Liquid crystal media

Abstract

This invention relates to liquid crystal media comprising at least one compound of formula I, wherein R 1 and R 1* Each of these groups independently represents an alkyl or alkoxy group having 1-15 carbon atoms, wherein one or more CH2 groups in these groups may be independently replaced by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, -O-CO- in such a way that the O atoms are not directly connected to each other, and wherein one or more H atoms may be replaced by halogens, L 1 and L 2 Each of these terms independently represents F, Cl, CF3, or CHF2 and relates to their use in active matrix displays, particularly displays based on VA, PSA, PA-VA, SS-VA, SA-VA, PS-VA, PALC, IPS, PS-IPS, FFS, or PS-FFS effects.

Description

[0001] This application is a divisional application of patent application number 201510426405.6. Technical Field

[0002] This invention relates to liquid crystal media comprising at least one compound of formula I.

[0003]

[0004] in

[0005] R 1 and R 1* Each of these groups independently represents an alkyl or alkoxy group having 1-15 carbon atoms, wherein one or more CH2 groups among these groups may be independently represented by -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, and -O-CO- are substitutions where the O atoms are not directly connected to each other, and additionally, one or more H atoms can be replaced by halogens.

[0006] L 1 and L 2 Each can be represented independently as F, Cl, CF3, or CHF2.

[0007] This type of media can be used, in particular, for electro-optic displays with active matrix addressing based on the ECB effect and for IPS (in-plane switching) or FFS (edge ​​field switching) displays. Background Technology

[0008] In 1971, the principle of electric field-controlled birefringence, namely the ECB effect or DAP (deformation of phase alignment) effect, was first proposed (M. F. Chieckel and K. Fahrenschon, "Deformation of nematic liquid crystals with vertical orientation in electrical fields", Appl. Phys. Lett. 19 (1971), 3912). Later, J. F. Kahn (Appl. Phys. Lett. 20 (1972), 1193) and G. Labrunie and J. Robert (J. Appl. Phys. 44 (1973), 4869) published papers.

[0009] Papers published by J. Robert and F. Clerc (SID 80 Digest Techn. Papers (1980), 30), J. Duchene (Displays 7 (1986), 3), and H. Schad (SID 82 Digest Techn. Papers (1982), 244) demonstrate that liquid crystal phases must possess a high elastic constant K3 / K1 ratio, a high optical anisotropy Δn value, and a dielectric anisotropy value Δε≤-0.5 to be suitable for high-information display elements based on the ECB effect. Electro-optical display elements based on the ECB effect have vertical edge alignment (VA technology = vertical alignment). Negative dielectric liquid crystal media can also be used in displays based on the so-called IPS or FFS effect.

[0010] Displays using the ECB effect, such as so-called VAN (vertically aligned nematic) displays, include MVA (multi-quadrant 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, CT 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) and PVA (vertically aligned nematic, 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). II, pp. 760-763), ASV (over-viewing angle, e.g., Shigeta, Mitzuhiro and Fukuoka, Hirofumi, paper 15.2: "Development of High Quality LCDTV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 754–757) modes, have all evolved themselves into one of the three most important recent liquid crystal displays, especially for television, in addition to IPS (in-plane switching) displays (e.g., Yeo, SD, paper 15.3: "An LC Display for the TV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 758 & 759) and the long-known TN (twisted nematic) displays.For example, the aforementioned techniques are compared in conventional form 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 significantly improved by using high-speed drive addressing methods, 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, pp. 106-109, progress in image-compatible response time, especially in gray-to-shade switching, remains an unsatisfactory problem.

[0011] The industrial application of this effect in electro-optical display elements requires LC phases, which must meet a variety of requirements. Of particular importance are resistance to moisture, chemical effects from air, and physical influences such as heat, infrared radiation, visible light, ultraviolet light, and DC and AC electric fields.

[0012] In addition, industrially usable LC phases need to have a liquid crystal mesocrystalline phase and low viscosity within a suitable temperature range.

[0013] None of the disclosed series of compounds with a liquid crystal mesocrystalline phase to date contains a single compound that satisfies all these requirements. Therefore, mixtures of 2-25, preferably 3-18, compounds are typically prepared to obtain a substance usable as an LC phase. However, it is not possible to easily prepare the most suitable phase in this way, because no usable liquid crystal material with significant negative dielectric anisotropy and sufficient long-term stability has yet been found.

[0014] A matrix liquid crystal display (MLC display) is known. Nonlinear elements capable of being switched individually for each pixel are, for example, active elements (e.g., transistors). The term "active matrix" is used below, where a distinction exists between two types:

[0015] 1. MOS (Metal-Oxide-Semiconductor) transistors on a silicon wafer as a substrate

[0016] 2. Thin-film transistors (TFTs) on a glass substrate.

[0017] In Type 1 cases, the electro-optical effects used are generally dynamic scattering or guest-host effects. The use of monocrystalline silicon as the substrate material limits the size of the display, and the integration of different display modules can also cause problems at the connection points.

[0018] In the preferred and more promising type 2 case, the electro-optic effect used is generally the TN effect.

[0019] The difference between the two technologies: TFTs containing compound semiconductors such as CdSe, or TFTs based on polycrystalline silicon or amorphous silicon. The latter technology has been the focus of research worldwide.

[0020] A TFT matrix is ​​applied inside one glass plate of the display, while another glass plate holds the transparent counter electrode. The TFTs are very small compared to the size of the pixel electrodes and have virtually no opposing effect on the image. This technology can also be extended to full-color displays, where mosaics of red, green, and blue filters are arranged such that the filter elements are opposite each switchable pixel.

[0021] Here, the term MLC display includes any matrix display with integrated nonlinear elements, that is, in addition to an active matrix, there are displays with passive elements such as variable resistors or diodes (MIM = Metal-Insulator-Metal).

[0022] These types of MLC displays are particularly suitable for TV applications (such as pocket TVs) or high-information displays in automotive or aircraft structures. Besides the angle-dependent issues regarding contrast and response time, insufficient specific resistivity of the liquid crystal mixture also causes problems in MLC displays [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, p. 141ff, Paris; STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, p. 145ff, Paris]. As the resistance decreases, the contrast of the MLC display deteriorates. The resistivity of the liquid crystal mixture generally decreases with the lifespan of an MLC display due to its interaction with the inner surface of the display. Therefore, a high (initial) resistance is very important for the display, and thus an acceptable resistance value must be achieved after long-term operation.

[0023] Therefore, there is still a great need for MLC displays with very high resistivity, a wide operating temperature range, short response time, and low threshold voltage, which can produce a variety of grayscale levels.

[0024] The disadvantages of commonly used MLC-TN displays are their relatively low contrast, relatively high viewing angle dependence, and difficulty in producing grayscale in these displays.

[0025] VA displays offer significantly better viewing angle dependence and are therefore primarily used in televisions and monitors. However, improvements in response time are still needed, especially for television applications with frame rates greater than 60Hz (image change frequency / repetition rate). However, this must be achieved without compromising properties such as low-temperature stability. Summary of the Invention

[0026] The object of this invention is to provide liquid crystal mixtures based on the ECB effect, IPS, or FFS effect, particularly for monitor and TV applications, which do not have the disadvantages described above, or have only a small degree of the disadvantages described above. Specifically, for monitors and televisions, it is necessary to ensure that they operate at very high and very low temperatures while simultaneously having very short response times and improved reliability behavior, particularly demonstrating no or significantly reduced image retention after long-term operation.

[0027] Surprisingly, if a general formula I polar compound is used in liquid crystal mixtures, particularly in LC mixtures with negative dielectric anisotropy, preferably for VA and FFS displays, the rotational viscosity value and thus the response time can be improved.

[0028] Therefore, the present invention relates to liquid crystal media comprising at least one compound of formula I. The present invention also relates to compounds of formula I.

[0029] Compounds of formula I are covered by general formula (I) in WO 02 / 055463 A1.

[0030] The mixtures according to the invention preferably exhibit a very wide nematic phase range, a clearing point ≥70°C, preferably ≥75°C, particularly ≥80°C, a very favorable capacitance threshold value, a relatively high retention rate, and simultaneously very good low-temperature stability at -20°C and -30°C, as well as a very low rotational viscosity and a short response time. The mixtures according to the invention are further distinguished by the fact that, in addition to improved rotational viscosity γ1, a relatively high elastic constant value K is also observed. 33 To improve response time. Compound of formula I is used in LC mixtures preferably with negative dielectric anisotropy, with rotational viscosity γ1 and elastic constant K. i The ratio decreased.

