Liquid crystal medium

Abstract

To provide a liquid crystal medium.SOLUTION: The present invention relates to liquid crystal (LC) media having negative dielectric anisotropy, to the use thereof in an electro-optical display, particularly in a display with passive matrix addressing, based on the VA, ECB, FFS or IPS effect, and to displays of this type, in particular to an energy saving PM-VA display with low voltage driving.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to liquid crystal (LC) media having negative dielectric anisotropy, their use in electro-optical displays, particularly in passive matrix addressing displays based on VA, ECB, FFS, or IPS effects, and to displays of this type. [Background technology]

[0002] One of the liquid crystal display (LCD) modes currently in use is the TN ("twisted nematic") mode. However, TN LCDs have the disadvantage that contrast is highly dependent on the viewing angle.

[0003] In addition, so-called VA ("vertically aligned") displays with wider viewing angles 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 (homeotropic) or have a tilt homeotropic orientation. When a voltage is applied to the two electrodes, the LC molecules re-orient parallel to the electrode surface.

[0004] 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.

[0005] Furthermore, so-called FFS ("fringe-field switching") displays have been reported (see SHJung et al., Jpn.J.Appl.Phys., Vol. 43, No. 3, 2004, p. 1028 (Non-Patent Literature 1) in particular), which have 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.

[0006] Furthermore, FFS displays have been disclosed that have electrode designs and layer thicknesses similar to FFS displays, but instead of an LC medium layer having positive dielectric anisotropy, they have 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)). LC media with negative dielectric anisotropy exhibit a more preferable director orientation with smaller tilt and higher twist orientation compared to LC media with positive dielectric anisotropy, resulting in these displays having 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. These displays require highly reliable LC media.

[0007] In more recent types of VA displays, the uniform orientation of LC molecules is limited to a number of relatively small domains within the LC cell. Discrinciple may exist between these domains, also known as tilt domains. VA displays with tilt domains have a wider, contrast-independent viewing angle and more intermediate tones compared to conventional VA displays. In addition, this type of display is easier to manufacture and no longer requires further treatment of the electrode surface, such as rubbing, to uniformly orient molecules when switched on. Instead, the preferred direction of the tilt angle or pre-tilt angle is controlled by a special design of the electrodes.

[0008] In so-called MVA ("multidomain vertical alignment") displays, this is typically achieved by electrodes with protrusions, which causes localized pre-tilt. As a result, when voltage is applied, LC molecules are oriented parallel to the electrode surface in various directions and in various specified areas of the cell. This achieves "controlled" switching and prevents the formation of coherent disclination lines. While this arrangement improves the viewing angle of the display, it results in reduced light transmittance. Further development of MVA involves using protrusions on only one electrode side, while the opposite electrode has a slit, thereby improving light transmittance. The slitted electrode generates a non-uniform electric field within the LC cell when voltage is applied, which means that controlled switching is still achieved. The distance between the slit and the protrusion can be increased to further improve light transmittance, but this results in a longer response time. In so-called PVA ("patterned VA") displays, the protrusions are completely superfluous, with both electrodes structured by slits on opposite sides. This results in increased contrast and improved light transmission, but it is technically difficult, and the display becomes more sensitive to mechanical influences (such as "tapping"). However, many applications, such as monitors, especially television screens, require faster response times and improved contrast and brightness (transparency) of the display.

[0009] From the perspective of mobile devices in particular, there is a great demand for highly transparent displays, which allows for the use of lower-intensity backlights and thus longer battery life. Alternatively, of course, higher brightness displays can be achieved by improving contrast, especially in ambient light.

[0010] Both VA and FFS displays can operate as active-matrix or passive-matrix displays. In active-matrix displays, individual pixels are typically addressed by integrated nonlinear active elements such as transistors (e.g., thin-film transistors ("TFTs")), while in passive-matrix displays, individual pixels are typically addressed in a multiplex manner.

[0011] The present invention is intended for use in displays and aims to provide a novel and suitable LC medium which may contain a reactive mesogen (RM), the LC medium having no or reduced degree of the above-mentioned drawbacks.

[0012] In particular, the present invention is based on the objective of providing an LC medium that enables a display that has high transmittance, very high resistivity, high VHR value, high reliability, low threshold voltage, short response time, and appropriate birefringence, and is useful in reducing or preventing the occurrence of "image sticking" and "ODF mura" in displays.

[0013] Passive-matrix (PM) displays, in particular, require improved liquid crystal materials. Specifically, lower threshold voltages, higher transparency points, and appropriate birefringence values ​​are required. Suitable media for negative dielectric anisotropy PM LC displays are described, for example, in European Patent Application Publication No. 2 182 046 (Patent Document 1) and European Patent Application Publication No. 3 130 650 (Patent Document 2). [Prior art documents] [Patent Documents]

[0014] [Patent Document 1] European Patent Application Publication No. 2 182 046 [Patent Document 2] European Patent Application Publication No. 3 130 650 [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] These objectives were achieved in accordance with the present invention by the materials and methods described in this application. Particularly surprising, it was found that the advantageous effects described above could be achieved by using the liquid crystalline host as described below. [Means for solving the problem]

[0017] The present invention relates to a liquid crystal medium comprising a) one or more compounds of formula I, b) one or more compounds selected from the group of formulas IIA, IIB, IIC, and IID, and c) one or more compounds of formula III.

[0018] [ka]

[0019] During the ceremony R 1 and R 2are, independently of one another, H, an alkyl or alkenyl group having 1 to 12 C atoms or 2 to 12 C atoms, respectively, which group is unsubstituted, monosubstituted with CN or CF3 or at least monosubstituted with halogen, provided that in addition, one or more CH2 groups in these groups are such that O atoms are not directly linked to one another, and are replaced by -O-, -S-,

Chemical formula

[0020]

Chemical formula

[0021] wherein R 1A 、R 1B 、R 1C 、R 1D 、R 2A 、R 2B 、R 2C and R 2D each independently of one another represent H, an alkyl or alkenyl group having 1 to 12 C atoms or 2 to 12 C atoms, respectively, which group is unsubstituted, monosubstituted with CN or CF3 or at least monosubstituted with halogen, provided that in addition, one or more CH2 groups in these groups are such that O atoms are not directly linked to one another, and are replaced by -O-, -S-,

Chemical formula

[0022] [ka]

[0023] During the ceremony R 31 and R 32 Each of these represents an alkyl or alkoxy group having H and 1 to 15 C atoms independently of each other, provided that one or more CH2 groups in these groups are arranged so that the O atoms are not directly bonded to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO- may be substituted for each other independently, and in the group, one or more H atoms may be replaced by halogens. A 31 Each of them appears independently of the others. a) A 1,4-cyclohexenylene or 1,4-cyclohexylene group, wherein one or two non-adjacent CH2 groups in the group may be replaced by -O- or -S-, b) A 1,4-phenylene group, in which one or two CH groups may be replaced by N, or c) Bases from the group of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl This represents, However, groups a), b), and c) may be monosubstituted or polysubstituted with halogen atoms. Z 31 Each of these terms independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond. L 31 and L 32 Each of these independently represents F, Cl, CF3, or CHF2, and n is 0, 1, or 2. [Modes for carrying out the invention]

[0024] The present invention further relates to an LC display including the LC media described above and below.

