Liquid crystal media

By incorporating polar compounds of formula I into liquid crystal mixtures with negative dielectric anisotropy, the challenges of achieving high resistivity, wide temperature range, short response times, and low threshold voltages are addressed, resulting in a stable and efficient liquid crystal mixture for electro-optical displays.

JP7676120B2Active Publication Date: 2025-05-14MERCK PATENT GMBH
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Patent Information

Application Number
JP2020134907
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2014-08-29
Filing Date
2020-08-07
Publication Date
2025-05-14
Estimated Expiration
2035-06-17

AI Technical Summary

Technical Problem

Existing liquid crystal mixtures for electro-optical display applications, particularly those based on the ECB, IPS, and FFS effects, face challenges in achieving high resistivity, wide operating temperature range, short response times, and low threshold voltages, while maintaining image stability over long operating times.

Method used

Incorporating one or more polar compounds of general formula I into liquid crystal mixtures with negative dielectric anisotropy, which improves rotational viscosity and elastic constants, thereby enhancing response times and phase stability across a wide temperature range.

Benefits of technology

The resulting liquid crystal mixture exhibits a wide nematic phase range, low rotational viscosity, short response times, and improved reliability, ensuring image stability even after long operating times, while maintaining high resistivity and low threshold voltages.

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Abstract

To provide a liquid crystal medium.SOLUTION: The present invention relates to a liquid crystal medium that comprises at least one compound of formula I, and use of the liquid crystal medium for an active matrix display, particularly for an active matrix display based on an effect of VA, PSA, PS-VA, PALC, FFS, PS-FFS, PS-IPS or IPS (where R1, R1* each denote a C1-15 alkyl or alkoxy, Z1, Z2 each denote a single bond, -CH2CH2-, -CH=CH-, -CH2O- or the like, L1-3 each denote F, Cl, CF3, OCF3 or CHF2).SELECTED DRAWING: None
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Description

[Technical field]

[0001] The present invention relates to a liquid-crystalline medium comprising at least one compound of the formula I.

[0002] [ka] During the ceremony, R 1 and R 1* each independently represent an alkyl or alkoxy group having 1 to 15 C atoms, with the proviso that in addition, one or more CH groups in these groups each independently represent one or more of -C≡C-, -CF2O-, -CH=CH-, ...C≡C-, -CF2O-, -CH=CH-, -C≡C-, -C≡C-, -C≡C-

[0003] [ka] may be replaced by -O-, -CO-O-, -O-CO-, provided that in addition one or more H atoms may be replaced by halogen; Z 1 and Z 2 represent, independently of one another, a single bond, -CHCH-, -CH=CH-, -CHO-, -OCH-, -CFO-, -OCF-, -COO-, -OCO-, -CF-, -C≡C-, -CF=CF-, or -CH=CHCHO-; L 1~3 each independently represents F, Cl, CF3, OCF3 or CHF2. [Background technology]

[0004] Media of this type can be used in particular for electro-optical display applications with active matrix addressing based on the ECB effect and for in-plane switching (IPS) or fringe field switching (FFS) display applications.

[0005] The principle of electrically controlled birefringence, i.e. the ECB (electrically controlled birefringence) effect or also the DAP (deformation of aligned phases) effect, was first disclosed in 1971 (MF Schieckel and K. Fahrenschon, "Deformation of nematic liquid crystals with vertical orientation in electrical fields", Appl. Phys. Lett. vol. 19 (1971), p. 3912 (Non-Patent Document 1)). This was followed by papers by JF Kahn (Appl. Phys. Lett. vol. 20 (1972), p. 1193 (Non-Patent Document 2)) and G. Labrunie and J. Robert (J. Appl. Phys. vol. 44 (1973), p. 4869 (Non-Patent Document 3)).

[0006] In the articles by J. Robert and F. Clerc (SID 80 Digest Techn. Papers (1980), p. 30 (Non-Patent Document 4)), J. Duchene (Displays vol. 7 (1986), p. 3 (Non-Patent Document 5)) and H. Schad (SID 82 Digest Techn. Papers (1982), p. 244 (Non-Patent Document 6)), it was shown that in order to be suitable for use in high-information display elements based on the ECB effect, liquid-crystalline phases must have high values ​​of the ratio of the elastic constants K3 / K1, high values ​​of the optical anisotropy Δn and values ​​of the dielectric anisotropy Δε below −0.5. Electro-optical display elements based on the ECB effect have homeotropic edge alignment (VA technology, i.e. vertically aligned). Dielectrically negative liquid-crystalline media can also be used in displays using the so-called IPS or FFS effect.

[0007] Displays using the ECB effect include so-called VAN (vertically aligned nematic) displays, such as MVA (multi-domain vertical alignment, e.g. Yoshide, H. et al., Paper 3.1: “MVA LCD for Notebook or Mobile PCs (omitted)”, SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6-9 (Non-Patent Document 7) and Liu, CT et al., Paper 15.1: “A 46-inch TFT-LCD HDTV Technology (omitted)”, SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 750-753 (Non-Patent Document 8)), 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. 750-753 (Non-Patent Document 9)). Symposium, Digest of Technical Papers, XXXV, Book II, pp. 760-763 (Non-Patent Document 9)), ASV (advanced super view, e.g. Shigeta, Mitsuhiro 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 (Non-Patent Document 10)), and 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 and 759 (Non-Patent Document 11)) and in addition to the long-known TN (twisted nematic) displays, the technology has been compared in a general way, for example, in the SID Seminar in Souk in June 2004, Seminar M-6: "Recent Advances in LCD Technology", Seminar Lecture Notes, M-6 / 1 to M-6 / 26 (Non-Patent Document 12) and Miller, Ian, SID Seminar 2004, Seminar M-7: "LCD-Television", Seminar Lecture Notes, M-7 / 1 to M-7 / 32 (Non-Patent Document 13). Although the response time of modern ECB displays has already been significantly improved by overdrive addressing methods, e.g. Kim, Hyeon Kyeong et al., Paper 9.1: "A57-in. Wide UXGA TFT-LCD for HDTV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 106-109 (Non-Patent Document 14), achieving video-compatible response times remains a problem that has yet to be satisfactorily solved, especially in switching grey levels (grey shades).

[0008] The industrial application of this effect in electro-optical display elements requires LC phases which satisfy a number of requirements, of particular importance here being chemical resistance to moisture, air, and physical influences such as heat, infrared, visible and ultraviolet radiation, and direct and alternating electric fields.

[0009] Furthermore, industrially usable LC phases are required to have a liquid crystal mesophase within a suitable temperature range and low viscosity.

[0010] The series of compounds having liquid crystal mesophases disclosed to date does not include a single compound that meets all these requirements. Therefore, to obtain a substance that can be used as an LC phase, a mixture of 2 to 25 compounds, preferably 3 to 18 compounds, is generally prepared. However, since liquid crystal materials with significantly negative dielectric anisotropy and suitable long-term stability have not been available until now, it has not been possible to easily prepare the optimal phase in this way.

[0011] Matrix liquid-crystal displays (MLC displays) are known. Non-linear elements that can be used to individually switch the individual pixels are, for example, active elements (i.e. transistors). The term "active matrix" is still used and two types can be distinguished: 1. MOS (metal oxide semiconductor) transistors on a silicon wafer as a substrate; 2. Thin-film transistor (TFT) on a glass plate as the substrate.

[0012] In the case of type 1, the electro-optical effect used is usually dynamic scattering or the guest-host effect. The use of single crystal silicon as substrate material limits the size of the display, as it results in problems at the connections even in the case of modular assembly of the various component displays.

[0013] In the case of the preferred and more likely type 2, the electro-optical effect used is usually the TN effect.

[0014] Two technologies are distinguished: TFTs containing compound semiconductors, for example CdSe, or TFTs based on polycrystalline or amorphous silicon. The latter technology is the subject of intensive research worldwide.

[0015] The TFT matrix is ​​applied to the inside surface of one glass plate of the display, while the other glass plate has a transparent counter electrode on its inside surface. Compared to the size of the pixel electrodes, the TFTs are very small and have virtually no adverse effect on the image. The technology can also be extended to full-color displays, in which a mosaic of red, green and blue filters is arranged so that a filter element faces each of the switchable pixels.

[0016] The term MLC display is used herein to cover any matrix display with integrated non-linear elements, i.e. displays which, in addition to the active matrix, also comprise passive elements such as varistors or diodes (MIM, i.e. metal-insulator-metal).

[0017] This type of MLC display is particularly suitable for television applications (e.g. pocket TVs) or for high-information displays in automobiles or aircraft. In addition to problems related to the angular dependence of contrast and response times, MLC displays also suffer from problems due to the liquid crystal mixture not having a sufficiently high resistivity [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay, Vol. 84, September 1984, A210-288, "Matrix LCD Controlled by Double Stage Diode Rings", p. 141ff, Paris (Non-Patent Document 15); STROMER, M., Proc. Eurodisplay, Vol. 84, September 1984, "Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays", p. 145ff, Paris (Non-Patent Document 16)]. As the resistance decreases, the contrast of the MLC display deteriorates.Since the resistivity of the liquid crystal mixture generally decreases over the lifetime of an MLC display due to interactions with the internal surfaces of the display, a high (initial) resistance is very important to ensure that the display has acceptable resistance values ​​over long periods of operation.

[0018] There remains a strong demand for MLC displays that have very high resistivity while at the same time have a wide operating temperature range, short response time and low threshold voltage, which allows the generation of a variety of grey levels (grey shades).

