Liquid-crystalline medium

Abstract

The present application relates to a liquid-crystalline (LC) medium as defined in claim 1 comprising a compound of formula (I) and one or more compounds of formula (II) and to its use for optical, electro-optical and electronic purposes, in particular for use in LC displays, especially in IPS, FFS, VA or PS-VA displays.

Description

[0001] This invention relates to a liquid crystal (LC) medium and its use for optical, electro-optical and electronic purposes, particularly for use in LC displays, especially in IPS, FFS, VA or PS-VA displays.

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

[0003] Additionally, there are known VA (Vertical Alignment) displays with wider viewing angles. The LC cell of a VA display contains a layer of LC dielectric between two transparent electrodes, where the LC dielectric typically has negative dielectric anisotropy. In the off-state, the molecules of the LC layer are aligned perpendicularly to the electrode surfaces (plane alignment) or have a tilted vertical alignment. When a voltage is applied to the two electrodes, a realignment of the LC molecules occurs parallel to the electrode surfaces.

[0004] Additionally, OCB ("Optically Compensated Curvature") displays are known, which are based on birefringence and have an LC layer (which has a so-called "curved" alignment and generally positive dielectric anisotropy). When a voltage is applied, the LC molecules undergo reorientation perpendicular to the electrode surface. Furthermore, OCB displays typically contain one or more birefringent optical retardation films to prevent undesirable light transmittance from the curved cell in the dark. OCB displays offer a wider viewing angle and a shorter response time compared to TN displays.

[0005] Also known are so-called IPS ("in-plane switching") displays, which contain an LC layer between two substrates, with two electrodes disposed on only one of the two substrates, and preferably having 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 thus generated between them. This causes the LC molecules to reorient within the layer plane.

[0006] Additionally, so-called FFS (edge ​​field switching) displays have been reported (see especially SH Jung et al., Jpn. J. Appl. Phys., Vol. 43, No. 3, 2004, 1028), which contain two electrodes on the same substrate, one structured in a comb-like manner and the other unstructured. This generates a strong so-called "edge field," i.e., a strong electric field near the edge of the electrode, and such an electric field throughout the cell, which has both strong vertical and strong horizontal components. FFS displays exhibit low contrast viewing angle dependence. FFS displays typically contain an LC dielectric with positive dielectric anisotropy and an alignment layer, typically a polyimide alignment layer, which provides planar alignment of the molecules of the LC dielectric.

[0007] FFS displays can operate as either active or passive matrix displays. In the case of an active matrix display, individual pixels are typically addressed by integrated nonlinear active elements such as transistors (e.g., thin-film transistors or "TFTs"), while in the case of a passive matrix display, individual pixels are typically addressed according to multiplexing methods known in the art.

[0008] Furthermore, FFS displays have been disclosed (see SH Lee et al., Appl. Phys. Lett. 73(20), 1998, 2882-2883 and SH Lee et al., Liquid Crystals 39(9), 2012, 1141-1148), which have similar electrode designs and layer thicknesses to FFS displays, but include a layer of LC dielectric with negative dielectric anisotropy instead of a layer of LC dielectric with positive dielectric anisotropy. Compared to LC dielectric with positive dielectric anisotropy, LC dielectric with negative dielectric anisotropy exhibits a more favorable director orientation, with less tilt and more twist, resulting in higher transmittance for these displays. The display also includes an alignment layer, preferably provided on at least one substrate as a polyimide, which contacts the LC dielectric and induces planar alignment of the LC molecules of the LC dielectric. These displays are also referred to as “Ultra-Brightness FFS (UB-FFS)” mode displays. These displays require LC dielectrics with high reliability.

[0009] The term "reliability" as used below refers to the quality of a display's performance over time and under varying stress loads, such as optical load, temperature, humidity, and voltage, and includes display effects such as image lag (surface and line image lag), color difference, and yogore, which are known to those skilled in the art of LC displays. As a standard parameter for classifying reliability, the voltage hold-up ratio (VHR) value is commonly used; it is a measure of maintaining a constant voltage in a tested display. Among other factors, a high VHR is a prerequisite for high reliability in LC media.

[0010] In newer types of VA displays, the uniform orientation of LC molecules is confined to a number of relatively small domains within the LC cell. Disclination, also known as tilted domains, can exist between these domains. VA displays with tilted domains offer greater contrast and viewing angle independence in grayscale compared to conventional VA displays. Furthermore, this type of display is easier to manufacture because it eliminates the need for additional electrode surface treatments (e.g., by friction) to ensure uniform molecular orientation in the on-state. Instead, the preferred orientation of the tilt angle or pretilt angle is controlled through special electrode design.

[0011] In so-called MVA (Multi-domain Vertical Alignment) displays, this is typically achieved using electrodes with protrusions that cause localized pre-tilting. This allows LC molecules to align parallel to the electrode surface in different orientations within different, defined cell regions when voltage is applied. This enables "controlled" switching and prevents the formation of interfering misalignment lines. While this arrangement improves the display's viewing angle, it results in reduced light transmittance. A further improvement to MVA uses protrusions on only one electrode side, with the opposing electrode having a slit, which improves light transmittance. This slit electrode generates a non-uniform electric field within the LC cell when voltage is applied, meaning controlled switching is still achieved. To further improve light transmittance, the spacing between the slit and the protrusion can be increased, but this conversely leads to an increased response time. In so-called PVA (“patterned VA”), protrusions are completely unnecessary because the two electrodes are structured on opposite sides through slits. This results in increased contrast and improved light transmittance, but it is technically difficult and makes the display more sensitive to mechanical influences (“tapping”, etc.). However, for many applications, such as monitors and especially TV screens, there is a demand for shorter display response times and improved contrast and brightness (transmittance).

[0012] Another development is the so-called PS (“polymer stabilized”) or PSA (“polymer stabilized alignment”) display, which is occasionally also referred to by the term “polymer stabilization”. In these, a small amount (e.g., 0.3 wt%, typically <1 wt%) of one or more polymerizable compounds, preferably polymerizable monomeric compounds, is added to the LC medium, and after the LC medium is filled into the display, it is polymerized or crosslinked in situ (usually by UV photopolymerization), while optionally a voltage is applied to the electrodes of the display. Polymerization is carried out at the temperature at which the liquid crystal phase of the LC medium is displayed, typically at room temperature. The addition of polymerizable mesocrystalline or liquid crystal compounds (also known as reactive mesocrystalline or “RM”) to the LC mixture has proven particularly suitable.

[0013] Unless otherwise stated, the term "PSA" will be used hereinafter when referring to displays of a general polymer-stabilized alignment type, and "PS" will be used when referring to a specific display mode (such as PS-VA, PS-TN, etc.).

[0014] In addition, unless otherwise stated, the term "RM" will be used below when referring to polymerizable mesocrystalline or liquid crystal compounds.

[0015] Meanwhile, the PS(A) principle is being used in various conventional LC display modes. Thus, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, and PS-TN displays are known, for example. In the case of PS-VA and PS-OCB displays, RM aggregation preferably occurs under an applied voltage, while in the case of PS-IPS displays, it occurs with or without, preferably without, an applied voltage. As can be verified in a test chamber, the PS(A) method results in pre-tilting within the chamber. In the case of PS-OCB displays, for example, the bending structure can be stabilized, thereby making the offset voltage unwanted or reduced. In the case of PS-VA displays, this pre-tilting has a positive effect on response time. For PS-VA displays, standard MVA or PVA pixel and electrode layouts can be used. However, alternatively, for example, using only a structured electrode side without protrusions can also be managed, which significantly simplifies production and simultaneously produces very good contrast and very good transmittance.

[0016] Furthermore, the so-called positive-VA display (“positive VA”) has proven to be a particularly advantageous mode. Similar to conventional VA displays, in a positive-VA display, the initial orientation of the LC molecules in the initial state when no voltage is applied is vertical, i.e., substantially perpendicular to the substrate. However, compared to conventional VA displays, positive-VA displays use an LC dielectric with positive dielectric anisotropy. Similar to commonly used IPS displays, the two electrodes in a positive-VA display are arranged on only one of the two substrates, and preferably exhibit an interlocking and comb-like (interdigitated) structure. By applying a voltage that generates an electric field substantially parallel to the LC dielectric layer to the interdigitated electrodes, the LC molecules are transformed to an orientation substantially parallel to the substrate. Polymer stabilization (by incorporating RM (which polymerizes in the display)) has also proven advantageous in positive-VA displays, thereby enabling a significant reduction in response time.

[0017] PS-VA displays are described, for example, in EP1 170 626 A2, US 6,861,107, US 7,169,449, US2004 / 0191428 A1, US 2006 / 0066793 A1, and US 2006 / 0103804 A1. PS-OCB displays are described, for example, in T.-J-Chen et al., Jpn.J.Appl.Phys.45, 2006, 2702-2704, and SHKim, L.-C-Chien, Jpn.J.Appl.Phys.43, 2004, 7643-7647. PS-IPS displays are described, for example, in US 6,177,972 and Appl.Phys.Lett.1999, 75(21), 3264. PS-TN displays are described, for example, in Optics Express 2004, 12(7), 1221.

[0018] Beneath the layer formed by phase separation and polymerization RM induced by the aforementioned pre-tilt angle, PSA displays typically contain an alignment layer, such as an alignment layer of polyimide, which provides initial alignment of LC molecules prior to the polymer stabilization step.

[0019] Friction-treated polyimide layers have long been used as alignment layers. However, the friction method introduces various problems, such as color difference, contamination, electrostatic discharge, and residue. Therefore, instead of friction-treated polyimide layers, it is proposed to use polyimide layers prepared by photo-alignment, utilizing the photo-induced orientation sequence of the alignment surface. This can be achieved using polarized light via photodecomposition, photodimerization, or photoisomerization.

[0020] However, a suitably derived polyimide layer containing photoreactive groups is still required. Generally speaking, the processing of the polyimide and the modified bump or polymer layer for producing this polyimide layer is relatively labor-intensive and costly.

[0021] Furthermore, unfavorable interactions between the polyimide alignment layer and certain compounds in the LC medium have been observed, often leading to a decrease in the display's resistance. At the cost of improving display parameters (such as viewing angle dependence, contrast ratio, and response time) through the use of such LC compounds, the number of suitable and available LC compounds is thus significantly reduced. Therefore, the polyimide alignment layer needs to be omitted.

[0022] For some display modes, this is achieved by adding a self-aligning agent or additive to the LC dielectric, which induces the desired alignment, such as vertical or planar alignment, in situ through a self-assembly mechanism. Therefore, the alignment layer on one or both of the substrates can be omitted. These display modes are also called "self-aligned" or "self-aligned" (SA) modes.

[0023] In SA displays, a small amount (typically 0.1% to 2.5%) of a self-aligning additive is added to the LC medium. Suitable self-aligning additives are, for example, compounds having an organic core group and one or more polar anchoring groups attached thereto, which can interact with the substrate surface, causing the additive on the substrate surface to align and also inducing the desired alignment in the LC molecules. Preferred self-aligning additives contain, for example, mesocrystalline groups and straight-chain or branched alkyl side chains terminated by one or more polar anchoring groups, such as those selected from hydroxyl, carboxyl, amino, or thiol groups. The self-aligning additive may also contain one or more polymerizable groups that can be polymerized under conditions similar to those used in the PSA process for RM.

[0024] SA-VA displays and SA-FFS displays have been disclosed to date. Suitable self-aligning additives for inducing vertical alignment, particularly for SA-VA mode displays, are disclosed, for example, in US 2013 / 0182202 A1, US 2014 / 0138581 A1, US 2015 / 0166890 A1 and US 2015 / 0252265 A1.

[0025] SA mode can also be used in combination with PSA mode. The LC media of the display used in this combined mode therefore contains both one or more RMs and one or more self-aligning additives.

[0026] Similar to conventional LC displays, PSA displays can operate as either active-matrix or passive-matrix displays. In the case of an active-matrix display, individual pixels are typically addressed by integrated nonlinear active elements such as transistors (e.g., thin-film transistors "TFTs"), while in the case of a passive-matrix display, they are typically addressed by multiplexing methods as known in the art.

[0027] PSA displays also include alignment layers on one or both substrates forming the display housing. The alignment layer is typically applied to electrodes (where such electrodes are located) to bring them into contact with the LC dielectric and induce the initial alignment of LC molecules. The alignment layer may also contain or be composed of, for example, polyimide, which may be rubbed or prepared by photoalignment.

[0028] Especially for monitors and particularly TV applications, there is a continuous demand for optimization of LCD response time, as well as contrast and brightness (and therefore transmittance). The PSA method can provide a key advantage in this regard. In particular, in the case of PS-VA, PS-IPS, PS-FFS, and PS-positive-VA displays, a reduction in response time related to pre-tilt, which can be measured in the test chamber, can be achieved without significantly detrimental effects on other parameters.

[0029] This invention is based on the objective of providing novel suitable materials for LC media optionally containing reactive mesomorphic (RM) crystals in displays, which do not have, or have to a lesser extent have, the disadvantages indicated above. In particular, there remains a need in the art for liquid crystal media with high reliability.

[0030] In addition, the objective of this invention is to provide alternative media to existing media known to those skilled in the art, thereby broadening the range of available materials and allowing for more specific optimization of a particular display.

[0031] A particular problem arises when a display requires exceptionally high contrast, because high contrast necessitates a low elastic constant for scattering, which can lead to a slower response time. The objective of this invention is to provide a liquid crystal medium with a faster response time.

[0032] These objectives have been achieved according to the present invention by means of materials and methods as described herein. In particular, it has been unexpectedly discovered that the advantageous effects mentioned above can be achieved using a liquid crystal substrate as described below.

[0033] This invention relates to a liquid crystal medium comprising one or more compounds of formula I.

[0034]

[0035] in

[0036] R 11 R 12 The same or different representations of H or straight-chain or branched alkyl groups having 1 to 15 C atoms, wherein one or more CH2 groups among these groups can be independently generated such that the O atoms are not directly connected to each other. The following substitutions are allowed: -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0037] Y represents H or CH3, preferably H.

