LCD Media

Abstract

We provide liquid crystal media. [Solution] The present invention relates to a liquid crystal medium comprising at least one compound of formula I, and to the use of the liquid crystal medium in an electro-optical liquid crystal display. TIFF2026143494000182.tif34142 (In the formula, R 1 represents an alkyl or alkoxy group having 1 to 15 carbon atoms, provided that one or more CH2 groups in these groups may be independently replaced by -C≡C-, -CF2O-, -CH=CH-, -O-, -CO-O-, etc., such that the oxygen atoms are not directly bonded to each other, and that one or more hydrogen atoms may be replaced by halogen atoms.

Description

[Technical Field]

[0001] The present invention relates to liquid crystal media (LC media), their use for electro-optical purposes, and LC displays containing these media. [Background technology]

[0002] Liquid crystals are primarily used as dielectrics in display devices because their optical properties can be altered by the applied voltage. Electro-optical devices based on liquid crystals are very well known to those skilled in the art and can be based on a variety of effects. Examples of such devices include cells with dynamic scattering, DAP (deformation of aligned phases) cells, guest / host cells, TN cells with a "twisted nematic structure," STN ("supertwisted nematic") cells, SBE ("superbirefringence effect") cells, and OMI ("optical mode interference") cells. The most common display devices are based on the Schadt-Helfrich effect and have a twisted nematic structure. In addition, there are also cells that operate with an electric field parallel to the substrate and the liquid crystal surface, such as IPS ("in-plane switching") cells. In particular, TN, STN, FFS (fringe field switching), and IPS cells are currently commercially interesting application areas for the media according to the present invention.

[0003] The liquid crystal material must have good chemical and thermal stability, as well as good stability against electric fields and electromagnetic radiation. Furthermore, the liquid crystal material must have low viscosity, resulting in a short address time, low threshold voltage, and high contrast within the cell.

[0004] The liquid crystal material must also have an intermediate phase suitable for the cell, such as a nematic or cholesteric intermediate phase, at normal operating temperatures, i.e., in as wide a range as possible above and below room temperature. Since liquid crystals are generally used as mixtures of multiple components, it is important that the components mix easily with each other. Further properties such as conductivity, dielectric anisotropy, and optical anisotropy must satisfy various requirements depending on the type of cell and application field. For example, a material for a cell with a twisted nematic structure must have positive dielectric anisotropy and low conductivity.

[0005] For example, for matrix liquid crystal displays (MLC displays) that have integrated nonlinear elements for switching individual pixels, a medium with large positive dielectric anisotropy, a broad nematic phase, a relatively low birefringence, very high resistivity, good UV and temperature stability, and a low vapor pressure is desired.

[0006] This type of matrix liquid crystal display is known. An example of a nonlinear element that can be used to switch individual pixels individually is an active element (i.e., a transistor). The term "active matrix" is then used, and two types can be distinguished: 1. MOS (metal oxide semiconductor) or other diodes on a silicon wafer as a substrate, 2. Thin-film transistors (TFTs) on a glass plate as a substrate.

[0007] Using single-crystal silicon as the substrate material results in connection problems even in modular assemblies of various component displays, thus limiting the size of the display.

[0008] In the preferred and more promising Type 2, the electro-optical effect used is typically the TN effect. Two distinct techniques are used: TFTs containing compound semiconductors such as CdSe, or TFTs based on polycrystalline or amorphous silicon. The latter technique has been the subject of globally focused research.

[0009] The TFT matrix is ​​located inside one of the glass plates of the display, while the other glass plate has transparent counter electrodes on its inside. Compared to the size of the pixel electrodes, the TFTs are very small and have virtually no adverse effect on the image. Furthermore, this technology can be extended to full-color displays, in which a mosaic of red, green, and blue filters is arranged so that a filter element faces each switchable pixel.

[0010] A TFT display typically operates as a TN cell with polarizers that intersect in transmission and is illuminated from behind.

[0011] In this specification, the term MLC display encompasses any matrix display having integrated nonlinear elements, i.e., active matrices as well as displays having passive elements such as varistors or diodes (MIM, i.e., metal-insulator-metal).

[0012] This type of MLC display is particularly suitable for television applications (e.g., pocket TVs) or computer applications (laptops) and for advanced information displays in automobiles or aircraft. In addition to problems related to the angular dependence of contrast and response time, MLC displays also face problems due to insufficient resistivity of the liquid crystal mixture [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H. and SHIMIZU, H., Proc. Eurodisplay, Vol. 84, September 1984, Nos. A210-288, "Matrix LCD Controlled by Double Stage Diode Rings", p. 141ff, Paris (Non-patent Literature 1); STROMER, M., Proc. Eurodisplay, Vol. 84, September 1984, "Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays", p. 145ff, Paris (Non-patent Literature 2)]. As resistivity decreases, the contrast of MLC displays deteriorates, and afterimage erasure problems may occur. The resistivity of liquid crystal mixtures generally decreases over the lifespan of an MLC display due to their interaction with the internal surface of the display; therefore, a high (initial) resistance is crucial for achieving an acceptable service life. In particular, achieving very high resistivity values ​​has traditionally been impossible for low-voltage mixtures. Furthermore, it is important that the resistivity shows the smallest possible increase after temperature rise and heating and / or UV exposure. The low-temperature characteristics of mixtures from the prior art are also particularly undesirable. It is required that crystallization and / or smectic phases do not occur even at low temperatures, and that the temperature dependence of viscosity is as low as possible. Therefore, MLC displays from the prior art do not meet today's requirements.

[0013] In addition to backlit liquid crystal displays, i.e., liquid crystal displays that operate transmissively and, if desired, semi-transmissively, there is particular interest in reflective liquid crystal displays. These reflective liquid crystal displays use ambient light for information display. They therefore consume significantly less energy than backlit liquid crystal displays of corresponding size and resolution. Because the TN effect is characterized by very good contrast, this type of reflective display can be read well even in bright ambient conditions. This is already known as a simple reflective TN display, as used, for example, in watches and pocket calculators. However, the principle can also be applied to high-quality, higher-resolution active-matrix-addressed displays, such as TFT displays. Here, as is generally the case in conventional transmissive TFT-TN displays, the use of liquid crystals with a low birefringence (Δn) is necessary to achieve low optical retardation (d·Δn). This low optical retardation results in a generally acceptable low viewing angle dependence of contrast (see German Patent No. 30 22 818 (Patent Document 1)). In reflective displays, the effective layer thickness through which light passes is almost twice that of transmissive displays with the same layer thickness; therefore, using low birefringence liquid crystals is even more important in reflective displays than in transmissive displays.

[0014] For television and video applications, displays with fast response times are necessary to reproduce multimedia content such as movies and video games with near-realistic quality. Such short response times can be achieved by using liquid crystal media with low viscosity, particularly rotational viscosity γ1, and high optical anisotropy (Δn).