[0031] Some preferred embodiments of the mixture according to the present invention are described below.

[0032] In compound I, R 1 and R 1* Preferably, each of the linear alkyl or alkoxy groups, particularly CH3, C2H5, C3H7, C4H9, and C5H, is independently represented. 11 C6H 13 C7H 15 , OCH3, n-C2H5O, n-OC3H7, n-OC4H9, n-OC5H 11 n-OC6H 13 n-OC7H 15, and alkenyl groups, especially CH2=CH2, CH2CH=CH2, CH2CH=CHCH3, CH2CH=CHC2H5, branched alkoxy groups, especially OC3H6CH(CH3)2, and alkenyl groups, especially OCH=CH2, OCH2CH=CH2, OCH2CH=CHCH3, OCH2CH=CHC2H5.

[0033] R 1 Particularly preferred are straight-chain alkyl or alkoxy groups having 1-7 carbon atoms. R 1* Particularly preferred are straight-chain alkoxy groups having 1-7 carbon atoms.

[0034] L in compound of formula I 1 and L 2 The preferred option is F.

[0035] The preferred compounds of formula I are compounds of formulas I-1 to I-10.

[0036]

[0037]

[0038]

[0039] in

[0040] alkyl and alkyl * Each of these terms independently represents a straight-chain alkyl group having 1-6 carbon atoms, alkenyl and alkenyl * Each of these independently represents a straight-chain alkenyl group having 2-7 carbon atoms, alkoxy and alkoxy * Each independently represents a straight-chain alkoxy group having 1-7 carbon atoms, and L... 1 and L 2 Each can be represented independently as F or Cl.

[0041] In compounds of formulas I-1 to I-10, L 1 and L 2 It is preferable that F or Cl be represented independently of each other, especially L. 1 =L 2 =F. Compounds of formula I-2 and I-6 are particularly preferred. Among compounds of formula I-2 and I-6, L is preferred. 1 =L 2 =F.

[0042] The mixtures according to the invention particularly preferably comprise at least one compound of formula I-1A, I-2A, I-4A, and I-6A.

[0043]

[0044] A very particularly preferred mixture comprises at least one compound of formulas I-2.1 to I-2.49 and I-6.1 to I-6.28.

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] In compounds I-2.1 to I-2.49 and I-6.1 to I-6.28, L 1 and L 2 Preferably, all components are fluorine. More preferably, liquid crystal mixtures comprising at least one compound of formula I-1.1 to I-1.28 are used.

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] Where L 1 and L 2 Each has independently the meaning given in claim 1. Among the compounds of formulas I-1.1 to I-1.28, L is preferred. 1 =L 2=F.

[0064] Compounds of Formula I can be prepared, for example, as described in WO 02 / 055463 A1. Compounds of Formula I are preferably prepared as follows:

[0065] Option 1:

[0066] R and R′ each independently represent a straight-chain or branched alkyl or alkenyl group.

[0067]

[0068] Option 2:

[0069] R and R′ each independently represent a straight-chain or branched alkyl or alkenyl group.

[0070]

[0071] The medium according to the invention preferably comprises one, two, three, four or more compounds, preferably one, two or three of Formula I compounds.

[0072] The compound of Formula I is preferably used in the liquid crystal medium in an amount of ≥1 wt%, preferably ≥3 wt%, based on the entire mixture. Particularly preferred are liquid crystal media containing 1-40 wt%, very particularly preferred are 2-30 wt%, of one or more compounds of Formula I.

[0073] A preferred embodiment of the liquid crystal medium according to the present invention is described below:

[0074] a) A liquid crystal medium that additionally contains one or more compounds selected from compounds of formulas IIA, IIB, and IIC.

[0075]

[0076]

[0077] in

[0078] R 2A R 2B and R 2C Each of these groups independently represents H, an alkyl or alkenyl group having up to 15 carbon atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more CH2 groups in these groups may be -O-, -S-, -C≡C-, -CF₂O-, -OCF₂-, -OC-O-, or -O-CO- are replaced by O atoms that are not directly connected to each other.

[0079] L 1-4Each can be independently represented as F, Cl, CF3, or CHF2.

[0080] Z 2 and Z 2’ Each of these independently represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-.

[0081] p represents 0, 1, or 2.

[0082] q represents 0 or 1, and

[0083] v represents 1-6.

[0084] In compounds of formulas IIA and IIB, Z 2 They can have the same or different meanings. In compounds of formula IIB, Z 2 and Z 2 'They can have the same or different meanings.'

[0085] In compounds of formulas IIA, IIB, and IIC, R 2A R 2B and R 2C Each preferably represents an alkyl group having 1-6 carbon atoms, particularly CH3, C2H5, n-C3H7, n-C4H9, n-C5H 11 .

[0086] In compounds of formulas IIA and IIB, L 1 L 2 L 3 and L 4 Preferred representation L 1 =L 2 =F and L 3 =L 4 =F, and L 1 =F and L 2 =Cl,L 1 =Cl and L 2 =F,L 3 =F and L 4 =Cl,L 3 =Cl and L 4 =F. In equations IIA and IIB, Z 2 and Z 2 'Preferredly, each represents a single bond and a -C2H4- bridge independently.'

[0087] If in equation IIB, Z 2 =-C2H4- or -CH2O-, then Z 2'Preferably a single bond, or if Z 2 If '=-C2H4- or -CH2O-, then Z 2 Preferably, it is a single bond. In compounds of formulas IIA and IIB, (O)C v H 2v+1 Preferred representation of OC v H 2v+1 and C v H 2v+1 In compounds of formula IIC, (O)C v H 2v+1 Preferred representation C v H 2v+1 In compounds of formula IIC, L 3 and L 4 Each is preferably represented by F.

[0088] Preferred compounds of formulas IIA, IIB and IIC are described below:

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] Among them alkyl and alkyl * Each of these terms independently represents a straight-chain alkyl group having 1-6 carbon atoms.

[0099] The particularly preferred mixtures according to the invention comprise one or more compounds of formula IIA-2, IIA-8, IIA-14, IIA-26, II-28, IIA-33, IIA-39, IIA-45, IIA-46, IIA-47, IIA-50, IIB-2, IIB-11, IIB-16 and IIC-1.

[0100] The proportion of compounds of formula IIA and / or IIB in the entire mixture is preferably at least 20 wt%.

[0101] A particularly preferred medium according to the invention comprises at least one compound of formula IIC-1.

[0102]

[0103] Among them alkyl and alkyl * With the above meaning, the preferred amount is >3 wt%, particularly >5 wt%, and especially preferably 5-25 wt%.

[0104] b) A liquid crystal medium that additionally contains one or more compounds of formula III,

[0105]

[0106] in

[0107] R 31 and R 32 Each of these independently represents a straight-chain alkyl, alkoxy, alkenyl, alkoxyalkyl, or alkoxy group having a maximum of 12 carbon atoms.

[0108] express

[0109] Z 3 The following are represented as single bonds: -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, and -CF=CF-.

[0110] Preferred compounds of formula III are described below:

[0111]

[0112] in

[0113] alkyl and alkyl * Each of these terms independently represents a straight-chain alkyl group having 1-6 carbon atoms.

[0114] The medium according to the invention preferably comprises at least one compound of formula IIIa and / or formula IIIb.

[0115] The proportion of compound III in the entire mixture is preferably at least 5 wt%.

[0116] c) Liquid crystal media additionally containing compounds of the following formula

[0117]

[0118] The preferred total amount is ≥5 wt%, especially ≥10 wt%.

[0119] A further preferred embodiment of the mixture according to the invention comprises the following compound (abbreviation: CC-3-V1).

[0120]

[0121] The preferred amount is 2-15 wt%.

[0122] The preferred mixture contains 5-60 wt%, preferably 10-55 wt%, and particularly 20-50 wt% of the following compound (abbreviation: CC-3-V).

[0123]

[0124] Further preferred are compounds containing the following formula (abbreviation: CC-3-V).

[0125]

[0126] A mixture of the following compound (abbreviation: CC-3-V1)

[0127]

[0128] The preferred amount is 10-60 wt%.

[0129] d) Liquid crystal media additionally comprising one or more tetracyclic compounds of the following formula

[0130]

[0131]

[0132] in

[0133] R 7-10 Each has independently possessing the capability to address R in claim 3. 2A One of the meanings is that w and x each represent 1-6 independently of each other.