[0038] p is 0 or 1, preferably 1, and

[0039] One or more compounds of formula II

[0040]

[0041] in

[0042] R 11 and R 12Each of these groups independently represents H, an alkyl or alkoxy group having 1 to 15 carbon atoms, wherein one or more CH2 groups among these groups can be independently generated in a manner in which the O atoms are not directly connected to each other. The following substitutions are allowed: -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0043] A 1 Each occurrence is represented independently.

[0044] a) 1,4-cyclohexeneyl or 1,4-cyclohexeneyl, wherein one or both non-adjacent CH2 groups may be substituted with -O- or -S-.

[0045] b) 1,4-Phenylidene, wherein one or both CH groups may be substituted with N, or

[0046] c) Groups derived from the groups spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo-[2.2.2]octyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl, and fluorene-2,7-diyl.

[0047] Groups a), b), and c) may be substituted with methyl, ethyl, and / or halogen atoms, preferably with fluorine mono- or poly-substituted groups.

[0048] n can be 0, 1, or 2, preferably 0 or 1.

[0049] Z 1 Each occurrence independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond, and

[0050] L 11 and L 12 Each of them independently represents H, F, Cl, CF3 or CHF2, preferably F, and

[0051] W represents O or S, preferably S.

[0052] Compounds of Formula I are described, for example, in US 2017 / 022415 A1 and US 2016 / 0002532 A1. Compounds of Formula II are described, for example, in EP 3 628 721 A1.

[0053] Surprisingly, by using compound of formula I and one or more compounds of formula II in the medium, a significantly shorter response time parameter γ1 / K1 can be achieved, which results in faster switching of the display containing the medium, while the contrast of the display is not negatively affected, and is even improved.

[0054] Preferably, the medium comprises one or more compounds of formula I wherein p is 0 and one or more compounds of formula I wherein p is 1.

[0055] Preferably, the medium comprises one or more compounds of formula I-1 and / or one or more compounds of formula I-2:

[0056]

[0057] Among them, Y and R 11 and R 12 It has the meaning given above for Equation I, and R 11 In each case, preferably, it represents an optionally fluorinated alkyl or alkoxy or alkenyl or alkenyloxy group having at most 7 carbon atoms, or a cycloalkyl or cycloalkoxy group having 3 to 5 carbon atoms, or a cycloalkylalkyl or cycloalkylalkoxy group having 3 to 7 carbon atoms, and R 12 Preferably, in each case, it refers to an alkyl or alkenyl group having at most 7 carbon atoms, or a cycloalkyl group having 3 to 5 carbon atoms, or a cycloalkylalkyl group having 3 to 7 carbon atoms, which are optionally fluorinated.

[0058] Preferred compounds of formula I-1 are selected from the following sub-formulas:

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] Where R 12 Having the meaning given above and preferably referring to an alkyl group having 1 to 5 carbon atoms.

[0066] The most preferred compounds of formula I-1 are compounds I-1-1 to I-1-17, and especially preferred are I-1-1 to I-1-7.

[0067] Preferred compounds of formula I-2 are selected from the following sub-formulas:

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] Where R 12 Having the meaning given above and preferably referring to an alkyl group having 1 to 5 carbon atoms.

[0075] The most preferred compounds of formula I-2 are compounds I-2-1 to I-2-17, especially I-2-1 to I-2-7.

[0076] Preferably, the medium comprises one or more compounds of formula II above, wherein W represents S and n is 0.

[0077] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula II-1 and / or II-2.

[0078]

[0079] The groups present therein have the same meaning as those given above according to Formula II, and preferably

[0080] R 11 and R 12 Each of these elements independently represents an alkyl, alkenyl, or alkoxy group having up to 15 carbon atoms; more preferably, one or both of these elements represent an alkoxy group.

[0081] L 11 and L 12 Each is preferably represented by F.

[0082] In a preferred embodiment, the medium comprises one or more compounds of formula II-1 selected from the group consisting of compounds of formula II-1-1 to II-1-10, preferably formula II-1-6.

[0083]

[0084]

[0085] Wherein alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl* each independently represent a straight-chain alkenyl group having 2 to 6 carbon atoms, alkoxy and alkoxy* each independently represent a straight-chain alkoxy group having 1 to 6 carbon atoms, and L 11 and L 12 Each can be represented independently as F or Cl, with F being the preferred choice.

[0086] In a preferred embodiment, the medium comprises one or more compounds of formula II-2 selected from the group consisting of compounds of formula II-2-1 to II-2-10, preferably formula II-2-6.

[0087]

[0088]

[0089] Wherein alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl* each independently represent a straight-chain alkenyl group having 2 to 6 carbon atoms, alkoxy and alkoxy* each independently represent a straight-chain alkoxy group having 1 to 6 carbon atoms, and L 1 and L 2 Each can be represented independently as F or Cl, with F being the preferred choice.

[0090] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula IIA-1 and / or IIA-2.

[0091]

[0092]

[0093] Where L 11 and L 12 It has the same meaning as given by Equation II.

[0094] m and n are the same or different, being 0, 1, 2, 3, 4, 5, or 6, preferably 1, 2, or 3, and most preferably 1. (O) represents O or a single bond.

[0095] Cy represents a cyclic aliphatic group having 3, 4 or 5 ring atoms, which is optionally substituted with an alkyl or alkenyl group each having up to 3 C atoms or with a halogen or CN, and preferably represents cyclopropyl, cyclobutyl or cyclopentyl.

[0096] The medium contains compounds of formula IIA-1 and / or IIA-2, other than or in addition to compounds of formula II, preferably other than compounds of formula II.

[0097] The most preferred compounds of formulas IIA-1 and IIA-2 are as follows:

[0098]

[0099] Here, alkoxy represents a straight-chain alkoxy group having 1 to 6 carbon atoms.

[0100] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula II-3.

[0101]

[0102] in

[0103] R 11 R 12 The same or different groups represent H or alkyl or alkoxy groups having 1 to 15 C atoms, wherein one or more CH2 groups of these groups are optionally arranged independently of each other such that the O atoms are not directly connected to each other. C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO- can be substituted, and in addition, one or more H atoms can be substituted by halogens.

[0104] In Equation II-3, R 11 Preferably, it refers to an alkyl, alkenyl, or alkoxy group having up to 7 carbon atoms, or a cycloalkyl group having 3 to 5 carbon atoms, or an alkyl group having 1 to 3 alkyl carbon atoms (C3 to C5 cycloalkyl) group.

[0105] In Equation II-3, R 11 Preferably, it represents an alkoxy group having up to 7 carbon atoms, or a cycloalkoxy group having 3 to 5 carbon atoms, or a (C3 to C5 cycloalkyl) alkoxy group having 1 to 3 alkyl carbon atoms.

[0106] Compounds of formula II-3 are preferably selected from the group consisting of compounds of formulas II-3-1 to II-3-11:

[0107]

[0108]

[0109]

[0110] Where R 12The alkyl group having 1 to 7 carbon atoms is preferred to be ethyl, n-propyl or n-butyl, or cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl.

[0111] In a preferred embodiment of the invention, the medium comprises one or more compounds of formulas II-4 to II-6, preferably formula II-5.

[0112]

[0113] The parameters have the meanings given above, R 11 Preferably, it represents a straight-chain alkyl group, and R 12 Preferably, alkoxy groups have 1 to 7 carbon atoms.

[0114] In a preferred embodiment, the medium comprises one or more compounds of formula II selected from the group consisting of compounds of formula II-7 to II-9, preferably formula II-8.

[0115]

[0116] Where R 11 and R 12 With the meaning given above, R 11 Preferably, it represents a straight-chain alkyl group, and R 12 Preferably, alkoxy groups are represented, each having 1 to 7 carbon atoms.

[0117] Preferably, the medium according to the invention comprises one or more compounds selected from the group consisting of compounds of formulas IIIA, IIIB, IIIC, IIID, and IIIE.

[0118]

[0119] in

[0120] R 2A R 2B R 2C R 2D and R 2E Each group independently represents H, an alkyl or alkenyl group having up to 15 carbon atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more CH2 groups in these groups can be connected in a manner such that the O atoms are not directly connected to each other via -O-, -S-, Replace with -C≡C-, -CF₂O-, -OCF₂-, -OC-O-, or -O-CO-.

[0121] express

[0122]

[0123] Preferred

[0124]

[0125] L 1 To L 4 Each can be independently represented as F, Cl, CF3, or CHF2.

[0126] Y may represent H, F, Cl, CF3, CHF2, or CH3, preferably H or CH3, and very preferably H.

[0127] Z 2A Each of these independently represents a single bond, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-.

[0128] Z 2 Z 2B and Z 2D Each of these independently represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-.

[0129] p represents 0, 1, or 2.

[0130] q represents 0 or 1, and

[0131] v represents 1, 2, 3, 4, 5, or 6.

[0132] In compounds of formulas IIIA, IIIB, and IIID, Z 2 They can have the same or different meanings. In compounds of formula IIIB, Z 2 and Z 2B They can have the same or different meanings. In compounds of formula IIID, Z 2 and Z 2D They can have the same or different meanings.

[0133] In compounds of formulas IIIA, IIIB, IIIC, IIID, and IIIE, R 2A R 2B R 2C R 2D and R 2EEach preferably represents an alkyl group having 1 to 6 carbon atoms, particularly CH3, C2H5, n-C3H7, n-C4H9, and n-C5H. 11 .

[0134] In compounds of formulas IIIA, IIIB, and IIID, L 1 L 2 L 3 and L 4 Preferably, L represents 1 =L 2 =F and L 3 =L 4 =F, in addition, 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 =F. Z in equations IIIA and IIIB 2 and Z 2B Preferably, each represents a single bond independently of the others; otherwise, it is a -C2H4- bridge.

[0135] If in equation IIIB, if Z 2 =-C2H4- or -CH2O-, then Z 2B Preferably a single bond, or if Z 2B =-C2H4- or -CH2O-, then Z 2 Single bonds are preferred.

[0136] In Equation IIID, Z 2D Single bonds are preferred.

[0137] In compounds of formulas IIIA, IIIB, and IIID, (O)C v H 2v+1 Preferably, OC is represented. v H 2v+1 In compounds of formula IIIC, (O)C v H 2v+1 Preferably, C v H 2v+1 .

[0138] In compounds of formula IIIC, L 3 and L 4 Preferably, each represents F.

[0139] The preferred compounds of formulas IIIA, IIIB, IIIC, and IIID are indicated below:

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] The parameter represents 1 or 2. alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 carbon atoms. cycloalkyl represents cyclopropyl, cyclobutyl, cyclopentyl, or cyclopentenyl. alkenyl represents a straight-chain 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-.

[0151] The mixtures according to the invention are particularly preferred to comprise one or more compounds of the formulas IIIA-2, IIIA-8, IIIA-10, IIIA-16, II-18, IIIA-40, IIIA-41, IIIA-42, IIIA-43, IIIB-2, IIIB-10, IIIB-16, IIIC-1, IIID-4 and IIIE-1.

[0152] The proportion of compounds of formula IIIA and / or IIIB in the overall mixture is preferably at least 20% by weight.

[0153] A particularly preferred medium of the present invention comprises at least one compound of formula IIC-1.

[0154]

[0155] Wherein alkyl and alkyl* have the meaning indicated above, preferably in an amount of >3% by weight, particularly >5% by weight and especially preferably 5 to 25% by weight.

[0156] In a preferred embodiment, the medium comprises one or more compounds of formula IV.

[0157]

[0158] in

[0159] R 41 This indicates an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably a n-alkyl group, and particularly preferably having 2, 3, 4 or 5 carbon atoms.

[0160] R 42 The term refers to 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 vinyl or 1-propenyl and especially vinyl.

[0161] Compounds of formula IV are preferably selected from the group consisting of compounds of formulas IV-1 to IV-4:

[0162]

[0163] in

[0164] alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably having 2 to 5 carbon atoms.

[0165] alkenyl indicates an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms.

[0166] 'alkenyl' indicates an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms.

[0167] alkoxy means an alkoxy group having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0168] Preferably, the medium comprises one or more compounds selected from the group consisting of compounds of formula IV-1-1 to IV-1-4.

[0169]

[0170]

[0171] Very preferably, the medium according to the invention comprises one or more compounds of formula IV-2-1 and / or IV-2-2.

[0172]

[0173] Most preferably, the medium according to the invention comprises a compound of formula IV-3, particularly compounds selected from formulas IV-3-1 to IV-3-5.

[0174]

[0175]

[0176] Most preferably, the medium according to the invention comprises a compound of formula IV-4, particularly compounds selected from formulas IV-4-1 and IV-4-2.

[0177]

[0178] The liquid crystal medium preferably further comprises one or more compounds of formula IVa.

[0179]

[0180] in

[0181] R 41 and R 42 Each of these independently represents a straight-chain alkyl, alkenyl, alkoxyalkyl, or alkoxy group having at most 12 carbon atoms. express or

[0182] Z 4 The following are represented as single bonds: -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, and -CF=CF-.

[0183] Preferred compounds of formula IVa are indicated below:

[0184]

[0185]

[0186] in

[0187] alkyl and

[0188] Alkyl* each independently represents a straight-chain alkyl group having 1 to 6 carbon atoms.

[0189] The medium according to the invention preferably comprises at least one compound of formula IVa-1 and / or formula IVa-2.

[0190] The proportion of the IVa compound in the overall mixture is preferably at least 5% by weight.

[0191] Preferably, the medium comprises one or more compounds of formula IVb-1 to IVb-3.

[0192]

[0193] in

[0194] alkyl and alkyl* each independently represent straight-chain alkyl groups having 1 to 6 carbon atoms, and

[0195] alkenyl and alkenyl* each independently represent straight-chain alkenyl groups having 2 to 6 carbon atoms.

[0196] The proportion of biphenyls of formulas IV-1 to IV-3 in the overall mixture is preferably at least 3% by weight, and particularly ≥5% by weight.

[0197] Of the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0198] Biphenyl is particularly preferred.

[0199]

[0200]

[0201] Wherein alkyl* represents an alkyl group having 1 to 6 carbon atoms, and preferably represents n-propyl. The media according to the invention particularly preferably comprise one or more compounds of formula IVb-1-1 and / or IVb-2-3.

[0202] In a preferred embodiment, the medium comprises one or more compounds of formula V.