[0015] To achieve a 3D effect using shutter glasses, high-speed switching mixtures with low rotational viscosity and correspondingly high optical anisotropy (Δn) are particularly used. An electro-optical lens system capable of switching a display's two-dimensional display to a three-dimensional naked-eye stereoscopic display can be achieved using a mixture with high optical anisotropy (Δn).

[0016] Therefore, there is a continued strong demand for MLC displays that possess extremely high resistivity while simultaneously having a wide operating temperature range, short response time even at low temperatures, and a low threshold voltage, and that either do not have these drawbacks or have them only to a reduced degree.

[0017] In the case of TN (Schadt-Helfrich) cells, a medium that facilitates the following advantages within the cell is desirable: - Extended nematic phase range (especially down to lower temperatures), - Switching capability at extremely low temperatures (outdoor use, automotive, aviation), - Increased resistance to UV radiation (longer lifespan), - Low threshold voltage.

[0018] It is not possible to achieve these advantages while simultaneously maintaining other parameters using media available from prior art.

[0019] For supertwisted nematic (STN) cells, a medium that allows for greater multiplexing capability and / or lower threshold voltage and / or a wider nematic phase range (especially at low temperatures) is desired. To this end, there is an urgent need to further expand the degrees of freedom of available parameters (transparency point, smectic-nematic phase transition or melting point, viscosity, dielectric parameters, elastic parameters).

[0020] One of the most important characteristics of modern LCDs is the correction and playback of video. If the response speed of the liquid crystal medium is too slow, undesirable artifacts will occur in such content on the display. The physical parameters that essentially determine the response time of a liquid crystal mixture are the rotational viscosity γ1 and the elastic constant. The latter is also particularly important for ensuring a good dark state in the LCD. However, it is generally observed that as the elastic constant increases, the transparency point of the mixture, and therefore the rotational viscosity of the mixture, also increases, which means that improvement in response time is impossible. In particular, for LC displays for television and video applications (e.g., LCD TVs, monitors, PDAs, laptops, game consoles), it is desirable to significantly reduce the response time. Theoretically, reducing the layer thickness d of the LC medium in the LC cell ("cell gap") results in a faster response time, but to ensure proper optical retardation (d·Δn), an LC medium with a higher birefringence Δn is required. However, LC materials with high birefringences, known from conventional technology, generally also possess high rotational viscosity, which negatively affects the response time.

[0021] Therefore, there is a demand for LC media that simultaneously possess fast response time, low rotational viscosity, and relatively high birefringence. [Prior art documents] [Patent Documents]

[0022] [Patent Document 1] German Patent No. 3022818 [Non-patent literature]

[0023] [Non-Patent Document 1] TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., and SHIMIZU, H., Proc. Eurodisplay, Vol. 84, September 1984, Nos. A210-288, "Matrix LCD Controlled by Double Stage Diode Rings," p. 141ff, Paris [Non-Patent Document 2] STROMER, M., Proc. Eurodisplay, Vol. 84, September 1984, "Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays," p. 145ff, Paris [Overview of the project] [Problems that the invention aims to solve]

[0024] The present invention is based on the objective of providing a medium for this type of MLC, TN, STN, OCB, positive VA, FFS, PS (polymer stabilized)-FFS, IPS, and PS-IPS displays that has the desired properties described above and does not exhibit the defects described above, or exhibits them only to a reduced degree. In particular, the LC medium must have a relatively high birefringence, along with a fast response time and low rotational viscosity. In addition, the LC medium must have a high transparency point, high dielectric anisotropy, a low threshold voltage, and very good low-temperature stability (LTS). [Means for solving the problem]

[0025] Here, it was found that this objective can be achieved by using an LC medium containing one or more compounds of formula I.

[0026] The present invention relates to a liquid crystal medium characterized by containing one or more compounds of formula I.

[0027] [ka] During the ceremony, R 1 represents an alkyl or alkoxy group having 1 to 15 carbon atoms, provided that in addition, one or more CH2 groups in these groups are independently linked to each other in such a way that the oxygen atoms are not directly bonded to each other, such as -C≡C-, -CF2O-, -CH=CH-,

[0028] [ka] The atoms may be replaced with -O-, -CO-O-, or -O-CO-, and in addition, one or more H atoms may be replaced with halogen atoms. [Modes for carrying out the invention]

[0029] As a result of compounding formula I, an LC mixture having the desired properties described above is obtained, in particular an LC mixture having very low rotational viscosity. The mixture according to the present invention has a very high elastic constant, and therefore a very good response time is possible. Furthermore, the mixture according to the present invention is stable at least at -20°C and does not show a tendency to crystallize. The rotational viscosity γ1 is generally less than 120 mPa·s. Furthermore, the mixture according to the present invention is distinguished by a very good ratio of rotational viscosity γ1 to the transparency point, a high optical anisotropy Δε and a high birefringence Δn, as well as a fast response time, a low threshold voltage, a high transparency point, high positive dielectric anisotropy and a broad nematic phase range. Furthermore, compound I is very easily soluble in liquid crystal media.

[0030] Compounds of formula I have a wide range of applications, particularly distinguished by their extremely high elastic constants. Depending on the selection of substituents, compounds of formula I can act as the primary base material constituting liquid crystal media, but liquid crystal base materials from other types of compounds can also be added to compounds of formula I, for example, to influence the dielectric and / or optical anisotropy of this type of dielectric and / or to optimize the threshold voltage and / or rotational viscosity of this type of dielectric. As a result, the LC mixtures according to the present invention, with their high elastic constants, support a good dark state of the display, which is important for display contrast, and at the same time, enable very good response times.

[0031] R in compounds of formula I and its subformulas 1 Preferably, represents a linear alkyl group having 3 to 5 carbon atoms. In a more preferred embodiment, one or more CH2 groups in the alkyl group may be replaced with -CH=CH-.

[0032] Particularly preferred compounds of formula I are shown below.

[0033] [ka] Compounds of formula I-2 are particularly preferred.

[0034] In its pure state, the compound of formula I is colorless and forms a liquid crystal intermediate phase within a temperature range favorable for electro-optical use. The compound of formula I is chemically, thermally, and lightly stable.

[0035] Compounds of formula I are prepared by methods known in themselves, as described in the literature (e.g., standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, and the City of Stuttgart), precisely under known reaction conditions suitable for the above reaction. Other methods known in themselves, though not described in more detail herein, may also be used. Compounds of formula I are preferably prepared from the following starting materials.

[0036] [ka] In the equations above and below, R 1 If represents an alkyl and / or alkoxy group, it may be linear or branched. It is preferably linear and has 2, 3, 4, 5, 6 or 7 carbon atoms, and therefore preferably represents ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, and furthermore, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradecoxy.

[0037] Oxaalkyl preferably represents linear 2-oxapropyl (i.e., methoxymethyl), 2-(i.e., ethoxymethyl) or 3-oxabutyl (i.e., 2-methoxyethyl), 2-, 3- or 4-oxaheptyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, or 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.