[0019] Disadvantages of frequently used MLC-TN displays are their relatively low contrast, relatively high viewing angle dependence, and the difficulty in producing grey levels (grey blocking) in these displays.

[0020] VA displays have a significantly better viewing angle dependence and are therefore mainly used for televisions and monitors. However, there is still a demand to improve the response time. At the same time, however, properties such as low temperature stability and reliability must not be compromised. [Prior art documents] [Non-patent literature]

[0021] [Non-Patent Document 1] M. F. Schieckel and K. Fahrenschon, "Deformation of nematic liquid crystals with vertical orientation in electrical fields," Appl. Phys. Lett. 19 (1971), 3912. [Non-Patent Document 2] JFKahn, Appl. Phys. Lett. vol. 20 (1972), p. 1193. [Non-Patent Document 3] G. Labrunie and J. Robert, J. Appl. Phys. 44 (1973), 4869 [Non-Patent Document 4] J. Robert and F. Clerc, SID 80 Digest Techn. Papers (1980), p. 30 [Non-Patent Document 5] J. Duchene, Displays vol. 7 (1986), p. 3 [Non-Patent Document 6] H. Schad, SID 82 Digest Techn. Papers (1982), 244 pages. [Non-Patent Document 7] Yoshide, H. et al., Paper 3.1: "MVA LCD for Notebook or Mobile PCs (omitted)" SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6-9 [Non-Patent Document 8] Liu, CT et al., Paper 15.1: "A 46-inch TFT-LCD HDTV Technology (omitted)", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 750-753 [Non-Patent Document 9] 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 [Non-Patent Document 10] Shigeta, Mitsuhiro 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. [Non-Patent Document 11] 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 [Non-Patent Document 12] Seminar M-6: "Recent Advances in LCD Technology", Seminar Lecture Notes, M-6 / 1~M-6 / 26 [Non-Patent Document 13] Miller, Ian, SID Seminar 2004, Seminar M-7: "LCD-Television", Seminar Lecture Notes, M-7 / 1~M-7 / 32 [Non-Patent Document 14] Kim, Hyeon Kyeong et al., Paper 9.1: "A57-in.Wide UXGA TFT-LCD for HDTV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 106-109 [Non-Patent Document 15] TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., "Matrix LCD Controlled by Double Stage Diode Rings", Proc. Eurodisplay, Vol. 84, September 1984, A210-288, pp. 141ff, Paris [Non-Patent Document 16] STROMER, M., "Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays", Proc. Eurodisplay, Vol. 84, September 1984, p. 145ff, Paris Summary of the Invention [Problem to be solved by the invention]

[0022] The present invention is based on the object of providing liquid crystal mixtures, in particular for monitor and television applications, based on the ECB effect or the IPS or FFS effect, which do not have the above-mentioned defects or only have them to a reduced extent. In particular, it must be ensured that the monitors and televisions also operate at extremely high and low temperatures and at the same time have short response times and at the same time have improved reliability behavior, in particular do not have or have significantly reduced image sticking after long operating times. [Means for solving the problem]

[0023] Surprisingly, when one or more, preferably at least one or two polar compounds of general formula I are used in liquid crystal mixtures, especially LC mixtures with negative dielectric anisotropy Δε, preferably for VA, IPS and FFS displays, it is possible to improve the rotational viscosity value and thus the response time.Using the compounds of formula I, it is possible to prepare liquid crystal mixtures, preferably VA, PS-VA, PSA, IPS and FFS mixtures, which have short response times and at the same time good phase properties and good low-temperature behavior.The liquid crystal mixtures according to the invention are characterized in particular by a very good ratio of rotational viscosity and elastic constant, preferably K3.

[0024] The invention therefore relates to a liquid-crystalline medium comprising at least one compound of the formula I. Effect of the Invention

[0025] The mixtures according to the invention show a very wide nematic phase range with a clearing point above 65° C., preferably above 70° C., in particular above 75° C., a very favorable capacity threshold, a relatively high value for the retention, and at the same time a very good low temperature stability at −20° C. and −30° C., as well as a very low rotational viscosity and short response times. The mixtures according to the invention further show, in addition to the improvement of the rotational viscosity γ1, a low elastic constant K 33 The compounds of the formula I are particularly suitable for the preparation of liquid-crystal mixtures having a negative Δε. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0026] Some preferred embodiments of the mixtures according to the invention are given below.

[0027] In the compounds of formula I, R 1 is preferably a linear alkyl, in particular CH3, C2H5, n-C3H7, n-C4H9, n-C5H 11 and n-CH 13 and furthermore alkenyl and alkoxy.

[0028] In the compounds of formula I, R 1* is preferably a linear alkoxy, in particular OC2H5, OC3H7, OC4H9, OC5H 11 , OC6H 13 , further alkenyloxy, in particular OCH2CH=CH2, OCH2CH=CHCH3, OCH2CH=CHC2H5, further alkyl, in particular n-C3H7, n-C4H9, n-C5H 11 , n-CH 13 Represents.

[0029] In the compounds of formula I, Z 1 and Z 2 preferably, each independently of one another, represents a single bond.

[0030] Base L 1 , L 2 and L 3 preferably, independently of each other, each represents F.

[0031] Z 1 and Z 2 Preferably, each of represents a single bond.

[0032] Preferred compounds of formula I are compounds of formulae Ia to Ih.

[0033] [ka]

[0034] Compounds of formula Ia are particularly preferred.

[0035] Particularly preferred compounds of formula I are shown below.

[0036] [ka]

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] Compounds of formula I are known, for example from EP 1 352 943 A1, and can be prepared by known methods.

[0041] Compounds of formula I can be prepared, for example, as follows:

[0042] [ka] During the ceremony, R 1 and R 1* each independently represent a linear or branched alkyl or alkoxy group having 1 to 15 C atoms, and L 1~3 each independently represents F, Cl, CF3, OCF3 or CHF2.

[0043] Particularly preferred compounds can be prepared, for example, as follows:

[0044] [ka] During the ceremony, R 1 represents a linear or branched alkyl or alkoxy group having 1 to 15 C atoms, and Alkyl represents an alkyl group having 1 to 15 C atoms.

[0045] The medium according to the invention preferably comprises one, two, three or more, preferably one or even two, compounds of formula I.

[0046] The compounds of the formula I are preferably used in the liquid-crystalline medium in an amount of 1 to 30% by weight, preferably 2 to 20% by weight, very particularly preferably 3 to 10% by weight.

[0047] Preferred embodiments of the liquid-crystalline media according to the invention are set out below: a) Liquid-crystalline medium which further comprises one or more compounds selected from the group of the compounds of the formulae IIA, IIB and IIC.

[0048] [ka] During the ceremony, R 2A , R 2B and R 2C each independently of the other represents H, an alkyl or alkenyl group having up to 15 C atoms which is not substituted or is monosubstituted by CN or CF3 or is at least monosubstituted by a halogen, provided that in addition, one or more CH2 groups in these groups are not linked directly to one another by -O-, -S-,

[0049] [ka] may be replaced by -C≡C-, -CF2O-, -OCF2-, -OC-O- or -O-CO-; L 1~4 each independently represents F, Cl, CF3 or CHF2, Z 2 and Z 2’ represent, independently of one another, a single bond, -CH2CH2-, -CH=CH-, CFO-, -OCF2-, -CHO-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -C≡C-, or -CH=CHCHO-; p represents 0, 1 or 2; q represents 0 or 1, and v represents 1 to 6.

[0050] In the compounds of formula IIA and IIB, Z 2 may have the same or different meanings. In the compound of formula IIB, Z 2 and Z 2’ may have the same or different meanings.

[0051] In the compounds of formula IIA, IIB and IIC, R 2A , R 2B and R 2C are each preferably alkyl having 1 to 6 C atoms, in particular CH3, C2H5, n-C3H7, n-C4H9, n-C5H 11 and further alkenyl, in particular CH2=CH, CH3CH=CH, C2H5CH=CH and C3H7CH=CH.

[0052] In the compounds of formula IIA and IIB, L 1 , L 2 , L 3 and L 4 is preferably L 1 =L 2 = F and L 3 =L 4 =F, and furthermore, 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 In formulas IIA and IIB, Z 2 and Z 2’ preferably each independently of one another represents a single bond or further a -CH2O- or -C2H4- bridge.

[0053] In formula IIB, Z 2 = -C2H4- or -CH2O-, Z 2’ is preferably a single bond, and Z 2’ = -C2H4- or -CH2O-, Z 2 is preferably a single bond. In the compounds of formula IIA and IIB, (O)Cv H 2v+1 Preferably, OC v H 2v+1 , and furthermore, C v H 2v+1 In the compound of formula IIC, (O)C v H 2v+1 is preferably C v H 2v+1 In the compound of formula IIC, L 3 and L 4 preferably each represents F.

[0054] Preferred compounds of formula IIA, IIB and IIC are shown below.

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka] In the formula, alkyl and alkyl *each independently represents a linear alkyl group having 1 to 6 C atoms.

[0062] Particularly preferred mixtures according to the invention comprise one or more compounds of formulae IIA-2, IIA-8, IIA-14, IIA-26, IIA-28, IIA-33, IIA-39, IIA-45, IIA-46, IIA-47, IIA-50, IIB-2, IIB-11, IIB-16 and IIC-1.

[0063] The proportion of compounds of formulae IIA and / or IIB in the overall mixture is preferably at least 20% by weight.

[0064] Particularly preferred media according to the invention comprise at least one compound of the formula IIC-1, preferably in an amount of more than 3% by weight, in particular more than 5% by weight, particularly preferably from 5 to 25% by weight.

