Liquid crystal medium and preparation and use thereof
Patent Information
- Application Number
- TW114152152
- Authority / Receiving Office
- TW · TW
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-07-03
- Filing Date
- 2021-07-02
- Publication Date
- 2026-10-21
- Estimated Expiration
- 2041-07-01
AI Technical Summary
Existing liquid crystal displays face challenges in achieving high contrast, wide viewing angles, and fast response times, particularly in display modes like PS-VA, PS-IPS, and PS-FFS, due to issues with polyimide alignment layers leading to reduced reliability and limited material options.
A liquid crystal medium comprising specific compounds of formulas I, IIA, IIB, IIC, IID, III, IIIA, IV, IVa, Va, and VI, which induce self-alignment and polymer stabilization, enhancing display performance without the need for traditional alignment layers.
The proposed liquid crystal medium achieves faster response times and improved contrast without adverse effects on other display parameters, broadening material options and optimizing display characteristics.
Abstract
Description
Technical Field
[0001] This invention relates to a liquid crystal (LC) medium and to its use for optical, electro-optical and electronic purposes, particularly for use in LC displays, especially in IPS, FFS, VA or PS-VA displays. Prior Technology
[0002] One of the liquid crystal display (LCD) modes 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] Furthermore, so-called VA ("vertical alignment") displays with a wider viewing angle are known. The LC cells of a VA display contain an LC dielectric layer between two transparent electrodes, where the LC dielectric typically exhibits negative dielectric anisotropy. In the off state, the molecules of the LC layer are orthogonally (perpendicularly) aligned to the electrode surfaces or have an inclined vertical alignment. When a voltage is applied to the two electrodes, a reorientation of the LC molecules parallel to the electrode surfaces occurs.
[0004] Furthermore, OCB (Optically Compensated Curvature) displays are known, which are based on birefringence and have an LC layer with so-called "curvature" alignment and generally positive dielectric anisotropy. Upon application of voltage, the LC molecules orthogonal to the electrode surface undergo reorientation. Additionally, OCB displays typically contain one or more birefringent light-blocking films to prevent insufficient light transmittance of the curved cells in the dark. Compared to TN displays, OCB displays offer wider viewing angles and shorter response times.
[0005] It is also known that so-called IPS ("coplanar switching") displays 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 generated therebetween. This causes the LC molecules in the layer plane to realign.
[0006] Furthermore, 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 of which is structured in a comb-like manner and the other is unstructured. This generates a strong so-called "edge field," that is, a strong electric field near the edge of the electrode, and an electric field throughout the cell with both strong vertical and strong horizontal components. The contrast of FFS displays has low viewing angle dependence. FFS displays typically contain an LC dielectric with positive dielectric anisotropy and an alignment layer, typically polyimide, which provides planar alignment to the molecules of the LC dielectric.
[0007] FFS displays can operate as active-matrix or passive-matrix displays. As is known from the prior art, 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, individual pixels are typically addressed by multiplexing methods.
[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 an LC dielectric layer with negative dielectric anisotropy instead of an LC dielectric layer with positive dielectric anisotropy. Compared to an LC dielectric with positive dielectric anisotropy, an LC dielectric with negative dielectric anisotropy exhibits a more favorable director orientation, i.e., less tilt and greater torsional orientation, and therefore these displays have higher transmittance. The display further includes an alignment layer disposed on at least one of the substrates, preferably a polyimide alignment layer, which contacts the LC dielectric and induces planar alignment of the LC molecules of the LC dielectric. These displays are also known as "Ultra Brightness FFS (UB-FFS)" mode displays. These displays require highly reliable LC media.
[0009] As used below, the term "reliability" refers to the performance quality of a display over a period of time under various stress loads, such as light load, temperature, humidity, and voltage, and includes display effects such as image retention (regional and line image retention), streaks, and yogore, which are known to those skilled in the art of LC displays. The voltage retention rate (VHR) value is commonly used as a standard parameter for classifying reliability; it is a measure of how constantly the voltage in the tested display remains constant. Among other factors, a higher VHR is a prerequisite for higher reliability of LC media.
[0010] In newer types of VA displays, the uniform alignment of LC molecules is confined to a plurality of relatively small domains within the LC cell. Discrepancy can exist between these domains, also known as tilted domains. Compared to conventional VA displays, VA displays with tilted domains offer greater viewing angle independence in terms of contrast and grayscale. Furthermore, this type of display is easier to manufacture because it eliminates the need for additional treatments to the electrode surfaces, such as friction, to ensure uniform molecular alignment in the on-state. Instead, the preferred orientation of the tilt or pre-tilt angle is controlled by a specific design of the electrodes.
[0011] In so-called MVA (Multi-Domain Vertical Alignment) displays, this is typically achieved by electrodes with protrusions that induce local pre-tilt. Therefore, upon application of voltage, LC molecules align parallel to the electrode surface in different directions within different defined regions of the cell. This achieves "controlled" switching and prevents the formation of interfering misalignments. While this configuration improves the display's viewing angle, it reduces its transmittance. Another development of MVA uses protrusions on only one electrode side, with slits on the opposing electrode, which improves transmittance. Upon application of voltage, the slit electrode generates a non-homogeneous electric field within the LC cell, meaning controlled switching is still achieved. Further improvements in transmittance can be achieved by increasing the spacing between the slit and the protrusion, but this increases the response time. In so-called fixed PVA ("patterned VA") displays, protrusions become completely redundant because both electrodes are structured using slits on opposite sides, resulting in increased contrast and improved transmittance, but this is technically more difficult and makes the display more sensitive to mechanical influences (such as "tapping"). However, for many applications, such as monitors and especially TV screens, there is a need for shorter response times and improved contrast and brightness (transmittance).
[0012] Further development leads to so-called PS ("polymer-continuous") or PSA ("polymer-continuously aligned") type displays, which are also sometimes referred to as "polymer-stabilized". In these displays, a small amount (e.g., 0.3% by weight, typically < 1% by weight) of one or more polymerizable compounds, preferably polymerizable monomeric compounds, is added to the LC medium. After the LC medium is filled into the display, in-situ polymerization or crosslinking is typically performed by UV photopolymerization, with voltage applied to the electrodes of the display as appropriate. Polymerization occurs at the temperature at which the liquid crystal phase is displayed in the LC medium, typically at room temperature. Adding polymerizable liquid crystal precursors or liquid crystal compounds, also known as reactive liquid crystal precursors or "RM", to the LC mixture has proven particularly suitable.
[0013] Unless otherwise indicated, the term "PSA" is generally used when referring to polymer continuous alignment displays, and the term "PS" is used when referring to specific display modes such as PS-VA, PS-TN and similar modes.
[0014] Similarly, unless otherwise indicated, the term "RM" will be used hereinafter when referring to polymerizable liquid crystal primordia or liquid crystal compounds.
[0015] Meanwhile, the PS(A) principle is used in various conventional LC display modes. Therefore, displays such as PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, and PS-TN are known. In the case of PS-VA and PS-OCB displays, RM aggregation is preferably performed using an applied voltage, while in the case of PS-IPS displays, RM aggregation may or may not be performed using an applied voltage (preferably, not). As can be demonstrated in test cells, the PS(A) method causes pre-tilt of the cell. For example, in the case of PS-OCB displays, the bent structure may be stabilized so that offset voltage is unnecessary or can be reduced. In the case of PS-VA displays, pre-tilt has a positive effect on response time. In the case of PS-VA displays, standard MVA or PVA pixel and electrode layouts can be used. However, it is also possible, for example, to manage with only one structured electrode side without protrusions, which significantly simplifies manufacturing and simultaneously produces excellent contrast and excellent light transmittance.
[0016] Furthermore, the so-called posi-VA display ("positive VA") has proven to be a particularly suitable mode. In a classic VA display, in its initial state without applied voltage, the initial orientation of the LC molecules in a posi-VA display is vertical, essentially orthogonal to the substrate. However, compared to a classic VA display, a posi-VA display uses an LC dielectric with positive dielectric anisotropy. As in commonly used IPS displays, the two electrodes in a posi-VA display are positioned on only one of the two substrates, exhibiting a better interlocking, comb-like (interdigitated) structure. By applying a voltage to the interdigitated electrodes, an electric field substantially parallel to the LC dielectric layer is generated, causing the LC molecules to shift to an orientation substantially parallel to the substrate. In posi-VA displays, the addition of polymeric polymers (RMs) polymerized within the display to the LC dielectric has also proven advantageous, resulting in a significant reduction in switching time.
[0017] PS-VA displays are described, for example, in EP 1 170 626 A2, US 6,861,107, US 7,169,449, US 2004 / 0191428 A1, US 2006 / 0066793 A1, and US 2006 / 0103804 A1. PSA-OCB displays are described, for example, in T.-J-Chen et al., Jpn. J. Appl. Phys. 45, 2006, 2702-2704 and SH Kim, 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] Underneath the layer formed by the phase-separated and polymerized RM that causes the aforementioned pre-tilt angle, PSA displays typically contain an alignment layer, such as a polyimide alignment layer, which provides initial alignment of LC molecules prior to the polymer stabilization step.
[0019] Triborealized polyimide layers have long been used as alignment layers. However, the triborealization process leads to various problems, such as streaks, contamination, electrostatic discharge, and debris. Therefore, instead of triborealized polyimide layers, it is proposed to use polyimide layers prepared by photo-alignment, utilizing the light-induced orientation and sorting of the alignment surface. This can be achieved by using polarized light through photodecomposition, photodimerization, or photoisomerization.
[0020] However, a suitable polyimide layer containing photoreactive groups is still required. Generally speaking, the workload and cost of processing the polyimide and the modified bump or polymer layer are relatively large in order to manufacture this polyimide layer.
[0021] Furthermore, unfavorable interactions between the polyimide alignment layer and certain compounds in the LC medium have been observed, typically leading to a decrease in the display's resistance. The number of suitable and usable LC compounds is thus significantly reduced, at the expense of display parameters intended to be improved through the use of such LC compounds, such as viewing angle dependence, contrast, and response time. 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 through a self-assembly mechanism, such as in-situ vertical or planar alignment. Therefore, the alignment layer on one or both of the substrates can be omitted. These display modes are also called "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 anchor groups attached thereto, which can interact with the substrate surface, thereby orienting the additive on the substrate surface and also inducing the desired orientation in the LC molecules. Preferred self-aligning additives contain, for example, liquid crystal primitive groups and straight or branched alkyl side chains terminated by one or more polar anchor groups, such as 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.
[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 in, for example, 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. Therefore, the LC medium of the display used in this combined mode contains one or more RMs and one or more self-aligning additives.
[0026] As described above, the conventional LC display can operate as an active matrix or passive matrix display. As is known from the prior art, 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, individual pixels are typically addressed by multiplexing methods.
[0027] PSA displays may also include alignment layers on one or both of the substrates forming the display units. Alignment layers are typically applied to electrodes (where such electrodes are present) to contact the LC medium and induce the initial alignment of LC molecules. Alignment layers may comprise, for example, polyimide or composed of the same, and polyimide may also be rubbed or prepared by photoalignment methods.
[0028] Specifically, for monitors, especially TV applications, there remains a need to optimize the response time, contrast, and brightness (and therefore, transmittance) of LC displays. The PSA method described in this paper offers significant advantages. Specifically, in the case of PS-VA, PS-IPS, PS-FFS, and PSA-posi-VA displays, a reduction in response time can be achieved without significantly adverse effects on other parameters, which is related to the measurable pre-tilt in the test cell. Summary of the Invention
[0029] The present invention is based on the objective of providing novel and suitable materials for LC media containing reactive liquid crystal primitives (RMs) for use in displays, which do not have or have to a lesser extent the disadvantages indicated above. Specifically, this technology still requires liquid crystal media with high reliability.
[0030] In addition, the objective of this invention is to provide alternative media to those 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 in displays requiring exceptionally high contrast, because high contrast necessitates a lower 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 the materials and methods 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. Implementation
[0033] This invention relates to a liquid crystal medium comprising one or more compounds of formula I. in R1 represents H, a straight-chain or branched alkyl or alkoxy group having 1 to 15 C atoms, wherein one or more of these groups (CH2 groups) can be formed independently of each other such that the O atoms are not directly connected to each other. The substituents include -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and additionally, one or more H atoms may be halogenated, preferably alkyl or alkenyl groups having up to 7 C atoms. express The better option is , Y1 represents H or CH3, preferably H. n can be 0 or 1, preferably 1. v is 1, 2, 3, 4, 5, or 6, and The medium further comprises one or more compounds selected from the group consisting of compounds of formulas IIA, IIB, IIC, and IID. in R2A, R2B, R2C R2D and each independently represent H, an alkyl or alkenyl group having up to 15 C atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more of these groups are CH2 groups that allow the O atoms to be not directly connected to each other via -O-, -S-, Replacement with -CF2O-, -OCF2-, -OC-O-, or -O-CO-. L1 to L4 each independently represent F, Cl, CF3, or CHF2. Y represents H, F, Cl, CF3, CHF2, or CH3, preferably H or CH3, and especially H. Z2, Z2B, and Z2D each independently represent a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-. p represents 0, 1, or 2. q represents 0 or 1, and v represents an integer from 1 to 6.
[0034] Surprisingly, by using a compound of formula I and one or more compounds of formulas IIA, IIB, IIC and / or IID 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.
[0035] Preferred compounds of formula I are selected from the following sub-formulas:
[0036] The best compounds of formula I are compounds I-1 to I-14.
[0037] In a preferred embodiment, the medium comprises one or more compounds of formula IA. The groups and parameters present therein have the meanings given above according to Equation I, and R2 indicates , where r is 0, 1, 2, 3, 4, 5 or 6, and s is 1, 2 or 3.
[0038] The preferred compounds of formula IA are compounds IA-1 to IA-14.
[0039] In compounds of formulas IIA, IIB, and IID, Z2 may have the same or different meanings. In compounds of formula IIB, Z2 and Z2B may have the same or different meanings. In compounds of formula IID, Z2 and Z2D may have the same or different meanings.
[0040] In compounds of formulas IIA, IIB, IIC and IID, R2A, R2B, R2C and R2D preferably represent alkyl groups having 1 to 6 C atoms, specifically CH3, C2H5, n-C3H7, n-C4H9 and n-C5H11.
[0041] In compounds of formulas IIA, IIB, and IID, L1, L2, L3, and L4 preferably represent L1 = L2 = F and L3 = L4 = F, and also L1 = F and L2 = Cl, L1 = Cl and L2 = F, L3 = F and L4 = Cl, and L3 = Cl and L4 = F. In formulas IIA and IIB, Z2 and Z2B preferably each represent a single bond independently, and are also -C2H4- bridges.
[0042] If in formula IIB, Z2 = -C2H4- or -CH2O-, then Z2B is preferably a single bond; or if Z2B = -C2H4- or -CH2O-, then Z2 is preferably a single bond.
[0043] In formula IID, Z2D is preferably a single bond.
[0044] In compounds of formulas IIA, IIB, and IID, (O)CvH2v+1 preferably represents OCvH2v+1. In compounds of formula IIC, (O)CvH2v+1 preferably represents CvH2v+1.
[0045] In the compound of formula IIC, L3 and L4 preferably represent F respectively.
[0046] Preferred compounds of formulas IIA, IIB, IIC, and IID are indicated below: Wherein parameter a represents 1 or 2, alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 carbon atoms, and 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-.
