LCD Media

Abstract

To provide liquid-crystal media.SOLUTION: The present invention relates to liquid-crystal (LC) media having a negative dielectric anisotropy comprising a compound of formula I as defined herein, and to the use of the LC media for optical, electro-optical and electronic purposes, in particular in energy-efficient LC displays, especially in IPS, FFS, VA or PS-VA displays.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a liquid crystal (LC) medium having negative dielectric anisotropy comprising a compound of formula I as defined herein, and to the use of the LC medium in optical, electro-optical and electronic purposes, and in particular in energy-efficient LC displays, especially IPS, FFS, VA, or PS-VA displays. [Background technology]

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

[0003] So-called VA ("vertically aligned") displays, which have a wide viewing angle, are known. The LC cell of a VA display has an LC medium layer between two transparent electrodes, where the LC medium usually has negative dielectric anisotropy. When the switch is off, the molecules in the LC layer are oriented perpendicular to the electrode surface, i.e., homeotropic or tilt homeotropic orientation. When a voltage is applied to the two electrodes, the LC molecules re-orient parallel to the electrode surface.

[0004] Further developments involve so-called PS ("polymer sustained") or PSA ("polymer sustained alignment") type displays, sometimes referred to as "polymer stabilized." In these displays, a small amount, e.g., 0.3% by weight, typically less than 1% by mass, of one or more polymerizable compounds (one or more), preferably polymerizable monomer compounds (one or more), is added to the LC medium. After filling the display with the LC medium, polymerization or crosslinking is carried out in situ, usually by UV photopolymerization, optionally while applying a voltage to the display electrodes. Polymerization is carried out at a temperature at which the LC medium exhibits a liquid crystal phase, usually at room temperature. Adding polymerizable mesogens or liquid crystal compounds, also known as reactive mesogens or "RM (reactive mesogen)," to the LC mixture has been proven to be particularly appropriate.

[0005] Furthermore, there are known displays called IPS ("in-plane switching") which have an LC layer between two substrates, in which the two electrodes are placed on only one of the two substrates and preferably have an interlocking comb-like structure. When a voltage is applied to the electrodes, an electric field with a significant component parallel to the LC layer is generated between the electrodes. This causes the LC molecules to be reoriented in the layer plane.

[0006] Furthermore, so-called FFS ("fringe-field switching") displays have been reported, particularly SHJung et al., Jpn.J.Appl.Phys., Vol. 43, No. 3, 2004, p. 1028 (Non-Patent Literature 1). This display has two electrodes on the same substrate, one of which is comb-shaped and the other is unstructured. This generates a strong so-called "fringe field," that is, a strong electric field near the electrode ends, and an electric field with both strong vertical and strong horizontal components is generated across the cell. FFS displays have low contrast dependence on the viewing angle. FFS displays typically contain an LC medium with positive dielectric anisotropy and an orientation layer, usually a polyimide orientation layer, which results in a planar orientation with respect to the molecules of the LC medium.

[0007] Further FFS displays have been disclosed that have electrode designs and layer thicknesses similar to conventional FFS displays, but instead of an LC medium layer having positive dielectric anisotropy, they feature an LC medium layer having negative dielectric anisotropy (see, for example, SHLee et al., Appl. Phys. Lett. Vol. 73 (No. 20), 1998, pp. 2882-2883 (Non-Patent Literature 2), and SHLee et al., Liquid Crystals Vol. 39 (No. 9), 2012, pp. 1141-1148 (Non-Patent Literature 3). Compared to LC mediums having positive dielectric anisotropy, LC mediums may exhibit a more preferable director orientation with smaller tilt and higher twist orientation, and as a result, these displays may exhibit higher transmittance. The display further includes an orientation layer, preferably a polyimide orientation layer provided on at least one of the substrates, which is in contact with the LC medium and causes a planar orientation of the LC molecules in the LC medium. These displays are also known as "Ultra Brightness FFS (UB-FFS)" mode displays.

[0008] Typical applications of in-plane switching (IPS) and fringe-field switching (FFS) technologies include monitors, laptops, televisions, mobile phones, and tablet PCs.

[0009] Both IPS and FFS technologies offer certain advantages over other LCD technologies, such as vertical alignment (VA) technology, including a wider range of improved contrast dependence across viewing angles.

[0010] Liquid crystal compositions suitable for LCDs, and especially FFS and IPS displays, are known from, for example, Japanese Patent Application Publication No. 07-181439 (Patent Document 1), European Patent No. 0667555 (Patent Document 2), European Patent No. 0673986 (Patent Document 3), German Patent No. 19509410 (Patent Document 4), German Patent No. 19528106 (Patent Document 5), German Patent No. 19528107 (Patent Document 6), International Publication No. 96 / 23851 (Patent Document 7), and International Publication No. 96 / 28521 (Patent Document 8). However, these compositions have certain drawbacks. Among other defects, most result in unfavorably long address times, inappropriate resistivity values, and / or require excessively high operating voltages. Improvement in both operating characteristics and storage is desirable.

[0011] The PS(A) principle is used in various conventional LC display modes. For example, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, and PS-TN displays are known. Polymerization of RM is preferably carried out with voltage applied in the case of PS-VA and PS-OCB displays, and with or without voltage applied, preferably without charge, in the case of PS-IPS displays.

[0012] Depending on the display mode, an LC medium may be added that induces a desired orientation, such as homeotropic or planar orientation, through a self-assembly mechanism in situ. This eliminates the need for conventional alignment layers on one or both substrates. These display modes are also known as "elf-aligned" or "self-aligning" (SA) modes.

[0013] There remains a need in the field for further liquid crystal media and their use in FFS and IPS applications, particularly for displays with high transmittance, good black levels, and high contrast ratios, as well as good low-temperature stability and fast address times. [Prior art documents] [Patent Documents]

[0014] [Patent Document 1] Japanese Patent Application Publication No. 07-181439 [Patent Document 2] European Patent No. 0667555 [Patent Document 3] European Patent No. 0673986 [Patent Document 4] German Patent No. 19509410 Specification [Patent Document 5] German Patent No. 195 28 106 Specification [Patent Document 6] German Patent No. 195 28 107 Specification [Patent Document 7] International Publication No. 96 / 23 851 [Patent Document 8] International Publication No. 96 / 28 521 [Non-patent literature]

[0015] [Non-Patent Document 1] SHJung et al., Jpn.J.Appl.Phys., Volume 43, No. 3, 2004, Page 1028 [Non-Patent Document 2] SHLee et al., Appl. Phys. Lett. Vol. 73 (No. 20), 1998, pp. 2882-2883 [Non-Patent Document 3] SHLee et al., Liquid Crystals Volume 39 (No. 9), 2012, pp. 1141-1148 [Overview of the Initiative] [Problems that the invention aims to solve]

[0016] Accordingly, the object of the present invention is to provide a liquid crystal medium that is particularly for FFS, UB-FFS, and IPS displays, but also for VA or PS-VA displays, and especially for active matrix displays such as those addressed by TFTs, that does not exhibit the above-mentioned drawbacks, or exhibits them to a lesser degree, preferably having high resistivity, low threshold voltage, appropriate dielectric anisotropy, good low-temperature stability (LTS), fast response time, and low rotational viscosity, enabling high brightness and high transmittance, in addition to exhibiting desirable reliability and stability.

[0017] A further object of the present invention is to provide a display having a high contrast ratio, high transmittance in one optical state, a fast address time, and particularly favorable stability at low and high temperatures. Further objects of the present invention will be immediately apparent to those skilled in the art from the following detailed description.

[0018] This objective is addressed by the subject matter defined in the independent claims, while preferred embodiments are described in their respective dependent claims and further explained below.

[0019] The present invention provides the following items, including particularly key aspects, preferred embodiments, and specific features, each of which, individually or in combination, contributes to solving the above objectives and ultimately provides additional advantages. [Means for solving the problem]

[0020] A first aspect of the present invention provides a liquid crystal medium having negative dielectric anisotropy and containing one or more compounds of formula I.

[0021] [ka]

[0022] During the ceremony R 1 This represents a linear or branched alkenyl group having 2 to 15 carbon atoms, provided that one or more CH2 groups are arranged so that the oxygen atoms are not directly linked to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -O-, -CO-O-, or -O-CO- may be substituted for each other independently, and in the group, one or more H atoms may be replaced by halogens. R 2 This represents a linear or branched alkyl or alkoxy group having H and 1 to 15 C atoms, provided that one or more CH2 groups in these groups are arranged so that the O atoms are not directly linked to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO- may be substituted for each other independently, and in the group, one or more H atoms may be replaced by halogens. Y 1 represents H, F, Cl, or CH3, preferably H or CH3, more preferably H.

[0023] It has been favorably recognized that using the liquid crystal medium according to the present invention enables advantageous optical and electro-optical performance, particularly fast response time, high brightness, and high contrast, in displays as described and claimed herein. In addition, the medium according to the present invention is remarkably favorable, exhibiting appropriately high optical anisotropy and excellent stability with respect to light, particularly UV light and heat, and even under extreme loads, particularly excellent reliability at high and low temperatures, and especially a favorable voltage holding ratio (VHR). The voltage holding ratio after UV light loading is particularly improved.

[0024] This makes it possible to provide LCD displays with high brightness, high transmittance, and short response times, especially in UB-FFS, FFS, and IPS modes.

[0025] The liquid crystal media according to the present invention is suitable for electro-optical displays such as large televisions and mobile applications such as mobile phones and PDAs, based on dielectrically negative liquid crystals and polymer-stabilized variants thereof.

[0026] Accordingly, another aspect of the present invention relates to a liquid crystal display comprising a liquid crystal medium according to the present invention, preferably a VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, SA-VA, PSA-PS-VA, PS-IPS, PS-FFS, or PS-UB-FFS display, or a polymer-stabilized SA-VA or polymer-stabilized SA-FFS display.

[0027] Further aspects of the present invention relate to the use of liquid crystal media according to the present invention in electro-optical switching applications, particularly in electro-optical displays, but also in optical shutters, switchable windows, or 3D applications. [Modes for carrying out the invention]

[0028] Without limiting itself thereto, the present invention is illustrated below by a detailed description of aspects, embodiments and specific features, with specific embodiments being described in more detail.

[0029] In this specification, halogen represents F, Cl, Br, or I, preferably F or Cl, more preferably F.

[0030] In this invention, all atoms also include their isotopes. In particular, one or more hydrogen atoms (H) may be replaced with deuterium (D), which is especially preferred in some embodiments; high deuteration enables or simplifies the analytical determination of the compound, especially at low concentrations.

[0031] In this specification, alkyl and / or alkoxy groups mean linear or branched alkyl groups. They are preferably linear and have 2, 3, 4, 5, 6 or 7 carbon atoms, and accordingly preferably represent ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, and further represent methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.

[0032] In this specification, oxaalkyl preferably represents linear 2-oxapropyl (=methoxymethyl), 2-(=ethoxymethyl) or 3-oxabutyl (=2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, or 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.

[0033] In this specification, alkenyls, i.e., alkyl groups in which one CH2 group is replaced with -CH=CH-, may be linear or branched. They are preferably linear and have 2 to 10 carbon atoms. Therefore, it represents vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, penta-1-, -2-, -3- or -4-enyl, hexa-1-, -2-, -3-, -4- or -5-enyl, hepta-1-, -2-, -3-, -4-, -5- or -6-enyl, octa-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, nona-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, deca-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or -9-enyl.

[0034] In this specification, alkyl or alkenyl groups that are at least monosubstituted with a halogen are preferably linear, and the halogen is preferably F or Cl. In the case of polysubstituted groups, the halogen is preferably F. Perfluoro groups are also among the resulting groups. In the case of monosubstituted groups, the fluorine or chlorine substituent may be at any desired position, but is preferably at the ω-position.

