(P)2. The most preferred formula I compound according to this preferred embodiment contains a group selected from the following formulas:

[0146] -X-alkyl-CHPP S1

[0147] -X-alkyl-CH((CH2) aa P)((CH2) bb P) S2

[0148] -XN((CH2) aa P)((CH2) bb P) S3

[0149] -X-alkyl-CHP-CH2-CH2P S4

[0150] -X-alkyl-C(CH2P)(CH2P)-C aa H 2aa+1 S5

[0151] -X-alkyl-CHP-CH2P S6

[0152] -X-alkyl-CPP-C aa H 2aa+1 S7

[0153] -X-alkyl-CHPCHP-C aa H 2aa+1 S8

[0154] Where P is defined as in Equation I.

[0155] Alkyl refers to a straight-chain or branched alkylene group with a single bond or 1-12 carbon atoms, which is unsubstituted or mono- or polysubstituted with F, Cl, or CN, and one or more non-adjacent CH2 groups may be independently bonded to each other such that the O and / or S atoms are not directly connected to each other. 0 )=C(R 0 )-、-C≡C-、-N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- substitution, where R 0 It has the meaning described above.

[0156] aa and bb can each independently represent 0, 1, 2, 3, 4, 5, or 6.

[0157] X has one of the meanings described for X", and is preferably O, CO, SO2, O-CO-, CO-O or a single bond.

[0158] The preferred spacer group Sp(P)2 is selected from formulas S1, S2 and S3.

[0159] The highly preferred spacer group Sp(P)2 is selected from the following formulas:

[0160] -CHPP S1a

[0161] -O-CHPP S1b

[0162] -CH2-CHPP S1c

[0163] -OCH2-CHPP S1d

[0164] -CH(CH2-P)(CH2-P) S2a

[0165] -OCH(CH2-P)(CH2-P) S2b

[0166] -CH2-CH(CH2-P)(CH2-P) S2c

[0167] -OCH2-CH(CH2-P)(CH2-P) S2d

[0168] -CO-NH((CH2)2P)((CH2)2P) S3a

[0169] P is preferably selected from ethylene oxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxobutane and epoxy groups, with acrylate and methacrylate being very preferred, and methacrylate being the most preferred.

[0170] Further preferably, all polymerizable groups P present in the same compound have the same meaning, and very preferably represent acrylate group or methacrylate group, most preferably methacrylate group.

[0171] Sp preferably represents a single bond or -(CH2). p1 -、-(CH2) p2 -CH=CH-(CH2) p3 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 Where p1 is 2, 3, 4, 5 or 6, preferably 2 or 3, p2 and p3 are independently 0, 1, 2 or 3, and if Sp is -O-(CH2). p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Then, the O-atom or CO-group is attached to the benzene ring.

[0172] Further preferably, at least one Sp group is a single bond.

[0173] Further preferably, at least one Sp group is different from a single bond, and is preferably selected from -(CH2). p1 -、-(CH2) p2 -CH=CH-(CH2) p3 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 Where p1 is 2, 3, 4, 5 or 6, preferably 2 or 3, p2 and p3 are independently 0, 1, 2 or 3, and if Sp is -O-(CH2). p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Then, the O-atom or CO-group is attached to the benzene ring.

[0174] The Sp atom is preferably different from a single bond and is selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2- and -CO-O-(CH)2-, wherein the O atom or CO group is attached to the benzene ring.

[0175] In Formula I and its sub-formulas as described in the context, P is preferably selected from ethyleneoxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxy, very preferably acrylate and methacrylate, and most preferably methacrylate.

[0176] Further preferred are compounds of formula I and its sub-formulas as described in the context, wherein all polymerizable groups P present in the compound have the same meaning, and very preferably represent acrylate or methacrylate groups, most preferably methacrylate groups.

[0177] Further preferred are compounds of formula I and its sub-formulas as described in the context, which contain one, two, three or four P-Sp groups, with two or three P-Sp groups being very preferred.

[0178] Further preferred are compounds of formula I and its derivatives as described in the context, wherein R b It is P-Sp-.

[0179] Further preferred compounds are those of formula I and its sub-formulas as described in the context, wherein Sp represents a single bond or -(CH2). p1 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 Where p1 is 2, 3, 4, 5 or 6, and if Sp is -O-(CH2) p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Then, the O-atom or CO-group is attached to the benzene ring.

[0180] Further preferred are compounds of formula I and its sub-formulas as described in the context, wherein at least one Sp group is a single bond.

[0181] Further preferred are compounds of formula I and its sub-formulas as described in the context, wherein at least one Sp group is different from a single bond and is selected from -(CH2). p1 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 or -CO-O-(CH2) p1 Where p1 is 2, 3, 4, 5 or 6, and if Sp is -O-(CH2) p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Then, the O-atom or CO-group is attached to the benzene ring.

[0182] Highly preferred are compounds of formula I and its sub-formulas as described in the context, wherein at least one Sp group is different from a single bond and is selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2- and -CO-O-(CH)2-, wherein the O atom or CO group is attached to the benzene ring.

[0183] In preferred formula I and its sub-formulas, A represents a thioalkyl group having 1-7 carbon atoms, preferably straight-chain or branched, most preferably straight-chain, and preferably selected from -SCH3, -SC2H5 and -SC3H7, very preferably -SCH3 or -SC2H5, and most preferably -SCH3. Further preferably, A is selected from -CH2-S-CH3 or -CH2-S-C2H5.

[0184] A in preferred formula I a and A b Selected from groups including 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarin, flavonoids (wherein one or more CH groups in these groups may be replaced by N), cyclohexane-1,4-diyl (wherein one or more non-adjacent CH2 groups may be replaced by O and / or S), 1,4-cyclohexene. Hexenyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, piperidine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indane-2,5-diyl, or octahydro-4,7-bridged methylene indane-2,5-diyl, all of which are optionally substituted with one or more groups A, L, or P-Sp-, and at least one of the groups A a Or A b Preferably, at least one aryl or heteroaryl A a Or A b It is substituted by at least one group A.

[0185] A in the most preferred formula I a and A b The group is selected from benzene, naphthalene, phenanthrene, anthracene, dibenzofuran, or dibenzothiophene, all of which are optionally substituted by one or more groups A, L, or P-Sp-, and at least one of the groups A a Or A b It is substituted by at least one group A.

[0186] In preferred form I, z is 0, 1, or 2, with 1 or 2 being highly preferred.

[0187] -A in preferred formula Ia -(Z a -A b ) z - represents benzene, biphenylene, p-terphenylene (1,4-diphenylbenzene), m-terphenylene (1,3-diphenylbenzene), naphthylene, 2-phenyl-naphthylene, phenanthrene or anthracene, dibenzofuran or dibenzothiophene, all of which are optionally substituted by one or more groups A, L or P-Sp- and at least monosubstituted by A.

[0188] Further preferably, it contains at least one unsubstituted group A. a Or A b Formula I and its sub-formula compounds.

[0189] Further preferred are compounds of formula I and its sub-formulas as described in the context, wherein -A a -(Z a -A b ) z -Selected from the following formula

[0190]

[0191] The single bonds depict the groups P-Sp and R in Formula I. b The linker group, wherein the benzene ring is optionally further substituted by one or more groups A, L or P-Sp- as defined in Formula I, and at least one benzene ring is substituted by at least one group A, and preferably at least one benzene ring is not substituted with any substituent A or L.

[0192] Preferred formulas A1, A2 and A5, more preferred formulas A1 and A2, and most preferred formula A1.

[0193] Preferred compounds of formula I are selected from the following sub-formulas

[0194]

[0195] Each group is independent of the others and, each time it appears, has the same or different meanings as follows:

[0196] A, P, Sp, R b It has one of the meanings given by Equation I or one of the preferred meanings given by the context.

[0197] L 11 -L 17 The metal is L or A, preferably F, Cl, OCH3, OCF3, CN, P-Sp or A.

[0198] r1, r2, r3, r4 are 0, 1, 2, 3, or 4, preferably 0, 1, or 2, and very preferably 0 or 1, wherein in equations I1, I2, and I5, r1 + r2 + r3 ≥ 1.

[0199] r5, r6, can be 0, 1, 2, or 3, preferably 0, 1, or 2, and very preferably 0 or 1, wherein r5 + r6 ≥ 1 in equation I3 and r4 + r5 + r6 ≥ 1 in equations I4a and I4b.

[0200] r7 can be 1, 2, 3, or 4, preferably 1 or 2, and very preferably 1.

[0201] The compound contains at least one L group of type A. 11 -L 17 .

[0202] The preferred compounds are I1, I2 and I5, the most preferred compounds are I1 and I2, and the most preferred compound is I1.

[0203] Further preferred formula I12 compound

[0204]

[0205] Where P, Sp, R b , L 11 , L 12 , L 13 r1, r2 and r3 have the meaning given in the context, r1+r2+r3≥ 1, and c is 0, 1 or 2, preferably 0 or 1.

[0206] The preferred sub-formulas of formula I12 include the preferred sub-formulas of formulas I1 and I2 listed below.

[0207] Further preferred compounds are those of formula I, I1-I6, and I12, wherein R b It represents P-Sp.

[0208] Further preferred compounds are those of formula I, I1-I6, and I12, wherein R b Unlike P-Sp, and preferably representing F, Cl, CN or a straight-chain, branched or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, and wherein one or more H atoms are optionally replaced by F or Cl.

[0209] Further preferred compounds are those of formula I1, I2, I5 (where at least one of r1, r2, and r3 is 0), those of formula I3 (where at least one of r4 and r5 is 0), those of formula I4a and I4b (where at least one of r4, r5, and r6 is 0), and those of formula I12 (where one of r1 and r2 is 0 if c is 0, and at least one of r1, r2, and r3 is 0 if c is 1 or 2).

[0210] Preferred compounds of formula I, I1-I6, and I12 are selected from the following sub-formulas:

[0211]

[0212]

[0213]

[0214]

[0215] in

[0216] R, P, Sp, L 11-17 r1-r7 have one of the meanings given in Equation I or as a preferred meaning given in the context.

[0217] L 18 , L 19 and L 20 Having for L 11 One of the meanings given is

[0218] r8 can be 0, 1, or 2, preferably 0 or 1.

[0219] r9 can be 0, 1, 2, or 3, preferably 0, 1, or 2, and very preferably 0 or 1.

[0220] r10 can be 1, 2, or 3, preferably 1 or 2, and very preferably 1.

[0221] Sp(P)2 represents a spacer group Sp that is replaced by two polymerizable groups P at the same or different positions, and

[0222] in

[0223] In equations I1A, I1C, and I1E, r1 + r2 ≥ 1.

[0224] In equations I1B, I1D, and I1F, r1 + r5 ≥ 1.

[0225] In equations I1G, I3A, and I3C, r5 + r6 ≥ 1.

[0226] In equations I2A, I2D, I2E, I5A, and I5C, r1 + r2 + r3 ≥ 1.

[0227] In equations I2B, I2C, I2F, I5B, and I5D, r1 + r3 + r5 ≥ 1.

[0228] In equation I2G, r3 + r5 + r6 ≥ 1,

[0229] In equations I4A, I4C, and I4E, r4 + r5 + r6 ≥ 1.

[0230] In equation I4D, r5 + r6 + r9 ≥ 1.

[0231] In equation I3B, r5 + r8 ≥ 1,

[0232] In equation I4B, r4 + r5 + r8 ≥ 1.

[0233] And the compound contains at least the L group representing A. 11 -L 20 .

[0234] Further preferred compounds of formula I and I12 are selected from the following sub-formulas.

[0235]

[0236] in

[0237] R, P, Sp, Sp(P)2, L 11-16 r1-r6 have one of the meanings given by Equation I2D or one of the preferred meanings given in the context.

[0238] c is 0, 1, or 2.

[0239] In equations I12A, I12D, and I12E, r1 + r2 + r3 ≥ 1.

[0240] In equations I12B, I12C, and I12F, r1 + r3 + r5 ≥ 1.

[0241] In equation I12G, r3 + r5 + r6 ≥ 1,

[0242] And the compound contains at least one A group L. 11 -L 16 .

[0243] Preferably, in compounds of formula I12A-I12G, if c is 0, then one of r1 and r2 is 0, and if c is 1 or 2, then at least one of r1, r2 and r3 is 0.

[0244] The highly preferred compound is I12A.

[0245] Further preferred compounds of formula I, I1-I6, I12, I1A–I6C, and I12A–I12G are selected from the following sub-formulas:

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294] Wherein R, P, Sp, Sp(P)2, A and L have one of the meanings given in Formula I or as preferred in the context, L is preferably F, Cl or CN, A is preferably a thioalkyl group having 1-7 C atoms, preferably a straight chain, more preferably -SCH3, -SC2H5 or -SC3H7, very preferably -SCH3, and even more preferably -CH2S-CH3 or -CH2-S-C2H5.

[0295] Compounds selected from formulas I1A-1 to I2G-4 are particularly preferred.

[0296] Further preferred compounds of formula I, I1-I6, I12, I1A–I5D, I12A–I12G, and I1A-1 to I6C-1 are selected from the following sub-formulas:

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403] Wherein A, L, R, P, Sp and Sp(P)2 have one of the meanings given in Formula I or the preferred meanings given in the context, and A is preferably a thioalkyl group having 1-7 C atoms, preferably a straight chain, more preferably -SCH3, -SC2H5 or -SC3H7, very preferably -SCH3, and even more preferably -CH2S-CH3 or -CH2-S-C2H5.

[0404] Compounds selected from formulas I1A-1-1 to I2D-30-4 are highly preferred.

[0405] The preferred compounds are I1A-1-1 to I1B-8-6, I1D-1-1 to I2C-15-4, I2E-1-1 to I5B-9-4 and I5D-1-1 to I5D-5-3.

[0406] Further preferred compounds are those of formulas I1A-1-1 to I1A-7-3, I2A-1-1 to I2A-18-12, I5A-1-1 to I5A-19-3, and I6A-1-1 to I6B-2-1, wherein all Sp groups are single bonds. Further preferred compounds are those of formulas I1A-1-1 to I1A-7-3, I2A-1-1 to I2A-18-2, I5A-1-1 to I5A-19-3, and I6A-1-1 to I6B-2-1, wherein one Sp group represents a single bond and the other Sp group is not a single bond.

[0407] Further preferred compounds are those of formulas I1B-1-1 to I1B-8-6, I1D-1-1 to I1G-3-1, I2B-1-1 to I2C-15-4, I2E-1-1 to I2G-4-1, I5B-1-1 to I5B-9-4, I5D-1-1 to I5D-5-3, and I6C-1-1, wherein all Sp groups are single bonds. Further preferred compounds are those of formulas I1B-1-1 to I1B-8-6, I1D-1-1 to I1G-3-1, I2B-1-1 to I2C-15-4, I2E-1-1 to I2G-4-1, I5B-1-1 to I5B-9-4, I5D-1-1 to I5D-5-3, and I6C-1-1, wherein one or two Sp groups represent single bonds and the other Sp groups are not single bonds. Further preferred compounds are those of the formulas I1B-1-1 to I1B-8-6, I1D-1-1 to I1G-3-1, I2B-1-1 to I2C-15-4, I2E-1-1 to I2G-4-1, I5B-1-1 to I5B-9-4, I5D-1-1 to I5D-5-3 and I6C-1-1, wherein one or two Sp groups are different from single bonds and the other Sp group represents a single bond.

[0408] Further preferred compounds are those of formulas I1C-1-1 to I1C-13-3, I2D-1-1 to I2D-30-4, and I5C-1-1 to I5C-28-3, wherein in the P-Sp group, the Sp group is a single bond. Further preferred compounds are those of formulas I1C-1-1 to I1C-13-3, I2D-1-1 to I2D-30-4, and I5C-1-1 to I5C-28-3, wherein all Sp groups are not single bonds.

[0409] Further preferred compounds are those of formulas I1A-1-1 to I6C-1-1, wherein A represents a thioalkyl group having 1 to 7 C atoms, preferably a straight chain, more preferably -SCH3, -SC2H5 or -SC3H7, most preferably -SCH3, and further preferably -CH2S-CH3 or -CH2-S-C2H5.

[0410] Further preferred compounds are those of formulas I1A-1-1 to I6C-1-1, wherein L represents F, Cl, CN or OCH3, with F being highly preferred.

[0411] Further preferred compounds are those of formulas I1A-1-1 to I6C-1-1, wherein P represents an acrylate group or a methacrylate group, with a methacrylate group being highly preferred.