[0203]

[0204] in

[0205] R 51 and R 52 Independent of each other, having a target for R 41 and R 42One of the given meanings, and preferably, refers to an alkyl group having 1 to 7 carbon atoms, preferably a n-alkyl group, and particularly preferably a n-alkyl group having 1 to 5 carbon atoms; an alkoxy group having 1 to 7 carbon atoms, preferably a n-alkoxy group, and particularly preferably a n-alkoxy group having 2 to 5 carbon atoms; or an alkoxyalkyl group, alkenyl group, or alkenyloxy group having 2 to 7 carbon atoms, preferably 2 to 4 carbon atoms, preferably an alkenyloxy group.

[0206] Same or different

[0207]

[0208]

[0209] in

[0210] Preferred representation

[0211] Z 51 Z 52 Each of these elements independently represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond, preferably -CH2-CH2-, -CH2-O-, or a single bond, and especially preferably a single bond.

[0212] n is 1 or 2.

[0213] Compounds of formula V are preferably selected from compounds of formulas V-1 to V-16:

[0214]

[0215]

[0216] Where R 1 and R 2 With the above for R 2A The meaning indicated. R 1 and R 2 Preferably, each represents a straight-chain alkyl or alkenyl group independently of the other.

[0217] The preferred medium comprises one or more compounds of formula V-1, V-3, V-4, V-6, V-7, V-10, V-11, V-12, V-14, V-15 and / or V-16.

[0218] The mixtures according to the invention very particularly preferably contain compounds of formula V-10, V-12, V-16 and / or IV-1, especially in amounts of 5 to 30%.

[0219] Preferred compounds of formula V-10 are indicated as follows:

[0220]

[0221] The medium according to the invention particularly preferably comprises a tricyclic compound of formula V-10a and / or formula V-10b and one or more bicyclic compounds of formula IV-1. The total proportion of the compounds of formula V-10a and / or V-10b and one or more bicyclohexyl compounds selected from formula IV-1 is 5 to 40%, very particularly preferably 15 to 35%.

[0222] The most particularly preferred mixture contains compounds V-10a and CC-2-3

[0223]

[0224] Based on the overall mixture, compounds V-10a and IV-1-1 are preferably present in the mixture at a concentration of 15 to 35%, particularly preferably 17 to 25%, and especially preferably 18 to 22%.

[0225] A very particularly preferred mixture comprises compounds V-10b and IV-1-1:

[0226]

[0227] Based on the overall mixture, compounds V-10b and IV-1-1 are preferably present in the mixture at a concentration of 15 to 35%, particularly preferably 17 to 25%, and especially preferably 18 to 22%.

[0228] The most particularly preferred mixture contains the following three compounds:

[0229]

[0230] Based on the overall mixture, compounds V-10a, V-10b and IV-1-1 are preferably present in the mixture at a concentration of 15 to 35%, particularly preferably 15 to 25%, and especially preferably 18 to 22%.

[0231] The preferred mixture comprises at least one compound selected from the group consisting of compounds V-6, V-7 and IV-1:

[0232]

[0233]

[0234] Where R 41 and R 42 and R 51 and R 52 It has the meaning indicated above. Preferably, in compounds V-6, V-7, and IV-1, R41 and R 51 These represent alkyl or alkenyl groups having 1 to 6 or 2 to 6 carbon atoms, respectively, and R 42 and R 52 This indicates an alkenyl group having 2 to 6 carbon atoms.

[0235] The preferred mixture comprises at least one compound of the formulas V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a, and IV-3b:

[0236]

[0237]

[0238] Where alkyl represents an alkyl group having 1 to 6 carbon atoms, and alkenyl represents an alkenyl group having 2 to 6 carbon atoms.

[0239] The compounds of formulas V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a and IV-3b are preferably present in the mixtures according to the invention in an amount of 1 to 40% by weight, preferably 5 to 35% by weight and very particularly preferably 10 to 30% by weight.

[0240] In a preferred embodiment, the medium comprises one or more Va compounds.

[0241]

[0242] in

[0243] R L Represents H, a straight-chain or branched alkyl or alkoxy group having 1 to 15 C atoms, wherein one or more CH2 groups of these groups can be independently coupled to each other in a manner in which the O atoms are not directly connected to each other. The following substitutions are allowed: -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0244] X L This indicates that F, Cl, CN, CHF2, CF3, OCF3, or have the same or different R L One of the meanings, and

[0245] Y L It represents H, F, Cl, or CH3.

[0246] Compounds of formula Va are preferably selected from the group consisting of compounds of formula Va-1 and Va-2:

[0247]

[0248] in

[0249] R L1 It has the meaning given above for Formula I, and preferably represents an alkyl or alkenyl group having 1 to 7 C atoms, wherein the CH2 group may be replaced by a cyclopropane-1,2-diyl group.

[0250] In a preferred embodiment, the medium comprises one or more Vb compounds selected from the following formulas:

[0251]

[0252] Where R L1 It has the meaning given above for the expression Va.

[0253] Very preferably, the medium comprises compound Vb-2, wherein R L1 This indicates an alkyl or alkenyl group having up to 7 carbon atoms, particularly a vinyl group.

[0254] In a preferred embodiment of the invention, the medium further comprises one or more compounds of formulas VI-1 to VI-9.

[0255]

[0256]

[0257] in

[0258] R 7 Each group independently represents H, an alkyl or alkenyl group having up to 15 carbon atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more CH2 groups in these groups can be connected in a manner such that the O atoms are not directly connected to each other via -O-, -S-, Replace with -C≡C-, -CF₂O-, -OCF₂-, -OC-O-, or -O-CO-.

[0259] ,and

[0260] w and x each represent 1 to 6 independently.

[0261] A mixture comprising at least one compound of formula VI-9 is particularly preferred.

[0262] In a preferred embodiment of the invention, the medium further comprises one or more compounds of formulas VII-1 to VII-21.

[0263]

[0264]

[0265]

[0266] in

[0267] R represents a straight-chain alkyl or alkoxy group having 1 to 6 C atoms, (O) represents -O- or a single bond, and m is 0, 1, 2, 3, 4, 5 or 6, and n is 0, 1, 2, 3 or 4.

[0268] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0269] The medium according to the invention preferably contains 2 to 30% by weight, particularly 5 to 20% by weight, of terphenyl of formula VII-1 to VII-21.

[0270] Particularly preferred are compounds of formulas VII-1, VII-2, VII-4, VII-20, and VII-21. In these compounds, R preferably represents an alkyl group, or an alkoxy group, each having 1 to 5 carbon atoms. In compounds of formula VII-20, R preferably represents an alkyl or alkenyl group, particularly an alkyl group. In compounds of formula VII-21, R preferably represents an alkyl group.

[0271] If the Δn value of the mixture is ≥0.1, then terphenyl is preferably used in the mixture according to the invention. A preferred mixture contains 2 to 20% by weight of one or more terphenyl compounds selected from the group consisting of compounds VII-1 to VII-21.

[0272] A more preferred implementation scheme is listed below:

[0273] a) A liquid crystal medium comprising at least one compound of formula Z-1 to Z-7,

[0274]

[0275]

[0276] Where R and alkyl have the meanings indicated above for formula II.

[0277] b) The preferred liquid crystal medium according to the invention comprises one or more substances containing tetrahydronaphthyl or naphthyl units, such as, for example, compounds of formulas N-1 to N-5.

[0278]

[0279]

[0280] Where R 1N and R 2N Each has its own independent characteristics targeting R. 2A The indicated meaning preferably represents a straight-chain alkyl, a straight-chain alkoxy, or a straight-chain alkenyl group, and

[0281] Z 1 and Z 2 Each of these can be represented independently as -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CH2-, or a single bond.

[0282] c) Preferred mixtures comprise one or more compounds selected from the group consisting of difluorodibenzo-chromium compounds of formula BC, chromium compounds of formula CR, fluorinated phenanthrenes of formulas PH-1 and PH-2, and fluorinated dibenzofurans of formulas BF-1 and BF-2.

[0283]

[0284] in

[0285] R B1 R B2 R CR1 R CR2 R 1 R 2 Each has its own R independently 2A The meaning of . c is 0, 1, or 2, and d represents 1 or 2. R 1 and R 2 Preferably, each represents an alkyl or alkoxy group having 1 to 6 carbon atoms independently. Compounds of formula BF-1 and BF-2 should not be equivalent to one or more compounds of formula I.

[0286] The mixture according to the invention preferably contains, in an amount of 3 to 20% by weight, particularly 5 to 15% by weight, a compound of the formula BC, CR, PH-1, PH-2 and / or BF.

[0287] Especially preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5.

[0288]

[0289]

[0290] in

[0291] alkyl and alkyl* each independently represent straight-chain alkyl groups having 1 to 6 carbon atoms, and

[0292] alkenyl and alkenyl* each independently represent straight-chain alkenyl groups having 2 to 6 carbon atoms.

[0293] Very particularly preferred are mixtures comprising one, two or three BC-2 compounds.

[0294] d) Preferred mixtures comprise one or more indene compounds of the formula In.

[0295]

[0296] in

[0297] R 11 R 12 R 13 Each of these groups independently represents a straight-chain alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1 to 6 carbon atoms.

[0298] R 12 and R 13 Additionally, halogen is preferred, especially F.

[0299]

[0300] i can be 0, 1, or 2.

[0301] Preferred In compounds are those of formulas In-1 to In-16 as indicated below:

[0302]

[0303]

[0304]

[0305] Compounds of formulas In-1, In-2, In-3 and In-4 are particularly preferred.

[0306] Compounds of formula In and its sub-formulas In-1 to In-16 are preferably used in mixtures according to the invention at a concentration of ≥5% by weight, particularly 7 to 30% by weight and very particularly preferably 10 to 25% by weight.

[0307] e) Preferred mixtures further comprise one or more compounds of formulas L-1 to L-11.

[0308] in

[0309] R and R1 Each independently possesses the properties of R in Equation IIIA above. 2A The meaning indicated is as follows, and alkyl refers to an alkyl group having 1 to 6 carbon atoms. The parameter s indicates 1 or 2.

[0310] Compounds of formula L-1 to L-5 are preferably used at concentrations of 5 to 50% by weight, particularly 8 to 40% by weight, and very especially preferably 10 to 40% by weight.

[0311] e) The preferred mixture further comprises one or more compounds of formula Y.

[0312]

[0313] Where R 11 and R 12 It has one of the meanings given in Equation I above, and L 1 and L 2 F or Cl can be represented in the same or different ways.

[0314] The preferred compound of formula Y is selected from the group consisting of the following formulas:

[0315]

[0316]

[0317] Wherein, Alkyl and Alkyl* each independently represent a straight-chain alkyl group having 1 to 6 carbon atoms, Alkoxy represents a straight-chain alkoxy group having 1 to 6 carbon atoms, Alkenyl and Alkenyl* each independently represent a straight-chain alkenyl group having 2 to 6 carbon atoms, and O represents an oxygen atom or a single bond. Alkenyl and Alkenyl* preferably represent 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-.

[0318] The preferred Y-type compound is selected from the group consisting of the following formulas:

[0319]

[0320] Alkoxy and Alkoxy* have the meanings defined above, and preferably represent methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0321] The liquid crystal medium according to the invention, also referred to herein as a liquid crystal host mixture, is suitable for use in polymer-stabilized displays. For this purpose, the medium according to the invention optionally comprises one or more polymerizable compounds of formula P.

[0322] P-Sp-A 1 -(Z 1 -A 2 ) z -RP

[0323] Each group, independently of the others and in the same or different manner each time it appears, has the following meaning:

[0324] P is a polymerizable group.

[0325] Sp can be a spacer group or a single bond.

[0326] A 1 A 2 Preferably, the aromatic group, heteroaromatic group, alicyclic group, or heterocyclic group has 4 to 25 ring atoms, and may also contain a fused ring, and is unsubstituted or monosubstituted or polysubstituted.

[0327] Z 1 is -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH2-CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 -or a single key,

[0328] R 0 R 00 It is H or an alkyl group having 1 to 12 carbon atoms.

[0329] R is H, L, or P-Sp-.

[0330] L is F, Cl, -CN, P-Sp- or a straight-chain, branched or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2- groups are optionally substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- in such a manner that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are optionally substituted with P-Sp-, F or Cl.

[0331] z is 0, 1, 2, or 3.

[0332] n1 can be 1, 2, 3 or 4.

[0333] As used herein, the terms “active layer” and “switchable layer” refer to a layer in an electro-optic display, such as an LC display, comprising one or more molecules (e.g., LC molecules) having structural and optical anisotropy, which change their orientation when subjected to external stimuli such as an electric or magnetic field, resulting in a change in the layer’s transmittance to polarized or unpolarized light.

[0334] As used herein, the terms “tilt” and “tilt angle” should be understood to refer to the tilted orientation of LC molecules of the LC medium relative to the cell surface in an LC display (preferably a PSA display). The tilt angle here represents the average angle (<90°) between the longitudinal molecular axis (LC director) of the LC molecules and the outer plate parallel to the plane forming the LC cell. Lower tilt angle values ​​(i.e., larger deviations from 90°) correspond to larger tilts. Suitable methods for measuring the tilt angle are given in the embodiments. Unless otherwise indicated, the tilt angle values ​​disclosed above and below relate to this measurement method.

[0335] As used herein, the terms “reactive mesocrystalline” and “RM” should be understood to mean a compound comprising a mesocrystalline or liquid crystal framework and one or more functional groups attached thereto suitable for polymerization, and said functional groups are also referred to as “polymerizable groups” or “P”.

[0336] Unless otherwise stated, the term “polymerizable compound” as used herein should be understood as a polymerizable monomeric compound.

[0337] As used herein, the term “low molecular weight compound” should be understood to mean a monomeric compound and / or a compound not prepared by polymerization, as opposed to “polymeric compound” or “polymer”.

[0338] As used herein, the term "non-polymerizable compound" should be understood to mean a compound that does not contain functional groups suitable for polymerization under the conditions typically applied to RM polymerization.