[0047] The preferred mixture according to the present invention comprises one or more compounds of the formulas IIA-2, IIA-8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1 and IID-4.
[0048] The proportion of compounds of formula IIA and / or IIB in the overall mixture is preferably at least 20% by weight.
[0049] The preferred medium of the present invention comprises at least one compound of formula IIC-1. , Wherein alkyl and alkyl* have the meaning indicated above, preferably in an amount of > 3% by weight, specifically > 5% by weight, and even more preferably 5 to 25% by weight.
[0050] In a preferred embodiment, the medium according to the invention comprises one or more compounds of formula III. in R11 and R12 each independently represent H, an alkyl or alkoxy group having 1 to 15 C atoms, wherein one or more of these groups (CH2 groups) can independently link the O atoms in a manner that prevents direct bonding between them. The hydrogen atom is replaced by -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more of the hydrogen atoms may be replaced by halogens. A1 is represented independently of each other in each occurrence. a) 1,4-Ph-cyclohexenyl or 1,4-Ph-cyclohexyl, wherein one or two non-adjacent CH2 groups may be substituted with -O- or -S-. b) 1,4-Phenylene, wherein one or two CH groups may be replaced by N, or c) Groups derived from the groups spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo-[2.2.2]epoxyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl, and fenenyl-2,7-diyl. These groups a), b), and c) can be mono- or poly-substituted with halogen atoms. n represents 0, 1, or 2, preferably 0 or 1. Z1, each time it appears, independently represents -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond, and L11 and L12 each independently represent F, Cl, CF3, or CHF2, preferably F, and W represents O or S, with S being preferred.
[0051] In one preferred embodiment of the present invention, the medium comprises one or more compounds of formula III-1 and / or III-2. The groups present therein have the same meaning as those given above according to Formula III, and preferably... R11 and R12 are each independently an alkyl, alkenyl, or alkoxy group having up to 15 carbon atoms; more preferably, one or both represent an alkoxy group. L11 and L12 each represent F.
[0052] In a preferred embodiment, the medium comprises one or more compounds of formula III-1 selected from the group consisting of compounds of formula III-1-1 to III-1-10, preferably formula III-1-6. , 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 L11 and L12 each independently represent F or Cl, preferably both being F.
[0053] In a preferred embodiment, the medium comprises one or more compounds of formula III-2 selected from the group consisting of compounds of formula III-2-1 to III-2-10, preferably formula III-2-6. , 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 L1 and L2 each independently represent F or Cl, preferably both being F.
[0054] In one preferred embodiment of the present invention, the medium comprises one or more compounds of formula IIIA-1 and / or IIIA-2. Where L11 and L12 have the same meaning as given according to Equation III, m and n can be the same or different as 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, and ideally 1. (O) indicates 0 or a single bond. Cy represents a cycloaliphatic group having 3, 4 or 5 ring atoms, which may be substituted with an alkyl or alkenyl group having up to 3 C atoms or with a halogen or CN, and preferably represents cyclopropyl, cyclobutyl or cyclopentyl.
[0055] The medium contains compounds of formula IIIA-1 and / or IIIA-2, in addition to or excluding compounds of formula III.
[0056] The following are excellent compounds of formulas IIIA-1 and IIIA-2: Here, alkoxy represents a straight-chain alkoxy group having 1 to 6 carbon atoms.
[0057] In one preferred embodiment of the present invention, the medium comprises one or more compounds of formula III-3. in R11 and R12 may represent H, an alkyl or alkoxy group having 1 to 15 carbon atoms, wherein one or more of these groups are independently connected via -C≡C-, -CF2O-, -OCF2-, or -CH=CH-, such that the O atoms are not directly connected to each other. The atoms are replaced by -O-, -CO-O-, or -O-CO-, and one or more H atoms may be replaced by halogens.
[0058] Compounds of formula III-3 are preferably selected from the group of compounds of formulas III-3-1 to III-3-11: R12 represents an alkyl group having 1 to 7 carbon atoms, preferably ethyl, n-propyl or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl.
[0059] In one preferred embodiment of the present invention, the medium comprises one or more compounds of formulas III-4 to III-6, preferably III-5. The parameters have the meanings given above, with R11 preferably representing a straight-chain alkyl group and R12 preferably representing an alkoxy group, each having 1 to 7 C atoms.
[0060] In a preferred embodiment, the medium comprises one or more compounds of formula III selected from the group consisting of compounds of formulas III-7 to III-9, preferably formula III-8. The parameters have the meanings given above, with R11 preferably representing a straight-chain alkyl group and R12 preferably representing an alkoxy group, each having 1 to 7 C atoms.
[0061] In a preferred embodiment, the medium comprises one or more formula IV compounds. in R41 represents 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. R42 represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkoxy group having 1 to 6 carbon atoms, both preferably having 2 to 5 carbon atoms, an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably having 2, 3 or 4 carbon atoms, more preferably vinyl or 1-propenyl, and specifically vinyl.
[0062] Compounds of formula IV are preferably selected from the group of compounds of formulas IV-1 to IV-4: in alkyl and alkyl' independently refer to alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. alkenyl indicates an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and most preferably 2 carbon atoms. 'alkenyl' indicates an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and most preferably 2 to 3 carbon atoms. alkoxy refers to an alkoxy group having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.
[0063] Preferably, the medium comprises one or more compounds selected from the group consisting of compounds of formulas IV-1-1 to IV-1-5.
[0064] Preferably, the medium according to the present invention comprises one or more compounds of formula IV-2-1 and / or IV-2-2.
[0065] Preferably, the medium according to the present invention comprises a compound of formula IV-3, specifically a compound selected from formulas IV-3-1 to IV-3-5.
[0066] Preferably, the medium according to the present invention comprises a compound of formula IV-4, specifically a compound selected from formulas IV-4-1 and IV-4-2.
[0067] The liquid crystal medium preferably further comprises one or more IVa compounds. in R41 and R42 each independently represent a straight-chain alkyl, alkenyl, alkoxyalkyl, or alkoxy group having up to 12 carbon atoms, and express , Z4 represents single bonds, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, and -CF=CF-.
[0068] Preferred compounds of formula IVa are indicated below: in alkyl and Alkyl* Each of these terms independently represents a straight-chain alkyl group having 1 to 6 carbon atoms.
[0069] The medium according to the present invention preferably comprises at least one compound of formula IVa-1 and / or formula IVa-2.
[0070] The proportion of the IVa compound in the overall mixture is preferably at least 5% by weight.
[0071] Preferably, the medium comprises one or more compounds of formula IVb-1 to IVb-3. in alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 carbon atoms, and alkenyl and alkenyl* each independently represent a straight-chain alkenyl group having 2 to 6 carbon atoms.
[0072] The proportion of biphenyls of formulas IV-1 to IV-3 in the overall mixture is preferably at least 3% by weight, specifically ≥ 5% by weight.
[0073] Among the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.
[0074] Yujia biphenyl is Wherein alkyl* represents an alkyl group having 1 to 6 carbon atoms, and preferably represents n-propyl. The medium according to the invention preferably comprises one or more compounds of formula IVb-1-1 and / or IVb-2-3.
[0075] In a preferred embodiment, the medium comprises one or more V compounds. in R51 and R52 independently have one of the meanings given for R41 and R42, and preferably represent an alkyl group having 1 to 7 carbon atoms, more preferably a n-alkyl group, and especially preferably a n-alkyl group having 1 to 5 carbon atoms; an alkoxy group having 1 to 7 carbon atoms, more preferably a n-alkoxy group, and especially 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, more preferably 2 to 4 carbon atoms, more preferably an alkenyloxy group. , Same or different in better representation , Z51 and Z52 each independently represent -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond, preferably -CH2-CH2-, -CH2-O-, or a single bond, and even more preferably a single bond. n is 1 or 2.
[0076] Compounds of formula V are preferably selected from compounds of formulas V-1 to V-17: R1 and R2 have the same meaning as indicated above for R2A. R1 and R2 preferably each independently represent a straight-chain alkyl or alkenyl group.
[0077] The preferred medium comprises one or more compounds of the forms V-1, V-3, V-4, V-6, V-7, V-10, V-11, V-12, V-14, V-15 and / or V-16.
[0078] The mixtures according to the invention preferably contain compounds of formula V-10, V-12, V-16 and / or IV-1, specifically in an amount of 5 to 30%.
[0079] The preferred V-10 compound is indicated below:
[0080] The medium according to the present invention 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 compound of formula V-10a and / or V-10b and one or more compounds selected from bicyclohexyl compounds of formula IV-1 is 5% to 40%, most preferably 15% to 35%.
[0081] An extremely preferred mixture contains compounds V-10a and IV-1-1
[0082] Based on the entire mixture, compounds V-10a and IV-1-1 are preferably present in the mixture at a concentration of 15 to 35%, more preferably 15 to 25%, and especially preferably 18 to 22%.
[0083] The most desirable mixture contains compounds V-10b and IV-1-1: .
[0084] On a whole, compounds V-10b and IV-1-1 are preferably present in the mixture at a concentration of 15 to 35%, more preferably 15 to 25%, and especially preferably 18 to 22%.
[0085] The best mixture contains the following three compounds: .
[0086] On a whole, compounds V-10a, V-10b and IV-1-1 are preferably present in the mixture at a concentration of 15 to 35%, more preferably 15 to 25% and especially preferably 18 to 22%.
[0087] The preferred mixture contains at least one compound selected from the group consisting of: , R41 and R42, as well as R51 and R52, have the meanings indicated above. Preferably, in compounds V-6, V-7, and IV-1, R41 and R51 represent alkyl or alkenyl groups having 1 to 6 or 2 to 6 carbon atoms, respectively, and R42 and R52 represent alkenyl groups having 2 to 6 carbon atoms.
[0088] The preferred mixture comprises at least one compound of formula V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a, and IV-3b: Where alkyl represents an alkyl group having 1 to 6 carbon atoms, and alkenyl represents an alkenyl group having 2 to 6 carbon atoms.
[0089] The compounds of formulas V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a and IV-3b are preferably present in the mixture according to the invention in an amount of 1 to 40% by weight, more preferably 5 to 35% by weight, and very preferably 10 to 30% by weight.
[0090] In a preferred embodiment, the medium comprises one or more Va compounds. in RL represents H, a straight-chain or branched alkyl or alkoxy group having 1 to 15 C atoms, wherein one or more of these groups (CH2 groups) can be formed independently of each other such that the O atoms are not directly connected to each other. The hydrogen atom is replaced by -C≡C-, -CF₂O-, -OCF₂-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more of the hydrogen atoms may be replaced by halogens. XL represents F, Cl, CN, CHF2, CF3, OCF3, or one of the following that has the same or different meanings as RL. YL represents H, F, Cl, or CH3.
[0091] Compounds of formula Va are preferably selected from the group of compounds of formula Va-1 and Va-2: in RL1 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 cyclopropane-1,2-dimethyl substitution.
[0092] In a preferred embodiment, the medium comprises one or more compounds selected from the following formulas: RL1 has the meaning given above for the expression Va.
[0093] Preferably, the medium comprises compound Vb-2, wherein RL1 represents an alkyl or alkenyl group having up to 7 carbon atoms, specifically a vinyl group.
[0094] In one preferred embodiment of the present invention, the medium further comprises one or more compounds of formulas VI-1 to VI-9. in Each of R7 independently has one of the meanings indicated by R2A in technical solution 5, and w and x each represent 1 to 6 independently.
[0095] A mixture comprising at least one compound of formula V-9 is preferred.
[0096] In one preferred embodiment of the present invention, the medium further comprises one or more compounds of formulas VII-1 to VII-21. in 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. R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.
[0097] The medium according to the invention preferably contains 2 to 30% by weight, specifically 5 to 20% by weight, of triphenylene of formula VII-1 to VII-21.
[0098] Especially 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 compound VII-20, R preferably represents an alkyl or alkenyl group, specifically an alkyl group. In compound VII-21, R preferably represents an alkyl group.
[0099] If the Δn value of the mixture is ≥ 0.1, then terphenyl is preferably used in the mixture according to the invention. The 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.
[0100] Preferred embodiments are listed below:
[0101] a) A liquid crystal medium comprising at least one compound of formula Z-1 to Z-7, R and alkyl have the meanings indicated above for formula III.
[0102] b) A preferred liquid crystal medium according to the present invention comprises one or more substances containing tetrahydronaphthyl or naphthyl units, such as, for example, compounds of formulas N-1 to N-5. R1N and R2N each independently have the meaning indicated by R2A, preferably representing a straight-chain alkyl, straight-chain alkoxy, or straight-chain alkenyl group, and Z1 and Z2 each independently represent -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CH2-, or a single bond.
[0103] c) A preferred mixture comprises one or more compounds selected from the group consisting of difluorodibenzofurans of formula BC, benzo[a]ane of formula CR, fluorinated phenanthrenes of formulas PH-1 and PH-2, and fluorinated dibenzofurans of formulas BF-1 and BF-2. in RB1, RB2, RCR1, RCR2, R1, and R2 each independently have the meaning of R2A. c is 0, 1, or 2, and d represents 1 or 2. R1 and R2 preferably independently represent alkyl or alkoxy groups having 1 to 6 carbon atoms. Compounds of formula BF-1 and BF-2 should not be equivalent to one or more compounds of formula I.
[0104] The mixture according to the invention preferably contains, in an amount of 3 to 20% by weight, specifically 3 to 15% by weight, a compound of the formula BC, CR, PH-1, PH-2 and / or BF.
[0105] The preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5. in alkyl and alkyl* each independently represent a straight-chain alkyl group having 1 to 6 carbon atoms, and alkenyl and each of the alkenyl* groups independently represents a straight-chain alkenyl group having 2 to 6 carbon atoms.
[0106] The most preferred is a mixture containing one, two or three BC-2 compounds.
[0107] d) A preferred mixture contains one or more indane compounds of the formula In. in R11, R12, R13, each independently representing a straight-chain alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1 to 6 carbon atoms, R12 and R13 also indicate halogens, with F being preferred. express , i represents 0, 1, or 2.
[0108] Preferred In compounds are those of formulas In-1 to In-16 as indicated below: .
[0109] Compounds of formulas In-1, In-2, In-3 and In-4 are particularly preferred.
[0110] Compounds of formula In and sub-formulas In-1 to In-16 are preferably used in the mixtures according to the invention at a concentration of ≥ 5% by weight, specifically 5 to 30% by weight and most preferably 5 to 25% by weight.
[0111] e) A preferred mixture further comprises one or more compounds of formulas L-1 to L-5, , in R and R1 each have their own independent meaning as indicated for R2A in Formula IIA above, and alkyl means an alkyl group having 1 to 6 carbon atoms. The parameter s means 1 or 2.
[0112] The compounds of formulas L-1 to L-5 are preferably used at concentrations of 5 to 50% by weight, specifically 5 to 40% by weight, and most preferably 10 to 40% by weight.
[0113] f) A preferred mixture further comprises one or more compounds of formula IIA-Y. R11 and R12 have one of the meanings given in Equation I above, and L1 and L2 represent F or Cl in the same or different ways.
[0114] Preferred compounds of formula IIA-Y are selected from the group consisting of the following formulas. 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-.
