Compounds, liquid-crystalline media and liquid-crystalline displays comprising the same
By optimizing the liquid crystal medium using a dielectric positive liquid crystal compound with a specific structure, the problems of transmittance, response time, and stability of liquid crystal displays have been solved, resulting in a high-efficiency liquid crystal display with low voltage and fast response, suitable for a variety of display devices.
Patent Information
- Application Number
- CN202180086040.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-12-22
- Filing Date
- 2021-12-20
- Publication Date
- 2026-02-27
- Estimated Expiration
- 2041-12-20
AI Technical Summary
Existing liquid crystal displays have shortcomings in terms of transmittance, response time, contrast ratio, and stability. In particular, the high operating voltage and long response time caused by the dielectric negative liquid crystal medium make it difficult to meet the diverse requirements of industrial applications.
By employing a liquid crystal medium containing at least one or more dielectric positive liquid crystal compounds with specific structures, the dielectric properties and rotational viscosity are optimized, thereby improving the stability and response speed of the liquid crystal mixture and enhancing the contrast and transmittance of the display.
It achieves a liquid crystal display with low threshold voltage, short response time, wide nematic phase range, good stability and high transmittance, and is suitable for a variety of applications, including monitors, televisions and mobile devices.
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Figure CN116670256B_ABST
Abstract
Description
[0001] The present application relates to novel liquid-crystalline media, in particular for energy-efficient liquid-crystalline displays, and to these liquid-crystalline displays, in particular to liquid-crystalline displays using the IPS (in-plane switching) or preferably FFS (fringe field switching) effect (both using dielectrically positive liquid crystals). The latter is occasionally also called XB-FFS (extra-bright FFS) effect.
[0002] For this effect, dielectrically positive liquid crystals are used, which comprise one or more compounds having a high dielectric constant both parallel and perpendicular to the molecular director, which leads to a large average dielectric constant and a high dielectric ratio and preferably simultaneously to a relatively small dielectric anisotropy. The liquid-crystalline medium optionally additionally comprises dielectrically negative compounds, dielectrically neutral compounds or both. The liquid-crystalline medium is used for an in-plane (i.e. planar) initial alignment. The liquid-crystalline medium of the present application has a positive dielectric anisotropy and comprises compounds having a large dielectric constant both parallel and perpendicular to the molecular director.
[0003] The media are characterized by a particularly good performance in the dark state, which is mainly due to their very low scattering. This in turn is caused, inter alia, by their high elastic constant.
[0004] The high elastic constant can also lead to higher values of the rotational viscosity (γ1). And thus to a higher ratio of the rotational viscosity (γ1) to the elastic constant of the splay deformation (k 22 ) of the twist deformation (k 22 , which in turn leads to higher response times. Since k 22 is approximately proportional to the elastic constant of the splay deformation k 11 (k 22 is usually about half the value of k 11 ), γ1 and k 11 can be easily and conveniently approximated.
[0005] The contrast of an LC display can be improved on the one hand by a higher transmittance, which can be achieved by the higher ε ⊥ in FFS cell layouts. And on the other hand, it can be improved by a better dark state. The latter, the dark state, is strongly influenced, inter alia, by the scattering parameters. Here, the liquid-crystalline media with high elastic constant reduce the scattering and thus improve the contrast of the LCD. This also leads to their superior performance in displays according to the present application.
[0006] IPS and FFS displays using dielectrically positive liquid crystals are well known in the art and have been widely adopted for various types of displays, such as desktop monitors and televisions, but also for mobile applications.
[0007] However, at present, IPS and, in particular, FFS displays using dielectrically negative liquid crystals are widely used. The latter are sometimes also called UB-FFS (ultra-bright FFS). Such displays are disclosed, for example, in US 2013 / 0207038 A1. These displays are characterized by a significantly increased transmittance compared to previously used IPS- and FFS displays using dielectrically positive liquid crystals. However, these displays using conventional dielectrically negative liquid crystals have the serious disadvantage that higher operating voltages are required compared to displays using dielectrically positive liquid crystals. Liquid-crystalline media for UB-FFS have a dielectric anisotropy of -0.5 or less and preferably -1.5 or less.
[0008] Liquid-crystalline media for HB-FFS (high brightness FFS) have a dielectric anisotropy of 0.5 or more and preferably 1.5 or more. Liquid-crystalline media for HB-FFS comprising both dielectrically negative and dielectrically positive liquid-crystalline compounds, or mesogenic compounds, are disclosed, for example, in US 2013 / 0207038 A1. These media are characterized by already quite large values of ε ⊥ and ε av. but their ratio (ε ⊥ / Δε) is relatively small.
[0009] However, according to the present application, IPS or FFS effects with dielectrically positive liquid-crystalline media aligned homogeneously are preferred.
[0010] The industrial use of this effect in electro-optical display elements requires liquid-crystalline phases which must satisfy a number of requirements. Of particular importance here are the chemical resistance and the physical influences, such as moisture, air, heat, radiation in the infrared, visible and ultraviolet regions, and direct current (DC) and alternating current (AC) electric fields.
[0011] Furthermore, an industrially useful liquid-crystalline phase requires a liquid-crystalline mesophase at a suitable temperature range and low viscosity.
[0012] None of the series of compounds having a liquid-crystalline mesophase which have been disclosed to date comprises a single compound which meets all these requirements. Therefore, usually mixtures of 2 to 25, preferably 3 to 18, compounds are prepared to obtain a substance which can be used as a liquid-crystalline phase.
[0013] Matrix liquid-crystalline displays (MLC displays) are known. Non-linear elements which can be used for the individual switching of the pixels are, for example, active elements (i.e. transistors). The term "active matrix" is then used, wherein usually thin-film transistors (TFT) are used, which are usually arranged on a glass plate as substrate.
[0014] The distinction between the two technologies is: TFTs containing compound semiconductors, such as CdSe, or metal oxides like ZnO, or TFTs based on polycrystalline and especially amorphous silicon. The latter technology has the greatest commercial importance worldwide at present.
[0015] The TFT matrix is applied to the inner side of one glass plate of the display, while the other glass plate carries a transparent counter electrode on its inner side. The TFTs are very small compared to the size of the pixel electrodes and have almost no adverse effect on the image. The technology can also be extended to full color functional displays, in which a mosaic of red, green and blue filters is arranged in such a way that the filter elements are arranged opposite each switchable pixel.
[0016] The TFT displays most commonly used to date generally use crossed polarizer operation in transmission and are backlit. For TV applications, ECB (or VAN) cells or FFS cells are used, while monitors generally use IPS cells or TN (twisted nematic) cells, and notebook, laptop and mobile applications generally use TN, VA or FFS cells.
[0017] The term MLC display here includes any matrix display with integrated nonlinear elements, i.e. in addition to active matrices, also displays with passive elements, such as varistors or diodes (MIM = metal-insulator-metal).
[0018] This type of MLC display is particularly suitable for TV applications, monitors and notebooks or for displays with high information density, for example in car manufacturing or aircraft construction. In addition to problems with the angle dependence of the contrast and the response time, some problems also arise in MLC displays due to the insufficiently high specific resistance of the liquid crystal mixture [TOGASHI, S., SEKI-GUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A210-288 Matrix LCD Controlled by Double Stage Diode Rings, pp. 141 ff., Paris; STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, p. 145, Paris]. With decreasing resistance, the contrast of the MLC display deteriorates. Since the specific resistance of the liquid crystal mixture usually decreases with the lifetime of the MLC display due to interactions with the inner surfaces of the display, a high (initial) resistance is of great importance for the display in order to have an acceptable resistance value over a long operating period.
[0019] In addition to IPS displays (for example: Yeo, S. D., Paper 15.3: "An LC Display for the TV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 758 and 759) and the long-known TN displays, displays using the ECB effect have established the so-called VAN (Vertically Aligned Nematic) displays as one of the three most important newer types of liquid crystal displays today, in particular for television applications.
[0020] Among the most important designs that can be mentioned here are MVA (multi-domain vertical alignment, e.g. Yoshide, H. et al., Paper 3.1 : "MVA LCD for Notebook or Mobile PCs... ", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6-9, and Liu, C. T. et al., Paper 15.1 : "A 46-inch TFT-LCD HDTV Technology... ", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 750-753), PVA (patterned vertical alignment, e.g. Kim, Sang Soo, Paper 15.4: "Super PVA Sets New State-of-the-Art for LCD-TV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 760-763) and ASV (advanced super view, e.g. Shigeta, Mitzuhiro and Fukuoka, Hirofumi, Paper 15.2: "Development of High Quality LCD TV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 754-757). More modern versions of the VA effect are the so-called PAVA (photo-alignment VA) and PSVA (polymer sustained VA).
[0021] In general terms, the techniques are compared, for example, in Souk, Jun, SID Seminar 2004, Seminar M-6: "Recent Advances in LCD Technology", Seminar Lecture Notes, M-6 / 1 to M-6 / 26, and Miller, Ian, SID Seminar 2004, Seminar M-7: "LCD-Television", Seminar Lecture Notes, M-7 / 1 to M-7 / 32. Although the response time of modern ECB displays has been improved significantly by addressing methods with overdrive, for example Kim, Hyeon Kyeong et al., Paper 9.1 : "A 57-in. Wide UXGA TFT-LCD for HDTV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pages 106 to 109, the implementation of a video-compatible response time, in particular in the switching of grey levels, remains an unsatisfactory problem.
[0022] ECB displays, like ASV displays, use liquid-crystalline media with negative dielectric anisotropy (Δε), whereas TN and hitherto all conventional IPS displays use liquid-crystalline media with positive dielectric anisotropy. However, there is an increasing demand for IPS and FFS displays which make use of liquid-crystalline media with negative dielectric anisotropy.
[0023] In this type of liquid-crystalline display, the liquid crystal is used as an electrical medium, the optical properties of which change reversibly when a voltage is applied.
[0024] Since, generally in displays, i.e. also in displays according to these mentioned effects, the operating voltage should be as low as possible, liquid-crystalline media which generally consist predominantly of liquid-crystalline compounds having the same sign of dielectric anisotropy and having the highest possible value of dielectric anisotropy are used. Generally, at most a relatively small proportion of neutral compounds and, if possible, no compounds having a dielectric anisotropy of opposite sign to the dielectric anisotropy of the medium are employed. In the case of liquid-crystalline media having a negative dielectric anisotropy, for example for ECB or UB-FFS displays, therefore predominantly compounds having a negative dielectric anisotropy are employed. The liquid-crystalline media employed generally consist predominantly and often even essentially of liquid-crystalline compounds having a negative dielectric anisotropy.
[0025] In the media used according to the present application, generally a significant amount of dielectrically positive liquid crystalline compounds is employed and generally only very small amounts of dielectrically negative compounds or even no dielectrically negative compounds at all, since generally the liquid crystal display is intended to have the lowest possible addressing voltage. At the same time, in certain cases it can be advantageous to use small amounts of dielectrically neutral compounds.
[0026] US 2013 / 0207038 A1 discloses liquid crystal media for HB-FFS displays, proposing to improve the performance of FFS displays using liquid crystals with positive dielectric anisotropy by additionally incorporating dielectrically negative liquid crystals. However, this leads to the need to compensate the negative contribution of these compounds to the overall dielectric anisotropy of the resulting media. For this, the concentration of dielectrically positive materials has to be increased, which in turn makes less space for using dielectrically neutral compounds as diluents in the mixture, or, alternatively, compounds with a stronger positive dielectric anisotropy have to be used. Both alternatives have the strong disadvantage of increasing the response time of the liquid crystals in the display.
[0027] Liquid crystal media with positive dielectric anisotropy for IPS and FFS displays have been disclosed. Some examples will be given below.
[0028] CN 104232105 A, WO 2014 / 192390 and WO 2015 / 007131 disclose liquid crystal media with positive dielectric anisotropy, some of which have a rather high dielectric constant perpendicular to the director.
[0029] The phase range of the liquid crystal mixture should be broad enough for the desired display application.
[0030] The response time of the liquid crystal media in the display must also be improved, i.e. reduced. This is particularly important for displays of televisions or multimedia applications. In order to improve the response time, it has been repeatedly proposed in the past to optimize the rotational viscosity (γ1) of the liquid crystal media, i.e. to obtain a medium with the lowest possible rotational viscosity. However, the results achieved here are insufficient for many applications, and it is therefore desirable to find a further optimization.
[0031] The sufficient stability of the media to extreme loads, in particular to UV exposure and heating, is of very particular importance. This can be critical, in particular in the case of applications in mobile devices, such as mobile phones.
[0032] In addition to their relatively poor transmittance and their relatively long response times, the MLC displays disclosed to date also have other disadvantages. These are, for example, their relatively low contrast, their relatively high viewing-angle dependence and the difficulty of reproducing gray scales in these displays, especially when viewed from an oblique viewing angle, and their insufficient VHR and their insufficient lifetime. Desired improvements in the transmittance of the displays and in their response times are required in order to improve their energy efficiency or their ability to render rapidly moving pictures, respectively.
[0033] There is therefore a great demand for MLC displays with very high specific resistance while at the same time large operating temperature ranges, short response times and relatively low threshold voltages, with the aid of which a large number of gray scales can be produced and which in particular have a good and stable VHR.
[0034] It is an object of the present application to provide MLC displays, not only for monitor and TV applications, but also for mobile applications, such as telephones and navigation systems, which are based on the ECB, IPS or FFS effect, without the above-mentioned disadvantages or with the above-mentioned disadvantages to a reduced extent, and at the same time have very high specific resistance values. In particular, it must be ensured for mobile telephones and navigation systems that they also operate at very high and very low temperatures.