[0412] Further preferred compounds are those of formulas I1A-1-1 to I6C-1-1, wherein when Sp is different from a single bond, it represents an alkylene with 2-6 C atoms.

[0413] Further preferred compounds are those of formulas I1A-1-1 to I6C-1-1, wherein all Sp groups represent single bonds, all P groups represent methacrylate groups, all A groups represent S-CH3, and all L groups represent F.

[0414] Preferred compounds of formulas I and II and their sub-formulas are selected from the following preferred embodiments, including any combination thereof:

[0415] - A compound containing a group A.

[0416] - Compounds containing two or more groups A,

[0417] - A compound containing one or more A groups and one or more L groups.

[0418] - Compounds containing two unfused or fused benzene rings, preferably unfused benzene rings.

[0419] - Compounds containing three or more, preferably three or four unfused or fused benzene rings.

[0420] - Compounds containing at least one benzene ring that is not substituted by A or L.

[0421] - A is a thioalkyl group having 1-7 carbon atoms, preferably a straight chain, more preferably -SCH3, -SC2H5 or -SC3H7, and very preferably -SCH3.

[0422] - A is either -CH2S-CH3 or -CH2-S-C2H5.

[0423] - A compound containing only one polymerizable group (represented by the group P).

[0424] - Compounds containing only two polymerizable groups (represented by the group P).

[0425] - Compounds containing only three polymerizable groups (represented by the group P).

[0426] - Compounds containing only four polymerizable groups (represented by the group P).

[0427] - P is selected from acrylate, methacrylate, and oxetane, with acrylate or methacrylate being most preferred.

[0428] - P is a methacrylate group.

[0429] - Pg is a hydroxyl group,

[0430] - Each Sp group represents a single bond.

[0431] - At least one Sp group is different from a single bond.

[0432] - At least one Sp group is a single bond and at least one Sp group is different from a single bond.

[0433] -Sp, when it differs from a single bond, is selected from -(CH2). p2 -、-(CH2) p2 -O-、-(CH2) p2 -CO-O-、-(CH2) p2 -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O- atom or CO- group is attached to the benzene ring.

[0434] -Sp, when not a single bond, is selected from -(CH2)2-, -(CH2)3-, -(CH2)4-, -O-(CH2)2-, -O-(CH2)3-, -O-CO-(CH2)2-, and -CO-O-(CH)2-, wherein the O atom or CO group is attached to the benzene ring.

[0435] - Sp represents a single bond or -(CH2). p2 -、-(CH2) p2 -O-、-(CH2) p2 -CO-O-、-(CH2) p2 -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O- atom or CO- group is attached to the benzene ring.

[0436] - Sp(P)2 is selected from subforms Sp1a-Sp3a,

[0437] - R b Indicates P-Sp-,

[0438] - R b It does not represent or contain polymerizable groups.

[0439] - R b The symbol represents F, Cl, CN, or a straight-chain, branched, or cyclic alkyl group having 1-25 carbon atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O-, such that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are optionally replaced by F or Cl.

[0440] - R represents F, Cl, CN, or a straight-chain, branched, or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O-, such that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are optionally replaced by F or Cl.

[0441] - Z 1 It is a single key.

[0442] - z can be 0, 1, 2, or 3, with 0 or 1 being the most preferred.

[0443] - L is selected from F, Cl, CN, alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy or alkoxy carbonyloxy, each having 1-6 C atoms, wherein one or more H atoms may optionally be replaced by F or Cl, preferably F, Cl, CN or OCH3, and very preferably F.

[0444] The most preferred formula I and its sub-formulas are selected from the following sub-formulas:

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455] Further preferred compounds of formulas I1A-1-1a to I2B-1-6b, wherein one, two, or three methacrylate groups are replaced by acrylate groups.

[0456] For use in PSA displays, the total proportion of polymerizable compounds of formula I and its sub-formulas in the LC medium is preferably 0.01-2.0%, very preferably 0.1-1.0%, and most preferably 0.2-0.8%.

[0457] For use in SA-VA displays, the total proportion of polymerizable compounds of formula I and its sub-formulas in the LC medium is preferably >0 to < 3%, very preferably >0 to < 2%, more preferably 0.05-2.0%, and most preferably 0.05-1.0%.

[0458] Compounds of Formula I can be prepared by methods similar to those known to those skilled in the art and described in standard works of organic chemistry, such as those in Houben-Weyl, Methoden der Organischen Chemie [Methods of OrganicChemistry], Thieme-Verlag, Stuttgart.

[0459] For example, acrylates or methacrylates can be produced by reacting them with a base such as pyridine or triethylamine, and 4-( N,N The corresponding alcohol is prepared by esterification with an acid derivative, such as (meth)acryloyl chloride or (meth)acrylic anhydride, in the presence of dimethylaminopyridine (DMAP). Alternatively, the ester can be prepared by dehydration with a dehydrating agent, such as dicyclohexylcarbodiimide (DCC) or N-(3-dimethylaminopropyl)- N' -Ethylcarbodiimide (EDC) or N-(3-dimethylaminopropyl)- N' The alcohol is prepared by esterification with (meth)acrylic acid in the presence of ethylcarbodiimide hydrochloride and DMAP.

[0460] Further suitable and preferred general synthetic methods for compounds of formula I are shown in Scheme 1 below.

[0461] Option 1

[0462]

[0463]

[0464] Where Z represents H or -R-OH, Y represents boronic ester, boric acid, or halogen, and X represents... 1,2,3 Halogens are indicated, preferably Br or Cl, R 1 ,2,3,4 represents a substituent, Pg represents a protecting group or H, and m ≥ 0 and m = 0 represent a single bond.

[0465] Compounds of formula I and its sub-forms with different substitution methods or different mesocrystalline groups can be prepared in a manner similar to scheme 1.

[0466] In addition to the polymerizable compounds described above, the LC medium used in the LC display of the present invention also comprises an LC mixture (“body mixture”) containing one or more, preferably two or more, LC compounds selected from non-polymerizable low molecular weight compounds, wherein at least one is a compound of formula II. These LC compounds are selected such that they are stable and / or non-reactive to the polymerization reaction under the polymerization conditions applied to the polymerizable compounds.

[0467] A particularly preferred embodiment of this LC medium is shown below.

[0468] Preferably, the LC medium contains one or more compounds of formula II selected from compounds of formulas IIA, IIB, IIC, and IID.

[0469]

[0470] in

[0471] R 2A and R 2B Each of these groups independently represents H, an alkyl or alkenyl group having up to 15 carbon atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more CH2 groups among these groups can be used such that the O atom is not directly attached to each other by -O-, -S-,

[0472]

[0473] Replace with -C≡C-, -CF₂O-, -OCF₂-, -OC-O-, or -O-CO-.

[0474] L 1 -L 4 Each can be independently represented as F, Cl, CF3, or CHF2.

[0475] Y represents H, F, Cl, CF3, CHF2, or CH3, with H or CH3 being preferred, and H being particularly preferred.

[0476] Z 2 Z 2B and Z 2D Each of these independently represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-.

[0477] p represents 0, 1, or 2, and

[0478] q represents either 0 or 1 each time it appears.

[0479] Preferred compounds of formulas IIA, IIB, IIC, and IID are those in which R 2B Those that represent alkyl or alkoxy groups having a maximum of 15 carbon atoms, and very preferably (O)C. v H 2v+1 , where (O) is an oxygen atom or a single bond and v is 1, 2, 3, 4, 5 or 6.

[0480] Further preferred compounds of formulas IIA, IIB, IIC, and IID are those in which R 2A Or R 2B Those that represent or contain cycloalkyl or cycloalkoxy groups are preferably selected from...

[0481]

[0482] Where S 1 C 1-5 -alkylene or C 2-5 - Idemenyl and S 2 For H, C 1-7 -alkyl or C 2-7 -Alkenyl, and very preferably selected from

[0483]

[0484] In a preferred embodiment, the LC medium comprises one or more compounds of formula IIA selected from IIA-1 to IIA-76.

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494] The index 'a' represents 1 or 2, and "alkyl" and "alkyl Each of these terms independently represents a straight-chain alkyl group having 1-6 carbon atoms, "alkenyl" represents a straight-chain alkenyl group having 2-6 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-.

[0495] Particularly preferred LC media of the present invention comprise one or more compounds selected from formulas IIA-2, IIA-8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42 and IIA-43.

[0496] In another preferred embodiment, the LC medium comprises one or more compounds of formula IIB selected from formulas IIB-1 to IIB-26.

[0497]

[0498]

[0499]

[0500] Among them, "alkyl" and "alkyl “,”, “alkenyl” and (O) have the meanings given above.

[0501] A particularly preferred LC medium of the present invention comprises one or more compounds selected from formulas IIB-2, IIB-10 and IIB-16.

[0502] In another preferred embodiment, the LC medium comprises one or more compounds of formula IIC-1.

[0503]

[0504] Among them, "alkyl" and "alkyl " and (O) have the meanings given above.

[0505] In another preferred embodiment, the LC medium comprises one or more IID compounds selected from formulas IID-1 to IID-10.

[0506]

[0507]

[0508] Among them, "alkyl" and "alkyl “,”, “alkenyl” and (O) have the meanings given above.

[0509] The particularly preferred LC medium of the present invention comprises one or more compounds of formula IID-4.

[0510] The proportion of compounds of formula IIA and / or IIB in the mixture as a whole is preferably at least 20 wt%.

[0511] In another preferred embodiment, the LC medium comprises one or more compounds of formula III.

[0512]

[0513] in

[0514] R 11 and R 12 Each of these groups independently represents H, an alkyl or alkoxy group having 1-15 carbon atoms, wherein one or more CH2 groups among these groups can be represented independently such that the O atom is not directly connected to each other.

[0515]

[0516] The following halogens can be substituted: -O-, -S-, -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -OC-O-, or -O-CO-, and in addition, one or more H atoms can be substituted by halogens.

[0517] A 3 Each occurrence represents an independent representation.

[0518] a) 1,4-cyclohexeneyl or 1,4-cyclohexeneyl, wherein one or both non-adjacent CH2 groups may be replaced by -O- or -S-.

[0519] b) 1,4-Phenylidene, wherein one or both CH groups may be replaced by N, or

[0520] c) A group selected from spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octyl, 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.

[0521] Groups a), b), and c) can be mono- or poly-substituted with halogen atoms.

[0522] n represents 0, 1, or 2, preferably 0 or 1.

[0523] Z1 Each occurrence independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond, and

[0524] L 11 and L 12 Each of these elements independently represents F, Cl, CF3, or CHF2, preferably H or F, with F being the most preferred.

[0525] W represents O or S.

[0526] In a preferred embodiment of the present invention, the LC medium comprises one or more compounds of formula III-1 and / or III-2.

[0527]

[0528] The groups appearing therein have the same meaning as given in Formula III above and are preferably...

[0529] R 11 and R 12 Each of the alkyl, alkenyl, or alkoxy groups having a maximum of 15 carbon atoms, more preferably one or both of them, represents an alkoxy group and...

[0530] L 11 and L 12 Each is preferred, represented by F.

[0531] In another preferred embodiment, the LC medium comprises one or more compounds of formula III-1 selected from formulas III-1-1 to III-1-10, preferably formula III-1-6.

[0532]

[0533] Among them, "alkyl" and "alkyl "Each independently represents a straight-chain alkyl group having 1-6 carbon atoms, 'alkenyl' and 'alkenyl'" "Each independently represents a straight-chain alkenyl group with 2-6 carbon atoms, "alkoxy" and "alkoxy" "Each independently represents a straight-chain alkoxy group having 1-6 carbon atoms, and L..." 11 and L 12 Each can be represented independently as F or Cl, with F being the preferred choice.

[0534] In another preferred embodiment, the LC medium comprises one or more compounds of formula III-2 selected from formulas III-2-1 to III-2-10, preferably formula III-2-6.

[0535]

[0536] Among them, "alkyl" and "alkyl "Each independently represents a straight-chain alkyl group having 1-6 carbon atoms, 'alkenyl' and 'alkenyl'" "Each independently represents a straight-chain alkenyl group with 2-6 carbon atoms, "alkoxy" and "alkoxy" "Each independently represents a straight-chain alkoxy group having 1-6 carbon atoms, and L..." 11 and L 12 Each can be represented independently as F or Cl, with F being the preferred choice.

[0537] In a highly preferred embodiment, the LC medium comprises one or more compounds selected from the following formulas.

[0538]

[0539] In another preferred embodiment of the invention, the LC medium comprises one or more compounds of formula IIIA-1 and / or IIIA-2.

[0540]

[0541] Where L 11 and L 12 Having the same meaning as given in Equation III, (O) represents O or a single bond.

[0542] R IIIA This refers to an alkyl or alkenyl group, or a Cy-C group, having a maximum of 7 carbon atoms. m H 2m+1 -,

[0543] m and n are the same or different from 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, and

[0544] Cy represents an alicyclic group having 3, 4 or 5 ring atoms, which may be alkyl or alkenyl groups having a maximum of 3 C atoms, or may be substituted with halogen or CN, and preferably represents cyclopropyl, cyclobutyl or cyclopentyl.

[0545] Compounds of formula IIIA-1 and / or IIIA-2 may replace compounds of formula III or be additionally contained in the LC medium, preferably additionally.

[0546] The most preferred compounds of formula IIIA-1 and IIIA-2 are as follows:

[0547]

[0548] Wherein “alkoxy” represents a straight-chain alkoxy group having 1-6 carbon atoms, and preferably represents n-propoxy, n-butyloxy, n-pentoxy or n-hexyloxy.

[0549] In a preferred embodiment of the present invention, the LC medium comprises one or more compounds of formula III-3.

[0550]

[0551] in

[0552] R 11 , R 12 The same or different representations of H, alkyl or alkoxy groups having 1-15 C atoms, wherein one or more CH2 groups of these groups are optionally independently represented such that the O atoms are not directly connected to each other by -C≡C-, -CF2O-, -OCF2-, -CH=CH-,

[0553]

[0554] -O-, -S-, -CO-O-, or -O-CO- are used as substitutes, and one or more H atoms may be substituted with halogens.

[0555] Compounds of formula III-3 are preferably selected from formulas III-3-1 to III-3-11:

[0556]

[0557]

[0558] Where R 12 The alkyl group having 1 to 7 carbon atoms is preferred to be ethyl, n-propyl, n-butyl, n-pentyl or n-hexyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl.

[0559] In another preferred embodiment of the invention, the LC medium comprises one or more compounds of formula III-4 to III-6, preferably formula III-5.

[0560]

[0561] The parameters have the meanings given above, R 11 Preferably, it represents straight-chain alkyl and R 12Preferably, alkoxy groups are used, each having 1-7 carbon atoms.

[0562] In another preferred embodiment, the LC medium comprises one or more compounds of formula I selected from formulas III-7 to III-9, preferably formula III-8.

[0563]

[0564] The parameters have the meanings given above, R 11 Preferably, it represents straight-chain alkyl and R 12 Preferably, alkoxy groups are used, each having 1-7 carbon atoms.

[0565] In a preferred embodiment, the medium comprises one or more compounds of formula IV.

[0566]

[0567] in

[0568] R 41 This refers to an unsubstituted straight-chain, branched, or cyclic alkyl group having 1-7 carbon atoms, or an unsubstituted alkenyl group having 2-7 carbon atoms, preferably. n -alkyl groups, particularly preferably having 2, 3, 4 or 5 carbon atoms, and

[0569] R 42 The term refers to an unsubstituted straight-chain, branched, or cyclic alkyl group having 1-7 carbon atoms, or an unsubstituted alkoxy group having 1-6 carbon atoms (preferably having 2-5 carbon atoms), an unsubstituted alkenyl group having 2-7 carbon atoms, preferably having 2, 3, or 4 carbon atoms, more preferably vinyl or 1-propenyl, and especially vinyl.

[0570] Compounds of formula IV are preferably selected from formulas IV-1 to IV-6.

[0571]

[0572] in

[0573] “alkyl” and “alkyl” "Each term independently represents an alkyl group having 1-7 carbon atoms, preferably having 2-5 carbon atoms."

[0574] "alkenyl" indicates an alkenyl group having 2-5 carbon atoms, preferably 2-4 carbon atoms, and particularly preferably 2 carbon atoms.

[0575] alkenyl "Indicates an alkenyl group having 2-5 carbon atoms, preferably 2-4 carbon atoms, particularly preferably 2-3 carbon atoms, and..."