[0035] In this specification, monofluorinated or polyfluorinated alkyl or alkoxy groups having one, two or three carbon atoms, or monofluorinated or polyfluorinated alkenyl groups having two or three carbon atoms, are particularly preferably F, Cl, CF3, CHF2, OCF3, OCHF2, OCFHCF3, OCFHCHF2, OCFHCHF2, OCF2CH3, OCF2CHF2, OCF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCFHCF2CF3, OCFHCF2CHF2, OCF2CF2CF3, OCF2CF2CClF2, OClFCF2CF3, OCH=CF2, or CH=CF2, very particularly preferably F or OCF3, and even more preferably CF3, OCF=CF2, OCHF2, or OCH=CF2.

[0036] In this specification, the 1,4-cyclohexylene ring and the 1,4-phenylene ring are represented as follows: [ka]

[0037] The cyclohexylene ring is a trans-1,4-cyclohexylene ring.

[0038] The liquid crystal medium according to the present invention has a negative dielectric anisotropy Δε.

[0039] In the upper and lower sections, Δε represents dielectric anisotropy, where Δε = ε ∥ -ε ⊥ The dielectric anisotropy Δε is preferably determined at 20°C and 1kHz.

[0040] In particular, the liquid crystal medium has a negative dielectric anisotropy Δε of preferably -0.5 or less, more preferably -1.5 or less, and even more preferably -2.5 or less. It is especially preferable that the liquid crystal medium exhibits a dielectric anisotropy Δε in the range of -6 to -2, more preferably -5.5 to -2.5, even more preferably -5 to -3, and particularly preferably -4.5 to -3.5.

[0041] The liquid crystal medium preferably has an optical anisotropy Δn of 0.08 or more, more preferably 0.09 or more, and even more preferably 0.10 or more.

[0042] In the upper and lower sections, Δn represents optical anisotropy, where Δn = n e -n o The optical anisotropy Δn is preferably determined at 20°C and a wavelength of 589.3 nm. The liquid crystal medium preferably has an optical anisotropy in the range of 0.08 to 0.13, particularly 0.10 to 0.12.

[0043] According to the present invention, the liquid crystal medium comprises one or more compounds of formula I as defined herein.

[0044] Preferably, R in formula I1 represents an alkenyl group having 2 to 7 carbon atoms, more preferably a linear alkenyl group having 2 to 7 carbon atoms. R 1 particularly 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-.

[0045] Preferably, R in formula I 2 represents an alkyl or alkoxy group having 1 to 7 carbon atoms, more preferably a linear alkyl group having 1 to 7 carbon atoms. R 2 particularly preferably represents methyl, ethyl, n-propyl, n-butyl or n-pentyl.

[0046] In one embodiment, the liquid crystal medium contains only one kind of the compound of formula I.

[0047] In another embodiment, the liquid crystal medium contains two or more kinds of the compound of formula I.

[0048] Preferably, one or more compounds of formula I and particularly their more preferred compounds are contained in the liquid crystal medium in a total amount of 10% by weight or less, more preferably 7% by weight or less, still more preferably 4% by weight or less. The total amount of one or more compounds of formula I and particularly their more preferred compounds contained in the liquid crystal medium is preferably in the range of 0.25% by weight to 8% by weight, more preferably 0.5% by weight to 5% by weight, particularly 1% by weight to 3% by weight.

[0049] The compound of formula I is preferably selected from the group of compounds of formulae I-1 to I-10.

[0050]

Chemical formula

[0051]

Chemical formula

[0052] In the formula, R 1 and R 2 This has the meaning given above in equation I, and, however, R 1 Preferably represents a linear alkenyl group having 2 to 7 C atoms, more preferably CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH-, or CH3-CH=CH-(CH2)2- and, however, R 2 preferably represents a linear alkyl group having 1 to 7 carbon atoms.

[0053] In a preferred embodiment, one or more compounds of formula I are selected from the group of compounds of formula Ia to If.

[0054] [ka]

[0055] In the formula, R 2 The ''> has the meaning given in formula I, preferably representing methyl, ethyl, n-propyl, methoxy, ethoxy, or n-propoxy, more preferably representing methyl or ethyl, and particularly representing methyl.

[0056] The liquid crystal medium is particularly preferably to contain a compound known as compound CLP-V-1, according to formula Ia-1 and the acronyms described below and in Tables A to C.

[0057] [ka]

[0058] Preferably, the compound of formula Ia-1 is contained in the liquid crystal medium in an amount of 10% by weight or less, more preferably 7% by weight or less, and even more preferably 4% by weight or less. The amount of the compound of formula Ia-1 contained in the liquid crystal medium is preferably in the range of 0.25% to 8% by weight, more preferably 0.5% to 5% by weight, and particularly preferably 1% to 3% by weight.

[0059] In one embodiment, the compound of formula Ia-1 is the only compound of formula I contained in the medium. However, according to another embodiment, in addition to the compound of formula Ia-1, the medium may also contain one or more compounds that conform to formula I.

[0060] In another embodiment, the liquid crystal medium comprises compound Ia-2.

[0061] [ka]

[0062] Preferably, the liquid crystal medium further comprises one or more compounds selected from the group of compounds of formulas IIA, IIB, IIC, and IID.

[0063] [ka]

[0064] During the ceremony, R 2A , R 2B , R 2C and R 2D Each represents an alkyl or alkenyl group having H and up to 15 C atoms independently, wherein the group is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, provided that one or more CH2 groups in these groups are -O-, -S-, such that the O atoms are not directly bonded to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CO-O-, or -O-CO- can be substituted, L 1 ~L 4 Each of these independently represents F, Cl, CF3, or CHF2. Y represents H, F, Cl, CF3, CHF2, or CH3. Z 2 , Z 2B and Z 2D These each independently represent a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, or -CH=CHCH2O-. p represents 0, 1, or 2. q represents 0 or 1, and v represents 1, 2, 3, 4, 5, or 6.

[0065] The medium contains one or more compounds selected from the group of compounds of formula IIA, IIB, IIC, and IID, preferably in a total amount of 5% by weight or more, more preferably 12.5% ​​by weight or more, even more preferably 25% by weight or more, and particularly 40% by weight or more. In a particular embodiment, the total amount of one or more compounds selected from the group of compounds of formula IIA, IIB, IIC, and IID contained in the liquid crystal medium, particularly the more preferred compounds, is in the range of 10% by weight to 60% by weight, more preferably 20% by weight to 55% by weight, and particularly 30% by weight to 50% by weight.

[0066] In compounds of formulas IIA, IIB, and IID, Z 2 These may have the same or different meanings. In the compound of formula IIB, Z 2 and Z 2B These may have the same or different meanings. In compounds of formula IID, Z 2 and Z 2D These terms may have the same or different meanings.

[0067] In compounds of formulas IIA, IIB, IIC, and IID, R 2A , R2B , R 2C and R 2D These are alkyl groups, each preferably having 1 to 6 carbon atoms, particularly CH3, C2H5, n-C3H7, n-C4H9, and n-C5H 11 It represents.

[0068] In compounds of formulas IIA, IIB, and IID, L 1 , L 2 , L 3 and L 4 Preferably, L 1 =L 2 =F and L 3 =L 4 = represents F. Furthermore, the base is preferably L. 1 =F and L 2 =Cl, L 1 =Cl and L 2 =F, L 3 =F and L 4 =Cl, L 3 =Cl and L 4 = Represents F. In equations IIA and IIB, Z 2 and Z 2B Preferably, each represents a single bond independently of the others, and further, a -C2H4-bridged group.

[0069] In equation IIB, Z 2 = -C2H4- or -CH2O-, Z 2B The bond is preferably a single bond, Z 2B = -C2H4- or -CH2O-, Z 2 It is preferably a single bond.

[0070] In formula IID, Z 2D Preferably, it is a single bond.

[0071] In compounds of formulas IIA, IIB, IIC, and IID, (O)C v H 2v+1 OC v H 2v+1 or C v H 2v+1 Represents one of the following: (O)C in compounds of formulas IIA, IIB, and IID.v H 2v+1 Preferably, OC v H 2v+1 This represents (O)C in compounds of formula IIC. v H 2v+1 Preferably, C v H 2v+1 It represents.

[0072] In compounds of formula IIC, L 3 and L 4 Preferably, each represents F.

[0073] Preferred compounds of formulas IIA, IIB, IIC, and IID are shown below.

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] [ka]

[0081] [Chemistry]

[0082] [Chemistry]

[0083] [Chemistry]

[0084] [Chemistry]

[0085] [Chemistry]

[0086] [Chemistry]

[0087] [Chemistry]

[0088] [Chemistry]

[0089] [Chemistry]

[0090] where the parameter a represents 1 or 2, alkyl and alkyl *Each of the following independently represents a linear alkyl group having 1 to 6 carbon atoms, alkenyl represents a linear alkenyl group having 2 to 6 carbon atoms, and (O) represents an oxygen atom or a single bond. Alkenyl preferably represents CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH-, or CH3-CH=CH-(CH2)2-.

[0091] The preferred liquid crystal mixture according to the present invention includes one or more compounds of the formulas IIA-2, IIA-8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, and IID-4.

[0092] The liquid crystal medium is particularly preferably composed of one or more compounds of formula IIA-2, IIA-10, and / or IIB-10. In a particularly preferred embodiment, the liquid crystal medium comprises at least one compound of formula IIA-2, at least one compound of formula IIA-10, and at least one compound of formula IIB-10.

[0093] The proportion of the compound of formula IIA and / or IIB in the whole mixture is preferably at least 20% by weight, more preferably at least 30% by weight, and even more preferably at least 40% by weight.

[0094] In one embodiment, the medium according to the present invention contains at least one compound of formula IIC-1, preferably in an amount greater than 3% by weight, and particularly greater than 5% by weight.

[0095] [ka]

[0096] In the formula, alkyl and alkyl * It has the meaning shown above.

[0097] In a particular embodiment, the liquid crystal medium according to the invention does not contain any compound of formula IID-4, more preferably does not contain any compound of formulae IID-4 and IID-5, and particularly does not contain any compound of formula IID.

[0098] In a preferred embodiment, the medium according to the invention contains one or more compounds of formula III.

[0099]

Chemical formula

[0100] wherein R 11 and R 12 each independently represents H, an alkyl or alkoxy group having 1 to 15 C atoms, provided that in these groups, one or more CH2 groups are arranged such that O atoms are not directly linked to each other,

Chemical formula

[0101] Preferably, one or more compounds of formula III and particularly more preferred compounds thereof are included in the liquid crystal medium in a total amount of 20% by weight or less, more preferably 15% by weight or less, and even more preferably 10% by weight or less. The total amount of one or more compounds of formula III and particularly more preferred compounds thereof included in the liquid crystal medium is preferably in the range of 2.5% by weight to 15% by weight, more preferably 5% by weight to 10% by weight, and particularly 6% by weight to 9% by weight.

[0102] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula III-1 and / or III-2.

[0103] [ka]

[0104] The bases appearing in the formula have the same meaning as those given in formula III above, and this means, R 11 and R 12represents an alkyl, alkenyl or alkoxy group having up to 15 carbon atoms each independently of one another, more preferably, one or both of them represent an alkoxy group, L 11 and L 12 each represent F.

[0105] In a preferred embodiment, the medium comprises one or more compounds of formula III-1, preferably of formula III-1-6, selected from the group of compounds of formulae III-1-1 to III-1-10.

[0106]

Chemical formula

[0107]

Chemical formula

[0108] wherein, alkyl and alkyl * each represent a linear alkyl group having 1 to 6 carbon atoms independently of one another, alkenyl and alkenyl * each represent a linear alkenyl group having 2 to 6 carbon atoms independently of one another, alkoxy and alkoxy * each represent a linear alkoxyl group having 1 to 6 carbon atoms independently of one another, and L 11 and L 12 each represent F or Cl independently of one another, preferably both represent F.

[0109] In a preferred embodiment, the medium comprises one or more compounds of formula III-2, preferably of formula III-2-6, selected from the group of compounds of formulae III-2-1 to III-2-10.

[0110]

Chemical formula

[0111]

Chem.