[0025] The present invention relates to an LC display comprising an LC medium according to the present invention, which is addressed by a passive matrix and is based on VA, ECB, FFS, or IPS, and more particularly to an energy-saving PM-VA display with very low load operation.

[0026] The present invention further relates to a method for preparing an LC medium as described above and below, comprising the step of mixing one or more compounds of formula I, one or more compounds selected from the group consisting of formulas IIA, IIB, IIC, and IID, and one or more compounds of formula III.

[0027] The present invention further relates to the use of an LC medium according to the present invention in an LC display.

[0028] The present invention relates to a method for manufacturing an LC display as described above and below, comprising the steps of: filling an LC medium, which may contain one or more polymerizable compounds, between substrates of a display or otherwise providing it; and an optional step of polymerizing the polymerizable compounds.

[0029] Preferred embodiments are the subject of the dependent claims and can also be addressed herein.

[0030] It has been surprisingly found that using the liquid crystal medium according to the present invention enables displays with improved transparency, reduced image fixation and ODF unevenness in displays, high reliability, high VHR value and generally fast response time, low threshold voltage, and high reliability when exposed to the environment when used outdoors.

[0031] In particular, the media according to the present invention is distinguished by its excellent low-temperature stability (LTS) under harsh conditions when used outdoors.

[0032] When used in VA or FFS displays, the LC medium according to the present invention exhibits the following advantageous characteristics: • Improved transparency of the display, • High elastic constants enable high-contrast displays. • High transparency, • High voltage retention rate, • Fast switch, • Sufficient stability against heat and / or UV rays, especially when used outdoors.

[0033] In particular, the liquid crystal medium according to the present invention exhibits a preferred relatively low ratio γ1 / K1 of rotational viscosity to the spray elasticity constant. This contributes to improved switching behavior at low drive voltages, which is particularly useful for enabling energy-saving displays.

[0034] The preferred compound of formula I is selected from the compounds of formula I-1 and formula I-2.

[0035] [ka]

[0036] In the formula, R 1 and R 2 This represents an alkyl group having 1 to 7 carbon atoms.

[0037] Preferably, the medium comprises one, two, or three or more compounds of formula I-1 and one, two, or three or more compounds of formula I-2.

[0038] The preferred compounds of formula I-1 are the compounds of formulas I-1-1 to I-1-8.

[0039] [ka]

[0040] [ka]

[0041] Compounds of formulas I-1-1, I-1-2, I-1-4, and I-1-5 are particularly preferred.

[0042] The preferred compound of formula I-2 is selected from the compounds of formulas I-2-1 to I-2-4.

[0043] [ka]

[0044] Preferred compounds of formulas IIA, IIB, IIC, and IID are shown below.

[0045] [ka]

[0046]

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[0047]

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[0048]

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[0049]

change

[0050]

change

[0051]

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[0052]

change

[0053]

change

[0054]

change

[0055]

change

[0056] [ka]

[0057] In the formula, parameter a represents 1 or 2, and alkyl and alkyl * Each of the following independently represents a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms, alkenyl represents a linear or branched alkenyl group having 2 to 6 carbon atoms, and (O) represents an oxygen atom or a single bond, preferably an oxygen atom. 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-.

[0058] A very preferred medium according to the present invention comprises one or more compounds of formula IIB-2.

[0059] [ka]

[0060] In the formula, alkyl and alkyl * Each of the elements represents a linear alkyl group having 1 to 6 carbon atoms independently of each other, and (O) represents an oxygen atom or a single bond, particularly compound IIB-2-1.

[0061] [ka]

[0062] In particular, the medium contains one or more compounds of formula IIA-2 selected from the following sub-formulas.

[0063] [ka]

[0064] Alternatively, preferably, in addition to the compounds of formulas IIA-2-1 to IIA-2-5, the medium contains one or more compounds of formulas IIA-2a-1 to IIA-2a-5.

[0065] [ka]

[0066] In particular, the medium contains one or more compounds of formula IIA-10 selected from the following sub-formulas.

[0067] [ka]

[0068] Alternatively, preferably, in addition to the compounds of formulas IIA-10-1 to IIA-10-5, the medium contains one or more compounds of formulas IIA-10a-1 to IIA-10a-5.

[0069] [ka]

[0070] In particular, the medium contains one or more compounds of formula IIB-10 selected from the following sub-formulas.

[0071] [ka]

[0072] Alternatively, preferably, in addition to the compounds of formulas IIB-10-1 to IIB-10-5, the medium contains one or more compounds of formulas IIB-10a-1 to IIB-10a-5.

[0073] [ka]

[0074] A very preferred compound of formula IID is selected from the compounds of formulas IID-4, IID-7, and IID-10, and in particular from the following sub-formulas.

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] In the formula, v is an integer between 1 and 6.

[0081] In a preferred embodiment, the medium comprises one or more compounds of formula IID-10a.

[0082] [ka]

[0083] In the formula, the bases and parameters that appear have the meanings given above in formula IID, and R 2D teeth, [ka] This represents a function where r is 0, 1, 2, 3, 4, 5, or 6, and s is 1, 2, or 3.

[0084] Preferred compounds of formula IID-10a are compounds IID-10a-1 to IID-10a-14.

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] A more preferred medium according to the present invention includes one or more compounds of the formulas IIA-2, IIA-8, IIA-10, IIA-16, IIA-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, IID-4, and IID-10.

[0089] The compound of formula III is preferably selected from the compounds of formula III-1.

[0090] [ka]

[0091] The bases appearing in the formula have the same meaning as those given in formula III above, and this means, R 31 and R 32 Each of these independently represents an alkyl or alkoxy group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, and more preferably, both of them represent an alkoxy group having 1 to 7 carbon atoms. L 11 and L 12 This preferably represents F.

[0092] The liquid crystal medium according to the present invention preferably contains one or more compounds of formula III-1.

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

[0094] [ka]

[0095] [ka]

[0096] During the ceremony, Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other, and alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other, and alkoxy and alkoxy * Each represents a linear alkoxyl group having 1 to 6 C atoms independently of each other, and L 31 and L 32 Each of these independently represents either F or Cl, preferably both representing F.

[0097] In a preferred embodiment, the medium according to the present invention further comprises one or more compounds of formula IIIA.

[0098] [ka]

[0099] In the formula, the base and parameter n have the meanings defined above in Equation III.

[0100] The preferred compound of formula IIIA is selected from the group of compounds of formula IIIA-1 to IIIA-10, preferably formula IIIA-6.

[0101] [ka]

[0102] [ka]

[0103] During the ceremony, Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other, and alkenyl and alkenyl * Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other, and alkoxy and alkoxy * Each represents a linear alkoxyl group having 1 to 6 C atoms independently of each other, and L 31 and L 32 Each of these independently represents either F or Cl, preferably both representing F.

[0104] The medium may contain one or more compounds of formula IIIB-1 and / or IIIB-2.