[0115] The preferred IIA-Y compounds are selected from the group consisting of the following formulas: Alkoxy and Alkoxy* have the meanings defined above, and preferably represent methoxy, ethoxy, propoxy, butoxy, or pentoxy.
[0116] The liquid crystal medium according to the present 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 present invention may, as appropriate, contain one or more polymerizable compounds of formula P. P-Sp-A1-(Z1-A2)zR P The individual groups, independently of each other and in the same or different manner each time they appear, have the following meanings: P is a polymerizable group. Sp spacer groups or single bonds, A1 and A2 preferably have an aromatic, heteroaromatic, alicyclic, or heterocyclic group with 4 to 25 ring atoms. They may also contain a fused ring, and are unsubstituted or monosubstituted or polysubstituted. Z1 -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-, -CR0R00- or single bond, R0, R00 H, or an alkyl group having 1 to 12 carbon atoms, RH, L or P-Sp-, LF, Cl, -CN, P-Sp- or a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2- groups are substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, or -O-CO-O- as appropriate, such that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are substituted with P-Sp-, F, or Cl as appropriate. z 0, 1, 2, or 3, n1 1, 2, 3 or 4.
[0117] As used herein, the terms "active layer" and "switchable layer" refer to a layer, such as in an electro-optic display in an LC display, which contains one or more molecules with structural and optical anisotropy, such as (e.g.) LC molecules, which change their orientation upon external stimulation such as an electric or magnetic field, thereby causing a change in the layer's transmittance to polarized or unpolarized light.
[0118] As used herein, the terms "tilt" and "tilt angle" should be understood to mean the tilted orientation of LC molecules of the LC medium relative to the surface of the cell in an LC display (preferably a PSA display). The tilt angle here represents the average angle (< 90°) between the longitudinal molecular axis of the LC molecule (LC director) and the surface of the plane parallel to the outer plate forming the LC cell. Low tilt angle values (i.e., large deviations from 90°) correspond to large tilts here. Suitable methods for measuring the tilt angle are given in the examples. Unless otherwise indicated, the tilt angle values disclosed above and below are related to this measurement method.
[0119] As used herein, the terms "reactive liquid crystal primordium" and "RM" should be understood to mean a compound containing a liquid crystal primordium or liquid crystal framework and one or more functional groups connected thereto, which are suitable for polymerization and are also referred to as "polymerizable groups" or "P".
[0120] Unless otherwise stated, the term "polymerizable compound" as used herein should be understood to mean polymerizable monomeric compound.
[0121] As used herein, the term "low molecular weight compound" should be understood to mean a monomer and / or a compound not prepared by polymerization, as opposed to "polymeric compound" or "polymer".
[0122] 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 conditions typically applied to RM polymerization.
[0123] As used herein, the term "liquid crystal atom group" is known to those skilled in the art and described in the literature, and means a group that, due to the anisotropy of its attractive and repulsive interactions, substantially contributes to the formation of a liquid crystal (LC) phase in low molecular weight or polymeric substances. A compound containing a liquid crystal atom group (liquid crystal atom compound) does not necessarily possess an LC phase itself. A liquid crystal atom compound may also exhibit LC phase behavior only after being mixed with other compounds and / or after polymerization. Typical liquid crystal atom groups are, for example, rigid rod-shaped or disc-shaped units. An overview of the terms and definitions used in conjunction with liquid crystal atom or LC compounds can be found in Pure Appl. Chem. 2001, 73(5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem.
[2004] The information is given in , 116, 6340-6368.
[0124] As used herein, the terms "optically active" and "opposite" are synonymous for materials capable of inducing helical spacing in the nematic host material (also known as "opposite dopants").
[0125] The term “spacer group” (hereinafter also referred to as “Sp”) as used herein 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 group" means a flexible group, such as an alkyl group, that connects a liquid crystal matrix group and a polymerizable group in a polymerizable liquid crystal matrix compound.
[0126] In the preceding and following text, It represents the trans-1,4-extrinsic hexyl ring.
[0127] In groups In this system, the single bond between the two ring atoms can be attached to any empty position on the benzene ring.
[0128] In the preceding and following text, "organic group" refers to a carbon-based or hydrocarbon-based group.
[0129] "Carbon-based" refers to a monovalent or polyvalent organic group containing at least one carbon atom, wherein the group does not contain other atoms (such as -C≡C-) or, as appropriate, 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-based" indicates a carbon-based group that additionally contains one or more H atoms and, as appropriate, one or more heteroatoms such as N, O, S, B, P, Si, Se, As, Te, or Ge.
[0130] "Halogen" refers to F, Cl, Br or I, preferably F or Cl.
[0131] -CO-, -C(=O)-, and -C(O)- represent carbonyl groups, that is, .
[0132] The carbonyl or hydrocarbon group can be saturated or unsaturated. Unsaturated groups are, for example, aryl, alkenyl, or alkynyl. Carbonyl or hydrocarbon groups having more than 3 carbon atoms can be straight-chain, branched-chain, and / or cyclic, and may also contain helical or fused rings.
[0133] The terms "alkyl", "aryl", and "heteroaryl" also encompass polyvalent groups, such as alkyl, aryl, and heteroaryl.
[0134] The term "aryl" means an aromatic carbonyl group or a group derived therefrom. The term "heteroaryl" means an "aryl" as defined above containing one or more heteroatoms, preferably selected from N, O, S, Se, Te, Si and Ge.
[0135] Preferred carbonyl and hydrocarbon groups are straight-chain, branched-chain, or cyclic alkyl, alkenyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, and alkoxycarbonyloxy groups having 1 to 40, more preferably 1 to 20, and most preferably 1 to 12 C atoms, which are optionally substituted; aryl or aryloxy groups having 5 to 30, more preferably 6 to 25 C atoms, which are optionally substituted; or alkylaryl, arylalkyl, alkylaryloxy, arylalkoxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy, and aryloxycarbonyloxy groups having 5 to 30, more preferably 6 to 25 C atoms, which are optionally substituted, wherein one or more C atoms may also be replaced by heteroatoms preferably selected from N, O, S, Se, Te, Si, and Ge.
[0136] Preferred carbon and hydrocarbon groups are C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 allyl, C4-C20 alkyldienyl, C4-C20 polyalkenyl, C6-C20 cycloalkyl, C4-C15 cycloalkenyl, C6-C30 aryl, C6-C30 alkylaryl, C6-C30 arylalkyl, C6-C30 alkylaryloxy, C6-C30 arylalkoxy, C2-C30 heteroaryl, and C2-C30 heteroaryloxy.
[0137] Preferred are C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C6-C25 aryl and C2-C25 heteroaryl.
[0138] More preferably, the carbonyl and hydrocarbon groups are straight-chain, branched-chain, or cyclic alkyl groups having 1 to 20, more preferably 1 to 12, C atoms, which are unsubstituted or monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and one or more of the non-adjacent CH2 groups are independently substituted with -C(Rx)=C(Rx)-, -C≡-, -N(Rx)-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, or -O-CO-O- in such a way that the O and / or S atoms are not directly connected to each other.
[0139] Rx preferably represents H, F, Cl, CN, a straight-chain, branched-chain, or cyclic alkyl chain having 1 to 25 C atoms, wherein one or more non-adjacent C atoms may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O-, and one or more H atoms may be substituted with F or Cl, or represents an aryl or aryloxy group having 6 to 30 C atoms, or a heteroaryl or heteroaryloxy group having 2 to 30 C atoms, substituted as appropriate.
[0140] Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, dibutyl, tert-butyl, 2-methylbutyl, n-pentyl, dibutyl, 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.
[0141] Preferred alkenyl groups include, for example, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, etc.
[0142] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octyynyl, etc.
[0143] Preferred alkoxy groups include, for example, methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, secondary butoxy, tertiary butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, etc.
[0144] Preferred amino groups include, for example, dimethylamino, methylamino, methylaniline, aniline, etc.
[0145] Aryl and heteroaryl groups can be monocyclic or polycyclic, that is, they can contain one ring (such as, for example, phenyl) or two or more rings, which can be fused (such as, for example, naphthyl) or covalently bonded (such as, for example, biphenyl), or contain a combination of fused rings and bonded rings. Heteroaryl groups contain one or more heteroatoms, preferably selected from O, N, S and Se.
[0146] Preferred are monocyclic, bicyclic, or tricyclic aryl groups having 6 to 25 carbon atoms and monocyclic, bicyclic, or tricyclic heteroaryl groups having 5 to 25 ring atoms, which may contain fused rings and be substituted as appropriate. Furthermore, 5-, 6-, or 7-membered aryl and heteroaryl groups are more preferred, wherein one or more CH groups may be substituted with N, S, or O in a manner that prevents the O and / or S atoms from being directly connected to each other.
[0147] Preferred aryl groups include, for example, phenyl, biphenyl, biphenylene, [1,1':3',1'']biphenyl-2'-yl, naphthyl, anthracene, binaphthalene, phenanthrene, 9,10-dihydro-phenanthrene, pyrene, dihydropyrene. Perylene, condensed tetraphenylene, condensed pentaphenylene, benzo[a]pyrene, fu, indene, indene-fu, spirodifu, etc.
[0148] 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, acetazole, isoacetazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-acediazole, 1,2,4-acediazole, 1,2,5-acediazole, 1,3,4-acediazole, and 1,2,3-thiadiazole. 1,2,4-Thiadiazole, 1,2,5-Thiadiazole, 1,3,4-Thiadiazole; a 6-membered ring, such as pyridine, pyrimidine, pyrimidine, 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 a fused group, such as indole, isoindole, indole Indazole, benzimidazole, benzotriazole, purine, naphthioimidazole, phenanthreneimidazole, pyridinimidazole, pyridoxineimidazole, quinolinimidazole, benzoxazole, naphthioimidazole, anthraquinone, phenanthreneimidazole, isobenzoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7, 8-Quinoline, benzoisoquinoline, acridine, phenanthrene, phenanthrene, benzopyrimidine, quinoline, phenanthrene, naphthidine, azacarbazole, benzocarbine, phenanthrene, phenanthrene, 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 ...
[0149] The aryl and heteroaryl groups mentioned above and below may also be substituted with alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl or other aryl or heteroaryl groups.
[0150] (Non-aromatic) alicyclic and heterocyclic groups encompass both saturated rings (i.e., rings containing only single bonds) and partially unsaturated rings (i.e., rings that may also contain multiple bonds). Heterocyclic groups contain one or more heteroatoms, preferably selected from Si, O, N, S, and Se.
[0151] (Non-aromatic) alicyclic and heterocyclic groups can be monocyclic, i.e., containing only one ring (such as, for example, cyclohexane); or polycyclic, i.e., containing multiple rings (such as, for example, decahydronaphthalene or bicyclooctane). Saturated groups are particularly preferred. Furthermore, monocyclic, bicyclic, or tricyclic groups having 5 to 25 ring atoms are more preferred, containing fused rings and, where appropriate, substituted rings. Furthermore, 5-, 6-, 7-, or 8-membered carbocyclic groups are more preferred, wherein one or more C atoms may be substituted with Si, and / or one or more CH groups may be substituted with N, and / or one or more non-adjacent CH2 groups may be substituted with -O- and / or -S-.
[0152] Preferred alicyclic and heterocyclic groups are, for example, 5-membered groups such as cyclopentane, tetrahydrofuran, tetrahydrothiofuran, and pyrrolidine; 6-membered groups such as cyclohexane, cyclohexylsilane, cyclohexene, tetrahydropiperan, tetrahydrothiopiperan, 1,3-dimethylalkane, 1,3-dithiamane, 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-methylbridged indane-2,5-diyl.
[0153] Preferred substituents are, for example, groups that promote dissolution, such as alkyl or alkoxy groups; electron-withdrawing groups, such as fluorine, nitro or nitrile groups; or substituents that increase the glass transition temperature (Tg) of the polymer, specifically bulky groups, such as tert-butyl or, where appropriate, substituted aryl groups.
[0154] Preferred substituents, also referred to as "L" below, include, for example, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(Rx)2, -C(=O)Y1, -C(=O)Rx, -N(Rx)2, and straight-chain or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy, or alkoxy carbonyloxy groups, each having 1 to 25 C atoms, wherein one or more H atoms may be replaced by F or Cl, by a silicon group having 1 to 20 Si atoms, or by an aryl group having 6 to 25, preferably 6 to 15, C atoms, as appropriate. Wherein Rx represents H, F, Cl, CN, or a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2- groups are substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- as appropriate, such that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are substituted with F, Cl, P-, or P-Sp- as appropriate. Y1 represents halogen.
[0155] "Substituted silyl or aryl" preferably means substituted with halogen, -CN, R0, -OR0, -CO-R0, -CO-O-R0, -O-CO-R0 or -O-CO-O-R0, where R0 represents H or an alkyl group having 1 to 20 C atoms.
[0156] Preferred substituents L are, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and others are phenyl.
[0157] A1 and A2 are excellent representations Where L has one of the meanings indicated above and r represents 0, 1, 2, 3 or 4, specifically Better , The polymerizable group P is a group suitable for polymerization reactions (such as, for example, radical or ionic chain polymerization, addition polymerization, or polycondensation) or similar polymer reactions (such as addition or condensation to the host polymer chain). Preferably, it is a group suitable for chain polymerization, specifically a group containing a C=C double bond or a -C≡C- linkage, and a group suitable for ring-opening polymerization, such as an oxetane or epoxy group. The preferred group P is selected from the following compositional groups: CH2=CW1-CO-O-, CH2=CW1-CO-, , CH2=CW2-(O)k3-, CW1=CH-CO-(O)k3-, CW1=CH-CO-NH-, CH2=CW1-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-CW2W3-, HS-CW2W3-, HW2N-, HO-CW2W3-NH-, CH2=CW1-CO-NH-, CH2=CH-(COO)k1-Phe-(O)k2-, CH2=CH-(CO)k1-Phe-(O)k2-, Phe-CH=CH- HOOC-, OCN-, and W4W5W6Si-, wherein W1 represents H, F, Cl, CN, CF3, a phenyl or alkyl group having 1 to 5 carbon atoms, specifically H, F, Cl, or CH3; W2 and W3 each independently represent H or an alkyl group having 1 to 5 carbon atoms, specifically H, methyl, ethyl, or n-propyl; W4, W5, and W6 each independently represent Cl, an oxaalkyl or oxacarbonylalkyl group having 1 to 5 carbon atoms; W7 and W8 each independently represent H, Cl, or an alkyl group having 1 to 5 carbon atoms; Phe represents 1,4-epenylphenyl, which, as appropriate, is substituted with one or more groups L as defined above, other than P-Sp-; k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10. The optimal group P is selected from the following compositional groups: CH2=CW1-CO-O-, CH2=CW1-CO-, , CH2=CW2-O-, CH2=CW2-, CW1=CH-CO-(O)k3-, CW1=CH-CO-NH-, CH2=CW1-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=CW1-CO-NH-, CH2=CH-(COO)k1-Phe-(O)k2-, CH2=CH-(CO)k1-Phe-(O)k2-, Phe-CH=CH- and W4 W5W6Si-, where W1 represents H, F, Cl, CN, CF3, a phenyl or alkyl group having 1 to 5 carbon atoms, specifically H, F, Cl, or CH3; W2 and W3 each independently represent H or an alkyl group having 1 to 5 carbon atoms, specifically H, methyl, ethyl, or n-propyl; W4, W5, and W6 each independently represent Cl, an oxaalkyl or oxacarbonylalkyl group having 1 to 5 carbon atoms; W7 and W8 each independently represent H, Cl, or an alkyl group having 1 to 5 carbon atoms; Phe represents 1,4-elongylphenyl; k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.