[0112] In the formula, alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 C atoms, alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 C atoms, alkoxy and alkoxy * each independently represents a linear alkoxyl group having 1 to 6 C atoms, and L 1 and L 2 each independently represents F or Cl, preferably both F.

[0113] In a preferred embodiment of the present invention, the medium contains one or more compounds of formula IIIA-1 and / or IIIA-2.

[0114]

Chem.

[0115] In the formula, L 11 and L 12 have the same meaning as given in formula III, (O) represents O or a single bond, R IIIA represents alkyl or alkenyl having up to 7 C atoms or the group Cy-C m H 2m+1 -, m and n are the same or different and are 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, more preferably 1, Cy represents an alicyclic group having 3, 4 or 5 ring atoms, which may be substituted with alkyl or alkenyl having up to 3 C atoms or halogen or CN, preferably represents cyclopropyl, cyclobutyl or cyclopentyl.

[0116] The compounds of formula IIIA-1 and / or IIIA-2 are included in the medium as an alternative or additional, preferably additional, to the compounds of formula III.

[0117] Particularly preferred compounds of formulas IIIA-1 and IIIA-2 are as follows:

[0118] [ka]

[0119] In the formula, alkoxy is a linear alkoxy group having 1 to 6 carbon atoms.

[0120] In a preferred embodiment of the present invention, the medium contains one or more compounds of formula III-3 in a total amount preferably ranging from 2.5% to 15% by weight, and more preferably from 5% to 10% by weight.

[0121] [ka]

[0122] During the ceremony, R 11 , R 12 -CH=CH- represents an alkyl or alkoxy group having the same or different H and 1 to 15 C atoms, provided that one or more CH2 groups in these groups are arranged so that the O atoms are not directly linked to each other, such as -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] -O-, -CO-O-, or -O-CO- may be substituted for each other independently, and one or more H atoms may be replaced with halogens.

[0123] Preferably, one or more compounds of formula III-3 are selected from the group of compounds of formula III-3-1 to III-3-10.

[0124] [ka]

[0125] [ka]

[0126] In the formula, R 12 represents an alkyl group having 1 to 7 carbon atoms, preferably ethyl, n-propyl, or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl, or cyclopentylmethyl.

[0127] The medium is particularly preferably composed of one or more compounds of formula III-3-2.

[0128] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formulas III-4 to III-6, preferably III-5.

[0129] [ka]

[0130] The parameters in the formula have the meaning given above, R 11 R preferably represents a linear alkyl group, 12 Preferably, represents an alkoxy, each having 1 to 7 C atoms.

[0131] In preferred embodiments, the medium comprises one or more compounds of formula III, preferably formula III-8, selected from the group of compounds of formula III-7 to III-9.

[0132] [ka]

[0133] The parameters in the formula have the meaning given above, R 11R preferably represents a linear alkyl group, 12 Preferably, represents an alkoxy, each having 1 to 7 C atoms.

[0134] In preferred embodiments, the medium comprises one or more compounds of formula IV.

[0135] [ka]

[0136] During the ceremony, R 41 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably an n-alkyl group, and particularly preferably having 2, 3, 4 or 5 carbon atoms. R 42 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkoxy group having 1 to 6 carbon atoms (both preferably having 2 to 5 carbon atoms), or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably 2, 3, or 4 carbon atoms, more preferably a vinyl group or a 1-propenyl group, particularly a vinyl group.

[0137] The liquid crystal medium contains one or more compounds of formula IV in a total amount preferably at least 10% by weight, more preferably at least 20% by weight, even more preferably at least 30% by weight, and especially at least 35% by weight.

[0138] The compound of formula IV is preferably selected from the group of compounds of formula IV-1 to IV-4.

[0139] [ka]

[0140] During the ceremony, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. Alkenyl represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms. 'alkenyl' represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms. The term "alkoxy" represents an alkoxy having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0141] Preferably, the medium contains one or more compounds selected from the compounds of formulas IV-1-1 to IV-1-5.

[0142] [ka]

[0143] Preferably, the medium according to the present invention comprises one or more compounds of formula IV-2-1 and / or IV-2-2.

[0144] [ka]

[0145] In a preferred embodiment, the liquid crystal medium according to the present invention comprises one or more compounds of formula IV-3 selected from compounds of formula IV-3-1 to IV-3-5.

[0146] [ka]

[0147] The liquid crystal medium contains one or more compounds of formulas IV-3-1 to IV-3-5 in a total amount, preferably at least 10% by weight, more preferably at least 20% by weight, even more preferably at least 30% by weight, and especially at least 35% by weight.

[0148] The medium is particularly preferably composed of one or more compounds selected from the compounds of formulas IV-3-1, IV-3-3, and IV-3-4. More preferably, the medium is composed of the compound of formula IV-3-1 and / or the compound of formula IV-3-3 in a total amount of at least 10% by weight, more preferably at least 20% by weight, and even more preferably at least 30% by weight.

[0149] Preferably, the medium according to the present invention comprises a compound of formula IV-4, selected particularly from compounds of formula IV-4-1 and IV-4-2.

[0150] [ka]

[0151] The liquid crystal medium preferably includes one or more compounds of formula IVa.

[0152] [ka]

[0153] During the ceremony, R 41 and R 42 Each represents a linear alkyl, alkoxy, alkenyl, alkoxyalkyl, or alkoxy group having up to 12 C atoms independently of each other, and [ka] Represents, and Z 4 -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, or -CF=CF-.

[0154] Preferred compounds of formula IVa are shown below.

[0155] [ka]

[0156] During the ceremony, Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other.

[0157] The medium according to the present invention preferably comprises at least one compound of formula IVa-1 and / or formula IVa-2.

[0158] In one embodiment, the proportion of the compound of formula IVa in the whole mixture is at least 5% by weight.

[0159] In a preferred embodiment, the liquid crystal medium comprises one or more compounds of formulas IVb-1 to IVb-3.

[0160] [ka]

[0161] During the ceremony, Alkyl and alkyl * Each represents a linear alkyl group having 1 to 6 C atoms independently of each other, and alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other.

[0162] The proportion of compounds of formulas IVb-1 to IVb-3 in the whole mixture is preferably at least 3% by weight, and more preferably 5% by weight or more.

[0163] Of the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0164] The following are particularly preferred compounds of formula IVb.

[0165] [ka]

[0166] In the formula, alkyl * represents an alkyl group having 1 to 6 C atoms, preferably representing n-propyl. The medium according to the present invention particularly preferably comprises one or more compounds of formula IVb-1-1 and / or IVb-2-3.

[0167] In a particularly preferred embodiment, the liquid crystal medium contains a compound of formula IVb-2-3, preferably in an amount of at least 3% by weight, and especially at least 5% by weight.

[0168] In a particularly preferred embodiment, the medium comprises one or more compounds of formula V.

[0169] [ka]

[0170] During the ceremony, R 51 and R 52 R in equation IV is independent of each other. 41 and R 42 It has one of the meanings given to it and preferably represents an alkyl having 1 to 7 carbon atoms, preferably an n-alkyl, particularly preferably an n-alkyl having 1 to 5 carbon atoms, an alkoxy having 1 to 7 carbon atoms, preferably an n-alkoxy, particularly preferably an n-alkoxy having 2 to 5 carbon atoms, an alkoxyalkyl having 2 to 7 carbon atoms, preferably an alkoxyalkyl having 2 to 4 carbon atoms, an alkenyl or alkenyloxy, preferably an alkenyloxy. [ka] however, [ka] Z 51 , Z 52Each 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, preferably a single bond. n is either 1 or 2.

[0171] The compound of formula V is preferably selected from the compounds of formulas V1 to V16.

[0172] [ka]

[0173] [ka]

[0174] In the formula, R 1 and R 2 In the above equation V, R 51 It has the meaning shown in R. 1 and R 2 Preferably, each represents a linear alkyl or alkenyl molecule independently of the others.

[0175] A preferred medium comprises one or more compounds of formulas V-1, V-3, V-4, V-6, V-7, V-10, V-11, V-12, V-14, V-15 and / or V-16.

[0176] The mixture according to the present invention preferably contains compounds of formula V-10, V-12, and / or V-16 in an amount of 5% to 30% by weight.

[0177] Preferred compounds for formula V-10 are shown below.

[0178] [ka]

[0179] In a preferred embodiment of the present invention, the medium further comprises one or more compounds of formulas VI-1 to VI-9.

[0180] [ka]

[0181] [ka]

[0182] During the ceremony, R 7 These are R, which is independent of each other in equation V. 51 It has one of the meanings shown, w and x each represent 1 through 6 independently of each other.

[0183] A mixture containing at least one compound of formula V-9 is particularly preferred.

[0184] In a preferred embodiment, the medium further includes one or more compounds of formulas VII-1 to VII-21.

[0185] [ka]

[0186] [ka]

[0187] [ka]

[0188] During the ceremony, R represents a linear alkyl or alkoxy group having 1 to 6 carbon atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5, or 6, and n is 1, 2, 3, or 4. R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0189] Further preferred embodiments are listed below.

[0190] a) A liquid crystal medium containing at least one compound of formulas Z-1 to Z-7.

[0191] [ka]

[0192] In the formula, R and alkyl are R in formula III above. 11 It has the meaning shown.

[0193] b) A preferred liquid crystal medium includes, for example, one or more substances containing tetrahydronaphthyl or naphthyl units, such as compounds of formula N-1 to N-5.

[0194] [ka]

[0195] R in the formula 1N and R 2N Each of these independently applies R to Equation III. 11 It has the meaning shown, and preferably represents a linear alkyl, linear alkoxy, or linear alkenyl. Z 1 and Z 2These each independently represent -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CH2-, or a single bond.

[0196] c) A preferred mixture comprises one or more compounds selected from the group consisting of difluorodibenzochromane compounds of formula BC, chromanes of formula CR, and fluorinated phenanthrenes of formulas PH-1 and PH-2.

[0197] [ka]

[0198] During the ceremony, R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 Each of these independently applies R to Equation III. 11 It has the meaning of and c is 0, 1, or 2. 1 and R 2 Preferably, each element represents an alkyl or alkoxy having 1 to 6 C atoms independently of each other.

[0199] The mixture according to the present invention preferably contains compounds of formulas BC, CR, PH-1, and PH-2 in an amount of 3 to 20% by weight, and particularly in an amount of 3 to 15% by weight.

[0200] Particularly preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5.

[0201] [ka]

[0202] [ka]

[0203] During the ceremony, Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other. alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other.

[0204] A mixture containing one, two, or three compounds of formula BC-2, BF-1, and / or BF-2 is very preferably preferred.

[0205] d) A preferred mixture comprises one or more indane compounds of formula In.

[0206] [ka]

[0207] During the ceremony, R 11 , R 12 , R 13 Each of these represents a linear alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1 to 6 carbon atoms independently of each other. R 12 and R 13 This is represented by adding a halogen, preferably F, [ka] This represents, i represents 0, 1, or 2.

[0208] Preferred compounds of formula In are the compounds of formula In-1 to In-16 shown below.

[0209] [ka]

[0210] [ka]

[0211] [ka]

[0212] Compounds of formulas In-1, In-2, In-3, and In-4 are particularly preferred.

[0213] Compounds of formula In and sub-formulas In-1 to In-16 are preferably used in the mixture according to the present invention at a concentration of 5% by weight or more, particularly 5 to 30% by weight, and very preferably 5 to 25% by weight.

[0214] e) A preferred mixture includes one or more compounds of formulas L-1 to L-5.

[0215] [ka]

[0216] [ka]

[0217] During the ceremony, R and R 1 Each of these independently applies R to equation III above. 11 The meaning shown is as follows: alkyl represents an alkyl group having 1 to 6 carbon atoms. The parameter s represents 1 or 2.

[0218] The compounds of formulas L1 to L5 are preferably used at a concentration of 5 to 50% by weight, particularly 5 to 40% by weight, and very preferably 10 to 40% by weight.

[0219] f) A preferred mixture includes one or more compounds of formula IIA-Y in addition.