[0134] A mixture comprising at least one compound of formula V-9 is particularly preferred.

[0135] e) A liquid crystal medium additionally comprising one or more compounds of formula Y-1 to Y-6,

[0136]

[0137]

[0138] Where R 14 -R 19 Each of the two groups independently represents an alkyl or alkoxy group having 1-6 carbon atoms; z and m each independently represent 1-6; x represents 0, 1, 2 or 3.

[0139] The medium according to the invention particularly preferably comprises one or more compounds of formula Y-1 to Y-6, preferably in an amount of ≥5 wt%.

[0140] f) A liquid crystal medium additionally containing one or more fluoroterphenyl compounds of formulas T-1 to T-21.

[0141]

[0142]

[0143]

[0144] in

[0145] R represents a straight-chain alkyl or alkoxy group having 1-7 carbon atoms, and m = 0, 1, 2, 3, 4, 5 or 6 and n represents 0, 1, 2, 3 or 4.

[0146] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0147] The medium according to the invention preferably contains terphenyl of formulas T-1 to T-21 in an amount of 2-30 wt%, particularly 5-20 wt%.

[0148] Particularly preferred are compounds of formulas T-1, T-2, T-4, T-20, and T-21. In these compounds, R preferably represents an alkyl group and an alkoxy group, each having 1-5 carbon atoms. In compound T-20, R preferably represents an alkyl or alkenyl group, particularly an alkyl group. In compound T-21, R preferably represents an alkyl group.

[0149] If the Δn value of the mixture is ≥0.1, then terphenyl is preferably used in the mixture according to the invention. The preferred mixture contains 2-20 wt% of one or more terphenyl compounds selected from compounds T-1 to T-21.

[0150] g) A liquid crystal medium additionally comprising one or more biphenyl compounds of formulas B-1 to B-3.

[0151]

[0152] in

[0153] alkyl and alkyl * Each independently represents a straight-chain alkyl group having 1-6 carbon atoms, and

[0154] alkenyl and alkenyl * Each of them independently represents a straight-chain alkenyl group having 2-6 C atoms.

[0155] The proportion of biphenyls of formula B-1 to B-3 in the entire mixture is preferably at least 3 wt%, and particularly ≥5 wt%.

[0156] Of the compounds of formulas B-1 to B-3, compound B-2 is particularly preferred.

[0157] The preferred diphenyl is

[0158]

[0159] alkyl * This indicates an alkyl group having 1-6 carbon atoms. The medium according to the invention particularly preferably comprises one or more compounds of formula B-1a and / or B-2c.

[0160] h) A liquid crystal medium comprising at least one compound of formula Z-1 to Z-7,

[0161]

[0162]

[0163] R and alkyl have the meanings described above.

[0164] i) A liquid crystal medium that additionally contains at least one compound of formula O-1 to O-18,

[0165]

[0166]

[0167]

[0168] Where R 1 and R 2 Having for R 2A The meaning of R. 1 and R 2 Preferably, each represents a straight-chain alkyl or alkenyl group independently of the other.

[0169] The preferred medium comprises one or more compounds of formula O-1, O-3, O-4, O-6, O-7, O-10, O-11, O-12, O-14, O-15, O-16 and / or O-17.

[0170] The mixtures according to the invention particularly preferably contain compounds of formula O-10, O-12, O-16 and / or O-17, particularly in amounts of 5-30%.

[0171] Preferred compounds of formulas O-10 and O-17 are described below:

[0172]

[0173] The medium according to the invention particularly preferably comprises a tricyclic compound of formula O-10a and / or formula O-10b, and one or more bicyclic compounds of formula O-17a to O-17d. The total proportion of the compounds of formula O-10a and / or O-10b and one or more compounds selected from the bicyclic compounds of formula O-17a to O-17d is 5-40%, very particularly preferably 15-35%.

[0174] The very particularly preferred mixture contains compounds O-10a and O-17a:

[0175]

[0176] Compounds O-10a and O-17a are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22% based on the whole mixture.

[0177] The very particularly preferred mixture contains compounds O-10b and O-17a:

[0178]

[0179] Compounds O-10b and O-17a are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25%, and especially preferably 18-22% based on the whole mixture.

[0180] The highly preferred mixture contains the following three compounds:

[0181]

[0182]

[0183] Compounds O-10a, O-10b and O-17a are preferably present in the mixture at a concentration of 15-35%, particularly preferably 15-25% and especially preferably 18-22% based on the whole mixture.

[0184] The preferred mixture contains at least one compound selected from the following compounds

[0185]

[0186] Where R 1 and R 2 It has the meaning described above. Preferably, in compounds O-6, O-7, and O-17, R 1 Indicates alkyl or alkenyl groups having 1-6 or 2-6 carbon atoms respectively, and R 2This indicates an alkenyl group having 2-6 carbon atoms.

[0187] Preferred mixtures comprise at least one compound of formula O-6a, O-6b, O-7a, O-7b, O-17e, O-17f, O-17g, and O-17h:

[0188]

[0189]

[0190] Where alkyl refers to an alkyl group having 1-6 carbon atoms.

[0191] The compounds of formulas O-6, O-7 and O-17e-h are preferably present in the mixtures according to the invention in an amount of 1-40 wt%, preferably 2-35 wt%, and very particularly preferably 2-30 wt%.

[0192] j) Preferably, the liquid crystal medium according to the invention comprises one or more substances containing tetrahydronaphthyl or naphthyl units, such as compounds of formula N-1 to N-5.

[0193]

[0194]

[0195] Where R 1N and R 2N Each has its own independent relation to R 2A The meaning shown preferably represents a straight-chain alkyl, a straight-chain alkoxy, or a straight-chain alkenyl group, and

[0196] Z 1 and Z 2 Each of these can be represented independently as -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CH2-, or a single bond.

[0197] k) Preferred mixtures comprise one or more compounds selected from formula BC difluorodibenzo-p-chromium, formula CR chromium, formula PH-1 and PH-2 fluorophenanthrene, and formula BF-1 and BF-2 fluorodibenzofurans.

[0198]

[0199]

[0200] in

[0201] R B1 R B2 R CR1 R CR2 R 1 R 2 Each has its own R independently 2A The meaning of . c is 0, 1, or 2. R 1 and R 2 Preferably, alkyl or alkoxy groups having 1-6 carbon atoms are represented independently of each other.

[0202] The mixture according to the invention preferably contains compounds of formula BC, CR, PH-1, PH-2 and / or BF in an amount of 3-20 wt%, particularly in an amount of 3-15 wt%.

[0203] Particularly preferred compounds of formulas BC and CR are compounds BC-1 to BC-7 and CR-1 to CR-5.

[0204]

[0205]

[0206] in

[0207] alkyl and alkyl * Each independently represents a straight-chain alkyl group having 1-6 carbon atoms, and

[0208] alkenyl and alkenyl * Each of them independently represents a straight-chain alkenyl group having 2-6 C atoms.

[0209] Very particularly preferred are mixtures comprising one, two or three compounds of the formula BC-2, BF-1 and / or BF-2.

[0210] l) Preferred mixtures contain one or more Ininium compounds.

[0211]

[0212] in

[0213] R 11 R 12 R 13 Each of these groups independently represents a straight-chain alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1-6 carbon atoms.

[0214] R 12 and R 13 Additional indication: halogen, preferably F.

[0215] express

[0216]

[0217] i represents 0, 1, or 2.

[0218] Preferred In compounds are those shown as In-1 to In-16:

[0219]

[0220]

[0221]

[0222] Compounds of formulas In-1, In-2, In-3 and In-4 are particularly preferred.

[0223] Compounds of formula In and sub-formulas In-1 to In-16 are preferably used in mixtures according to the invention at concentrations of ≥5 wt%, particularly 5-30 wt%, and very particularly preferably 5-25 wt%.

[0224] m) Preferred mixtures additionally contain one or more compounds of formula L-1 to L-11.

[0225]

[0226]

[0227] in

[0228] R, R 1 and R 2 Each has independently possessing the capability to address R in claim 5. 2A The symbols indicate the meanings: alkyl represents an alkyl group having 1-6 carbon atoms. s indicates 1 or 2.

[0229] Especially preferred are compounds of formulas L-1 and L-4, particularly L-4 compounds.

[0230] Compounds of formula L-1 to L-11 are preferably used at a concentration of 5-50 wt%, particularly 5-40 wt%, and very particularly preferably 10-40 wt%.