[0065] [ka] In the formula, alkyl and alkyl * has the meaning given above.

[0066] b) Liquid-crystalline medium additionally comprising one or more compounds of the formula III.

[0067] [ka] During the ceremony, R 31 and R 32 each independently of one another represents a straight-chain alkyl, alkoxy, alkenyl, alkoxyalkyl or alkenyloxy group having up to 12 C atoms, and

[0068] [ka] Z 3represents a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, -C≡C-, or -CF=CF-.

[0069] Preferred compounds of formula III are shown below.

[0070] [ka] During the ceremony, Alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 C atoms.

[0071] alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 C atoms.

[0072] c) Liquid-crystalline medium additionally comprising one or more tetracyclic compounds of the following formula:

[0073] [ka]

[0074] [ka] During the ceremony, R 7~10 are each independently of one another in claim 5. 2A has one of the meanings given in w and x each independently represent 1 to 6.

[0075] Particularly preferred are mixtures comprising at least one compound of formula V-9 and / or formula V-10.

[0076] d) Liquid-crystalline medium additionally comprising one or more compounds of the formulae Y-1 to Y-6.

[0077] [ka] In the formula, R 14 ~R 19 each independently of one another represents an alkyl or alkoxy group having 1 to 6 C atoms; z and m each independently of the other represents 1 to 6; x represents 0, 1, 2 or 3.

[0078] The medium according to the invention particularly preferably comprises one or more compounds of the formulae Y-1 to Y-6, preferably in an amount of 5% by weight or more.

[0079] e) Liquid-crystalline medium additionally comprising one or more fluorinated terphenyls of the formulae T-1 to T-21.

[0080] [ka]

[0081] [ka]

[0082] [ka] During the ceremony, R represents a linear alkyl or alkoxy group having 1 to 7 C atoms, m=0, 1, 2, 3, 4, 5 or 6, and n represents 0, 1, 2, 3 or 4.

[0083] R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.

[0084] The medium according to the invention preferably comprises terphenyls of the formulae T-1 to T-21 in an amount of 2 to 30% by weight, in particular 5 to 20% by weight.

[0085] Particularly preferred are compounds of formulae T-1, T-2, T-19 and T-20. In these compounds, R preferably represents alkyl, furthermore alkoxy, each having 1 to 6 C atoms. In compounds of formula T-19, R preferably represents alkyl or alkenyl, in particular alkyl. In compounds of formula T-20, R preferably represents alkyl.

[0086] If a Δn value of the mixture is intended to be 0.1 or more, terphenyls are preferably used in the mixture according to the invention. Preferred mixtures contain 2 to 20% by weight of one or more terphenyl compounds selected from the compound groups T-1 to T-21.

[0087] f) Liquid-crystalline medium additionally comprising one or more biphenyls of the formulae B-1 to B-3.

[0088] [ka] During the ceremony, Alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, and alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 C atoms.

[0089] The proportion of biphenyls of the formulae B-1 to B-3 in the entire mixture is preferably at least 3% by weight, in particular 5% by weight or more.

[0090] Among the compounds of the formulae B-1 to B-3, the compounds of the formulae B-1 and B-2 are particularly preferred.

[0091] Particularly preferred biphenyls are:

[0092] [ka] In the formula, alkyl *denotes an alkyl group having 1 to 6 C atoms. The medium according to the invention particularly preferably comprises one or more compounds of the formulae B-1a and / or B-2c.

[0093] Preferred compounds of the formula B-1a are especially those of the following formula:

[0094] [ka]

[0095] g) Liquid-crystalline medium additionally comprising at least one compound of the formulae Z-1 to Z-9.

[0096] [ka]

[0097] [ka] In the formula, R is R 2A and alkyl denotes an alkyl group having 1 to 6 C atoms.

[0098] h) Liquid-crystalline medium additionally comprising at least one compound of the formulae O-1 to O-17.

[0099] [ka]

[0100] [ka] In the formula, R 1 and R 2 is R 2A R 1 and R 2 preferably each independently of one another denotes straight-chain alkyl or alkenyl.

[0101] Preferred media comprise 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.

[0102] The mixtures according to the invention very particularly preferably comprise compounds of the formulae O-10, O-12, O-16 and / or O-17, in particular in amounts of 5 to 30% by weight.

[0103] Preferred compounds of formula O-17 are selected from the group of compounds of the following formulae:

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] [ka]

[0108] Further preferred are compounds of formula O-17 which contain a non-terminal double bond in the alkenyl side chain:

[0109] [ka]

[0110] The proportion of compounds of formula O-17 in the overall mixture is preferably at least 5% by weight.

[0111] i) Liquid-crystalline medium additionally comprising at least one compound of the following formulae, preferably in a total amount of 5% or more by weight, in particular 10% or more by weight:

[0112] [ka]

[0113] Further preference is given to mixtures according to the invention which contain the following compound (acronym: CC-3-V1), preferably in an amount of 2 to 15% by weight:

[0114] [ka]

[0115] Preferred mixtures contain 5 to 60% by weight, preferably 10 to 55% by weight, in particular 20 to 50% by weight, of a compound of the following formula (acronym: CC-3-V):

[0116] [ka]

[0117] Compound of the formula (acronym: CC-3-V)

[0118] [ka] and the compound of the formula (acronym: CC-3-V1)

[0119] [ka] More preferred is a mixture containing the above in an amount of preferably 10 to 60% by weight.

[0120] j) Liquid-crystalline medium additionally comprising at least one compound of the formula O-10 and at least one compound of the formula O-17, selected from the following group of compounds:

[0121] [ka] The medium according to the invention particularly preferably comprises a tricyclic compound of the formula O-10a and / or O-10b in combination with one or more bicyclic compounds of the formulae O-17a to O-17d. The total proportion of compounds of the formulae O-10a and / or O-10b in combination with one or more compounds selected from the bicyclic compounds of the formulae O-17a to O-17d is 5 to 40%, very particularly preferably 15 to 35%.

[0122] A very particularly preferred mixture comprises the compounds O-10a and O-17a.

[0123] [ka] The compounds O-10a and O-17a are preferably present in the mixture in a concentration of 15 to 35%, particularly preferably 15 to 25%, particularly preferably 18 to 22%, based on the mixture as a whole.

[0124] A very particularly preferred mixture comprises the compounds O-10b and O-17a.

[0125] [ka] The compounds O-10b and O-17a are preferably present in the mixture in a concentration of 15 to 35%, particularly preferably 15 to 25%, particularly preferably 18 to 22%, based on the mixture as a whole.

[0126] Very particularly preferred mixtures comprise the following three types of compounds:

[0127] [ka] The compounds O-10a, O-10b and O-17a are preferably present in the mixture in a concentration of 15 to 35%, particularly preferably 15 to 25%, particularly preferably 18 to 22%, based on the mixture as a whole.

[0128] A preferred mixture comprises at least one compound selected from the following group of compounds:

[0129] [ka] In the formula, R 1 and R 2 has the meaning given above. In compounds O-6, O-7 and O-17, R 1 preferably denotes alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms, respectively, and R 2 preferably denotes alkenyl having 2 to 6 C atoms. In the compounds of formula O-10, R 1 preferably denotes alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms, respectively, and R 2 preferably denotes alkyl having 1 to 6 C atoms.

[0130] Preferred mixtures comprise at least one compound selected from the group of compounds of formulae O-6a, O-6b, O-7a, O-7b, O-17e, O-17f, O-17g and O-17h.

[0131] [ka] In the formula, alkyl represents an alkyl group having 1 to 6 C atoms.

[0132] The compounds of the formulae O-6, O-7 and O-17e-h are preferably present in the mixtures according to the invention in amounts of 1 to 40% by weight, in particular 2 to 35% by weight and very particularly preferably 2 to 30% by weight.

[0133] k) Preferred liquid crystal media according to the invention comprise one or more substances which contain a tetrahydronaphthyl or naphthyl unit, such as, for example, compounds of the formulae N-1 to N-5.

[0134] [ka] In the formula, R 1N and R 2N are each independently 2A and preferably denotes straight-chain alkyl, straight-chain alkoxy or straight-chain alkenyl, and Z 1 and Z 2 each independently represents -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CHO-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -C≡C-, -CF2O-, -OCF2-, -CH2- or a single bond.

[0135] l) Preferred mixtures comprise one or more compounds selected from the group of compounds of formulae BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1 and BS-2.

[0136] [ka] During the ceremony, R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 are each independently 2A where c is 0, 1 or 2, and d is 1 or 2. 1 and R 2 preferably independently of one another denote alkyl, alkoxy, alkenyl or alkenyloxy, each having 1 or 2 to 6 C atoms.

[0137] The mixtures according to the invention preferably comprise compounds of the formulae BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1 and / or BS-2 in an amount of 3 to 20% by weight, in particular in an amount of 3 to 15% by weight.

[0138] Particularly preferred compounds of the formulae BC, CR, BF-1 and BS-1 are the compounds BC-1 to BC-7, CR-1 to CR-5, BF-1a to BF-1c, BS-1a to BS-1c.

[0139] [ka]

[0140] [ka]

[0141] [ka] During the ceremony, Alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, and alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 C atoms.

[0142] Mixtures comprising one, two or three compounds of the formulae BC-2, BF-1 and / or BF-2 are very particularly preferred.

[0143] m) Preferred mixtures comprise one or more indane compounds of formula In.