[0576] “alkoxy” refers to an alkoxy group having 1-5 carbon atoms, preferably having 2-4 carbon atoms.

[0577] Preferably, the LC medium comprises one or more compounds selected from formulas IV-1-1 to IV-1-9.

[0578]

[0579]

[0580] Among them, propyl, butyl, and pentyl are straight-chain groups.

[0581] Most preferably, the LC medium of the present invention comprises one or more compounds of formula IV-2-1 and / or IV-2-2.

[0582]

[0583] Most preferably, the LC medium of the present invention comprises a compound of formula IV-3, particularly selected from formulas IV-3-1 to IV-3-6.

[0584]

[0585] Most preferably, the LC medium of the present invention comprises a compound of formula IV-4, particularly selected from formulas IV-4-1 and IV-4-2.

[0586]

[0587] LC media preferably additionally contain one or more compounds of formula IVa.

[0588]

[0589] in

[0590] R 41 and R 42 Each of these independently represents a straight-chain alkyl, alkoxy, alkenyl, alkoxyalkyl, or alkoxy group having a maximum of 12 carbon atoms.

[0591] express , , , or ,

[0592] Z 4It represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, or -CF=CF-.

[0593] Preferred compounds of formula IVa are shown below:

[0594]

[0595] Among them alkyl and alkyl Each of these terms independently represents a straight-chain alkyl group having 1-6 carbon atoms.

[0596] The LC medium of the present invention preferably contains at least one compound of formula IVa-1 and / or formula IVa-2.

[0597] The proportion of the IVa compound in the mixture as a whole is preferably at least 5 wt%.

[0598] Preferably, the LC medium comprises one or more compounds of formula IVb-1 to IVb-3.

[0599]

[0600] in

[0601] “alkyl” and “alkyl” "Each independently represents a straight-chain alkyl group having 1-6 carbon atoms, and..."

[0602] “alkenyl” and “alkenyl” Each of these groups independently represents a straight-chain alkenyl group having 2-6 carbon atoms.

[0603] The proportion of biphenyls of formula IV-1 to IV-3 in the mixture as a whole is preferably at least 3 wt%, especially 5wt%.

[0604] Of the compounds of formulas IVb-1 to IVb-3, compound IVb-2 is particularly preferred.

[0605] The preferred biphenyl is

[0606]

[0607] Among them, "alkyl" "" indicates an alkyl group having 1-6 carbon atoms, and preferably n-propyl.

[0608] The LC media of the present invention particularly preferably contain one or more compounds of the formula IVb-1-1 and / or IVb-2-3.

[0609] In a preferred embodiment, the LC medium comprises one or more compounds of formula V.

[0610]

[0611] in

[0612] R 51 and R 52 They are independent of each other for R 41 and R 42 The term "alkyl" is given in one of the following meanings and is preferably interpreted as having 1-7 carbon atoms, preferably n-alkyl, particularly preferably n-alkyl having 1-5 carbon atoms; alkoxy having 1-7 carbon atoms, preferably n-alkoxy, particularly preferably n-alkoxy having 2-5 carbon atoms; or alkoxyalkyl, alkenyl, or alkenyloxy having 2-7 carbon atoms, preferably having 2-4 carbon atoms, preferably alkenyloxy.

[0613]

[0614] in

[0615]

[0616] 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, and particularly preferably a single bond.

[0617] n is 1 or 2.

[0618] Compounds of formula V are preferably selected from formulas V-1 to V-16:

[0619]

[0620] Where R 1 and R 2 Having the above for R 2A The meaning stated.

[0621] R 1 and R 2 Preferably, each represents a straight-chain alkyl or alkenyl group independently of the other.

[0622] Preferred LC media comprise 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.

[0623] The LC media of the present invention particularly preferably contain compounds of formula V-10, V-12, V-16 and / or IV-1, especially in amounts of 5-30%.

[0624] Preferred compounds of formula V-10 are shown below:

[0625]

[0626] The LC medium of the present invention particularly preferably comprises a combination of a tricyclic compound of formula V-10a and / or formula V-10b and one or more bicyclic compounds of formula IV-1. The total proportion of the combination of the compound of formula V-10a and / or V-10b and one or more compounds selected from the dicyclohexyl compound of formula IV-1 is 5-40%, very particularly preferably 15-35%.

[0627] The most particularly preferred LC media contain compounds V-10a and IV-1-1 (CC-2-3).

[0628]

[0629] 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%, based on the mixture as a whole.

[0630] The most particularly preferred LC media contain compounds V-10b and IV-1-1:

[0631]

[0632] 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%, based on the mixture as a whole.

[0633] The most particularly preferred LC media contain one, two, or three of the following three compounds:

[0634]

[0635] 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%, based on the mixture as a whole.

[0636] Preferred LC media contain at least one compound selected from the following formula

[0637]

[0638] Where R 41 and R 42and R 51 and R 52 It has the meaning described above. Preferably, in compounds V-6, V-7, and IV-1, R 41 and R 51 This indicates an alkyl or alkenyl group having 1-6 carbon atoms or 2-6 carbon atoms, and R 42 and R 52 This indicates an alkenyl group having 2-6 carbon atoms.

[0639] Preferred LC media comprise at least one compound of formula V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a, and IV-3b:

[0640]

[0641] Where alkyl represents an alkyl group having 1-6 carbon atoms and alkenyl represents an alkenyl group having 2-6 carbon atoms.

[0642] 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 LC medium of the present invention in an amount of 1-40 wt%, preferably 5-35 wt% and very particularly preferably 10-30 wt%.

[0643] In a preferred embodiment of the invention, the LC medium additionally comprises one or more compounds selected from formulas VI-1 to VI-9.

[0644]

[0645] in

[0646] R 7 Each has its own independent property regarding R in Equation IIA 2A One of the meanings, and

[0647] w and x each represent 1-6 independently.

[0648] Particularly preferred is that the LC medium contains at least one compound of formula V-9.

[0649] In a preferred embodiment of the invention, the LC medium further comprises one or more compounds selected from formulas VII-1 to VII-25.

[0650]

[0651]

[0652]

[0653] in

[0654] R represents a straight-chain alkyl or alkoxy group with 1-6 carbon atoms, (O) represents -O- or a single bond, X represents F, Cl, OCF3 or OCHF2, and L represents... x It represents H or F, where m is 0, 1, 2, 3, 4, 5 or 6 and n is 0, 1, 2, 3 or 4.

[0655] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0656] X preferably represents F or OCH3, with F being the most preferred.

[0657] The LC medium of the present invention preferably contains terphenyl of formulas VII-1 to VII-25 in an amount of 2-30 wt%, particularly 5-20 wt%.

[0658] Particularly preferred are compounds of formulas VII-1, VII-2, VII-4, VII-20, VII-21, and VII-22, wherein X represents F. In these compounds, R preferably represents an alkyl group and an alkoxy group, each having 1-5 carbon atoms. 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.

[0659] If the mixture n value If the content is 0.1, then terphenyl compounds of formulas VII-1 to VII-25 are preferably used in the LC medium of the present invention. The preferred LC medium contains 2-20 wt% of one or more terphenyl compounds selected from formulas VII-1 to VII-25.

[0660] Further preferred implementation schemes are listed below:

[0661] a) The LC medium contains at least one compound selected from formulas Z-1 to Z-14.

[0662]

[0663]

[0664] R, (O) and "alkyl" have the meanings described above for Formula III.

[0665] b) Preferably, the LC medium of the present invention comprises one or more substances containing a tetrahydronaphthyl or naphthyl unit, such as compounds of formula N-1 to N-5.

[0666]

[0667] Where R 1N and R 2N Each independently possesses the above-mentioned characteristics for R. 2A The meaning of the above preferably refers to a straight-chain alkyl, a straight-chain alkoxy, or a straight-chain alkenyl group, and

[0668] Z 1 and Z 2 Each of these can be represented independently as -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.

[0669] c) Preferred LC media comprise one or more compounds selected from those of formula BC difluorodibenzo-p-chromium, formula CR chromium, and fluorophenanthrene compounds of formulas PH-1 and PH-2.

[0670]

[0671] in

[0672] R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 Each has its own R independently 2A Meaning. c can be 0, 1, or 2. R 1 and R 2 Preferably, alkyl or alkoxy groups having 1-6 carbon atoms are represented independently of each other.

[0673] The LC medium of the present invention preferably contains compounds of formula BC, CR, PH-1, and PH-2 in an amount of 3-20 wt%, particularly in an amount of 3-15 wt%.

[0674] Particularly preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5.

[0675]

[0676]

[0677] in

[0678] “alkyl” and “alkyl” "Each independently represents a straight-chain alkyl group having 1-6 carbon atoms, and..."

[0679] “alkenyl” and

[0680] alkenyl Each of these groups independently represents a straight-chain alkenyl group having 2-6 carbon atoms.

[0681] It is particularly preferred that the LC medium contains one, two or three compounds of the form BC-2, BF-1 and / or BF-2.

[0682] d) The preferred LC medium comprises one or more Ininium compounds.

[0683] In

[0684] in

[0685] R 11 , R 12 ,

[0686] R 13 Each of these terms independently represents a straight-chain alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1-6 carbon atoms.

[0687] R 12 and R 13 Additional indication: halogen, preferably F.

[0688] express

[0689]

[0690] i represents 0, 1, or 2.

[0691] Preferred In compounds are those of formulas In-1 to In-16 as described below:

[0692]

[0693]

[0694] Compounds of formulas In-1, In-2, In-3 and In-4 are particularly preferred.

[0695] Compounds of formula In and sub-formulas In-1 to In-16 are preferably used in the LC media of the present invention at a concentration of ≥ 5 wt%, particularly 5-30 wt% and very particularly preferably 5-25 wt%.

[0696] e) Preferred LC media additionally comprise one or more compounds of formula L-1 to L-5.

[0697]

[0698] in

[0699] R and R 1 Each of them independently possesses the above-mentioned characteristics for R in Equation IIA. 2A The meanings are as follows: alkyl indicates an alkyl group having 1-6 carbon atoms. The parameter s indicates 1 or 2.

[0700] Compounds of formulas L-1 to L-5 are preferably used at a concentration of 5-50 wt%, particularly 5-40 wt%, and very particularly preferably 10-40 wt%.

[0701] f) Preferred LC media additionally contain one or more compounds of formula IIA-Y.

[0702]

[0703] Where R 11 and R 12 Having the above for R in Equation IIA 2A One of the given meanings, and L 1 and L 2 F or Cl can be represented in the same or different ways.

[0704] Preferred compounds of formula IIA-Y are selected from the following sub-formulas.

[0705]

[0706]

[0707] Among them, Alkyl and Alkyl Each of these terms independently represents a straight-chain alkyl group having 1-6 carbon atoms; Alkoxy represents a straight-chain alkoxy group having 1-6 carbon atoms; Alkenyl and Alkenyl Each of these characters independently represents a straight-chain alkenyl group with 2-6 carbon atoms, and O represents an oxygen atom or a single bond. Alkenyl and Alkenyl The preferred representations are 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-.

[0708] The particularly preferred compounds of formula IIA-Y are selected from the following sub-formulas:

[0709]

[0710] Alkoxy and Alkoxy It has the meaning defined above and preferably represents methoxy, ethoxy, n-propyloxy, n-butyloxy or n-pentoxy.

[0711] g) An LC medium additionally comprising one or more compounds selected from the following tetraphenyl compounds:

[0712]

[0713] in

[0714] R Q It is an alkyl, alkoxy, oxalyl, or alkoxyalkyl group having 1-9 carbon atoms, or an alkenyl or alkenoxy group having 2-9 carbon atoms, all of which may optionally be fluorinated.

[0715] X Q It is F, Cl, a haloalkyl or alkoxy group having 1-6 carbon atoms, or a haloalkenyl or alkenoxy group having 2-6 carbon atoms.

[0716] L Q1 -L Q6 Each is independently H or F, where L Q1 -L Q6 At least one of them is F.

[0717] The preferred compound of formula Q is wherein R Q Those that represent straight-chain alkyl groups having 2-6 C- atoms are very preferred, with ethyl, n-propyl or n-butyl being the most preferred.

[0718] The preferred compound of formula Q is wherein L Q3 and L Q4 Those that are F. A further preferred formula Q compound is one in which L... Q3 L Q4 and L Q1 and L Q2 Those whose one or two are F.

[0719] The preferred compound of formula Q is wherein X Q For those representing F or OCF3, F is highly preferred.

[0720] Compound Q is preferably selected from the following sub-formulas

[0721]

[0722] Where R Q It has one of the meanings of formula Q or one of its preferred meanings given in the context, and preferably ethyl, n-propyl or n-butyl.

[0723] The preferred compound is of formula Q1, especially R. Q Those that are n-propyl.

[0724] Preferably, the proportion of compound Q in the LC main mixture is > 0 to ≤ 5 wt%, very preferably 0.05-2 wt%, more preferably 0.1-1 wt%, and most preferably 0.1-0.8 wt%.

[0725] The preferred LC medium contains 1-5 compounds, preferably 1 or 2 compounds of formula Q.

[0726] Adding a Q-type tetraphenyl compound to the LC host mixture can reduce ODF inhomogeneity while maintaining high UV absorption, enabling rapid and complete polymerization, producing a strong and fast tilt angle, and improving the UV stability of the LC medium.

[0727] Furthermore, adding a Q-type compound with positive dielectric anisotropy to an LC dielectric with negative dielectric anisotropy allows for better control of the dielectric constant ε. and ε The value of ε can be achieved, especially high dielectric constant ε. The value of is adjusted, and the dielectric anisotropy Δε is kept constant, thereby reducing the recoil voltage and reducing image stickiness.

[0728] The LC medium of the present invention preferably includes

[0729] - One or more polymerizable compounds of formula I or its sub-formulas, preferably at a concentration of 0.01%-2.0%, more preferably 0.05%-1.0%, and most preferably 0.2%-0.8%.

[0730] and / or

[0731] - One or more compounds of formula IIA, preferably at a concentration of 5%-30%, more preferably 7%-25%, and particularly preferably 10%-20%;

[0732] and / or

[0733] - One or more compounds of formula IIA and IIB, preferably at a concentration of 30%-45%;

[0734] and / or

[0735] - One or more compounds of formula IV, preferably at a concentration of 35%-70%, more preferably 40%-65%, and particularly preferably 45%-60%;

[0736] and / or

[0737] - One or more of the formula IV-3 compounds, preferably at a concentration of 35%-60%, more preferably 40%-55%, and particularly preferably 45%-50%;

[0738] and / or

[0739] - One or more compounds of formula III-2, preferably formula III-2-6, preferably at a concentration of 2%-25%, more preferably 5%-15%, and particularly preferably 5-12%.

[0740] In particular, the medium contains

[0741] - One or more compounds CY-n-Om, particularly CY-3-O4, CY-5-O4 and / or CY-3-O2, preferably at a concentration of 5%-30%, more preferably 10%-20%;

[0742] and / or

[0743] - One or more compounds PY-n-Om, particularly PY-3-O2 and / or PY-1-O2, preferably at a concentration of 5%-30%, more preferably 5%-20%;

[0744] and / or

[0745] - CPY-n-Om, particularly CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably at a concentration > 5%, particularly 7%-20%, based on the mixture as a whole.

[0746] and / or

[0747] - One or more compounds CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, preferably at a concentration of > 3%, particularly 5-15%, based on a mixture as a whole;

[0748] and / or

[0749] - One or more compounds CPY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2, preferably at a concentration of > 3%, particularly 5-15%, based on a mixture as a whole;

[0750] and / or

[0751] - CLY-n-Om, preferably CLY-2-O4, CLY-3-O2 and / or CLY-3-O3, preferably with a concentration > 5%, particularly 10-30%, very preferably 15-20%, based on the mixture as a whole;

[0752] and / or

[0753] - CPY-n-Om and CY-n-Om, preferably at a concentration of 10-80%, based on a mixture as a whole.

[0754] and / or

[0755] - CPY-n-Om and PY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2 and PY-3-O2 or PY-1-O2, preferably at a concentration of 5-20%, more preferably 10-15%, based on the mixture as a whole.

[0756] and / or

[0757] - CC-3-V, preferably at a concentration of 5-50%, based on the mixture as a whole.

[0758] and / or

[0759] - A compound of formula CC-3-V1, with a total concentration of 5-40%, more preferably 15%-35%, and particularly preferably 20%-30%.

[0760] and / or

[0761] - 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 at a concentration of 2-12%.