[0220] [ka]

[0221] R in the formula 11 and R 12 Add R to equation III above. 11 It has one of the meanings given to L 1 and L 2 These represent F or Cl, either identical or different.

[0222] The preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0223] [ka]

[0224] [ka]

[0225] Alkyl and Alkyl * Each of these independently represents a linear alkyl group having 1 to 6 carbon atoms, Alkoxy represents a linear alkoxy group having 1 to 6 carbon atoms, and Alkenyl and Alkenyl * Each represents a linear alkenyl group having 2 to 6 C atoms independently of each other, and O represents an oxygen atom or a single bond. * Preferably, CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH-, or CH3-CH=CH-(CH2)2-.

[0226] Particularly preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0227] [ka]

[0228] In the formula, Alkoxy and Alkoxy * The terms have the meanings defined above, and preferably represent methoxy, ethoxy, n-propyloxy, n-butyloxy, or n-pentyloxy.

[0229] The liquid crystal medium according to the present invention is suitable for use in polymer-stabilized displays.

[0230] Therefore, in this embodiment, the liquid crystal medium contains one or more polymerizable compounds of formula P.

[0231] [ka]

[0232] In the formula, each base, independently of the others, has the following meanings, whether identical or different in each instance: P is a polymerizable group, Sp is a spacer group or a single bond, A 1 , A 2 is an aromatic, heteroaromatic, alicyclic, or heterocyclic group, preferably having 4 to 25 ring atoms, and the group may also include a fused ring, and the group is unsubstituted, monosubstituted, or polysubstituted with L. Z 1 -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 single bond, R0 , R 00 It is an alkyl having H or 1 to 12 C atoms, R is H, L, or P-Sp-. L is a linear, branched, or cyclic alkyl group having F, Cl, -CN, P-Sp-, or 1 to 25 C atoms, wherein one or more non-adjacent CH2 groups may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that the O and / or S atoms are not directly linked to each other independently, and one or more H atoms may be replaced with P-Sp-, F, or Cl. z is 0, 1, 2, or 3, and n1 is 1, 2, 3, or 4.

[0233] As used herein, the terms “active layer” and “switchable layer” refer to layers in electro-optical displays, such as LC displays, that contain one or more molecules having structural and optical anisotropy, such as LC molecules, whose orientation changes in response to external stimuli, such as electric or magnetic fields, resulting in a change in the transparency of the layer to polarized or unpolarized light.

[0234] As used herein, the terms “tilt” and “tilt angle” mean the tilted orientation of LC molecules in an LC medium relative to the cell surface in an LC display (preferably a PSA display). In this specification, the tilt angle means the average angle (less than 90°) between the molecular long axis (LC director) of the LC molecule and the surface of the flat, parallel outer plate forming the LC cell. In this specification, a low tilt angle (i.e., far from 90°) corresponds to a large tilt.

[0235] As used herein, the terms “reactive mesogen” and “RM (reactive mesogen)” are understood to mean a compound containing a mesogen or liquid crystal skeleton and one or more functional groups linked to that skeleton and suitable for polymerization, and the functional group is also referred to as a “polymerizable group” or “P”.

[0236] Unless otherwise specified, the term "polymerizable compound" in this specification shall be understood to mean a polymerizable monomer compound.

[0237] As used herein, the term "low molecular weight compound" is understood to mean a monomer and / or a compound not prepared by polymerization, as opposed to "polymer compound" or "polymer."

[0238] As used herein, the term "non-polymerizable compound" is understood to mean a compound that does not contain functional groups suitable for polymerization under the conditions normally applied for the polymerization of RM.

[0239] As used herein, the term “mesogenic group” refers to a group known to those skilled in the art and documented in the literature, which, due to the anisotropy of its attractive and repulsive interactions, essentially contributes to the formation of a liquid-crystalline (LC) phase in low-molecular-weight or high-molecular-weight materials. Compounds containing mesogenic groups (mesogenic compounds) do not necessarily have an LC phase themselves. It is also possible for mesogenic compounds to exhibit LC phase behavior only after mixing with other compounds and / or polymerization. Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units. An overview of the terms and definitions used with respect to mesogenic or LC compounds is given in Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368.

[0240] As used herein, the terms "optically active" and "chiral" are synonymous with materials that can induce a helical pitch in a nematic host material, and are also referred to as "chiral dopant."

[0241] As used herein, the term “spacer group” is also hereafter referred to as “Sp,” and is known to those skilled in the art and described in the literature, see, for example, Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368. As used herein, the term “spacer group” or “spacer” means a flexible group, such as an alkylene group, that links a mesogenic group and one or more polymerizable groups in a polymerizable mesogenic compound.

[0242] Above and below, [ka] This represents a trans-1,4-cyclohexylene ring.

[0243] basis [ka] In this example, the single bond between the two ring atoms can be linked to any unbonded position on the benzene ring.

[0244] In the above and below, "organic group" refers to a carbon or hydrocarbon group.

[0245] The term "carbon group" refers to a monovalent or polyvalent organic group containing at least one carbon atom, which may either contain no further atoms (e.g., -C≡C-) or may contain one or more further atoms (e.g., carbonyl), such as N, O, S, B, P, Si, Se, As, Te, or Ge. The term "hydrocarbon group" refers to a carbon group that additionally contains one or more H atoms and may contain one or more heteroatoms, such as N, O, S, B, P, Si, Se, As, Te, or Ge.

[0246] "Halogen" represents F, Cl, Br, or I, preferably F or Cl.

[0247] -CO-, -C(=O)-, and -C(O)- are carbonyl groups, i.e., [ka] It represents.

[0248] The carbon or hydrocarbon group may be either saturated or unsaturated. Unsaturated groups include, for example, aryl, alkenyl, or alkynyl groups. Carbon or hydrocarbon groups having more than three C atoms may be linear, branched, and / or cyclic, and may also contain spirolinks or fused rings.

[0249] Furthermore, terms such as "alkyl," "aryl," and "heteroaryl" also encompass polyvalent groups, such as alkylenes, arylenes, and heteroarylenes.

[0250] The term "aryl" refers to an aromatic carbon group or a group derived therefrom. The term "heteroaryl" refers to an "aryl" as defined above, containing one or more heteroatoms (preferably selected from N, O, S, Se, Te, Si, and Ge).

[0251] Preferred carbon and hydrocarbon groups are linear, branched, or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy groups having 1 to 40, preferably 1 to 20, and particularly preferably 1 to 12 carbon atoms, which may be substituted; aryl or aryloxy groups having 5 to 30, preferably 6 to 25 carbon atoms, which may be substituted; or alkylaryl, arylalkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy groups having 5 to 30, preferably 6 to 25 carbon atoms, wherein one or more carbon atoms may be replaced by heteroatoms selected from N, O, S, Se, Te, Si, and Ge.

[0252] Further preferred carbon and hydrocarbon groups are C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkinyl, C3~C 20 Allyl, C4~C 20 Alkyldienyl, C4~C 20 Polyenyl, C6~C 20 Cycloalkyl, C4~C 15 Cycloalkenyl, C6~C 30 Aryl, C6~C 30 Alkylaryl, C6~C 30 Arylalkyl, C6~C 30 Alkylaryloxy, C6~C 30 Arylalkyloxy, C2~C 30 Heteroaryl, C2~C 30 It is a heteroaryloxy.

[0253] C1~C 12 Alkyl, C2~C 12 Alkenyl, C2~C 12 Alkinyl, C6~C 25 Aryl and C2~C 25 Heteroaryls are particularly preferred.

[0254] Further preferred carbon and hydrocarbon groups are linear, branched, or cyclic alkyl groups having 1 to 20, preferably 1 to 12 C atoms, the group being unsubstituted or monosubstituted or polysubstituted with F, Cl, Br, I, or CN, wherein one or more non-adjacent CH2 groups are independently linked to each other such that the O and / or S atoms are not directly linked to one another, and each is -C(R x )=C(R x )-, -C≡C-, -N(R x )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- should be replaced with these.

[0255] R x Preferably, represents H, F, Cl, CN, a linear, branched, or cyclic alkyl chain having 1 to 25 carbon atoms (wherein one or more non-adjacent carbon atoms may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and one or more H atoms may be replaced by F or Cl), or an aryl or aryloxy group having 6 to 30 carbon atoms, which may be substituted, or a heteroaryl or heteroaryloxy group having 2 to 30 carbon atoms, which may be substituted.

[0256] Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecanyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, and perfluorohexyl.

[0257] Preferred alkenyl groups include, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, and cyclooctenyl.

[0258] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, and octinyl.

[0259] Preferred alkoxy groups include, for example, methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, and n-dodecoxy.

[0260] Preferred amino groups include, for example, dimethylamino, methylamino, methylphenylamino, and phenylamino.

[0261] The aryl and heteroaryl groups may be monocyclic or polycyclic; that is, they may contain one ring (e.g., phenyl) or two or more rings, and the group may be condensed (e.g., naphthyl) or covalently linked (e.g., biphenyl), or may contain a combination of condensed and linked rings. The heteroaryl group preferably contains one or more heteroatoms selected from O, N, S, and Se.

[0262] Monocyclic, bicyclic, or tricyclic aryl groups having 6 to 25 carbon atoms and monocyclic, bicyclic, or tricyclic heteroaryl groups having 5 to 25 ring atoms are particularly preferred, and these groups may contain fused rings or be substituted. Furthermore, 5-membered, 6-membered, or 7-membered aryl and heteroaryl groups are preferred, however, one or more CH groups may be replaced with N, S, or O such that the O atoms and / or S atoms are not directly linked to each other.

[0263] Preferred aryl groups include, for example, phenyl, biphenyl, terphenyl, [1,1':3',1”]terphenyl-2'-yl, naphthyl, anthracene, binaphthyl, phenanthrene, 9,10-dihydrophenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene, and spirobifluorene.

[0264] Preferred heteroaryl groups include, for example, pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, furan, thiophene, selenofen, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4- Five-membered rings such as thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole; six-membered rings such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, and 1,2,3,5-tetrazine; or indole, isoindole, indidine, indazole, benzimidazole, benzotriazole, pli Naphthymidazole, phenanthroidazole, pyridymidazole, pyrazineimidazole, quinoxalineimidazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, benzo- Condensation groups such as soquinoline, acridine, phenothiazine, phenoxazine, benzopyridazine, benzopyrimidine, quinoxaline, phenazine, naphthyridine, azacarbazole, benzocarbolin, phenantholidine, phenanthroline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, isobenzothiophene, dibenzothiophene, benzothiadiazothiophene; or combinations thereof.

[0265] Furthermore, the aryl and heteroaryl groups described above and below may be substituted with alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl, or further aryl or heteroaryl groups.

[0266] (Non-aromatic) alicyclic and heterocyclic groups include both saturated rings, i.e., those containing exclusively single bonds, and partially unsaturated rings, i.e., those which may also contain multiple bonds. Heterocyclic rings preferably contain one or more heteroatoms selected from Si, O, N, S, and Se.

[0267] (Non-aromatic) alicyclic and heterocyclic groups may be monocyclic, i.e., containing only one ring (e.g., cyclohexane), or polycyclic, i.e., containing multiple rings (e.g., decahydronaphthalene or bicyclooctane). Saturated groups are particularly preferred. Furthermore, monocyclic, bicyclic, or tricyclic groups having 5 to 25 ring atoms are preferred, and these groups may contain fused rings or be substituted. Furthermore, 5-membered, 6-membered, 7-membered, or 8-membered carbocyclic groups are preferred, provided that one or more C atoms are replaced by Si, and / or one or more CH groups are replaced by N, and / or one or more non-adjacent CH2 groups are replaced by -O- and / or -S-.

[0268] Preferred alicyclic and heterocyclic groups include, for example, five-membered groups such as cyclopentane, tetrahydrofuran, tetrahydrothiofuran, and pyrrolidine; six-membered groups such as cyclohexane, silinane, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, and piperidine; seven-membered groups such as cycloheptane; and condensation groups such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, and octahydro-4,7-methanoindan-2,5-diyl.