[0035] Surprisingly, it has been found that if a nematic liquid-crystalline medium as described below is used in these display elements, liquid-crystal displays, in particular IPS and FFS displays, can be obtained which have a low threshold voltage and a short response time, a sufficiently wide nematic phase, an advantageous birefringence (Δn) and at the same time a high transmittance, a high contrast, a good stability against decomposition by heating and UV exposure, and a stable high VHR, wherein the nematic liquid-crystalline medium comprises at least one, preferably two or more, compounds of the formula C, preferably selected from the compounds of the subformulae C-1 to C-4, particularly preferably of the subformulae C-1 and / or C-3, more preferably of the formula C-3, and preferably additionally one or more, preferably two or more, compounds of the formula B, preferably selected from the compounds of the formulae B-1 to B-4, preferably both of the formulae B-2 and B-4.
[0036] In a preferred embodiment, the liquid-crystalline medium comprises one or more compounds of the formula I, preferably selected from the compounds of the subformulae I-1 and I-2, particularly preferably one or more of both of the formulae I-1 and I-2.
[0037] In a further preferred embodiment, the liquid-crystalline medium comprises one or more compounds selected from the formulae II and III, while the former preferably is of the formulae II-1 and / or II-2, and / or one or more, preferably two or more, compounds selected from the formulae IV and / or V, and preferably one or more compounds selected from the formulae VI to IX (all formulae are defined herein below).
[0038] This type of medium can be used in particular for electro-optical displays with active matrix addressing, such as IPS- or FFS-displays.
[0039] The medium according to the application preferably additionally comprises one or more compounds selected from the group consisting of compounds of formulae II and III, preferably one or more compounds of formula II, more preferably additionally one or more compounds of formula III, and most preferably additionally one or more compounds selected from the group consisting of compounds of formulae IV and V and again preferably one or more compounds selected from the group consisting of compounds of formulae VI to IX (all formulae as defined below).
[0040] The mixtures according to the application exhibit a very wide nematic phase range (clearing point > 70°C), a very advantageous threshold for capacitance, a relatively high value for the retention ratio and at the same time a good low-temperature stability at -20°C and -30°C, and a very low rotational viscosity. The mixtures according to the application are further characterized by a good ratio of clearing point to rotational viscosity and a relatively high positive dielectric anisotropy.
[0041] It has now surprisingly been found that FFS type LCDs using liquid crystals with a positive dielectric anisotropy can be realized by using specifically selected liquid crystal media. These media are characterized by a specific combination of physical properties. Most decisive among these are their dielectric properties and here the high average dielectric constant (ε av. ), the high dielectric constant perpendicular to the director of the liquid crystal molecules (ε ⊥ ), and in particular the relatively high ratio of these two latter values: (ε ⊥ / Δε).
[0042] On the one hand, the liquid crystal media according to the application preferably have a dielectric anisotropy value of 1.5 or more, preferably 2.5 or more. On the other hand, they preferably have a dielectric anisotropy of 26 or less, preferably 15 or less, most preferably 10 or less.
[0043] In a preferred embodiment, the liquid crystal media according to the application have a positive dielectric anisotropy, preferably of 1.5 or more to 20.0 or less, more preferably of 2.0 or more to 15.0 or less and most preferably of 2.0 or more to 12.0.
[0044] The liquid crystal media of the present application preferably exhibit a nematic phase and comprise
[0045] a) one or more compounds of formula C, preferably in a concentration range of 1% to 40%, more preferably of 2% to 30%, particularly preferably of 3% to 20%,
[0046]
[0047] wherein
[0048] denotes
[0049]
[0050] preferably denotes
[0051]
[0052] independently of one another in each occurrence denote
[0053]
[0054]
[0055] preferably denotes
[0056] most preferably denotes
[0057] R C1 and R C2 independently of one another denote alkyl having 1 to 15 C atoms, wherein one or more CH2 groups, preferably one CH2 group, of these radicals can each be replaced, independently of one another, by -CH=CH-, -C≡C-, -CF2O-, -OCF2-, -O-, -(CO)-O-, -O-(C=O)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentenylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentenylene, the above replacements being made in such a way that O atoms are not directly connected to one another, and wherein one or more H atoms can be replaced by halogen, and
[0058] wherein each ring, preferably the phenylene ring, optionally can each be substituted by one or two alkyl groups, preferably by methyl and / or ethyl, preferably by one methyl group, and
[0059] b) optionally, preferably compulsorily, one or more compounds of the formula B, preferably selected from the group of the compounds of the formulae B-1 to B-4, preferably in a concentration in the range from 1 to 60 %, more preferably from 2 to 40 %, particularly preferably from 3 to 35 %, most preferably from 3 to 20 %,
[0060]
[0061] wherein
[0062] denotes
[0063]
[0064] independently of one another in each occurrence
[0065]
[0066]
[0067] preferably denotes
[0068] most preferably denotes
[0069] n denotes 1 or 2, preferably 1,
[0070] R 1 has one of the meanings given for R C1 one or more CH2 groups, preferably one CH2 group, of these radicals can each be replaced, independently of one another, by -CH=CH-, -C≡C-, -CF2O-, -OCF2-, -O-, -(CO)-O-, -O-(C=O)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentenylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably by cyclopropylene or 1,3-cyclopentenylene, the above replacements being made in such a way that O atoms are not linked directly to one another, and in which one or more H atoms can be replaced by halogen, and
[0071] X 1 denotes F, Cl, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the four latter radicals preferably having 1 to 4 C atoms, more preferably F, Cl, CF3 or OCF3, and
[0072] wherein each ring, preferably the phenylene ring, can optionally be substituted by one or two alkyl groups, preferably by methyl and / or ethyl, preferably by one methyl group, and
[0073] and one or more further compounds, preferably selected from the group of compounds according to the following conditions c) to f):
[0074] c) one or more preferably dielectrically positive compounds selected from the group of compounds of the formulae II and III, preferably compounds each having a dielectric anisotropy of greater than 3, preferably one or more compounds of the formula II:
[0075]
[0076] wherein
[0077] R 2 has one of the meanings given for R C1 and preferably denotes alkyl, alkoxy, fluoroalkyl or fluoroalkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, and preferably alkyl or alkenyl,
[0078]
[0079] independently of one another in each occurrence denote
[0080]
[0081] preferably
[0082]
[0083] L 21 and L 22 denote H or F, preferably L 21 denotes F,
[0084] X 2 denotes halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, preferably F, CI, -OCF3, -O-CH2CF3, -O-CH=CH2, -O-CH=CF2 or -CF3, very preferably F, CI, -O-CH=CF2 or -OCF3,
[0085] m denotes 0, 1, 2 or 3, preferably 1 or 2, and particularly preferably 2,
[0086] R 3 has one of the meanings given for R C1 and preferably denotes alkyl, alkoxy, fluoroalkyl or fluoroalkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, and preferably n-alkyl, cyclopropyl, cyclopentyl or alkenyl,
[0087]
[0088] independently of one another in each occurrence
[0089]
[0090] preferably
[0091]
[0092] L 31 and L 32 independently of one another H or F, preferably L 31 denotes F,
[0093] X 3 denotes halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, F, CI, -OCF3, -OCHF2, -O-CH2CF3, -O-CH=CF2, -O-CH=CH2 or -CF3, very preferably F, CI, -O-CH=CF2, -OCHF2 or -OCF3,
[0094] Z 3 denotes -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O- or a single bond, preferably -CH2CH2-, -COO-, trans-CH=CH- or a single bond, and very preferably -COO-, trans-CH=CH- or a single bond, and
[0095] n denotes 0, 1, 2 or 3, preferably 1, 2 or 3 and particularly preferably 1,
[0096] wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl, preferably by one methyl group,
[0097] and wherein especially the ring
[0098] may be replaced by
[0099] and especially the ring
[0100] may be replaced by
[0101] d) optionally, preferably mandatorily, one or more compounds selected from the group consisting of formulae IV and V:
[0102]
[0103] wherein
[0104] R 41 and R 42 independently of one another have one of the meanings given for R C1 and preferably R 41 denotes alkyl and R 42 denotes alkyl or alkoxy or R 41 denotes alkenyl and R 42 denotes alkyl,
[0105]
[0106] independently of one another and if
[0107] occur twice
[0108] these also independently of one another denote,
[0109]
[0110] preferably,
[0111] one or more of the groups
[0112]
[0113] Z 41 and Z 42 independently of one another and if Z 41 occur twice, these also independently of one another denote -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, -CF2O-, -C≡C- or a single bond, preferably one or more of the groups represent a single bond, and
[0114] p denotes 0, 1 or 2, preferably 0 or 1, and
[0115] R 51 and R 52 independently of one another have one of the meanings given for R C1 and preferably R 51 and R 52 denote alkyl having 1 -7 C atoms, preferably n-alkyl, particularly preferably n-alkyl having 1 -5 C atoms, alkoxy having 1 -7 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy having 2-5 C atoms, alkoxyalkyl, alkenyl or alkenyloxy having 2-7 C atoms, preferably alkoxyalkyl, alkenyl or alkenyloxy having 2-4 C atoms, preferably alkenyloxy,
[0116] to
[0117] if present, each independently of the other(s)
[0118]
[0119]
[0120] preferably
[0121]
[0122] preferably
[0123] denotes
[0124] and if present, each independently of the other(s)
[0125] preferably denotes
[0126] Z 51 to Z 53 each independently of the other(s) denotes -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO- or a single bond, preferably -CH2-CH2-, -CH2-O- or a single bond and particularly preferably a single bond,
[0127] i and j each independently of the other(s) denote 0 or 1,
[0128] (i + j) preferably denotes 0, 1 or 2, more preferably 0 or 1, and most preferably 1,
[0129] wherein each ring, preferably the phenylene ring, optionally can each be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and
[0130] e) again optionally, preferably mandatorily, or alternatively or in addition, one or more compounds of dielectric negativity selected from the group consisting of formulae VI-IX:
[0131]
[0132] wherein
[0133] R 61 has the meaning for R C1One of the given meanings, and preferably, indicates an unsubstituted alkyl group having 1-7 carbon atoms, preferably a straight-chain alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl; an unsubstituted alkenyl group having 2-7 carbon atoms, preferably a straight-chain alkenyl group, particularly preferably having 2-5 carbon atoms; an unsubstituted alkoxy group having 1-6 carbon atoms; or an unsubstituted alkenoxy group having 2-6 carbon atoms.
[0134] R 62 Having for R C1 One of the given meanings, and preferably, indicates an unsubstituted alkyl group having 1-7 carbon atoms, an unsubstituted alkoxy group having 1-6 carbon atoms, or an unsubstituted olefinic group having 2-6 carbon atoms, and
[0135] l represents 0 or 1.
[0136] R 71 Having for R C1 One of the given meanings, and preferably, indicates an unsubstituted alkyl group having 1-7 carbon atoms, preferably a straight-chain alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, or an unsubstituted alkenyl group having 2-7 carbon atoms, preferably a straight-chain alkenyl group, particularly preferably having 2-5 carbon atoms.
[0137] R 72 Having for R C1 One of the given meanings, and preferably, it refers to an unsubstituted alkyl group having 1-7 carbon atoms, preferably having 2-5 carbon atoms, an unsubstituted alkoxy group having 1-6 carbon atoms, preferably having 1, 2, 3, or 4 carbon atoms, or an unsubstituted olefinic group having 2-6 carbon atoms, preferably having 2, 3, or 4 carbon atoms, and...
[0138] express
[0139]
[0140] R 81 Having for R C1 One of the given meanings, and preferably, indicates an unsubstituted alkyl group having 1-7 carbon atoms, preferably a straight-chain alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, or an unsubstituted alkenyl group having 2-7 carbon atoms, preferably a straight-chain alkenyl group, particularly preferably having 2-5 carbon atoms.
[0141] R 82 Having for R C1one of the meanings given above and preferably denotes an unsubstituted alkyl group with 1 to 7 C atoms, preferably with 2 to 5 C atoms, an unsubstituted alkoxy group with 1 to 6 C atoms, preferably with 1, 2, 3 or 4 C atoms, or an unsubstituted alkenyloxy group with 2 to 6 C atoms, preferably with 2, 3 or 4 C atoms,
[0142] denotes
[0143]
[0144] preferably
[0145]
[0146] more preferably
[0147]
[0148] Z 8 denotes -(C=0)-0-, -CH2-0-, -CF2-0- or -CH2-CH2-, preferably -(C=0)-0- or -CH2-0-, and
[0149] o denotes 0 or 1,
[0150] R 91 and R 92 each, independently of one another, have one of the meanings given above for R C1 and
[0151] R 91 preferably denotes an alkyl group with 2 to 5 C atoms, preferably with 3 to 5 C atoms,
[0152] R 92 preferably denotes an alkyl or alkoxy group with 2 to 5 C atoms, more preferably an alkoxy group with 2 to 4 C atoms, or an alkenyloxy group with 2 to 4 C atoms,
[0153] denotes
[0154] p and q each, independently of one another, denote 0 or 1, and
[0155] (p+q) preferably denotes 0 or 1,
[0156] if
[0157] denotes
[0158] optionally, preferably p = q = 1,
[0159] wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and wherein the compounds of the formula VII are excluded from the compounds of the formula IX,
[0160] and wherein in the formulae VI to IX, especially the rings
[0161] may alternatively be substituted by instead,
[0162] f) optionally, preferably mandatorily, alternatively or in addition, one or more compounds of the formula I,
[0163]
[0164] wherein
[0165] denotes
[0166]
[0167]
[0168] denotes
[0169]
[0170] preferably
[0171]
[0172] n denotes 0 or 1,
[0173] R 11 and R 12 each, independently of one another, denote alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one CH2group can be replaced by 1,2-cyclopropyl, by 1,3-cyclopentyl or by 1,3-cyclopentenylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkyl, alkoxy or alkenyloxy, and R 11 optionally denote R 1 and R 12 optionally denote X 1 ,
[0174] R 1represents alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one CH2group can be replaced by 1,2-cyclopropyl, by 1,3-cyclopentyl or by 1,3- cyclopentenylene, preferably alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl, preferably having 2 to 7 C atoms, and preferably alkyl or alkenyl, and
[0175] X 1 represents F, CI, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the latter four radicals preferably having 1 to 4 C atoms, more preferably F, CI, CF3or OCF3,
[0176] wherein each ring, preferably a phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl, preferably by one methyl group,
[0177] Compounds of the formulae B, VII and IX are not included therein.