[0762] and / or

[0763] - 0.1%-3% of the compound PPGU-3-F,

[0764] and / or

[0765] - Compound B(S)-(c5)1O-O2:

[0766] .

[0767] The LC dielectric of the present invention preferably has negative dielectric anisotropy.

[0768] More preferably, the LC dielectric of the present invention does not contain compounds having positive dielectric anisotropy, except for compounds of formula Q described below. Most preferably, the LC dielectric does not contain compounds having positive dielectric anisotropy.

[0769] In another preferred embodiment, the LC medium of the present invention does not contain compound of formula G.

[0770]

[0771] Each group, when appearing in the same or different manner, and independently of each other, has the following meaning:

[0772]

[0773] R0 This refers to a straight-chain or branched alkyl or alkoxy group having 1-15 carbon atoms, wherein one or more CH2 groups among these groups can be independently arranged such that the O atoms are not directly connected to each other. , , , , -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO- can be substituted, and wherein, in addition, one or more H atoms may be substituted with halogens, preferably with F.

[0774] X 0 This refers to F, Cl, CN, SF5, SCN, NCS, haloalkyl, haloalkenyl, haloalkoxy, or haloalkenoxy groups having up to 6 carbon atoms.

[0775] Z 0 It represents -C2H4-, -CH2O-, CF2O, -CH=CH-, or a single bond.

[0776] The present invention further relates to an active matrix addressing electro-optic display, characterized in that it contains the LC medium of the present invention as the dielectric, and 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-posi-VA, PS-TN, polymer-stabilized SA-VA, or polymer-stabilized SA-FFS display.

[0777] Advantageous for the liquid crystal medium of the present invention is that it preferably has the following characteristics. -20°C to 70°C, preferably -30°C to 80°C, a very special and preferred temperature. -40°C to Nematic phase at 90°C.

[0778] The medium of the present invention preferably has a clearing temperature of 70°C or higher, and very preferably 74°C or higher.

[0779] The LC medium preferably has a nematic LC phase.

[0780] The phrase "possessing a nematic phase" here means, on the one hand, that no smectic phase or crystallization was observed at the corresponding temperature at low temperatures, and on the other hand, that the nematic phase did not become clear upon heating. Low-temperature studies were conducted in a flow viscometer at the corresponding temperature and verified by storage for at least 100 hours in a test chamber with a layer thickness corresponding to the electro-optic application. If the storage stability in the corresponding test chamber at -20°C is 1000 hours or more, the medium is said to be stable at that temperature. The response times were 500 hours and 250 hours at -30°C and -40°C, respectively. At high temperatures, the clearing point was measured in a capillary using conventional methods.

[0781] The LC medium preferably has a nematic phase range of at least 60 K and a maximum of 30 mm at 20°C. 2 s -1 Flow viscosity 20 .

[0782] The LC medium is preferably nematic at -20°C or lower, more preferably at -30°C or lower, and very preferably at -40°C or lower.

[0783] The birefringence Δn value of the LC medium of the present invention is typically 0.07-0.16, preferably 0.08-0.15, and very preferably 0.09-0.14.

[0784] In a preferred embodiment, the birefringence of the LC medium of the present invention is 0.090-0.110, preferably 0.095-0.105, and particularly 0.100-0.105.

[0785] In another preferred embodiment, the LC medium of the present invention has a birefringence of 0.120 or higher, preferably 0.125-0.145, more preferably 0.130-0.140.

[0786] The LC dielectric of the present invention preferably has a dielectric anisotropy Δε of -1.5 to -8.0, more preferably -2.0 to -4.0, and particularly -2.5 to -3.5.

[0787] The LC medium of the present invention preferably has the following properties at 20°C. 120 mPa rotational viscosity of s 1, especially 100 mPa s.

[0788] In a preferred embodiment, the rotational viscosity at 20°C 1 is 100 mPa s, especially 95 mPa s.

[0789] The LC dielectrics of this invention preferably have relatively low threshold voltages (V0). They are preferably 1.7 V to 3.0 V, and particularly preferred. 2.7 V and a very special preferred option 2.5 V.

[0790] For the purposes of this invention, unless otherwise explicitly stated, the term “threshold voltage” refers to the capacitive threshold (V0), also known as the Freedericks threshold.

[0791] The LC dielectric of the present invention preferably has a high voltage retention rate in the liquid crystal cell.

[0792] Typically, LC dielectrics with low addressing voltages or threshold voltages exhibit lower voltage retention rates than those with higher addressing voltages or threshold voltages, and vice versa.

[0793] For the purposes of this invention, the term "dielectric positive compound" refers to a compound having... Compounds with a dielectric strength > 1.5 are referred to by the term "dielectrically neutral compound" as having a dielectric strength of -1.5. The terms 1.5 and "dielectric-negative compound" indicate that they possess... Those <-1.5. Here, the dielectric anisotropy of the compound is determined by dissolving 10% of the compound in the liquid crystal body in at least one test cell and measuring the capacitance of the resulting mixture. In each case, the test cell has a layer thickness of 20 µm and has vertical and surface alignment at 1 kHz. The measurement voltage is typically 0.5 V–1.0 V, but is always below the capacitance threshold of each liquid crystal mixture studied.

[0794] All temperature values ​​described in this invention are in °C.

[0795] The LC dielectrics of this invention are suitable for all VA-TFT (vertically aligned thin-film transistor) applications, such as VAN (vertically aligned nematic), MVA (multi-domain VA), (S)-PVA (super-patterned VA), ASV (advanced super-view or axisymmetric VA), PSA (polymer-stabilized VA), and PS-VA (polymer-stabilized VA). Furthermore, they are also suitable for IPS (in-plane switching) and FFS (edge-field switching) applications with negative Δε.

[0796] The nematic LC media in the display of the present invention typically comprises two components, NA and NB, which are themselves composed of one or more separate compounds.

[0797] The NA component exhibits significant negative dielectric anisotropy, and makes the dielectric anisotropy of the nematic phase... -0.5. In addition to one or more compounds of formula I, it preferably includes compounds of formula IIA, IIB and / or IIC, and one or more compounds of formula IV-1.

[0798] The proportion of component NA is preferably 45-100%, especially 60-85%.

[0799] For component NA, it is preferable to select one with One or more individual compounds with a Δε value of -0.8. The smaller the proportion of NA in the mixture as a whole, the more negative this value will be.

[0800] Component NB exhibits significant nematogeneity, and its flow viscosity at 20°C is no greater than 30 mm. 2 s -1 Preferably no larger than 25 mm 2 s -1 .

[0801] A particularly preferred single compound in component NB is a nematic liquid crystal with extremely low viscosity, having a flow viscosity of no more than 18 mm at 20°C. 2 s -1 Preferably no larger than 12 mm 2 s -1 .

[0802] Component NB is a monotropically or enantiotropically nematic, lacks a smectic phase, and can prevent the formation of a smectic phase in LC media at very low temperatures. For example, if various high-nematic materials are added to a smectic liquid crystal mixture, the nematic states of these materials can be compared by suppressing the degree to which a smectic phase is formed.

[0803] The mixture may also optionally include component NC, which contains components having Δε Compounds with a dielectric anisotropy of 1.5. These so-called positive compounds are usually... A 20 wt% amount is present in the mixture of negative dielectric anisotropy, based on the mixture as a whole.

[0804] In addition to one or more compounds of formula I or its sub-formulas, the medium preferably contains 4-15, particularly 5-12, and especially preferably <10 compounds of formula IIA, IIB and / or IIC, and optionally one or more compounds of formula IV-1.

[0805] In addition to compounds of formula I or its sub-formulas and compounds of formulas IIA, IIB and / or IIC and optional IV-1, other components may also be present in an amount of up to 45% of the mixture as a whole, but preferably up to 35%, and particularly up to 10%.

[0806] Other components are preferably selected from nematogenic substances, particularly from known substances of the following categories: azobenzene, benzenemethylaniline, biphenyl, terphenyl, phenyl benzoate or cyclohexyl benzoate, phenyl cyclohexanecarboxylate or cyclohexanecarboxylate, phenylcyclohexane, cyclohexylbiphenyl, cyclohexylcyclohexane, cyclohexylnaphthalene, 1,4-bicyclohexylbiphenyl or cyclohexylpyrimidine, phenyl dioxane or cyclohexyldioxane, optionally halogenated. , benzyl phenyl ether, diphenylacetylene and substituted cinnamic acid esters.

[0807] The most important compounds suitable as components of this type of liquid crystal phase can be characterized by the following formula IV.

[0808] R 20 -LGER 21 IV

[0809] Where L and E each refer to a carbocyclic or heterocyclic system derived from the following groups: 1,4-disubstituted benzene rings and cyclohexane rings, 4,4'-disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidine and 1,3-dioxane rings, 2,6-disubstituted naphthalene, dihydronaphthalene and tetrahydronaphthalene, quinazoline and tetrahydroquinazoline.

[0810] G represents -CH=CH- -N(O)=N-

[0811] -CH=CQ- -CH=N(O)-

[0812] -C C- -CH2-CH2-

[0813] -CO-O- -CH2-O-

[0814] -CO-S- -CH2-S-

[0815] -CH=N- -COO-Phe-COO-

[0816] -CF2O- -CF=CF-

[0817] -OCF2- -OCH2-

[0818] -(CH2)4- -(CH2)3O-

[0819] Or a CC single bond, Q refers to halogen, preferably chlorine or -CN, and R 20 and R 21 Each refers to an alkyl, alkenyl, alkoxy, alkoxyalkyl or alkoxycarbonyl group having up to 18, preferably up to 8, carbon atoms, or one of these groups refers to CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl or Br.

[0820] In most of these compounds, R 20 and R 21 These substances differ from one another; one of these groups is typically alkyl or alkoxy. Other variations 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.

[0821] It will be self-evident to those skilled in the art that the VA, IPS or FFS mixtures according to the present invention may also contain compounds in which, for example, H, N, O, Cl and F are substituted with corresponding isotopes.

[0822] The combination of the compounds of the preferred embodiments mentioned above with the aforementioned polymeric compounds results in a low threshold voltage, low rotational viscosity, and very good low-temperature stability in the LC medium of the present invention, while maintaining high-definition bright spots and high HR values, and allowing for the rapid establishment of particularly low tilt angles (i.e., large tilt angles) in PSA displays. In particular, compared with LC media from the prior art, this LC medium exhibits a significantly shorter response time in PSA displays, especially grayscale response time.

[0823] The LC medium of this invention may also contain other 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 non-polymerizable. Polymerizable additives are correspondingly classified as polymerizable components or component A). Correspondingly, non-polymerizable additives are classified as non-polymerizable components or component B.

[0824] The present invention further relates to an LC display as described above, wherein the polymerizable compound of formula I or its sub-formulas and other polymerizable compounds contained in the LC medium are present in polymeric form.

[0825] The LC display is preferably a PSA or SA display, and very preferably a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS or SA-VA display.

[0826] In order to produce PSA or polymer-stabilized SA displays, polymerizable compounds contained in the LC medium are polymerized in situ in the LC medium between the LC display substrates, preferably with voltage applied to the electrodes simultaneously.

[0827] As described in the prior art cited at the outset, the structure of the display of the present invention corresponds to the typical geometry of a PSA display. Preferred geometries are those without protrusions, particularly those in which the electrodes on the color filter side are unstructured and only the electrodes on the TFT side have slots. For example, a particularly suitable and preferred electrode structure for a PS-VA display is described in US 2006 / 0066793 A1.

[0828] The preferred PSA-type LC display of the present invention includes:

[0829] - A first substrate, comprising a pixel electrode defining a pixel region, the pixel electrode being connected to a switching element disposed in each pixel region and optionally including a microslit pattern, and an optional first alignment layer disposed on the pixel electrode.

[0830] - A second substrate, including a common electrode layer disposed on the entire portion of the second substrate facing the first substrate, and an optional second alignment layer.

[0831] - An LC layer disposed between a first substrate and a second substrate and including an LC medium as described in the context, wherein the polymerizable compound may also be present in a polymerizable form.

[0832] The first and / or second alignment layers control the alignment orientation of the LC molecules in the LC layer. For example, in a PS-VA display, the alignment layers are selected to impart vertical (or vertically aligned) (i.e., perpendicular to the surface) or tilted alignment to the LC molecules. Such alignment layers may, for example, contain polyimide, which may also be rubbed or prepared by photoalignment methods.

[0833] An LC layer with an LC dielectric can be deposited between the substrates of a display using methods commonly used by display manufacturers, such as the so-called one-drop-filling (ODF) method. The polymerizable components of the LC dielectric are then polymerized, for example, by UV photopolymerization. Polymerization can be performed in one step or in two or more steps.

[0834] A PSA display may include other components such as color filters, black matrices, passivation layers, optical delay layers, transistor elements for addressing individual pixels, etc., which are well known to those skilled in the art and can be used without inventive skills.

[0835] Electrode structures can be designed by engineers based on the specific display type. For example, for PS-VA displays, multi-domain orientation of LC molecules can be induced by providing electrodes with slits and / or protrusions or bumps to produce two, four, or more distinct tilt alignment directions.

[0836] Following polymerization, the polymerizable compound forms a copolymer, resulting in a certain tilt angle for the LC molecules in the LC medium. Without being bound by specific theories, it is believed that at least a portion of the crosslinked polymer formed by the polymerizable compound will separate from or precipitate from the LC medium phase and form a polymer layer on the substrate or electrode, or an alignment layer thereon. Microscopic measurements (such as SEM and AFM) have confirmed that at least a portion of the formed polymer accumulates at the LC / substrate interface.

[0837] Polymerization can be carried out in one step. Alternatively, polymerization may be performed first in a first step to create a tilt angle, optionally with voltage applied simultaneously, followed by polymerization or crosslinking of the unreacted compound from the first step in a second polymerization step without voltage applied (“final curing”).

[0838] Suitable and preferred polymerization methods include, for example, thermal polymerization or photopolymerization, with photopolymerization being preferred, especially UV-induced photopolymerization, which can be achieved by exposing the polymerizable compound to UV irradiation.

[0839] Optionally, one or more polymerization initiators are added to the LC medium. Suitable polymerization conditions, as well as suitable initiator types and amounts, are known to those skilled in the art and described in the literature. Suitable initiators for free radical polymerization include, for example, commercially available photoinitiators such as Irgacure 651®, Irgacure 184®, Irgacure 907®, Irgacure 369®, or Darocure 1173® (Ciba AG). If a polymerization initiator is used, its proportion is preferably 0.001-5 wt%, particularly preferably 0.001-1 wt%.

[0840] The polymerizable compounds of this invention are also suitable for polymerization without an initiator, which has significant advantages, such as lower material costs, and especially less contamination of the LC medium by possible residual initiator or its degradation products. Therefore, polymerization can also be carried out without the addition of an initiator. Thus, in a preferred embodiment, the LC medium does not contain a polymerization initiator.

[0841] The LC medium may also contain one or more stabilizers to prevent unwanted spontaneous polymerization of RM, for example, during storage or transport. Suitable types and amounts of stabilizers are known to those skilled in the art and described in the literature. Particularly suitable are, for example, commercially available stabilizers from the Irganox® series (Ciba AG), such as Irganox® 1076. If stabilizers are used, their proportion, based on the total amount of RM or polymerizable component (component A), is preferably 10-50,000 ppm, particularly preferably 50-5,000 ppm.

[0842] In a preferred embodiment, the LC medium contains one or more chiral dopants, preferably at a concentration of 0.01-1 wt%, very preferably 0.05-1.0 wt%. The chiral dopants are preferably selected from compounds in Table B below, and very preferably R- or S-1011, R- or S-2011, R- or S-3011, R- or S-4011 and R- or S-5011.

[0843] In another preferred embodiment, the LC medium contains a racemic form of one or more chiral dopants, preferably selected from the chiral dopants mentioned in the previous paragraph.

[0844] In another preferred embodiment of the invention, the LC medium contains one or more other stabilizers, preferably selected from the following formula.

[0845]

[0846] Each group is independent of the others and, each time it appears, has the same or different meanings as follows:

[0847] R a-d It is a straight-chain or branched alkyl group having 1-10, preferably 1-6, and very preferably 1-4 carbon atoms, with methyl being the most preferred.

[0848] X S It can be H, CH3, OH or O ● ,

[0849] A S It is a straight-chain, branched, or cyclohememyl group having 1-20 carbon atoms, which may be optionally substituted.

[0850] n is an integer from 1 to 6, preferably 3.

[0851] Preferred S3 stabilizers are selected from S3A.