[0231] The concept of particularly preferred mixtures is described below: (The abbreviations used are explained in Table A. Here, n and m each represent 1-15 independently, preferably 1-6).

[0232] The mixture according to the invention preferably contains

[0233] - One or more compounds of formula I, wherein L1 =L 2 =F and R 1 =R 1* =alkoxy group;

[0234] -CPY-n-Om, particularly CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably based on a concentration of >5%, particularly 10-30%, throughout the mixture.

[0235] and / or

[0236] -CY-n-Om, preferably CY-3-O2, CY-3-O4, CY-5-O2 and / or CY-5-O4, preferably based on a concentration of >5%, particularly 15-50%, throughout the mixture.

[0237] and / or

[0238] -CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, preferably with a concentration of >5%, particularly 10-30%, based on the entire mixture.

[0239] and / or

[0240] -CLY-n-Om, preferably CLY-2-O4, CLY-3-O2 and / or CLY-3-O3, preferably based on a concentration of >5%, particularly 10-30%, throughout the mixture.

[0241] and / or

[0242] -CK-nF, preferably CK-3-F, CK-4-F and / or CK-5-F, preferably based on a concentration of >5%, particularly 5-25%, throughout the mixture.

[0243] A further preferred embodiment of the present invention is a mixture comprising the following mixture concept:

[0244] (n and m each represent 1-6 independently.)

[0245] -CPY-n-Om and CY-n-Om, preferably based on a concentration of 10-80% throughout the mixture,

[0246] and / or

[0247] -CPY-n-Om and CK-nF, preferably based on a concentration of 10-70% throughout the mixture,

[0248] and / or

[0249] -CPY-n-Om and PY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2 and PY-3-O2, preferably based on a concentration of 10-45% throughout the mixture,

[0250] and / or

[0251] -CPY-n-Om and CLY-n-Om, preferably based on a concentration of 10-80% throughout the mixture,

[0252] and / or

[0253] -CCVC-nV, preferably CCVC-3-V, preferably based on a concentration of 2-10% throughout the mixture.

[0254] and / or

[0255] -CCC-nV, preferably CCC-2-V and / or CCC-3-V, preferably based on a concentration of 2-10% throughout the mixture,

[0256] and / or

[0257] -CC-VV, preferably based on a concentration of 5-50% throughout the mixture.

[0258] The present invention further relates to an electro-optic display with active matrix addressing based on ECB, VA, PS-VA, PA-VA, IPS, PS-IPS, FFS or PS-FFS effect, characterized in that it contains a liquid crystal medium as a dielectric according to one or more of claims 1-15.

[0259] The liquid crystal medium according to the present invention preferably has a nematic phase with a temperature of ≤-20°C to ≥70°C, particularly preferably ≤-30°C to ≥80°C, and very particularly preferably ≤-40°C to ≥90°C.

[0260] The phrase "possessing a nematic phase" here means, on the one hand, that no smectic phase or crystallization was observed at the corresponding temperature at low temperatures, and on the other hand, that the nematic phase did not become clear upon heating. Low-temperature studies were conducted in a flow viscometer at the corresponding temperature and verified by storage in a test chamber having a layer thickness corresponding to at least 100 hours of electro-optical application. If the storage stability in the corresponding test chamber at -20°C is 1000 hours or more, the medium is said to be stable at that temperature. At -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the clearing point was measured in a capillary using conventional methods.

[0261] The liquid crystal mixture preferably has a nematic phase range of at least 60K and a maximum thickness of 30mm at 20°C. 2 ·s -1 Flow viscosity ν20 .

[0262] The birefringence value Δn in the liquid crystal mixture is typically 0.07-0.16, preferably 0.08-0.13.

[0263] The liquid crystal mixture according to the invention has a Δε of -0.5 to -8.0, particularly -2.5 to -6.0, where Δε represents dielectric anisotropy. The rotational viscosity γ1 at 20°C is preferably ≤150 mPa·s, particularly ≤120 mPa·s.

[0264] The liquid crystal medium according to the invention has a relatively low threshold voltage value (V0). Its preferred range is 1.7V-3.0V, particularly preferred is ≤2.5V and very particularly preferred is ≤2.3V.

[0265] For the purposes of this invention, the term “threshold voltage” refers to the capacitance threshold (V0), also known as the Freedericks threshold, unless otherwise explicitly stated.

[0266] Furthermore, the liquid crystal medium according to the present invention has a high voltage retention rate value in the liquid crystal cell.

[0267] Typically, liquid crystal media with low addressing voltages or threshold voltages exhibit lower voltage retention rates than those with higher addressing voltages or threshold voltages, and vice versa.

[0268] For the purposes of this invention, the term "positive dielectric compound" refers to a compound having Δε > 1.5, the term "neutral dielectric compound" refers to those having -1.5 ≤ Δε ≤ 1.5, and the term "negative dielectric compound" refers to those having Δε < -1.5. Here, the dielectric anisotropy of the compound is determined by dissolving 10% of the compound in a liquid crystal matrix in at least one test cell and measuring the capacitance of the resulting mixture. In each case, the test cell has a layer thickness of 20 μm and has vertical and uniform surface alignment at 1 kHz. The measurement voltage is typically 0.5 V–1.0 V, but is always below the capacitance threshold of each liquid crystal mixture studied.

[0269] All temperature values ​​described in this invention are expressed in °C.

[0270] The mixtures according to the invention are suitable for all VA-TFT applications, such as VAN, MVA, (S)-PVA, ASV, PSA (polymer-stabilized VA), and PS-VA (polymer-stabilized VA). They are also suitable for IPS with negative Δε. In-plane Change ) and FFS ( Edge field switching )application.

[0271] The nematic liquid crystal mixture in the display according to the invention typically contains two components A and B, which are composed of one or more of their respective compounds.

[0272] Component A has significant negative dielectric anisotropy and imparts dielectric anisotropy of ≤-0.5 to the nematic phase. In addition to one or more compounds of formula I, it preferably includes compounds of formula IIA, IIB and / or IIC, and one or more compounds of formula O-17.

[0273] The proportion of component A is preferably 45-100%, especially 60-100%.

[0274] For component A, it is preferable to select one (or more) compounds each having a value of Δε ≤ -0.8. The smaller the proportion of A in the entire mixture, the more negative this value must be.

[0275] Component B exhibits significant nematogeneity and a diameter not exceeding 30 mm at 20°C. 2 ·s -1 Preferably no larger than 25mm 2 ·s -1 The flow viscosity.

[0276] Those skilled in the art will recognize from the literature a variety of suitable substances. Compounds of formula O-17 are particularly preferred.

[0277] The compounds particularly preferred in component B are nematic liquid crystals with very low viscosity, exhibiting a viscosity of no more than 18 mm at 20°C. 2 ·s -1 The flow viscosity is preferably not greater than 12 mm. 2 ·s -1 .

[0278] Component B is a unidirectional or tautomerized nematic phase, lacking a smectic phase, and is able to prevent the formation of a smectic phase when cooled to very low temperatures in the liquid crystal mixture. For example, if multiple highly nematic materials are added to a smectic liquid crystal mixture, the nematicity of these materials can be compared by the degree of suppression of the smectic phase achieved.

[0279] The mixture may also optionally contain component C, which comprises a compound having a dielectric anisotropy of Δε ≥ 1.5. These so-called positive compounds are typically present in the negatively dielectric anisotropic mixture in an amount of ≤ 20 wt% based on the total mixture.

[0280] If the mixture according to the invention comprises one or more compounds having a dielectric anisotropy of Δε ≥ 1.5, it is preferably one or more compounds selected from formulas P-1 to P-4.

[0281]

[0282] in

[0283] R represents a straight-chain alkyl, alkoxy, or alkenyl group, each having 1 or 2 to 6 carbon atoms.

[0284] X represents F, Cl, CF3, OCF3, OCHFCF3 or CCF2CHFCF3, with F or OCF3 being preferred.

[0285] Compounds of formulas P-1 to P-4 are preferably used in mixtures according to the invention at a concentration of 2-15%, particularly 2-10%.

[0286] The following compounds are particularly preferred.

[0287]

[0288] It is preferably used in the mixture according to the invention at an amount of 2-15%.

[0289] In addition, these liquid crystal phases may contain more than 18 components, preferably 18-25 components.

[0290] In addition to one or more compounds of formula I, the phase preferably contains 4-15, particularly 5-12, and especially preferably <10 compounds of formula IIA, IIB and / or IIC, and optionally one or more compounds of formula O-17.