[0158] The preferred group P is selected from the following group: CH2=CW1-CO-O-, specifically CH2=CH-CO-O-, CH2=C(CH3)-CO-O-, and CH2=CF-CO-O-, as well as CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, and so on. .
[0159] The polymerizable group P is preferably selected from the group consisting of: vinyloxy groups, acrylates, methacrylates, fluoroacrylates, chloroacrylates, oxides and epoxides, preferably selected from acrylates and methacrylates.
[0160] If the spacer group Sp is different from the single bond, it preferably has the formula Sp"-X, such that each individual group P-Sp- conforms to the formula R-Sp"-X"-, where "Sp" indicates a straight-chain or branched alkyl group having 1 to 20, preferably 1 to 12, carbon atoms, which may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and wherein one or more non-adjacent CH2 groups may be independently substituted with -O-, -S-, -NH-, -N(R0)-, -Si(R0R00)-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R00)-CO-O-, -O-CO-N(R0)-, -N(R0)-CO-N(R00)-, -CH=CH-, or -C≡C-. "X" represents -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R0)-, -N(R0)-CO-, -N(R0)-CO-N(R00)-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR0-, -CY2=CY3-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or a single bond. R0 and R00 each independently represent H or an alkyl group having 1 to 20 carbon atoms, and Y2 and Y3 each independently represent H, F, Cl, or CN.
[0161] X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR0-, -NR0-CO-, -NR0-CO-, or a single bond.
[0162] 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 -(SiR0R00-O)p1-, where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R0 and R00 have the meanings indicated above.
[0163] The 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 indicated above.
[0164] In all cases, the preferred group Sp" is linear ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, octadecyl, ethyloxyethyl, methyleneoxybutyl, ethylthioethyl, ethyl-N-methyliminoethyl, 1-methylalkyl, vinyl, propylene, and butenyl.
[0165] In one preferred embodiment of the present invention, compounds of formula P and its sub-formulas contain spacer groups Sp substituted with one or more polymerizable groups P, such that the group Sp-P corresponds to Sp(P)s, where s ≥ 2 (branched polymerizable groups).
[0166] The preferred P compound according to this preferred embodiment is a compound in which s is 2, that is, a compound containing the group Sp(P)2. The preferred P compound according to this preferred embodiment contains a group selected from the following formula: -X-alkyl-CHPP S1 -X-alkyl-CH((CH2)aaP)((CH2)bbP) S2 -XN((CH2)aaP)((CH2)bbP) S3 -X-alkyl-CHP-CH2-CH2P S4 -X-alkyl-C(CH2P)(CH2P)-CaaH2aa+1 S5 -X-alkyl-CHP-CH2P S6 -X-alkyl-CPP-CaaH2aa+1 S7 -X-alkyl-CHPCHP-CaaH2aa+1 S8 Where P is defined as in equation P, Alkyl refers to a straight-chain or branched alkyl group with a single bond or 1 to 12 carbon atoms, which is unsubstituted or monosubstituted or polysubstituted with F, Cl, or CN, and in which one or more non-adjacent CH2 groups are independently substituted with -C(R0)=C(R0)-, -C≡C-, -N(R0)-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O-, where R0 has the meaning indicated above. aa and bb each independently represent 0, 1, 2, 3, 4, 5, or 6. X has one of the meanings indicated by "X", and is preferably O, CO, SO2, O-CO-, CO-O or a single bond.
[0167] Preferred spacer groups Sp(P)2 are selected from formulas S1, S2 and S3.
[0168] The excellent spacer group Sp(P)2 is selected from the following formulas: -CHPP S1a -O-CHPP S1b -CH2-CHPP S1c -OCH2-CHPP S1d -CH(CH2-P)(CH2-P) S2a -OCH(CH2-P)(CH2-P) S2b -CH2-CH(CH2-P)(CH2-P) S2c -OCH2-CH(CH2-P)(CH2-P) S2d -CO-NH((CH2)2P)((CH2)2P) S3a
[0169] 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, oxy groups and epoxides, most preferably selected from acrylates and methacrylates.
[0170] 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 preferably represent acrylates or methacrylates, most preferably methacrylates.
[0171] In compounds of formula P and its sub-formulas as described above and below, R preferably represents P-Sp-.
[0172] More preferably, compounds of formula P and its sub-formulas 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.
[0173] 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.
[0174] More preferably, compounds of formula P and its sub-formulas as described above and below, wherein at least one group Sp 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, wherein 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.
[0175] The preferred group in formula P, -A1-(Z-A2)z-, is selected from the following formulas. At least one benzene ring is substituted with at least one L group, and the benzene ring may be additionally substituted with one or more L or P-Sp- groups, depending on the case.
[0176] Preferred compounds of formula P and its sub-formulas are selected from the following preferred embodiments, including any combination thereof: - All groups P in the compound have the same meaning. - -A1-(Z-A2)z- is selected from formulas A1, A2, and A5. - The compound contains exactly two polymerizable groups (represented by the group P). - The compound contains exactly three polymerizable groups (represented by the group P). - P is selected from the group consisting of: acrylates, methacrylates, and oxides, preferably acrylates or methacrylates. - P represents methacrylate. - All Sp groups are single bonds. - At least one of the Sp groups is a single bond and at least one of the Sp groups is different from a single bond. - When it differs from a single bond, Sp is -(CH2)p2-, -(CH2)p2-O-, -(CH2)p2-CO-O-, or -(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. - 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. - R represents P-Sp-, - R does not indicate or contains a polymerizable group. - R does not represent or contain a polymerizable group, and represents a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2- groups are substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- as appropriate, such that the O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are substituted with F, Cl, or La as appropriate. - L or L' indicates F, Cl, or CN. - L is F.
[0177] Suitable and preferred compounds of formula P are selected from the following: Some of these groups have the following meanings: P1, P2, and P3 each independently represent acrylate or methacrylate groups. Sp1, Sp2, and Sp3 each independently represent a single bond or a spacer group having one of the meanings indicated by Sp above and below, and preferably 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. Additionally, one or more of the groups P1-Sp1-, P2-Sp2-, and P3-Sp3- can represent Raa, provided that at least one of the P1-Sp1-, P2-Sp2-, and P3-Sp3- groups is different from Raa. Raa represents H, F, Cl, CN, or a straight-chain or branched alkyl group having 1 to 25 carbon atoms, wherein one or more non-adjacent CH2 groups may be independently substituted with C(R0)=C(R00)-, -C≡C-, -N(R0)-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, and -O-CO-O-, and wherein one or more H atoms may be substituted with F, Cl, CN, or P1-Sp1-, preferably straight-chain or branched alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy (wherein the alkenyl and alkynyl groups have at least two carbon atoms and the branched groups have at least three carbon atoms) as appropriate, with monofluorination or polyfluorination. R0 and R00, each when appearing independently and identically or differently, represent H or an alkyl group having 1 to 12 carbon atoms. Ry and Rz each independently represent H, F, CH3, or CF3. X1, X2, and X3 each independently represent -CO-O-, -O-CO-, or a single bond. Z1 represents -O-, -CO-, -C(RyRz)-, or -CF2CF2-. Z2 and Z3 each independently represent -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2)n-, where n is 2, 3, or 4. L, in each occurrence, may represent F, Cl, CN, or a straight or branched chain having 1 to 12 C atoms, and, where applicable, a monofluorinated or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, or alkoxycarbonyloxy group, preferably F. L' and L" each independently represent H, F, or Cl. k represents 0 or 1, r represents 0, 1, 2, 3, or 4. s represents 0, 1, 2, or 3. t represents 0, 1, or 2. x represents 0 or 1.
[0178] The preferred compounds are those of formulas P2, P13, P17, P22, P23, P24, P30, P31 and P32.
[0179] More preferably, tri-reactive compounds P15 to P30, specifically P17, P18, P19, P22, P23, P24, P25, P26, P30, P31 and P32.
[0180] In compounds of formulas P1 to P32, the group The better location is , Wherein L has the same or different 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-, most preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, even more preferably F, Cl, CH3, OCH3, COCH3 or OCF3, especially F or CH3.
[0181] The medium according to the invention comprises one or more antagonistic dopants. Preferably, the absolute value of the helical twisting power (HTP) of these antagonistic dopants is in the range of 1 μm⁻¹ to 150 μm⁻¹, more preferably in the range of 10 μm⁻¹ to 100 μm⁻¹. In the case where the medium comprises two or more antagonistic dopants, their HTP values may have opposite signs. This condition is preferred for some specific embodiments because it allows for some degree of compensation for the antagonism of individual compounds, and thus can be used to compensate for various temperature-dependent characteristics of the resulting medium in the device. However, in general, it is preferable that the HTP values of all antagonistic compounds present in the medium according to the invention preferably have the same sign.
[0182] Preferably, the dopant present in the medium according to this application is a liquid crystal primary compound, and most preferably, it independently exhibits a mesophase.
[0183] In one preferred embodiment of the present invention, the medium comprises two or more palmar compounds, each having the same HTP algebraic notation.
[0184] The temperature dependence of HTP in individual compounds can be high or low. The temperature dependence of the distance between media can be compensated by mixing compounds with different HTP temperature dependencies in corresponding ratios.
[0185] For optically active components, those skilled in this technique can use a wide range of antagonistic dopants, 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).
[0186] Particularly suitable dopants are compounds containing one or more antiplatelet groups and one or more liquid crystal primitive groups, or one or more aromatic or alicyclic groups that form liquid crystal primitive groups with the antiplatelet groups.
[0187] Suitable anticoiled groups are, for example, anticoiled branched chain hydrocarbons, anticoiled ethylene glycols, binaphthols, or dioxanes, and are also monovalent or polyvalent anticoiled groups selected from the group consisting of: sugar derivatives, sugar alcohols, sugar acids, lactic acids, anticoiled substituted diols, steroid derivatives, terpene derivatives, amino acids, or sequences of a few, preferably 1 to 5 amino acids.
[0188] Preferred anticoagulant groups are sugar derivatives, such as glucose, mannose, galactose, fructose, arabinose, and dextrose; sugar alcohols, such as (e.g.) sorbitol, mannitol, iditol, galactitol, or their dehydrated derivatives, specifically disohydrated hexotols, such as disohydrated sorbitol (1,4:3,6-disohydrated-D-sorbitol, isosorbitol), disohydrated mannitol (isosorbitol), or disohydrated iditol (iso-iditol); and sugar acids, such as (e.g.) gluconic acid, gulonic acid, and ketogulonic acid. acid); a diol group with alkyl substituted groups, such as (e.g.) monoethylene glycol or oligoethylene glycol or propylene glycol, wherein one or more CH2 groups are substituted with alkyl or alkoxy groups; amino acids, such as (e.g.) alanine, valine, phenylglycine or phenylalanine, or a sequence of 1 to 5 such amino acids; steroid derivatives, such as (e.g.) cholesterol or cholic acid groups; terpene derivatives, such as (e.g.) menthyl, neomenthyl, campheyl, pinenyl... pineyl), terpineyl, isolongifolyl, fenchyl, carreyl, myrthenyl, nopyl, geraniyl, linaloyl, neryl, citronellyl, or dihydrocitronellyl.
[0189] The medium according to the invention preferably comprises an antipodal dopant selected from the group of known antipodal dopants. Suitable antipodal groups and liquid crystal primitive antipodal 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.
[0190] Preferably, the palmar compound used according to the present invention is selected from the group of formulas shown below.
[0191] Preferably, palmar dopants are selected from the group consisting of compounds of the following formulas: Al to A-III and A-Ch. in Ra11, Ra12, and Rb12 independently represent alkyl groups having 1 to 15 carbon atoms, wherein one or more non-adjacent CH2 groups are each independently substituted with -C(Rz)=C(Rz)-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -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 substituted with F, Cl, Br, I, or CN, preferably alkyl, more preferably n-alkyl, the limiting condition being that Ra12 and Rb12 are different. Ra21 and Ra22 independently represent alkyl groups having 1 to 15 carbon atoms, wherein one or more non-adjacent CH2 groups are each independently substituted with -C(Rz)=C(Rz)-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -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 substituted with F, Cl, Br, I, or CN, preferably both being alkyl groups, more preferably being n-alkyl groups. Ra31, Ra32, and Rb32 independently represent straight-chain or branched alkyl groups having 1 to 15 C atoms, wherein one or more non-adjacent CH2 groups are each independently substituted with C(Rz)=C(Rz)-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- such that the O and / or S atoms are not directly connected to each other, and wherein one or more H atoms are substituted with F, Cl, Br, I, or CN, preferably alkyl, more preferably n-alkyl, wherein Ra32 and Rb32 are different; Rz represents H, CH3, F, Cl, or CN, with H or F being preferred. R8 has one of the meanings of Ra11 given above, preferably an alkyl group, and more preferably a n-alkyl group having 1 to 15 carbon atoms. Z8 represents -C(O)O-, CH2O, CF2O, or a single bond, with -C(O)O- being preferred. A11 As defined below A12, or alternatively represented A12 express , The better location is , in L12, each time appearing independently, represents a halogen, CN, or an alkyl, alkenyl, alkoxy, or alkenyloxy group having up to 12 carbon atoms, wherein one or more H atoms are halogenated as appropriate, preferably methyl, ethyl, Cl, or F, with F being particularly preferred. A21 express A22 It has the meaning given for A12. A31 It has the meaning given in A11. Or alternatively represent A32 It has the meaning given for A12. n2 is 0, 1, or 2 each time it appears, and n3 is 1, 2, or 3, and r can be 0, 1, 2, 3 or 4.
[0192] Dopants selected from the group consisting of compounds of the following formula are preferred: in m is an integer from 1 to 9, either identically or differently, in each occurrence. n is an integer from 2 to 9, either the same or different, each time it appears.
[0193] The preferred compound of formula A is compound of formula A-III.
[0194] Preferred dopants are isosorbide, isomannitol, or derivatives of iso-idotitol of formula A-IV: Among them, groups for (desorbitol), (disohydrated mannitol), or (disohydrated idutitol), The preferred option is dehydrated sorbitol. And ethylene glycols such as (for example) diphenylethylene glycol (hydrobenzoin), specifically, liquid crystal atom-hydrobenzoin derivatives of formula AV: Including unshown (S,S) mirror isomers, in and Each is independently 1,4-epenylphenyl, which can also be mono-, di-, or tri-substituted; or 1,4-epenylcyclohexyl. L is H, F, Cl, CN, or, as appropriate, a halogenated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkoxycarbonyloxy group having 1 to 7 carbon atoms. c is 0 or 1. X is CH2 or -C(O)-. Z0 is -COO-, -OCO-, -CH2CH2- or a single bond, and R0 is an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, or alkyl carbonyloxy group having 1 to 12 carbon atoms.
[0195] Examples of compounds of formula IV are:
[0196] Compounds of formula A-IV are described in WO 98 / 00428. Compounds of formula AV are described in GB-A-2,328,207.
[0197] Preferred dopants are palmate binaphthyl derivatives, as described in WO 02 / 94805; palmate binaphthol acetal derivatives, as described in WO 02 / 34739; palmate TADDOL derivatives, as described in WO 02 / 06265; and palmate dopants having at least one fluorinated bridging group and terminal or central palmate groups, as described in WO 02 / 06196 and WO 02 / 06195.