[0852]

[0853] Where n2 is an integer from 1 to 12, and the group (CH2) is included. n2One or more H atoms in the H atom may be optionally replaced by methyl, ethyl, propyl, butyl, pentyl or hexyl.

[0854] The preferred stabilizer is selected from the following formula

[0855]

[0856]

[0857] In a preferred embodiment, the liquid crystal medium contains one or more stabilizers selected from formulas S1-1, S2-1, S3-1, S3-1, and S3-3.

[0858] In a preferred embodiment, the liquid crystal medium comprises one or more stabilizers selected from Table C below.

[0859] The stabilizer in the liquid crystal medium is preferably in the proportion of formulas S1-S3 and their derivatives, which is 10-500 ppm, and very preferably 20-100 ppm.

[0860] In another preferred embodiment, the LC medium of the present invention contains a self-aligning (SA) additive, preferably at a concentration of 0.1-2.5%.

[0861] In another preferred embodiment, the LC medium of the present invention contains a self-aligning (SA) additive, preferably at a concentration of 0.1-2.5%.

[0862] In a preferred embodiment, the SA-VA display of the present invention does not contain a polyimide alignment layer. In another preferred embodiment, the SA-VA display according to the preferred embodiment contains a polyimide alignment layer.

[0863] The preferred SA additive used in this preferred embodiment is selected from compounds containing mesocrystalline groups and straight-chain or branched alkyl side chains capped by one or more polar anchoring groups selected from hydroxyl, carboxyl, amino, or thiol groups.

[0864] Further preferred SA additives contain one or more polymerizable groups, optionally linked to mesocrystalline groups via spacer groups. These polymerizable SA additives can be polymerized in an LC medium under conditions similar to those used for RM in the PSA process.

[0865] Suitable SA additives for inducing vertical alignment, particularly SA additives for SA-VA mode displays, are disclosed, for example, in US 2013 / 0182202 A1, US 2014 / 0838581 A1, US 2015 / 0166890 A1 and US 2015 / 0252265 A1.

[0866] In another preferred embodiment, the LC media or polymer-stabilized SA-VA display of the present invention contains one or more self-aligning additives selected from Table E below.

[0867] In another preferred embodiment, the LC medium of the present invention contains one or more SA additives, preferably selected from Table E, at a concentration of 0.1-5%, very preferably 0.2-3%, and most preferably 0.2-1.5%.

[0868] Formula I and its derivative polymerizable compounds do indeed exhibit good UV absorption and are therefore particularly suitable for methods of preparing PSA displays, said methods comprising one or more of the following features:

[0869] - In a two-step method, the polymerizable medium is exposed to UV light in a display. The method includes a first UV exposure step (“UV1 step”), in which a voltage is applied to create a tilt angle, and a second UV exposure step (“UV2 step”), in which no voltage is applied to complete the polymerization.

[0870] - Preferably, at least in the UV2 step, and more preferably in both the UV1 and UV2 steps, the polymerizable medium is exposed in the display to UV light generated by a UV-LED lamp.

[0871] - The polymerizable medium is exposed in the display to UV light generated by a UV lamp with an irradiation spectrum shifted to a longer wavelength, preferably ≥ 340 nm, more preferably 350 to < 370 nm, and very preferably 355-368 nm, to avoid short-term UV light exposure in the PS-VA method.

[0872] Using lower intensity and shifting UV to a longer wavelength can both protect the organic layer from damage that may be caused by UV light.

[0873] A preferred embodiment of the present invention relates to a method for manufacturing a PSA display as described in the context, the method comprising one or more of the following features:

[0874] - In the two-step method, the polymerizable LC medium is irradiated with UV light, including a first UV exposure step (“UV1 step”), in which a voltage is applied to create a tilt angle, and a second UV exposure step (“UV2 step”), in which no voltage is applied to complete the polymerization.

[0875] - Using a strength of 0.5 mW / cm 2 -10 mW / cm 2 UV light irradiation from a UV lamp with a wavelength of 300-380 nm can polymerize LC media, preferably in the UV2 step, and optionally also in the UV1 step.

[0876] - Irradiate polymerizable LC media with UV light at wavelengths ≥340 nm, and preferably ≤420 nm, very preferably 340-380 nm, more preferably 350 to <370 nm, and most preferably 355-368 nm.

[0877] - While applying voltage to the electrodes of the display, polymerizable LC dielectric is irradiated with UV light.

[0878] - Use UV-LED lamps for UV irradiation.

[0879] This preferred method can be achieved, for example, by using the desired UV lamp or by using bandpass and / or cutoff filters that are substantially transmissive to UV light of each desired wavelength and substantially blocking to each undesirable wavelength. For instance, when UV irradiation with wavelengths λ of 300-400 nm is required, a broadband filter that is substantially transmissive to wavelengths 300 nm < λ < 400 nm can be used for UV exposure. When UV irradiation with wavelengths λ greater than 340 nm is required, a cutoff filter that is substantially transmissive to wavelengths λ > 340 nm can be used for UV irradiation.

[0880] Preferably, UV-LED lamps are used for UV irradiation.

[0881] In the PSA process, using UV-LED lamps with only a narrow emission peak offers several advantages, such as more efficient transfer of light energy to polymerizable compounds in the LC medium, depending on the selection of suitable polymerizable compounds that exhibit absorption at the LED lamp's emission wavelength. This allows for reductions in UV intensity and / or UV irradiation time, thereby enabling shorter cycle times and saving energy and production costs. Another advantage is the narrow emission spectrum of the lamp, which makes it easier to select appropriate wavelengths for photopolymerization.

[0882] Very preferably, the UV light source is a UV-LED lamp emitting wavelengths of 340-400 nm, more preferably 340-380 nm, even more preferably 350 to <370 nm, and most preferably 355-368 nm. Particularly preferred are UV-LED lamps emitting UV light with a wavelength of 365 nm.

[0883] Preferably, the UV-LED lamp emits light with an emission peak having a full width at half maximum (FWHM) of 30 nm or less.

[0884] UV-LED lamps are commercially available from sources such as Dr. Hoenle AG, Primelite GmbH, or IST Metz GmbH in Germany, with emission wavelengths of, for example, 365, 385, 395, and 405 nm.

[0885] This preferred method enables the manufacture of displays by using longer UV wavelengths, thereby reducing or even avoiding the harmful and destructive effects of short UV components.

[0886] UV irradiation energy is typically 6-100 J, depending on the production process conditions.

[0887] The LC medium of the present invention may additionally contain one or more other components or additives, preferably selected from the following list, including but not limited to comonomers, chiral dopants, polymerization initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricants, dispersants, hydrophobic agents, binders, flow improvers, defoamers, degassing agents, diluents, reactive diluents, auxiliaries, colorants, dyes, pigments and nanoparticles.

[0888] In another preferred embodiment, in addition to the polymerizable compound of Formula I or its sub-formulas, the LC medium also contains one or more other polymerizable compounds (“comonomers”) preferably selected from RM.

[0889] Suitable and preferred polymerizable compounds for use as comonomers are selected from the following formula:

[0890]

[0891]

[0892]

[0893]

[0894] Each group, when appearing in the same or different manner, and independently of each other, has the following meaning:

[0895] P 1 , P 2 , P 3 The polymerizable group is preferably selected from ethyleneoxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxy groups.

[0896] Sp 1 Sp 2 Sp 3 It is a single bond or a spacer group, wherein, in addition, P 1 -Sp 1 -、P 1 -Sp 2 -and P 3 -Sp 3 One or more groups in - can represent R aa The condition is that P exists. 1-Sp 1 -、P 2 -Sp 2 and P 3 -Sp 3 At least one group in - is different from R aa Preferred -(CH2) p1 -、-(CH2) p1 -O-、-(CH2) p1 -CO-O- or -(CH2) p1 -O-CO-O-, where p1 is an integer from 1 to 12.

[0897] R aa It is H, F, Cl, CN, or a straight-chain or branched alkyl group having 1-25 C atoms, wherein, in addition, one or more non-adjacent CH2 groups may be independently coupled to each other such that the O and / or S atoms are not directly connected to each other by -C(R) 0 )=C(R 00 )-、-C≡C-、-N(R 0 -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O-, and in addition, one or more H atoms may be replaced by F, Cl, CN or P. 1 -Sp 1 - Alternatively preferred are straight-chain or branched, optionally mono- or polyfluoroalkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy groups having 1-12 carbon atoms (wherein the alkenyl and alkynyl groups have at least two carbon atoms and the branched groups have at least three carbon atoms), and wherein R aa Does not represent or contain the group P 1 P 2 or P 3 ,

[0898] R 0 , R 00 It is H or an alkyl group having 1-12 carbon atoms.

[0899] R y and R z It can be H, F, CH3 or CF3.

[0900] X 1 X 2 X 3 It can be -CO-O-, -O-CO-, or a single bond.

[0901] Z M1 -O-, -CO-, -C(R) y R z - or -CF2CF2-,

[0902] Z M2 Z M3 It can be -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2). n - where n is 2, 3, or 4.

[0903] L is F, Cl, CN, or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, or alkoxycarbonyloxy group having 1-12 C atoms.

[0904] L', L" are H, F, or Cl.

[0905] k is 0 or 1,

[0906] r is 0, 1, 2, 3 or 4.

[0907] s is 0, 1, 2 or 3.

[0908] t is 0, 1, or 2.

[0909] x is 0 or 1.

[0910] The compounds M2 and M13 are highly preferred, especially those containing exactly two polymerizable groups P. 1 and P 2 Bireactive compounds.

[0911] Further preferred are compounds selected from formulas M17-M32, especially formulas M20, M22, M24, M27, M30, and M32, particularly those containing three polymerizable groups P. 1 P 2 and P 3 Tri-reactive compounds.

[0912] In compounds of formulas M1-M32

[0913]

[0914] The L, each time it appears, has one of the meanings given in the context, and is preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, OCH3, COCH3 or OCF3, and most preferably F or OCH3.

[0915] Preferred compounds of formulas M1-M32 are those in which P 1 P 2 and P 3 Those representing acrylate group, methacrylate group, oxetane or epoxy group are very preferred, acrylate group or methacrylate group is most preferred.

[0916] Further preferred compounds of formulas M1-M32 are those in which Sp 1 Sp 2 and Sp 3 Those that are single keys.

[0917] Further preferred compounds of formulas M1-M32 are those in which Sp 1 Sp 2 and Sp 3 One of them is a single bond and Sp 1 Sp 2 and Sp 3 Another one that differs from single bonds.

[0918] Further preferred compounds of formulas M1-M32 are those with Sp groups that are different from single bonds. 1 Sp 2 and Sp 3 It represents -(CH2) s1 Those with -X"-, where s1 is an integer from 1 to 6, preferably 2, 3, 4 or 5, and X" is the connection to the benzene ring and is -O-, -O-CO-, -CO-O, -O-CO-O- or a single bond.

[0919] Further preferred compounds of formula M are those selected from those in Table D below, especially those 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-92, RM-102, RM-103, RM-109, RM-116, RM-117, RM-120, RM-121, RM-122, RM-139, RM-142, RM-153, RM-155, RM-158 and RM-159.

[0920] LC media containing one, two, or three polymerizable compounds of formula M are particularly preferred.

[0921] Further preferred are LC media containing two or more bireactive polymerizable compounds of formula M, preferably selected from formulas M1-M16, and very preferably selected from formulas M2 and M13.

[0922] Further preferred are LC media comprising one or more bireactive polymerizable compounds of formula M, preferably selected from formulas M1-M16, very preferably formulas M2 and M13, and one or more trireactive polymerizable compounds of formula M, preferably selected from formulas M17-M32, very preferably formulas M20, M22, M24, M27, M30 and M32.

[0923] Further preferred are LC media comprising one or more polymerizable compounds of formula M, wherein at least one r is not 0, or at least one of s and t is not 0, very preferably selected from formulas M2, M13, M22, M24, M27, M30 and M32, and wherein L is selected from the preferred groups shown above, most preferably F and OCH3.

[0924] Further preferred are LC media comprising one or more polymerizable compounds that exhibit absorption at wavelengths of 320-380 nm, preferably selected from formula M, and very preferably formulas M1-M32.

[0925] Further preferred are LC media comprising one or more polymerizable compounds selected from Table D. Among these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121, RM-122, and RM-145 to RM-152 are particularly preferred.

[0926] In another preferred embodiment, in addition to polymerizable compounds of formula I or its sub-formulas, the LC medium comprises one or more polymerizable compounds having two polymerizable groups, selected from formula C.

[0927]

[0928] Each group, when appearing in the same or different manner, and independently of each other, has the following meaning:

[0929] P, Sp are one of the meanings given by equation I or its sub-equations, or one of their preferred meanings as given by the context.

[0930] L is F, Cl, CN, or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, or alkoxycarbonyloxy group having 1-12 C atoms.

[0931] r1 and r2 are 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and very preferably 0 or 1.

[0932] Preferred CM compounds are selected from the following sub-formulas.

[0933]

[0934] Where p and Sp, L, r1 and r2 independently have one of the meanings given in formula CM or one of their preferred meanings as given in the context, and Sp' has one of the meanings given for Sp that is different from that of a single bond.

[0935] Ideally, at least one of r1 and r2 should not be 0.

[0936] P is preferably acrylate or methacrylate, and very preferably methacrylate. In preferred formulas CM, CM-1, and CM-2, all groups P have the same meaning, and very preferably represents 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-, wherein the O atom or CO group is attached to the benzene ring.

[0937] L is preferably selected from F, CH3, OCH3, OC2H5, C2H5, CH=CH2 and C(CH3)=CH2, with F being highly preferred.

[0938] The highly preferred compound is CM-1.

[0939] More preferred CM compounds are selected from the following sub-formulas.

[0940]

[0941]

[0942] Wherein P, Sp', and L have one of the meanings given in formulas CM-1 and CM-2. P is preferably acrylate or methacrylate, and very preferably methacrylate. All groups P in formulas CM-1-1 to CM-2-9 preferably 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-, wherein the O atom or CO group is attached to the benzene ring. L is preferably selected from F, CH3, OCH3, OC2H5, C2H5, CH=CH2, and C(CH3)=CH2, and very preferably F and OCH3.

[0943] Very preferred compounds are CM-1-2, CM-1-3, CM-1-4, CM-1-5, CM-1-6 and their derivatives. Most preferred compound is CM-1-1.

[0944] The most preferred CM compounds are selected from the following sub-formulas:

[0945]

[0946]

[0947]

[0948] The most preferred compounds are CM-1-1a, CM-1-2a, and CM-1-3a. The most preferred compound is CM-1-1a.

[0949] Further preferred compounds of formulas CM-1-1a to CM-2-9a, wherein one or two methacrylate groups are replaced by acrylate groups, and compounds of formulas CM-1-1a to CM-2-9a, wherein all methacrylate groups are replaced by acrylate groups.

[0950] Further preferred CM compounds are selected from Table D below.

[0951] In another preferred embodiment, in addition to polymerizable compounds of formula I or its sub-formulas, the LC medium comprises one or more polymerizable compounds selected from formula MT having three polymerizable groups.

[0952]

[0953] Wherein P, Sp, L, r1 and r2 each independently have one of the meanings given in formula CM or as the context suggests, k is 0 or 1, and r3 is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and very preferably 0 or 1.

[0954] Preferred MT compounds are selected from the following sub-formulas.

[0955]

[0956] Wherein P, Sp, L, r1, r2 and r3 independently have one of the meanings given in formula MT or one of their preferred meanings as given in the context.

[0957] Preferably, at least one of r1, r2, and r3 is not 0.

[0958] P is preferably acrylate or methacrylate, with methacrylate being the most preferred group.

[0959] L is preferably selected from F, CH3, OCH3, OC2H5, C2H5, CH=CH2 and C(CH3)=CH2, with F being highly preferred.

[0960] In preferred formulations MT and MT-1 to MT-6, all groups P have the same meaning, and very preferably represent methacrylate groups.

[0961] Highly preferred compounds are MT-1, MT-4 and MT-5.

[0962] More preferably, NM compounds are selected from the following sub-formulas.

[0963]

[0964]

[0965]

[0966]

[0967]

[0968]

[0969]

[0970]

[0971] Wherein P, Sp, and L have one of the meanings given in formula MT, and Sp' has one of the meanings given for Sp that differs from that of a single bond. P is preferably acrylate or methacrylate, and very preferably methacrylate. All groups P in preferred formulas MT-1-1 to MT-6-12 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-, wherein the O atom or CO group is attached to the benzene ring. L is preferably selected from F, CH3, OCH3, OC2H5, C2H5, CH=CH2, and C(CH3)=CH2, and very preferably F and OCH3.