[0269] Preferred substituents include, for example, dissolution-promoting groups such as alkyl or alkoxy groups, electron-withdrawing groups such as fluorine, nitro or nitrile groups, or substituents that increase the glass transition temperature (Tg) in the polymer, particularly bulky groups such as t-butyl or optionally substituted aryl groups.

[0270] Preferred substituents are referred to as "L" below. S It is also called, 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. A linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms each (wherein one or more H atoms may be replaced with F or Cl), a silyl having 1 to 20 Si atoms which may be substituted, or an aryl having 6 to 25, preferably 6 to 15 C atoms which may be substituted.

[0271] In the formula, R x represents an alkyl chain having 1 to 25 carbon atoms, wherein one or more non-adjacent CH2 groups may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, such that the O- and / S- atoms are not directly linked to each other, wherein one or more H atoms may be replaced with F, Cl, P- or P-Sp-, and Y 1 This represents halogen.

[0272] "Substituted silyl or aryl" is preferably a halogen, -CN, R 0 , -OR 0 ,-CO-R 0 , -CO-OR 0 ,-O-CO-R 0 or -O-CO-OR 0This means substitution by R, however, 0 represents an alkyl group having H or 1 to 20 C atoms.

[0273] Particularly preferred substituents L include, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and phenyl.

[0274] A 1 and A 2 Very preferably [ka] This represents, where L has one of the meanings shown above, and r represents 0, 1, 2, 3 or 4, in particular [ka] That is the case.

[0275] The polymerizable group P is suitable for polymerization reactions such as free radical or ionic chain polymerization, polyaddition or polycondensation, or for polymer-like reactions such as addition or condensation onto a polymer backbone. Groups for chain polymerization, particularly those containing a C=C double bond or a C≡C triple bond, and groups suitable for ring-opening polymerization, such as oxetane or epoxide groups, are especially preferred.

[0276] The preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -(O) k3 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1-CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -, HS-CW 2 W 3 -, HW 2 N-, HO-CW 2 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 Selected from the group consisting of Si-, in the formula, W 1 This represents H, F, Cl, CN, CF3, phenyl, or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, and W 2 and W 3 Each of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 k1, k2, and k3 each independently represent H, Cl, or an alkyl group having 1 to 5 C atoms; Phe represents 1,4-phenylene which may be substituted with one or more groups L as defined above, other than P-Sp-; k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0277] A very preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -O-, CH2=CW 2 -, CW 1 =CH-CO-(O) k3 -, CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH- and W 4 W 5 W 6 Selected from the group consisting of Si-, in the formula, W 1 This represents H, F, Cl, CN, CF3, phenyl, or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH3, and W 2 and W 3 Each of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 k1, k2, and k3 each independently represent H, Cl, or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene, k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0278] A particularly preferred group P is CH2=CW 1-CO-O-, in particular CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, and furthermore CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, [ka] Select from the group consisting of [the specified characters].

[0279] A more preferred polymerizable group P is selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide groups, and most preferably selected from acrylate and methacrylate.

[0280] When the spacer group Sp is different from the single bond, Sp is preferably of the formula Sp"-X", where Sp" and X" have the following meanings, such that each group P-Sp- corresponds to the formula R-Sp"-X"-.

[0281] Sp'' represents a linear or branched alkylene having 1 to 20, preferably 1 to 12, carbon atoms, the group may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, except that one or more non-adjacent CH2 groups are independently -O-, -S-, -NH-, -N(R) such that the O and / or S atoms are not directly linked to each other. 0 )-,-Si(R 0 R 00 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 )-CO-O-,-O-CO-N(R 0 )-,-N(R 0 )-CO-N(R 00 )-, -CH=CH- or -C≡C- may also be used as substitutes. “X” is -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-,-N(R 0 )-CO-, -N(R 0)-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -, -CY 2 =CY 3 - represents -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, or a single bond. R 0 and R 00 Each of these independently represents an alkyl group having either H or 1 to 20 C atoms. Y 2 and Y 3 Each of these elements independently represents either H, F, Cl, or CN.

[0282] X" is sometimes -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 -or it is a single bond.

[0283] Typical spacer bases Sp and -Sp”-X”- are, for example, -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, -(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR 0 R 00 -O) p1 -In the formula, p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, R 0 and R 00 The above has the meanings shown.

[0284] Particularly preferred spacer bases Sp and -Sp”-X”- are -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, where p1 and q1 have the meanings shown above.

[0285] Particularly preferred groups Sp'' in their linear forms are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, etenylene, propenylene, and butenylene.

[0286] In a preferred embodiment of the present invention, compounds of formula P and its subformulas are such that the group Sp-P is Sp(P) s It contains a spacer group Sp (branched polymerizable group) substituted with one or more polymerizable groups P to correspond to (where s is 2 or greater).

[0287] A preferred compound of formula P according to this preferred embodiment is one in which s is 2, i.e., a compound containing the group Sp(P)2. A very preferred compound of formula P according to this preferred embodiment contains a group selected from the following formulas.

[0288] [ka]

[0289] In the formula, P is defined as in formula P, Alkyl groups represent linear or branched alkylenes having single bonds or 1 to 12 carbon atoms, and the group is either unsubstituted or monosubstituted or polysubstituted with F, Cl, or CN, provided that one or more non-adjacent CH2 groups are each independently bonded to each other such that the O and / or S atoms are not directly bonded to each other, and -C(R 0 )=C(R 0 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- may be substituted, however R 0 It has the meaning shown above, aa and bb each independently represent 0, 1, 2, 3, 4, 5, or 6. X has one of the meanings shown in "X", and is preferably O, CO, SO2, O-CO-, CO-O, or a single bond.

[0290] The preferred spacer base Sp(P)2 is selected from formulas S1, S2, and S3.

[0291] A highly preferred spacer base Sp(P)2 is selected from the following sub-formulas.

[0292] [ka]

[0293] In the compounds of formula P and its subformulas as described above and below, P is preferably selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide, most preferably from acrylate and methacrylate.

[0294] All polymerizable groups P present in the compound have the same meaning, and compounds of formula P and its subformulas as described above and below are more preferably acrylate or methacrylate, most preferably methacrylate.

[0295] In the compounds of formula P and its sub-formulas as described above and below, R preferably represents P-Sp.

[0296] Sp is a single bond or -(CH2) p1 -, -O-(CH2) p1 -,-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 This represents, where p1 is 2, 3, 4, 5 or 6, and Sp is -O-(CH2) p1 -,-O-CO-(CH2) p1 or -CO-O-(CH2) p1 In this case, compounds of formula P and its sub-formulas as described above and below, in which the O atom or CO group is linked to a benzene ring, are even more preferred.

[0297] Compounds of formula P and its subformulas as described above and below, in which at least one group Sp is a single bond, are even more preferred.

[0298] At least one group Sp differs from a single bond, preferably -(CH2) p1 -, -O-(CH2) p1 -,-O-CO-(CH2) p1 or -CO-O-(CH2) p1 Selected from, where p1 is 2, 3, 4, 5 or 6, and Sp is -O-(CH2) p1 -,-O-CO-(CH2) p1 or -CO-O-(CH2) p1 In this case, compounds of formula P and its sub-formulas as described above and below, in which the O atom or CO group is linked to a benzene ring, are even more preferred.

[0299] A highly preferred base in formula P -A 1 -(ZA 2 ) z - is selected from the following formula.

[0300] [ka]

[0301] In the formula, at least one benzene ring is substituted with at least one group L, and the benzene ring may be further substituted with one or more groups L or P-Sp-.

[0302] Preferred compounds of formula P and its subformulas are selected from the following preferred embodiments (including any combination thereof): • All groups P in a compound have the same meaning. ·-A 1 -(ZA 2 ) z - is selected from A1, A2, and A5. The compound has exactly two polymerizable groups (represented by group P). The compound has exactly three polymerizable groups (represented by group P). P is selected from the group consisting of acrylate, methacrylate, and oxetane, and is very preferably acrylate or methacrylate. P is methacrylate. • All Sp groups are single bonds. • At least one of the Sp groups is a single bond, and at least one of the Sp groups is not a single bond. • If Sp is different from a single bond, -(CH2) p2 -,-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 The compound is -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O atom or CO group is linked to the benzene ring. • Sp is a single bond, or -(CH2) p2 -,-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 The formula represents -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O atom or CO group is linked to a benzene ring. ·R represents P-Sp- • R does not represent or does not contain a polymerizable group. • R does not represent or does not contain a polymerizable group, and represents an alkyl group having 1 to 25 C atoms in a linear, branched, or cyclic structure, wherein one or more non-adjacent CH2 groups may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, such that the O and / or S atoms are not directly linked to each other, wherein one or more H atoms are each F, Cl, or L a It can be replaced with this. L or L' represents F, Cl, or CN. L is F.

[0303] A suitable and preferred compound for formula P is selected from the following formulas.

[0304] [ka]

[0305] [ka]

[0306] [ka]

[0307] [ka]

[0308] [ka]

[0309] [ka]

[0310] In the formula, each base has the following meaning: P1 , P 2 and P 3 Each of these independently represents an acrylate or methacrylate group. Sp 1 , Sp 2 and Sp 3 Each represents a spacer that independently has one of the meanings indicated above and below a single bond or Sp, and is particularly preferably -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO- or -(CH2) p1 -O-CO-O- represents -O-CO-O-, where p1 is an integer between 1 and 12. However, in addition, there exists base P 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 - At least one of R aa One or more base P 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 - is R aa It may also represent, R aa This refers to H, F, Cl, CN, or linear or branched alkyl groups having 1 to 25 C atoms (however, one or more non-adjacent CH2 groups are independently linked to each other such that the O and / or S atoms are not directly linked to each other, and each is C(R) 0 )=C(R 00 )-, -C≡C-, -N(R 0 ) may be replaced by -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, in addition, one or more H atoms may be replaced by F, Cl, CN or P 1 -Sp 1- may be replaced by ), particularly preferably an alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, which may be linear or branched and monofluorinated or polyfluorinated (wherein alkenyl and alkynyl groups have at least 2 C atoms, and branched groups have at least 3 C atoms). R 0 , R 00 Each of these independently represents an alkyl group having H or 1 to 12 C atoms, identical or different in each occurrence. R y and R z Each of these independently represents H, F, CH3, or CF3. X 1 , X 2 and X 3 These each represent, independently of each other, -CO-O-, -O-CO-, or a single bond. Z 1 -O-, -CO-, -C(R y R z )- or -CF2CF2- represents, Z 2 and Z 3 These are, independently of each other, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2) n - represents, where n is 2, 3, or 4. L, in each instance, may be the same or different, representing F, Cl, CN, or an alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, whether linear or branched and monofluorinated or polyfluorinated, preferably F. L' and L'' each represent H, F, or Cl independently of each other. k represents 0 or 1, r represents 0, 1, 2, 3, or 4. s represents 0, 1, 2, or 3. t represents 0, 1, or 2. x represents either 0 or 1.

[0311] Compounds of formulas P2, P13, P17, P22, P23, P24, P30, P31, and P32 are particularly preferred.

[0312] Furthermore, trireactive compounds P15 to P30 are preferred, particularly P17, P18, P19, P22, P23, P24, P25, P26, P30, P31, and P32.

[0313] In compounds of formulas P1 to P32, the group [ka] And,

[0314] However, L has one of the meanings given above and below, whether the same or different in each occurrence, preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, OCH3, COCH3 or OCF3, in particular F or CH3.

[0315] In one embodiment, a liquid crystal medium is provided in which one or more polymerizable compounds of formula P are polymerized.