[0144] [ka] During the ceremony, R 11 , R 12 , R 13 each independently represent a straight-chain alkyl, alkoxy, alkoxyalkyl or alkenyl group having 1 to 6 C atoms, R 12 and R 13 represents additionally a halogen, preferably F,

[0145] [ka] represents i represents 0, 1 or 2.

[0146] Preferred compounds of formula In are compounds of formulae In-1 to In-16 shown below.

[0147] [ka]

[0148] [ka] Particularly preferred are the compounds of formulae In-1, In-2, In-3 and In-4.

[0149] In the mixtures according to the invention, the compounds of the formula In and the subformulae In-1 to In-16 are preferably used in a concentration of more than 5% by weight, in particular 5 to 30% by weight, very particularly preferably 5 to 25% by weight.

[0150] n) Preferred mixtures additionally contain one or more compounds of formulae L-1 to L-11.

[0151] [ka]

[0152] [ka] During the ceremony, R, R 1 and R 2 are each independently of one another in claim 5. 2A where alkyl represents an alkyl group having 1 to 6 C atoms. s represents 1 or 2.

[0153] Particularly preferred are compounds of formulae L-1 and L-4, especially L-4.

[0154] The compounds of the formulae L-1 to L-11 are preferably used in concentrations of 5 to 50% by weight, in particular 5 to 40% by weight, very particularly preferably 10 to 40% by weight.

[0155] Particularly preferred mixture concepts are given below: (The acronyms used are explained in Table B, n and m each independently represent 1 to 15, preferably 1 to 6.)

[0156] The mixture according to the invention preferably comprises L 1 =L 2 = F and R 1 =R 1* = one or more compounds of formula I, CPY-n-Om, in particular CPY-2-O2, CPY-3-O2 and / or CPY-5-O2, preferably in a concentration of more than 5%, in particular 10 to 30%, based on the entire mixture, and / or CY-n-Om, preferably CY-3-O2, CY-3-O4, CY-5-O2 and / or CY-5-O4, preferably in a concentration of more than 5%, in particular 15 to 50%, based on the entire mixture, and / or CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, preferably in a concentration of more than 5%, in particular 10-30%, based on the entire mixture, and / or CLY-n-Om, preferably CLY-2-O4, CLY-3-O2 and / or CLY-3-O3, preferably in a concentration of more than 5%, in particular 10-30%, based on the total mixture, and / or CK-nF, preferably CK-3-F, CK-4-F and / or CK-5-F, preferably in an amount of more than 5%, in particular 5 to 25%, based on the entire mixture, include.

[0157] Furthermore, the mixtures according to the invention are preferred which comprise the following mixture concepts (n and m each independently represent 1 to 6): CPY-n-Om and CY-n-Om, preferably at a concentration of 10-80%, based on the total mixture, and / or CPY-n-Om and CK-nF, preferably at a concentration of 10-70%, based on the total mixture, and / or Y-nO-Om, preferably Y-4O-O4, in particular in concentrations of 2 to 20%, based on the total mixture, and / or CPY-n-Om and PY-n-Om, preferably CPY-2-O2 and / or CPY-3-O2 and PY-3-O2, preferably in a concentration of 10 to 45%, based on the total mixture, and / or CPY-n-Om and CLY-n-Om, preferably at a concentration of 10-80% based on the total mixture, and / or CCVC-nV, preferably CCVC-3-V, preferably in a concentration of 2-10%, based on the total mixture, and / or CCC-nV, preferably CCC-2-V and / or CCC-3-V, preferably in a concentration of 2-10%, based on the total mixture, and / or CC-VV, preferably at a concentration of 5-50% based on the total mixture include.

[0158] In a preferred embodiment, the medium according to the invention comprises, in addition to one or more compounds of formula I, at least one compound selected from the group of compounds of formulae T-20, T-21, IIA-26, IIA-28, IIIA-33, IIA-39, IIA-50, IIA-51, IIB-16, BF-1, BF-2, V-10, O-6a, L-4, CC-3-V, CC-3-V1, IIB-11 and Z-9.

[0159] [ka]

[0160] [ka] During the ceremony, R, R 1 , R 2 and R 10 are each independently 2A has the meaning Alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 C atoms, alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 C atoms, (O)alkyl, (O)-alkyl and (O)alkyl * each independently represents alkyl or O-alkyl, m represents 0, 1, 2, 3, 4, 5 or 6; n represents 0, 1, 2, 3 or 4; x represents 1 to 6; c represents 0, 1 or 2; d represents 1 or 2.

[0161] The invention furthermore relates to an electro-optical display with active matrix addressing based on the ECB, VA, PS-VA, PA-VA, IPS, PS-IPS, FFS or PS-FFS effect, characterized in that it contains a liquid-crystalline medium as claimed in any one of claims 1 to 17 as dielectric.

[0162] The liquid crystal medium according to the invention preferably has a nematic phase at -20°C or lower and 70°C or higher, particularly preferably at -30°C or lower and 80°C or higher, very particularly preferably at -40°C or lower and 90°C or higher.

[0163] In this document, the expression "having a nematic phase" means, on the one hand, that no smectic phase and no crystallization are observed at low temperatures at the corresponding temperatures, and, on the other hand, that no clearing still occurs when heated from the nematic phase. The low-temperature studies are carried out in a flow viscometer at the corresponding temperatures and are checked by storage for at least 100 hours in test cells with layer thicknesses corresponding to electro-optical use. If the storage stability at a temperature of -20°C in the corresponding test cells is 1000 hours or more, the medium is considered stable at this temperature. At temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the clearing point is measured by conventional methods in capillaries.

[0164] The liquid crystal mixture preferably has a nematic phase range of at least 60K and a maximum melting point of 30mm at 20°C. 2 ·s -1 Flow viscosity ν 20 has.

[0165] The value of the birefringence Δn in the liquid crystal mixture is generally between 0.07 and 0.16, preferably between 0.08 and 0.13.

[0166] The liquid crystal mixture according to the invention has a Δε of −0.5 to −8.0, in particular −2.5 to −6.0, where Δε denotes the dielectric anisotropy. The rotational viscosity γ1 at 20° C. is preferably ≦150 mPa·s, in particular ≦120 mPa·s.

[0167] The liquid-crystalline media according to the invention have relatively low values ​​for the threshold voltage (V0): they are preferably in the range from 1.7 V to 3.0 V, particularly preferably below 2.5 V, very particularly preferably below 2.3 V.

[0168] In the present invention, the term "threshold voltage" relates to the capacitive threshold (V0), also known as the Freedericks threshold, unless otherwise stated.

[0169] In addition, the liquid-crystal media according to the invention have high values ​​for the voltage holding ratio in a liquid-crystal cell.

[0170] In general, liquid crystal media having a low addressing voltage or threshold voltage show a lower voltage holding ratio than those having a higher addressing voltage or threshold voltage and vice versa.

[0171] In the present invention, the term "dielectrically positive compounds" refers to compounds with Δε>1.5, the term "dielectrically neutral compounds" refers to those with -1.5≦Δε≦1.5, and the term "dielectrically negative compounds" refers to those with Δε<-1.5. Herein, the dielectric anisotropy of the compounds is determined by dissolving 10% of the compounds in a liquid crystal host and determining the capacitance of the resulting mixture at 1 kHz in at least one test cell with homeotropic and homogeneous surface alignment in each case with a layer thickness of 20 μm. The measuring voltage is typically between 0.5 V and 1.0 V, but always below the capacitance threshold of the respective liquid crystal mixture under consideration.

[0172] All temperature values ​​given in this invention are in °C.

[0173] The mixtures according to the invention are suitable for all VA-TFT applications, such as, for example, VAN, MVA, (S)-PVA, ASV, PSA (polymer sustained VA) and PS-VA (polymer stabilized VA). They are furthermore suitable for IPS (in-plane switching) and FFS (fringe field switching) applications with negative Δε.

[0174] The nematic liquid crystal mixtures in the displays according to the invention generally comprise two components A and B which themselves consist of one or more individual compounds.

[0175] Component A has a significant negative dielectric anisotropy and imparts a dielectric anisotropy of -0.5 or less to the nematic phase. In addition to one or more compounds of formula I, component A preferably comprises compounds of formula IIA, IIB and / or IIC, and further one or more compounds of formula O-17.

[0176] The proportion of component A is preferably between 45 and 100%, in particular between 60 and 100%.

[0177] For component A, one (or more) individual compound(s) are preferably selected that have a Δε value less than or equal to −0.8. The smaller the proportion A in the overall mixture, the more negative this value must be.

[0178] Component B is clearly nematogenic and has a viscosity of 30 mm at 20°C. 2 ·s -1 Less than 25mm, preferably 2 ·s -1 It has the following flow viscosity:

[0179] Many suitable materials are known to those skilled in the art from the literature. Compounds of formula O-17 are particularly preferred.

[0180] Particularly preferred individual compounds in component B have a viscosity of 18 mmHg at 20° C. 2 ·s -1 Less than 12mm, preferably 2 ·s -1 It is a very low viscosity nematic liquid crystal having a flow viscosity of

[0181] Component B is a monotropic or enantiotropic nematic, has no smectic phase, and can prevent the occurrence of smectic phases in liquid crystal mixtures up to very low temperatures. For example, when various highly nematogenic materials are added to a smectic liquid crystal mixture, the nematogenicity of these materials can be compared through the degree of inhibition of the smectic phase that is achieved.

[0182] The mixture may also contain a component C which comprises compounds having a dielectric anisotropy of Δε of 1.5 or more. These so-called positive compounds are generally present in mixtures of negative dielectric anisotropy in amounts of up to 20% by weight, based on the entire mixture.