[0972] Highly preferred formulations MT-1-1, MT-1-6, MT-5-1 and their derivative compounds.

[0973] The most preferred MT compounds are selected from the following sub-formulas:

[0974]

[0975]

[0976]

[0977]

[0978]

[0979]

[0980]

[0981]

[0982]

[0983]

[0984]

[0985]

[0986]

[0987]

[0988]

[0989] Among the compounds of formulas MT-1 to MT-3, compounds of formulas MT-1-1a, MT-1-2a, MT-1-2b, MT-2-1a, MT-2-2a, MT-2-2b, MT-3-1a, MT-3-2a, and MT-3-2b are very preferred. Compounds of formulas MT-1-1a, MT-1-2a, MT-1-2b, MT-2-1a, MT-2-2a, and MT-2-2b are most preferred.

[0990] Among the compounds of formulas MT-4 to MT-6, compounds of formulas MT-4-1a, MT-4-2a, MT-4-3a, MT-4-4a, MT-4-5a, MT-4-6a, MT-4-7a, MT-4-7b, MT-4-8a, MT-4-9a, MT-4-10a, MT-4-11a, MT-4-12a, MT-5-1a, MT-5-2a, MT-5-4a, MT-5-5a, MT-5-6a, MT-5-7a, MT-5-7b, MT-5-8a, MT-5-9a, MT-5-10a, MT-5-11a, and MT-5-12a are highly preferred. Compounds of formulas MT-4-1a, MT-4-7a, MT-4-7b, MT-5-1a, MT-5-7a, and MT-5-7b are most preferred.

[0991] Further preferred compounds are MT-1-1a to MT-6-11a, wherein one or both methacrylate groups are replaced by acrylate groups. Further preferred compounds are MT-1-1a to MT-6-11a, wherein all methacrylate groups are replaced by acrylate groups.

[0992] Further preferred MT compounds are selected from Table D below.

[0993] In addition, 0 to 15% by weight of a pleochroic dye, nanoparticles, conductive salts, preferably ammonium ethyl dimethyl dodecyl 4-hexyloxybenzoate, ammonium tetrabutyltetraphenylborate, or complex salts of crown ethers can be added to the LC medium (see, for example, Haller et al., Mol. Cryst. Liq. Cryst.). 24 , 249-258 (1973)) are used to improve conductivity, or to add substances to modify the dielectric anisotropy, viscosity and / or orientation of the nematic phase. Such substances are described, for example, in DE-A 22 09 127, 22 40864, ​​23 21 632, 23 38 281, 24 50 088, 26 37 430 and 28 53 728.

[0994] The individual components of the preferred embodiments of the LC media listed above according to the invention are known, or the methods for preparing them can be obtained from the prior art by those skilled in the art, as they are based on standard methods described in the literature. For example, corresponding compounds of formula CY are described in EP-A-0 364 538. For example, corresponding compounds of formula ZK are described in DE-A-26 36 684 and DE-A-33 21 373.

[0995] The LC media used according to the invention can be prepared by conventional methods, for example by mixing one or more of the compounds mentioned above with one or more polymerizable compounds as defined above, and optionally with other liquid crystal compounds and / or additives. Typically, a desired amount of the component used in a small quantity is dissolved in the component constituting the main component, which is advantageously carried out at elevated temperatures. The solution of the components can also be mixed in an organic solvent such as acetone, chloroform, or methanol, and the solvent is removed again, for example by distillation after thorough mixing. The invention also relates to a method for preparing the LC media according to the invention.

[0996] It will be self-evident to those skilled in the art that the LC medium according to the present invention may also contain, for example, compounds in which H, N, O, Cl, and F are replaced by corresponding isotopes such as deuterium.

[0997] The following examples illustrate the invention but do not limit it. However, they demonstrate to those skilled in the art preferred mixture concepts, as well as preferred compounds used and their respective concentrations, and combinations thereof. Furthermore, the examples clarify which properties and combinations of properties are available. Preferred mixture compositions are shown in Table A below.

[0998] Table A

[0999] In Table A, m and n are independent integers from 1 to 12, preferably 1, 2, 3, 4, 5, or 6, k is 0, 1, 2, 3, 4, 5, or 6, and (O)C m H 2m+1 Indicate C m H 2m+1 or OC m H 2m+1 .

[1000]

[1001]

[1002]

[1003]

[1004]

[1005]

[1006]

[1007]

[1008]

[1009]

[1010]

[1011]

[1012]

[1013]

[1014]

[1015]

[1016]

[1017]

[1018]

[1019]

[1020]

[1021]

[1022]

[1023] In a preferred embodiment of the present invention, the LC medium of the present invention comprises one or more compounds selected from the compounds in Table A.

[1024] Table B

[1025] Table B shows the chiral dopants that can be added to the LC media of this invention.

[1026]

[1027]

[1028] The LC dielectric preferably contains 0-10 wt%, particularly 0.01-5 wt%, and especially preferably 0.1-3 wt% of dopant. The LC dielectric preferably contains one or more dopants selected from the compounds in Table B.

[1029] Table C

[1030] Table C shows possible stabilizers that can be added to the LC media of the present invention. Here, n represents an integer from 1 to 12, preferably 1, 2, 3, 4, 5, 6, 7 or 8, and the terminal methyl group is not shown.

[1031]

[1032]

[1033]

[1034]

[1035]

[1036] The LC medium preferably contains 0-10 wt%, particularly 1 ppm-5 wt%, especially preferably 1 ppm-1 wt% of a stabilizer. The LC medium preferably contains one or more stabilizers selected from the compounds in Table C.

[1037] Table D

[1038] Table D shows exemplary reactive mesocrystalline compounds that can be used in the LC media of this invention.

[1039]

[1040]

[1041]

[1042]

[1043]

[1044]

[1045]

[1046]

[1047]

[1048]

[1049]

[1050]

[1051]

[1052]

[1053]

[1054]

[1055]

[1056]

[1057]

[1058] In a preferred embodiment, the mixture of the present invention comprises one or more polymerizable compounds, preferably selected from polymerizable compounds of formulas RM-1 to RM-144. Among these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-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, and RM-146 to RM-153 are particularly preferred.

[1059] In another preferred embodiment, the mixture of the present invention comprises one or more polymerizable compounds selected from formulas RM-146 to RM-153, with formulas RM-148 to RM-153 being particularly preferred.

[1060] Table E

[1061] Table E shows the self-aligning additives for vertical alignment, which can be used together with the polymerizable compounds of Formula I in the LC media of the SA-VA and SA-FFS displays of the present invention:

[1062]

[1063]

[1064]

[1065]

[1066]

[1067]

[1068]

[1069]

[1070]

[1071]

[1072] In a preferred embodiment, the LC medium of the SA-VA and SA-FFS displays of the present invention comprises one or more SA additives selected from SA-1 to SA-48 (preferably selected from SA-14 to SA-48, very preferably SA-20 to SA-34 and SA-44) and one or more RMs of formula I.

[1073] Example

[1074] The following examples illustrate the invention but do not limit it. However, they demonstrate to those skilled in the art the concept of preferred mixtures and the preferred compounds used, their corresponding concentrations, and combinations thereof. Furthermore, the examples illustrate the available properties and combinations of properties.

[1075] In addition, the following abbreviations and symbols were used:

[1076] V0 represents the threshold voltage at 20℃, capacitive [V].

[1077] n e This indicates the unusual refractive index at 20°C and 589 nm.

[1078] n o This represents the ordinary refractive index at 20°C and 589 nm.

[1079] n represents the optical anisotropy at 20℃ and 589 nm.

[1080] ε This represents the dielectric constant perpendicular to the director at 20℃ and 1 kHz.

[1081] ε This represents the dielectric constant parallel to the director at 20℃ and 1 kHz.

[1082] Δε represents the dielectric anisotropy at 20 °C and 1 kHz.

[1083] cl.p., T(N,I) represents the clearing point [°C].

[1084] 1 represents the rotational viscosity at 20°C [mPa]. s],

[1085] K1 represents the elastic constant at 20℃, and the "oblique stretching" deformation [pN].

[1086] K2 represents the elastic constant at 20℃, and the "torsional" deformation [pN].

[1087] K3 represents the elastic constant at 20°C, and the bending deformation [pN].

[1088] Unless otherwise expressly stated, all concentrations in this application are given as weight percentages and refer to the entire mixture in question, which contains all solid or liquid crystal components (without solvent).

[1089] Unless otherwise stated, all temperature values ​​indicated in this application, such as melting point T(C,N), transformation from smectic (S) to nematic (N) T(S,N), and clearing point T(N,I), are expressed in degrees Celsius (°C). Mp represents the melting point, and cl.p. = clearing point. Furthermore, C = liquid crystal phase, N = nematic phase, S = smectic phase, and I = isotropic phase. The data between these symbols represent the transformation temperature.

[1090] All physical properties are and have been determined according to “Merck Liquid Crystals, Physical Properties of Liquid Crystals” Status November 1997, Merck KGaA, Germany, and are applicable to a temperature of 20°C, with Δn measured at 589 nm and Δε measured at 1 kHz, unless otherwise explicitly stated in each case.

[1091] The term "threshold voltage" used in this invention refers to the capacitive threshold (V0), which is also known as the Freedericks threshold, unless otherwise stated. In embodiments, the optical threshold is also, as is generally the case, for 10% relative contrast (V0). 10 (This is given.)

[1092] Unless otherwise stated, the method of polymerizing polymerizable compounds in a PSA display as described in the context, wherein the LC medium is in the form of a liquid crystal phase, preferably a nematic phase, is carried out at a temperature, and most preferably at room temperature.

[1093] Unless otherwise stated, the preparation of test kits and the measurement of their electro-optic and other properties shall be carried out by the methods described below or similar methods.

[1094] The display used to measure capacitive threshold voltage consists of two planar parallel glass outer plates spaced 25 µm apart. Each outer plate has an electrode layer on its inner side and an unrubbed polyimide alignment layer on its top, which results in vertical edge alignment of the liquid crystal molecules.

[1095] A PSVA display or PSVA test chamber for measuring tilt angles consists of two planar parallel glass outer plates spaced approximately 3.3 µm apart. Unless otherwise specified, each outer plate has an electrode layer on its inner side and a top-mounted polyimide alignment layer, wherein the two polyimide layers rub against each other antiparallel, resulting in vertical edge alignment of the liquid crystal molecules. The PSVA display or test chamber may have one or no polyimide alignment layer and a patterned electrode structure resulting in two or more LC alignment orientation domains. For tilt measurements, light from a single domain is transmitted using a light-blocking layer or shielding.

[1096] Polymerizable compounds are polymerized in a display or test chamber by irradiating the display with UV light of a defined intensity for a predetermined time while simultaneously applying a voltage (typically 10V-30V AC, 1 kHz) to the display. In the examples, unless otherwise specified, a metal halide lamp and an intensity of 100 mW / cm² are used for polymerization. The intensity is measured using a standard instrument (the high end of a Hoenle UV meter with a UV sensor).

[1097] The tilt angle was determined using Axometrics' Mueller Matrix Polarimeter "AxoScan". Smaller values ​​(i.e., larger deviations relative to a 90° angle) correspond to larger tilts in this case.

[1098] The tilt angle can also be determined using the RETS polarimeter from Otsuka Electronics Co., Ltd. In the case of VA mode, the tilt angle is small for small retardation values, meaning the LC director is close to vertical (vertical) alignment.

[1099] Unless otherwise stated, the term "tilt angle" means the angle between the LC director and the substrate, and "LC director" means the preferred orientation of the optical principal axis of the LC molecules in a layer of LC molecules with uniform orientation, corresponding to the long axis of the molecules in the case of rod-shaped, uniaxial positive birefringent LC molecules.

[1100] Example 1

[1101] The nematic LC bulk mixture N1 is prepared as follows:

[1102]

[1103] The polymerizable mixture P1 was prepared by adding 0.4% polymerizable compound M1 and 50 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1104]

[1105] Example 2

[1106] The nematic LC bulk mixture N2 is prepared as follows:

[1107]

[1108] The polymerizable mixture P2 was prepared by adding 0.3% of the polymerizable compound M1 and 100 ppm of the stabilizer S1-1 to the nematic LC host mixture N2.

[1109] Example 3.1

[1110] The nematic LC bulk mixture N3 is prepared as follows:

[1111]

[1112] The polymerizable mixture P3 was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N3.

[1113] Example 3.2

[1114] The chiral nematic host mixture C3 was prepared by adding 0.91% of the chiral dopant S-4011 to the nematic host mixture N3.

[1115] The polymerizable mixture P3c was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the chiral nematic LC host mixture C3.

[1116] Example 4

[1117] The nematic LC bulk mixture N4 is prepared as follows:

[1118]

[1119] The polymerizable mixture P4 was prepared by adding 0.3% of the polymerizable compound M2 to the nematic LC host mixture N4.

[1120]

[1121] Example 5

[1122] The nematic LC bulk mixture N5 is prepared as follows:

[1123]

[1124] The polymerizable mixture P5 was prepared by adding 0.3% of the polymerizable compound M2 and 50 ppm of the stabilizer S1-1 to the nematic LC host mixture N5.

[1125] Example 6

[1126] The nematic LC bulk mixture N6 is prepared as follows:

[1127]

[1128] The polymerizable mixture P6 was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N6.

[1129] Example 7

[1130] The nematic LC bulk mixture N7 is prepared as follows:

[1131]

[1132] The polymerizable mixture P7 was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S2-1 to the nematic LC host mixture N7.

[1133]

[1134] Example 8

[1135] The nematic LC bulk mixture N8 is prepared as follows:

[1136]

[1137] The polymerizable mixture P8 was prepared by adding 0.3% of polymerizable compound M3 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N8.

[1138]

[1139] Example 9

[1140] The nematic LC bulk mixture N9 is prepared as follows:

[1141]

[1142] The polymerizable mixture P9 was prepared by adding 1.0% of polymerizable compound M1 and 0.6% of SA additive SA23 to the nematic LC host mixture N9.

[1143]

[1144] Example 10

[1145] The nematic LC bulk mixture N10 is prepared as follows:

[1146]

[1147] The polymerizable mixture P10 was prepared by adding 0.4% polymerizable compound M3 and 50 ppm stabilizer S1-1 to the nematic LC host mixture N10.

[1148] Example 11

[1149] The nematic LC bulk mixture N11 is prepared as follows:

[1150]

[1151] The polymerizable mixture P11 was prepared by adding 0.4% polymerizable compound M1 and 50 ppm stabilizer S2-1 to the nematic LC host mixture N11.

[1152] Example 12

[1153] The nematic LC bulk mixture N12 is prepared as follows:

[1154]

[1155] The polymerizable mixture P12 was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N12.

[1156] Example 13

[1157] The nematic LC bulk mixture N13 is prepared as follows:

[1158]

[1159] The polymerizable mixture P13 was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N13.

[1160] Example 14

[1161] The nematic LC bulk mixture N14 is prepared as follows:

[1162]

[1163] The polymerizable mixture P14 was prepared by adding 0.4% of polymerizable compound M1 and 50 ppm of stabilizer S2-1 to the nematic LC host mixture N14.

[1164] Example 15

[1165] The nematic LC bulk mixture N15 is prepared as follows:

[1166]

[1167] The polymerizable mixture P15 was prepared by adding 0.4% of polymerizable compound M1 and 50 ppm of stabilizer S3-1 to the nematic LC host mixture N15.

[1168]

[1169] Example 16

[1170] The nematic LC bulk mixture N16 is prepared as follows:

[1171]

[1172] The polymerizable mixture P16 was prepared by adding 0.4% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N16.

[1173] Example 17

[1174] The nematic LC bulk mixture N17 is prepared as follows:

[1175]

[1176] The polymerizable mixture P17 was prepared by adding 0.4% polymerizable compound M1 and 50 ppm stabilizer S3-2 to the nematic LC host mixture N17.

[1177]

[1178] Example 18

[1179] The nematic LC bulk mixture N18 is prepared as follows:

[1180]

[1181] The polymerizable mixture P18 was prepared by adding 0.4% polymerizable compound M1 and 50 ppm stabilizer S1-1 to the nematic LC host mixture N18.

[1182] Example 19

[1183] The nematic LC bulk mixture N19 is prepared as follows:

[1184]

[1185] The polymerizable mixture P19 was prepared by adding 0.4% polymerizable compound M2 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N19.