[0198] The preferred type is the palmar compound of formula A-VI. in X1, X2, Y1, and Y2 are each independently F, Cl, Br, I, CN, SCN, SF5, straight-chain or branched alkyl groups having 1 to 25 carbon atoms, unsubstituted or monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and wherein one or more non-adjacent CH2 groups are independently substituted with -O-, -S-, -NH-, -NRx-, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH-, or -C≡C-, such that the O and / or S atoms are not directly connected to each other, and are polymerizable groups or cycloalkyl or aryl groups having up to 20 carbon atoms, which may be halogenated, preferably F, or monosubstituted or polysubstituted with polymerizable groups, as appropriate. x1 and x2 are each independently 0, 1, or 2. y1 and y2 are each independently 0, 1, 2, 3 or 4. B1 and B2 are each independently an aromatic or partially or fully saturated aliphatic six-membered ring, wherein one or more CH groups may be substituted with N and one or more non-adjacent CH2 groups may be substituted with O or S. W1 and W2 are each independently -Z1-A1-(Z2-A2)mR, and one of them is either R1 or A3, but they are not both H at the same time. for or , U1 and U2 are each independently CH2, O, S, CO, or CS. V1 and V2 are each independently (CH2)n, where one to four non-adjacent CH2 groups can be substituted with O or S, or single bonds, and n is 1, 2, or 3. Z1 and Z2 are each independently a combination of two of the following groups: -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NRx-, -NRx-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-, etc., wherein there are no two O and / or S and / or N atoms directly bonded to each other, preferably -CH=CH-COO- or -COO-CH=CH-, or a single bond. Rx represents an alkyl group having 1 to 6 carbon atoms. A1, A2, and A3 are each independently 1,4-epoxyphenyl, wherein one or two non-adjacent CH groups may be substituted with N; 1,4-epoxycyclohexyl, wherein one or two non-adjacent CH2 groups may be substituted with O or S; 1,3-dioxapentane-4,5-diyl; 1,4-epoxycyclohexenyl; 1,4-bicyclo[2.2.2]epoxyoctyl; piperidine-1,4-diyl; naphth-2,6-diyl; decahydronaphth-2,6-diyl; or 1,2,3,4-tetrahydronaphth-2,6-diyl, wherein each of these groups may be mono- or poly-substituted with L, and furthermore, A1 is a single bond. L is a halogen atom, preferably F, CN, NO2, or an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, or alkoxy carbonyloxy group having 1 to 7 carbon atoms, wherein one or more H atoms may be replaced by F or Cl. m is independently 0, 1, 2, or 3 in each case, and R and R1 are each independently H, F, Cl, Br, I, CN, SCN, SF5, straight-chain or branched alkyl groups having 1 or 3 to 25 carbon atoms, which may be monosubstituted or polysubstituted by F, Cl, Br, I or CN as appropriate, and one or more non-adjacent CH2 groups may be substituted by -O-, -S-, -NH-, -NR0-, -CO-, -COO-, -OCO-, -O-COO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C-, wherein there are no two O and / or S atoms directly bonded to each other, or polymerizable groups.
[0199] The preferred one is the palmar binaphthalene derivative of formula A-VI-1. Where rings B, R0, and Z0 are as defined for equations A-IV and AV, and b is 0, 1, or 2. Specifically, those selected from the following formulas A-VI-1a to A-VI-1c: Where rings B, R0, and Z0 are as defined with respect to equation A-VI-1, and R0, as defined for formulas A-IV, is either H or an alkyl group having 1 to 4 carbon atoms, and b is 0, 1, or 2. Specifically, Z0 is either -OCO- or a single bond.
[0200] The concentration of one or more palm-shaped 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 palm-shaped dopants S-4011 or R-4011 (both from Merck KGaA) and to palm-shaped dopants having the same or similar HTP. For palm-shaped dopants with higher or lower absolute HTP values compared to S-4011, these preferred concentrations must be reduced, respectively, and increased proportionally according to the ratio of their HTP value to the HTP value of S-4011.
[0201] The distance p between the LC media or the main mixture according to the present invention is preferably in the range of 5 to 50 μm, more preferably 8 to 30 μm, and even more preferably 10 to 20 μm.
[0202] Preferably, the medium according to the invention comprises a stabilizer selected from the group of compounds of formulas ST-1 to ST-19. in RST represents H, an alkyl or alkoxy group having 1 to 15 carbon atoms, wherein one or more of these groups are CH2 groups that allow the O atoms to be independently bonded to each other via -C≡C-, -CF2O-, -OCF2-, -CH=CH-, etc., without direct connection between the O atoms. The substitutions include -O-, -CO-O-, and -O-CO-, and one or more H atoms may be halogenated. express ZST represents each of the following independently: -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. L1 and L2 each independently represent F, Cl, CF3, or CHF2. p represents 1 or 2, q represents 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
[0203] Among the compounds of formula ST, compounds of the following formula are particularly preferred. Where n = 1, 2, 3, 4, 5, 6, or 7, preferably n = 1 or 7. Where n = 1, 2, 3, 4, 5, 6, or 7, preferably n = 3. Where n = 1, 2, 3, 4, 5, 6, or 7, preferably n = 3.
[0204] In compounds of formula ST-3a and ST-3b, n preferably represents 3. In compound of formula ST-2a, n preferably represents 7.
[0205] The preferred mixture according to the present invention comprises one or more stabilizers from the group of compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1 and ST-12:
[0206] Based on the mixture, the compounds of formulas ST-1 to ST-19 are preferably present in the liquid crystal mixture according to the present invention in an amount of 0.005% to 0.5%.
[0207] If the mixture according to the invention comprises two or more compounds from the group of compounds of formula 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%.
[0208] However, based on the mixtures according to the present invention, the total proportion of compounds of formulas ST-1 to ST-18 should not exceed 2%.
[0209] The mixture according to the invention preferably contains - One or more compounds of formula I, preferably selected from formulas I-1 to I-14, most preferably I-1 to I-5, wherein the total concentration is preferably in the range of > 0% to 20%, more preferably 2% to 15% or 3% to 14%, and even more preferably 8% to 12%. and / or - One or more IIA compounds, preferably in the range of 3% to 25%, more preferably 6% to 20%, and even more preferably 8% to 15%; and / or - One or more compounds of formulas IIA and IIB, wherein the total concentration is preferably in the range of 5% to 30%, more preferably 8% to 25%, and even more preferably 10% to 20%; and / or - One or more compounds of formula I and formula IV, wherein the total concentration is preferably in the range of 35% to 75%, more preferably 40% to 65%, and even more preferably 45% to 55%; and / or - One or more compounds of formulas I, IV and IVb, wherein the total concentration is preferably in the range of 35% to 70%, more preferably 40% to 65%, and even more preferably 45% to 60%; and / or - One or more compounds of formula IIA and / or IIB and III, preferably III-2 and / or III-3, wherein the total concentration is preferably in the range of 10% to 40%, more preferably 12% to 35%, and even more preferably 15% to 30%.
[0210] Specifically, the medium includes - One or more compounds CY-n-Om, specifically CY-3-O4, CY-5-O4 and / or CY-3-O2, wherein the total concentration is preferably in the range of 1% to 20%, more preferably 2% to 15%, most preferably 3% to 10% or 3% to 8%; and / or - CPY-n-Om, specifically CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably at a concentration > 5%, specifically 7% to 20%. and / or - One or more compounds CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, preferably at a concentration > 3%, specifically 5 to 15%. and / or - CLY-n-Om, preferably CLY-2-O4, CLY-3-O2 and / or CLY-3-O3, having a concentration preferably > 5% on a total basis, specifically 15 to 30%, and most preferably 20 to 25%; and / or - The concentrations of CLY-n-Om and CY-n-Om, on a total mixture basis, are preferably 10% to 80%. and / or - 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%, more preferably 15 to 33%, based on the overall mixture. and / or - CC-VV, on a total mixture basis, preferably has a concentration of 5 to 50%. and / or - 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 even more preferably 20% to 30%. and / or - One or more compounds of the form B-nO-Om and / or B(S)-nO-Om, specifically compound B(S)-2O-O5, having a concentration preferably in the range of 2 to 10%, and compounds CC-3-V1 and / or compound CC-4-V1, having a total concentration in the range of 10 to 30%, preferably 15 to 20%. and / or - 0.1% to 3% of the compound PPGU-3-F and / or - > 0% to 10% of the compound PGIY-nO-Om.
[0211] 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 in technical solution 1 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.
[0212] Advantageously, the liquid crystal medium according to the present invention preferably has a nematic phase with a temperature range of ≤ -20°C to ≥ 70°C, more preferably ≤ -30°C to ≥ 80°C, and extremely preferably ≤ -40°C to ≥ 90°C.
[0213] The medium according to the present invention has a clarification temperature of 70°C or higher, preferably 74°C or higher.
[0214] The phrase "possessing a nematic phase" in this paper means, on the one hand, that no smectic phase or crystallization is observed at the corresponding temperature at low temperatures, and on the other hand, that the nematic phase does not clarify upon heating. Low-temperature studies were conducted at the corresponding temperatures using a flow-rate viscometer and verified by storing the medium in a test unit with a layer thickness corresponding to the electro-optical application for at least 100 hours. If the storage stability at -20°C in the corresponding test unit is 1000 h or longer, the medium is considered stable at this temperature. The corresponding times are 500 h and 250 h at -30°C and -40°C, respectively. At high temperatures, the clarifying point was measured in a capillary using conventional methods.
[0215] The liquid crystal mixture preferably has a nematic phase range of at least 60 K and a flow viscosity ν20 of up to 30 mm2 s-1 at 20 °C.
[0216] The mixture is nematic at temperatures of -20°C or lower, preferably -30°C or lower, and most preferably -40°C or lower.
[0217] The birefringence Δn value of liquid crystal mixtures is typically between 0.07 and 0.16, preferably between 0.08 and 0.15, and extremely preferably between 0.09 and 0.14.
[0218] In one preferred embodiment of the invention, the birefringence of the medium is in the range of 0.085 to 0.105, more preferably 0.090 to 0.100, and specifically 0.092 to 0.094.
[0219] The liquid crystal mixture according to the present invention has a dielectric anisotropy Δε of -1.5 to -8.0, preferably -3.0 to -5.0, and specifically -3.5 to -4.5.
[0220] The rotational viscosity γ1 at 20°C is preferably ≤ 160 mPa·s, specifically ≤ 130 mPa·s.
[0221] The medium according to the invention has a mean elastic constant Kavg of 15 or greater, preferably 15.3 or greater, most preferably 15.4 or greater, and specifically 15.5 or greater than 15.6.
[0222] The medium according to the invention has a value 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 specifically 6.8 or less.
[0223] Furthermore, the liquid crystal medium of the present invention has a high voltage retention rate in the liquid crystal cell.
[0224] Generally speaking, compared to liquid crystal media with higher address voltage or threshold voltage, liquid crystal media with lower address voltage or threshold voltage exhibit lower voltage retention rate, and vice versa.
[0225] For the purposes of this invention, the term "dielectrically positive compound" refers to a compound with Δε > 1.5, the term "dielectrically neutral compound" refers to a compound with -1.5 ≤ Δε ≤ 1.5, and the term "dielectrically negative compound" refers to a compound with Δε < -1.5. The dielectric anisotropy of the compound is determined here by dissolving 10% of the compound in a liquid crystal matrix and measuring the capacitance of the resulting mixture in at least one test cell. The test cell has a layer thickness of 20 µm in all cases and has a perpendicular and homogeneous surface orientation at 1 kHz. The measurement voltage is typically from 0.5 V to 1.0 V, but always below the capacitance threshold of the individual liquid crystal mixtures studied.
[0226] All temperature values indicated in this invention are in °C.
[0227] The mixtures according to the present invention are suitable for all VA-TFT applications, such as (e.g.) 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.
[0228] The nematic liquid crystal mixture in the display according to the present invention generally comprises two components: A and B, each consisting of one or more individual compounds.
[0229] Component A exhibits significant negative dielectric anisotropy and imparts dielectric anisotropy of ≤ -0.5 to the nematic phase. It preferably comprises compounds of formulas IIA, IIB, and / or IIC, in addition to one or more compounds of formula I, and further comprises one or more compounds of formula IV-1.
[0230] The proportion of component A is preferably between 45% and 100%, specifically between 60% and 85%.
[0231] For component A, it is preferable to select one (or more) individual compounds with a Δε value ≤ -0.8. Certainly, the more negative this value, the smaller the proportion of A in the overall mixture.
[0232] Component B exhibits a distinct nematic state and, at 20°C, has a flow viscosity not exceeding 30 mm²·s⁻¹, preferably not exceeding 25 mm²·s⁻¹.
[0233] Various suitable materials are known from the literature to those skilled in this technique. Compounds of formula O-17 are particularly preferred.
[0234] The preferred individual compounds in component B are extremely low viscosity nematic liquid crystals with a flow viscosity of not more than 18 mm2 ·s-1, more preferably not more than 12 mm2 ·s-1 at 20°C.
[0235] Component B is a single-variable or tautomorphic nematic, free of smectic phases and capable of preventing the formation of smectic phases in liquid crystal mixtures at very low temperatures. For example, if various high-nematic materials are added to smectic liquid crystal mixtures, the nematic states of these materials can be compared by the degree of smectic phase suppression achieved.
[0236] The mixture may also include component C, which contains compounds with dielectric anisotropy of Δε ≥ 1.5. On a total basis, these so-called positive compounds are typically present in the mixture of negative dielectric anisotropy in an amount of ≤ 20% by weight.
[0237] In addition to one or more compounds of formula I, the medium preferably contains 4 to 15, specifically 5 to 12, and more preferably < 10 compounds of formula IIA, IIB and / or IIC, and, as appropriate, one or more compounds of formula IV-1.
[0238] In addition to compounds of formula IB and compounds of formula IIA, IIB and / or IIC and, where appropriate, IV-1, other components may also be present in an amount of, for example, up to 45%, but more preferably up to 35%, and specifically up to 10%, of the whole mixture.
[0239] Other components are preferably selected from nematic or nematic atomistic substances, specifically from known substances of the following categories: oxoazobenzene, benzenemethylaniline, biphenyl, terphenyl, phenyl benzoate or cyclohexyl benzoate, phenyl cyclohexanecarboxylate or cyclohexanecarboxylate, phenylcyclohexane, cyclohexylbiphenyl, cyclohexylcyclohexane, cyclohexylnaphthalene, 1,4-bicyclohexylbiphenyl or cyclohexylpyrimidine, phenyl diacetyl or cyclohexyl diacetyl, halogenated stilbene, benzyl phenyl ether, diphenylacetylene and substituted cinnamates.
[0240] The most important compounds suitable as components of this type of liquid crystal phase can be characterized by the following formula IV: R20-LGE-R21 IV Where L and E each represent carbocyclic or heterocyclic systems derived from the following groups: 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidine and 1,3-dialkyl rings, 2,6-disubstituted naphthalene, dihydronaphthalene and tetrahydronaphthalene, quinazoline and tetrahydroquinazoline, G represents -CH=CH- -N(O)=N- -CH=CQ- -CH=N(O)- -C≡C- -CH2-CH2- -CO-O- -CH2-O- -CO-S- -CH2-S- -CH=N- -COO-Phe-COO- -CF2O- -CF=CF- -OCF2- -OCH2- -(CH2)4- -(CH2)3O- Or a CC single bond, Q represents a halogen, preferably chlorine or -CN, and R20 and R21 each represent an alkyl, alkenyl, alkoxy, alkoxyalkyl or alkoxycarbonyl group having up to 18, preferably up to 8, carbon atoms, or one of these groups representing CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl or Br.