[0178] Throughout the present application, 1,3-cyclopentenylene is a moiety selected from the group consisting of
[0179]
[0180] Preferably
[0181]
[0182] Most preferably
[0183]
[0184] The liquid-crystalline medium according to the present application preferably exhibits a nematic phase and is preferably in the nematic phase at an ambient temperature of 20 to 25 °C.
[0185] Examples of preferably used compounds of the formula C are those selected from the group consisting of the following formulae.
[0186] Preferably, the medium according to the present application comprises one or more compounds of the formula C selected from the group consisting of the formulae C-1 to C-4, preferably of the formulae C-1 and / or C-3, most preferably of the formula C-3
[0187]
[0188] wherein the parameters have the respective meanings given above, including the respective preferred meanings.
[0189] Especially preferred are the following compounds, wherein
[0190] R C1 represents an alkyl group having 1 to 15 C atoms, more preferably 2 to 7 C atoms and most preferably 2, 3 or 4 C atoms, and
[0191] R C2 represents an alkoxy radical having 1 to 15 C atoms, more preferably 1 to 7 C atoms and most preferably 3, 4 or 5 C atoms.
[0192] Particularly preferred compounds used are compounds of the formulae C-1 and C-3, most preferred are those of the formula C-3.
[0193] In one embodiment, the medium according to the present application comprises one or more compounds selected from the group consisting of the formulae C-5 to C-16
[0194]
[0195]
[0196] where the parameters have the respective meanings given above, including the respective preferred meanings.
[0197] The liquid-crystalline medium according to the present application preferably has a nematic phase.
[0198] Throughout the present application, especially for the definitions of R C1 and R C2 alkyl means an alkyl group which can be linear or branched. Each of these groups is preferably linear and preferably has 1, 2, 3, 4, 5, 6, 7 or 8 C atoms, thus preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.
[0199] In case alkyl denotes a branched alkyl group, it preferably denotes a 2-alkyl, 2-methylalkyl or 2-(2-ethyl)-alkyl group, preferably 2-butyl (= 1 -methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular 2-methylbutyl, 2-methylbutoxy, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl and 2-dodecyl. Most preferred among these groups are 2-hexyl and 2-octyl.
[0200] each branched group, in particular for R C1 and R C2 which leads to chiral compounds, are also referred to as chiral groups in the present application. Particularly preferred chiral groups are 2-alkyl, 2-alkoxy, 2-methylalkyl, 2-methylalkoxy, 2-fluoroalkyl, 2-fluoroalkoxy, 2-(2-ethynyl)-alkyl, 2-(2-ethynyl)-alkoxy, 1,1,1 -trifluoro-2-alkyl and 1,1,1 -trifluoro-2-alkoxy.
[0201] Particularly preferred chiral groups are, for example, 2-butyl (= 1 -methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular 2-methylbutyl, 2-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 2-ethylhexyloxy, 1 -methylhexyloxy, 2-octyloxy, 2-oxy-3-methylbutyl, 3-oxy-4-methylpentyl, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl, 2-dodecyl, 6-methoxyoctyloxy, 6-methyloctyloxy, 6-methyloctanoyloxy, 5-methylheptyloxycarbonyl, 2-methylbutyryloxy, 3-methylvaleroyloxy, 4-methylhexanoyloxy, 2-chloropropionyloxy, 2-chloro-3-methylbutyryloxy, 2-chloro-4-methylvaleroyloxy, 2-chloro-3-methylvaleroyloxy, 2-methyl-3-oxapentyl, 2-methyl-3-oxahexyl, 1 -methoxypropyl-2-oxy, 1 -ethoxypropyl-2-oxy, 1 -propoxypropyl-2-oxy, 1 -butoxypropyl-2-oxy, 2-fluorooctyloxy, 2-fluorodecyloxy, 1,1,1 -trifluoro-2-octyloxy, 1,1,1 -trifluoro-2-octyl, 2-fluoromethyloctyloxy. Very preferred are 2-hexyl, 2-octyl, 2-octyloxy, 1,1,1 -trifluoro-2-hexyl, 1,1,1 -trifluoro-2-octyl and 1,1,1 -trifluoro-2-octyloxy.
[0202] Throughout the present application, in particular for the definition of R D Alkenyl means an alkenyl group which can be straight-chain or branched, preferably straight-chain, and preferably has 2, 3, 4, 5, 6 or 7 or 8 carbon atoms. Preferably, it is a vinyl group, a 1 -E-alkenyl group or a 3-E-alkenyl group, most preferably it is a vinyl group, a 1 -E-propenyl group, a 1 -E-butenyl group, a 1 -E-pentenyl group, a 3-butenyl group or a 3-E-pentenyl group.
[0203] The application furthermore relates to a liquid-crystalline display, in particular an IPS or FFS display, particularly preferably an FFS or SG-FFS display, comprising a liquid-crystalline medium according to the application.
[0204] The application furthermore relates to a liquid-crystalline display of the IPS or FFS type comprising a liquid cell consisting of two substrates, at least one of which is transparent to light and at least one of which has an electrode layer, and a layer of a liquid-crystalline medium located between the substrates, the liquid-crystalline medium comprising a polymerised component and a low-molecular-weight component, wherein the polymerised component is obtainable by polymerisation of one or more polymerisable compounds in the liquid-crystalline medium between the substrates of the liquid cell, preferably by application of a voltage, and wherein the low-molecular-weight component is a liquid-crystalline mixture according to the application as described above and below.
[0205] The display according to the present application is preferably addressed by an active matrix (active matrix LCD, for short AMD), preferably by a matrix of thin film transistors (TFT). However, the liquid crystals according to the present application can also be used in a display having other known addressing modes in an advantageous manner.
[0206] The present application furthermore relates to a process for the preparation of a liquid-crystalline medium according to the present application by mixing one or more compounds of formula C, preferably selected from the group consisting of compounds of formulae C-1 to C-4, most preferably selected from the group consisting of compounds of formulae C-1 and C-3, with one or more low-molecular-weight liquid-crystalline compounds or liquid-crystalline mixtures and, optionally, with further liquid-crystalline compounds and / or additives.
[0207] The following meanings apply in the context:
[0208] The term "FFS" is used to denote both FFS and SG-FFS displays, unless otherwise specified.
[0209] The term "mesogenic group" is known to the person skilled in the art and is described in the literature and denotes a group which, due to its anisotropy of attraction and repulsion interactions, contributes essentially to the induction of a liquid-crystalline (LC) phase in low-molecular-weight or polymeric substances. A compound containing mesogenic groups (mesogenic compound) does not necessarily have a liquid-crystalline phase itself. A mesogenic compound can also only exhibit liquid-crystalline behaviour in mixture with other compounds and / or after polymerisation. Typical mesogenic groups are, for example, rigid rod-like or disc-like units. A review of the terminology and definitions used in connection with mesogenic or liquid-crystalline compounds is given in Pure Appl. Chem. 73(5), 888 (2001 ) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368.
[0210] The term "spacer group" or simply "spacer" (in the context also referred to as "Sp") is known to the person skilled in the art and is described in the literature, see for example Pure Appl. Chem. 73(5), 888 (2001 ) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. Unless otherwise indicated, the term "spacer group" or "spacer" in the context denotes a flexible group which links the mesogenic group and the polymerisable group(s) to each other in a polymerisable mesogenic compound.
[0211] For the purposes of the present application, the term "liquid-crystalline medium" is intended to mean a medium comprising a liquid-crystalline mixture and one or more polymerisable compounds, for example reactive mesogens. The term "liquid-crystalline mixture" (or "host mixture") is intended to mean a liquid-crystalline mixture consisting exclusively of non-polymerisable low-molecular-weight compounds, preferably two or more liquid-crystalline compounds and optionally further additives, for example chiral dopants or stabilisers.
[0212] Particular preference is given to liquid-crystalline mixtures and liquid- crystalline media which have a nematic phase, in particular at room temperature.
[0213] In a preferred embodiment of the application, the liquid-crystalline medium comprises one or more preferably dielectrically positive compounds having a dielectric anisotropy of greater than 3, preferably selected from the group consisting of compounds of formulae II-1 and II-2:
[0214]
[0215] where the parameters have the respective meanings indicated above under formula II, and L 23 and L 24 independently of one another, denote H or F, preferably L 23 denotes F, and
[0216] have one of the meanings given for
[0217] and, in the case of formulae II-1 and II-2, X 2 preferably denotes F or OCF3, particularly preferably F, and, in the case of formula II-2,
[0218]
[0219] independently of one another, preferably denote
[0220]
[0221] and where each ring, preferably a phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and where in particular the ring
[0222] may be replaced by
[0223] and / or selected from the group consisting of compounds of formulae III-1 and III-2:
[0224]
[0225] where the parameters have the meanings given under formula III,
[0226] and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and wherein especially the ring may be replaced,
[0227] and the medium according to the present application comprises one or more compounds of formula III-3 instead of or in addition to compounds of formula III-1 and / or III-2
[0228]
[0229] wherein the parameters have the respective meanings indicated above, and the parameters L 31 and L 32 independently of each other and of the other parameters, denote H or F,
[0230] and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and wherein especially the ring may be replaced.
[0231] The liquid-crystalline medium preferably comprises one or more compounds selected from compounds of formulae II-1 and II-2, wherein L 21 and L 22 and / or L 23 and L 24 each denote F.
[0232] In a preferred embodiment, the liquid-crystalline medium comprises one or more compounds selected from compounds of formulae II-1 and II-2, wherein L 21 , L 22 , L 23 and L 24 all denote F.
[0233] The liquid-crystalline medium preferably comprises one or more compounds of formula II-1. The compounds of formula II-1 are preferably selected from compounds of formulae II-1 a to II-1 e, preferably one or more compounds of formulae II-1 a and / or II-1 b and / or II-1 d, preferably compounds of formulae II-1 a and / or II-1 d or II-1 b and / or II-1 d, most preferably compounds of formula II-1 d:
[0234]
[0235]
[0236] wherein the parameters have the respective meanings indicated above, and the parameters L 25 and L26 independently of one another and of the other parameters, denote H or F, and preferably
[0237] in formulae II-1 a and II-1 b,
[0238] L 21 and L 22 each denote F,
[0239] in formulae II-1 c and II-1 d,
[0240] L 21 and L 22 each denote F and / or L 23 and L 24 each denote F, and
[0241] in formula II-1 e,
[0242] L 21 , L 22 and L 23 denote F,
[0243] and wherein each ring, preferably the phenylene ring, optionally can each be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and wherein especially the ring
[0244] may be replaced.
[0245] In one embodiment, the medium comprises one or more compounds selected from the group of the following formulae:
[0246]
[0247]
[0248] wherein R 2 and X 2 have the meaning given in formula II or one of the preferred meanings given above and below.
[0249] The liquid-crystalline medium preferably comprises one or more compounds of formula II-2, which are preferably selected from the group consisting of the compounds of formulae II-2a to II-2k, preferably one or more compounds of each of formulae II-2a and / or II-2h and / or II-2j:
[0250]
[0251]
[0252] wherein the parameters have the respective meanings described above, and L 25 to L 28independently of one another H or F, preferably L 27 and L 28 both denote H, particularly preferably L 26 denotes H,
[0253] and wherein each ring, preferably a phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and wherein especially the ring
[0254] may be replaced.
[0255] The liquid-crystalline medium preferably comprises compounds selected from the group of compounds of formulae II-2a to II-2k, wherein L 21 and L 22 both denote F and / or L 23 and L 24 both denote F.
[0256] In a preferred embodiment, the liquid-crystalline medium comprises compounds selected from the group of compounds of formulae II-2a to II-2k, wherein L 21 , L 22 , L 23 and L 24 all denote F.
[0257] Especially preferred compounds of formula II-2 are the compounds of the following formulae, particularly preferably formulae II-2a-1 and / or II-2h-1 and / or II-2k-2:
[0258]
[0259]
[0260]
[0261] wherein R 2 and X 2 have the above described meanings, and X 2 preferably denotes F,
[0262] and wherein each ring, preferably a phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group, and wherein especially the ring
[0263] may be replaced.