[0316] The compound of formula P may be added to the medium at a concentration of preferably 0.01% to 5% by weight, and particularly preferably 0.2% to 2% by weight, relative to the mixture. These mixtures may also include initiators, for example, as described in U.S. Patent No. 6,781,665. Initiators, such as Irganox-1076 from BASF, are preferably added to the mixture containing the polymerizable compound in an amount of 0 to 1% by weight. This type of mixture can be used in so-called polymer-stabilized VA (PS-VA) or polymer-sustained VA (PSA), in which polymerization of the reactive mesogen is intended to occur in the liquid crystal mixture after filling the display panel. A prerequisite for this is that the liquid crystal compound of the so-called LC host does not react under the polymerization conditions of the reactive mesogen, i.e., when exposed to UV in the wavelength range of generally 320 to 360 nm. For example, liquid crystal compounds containing alkenyl side chains, such as CC-3-V, do not react under the polymerization conditions of RM (UV polymerization); therefore, in this specification, such compounds are not considered RM.

[0317] In a preferred embodiment, the liquid crystal medium comprises one or more chiral compounds, particularly one or more chiral dopants.

[0318] Preferably, these chiral dopants are 1 μm -1 ~150μm -1 A range of preferably 10 μm -1 ~100μm -1 The absolute value of the helical twisting power (HTP) is within the range. If the medium contains two or more chiral dopants, these may have opposite signs in their HTP values. This condition is preferable for some specific embodiments because it allows for some degree of compensation for the chirality of each compound, and can be used to compensate for various temperature-dependent properties of the medium obtained in the device. However, generally, it is preferable that most, preferably all, of the chiral compounds present in the medium have the same sign in their HTP values.

[0319] Preferably, the chiral dopants present in the medium are mesogenic compounds, and most preferably, they exhibit a mesophase on their own.

[0320] In a preferred embodiment of the present invention, the medium comprises two or more chiral compounds, all having the same arithmetic sign of HTP.

[0321] In principle, the temperature dependence of the HTP of individual compounds can be high or low. The temperature dependence of the pitch of the medium can be compensated for by mixing compounds with different HTP temperature dependencies in corresponding proportions.

[0322] For example, a number of commercially available chiral dopants are available to those skilled in the art, some of which include cholesteryl nonanoate, R- and S-811, R- and S-1011, R- and S-2011, R- and S-3011, R- and S-4011, or CB15 (all from Merck, Darmstadt).

[0323] Particularly suitable chiral dopants are compounds containing one or more chiral groups and one or more mesogenic groups, or one or more aromatic or alicyclic groups that form a mesogenic group together with a chiral group.

[0324] Suitable chiral groups include, for example, chiral branched hydrocarbon groups, chiral ethanediols, binaphthols or dioxolanes, as well as monovalent or polyvalent chiral groups selected from the group consisting of sugar derivatives, sugar alcohols, sugar acids, lactic acid, chiral-substituted glycols, steroid derivatives, terpene derivatives, amino acids, or sequences of several, preferably 1 to 5, amino acids.

[0325] Preferred chiral groups include sugar derivatives, such as glucose, mannose, galactose, fructose, arabinose, and dextrose; sugar alcohols, such as sorbitol, mannitol, isitol, galactitol, or their anhydro derivatives, particularly dianhydrohexitol, such as dianhydrosorbide (1,4:3,6-dianhydro-D-sorbide, isosorbide), dianhydromannitol (isosorbitol), or dianhydroiditol (isoiditol); sugar acids, such as gluconic acid, gulonic acid, and ketoguronic acid; and chiral-substituted glycol groups. For example, mono- or oligoethylene or propylene glycol in which one or more CH2 groups are substituted with alkyl or alkoxy groups; amino acids, such as alanine, valine, phenylglycine or phenylalanine, or sequences of 1 to 5 of these amino acids; steroid derivatives, such as cholesteryl or cholic acid groups; terpene derivatives, such as menthyl, neomentyl, campheyl, pinail, terpineil, isolongifolyl, phenthyl, kalyl, myrtenyl, nopyl, geranyl, linaloyl, neryl, citronellyl or dihydrocitronellyl.

[0326] Suitable chiral groups and mesogenic chiral compounds are described, for example, in German Patent Nos. 3425503, 3534777, 3534778, 3534779, 3534780, 4342280, European Patent No. 01038941, and 19541820. Further examples are the compounds listed in Table E below.

[0327] Further preferred chiral compounds are selected from the group consisting of the formulas shown below.

[0328] Chiral dopants selected from the group consisting of compounds of the following formulas AI~A-III and A-Ch are particularly preferred.

[0329] [ka]

[0330] During the ceremony, R a11 , R a12 and R b12 This represents an alkyl group having 1 to 15 carbon atoms independently of each other, where furthermore, one or more non-adjacent CH2 groups are independently of each other such that the oxygen and / or sulfur atoms are not directly bonded to each other, -C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, where one or more H atoms may be replaced by F, Cl, Br, I or CN. Preferably, it represents alkyl, more preferably n-alkyl, however, R a12 is R b12 Unlike, R a21 and R a22 This represents an alkyl group having 1 to 15 carbon atoms independently of each other, where furthermore, one or more non-adjacent CH2 groups are independently of each other such that the oxygen and / or sulfur atoms are not directly bonded to each other, -C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, where one or more H atoms may be replaced by F, Cl, Br, I or CN. Preferably both represent alkyl, more preferably n-alkyl. R a31 , R a32 and R b32 This represents a linear or branched alkyl group having 1 to 15 C atoms independently of each other, where furthermore, one or more non-adjacent CH2 groups are independently of each other such that the O and / or S atoms are not directly bonded to each other, and -C(R z )=C(R z)-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, where one or more H atoms may be replaced by F, Cl, Br, I or CN. Preferably, it represents alkyl, more preferably n-alkyl, however, R a32 is R b32 Unlike, R z represents H, CH3, F, Cl, or CN, preferably H or F. R 8 This is the R given above. a11 One of the meanings is an alkyl group having 1 to 15 C atoms, more preferably an n-alkyl group. Z 8 This represents -C(O)O-, -CH2O-, -CF2O- or a single bond, preferably -C(O)O-. A 11 A is below 12 As defined in, or [ka] This represents, A 12 teeth, [ka] Preferably [ka] This represents, During the ceremony, L 12 Each instance independently represents a halogen, CN, or an alkyl, alkenyl, alkoxy, or alkenyloxy having up to 12 C atoms, wherein one or more H atoms may be replaced by a halogen, preferably methyl, ethyl, Cl, or F, and particularly preferably F. A 21 teeth, [ka] This represents, A 22 is, A 12 It has meaning to be given to, A 31 is, A 11 It has meaning to be given to, or [ka] This represents, A 32 is, A 12 It has meaning to be given to, n2 is 0, 1, or 2, and is either the same or different in each occurrence. n3 is 1, 2, or 3. r is 0, 1, 2, 3, or 4.

[0331] A chiral dopant selected from the group consisting of compounds of the following formula is particularly preferred.

[0332] [ka]

[0333] [ka]

[0334] During the ceremony, m is an integer from 1 to 9, and n is an integer between 2 and 9, which may be the same or different in each occurrence.

[0335] Further preferred chiral dopants are derivatives of isosorbide, isomannitol, or isoiditol of the following formulas A-IV.

[0336] [ka]

[0337] In the formula, the group [ka] teeth, [ka] The most preferred is dianhydrosorbitol.

[0338] Furthermore, it includes chiral ethanediols such as diphenylethanediol (hydrobenzoin), particularly mesogenic hydrobenzoin derivatives of the following formula AV, which are (S,S) enantiomers not shown.

[0339] [ka]

[0340] During the ceremony, [ka] Each of these is 1,4-phenylene or 1,4-cyclohexylene, which may be monosubstituted, disubstituted, or trisubstituted at L, independently of each other. L is H, F, Cl, CN, or an alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy having 1 to 7 carbon atoms that may be halogenated. c is either 0 or 1. X is either CH2 or -C(O)-, Z 0 These are -COO-, -OCO-, -CH2CH2-, or single bonds. R 0 These are alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy compounds having 1 to 12 carbon atoms.

[0341] Examples of compounds of formulas A-IV are shown.

[0342] [ka]

[0343] [ka]

[0344] Compounds of formulas A-IV are described in International Publication No. 98 / 00428. Compounds of formula AV are described in British Patent Application Publication No. 2,328,207.

[0345] Particularly preferred chiral dopants are the chiral binaphthyl derivatives described in International Publication No. 02 / 94805, the chiral binaphthol acetal derivatives described in International Publication No. 02 / 34739, the chiral TADDOL derivatives described in International Publication No. 02 / 06265, and the chiral dopants having at least one fluorinated crosslinking group and a terminal or central chiral group described in International Publication Nos. 02 / 06196 and International Publication No. 02 / 06195.

[0346] Chiral compounds of formulas A-VI are particularly preferred.

[0347] [ka]

[0348] During the ceremony, X 1 , X 2 , Y 1 and Y 2 Each of these groups is independently of the others, and consists of F, Cl, Br, I, CN, SCN, SF5, and linear or branched alkyl groups having 1 to 25 carbon atoms (which may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, where furthermore, one or more non-adjacent CH2 groups are independently of each other, such that the O and / or S atoms are not directly bonded to each other, and consist of -O-, -S-, -NH-, NR 0-, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C- (which may be replaced by a polymerizable group or a cycloalkyl or aryl having up to 20 carbon atoms (which may be monosubstituted or polysubstituted with a halogen, preferably F, or a polymerizable group), x 1 and x 2 Each of these is independently 0, 1, or 2. y 1 and y 2 Each of these is independently 0, 1, 2, 3, or 4. B 1 and B 2 Each of these is an aromatic, partially saturated, or fully saturated aliphatic six-membered ring, where one or more CH groups may be replaced by N atoms, and one or more non-adjacent CH2 groups may be replaced by O and / or S atoms. W 1 and W 2 These are, independently of each other, -Z 1 -A 1 -(Z 2 -A 2 ) m -R, or one of the two is R 1 Or A 3 However, neither is H at the same time, or [ka] teeth, [ka] And, U 1 and U 2 Each of these is independently CH2, O, S, CO, or CS. V 1 and V 2 Each of them operates independently of the other, (CH2) n(Here, 1 to 4 non-adjacent CH2 groups may be replaced by O and / or S), V 1 and V 2 One of them is, [ka] but, [ka] If that is the case, both are single bonds, n is 1, 2, or 3. Z 1 and Z 2 These are -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, and -CO-NR, each independent of the others. 0 -, -NR 0 -CO-, -O-CH2-, -CH2-O-, -S-CH2-, -CH2-S-, -CF2-O-, -O-CF2-, -CF2-S-, -S-CF2-, -CH2-CH2-, -CF2-CH2-, -CH2-CF2-, -CF2-CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, two combinations of these groups (where two O and / or S and / or N atoms are not directly bonded to each other), (preferably -CH=CH-COO- or -COO-CH=CH-), or single bonds, R x This represents an alkyl group having 1 to 6 carbon atoms. A 1 , A 2 and A 3Each of these is independently 1,4-phenylene, in which one or two non-adjacent CH groups may be replaced by N; 1,4-cyclohexylene, 1,3-dioxolane-4,5-diyl, 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl (each of these groups may be monosubstituted or polysubstituted with L); and further A 1 It can be a single bond, L is a halogen atom, preferably F, CN, NO2, an alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy having 1 to 7 carbon atoms (where one or more H atoms may be replaced by F or Cl), m is independently 0, 1, 2, or 3. R and R 1 Each of these is independently a linear or branched alkyl group having 1 or 3 to 25 carbon atoms, consisting of H, F, Cl, Br, I, CN, SCN, SF5 (which may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and one or more non-adjacent CH2 groups are -O-, -S-, -NH-, -NR such that two O and / or S atoms are not directly bonded to each other). 0 -, -CO-, -COO-, -OCO-, -O-COO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C- may be substituted, or it is a polymerizable group.

[0349] Chiral binaphthyl derivatives of formula A-VI-1 are particularly preferred.

[0350] [ka]

[0351] In the formula, rings B, R 0 and Z0 This is as defined for equations A-IV and AV, where b is 0, 1, or 2.

[0352] In particular, it must be selected from the following equations A-VI-1a to A-VI-1c.