[0339] As used herein, the term "mesocrystalline group" is known to those skilled in the art and described in the literature, and it refers to a group that substantially contributes to the formation of a liquid crystal (LC) phase in a low molecular weight or polymeric substance due to the anisotropy of its attractive and repulsive interactions. A compound containing a mesocrystalline group (mesocrystalline compound) does not necessarily have an LC phase by itself. Mesocrystalline compounds may also exhibit LC phase behavior only when mixed with other compounds and / or after polymerization. Typical mesocrystalline groups are, for example, rigid rod-shaped or disk-shaped units. The terms and definitions used in relation to mesocrystalline or LC compounds are given in Pure Appl. Chem. 2001, 73(5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368.

[0340] As used herein, the terms “optically active” and “chiral” are synonymous for materials that can induce helical pitch in nematic host materials, also known as “chiral dopants”.

[0341] As used herein, the term "spacer group" (hereinafter also referred to as "Sp") is known to those skilled in the art and described in the literature, see, for example, Pure Appl. Chem. 2001, 73(5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. As used herein, the term "spacer group" or "spacer base" means a flexible group, such as an alkylene group, attached to a mesocrystalline group or polymerizable group (one or more) in a polymerizable mesocrystalline compound.

[0342] In the context, It represents the trans-1,4-cyclohexyl ring.

[0343] In groups In the diagram, it is shown that the single bond between two ring atoms can be attached to any free position on the benzene ring.

[0344] In this context, "organic group" refers to a carbon or hydrocarbon group.

[0345] "Carbon group" refers to a monovalent or polyvalent organic group containing at least one carbon atom, wherein the group does not contain other atoms (e.g., -C≡C-) or optionally contains one or more other atoms, such as N, O, S, B, P, Si, Se, As, Te, or Ge (e.g., carbonyl group). The term "hydrocarbon group" refers to a carbon group that additionally contains one or more H atoms and optionally one or more heteroatoms, such as N, O, S, B, P, Si, Se, As, Te, or Ge.

[0346] "Halogen" means F, Cl, Br or I, with F or Cl preferred, and F being very preferred.

[0347] -CO-, -C(=O)-, and -C(O)- represent carbonyl groups, i.e.

[0348] The carbon or hydrocarbon group can be saturated or unsaturated. Unsaturated groups are, for example, aryl, alkenyl, or alkynyl groups. Carbon or hydrocarbon groups having more than 3 carbon atoms can be straight-chain, branched, and / or cyclic, and may also contain spirolinked or fused rings.

[0349] The terms "alkyl", "aryl", and "heteroaryl" also include polyvalent groups, such as alkylene, arylene, and heteroarylene.

[0350] The term "aryl" refers to an aromatic carbon group or a group derived therefrom. The term "heteroaryl" refers to an "aryl" group as defined above that contains one or more heteroatoms (preferably selected from N, O, S, Se, Te, Si, and Ge).

[0351] Preferred carbon and hydrocarbon groups are optionally substituted, and are straight-chain, branched, or cyclic alkyl, alkenyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyl, and alkoxy carbonyloxy groups having 1 to 40, preferably 1 to 20, very preferably 1 to 12 C atoms; optionally substituted aryl or aryloxy groups having 5 to 30, preferably 6 to 25 C atoms; or optionally substituted alkylaryl, aralkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy, and aryloxycarbonyloxy groups having 5 to 30, preferably 6 to 25 C atoms, wherein one or more C atoms may also be replaced by heteroatoms (preferably selected from N, O, S, Se, Te, Si, and Ge).

[0352] Further preferred carbon and hydrocarbon groups are C1-C. 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl group, C3-C 20 Allyl, C4-C 20 Alkyl diene group, C4-C 20 Polyene, C6-C 20 cycloalkyl, C4-C 15 Cycloalkenyl, C6-C 30 Aryl, C6-C 30 Alkyl aryl, C6-C 30 Aryl group, C6-C 30 Alkyl aryloxy, C6-C 30 arylalkoxy, C2-C 30 heteroaryl, C2-C 30heteroaryloxyl.

[0353] C1-C is particularly preferred. 12 Alkyl, C2-C 12 alkenyl, C2-C 12 alkynyl group, C6-C 25 Aryl and C2-C 25 Mixed aromatic compounds.

[0354] Further preferred carbonyl and hydrocarbon groups are straight-chain, branched, or cyclic alkyl groups having 1-20, preferably 1-12 C atoms, which are unsubstituted or mono- or polysubstituted with F, Cl, Br, I, or CN, and one or more non-adjacent CH2 groups may be independently converted to -C(R) x )=C(R x )-、-C≡-、-N(R x -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O- are used to replace O and / or S atoms in a way that prevents them from being directly connected to each other.

[0355] R x Preferably, it represents H, F, Cl, CN, a straight-chain, branched, or cyclic alkyl chain having 1 to 25 C atoms, wherein one or more non-adjacent C 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 it represents an optionally substituted aryl or aryloxy group having 6 to 30 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 30 C atoms.

[0356] Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecyl, trifluoromethyl, perfluoron-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, perfluorohexyl, etc.

[0357] Preferred alkenyl groups include, for example, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, etc.

[0358] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, penynyl, hexynyl, octyynyl, etc.

[0359] Preferred alkoxy groups include, for example, methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, etc.

[0360] Preferred amino groups include, for example, dimethylamino, methylamino, methylphenylamino, phenylamino, etc.

[0361] Aryl and heteroaryl groups can be monocyclic or polycyclic, meaning they can contain one ring (e.g., phenyl) or two or more rings, and can be fused (e.g., naphthyl) or covalently bonded (e.g., biphenyl), or a combination of fused and linking rings. Heteroaryl groups contain one or more heteroatoms, preferably selected from O, N, S, and Se.

[0362] Particularly preferred are mono-, di-, or tricyclic aryl groups having 6-25 carbon atoms and mono-, di-, or tricyclic heteroaryl groups having 5-25 ring atoms, optionally containing a fused ring and optionally substituted. Further preferred are 5-, 6-, or 7-membered aryl and heteroaryl groups, wherein one or more CH groups may be replaced by N, S, or O in such a manner that the O atoms and / or S atoms are not directly linked to each other.

[0363] Preferred aryl groups include, for example, phenyl, biphenyl, terphenyl, [1,1':3',1”]-terphenyl-2'-yl, naphthyl, anthracene, bidinaphthyl, phenanthryl, 9,10-dihydro-phenanthryl, pyrene, dihydropyrene, Dinaphthylbenzene, tetraphenylbenzene, pentaphenylbenzene, benzo[a]pyrene, fluorene, indene, indo[a]fluorene, spirobifluorene, etc.

[0364] Preferred heteroaryl groups are, for example, 5-membered rings, such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazolium, furan, thiophene, selenophene, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 6-membered rings, such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5-tetraazine, 1,2,3,4-tetraazine, 1,2,3,5-tetraazine, or fused groups, such as indole, isoindole, indole Azine, Indazole, Benzimidazole, Benzitriazole, Purine, Naphthemidazole, Phenylenazole, Pyridinazole, Pyrazinazole, Quinoxaline, Benzooxazole, Naphthemidazole, Anthrazooxazole, Phenylenazole, Isoxazole, Benzothiazolazole, Benzofuran, Isobenzofuran, Dibenzofuran, Quinoline, Isoquinoline, Pteridine, Benzo-5,6-quinoline, Benzo-6,7-quinoline, Benzo- 7,8-quinoline, benzoisoquinoline, acridine, phenothiazine, phenothiazine, benzopyridinium, quinoxaline, phenothiazine, naphthidine, azacarbazole, benzocarbine, phenanthridine, phenanthroxaline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithieno[2,3b]thiophene, isobenzo[2,3b]thiophene, dibenzo[2,3b]thiophene, benzo[2,3b]thiophene, benzo[2,3b]thiophene, di[2,3b]thiophene, isobenzo[2,3b]thiophene, dibenzo[2,3b]thiophene, ... or combinations thereof.

[0365] The aryl and heteroaryl groups mentioned in the context may also be substituted by alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl or other aryl or heteroaryl groups.

[0366] (Non-aromatic) alicyclic and heterocyclic groups can include both saturated rings (i.e., rings containing only single bonds) and partially unsaturated rings (i.e., those containing multiple bonds). Heterocyclic groups contain one or more heteroatoms, preferably selected from Si, O, N, S, and Se.

[0367] The (non-aromatic) alicyclic and heterocyclic groups can 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, mono-, bi-, or tricyclic groups having 5-25 ring atoms are preferred, optionally containing fused rings and optionally substituted. Further preferred are 5-, 6-, 7-, or 8-membered carbocyclic groups, wherein one or more C atoms may be replaced by Si and / or one or more CH groups may be replaced by N and / or one or more non-adjacent CH2 groups may be replaced by -O- and / or -S-.

[0368] Preferred alicyclic and heterocyclic groups are, for example, 5-membered groups, such as cyclopentane, tetrahydrofuran, tetrahydrothiophene, and pyrrolidine; 6-membered groups, such as cyclohexane, silinane, cyclohexene, tetrahydropyran, tetrahydrothioran, 1,3-dioxane, 1,3-dithiane, and piperidine; 7-membered groups, such as cycloheptane; and fused groups, such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, and octahydro-4,7-bridged methylene indane-2,5-diyl.

[0369] Preferred substituents are, for example, solubility-promoting groups, such as alkyl or alkoxy groups; electron-withdrawing groups, such as fluorine, nitro or nitrile groups; or substituents used to increase the glass transition temperature (Tg) of the polymer, especially bulky groups, such as tert-butyl or optionally substituted aryl groups.

[0370] Preferred substituents, hereinafter also referred to as "L" S ", 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 straight-chain or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy or alkoxy carbonyloxy having 1 to 25 C atoms, wherein one or more H atoms may optionally be replaced by F or Cl, an optionally substituted silyl having 1 to 20 Si atoms, or an optionally substituted aryl having 6 to 25, preferably 6 to 15 C atoms.

[0371] Where R x Represents H, F, Cl, CN, or a straight-chain, branched, or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2- groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are each optionally replaced by F, Cl, P-, or P-Sp-, and

[0372] Y 1 It represents halogens.

[0373] "Substituted silyl or aryl" preferably indicates that it is substituted with halogen, -CN, R 0 -OR 0 -CO-R 0 -CO-OR 0-O-CO-R 0 OR-O-CO-OR 0 Replace, where R 0 It represents H or an alkyl group having 1 to 20 carbon atoms.

[0374] Particularly preferred substituents L include, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and also phenyl.

[0375] A 1 and A 2 Very preferably means Where L has one of the meanings indicated above and r represents 0, 1, 2, 3 or 4, in particular

[0376] Preferred

[0377]

[0378] The polymerizable group P is a group suitable for polymerization reactions (e.g., free radical or ionic chain polymerization, addition polymerization, or condensation polymerization), or a group suitable for polymer-analogous reactions (e.g., addition or condensation on the polymer backbone). Groups suitable for chain polymerization are particularly preferred, especially those containing C=C double bonds or -C≡C- triple bonds, and groups suitable for ring-opening polymerization, such as oxobutyl or epoxy groups.

[0379] The preferred group P is selected from the group consisting of: CH2=CW 1 -CO-O-、CH2=CW 1 -CO-、 CH2=CW 2 -(O) k3 -、CW 1 =CH-CO-(O) k3 -、CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -、HS-CW 2 W 3 -、HW2 N-, HO-CW 2 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 - CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 Si-, where W 1 It represents H, F, Cl, CN, CF3, phenyl, or alkyl groups having 1 to 5 carbon atoms, especially H, F, Cl, or CH3, W 2 and W 3 Each independently represents H or an alkyl group having 1 to 5 carbon atoms, particularly H, methyl, ethyl, or n-propyl, W 4 W 5 and W 6 Each independently represents Cl, an oxaalkyl or oxacarbonylalkyl group having 1 to 5 carbon atoms, and W. 7 and W 8 Each of the above independently represents H, Cl or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene, which is optionally substituted by one or more groups L different from P-SP- as defined above, k1, k2 and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0380] The preferred group P is selected from the group consisting of: CH2=CW 1 -CO-O-、CH2=CW 1 -CO-、 CH2=CW 2 -O-、CH2=CW 2 -、CW 1 =CH-CO-(O) k3 -、CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2- CH2=CH-(CO) k1 -Phe-(O) k2 - Phe-CH=CH- and W 4 W 5 W 6 Si-, where W 1 It represents H, F, Cl, CN, CF3, phenyl, or alkyl groups having 1 to 5 carbon atoms, especially H, F, Cl, or CH3, W 2 and W 3 Each independently represents H or an alkyl group having 1 to 5 carbon atoms, particularly H, methyl, ethyl, or n-propyl, W 4 W 5 and W 6 Each independently represents Cl, an oxaalkyl or oxacarbonylalkyl group having 1 to 5 carbon atoms, and W. 7 and W 8 Each of them independently represents 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.

[0381] The most particularly preferred group P is selected from the group consisting of: CH2=CW 1 -CO-O-, especially CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, as well as CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-,

[0382] Other particularly preferred polymerizable groups P are selected from ethylene oxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxobutyl, and epoxy groups, with the most preferred groups being acrylate and methacrylate.

[0383] If the spacer group Sp is different from a single bond, it is preferably of the formula Sp"-X, such that each group P-Sp- is equivalent to the formula R-Sp"-X"-, wherein

[0384] "Sp" represents a straight-chain or branched alkylene group having 1 to 20, preferably 1 to 12, carbon atoms, optionally mono- or polysubstituted with F, Cl, Br, I, or CN, and wherein one or more non-adjacent CH2 groups are each independently substituted with -O-, -S-, -NH-, or -N(R) 0 )-、-Si(R 0 R 00)-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 -CO-O-、-O-CO-N(R) 0 )-、-N(R 0 )-CO-N(R 00 -, -CH=CH-, or -C≡C- are replaced by O and / or S atoms that are not directly connected to each other.

[0385] X" means -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-、-N(R 0 )-CO-、-N(R 0 )-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -、-CY 2 =CY 3 -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or single bonds

[0386] R 0 and R 00 Each independently represents H or an alkyl group having 1-20 carbon atoms, and

[0387] Y 2 and Y 3 Each can be represented independently as H, F, Cl, or CN.

[0388] X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, or -CO-NR. 0 -、-NR 0 -CO-、-NR 0 -CO-NR 00 - or a single key.