[0264] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1. The compounds of formula III-1 are preferably selected from compounds of formulae III-1 a to III-1 j, preferably from formulae III-1 c, III-1 f, III-1 g and III-1 j:
[0265]
[0266]
[0267]
[0268] wherein the parameters have the meanings given above and preferably wherein the parameters have the respective preferred meanings described above, the parameter L 33 and L 34 independently of each other and of the other parameters, denote H or F, and the parameter L 35 and L 36 independently of each other and of the other parameters, denote H or F,
[0269] and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0270] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 c, which are preferably selected from compounds of formulae III-1 c-1 to III-1 c-5, preferably of formulae III-1 c-1 and / or III-1 c-2, most preferably of formula III-1 c-1 :
[0271]
[0272] wherein R 3 has the meanings described above and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0273] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 f, which are preferably selected from compounds of formulae III-1 f-1 to III-1 f-6, preferably of formulae III-1 f-1 and / or III-1 f-2 and / or III-1 f-3 and / or III-1 f-6, more preferably of formulae III-1 f-3 and / or III-1 f-6, more preferably of formula III-1 f-6:
[0274]
[0275]
[0276] wherein R 3with the above given meanings and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0277] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 g, which are preferably selected from compounds of formulae III-1 g-1 to III-1 g-5, preferably of formula III-1 g-3:
[0278]
[0279] wherein the parameters have the above given meanings, and X 3 with the above given meanings and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0280] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 h, which are preferably selected from compounds of formulae III-1 h-1 to III-1 h-3, preferably of formula III-1 h-3:
[0281]
[0282] wherein the parameters have the above given meanings, and X 3 with the above given meanings and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0283] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 i, which are preferably selected from compounds of formulae III-1 i-1 and III-1 i-2, preferably of formula III-1 i-2:
[0284]
[0285]
[0286] wherein the parameters have the above given meanings, and X 3 with the above given meanings and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0287] The liquid-crystalline medium preferably comprises one or more compounds of formula III-1 j, which are preferably selected from compounds of formulae III-1 j-1 and III-1 j-2, preferably of formula III-1 j-1:
[0288]
[0289] wherein the parameters have the meanings given above and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0290] The liquid-crystalline medium preferably comprises one or more compounds of formula III-2. The compounds of formula III-2 are preferably selected from compounds of formulae III-2a and III-2b, preferably of formula III-2b:
[0291]
[0292]
[0293] wherein the parameters have the meanings described above and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group. 33 and L 34 , independently of one another and independently of the other parameters, denote H or F, and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0294] The liquid-crystalline medium preferably comprises one or more compounds of formula III-2a, which are preferably selected from compounds of formulae III-2a-1 to III-2a-6:
[0295]
[0296]
[0297] wherein R 3 have the meanings described above and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0298] The liquid-crystalline medium preferably comprises one or more compounds of formula III-2b, which are preferably selected from compounds of formulae III-2b-1 to III-2b-4, preferably of formula III-2b-4:
[0299]
[0300] wherein R 3 have the meanings described above and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0301] Instead of or in addition to compounds of formulae III-1 and / or III-2, the medium according to the application can also comprise one or more compounds of formula III-3
[0302]
[0303] wherein the parameters have the respective meanings indicated above for formula II. I and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0304] These compounds are preferably selected from formulae III-3a and III-3b:
[0305]
[0306] wherein R 3 have the meanings indicated above, and wherein each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl groups, preferably by methyl and / or ethyl groups, preferably by one methyl group.
[0307] The liquid-crystalline medium according to the application preferably comprises one or more dielectrically neutral compounds having a dielectric anisotropy of -1.5 to 3, preferably selected from compounds of formulae VI, VII, VIII and IX.
[0308] In the present application, the elements include all isotopes of the respective elements. In particular, one or more H in the compounds can be replaced by D, and this is particularly preferred in certain embodiments. A high degree of tritiation of the respective compounds can, for example, detect and identify the compounds. This is very useful in certain cases, in particular in the case of compounds of formula I.
[0309] In the present application,
[0310] alkyl preferably denotes straight-chain alkyl, in particular CH3-, C2H5-, n-C3H7-, n-C4H9- or n-C5H 11 - and
[0311] alkenyl preferably denotes CH2=CH-, E-CH3-CH=CH-, CH2=CH-CH2-CH2-, E-CH3-CH=CH-CH2-CH2- or E-(n-C3H7)-CH=CH-.
[0312] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of formula VI, selected from compounds of formulae VI-1 and VI-2, preferably one or more compounds of formula VI-1 and one or more compounds of formula VI-2,
[0313]
[0314] wherein the parameters have the respective meanings given above for formula VI, and preferably in formula VI-1
[0315] R61 and R 62 independently of one another denote methoxy, ethoxy, propoxy, butoxy and also pentoxy, preferably ethoxy, butoxy or pentoxy, more preferably ethoxy or butoxy, and most preferably butoxy;
[0316] in formula VI-2
[0317] R 61 preferably denote vinyl, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl and n-propyl or n-pentyl, and
[0318] R 62 denote an unsubstituted alkyl radical having 1-7 C atoms, preferably having 2-5 C atoms, or preferably is an unsubstituted alkoxy radical having 1-6 C atoms, particularly preferably having 2 or 4 C atoms, and most preferably ethoxy, and
[0319] In a preferred embodiment of the application, the medium according to the application in each case comprises one or more compounds of the formula VII, selected from the group of the compounds of the formulae VII-1 to VII-3, preferably one or more compounds each of the formula VII-1 and one or more compounds of the formula VII-2,
[0320]
[0321]
[0322] in which the parameters have the respective meanings given above in formula VII, and preferably,
[0323] R 71 denote vinyl, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, n-propyl or n-pentyl and
[0324] R 72 denote an unsubstituted alkyl radical having 1-7 C atoms, preferably having 2-5 C atoms, or preferably is an unsubstituted alkoxy radical having 1-6 C atoms, particularly preferably having 2 or 4 C atoms, and most preferably ethoxy,
[0325] and in which each ring, preferably the phenylene ring, optionally can be substituted by one or two alkyl radicals, preferably by methyl and / or ethyl, preferably by one methyl group.
[0326] In a preferred embodiment of the application, the medium according to the application in each case comprises one or more compounds of the formula VI-1, selected from the following compounds:
[0327]
[0328] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VI-2, selected from the following compounds:
[0329]
[0330] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VII-1, selected from the following compounds:
[0331]
[0332] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VII-2, selected from the following compounds:
[0333]
[0334]
[0335] In addition to compounds of the formula B or preferred subformulae thereof, the medium according to the application preferably also comprises one or more dielectrically negative compounds selected from the group of the compounds of the formulae VI and VII, preferably in a total concentration of 5% or more to 90% or less, preferably 10% or more to 80% or less, particularly preferably 20% or more to 70% or less.
[0336] In a preferred embodiment of the present application, the medium according to the application in each case comprises one or more compounds of the formula VIII selected from the group of the compounds of the formulae VIII-1 to VIII-3, preferably one or more compounds each of the formula VIII-1 and / or one or more compounds of the formula VIII-3,
[0337]
[0338] in which the parameters have the respective meanings given in formula VIII above, and preferably
[0339] R 81 denotes vinyl, 1-E-propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, ethyl, n-propyl or n-pentyl, alkyl, preferably ethyl, n-propyl or n-pentyl, and
[0340] R 82 denotes an unsubstituted alkyl radical having 1 -7 C atoms, preferably having 1 -5 C atoms, or an unsubstituted alkoxy radical having 1 -6 C atoms.
[0341] In the formulae VIII-1 and VIII-2, R82 Preferably, alkoxy denotes an alkoxy group having 2 or 4 C atoms and, most preferably, ethoxy and, in its preferred meaning in formula VIII-3, alkyl, preferably methyl, ethyl or n-propyl, most preferably methyl.
[0342] In a further preferred embodiment, the medium comprises one or more compounds selected from the group consisting of formulae VI to IX, which is selected from the group consisting of the following compounds:
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350]
[0351]
[0352]
[0353]
[0354] wherein
[0355] a denotes 1 or 2,
[0356] alkyl and alkyl * each, independently of one another, denotes a straight-chain alkyl radical having 1 -6 C atoms,
[0357] (O) denotes an oxygen atom or a single bond, and
[0358] alkenyl denotes a straight-chain alkenyl radical having 2-7 C atoms and preferably CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH- or CH3-CH=CH-(CH2)2-.
[0359] In a further preferred embodiment, the medium comprises one or more compounds of formula IV, preferably of formula IVa,
[0360]
[0361] wherein
[0362] R 41 denotes an unsubstituted alkyl radical having 1 -7 C atoms or an unsubstituted alkenyl radical having 2-7 C atoms, preferably an n-alkyl radical, particularly preferably having 2, 3, 4 or 5 C atoms, and
[0363] R 42 denotes an unsubstituted alkyl radical having 1 -7 C atoms, an unsubstituted alkenyl radical having 2-7 C atoms, or an unsubstituted alkoxy radical having 1 -6 C atoms, all preferably an unsubstituted alkenyl radical having 2-5 C atoms, preferably having 2, 3 or 4 C atoms, more preferably a vinyl radical or a 1 -propenyl radical, and in particular a vinyl radical.
[0364] In a particularly preferred embodiment, the medium comprises one or more compounds of the formula IV selected from the group consisting of the compounds of the formulae IV-1 to IV-6, preferably of the formulae IV-1 and / or IV-6,
[0365]
[0366] wherein
[0367] alkyl and alkyl' independently of one another denote an alkyl radical having 1 -7 C atoms, preferably having 2-5 C atoms,
[0368] alkenyl and alkenyl' independently of one another denote an alkenyl radical having 2-5 C atoms, preferably having 2-4 C atoms, particularly preferably 2 C atoms,
[0369] alkenyl' preferably denotes an alkenyl radical having 2-5 C atoms, preferably having 2-4 C atoms, particularly preferably having 2 to 3 C atoms, and
[0370] alkoxy denotes an alkoxy radical having 1 -5 C atoms, preferably having 2-4 C atoms.
[0371] In a particularly preferred embodiment, the medium according to the application comprises one or more compounds of the formula IV-1 and / or one or more compounds of the formula IV-2.
[0372] Particularly preferred compounds of the formula IV are selected from the following subformulae:
[0373]
[0374]
[0375] wherein the propyl, butyl and pentyl groups are straight-chain radicals.
[0376] Most preferred are compounds selected from the group consisting of the following formulae
[0377]
[0378] wherein the propyl group is a straight-chain radical.
[0379] In a further preferred embodiment, the medium comprises one or more compounds of the formula V.
[0380] In a further preferred embodiment, the medium comprises one or more compounds of the formula I selected from the group consisting of the compounds of the formulae I-1 and I-2:
[0381]
[0382] wherein
[0383] R 11 and R 12 independently of one another, alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one CH2 group can be replaced by 1,2-cyclopropyl, by 1,3-cyclopentyl or by 1,3-cyclopentenylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,
[0384] R 1 alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, wherein one CH2 group can be replaced by 1,2-cyclopropyl, by 1,3-cyclopentyl or by 1,3-cyclopentenylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, and
[0385] X 1 F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the last four radicals preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably CF3 or OCF3.
[0386] In a further preferred embodiment, the medium comprises one or more compounds of the formula I selected from the group consisting of the compounds of the formulae I-1-1 to I-1-12:
[0387]
[0388]
[0389] In a further preferred embodiment, the medium comprises one or more compounds of formula I, which are selected from the group consisting of compounds of formulae I-3 and I-4:
[0390]
[0391] wherein
[0392] R 11 and R 12 independently of one another, alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, where one CH2 group can be replaced by 1,2-cyclopropyl, by 1,3-cyclopentyl or by 1,3-cyclopentenylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,
[0393] R 1 alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, where one CH2 group can be replaced by 1,2-cyclopropyl, by 1,3-cyclopentyl or by 1,3-cyclopentenylene, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl, and
[0394] X 1 F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the latter four radicals preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, more preferably F, CF3 or OCF3, most preferably CF3 or OCF3.
[0395] In a further preferred embodiment, the medium comprises one or more compounds of formula I, which are selected from the group consisting of compounds of formulae I-3-1 to I-3-12:
[0396]
[0397]
[0398]
[0399] In a further preferred embodiment, the medium comprises one or more compounds of formula B, which are preferably selected from the group consisting of compounds of formulae B-1 and B-2:
[0400]
[0401] wherein
[0402] R 1alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms and preferably alkyl or alkenyl, and
[0403] X 1 F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the latter four preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, more preferably F, CF3, or OCF3, and most preferably OCF3 or CF3.
[0404] In a further preferred embodiment, the medium can alternatively or in addition comprise one or more compounds of formula B selected from the group consisting of compounds of formulae B-3 and B-4:
[0405]
[0406] wherein
[0407] R 1 alkyl, alkoxy, fluoroalkyl or fluoroalkoxy, preferably having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluoroalkenyl having 2 to 7 C atoms and preferably alkyl or alkenyl, and
[0408] X 1 F, CI, CN, NCS, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the latter four preferably having 1 to 4 C atoms, preferably F, CI, CF3 or OCF3, more preferably F, CF3, or OCF3, and most preferably OCF3 or CF3.
[0409] In one embodiment, the medium can alternatively or in addition comprise one or more compounds of formulae B-1-1, B-2-1, B-2-2, B-3-1, B-4-1 and B-4-2:
[0410]
[0411]
[0412] wherein the parameters have the respective meanings given above.