[0105] [ka]

[0106] In the formula, L 31 and L 32 (O) has the same meaning as given in equation III, where (O) represents O or a single bond. R IIIA This refers to an alkyl or alkenyl group having up to 7 C atoms or a Cy-C group. m H 2m+1 - represents, m and n are the same or different, and are 0, 1, 2, 3, 4, 5, or 6, preferably 1, 2, or 3, and very preferably 1. Cy represents an alicyclic group having 3, 4, or 5 ring atoms, which may be substituted with an alkyl or alkenyl group or halogen or CN, each having up to 3 C atoms, preferably representing cyclopropyl, cyclobutyl, or cyclopentyl.

[0107] The compounds of formula IIIB-1 and / or IIIB-2 are included in the medium either as an alternative or additional to the compounds of formula III, preferably additionally.

[0108] The following are highly preferred compounds of formulas IIIB-1 and IIIB-2.

[0109] [ka]

[0110] In the formula, alkoxy is a linear alkoxy group having 1 to 6 C atoms, or alternatively, -(CH2) n F (wherein n is 2, 3, 4, or 5), preferably representing C2H4F.

[0111] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula III-2.

[0112] [ka]

[0113] During the ceremony, R 31 , R 32 -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 such 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.

[0114] The compound of formula III-2 is preferably selected from the group of compounds of formula III-2-1 to III-2-10.

[0115] [ka]

[0116] [ka]

[0117] In the formula, R 32 is an alkyl group having 1 to 7 C atoms, preferably ethyl, n-propyl, or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl, or cyclopentylmethyl, or alternatively -(CH2) n F (wherein n is 2, 3, 4, or 5), preferably representing C2H4F.

[0118] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formulas III-3 to III-5, preferably formula III-4.

[0119] [ka]

[0120] The parameters in the formula have the meaning given above, R 31 R preferably represents a linear alkyl group having 1 to 7 C atoms, 32 This preferably represents a linear alkoxy having 1 to 7 carbon atoms.

[0121] In a preferred embodiment, the medium according to the present invention comprises one or more compounds of formula III, preferably formula III-7, selected from the group of compounds of formula III-6 to III-8.

[0122] [ka]

[0123] The parameters in the formula have the meaning given above, R 31 R preferably represents a linear alkyl group having 1 to 7 C atoms, 32 This preferably represents a linear alkoxy having 1 to 7 carbon atoms.

[0124] In preferred embodiments, the medium comprises one or more compounds of formula IV.

[0125] [ka]

[0126] During the ceremony, R 41 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably an n-alkyl group, and particularly preferably having 2, 3, 4 or 5 carbon atoms. R 42 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkoxy group having 1 to 6 carbon atoms (both preferably having 2 to 5 carbon atoms), an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably having 2, 3, or 4 carbon atoms, more preferably a vinyl group or a 1-propenyl group, particularly a vinyl group.

[0127] The compound of formula IV is preferably selected from the group of compounds of formula IV-1 to IV-4.

[0128] [ka]

[0129] In the formula, alkyl and alkyl’ each independently represent an alkyl having 1 to 7 C atoms, preferably an alkyl having 2 to 5 C atoms, alkenyl represents an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 C atoms, alkenyl’ represents an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 to 3 C atoms, alkoxy represents an alkoxy having 1 to 5 C atoms, preferably 2 to 4 C atoms.

[0130] The compound of formula IV is preferably selected from the compounds of formulae IV-1-1 to IV-1-4.

[0131] [Chemical formula]

[0132] The compound of formula IV-2 is preferably selected from the compounds of formulae IV-2-:1 and / or IV-2-2.

[0133] [Chemical formula]

[0134] The compound of formula IV-3 is preferably selected from the compounds of formulae IV-3-1 to IV-3-9.

[0135] [Chemical formula]

[0136] The compound of formula IV-4 is preferably selected from the compounds of formulae IV-4-1 to IV-4-3, preferably the compound of formula IV-4-3.

[0137] [Chemical formula]

[0138] The liquid crystal medium according to the invention preferably contains one or more compounds of formula IVa.

[0139]

Chemical formula

[0140] In the formula, R 41 and R 42 each independently represents a linear alkyl, alkoxy, alkenyl, alkoxyalkyl or alkenyloxy group having up to 12 carbon atoms, and

Chemical formula

[0141] Preferred compounds of formula IVa are shown below.

[0142]

Chemical formula

[0143] In the formula, alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 carbon atoms.

[0144] The medium according to the invention preferably contains at least one compound of formula IVa-1 and / or formula IVa-2, very preferably at least one compound of formula IVa-2, in particular a compound IVa-2 in which alkyl represents n-propyl and alkyl * represents methyl.

[0145] The proportion of the compound of formula IVa in the whole mixture is preferably less than 5% by weight, and very preferably less than 2% by weight.

[0146] Preferably, the medium contains one or more compounds of formulas IVb-1 to IVb-3.

[0147] [ka]

[0148] 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.

[0149] The proportion of compounds of formulas IV-1 to IV-3 in the whole mixture is preferably less than 3% by weight, and more particularly less than 2% by weight.

[0150] Of the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0151] These are highly desirable biphenyls.

[0152] [ka]

[0153] In the formula, alkyl * represents an alkyl group having 1 to 6 C atoms, preferably n-propyl or n-butyl. The medium according to the present invention particularly preferably comprises one or more compounds of formula IVb-1-1 and / or IVb-2-4.

[0154] In a particularly preferred embodiment, the medium according to the present invention comprises one or more compounds of formula V.

[0155] [ka]

[0156] During the ceremony, R 51 , R 52 This refers to an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkoxyalkyl group having 2 to 7 carbon atoms, an alkenyl group, or an alkenyloxy group. [ka] Z 51 , Z 52 These each independently represent -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond, and n is either 1 or 2, and Compounds of formula I are excluded.

[0157] The compound of formula V is preferably selected from the compounds of formulas V-1 to V-16.

[0158] [ka]

[0159] [ka]

[0160] In the formula, R 51 and R 52 R has the meaning shown in equation V above. 51 and R 52 Preferably, each represents an alkyl group having 1 to 7 linear carbon atoms or an alkenyl group having 2 to 7 carbon atoms, independently of each other.

[0161] Preferred media include one or more compounds of formulas V-1, V-3, V-5, V-6, V-9, V-10, V-11, V-13, V-14 and / or V-15, particularly V-9.

[0162] In a preferred embodiment of the present invention, the medium further comprises one or more compounds of formula VI.

[0163] [ka]

[0164] In the formula, R 6 and R 62 R is defined in claim 1. 2A It has the meaning of, or R 62 represents F, Cl, CF3 or OCF3, preferably F, and L 61 , L 62 , L 63 , L 64 , L 65 and L 66 Each independently represents H or F, except for at least one L 61 , L 62 , L 63 , L 64 , L 65 and L 66 This represents F.

[0165] The compounds of formula VI are preferably selected from formulas VI-1 to VI-21, and particularly from formula VI-4.

[0166] [ka]

[0167] [ka]

[0168] [ka]

[0169] In the formula, R 6 represents a linear alkyl or alkoxy group having 1 to 6 C 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.

[0170] R 6 preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy.