[0183] If the mixture according to the invention comprises one or more compounds having a dielectric anisotropy Δε of ≧1.5, these are preferably one or more compounds selected from the group of compounds of the formulae P-1 to P-4.

[0184] [ka] During the ceremony, R represents a linear alkyl, alkoxy or alkenyl, each having 1 or 2 to 6 C atoms, X represents F, Cl, CF3, OCF3, OCHFCF3 or CCF2CHFCF3, preferably F or OCF3.

[0185] The compounds of the formulae P-1 to P-4 are preferably used in the mixtures according to the invention in a concentration of from 2 to 15%, in particular in a concentration of from 2 to 10%.

[0186] Particularly preferred are the compounds of the following formulae, which are preferably used in the mixtures according to the invention in amounts of 2 to 15%:

[0187] [ka]

[0188] In addition, these liquid crystal phases may also contain more than 18 components, preferably 18 to 25 components.

[0189] In addition to one or more compounds of formula I, these phases preferably contain 4 to 15, in particular 5 to 12, particularly preferably less than 10 compounds of formulae IIA, IIB and / or IIC and, optionally, one or more compounds of O-17.

[0190] In addition to the compounds of formula I and the compounds of formula IIA, IIB and / or IIC and optionally O-17, other components may also be present, for example in amounts of up to 45%, but preferably up to 35%, in particular up to 10%, of the total mixture.

[0191] The further constituents are preferably selected from the known substances which are classified as nematic or nematogenic substances, in particular the azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl cyclohexanecarboxylates, phenylcyclohexanes, cyclohexylbiphenyls, cyclohexylcyclohexanes, cyclohexylnaphthalenes, 1,4-biscyclohexylbiphenyls or cyclohexylpyrimidines, phenyl or cyclohexyldioxanes, optionally halogenated stilbenes, benzyl phenyl ethers, tolanes and substituted cinnamic esters.

[0192] The most important compounds suitable as components of liquid crystal phases of this type can be characterized by formula IV.

[0193] [ka] in which L and E respectively represent carbon or heterocyclic ring structures from the group formed by 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane structures, 2,5-disubstituted pyrimidine and 1,3-dioxane rings, 2,6-disubstituted naphthalene, di- and tetrahydronaphthalene, quinazoline and tetrahydroquinazoline, G represents -CH=CH-, -N(O)=N-, -CH=CQ-, -CH=N(O)-, -C≡C-, -CH2-CH2-, -CO-O-, -CH2-O-, -CO-S-, -CH2-S-, -CH=N-, -COO-Phe-COO-, -CF2O-, -CF=CF-, -OCF2-, -OCH2-, -(CH2)4-, -(CH2)3O- or a CC single bond, Q represents a halogen, preferably chlorine or -CN, and R 20 and R 21 represents alkyl, alkenyl, alkoxy, alkoxyalkyl or alkoxycarbonyloxy, each having up to 18, preferably up to 8, carbon atoms, or one of these groups represents CN, NC, NO2, NCS, CF3, SF5, OCF3, F, Cl or Br.

[0194] In most of these compounds, R 20 and R 21 are different from each other, one of these groups is usually an alkyl or alkoxy group. Also, variations beyond the suggested substituents are common. Many such materials or mixtures thereof are also commercially available. All these materials can be prepared by methods known from the literature.

[0195] It will also be appreciated by those skilled in the art that the VA, IPS or FFS mixtures according to the invention may also contain compounds in which, for example, H, N, O, Cl and F are replaced by the corresponding isotopes.

[0196] Polymerizable compounds, so-called reactive mesogens (RM), as disclosed, for example, in US Pat. No. 6,861,107, may be added to the mixtures according to the invention, preferably in a concentration of 0.01 to 5% by weight, particularly preferably 0.2 to 2% by weight, based on the mixture. These mixtures may also comprise initiators, for example, as described in US Pat. No. 6,781,665. Initiators, for example Irganox-1076 from BASF, are preferably added in an amount of 0 to 1% to the mixtures containing the polymerizable compounds. Mixtures of this type can be used for the so-called polymer-stabilized VA mode (PS-VA) or PSA (polymer sustained VA), in which polymerization of the reactive mesogens is intended to take place in the liquid crystal mixture. A prerequisite for this is that the liquid crystal mixture does not contain any polymerizable components which also polymerize under conditions in which the RM polymerizes. The polymerization is preferably carried out under the following conditions:

[0197] A UV-A lamp of a given intensity is used for a given period of time to polymerize the polymerizable component in the cell while applying a voltage (generally an AC voltage of 10 V to 30 V, with a frequency in the range of 60 Hz to 1 kHz). The UV-A light source generally has an output of 50 mW / cm. 2 The lamp is a metal halide lamp or a high-pressure mercury lamp having an intensity of 10 ...

[0198] These are conditions under which, for example, liquid crystal compounds containing alkenyl or alkenyloxy side chains, such as those of the formula: do not polymerize.

[0199] [ka]

[0200] In a preferred embodiment of the invention, the polymerizable compound is selected from compounds of formula M

[0201] [ka] In the formula, each group has the following meaning: R Ma and R Mb each independently of the other denotes P, P-Sp-, H, halogen, SF5, NO2, an alkyl, alkenyl or alkynyl group, provided that at least the group R Ma and R Mb preferably represents or contains the group P or P-Sp-, P represents a polymerizable group; Sp represents a spacer group or a single bond; A M1 and A M2 denote, each independently of one another, an aromatic, heteroaromatic, alicyclic or heterocyclic group which preferably has 4 to 25 ring atoms, preferably C atoms, which may also include or contain fused rings and which may be mono- or polysubstituted by L, L is 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 x )2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms (however, in addition, one or more H atoms in these groups may be replaced by F, Cl, P or P-Sp-), preferably P, P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, alkyl, alkenyl or alkynyl group, Y 1 represents a halogen, Z M1 -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 bond, R 0 and R 00 each independently represent H or alkyl having 1 to 12 C atoms, R x represents P, P-Sp-, H, halogen, linear, branched or cyclic alkyl having 1 to 25 C atoms (with the proviso that in addition, one or more non-adjacent CH 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 linked to each other, and with the proviso that in addition, one or more H atoms may be replaced by F, Cl, P or P-Sp-), an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms, m1 represents 0, 1, 2, 3 or 4; and n1 represents 1, 2, 3 or 4; However, the group R Ma , R Mb and at least one, preferably one, two or three, particularly preferably one or two, of the substituents L present denotes or contains at least one of the groups P or P-Sp-.

[0202] Particularly preferred compounds of formula M are R Ma and R Mbare each independently of one another P, P-Sp-, H, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, SF5, or a linear or branched alkyl having 1 to 25 C atoms (provided that in addition, one or more non-adjacent CH2 groups are each independently of one another -C(R 0 )=C(R 00 )-, -C≡C-, -N(R 00 ) may be replaced by -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, provided that in addition, one or more H atoms may be replaced by F, Cl, Br, I, CN, P or P-Sp-; Ma and R Mb at least one of the groups preferably represents or contains the group P or P-Sp-, A M1 and A M2 are each independently 1,4-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarin, flavone (in addition, one or more CH groups in these groups may be replaced by N), cyclohexane-1,4-diyl (in addition, one or more non-adjacent CH groups may be replaced by O and / or S), 1,4-cyclohexane-1,4-diyl, 1,4-cyclohexane-2,6-diyl, phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarin, flavone (in addition, one or more non-adjacent CH groups may be replaced by O and / or S), 1,4-cyclohexane-1,4-diyl, 1,4-cyclohexane-2,6-diyl, phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7 ... bicyclo[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, indan-2,5-diyl or octahydro-4,7-methanoindan-2,5-diyl, all of which may be unsubstituted or mono- or polysubstituted by L; L is P, P-Sp-, OH, CH2OH, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x )2, -C(=O)Y1 , -C(=O)R x , -N(R x )2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms (however, in addition, one or more H atoms in these groups may be replaced by F, Cl, P or P-Sp-), P represents a polymerizable group; Y 1 represents a halogen, R x represents P, P-Sp-, H, halogen, linear, branched or cyclic alkyl having 1 to 25 C atoms (with the proviso that in addition, 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 linked to each other, and with the proviso that in addition, one or more H atoms may be replaced by F, Cl, P or P-Sp-), an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms; It is something.