[0291] Other components may be present, in addition to compounds of formula I and formulas IIA, IIB and / or IIC and optional O-17 compounds, for example, in an amount of up to 45% of the whole mixture, but preferably up to 35%, and especially up to 10%.

[0292] Other components are preferably selected from nematic or nematic substances, especially known substances, derived from azobenzene, benzyl aniline, biphenyl, terphenyl, phenylbenzoate or cyclohexylbenzoate, phenylcyclohexane carboxylate or cyclohexylcyclohexane carboxylate, phenylcyclohexane, cyclohexylbiphenyl, cyclohexylcyclohexane, cyclohexylnaphthalene, 1,4-bicyclohexylbiphenyl or cyclohexylpyrimidine, phenyl diphenyl Alkane or cyclohexyl di Alkane, optionally halogenated stilbene, benzyl phenyl ether, diphenylacetylene, and substituted cinnamic esters.

[0293] The most important compounds suitable as components of this type of liquid crystal phase can be characterized by Formula IV.

[0294] R 20 -LGER 21 IV

[0295] Where L and E respectively represent those selected from 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyls, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidines and 1,3-diphenylcyclohexane rings. Carbocyclic or heterocyclic systems of alkyl rings, 2,6-disubstituted naphthalenes, di- and tetrahydronaphthalenes, quinazolines, and tetrahydroquinazolines.

[0296] G represents -CH=CH-, -N(O)=N-, -CH=CQ-, -CH=N(O)-, -C≡C-, -CH2-CH2-, -CO-O-, -CH2-O-, -CO-S-, -CH2-S-, -CH=N-, -COO-Phe-COO-, -CF2O-, -CF=CF-, -OCF2-, -OCH2-, -(CH2)4-, -(CH2)3O-, or a CC single bond; Q represents a halogen, preferably chlorine, or -CN, and R 20 and R 21 Each group represents an alkyl, alkenyl, alkoxy, alkoxyalkyl or alkoxycarbonyl group having a maximum of 18, preferably a maximum of 8, carbon atoms, or one of these groups alternatively representing CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl or Br.

[0297] In the vast majority of these compounds, R 20 and R 21 These substances differ from one another; one of these groups is typically alkyl or alkoxy. Other variations of the proposed substituents are also common. Many of these substances, or mixtures thereof, are commercially available. All of these substances can be prepared using methods known in the literature.

[0298] It will be self-evident to those skilled in the art that the mixtures according to the invention are preferably used for VA, PS-VA, SS-VA (surface-stabilized VA), SA-VA (self-aligned VA), PA-VA (photo-aligned VA), IPS, FFS, UB-FFS (ultra-high brightness FFS) and PALC applications, and may also contain compounds in which, for example, H, N, O, Cl and F have been replaced by their respective isotopes.

[0299] Polymerizable compounds, so-called reactive mesomorphs (RMs), such as those disclosed in US 6,861,107, may be further added to the mixture according to the invention at a concentration preferably 0.01-5 wt%, particularly preferably 0.2-2 wt%, based on the mixture. These mixtures may also optionally contain an initiator, such as that described in US 6,781,665. An initiator, such as Irganox-1076 from BASF, is preferably added to the mixture containing the polymerizable compound at an amount of 0-1%. This type of mixture can be used in so-called polymer-stabilized VA mode (PS-VA) or PSA (polymer-stabilized VA), where polymerization of the reactive mesomorphs is intended to occur in the liquid crystal mixture. The prerequisite is that the liquid crystal mixture itself does not contain any polymerizable components.

[0300] In a preferred embodiment of the present invention, the polymerizable compound is selected from compounds of formula M.

[0301] R Ma -A M1 -(Z M1 -A M2 ) m1 -R Mb M

[0302] Each group has the following meaning:

[0303] R Ma and R Mb Each of these groups independently represents P, P-Sp-, H, halogen, SF5, NO2, alkyl, alkenyl, or alkynyl, wherein the group R Ma and R Mb At least one of them preferably represents or contains the group P or P-Sp-,

[0304] P represents a polymerizable group.

[0305] Sp represents a spacer group or a single bond.

[0306] A M1 and A M2 Each group independently represents an aryl, heteroaryl, alicyclic, or heterocyclic group, preferably having 4-25 ring atoms, preferably C atoms, and may also include or contain fused rings and may optionally be mono- or poly-substituted with L atoms.

[0307] L represents P, P-Sp-, OH, CH2OH, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x )2、-C(=O)Y 1 -C(=O)R x -N(R) x2. Optionally substituted silyl groups, optionally substituted aryl groups having 6-20 carbon atoms, or straight-chain or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy, or alkoxy carbonyloxy groups having 1-25 carbon atoms, wherein one or more H atoms may be substituted with F, Cl, P, or P-Sp-, preferably P, P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, alkyl, alkenyl, or alkynyl groups.

[0308] Y 1 Indicates halogen,

[0309] Z M1 Represents -O-, -S-, -CO-, -CO-O-, -OCO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -C≡C-, -CH=CH-, -COO-, -OCO-CH=CH-, CR 0 R 00 Or a single key,

[0310] R 0 and R 00 Each can independently represent H or an alkyl group having 1-12 carbon atoms.

[0311] R x The designation represents P, P-Sp-, H, halogen, a straight-chain, branched, or cyclic alkyl group having 1-25 carbon atoms, wherein one or more non-adjacent CH2 groups may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that the O and / or S atoms are not directly connected to each other, and wherein one or more H atoms may be replaced by F, Cl, P, or P-Sp-, an optionally substituted aryl or aryloxy group having 6-40 carbon atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2-40 carbon atoms.

[0312] m1 represents 0, 1, 2, 3 or 4 and

[0313] n1 represents 1, 2, 3, or 4.

[0314] The group R present therein Ma ,R Mb It contains at least one, two, or three substituents L, preferably one or two representing groups P or P-Sp- or containing at least one group P or P-Sp-.

[0315] Particularly preferred compounds of formula M are those of the following.

[0316] R Ma and R Mb Each of these groups independently represents P, P-Sp-, H, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, SF5, or a straight-chain or branched alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups may be independently represented by -C(R) 0 )=C(R 00 )-、-C≡C-、-N(R 00 -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O- are substituted in such a way that the O and / or S atoms are not directly connected to each other, and in addition, one or more H atoms may be substituted by F, Cl, Br, I, CN, P or P-Sp-, wherein the group R Ma and R Mb At least one of them preferably represents or contains the group P or P-Sp-,

[0317] A M1 and A M2 Each of these groups independently represents 1,4-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarin, flavonoid, wherein one or more CH groups in these groups may be replaced by N, cyclohexane-1,4-diyl, wherein one or more non-adjacent CH2 groups may be replaced by O and / or S, 1,4-cyclohexenyl, bis(2,4-diyl) Cyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, piperidine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indane-2,5-diyl, or octahydro-4,7-bridged methylene indane-2,5-diyl, wherein all of these groups may be unsubstituted or mono- or polysubstituted with L.

[0318] L represents P, P-Sp-, OH, CH2OH, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x )2、-C(=O)Y 1 -C(=O)R x -N(R) x2. Optionally substituted silyl groups, optionally substituted aryl groups having 6-20 carbon atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy groups having 1-25 carbon atoms, wherein, in addition, one or more H atoms may be substituted by F, Cl, P, or P-Sp-.

[0319] P represents a polymerizable group.

[0320] Y 1 Indicates halogen,

[0321] R x The symbol represents P, P-Sp-, H, halogen, a straight-chain, branched, or cyclic alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a way that the O and / or S atoms are not directly connected to each other, and wherein one or more H atoms may be replaced by F, Cl, P, or P-Sp-, an optionally substituted aryl or aryloxy group having 6-40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2-40 C atoms.

[0322] R is a particularly preferred option. Ma and R Mb One or both of them represent compounds of formula M, which are P or P-Sp-.

[0323] Suitable and preferred RM or monomers or comonomers for use in the liquid crystal medium and PS-VA or PSA display according to the present invention are selected from, for example, the following formulas:

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330] Each group has the following meaning:

[0331] P 1 P 2 and P 3Each may represent a polymerizable group, either identically or differently, preferably having one of the meanings described in the context of P, particularly preferably acrylate, methacrylate, fluoroacrylate, oxetyl, ethyleneoxy, or epoxy groups.