[0171] Compounds of formula VI-1, VI-2, VI-4, VI-20 and VI-21 are particularly preferred.

[0172] Very preferably, the medium according to the invention comprises a compound of formula IV-4, particularly a compound of formula IV-4-1.

[0173]

Chemical formula

[0174] In the formula, R 6 and m have the meanings defined above, preferably R 6 represents methyl, ethyl, n-propyl, n-butyl or n-pentyl, and m is 2, 3 or 4.

[0175] In a preferred embodiment of the invention, the medium additionally comprises one or more compounds of formula VII-1 to VII-9.

[0176]

Chemical formula

[0177]

Chemical formula

[0178] In the formula, R 7represents a linear alkyl or alkoxy group having 1 to 6 carbon atoms or a linear alkenyl group having 2 to 6 carbon atoms, w is an integer from 1 to 6.

[0179] A mixture containing at least one compound of formula VII-9 is particularly preferred.

[0180] Even more preferred embodiments are listed below.

[0181] a) A liquid crystal medium containing at least one compound of formulas Z-1 to Z-7.

[0182]

Chemical formula

[0183] In the formula, R and alkyl have the meanings shown in formula III above.

[0184] b) Preferred liquid crystal media according to the present invention contain one or more substances containing tetrahydronaphthyl or naphthyl units, such as compounds of formulas N-1 to N-5.

[0185]

Chemical formula

[0186] In the formula, R 1N and R 2N each independently have the meaning shown for R 2A and preferably represent 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.

[0187] 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.

[0188] [ka]

[0189] During the ceremony, R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 Each of them is R independently of the others. 2A It has the meaning of 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.

[0190] Particularly preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5.

[0191] [ka]

[0192] [ka]

[0193] 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.

[0194] A mixture containing one, two, or three compounds of formula BC-2, BF-1, and / or BF-2 is very preferably preferred.

[0195] d) A preferred mixture comprises one or more indane compounds of formula In.

[0196] [ka]

[0197] During the ceremony, R 11 , R 12 and 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 a halogen, preferably F, [ka] This represents, i represents 0, 1, or 2.

[0198] Preferred compounds of formula In are the compounds of formula In-1 to In-16 shown below.

[0199] [ka]

[0200] [ka]

[0201] [ka]

[0202] Compounds of formulas In-1, In-2, In-3, and In-4 are particularly preferred.

[0203] e) A preferred mixture includes one or more compounds of formulas L-1 to L-11.

[0204] [ka]

[0205] [ka]

[0206] [ka]

[0207] During the ceremony, R, R 1 and R 2 Each of these independently of the other in equation IIA is R 2A The meaning shown is as follows: alkyl represents an alkyl group having 1 to 6 carbon atoms. The parameter s represents 1 or 2.

[0208] The compounds of formulas L1 to L9 are preferably used at a concentration of 5 to 15% by weight, particularly 5 to 12% by weight, and very preferably 8 to 10% by weight.

[0209] f) A preferred mixture includes one or more compounds of formula IIA-Y in addition.

[0210] [ka]

[0211] R in the formula 11and R 12 In equation IIA above, R 2A It has one of the meanings that can be given to L 1 and L 2 These represent F or Cl, either identical or different.

[0212] The preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0213] [ka]

[0214] [ka]

[0215] Alkyl and Alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other, 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-.

[0216] Particularly preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas.

[0217] [ka]

[0218] 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.

[0219] Preferably, the medium according to the present invention comprises one or more compounds of formula H.

[0220] [ka]

[0221] During the ceremony, Ar represents an aromatic or heteroaromatic hydrocarbon group having 4 to 40 carbon atoms, preferably 6 to 30 carbon atoms; Sp represents a spacer group; R S H represents an alkyl group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms; Z S -O-, -C(O)O-, -(CH2) z -or-(CH2) z O- or represents a single bond; HA is [ka] It represents; R H H, O · , CH3, OH or OR S Preferably H or O · It represents; R S1 , R S2 , R S3 and R S4 These represent the same or different alkyl groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, and very preferably CH3; G is either H or R S or base Z S - Represents HA; z is an integer from 1 to 6; and q is either 3 or 4.

[0222] In formula H, the aryl preferably comprises a fused ring which may be linked directly or via an alkylene linking group having 1 to 12 carbon atoms, and represents an aromatic or heteroaromatic hydrocarbon group which comprises 1, 2, 3 or 4 aromatic rings and has 1 to 40 carbon atoms, and one or more H atoms in the group may be replaced by an alkyl or alkoxy having 1 to 6 carbon atoms or an alkenyl having 2 to 6 carbon atoms, or by CN, CF3 or halogen, and one or more CH2 groups in the group may be independently replaced by -O-, -S-, -NH-, -N(C1~C4-alkyl)-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH- or -C≡C-, such that the O or S atoms are not directly linked to each other.

[0223] Preferred aryl groups are benzene, naphthalene, anthracene, biphenyl, m-terphenyl, p-terphenyl, and (phenylalkyl)benzene, where the alkyl group is a linear alkyl having 1 to 12 carbon atoms.

[0224] Compounds of formula H are described in European Patent Application Publication No. 3354710 and European Patent Application Publication No. 3354709.

[0225] The compound of formula H is preferably selected from the compounds of formulas H-1, H-2, and H-3.

[0226] [ka]

[0227] [ka]

[0228] During the ceremony, R H This has the meaning given above, preferably H or O · It represents; n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7; and Sp represents a spacer group, preferably an alkylene having 1 to 12 carbon atoms in which one or more non-adjacent -CH2- groups may be replaced by -O- groups.

[0229] The preferred compound of formula H-1 is selected from the compounds of formula H-1-1.

[0230] [ka]

[0231] In the formula, R H The above has the meaning, preferably H or O · This represents n being an integer between 0 and 12, preferably 5, 6, 7, 8, or 9, and very preferably 7.

[0232] The preferred compound of formula H-2 is selected from the compounds of formula H-2-1.

[0233] [ka]

[0234] In the formula, R H The above has the meaning, preferably H or O · Represents; and n2 is an integer from 0 to 12, preferably 2, 3, 4, 5, or 6, preferably 3, and R is identical or different in each occurrence; and R is an integer from 0 to 12, preferably 2, 3, 4, 5, or 6, preferably 3; and S Each occurrence represents an alkyl group having the same or different carbon atoms, preferably the same, and preferably n-butyl, with 1 to 6 carbon atoms.

[0235] The preferred compound of formula H-3 is selected from the compounds of formula H-3-1.

[0236] [ka]

[0237] In the formula, R H The above has the meaning, preferably H or O · This represents n being an integer between 0 and 12, preferably 5, 6, 7, 8, or 9, and very preferably 7.

[0238] Preferably, the medium according to the present invention comprises a compound selected from the group of compounds of formulas ST-1 to ST-18.