[0038] R 1However, when a single CH2 group represents an alkyl group in which -CH=CH- is replaced, it may be either linear or branched. Preferably, it is linear and has 2 to 10 carbon atoms. Therefore, it represents, in particular, vinyl, propa-1- or propa-2-enyl, buta-1-, -2- or buta-3-enyl, penta-1-, -2-, -3- or penta-4-enyl, hexa-1-, -2-, -3-, -4- or hexa-5-enyl, hepta-1-, -2-, -3-, -4-, -5- or hepta-6-enyl, octa-1-, -2-, -3-, -4-, -5-, -6- or octa-7-enyl, nona-1-, -2-, -3-, -4-, -5-, -6-, -7- or nona-8-enyl, or deca-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or deca-9-enyl. Furthermore, these groups may be monohalogenated or polyhalogenated. Preferred halogenated groups are CH=CF2, CF=CF2, CF=CHF, and CH=CHF.

[0039] R 1 However, when representing an alkyl or alkenyl group that is at least one-substituted with a halogen, the group is preferably linear, and the halogen is preferably F or Cl. In the case of polysubstituted groups, the halogen is preferably F. The resulting group also includes perfluorinated groups. In the case of monosubstituted groups, the fluorine or chlorine substituent may be at any desired position, but is preferably at the ω position.

[0040] A more preferred embodiment is shown below.

[0041] The medium further comprises one or more neutral compounds of formula II and / or III.

[0042] [ka] During the ceremony, A represents 1,4-phenylene or trans-1,4-cyclohexylene. a is either 0 or 1, R 3represents alkenyl having 2 to 9 carbon atoms, and R 4 has the meaning indicated for R 1 in formula I, and preferably represents alkyl having 1 to 12 carbon atoms or alkenyl having 2 to 9 carbon atoms.

[0043] · The compound of formula II is preferably selected from the following formulae.

[0044]

Chemical Structure

[0045] Further, compounds of formula II having a non-terminal double bond in the alkenyl side chain are preferred.

[0046]

Chemical Structure

[0047]

Chemical Structure

[0048]

Chemical Structure

[0049] In addition to one or more compounds of formula I, the liquid crystal medium according to the present invention preferably contains 5 to 70% by weight, particularly 10 to 50% by weight, and very preferably 20 to 45% by weight of the compound of the following formula.

[0050] [ka] The compound of formula III is preferably selected from the following formulas.

[0051] [ka] In the formula, "alkyl" and R 3a It has the meaning shown above, R 3a This preferably represents H or CH3. Compounds of formula IIIb are particularly preferred.

[0052] The compound of formula IIIb-1 is very particularly preferred.

[0053] [ka] In the formula, "alkyl" has the meaning shown above, and preferably represents CH3, and more preferably C2H5 or n-C3H7.

[0054] The medium preferably additionally contains one or more compounds selected from the following formulas IV to VIII.

[0055] [ka] During the ceremony, R 0 This has the meaning shown in claim 6, X 0 This represents an alkyl or alkoxy group having 1 to 6 carbon atoms in the case of F and Cl, respectively, and an alkenyl or alkenyloxy group having 2 to 6 carbon atoms in the case of F and Cl, respectively, which are monofluorinated or polyfluorinated. Y 1~6 Each of these independently represents either H or F. Z 0 This represents -C2H4-, -(CH2)4-, -CH=CH-, -CF=CF-, -C2F4-, -CH2CF2-, -CF2CH2-, -CH2O-, -OCH2-, -COO-, -CF2O- or -OCF2-, and in formulas V and VI, it also represents a single bond, and r represents either 0 or 1.

[0056] In the above equation, X 0 Preferably, this is F, Cl, or a monofluorinated or polyfluorinated alkyl or alkoxy group having one, two, or three carbon atoms, or a monofluorinated or polyfluorinated alkenyl or alkenyloxy group having two or three carbon atoms. 0 Particularly preferred are F, Cl, CF3, CHF2, OCF3, OCHF2, OCHFCF3, OCHFCHF2, OCHFCH2F, OCF2CH3, OCF2CHF2, OCF2CH2F, OCF2CF2CHF2, OCF2CF2CH2F, OCFHCF2CF3, OCFHCF2CHF2, OCH=CF2, OCF=CF2, OCF2CHFCF3, OCF2CF2CF3, OCF2CF2CClF2, OClFCF2CF3, CF=CF2, CF=CHF, OCH=CF2, OCF=CF2, or CH=CF2.

[0057] In the compounds of formulas IV to VIII, X 0 This preferably represents F or OCF3, and more preferably OCHF2, CF3, CF2H, Cl, or OCH=CF2. 0 Preferably, it is a linear alkyl or alkenyl having up to 6 carbon atoms.

[0058] The compound of formula IV is preferably selected from the following formulas.

[0059] [ka] In the formula, R0 and X 0 This has the meaning set forth in claim 6.

[0060] Preferably, R in formula IV 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 represents F, Cl, OCHF2 or OCF3, and also OCH=CF2. In the compound of formula IVb, R 0 X preferably represents an alkyl or alkenyl group. In a compound of formula IVd, X 0 This preferably represents Cl, and more preferably, F.

[0061] The compound of formula V is preferably selected from formulas Va to Vj.

[0062] [ka]

[0063] [ka] In the formula, R 0 and X 0 has the meaning set forth in claim 6. Preferably, R in formula V. 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 represents F, OCF3, or OCH=CF2.

[0064] The medium contains one or more compounds of formula VI-1.

[0065] [ka] Particularly preferred is a selection from the following formulas.

[0066] [ka] In the formula, R 0 and X 0has the meaning set forth in claim 6. Preferably, R in formula VI 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 This represents F, and furthermore, CF3 and OCF3.

[0067] The medium contains one or more compounds of formula VI-2.

[0068] [ka] Particularly preferred is a selection from the following formulas.

[0069] [ka] In the formula, R 0 and X 0 has the meaning set forth in claim 6. Preferably, R in formula VI 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 This represents F.

[0070] The medium is preferably Z 0 The compound comprises one or more compounds of formula VII where -CF2O-, -CH2CH2-, or -COO-, particularly preferably selected from the following formulas.

[0071] [ka] In the formula, R 0 and X 0 has the meaning set forth in claim 6. Preferably, R in formula VII 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 This represents F, and furthermore, OCF3 and CF3.

[0072] The compound of formula VIII is preferably selected from the following formulas.

[0073] [ka] In the formula, R 0 and X 0 R has the meaning shown above. 0 Preferably, represents a linear alkyl group having 1 to 8 C atoms, X 0 This preferably represents F.