[0332] Sp 1 Sp 2 and Sp 3 Each represents a single bond or spacer group independently of the others, preferably having context for Sp a One of the meanings shown is, and a particularly preferred one is (CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -CO-O- or -(CH2) p1 -O-CO-O-, where p1 is an integer from 1 to 12, and the connection between the group mentioned later and the adjacent ring occurs via the O atom.

[0333] Wherein group P 1 -Sp 1 -、P 2 -Sp 2 -and P 3 -Sp 3 One or more of - can also represent R aa The condition is that the group P exists. 1 -Sp 1 -、P 2 -Sp 2 -and P 3 -Sp 3 - at least one does not represent R aa ,

[0334] R aa Represents H, F, Cl, CN, or a straight-chain or branched alkyl group having 1-25 C atoms, wherein one or more non-adjacent CH2 groups may be independently bounded by C(R) 0 )=C(R 00 )-、-C≡C-、-N(R 0 -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O- are replaced by O and / or S atoms that are not directly connected to each other, and in addition, one or more H atoms may be replaced by F, Cl, CN or P. 1 -Sp 1 - Alternatively preferred are straight-chain or branched groups having 1-12 carbon atoms, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy groups (wherein the alkenyl and alkynyl groups have at least two carbon atoms and the branched groups have at least three carbon atoms).

[0335] R 0 R 00 Each of these terms is independent of the others and, each time it appears, may represent H or an alkyl group having 1-12 carbon atoms, either identically or differently.

[0336] R y and R z Each can independently represent H, F, CH3, or CF3.

[0337] X 1 X 2 and X 3 Each can be independently represented as -CO-O-, O-CO-, or a single bond.

[0338] Z 1 Represents -O-, -CO-, -C(R) y R z - or -CF2CF2-,

[0339] Z 2 and Z 3 Each can be independently represented as -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2). n - where n is 2, 3, or 4.

[0340] Each occurrence of L may represent F, Cl, CN, SCN, SF5, or a straight or branched alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyl, or alkoxycarbonyl group having 1-12 C atoms, preferably F.

[0341] L' and L″ each independently represent H, F, or Cl.

[0342] r represents 0, 1, 2, 3, or 4.

[0343] s represents 0, 1, 2, or 3.

[0344] t represents 0, 1, or 2.

[0345] x represents 0 or 1.

[0346] In compounds of formulas M1-M36,

[0347] Preferred representation

[0348]

[0349] Each time L appears, it has one of the above meanings, either the same or different, and preferably represents F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, particularly preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, very particularly preferably F, Cl, CH3, OCH3, COCH3 or OCF3, especially F or CH3.

[0350] Suitable polymerizable compounds are listed, for example, in Table D.

[0351] The liquid crystal medium according to this application preferably contains a total of 0.1-10%, more preferably 0.2-4.0%, and particularly preferably 0.2-2.0% of a polymerizable compound.

[0352] Particularly preferred are polymerizable compounds of formula M and formulas RM-1 to RM-94.

[0353] The mixtures according to the invention may further contain conventional additives, such as stabilizers, antioxidants, UV absorbers, nanoparticles, microparticles, etc.

[0354] The structure of the liquid crystal display according to the present invention conforms to general geometry as described, for example, in EP-A 0 240379.

[0355] The following examples are intended to explain the invention and not to limit it. In this context, percentage data represent weight percentages; all temperatures are expressed in degrees Celsius.

[0356] Throughout this application, the 1,4-cyclohexylene ring and the 1,4-phenylene ring are depicted as follows:

[0357]

[0358] The cyclohexyl ring is trans-1,4-cyclohexyl ring.

[0359] Throughout this application and the working embodiments, the structures of the liquid crystal compounds are expressed using abbreviations. Unless otherwise stated, they are converted to chemical formulas according to Tables 1-3. All functional groups C n H 2n+1 C m H 2m+1 and C m 'H 2m′+1 Or C n H 2n and C m H 2mThe alkyl or alkylene groups are straight-chain alkyl groups, each containing n, m, m', or z C atoms. n, m, m', and z each independently represent 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, preferably 1, 2, 3, 4, 5, or 6. Table 1 encodes the ring units of each compound, Table 2 lists the bridging elements, and Table 3 explains the meaning of the symbols for the left-hand or right-hand side chains of the compounds.

[0360] Table 1: Ring Units

[0361]

[0362]

[0363]

[0364] Table 2: Bridge Elements

[0365]

[0366] Table 3: Sidechains

[0367]

[0368] In addition to the compounds of Formula I, the mixtures according to the invention preferably contain one or more of the compounds mentioned in Table A below.

[0369] Table A

[0370] Use the following abbreviations:

[0371] (n, m, m', z: each is independently 1, 2, 3, 4, 5 or 6;

[0372] (O)C m H 2m+1 Meaning OC m H 2m+1 Or C m H 2m+1 )

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394] The liquid crystal mixtures that can be used according to the invention are prepared in their conventional manner. Typically, the required amount of the component is dissolved in a smaller amount in the component constituting the main component, advantageously at elevated temperatures. Alternatively, the component can be mixed in an organic solvent such as acetone, chloroform, or methanol, and the solvent can be removed again after thorough mixing, for example by distillation.

[0395] By using suitable additives, the liquid crystal phases according to the invention can be improved in any way that allows them to be used in, for example, ECB, VAN, IPS, GH, or ASM-VA LCD displays that have been disclosed to date.

[0396] The dielectric may further contain additives known to those skilled in the art and described in the literature, such as UV absorbers, antioxidants, nanoparticles, and free radical scavengers. For example, 0-15% of pleochroic dyes, stabilizers, or chiral dopants may be added. Suitable stabilizers for mixtures according to the invention are particularly those listed in Table B.

[0397] For example, 0-15% of pleochroic dyes may be added, as well as conductive salts, preferably complex salts of ethyl dimethyl dodecyl 4-hexyloxybenzoate, tetrabutyltetraphenylborate, or crown ethers (see, for example, Haller et al., Mol. Cryst. Liq. Cryst., Vol. 10). 24 Volume, pp. 249-258 (1973)), to improve conductivity or to add substances to improve the dielectric anisotropy, viscosity and / or orientation of the nematic phase. Such substances are described, for example, in DE-A 22 09 127, 22 40864, ​​23 21 632, 23 38 281, 24 50 088, 26 37 430 and 28 53 728.

[0398] Table B shows the possible dopants that can be added to the mixtures according to the invention. If the mixture contains a dopant, it is used in an amount of 0.01-4 wt%, preferably 0.1-1.0 wt%.

[0399] Table B

[0400] Table B illustrates the possible dopants typically added to the mixtures according to the invention. The mixture preferably contains 0-10 wt%, particularly 0.01-5 wt%, and especially preferably 0.01-3 wt% of dopants.

[0401]

[0402]

[0403] Table C

[0404] The stabilizer of the mixture according to the invention may be added, for example, in an amount of 0-10 wt%, as shown below.

[0405]

[0406]

[0407]

[0408]

[0409]

[0410] Table D

[0411] Table D shows example compounds that can be preferably used as reactive mesocrystalline compounds in the LC medium according to the invention. If the mixture according to the invention contains one or more reactive compounds, they are preferably used in an amount of 0.01-5 wt%. It may also be necessary to add an initiator or a mixture of two or more initiators for polymerization. The initiator or initiator mixture is preferably added in an amount of 0.001-2 wt% based on the mixture. Suitable initiators are, for example, Irgacure (BASF) or Irganox (BASF).

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425] In a preferred embodiment, the mixture according to the invention comprises one or more polymerizable compounds, preferably selected from polymerizable compounds of formulas RM-1 to RM-94. This type of medium is suitable, in particular, for PS-FFS and PS-IPS applications. Among the reactive mesocrystalline compounds shown in Table D, compounds RM-1, RM-2, RM-3, RM-4, RM-5, RM-11, RM-17, RM-35, RM-41, RM-44, RM-62, and RM-81 are particularly preferred. Detailed Implementation

[0426] Working Example:

[0427] The following embodiments are intended to explain the invention and not to limit it. In the embodiments, mp represents the melting point and C represents the clearing point of the liquid crystal material in degrees Celsius; the boiling temperature is expressed as mp. Further: C represents crystalline solid state, S represents smectic phase (index indicates phase type), N represents nematic phase, Ch represents cholesterol phase, I represents isotropic phase, T represents... g The symbol indicates the glass transition temperature. The numerical value between the two symbols represents the transition temperature in degrees Celsius.