[0413] The medium according to the application preferably comprises the following compounds at the indicated total concentration:
[0414] 1 to 30 wt% of one or more compounds selected from the group consisting of compounds of formula C, and
[0415] 0 to 30 wt% of one or more compounds of formula I, preferably selected from the group consisting of compounds of formulae I-1 and I-2, most preferably selected from the group consisting of compounds of formula I-2, and / or
[0416] 2 to 60 wt.-% of one or more compounds of the formula II, preferably selected from the group consisting of the compounds of the formulae II-1 and II-2, and / or
[0417] 1 to 60 wt.-% of one or more compounds of the formula III, and / or
[0418] 20 to 80 wt.-% of one or more compounds of the formula IV, and / or
[0419] 0 to 25 wt.-% of one or more compounds of the formula V, and / or
[0420] 0 to 25 wt.-% of one or more compounds of the formula VI, and / or
[0421] 0 to 20 wt.-% of one or more compounds of the formula VII, and / or
[0422] 0 to 30 wt.-% of one or more compounds of the formula VIII, preferably selected from the group consisting of the compounds of the formulae VIII-1 and VIII-2, and / or
[0423] 0 to 60 wt.-% of one or more compounds of the formula IX, and / or
[0424] 0 to 30 wt.-% of one or more compounds selected from the group of the formula B,
[0425] wherein the total content of all compounds of the formulae C, B and I to IX present in the medium is preferably 95 % or more, more preferably 97 % or more and most preferably 100 %.
[0426] The latter condition applies to all media according to the application.
[0427] In a further preferred embodiment, the media according to the application comprise, in addition to the compounds of the formula C or its preferred subformulae and the compounds of the formulae I and / or B and / or II and / or III and / or VI and / or VII and / or VIII and / or IX, preferably also one or more dielectrically neutral compounds selected from the group of the compounds of the formulae IV and V, preferably in a total concentration of 5 % or more to 90 % or less, preferably 10 % or more to 80 % or less, particularly preferably 20 % or more to 70 % or less.
[0428] In a particularly preferred embodiment, the media according to the application comprise
[0429] one or more compounds of the formula C in a total concentration of 3 % or more to 50 % or less, preferably 5 % or more to 30 % or less, and
[0430] one or more compounds of the formula II in a total concentration of 5 % or more to 50 % or less, preferably 10 % or more to 40 % or less, and / or
[0431] one or more compounds of the formula VII-1 in a total concentration of 5% or more to 30% or less, and / or
[0432] one or more compounds of the formula VII-2 in a total concentration of 3% or more to 30% or less, and / or
[0433] one or more compounds of the formula I in a total concentration of 3% or more to 50% or less, preferably 5% or more to 30% or less, and / or
[0434] one or more compounds of the formula B in a total concentration of 3% or more to 50% or less, preferably 5% or more to 30% or less.
[0435] The concentration of the compounds of the formula C in the medium according to the application is preferably 1% or more to 20% or less, more preferably 1.5% or more to 20% or less, most preferably 2% or more to 10% or less.
[0436] In a preferred embodiment of the application, the concentration of the compounds of the formula II in the medium is 3% or more to 60% or less, more preferably 5% or more to 55% or less, more preferably 10% or more to 50% or less and most preferably 15% or more to 45% or less.
[0437] In a preferred embodiment of the application, the concentration of the compounds of the formula VII in the medium is 2% or more to 50% or less, more preferably 5% or more to 40% or less, more preferably 10% or more to 35% or less and most preferably 15% or more to 30% or less.
[0438] In a preferred embodiment of the application, the concentration of the compounds of the formula VII-1 in the medium is 1% or more to 40% or less, more preferably 2% or more to 35% or less or, alternatively, 15% or more to 25% or less.
[0439] In a preferred embodiment of the application, the concentration of the compounds of the formula VII-2, if present, in the medium is 1% or more to 40% or less, more preferably 5% or more to 35% or less and most preferably 10% or more to 30% or less.
[0440] The concentration of the compounds of the formula B in the medium according to the application is preferably 1% or more to 60% or less, more preferably 3% or more to 40% or less, most preferably 5% or more to 35% or less.
[0441] In a preferred embodiment of the present application, the concentration of the compound of formula I in the medium according to the present application is 1 % or more to 60 % or less, more preferably 2 % or more to 40 % or less, most preferably 3 % or more to 35 % or less.
[0442] The present application also relates to an electro-optical display or electro-optical component comprising the liquid-crystalline medium according to the present application. Preferred are electro-optical displays based on the VA, ECB, IPS or FFS effect, preferably based on the VA, IPS or FFS effect, and in particular those which are addressed by active matrix addressing devices.
[0443] Accordingly, the present application likewise relates to the use of a liquid-crystalline medium according to the present application in an electro-optical display or electro-optical component, and to a process for the preparation of a liquid-crystalline medium according to the present application, characterized in that one or more compounds of formula B are mixed with one or more compounds of formula I, preferably with one or more compounds of the subformulae I-1 and / or I-2, preferably with a compound of formula I-2, and / or with one or more compounds of formula II, preferably with one or more compounds of the subformulae II-1 and / or II-2, with one or more compounds of formula VII, preferably with one or more compounds of the subformulae VII-1 and / or VII-2, particularly preferably with two or more, preferably three or more, and very particularly preferably with all four of the compounds from their different formulae selected from these formulae II-1, II-2, VII-1 and VII-2 and one or more further compounds, preferably compounds selected from formulae IV and V, more preferably with one or more compounds of formula IV and formula V.
[0444] In a further preferred embodiment, the medium comprises one or more compounds of formula IV selected from the group consisting of the compounds of formulae IV-2 and IV-3,
[0445]
[0446] wherein the parameters have the meanings given above in formula V, and preferably
[0447] alkyl and alkyl' independently of one another denote an alkyl group having 1 -7 C atoms, preferably having 2-5 C atoms,
[0448] alkoxy denotes an alkoxy group having 1 -5 C atoms, preferably having 2-4 C atoms.
[0449] In a further preferred embodiment, the medium comprises one or more compounds of formula V selected from the group consisting of the compounds of formulae V-1 and V-2, preferably of formula V-1,
[0450]
[0451] wherein the parameters have the meanings given above in formula V, and preferably
[0452] R 51 denotes alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms, and
[0453] R 52 denotes alkyl having 1 to 7 C atoms, alkenyl having 2 to 7 C atoms, or alkoxy having 1 to 6 C atoms, preferably alkyl or alkenyl, particularly preferably alkyl.
[0454] In a further preferred embodiment, the medium comprises one or more compounds of formula V-1 selected from the group consisting of compounds of formulae V-1a and V-1b,
[0455]
[0456]
[0457] wherein
[0458] alkyl and alkyl' independently of one another denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, and
[0459] alkenyl denotes alkenyl having 2 to 7 C atoms, preferably having 2 to 5 C atoms.
[0460] The application furthermore relates to a method for reducing the wavelength scattering of birefringent liquid crystal media, which comprise one or more compounds of formula II, optionally one or more compounds selected from the group consisting of compounds of formulae VII-1 and VII-2 and / or one or more compounds of formula IV and / or one or more compounds of formula V, characterised in that one or more compounds of formula B are used in the medium.
[0461] In addition to the compounds of formulae C, B and I to IX, other constituents can also be present, for example in an amount of at most 45 %, but preferably at most 35 %, in particular at most 10 %, based on the overall mixture.
[0462] The medium according to the application can also optionally comprise dielectrically positive compounds, the total concentration of which is preferably 20 % or less, more preferably 10 % or less, based on the overall medium.
[0463] In a preferred embodiment, the liquid crystal medium according to the application comprises in total, based on the overall mixture:
[0464] 1 % or more to 30 % or less, preferably 1.5 % or more to 20 % or less, particularly preferably 2 % or more to 10 % or less, of compounds of formula C, and / or
[0465] 1 % or more to 20 % or less, preferably 1 % or more to 15 % or less, particularly preferably 2 % or more to 12 % or less, of compounds of formula B, and / or
[0466] 0 % or more to 20 % or less, preferably 0 % or more to 15 % or less, particularly preferably 0 % or more to 12 % or less, of compounds of formula I, and / or
[0467] 3 % or more to 50 % or less, preferably 4 % or more to 45 % or less, particularly preferably 5 % or more to 40 % or less, of compounds of formula II and / or III, and / or
[0468] 0 % or more to 35 % or less, preferably 2 % or more to 30 % or less, particularly preferably 3 % or more to 25 % or less, of compounds of formula IV and / or V, and / or
[0469] 5 % or more to 50 % or less, 10 % or more to 45 % or less, preferably 15 % or more to 40 % or less, of compounds of formula VI and / or VII and / or VIII and / or IX.
[0470] The liquid-crystalline medium according to the present application can comprise one or more chiral compounds.
[0471] Particularly preferred embodiments of the present application meet one or more of the following conditions:
[0472] wherein the abbreviations (short forms) are explained in Tables A to C and illustrated by examples in Table D.
[0473] The medium according to the present application preferably meets one or more of the following conditions.
[0474] i. The liquid-crystalline medium has a birefringence of 0.060 or more, particularly preferably of 0.070 or more.
[0475] ii. The liquid-crystalline medium has a birefringence of 0.200 or less, particularly preferably of 0.180 or less.
[0476] iii. The liquid-crystalline medium has a birefringence of 0.090 or more to 0.160 or less.
[0477] iv. The liquid-crystalline medium comprises one or more particularly preferred compounds of formula C, preferably selected from (sub-)formulae C-1 to C-4, most preferably from (sub-)formulae C-1 and / or C-3.
[0478] v. The liquid-crystalline medium comprises one or more particularly preferred compounds of formula B, preferably selected from (sub-)formulae B-1 to B-4, most preferably from (sub-)formulae B-2 and / or B-4.
[0479] vi. The liquid-crystalline medium comprises one or more compounds of formula I, preferably selected from (sub-)formulae I-1 and I-2, most preferably selected from (sub-)formula I-2.
[0480] vii. The total concentration of compounds of formula II in the mixture as a whole is 25% or more, preferably 30% or more, and preferably 25% or more to 49% or less, particularly preferably 29% or more to 47% or less, and very particularly preferably 37% or more to 44% or less.
[0481] viii. The liquid-crystalline medium comprises one or more compounds of formula IV selected from the group consisting of CC-n-V and / or CC-n-Vm and / or CC-V-V and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably CC-3-V, preferably in a concentration of at most 60% or less, particularly preferably at most 50% or less, and optionally further CC-3-V1, preferably in a concentration of at most 15% or less, and / or CC-4-V, preferably in a concentration of at most 40% or less, particularly preferably at most 30% or less.
[0482] ix. The medium comprises compounds of formula CC-n-V, preferably CC-3-V, preferably in a concentration of 1% or more to 60% or less, more preferably in a concentration of 3% or more to 35% or less.
[0483] x. The total concentration of compounds of formula CC-3-V in the mixture as a whole is preferably 15% or less, preferably 10% or less or 20% or more, preferably 25% or more.
[0484] xi. The total concentration of compounds of formula Y-nO-Om in the mixture as a whole is 2% or more to 30% or less, preferably 5% or more to 15% or less.
[0485] xii. The total concentration of compounds of formula CY-n-Om in the mixture as a whole is 5% or more to 60% or less, preferably 15% or more to 45% or less.
[0486] xiii. The total concentration of compounds of formulae CCY-n-Om and / or CCY-n-m, preferably CCY-n-Om, in the mixture as a whole is 5% or more to 40% or less, preferably 1% or more to 25% or less.
[0487] xiv. The total concentration of compounds of formula CLY-n-Om in the mixture as a whole is 5% or more to 40% or less, preferably 10% or more to 30% or less.
[0488] xv. The liquid-crystalline medium comprises one or more compounds of formula IV, preferably of formula IV-1 and / or IV-2, preferably in a total concentration of 1 % or more, in particular 2 % or more, and very particularly preferably 3 % or more to 50 % or less, preferably 35 % or less.
[0489] xvi. The liquid-crystalline medium comprises one or more compounds of formula V, preferably of formula V-1 and / or V-2, preferably in a total concentration of 1 % or more, in particular 2 % or more, and very particularly preferably 15 % or more to 35 % or less, preferably to 30 % or less.
[0490] xvii. The total concentration of compounds of formula CCP-V-n, preferably CCP-V-1, in the mixture as a whole is preferably 5 % or more to 30 % or less, preferably 15 % or more to 25 % or less.
[0491] xviii. The total concentration of compounds of formula CCP-V2-n, preferably CCP-V2-1, in the mixture as a whole is preferably 1 % or more to 15 % or less, preferably 2 % or more to 10 % or less.
[0492] The application further relates to an electro-optical display having active matrix addressing on the basis of the VA, ECB, IPS, FFS or UB-FFS effect, characterized in that it contains, as dielectric, a liquid-crystalline medium according to the application.
[0493] The liquid-crystalline mixture preferably has a nematic phase range of at least 70 degrees in width.
[0494] The rotational viscosity γ1 is preferably 350 mPa-s or less, preferably 250 mPa-s or less and in particular 150 mPa-s or less.
[0495] The mixtures according to the application are suitable for all IPS and FFS-TFT applications using dielectrically positive liquid-crystalline media, for example XB-FFS.
[0496] The liquid-crystalline medium according to the application preferably consists essentially entirely of 4 to 15, in particular 5 to 12, and particularly preferably 10 or fewer compounds. These are preferably selected from the group of compounds of formulae C, B, I, II, III, IV, V, VI, VII, VIII and IX.
[0497] The liquid-crystalline medium according to the application can also optionally comprise more than 18 compounds. In this case, they preferably comprise 18 to 25 compounds.
[0498] In a preferred embodiment, the liquid-crystalline medium according to the application consists essentially of, preferably consists substantially of and most preferably consists essentially entirely of compounds which do not comprise a cyano group.