[0074] The medium additionally contains one or more compounds of the following formula:

[0075] [ka] In the formula, R 0 , X 0 , Y 1 and Y 2 This has the meanings shown above, and

[0076] [ka] This represents, However, rings A and B do not both simultaneously represent 1,4-cyclohexylene.

[0077] The compound of formula IX is preferably selected from the following formulas.

[0078] [ka] In the formula, R 0 and X 0 has the meaning shown in claim 6. Preferably, R in formula IX 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 represents F. Compounds of formula IXa are particularly preferred.

[0079] The medium additionally contains one or more compounds selected from the following formula.

[0080] [ka] In the formula, R0 , X 0 and Y 1~4 has the meaning shown in claim 6, and

[0081] [ka] It represents.

[0082] The compounds of formulas X and XI are preferably selected from the following formulas.

[0083] [ka]

[0084] [ka] In the formula, R 0 and X 0 has the meaning set forth in claim 6. Preferably, R 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 represents F. Particularly preferred compounds are Y. 1 This represents F, and Y 2 This represents H or F, preferably F.

[0085] The medium further contains one or more compounds of the following formula XII.

[0086] [ka] In the formula, R 1 and R 2 Each of these independently represents an alkyl, alkenyl, alkoxy, oxaalkyl, fluoroalkyl, or alkenyloxy group having up to nine carbon atoms, and preferably each independently represents an alkyl or alkenyl group having 1 to 8 carbon atoms or 2 to 8 carbon atoms.

[0087] The preferred compounds of formula XII are those of the following formula.

[0088] [ka] During the ceremony, Alkyl and alkyl * Each of these independently represents a linear alkyl group having 1 to 8 carbon atoms, and alkenyl and alkenyl * Each of these independently represents a linear alkenyl group having 2 to 8 carbon atoms.

[0089] Compounds of formulas XII-2 and XII-4 are particularly preferred.

[0090] Particularly preferred compounds of formula XII-2 are those of formulas XII-2a, XII-2b, and XII-2c.

[0091] [ka] Particularly preferred compounds of formula XII-4 are those of formulas XII-4a, XII-4b, and XII-4c.

[0092] [ka] The compound of formula XII is preferably used in an amount of 3 to 40% by weight.

[0093] The medium additionally contains one or more compounds selected from the following formula.

[0094] [ka] In the formula, R 0 , X 0 , Y 1 and Y 2 has the meaning set forth in claim 6. Preferably, R 0 X represents an alkyl group having 1 to 8 carbon atoms, and X0 represents F or Cl.

[0095] The compounds of formulas XIII and XIV are preferably selected from the compounds of the following formulas.

[0096] [ka] In the formula, R 0 and X 0 R has the meaning shown in claim 6. 0 Preferably, represents an alkyl group having 1 to 8 carbon atoms. In a compound of formula XIII, X 0 Preferably, represents F or Cl.

[0097] The medium further comprises one or more compounds of formulas D1, D2, D3, D4 and / or D5.

[0098] [ka] In the formula, Y 1 , Y 2 , R 0 and X 0 has the meaning set forth in claim 6. Preferably, R 0 X represents an alkyl group having 1 to 8 carbon atoms, and X 0 This represents F.

[0099] The following compound is particularly preferred.

[0100] [ka] In the formula, R 0 The above has the meaning, and preferably a linear alkyl having 1 to 6 C atoms, particularly C2H5, n-C3H7 or n-C5H 11 It represents.

[0101] The medium further contains one or more compounds of the following formula XVII.

[0102]

Chem.

[0103] · The medium additionally comprises one or more compounds of the following formula:

[0104]

Chem.

[0105]

Chem.

[0106] · The medium additionally comprises one or more tetracyclic compounds selected from formulae XIX to XXVIII.

[0107]

Chem.

[0108]

Chem.

[0109] In compounds of formulas XIX to XXVIII, R 0 X preferably represents a linear alkyl group. 0 This preferably represents F or OCF3, and more preferably CF3. 1 and Y 2 Preferably, Y 1 =F and Y 2 =H or Y 1 =Y 2 = represents F

[0110] Particularly preferred compounds of formulas XIX to XXVIII are X 0 However, it is preferably F, and more preferably a compound of formula XXV representing OCF3.

[0111] A preferred mixture contains at least one compound from groups S-1, S-2, S-3, and S-4, because these compounds, in particular, help suppress the smectic phase of the mixture.

[0112] [ka] The medium preferably contains one or more neutral compounds of general formula N.

[0113] [ka] During the ceremony, R N1 and R N2Each of these independently represents an alkyl or alkoxy group having 1 to 15 carbon atoms, except that one or more CH2 groups in these groups are independently bonded to each other such that the oxygen atoms are not directly bonded to each other, such as -C≡C-, -CF2O-,

[0114] [ka] Substitutions may include -O-, -CO-O-, and -O-CO-, and in addition, one or more H atoms may be replaced by halogens. Ring A N1 , A N2 and A N3 Each of these independently represents 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, trans-1,4-cyclohexylene (wherein one or two CH2 groups may be replaced by -O-), or 1,4-cyclohexenylene. Z N1 and Z N2 Each of these independently represents a single bond, -CH2CH2-, -COO-, -OCO-, -C≡C-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -CH=CH-. n represents 0, 1, or 2.

[0115] Preferred compounds of formula N are shown below.

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] [ka] During the ceremony, Alkyl and alkyl * Each of these independently represents a linear alkyl group having 1 to 9 carbon atoms, preferably 2 to 6 carbon atoms, and is represented by alkenyl and alkenyl * Each of these independently represents a linear alkyl group having 2 to 6 carbon atoms.

[0120] Among the compounds of formula N, compounds of formula N-1, N-2, N-3, N-4, N-8, N-9, N-14, N-15, N-17, N-18, N-19, N-20, N-21, N-22, N-23, N-24, N-25, N-31, N-33, and N-36 are particularly preferred.

[0121] The medium additionally contains one or more compounds of formulas St-1 to St-3.

[0122] [ka] In the formula, R 0 , Y 1 , Y 2 and X 0 R has the meaning set forth in claim 6. 0 This preferably represents a linear alkyl group having 1 to 6 carbon atoms. 0 Preferably, it is F, CF3, or OCF3. 1 This preferably represents F. 2 This preferably represents F. Furthermore, Y 1 =F and Y 2 Compounds with =H are preferred. Compounds of formulas St-1 to St-3 are preferably used in the mixture according to the present invention at a concentration of 3 to 30% by weight, particularly 5 to 25% by weight.

[0123] The medium further contains one or more pyrimidine or pyridine compounds of formulas Py-1 to Py-5.

[0124] [ka] In the formula, R 0 The pyrimidine compound is preferably a linear alkyl having 2 to 5 carbon atoms. x represents 0 or 1, preferably x=1. A preferred mixture contains 3 to 30% by weight, particularly 5 to 20% by weight, of these pyrimidine compounds (one or more).