[0241] In most of these compounds, R20 and R21 are distinct from each other, and one of these groups is typically alkyl or alkoxy. Other variations of the proposed substituents are also common. Many of these substances or mixtures thereof are commercially available. All of these substances can be prepared by methods known in the literature.
[0242] It goes without saying to those familiar with this technology that the VA, IPS or FFS mixture according to the present invention may also contain compounds in which, for example, H, N, O, Cl and F have been replaced with corresponding isotopes.
[0243] Based on the mixture, the compound of formula P is added to the mixture according to the invention at a concentration preferably from 0.01 to 5% by weight, more preferably from 0.2 to 2% by weight, as appropriate. Such mixtures may also 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 it is intended to polymerize reactive liquid crystal primordia 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 the polymerization conditions of reactive liquid crystal primordia (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 (e.g.) CC-3-V, do not exhibit reactivity under the polymerization conditions (UV polymerization) used for RM; therefore, such compounds are not considered RM herein.
[0244] The compounds according to the invention can be synthesized under known reaction conditions suitable for such reactions by or similar to methods described in the literature (e.g., in standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart). Variations known herein but not mentioned herein may also be used. Specifically, 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 by example.
[0245] Other liquid crystal precursor compounds not explicitly mentioned above may also be used, as appropriate and advantageously, in the media according to the invention. Such compounds are known to those skilled in the art.
[0246] The following examples illustrate the invention but do not limit it. However, they demonstrate to those skilled in the art the concept of preferred mixtures and preferred compounds, their individual concentrations, and combinations thereof. Furthermore, the examples illustrate the achievable properties and combinations thereof.
[0247] For the purposes of this invention and in the following examples, the structure of the liquid crystal compound is indicated by acronyms, wherein the chemical formula is converted according to Tables A to C below. All groups CnH2n+1, CmH2m+1, and ClH2l+1 or CnH2n, CmH2m, and ClH2l are straight-chain alkyl or extended alkyl groups, each having n, m, and l C atoms respectively. Preferably, n, m, and l are 1, 2, 3, 4, 5, 6, or 7 independently of each other. Table A shows the codes of the ring elements of the compound core, Table B lists the bridging units, and Table C lists the meanings of the symbols of the left and right end groups of the molecule. The acronyms consist of the following: the code of the ring element with the connecting group selected as appropriate, followed by the first hyphen and the code of the left end group, and the second hyphen and the code of the right end group. Table D shows the illustrative structure of the compound and its individual abbreviations. [surface] [A] [:cyclic elements] [, , ] [, , ] [, , ] [, , ] [, , ] [surface] [B] [Bridge Connection Unit] [, , ] [E] -CH2-CH2- [V] -CH=CH- [T] -C≡C- [W] -CF2-CF2- [B] -CF=CF- [Z] -CO-O- [ZI] -O-CO- [X] -CF=CH- [XI] -CH=CF- [O] -CH2-O- [OI] -O-CH2- [Q] -CF2-O- [QI] -O-CF2- [surface] [C] [:] [Terminal base] [, , ] [Alone on the left side or in combination] [Alone on the right side or in combination] [-n-] CnH2n+1- [-n] -CnH2n+1 [-nO-] CnH2n+1-O- [-On] -O- CnH2n+1 [-V-] CH2=CH- [-V] -CH=CH2 [-nV-] CnH2n+1-CH=CH- [-nV] -CnH2n-CH=CH2 [-Vn-] CH2=CH- CnH2n- [-Vn] -CH=CH-CnH2n+1 [-nVm-] CnH2n+1-CH=CH-CmH2m- [-nVm] - CnH2n-CH=CH-CmH2m+1 [-N-] N≡C- [-N] -C≡N [-S-] S=C=N- [-S] -N=C=S [-F-] F- [-F] -F [-CL-] Cl- [-CL] -Cl [-M-] CFH2- [-M] -CFH2 [-D-] CF2H- [-D] -CF2H [-T-] CF3- [-T] -CF3 [-MO-] CFH2O - [-OM] -OCFH2 [-DO-] CF2HO - [-OD] -OCF2H [-TO-] CF3O - [-OT] -OCF3 [-A-] H-C≡C- [-A] -C≡C-H [-nA-] CnH2n+1-C≡C- [-An] -C≡C-CnH2n+1 [-NA-] N≡C-C≡C- [-AN] -C≡C-C≡N [-(cn)-] [-(cn)] [-(cn)m-] [-m(cn)] [Only in combination on the left] [Only in combination on the right side] [-…n…-] -CnH2n- [-…n…] -CnH2n- [-…M…-] -CFH- [-…M…] -CFH- [-…D…-] -CF2- [-…D…] -CF2- [-…V…-] -CH=CH- [-…V…] -CH=CH- [-…Z…-] -CO-O- [-…Z…] -CO-O- [-…ZI…-] -O-CO- [-…ZI…] -O-CO- [-…K…-] -CO- [-…K…] -CO- [-…W…-] -CF=CF- [-…W…] -CF=CF- Where n and m are integers, and the three dots "..." are placeholders for other abbreviations from this table.
[0248] In addition to compounds of formulas I, IIA, IIB, IIC and / or IID, mixtures according to the present invention preferably contain one or more of the compounds mentioned below.
[0249] Use the following abbreviations: (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, preferably 0 to 4, more preferably 0 or 2, and best of all 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".) [surface] [D] [, , ] [surface] [E] [, , ] Table E shows the palm-shaped dopants that can be added to the LC media according to the present invention. [surface] [F] [, , ] Table F shows illustrative reactive liquid crystal precursor compounds that can be used in LC media according to the present invention.
[0250] 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.
[0251] In another preferred embodiment, the mixture according to the invention comprises one or more polymerizable compounds selected from RM-145 to RM-152, preferably selected from RM-147 to RM-152. [surface] [G] [, , ] 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:
[0252] In a preferred embodiment, the LC medium, SA-VA and SA-FFS display and one or more types of P RM combination according to the present invention include one or more SA additives selected from SA-1 to SA-48, preferably selected from SA-14 to SA-48, and most preferably selected from SA-20 to SA-34 and SA-44.
[0253] [Work Example] [:] [ ] The following examples are intended to explain the invention but not to limit it. In these examples, mp represents the melting point of the liquid crystal material (in degrees Celsius) and C represents the clarifying point of the liquid crystal material (in degrees Celsius); the boiling point 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 Tg represents the glass transition temperature. The number between the two symbols indicates the transition temperature in degrees Celsius.
[0254] The bulk 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 observing the change in dielectric constant of the bulk mixture after the addition of the compound under investigation and by interpolation to 100% of the compound used. Generally, depending on solubility, 10% of the compound under investigation was dissolved in the bulk mixture.
[0255] Unless otherwise indicated, part or percentage data are expressed as parts by weight or weight percentage.
[0256] In the preceding and following text: Vo represents the capacitor's critical voltage limit [V] at 20℃. ne represents the anomalous refractive index at 20℃ and 589 nm. "no" indicates the general refractive index at 20℃ and 589 nm. Δn represents the optical anisotropy at 20℃ and 589 nm. ε⊥ represents the dielectric permittivity orthogonal to the director at 20℃ and 1 kHz. ε|| represents the dielectric permittivity parallel to the director at 20℃ and 1 kHz. Δε represents the dielectric anisotropy at 20℃ and 1 kHz. cl.p., T(N,I) represents the clarification point [°C]. γ1 represents the rotational viscosity [mPa·s] measured at 20°C. K1 represents the elastic constant, the "bending" deformation at 20℃ [pN]. K2 represents the elastic constant, the torsional deformation at 20°C [pN]. K3 represents the elastic constant, the bending deformation [pN] at 20℃. Kavg. indicates that it is defined as Kavg. = The mean elastic constant of (1.5·K1 + K3) LTS indicates the low-temperature stability (nematic phase) measured in the test unit or the whole as specified.
[0257] Unless otherwise expressly stated, all values indicated in this application for temperatures (such as melting point T(C,N), the transition from smectic (S) to nematic (N) phase T(S,N), and the refining 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 indicate the transition temperature.
[0258] Unless otherwise explicitly indicated, the term "threshold voltage" used in this invention refers to the capacitive threshold (V0), also known as the Freedericks threshold. In practice, as is commonly used, the optical threshold (V10) may also be indicated for 10% relative contrast.
[0259] The display used to measure the capacitance threshold voltage consists of two parallel glass plates spaced 20 µm apart. Each plate has an electrode layer on its inner side and an unrubbed polyimide alignment layer on its top, which causes vertical edge alignment of the liquid crystal molecules.
[0260] The display or test unit used to measure tilt angle consists of two parallel glass plates with a spacing of 4 µm. Each plate has 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 liquid crystal molecules.
[0261] Unless otherwise indicated, VHR should be measured after 5 minutes in an oven at 20°C (VHR20) and 100°C (VHR100) using a commercially available instrument model LCM-1 (O0004) from TOYO Corporation, Japan. Unless otherwise specified, the frequency of the voltage used should be in the range of 1 Hz to 60 Hz.
[0262] The accuracy of VHR measurements depends on the individual VHR value. Accuracy decreases as the value decreases. The deviations typically observed for values across various order of magnitude are compiled in the table below, organized by their order of magnitude. VHR range Deviation (relative) VHR value ΔGVHR / VHR / % since to about 99.6% 100% + / - 0.1 99.0% 99.6% + / - 0.2 98% 99% + / - 0.3 95% 98% + / - 0.5 90% 95% + / - 1 80% 90% + / - 2 60% 80% + / - 4 40% 60% + / - 8 20% 40% + / - 10 10% 20% + / - 20
[0263] 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 units were irradiated for 2.0 h without additional heating. The irradiation power was 765 W / m² V across the wavelength range of 300 nm to 800 nm. UV "truncation" filters with a 310 nm edge wavelength were used sequentially to simulate a so-called window glass pattern. In each series of experiments, at least four test units were studied under each condition, and each result was indicated as the average of the corresponding individual measurements.
[0264] 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): .
[0265] To study low-temperature stability, also known as "LTS," which refers to the stability of individual components in a LC mixture at low temperatures for spontaneous crystallization or the emergence of smectic phases, 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 individual LTS.
[0266] Ion density was measured using a commercially available LC material characterization system (model 6254) from Toyo Corporation, Japan, with a VHR test unit made of AL16301 polyimide (JSR Corp., Japan) having a 3.2 µm unit gap, and resistivity was calculated accordingly. Measurements were performed after storage in an oven at 60°C or 100°C for 5 minutes.
[0267] The term "HTP" refers to the helical torsion force (in µm) of an optically active or antagonistic material in an LC medium. Unless otherwise specified, HTP is measured at 20°C in a commercially available nematic LC bulk mixture MLD-6260 (Merck KGaA).
[0268] The resolving point was measured using a Mettler Thermosystem FP900. Optical anisotropy (Δn) was measured using an Abbe Refractometer 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) (with ε-parallel cells of JALS 2096-R1). Turn-on voltage (V0) was measured at 20°C using an LCR-Meter E4980A / Agilent (G005) (with ε-parallel cells of JALS 2096-R1). Rotational viscosity (γ1) was measured at 20°C using TOYO LCM-2 (0002) (with γ1 negative elements of JALS-2096-R1). Elastic constant (K1, development) was measured at 20°C using LCR-Meter E4980A / Agilent (G005) (with ε-parallel elements of JALS 2096-R1). K3: Elastic constant (K3, bending) was measured at 20°C using LCR-Meter E4980A / Agilent (G005) (with ε-parallel elements of JALS 2096-R1).
[0269] Unless otherwise expressly stated, all concentrations in this application are indicated as weight percentages and relate to the corresponding mixture (solvent-free) containing 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.
[0270] The following examples of mixtures with negative dielectric anisotropy are particularly suitable for liquid crystal displays having at least one planar alignment layer, such as (for example) IPS and FFS displays, specifically UB-FFS (=Ultra-bright FFS), and are also suitable for VA displays.