[0239] [ka]

[0240] [ka]

[0241] [ka]

[0242] [ka]

[0243] During the ceremony R ST -CH=CH- represents an alkyl or alkoxy group having H and 1 to 15 C atoms, provided that in addition, one or more CH2 groups in these groups are arranged such that the O atoms are not directly linked to each other, such as -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] -O-, -CO-O-, and -O-CO- may be substituted for each other independently, and in the group, one or more H atoms may be replaced by halogens. [ka] In each appearance, they are the same or different. [ka] This represents, Z ST These 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, CH3, CF3, or CHF2. p represents 0, 1, or 2. q represents 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0244] Among the compounds of formula ST, the compound of formula ST-3 is particularly preferred.

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248] 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.

[0249] A particularly 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.

[0250] [ka]

[0251] [ka]

[0252] 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% based on the mixture.

[0253] If the mixture according to the present invention contains two or more compounds from the group of compounds of formula ST-1 to ST-18, the concentration increases accordingly, based on the mixture, to 0.01 to 1% in the case of two compounds.

[0254] However, it is preferable that the total proportion of compounds of formulas ST-1 to ST-18 based on the mixture according to the present invention does not exceed 2%.

[0255] The medium according to the present invention preferably has negative dielectric anisotropy. In a preferred embodiment, the medium further comprises one or more compounds, preferably having positive dielectric anisotropy.

[0256] As used in this book, the term "reliability" refers to the quality of a display's performance over time, encompassing various stress loads such as light load, temperature, humidity, and voltage, as well as display effects known to those skilled in the art in the field of liquid crystal displays, such as image fixation (area and line image fixation), unevenness, and blemishes. A standard parameter used to classify reliability is typically the voltage holding ration (VHR), which is a measure of maintaining a constant electrical voltage in a test display. A high VHR is a prerequisite for high reliability of the LC medium.

[0257] From here on, unless otherwise specified, the term "PSA" will be used to refer to polymer-maintained orientation displays in general, and the term "PS" will be used to refer to specific display modes such as PS-VA and PS-TN.

[0258] Furthermore, unless otherwise specified, the term "RM" will be used below to refer to polymerizable mesogenic compounds or liquid crystalline compounds.

[0259] 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.

[0260] 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”.

[0261] Unless otherwise specified, the term "polymerizable compound" in this specification shall be understood to mean a polymerizable monomer compound.

[0262] 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."

[0263] 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.

[0264] 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.

[0265] 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."

[0266] 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.

[0267] Above and below, [ka] This represents a trans-1,4-cyclohexylene ring.

[0268] base [ka] In this example, the single bond between the two ring atoms can be linked to any unbonded position on the benzene ring.

[0269] In the above and below, "organic group" refers to a carbon or hydrocarbon group.

[0270] 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.

[0271] "Halogen" represents F, Cl, Br, or I, preferably F or Cl.

[0272] -CO-, -C(=O)-, and -C(O)- are carbonyl groups, i.e., [ka] It represents.

[0273] 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.

[0274] Furthermore, terms such as "alkyl," "aryl," and "heteroaryl" also encompass polyvalent groups, such as alkylenes, arylenes, and heteroarylenes.

[0275] 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).

[0276] In this specification, alkyl is linear or branched and has 1 to 15 carbon atoms, preferably linear and, unless otherwise specified, has 1, 2, 3, 4, 5, 6 or 7 carbon atoms, and accordingly preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0277] In this specification, branched alkyl refers to alkyl having secondary and / or tertiary, preferably secondary, carbon atoms, and is preferably isopropyl, s-butyl, isobutyl, isopentyl, 2-methylhexyl or 2-ethylhexyl, 2-methylpropyl, 2-pentyl, 3-pentyl, 2-methylbutyl, or 3-methylbutyl.

[0278] In this specification, a cyclic alkyl group means an alkyl group in which an alicyclic group or a methylene group is substituted with an alicyclic group (i.e., a cycloalkylalkyl or alkylcycloalkylalkyl), which may be saturated or partially unsaturated, and preferably represents cyclopropyl, methylcyclopropyl, cyclobutyl, methylcyclobutyl, cyclopentyl, methylcyclopentyl, cyclopento-1-enyl, cyclopropylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentoylethyl, or cyclopento-1-enylmethyl.

[0279] In this specification, the alkoxy group is linear or branched and contains 1 to 15 carbon atoms. Preferably linear and, unless otherwise indicated, has 1, 2, 3, 4, 5, 6, or 7 carbon atoms, and is preferably methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, or n-heptoxy.

[0280] In this specification, the alkenyl group is preferably an alkenyl group having 2 to 15 carbon atoms, being linear or branched, and containing at least one carbon-C double bond. Preferably linear and having 2 to 7 carbon atoms. Thus preferably vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pento-1-, -2-, -3- or -4-enyl, hexa-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl. If two carbon atoms of the carbon-C double bond are substituted, the alkenyl group may be in the form of E and / or Z isomers (trans / cis). Generally, each E isomer is preferred. Among the alkenyl groups, prop-2-enyl, but-2- and -3-enyl, and pento-3- and -4-enyl are particularly preferred.

[0281] In this specification, "alkynyl" is interpreted to mean an alkynyl radical having 2 to 15 carbon atoms, being linear or branched, and containing at least one carbon-carbon triple bond. 1- and 2-propynyl and 1-, 2- and 3-butynyl are preferred.

[0282] 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.

[0283] 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.

[0284] C1~C 12 Alkyl, C2~C 12 Alkenyl, C2~C 12 Alkinyl, C6~C 25 Aryl and C2~C 25 Heteroaryls are particularly preferred.

[0285] 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.

[0286] 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.

[0287] 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.

[0288] Preferred alkenyl groups include, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, and cyclooctenyl.

[0289] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, and octinyl.

[0290] 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.

[0291] Preferred amino groups include, for example, dimethylamino, methylamino, methylphenylamino, and phenylamino.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] 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.

[0296] 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.

[0297] (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.

[0298] (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-.

[0299] 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.

[0300] Preferred substituents include, for example, dissolution-promoting groups such as alkyl or alkoxy groups, and electron-withdrawing groups such as fluorine, nitro, or nitrile groups.

[0301] Preferred substituents will also be referred to as "L" hereafter, 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.

[0302] 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.

[0303] "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 0 This means substitution by R, however, 0 represents an alkyl group having H or 1 to 20 C atoms.

[0304] 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.

[0305] To manufacture a PSA display, polymerizable compounds contained in the LC medium are polymerized or crosslinked (when one compound contains two or more polymerizable groups) by in-situ polymerization between the substrates of the LC display while optionally applying a voltage to the electrodes.

[0306] The structure of the PSA display according to the present invention corresponds to the conventional configuration of a PSA display as described in the prior art cited at the beginning. A configuration without protrusions is preferred, and in particular, it is preferred that the electrodes on the color filter side are not structured, and only the electrodes on the TFT side have slits. A particularly suitable and preferred electrode structure for PS-VA displays is described, for example, in U.S. Patent Application Publication No. 2006 / 0066793.

[0307] The LC medium according to the present invention may preferably further contain one or more additional components or additives selected without limitation from the list including comonomers, chiral dopants, polymerization initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricants, dispersants, hydrophobic agents, adhesives, flow improvers, defoamers, deaeration agents, diluents, reactive diluents, auxiliary agents, colorants, dyes, pigments, and nanoparticles.