[0125] The medium further comprises one or more compounds selected from the group of compounds of formulas Y-1, Y-2, Y-3, and Y-4.

[0126] [ka] During the ceremony, R 2A represents an alkyl or alkoxy group having H and 1 to 15 C atoms, provided that in addition, one or more CH2 groups in these groups are independently bonded to each other such that the O atoms are not directly bonded to each other, such as -C≡C-, -CF2O-, and -CH=CH-.

[0127] [ka] Substitutions may include -O-, -CO-O-, and -O-CO-, and in addition, one or more H atoms may be replaced by halogens. L 1~4 and L 2 Each of these independently represents F, Cl, CF3, or CHF2, preferably F, Z 2 and Z 2’ These represent, independently of each other, 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, (O)Cv H 2v+1 , OC v H 2v+1 or C v H 2v+1 This represents, v represents 1 through 6.

[0128] Particularly preferred compounds of formulas Y-1 to Y-4 are shown below.

[0129] [ka]

[0130] [ka]

[0131] [ka]

[0132] [ka] Among the compounds listed above, the compounds of formulas Y-1a, Y-1c, Y-1e, Y-1g, Y-1j, Y-1r, Y-1t, Y-2b, Y-2h, Y-2j, and Y-3a are particularly preferred.

[0133] In the mixture according to the present invention, the proportion of compounds of formulas Y-1 to Y-3 is preferably 0 to 30% by weight.

[0134] In the equations given above and below,

[0135] [ka] It represents.

[0136] ·R 0 Preferably, it is a linear alkyl or alkenyl having 2 to 7 carbon atoms.

[0137] ·X 0 is preferably F, more preferably OCF3, OCH=CF2, Cl or CF3.

[0138] ·The medium preferably comprises one, two or three compounds of formula I.

[0139] ·The medium preferably comprises one or more compounds selected from the group of compounds of formulae I, II, III, V, VI-1, VI-2, XII, XIII, XIV, XVII, XXIII and XXV.

[0140] ·The medium preferably comprises one or more compounds of formula VI-1.

[0141] ·The medium preferably comprises one or more compounds of formula VI-2.

[0142] ·The medium comprises 1 to 30 wt%, preferably 2 to 20 wt%, particularly preferably 2 to 15 wt% of the compound of formula I.

[0143] ·The proportion of the compounds of formulae II to XXVII in the entire mixture is preferably 20 to 99% by weight.

[0144] ·The medium comprises 25 to 80 wt%, particularly preferably 30 to 70 wt% of the compound(s) of formula II and / or III.

[0145] ·The medium comprises 0 to 70 wt%, particularly preferably 20 to 60 wt% of the compound of formula IIa-1.

[0146] ·The medium comprises 0 to 25 wt%, particularly preferably 5 to 25 wt% of the compound of formula IIa-2.

[0147] ·The medium comprises 0 to 30 wt%, particularly preferably 5 to 25 wt% of the compound of formula IIa-3.

[0148] The medium preferably contains 0 to 25% by weight, and particularly preferably 5 to 25% by weight, of the compound of formula IIa-5.

[0149] The medium preferably contains 5 to 40% by weight, and particularly preferably 10 to 30% by weight, of the compound of formula V.

[0150] The medium preferably contains 3 to 30% by weight, and particularly preferably 6 to 25% by weight, of the compound of formula VI-1.

[0151] The medium preferably contains 2 to 30% by weight, and particularly preferably 4 to 25% by weight, of the compound of formula VI-2.

[0152] The medium preferably contains 5 to 40% by weight, and particularly preferably 10 to 30% by weight, of the compound of formula XII.

[0153] The medium preferably contains 1 to 25% by weight, and particularly preferably 2 to 15% by weight, of the compound of formula XIII.

[0154] The medium preferably contains 5 to 45% by weight, and particularly preferably 10 to 35% by weight, of the compound of formula XIV.

[0155] The medium preferably contains 1 to 20% by weight, and particularly preferably 2 to 15% by weight, of the compound of formula XVI.

[0156] The medium is preferably 5-30% by weight, particularly preferably 8-22% by weight of formula Va (where X 0 It contains compounds of OCH=CF2.

[0157] Even in relatively small proportions, mixing the compound of formula I with conventional liquid crystal materials, but especially with one or more compounds of formulas II to XXVIII, results in increased low-temperature stability with little to no effect on rotational viscosity γ1. The liquid crystal medium according to the present invention is further distinguished by its relatively high birefringence and photostability, along with the observation of a wide range of nematic phases with low smectic-nematic transition temperatures, and simultaneously, improved storage life. At the same time, the mixture exhibits a very low threshold voltage and a very good VHR value when exposed to UV.

[0158] Expression "alkyl (alkyl)" or "alkyl * (alkyl * In this application, ")" includes linear and branched alkyl groups having 1 to 7 carbon atoms, particularly the linear groups methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl. Groups having 1 to 6 carbon atoms are generally preferred.

[0159] In this application, the expression "O-alkyl" includes both linear and branched alkoxy groups.

[0160] The expression "alkenyl" or "alkenyl" * (alkenyl *In this application, ")" includes linear and branched alkenyl groups having 2 to 7 carbon atoms, particularly linear groups. Preferred alkenyl groups are C2-C7-1E-alkenyls, C4-C7-3E-alkenyls, C5-C7-4-alkenyls, C6-C7-5-alkenyls and C7-6-alkenyls, particularly C2-C7-1E-alkenyls, C4-C7-3E-alkenyls and C5-C7-4-alkenyls. Particularly preferred examples of alkenyl groups include vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl, and 6-heptenyl. Groups having up to five carbon atoms are generally preferred.

[0161] In this application, the expression "fluoroalkyl" includes linear groups having at least one fluorine atom, preferably terminally fluorine, namely fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, and 7-fluoroheptyl. However, this does not exclude other positions of fluorine.

[0162] The expressions "oxaalkyl" or "alkoxy" in this application refer to formula C n H 2n+1 -O-(CH2) m The formula includes linear groups, where n and m each independently represent 1 to 6. m may also represent 0. Preferably, n is 1 and m is 1 to 6, or m is 0 and n is 1 to 3.

[0163] R in Equation I 1 and R 2By appropriately selecting the meaning of the terms, the address time, threshold voltage, and steepness of the transmission characteristic curve can be modified to the desired form. For example, 1E-alkenyl groups, 3E-alkenyl groups, and 2E-alkenyloxy groups generally exhibit shorter address times, improved nematic properties, and elastic constant k compared to alkyl and alkoxy groups. 33 (Bend) and k 11 This results in a higher ratio between (spray). 4-Alkenyl groups, 3-Alkenyl groups, etc., generally have lower threshold voltages and lower k values ​​compared to alkyl and alkoxy groups. 33 / k 11 The mixture according to the present invention is particularly distinguished by its high k1 value, and therefore has a much faster response time than mixtures from the prior art.