[0389] Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -O-CO-、-(CH2) p1 -CO-O-、-(CH2) p1 -O-CO-O-、-(CH2CH2O)q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR) 0 R 00 -O) p1 - where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 It has the meaning mentioned above.

[0390] The particularly preferred groups Sp and -Sp"-X"- are -(CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -O-CO-、-(CH2) p1 -CO-O-、-(CH2) p1 -O-CO-O-, where p1 and q1 have the meanings stated above.

[0391] The particularly preferred group Sp" in each case is a straight-chain ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methylimino-ethylene, 1-methylalkylene, vinylene, propenylene, and butenylene.

[0392] In a preferred embodiment of the invention, compounds of formula P and its subforms contain spacer groups Sp substituted with one or more polymerizable groups P, such that the group Sp-P corresponds to Sp(P). s s is ≥2 (branched polymerizable groups).

[0393] The preferred P compound according to this preferred embodiment is one in which s is 2, i.e., a compound containing the group Sp(P)2. The most preferred P compound according to this preferred embodiment contains a group selected from the following formulas:

[0394] -X-alkyl-CHPP S1

[0395] -X-alkyl-CH((CH2) aa P)((CH2) bb P) S2

[0396] -XN((CH2) aa P)((CH2) bb P) S3

[0397] -X-alkyl-CHP-CH2-CH2P S4

[0398] -X-alkyl-C(CH2P)(CH2P)-C aa H 2aa+1 S5

[0399] -X-alkyl-CHP-CH2P S6

[0400] -X-alkyl-CPP-C aa H 2aa+1 S7

[0401] -X-alkyl-CHPCHP-C aa H 2aa+1 S8

[0402] Where P is defined as in equation P.

[0403] Alkyl refers to a straight-chain or branched alkylene group with a single bond or 1 to 12 carbon atoms, which is unsubstituted or monosubstituted or polysubstituted with F, Cl or CN, and wherein one or more non-adjacent CH2 groups are each independently bonded to each other in such a manner that the O atom and / or S atom are not directly connected to each other via -C(R) 0 )=C(R 0 )-、-C≡C-、-N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- substitution, where R 0 It has the meaning indicated above.

[0404] aa and bb each independently represent 0, 1, 2, 3, 4, 5, or 6.

[0405] X has one of the meanings indicated by X", and is preferably O, CO, SO2, O-CO-, CO-O or a single bond.

[0406] The preferred spacer group Sp(P)2 is selected from formulas S1, S2 and S3.

[0407] The highly preferred spacer group Sp(P)2 is selected from the following formulas:

[0408] -CHPP S1a

[0409] -O-CHPP S1b

[0410] -CH2-CHPP S1c

[0411] -OCH2-CHPP S1d

[0412] -CH(CH2-P)(CH2-P) S2a

[0413] -OCH(CH2-P)(CH2-P) S2b

[0414] -CH2-CH(CH2-P)(CH2-P) S2c

[0415] -OCH2-CH(CH2-P)(CH2-P) S2d

[0416] -CO-NH((CH2)2P)((CH2)2P) S3a

[0417] In compounds of formula P and its sub-formulas as described above and below, P is preferably selected from the group consisting of: vinyloxy groups, acrylates, methacrylates, fluoroacrylates, chloroacrylates, oxetanes and epoxides, and most preferably selected from acrylates and methacrylates.

[0418] More preferably, compounds of formula P and its sub-formulas as described above and below, wherein all polymerizable groups P present in the compound have the same meaning, and very preferably represent acrylate or methacrylate, most preferably methacrylate.

[0419] In compounds of formula P and its sub-formulas as described above and below, R preferably represents P-Sp-.

[0420] More preferably, compounds of formula P and its derivatives as described above and below, wherein Sp represents a single bond or -(CH2). p1 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Where p1 is 2, 3, 4, 5 or 6, and if Sp is -O-(CH2) p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Then, the O-atom or CO-group is attached to the benzene ring, respectively.

[0421] More preferably, compounds of formula P and its sub-formulas as described above and below, wherein at least one Sp group is a single bond.

[0422] More preferably, compounds of formula P and its sub-formulas as described above and below, wherein at least one Sp group is different from a single bond and is preferably selected from -(CH2). p1 -、-O-(CH2) p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Where p1 is 2, 3, 4, 5 or 6, and if Sp is -O-(CH2)p1 -、-O-CO-(CH2) p1 Or -CO-O-(CH2) p1 Then, the O-atom or CO-group is attached to the benzene ring, respectively.

[0423] The highly preferred group -A in formula P 1 -(ZA 2 ) z -Selected from the following formula

[0424]

[0425] At least one benzene ring is substituted with at least one L group and the benzene ring is optionally further substituted with one or more L or P-Sp groups.

[0426] Preferred formula P and its sub-formula compounds are selected from the following preferred embodiments, including any combination thereof:

[0427] - All the P groups in this compound have the same meaning.

[0428] --A 1 -(ZA 2 ) z -Selected from formulas A1, A2, and A5,

[0429] - This compound happens to contain two polymerizable groups (represented by the group P).

[0430] - This compound contains exactly three polymerizable groups (represented by the group P).

[0431] -P is selected from the group consisting of acrylates, methacrylates, and oxetanes, with acrylates or methacrylates being particularly preferred.

[0432] -P stands for methacrylate.

[0433] - All Sp groups are single bonds.

[0434] - At least one of the Sp groups is a single bond and at least one of the Sp groups is different from a single bond.

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

[0436] -Sp represents a single bond or -(CH2). p2-、-(CH2) p2 -O-、-(CH2) p2 -CO-O-、-(CH2) p2 -O-CO-, where p2 is 2, 3, 4, 5 or 6, and the O atom or CO- group is attached to the benzene ring.

[0437] -R indicates P-Sp-,

[0438] -R does not indicate or contains a polymerizable group.

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

[0440] -L or L' indicates F, Cl, or CN.

[0441] -L is F.

[0442] Suitable and preferred compounds of formula P are selected from the following formula:

[0443]

[0444]

[0445]

[0446]

[0447] Each group has the following meaning:

[0448] P 1 P 2 and P 3 Each can be represented independently as an acrylate group or a methacrylate group.

[0449] Sp 1 Sp 2 and Sp 3 Each of these groups independently represents a single bond or a spacer group (having one of the meanings described in the context for Sp), and is particularly preferred to represent -(CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -CO-O-、-(CH2) p1 -O-CO- or -(CH2) p1-O-CO-O-, where p1 is an integer from 1 to 12, and furthermore, the group P 1 -Sp 1 -、P 2 -Sp 2 -and P 3 -Sp 3 One or more of - can represent R aa The condition is the presence of the group P. 1 -Sp 1 -、P 2 -Sp 2 -and P 3 -Sp 3 - at least one of them is different from R aa ,

[0450] R aa Represents H, F, Cl, CN, or a straight-chain or branched alkyl group having 1 to 25 C atoms, wherein one or more other non-adjacent CH2 groups may also be independently separated by C(R) 0 )=C(R 00 )-、-C≡C-、-N(R 0 -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O- can be substituted in such a way that the O and / or S atoms are not directly connected to each other, and one or more of the other H atoms can be replaced by F, Cl, CN or P. 1 -Sp 1 - Alternatively preferred are straight-chain or branched, optionally mono- or polyfluoroalkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy groups having 1 to 12 carbon atoms, wherein the alkenyl and alkynyl groups have at least two carbon atoms and the branched groups have at least three carbon atoms.

[0451] R 0 R 00 Each of these terms independently, and each instance may be identical or different, representing H or an alkyl group having 1 to 12 carbon atoms.

[0452] R y and R z Each can be independently represented as H, F, CH3, or CF3.

[0453] X 1 X 2 and X 3 Each can independently represent -CO-O-, -O-CO-, or a single bond.

[0454] Z 1 Represents -O-, -CO-, -C(R) y R z- or -CF2CF2-,

[0455] Z 2 and Z 3 Each can be independently represented as -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2). n - where n is 2, 3, or 4.

[0456] L, each time appearing, may represent F, Cl, CN, or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy group having 1 to 12 C atoms, preferably F.

[0457] L' and L” each independently represent H, F, or Cl.

[0458] k represents 0 or 1,

[0459] r represents 0, 1, 2, 3, or 4.

[0460] s represents 0, 1, 2, or 3.

[0461] t represents 0, 1, or 2.

[0462] x represents 0 or 1.

[0463] Compounds of formulas P2, P13, P17, P22, P23, P24, P30, P31 and P32 are particularly preferred.

[0464] More preferably are trireactive compounds P15 to P30, especially P17, P18, P19, P22, P23, P24, P25, P26, P30, P31 and P32.

[0465] In compounds from P1 to P32, the group

[0466] Preferred

[0467]

[0468] Wherein L has one of the meanings given above or below each time it appears, and is preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, OCH3, COCH3 or OCF3, especially F or CH3.

[0469] The medium according to the invention comprises one or more chiral dopants. Preferably, the absolute value of the helical twist force (HTP) of these chiral dopants is in the range of 1 μm. -1 Up to 150μm -1 Within the range, preferably within 10 μm -1 Up to 100μm -1 Within the range. In the case that the medium contains two or more chiral dopants, these may have opposite signs for their HTP values. For some specific embodiments, this condition is preferred because it allows for some compensation of the chirality of the corresponding compounds, and thus can be used to compensate for various temperature-dependent properties of the resulting medium in the apparatus. However, generally, it is preferred that most, preferably all, chiral compounds present in the medium according to the invention have the same sign for their HTP values.

[0470] Preferably, the chiral dopants present in the medium according to this application are mesocrystalline compounds, and most preferably they themselves exhibit a mesocrystalline phase.

[0471] In a preferred embodiment of the invention, the medium comprises two or more chiral compounds that all have the same algebraic symbol for HTP.

[0472] The temperature dependence of HTP on individual compounds can be high or low. The temperature dependence of the pitch of the medium can be compensated by mixing compounds with different HTP temperatures in appropriate ratios.

[0473] For optically active components, a wide range of chiral dopants can be used by those skilled in the art, some of which are commercially available, such as cholesterol nonanoate, R-811 and S-811, R-1011 and S-1011, R-2011 and S-2011, R-3011 and S-3011, R-4011 and S-4011, or CB15 (all from Merck KGaA, Darmstadt).

[0474] Particularly suitable dopants are compounds containing one or more chiral groups and one or more mesomorphic groups, or one or more aromatic or alicyclic groups that form mesomorphic groups with chiral groups.

[0475] Suitable chiral groups are, for example, chiral branched hydrocarbon groups, chiral ethylene glycol, binaphthol, or dioxolane, and are also selected from mono- or polyvalent chiral groups such as sugar derivatives, sugar alcohols, sugar acids, lactic acids, chiral substituted diols, steroid derivatives, terpene derivatives, amino acids, or sequences of several (preferably 1 to 5) amino acids.

[0476] Preferred chiral groups are sugar derivatives, such as glucose, mannose, galactose, fructose, arabinose, and dextrose; sugar alcohols, such as sorbitol, mannitol, idoteol, galactitol, or their dehydrated derivatives, particularly disohydrated hexotols, such as disohydrated sorbitol (1,4:3,6-disohydrated-D-sorbitol, isosorbitol), disohydrated mannitol (isosorbitol), or disohydrated idoteol (isoidoteol); sugar acids, such as gluconic acid, gulonic acid, and ketogulonic acid; chiral substituted glycol groups, such as mono- or oligomeric polyethylene glycol or propylene glycol, wherein one or more CH2 groups are substituted with alkyl or alkoxy groups; and amino acids, such as alanine, valine, and phenylglycerol. A sequence of amino acids or phenylalanine or 1 to 5 of these amino acids; a steroid derivative, such as a cholesterol group or a bile acid group; a terpene derivative, such as menthol, neomenthol, campheyl, pineneyl, terpineyl, isolongifolyl, flavone, carreyl, myrthenyl, nopyl, geraniyl, linaloyl, neryl, citronellyl, or dihydrocitronellyl.

[0477] The medium according to the invention preferably comprises a chiral dopant selected from the group of known chiral dopants. Suitable chiral groups and mesocrystalline chiral compounds are described, for example, in DE 34 25 503, DE 35 34 777, DE 35 34 778, DE 35 34 779 and DE 35 34 780, DE 43 42 280, EP 01 038 941 and DE 195 41 820. Examples are also compounds listed in Table F below.

[0478] Preferably, the chiral compounds used according to the present invention are selected from the group consisting of the formulas shown below.

[0479] Chiral dopants selected from the group consisting of compounds of the following formulas: Al to A-III and A-Ch are particularly preferred.

[0480]

[0481] in

[0482] R a11 R a12 and R b12 Each of the above can independently represent an alkyl group having 1-15 carbon atoms, wherein, in addition, one or more non-adjacent CH2 groups can each be independently represented by -C(R) z )=C(R z -, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- are substituted in such a way that the O and / or S atoms are not directly connected to each other, and wherein, in addition, one or more H atoms may be substituted by F, Cl, Br, I or CN, preferably alkyl, more preferably n-alkyl, provided that R a12 With R b12 different

[0483] R a21 and R a22 Each of the above can independently represent an alkyl group having 1-15 carbon atoms, wherein, in addition, one or more non-adjacent CH2 groups can each be independently represented by -C(R) z )=C(R z -, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- are substituted in such a way that the O and / or S atoms are not directly connected to each other, and wherein, in addition, one or more H atoms can be replaced by F, Cl, Br, I or CN, preferably both being alkyl, more preferably n-alkyl.

[0484] R a31 R a32 and R b32 Each of the above independently represents an alkyl group having a straight chain and branches of 1-15 C atoms, wherein, in addition, one or more non-adjacent CH2 groups may each be independently represented by -C(R) z )=C(R z -, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- are substituted in such a way that the O and / or S atoms are not directly connected to each other, and wherein, in addition, one or more H atoms can be substituted by F, Cl, Br, I, or CN.

[0485] Alkyl groups are preferred, and n-alkyl groups are more preferred, provided that R a32 With R b32 different,

[0486] R z It can be represented by H, CH3, F, Cl, or CN, with H or F being preferred.

[0487] R 8 With the R given above a11 One meaning is that alkyl is preferred, and more preferably a n-alkyl group having 1-15 carbon atoms.