[0308] The LC medium according to the present invention preferably comprises one, two, or three types of chiral dopants, and very preferably one type of chiral dopant.

[0309] LC media containing one, two, or three polymerizable compounds, also known as reactive mesogens (RM), are particularly preferred.

[0310] An LC medium having a chiral nematic LC phase is even more preferred.

[0311] Preferably, the proportion of polymerizable compounds (RM) in the LC medium is greater than 0% but less than 5%, very preferably greater than 0% but less than 1%, and most preferably 0.01 to 0.5%.

[0312] Preferred embodiments, either individually or in combination, are listed below. The medium according to the present invention preferably includes the following:

[0313] • One or more compounds of formula I in a concentration of 5% to 30%, preferably 10% to 20%, and very preferably 12% to 17%;

[0314] • One or more compounds of formula I in a concentration of 10% to 35%, preferably 15% to 33%, and very preferably 20% to 30%;

[0315] • One or more compounds of formula I-1 in a concentration of 2% to 11%, preferably 3% to 10%, and very preferably 4% to 9%;

[0316] • One or more compounds of formula I-1 in a concentration of 5% to 20%, preferably 6% to 17%, and very preferably 7% to 15%;

[0317] • One or more compounds of formula I-2 in a concentration of 2% to 15%, preferably 3% to 14%, and very preferably 4% to 13%;

[0318] • One or more compounds of formula IIA and optionally IIA-Y in a total concentration of 30% to 67%, more preferably 35% to 62%, very preferably 38% to 55%, and especially 40% to 50%;

[0319] • One or more compounds of formula IIA-2 in a total concentration of 14% to 34%, more preferably 15% to 31%, very preferably 16% to 28%, and especially 17% to 25%;

[0320] • One or more compounds of formulas IIA-2 and IIA-Y in a total concentration of 8% to 40%, more preferably 9% to 38%, very preferably 11% to 33%, and especially 12% to 30%;

[0321] • One or more compounds of formula IIA-10 in a total concentration of 15% to 34%, more preferably 18% to 31%, very preferably 19% to 28%, and especially 20% to 26%;

[0322] • One or more compounds of formula IIA-Y in a total concentration of 2% to 15%, preferably 5% to 13%, more preferably 7% to 12%;

[0323] One or more compounds of formula IIB, preferably formula IIB-2 and / or IIB-10, very preferably IIB-10, in a total concentration of 1% to 17%, more preferably 3% to 16%, very preferably 5% to 15%;

[0324] • One or more compounds of formula IID, preferably formula IID-4, in a total concentration of 1% to 10%, preferably 2% to 8%, and very preferably 2% to 7%;

[0325] • One or more compounds of formulas IID-4 and IID-10 in a total concentration of 5% to 20%, preferably 8% to 18%, and very preferably 10% to 15%;

[0326] One, two, or three or more compounds of formula III, preferably formula III-1 and / or formula III-2 and formula IIIA, in a total concentration of 1% to 12%, more preferably 2% to 11%, and very preferably 3% to 10%;

[0327] • One or more compounds selected from compounds of formula IV, preferably formulas IV-2 and IV-3, more preferably formulas IV-3-4 and / or IV-3-5, in a total concentration of 12% to 35%, more preferably 15% to 30%, and very preferably 18% to 25%;

[0328] One or more compounds of formula V, preferably formula V-9, in a total concentration of 1% to 10%, more preferably 1% to 7%, and very preferably 1.5% to 5%.

[0329] The liquid crystal medium according to the present invention is advantageous in that it preferably has a nematic phase with a temperature range of -20°C or lower to 95°C or higher, particularly preferably -30°C or lower to 97°C or higher, and very particularly preferably -40°C or lower to 99°C or higher.

[0330] In a preferred embodiment, the medium according to the present invention has a transparency temperature of 95°C or higher, more preferably 97°C or higher, and particularly 99°C or higher.

[0331] In this specification, the expression "having a nematic phase" at a given temperature means that the smectic phase and crystallization are not observed at low temperatures, and that, conversely, no transparency (transition to an isotropic phase) occurs when the nematic phase is heated at a given temperature. Low-temperature studies are performed using a fluid viscometer at the corresponding temperature and confirmed by storing the sample in a test cell with a layer thickness suitable for electro-optical applications for at least 100 hours. 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.

[0332] The liquid crystal mixture preferably has a nematic phase range of at least 100K and a maximum of 30mm at 20°C. 2 ·Seconds -1 The fluid viscosity ν 20 It has.

[0333] The mixture is nematic at temperatures below -20°C, preferably below -30°C, and very preferably below -40°C.

[0334] The medium according to the present invention has a birefringence in the range of 0.080 to 0.110, preferably 0.082 to 0.105, and particularly 0.085 to 0.100.

[0335] In a preferred embodiment, the medium has a birefringence in the range of 0.0890 to 0.1000, preferably 0.0940 to 0.0970, and particularly 0.0950 to 0.0960.

[0336] In another preferred embodiment, the medium has a birefringence in the range of 0.0830 to 0.0900, preferably 0.0840 to 0.0880, and particularly 0.0850 to 0.0870.

[0337] In a preferred embodiment, the medium according to the present invention has a dielectric anisotropy Δε of -3.5 to -7.0, preferably -4.0 to -6.0, and particularly -4.5 to -5.5.

[0338] In a very preferred embodiment, the liquid crystal mixture according to the present invention has a dielectric anisotropy Δε of -4.8 to -5.2.

[0339] The rotational viscosity γ1 at 20°C is preferably in the range of 150 to 300 mPa·s, more preferably 200 to 250 mPa·s.

[0340] The rotational viscosity γ1 at 20°C is preferably 230 mPa-sec or less.

[0341] The medium according to the present invention has an elastic constant K1 in the range of 14 to 16.

[0342] In a preferred embodiment, the medium according to the present invention is 15 mPa·s·pN -1 The following ratio of rotational viscosity to spray elastic constant γ1 / K1 is observed.

[0343] The liquid crystal medium according to the present invention has a relatively low threshold voltage (V0). These values ​​are preferably in the range of 1.5V to 2.5V, particularly preferably 2.2V or less, and very particularly preferably 2.0V or less.

[0344] In this invention, the term "threshold voltage" refers to the capacitive threshold (V0), also known as the Fredericks threshold, unless otherwise explicitly indicated.

[0345] In addition, the liquid crystal medium according to the present invention has a high voltage retention rate in liquid crystal cells.

[0346] Generally, liquid crystal media with a low address voltage or threshold voltage exhibit a lower voltage retention rate than those with a high address voltage or threshold voltage, and vice versa.

[0347] In this invention, the term "dielectrically positive compound" refers to a compound having a Δε greater than 1.5, the term "dielectrically neutral compound" refers to a compound having a Δε of -1.5 or more and 1.5 or less, and the term "dielectrically negative compound" refers to a compound having a Δε less than -1.5.

[0348] The dielectric anisotropy of a compound is determined by dissolving 10% of the compound in a liquid crystal host and measuring the capacitance of the mixture obtained in at least one test cell with a homeotropic and homogeneous surface orientation, each having a layer thickness of 20 μm, at 1 kHz. The measurement voltage is typically 0.5 V to 1.0 V, but is always kept lower than the capacitance threshold of the liquid crystal mixture under consideration.