[0203] R Ma and R Mb Very particular preference is given to compounds of the formula M, in which one or both of

[0204] Suitable and preferred RM or monomers or comonomers for use in the liquid crystal media according to the invention and in PS-VA or PSA displays are, for example, selected from the following formulae:

[0205] [ka]

[0206] [ka]

[0207] [ka]

[0208] [ka]

[0209] [ka]

[0210] [ka] In the formula, each group has the following meaning: P 1 , P 2 and P 3 are each identical or different and represent a polymerizable group (preferably having one of the meanings given above and below for P), particularly preferably an acrylate, methacrylate, fluoroacrylate, oxetane, vinyloxy or epoxide group, Sp 1 , Sp 2 and Sp 3 are each independently a single bond or, preferably, Sp a represents a spacer group having one of the meanings given above and below for -(CH2) p1 -, -(CH2) p1 -O-, -(CH2) p1 -CO-O-, or -(CH2) p1 represents -O-CO-O-, where p1 is an integer from 1 to 12, provided that the bond to the adjacent ring in the group described below occurs via an O atom; However, the group P 1 -Sp 1 -, P 2 -Sp 2- and P 3 -Sp 3 -At least one of R aa one or more groups P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - is R aa may also represent R aa is H, F, Cl, CN, or a linear or branched alkyl having 1 to 25 C atoms (provided that in addition, one or more non-adjacent CH groups may each be independently C(R) such that O and / or S atoms are not directly linked to each other). 0 )=C(R 00 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, provided that in addition, one or more H atoms may be replaced by F, Cl, CN or P 1 -Sp 1 -), particularly preferably linear or branched, optionally monofluorinated or polyfluorinated, alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy having 1 to 12 C atoms, with the proviso that alkenyl and alkynyl groups have at least 2 C atoms and branched groups have at least 3 C atoms, R 0 , R 00 each, independently of one another, identically or differently at each occurrence, represents H or alkyl having 1 to 12 C atoms, R y and R z each independently represents H, F, CH3 or CF3, X 1 , X 2 and X 3 each independently represents -CO-O-, -O-CO- or a single bond, Z 1-O-, -CO-, -C(R y R z )- or -CF2CF2-, Z 2 and Z 3 are each independently -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2- or -(CH2) n -, where n is 2, 3 or 4; L is, identically or differently, in each occurrence, F, Cl, CN, SCN, SF5 or an alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, which may be linear or branched and mono- or polyfluorinated, and has 1 to 12 C atoms, preferably F; L' and L" each independently represent H, F or Cl; r represents 0, 1, 2, 3 or 4; s represents 0, 1, 2 or 3; t represents 0, 1 or 2; x represents 0 or 1.

[0211] In the compounds of formulae M1 to M36,

[0212] [ka] with L, identically or differently in each occurrence, having one of the above meanings and preferably representing 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, in particular F or CH3.

[0213] Suitable polymerizable compounds are listed in Table E, for example.

[0214] The liquid crystal medium according to the present application preferably comprises from 0.1 to 10%, preferably from 0.2 to 4.0%, particularly preferably from 0.2 to 2.0%, of a total amount of polymerizable compounds.

[0215] The polymerizable compounds of formula M and formulae RM-1 to RM98 are particularly preferred.

[0216] The mixtures according to the invention may further comprise conventional additives, such as, for example, stabilizers, antioxidants, UV absorbers, nanoparticles, microparticles, and the like.

[0217] The structure of the liquid crystal display according to the invention corresponds to a conventional configuration, for example as described in EP 0 240 379 A1.

[0218] The following examples are intended to illustrate the invention without limiting it in any way. Above and below, the percentage data represent percentages by weight and all temperatures are given in degrees Celsius.

[0219] Throughout this patent application, 1,4-cyclohexylene and 1,4-phenylene rings are represented as follows:

[0220] [ka]

[0221] The cyclohexylene ring is a trans-1,4-cyclohexylene ring.

[0222] Throughout this patent application and in the examples, the structures of liquid crystal compounds are designated by acronyms.

[0223] Unless otherwise indicated, the conversion of the chemical formulae is carried out according to Tables 1 to 3. All groups C n H 2n+1 , Cm H 2m+1 and C m’ H 2m’+1 or C n H 2n and C m H 2m are each a linear alkyl or alkylene group. 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 lists the ring elements of each compound, Table 2 lists the bridge elements, and Table 3 shows the meaning of the symbols for the left and right chains of the compounds.

[0224] [Table 1]

[0225] [Table 2]

[0226] [Table 3]

[0227] [Table 4]

[0228] Preferred blend components are shown in Tables A and B.

[0229] [Table 5]

[0230] [Table 6]

[0231] In addition to the compounds of the formula I, the mixtures according to the invention very particularly preferably comprise one or more compounds of table B.

[0232] The following abbreviations are used:

[0233] (n, m, m', z: each independently 1, 2, 3, 4, 5 or 6; (O)C m H 2m+1 OC m H 2m+1 or C m H 2m+1 It means.)

[0234] [Table 7]

[0235] [Table 8]

[0236] [Table 9]

[0237] [Table 10]

[0238] [Table 11]

[0239] [Table 12]

[0240] [Table 13]

[0241]

Table 14

[0242]

Table 15

[0243]

Table 16

[0244]

Table 17

[0245]

Table 18

[0246]

Table 19

[0247]

Table 20

[0248]

Table 21

[0249]

Table 22

[0250] The liquid crystal mixture that can be used according to the present invention is prepared in a conventional manner.Generally, the desired amount of the component that is used in a smaller amount is dissolved in the component that constitutes the main composition, advantageously at elevated temperature.It is also possible to mix the solutions of the components in organic solvents, for example acetone, chloroform or methanol, and then remove the solvent again after thorough mixing, for example by distillation.

[0251] By utilizing suitable additives, the liquid crystal phase according to the present invention can be modified so that it can be used in, for example, any type of ECB, VAN, IPS, GH or ASM-VA LCD display disclosed thus far.

[0252] The dielectric may also contain further additives known to those skilled in the art and described in the literature, such as, for example, UV absorbers, antioxidants, nanoparticles and free radical scavengers. For example, 0-15% of pleochroic dyes, stabilizers such as phenols, HALS (hindered amine light stabilizers), for example Tinuvin 770 (=bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate) or chiral dopants can be added. Stabilizers suitable for the mixtures according to the invention are in particular those listed in Table D.

[0253] For example, 0-15% of pleochroic dyes can be added, and furthermore conductive salts, preferably ethyldimethyldodecylammonium 4-hydroxybenzoate, tetrabutylammonium tetraphenylboronate or complex salts of crown ethers (see, for example, Haller et al., Mol. Cryst. Liq. Cryst. vol. 24, pp. 249-258 (1973)), can be added to improve the electrical conductivity, or substances can be added to modify the dielectric anisotropy, the viscosity and / or the orientation of the nematic phase. Substances of this type are described, for example, in DE-A-22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430 and 28 53 728.

[0254] Table C shows dopants that can be added to the mixture according to the invention. If the mixture contains a dopant, it is used in an amount of 0.01 to 4% by weight, preferably 0.1 to 1.0% by weight.

[0255] Table C shows possible dopants which are generally added to the mixtures according to the invention. The mixtures preferably contain 0 to 10% by weight, in particular 0.01 to 5% by weight, particularly preferably 0.01 to 3% by weight, of dopant.

[0256] [Table 23]

[0257] Stabilizers which can be added to the mixture according to the invention, for example in amounts of 0 to 10% by weight, are given below.

[0258] [Table 24]

[0259] [Table 25]

[0260] [Table 26]

[0261] [Table 27]

[0262] [Table 28]

[0263] Table E shows exemplary compounds which are preferably used as reactive mesogenic compounds in the LC media according to the invention. If the mixture according to the invention comprises one or more reactive compounds, they are preferably used in an amount of 0.01 to 5% by weight. For the polymerization, it may be necessary to add an initiator or a mixture of two or more initiators. The initiator or mixture of initiators is preferably added in an amount of 0.001 to 2% by weight, based on the mixture. Suitable initiators are, for example, Irgacure (BASF) or Irganox (BASF).

[0264] [Table 29]

[0265] [Table 30]

[0266] [Table 31]

[0267] [Table 32]

[0268] [Table 33]

[0269] [Table 34]

[0270] [Table 35]

[0271] [Table 36]

[0272] [Table 37]

[0273] [Table 38]

[0274] [Table 39]

[0275] [Table 40]

[0276] In a preferred embodiment, the mixture according to the invention comprises one or more polymerizable compounds, preferably selected from the polymerizable compounds of formulae RM-1 to RM-98. This type of medium is particularly suitable for PS-FFS and PS-IPS applications. Among the reactive mesogens shown in table E, 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. EXAMPLES

[0277] The following examples are intended to illustrate the invention without limiting it. In the examples, mp denotes the melting point in degrees Celsius, C denotes the clearing point of the liquid crystal substance in degrees Celsius; the boiling point is expressed in bp. Furthermore: C denotes the crystalline solid state, S denotes the smectic phase (the subscript denotes the type of phase), N denotes the nematic state, Ch denotes the cholesteric phase, I denotes the isotropic phase, and Tg denotes the glass transition point. The number between the two symbols indicates the transition temperature in degrees Celsius.

[0278] The host mixture used to determine the optical anisotropy Δn of the compound of formula I is the commercially available mixture ZLI-4792 (Merck). The dielectric anisotropy Δε is determined using the available mixture ZLI-2857. The physical data of the compound to be studied is obtained from the change in the dielectric constant of the host mixture after adding the compound to be studied and extrapolating to 100% of the compound used. Depending on the solubility, generally 10% of the compound to be studied is dissolved in the host mixture.

[0279] Unless otherwise indicated, parts or percentage data refer to parts by weight or percentages by weight.

[0280] Above and below, V0 represents the capacitance threshold voltage [V] at 20°C. n e represents the extraordinary refractive index at 20° C. and 589 nm, n0 represents the ordinary refractive index at 20° C. and 589 nm; Δn represents the optical anisotropy at 20° C. and 589 nm; ε ⊥ represents the dielectric constant perpendicular to the director at 20°C and 1 kHz, ε ∥ represents the dielectric constant parallel to the director at 20 °C and 1 kHz, Δε represents the dielectric anisotropy at 20° C. and 1 kHz; cl.p.,T(N,I) represents the clearing point [℃], γ1 represents the rotational viscosity [mPa·s] measured at 20 °C, determined by the rotation method in a magnetic field; K1 represents the elastic constant for "splay" deformation at 20°C [pN], K2 represents the elastic constant [pN] for the "twist" deformation at 20°C, K3 represents the elastic constant [pN] for "bend" deformation at 20°C, LTS stands for low temperature stability (nematic phase) determined in a test cell.