[0488] Z 8 It represents -C(O)O-, -CH2O-, -CF2O- or a single bond, preferably -C(O)O-.

[0489] A 11 As shown in text A 12 Defined, or alternatively represented

[0490]

[0491] A 12 express

[0492]

[0493] Preferred

[0494]

[0495] in

[0496] L 12 Each occurrence independently represents a halogen, CN, or an alkyl, alkenyl, alkoxy, or alkenyloxy group having up to 12 carbon atoms, and one or more H atoms are optionally replaced by a halogen, preferably methyl, ethyl, Cl, or F, with F being particularly preferred.

[0497] A 21 express

[0498]

[0499] A 22 With targeting A 12 The meaning given

[0500] A 31 With targeting A 11 The given meaning, or alternative representation

[0501]

[0502] A 32 With targeting A 12 The meaning given.

[0503] n2 is 0, 1, or 2 each time it appears, and n3 is 1, 2, or 3, and...

[0504] r can be 0, 1, 2, 3, or 4.

[0505] Dopants selected from the group consisting of compounds of the following formula are particularly preferred:

[0506]

[0507]

[0508] in

[0509] Each time m appears, it is either the same or different integer from 1 to 9.

[0510] n is an integer from 2 to 9 each time it appears.

[0511] The preferred compound of formula A is the compound of formula A-III.

[0512] Further preferred dopants are derivatives of isosorbide, isomannitol, or isoadurel of formula A-IV:

[0513]

[0514] Among them, groups yes

[0515] (desaturated sorbitol),

[0516] (Disohydrated mannitol), or

[0517] (disohydrated idutol),

[0518] The preferred option is dehydrosorbitol.

[0519] And chiral ethylene glycols, such as diphenylethylene glycol (hydrogenated benzoin), especially mesocrystalline hydrogenated benzoin derivatives of the following formula AV:

[0520]

[0521] Including (S,S) enantiomers not shown,

[0522] in

[0523]

[0524] and

[0525] Each is independently 1,4-phenylene (which can also be composed of L-mono-,

[0526] Di- or tri-substituted) or 1,4-cyclohexylene,

[0527] L is H, F, Cl, CN, or an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, or alkoxy carbonyl group having 1 to 7 carbon atoms, optionally halogenated.

[0528] c is 0 or 1.

[0529] X is CH2 or -C(O)-.

[0530] Z 0 For -COO-, -OCO-, -CH2CH2- or single bonds, and

[0531] R 0 It is an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl or alkyl carbonyloxy group having 1-12 carbon atoms.

[0532] Examples of compounds of formula IV are:

[0533]

[0534]

[0535] Compounds of formulas A-IV are described in WO 98 / 00428. Compounds of formula AV are described in GB-A-2,328,207.

[0536] Very particularly preferred dopants are chiral binaphthyl derivatives as described in WO 02 / 94805, chiral binaphthol acetal derivatives as described in WO 02 / 34739, chiral TADDOL derivatives as described in WO 02 / 06265, and chiral dopants having at least one fluorinated bridging group and a terminal or central chiral group as described in WO 02 / 06196 and WO 02 / 06195.

[0537] Chiral compounds of formula A-VI are particularly preferred.

[0538]

[0539] in

[0540] X 1 X 2 Y 1 and Y 2Each of the following is an independent straight-chain or branched alkyl group consisting of F, Cl, Br, I, CN, SCN, SF5, having 1-25 carbon atoms, which is unsubstituted or mono- or poly-substituted with F, Cl, Br, I, or CN, and wherein one or more non-adjacent CH2 groups may be independently substituted with -O-, -S-, -NH-, or -NR. x -, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH-, or -C≡C- are substituted in such a way that the O and / or S atoms are not directly bonded to each other, polymerizable groups or cycloalkyl or aryl groups having up to 20 C atoms, which may optionally be halogenated, preferably F, or mono- or poly-substituted with polymerizable groups.

[0541] x 1 and x 2 Each is independently 0, 1, or 2.

[0542] y 1 and y 2 Each is independently 0, 1, 2, 3, or 4.

[0543] B 1 and B 2 Each is an aromatic or partially or fully saturated aliphatic six-membered ring, wherein one or more CH groups can be substituted with N and one or more non-adjacent CH2 groups can be substituted with O or S.

[0544] W 1 and W 2 Each is independent of the others as -Z 1 -A 1 -(Z 2 -A 2 ) m -R, and one of the two alternatively, R. 1 Or A 3 However, the two cannot both be H, or

[0545] for

[0546] or

[0547]

[0548] U 1 and U 2 Each can be independently represented as CH2, O, S, CO, or CS.

[0549] V 1 and V 2 Each is independent of the other (CH2). nOne to four non-adjacent CH2 groups can each be replaced by O or S, and V 1 and V 2 One of them

[0550] for

[0551] Both are single bonds.

[0552] n is 1, 2, or 3

[0553] Z 1 and Z 2 Each is independently of the others: -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR x -,-NR x The following groups are combinations of two of the following: -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-, where no two O and / or S and / or N atoms are directly bonded to each other, preferably -CH=CH-COO- or -COO-CH=CH- or a single bond.

[0554] R x Indicates an alkyl group having 1 to 6 carbon atoms.

[0555] A 1 A 2 and A 3 Each is independently 1,4-phenylene, wherein one or two non-adjacent CH groups may be substituted with N; 1,4-cyclohexylene, wherein one or two non-adjacent CH2 groups may be substituted with O or S; 1,3-dioxolane-4,5-diyl, 1,4-cyclohexenyl, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthyl-2,6-diyl, decahydronaphthyl-2,6-diyl or 1,2,3,4-tetrahydronaphthyl-2,6-diyl, wherein each of these groups may be mono- or poly-substituted with L, and additionally A 1 It can be a single key.

[0556] L is a halogen atom, preferably F, CN, or NO2, and is an alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkoxycarbonyloxy group having 1-7 carbon atoms, wherein one or more H atoms may be replaced by F or Cl.

[0557] m is independently 0, 1, 2, or 3 in each case, and

[0558] R and R 1 Each of the following is an independent straight-chain or branched alkyl group having 1 or 3 to 25 carbon atoms: H, F, Cl, Br, I, CN, SCN, SF5, which may optionally be mono- or poly-substituted by F, Cl, Br, I, or CN, and one or more non-adjacent CH2 groups may be respectively substituted by -O-, -S-, -NH-, or -NR. 0 -, -CO-, -COO-, -OCO-, -O-COO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C- substitutions, wherein there are no two O and / or S atoms directly bonded to each other; or polymerizable groups.

[0559] Especially preferred are chiral binaphthyl derivatives of formula A-VI-1.

[0560]

[0561] Among them, rings B and R 0 and Z 0 As defined for equations A-IV and AV, and b is 0, 1, or 2.

[0562] In particular, those selected from formulas A-VI-1a to A-VI-1c:

[0563]

[0564] Among them, rings B and R 0， and Z 0 As defined for formula A-VI-1, and

[0565] R 0 As defined in formulas A-IV, or H or an alkyl group having 1-4 carbon atoms, and

[0566] b is 0, 1, or 2.

[0567] and Z 0 Specifically for -OC(O)- or single bonds.

[0568] The concentration of one or more chiral dopants in the LC medium is preferably in the range of 0.001% to 20%, more preferably 0.05% to 5%, more preferably 0.1% to 2%, and most preferably 0.5% to 1.5%. These preferred concentration ranges are particularly applicable to chiral dopants S-4011 or R-4011 (both from Merck KGaA) and to chiral dopants having the same or similar HTP. For chiral dopants with higher or lower absolute HTP values ​​compared to S-4011, these preferred concentrations must be decreased proportionally or increased proportionally (based on the ratio of their HTP value to the HTP value of S-4011).

[0569] The spacing p of the LC medium or bulk mixture according to the invention is preferably in the range of 5 to 50 μm, more preferably 8 to 30 μm, and especially preferably 10 to 20 μm.

[0570] Preferably, the medium according to the invention comprises a stabilizer selected from the group consisting of compounds of formulas ST-1 to ST-19.

[0571]

[0572]

[0573]

[0574]

[0575] in

[0576] R ST H represents an alkyl or alkoxy group having 1-15 carbon atoms, wherein one or more of these groups may be independently converted to -C≡C-, -CF₂O-, -OCF₂-, or -CH=CH-. -O-, -CO-O-, -O-CO- are substituted in such a way that the O atoms are not directly connected to each other, and in addition, one or more H atoms may be substituted with halogens.

[0577] express

[0578]

[0579]

[0580] Z STEach of these can be independently represented as -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.

[0581] L 1 and L 2 Each can be represented independently as F, Cl, CF3, or CHF2.

[0582] p represents 1 or 2,

[0583] q represents 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0584] Among compounds of formula ST, compounds of the following formula are particularly preferred.

[0585]

[0586] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n

[0587] =1 or 7

[0588]

[0589] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n = 3

[0590]

[0591] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n = 3

[0592]

[0593]

[0594] In compounds of formula ST-3a and ST-3b, n preferably represents 3. In compounds of formula ST-2a, n preferably represents 7.

[0595] A particularly preferred mixture according to the invention comprises one or more stabilizers selected from compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1, and ST-12:

[0596]

[0597]

[0598] Based on the mixture, the compounds of formulas ST-1 to ST-19 are preferably present in the liquid crystal mixture according to the invention in an amount of 0.005% to 0.5% respectively.

[0599] If the mixture according to the invention comprises two or more compounds from the group consisting of compounds of formulas ST-1 to ST-18, then in the case of two compounds, the concentration, based on the mixture, is correspondingly increased to 0.01 to 1%.

[0600] However, based on the mixtures according to the invention, the total proportion of compounds of formulas ST-1 to ST-18 should not exceed 2%.

[0601] The mixture according to the invention contains

[0602] - One or more compounds of Formula I, preferably compounds of Formula I-1 and I-2, wherein the total concentration is preferably in the range of >0% to 30%, more preferably 2% to 25% or 3% to 23%, and particularly preferably 5% to 22%.

[0603] The mixture according to the invention preferably contains

[0604] - One or more compounds of formula I-1, wherein the total concentration is in the range of 1% to 20%, preferably 4% to 15%, particularly 5% to 12%;

[0605] and / or

[0606] - One or more compounds of formula I-2, wherein the total concentration is in the range of 3% to 30%, preferably 4% to 25%, particularly 5% to 22%;

[0607] and / or

[0608] - One or more compounds of formula II and / or IIA-1 and / or IIA-2, preferably compounds of formula II-2 and / or II-3, wherein the total concentration is preferably in the range of 2% to 25%, more preferably 6% to 23%, and particularly preferably 7% to 20%.

[0609] and / or

[0610] - One or more compounds of formula IIIA, wherein the total concentration is preferably in the range of 2% to 30%, more preferably 3% to 25%, and particularly preferably 4% to 20%;

[0611] and / or

[0612] - One or more compounds of formula IIIA and IIIB, wherein the total concentration is preferably in the range of 8% to 35%, more preferably 12% to 30%, and particularly preferably 15% to 26%;

[0613] and / or

[0614] - One or more IIID compounds, the total concentration of which is preferably in the range of 5% to 45%, more preferably 8% to 40%, and particularly preferably 10% to 35%;

[0615] and / or

[0616] - One or more compounds of formula IIIA and IIID, wherein the total concentration is preferably in the range of 8% to 35%, more preferably 12% to 30%, and particularly preferably 15% to 26%;

[0617] and / or

[0618] - One or more compounds of formula IV, wherein the total concentration is preferably in the range of 35% to 75%, more preferably 40% to 65%, and particularly preferably 45% to 55%;

[0619] and / or

[0620] - One or more compounds of formula IV and IVb, wherein the total concentration is preferably in the range of 15% to 70%, more preferably 20% to 65%, and particularly preferably 25% to 60%;

[0621] and / or

[0622] One or more compounds of formula IIA-Y, wherein the total concentration is preferably in the range of >0% to 10%, more preferably 0.5% to 7%, and particularly 1% to 5%.

[0623] Preferably, the medium comprises one or more compounds selected from the group consisting of formulas I, II, IIA-1, IIA-2, III and IV, with a total concentration in the range of 80% to 100% or 85% to 99%, more preferably 90% to 98%, and particularly 93% to 97%.

[0624] In particular, the medium contains

[0625] - One or more compounds CY-n-Om, particularly CY-3-O4, CY-5-O4 and / or CY-3-O2, wherein the total concentration is preferably in the range of 1% to 20%, preferably 2% to 15%, very preferably 3% to 10% or 3% to 8%;

[0626] and / or

[0627] -CPY-n-Om, particularly CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably at a concentration >5%, particularly 7% to 20%.

[0628] and / or

[0629] - One or more compounds CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, with a concentration preferably >3%, particularly 5 to 15%.

[0630] and / or

[0631] -CLY-n-Om, preferably CLY-2-O4, CLY-3-O2 and / or CLY-3-O3, has a concentration of preferably >5%, particularly 15 to 30%, and very preferably 20 to 25% based on the overall mixture;

[0632] and / or

[0633] -CLY-n-Om and PY-n-Om, preferably CLY-3-O2 and / or CLY-3-O3 and / or CLY-4-O2 and PY-3-O2 and / or PY-1-O2, have a concentration of 5 to 35% based on the overall mixture, more preferably 15 to 33%.

[0634] and / or

[0635] -CC-VV, on a total basis, preferably has a concentration of 5 to 50%.

[0636] and / or

[0637] Compounds of formula CC-3-V1 and / or CC-4-V1, wherein the total concentration is in the range of 5% to 40%, more preferably 15% to 35%, and particularly preferably 20% to 30%,

[0638] and / or

[0639] - One or more compounds of the formula B-nO-Om and / or B(S)-nO-Om, particularly compound B(S)-2O-O5, whose concentration is preferably in the range of 2 to 10%, and compounds CC-3-V1 and / or compound CC-4-V1, whose total concentration is in the range of 10 to 30%, preferably 15 to 20%.

[0640] and / or

[0641] -0.1% to 3% of the compound PPGU-3-F

[0642] and / or

[0643] -> 0% to 10%, preferably 4% to 8% of the compound PGIY-nO-Om.