[0428] The host mixture used to determine the optical anisotropy Δn of Formula I compounds was the commercially available mixture ZLI-4792 (Merck KGaA). Dielectric anisotropy Δε was determined using the commercially available mixture ZLI-2857. Physical data for the compounds under investigation were obtained from the change in dielectric constant of the host mixture after the addition of the compound under investigation and extrapolated to 100% of the compound used. Typically, depending on solubility, 10% of the compound under investigation is soluble in the host mixture.

[0429] Unless otherwise stated, part or percentage data are expressed as part by weight or percentage by weight.

[0430] In the context:

[0431] V0 represents the threshold voltage, capacitive [V], at 20℃.

[0432] n e This indicates the unusual refractive index at 20°C and 589 nm.

[0433] n o This represents the ordinary refractive index at 20°C and 589 nm.

[0434] △n represents the optical anisotropy at 20℃ and 589nm.

[0435] ε ⊥ This represents the dielectric constant perpendicular to the director at 20℃ and 1kHz.

[0436] ε || This represents the dielectric constant parallel to the director at 20℃ and 1kHz.

[0437] Δε represents the dielectric anisotropy at 20℃ and 1kHz.

[0438] cl.p.,T(N,I) represents the clearing point [°C].

[0439] γ1 represents the rotational viscosity [mPa·s] at 20℃, determined by rotation in a magnetic field.

[0440] K1 represents the elastic constant, and the "oblique expansion" deformation [pN] at 20℃.

[0441] K2 represents the elastic constant, and the "torsional" deformation [pN] at 20℃.

[0442] K3 represents the elastic constant, and the "bending" deformation [pN] at 20°C.

[0443] LTS indicates low-temperature stability (nematic phase), measured in a test kit.

[0444] Unless otherwise expressly stated, all temperature values ​​specified in this application, such as melting point T(C,N), transformation from smectic (S) to nematic (N) phase T(S,N), and clearing point T(N,I), are expressed in Celsius (°C). Mp represents the melting point, and cl.p. = clearing point. Furthermore, Tg = glassy phase, C = crystalline state, N = nematic phase, S = smectic phase, and I = isotropic phase. The data between these symbols represent transformation temperatures.

[0445] All physical properties are based on “Merck Liquid Crystals, Physical Properties of Liquid Crystals”, Status November 1997, measured by Merck KGaA (Germany) and applicable at a temperature of 20°C, with Δn at 589 nm and Δε at 1 kHz, unless otherwise specified in each case.

[0446] For the purposes of this invention, the term "threshold voltage" refers to the capacitive threshold (V0), also known as the Freedericksz threshold, unless otherwise explicitly stated. In embodiments, as is generally the case, an optical threshold (V0) for 10% relative contrast may also be given. 10 ).

[0447] The display used to measure capacitive threshold voltage consists of two parallel glass outer plates spaced 20 μm apart. Each outer plate has an electrode layer on its inner side and an unrubbed polyimide alignment layer on top, which causes vertical edge alignment of liquid crystal molecules.

[0448] The display or test box used to measure tilt angle consists of two parallel glass outer plates spaced 4 μm apart. Each outer plate has an electrode layer on its inner side and a polyimide alignment layer on top. The two polyimide layers are rubbed against each other in opposite parallel directions, resulting in vertical edge alignment of liquid crystal molecules.

[0449] Polymerizable compounds are polymerized in a display or test chamber by irradiating the display with UVA light of a certain intensity (typically 365 nm) for a predetermined time while simultaneously applying a voltage (typically 10V–30V AC, 1 kHz) to the display. In the examples, unless otherwise specified, 50 mW / cm² is used. 2 The intensity was measured using a mercury vapor lamp and a standard UV meter (makeUshio UNI meter) equipped with a 365nm bandpass filter.

[0450] The tilt angle was determined by rotating the crystal (Autronic-Melchers TBA-105). Smaller values ​​(i.e., larger deviations relative to a 90° angle) correspond to larger tilts in this case.

[0451] VHR values ​​were measured as follows: 0.3% of the polymerizable monomer compound was added to the LC bulk mixture, and the resulting mixture was introduced into a TN-VHR test chamber (90° friction, alignment layer TN polyimide, layer thickness d≈6μm). HR values ​​were measured before and after 2 hours of UV exposure at 1V, 60Hz, 64μs pulse (sunlight test) at 100°C for 5 minutes (measuring instrument: Autronic-Melchers VHRM-105).

[0452] To study low-temperature stability, also known as "LTS," which refers to the stability of LC mixtures against the spontaneous crystallization of individual components at low temperatures, bottles containing 1g of LC / RM mixture were stored at -10°C, and the mixture was regularly checked to see if crystallization had occurred.

[0453] The term "HTP" refers to the helical torsion force (in μm) of an optically active or chiral substance in an LC medium. Unless otherwise specified, HTP is measured at 20°C in a commercially available nematic LC host mixture MLD-6260 (Merck KGaA).

[0454] Unless otherwise expressly stated, all concentrations in this application are expressed as weight percentages and relative to the whole corresponding mixture, including all solid or liquid crystal components but excluding solvents. All physical properties were determined according to "Merck LiquidCrystals, Physical Properties of Liquid Crystals", Status November 1997, Merck KGaA, Germany, and applied at a temperature of 20°C, unless otherwise expressly stated.

[0455] Mixture Examples

[0456] Example M1

[0457]

[0458] Example M2

[0459]

[0460]

[0461] Example M3

[0462]

[0463] Example M4

[0464]

[0465]

[0466] Example M5

[0467]

[0468] Example M6

[0469]

[0470]

[0471] Example M7

[0472]

[0473] Example M8

[0474]

[0475] Example M9

[0476] To prepare the PS-VA mixture, 99.7% of the mixture according to Example M1 was mixed with 0.3% of the polymerizable compound of the following formula.

[0477]

[0478] Example M10

[0479] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M1 was mixed with 0.25% of the polymerizable compound of the following formula.

[0480]

[0481] Example M11

[0482] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M2 was mixed with 0.2% of the polymerizable compound of the following formula.

[0483]

[0484] Example M12

[0485] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M4 was mixed with 0.25% of the polymerizable compound of the following formula.

[0486]

[0487] Example M13

[0488] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M4 was mixed with 0.25% of the polymerizable compound of the following formula.

[0489]

[0490] Example M14

[0491] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M1 was mixed with 0.25% of the polymerizable compound of the following formula.

[0492]

[0493] Example M15

[0494] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M1 was mixed with 0.2% of the polymerizable compound of the following formula.

[0495]

[0496] Example M16

[0497] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M5 was mixed with 0.25% of the polymerizable compound of the following formula.

[0498]

[0499] Example M17

[0500]

[0501]

[0502] Example M18

[0503]

[0504] Example M19

[0505]

[0506] Example M20

[0507]

[0508]

[0509] Example M21

[0510]

[0511] Example M22

[0512]

[0513]

[0514] Example M23

[0515]

[0516] Example M24

[0517]

[0518]

[0519] Example M25

[0520]

[0521] Example M26

[0522]

[0523]

[0524] Example M27

[0525]

[0526] Example M28

[0527]

[0528] Example M29

[0529]

[0530] Example M30

[0531]

[0532] Example M31

[0533]

[0534]

[0535] Example M32

[0536]

[0537] Example M33

[0538]

[0539]

[0540] Example M34

[0541]

[0542] Example M35

[0543]

[0544]

[0545] Example M36

[0546] To prepare the PS-VA mixture, 99.7% of the mixture according to Example M17 was mixed with 0.3% of the polymerizable compound of the following formula.

[0547]

[0548] Example M37

[0549] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M17 was mixed with 0.25% of the polymerizable compound of the following formula.

[0550]

[0551] Example M38

[0552] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M17 was mixed with 0.2% of the polymerizable compound of the following formula.

[0553]

[0554] Example M39

[0555] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M17 was mixed with 0.25% of the polymerizable compound of the following formula.

[0556]

[0557] Example M40

[0558] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M17 was mixed with 0.25% of the polymerizable compound of the following formula.

[0559]

[0560] Example M41

[0561] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M17 was mixed with 0.25% of the polymerizable compound of the following formula.

[0562]

[0563] Example M42

[0564] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M17 was mixed with 0.2% of the polymerizable compound of the following formula.

[0565]

[0566] Example M43

[0567] To prepare the PS-VA mixture, 99.7% of the mixture according to Example M19 was mixed with 0.3% of the polymerizable compound of the following formula.