[0499] In a preferred embodiment, the liquid-crystalline medium according to the present application comprises compounds selected from the group consisting of compounds of formulae C, B, I, II and III, IV and V and VI to IX, preferably compounds selected from the group consisting of formulae C-1, C-2, C-3, C-4, B-1, B-2, B-3, B-4, I-1, I-2, II-1, II-2, III-1, III-2, IV, V, VII-1, VII-2, VIII and IX; they preferably consist mainly, particularly preferably essentially and very particularly preferably substantially completely of compounds of said formulae.
[0500] The liquid-crystalline medium according to the present application preferably has a nematic phase in each case at least at -10°C or less to 70°C or more, particularly preferably at -20°C or less to 80°C or more, very particularly preferably at -30°C or less to 85°C or more and most preferably at -40°C or less to 90°C or more.
[0501] The expression "having a nematic phase" here means on the one hand that no smectic phase and no crystallization is observed at the respective temperature at low temperature and on the other hand that no clearing occurs on heating from the nematic phase. The investigation at low temperature is carried out in a flow viscosimeter at the respective temperature and checked by storage in a test cell having a cell gap corresponding to an electro-optical application of at least 100 hours. The medium is regarded as stable at the temperature if the storage stability at a temperature of -20°C is 1,000 h or more in the respective test cell. At temperatures of -30°C and -40°C, the respective times are 500 h and 250 h, respectively. At high temperature, the clearing point is measured in a capillary by conventional methods.
[0502] In a preferred embodiment, the liquid-crystalline medium according to the present application is characterized by values of the optical anisotropy in the moderate to low range. The birefringence values are preferably 0.075 or more to 0.130 or less, particularly preferably 0.085 or more to 0.120 or less and very particularly preferably 0.090 or more to 0.115 or less.
[0503] In this embodiment, the liquid-crystalline medium according to the present application has a positive dielectric anisotropy Δε which is preferably 2.0 or more to 20 or less, more preferably to 15 or less, more preferably 2.0 or more to 10 or less, particularly preferably 2.0 or more to 9.0 or less and very particularly preferably 2.5 or more to 8.0 or less.
[0504] The liquid-crystalline medium according to the present application preferably has a relatively low threshold voltage (V0) value in the range from 1.0 V or more to 5.0 V or less, preferably to 2.5 V or less, preferably 1.2 V or more to 2.2 V or less, particularly preferably 1.3 V or more to 2.0 V or less.
[0505] Furthermore, the liquid-crystalline medium according to the present application has a high VHR value in a liquid-crystalline cell.
[0506] Generally, liquid-crystalline media having a low addressing voltage or threshold voltage here have a lower VHR than those having a higher addressing voltage or threshold voltage, and vice versa.
[0507] These preferred values of the individual physical properties are also preferably maintained in conjunction with one another by the medium according to the present application in each case.
[0508] In the present application, the term "compound", also written as "one or more compounds", refers to both a single compound and to a plurality of compounds, unless explicitly stated otherwise.
[0509] In a preferred embodiment, the liquid-crystalline medium according to the present application comprises
[0510] one or more compounds of the formula C, and
[0511] one or more compounds of the formula B, preferably selected from the group consisting of the formulae CB-n-F, CB-n-OT, CB-n-T, LB-n-F, LB-n-OT and LB-n-T, more preferably selected from the group consisting of the formulae CB-n-OT, CB-n-T, LB-n-OT and LB-n-T, preferably selected from the group consisting of the formulae CB-n-OT, CB-n-T, and / or
[0512] one or more compounds of the formula II, preferably selected from the group consisting of the formulae PUQU-n-F, CDUQU-n-F, APUQU-n-F and PGUQU-n-F, and / or
[0513] one or more compounds of the formula III, preferably selected from the group consisting of the formulae CCP-n-OT, CGG-n-F and CGG-n-OD, and / or
[0514] one or more compounds of the formulae IV and / or V, preferably selected from the group consisting of the formulae CC-n-V, CCP-n-m, CCP-V-n, CCP-V2-n and CGP-n-n and / or
[0515] one or more compounds of the formula VI, preferably of the formulae Y-n-Om, Y-nO-Om and / or CY-n-Om, selected from the group consisting of the formulae Y-3-O1, Y-4O-O4, CY-3-O2, CY-3-O4, CY-5-O2 and CY-5-O4, and / or
[0516] Optionally, preferably mandatorily, one or more compounds of formula VII-1, preferably selected from the group consisting of compounds of formula CCY-n-m and CCY-n-Om, preferably of formula CCY-n-Om, preferably selected from the group consisting of compounds of formula CCY-3-O2, CCY-2-O2, CCY-3-O1, CCY-3-O3, CCY-4-O2, CCY-3-O2 and CCY-5-O2, and / or
[0517] Optionally, preferably mandatorily, one or more compounds of formula VII-2, preferably of formula CLY-n-Om, preferably selected from the group consisting of compounds of formula CLY-2-O4, CLY-3-O2, CLY-3-O3, and / or
[0518] one or more compounds of formula VIII, preferably selected from the group consisting of compounds of formulae CZY-n-On and CCOY-n-m and / or
[0519] one or more compounds of formula IX, preferably selected from the group consisting of compounds of formulae PYP-n-m, PYP-n-mVI and PYP-n-mVI, preferably selected from the group consisting of compounds of formulae PYP-2-3, PYP-2-4, PYP-2-5, PYP-2-V and PYP-2-2V1, and / or
[0520] one or more compounds selected from the group consisting of compounds of formulae PGP-n-m, PGP-n-V, PGP-n-Vm, PGP-n-mV and PGP-n-mV1, preferably selected from the group consisting of compounds of formulae PGP-2-3, PGP-2-4, PGP-2-5, PGP-1-V, PGP-2-V and PGP-2-2V1, and / or
[0521] Optionally, preferably mandatorily, one or more compounds of formula IV, preferably selected from the group consisting of compounds of formulae CC-n-V, CC-n-Vm, CC-n-mVI and CC-nV-Vm, preferably CC-3-V, CC-3-V1, CC-4-V, CC-5-V, CC-3-2V1 and CC-V-V, particularly preferably selected from the group consisting of compounds CC-3-V, CC-3-V1, CC-4-V, CC-3-2V1 and CC-V-V, very particularly preferably the compound CC-3-V, and optionally additionally the compounds CC-4-V and / or CC-3-V1 and / or CC-3-2V1 and / or CC-V-V, and / or
[0522] Optionally, preferably mandatorily, one or more compounds of formula V, preferably selected from the group consisting of compounds of formulae CCP-V-1 and / or CCP-V2-1.
[0523] In a particularly preferred embodiment of the application, the medium according to the application comprises one or more compounds of formula IX,
[0524] Compounds of formula IX are also highly suitable as stabilizers in liquid-crystalline mixtures, especially in the case where p = q = 1 and ring A = 1,4-phenylene. In particular, they stabilize the mixtures against VHR upon UV exposure. 9 = 1,4-phenylene. In particular, they stabilize the mixtures against VHR upon UV exposure.
[0525] In a preferred embodiment, the medium according to the present application comprises one or more compounds of formula IX, very particularly preferably one or more compounds of formulae IX-1 to IX-4,
[0526]
[0527] wherein the parameters have the meanings given in formula IX.
[0528] In a further preferred embodiment, the medium comprises one or more compounds of formula IX-3, preferably of formula IX-3-a,
[0529]
[0530] wherein
[0531] alkyl and alkyl' independently of one another denote alkyl having 1 -7 C atoms, preferably having 2-5 C atoms,
[0532] In the case where compounds of formula IX are used in the liquid-crystalline medium according to the present application, they are preferably present in a concentration of 20% or less, more preferably 10% or less and most preferably 5% or less and for each (homologous) compound preferably a concentration of 10% or less and more preferably 5% or less.
[0533] For the present application, the following definitions apply to describe the composition of the compositions, unless indicated otherwise in each case:
[0534] "comprise": the concentration of the component in question in the composition is preferably 5% or more, particularly preferably 10% or more and very particularly preferably 20% or more,
[0535] "consists essentially of": the concentration of the component in question in the composition is preferably 50% or more, particularly preferably 55% or more and very particularly preferably 60% or more,
[0536] "consists essentially of": the concentration of the component in question in the composition is preferably 50% or more, particularly preferably 55% or more and very particularly preferably 60% or more,
[0537] "consists essentially of": the concentration of the component in question in the composition is preferably 50% or more, particularly preferably 55% or more and very particularly preferably 60% or more,
[0538] This applies both to the medium as a composition with its constituents, which can be a group of compounds as well as individual compounds, and also to the group of compounds with its respective constituents. The term "comprising" means that the concentration of the compound or compounds in question is preferably 1 % or more, particularly preferably 2% or more, very particularly preferably 4% or more, only when the concentration of the individual compounds relative to the entire medium is concerned.
[0539] For the present application, "<" means less than or equal to, preferably less than, and ">" means greater than or equal to, preferably greater than.
[0540] For the present application,
[0541]
[0542] denotes trans-1,4-cyclohexylene,
[0543]
[0544] denotes a mixture of both cis-1,4-cyclohexylene and trans-1,4-cyclohexylene, and
[0545]
[0546] denotes 1,4-phenylene.
[0547] For the present application, the expression "dielectrically positive compound" means a compound with Δε > 1.5, the expression "dielectrically neutral compound" means a compound with -1.5 < Δε < 1.5 and the expression "dielectrically negative compound" means a compound with Δε < -1.5. The dielectric anisotropy of a compound here is determined by dissolving 10% of the compound in a liquid crystal host and measuring the capacitance of the resulting mixture in each case in at least one test cell with a 20 pm cell thickness at 1 kHz in a test cell with homeotropic surface alignment and along the surface alignment. The measurement voltage is typically 0.5 V to 1.0 V, but is always below the threshold of the capacitance of the respective liquid crystal mixture investigated.
[0548] The host mixture for dielectrically positive and dielectrically neutral compounds is ZLI-4792 and the host mixture for dielectrically negative compounds is ZLI-2857, both from Merck KGaA, Germany. The value of each compound to be investigated is obtained from the change in the dielectric constant of the host mixture after addition of the compound to be investigated and extrapolated to 100% of the compound employed. The compound to be investigated is dissolved in the host mixture in an amount of 10%. If the solubility of the substance is too low for this purpose, the concentration is halved stepwise until the investigation can be carried out at the desired temperature.
[0549] If necessary, the liquid-crystalline media according to the application can also comprise further additives, such as stabilizers and / or pleochroic dyes, such as dichroic dyes and / or chiral dopants, in usual amounts. The amounts of these additives employed preferably add up to 0% or more to 10% or less, based on the amount of the entire mixture, particularly preferably 0.1% or more to 6% or less. The concentration of the individual compounds employed is preferably 0.1% or more to 3% or less. When specifying the concentration and concentration ranges of the liquid-crystalline compounds in the liquid-crystalline media, the concentration of these and similar additives is generally not taken into account.
[0550] In a preferred embodiment, the liquid-crystalline media according to the application comprise polymer precursors, which comprise one or more reactive compounds, preferably reactive mesogens, and if necessary further additives, such as polymerization initiators and / or polymerization moderators, in usual amounts. The amounts of these additives employed add up to 0% or more to 10% or less, preferably 0.1% or more to 2% or less, based on the amount of the entire mixture. When specifying the concentration and concentration ranges of the liquid-crystalline compounds in the liquid-crystalline media, the concentration of these and similar additives is not taken into account.
[0551] The composition consists of a plurality of compounds, preferably 3 or more to 30 or less, particularly preferably 6 or more to 20 or less and very particularly preferably 10 or more to 16 or less compounds, which are mixed in a customary manner. Usually, the desired amounts of the compounds used in smaller amounts are dissolved in the compounds which constitute the main constituents of the mixture. This is advantageously carried out at elevated temperature. If the temperature chosen is above the clearing point of the main constituents, the completion of the dissolution operation is particularly easily observed. However, the liquid-crystalline mixtures can also be prepared in other customary manner, for example using premixes or from so-called "multi-bottle systems".
[0552] The mixtures according to the application exhibit a very broad nematic phase range with a clearing point of 65°C or more, a very advantageous threshold of capacitance, a relatively high value of the retention ratio and at the same time a very good low-temperature stability at -30°C and -40°C. Furthermore, the mixtures according to the application are characterized by a low rotational viscosity γ1.
[0553] It is self-evident to the person skilled in the art that the media according to the application for VA, IPS, FFS or PALC displays can also comprise compounds in which, for example, H, N, O, CI, F has been replaced by the corresponding isotope.
[0554] The structure of the liquid-crystalline display according to the application corresponds to the general geometry as described, for example, in EP-A 0 240 379.
[0555] The liquid crystalline phases according to the present application can be varied by suitable additives in a manner that they can be used in any type of the hitherto disclosed displays, for example IPS and FFS LCD displays.
[0556] The following table E indicates possible dopants that can be added to the mixtures according to the present application. If the mixture comprises one or more dopants, it / they is / are employed in an amount of 0.01 % to 4 %, preferably 0.1 % to 1.0 %.
[0557] For example, stabilizers that can be preferably added to the mixtures according to the present application in an amount of 0.01 % to 6 %, in particular 0.1 % to 3 %, are indicated in the following table F.
[0558] For the purposes of the present application, all concentrations are indicated in percent by weight, unless explicitly stated otherwise, and all concentrations are relative to the entire respective mixture or relative to the entire respective mixture component, unless explicitly stated otherwise. In the present context, the term "mixture" describes a liquid crystalline medium.