[0644] Furthermore, the present invention relates to an electro-optic display with active matrix addressing, characterized in that it contains a liquid crystal medium as described above as a dielectric, and wherein the display is a VA, SA-VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-posi-VA, PS-TN, polymer-stabilized SA-VA, or polymer-stabilized SA-FFS display.

[0645] Advantageously, the liquid crystal medium according to the invention preferably has a nematic phase with a temperature of ≤-20°C to ≥70°C, particularly preferably ≤-30°C to ≥80°C, and very particularly preferably ≤-40°C to ≥90°C.

[0646] The medium according to the invention has a clearing temperature of 70°C or 75°C or higher, preferably 80°C or higher, more preferably 85°C or 90°C or higher, and especially 95°C or higher.

[0647] The liquid crystal mixture preferably has a nematic phase range of at least 60K and a maximum thickness of 30mm at 20°C. 2 ·s -1 Flow viscosity ν 20 .

[0648] The mixture is nematic at temperatures of -20°C or lower, preferably -30°C or lower, and most preferably -40°C or lower.

[0649] The phrase "possessing a nematic phase" here means, on the one hand, that no smectic phase or crystallization was observed at the corresponding temperature at low temperatures, and on the other hand, that the nematic phase did not become clear upon heating. Low-temperature studies were conducted in a flow viscometer at the corresponding temperature and verified by storage for at least 100 hours in a test chamber with a layer thickness corresponding to the electro-optic application. If the storage stability in the corresponding test chamber at -20°C is 1000 hours or more, the medium is said to be stable at that temperature. The response times were 500 hours and 250 hours at -30°C and -40°C, respectively. At high temperatures, the clearing point was measured in a capillary using conventional methods.

[0650] The birefringence Δn value of the liquid crystal mixture is typically between 0.07 and 0.16, preferably between 0.08 and 0.15, and most preferably between 0.09 and 0.14.

[0651] In a preferred embodiment of the invention, the birefringence of the medium is in the range of 0.085 to 0.105, preferably 0.090 to 0.100, and particularly 0.092 to 0.094.

[0652] In another preferred embodiment, the medium has a birefringence in the range of 0.095 to 0.106, preferably 0.100 to 0.105, and particularly 0.101 to 0.103.

[0653] The liquid crystal mixture according to the invention has a dielectric anisotropy Δε of -1.5 to -8.0, preferably -2.7 to -5.0, and particularly -3.3 to -4.8.

[0654] The rotational viscosity γ1 at 20°C is preferably ≤160 mPa·s, and especially ≤130 mPa·s.

[0655] The medium according to the invention has an average elastic constant K of 15 or greater, preferably 15.3 or greater, very preferably 15.4 or greater, and particularly 15.5 or greater than 15.6. avg .

[0656] The medium according to the invention has a value of γ1 / K1 of 7.9 or 7.8 or 7.7 or 7.6 or less, preferably 7.0 or less, more preferably 6.9 or less, and especially 6.8 or less.

[0657] Furthermore, the liquid crystal medium according to the present invention has a high voltage retention rate in the liquid crystal cell.

[0658] Typically, liquid crystal media with low addressing voltage or threshold voltage exhibit lower voltage retention than those with higher addressing voltage or threshold voltage, and vice versa.

[0659] For the purposes of this invention, the term "dielectrically positive compound" refers to a compound having Δε > 1.5, the term "dielectrically neutral compound" refers to those having -1.5 ≤ Δε ≤ 1.5, and the term "dielectrically negative compound" refers to those having Δε < -1.5. Here, the dielectric anisotropy of the compound is determined by dissolving 10% of the compound in a liquid crystal body in at least one test cell and measuring the capacitance of the resulting mixture. In each case, the test cell has a layer thickness of 20 μm and has vertical and surface alignment at 1 kHz. The measurement voltage is typically 0.5 V–1.0 V, but is always below the capacitance threshold of each liquid crystal mixture studied.

[0660] All temperature values ​​described in this invention are in °C.

[0661] The mixtures according to the invention are suitable for all VA-TFT applications, such as, for example, VAN, MVA, (S)-PVA, ASV, PSA (polymer-continuous VA), and PS-VA (polymer-stabilized VA). They are also suitable for IPS (coplanar switching) and FFS (edge-field switching) applications with negative Δε.

[0662] The nematic liquid crystal mixture in the display of the present invention typically contains two components, A and B, which are themselves composed of one or more separate compounds.

[0663] Component A exhibits significant negative dielectric anisotropy, and makes the dielectric anisotropy of the nematic phase ≤-0.5. In addition to one or more compounds of formula I, it preferably comprises compounds of formula IIIA, IIIB, and / or IIIC, and one or more compounds of formula IV-1.

[0664] The proportion of component A is preferably 45-100%, particularly 60-85%.

[0665] For component A, it is preferable to select one or more individual compounds with a Δε value of ≤-0.8. The smaller the proportion of A in the mixture as a whole, the more negative this value will be.

[0666] Component B exhibits significant nematogeneity, and its flow viscosity at 20°C is no greater than 30 mm. 2 ·s -1 Preferably no larger than 25mm 2 ·s -1 .

[0667] Many suitable materials are known to those skilled in the art from the literature. Compounds of formula O-17 are particularly preferred.

[0668] A particularly preferred single compound in component B is a nematic liquid crystal with extremely low viscosity, having a flow viscosity of no more than 18 mm at 20°C. 2 ·s -1 Preferably no larger than 12mm 2 ·s -1 .

[0669] Component B is a monotropically or enantiotropically nematic, lacks a smectic phase, and can prevent the formation of a smectic phase in the liquid crystal mixture at very low temperatures. For example, if various high-nematic materials are added to a smectic liquid crystal mixture, the nematic states of these materials can be compared by suppressing the degree to which a smectic phase is formed.

[0670] The mixture may also optionally contain component C, which comprises a compound having a dielectric anisotropy of Δε ≥ 1.5. These so-called positive compounds are typically present in the mixture of negative dielectric anisotropy in an amount of ≤ 20 wt%, based on the mixture as a whole.

[0671] In addition to one or more compounds of formula I and formula II, the medium preferably contains 4 to 15, particularly 5 to 12, and especially preferably <10 compounds of formula IIIA, IIIB and / or IIIC, and optionally one or more compounds of formula IV-1.

[0672] In addition to compounds of formula IIIB and / or IIIA, IIIB and / or IIIC and optionally IV-1, other components may also be present, for example, in an amount of up to 45%, but preferably up to 35%, particularly up to 10%, of the whole mixture.

[0673] Other components are preferably selected from nematogenic substances, particularly from known substances of the following classes: azobenzene, benzenemethylaniline, biphenyl, terphenyl, phenyl benzoate or cyclohexyl benzoate, phenyl cyclohexanecarboxylate or cyclohexanecarboxylate, phenylcyclohexane, cyclohexylbiphenyl, cyclohexylcyclohexane, cyclohexylnaphthalene, 1,4-bicyclohexylbiphenyl or cyclohexylpyrimidine, phenyl dioxane or cyclohexyldioxane, optionally halogenated piracene, benzyl phenyl ether, diphenylacetylene, and substituted cinnamates.

[0674] The most important compounds suitable as components of this type of liquid crystal phase can be characterized by the following formula IV.

[0675] R 20 -LGER 21 IV

[0676] Where L and E each refer to a carbocyclic or heterocyclic system derived from the following groups: 1,4-disubstituted benzene rings and cyclohexane rings, 4,4'-disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidine and 1,3-dioxane rings, 2,6-disubstituted naphthalene, dihydronaphthalene and tetrahydronaphthalene, quinazoline and tetrahydroquinazoline.

[0677] G represents -CH=CH--N(O)=N-

[0678] -CH=CQ--CH=N(O)-

[0679] -C≡C--CH2-CH2-

[0680] -CO-O--CH2-O-

[0681] -CO-S--CH2-S-

[0682] -CH=N--COO-Phe-COO-

[0683] -CF2O--CF=CF-

[0684] -OCF2--OCH2-

[0685] -(CH2)4--(CH2)3O-

[0686] Or a CC single bond, Q refers to halogen, preferably chlorine or -CN, and R 20 and R 21 Each refers to an alkyl, alkenyl, alkoxy, alkoxyalkyl or alkoxycarbonyl group having up to 18, preferably up to 8, carbon atoms, or one of these groups refers to CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl or Br.

[0687] In most of these compounds, R 20 and R 21 These substances differ from one another; one of these groups is typically alkyl or alkoxy. Other variations of the proposed substituents are also common. Many such substances, or mixtures thereof, are commercially available. All of these substances can be prepared by methods known from the literature.

[0688] It will be self-evident to those skilled in the art that the VA, IPS or FFS mixtures according to the present invention may also contain compounds in which, for example, H, N, O, Cl and F are substituted with corresponding isotopes.

[0689] Optionally, compounds of formula P are added to the mixtures according to the invention at a concentration preferably from 0.01 to 5% by weight, particularly preferably from 0.2 to 2% by weight, based on the mixture. These mixtures may also optionally contain an initiator, such as that described, for example, in US 6,781,665. Preferably, an initiator (e.g., Irganox-1076 from BASF) is added to the mixture containing the polymerizable compound at an amount of 0 to 1%. Mixtures of this type can be used in so-called polymer-stabilized VA mode (PS-VA) or PSA (polymer-sustaining VA), where reactive mesocrystalline polymerization is intended to occur in the liquid crystal mixture after filling the display panel. This is contingent upon the liquid crystal compound of the LC body not reacting under reactive mesocrystalline polymerization conditions (i.e., generally when exposed to UV in the wavelength range of 320 to 360 nm). Liquid crystal compounds containing alkenyl side chains, such as, for example, CC-3-V, do not exhibit reactivity under the polymerization conditions (UV polymerization) used for RM; therefore, such compounds are not considered RM herein.

[0690] The compounds according to the invention can be synthesized under known reaction conditions suitable for the reactions described herein by or similar to methods described in the literature (e.g., in standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart). Variations known herein but not mentioned herein may also be used. In particular, they can be prepared as described in or similar to the reaction flow below. Other methods for preparing the compounds of the invention are available from examples.

[0691] Other mesocrystalline compounds not explicitly mentioned above may also be optionally and advantageously used in the media according to the invention. Such compounds are known to those skilled in the art.

[0692] The following examples illustrate the invention but do not limit it. However, they demonstrate to those skilled in the art the preferred mixture concept, the preferred compounds used and their respective concentrations, and combinations thereof. Furthermore, the examples clarify which properties and combinations of properties are available.

[0693] For the purposes of this invention and in the following embodiments, the structures of the liquid crystal compounds are represented by abbreviations and converted to chemical formulas according to Tables A to C below. All groups CnH2n+1, CmH2m+1, and C... l H 2l+1 Or CnH2n, CmH2m and C l H 2l The groups are straight-chain alkyl or alkylene groups, each having n, m, and l C atoms in various cases. Preferably, n, m, and l are independently 1, 2, 3, 4, 5, 6, or 7. Table A shows the codes for the ring elements of the compound core, Table B lists the bridging units, and Table C lists the symbol meanings of the left-hand and right-hand end groups of the molecule. Abbreviations consist of the code for the ring element with an optional connecting group, followed by a first hyphen and the code for the left-hand end group, and a second hyphen and the code for the right-hand end group. Table D shows exemplary structures of the compounds and their respective abbreviations.

[0694] Table A: Ring Elements

[0695]

[0696]

[0697]

[0698] Table B: Bridging Units

[0699]

[0700] Table C: End groups

[0701]

[0702]

[0703] Where n and m are integers, and the three dots “…” are placeholders for other abbreviations from this table.

[0704] In addition to compounds of formulas I, IIIA, IIIB, IIIC and / or IIID, the mixtures according to the invention preferably contain one or more of the compounds mentioned below.

[0705] Use the following abbreviations:

[0706] (n, m, k, and l are each independent integers, preferably 1 to 9, more preferably 1 to 7; k and l may also be 0, but are preferably 0 to 4, more preferably 0 or 2, and most preferably 2; n is preferably 1, 2, 3, 4, or 5; in the combination "-nO-", it is preferably 1, 2, 3, or 4, more preferably 2 or 4; m is preferably 1, 2, 3, 4, or 5; in the combination "-Om", it is preferably 1, 2, 3, or 4, more preferably 2 or 4. The combination "-lVm" is preferably "2V1".) Table D

[0707]

[0708]

[0709]

[0710]

[0711]

[0712]

[0713]

[0714]

[0715]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723]

[0724]

[0725] Table E

[0726] Table E shows chiral dopants that can be added to the LC media according to the present invention.

[0727]

[0728]

[0729]

[0730]

[0731]

[0732] Table F

[0733] Table F shows illustrative reactive mesocrystalline compounds that can be used in LC media according to the present invention.

[0734]

[0735]

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750]

[0751]

[0752]

[0753]

[0754] In a preferred embodiment, the mixture according to the invention comprises one or more polymerizable compounds, preferably selected from polymerizable compounds of formulas RM-1 to RM-144. Among these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121, RM-122, and RM-145 to RM-152 are particularly preferred.

[0755] In another preferred embodiment, the mixture according to the invention comprises one or more polymerizable compounds selected from formulas RM-145 to RM-152, and very preferably selected from formulas RM-147 to RM-152.

[0756] Table G

[0757] Table G shows self-aligning additives for vertical alignment, which can be used together with polymerizable compounds of formula P in the LC media of SA-VA and SA-FFS displays according to the present invention:

[0758]

[0759]

[0760]

[0761]

[0762]

[0763]

[0764]

[0765]

[0766]

[0767]

[0768]

[0769]

[0770] In a preferred embodiment, the LC media, SA-VA and SA-FFS displays according to the present invention comprise one or more SA additives selected from SA-1 to SA-48, preferably selected from SA-14 to SA-48, and very preferably selected from SA-20 to SA-34 and SA-44, in combination with one or more RMs of formula P.

[0771] Working Example:

[0772] The following embodiments are intended to explain the invention but not to limit it. In the embodiments, mp represents the melting point of the liquid crystal material (in degrees Celsius) and C represents the clearing point of the liquid crystal material (in degrees Celsius); the boiling temperature is represented by mp. Furthermore: C represents the crystalline solid state, S represents the smectic phase (the index indicates the phase type), N represents the nematic state, Ch represents the cholesterol-like liquid crystal phase, I represents the isotropic phase, and T... g This indicates the glass transition temperature. The number between the two symbols indicates the transition temperature in degrees Celsius.