[0349] All temperature values ​​shown in this invention are in °C.

[0350] The mixtures according to the present invention are suitable for all VA-TFT applications, such as VAN, MVA, (S)-PVA, ASV, PSA (polymer sustained VA), and PS-VA (polymer stabilized VA), as well as for passive matrix VA (PM (passive matrix)-VA). They are also suitable for in-plane switching (IPS) and fringe field switching (FFS) applications with negative Δε.

[0351] It goes without saying to those skilled in the art that the medium according to the present invention may also include, for example, compounds in which H, N, O, Cl, and F are substituted with the corresponding isotopes.

[0352] The compounds according to the present invention can be synthesized by known methods described in the literature (e.g., standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, and Stuttgart) or by similar methods under known reaction conditions suitable for the aforementioned reaction. Although not mentioned herein, known variations can also be used herein.

[0353] Other mesogenic compounds not explicitly mentioned above can also be advantageously used in media according to the present invention. Such compounds are known to those skilled in the art.

[0354] 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. m H 2m+1 , C n H 2n+1 , and C l H 2l+1 or C m H 2m-1 , C n H 2n-1 and andC l H 2l-1 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.

[0355] <Table A: Ring elements>

[0356] [Table 1]

[0357] [Table 2]

[0358] [Table 3]

[0359] <Table B: Bridge Units>

[0360] [Table 4]

[0361] <Table C: Terminal group>

[0362] [Table 5]

[0363] [Table 6]

[0364] In the table, n and m are integers, and the three dots "..." are spaces for other abbreviations from this table.

[0365] Apart from the compounds of formulas I, IIA, IIB, IIC and / or IID and III, the mixture according to the present invention preferably comprises one or more compounds of the compounds described below.

[0366] Use the following abbreviations: (n, m, k, and l are each independent integers, preferably 1 to 9, 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, and in the combination "-nO-", 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", preferably 1, 2, 3, or 4, more preferably 2 or 4; the combination "-lVm" is preferably "2V1".)

[0367]

[0368] [Table 7]

[0369] [Table 8]

[0370] [Table 9]

[0371] [Table 10]

[0372] [Table 11]

[0373] [Table 12]

[0374] [Table 13]

[0375] Table 14

[0376] Table 15

[0377] Table 16

[0378] Table 17

[0379] Table 18

[0380] Table 19

[0381] Table 20

[0382] Table 21

[0383] Table 22

[0384] Table 23

[0385] Table 24

[0386] [Table 25]

[0387] [Table 26] [Examples]

[0388] The present invention is described in detail by the following non-limiting embodiments.

[0389] Use the following abbreviations and symbols: V0 is the capacitance threshold voltage [V] at 20°C. n e This is an anomalous refractive index at 20°C and 589nm. n0 is the typical refractive index at 20°C and 589nm. Δn is the optical anisotropy at 20°C and 589 nm. ε ⊥ The dielectric constant perpendicular to the director at 20°C and 1kHz is ε ∥ The dielectric constant parallel to the director at 20°C and 1kHz, Δε is the dielectric anisotropy at 20°C and 1kHz. cl.p., T(N,I) is the point of transparency [°C]. γ1 is the rotational viscosity [mPa·s] at 20℃. K1 is the elastic constant [pN] for "splay" deformation at 20°C. K2 is the elastic constant [pN] for "twist" deformation at 20°C. K3 is the elastic constant [pN] for "bend" deformation at 20°C.

[0390] Unless explicitly stated otherwise, all concentrations in this application are given in weight percent and refer to the corresponding mixture as a whole, consisting of all solid or liquid crystal components, without regard to the solvent.

[0391] Unless explicitly stated otherwise, all temperature values ​​expressed in this application, such as the melting point T(C,N), the transition from the smectic (S) phase to the nematic (N) phase T(S,N), and the transparency point T(N,I), are cited in degrees Celsius (°C). Mp is the melting point, and cl.p. is the transparency point. Furthermore, C is the crystalline state, N is the nematic phase, S is the smectic phase, and I is the isotropic phase. The data between these symbols represents the transition temperature.

[0392] All physical properties are determined or have been determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals," published November 1997 by Merck, Germany, applicable at a temperature of 20°C, with Δn being 589 nm and Δε being 1 kHz unless otherwise explicitly indicated.

[0393] In this invention, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Frederick's threshold, unless otherwise specified. Furthermore, in the example, although generally typical, 10% relative contrast (V0) is used. 10 The optical threshold for ) may also be indicated.

[0394] Unless otherwise specified, the method for preparing test cells and the method for measuring electro-optical properties, etc., shall be carried out by the method described below or a similar method.

[0395] The display used for measuring capacitance threshold voltage consists of two planar parallel glass outer plates spaced 25 μm apart, each with an electrode layer on the inside and an unrubbed polyimide orientation layer on the top that brings about homeotropic orientation of liquid crystal molecules.

[0396] Unless otherwise clearly stated, VHR is 20℃ (VHR 20) and after 5 minutes in a 100°C oven (VHR 100 This is determined in the equipment model LCM-1(O0004) commercially available from Toyo Technica Co., Ltd. in Japan. Unless otherwise specified, the voltage used has a frequency in the range of 1Hz to 60Hz.

[0397] The stability against UV irradiation will be examined using the Heraeus "Suntest CPS+" system from Germany, which utilizes a xenon lamp NXE1500B. Sealed test cells will be irradiated for 2.0 hours without additional heating unless otherwise specified. The irradiation power in the wavelength range of 300nm to 800nm ​​will be 765W / m². 2 V. To simulate the so-called window glass mode, a UV "cutoff" filter with an edge wavelength of 310 nm is used. In each series of experiments, at least four test cells are examined for each condition, and the results are presented as the average of the corresponding individual measurements.

[0398] To investigate the low-temperature stability, also known as "LTS (low-temperature stability)," i.e., the stability of bulk LC mixtures against spontaneous crystallization or smectic phase formation of individual components at low temperatures, several sealed bottles, each containing approximately 1 g of material, are stored at one or more predetermined temperatures, typically -10°C, -20°C, -30°C, and / or -40°C, and visually inspected at regular intervals to see if a phase transition is observed. The time is recorded when the first sample shows a change at a predetermined temperature. The time until the last inspection in which no change is observed is recorded as the respective LTS.

[0399] The ion density for calculating resistivity is measured using the LC material property measurement system Model 6254, commercially available from Toyo Technica Co., Ltd. in Japan, with a VHR test cell (cell gap 3.2 μm) using AL16301 polyimide (JSR Corporation, Japan). The measurement is performed after storing the sample in an oven at 60°C or 100°C for 5 minutes.