[0164] The optimal mixing ratio of the compound in the above formula depends substantially on the desired properties, the selection of the components in the above formula, and the selection of any further components, if any, are present.

[0165] The appropriate mixing ratio within the range shown above can be easily determined on a case-by-case basis.

[0166] The total amount of the compound of the above formula in the mixture according to the present invention is not definitive. Therefore, the mixture may contain one or more additional components for the purpose of optimizing various properties. However, the observed effect in the desired improvement of the properties of the mixture generally increases as the total concentration of the compound of the above formula increases.

[0167] In a particularly preferred embodiment, the medium according to the present invention is X 0 However, these include compounds of formulas IV to VIII, representing F, OCF3, OCHF2, OCH=CF2, OCF=CF2, or OCF2-CF2H. Particularly advantageous properties result from favorable synergistic effects with compounds of formula I. In particular, mixtures containing compounds of formulas I and VI, or I and XI, or I, VI, and XI, stand out due to their low threshold voltages.

[0168] The individual compounds of the above-mentioned formulas and their sub-formulas that can be used in the medium according to the present invention are either known or can be prepared analogously to known compounds.

[0169] The present invention also relates to an electro-optical display containing a medium of this type, which comprises two flat parallel outer plates forming a cell together with an outer frame, integrated non-linear elements on the outer plates for switching individual pixels, and a nematic liquid crystal mixture disposed in the cell having positive dielectric anisotropy and high specific resistivity, for example in TN, STN, TFT, OCB, IPS, PS-IPS, FFS, PS-FFS, positive VA or MLC displays, and to the use of these media for electro-optical purposes.

[0170] Furthermore, the mixtures according to the present invention are also suitable for positive VA applications, also referred to as HT-VA applications. These mean electro-optical displays having an in-plane driving electrode arrangement and homeotropic alignment of a liquid crystal medium having positive dielectric anisotropy. The mixtures according to the present invention are particularly preferably suitable for TN-TFT display applications having low operating voltages, i.e., particularly preferably for notebook personal computer applications.

[0171] The liquid crystal mixture according to the present invention can significantly expand the degree of freedom of available parameters. The achievable combination of clearing point, viscosity at low temperatures, thermal and UV stability and high optical anisotropy is far superior to conventional materials from the prior art.

[0172] The mixtures according to the present invention are particularly suitable for portable applications such as PDAs, notebook personal computers, LCD televisions and monitors, and TFT applications with high Δn.

[0173] The liquid crystal mixture according to the present invention makes it possible to achieve a rotational viscosity γ1 of 120 mPa·s or less, particularly preferably 60 mPa·s or less, while simultaneously maintaining a nematic phase down to -20°C, preferably down to -30°C, and particularly preferably down to -40°C, and a transparency point of 70°C or higher, preferably 74°C or higher, thereby enabling the creation of an excellent MLC display with a fast response time.

[0174] The dielectric anisotropy Δε of the liquid crystal mixture according to the present invention is preferably +3 or higher, and particularly preferably +4 or higher. In addition, the mixture is characterized by a low operating voltage. The threshold voltage of the liquid crystal mixture according to the present invention is preferably 2.5V or lower, and particularly 2.2V or lower.

[0175] The birefringence Δn of the liquid crystal mixture according to the present invention is preferably 0.08 or higher, and particularly 0.10 or higher.

[0176] The nematic phase of the liquid crystal mixture according to the present invention preferably has a width of at least 90°, and more particularly, at least 100°. This range preferably extends from at least -20°C to +70°C.

[0177] When the mixture according to the present invention is used in IPS or FFS applications, the mixture preferably has a dielectric anisotropy value of 3 to 20 and an optical anisotropy value of 0.07 to 0.13.

[0178] Needless to say, by appropriately selecting the components of the mixture according to the present invention, it is possible to achieve a higher transparency point (e.g., above 100°C) at a higher threshold voltage, or a lower transparency point at a lower threshold voltage, while maintaining other advantageous properties. It is also possible to obtain a mixture having a higher Δε and therefore a lower threshold voltage with only a slight corresponding increase in viscosity. The MLC display according to the present invention preferably operates at the first-order transmission minimum of Gooch and Hatarry [CH Gooch and Hatarry, Electron. Lett., Vol. 10, pp. 2-4, 1974; CH Gooch and Hatarry, Appl. Phys., Vol. 8, pp. 1575-1584, 1975], in which case, in addition to particularly desirable electro-optical properties such as high steepness of characteristic lines and low angular dependence of contrast (German Patent No. 30 22 818), a lower dielectric anisotropy is sufficient to obtain the same threshold voltage as a similar display at the second-order minimum. For this reason, by using the mixture according to the present invention at the first-order minimum, a much higher resistivity can be achieved than in the case of a mixture containing cyano compounds. Through the appropriate selection of the individual components and their mass ratios, those skilled in the art can set the required birefringence for a predetermined layer thickness of the MLC display using simple everyday methods.

[0179] The configuration of the MLC display according to the present invention, consisting of a polarizer, an electrode substrate, and surface-treated electrodes, corresponds to a typical design of this type of display. The term "typical design" is used herein in a broad sense and also encompasses all derivatives and modifications of MLC displays, in particular matrix display elements based on polycrystalline silicon TFTs or MIMs, and more particularly, semi-transmissive and reflective displays.

[0180] However, a major difference between the display according to the present invention and conventional displays based on twisted nematic cells lies in the selection of liquid crystal parameters for the liquid crystal layer.

[0181] The liquid crystal mixtures usable according to the present invention are, for example, prepared in a conventional manner by mixing one or more compounds of formula I with one or more compounds of formulas II to XXVII, or with further liquid crystal compounds and / or additives. Generally, the desired amount of a component used in smaller quantities is dissolved in the components constituting the main composition, preferably by heating. Alternatively, the component solutions in an organic solvent, for example acetone, chloroform, or methanol, can be mixed, and after complete mixing, the solvent can be removed again, for example, by distillation.

[0182] Furthermore, the dielectric may contain additional additives known to those skilled in the art and documented in the literature, such as UV stabilizers, antioxidants, free radical scavengers, and nanoparticles, such as Tinuvin®, particularly Tinuvin® 770, manufactured by Ciba Chemicals. For example, 0-15% of a polychromatic dye or chiral dopant may be added. Suitable stabilizers and dopants are listed in Tables C and D below.

[0183] To set a desired tilt angle, polymerizable compounds, i.e., so-called "reactive mesogens," may also be added to the mixture according to the present invention. Preferred polymerizable compounds are listed in Table E.

[0184] In this application and the examples below, the structures of liquid crystal compounds are shown by abbreviations, and their conversion to chemical formulas is performed according to Table A below. All groups C n H 2n+1 and C m H 2m+1 is a linear alkyl group having n and m carbon atoms, respectively, where n, m, and k are integers, preferably representing 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. The codes in Table B are self-explanatory. In Table A, only abbreviations related to the parent structure are shown. In each case, after this abbreviation of the parent structure, separated by a dash, is the substituent R 1* , R 2* , L 1* and L 2* The code for this follows.