[0271] [Examples and Comparative Examples of Mixtures] The mixtures C-1 and C-2 and the mixture examples N-1 to N-65 have the composition and properties given in the table below. [Compare mixtures] [C1] B(S)-2O-O5 4.0% Clarification point / ℃: 98.0 CC-3-V 24.0% Δn (589 nm, 20℃): 0.0934 CC-3-V1 8.0% ne (589 nm, 20℃): 1.5743 CC-3-5 7.0% no (589 nm, 20℃): 1.4809 CCY-3-1 5.0% Δε (1 kHz, 20℃): -3.9 CCY-3-O1 5.0 % ε|| (1 kHz, 20°C): 3.4 CCY-3-O2 6.0 % ε⊥ (1 kHz, 20°C): 7.3 CCY-3-O3 5.0 % γ1 (20°C) / mPa·s: 139 CLY-3-O2 8.0 % K1 (pN, 20°C): 18.5 CLY-3-O3 6.0 % K3 (pN, 20°C): 19.8 CLY-4-O2 5.0 % Kavg (pN, 20°C): 19.2 CLY-5-O2 5.0 % Overall LTS (h, 20°C) 528 CY-3-O2 9.0 % PY-1-O2 [ 3.0 %] Σ 100.0 % [Compare mixtures] [C2] B(S)-2O-O5 3.0% Clarification point / ℃: 98.5 CC-3-V 29.5% Δn (589 nm, 20℃): 0.0926 CC-3-V1 8.0% ne (589 nm, 20℃): 1.5731 CC-3-5 5.5% no (589 nm, 20℃): 1.4805 CCY-3-O1 6.0% Δε (1 kHz, 20℃): -3.9 CCY-3-O2 8.0% ε|| (1 kHz, 20℃): 3.4 CLY-3-O2 9.0% ε⊥ (1 kHz, 20℃): 7.3 CLY-3-O3 6.0% γ1 (20℃) / mPa·s: 133 CLY-4-O2 5.0% K1 (pN, 20℃): 18.4 CLY-5-O2 5.0% K3 (pN, 20℃): 19.3 COB(S)-2-O4 5.0% Overall LTS (h, 20℃) 432 CY-3-O2 [10.0%] Σ 100.0% [mixture] [N1] [ ] B(S)-2O-O5 3.0% Clarification point / ℃: 98.5 CC-3-V 31.0% Δn (589 nm, 20℃): 0.0929 CC-3-V1 12.0% ne (589 nm, 20℃): 1.5737 CC-3-5 4.0% no (589 nm, 20℃): 1.4808 CCY-3-O2 8.0% Δε (1 kHz, 20℃): -3.8 CLY-3-O2 9.0% ε|| (1 kHz, 20℃): 3.3 CLY-3-O3 6.0 % ε⊥ (1 kHz, 20℃): 7.1 CLY-4-O2 5.0 % γ1 (20℃) / mPa·s: 125 COB(S)-2-O4 5.0 % K1 (pN, 20℃): 18.4 CY-3-O2 4.0 % K3 (pN, 20℃): 19.9 PY-3-O2 3.0 % CLOY-3-O2 [ 10.0 %] Σ 100.0 % [Table] [1] [ ] Mixture γ1 / K1 Kavg C-1 7.5 15.7 C-2 7.2 15.6 N-1 6.8 15.8
[0272] Comparative examples C-1 and C-2 are very similar to mixture N-1 in composition, clarification temperature, dielectric anisotropy, and birefringence, but do not contain the compound of formula I. A comparison of mixture example N-1 with C-1 and C-2 unexpectedly shows that, due to the use of the compound of formula I, the γ1 / K1 value of the liquid crystal medium according to the present invention is significantly increased (decreased), resulting in faster switching of the display containing the medium (Table 1). Furthermore, the Kavg value remains almost unchanged or even higher, corresponding to an unchanged high contrast ratio. [mixture] [N2] [ ] B(S)-2O-O5 3.0% Clarification point / ℃: 88.5 CC-3-V 31.5% Δn (589 nm, 20℃): 0.0934 CC-3-V1 6.5% ne (589 nm, 20℃): 1.5742 CC-3-5 5.0% no (589 nm, 20℃): 1.4808 CCY-3-O2 8.0% Δε (1 kHz, 20℃): -4.2 CLY-3-O2 9.0% ε|| (1 kHz, 20℃): 3.5 CLY-3-O3 6.0% ε⊥ (1 kHz, 20℃): 7.7 CLY-4-O2 5.0% γ1 (20℃) / mPa·s: 127 COB(S)-2-O4 5.0% K1 (pN, 20℃): 17.3 CY-3-O2 8.0% K3 (pN, 20℃): 18.9 PY-3-O2 3.0% Overall LTS (h, 20℃) 768 CLOY-3-O2 [10.0%] Σ 100.0% [mixture] [N3] [ ] B(S)-2O-O5 3.0% Clarification point / ℃: 86.0 CC-3-V 31.5% Δn (589 nm, 20℃): 0.0929 CC-3-V1 6.5% Δε (1 kHz, 20℃): -4.1 CC-3-5 5.0% CCY-3-O2 8.0% CLY-3-O2 9.0% CLY-3-O3 6.0% CLY-4-O2 5.0% COB(S)-2-O4 5.0% CY-3-O2 8.0% PY-3-O2 3.0% CLOY-(c3)1-O2 5.0% CLOY-3-O2 [5.0%] Σ 100.0% [mixture] [N4] [ ] B(S)-2O-O5 3.0 % Clarity point / °C: 85.5 CC-3-V 31.5 % Δn (589 nm, 20°C): 0.0921 CC-3-V1 6.5 % Δε (1 kHz, 20°C): -4.1 CC-3-5 5.0 % CCY-3-O2 8.0 % CLY-3-O2 9.0 % CLY-3-O3 6.0 % CLY-4-O2 5.0 % B(S)-(c5)1O-O2 5.0 % CY-3-O2 8.0 % PY-3-O2 3.0 % CLOY-3-O2 [ 10.0 %] Σ 100.0%
[0273] The following mixtures N-5 to N-40 also contain stabilizers as indicated above. The total amounts of the main mixture and stabilizers given in the table are 100% by weight. Table 1: Mixtures containing stabilizers. mixture Main mixture Stabilizer (percentage in the mixture) N-5 N-1 0.03% of ST-3a-1 N-6 N-2 0.02% of ST-12 N-7 N-3 0.01% of ST-3b-1 N-8 N-4 0.03% of ST-2a-1 and 0.02% of ST-3a-1 N-9 N-1 0.03% of ST-2a-1 N-10 N-2 0.015% of ST-9-1 N-11 N-3 0.015% of ST-8-1 N-12 N-4 0.03% of ST-12 N-13 N-1 0.03% of ST-8-1 N-14 N-2 0.25% of ST-3a-1 N-15 N-3 0.02% of ST-8-1 and 0.01% of ST-3a-1 N-16 N-4 0.02% of ST-8-1 and 0.1% of ST-3a-1 N-17 N-1 0.01% of ST-3a-1 N-18 N-2 0.025% of ST-8-1 N-19 N-3 0.025% of ST-12 N-20 N-4 0.02% of ST-9-1 and 0.02% of ST-3b-1 N-21 N-1 0.04% of ST-3b-1 and 0.01% of ST-9-1 N-22 N-2 0.02% of ST-3a-1 and 0.05% of ST-3b-1 N-23 N-3 0.02% of ST-3a-1 and 0.01% of ST-8-1 N-24 N-4 0.02% of ST-3a-1 and 0.3% of the following compound N-25 N-1 0.01% of ST-17 N-26 N-2 0.05% of ST-3b-1 and 0.15% of ST-12 N-27 N-3 0.02% of ST-8-1 N-28 N-4 0.02% of ST-12 N-29 N-1 0.01% of ST-3b-1 N-30 N-2 0.03% of ST-2a-1 and 0.02% of ST-3a-1 N-31 N-3 0.03% of ST-2a-1 N-32 N-4 0.015% of ST-9-1 N-33 N-1 0.015% of ST-8-1 N-34 N-2 0.03% of ST-12 N-35 N-3 0.03% of ST-8-1 N-36 N-4 0.25% of ST-3a-1 N-37 N-1 0.02% of ST-8-1 and 0.01% of ST-3a-1 N-38 N-2 0.02% of ST-8-1 and 0.1% of ST-3a-1 N-39 N-3 0.01% of ST-3a-1 N-40 N-4 0.025% of ST-8-1
[0274] The palmar nematic mixture N-41 consists of 99.20% mixture N-5 and 0.80% palmar admixture S-2011.
[0275] The N-41 mixture stands out for its extremely high stability under UV load and demonstrates improved switchover time. [mixture] [N42] [ ] B(S)-2O-O5 3.0 Clarity point [°C]: 117.9 B(S)-2O-O6 4.0 Δn [589 nm, 20°C]: 0.0973 CC-3-V 3.5 ne [589 nm, 20°C]: 1.5782 CC-3-V1 8.5 no [589 nm, 20°C]: 1.4809 CC-4-V1 8.0 F Δε [1 kHz, 20°C]: -4.9 CC-3-4 6.0<00025^{}17> ε|| [1 kHz, 20°C]: 3.3 CC-3-5 [[ID=
[57] ] 9.0 ε⊥ [1 kHz, 20°C]: 8.2 CCPC-35 1.5 γ1 [mPa s, 20°C]: 250 CCY-3-O1 4.0 K1 [pN, 20°C]: 25.9 CCY-3-O2 7.0 K3 [pN, 20°C]: It should be noted that there may be some inaccuracies in the translation due to the lack of clear context for some of these terms, especially in the chemical and physical property notations. The above translation is mainly based on literal conversion while trying to maintain the integrity of the original information.24.1 CCY-3-O3 4.0 CCY-4-O2 4.0 CCY-5-O2 4.0 CLOY-3-O2 10.0 CLY-2-O4 3.0 CLY-3-O2 8.0 CLY-3-O3 3.0 CLY-4-O2 3.0 CLY-5-O2 3.0 CY-3-O2 3.5 Σ 100.0 [Mixture] [N43] B(S)-2O-O4 4.0 Clarification point [°C]: 124.4 B(S)-2O-O6 4.0 Δn [589 nm, 20°C]: 0.1024 CC-3-V 2.0 ne [589 nm, 20°C]: 1.5877 CC-3-V1 8.0 no [589 nm, 20°C]: 1.4853 CC-4-V1 8.0 Δε [kHz, 20°C]: -4.3 CC-3-O3 2.0 ε|| [kHz, 20°C]: 3.2 CC-3-4 2.0 ε⊥ [kHz, 20°C]: Description 7.5 CC-3-5 8.0 γ1 [mPa s, 20°C]: 247 CCP-3-1 8.0 K1 [pN, 20°C]: 28.8 CCP-V2-1 8.0 K3 [pN, 20°C]: 28.3 CCY-3-O2 [[ID= CCY-5-O2 6.0 CLOY-3-O2 12.0 CLY-3-O2 9.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Y-4O-O4 1.0 Σ 100.0 [mixture] [N44] B(S)-2O-O4 2.5 Clarification point [°C]: 98 B(S)-2O-O5 5.0 Δn [589 nm, 20℃]: 0.0938 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5749 CC-3-V 31.0 no [589 nm, 20℃]: 1.4811 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.1 CC-3-5 8.0 ε|| [1 kHz, 20℃]: 3.4 CLOY-3-O2 10.0 ε⊥ [1 kHz, 20℃]: 7.5 CCY-3-O1 8.0 γ1 [mPa s, 20℃]: 146 CCY-3-O2 11.0 K1 [pN, 20℃]: 20.4 CLY-3-O2 9.0 K3 [pN, 20℃]: 21.1 CLY-5-O2 3.5 Σ 100.0 [mixture] [N45] B(S)-2O-O5 4.0 Clarification point [°C]: 100.2 B(S)-2O-O6 4.0 Δn [589 nm, 20℃]: 0.0933 CC-3-V 27.5 ne [589 nm, 20℃]: 1.5739 CC-3-V1 8.0 no [589 nm, 20℃]: 1.4806 CC-4-V1 4.0 Δε [1 kHz, 20℃]: -3.9 CC-3-5 5.0 ε|| [1 kHz, 20℃]: 3.3 CCY-3-O1 5.0 ε⊥ [1 kHz, 20℃]: 7.2 CCY-3-O2 6.0 γ1 [mPa s, 20℃]: 144 CCY-4-O2 3.0 K1 [pN, 20℃]: 19.9 CLOY-3-O2 5.0 K3 [pN, 20℃]: 19.9 CLY-2-O4 1.5 CLY-3-O2 8.0 CLY-3-O3 5.0 CLY-4-O2 5.0 CLY-5-O2 5.0 CY-3-O2 4.0 Σ 100.0 [mixture] [N46] B(S)-2O-O4 4.0 Clarification point [°C]: 96.6 B(S)-2O-O5 1.5 Δn [589 nm, 20℃]: 0.0937 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5751 CC-3-V 30.5 no [589 nm, 20℃]: 1.4814 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.0 CC-4-V1 4.0 ε|| [1 kHz, 20℃]: 3.3 CC-3-5 5.0 ε⊥ [1 kHz, 20℃]: 7.4 CCY-3-O2 8.0 γ1 [mPa s, 20℃]: 146 CLOY-3-O2 15.0 K1 [pN, 20℃]: 20.1 CLY-3-O2 8.0 K3 [pN, 20℃]: 21.4 CLY-3-O3 2.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N47] B(S)-2O-O4 4.0 Clarification point [°C]: 97.9 B(S)-2O-O5 1.5 Δn [589 nm, 20℃]: 0.0934 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5743 CC-3-V 30.5 no [589 nm, 20℃]: 1.4809 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.9 CC-4-V1 4.0 ε|| [1 kHz, 20℃]: 3.3 CC-3-5 5.0 ε⊥ [1 kHz, 20℃]: 7.3 CCY-3-O1 4.0 γ1 [mPa s, 20℃]: 145 CCY-3-O2 6.5 K1 [pN, 20℃]: 19.8 CLOY-3-O2 12.5 K3 [pN, 20℃]: 21.2 CLY-3-O2 8.0 CLY-3-O3 2.5 CLY-4-O2 4.5 CLY-5-O2 5.0 Σ 100.0 [mixture] [N48] B(S)-2O-O4 4.0 Clarification point [°C]: 97.8 B(S)-2O-O5 1.0 Δn [589 nm, 20℃]: 0.0931 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5741 CC-3-V 30.0 no [589 nm, 20℃]: 1.4810 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.0 CC-4-V1 4.0 ε|| [1 kHz, 20℃]: 3.3 CC-3-5 5.0 ε⊥ [1 kHz, 20℃]: 7.4 CCY-3-O2 11.0 γ1 [mPa s, 20℃]: 151 CLOY-3-O2 15.0 K1 [pN, 20℃]: 20.5 CLY-3-O2 8.0 K3 [pN, 20℃]: 21.8 CLY-4-O2 5.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N49] B(S)-2O-O4 4.0 Clarification point [°C]: 98.7 B(S)-2O-O5 1.0 Δn [589 nm, 20℃]: 0.0935 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5743 CC-3-V 30.5 no [589 nm, 20℃]: 1.4808 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.9 CC-4-V1 4.0 ε|| [1 kHz, 20℃]: 3.3 CC-3-5 5.0 ε⊥ [1 kHz, 20℃]: 7.2 CCY-3-O2 10.5 γ1 [mPa s, 20℃]: 147 CLOY-3-O2 12.5 K1 [pN, 20℃]: 20.1 CLY-3-O2[[ID=[N50] B(S)-2O-O4 3.0 Clarity point [°C]: 99.9 B(S)-2O-O5 3.0 Δn [589 nm, 20°C]: 0.0913 B(S)-2O-O6 2.5 ne [589 nm, 20°C]: 1.5720 CC-3-V 30.5 no [589 nm, 20°C]: 1.4807 CC-3-V1 8.0 Δε [1 kHz, 20°C]:[[ID=?]] -3.8 CC-3-5 9.0 ε|| [1 kHz, 20°C]: 3.3 CLOY-3-O2 10.0 ε⊥ [1 kHz, 20°C]: 7.1 CCY-3-O1 8.0 γ1 [mPa s, 20°C]: 147 CCY-3-O2 11.0 K1 [pN, 20°C]: 20.1 CLY-3-O2 9.0 K3 [pN, 20°C]: Note: There seems to be a tag "? " in the original text which might be an error. I've left it as is in the translation for the sake of following the rules. 21.6 CLY-3-O3 3.0 CLY-5-O2 3.0 Σ 100.0 [mixture] [N51] B(S)-2O-O4 4.0 Clarification point [°C]: 120.2 B(S)-2O-O5 4.0 Δn [589 nm, 20℃]: 0.1042 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5886 CC-3-V 9.5 no [589 nm, 20℃]: 1.4844 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.2 CC-4-V1 10.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-4 4.0 ε⊥ [1 kHz, 20℃]: 7.5 CC-3-5 5.0 γ1 [mPa s, 20℃]: 208 CCP-3-1 9.5 K1 [pN, 20℃]: 27.0 CCY-3-O2 8.0 K3 [pN, 20℃]: 24.9 CCY-5-O2 6.0 CLOY-3-O2 5.0 CLY-3-O2 9.0 CLY-3-O3 5.0 CLY-4-O2 4.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N52] B(S)-2O-O4 4.0 Clarification point [°C]: 118.7 B(S)-2O-O5 4.0 Δn [589 nm, 20℃]: 0.1045 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5895 CC-3-V 8.0 no [589 nm, 20℃]: 1.4850 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.1 CC-4-V1 10.0 ε|| [1 kHz, 20℃]: 3.3 CC-3-4 4.0 ε⊥ [1 kHz, 20℃]: 7.4 CC-3-5 5.0 γ1 [mPa s, 20℃]: 215 CCP-3-1 9.0 K1 [pN, 20℃]: 26.4 CCP-V2-1 5.0 K3 [pN, 20℃]: 25.3 CCY-3-O2 8.5 CCY-5-O2 4.0 CLOY-3-O2 10.0 CLY-3-O2 7.0 CLY-4-O2 4.5 CLY-5-O2 5.0 Σ 100.0 [mixture] [N53] B(S)-2O-O4 4.0 Clarification point [°C]: 98.2 B(S)-2O-O5 5.0 Δn [589 nm, 20℃]: 0.0950 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5765 CC-3-V 15.5 no [589 nm, 20℃]: 1.4815 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.1 CC-4-V1 8.0 ε|| [1 kHz, 20℃]: 3.4 CC-3-4 5.0 ε⊥ [1 kHz, 20℃]: 7.6 CC-3-5 8.0 K1 [pN, 20℃]: 21.2 CCP-V2-1 5.5 K3 [pN, 20℃]: 20.7 CCY-3-O1 8.0 CCY-3-O2 11.0 CLOY-3-O2 10.0 CLY-3-O2 6.0 Y-4O-O4 2.0 Σ 100.0 [Mixture] [N54] B(S)-2O-O5 3.0 Clarification point [°C]: 100.1 B(S)-2O-O6 2.0 Δn [589 nm, 20°C]: 0.0900 CC-3-V 25.0 ne [589 nm, 20°C]: 1.5695[[ID= 4.