[0281] Unless expressly stated otherwise, all temperature values ​​given in this application, such as the melting point T(C,N), the transition point T(S,N) from the smectic phase (S) to the nematic phase (N) and the clearing point T(N,I), are given in degrees Celsius (°C). Mp stands for melting point and cl.p. is the clearing point. Furthermore, Tg=glassy state, C=crystalline state, N=nematic phase, S=smectic phase and I=isotropic phase. The numbers between these symbols indicate the transition temperatures.

[0282] In each case, unless expressly indicated otherwise, all physical properties are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", November 1997, Merck KGaA, Germany, and apply for a temperature of 20° C., Δn is determined at 589 nm and Δε is determined at 1 kHz.

[0283] In the present invention, the term "threshold voltage" refers to the capacitive threshold (V0), also known as the Freedericks threshold, unless otherwise specified. In the present invention, as is common and customary, the optical threshold is determined at 10% relative contrast (V 10 ) is also shown.

[0284] The display used to measure the capacitive threshold voltage consists of two flat parallel glass outer panels spaced 20 μm apart, each panel having an electrode layer on its inner side and a polyimide alignment layer on top, which produces a homeotropic edge alignment of the liquid crystal molecules.

[0285] The display used to measure the tilt angle consists of two flat parallel glass outer plates spaced 4 μm apart, each plate having an electrode layer on its inner side and a polyimide alignment layer on top, the two polyimide layers rubbed antiparallel to each other to produce a homeotropic edge alignment of the liquid crystal molecules.

[0286] The polymerizable compound is polymerized in the display or test cell by irradiating it with UVA light of a given intensity (usually 365 nm) for a predetermined time with a voltage applied to the display (usually 10 V to 30 V AC, 1 kHz). In the examples, unless otherwise stated, 50 mW / cm 2 A mercury lamp is used and its intensity is measured using a standard UV meter (model Ushio UNI meter) adjusted with a 365 nm bandpass filter.

[0287] The tilt angle is measured by a rotational crystal test (Autronic Melchers TBA-105). Low values ​​(i.e. large deviations from the 90° angle) correspond to large tilt in this specification.

[0288] The VHR values ​​are measured as follows: 0.3% of a polymerizable monomer compound is added to the LC host mixture and the resulting mixture is introduced into a TN-VHR test cell (rubbed at 90°, TN polyimide alignment layer, layer thickness d is about 6 μm). The HR values ​​are determined at 1 V, 60 Hz, 64 μs pulses after 5 min at 100° C. before and after 2 h of UV exposure (sunlight test) (measuring device: Autronic-Melchers VHRM-105).

[0289] To study the low-temperature stability (LTS), i.e., the stability of the LC mixture against spontaneous crystallization and precipitation of the individual components at low temperatures, a bottle containing 1 g of the LC / RM mixture was placed in storage at -10°C and periodically checked for the mixture crystallizing and precipitation.

[0290] The so-called "HTP" (helical twisting power) describes the helical twisting power (μm) of an optically active or chiral substance in an LC medium. Unless otherwise indicated, HTP is measured in the commercially available nematic LC host mixture MLD-6260 (Merck) at a temperature of 20° C.

[0291] Unless otherwise stated, all concentrations in this application are given in weight percent and relate to the corresponding whole mixture, including all solid or liquid crystal components, excluding the solvent. All physical properties are determined as described in "Merck Liquid Crystals, Physical Properties of Liquid Crystals", November 1997, Merck KGaA, Germany, and apply to a temperature of 20° C., unless otherwise expressly stated.

[0292] The following example mixtures with negative dielectric anisotropy are particularly suitable for liquid crystal displays with at least one planar alignment layer, such as IPS and FFS displays, in particular UB-FFS (=Ultra Bright FFS), and VA displays.

[0293] The following mixture examples may additionally contain a stabilizer, for example Tinuvin 770 (=bis(2,2,6,6-tetraethyl-4-piperidyl)sebacate), preferably in an amount of 0 to 1%.

[0294] <Mixture example>

[0295] [Table 41]

[0296] [Table 42]

[0297] [Table 43]

[0298] [Table 44]

[0299] [Table 45]

[0300]

Table 46

[0301]

Table 47

[0302]

Table 48

[0303]

Table 49

[0304]

Table 50

[0305]

Table 51

[0306]

Table 52

[0307]

Table 53

[0308]

Table 54

[0309]

Table 55

[0310]

Table 56

[0311] [Table 57]

[0312] [Table 58]

[0313] [Table 59]

[0314] [Table 60]

[0315] [Table 61]

[0316] [Table 62]

[0317] [Table 63]

[0318] <Example M24> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M1 is mixed with 0.3% of a polymerizable compound of the following formula:

[0319] [ka]

[0320] <Example M25> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M1 is mixed with 0.25% of a polymerizable compound of the following formula:

[0321] [ka]

[0322] <Example M26> For the preparation of a PS-VA mixture, 99.8% of the mixture according to example M1 is mixed with 0.2% of a polymerizable compound of the following formula:

[0323] [ka]

[0324] <Example M27> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M5 is mixed with 0.25% of a polymerizable compound of the following formula:

[0325] [ka]

[0326] <Example M28> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M11 is mixed with 0.25% of a polymerizable compound of the following formula:

[0327] [ka]

[0328] <Example M29> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M17 is mixed with 0.25% of a polymerizable compound of the following formula:

[0329] [ka]

[0330] <Example M30> For the preparation of a PS-VA mixture, 99.8% of the mixture according to example M18 is mixed with 0.2% of a polymerizable compound of the following formula:

[0331] [ka]

[0332] <Example M31> For the preparation of a PS-VA mixture, 99.8% of the mixture according to example M19 is mixed with 0.2% of a polymerizable compound of the following formula:

[0333] [ka]

[0334] <Example M32> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M20 is mixed with 0.25% of a polymerizable compound of the following formula:

[0335] [ka]

[0336] <Example M33> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M21 is mixed with 0.3% of a polymerizable compound of the following formula:

[0337] [ka]

[0338] <Example M34> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M2 is mixed with 0.3% of a polymerizable compound of the following formula:

[0339] [ka]

[0340] <Example M35> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M2 is mixed with 0.25% of a polymerizable compound of the following formula:

[0341] [ka]

[0342] <Example M36> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M2 is mixed with 0.3% of a polymerizable compound of the following formula:

[0343] [ka]

[0344] <Example M37> For the preparation of a PS-VA mixture, the mixture according to example M2 is mixed with a polymerizable compound RM-1 of the following formula:

[0345] [ka]

[0346] [Table 64]

[0347] [Table 65] Compared with the prior art, the mixtures according to the invention show a significantly higher rate of polymerization and at the same time a rapid establishment of the tilt angle.

[0348] <Example M38> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M2 is mixed with 0.25% of a polymerizable compound of the following formula:

[0349] [ka]

[0350] <Example M39> For the preparation of a PS-VA mixture, the mixture according to example M2 is mixed with the polymerizable compound RM-88 of the following formula:

[0351] [ka]

[0352] [Table 66]

[0353] [Table 67] Compared with the prior art, the mixtures according to the invention show a significantly higher rate of polymerization and at the same time a rapid establishment of the tilt angle.

[0354] <Example M40> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M3 is mixed with 0.25% of a polymerizable compound of the following formula:

[0355] [ka]

[0356] <Example M41> For the preparation of a PS-VA mixture, 99.8% of the mixture according to example M3 is mixed with 0.2% of a polymerizable compound of the following formula:

[0357] [ka]

[0358] <Example M42> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M3 is mixed with 0.3% of a polymerizable compound of the following formula:

[0359] [ka]

[0360] <Example M43> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M3 is mixed with 0.3% of a polymerizable compound of the following formula:

[0361] [ka]

[0362] <Example M44> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M3 is mixed with 0.3% of a polymerizable compound of the following formula:

[0363] [ka]

[0364] <Example M45> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M3 is mixed with 0.3% of a polymerizable compound of the following formula:

[0365] [ka]

[0366] <Example M46> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M4 is mixed with 0.3% of a polymerizable compound of the following formula:

[0367] [ka]

[0368] <Example M47> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M4 is mixed with 0.25% of a polymerizable compound of the following formula:

[0369] [ka]

[0370] <Example M48> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M4 is mixed with 0.25% of a polymerizable compound of the following formula:

[0371] [ka]

[0372] <Example M49> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M4 is mixed with 0.3% of a polymerizable compound of the following formula:

[0373] [ka]

[0374] <Example M50> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M5 is mixed with 0.25% of a polymerizable compound of the following formula:

[0375] [ka]

[0376] <Example M51> For the preparation of a PS-VA mixture, the mixture according to example M6 is mixed with a polymerizable compound RM-1 of the following formula:

[0377] [ka]

[0378] [Table 68]

[0379] [Table 69] Compared with the prior art, the mixtures according to the invention show a significantly higher rate of polymerization and at the same time a rapid establishment of the tilt angle.