[1186] Example 20

[1187] The nematic LC bulk mixture N20 is prepared as follows:

[1188]

[1189] The polymerizable mixture P20 was prepared by adding 0.4% of the polymerizable compound M3 and 50 ppm of the stabilizer S1-1 to the nematic LC host mixture N20.

[1190]

[1191] Example 21

[1192] The nematic LC bulk mixture N21 is prepared as follows:

[1193]

[1194] The polymerizable mixture P21 was prepared by adding 0.4% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N21.

[1195] Example 22

[1196] The nematic LC bulk mixture N22 is prepared as follows:

[1197]

[1198] The polymerizable mixture P22 was prepared by adding 1.0% of polymerizable compound M1 and 0.6% of SA additive SA32 to the nematic LC host mixture N22.

[1199]

[1200] Example 23

[1201] The nematic LC bulk mixture N23 is prepared as follows:

[1202]

[1203] The polymerizable mixture P23 was prepared by adding 0.4% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N23.

[1204] Example 24

[1205] The nematic LC bulk mixture N24 is prepared as follows:

[1206]

[1207] The polymerizable mixture P24 was prepared by adding 0.4% of polymerizable compound M1 and 100 ppm of stabilizer S2-1 to the nematic LC host mixture N24.

[1208] Example 25

[1209] The nematic LC bulk mixture N25 is prepared as follows:

[1210]

[1211] The polymerizable mixture P25 was prepared by adding 0.4% of the polymerizable compound M2 and 50 ppm of the stabilizer S1-1 to the nematic LC host mixture N25.

[1212] Example 26

[1213] The nematic LC bulk mixture N26 is prepared as follows:

[1214]

[1215] The polymerizable mixture P26 was prepared by adding 0.4% of polymerizable compound M1 and 50 ppm of stabilizer S3-1 to the nematic LC host mixture N26.

[1216] Example 27

[1217] The nematic LC bulk mixture N27 is prepared as follows:

[1218]

[1219] The polymerizable mixture P27 was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S3-3 to the nematic LC host mixture N27.

[1220] Example 28

[1221] The nematic LC bulk mixture N28 is prepared as follows:

[1222]

[1223] The polymerizable mixture P28 was prepared by adding 0.3% of polymerizable compound M3 and 50 ppm of stabilizer S2-1 to the nematic LC host mixture N28.

[1224] Example 29

[1225] The nematic LC bulk mixture N29 is prepared as follows:

[1226]

[1227] The polymerizable mixture P29 was prepared by adding 0.4% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N29.

[1228] Example 30

[1229] The nematic LC bulk mixture N30 is prepared as follows:

[1230]

[1231] The polymerizable mixture P30 was prepared by adding 0.3% of polymerizable compound M1 and 50 ppm of stabilizer S1-1 to the nematic LC host mixture N30.

[1232] Example 31

[1233] The nematic LC bulk mixture N31 is prepared as follows:

[1234]

[1235] The polymerizable mixture P31 was prepared by adding 1.0% of polymerizable compound M1 and 0.6% of SA additive SA23 to the nematic LC host mixture N31.

[1236] Example 32

[1237] The nematic LC bulk mixture N32 is prepared as follows:

[1238]

[1239] The polymerizable mixture P32 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA23 and 50 ppm stabilizer S3-3 to the nematic LC host mixture N32.

[1240] Example 33

[1241] The nematic LC bulk mixture N33 is prepared as follows:

[1242]

[1243] The polymerizable mixture P33 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA32 and 50 ppm stabilizer S3-1 to the nematic LC host mixture N33.

[1244] Example 34

[1245] The nematic LC bulk mixture N34 is prepared as follows:

[1246]

[1247] The polymerizable mixture P34 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA32 and 50 ppm stabilizer S3-2 to the nematic LC host mixture N34.

[1248] Example 35

[1249] The nematic LC bulk mixture N35 is prepared as follows:

[1250]

[1251] The polymerizable mixture P35 was prepared by adding 1.0% polymerizable compound M2, 0.6% SA additive SA23 and 50 ppm stabilizer S3-3 to the nematic LC host mixture N35.

[1252] Example 36

[1253] The nematic LC bulk mixture N36 is prepared as follows:

[1254]

[1255] The polymerizable mixture P36 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA23 and 50 ppm stabilizer S1-1 to the nematic LC host mixture N36.

[1256] Example 37

[1257] The nematic LC bulk mixture N37 is prepared as follows:

[1258]

[1259] The polymerizable mixture P37 was prepared by adding 1.0% polymerizable compound M3, 0.6% SA additive SA23 and 50 ppm stabilizer S1-1 to the nematic LC host mixture N37.

[1260] Example 38

[1261] The nematic LC bulk mixture N38 is prepared as follows:

[1262]

[1263] The polymerizable mixture P38 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA32 and 50 ppm stabilizer S3-3 to the nematic LC host mixture N38.

[1264] Example 39

[1265] The nematic LC bulk mixture N39 is prepared as follows:

[1266]

[1267] The polymerizable mixture P39 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA23 and 50 ppm stabilizer S3-2 to the nematic LC host mixture N39.

[1268] Example 40

[1269] The nematic LC bulk mixture N40 is prepared as follows:

[1270]

[1271] The polymerizable mixture P40 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA32 and 50 ppm stabilizer S3-3 to the nematic LC host mixture N40.

[1272] Example 41

[1273] The nematic LC bulk mixture N41 is prepared as follows:

[1274]

[1275] The polymerizable mixture P41 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA32 and 50 ppm stabilizer S1-1 to the nematic LC host mixture N41.

[1276] Example 42

[1277] The nematic LC bulk mixture N42 is prepared as follows:

[1278]

[1279] The polymerizable mixture P42 was prepared by adding 1.0% polymerizable compound M2, 0.6% SA additive SA32 and 50 ppm stabilizer S2-1 to the nematic LC host mixture N42.

[1280] Example 43

[1281] The nematic LC bulk mixture N43 is prepared as follows:

[1282]

[1283] The polymerizable mixture P43 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA23 and 50 ppm stabilizer S3-2 to the nematic LC host mixture N43.

[1284] Example 44

[1285] The nematic LC bulk mixture N44 is prepared as follows:

[1286]

[1287] The polymerizable mixture P44 was prepared by adding 1.0% polymerizable compound M3, 0.6% SA additive SA23 and 50 ppm stabilizer S3-3 to the nematic LC host mixture N44.

[1288] Example 45

[1289] The nematic LC bulk mixture N45 is prepared as follows:

[1290]

[1291] The polymerizable mixture P45 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA32 and 50 ppm stabilizer S3-1 to the nematic LC host mixture N45.

[1292] Example 46

[1293] The nematic LC bulk mixture N46 is prepared as follows:

[1294]

[1295] The polymerizable mixture P46 was prepared by adding 1.0% polymerizable compound M2, 0.6% SA additive SA32 and 50 ppm stabilizer S2-1 to the nematic LC host mixture N46.

[1296] Example 47

[1297] The nematic LC bulk mixture N47 is prepared as follows:

[1298]

[1299] The polymerizable mixture P47 was prepared by adding 1.0% polymerizable compound M1, 0.6% SA additive SA32 and 50 ppm stabilizer S3-3 to the nematic LC host mixture N47.

[1300] Example 48

[1301] The nematic LC bulk mixture N48 is prepared as follows:

[1302]

[1303] The polymerizable mixture P48 was prepared by adding 0.4% of the polymerizable compound M1 to the nematic LC host mixture N48.

[1304] Example 49

[1305] The polymerizable mixture P49 was prepared by adding 0.2% of polymerizable compound RM-1 and 0.5% of polymerizable compound M1 to the nematic LC host mixture N4.

[1306]

[1307] Example 50

[1308] The polymerizable mixture P50 was prepared by adding 0.2% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N6.

[1309] Example 51

[1310] The polymerizable mixture P51 was prepared by adding 0.2% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N7.

[1311] Example 52

[1312] The polymerizable mixture P52 was prepared by adding 0.2% of polymerizable compound RM-1 and 0.5% of polymerizable compound M1 to the nematic LC host mixture N10.

[1313] Example 53

[1314] The polymerizable mixture P53 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N11.

[1315] Example 54

[1316] The polymerizable mixture P54 was prepared by adding 0.2% of polymerizable compound RM-1 and 0.5% of polymerizable compound M1 to the nematic LC host mixture N16.

[1317] Example 55

[1318] The polymerizable mixture P55 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N23.

[1319] Example 56

[1320] The polymerizable mixture P56 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N25.

[1321] Example 57

[1322] The polymerizable mixture P57 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N34.

[1323] Example 58

[1324] The polymerizable mixture P58 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N41.

[1325] Example 59

[1326] The polymerizable mixture P59 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N45.

[1327] Example 60

[1328] The polymerizable mixture P60 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M3 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N45.

[1329] Example 61

[1330] The polymerizable mixture P61 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M2 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1331] Example 62

[1332] The polymerizable mixture P62 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M3 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N2.

[1333] Example 63

[1334] The polymerizable mixture P63 was prepared by adding 0.3% polymerizable compound RM-1, 0.5% polymerizable compound M2 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N4.

[1335] Example 64

[1336] The polymerizable mixture P64 was prepared by adding 0.2% polymerizable compound RM-17, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1337]

[1338] Example 65

[1339] The polymerizable mixture P65 was prepared by adding 0.3% polymerizable compound RM-19, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N2.

[1340]

[1341] Example 66

[1342] The polymerizable mixture P66 was prepared by adding 0.2% polymerizable compound RM-64, 0.5% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1343]

[1344] Example 67

[1345] The polymerizable mixture P67 was prepared by adding 0.2% polymerizable compound RM-64, 0.5% polymerizable compound M2 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1346] Example 68

[1347] The polymerizable mixture P68 was prepared by adding 0.2% polymerizable compound RM-139, 0.3% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1348]

[1349] Example 69

[1350] The polymerizable mixture P69 was prepared by adding 0.2% polymerizable compound RM-142, 0.3% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1351]

[1352] Example 70

[1353] The polymerizable mixture P70 was prepared by adding 0.2% of polymerizable compound RM-142, 0.3% of polymerizable compound M2 and 100 ppm of stabilizer S1-1 to the nematic LC host mixture N1.

[1354] Example 71

[1355] The polymerizable mixture P71 was prepared by adding 0.2% polymerizable compound RM-139, 0.3% polymerizable compound M3 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1356] Example 72

[1357] The polymerizable mixture P72 was prepared by adding 0.2% polymerizable compound RM-142, 0.3% polymerizable compound M3 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N2.

[1358] Example 73

[1359] The polymerizable mixture P73 was prepared by adding 0.2% polymerizable compound RM-120, 0.3% polymerizable compound M1 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N1.

[1360]

[1361] Example 74

[1362] The polymerizable mixture P74 was prepared by adding 0.2% polymerizable compound RM-120, 0.3% polymerizable compound M2 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N2.

[1363] Example 75

[1364] The polymerizable mixture P75 was prepared by adding 0.2% polymerizable compound RM-120, 0.3% polymerizable compound M3 and 100 ppm stabilizer S1-1 to the nematic LC host mixture N4.

[1365] Application Example A

[1366] A1) Comparison of physical properties

[1367] The absorption wavelength λ at extinction coefficient E = 0.5 was determined for polymerizable compound M1 and compounds RM-1 and RM-35 at concentrations of 3 g / L and 5 g / L in DCM solution, respectively.

[1368] Absorption wavelengths can be used to characterize the wavelength dependence of UV photopolymerization of compounds.

[1369]

[1370] The melting points and UV absorption wavelengths of the polymerizable compound M1 of this invention and the prior art reference compounds RM-1 and RM-35 are summarized in Table 1.

[1371] Table 1 - Melting Point and UV Absorption

[1372]

[1373] As can be seen from Table 1, the polymerizable compound M1 of the present invention has the lowest melting point, which is particularly advantageous because it indicates that the monomer dissolves faster (resulting in a shorter production cycle) and has higher solubility in LC media compared to RM-1 and RM-35.

[1374] As can also be seen from Table 1, the polymerizable compound M1 of the present invention has the longest absorption wavelength and is therefore particularly suitable for UV photopolymerization at longer wavelengths or for faster polymerization at shorter wavelengths.

[1375] A2) Polymerizable mixtures

[1376] The polymerizable mixtures of the present invention are prepared by adding polymerizable compound M1 and optionally polymerizable compound RM-1 to nematic LC host mixtures N1, N2 and chiral nematic LC host mixture C3. A polymerizable reference mixture is prepared by adding polymerizable compound RM-1 or RM-35 to nematic LC host mixtures N1, N2 and chiral nematic LC host mixture C3.

[1377] The composition of the polymerizable mixtures is shown in Table 1. Among them, P1-1, P1-2, P1-3, P2-1, P2-2, P2-3, P2-4, P3-1, P3-2, P3-3, and P3-4 are mixtures of the present invention. Mixtures C1-1, C1-2, C2-1, C2-2, C3-1, and C3-2 are reference mixtures.

[1378] Table 2 - Composition of polymerizable mixtures

[1379]

[1380] A3) Voltage Holding Rate (VHR)

[1381] To measure VHR, a polymerizable mixture is filled into an electro-optic test chamber consisting of two planar parallel glass substrates, each substrate having an ITO electrode layer and a polyimide alignment layer on its inner side, wherein the two polyimide layers rub against each other antiparallel and cause vertical edge alignment of LC molecules.

[1382] To elucidate the effect of UV light on different LC host mixtures, the VHR of the host mixtures was measured at 60°C without the use of polymerizable compounds, using two different UV lamps with a voltage of 1 V / 0.6 Hz applied before and after UV exposure (Type B fluorescent UV lamp, short wavelength cutoff at 330 nm, and Type C fluorescent UV lamp, short wavelength cutoff at 310 nm). Photostress generally leads to a decrease in VHR in LC mixtures; therefore, the smaller the absolute decrease in VHR value after stress, the better the performance for display applications.

[1383] The results for the pure bulk mixture are shown in Table 3.

[1384] Table 3 – VHR of the main mixture

[1385]

[1386] As shown in Table 3, for LC host mixture N1, there was no significant difference in VHR after exposure to type B and type C lamps. However, for LC host mixtures N2 and C3, there were significant differences in VHR values ​​when irradiated with type B or type C lamps. This indicates that the UV spectrum has a significant impact on different LC host mixtures.

[1387] As described above, the VHR values ​​of polymerizable mixtures based on the host mixtures N1, N2, or C3 were measured respectively. Considering the different absorption wavelengths of the polymerizable compounds, to ensure optimal UV absorption, a UV C-type lamp was used for mixtures containing polymerizable compound RM-1, while a UV B-type lamp was used for mixtures containing polymerizable compounds RM-35 or M1.

[1388] The results are shown in Tables 4, 5, and 6.

[1389] Table 4 – VHR of polymerizable mixtures based on bulk mixture N1

[1390]

[1391] As shown in Table 4, all polymerizable mixtures exhibited good VHR values ​​after UV exposure.

[1392] Table 5 – VHR of polymerizable mixtures based on bulk mixture N2

[1393]

[1394] As shown in Table 4, compared with reference mixtures C2-1 and C2-2, the polymerizable mixtures P2-1, P2-2, P2-3 and P2-4 of the present invention exhibit significantly higher VHR after UV exposure.

[1395] Table 6 – VHR of polymerizable blends based on bulk blend C3

[1396]

[1397] As shown in Table 6, the polymerizable mixtures P31, P32, P3-3, and P3-4 of the present invention exhibit significantly higher VHRs after UV exposure than the reference mixtures C3-1 and C3-2. It is also observed that the polymerizable mixtures P3-2, P3-3, and P3-4, containing polymerizable compound M1 and polymerizable compound RM-1, show a further increase in VHR after UV exposure.

[1398] Tilt angle stability

[1399] The polymerizable mixture was filled into a PSVA test chamber with a gap of approximately 3.3 µm, and then exposed to UV light using a Type C lamp for the UV1 step and a Type C or Type B lamp for the UV2 step. During the UV1 step, a voltage (20 V, DC) was simultaneously applied to the electrodes of the test chamber. No voltage was applied during the UV2 step. Other conditions were as follows:

[1400] UV1 intensity: 4.3 mW / cm² at room temperature, with the duration of irradiation adjusted to achieve a tilt angle of 2°.