[0185] [Table 1] Preferred mixture components are shown in Tables A and B.

[0186] [Table 2]

[0187] [Table 3]

[0188] [Table 4]

[0189] [Table 5]

[0190] [Table 6]

[0191] [Table 7]

[0192] [Table 8]

[0193] [Table 9]

[0194] [Table 10] (n=1~15; (O)C n H2n+1 C n H 2n+1 or OC n H 2n+1 (This means...) A liquid crystal mixture containing at least one, two, three, or four or more compounds from Table B in addition to the compound of formula I is particularly preferred.

[0195] Table C shows the dopants that can generally be added to the mixture according to the present invention. The mixture preferably contains 0 to 10% by weight, particularly 0.01 to 5% by weight, and especially preferably 0.01 to 3% by weight of the dopant.

[0196] [Table 11] For example, stabilizers that can be added to the mixture according to the present invention in an amount of 0 to 10% by weight are described below.

[0197] [Table 12]

[0198] [Table 13]

[0199] [Table 14]

[0200] [Table 15] Table E shows example compounds that can be used in the LC medium according to the present invention, preferably as reactive mesogenic compounds. When the mixture according to the present invention contains one or more reactive compounds, they are preferably used in amounts of 0.01 to 5% by weight. It may also be necessary to add an initiator for polymerization or a mixture of two or more initiators. The initiator or initiator mixture is preferably added in amounts of 0.001 to 2% by weight based on the mixture. Suitable initiators are, for example, Irgacure (BASF) and Irganox (BASF).

[0201] [Table 16]

[0202] [Table 17]

[0203] [Table 18]

[0204] [Table 19]

[0205] [Table 20]

[0206] [Table 21]

[0207] [Table 22]

[0208] [Table 23]

[0209] [Table 24]

[0210] [Table 25] In a preferred embodiment, the mixture according to the present invention preferably comprises one or more polymerizable compounds selected from polymerizable compounds of formulas RM-1 to RM-83. This type of medium is particularly suitable for PS-FFS and PS-IPS applications. Among the reactive mesogens described in Table E, compounds RM-1, RM-2, RM-3, RM-4, RM-5, RM-11, RM-17, RM-35, RM-41, RM-61, and RM-80 are particularly preferred. [Examples]

[0211] The following examples are intended to illustrate the present invention without limiting it.

[0212] In the above and below, percentage data represents weight percentage. All temperatures are given in degrees Celsius. mp represents the melting point, and cl.p. represents the transparency point. Furthermore, C represents the crystalline state, N represents the nematic phase, S represents the smectic phase, and I represents the isotropic phase. The data between these symbols represents the transition temperature. Furthermore, V0 represents the capacitance threshold voltage [V] at 20°C. Δn represents the optical anisotropy measured at 20°C and 589 nm. Δε represents the dielectric anisotropy at 20°C and 1kHz. cp. represents the point of transparency [°C], K1 represents the elastic constant [pN] for "splay" deformation at 20°C. K3 represents the elastic constant [pN] for "bend" deformation at 20°C. γ1 represents the rotational viscosity [mPa·s] measured at 20°C, and is determined by the rotational method in a magnetic field. LTS stands for low-temperature stability (nematic phase) and is determined in a test cell.

[0213] <Example of synthesis> "Conventional method" means adding water as needed, extracting the mixture with methylene chloride, diethyl ether, methyl t-butyl ether or toluene, separating the phases, drying and evaporating the organic phase, and purifying the product by vacuum distillation or crystallization and / or chromatography.

[0214] <Example 1> The compound shown below,

[0215] [ka] Prepare according to the following scheme.

[0216] [ka]

[0217] [Table 26] Similarly, the following compounds are prepared.

[0218] [ka] <Mixture example> Unless otherwise specified, electro-optical data are measured in a TN cell at 20°C with a first minimum (i.e., a d·Δn value of 0.5 μm). Unless otherwise specified, optical data are measured at 20°C. All physical properties are determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals," November 1997, Merck AG, Germany, and unless otherwise specified, a temperature of 20°C is applied.

[0219] [Table 27] <Example 2> To prepare the PS-IPS mixture, 0.25% of compound RM-1 is added to mixture M1.

[0220] [ka]

[0221] [Table 28] <Example M4> To prepare the PS-FFS mixture, 0.3% of compound RM-41 is added to mixture M3.

[0222] [ka]

[0223] [Table 29] <Example M6> To prepare the PS-FFS mixture, 0.25% of compound RM-1 is added to mixture M5.

[0224] [ka] <Example M7> To prepare the PS-IPS mixture, 0.25% of compound RM-17 is added to mixture M5.

[0225] [ka]

[0226] [Table 30] <Example M9> To prepare the PS-FFS mixture, 0.25% of compound RM-1 is added to mixture M8.

[0227] [ka] <Example M10> To prepare the PS-FFS mixture, 0.2% of compound RM-61 is added to mixture M8.

[0228] [ka]

[0229] [Table 31] <Example M12> To prepare the PS-FFS mixture, 0.25% of compound RM-1 is added to mixture M11.

[0230] [ka] <Example M13> To prepare the PS-IPS mixture, 0.3% of compound RM-80 is added to mixture M11.

[0231] [ka]

[0232] [Table 32] <Example M12> To prepare the PS-IPS mixture, 0.25% of compound RM-17 is added to mixture M12.

[0233] [ka]

[0234] [Table 33] <Example M14> To prepare the PS-FFS mixture, 0.25% of compound RM-1 is added to mixture M13.

[0235] [ka]

[0236] [Table 34]

[0237] [Table 35]

[0238] [Table 36] <Example M18> To prepare the PS-FFS mixture, 0.25% of compound RM-1 is added to mixture M17.

[0239] [ka]

[0240] [Table 37]

[0241] [Table 38]

[0242] [Table 39]

[0243] Table 40

[0244] Table 41

[0245] Table 42

[0246] Table 43

[0247] Table 44

[0248] Table 45

[0249] Table 46

[0250] Table 47

[0251] Table 48

[0252] Table 49

[0253] Table 50

[0254] Table 51

[0255] Table 52

[0256] Table 53

[0257] Table 54

[0258] Table 55

[0259] Table 56

[0260] Table 57

[0261] Table 58

[0262] Table 59

[0263] Table 60

[0264] Table 61

[0265] Table 62

[0266] Table 63

[0267] Table 64

[0268] Table 65

[0269] Table 66

[0270] Table 67

[0271] Table 68

[0272] Table 69

[0273] Table 70

[0274] Table 71

[0275] [Table 72]

[0276] [Table 73]

[0277] [Table 74] <Example M57> To prepare the PS-IPS mixture, 0.3% of compound RM-1 is added to mixture M56.