[0400] The transparency point is measured using a Mettler Thermosystem FP900. Optical anisotropy (n) is measured using an Abbe refractometer H005 (sodium spectral lamp Na10, 589 nm, at 20°C). Dielectric anisotropy (Δε) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell equipped with JALS2096-R1). Start-up voltage (V0) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell equipped with JALS2096-R1). Rotational viscosity (γ1) is measured at 20°C using a Toyo Technica LCM-2 (0002) (gamma 1 negative cell equipped with JALS-2096-R1). The elastic constant (K1, spray) is measured at 20°C using an LCR meter E4980A / Agilent Corporation (G005) (ε-parallel cell equipped with JALS2096-R1). K3: The elastic constant (K3, bend) is measured at 20°C using an LCR meter E4980A / Agilent Corporation (G005) (ε-parallel cell equipped with JALS2096-R1).

[0401] The following examples of mixtures having negative dielectric anisotropy are particularly suitable for IPS and FFS displays, especially liquid crystal displays having at least one planar alignment layer such as UB-FFS (ultra-high brightness FFS), as well as VA displays.

[0402] <Mixture example> Nematic LC host mixtures M1 to M19 have the composition and physical properties given in the following table.

[0403] <Mixture M1>

[0404] [Table 27]

[0405] <Mixture M2>

[0406] [Table 28]

[0407] <Mixture M3>

[0408] Table 29

[0409] <Mixture M4>

[0410] Table 30

[0411] <Mixture M5>

[0412] Table 31

[0413] <Mixture M6>

[0414] Table 32

[0415] <Mixture M7>

[0416] Table 33

[0417] <Mixture M8>

[0418] Table 34

[0419] <Mixture M9>

[0420] Table 35

[0421] Mixture M9 contains compound B(S)-(c5)1O-O2.

[0422] [ka]

[0423] <Mixture M10>

[0424] [Table 36]

[0425] <Mixture M11> Mixture M11 consists of 98.87% mixture M1, 0.03% compound ST-3a-1, and 0.10% compound H-1-1.

[0426] [Table 37]

[0427] <Mixture M12> Mixture M12 consists of 98.965% mixture M1, 0.03% compound ST-3a-1, and 0.005% compound H-2-1a.

[0428] [Table 38]

[0429] <Mixture M13>

[0430] [Table 39]

[0431] <Mixture M14>

[0432] Table 40

[0433] <Mixture M15>

[0434] Table 41

[0435] <Mixture M16>

[0436] Table 42

[0437] <Mixture M17>

[0438] Table 43

[0439] <Mixture M18>

[0440] Table 44

[0441] Mixture M18 contains the compound CCY-(c5)-O2.

[0442]

change

[0443] <Mixture M19>

[0444] Table 45

[0445] Mixture M19 contains compound B(S)-(c5-3en)1O-O2.

[0446]

change

Claims

1. a) a liquid crystal medium comprising one or more compounds of formula I, b) one or more compounds selected from the group of compounds of formulas IIA, IIB, IIC, and IID, and c) one or more compounds of formula III. 【Chemistry 1】 (In the ceremony R １ and R ２ Each of these groups independently represents H, an alkyl or alkenyl group having 1 to 12 carbon atoms, or 2 to 12 carbon atoms, wherein the group is unsubstituted or at least one-substituted with a halogen, and furthermore, 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-, 【Chemistry 2】 -C≡C-, -CF ２ O-, -OCF ２ -, -CO-O- or -O-CO- may be replaced, and in the group one or more H atoms may be replaced with halogens, n is either 0 or 1. 【Transformation 3】 (In the ceremony R １Ａ 、 R １Ｂ 、 R １Ｃ 、 R １Ｄ 、 R ２Ａ 、 R ２Ｂ 、 R ２Ｃ and R ２Ｄ each independently represents H, an alkyl or alkenyl group having 1 to 12 C atoms or 2 to 12 C atoms, which group is unsubstituted, monosubstituted with CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ groups in these groups are such that O atoms are not directly connected to each other, -O-, -S-, 【Chemistry 4】 -C≡C-, -CF ２ O-, -OCF ２ -, -CO-O- or -O-CO- may be used as substitutes. L １ and L ２ These are F, Cl, and CF, which are independent of each other. ３ or CHF ２ This represents, Y is the same or different in each occurrence as H, F, Cl, CF ３ CHF ２ or CH ３ This represents, Z １ Z １Ｂ and Z １Ｄ 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, and q represents either 0 or 1. 【Transformation 5】 (In the ceremony R ３１ and R ３２ Each represents an alkyl or alkoxy group having H and 1 to 15 C atoms independently of each other, 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 6】 -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 with halogens. A ３１ Each of them appeared independently of the others. a) A 1,4-cyclohexenylene or 1,4-cyclohexylene group, with one or two non-adjacent CH groups in the group. ２ The base can be replaced with -O- or -S-. b) A 1,4-phenylene group, in which one or two CH groups may be replaced by N, or c) Groups from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl, and fluorene-2,7-diyl This represents, However, groups a), b), and c) may be monosubstituted or polysubstituted with halogen atoms. Z ３１ In each occurrence, -CO-O-, -O-CO-, and -CF appear independently of each other. ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -ien-CH ２ -ien-CH ２ CH ２ -, - (CH ２ ) ４ -, -CH=CH-CH ２ O-, -C ２ F ４ -ien-CH ２ CF ２ -, -CF ２ CH ２ -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or single bond, L ３１ and L ３２ These are F, Cl, and CF, which are independent of each other. ３ or CHF ２ Represents, and n is 0, 1, or 2.

2. The medium according to claim 1, comprising one or more compounds of formula IID selected from the group consisting of formula IID-4, IID-7, and IID-10. 【Transformation 7】 (In the formula, "alkyl" represents a linear alkyl group having 1 to 6 carbon atoms, and "(O)" represents an oxygen atom or a single bond.)

3. The medium according to claim 2, comprising a compound of formula IID-10.

4. The medium according to claim 1, comprising one, two, or three or more compounds of formula I-1 and one, two, or three or more compounds of formula I-2. 【Transformation 8】 (In the formula, R １ and R ２ (This represents an alkyl group having 1 to 7 carbon atoms.)

5. The medium according to claim 1, comprising a compound of formula I as defined in claim 1 in a total concentration ranging from 5% to 30% by weight.

6. The medium according to claim 1, comprising one or more compounds of formula IV. 【Chemistry 9】 (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. 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.)

7. The medium according to claim 6, wherein the compound of formula IV is selected from the group of compounds of the following formulas. 【Chemistry 10】

8. The medium according to claim 6, wherein the concentration of one or more compounds of formula IV is in the range of more than 0% by weight to 25% by weight.

9. The medium according to claim 1, having a transparency point of 95°C or higher.

10. The medium according to claim 1, which, when measured with light of a wavelength of 589.9 nm at 20°C, has a birefringence in the range of 0.080 to 0.

100.

11. A method for preparing an LC medium according to claim 1, comprising the step of mixing one or more compounds of formula I with one or more compounds selected from the group consisting of formulas IIA, IIB, IIC, and IID, and one or more compounds of formula III.

12. An LC display comprising the medium described in claim 1.

13. The display according to claim 12, which is a VA, PSA, PS-VA, PVA, MVA, PM-VA, FFS, UB-FFS, PS-FFS, IPS, or PS-IPS display.

14. The display according to claim 13, which is a passive matrix VA display.

15. Use of the liquid crystal medium described in claim 1 in an electro-optical display.

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