[0559] Unless explicitly stated otherwise, all temperatures stated in the present application, for example melting point T(C,N), transition from smectic (S) to nematic (N) phase T(S,N) and clearing point T(N,I), are indicated in degrees Celsius (°C) and all temperature differences accordingly in differential degrees (° or degree).
[0560] For the purposes of the present application, the term "threshold voltage" refers to the capacitive threshold (V0), also called Freedericksz-threshold, unless explicitly stated otherwise.
[0561] All physical properties are and have been determined in accordance with "Merck Liquid Crystals, physical properties of Liquid Crystals", Status November 1997, Merck KGaA (Germany) and are valid for a temperature of 20 °C, and Δn is determined at 436 nm, 589 nm and 633 nm and Δε is determined at 1 kHz, unless explicitly stated otherwise in each case.
[0562] Electro-optical properties, for example threshold voltage (V0) (capacitive measurement) (which is the switching behavior), are measured in a test cell produced by Merck Japan. The measurement cell has a soda lime glass substrate and is constructed in an ECB or VA configuration (with diluent ** 26 of SE-1211 (mixing ratio 1 : 1 ), both from Nissan Chemicals, Japan), which have been rubbed perpendicular to each other and influence the homeotropic alignment of the liquid crystal. The surface area of the transparent, almost square ITO electrodes is 1 cm 2 .
[0563] Unless otherwise stated, no chiral dopant is added to the liquid crystal mixture used, but the latter is also particularly suitable for use in applications where this type of doping is necessary.
[0564] The rotational viscosity is measured using the rotating permanent magnet method and the flow viscosity in a modified Ubbelohde viscometer. For the liquid crystal mixtures ZLI-2293, ZLI-4792 and MLC-6608 (all products from Merck KGaA, Darmstadt, Germany) the rotational viscosity values measured at 20 °C are 161 mPa-s, 133 mPa-s and 186 mPa-s, respectively, and the flow viscosity values (v) are 21 mm 2 ·s -1 , 14 mm 2 ·s -1 and 27 mm 2 ·s -1 , respectively.
[0565] For practical purposes, the dispersion of a material can be conveniently characterized in the following way, which is used throughout the present invention, unless explicitly stated otherwise. The birefringence values are determined at a temperature of 20 °C at several fixed wavelengths using a modified Abbe refractometer, in which a homeotropically aligned surface is in contact with the material on the side of the prism. The birefringence values are determined at the specific wavelength values of 436 nm (individual selected spectral lines of a low-pressure mercury lamp), 589 nm (sodium "D" line) and 633 nm (wavelength of a HE-Ne laser, which is used in combination with an attenuator / diffuser to prevent eye damage to the observer). In the following table, Δn is given at 589 nm and Δ(Δn) is given as Δ(Δn) = Δn(436 nm) - Δn(633 nm).
[0566] The following symbols are used, unless explicitly stated otherwise:
[0567] V0threshold voltage, capacitive [V], at 20 °C,
[0568] n e extraordinary refractive index measured at 20 °C and 589 nm,
[0569] n o ordinary refractive index measured at 20 °C and 589 nm,
[0570] Δnoptical anisotropy measured at 20 °C and 589 nm,
[0571] λwavelength λ [nm],
[0572] Δn(λ)optical anisotropy measured at 20 °C and wavelength λ,
[0573] Δ(Δn) change in optical anisotropy, defined as:
[0574] Δn(20°C, 436 nm) - Δn(20°C, 633 nm),
[0575] Δ(Δn * ) "relative change in optical anisotropy", defined as:
[0576] Δ(Δn) / Δn(20°C, 589 nm),
[0577] ε ⊥ dielectric permittivity of the medium perpendicular to the director at 20°C and 1 kHz,
[0578] ε || dielectric permittivity of the medium parallel to the director at 20°C and 1 kHz,
[0579] Δε dielectric anisotropy at 20°C and 1 kHz,
[0580] T(N, I) or clp. clearing point [°C],
[0581] ν flow viscosity measured at 20°C [mm 2 ·s -1 ],
[0582] γ1 rotary viscosity measured at 20°C [mPa·s],
[0583] k 11 elastic constant, "splay" deformation at 20°C [pN],
[0584] k 22 elastic constant, "twist" deformation at 20°C [pN] (k 22 ≈ 1 / 2 k 11 ),
[0585] k 33 elastic constant, "bend" deformation at 20°C [pN],
[0586] k av. average elastic constant, here defined as [pN]
[0587] k av. ≡ (3 / 2 k 11 + k 33 ) / 3 ≈ (k 11 + k 22 + k 33 ) / 3
[0588] LTS low temperature stability of the phase, measured in a test cell,
[0589] VHR voltage holding ratio,
[0590] AVHR decrease in voltage holding ratio, and
[0591] S rel relative stability of VHR.
[0592] The following examples illustrate the present application without limiting it. They show, however, to the person skilled in the art the concept of preferred mixtures of compounds to be used and their respective concentrations as well as their combinations with each other. Furthermore, the examples elucidate the properties and property combinations which can be obtained.
[0593] For the present application and in the following examples, the structure of the liquid crystalline compounds is indicated by a short code which is translated into a chemical formula according to the following Tables A to C. All groups C n H 2n+1 , C m H 2m+1 and C l H 2l+1 or C n H 2n , C m H 2m and C l H 2l are linear alkyl groups or alkylene groups, each having n, m and I C atoms in each case. Preferably, n, m and I are independently of each other 1, 2, 3, 4, 5, 6 or 7. Table A shows the code of the ring elements of the core of the compounds, Table B lists the bridging units, and Table C lists the symbolic meaning of the left-hand and right-hand end groups. The short code consists of the code of the ring elements with optional linking groups, followed by a first hyphen and the code of the left-hand end group, and a second hyphen and the code of the right-hand end group. Table D shows exemplary structures of the compounds and their respective short codes.
[0594] Table A: Ring elements
[0595]
[0596]
[0597]
[0598]
[0599] Table B: Bridging units
[0600]
[0601] Table C: End groups
[0602]
[0603]
[0604]
[0605]
[0606] wherein n and m are each an integer, and the three dots "..." are a placeholder for further abbreviations from the table.
[0607] In addition to the compounds of the formula B, the mixtures according to the application preferably also comprise one or more of the following-mentioned compounds.
[0608] The following abbreviations are used:
[0609] (n, m, k and I are each, independently of the others, an integer, preferably 1 to 9, preferably 1 to 7, k and I can also be 0 and are preferably 0 to 4, more preferably 0 or 2, and most preferably 2, n is preferably 1, 2, 3, 4 or 5, in the combination "-nO-", it is preferably 1, 2, 3 or 4, 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 "-IVm" is preferably "2V1 ").
[0610] Table D
[0611] Exemplary, preferred compounds of the formula C
[0612]
[0613]
[0614] Exemplary, preferred compounds of the formula B with high ε ⊥
[0615]
[0616]
[0617]
[0618] Exemplary, preferred compounds of the formula I with high ε ⊥
[0619]
[0620]
[0621] Exemplary, preferred compounds of the formula I with high ε⊥ Compounds of formula I:
[0622]
[0623]
[0624]
[0625]
[0626] Exemplary, preferred dielectric positive compounds: ⊥ Compounds of formula B:
[0627]
[0628]
[0629]
[0630] Exemplary, preferred dielectric neutral compounds:
[0631]
[0632]
[0633]
[0634]
[0635]
[0636]
[0637]
[0638]
[0639] Exemplary, preferred dielectric neutral compounds:
[0640]
[0641]
[0642]
[0643]
[0644]
[0645]
[0646] Other dielectrically neutral compounds
[0647]
[0648]
[0649]
[0650] Exemplary, preferred dielectrically negative compounds:
[0651]
[0652]
[0653]
[0654]
[0655]
[0656]
[0657]
[0658]
[0659]
[0660] Table E shows chiral dopants which can preferably be employed in the mixtures according to the application.
[0661] Table E
[0662]
[0663]
[0664]
[0665] In a preferred embodiment of the application, the medium according to the application comprises one or more compounds selected from the group of the compounds of Table E.
[0666] Table F shows stabilizers which can preferably be employed in the mixtures according to the application in addition to the compounds of the formula B. Here, the parameter n denotes an integer from 1 to 12. In particular, the shown phenolic derivatives can be employed as further stabilizers since they act as antioxidants.
[0667] Table F
[0668]
[0669]
[0670]
[0671]
[0672]
[0673] In a preferred embodiment of the application, the medium according to the application comprises one or more compounds selected from the group of compounds of Table F, in particular one or more compounds selected from the group of compounds of the following two formulae
[0674] Examples
[0675] The following examples illustrate the application without limiting it in any way. However, the physical properties make it clear to the person skilled in the art which properties can be achieved and in which ranges they can be adjusted. In particular, the combination of a plurality of properties which can thus be achieved with preference is well defined for the person skilled in the art.
[0676] In the following tables, the following end group abbreviations are used
[0677]
[0678] The physical properties are given at a temperature of 20°C and the unit for γ1 is mPa s. Compound examples / preferably used Examples of compounds used
[0679]
[0680]
[0681]
[0682] Examples of other compounds / preferably used
[0683]
[0684]
[0685]
[0686]
[0687] Examples of mixtures
[0688] The following disclose exemplary mixtures.
[0689] Comparative Example 1
[0690] The following mixture (CM-1) was prepared and studied
[0691]
[0692] This mixture, mixture CM-1, provided a fairly high transmittance.
[0693] Example 1
[0694] The following mixture (M-1) was prepared and studied
[0695]
[0696]
[0697] This mixture, mixture M-1, had a faster response time parameter and a high transmittance.
[0698] Example 2
[0699] The following mixture (M-2) was prepared and studied
[0700]
[0701] This mixture, mixture M-2, had a higher transmittance.
[0702] Example 3
[0703] The following mixture (M-3) was prepared and studied
[0704]
[0705]
[0706] This mixture, mixture M-3, had a faster response time and a high transmittance.
[0707] Example 4
[0708] The following mixture (M-4) was prepared and studied
[0709]
[0710] This mixture, mixture M-4, had a good combination of properties.
[0711] Example 5
[0712] The following mixture (M-5) was prepared and studied
[0713]
[0714] This mixture, Mixture M-5, has a good combination of properties.
[0715] Example 6
[0716] The following mixture (M-6) was prepared and investigated
[0717]
[0718]
[0719] This mixture, Mixture M-6, has a good combination of properties.
[0720] Example 7
[0721] The following mixture (M-7) was prepared and investigated
[0722]
[0723] This mixture, Mixture M-7, has a good combination of properties.
[0724] Example 8
[0725] The following mixture (M-8) was prepared and investigated
[0726]
[0727]
[0728] This mixture, Mixture M-8, has a good combination of properties.
[0729] Example 9
[0730] The following mixture (M-9) was prepared and investigated
[0731]
[0732] This mixture, Mixture M-9, has a good combination of properties.
[0733] Example 10
[0734] The following mixture (M-10) was prepared and investigated
[0735]
[0736]
[0737] This mixture, Mixture M-10, has good combination of properties.
[0738] Example 11
[0739] The following mixture (M-11) was prepared and studied
[0740]
[0741] This mixture, Mixture M-11, has good combination of properties.
[0742] Example 12
[0743] The following mixture (M-12) was prepared and studied
[0744]
[0745] This mixture, Mixture M-12, has good combination of properties.
[0746] Example 13
[0747] The following mixture (M-13) was prepared and studied
[0748]
[0749] This mixture, Mixture M-13, has good combination of properties.
[0750] Example 14
[0751] The following mixture (M-14) was prepared and studied
[0752]
[0753] This mixture, Mixture M-14, has good combination of properties.
[0754] Example 15
[0755] The following mixture (M-15) was prepared and studied
[0756]
[0757] This mixture, Mixture M-15, has good combination of properties.
[0758] Example 16
[0759] The following mixture (M-16) was prepared and studied
[0760]
[0761] This mixture, Mixture M-16, has good combination of properties.
[0762] Example 17
[0763] The following mixture (M-17) was prepared and studied
[0764]
[0765]
[0766] This mixture, Mixture M-17, has good combination of properties.
[0767] Example 18
[0768] The following mixture (M-18) was prepared and studied
[0769]
[0770] This mixture, Mixture M-18, has good combination of properties.
[0771] Example 19
[0772] The following mixture (M-19) was prepared and studied
[0773]
[0774]
[0775] This mixture, Mixture M-19, has good combination of properties.
[0776] Example 20
[0777] The following mixture (M-20) was prepared and studied
[0778]
[0779] This mixture, Mixture M-20, has good combination of properties.
[0780] Example 21
[0781] The following mixture (M-21) was prepared and studied
[0782]
[0783]
[0784] This mixture, Mixture M-21, has a good combination of properties.
[0785] Example 22
[0786] The following mixture (M-22) was prepared and investigated
[0787]
[0788] This mixture, Mixture M-22, has a good combination of properties.
[0789] Example 23
[0790] The following mixture (M-23) was prepared and investigated
[0791]
[0792]
[0793] This mixture, Mixture M-23, has a good combination of properties.
[0794] Example 24
[0795] The following mixture (M-24) was prepared and investigated
[0796]
[0797] This mixture, Mixture M-24, has a good combination of properties.
[0798] Example 25
[0799] The following mixture (M-25) was prepared and investigated
[0800]
[0801]
[0802] This mixture, Mixture M-25, has a good combination of properties.
[0803] Example 26
[0804] The following mixture (M-26) was prepared and investigated
[0805]
[0806]
[0807] This mixture, Mixture M-26, has a good combination of properties.