[0278] [ka] <Example M58> To prepare the PS-FFS mixture, 0.3% of compound RM-41 is added to mixture M56.

[0279] [ka]

[0280] [Table 75]

[0281] [Table 76]

[0282] [Table 77]

[0283] [Table 78] LC mixture M62 is particularly suitable for 3D lens display applications.

Claims

1. A liquid crystal medium characterized by containing one or more compounds of formula I. 【Chemistry 1】 (In the formula, R １ represents an alkyl or alkoxy group having 1 to 15 carbon atoms, in addition to one or more CH groups. ２ The groups are arranged independently of each other, with the oxygen atoms not directly bonded to one another, such as -C≡C- and -CF ２ O-, -CH=CH-, 【Chemistry 2】 (The atoms may be replaced with -O-, -CO-O-, or -O-CO-, and in addition, one or more H atoms may be replaced with halogen atoms.)

2. R in equation I １ represents a linear alkyl group, in addition to one or more CH ２ The liquid crystal medium according to claim 1, characterized in that the base may be replaced with -CH=CH-.

3. The liquid crystal medium according to claim 1 or 2, characterized by comprising at least one compound from the group of compounds of formulas I-1 to I-5. 【Transformation 3】

4. A liquid crystal medium according to any one of claims 1 to 3, characterized in that it additionally contains one or more compounds of formula II and / or III. 【Chemistry 4】 (In the formula, A represents 1,4-phenylene or trans-1,4-cyclohexylene. a represents 0 or 1, R ３ This represents an alkenyl having 2 to 9 C atoms, and R ４ In claim 1, R １ (It has the meaning shown.)

5. A liquid crystal medium according to any one of claims 1 to 4, characterized in that it additionally contains one or more compounds selected from the compounds of the following formula. 【Transformation 5】 【Transformation 6】 (wherein R ３ａ and R ４ａ are each independently selected from H, CH ３ , C ２ H ５ or C ３ H ７ , and "alkyl" represents a linear alkyl group having 1 to 8 C atoms.)

6. A liquid crystal medium according to any one of claims 1 to 5, characterized in that it additionally contains one or more compounds selected from the compounds of formulas IV to VIII. 【Transformation 7】 (In the formula, R ０ represents an alkyl or alkoxy group having 1 to 15 carbon atoms, in addition to one or more CH groups. ２ The groups are arranged independently of each other, with the oxygen atoms not directly bonded to one another, such as -C≡C- and -CF ２ O-, -CH=CH-, 【Transformation 8】 It may be replaced with -O-, -CO-O-, or -O-CO-, and in addition, one or more H atoms may be replaced with halogen atoms. X ０ This represents F, Cl, an alkyl or alkoxy group having 1 to 6 carbon atoms and being monofluorinated or polyfluorinated, or an alkenyl or alkenyloxy group having 2 to 6 carbon atoms and being monofluorinated or polyfluorinated. Y １～６ Each of these independently represents either H or F. Z ０ is, -C ２ H ４ -, - (CH ２ ) ４ -, -CH=CH-, -CF=CF-, -C ２ F ４ -ien-CH ２ CF ２ -, -CF ２ CH ２ -ien-CH ２ O-, -OCH ２ -, -COO-, -CF ２ O- or -OCF ２ It represents -, and in formulas V and VI, it also represents a single bond, and r represents either 0 or 1.

7. A liquid crystal medium according to any one of claims 1 to 6, characterized in that it additionally contains one or more compounds selected from the compounds of formulas Va to Vj. 【Chemistry 9】 【Chemistry 10】 (In the formula, R ０ and X ０ (This has the meaning shown in claim 6.)

8. A liquid crystal medium according to any one of claims 1 to 7, characterized in that it further comprises one or more compounds selected from the compounds of formulas VI-1a to VI-1d. 【Chemistry 11】 (In the formula, R ０ and X ０ (This has the meaning shown in claim 6.)

9. A liquid crystal medium according to any one of claims 1 to 8, characterized in that it further comprises one or more compounds selected from the compounds of formulas VI-2a to VI-2f. 【Chemistry 12】 (In the formula, R ０ and X ０ (This has the meaning shown in claim 6.)

10. A liquid crystal medium according to any one of claims 1 to 9, characterized in that it further comprises one or more compounds selected from the compounds of formula X and / or XI. 【Chemistry 13】 (In the formula, R ０ and X ０ This has the meaning shown in claim 6, Y １～４ Each represents H or F independently of the other, and 【Chemistry 14】 (This represents...)

11. A liquid crystal medium according to any one of claims 1 to 10, characterized in that it additionally contains one or more compounds selected from the compounds of formula XII. 【Chemistry 15】 (In the formula, R １ and R ２ Each of these independently represents an alkyl, alkenyl, alkoxy, oxaalkyl, fluoroalkyl, or alkenyloxy group having up to nine carbon atoms, and Y １ (This represents H or F.)

12. A liquid crystal medium according to any one of claims 1 to 11, characterized in that it additionally contains one or more compounds selected from the compounds of formulas XIII to XVI. 【Chemistry 16】 (In the formula, R ０ , X ０ , Y １ and Y ２ (This has the meaning shown in claim 6.)

13. A liquid crystal medium according to any one of claims 1 to 12, characterized by containing 1 to 30% by weight of the compound of formula I.

14. A liquid crystal medium according to any one of claims 1 to 13, characterized in that it additionally contains one or more UV stabilizers and / or antioxidants.

15. A liquid crystal medium according to any one of claims 1 to 14, characterized in that it additionally contains one or more polymerizable compounds.

16. The liquid crystal medium according to any one of claims 1 to 15, characterized in that the polymerizable compound is selected from the group RM-1 to RM-83. 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】

17. A method for preparing a liquid crystal medium according to any one of claims 1 to 16, characterized by mixing one or more compounds of formula I with at least one further mesogenic compound and, as an optional component, one or more additives (one or more) and / or one or more polymerizable compounds.

18. Use of a liquid crystal medium according to any one of claims 1 to 16 for electro-optical purposes.

19. Use of the liquid crystal medium according to claim 18 in TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS displays, shutter glasses, LC lenses, and positive VA displays.

20. An electro-optical liquid crystal display containing the liquid crystal medium described in any one of claims 1 to 16.

21. Compound of formula I. 【Chemistry 27】 (In the formula, R １ represents an alkyl or alkoxy group having 1 to 15 carbon atoms, in addition to one or more CH groups. ２ The groups are arranged independently of each other, with the oxygen atoms not directly bonded to one another, such as -C≡C- and -CF ２ O-, -CH=CH-, 【Chemistry 28】 (The atoms may be replaced with -O-, -CO-O-, or -O-CO-, and in addition, one or more H atoms may be replaced with halogen atoms.)

22. The compound according to claim 21 of formulas I-1 to I-5. 【Chemistry 29】

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