[0353] [ka]

[0354] In the formula, rings B, R 0 and Z 0 This is as defined for equation A-VI-1, R 0 This is either as defined for formulas A-IV, or an alkyl group having H or 1 to 4 carbon atoms. b is 0, 1, or 2. Z 0 These are specifically -OC(O)- or single bonds.

[0355] The concentration of one or more chiral dopants that may be included in the LC medium is preferably in the range of 0.001% to 20% by weight, preferably 0.05% to 5% by weight, more preferably 0.1% to 2% by weight, and most preferably 0.5% to 1.5% by weight. These preferred concentration ranges apply in particular to chiral dopants S-4011 or R-4011 (both manufactured by Merck) and chiral dopants having the same or similar HTP. For chiral dopants with a higher or lower absolute value of HTP compared to S-4011, these preferred concentrations may be proportionally decreased or increased, respectively, according to the ratio of their HTP values ​​to the HTP value of S-4011.

[0356] The pitch p of the LC medium is preferably in the range of 5 μm to 50 μm, more preferably 8 μm to 30 μm, and particularly preferably 10 μm to 20 μm.

[0357] Preferably, the medium according to the present invention comprises one or more stabilizers selected from the group of compounds of formula ST-1 to ST-19.

[0358] [ka]

[0359] [ka]

[0360] [ka]

[0361] [ka]

[0362] [ka] During the ceremony, R ST represents an alkyl or alkoxy group having H and 1 to 15 C atoms, where furthermore, one or more non-adjacent CH2 groups in these groups are independently of each other such that the O atoms are not directly bonded to one another, and are -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] -O-, -CO-O- or -O-CO-O- may be substituted, and furthermore, one or more H atoms may be substituted with halogens. [ka] [ka] This represents, Z STThese each independently represent -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 1 and L 2 Each of these independently represents F, Cl, CF3, or CHF2. p is 1 or 2, and q is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0363] Among the compounds of formulas ST-1 to ST-19, the compound of the following formula is particularly preferred.

[0364] [ka]

[0365] [ka]

[0366] [ka]

[0367] In the compounds of formulas ST-3a and ST-3b, n preferably represents 3. In the compound of formula ST-2a, n preferably represents 7.

[0368] A particularly very preferred mixture according to the present invention comprises one or more stabilizers from the group of compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1, and ST-12.

[0369] [ka]

[0370] [ka]

[0371] The compounds of formulas ST-1 to ST-19 are preferably present in the liquid crystal mixture according to the present invention in an amount of 0.005% to 0.5% by weight relative to the mixture.

[0372] When the mixture according to the present invention contains two or more compounds from the group of compounds of formula ST-1 to ST-19, the concentration of the two compounds increases from 0.01% by weight to 1% by weight based on the mixture.

[0373] However, the total proportion of compounds of formulas ST-1 to ST-19 based on the mixture according to the present invention should not exceed 2% by weight.

[0374] It has been remarkably found that the liquid crystal media currently available can contribute advantageously to achieving superior electro-optical device performance, for example, in terms of achievable contrast and high light transmittance, while demonstrating functionality, reliability, and stability even at high and low temperatures.

[0375] The definitions of the abbreviations, also called acronyms for preferred compounds, are given in Tables A to C below.

[0376] In a more preferred embodiment, the medium according to the present invention is • A total amount of one or more compounds of formula I and its particularly more preferred compounds, in an amount of 10% by weight or less, more preferably 7% by weight or less, even more preferably 4% by weight or less, preferably 0.25% to 8% by weight, more preferably 0.5% to 5% by weight, and especially 1% to 3% by weight. and / or

[0377] Preferably, the compound of formula Ia-1 is present in an amount within the range of 10% by weight or less, more preferably 7% by weight or less, even more preferably 4% by weight or less, preferably 0.25% to 8% by weight, more preferably 0.5% to 5% by weight, and particularly within the range of 1% to 3% by weight. and / or

[0378] Preferably 5% by weight or more, more preferably 12.5% ​​by weight or more, even more preferably 25% by weight or more, particularly 40% by weight or more, preferably 10% to 60% by weight, more preferably 20% to 55% by weight, particularly 30% to 50% by weight, containing one or more compounds selected from the group of compounds of formulas IIA, IIB, IIC, and IID, and particularly more preferred compounds thereof, and / or

[0379] Preferably, at least 20% by weight, more preferably at least 30% by weight, and even more preferably at least 40% by weight, one or more compounds of formula IIA and / or IIB, and / or

[0380] Preferably, a total amount of one or more compounds of formula III and particularly more preferred compounds thereof, in the range of 20% by weight or less, more preferably 15% by weight or less, even more preferably 10% by weight or less, preferably 2.5% to 15% by weight, more preferably 5% to 10% by weight, and especially 6% to 9% by weight. and / or

[0381] Preferably, at least 10% by weight, more preferably at least 20% by weight, even more preferably at least 30% by weight, and especially at least 35% by weight, one or more compounds of formula IV, and / or

[0382] Preferably, at least 10% by weight, more preferably at least 20% by weight, even more preferably at least 30% by weight, and especially at least 35% by weight, one or more compounds of formulas IV-3-1 to IV-3-5, and / or

[0383] Preferably at least 10% by weight, more preferably at least 20% by weight, and even more preferably at least 30% by weight in total, a compound selected from one or more compounds of formula IV-3-1, IV-3-3, and IV-3-4, preferably a compound of formula IV-3-1 and / or a compound of formula IV-3-3, and / or

[0384] Preferably, at least 3% by weight, and especially 5% by weight or more, one or more compounds of formula IVb-1 to IVb-3, and / or

[0385] Preferably, at least 3% by weight, and especially at least 5% by weight, of the compound of formula IVb-2-3, and / or

[0386] Compound CLP-V-1 in an amount ranging from 0.25% to 8% by weight, and compound PP-1-2V1 in an amount ranging from 3% to 8% by weight. Includes.

[0387] The present invention further relates to an electro-optical display having an active matrix address, wherein the liquid crystal medium described in claim 1 is used as the dielectric, and preferably 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, polymer-stabilized SA-VA, or polymer-stabilized SA-FFS display.

[0388] It is advantageous for the liquid crystal medium to have a nematic phase that is preferably -20°C or lower to 70°C or higher, particularly preferably -30°C or lower to 80°C or higher, and very preferably -40°C or lower to 90°C or higher.

[0389] The medium according to the present invention preferably has a transparency temperature of 70°C or higher, more preferably 77°C or higher.

[0390] The expression "having a nematic phase" means, on the one hand, that the smectic phase and crystallization are not observed at temperatures lower than the corresponding temperature, and on the other hand, that transparency still does not occur upon heating from the nematic phase. Low-temperature studies are performed using a fluid viscometer at the corresponding temperature and confirmed by storing the sample for at least 100 hours in a test cell with a layer thickness suitable for electro-optical applications. If the storage stability in the test cell at -20°C is 1000 hours or more, the medium is said to be stable at this temperature. For temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the transparency point is measured in a capillary tube using conventional methods.

[0391] The liquid crystal mixture preferably has a nematic phase range of at least 60K and a maximum of 30mm at 20°C. 2 ·Seconds -1 The fluid viscosity ν 20 It has.

[0392] The mixture is preferably nematic at a temperature of -20°C or lower, preferably -30°C or lower, and very preferably -40°C or lower.

[0393] The rotational viscosity γ1 of the medium at 20°C is preferably 120 mPa·s or less, more preferably 100 mPa·s or less, and particularly 95 mPa·s or less.

[0394] The liquid crystal medium according to the present invention preferably has a relatively low threshold voltage (V0). These are preferably in the range of 1.7V to 3.0V, particularly preferably 2.7V or less, and very particularly preferably 2.5V or less.

[0395] In this invention, unless otherwise specified, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Fredericks threshold.

[0396] In addition, the liquid crystal medium according to the present invention preferably and advantageously has a high voltage retention rate in the liquid crystal cell.

[0397] All temperature values ​​shown in this invention are in °C.

[0398] The mixtures according to the present invention are suitable for VA-TFT applications such as VAN, MVA, (S)-PVA, ASV, PSA (polymer sustained VA), and PS-VA (polymer stabilized VA). They are also suitable for IPS (in-plane-switching) and FFS (fringe field switching) applications using media with negative Δε.

[0399] Depending on the embodiment, the mixture may also contain one or more compounds having a dielectric anisotropy Δε of 1.5 or more. These so-called positive compounds are generally present in the mixture with negative dielectric anisotropy in an amount of 20% by weight or less, based on the whole mixture.

[0400] In addition to one or more compounds of formula I, the medium preferably comprises 4 to 15 types, particularly 5 to 12 types, and especially preferably less than 10 types of compounds of formula IIA, IIB and / or IIC, and optionally one or more compounds of formula IV-3.

[0401] The compounds according to the present invention can be synthesized by known methods or similar methods described in standard publications such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, and Stuttgart, under known reaction conditions suitable for the aforementioned reaction. Variations known to themselves, though not mentioned herein, can also be used herein.

[0402] The following examples illustrate the present invention without limiting it. However, they will be helpful to those skilled in the art to understand preferred mixing concepts, along with preferred compounds, their respective concentrations, and combinations thereof. In addition, the examples illustrate the available properties and combinations of properties.

[0403] In the present invention and the following examples, the structure of the liquid crystal compound is indicated by an acronym, and its conversion to a chemical formula is performed according to Tables A to C below. n H 2n+1 , C m H 2m+1 and C l H2 l+1 or C n H 2n and C m H 2m These are linear alkyl or alkylene groups having n, m, and l carbon atoms, respectively. Preferably, n, m, and l are 1, 2, 3, 4, 5, 6, or 7, independently of each other. Table A shows the codes of the ring elements of the core of the compound, Table B lists the bridging units, and Table C lists the meanings of the symbols of the left- and right-end groups of the molecule. The acronym consists of the code of the ring element having any linking group, followed by a first hyphen and the code of the left-end group, and a second hyphen and the code of the right-end group. Table D shows structural examples of the compound along with their respective abbreviations.

[0404] <Table A: Ring elements>

[0405] [Table 1]

[0406] [Table 2]

[0407] [Table 3]

[0408] [Table 4]

[0409] <Table B: Bridge Units>

[0410] [Table 5]

[0411] <Table C: Terminal group>

[0412] [Table 6]

[0413] In the table, n and m are integers, and the three dots "..." are spaces for other abbreviations from this table.

[0414] In addition to one or more compounds of formula I, and optionally one or more compounds of formulas IIA, IIB, IIC, and / or IID, the mixture according to the present invention preferably comprises one or more compounds of the compounds described below.

[0415] Use the following abbreviations: n, m, k, and l are each an integer independently of each other, preferably 1 to 9, more preferably 1 to 7, and k and l may also be 0, preferably 0 to 4, more preferably 0 or 2, most preferably 2, n is preferably 1, 2, 3, 4, or 5, in the combination "-nO-" n is preferably 1, 2, 3, or 4, more preferably 2 or 4, m is preferably 1, 2, 3, 4, or 5, and in the combination "-Om" m is preferably 1, 2, 3, or 4, more preferably 2 or 4. The combination "-lVm" is preferably "2V1".

[0416]

[0417] Table 7

[0418] Table 8

[0419] Table 9

[0420] Table 10

[0421] Table 11

[0422] Table 12

[0423] Table 13

[0424] Table 14

[0425] Table 15

[0426] Table 16

[0427] Table 17

[0428] Table 18

[0429] Table 19

[0430] Table 20

[0431] Table 21

[0432] Table 22

[0433] Table 23

[0434] Table 24

[0435] Table 25

[0436] Table 26

[0437] Table 27

[0438] Table E shows the chiral dopants that can be added to the LC medium according to the present invention.

[0439] [Table 28]

[0440] [Table 29]

[0441] [Table 30]

[0442] [Table 31]

[0443] [Table 32]

[0444] Table F shows exemplary reactive mesogenic compounds (RMs) that can be used in the LC medium according to the present invention.