[0773] The host mixture used to determine the optical anisotropy Δn of a single compound was the commercially available mixture ZLI-4792 (Merck KGaA). The dielectric anisotropy Δε was determined using the commercially available mixture ZLI-2857. Physical data for the compounds under investigation were obtained by extrapolating the change in dielectric constant of the host mixture after the addition of the compound under investigation to 100% of the compound used. Generally, depending on solubility, 10% of the compound under investigation was dissolved in the host mixture.

[0774] Unless otherwise indicated, part or percentage data are expressed as parts by weight or weight percentage.

[0775] In the preceding and following text:

[0776] V o This represents the capacitor threshold voltage [V] at 20℃.

[0777] n e This indicates the unusual refractive index at 20°C and 589 nm.

[0778] n o This indicates the ordinary refractive index at 20°C and 589 nm.

[0779] Δn represents the optical anisotropy at 20℃ and 589nm.

[0780] ε ⊥ ε represents the dielectric permittivity perpendicular to the director at 20°C and 1 kHz. || This represents the dielectric permittivity parallel to the director at 20°C and 1 kHz.

[0781] Δε represents the dielectric anisotropy at 20℃ and 1kHz.

[0782] cl.p.,T(N,I) represents the clearing point [°C].

[0783] γ1 represents the rotational viscosity [mPa·s] measured at 20℃.

[0784] K1 represents the elastic constant, and the "bending" deformation [pN] at 20℃.

[0785] K2 represents the elastic constant, which is [pN] representing the "torsional" deformation at 20℃.

[0786] K3 represents the elastic constant, the bending deformation [pN] at 20℃.

[0787] K avg. The representation is defined as follows: average elastic constant

[0788] LTS indicates the low-temperature stability (nematic phase) measured in the test box or body as specified.

[0789] Unless otherwise expressly stated, all values ​​indicated in this application for temperatures (such as, for example, melting point T(C,N), transformation from smectic (S) phase to nematic (N) phase T(S,N), and clearing point T(N,I) or cl.p.) are indicated in degrees Celsius (°C). Mp represents the melting point. Furthermore, Tg = glassy state, C = crystalline state, N = nematic phase, S = smectic phase, and I = isotropic phase. The numbers between these symbols represent the transformation temperature.

[0790] Unless otherwise explicitly indicated, the term "threshold voltage" used in this invention refers to the capacitance threshold (V0), also known as the Freedericks threshold. In embodiments, as is commonly used, the optical threshold (V0) may also be indicated for 10% relative contrast. 10 ).

[0791] The display used to measure the capacitance threshold voltage consists of two planar parallel glass plates spaced 20 μm apart, each with an electrode layer on its inner side and an unrubbed polyimide alignment layer on top, which causes vertical edge alignment of the liquid crystal molecules.

[0792] The display or test box used to measure the tilt angle consists of two parallel glass outer plates with a spacing of 4 μm, each having an electrode layer on its inner side and a polyimide alignment layer on its top. The two polyimide layers rub against each other in opposite parallel directions, causing vertical edge alignment of the liquid crystal molecules.

[0793] Unless otherwise indicated, at 20°C (VHR) 20 ) and at 100℃ (VHR) 100 VHR was measured after 5 minutes in an oven at a temperature of 1 Hz in a commercially available instrument model LCM-1 (O0004) from TOYOC Corporation, Japan. Unless otherwise specified, the frequency of the voltage used is in the range of 1 Hz to 60 Hz.

[0794] Stability to UV irradiation was studied using the commercially available Suntest CPS+ instrument from Heraeus, Germany, equipped with an NXE1500B xenon lamp. Unless explicitly instructed otherwise, the sealed test chamber was irradiated for 2.0 hours without additional heating. The irradiation power was 765 W / m² in the wavelength range of 300 nm to 800 nm. 2 V. UV “cutoff” filters with an edge wavelength of 310 nm were used sequentially to simulate a so-called window glass pattern. In each series of experiments, at least four test boxes were studied for each condition, and each result was indicated as the average of the corresponding measurements.

[0795] The decrease in voltage retention rate (ΔVHR) caused by exposure (e.g., by UV irradiation or by LCD backlighting) is usually determined according to the following equation (1):

[0796] ΔVHR(t)=VHR(t)-VHR(t=0)(1).

[0797] To study low-temperature stability, also known as "LTS," this refers to the stability of the LC mixture in bulk at low temperatures for the spontaneous crystallization or smectic phase formation of each component. Depending on the specific circumstances, several sealed vials, each containing approximately 1 g of material, are stored at one or more given temperatures, typically -10°C, -20°C, -30°C, and / or -40°C, and visually inspected at regular intervals for any observed phase transitions. Once the first sample shows a change at a given temperature, the time is marked. The time during which no change is observed until the final test is marked as the corresponding LTS.

[0798] Ion density was measured using a commercially available LC material characterization system (model 6254) from Toyo Corporation, Japan, with a VHR test cell made of AL16301 polyimide (JSR Corp., Japan) and a 3.2 μm cell gap. Resistivity was calculated from this measurement. Measurements were performed after storage in an oven at 60°C or 100°C for 5 minutes.

[0799] The term "HTP" refers to the helical twisting force (in μm) of an optically active or chiral substance in an LC medium. Unless otherwise indicated, HTP is measured at 20°C in a commercially available nematic LC host mixture MLD-6260 (Merck KGaA).

[0800] Clearance point was measured using a Mettler Thermosystem FP900. Optical anisotropy (Δn) was measured using an Abbe-Refraktometer H005 (Na10 sodium spectral lamp at 589 nm, 20°C). Dielectric anisotropy (Δε) was measured at 20°C using an LCR-Meter E4980A / Agilent (G005) (ε parallel cell with JALS2096-R1). Turn-on voltage (V0) was measured at 20°C using an LCR-Meter E4980A / Agilent (G005) (ε parallel cell with JALS2096-R1). Rotational viscosity (γ1) was measured at 20°C using a TOYO LCM-2 (0002) (γ1 negative cell with JALS-2096-R1). The elastic constant (K1, development) was measured at 20°C using an LCR-Meter E4980A / Agilent (G005) (with an ε-parallel cell of JALS2096-R1). K3: The elastic constant (K3, bending) was measured at 20°C using an LCR-Meter E4980A / Agilent (G005) (with an ε-parallel cell of JALS2096-R1).

[0801] Unless otherwise expressly stated, all concentrations in this application are indicated as weight percentages and relate to the corresponding mixture (solvent-free) comprising all solid or liquid crystal components as a whole. Unless otherwise expressly stated, all physical properties were determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", Status November 1997, Merck KGaA, Germany, and are applicable at a temperature of 20°C.

[0802] The following hybrid embodiments with negative dielectric anisotropy are particularly suitable for liquid crystal displays having at least one planar alignment layer, such as IPS and FFS displays, especially UB-FFS (= Ultra Bright FFS), and are also suitable for VA displays.

[0803] Mixture Examples and Comparative Examples

[0804] Comparative mixture C-1 and mixture examples N-1 to N-64 have the composition and characteristics given in the table below.

[0805] Comparison of mixture C1

[0806]

[0807]

[0808] Mixture N-1

[0809]

[0810] Mixture N-2

[0811]

[0812]

[0813] Mixture N-3

[0814]

[0815] A comparison of media N-1, N-2, and N-3 with media C-1, which contains compound II but not compound I, unexpectedly shows that, due to the use of compound I, the γ1 / K1 value of the liquid crystal medium according to the present invention is significantly improved (reduced), resulting in faster switching of the display containing the medium (see Table 1 below). Furthermore, K... avgThe value of γ1 / K1 remains almost constant, which corresponds to an unchanged high contrast. Particularly advantageously, a low value of γ1 / K1 is achieved by using both compounds of formula I-1 and I-2 (mixtures N-2 and N-3).

[0816] Table 1

[0817] mixture [gamma]1 / K1 K avg ]]> C-1 7.2 15.6 N-1 7.0 15.7 N-2 6.7 15.5 N-3 6.5 15.7

[0818] Mixture N-4

[0819]

[0820] Mixture N-5

[0821]

[0822]

[0823] Mixture N-6

[0824]

[0825] Mixture N-7

[0826]

[0827] Mixture N-8

[0828]

[0829]

[0830] Mixture N-9

[0831]

[0832] Mixture N-10

[0833]

[0834]

[0835] Mixture N-11

[0836]

[0837] Mixture N-12

[0838]

[0839]

[0840] Mixture N-13

[0841]

[0842] Mixture N-14

[0843]

[0844]

[0845] Mixture N-15

[0846]

[0847] Mixture N-16

[0848]

[0849]

[0850] Mixture N-17

[0851]

[0852] Mixture N-18

[0853]

[0854]

[0855] Mixture N-19

[0856]

[0857] Mixture N-20

[0858]

[0859]

[0860] Mixture N-21

[0861]

[0862] Mixture N-22

[0863]

[0864] Mixture N-23

[0865]

[0866] Mixture N-24

[0867]

[0868] Mixture N-25

[0869]

[0870]

[0871] Mixture N-26

[0872]

[0873] The following mixtures N-27 to N-63 further contain stabilizers as indicated above. The total amounts of the main mixture and stabilizers given in the table are 100% by weight.

[0874] Table 2: Mixtures containing stabilizers.

[0875]

[0876]

[0877]

[0878] Chiral nematic mixture N-64 consists of 99.20% mixture N-27 and 0.80% chiral dopant S-2011.

[0879]

[0880] The N-64 mixture is characterized by very high stability under UV load and exhibits improved switching time.

Claims

1. A liquid crystal medium comprising one or more compounds of formula I. in R 11 R 12 The same or different representations of H or straight-chain or branched alkyl groups having 1 to 15 C atoms, wherein one or more CH2 groups among these groups can be independently generated such that the O atoms are not directly connected to each other. , , , , The hydrogen atoms can be substituted with -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more of the hydrogen atoms can be substituted with halogens. Y represents H or CH3. p is 0 or 1; The compound of formula I includes one or more compounds of formula I-1 and one or more compounds of formula I-2. Among them, Y and R 11 and R 12 It has the meaning given for Equation I above, One or more of Formula I-1 compounds and one or more of Formula I-2 compounds are used at a total concentration ranging from 2% to 25%. and One or more compounds of formula II-2 and one or more compounds of formula II-3, in R 11 and R 12 The same or different representations of H, straight-chain or branched alkyl or alkoxy groups having 1 to 15 C atoms, wherein one or more CH2 groups among these groups can be independently generated such that the O atoms are not directly connected to each other. , , , The hydrogen atoms can be substituted with -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more of the hydrogen atoms can be substituted with halogens. L 11 and L 12 Each can be independently represented as H, F, Cl, CF3, or CHF2. The liquid crystal medium contains one or more compounds, CCY-n-Om, at a concentration of 5% to 15%. Where n and m are each an integer from 1 to 9, independent of each other.

2. The liquid crystal medium according to claim 1, wherein the liquid crystal medium comprises one or more compounds selected from the group consisting of compounds of formulas IIA, IIB, IIC, IID, and IIE. in R 2A R 2B R 2C R 2D and R 2E Each group independently represents H, an alkyl or alkenyl group having up to 15 carbon atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more CH2 groups in these groups can be connected in a manner such that the O atoms are not directly connected to each other via -O-, -S-, , , , , Replace with -C≡C-, -CF₂O-, -OCF₂-, -OC-O-, or -O-CO-. L 1 To L 4 Each can be independently represented as F, Cl, CF3, or CHF2. Y represents H, F, Cl, CF3, CHF2, or CH3. Z 2A Each of these independently represents a single bond, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-. Z 2 Z 2B and Z 2D Each of these can 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 an integer from 1 to 6. Compounds of Formula I are not included.

3. The liquid crystal medium according to claim 1 or 2, wherein the liquid crystal medium comprises one or more compounds selected from the group consisting of:

4. The liquid crystal medium according to claim 1 or 2, wherein the liquid crystal medium comprises a chiral dopant.

5. The liquid crystal medium according to claim 1 or 2, wherein the liquid crystal medium comprises one or more polymerizable compounds of formula P. P-Sp-A 1 -(Z 1 -A 2 ) z -R P in P represents a polymerizable group. Sp represents a spacer group or a single bond. A 1 A 2 The same or different groups may represent aromatic groups, heteroaromatic groups, alicyclic groups, or heterocyclic groups, and may also contain fused rings, and may be unsubstituted or monosubstituted or polysubstituted. L represents F, Cl, -CN, P-Sp- or a straight-chain, branched or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2- groups are optionally substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- in such a manner that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are optionally substituted with P-Sp-, F or Cl. Z 1 Represents -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH2-CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 -or a single key, R 0 R 00 The same or different representations of H or alkyl groups having 1 to 12 carbon atoms, R represents H, L, or P-Sp-. z is 0, 1, 2, or 3. n1 can be 1, 2, 3 or 4.

6. The liquid crystal medium according to claim 5, wherein A 1 A 2 The aromatic, heteroaromatic, alicyclic, or heterocyclic groups described in the definition have 4 to 25 ring atoms.

7. The liquid crystal medium according to claim 5, wherein the polymerizable compound of formula P is polymerized.

8. A method for preparing a liquid crystal medium according to any one of claims 1 to 7, comprising the step of mixing one or more compounds selected from the group consisting of formulas I, IIA, IIB, IIC, IID and IIE according to claim 1 with one or more mesocrystalline or liquid crystal compounds, optionally with a polymerizable compound according to claim 5 or 6, and optionally with one or more additives.

9. An LC display comprising a liquid crystal medium according to any one of claims 1 to 7.

10. The LC display of claim 9, wherein the display is a PSA display.

11. The LC display of claim 10, wherein the display is a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS, polymer-stabilized SA-VA, or polymer-stabilized SA-FFS display.

12. The LC display of claim 9, wherein the display is a VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS or SA-VA display.

13. Use of a liquid crystal medium according to any one of claims 1 to 7, for use in an electro-optical display.

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