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Y-4O-O4 3.5 Σ 100.0 [mixture] [N55] B(S)-2O-O4 4.0 Clarification point [°C]: 121.7 B(S)-2O-O5 3.5 Δn [589 nm, 20℃]: 0.1030 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5875 CC-3-V 7.0 no [589 nm, 20℃]: 1.4845 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.7 CC-4-V1 11.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-5 9.0 ε⊥ [1 kHz, 20℃]: 6.9 CCP-3-1 8.0 γ1 [mPa s, 20℃]: 210 CCP-3-3 6.0 K1 [pN, 20℃]: 28.6 CCP-V2-1 2.5 K3 [pN, 20℃]: 26.5 CCY-3-O2 8.0 CCY-5-O2 5.0 CLOY-3-O2 7.0 CLY-3-O2 7.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N56] B(S)-2O-O4 4.0 Clarification point [°C]: 121 B(S)-2O-O5 3.0 Δn [589 nm, 20℃]: 0.1039 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5899 CC-3-V 15.0 no [589 nm, 20℃]: 1.4860 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.9 CC-4-V1 4.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-5 6.0 ε⊥ [1 kHz, 20℃]: 7.2 CCP-3-1 8.0 γ1 [mPa s, 20℃]: 211 CCP-3-3 1.5 K1 [pN, 20℃]: 25.7 CCP-V2-1 6.5 K3 [pN, 20℃]: 25.5 CCY-3-O2 8.0 CCY-5-O2 6.0 CLOY-3-O2 7.0 CLY-3-O2 9.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N57] B(S)-2O-O4 4.0 Clarification point [°C]: 119.6 B(S)-2O-O5 4.0 Δn [589 nm, 20℃]: 0.1028 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5878 CC-3-V 7.5 no [589 nm, 20℃]: 1.4850 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.8 CC-4-V1 11.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-5 9.0 ε⊥ [1 kHz, 20℃]: 7.0 CCP-3-1 8.0 γ1 [mPa s, 20℃]: 209 CCP-3-3 6.0 K1 [pN, 20℃]: 27.6 CCP-V2-1 2.0 K3 [pN, 20℃]: 25.8 CCY-3-O2 8.0 CCY-5-O2 5.0 CLOY-3-O2 8.5 CLY-3-O2 7.0 CLY-4-O2 3.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N58] B(S)-2O-O4 4.0 Clarification point [°C]: 121.6 B(S)-2O-O5 2.5 Δn [589 nm, 20℃]: 0.1037 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5894 CC-3-V 11.5 no [589 nm, 20℃]: 1.4857 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.9 CC-4-V1 8.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-5 5.0 ε⊥ [1 kHz, 20℃]: 7.1 CCP-3-1 8.0 γ1 [mPa s, 20℃]: 218 CCP-3-3 5.0 K1 [pN, 20℃]: 26.2 CCP-V2-1 4.0 K3 [pN, 20℃]: 25.7 CCY-3-O2 8.0 CCY-5-O2 4.5 CLOY-3-O2 8.5 CLY-3-O2 8.0 CLY-3-O3 3.0 CLY-4-O2 4.0 CLY-5-O2 4.0 Σ 100.0 [Mixture] [N59] B(S)-2O-O5 3.0 Clarification point [°C]: 117.7 B(S)-2O-O6 4.0 Δn [589 nm, 20°C]: 0.0972 CC-3-V 3.5 ne [589 nm, 20°C]: 1.5781 CC-3-V1 8.5 no [589 nm, 20°C]: 1.4809 CC-4-V1 8.0 Δε [1 kHz, 20°C]: -4.9 CC-3-4 6.0 ε|| [1 kHz, 20°C]: 3.3 CC-3-5 9.0 ε⊥ [1 kHz, 20°C]: 8.2 CCPC-35 1.5 γ1 [mPa s, 20°C]: 255 CCY-3-O1 4.0 K1 [pN, 20°C]: 25.7<� CCY-3-O2 7.0 K3 [pN, 20°C]: 24.0 CCY-3-O3 4.0 CCY-4-O2 4.0 CCY-5-O2 4.0 CLOY-3-O2 10.0 CLY-2-O4 3.0 CLY-3-O2 8.0 CLY-3-O3 3.0 CLY-4-O2 3.0 CLY-5-O2 3.0 CY-3-O2 3.5 Σ 100.0 [mixture] [N60] B(S)-2O-O4 4.0 Clarification point [°C]: 117 B(S)-2O-O5 4.0 Δn [589 nm, 20℃]: 0.1026 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5867 CC-3-V 8.0 no [589 nm, 20℃]: 1.4841 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.0 CC-4-V1 12.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-5 9.0 ε⊥ [1 kHz, 20℃]: 7.2 CCP-3-1 9.0 γ1 [mPa s, 20℃]: 212 CCP-3-3 4.0 K1 [pN, 20℃]: 26.7 CCY-3-O2 9.0 K3 [pN, 20℃]: 25.4 CCY-5-O2 4.0 CLOY-3-O2 10.0 CLY-3-O2 7.0 CLY-4-O2 3.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N61] B(S)-2O-O4 4.0 Clarification point [°C]: 114.9 B(S)-2O-O5 4.0 Δn [589 nm, 20℃]: 0.1024 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5874 CC-3-V 13.5 no [589 nm, 20℃]: 1.4850 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.8 CC-4-V1 12.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-5 4.5 ε⊥ [1 kHz, 20℃]: 7.0 CCP-3-1 9.0 γ1 [mPa s, 20℃]: 185 CCP-3-3 2.0 K1 [pN, 20℃]: 24.6 CCP-V2-1 3.0 K3 [pN, 20℃]: 24.2 CCY-3-O2 9.5 CLOY-3-O2 8.5 CLY-3-O2 8.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Σ 100.0 [Mixture] [N62] B(S)-2O-O4 4.0 Clarification point [℃]: 117.5 B(S)-2O-O5 4.0 Δn [589 nm, 20℃]: 0.1019 B(S)-2O-O6 4.0 ne [589 nm, 20℃]: 1.5856 CC-3-V 5.5 no [589 nm, 20℃]: 1.4837 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -4.0 CC-4-V1 12.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-4 4.0 ε⊥ [1 kHz, 20℃]: 7.2 CC-3-5 9.0 γ1 [mPa s, 20℃]: 204 CCP-3-1 9.0 K1 [pN, 20℃]: 27.5 CCP-V2-1 2.0 K3 [pN, 20℃]: 26.2 CCY-3-O2 9.0 CCY-5-O2 3.0 CLOY-3-O2 8.5 CLY-3-O2 8.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Σ 100.0 [mixture] [N63] B(S)-2O-O4 3.0 Clarification point [°C]: 92 B(S)-2O-O5 3.0 Δn [589 nm, 20℃]: 0.0942 B(S)-2O-O6 3.0 ne [589 nm, 20℃]: 1.5760 CC-3-V 39.0 no [589 nm, 20℃]: 1.4818 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.7 CCP-3-1 2.0 ε|| [1 kHz, 20℃]: 3.4 CCY-3-O1 4.0 ε⊥ [1 kHz, 20℃]: 7.1 CCY-3-O2 7.0 γ1 [mPa s, 20℃]: 120 CLY-3-O2 8.0 K1 [pN, 20℃]: 18.3 CLY-4-O2 5.0 K3 [pN, 20℃]: 19.8 CLY-5-O2 5.0 PY-3-O2 3.0 CLOY-3-O2<00043-14> 10.0 Σ 100.0 [Mixture] [N64] B(S)-2O-O5 3.0 Clarification point [°C]: 92.1 CC-3-V 31.0 Δn [589 nm, 20°C]: 0.0928 CC-3-V1 12.0 ne [589 nm, 20°C]: 1.5734 CC-3-5 4.0 no [589 nm, 20°C]: 1.4806 CCY-3-O2 8.0 Δε [1 kHz, 20°C]: -3.8 CLY-3-O2 9.0 ε|| [1 kHz, 20°C]: 3.3 CLY-3-O3 6.0 ε⊥ [1 kHz, 20°C]: 7.1 CLY-4-O2 5.0 [[ID=6�]] γ1 [mPa s, 20°C]: 128 COB(S)-2-O4 5.0 K1 [pN, 20°C]: 18.4 CY-3-O2 4.0 K3 [pN, 20°C]: 19.8 PY-3-O2 3.0 CLOY-3-O2 10.0 Σ 100.0 [mixture] [N65] B(S)-2O-O4 3.0 Clarification point [°C]: 117.6 B(S)-2O-O5 4.0 Δn [589 nm, 20℃]: 0.1008 B(S)-2O-O6 3.0 ne [589 nm, 20℃]: 1.5842 CC-3-V 6.5 no [589 nm, 20℃]: 1.4834 CC-3-V1 8.0 Δε [1 kHz, 20℃]: -3.9 CC-4-V1 12.0 ε|| [1 kHz, 20℃]: 3.2 CC-3-4 4.0 ε⊥ [1 kHz, 20℃]: 7.1 CC-3-5 8.0 γ1 [mPa s, 20℃]: 201 CCP-3-1 8.5 K1 [pN, 20℃]: 27.5 CCP-V2-1 1.5 K3 [pN, 20℃]: 26.4 CCY-3-O2 8.0 CCY-5-O2 1.5 CLOY-3-O2 8.5 CLY-2-O4 2.5 CLY-3-O2 8.0 CLY-3-O3 3.0 CLY-4-O2 5.0 CLY-5-O2 5.0 Σ 100.0
Claims
1. A liquid crystal medium comprising one or more compounds of formula I, wherein R1 represents H, a straight-chain or branched alkyl or alkoxy group having 1 to 15 C atoms, wherein one or more CH2 groups among these groups are each independently substituted with -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO- in such a manner that the O atoms are not directly connected to each other, and wherein one or more H atoms are halogenated, wherein Y1 represents H or CH3, n is 0 or 1, and v is 1, 2, 3, 4, 5, or 6; and one or more compounds selected from the group of compounds of formulas IIA, IIB, IIC, and IID, wherein R2A, R2B, R2C, and R2D Each of these groups independently represents H, an alkyl or alkenyl group having up to 15 carbon atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen. Additionally, one or more of these CH2 groups may be substituted with -O-, -S-, -C≡C-, -CF2O-, -OCF2-, -OC-O-, or -O-CO- to prevent direct connection of O atoms. L1 to L4 each independently represent F, Cl, CF3, or CHF2. Y represents H, F, Cl, CF3, CHF2, or CH3. Z2, Z2B, and Z2D each independently represent a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, or -CH=CHCH2O-. p represents 0, 1, or 2. q Represents 0 or 1, and v represents an integer from 1 to 6, wherein Formula IID does not include compounds of Formula I, and one or more compounds of Formula III-2: wherein R11 and R12 each independently represent H, an alkyl or alkoxy group having 1 to 15 C atoms, wherein one or more of these groups are independently substituted with -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that the O atoms are not directly bonded to each other, and wherein one or more H atoms are substituted with halogens, and L11 and L12 each independently represent F, Cl, CF3 or CHF2.
2. The medium of claim 1, wherein the medium contains one or more compounds of formula IIA at a total concentration of 3% to 25%.
3. The medium of claim 1, wherein the medium comprises one or more compounds of formula IIA and one or more compounds of formula III-2 in a total concentration of 10% to 40%.
4. The medium of claim 1, wherein the medium comprises one or more compounds of formula IID selected from compounds of formula CLY-n-Om at a total concentration of >5% to 30%, wherein n and m are integers from 1 to 9, which are independent of each other.
5. The medium as requested in item 1, wherein in formula I 6. The medium of claim 1, wherein the medium comprises one or more compounds of formula IV, wherein R41 represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms, and R42 represents an alkyl group having 1 to 7 carbon atoms or an alkoxy group having 1 to 6 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.
7. The medium as claimed in claim 6, wherein the medium comprises one or more compounds selected from the group consisting of: .
8. The medium of claim 1, wherein the medium comprises one or more compounds of formula V, wherein R51, R52 represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkoxyalkyl group having 2 to 7 carbon atoms, an alkenyl group, or an alkenoxy group, Z51, Z52 each independently represent -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond, and n is 1 or 2.
9. The medium of claim 8, wherein the medium comprises one or more compounds selected from formulas V-1 to V-17: wherein R1 and R2 have the meanings specified for R2A in claim 1.
10. A medium as claimed in any of claims 1 to 9, wherein the medium comprises one or more polymerizable compounds of formula P-Sp-A1-(Z1-A2)zR P, wherein P represents a polymerizable group, Sp represents a spacer group or a single bond, A1 and A2 represent, respectively, an aromatic group, heteroaromatic group, alicyclic group or heterocyclic group having 4 to 25 ring atoms, which may also contain a fused ring, and is unsubstituted or monosubstituted or polysubstituted with L, L represents F, Cl, -CN, P-Sp- or a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2- groups are substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O- as appropriate, such that O- and / or S- atoms are not directly connected to each other, and wherein one or more H atoms are substituted with P-Sp-, F or Cl as appropriate, Z1 -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-, -CR0R00- or a single bond, R0 and R00 represent H or an alkyl group having 1 to 12 C atoms, R represents H, L or P-Sp-, z n1 can be 0, 1, 2 or 3, and n1 can be 1, 2, 3 or 4.
11. The medium of claim 10, wherein the polymerizable compound of equation P is polymerized.
12. A method for preparing an LC medium as claimed in any one of claims 1 to 11, comprising mixing one or more compounds of formula I with one or more compounds selected from the group consisting of formulas IIA, IIB, IIC and IID as claimed in claim 1, and one or more compounds of formula III-2 as claimed in claim 1, and, if appropriate, mixing with one or more liquid crystal precursors or liquid crystal compounds and / or polymerizable compounds as claimed in claim 10, and, if appropriate, mixing with one or more additives.
13. An LC display comprising a medium as claimed in any one of claims 1 to 11.
14. The display as requested in item 13, wherein the display is a PSA display.
15. The display as claimed in claim 14, wherein the display is a PS-VA, PS-IPS, PS-FFS, PS-UB-FFS, polymer-stabilized SA-VA, or polymer-stabilized SA-FFS display.
16. The display as requested in item 13, wherein the display is a VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, or SA-VA display.
17. An application of a liquid crystal medium as claimed in any one of claims 1 to 11, for use in an electro-optical display.
Citation Information
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