[0445] [Table 33]

[0446] [Table 34]

[0447] [Table 35]

[0448] [Table 36]

[0449] Table 37

[0450] Table 38

[0451] Table 39

[0452] Table 40

[0453] Table 41

[0454] Table 42

[0455] Table 43

[0456] Table 44

[0457] Table 45

[0458] Table 46

[0459] Table 47

[0460] Table 48

[0461] Table 49

[0462] Table 50

[0463] Table 51

[0464] Table 52

[0465] Table 53

[0466] Table 54

[0467] Table 55

[0468] Table 56

[0469] In a preferred embodiment, the mixture according to the present invention preferably comprises one or more polymerizable compounds selected from polymerizable compounds of formulas RM-1 to RM-155. Of these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121, RM-122, and RM-145 to RM-153 are particularly preferred.

[0470] In another preferred embodiment, the mixture according to the present invention comprises one or more polymerizable compounds selected from formulas RM-145 to RM-152, and very preferably from formulas RM-147 to RM-152.

[0471] Table G shows self-aligning additives for vertical orientation that can be used in conjunction with polymerizable compounds of formula P, in particular in LC media for SA-VA and SA-FFS displays according to the present invention.

[0472] [Table 57]

[0473] [Table 58]

[0474] [Table 59]

[0475] [Table 60]

[0476] [Table 61]

[0477] [Table 62]

[0478] [Table 63]

[0479] [Table 64]

[0480] [Table 65]

[0481] [Table 66]

[0482] [Table 67]

[0483] [Table 68]

[0484] [Table 69]

[0485] In a preferred embodiment, the LC medium, SA-VA, and SA-FFS display according to the present invention preferably contains one or more SA additives selected from formulas SA-1 to SA-48, preferably from formulas SA-14 to SA-48, and very preferably from formulas SA-20 to SA-34 and SA-44, in combination with one or more RMs of formula P.

[0486] The following examples are merely illustrative of the present invention and should not be considered to limit the scope of the invention in any way. Examples and modifications or other equivalents will be apparent to those skilled in the art in light of this disclosure.

[0487] However, the following physical properties and compositions illustrate what characteristics can be achieved and within what range they can be modified. The various combinations of characteristics that can be particularly favorably achieved are thus well defined. [Examples]

[0488] Unless otherwise specified, all concentrations herein are expressed in weight percent and refer to the corresponding mixture as a whole, containing all solid or liquid crystal components, excluding the solvent. All physical properties are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals," published November 1997, Merck, Germany, and apply at a temperature of 20°C, unless otherwise specified.

[0489] The symbols and abbreviations have the following meanings: Fredericks capacitance threshold voltage [V] at 20°C, V 10 Voltage at 10% transmission [V] n e Anomalous refractive index measured at 20°C and 589nm, The typical refractive index measured at 20°C and 589nm. Δn Optical anisotropy measured at 20℃ and 589nm, ε ⊥ The dielectric constant (or "dielectric constant") perpendicular to the long axis of the molecule at 20°C and 1kHz, ε ∥ The dielectric constant (or "dielectric constant") parallel to the major axis of the molecule at 20°C and 1kHz, Δε Dielectric anisotropy at 20℃ and 1kHz, cl.p. or T(N,I) transparency point [°C], ν is the fluid viscosity measured at 20°C [mm²] 2 ·s -1 ], γ Rotational viscosity [mPa·s] measured at 120℃, K 11 Elastic constant [pN] for "spray" deformation at 20°C, K 22 Elastic constant [pN] for "twist" deformation at 20°C, K 33 Elastic constant [pN] for "bend" deformation at 20°C, LTS (low-temperature stability) is the low-temperature stability of the phase determined by the bulk, and VHR (voltage holding ratio) Voltage holding ratio.

[0490] For the purposes of this invention, the term "threshold voltage" refers to the capacitance threshold (V0) unless explicitly indicated otherwise. In the example, it is generally the optical threshold, e.g., 10% relative contrast (V0), as is common in other contexts. 10 ) may also be shown.

[0491] <Examples and comparative examples>

[0492] <Examples of mixtures and comparative mixtures>

[0493] <Comparative mixture C1> [Table 70]

[0494] <Comparative mixture C2> [Table 71]

[0495] <Comparative mixture C3> [Table 72]

[0496] <Comparative mixture C4> [Table 73]

[0497] <Comparative mixture C5> [Table 74]

[0498] <Mixture M1> [Table 75]

[0499] <Mixture M2> [Table 76]

[0500] <Mixture M3> [Table 77]

[0501] <Mixture M4> [Table 78]

[0502] <Mixture M5> Compound Ia-2 is identified and the following mixture as described above is prepared. [Table 79]

[0503] <Mixture M6> [Table 80]

[0504] <Mixtures M7, M8, and M9> Each of mixtures M7, M8, and M9 is prepared by mixing 99.70% of the above mixtures M1, M2, and M3 with 0.30% of the compound of the following formula.

Chemical formula

[0505] <Mixture M10> Mixture M10 is prepared by mixing 99.51% of mixture M7 with 0.49% of chiral dopant S-811 available from Merck KGaA, Darmstadt, Germany.

[0506] <Mixture M11> Mixture M11 is prepared by mixing 99.70% of mixture M8 and 0.30% of the compound of the following formula.

Chemical formula

[0507] <Mixture M12> Mixture M12 is prepared by mixing 99.60% of mixture M9 and 0.40% of the compound of the following formula.

Chemical formula

[0508] Mixtures M1 to M12 having negative dielectric anisotropy are suitable for liquid crystal displays, particularly IPS, FFS, UB-FFS (ultra-high brightness FFS), and VA displays. <00​​​​​

[0510] [Table 81]

[0511] The comparison demonstrates the preferred VHR characteristics of the liquid crystal medium according to the present invention, while simultaneously showing suitable electro-optical performance.

[0512] Surprisingly, it is found that the compound of formula I can contribute to a stabilizing effect that gives the medium desirable reliability.

Claims

1. Having negative dielectric anisotropy, one or more compounds of formula I, and One or more compounds selected from compounds represented by formulas III and IVb-1 to IVb-3. Liquid crystal media including liquid crystal. 【Chemistry 1】 (In the ceremony R １ This represents a linear or branched alkenyl group having 2 to 15 carbon atoms, provided that one or more CH groups are present. ２ The group is designed so that the oxygen atoms are not directly bonded to each other. 【Chemistry 2】 -C≡C-, -CF ２ O-, -OCF ２ -, -O-, -CO-O-, or -O-CO- may be substituted for each other independently, and in the group, one or more H atoms may be replaced with halogens. R ２ represents a linear or branched alkyl or alkoxy group having H and 1 to 15 C atoms, provided that one or more CH groups are present in these groups. ２ The group is designed so that the oxygen atoms are not directly bonded to each other. 【Transformation 3】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO- may be substituted for each other independently, and in the group one or more H atoms may be replaced by halogens, Y １ represents H or CH₃.) 【Transformation 6】 (In the formula, R11 and R12 each independently represent an alkyl or alkoxy group having H and 1 to 15 C atoms, provided that in these groups, one or more CH2 groups are arranged such that the O atoms are not directly bonded to each other. 【Transformation 7】 -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O- or -O-CO- may be substituted, provided that one or more H atoms are also substituted with halogens. A1, in each appearance, independently of each other, a) A 1,4-cyclohexenylene or 1,4-cyclohexylene group in which one or two non-adjacent CH2 groups may be replaced by -O- or -S-, b) A 1,4-phenylene group in which one or two CH groups may be replaced by N, c) Groups from the group spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl This represents, However, the groups specified in a), b), and c) may be monosubstituted or polysubstituted with halogen atoms. n is 1, Each instance of Z1 independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond. L11 and L12 each independently represent F, Cl, CF3 or CHF2, and (W represents O or S.) 【Chemistry 10】 (In the formula, alkyl and alkyl* each independently represent an alkyl group having 1 to 6 carbon atoms, and alkenyl and alkenyl* each represent an alkenyl molecule having 2 to 6 carbon atoms, independently of each other.

2. The liquid crystal medium according to claim 1, comprising one or more compounds selected from the group of compounds of formulas IIA, IIB, IIC, and IID. 【Chemistry 4】 (In the formula, R ２Ａ , R ２Ｂ , R ２Ｃ and R ２Ｄ Each represents an alkyl or alkenyl group having H and up to 15 C atoms, and the group is either unsubstituted or CN or CF ３ It is monosubstituted with or at least monosubstituted with a halogen, and in addition, one or more CH groups are present in these groups. ２ The group is formed so that the oxygen atoms are not directly bonded to each other, -O-, -S-, 【Transformation 5】 -C≡C-, -CF ２ O-, -OCF ２ -, -CO-O- or -O-CO- may be used as substitutes. L １ ~L ４ These are F, Cl, and CF, which are independent of each other. ３ or CHF ２ This represents, Y is H, F, Cl, CF ３ CHF ２ or CH ３ This represents, Z ２ Z ２Ｂ and Z ２Ｄ Each of them is independently bonded to the other by a single bond, -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -COO-, -OCO-, -C ２ F ４ -, -CF=CF- or -CH=CHCH ２ Represents O-, p represents 0, 1, or 2. q represents 0 or 1, and (v represents 1, 2, 3, 4, 5, or 6.)

3. The medium according to claim 1 or 2, comprising one or more compounds of formula III as defined in claim 1.

4. A medium according to any one of claims 1 to 3, comprising one or more compounds of formula IV. 【Transformation 8】 (In the formula, R ４１ This represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms, and R ４２ (This represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.)

5. The medium according to any one of claims 1 to 4, comprising one or more compounds selected from the group of compounds of the following formula. 【Chemistry 9】

6. The medium according to any one of claims 1 to 5, comprising one or more compounds of formula IVb-1 to IVb-3 as defined in claim 1.

7. A medium according to any one of claims 1 to 6, comprising one or more compounds of formula V. 【Chemistry 11】 (In the formula, R ５１ and R ５２ Each of these independently represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkoxyalkyl group, alkenyl group, or alkenyloxy group having 2 to 7 carbon atoms. 【Chemistry 12】 This represents, Z ５１ and Z ５２ Each of them is independently of the other -CH ２ -CH ２ -ien-CH ２ -O-, -CH=CH-, -C≡C-, -COO- or single bond, and n is either 1 or 2.

8. A medium according to any one of claims 1 to 7, comprising a chiral dopant.

9. A medium according to any one of claims 1 to 8, comprising one or more polymerizable compounds of formula P. 【Chemistry 13】 (In the formula, P represents a polymerizable group, Sp represents a spacer group or a single bond. A １ and A ２ These are identical or distinct groups representing aromatic, heteroaromatic, alicyclic, or heterocyclic groups, and the group may include a fused ring, and the group is unsubstituted or monosubstituted or polysubstituted with L. L represents F, Cl, -CN, P-Sp-, or a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, provided that one or more non-adjacent CH groups are present. ２ The group may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- such that the O and / or S atoms are not directly linked to each other, except that one or more H atoms may be replaced with P-Sp-, F or Cl. Z １ represents -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH ２ -, -CH ２ O-, -SCH ２ -, -CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -(CH ２ ) ｎ１ -, -CF ２ CH ２ -, -CH ２ CF ２ -, -(CF ２ ) ｎ１ -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH ２ -CH ２ -CO-O-, -O-CO-CH ２ -CH ２ -, -CR ０ R ００ - or represents a single bond, R ０ and R ００ These represent alkyl groups having the same or different H or 1 to 12 C atoms. R represents H, L, or P-Sp-, z is 0, 1, 2 or 3, and n1 is 1, 2, 3, or 4.

10. The medium according to claim 9, wherein one or more polymerizable compounds of formula P are polymerized.

11. A liquid crystal display comprising the medium described in any one of claims 1 to 10.

12. The display according to claim 11, which is a PSA display.

13. The display according to claim 12, wherein the display is a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS, polymerization-stabilized SA-VA, or polymerization-stabilized SA-FFS display.

14. The display according to claim 11, which is a VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, or SA-VA display.

15. Use of a liquid crystal medium according to any one of claims 1 to 10 in an electro-optical display.

Images