[1401] UV2 intensity: 1.7 mW / cm² at room temperature, for 120 minutes

[1402] After UV polymerization, the change in tilt angle was measured in the test chamber using Otsuka Electronics' RET system, and at 60 V. 峰-峰 Apply electrical stress for 72 hours under a 60 Hz square wave, illuminate with the monitor backlight, then relax for 10-20 minutes before taking measurements.

[1403] Tilt stability, which is the change in tilt angle after a period of electric field stress, is a measure of image viscosity. A low change in tilt angle indicates high tilt stability and low image viscosity.

[1404] The change in tilt angle is determined according to equation (1). Δ tilt

[1405] tilt 应力后 – tilt 产生倾斜后 = Δ tilt (1)

[1406] And shown in Table 7 below.

[1407] Δ tilt The lower the value, the higher the tilt stability.

[1408] Table 7 – Tilt Stability

[1409]

[1410] As can be seen from Table 7, the polymerizable mixtures of the present invention exhibit good tilt stability.

Claims

1. An LC medium, characterized in that it comprises one or more polymerizable compounds of formula I. P-Sp-A a -(Z a -A b ) z -R b I Each group is independent of the others and, each time it appears, has the same or different meanings as follows: R b For P-Sp- or R, R is F, Cl, -CN, or a straight-chain, branched, or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups are optionally represented by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O-, CR in such a manner that the O- and / or S- atoms are not directly connected to each other. 0 =CR 00 -、-C≡C-、 Furthermore, one or more H atoms are each optionally replaced by F, Cl, or P-Sp-. P is a polymerizable group. Sp is an optional spacer group substituted with P, or a single bond. A a A b It is an alicyclic, heterocyclic, aromatic, or heteroaromatic ring group having 4-20 ring atoms, which is monocyclic or polycyclic and optionally substituted by one or more A, L, or P-Sp- groups. Z a is -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH2-CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 - or a single bond, R 0 , R 00 It is H or an alkyl group having 1-12 carbon atoms. A is an alkyl group having 2-12, preferably 2-8, carbon atoms, wherein one or more, preferably non-terminal CH2 groups are replaced by S, such that the S atoms are not directly connected to each other. L is F, Cl, -CN, P-Sp- or a straight-chain, branched or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups are optionally represented by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O-, CR-, etc., such that the O- and / or S- atoms are not directly connected to each other. 0 =CR 00 -、-C≡C-、 Furthermore, one or more H atoms are each optionally replaced by P-Sp-, F, or Cl. z is 0, 1, 2, 3 or 4. n1 is 1, 2, 3, or 4. The compound of formula I contains at least one group A. a Or A b It is substituted by at least one group A. It also contains one or more compounds of formula II. Each group is independent of the others and, each time it appears, has the same or different meanings as follows: R 1 , R 2 It is a straight-chain, branched, or cyclic alkyl group having 1-25 carbon atoms, wherein one or more non-adjacent CH2 groups are optionally configured such that the O- and / or S- atoms are not directly connected to each other by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O-, CR 0 =CR 00 -、-C≡C-、 Furthermore, one or more H atoms are each optionally replaced by F or Cl. A 1 A 2 Groups selected from the following formulas Each group is independent of the others and, each time it appears, has the same or different meanings as follows: Z 1 Z 2 For -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2F4-, -CF=CF-, -CH=CH-CH2O-, or single bonds. L 1 , L 2 , L 3 , L 4 It can be F, Cl, OCF3, CF3, CH3, CH2F, or CHF2. Y is H, F, Cl, CF3, CHF2, or CH3. L C It is CH3 or OCH3. a1 is 1 or 2. a2 is 0 or 1. It is characterized by containing one or more additional polymerizable compounds selected from the following formula: Each group, when appearing in the same or different manner, and independently of each other, has the following meaning: P 1 , P 2 , P 3 The polymerizable group is preferably selected from ethyleneoxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxy groups. Sp 1 Sp 2 Sp 3 It is a single bond or a spacer group, wherein in addition, the group P 1 -Sp 1 -、P 1 -Sp 2 -and P 3 -Sp 3 One or more of the representations R in - aa The condition is that the group P exists. 1 -Sp 1 -、P 2 -Sp 2 and P 3 -Sp 3 - at least one of them is different from R aa Preferred -(CH2) p1 -、-(CH2) p1 -O-、-(CH2) p1 -CO-O- or -(CH2) p1 -O-CO-O-, where p1 is an integer from 1 to 12. R aa It is H, F, Cl, CN, or a straight-chain or branched alkyl group having 1-25 C atoms, wherein, in addition, one or more non-adjacent CH2 groups may be independently coupled to each other such that the O and / or S atoms are not directly connected to each other by -C(R) 0 )=C(R 00 )-、-C≡C-、-N(R 0 -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O-, and wherein, in addition, one or more H atoms may be replaced by F, Cl, CN or P. 1 -Sp 1 - Alternatively preferred are straight-chain or branched, optionally mono- or polyfluoroalkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy groups having 1-12 carbon atoms (wherein the alkenyl and alkynyl groups have at least two carbon atoms and the branched groups have at least three carbon atoms), and wherein R aa Does not represent or contain the group P 1 P 2 or P 3 , R 0 , R 00 It is H or an alkyl group having 1-12 carbon atoms. R y and R z It can be H, F, CH3 or CF3. X 1 , X 2 , X 3 It can be -CO-O-, -O-CO-, or a single bond. Z M1 -O-, -CO-, -C(R) y R z - or -CF2CF2-, Z M2 Z M3 It can be -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2). n -, where n is 2, 3, or 4. L is F, Cl, CN, or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, or alkoxycarbonyloxy group having 1-12 C atoms. L', L" represents H, F, or Cl. k is 0 or 1. r can be 0, 1, 2, 3, or 4. s is 0, 1, 2 or 3. t is 0, 1, or 2. x is 0 or 1.

2. The LC medium according to claim 1, characterized in that group A in formula I represents a thioalkyl group having 1-7 C atoms.

3. The LC medium according to claim 1 or 2, characterized in that group A in formula I represents SCH3.

4. The compound according to any one of claims 1-3, characterized in that the compound of formula I is selected from the following sub-formulas: Each group is independent of the others and, each time it appears, has the same or different meanings as follows: A, P, Sp, R b It has one of the meanings given in claim 1, 2 or 3. L 11 -L 17 For L or A, r1, r2, r3, r4 are 0, 1, 2, 3, or 4, where r1 + r2 + r3 ≥ 1 in equations I1, I2, and I5, and r1 + r2 + r3 ≥ 1 in equation I12. r5, r6, can be 0, 1, 2, or 3, where r5 + r6 ≥ 1 in equation I3 and r4 + r5 + r6 ≥ 1 in equations I4a and I4b. r7 can be 1, 2, 3, or 4. c is 0, 1, or 2. The compound contains at least one L group of type A. 11 -L 17 .

5. The LC medium according to any one of claims 1-4, characterized in that the compound of formula I is selected from the following sub-formulas: in R, P, Sp, L 11-17 r1-r7 have the meaning given in any one of claims 1-5. L 18 , L 19 and L 20 Having for L 11 One of the meanings given is r8 is 0, 1, or 2. r9 can be 0, 1, 2, or 3. r10 is 1, 2, or 3. c is 0, 1, or 2. Sp(P)2 represents a spacer group Sp in which two polymerizable groups P are replaced at the same or different positions. and among them In equations I1A, I1C, and I1E, r1+r2 ≥1. In equations I1B, I1D, and I1F, r1+r5 ≥1. In equations I1G, I3A, and I3C, r5 + r6 ≥ 1. In equations I2A, I2D, I2E, I5A, and I5C, r1+r2+r3 ≥1. In equations I2B, I2C, I2F, I5B, and I5D, r1+r3+r5 ≥1. In equation I2G, r3+r5+r6 ≥1. In equations I4A, I4C, and I4E, r4+r5+r6 ≥1. In equation I4D, r5+r6+r9 ≥1. In equation I3B, r5 + r8 ≥ 1. In equation I4B, r4+r5+r8 ≥1. In equations I12A, I12D, and I12E, r1+r2+r3 ≥1. In equations I12B, I12C, and I12F, r1+r3+r5 ≥1. In equation I12G, r3+r5+r6 ≥1. And the compound contains at least one L group representing A. 11 -L 20 .

6. The LC medium according to one or more of claims 1-5, wherein the additional polymerizable compound is selected from the formula CM Each group, when appearing in the same or different manner, and independently of each other, has the following meaning: P and Sp have one of the meanings given in claim 1. L is F, Cl, CN, or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, or alkoxycarbonyloxy group having 1-12 C atoms. k is 0 or 1. r1 and r2 are 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and very preferably 0 or 1.

7. The LC medium according to one or more of claims 1-6, wherein the additional polymerizable compound is selected from formula MT. Each group, when appearing in the same or different manner, and independently of each other, has the following meaning: P and Sp have one of the meanings given in claim 1. L is F, Cl, CN, or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, or alkoxycarbonyloxy group having 1-12 C atoms. k is 0 or 1. r1, r2, r3 can be 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and very preferably 0 or 1.

8. An LC medium according to one or more of claims 1-7, characterized in that it contains one or more compounds of formula II selected from compounds of formulas IIA, IIB, IIC and IID. in R 2A and R 2B Each of these groups independently represents H, an unsubstituted alkyl or alkenyl group having up to 15 C atoms, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more CH2 groups among these groups can be used such that the O atom is not directly connected to each other by -O-, -S-, Replace with -C≡C-, -CF₂O-, -OCF₂-, -OC-O-, or -O-CO-. L 1 -L 4 Each can be independently represented as F, Cl, CF3, or CHF2. Y represents H, F, Cl, CF3, CHF2, or CH3, with H or CH3 being preferred, and H being particularly preferred. Z 2 Z 2B and Z 2D Each of these independently represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-. p represents 0, 1, or 2, and Each occurrence of q represents either 0 or 1, either the same or different.

9. The LC medium according to any one of claims 1-8, characterized in that it additionally comprises one or more compounds of formula III. in R 11 and R 12 Each of these groups independently represents H, an alkyl or alkoxy group having 1-15 carbon atoms, wherein one or more CH2 groups among these groups can be represented independently such that the O atom is not directly connected to each other. -O-, -S-, -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -OC-O-, or -O-CO- are substitutes, and among them, In addition, one or more H atoms can be replaced by halogens. A 3 Each occurrence represents an independent representation. a) 1,4-cyclohexeneyl or 1,4-cyclohexeneyl, wherein one or both non-adjacent CH2 groups may be replaced by -O- or -S-. b) 1,4-Phenylidene, wherein one or both CH groups may be replaced by N, or c) A group selected from spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octyl, 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. Groups a), b), and c) can be mono- or poly-substituted with halogen atoms. n represents 0, 1, or 2, preferably 0 or 1. Z 1 Each occurrence independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond. L 11 and L 12 Each of these elements independently represents F, Cl, CF3, or CHF2, preferably H or F, with F being the most preferred. W represents O or S.

10. The LC medium according to one or more of claims 1 to 9, characterized in that... The LC medium comprises one or more compounds of formula IIB as defined in claim 8.

11. The LC medium according to one or more of claims 1 to 10, characterized in that... The LC medium comprises one or more compounds of formula IIC as defined in claim 8.

12. The LC medium according to one or more of claims 1 to 11, characterized in that... The LC medium comprises one or more compounds of formula IID as defined in claim 8.

13. The LC medium according to one or more of claims 1 to 12, characterized in that... The LC medium contains one or more compounds selected from formulas III-1 and III-2. The groups appearing therein have the same meaning as given in Formula III of claim 9.

14. The LC medium according to one or more of claims 1 to 13, characterized in that... The LC medium contains one or more compounds selected from formulas IIIA-1 and IIIA-2. Where L 11 and L 12 Having the same meaning as given in formula III of claim 9, (O) represents O or a single bond. R IIIA This refers to an alkyl or alkenyl group, or a Cy-C group, having a maximum of 7 carbon atoms. m H 2m+1 -, m and n are the same or different from 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, and Cy represents an alicyclic group having 3, 4, or 5 ring atoms, which may be optionally alkyl or alkenyl groups having a maximum of 3 C atoms, or substituted with halogen or CN, and preferably represents cyclopropyl, cyclobutyl, or cyclopentyl.

15. The LC medium according to one or more of claims 1 to 14, characterized in that... The LC medium contains one or more compounds selected from formula III-3. in R 11 , R 12 The same or different representations of H, alkyl or alkoxy groups having 1-15 C atoms, wherein one or more CH2 groups of these groups are optionally independently represented such that the O atoms are not directly connected to each other by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -S-, -CO-O-, or -O-CO- are substituted, and in addition, one or more H atoms may be substituted with halogens.

16. The LC medium according to one or more of claims 1 to 15, characterized in that... The LC medium contains one or more compounds selected from formulas IV-1 to IV-6. in "alkyl" and "alkyl" "Each of the above can be independently represented as an alkyl group having 1-7 carbon atoms, preferably having 2-5 carbon atoms." "alkenyl" indicates an alkenyl group having 2-5 carbon atoms, preferably 2-4 carbon atoms, and particularly preferably 2 carbon atoms. alkenyl "Indicates an alkenyl group having 2-5 carbon atoms, preferably 2-4 carbon atoms, particularly preferably 2-3 carbon atoms, and..." "alkoxy" refers to an alkoxy group having 1-5 carbon atoms, preferably having 2-4 carbon atoms.

17. The LC medium according to one or more of claims 1 to 16, characterized in that... The LC medium contains one or more compounds selected from formulas V-10a, V-10b, and V-10c.

18. The LC medium according to any one of claims 1-17, characterized in that it additionally comprises one or more compounds of formula IV. in R 41 This indicates an unsubstituted alkyl group having 1-7 carbon atoms or an unsubstituted alkenyl group having 2-7 carbon atoms, preferably. n -alkyl groups, particularly preferably having 2, 3, 4 or 5 carbon atoms, and R 42 The term refers to an unsubstituted alkyl group having 1-7 carbon atoms or an unsubstituted alkoxy group having 1-6 carbon atoms, preferably having 2-5 carbon atoms, an unsubstituted alkenyl group having 2-7 carbon atoms, preferably having 2, 3 or 4 carbon atoms, more preferably vinyl or 1-propenyl and especially vinyl.

19. The LC medium according to any one of claims 1-18, characterized in that it additionally comprises one or more compounds of formula V. in R 51 and R 52 They are independent of each other for R 41 and R 42 One of the given meanings and preferred meanings refers to an alkyl group having 1-7 carbon atoms, preferably an n-alkyl group, particularly preferably an n-alkyl group having 1-5 carbon atoms; an alkoxy group having 1-7 carbon atoms, preferably an n-alkoxy group, particularly preferably an n-alkoxy group having 2-5 carbon atoms; and an alkoxyalkyl, alkenyl, or alkenyloxy group having 2-7 carbon atoms, preferably having 2-4 carbon atoms, preferably an alkenyloxy group. in 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, and particularly preferably a single bond. n is 1 or 2.

20. The LC medium according to any one of claims 1-19, characterized in that it additionally comprises one or more additives selected from stabilizers, chiral dopants, polymerization initiators and self-aligning additives.

21. A method for preparing an LC medium according to one or more of claims 1-20, comprising the steps of: mixing one or more polymerizable compounds of formula I as defined in one or more of claims 1-5 with one or more compounds of formula II, III, IV and / or V as defined in one or more of claims 1 or 8-9, and optionally mixing with one or more additional polymerizable compounds as defined in claim 1, and optionally mixing with other liquid crystal compounds and / or additives, and optionally polymerizing the polymerizable compounds.

22. An LC display comprising an LC medium as defined in any one or more of claims 1-20.

23. The LC display according to claim 22, wherein it is a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS or SA-VA display.

24. The LC display according to claim 22 or 23, characterized in that it comprises two substrates, at least one of which is transparent to light, an electrode disposed on each substrate, or two electrodes disposed on only one substrate, and a layer of LC dielectric according to one or more of claims 1-20 located between the substrates, wherein the polymerizable compound is polymerized between the substrates of the display by UV light polymerization.

25. A method for preparing an LC display according to claim 24, comprising the steps of: providing an LC medium according to one or more of claims 1-20 between substrates of the display, and polymerizing a polymerizable compound by UV light irradiation, preferably simultaneously applying a voltage to electrodes of the display.

26. The method of claim 25, characterized in that the wavelength of the UV light is 350 to <370 nm.

27. The method according to claim 25 or 26, characterized in that UV-LED lamps are used for UV irradiation.

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