[0808] Example 27
[0809] The following mixture (M-27) was prepared and studied
[0810]
[0811] This mixture, Mixture M-27, has a good combination of properties.
[0812] Example 28
[0813] The following mixture (M-28) was prepared and studied
[0814]
[0815]
[0816] This mixture, Mixture M-28, has a good combination of properties.
[0817] Example 29
[0818] The following mixture (M-29) was prepared and studied
[0819]
[0820] This mixture, Mixture M-29, has a good combination of properties.
[0821] Example 30
[0822] The following mixture (M-30) was prepared and studied
[0823]
[0824]
[0825] This mixture, Mixture M-30, has a good combination of properties.
[0826] Example 31
[0827] The following mixture (M-31) was prepared and studied
[0828]
[0829] This mixture, Mixture M-31, has a good combination of properties.
[0830] Example 32
[0831] The following mixture (M-32) was prepared and studied
[0832]
[0833]
[0834] This mixture, Mixture M-32, has good combination of properties.
[0835] Example 33
[0836] The following mixture (M-33) was prepared and investigated
[0837]
[0838] This mixture, Mixture M-33, has good combination of properties.
[0839] Example 34
[0840] The following mixture (M-34) was prepared and investigated
[0841]
[0842]
[0843] This mixture, Mixture M-34, has good combination of properties.
[0844] Example 35
[0845] The following mixture (M-35) was prepared and investigated
[0846]
[0847] This mixture, Mixture M-35, has good combination of properties.
[0848] Example 36
[0849] The following mixture (M-36) was prepared and investigated
[0850]
[0851]
[0852] This mixture, Mixture M-36, has good combination of properties.
[0853] Example 37
[0854] The following mixture (M-37) was prepared and investigated
[0855]
[0856] This mixture, Mixture M-37, has a good combination of properties.
[0857] Example 38
[0858] The following mixture (M-38) was prepared and investigated
[0859]
[0860] This mixture, Mixture M-38, has a good combination of properties.
[0861] Examples 39.1 to 39.4
[0862] Example 39.1
[0863] To Mixture M-1 of Example 1 was added 100 ppm of compound S-1
[0864]
[0865] The resulting mixture exhibited excellent stability.
[0866] Example 39.2
[0867] To Mixture M-1 of Example 1 was added 100 ppm of compound S-2
[0868]
[0869] The resulting mixture exhibited excellent stability.
[0870] Example 39.3
[0871] To Mixture M-1 of Example 1 was added 100 ppm of compound S-3
[0872]
[0873] wherein n is 3. The resulting mixture exhibited excellent stability.
[0874] Example 39.4
[0875] To Mixture M-1 of Example 1 was added 100 ppm of compound S-4
[0876]
[0877] wherein n is 3. The resulting mixture exhibited excellent stability.
[0878] Examples 40.1 to 40.4
[0879] Example 40.1
[0880] To mixture M-2 of Example 2 was added 100 ppm of compound S-1. The resulting mixture exhibited excellent stability.
[0881] Example 40.2
[0882] To mixture M-2 of Example 2 was added 100 ppm of compound S-2. The resulting mixture exhibited excellent stability.
[0883] Example 40.3
[0884] To mixture M-2 of Example 2 was added 100 ppm of compound S-3. The resulting mixture exhibited excellent stability.
[0885] Example 40.4
[0886] To mixture M-2 of Example 2 was added 100 ppm of compound S-4. The resulting mixture exhibited excellent stability.
[0887] Examples 41.1 to 41.4
[0888] Example 41.1
[0889] To mixture M-3 of Example 3 was added 100 ppm of compound S-1. The resulting mixture exhibited excellent stability.
[0890] Example 41.2
[0891] To mixture M-3 of Example 3 was added 100 ppm of compound S-2. The resulting mixture exhibited excellent stability.
[0892] Example 41.3
[0893] To mixture M-3 of Example 3 was added 100 ppm of compound S-3. The resulting mixture exhibited excellent stability.
[0894] Example 41.4
[0895] To mixture M-3 of Example 3 was added 100 ppm of compound S-4. The resulting mixture exhibited excellent stability.
[0896] Examples 42.1 to 42.4
[0897] Example 42.1
[0898] To mixture M-28 of Example 28 was added 100 ppm of compound S-1. The resulting mixture exhibited excellent stability.
[0899] Example 42.2
[0900] To mixture M-28 of Example 28 was added 100 ppm of compound S-2. The resulting mixture exhibited excellent stability.
[0901] Example 42.3
[0902] To mixture M-28 of Example 28 was added 100 ppm of compound S-3. The resulting mixture exhibited excellent stability.
[0903] Example 42.4
[0904] To mixture M-28 of Example 28 was added 100 ppm of compound S-4. The resulting mixture exhibited excellent stability.
[0905] Example 43
[0906] The following mixture (M-43) was prepared and investigated
[0907] Mixture M-43
[0908]
[0909] This mixture, Mixture M-43, has a good combination of properties.
[0910] To mixture M-43 was added 0.04% of compound S-4. The resulting mixture exhibited excellent stability.
[0911] To mixture M-43 was added 0.040% of compound S-4 and 0.005% of compound S-5
[0912] The resulting mixture exhibited very excellent stability.
[0913] Example 44
[0914] The following mixture (M-44) was prepared and investigated
[0915] Mixture M-44
[0916]
[0917] This mixture, Mixture M-44, has a good combination of properties.
[0918] Example 45
[0919] The following mixture (M-45) was prepared and studied
[0920] Mixture M-45
[0921]
[0922] This mixture, Mixture M-45, has a good combination of properties.
[0923] Example 46
[0924] The following mixture (M-46) was prepared and studied
[0925] Mixture M-46
[0926]
[0927] This mixture, Mixture M-46, has a good combination of properties.
[0928] Example 47
[0929] The following mixture (M-47) was prepared and studied
[0930] Mixture M-47
[0931]
[0932] This mixture, Mixture M-47, has a good combination of properties.
[0933] Example 48
[0934] The following mixture (M-48) was prepared and studied
[0935] Mixture M-48
[0936]
[0937]
[0938] This mixture, Mixture M-48, has a good combination of properties.
[0939] Example 49
[0940] The following mixture (M-49) was prepared and studied
[0941] Mixture M-49
[0942]
[0943] This mixture, Mixture M-49, has good combination of properties.
[0944] Example 50
[0945] The following mixture (M-50) was prepared and studied
[0946] Mixture M-50
[0947]
[0948]
[0949] This mixture, Mixture M-50, has good combination of properties.
[0950] Example 51
[0951] The following mixture (M-51) was prepared and studied
[0952] Mixture M-51
[0953]
[0954] This mixture, Mixture M-51, has good combination of properties.
[0955] Example 52
[0956] The following mixture (M-52) was prepared and studied
[0957] Mixture M-52
[0958]
[0959] This mixture, Mixture M-52, has good combination of properties.
[0960] Example 53
[0961] The following mixture (M-53) was prepared and studied
[0962] Mixture M-53
[0963]
[0964] This mixture, Mixture M-53, has good combination of properties.
[0965] Example 54
[0966] The following mixture (M-54) was prepared and studied
[0967] Mixture M-54
[0968]
[0969]
[0970] This mixture, Mixture M-54, has good combination of properties.
[0971] Example 55
[0972] The following mixture (M-55) was prepared and studied
[0973] Mixture M-55
[0974]
[0975] This mixture, Mixture M-55, has good combination of properties.
[0976] To Mixture M-55 was added 0.04% of Compound S-3. The resulting mixture showed excellent stability.
[0977] Example 56
[0978] The following mixture (M-56) was prepared and studied
[0979] Mixture M-56
[0980]
[0981]
[0982] This mixture, Mixture M-56, has good combination of properties.
[0983] To Mixture M-56 was added 0.04% of Compound S-3. The resulting mixture showed excellent stability.
[0984] Example 57
[0985] The following mixture (M-57) was prepared and studied
[0986] Mixture M-57
[0987]
[0988]
[0989] This mixture, Mixture M-57, has good combination of properties.
[0990] Example 58
[0991] The following mixture (M-58) was prepared and investigated
[0992] Mixture M-58
[0993]
[0994] This mixture, Mixture M-58, has a good combination of properties.
[0995] Example 59
[0996] The following mixture (M-59) was prepared and investigated
[0997] Mixture M-59
[0998]
[0999]
[1000] This mixture, Mixture M-59, has a good combination of properties.
Claims
1. A liquid-crystalline medium, characterised in that which comprises one or more compounds of the formula C wherein represents independently of each other at each occurrence represent R C1 and R C2 independently of one another, alkyl having 1 to 15 C atoms, wherein one or more CH2groups in these radicals can each be replaced, independently of one another, by -CH=CH-, -C≡C-, -CF2O-, -OCF2-, -O-, -(CO)-O-, -O-(CO)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, alkenyl having 2 to 7 C atoms, alkenyloxy, alkoxalkyl or fluorinated alkenyl, wherein one -CH2- group can be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, the above replacements being made in such a way that O atoms are not linked directly to one another, and wherein one or more H atoms can be replaced by halogen, and wherein each ring can be optionally substituted by one or two alkyl groups, and one or more compounds of the formula B, wherein represents independently of each other at each occurrence represent n denotes 1 or 2, R 1 has one of the meanings given for R C1 and X 1 denotes F, CI, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the last four radicals having 1 to 4 C atoms.
2. The medium of claim 1, wherein which comprises one or more compounds selected from the group consisting of the compounds of the formulae II and III wherein R 2 has one of the meanings given for R C1 in claim 1, independently of one another in each occurrence L 21 and L 22 represents H or F, X 2 represents halogen, halogenated alkyl or alkoxy with 1-3 C atoms, or halogenated alkenyl or alkenyloxy with 2 or 3 C atoms, m denotes 0, 1, 2 or 3, R 3 has one of the meanings given for R C1 in claim 1, independently of one another in each occurrence L 31 and L 32 independently of one another H or F, X 3 represents halogen, halogenated alkyl or alkoxy with 1-3 C atoms, or halogenated alkenyl or alkenyloxy with 2 or 3 C atoms, Z 3 represents -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O- or a single bond, and, n denotes 0, 1, 2 or 3, wherein each ring, optionally, is each substituted by one or two alkyl groups.
3. The medium of claim 1 or 2, wherein which comprises one or more compounds selected from the group consisting of the compounds of the formulae IV and V: wherein R 41 and R 42 each independently of one another have the meanings indicated in claim 1 for R C1 R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 independently of one another and if occurs twice these also denote, independently of one another, Z 41 and Z 42 independently of one another and if Z 41 occur twice, these also denote, independently of one another, -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, -CF2O-, -C≡C- or a single bond, p denotes 0, 1 or 2, R 51 and R 52 each independently of one another have one of the meanings given above for R 41 and R 42 each independently of one another have one of the meanings given above for R To denote, independently of one another, if present Z 51 to Z 53 each, independently of one another, denotes -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO- or a single bond, and i and j each, independently of one another, denote 0 or 1, wherein each ring, optionally, is each substituted by one or two alkyl groups.
4. The medium of claim 1 or 2, wherein which comprises one or more compounds of the formula B, wherein representing representing n denotes 1 or 2, R 1 one of the meanings given for R C1 in claim 1, and X 1 represents F, Cl, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy.
5. The medium of claim 1 or 2, wherein which further comprises one or more compounds of the formula I: wherein denotes represents n denotes 0 or 1, R 11 and R 12 each independently of one another have one of the meanings given in claim 1 for R C1 R R 1 has one of the meanings given for R C1 in claim 1, and X 1 represents F, Cl, fluoroalkyl, fluoroalkenyl, fluoroalkoxy or fluoroalkenyloxy, the compounds of the formulae B, VII and IX are not contained therein, and wherein each ring, optionally, is each substituted by one or two alkyl groups.
6. The medium of claim 1 or 2, wherein which comprises one or more compounds selected from the group consisting of the compounds of the formulae VI to IX: wherein R 61 has one of the meanings given for R C1 in claim 1, R 62 has one of the meanings given for R C1 in claim 1, and l denotes 0 or 1, R 71 has one of the meanings given for R C1 in claim 1, R 72 has one of the meanings given for R C1 in claim 1, represents R 81 has one of the meanings given for R C1 in claim 1, R 82 has one of the meanings given for R C1 in claim 1, representing Z 8 represents -(C=0)-0-, -CH2-0-, -CF2-0- or -CH2-CH2-, o denotes 0 or 1, R 91 and R 92 independently of one another have the meanings indicated above for R 71 , denotes p and q each, independently of one another, denote 0 or 1, and wherein each ring, optionally, is each substituted by one or two alkyl groups, and the compounds of the formula VII are excluded from the compounds of the formula IX.
7. The medium of claim 1 or 2, wherein The total concentration of the compounds of the formula B in the entire medium is 1 % or more to 60% or less.
8. The medium of claim 1 or 2, wherein which further comprises one or more chiral compounds and / or one or more stabilizers.
9. An electro-optical display or electro-optical assembly, characterized in that which comprises the liquid-crystalline medium according to any of claims 1 to 8.
10. The display of claim 9, wherein which is based on the IPS- or FFS mode.
11. The display of claim 9 or 10, wherein which contains an active matrix addressing device.
12. Use of the medium according to any of claims 1 to 8 in an electro-optical display or an electro-optical component.
13. Process for the preparation of a liquid-crystalline medium according to any of claims 1 to 8, characterised in that one or more compounds of the formula C are mixed with one or more further mesogenic compounds and optionally one or more additives.
Citation Information
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