[0568]

[0569] Example M44

[0570] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M19 was mixed with 0.25% of the polymerizable compound of the following formula.

[0571]

[0572] Example M45

[0573] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M19 was mixed with 0.2% of the polymerizable compound of the following formula.

[0574]

[0575] Example M46

[0576] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M19 was mixed with 0.001% Irganox 1076 and 0.25% of the polymerizable compound of the following formula.

[0577]

[0578] Example M47

[0579] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M19 was mixed with 0.25% of the polymerizable compound of the following formula.

[0580]

[0581] Example M48

[0582] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M19 was mixed with 0.25% of the polymerizable compound of the following formula.

[0583]

[0584] Example M49

[0585] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M19 was mixed with 0.2% of the polymerizable compound of the following formula.

[0586]

[0587] Example M50

[0588] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M19 was mixed with 0.25% of the polymerizable compound of the following formula.

[0589]

[0590] Example M51

[0591] To prepare the PS-VA mixture, 99.7% of the mixture according to Example M22 was mixed with 0.3% of the polymerizable compound of the following formula.

[0592]

[0593] Example M52

[0594] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M22 was mixed with 0.25% of the polymerizable compound of the following formula.

[0595]

[0596] Example M53

[0597] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M22 was mixed with 0.2% of the polymerizable compound of the following formula.

[0598]

[0599] Example 54

[0600] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M22 was mixed with 0.25% of the polymerizable compound of the following formula.

[0601]

[0602] Example M55

[0603] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M22 was mixed with 0.25% of the polymerizable compound of the following formula.

[0604]

[0605] Example M56

[0606] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M22 was mixed with 0.25% of the polymerizable compound of the following formula.

[0607]

[0608] Example M57

[0609] To prepare the PS-VA mixture, 99.8% of the mixture according to Example M22 was mixed with 0.2% of the polymerizable compound of the following formula.

[0610]

[0611] Example M58

[0612] To prepare the PS-VA mixture, 99.6% of the mixture according to Example M28 was mixed with 0.2% of the polymerizable compound of the following formula.

[0613]

[0614] Example M59

[0615] To prepare the PS-VA mixture, 99.75% of the mixture according to Example M28 was mixed with 0.25% of the polymerizable compound of the following formula.

[0616]

[0617] Example M60

[0618] To prepare the PS-VA mixture, 99.7% of the mixture according to Example M33 was mixed with 0.3% of the polymerizable compound of the following formula.

[0619]

[0620] Example M61

[0621] To prepare the PS-VA mixture, 99.7% of the mixture according to Example M33 was mixed with 0.3% of the polymerizable compound of the following formula.

[0622]

[0623] Example 62

[0624] To prepare the PS-VA mixture, 99.6% of the mixture according to Example M33 was mixed with 0.2% of the polymerizable compound of the following formula.

[0625]

[0626] Mix with 0.2% of the following polymerizable compound

[0627]

Claims

1. A liquid crystal medium based on a mixture of polar compounds, the liquid crystal medium having negative dielectric anisotropy, characterized in that it comprises at least one compound selected from formulas I-1 to I-10, the amount of said at least one compound selected from formulas I-1 to I-10 being 2-30% by weight. in alkyl and alky Each of these terms independently represents a straight-chain alkyl group having 1-6 carbon atoms. alkenyl and alkeny Each of these groups independently represents a straight-chain alkenyl group with 2-6 carbon atoms. alkoxy and alkox Each independently represents a straight-chain alkoxy group having 1-6 carbon atoms, and L 1 and L 2 Each is represented independently of the other, and It additionally contains one or more compounds selected from compounds of formulas IIA, IIB, and IIC. IIA IIB IIC in R 2A R 2B and R 2C Each of these groups independently represents H, an alkyl or alkenyl group having up to 15 carbon atoms, which is unsubstituted, monosubstituted with CN or CF3, or at least monosubstituted with a halogen, wherein one or more CH2 groups among these groups may be -O-, -S-, -C C-, -CF2O-, -OCF2-, -OC-O-, or -O-CO- are replaced by O atoms that are not directly connected to each other. L 1-4 Each can be independently represented as F, Cl, CF3, or CHF2. Z 2 and Z 2’ Each of these independently represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, and -CH=CHCH2O-. p represents 0, 1, or 2. q represents 0 or 1, and v represents 1-6, The amount of the compounds of formula IIA and / or IIB is at least 20 wt%, based on the entire mixture; The medium further comprises one or more compounds of formulas O-1 to O-18. in R 1 and R 2 Each independently possesses the above-mentioned characteristics for R. 2A The meaning shown, and Compounds of formula CC-3-V The amount is 5-60 wt%, based on the whole mixture.

2. The liquid crystal medium according to claim 1, characterized in that the medium comprises at least one compound selected from compounds of formulas I-2.1 to I-2.49 and I-6.1 to I-6.

28. Where L 1 and L 2 It has the meaning shown in claim 1.

3. The liquid crystal medium according to claim 1 or 2, characterized in that the medium additionally comprises one or more compounds of formula III. III in R 31 and R 32 Each of these independently represents a straight-chain alkyl, alkenyl, alkoxy, alkoxyalkyl, or alkoxy group having a maximum of 12 carbon atoms. Z 3 The following are represented as single bonds, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H9-, and -CF=CF-.

4. The liquid crystal medium according to claim 1 or 2, characterized in that the medium further comprises one or more compounds of formula L-1 to L-11. L-1 L-2 L-3 L-4 L-5 L-6 L-7 L-8 L-9 L-10 L-11, in R, R 1 and R 2 Each has independently possessing the same characteristics as R in claim 1. 2A The meanings shown are as follows: alkyl represents an alkyl group having 1-6 carbon atoms, and... s represents 1 or 2.

5. The liquid crystal medium according to claim 1 or 2, characterized in that the medium additionally comprises one or more terphenyl compounds of formulas T-1 to T-21. T-1 T-2 T-3 T-4 T-5 T-6 T-7 T-8 T-9 T-10 T-11 T-12 T-13 T-14 T-15 T-16 T-17 T-18 T-19 T-20 T-21 in R represents a straight-chain alkyl or alkoxy group having 1-7 carbon atoms, and m represents 1-6.

6. The liquid crystal medium according to claim 1 or 2, characterized in that the medium additionally comprises one or more compounds selected from compounds of formula O-6, O-7 and O-17. in R 1 It indicates an alkyl or alkenyl group having 1-6 or 2-6 carbon atoms, and R 2 This indicates an alkenyl group having 2-6 carbon atoms.

7. The liquid crystal medium according to claim 1 or 2, characterized in that the medium additionally comprises one or more indene compounds of the formula In. In in R 11 R 12 R 13 This refers to a straight-chain alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1-5 carbon atoms. R 12 and R 13 It also indicates halogen. express i represents 0, 1, or 2.

8. The liquid crystal medium according to claim 1 or 2, characterized in that the medium additionally comprises one or more compounds of formula BF-1 and BF-2. BF-1 BF-2 in R 1 and R 2 Each has its own R independently 2A The meaning, and c represents 0, 1, or 2.

9. The liquid crystal medium according to claim 1 or 2, characterized in that the clearing point of the liquid crystal medium is ≥75°C.

10. The liquid crystal medium according to claim 1 or 2, characterized in that the medium comprises at least one polymerizable compound.

11. The liquid crystal medium according to claim 1 or 2, characterized in that the medium comprises one or more additives.

12. The liquid crystal medium according to claim 1 or 2, characterized in that the additive is selected from free radical scavengers, antioxidants and / or UV stabilizers.

13. A method for preparing a liquid crystal medium according to any one of claims 1-12, characterized in that at least one compound selected from formulas I-1 to I-10 is mixed with one or more compounds selected from formulas IIA, IIB and IIC, one or more compounds from formulas O-1 to O-18, compounds of formula CC-3-V, and at least one other liquid crystal compound, and optionally one or more additives, and optionally at least one polymerizable compound is added.

14. Use of the liquid crystal medium according to any one of claims 1-12 in an electro-optical display.

15. An electro-optic display with active matrix addressing, characterized in that it contains a liquid crystal medium as a dielectric according to any one of claims 1-12.

16. The electro-optical display according to claim 15, characterized in that it is a VA, PSA, PA-VA, SS-VA, SA-VA, PS-VA, PALC, IPS, PS-IPS, FFS or PS-FFS display.

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