[0380] <Example M52> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M6 is mixed with 0.3% of a polymerizable compound of the following formula:

[0381] [ka]

[0382] <Example M53> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M8 is mixed with 0.25% of a polymerizable compound of the following formula:

[0383] [ka]

[0384] <Example M54> For the preparation of a PS-VA mixture, 99.8% of the mixture according to example M8 is mixed with 0.2% of a polymerizable compound of the following formula:

[0385] [ka]

[0386] <Example M55> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M9 is mixed with 0.25% of a polymerizable compound of the following formula:

[0387] [ka]

[0388] <Example M56> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M10 is mixed with 0.25% of a polymerizable compound of the following formula:

[0389] [ka]

[0390] <Example M57> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M12 is mixed with 0.25% of a polymerizable compound of the following formula:

[0391] [ka]

[0392] <Example M58> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M12 is mixed with 0.25% of a polymerizable compound of the following formula:

[0393] [ka]

[0394] [Table 70]

[0395] [Table 71]

[0396] [Table 72]

[0397]

Table 73

[0398]

Table 74

[0399]

Table 75

[0400]

Table 76

[0401]

Table 77

[0402]

Table 78

[0403]

Table 79

[0404]

Table 80

[0405]

Table 81

[0406]

Table 82

[0407]

Table 83

[0408]

Table 84

[0409]

Table 85

[0410]

Table 86

[0411]

Table 87

[0412]

Table 88

[0413]

Table 89

[0414]

Table 90

[0415]

Table 91

[0416]

Table 92

[0417]

Table 93

[0418] [Table 94]

[0419] [Table 95]

[0420] [Table 96]

[0421] [Table 97]

[0422] [Table 98]

[0423] [Table 99]

[0424] [Table 100]

[0425] <Example M90> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M61 is mixed with 0.3% of a polymerizable compound of the following formula:

[0426] [ka]

[0427] <Example M91> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M64 is mixed with 0.25% of a polymerizable compound of the following formula:

[0428] [ka]

[0429] <Example M92> For the preparation of a PS-VA mixture, 99.8% of the mixture according to example M68 is mixed with 0.2% of a polymerizable compound of the following formula:

[0430] [ka]

[0431] <Example M93> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M69 is mixed with 0.25% of a polymerizable compound of the following formula:

[0432] [ka]

[0433] <Example M94> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M70 is mixed with 0.25% of a polymerizable compound of the following formula:

[0434] [ka]

[0435] <Example M95> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M72 is mixed with 0.25% of a polymerizable compound of the following formula:

[0436] [ka]

[0437] <Example M96> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M72 is mixed with 0.25% of a polymerizable compound of the following formula:

[0438] [ka]

[0439] [Table 101]

[0440] [Table 102]

[0441] [Table 103]

[0442] [Table 104]

[0443] <Example M101> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M97 is mixed with 0.25% of a polymerizable compound of the following formula:

[0444] [ka]

[0445] <Example M102> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M98 is mixed with 0.25% of a polymerizable compound of the following formula:

[0446] [ka]

[0447] <Example M103> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M99 is mixed with 0.25% of a polymerizable compound of the following formula:

[0448] [ka]

[0449] <Example M104> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M99 is mixed with 0.3% of a polymerizable compound of the following formula:

[0450] [ka]

[0451] <Example M105> For the preparation of a PS-VA mixture, 99.7% of the mixture according to example M100 is mixed with 0.3% of a polymerizable compound of the following formula:

[0452] [ka]

[0453] [Table 105]

[0454] [Table 106]

[0455] [Table 107]

[0456] <Example M109> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M108 is mixed with 0.3% of a polymerizable compound of the following formula:

[0457] [ka]

[0458] [Table 108]

[0459] [Table 109]

[0460] [Table 110]

[0461] [Table 111]

[0462] <Example M114> For the preparation of a PS-VA mixture, 99.75% of the mixture according to example M113 is mixed with 0.3% of a polymerizable compound of the following formula:

[0463] [ka]

Claims

1. comprising at least one compound of formula I, may comprise at least one compound selected from the group of compounds represented by formulae IIA-13 to IIA-31, IIA-44 to IIA-52, IIB-7 to IIB-10, L-1 to L-11, T-1 to T-12, T14 to T-21, BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1, BS-2, O-6, P-1 to P-4, Z-1 to Z-9 and B-1a; However, it may contain at least one compound selected from the group of compounds represented by formulae IIA-13, IIA-14, IIA-19 to IIA-23, IIA-26 to IIA-31, IIA-44 to IIA-52, L-1 to L-11, BF-1, BF-2, BS-1, BS-2, O-6, P-1 to P-4, Z-1 to Z-9, and B-1a, However, the compound represented by the acronym CC-3-V in the formula [Chemical Formula 24] is included. A liquid crystal medium comprising: 【Chemistry 1】 (In the formula, R 1 and R 1* each independently of the other represents alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH 2 The groups are -C≡C-, -CF so that the O atoms are not directly linked to each other. 2 O-, -CH=CH-, 【Chemistry 2】 may be replaced by -O-, -CO-O-, or -O-CO-, provided that in addition, one or more H atoms may be replaced by halogen; Z 1 and Z 2 are each independently a single bond, -CH 2 CH 2 -, -CH=CH-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -COO-, -OCO-, -C 2 F 4 -, -C≡C-, -CF=CF-, or -CH=CHCHO-; L 1~3 are each independently F, Cl, CF 3 , O.C.F. 3 or CHF 2 Represents.) 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 (In the formula, alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, Alkenyl and alkenyl * each independently represent a straight-chain alkenyl group having 2 to 6 C atoms, p represents 0, 1 or 2, and (O) represents a single bond or -O-.) 【Chemistry 9】 【Chemistry 10】 (In the formula, R, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 11】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, (O) represents a single bond or -O-; alkyl represents an alkyl group having 1 to 6 C atoms, and s represents 1 or 2. 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 (In the formula, R represents a straight-chain alkyl or alkoxy group having 1 to 7 C atoms or an alkenyl group having 2 to 6 C atoms, (O) represents a single bond or -O-; m represents 0, 1, 2, 3, 4, 5 or 6; n represents 0, 1, 2, 3 or 4. 【Chemistry 15】 (In the formula, R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 16】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, c represents 0, 1 or 2; d represents 1 or 2. 【Chemistry 17】 (In the formula, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 18】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by --, --OC--O-- or --O--CO--.) 【Chemistry 19】 (In the formula, R represents straight-chain alkyl, alkoxy or alkenyl, each having up to 6 C atoms, X is F, Cl, CF 3 , O.C.F. 3 , OCHFCF 3 or CCF 2 CHFCF 3 Represents.) 【Chemistry 20】 【Chemistry 21】 (In the formula, R is H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemical 22】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, (O) represents a single bond or -O-; alkyl represents an alkyl group having 1 to 6 C atoms. 【Chemistry 23】 (In the formula, alkyl * represents an alkyl group having 1 to 6 C atoms. 【Chemistry 24】

2. 2. The liquid-crystalline medium according to claim 1, characterized in that the proportion of compounds of the acronym CC-3-V in the liquid-crystalline medium as a whole is 5 to 60%.

3. 3. The liquid-crystalline medium according to claim 2, characterized in that the proportion of compounds of the acronym CC-3-V as a whole in the liquid-crystalline medium is 10 to 55%.

4. comprising at least one compound of formula I, may comprise at least one compound selected from the group of compounds represented by formulae IIA-13 to IIA-31, IIA-44 to IIA-52, IIB-7 to IIB-10, L-1 to L-11, T-1 to T-12, T14 to T-21, BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1, BS-2, O-6, P-1 to P-4, Z-1 to Z-9 and B-1a; However, it may contain at least one compound selected from the group of compounds represented by formulae IIA-13, IIA-14, IIA-19 to IIA-23, IIA-26 to IIA-31, IIA-44 to IIA-52, L-1 to L-11, BF-1, BF-2, BS-1, BS-2, O-6, P-1 to P-4, Z-1 to Z-9, and B-1a, However, the compound contains at least one compound selected from the group of compounds represented by formulas L-4, BF-1, BS-1, IIA-50, or O-6. A liquid crystal medium comprising: 【Chemistry 25】 (In the formula, R 1 and R 1* each independently of the other represents alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH 2 The groups are -C≡C-, -CF so that the O atoms are not directly linked to each other. 2 O-, -CH=CH-, 【Chemistry 26】 may be replaced by -O-, -CO-O-, or -O-CO-, provided that in addition, one or more H atoms may be replaced by halogen; Z 1 and Z 2 are each independently a single bond, -CH 2 CH 2 -, -CH=CH-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -COO-, -OCO-, -C 2 F 4 -, -C≡C-, -CF=CF-, or -CH=CHCHO-; L 1~3 are each independently F, Cl, CF 3 , O.C.F. 3 or CHF 2 Represents.) 【Chemical 27】 【Chemistry 28】 【Chemical formula 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 (In the formula, alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, Alkenyl and alkenyl * each independently represent a straight-chain alkenyl group having 2 to 6 C atoms, p represents 0, 1 or 2, and (O) represents a single bond or -O-.) 【Chemical 33】 【Chemical 34】 (In the formula, R, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 35】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, (O) represents a single bond or -O-; alkyl represents an alkyl group having 1 to 6 C atoms, and s represents 1 or 2. 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 (In the formula, R represents a straight-chain alkyl or alkoxy group having 1 to 7 C atoms or an alkenyl group having 2 to 6 C atoms, (O) represents a single bond or -O-; m represents 0, 1, 2, 3, 4, 5 or 6; n represents 0, 1, 2, 3 or 4. 【Chemical 39】 (In the formula, R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 40】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, c represents 0, 1 or 2; d represents 1 or 2. 【Chemistry 41】 (In the formula, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 42】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by --, --OC--O-- or --O--CO--.) 【Chemistry 43】 (In the formula, R represents straight-chain alkyl, alkoxy or alkenyl, each having up to 6 C atoms, X is F, Cl, CF 3 , O.C.F. 3 , OCHFCF 3 or CCF 2 CHFCF 3 Represents.) 【Chemistry 44】 【Chemistry 45】 (In the formula, R is H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 46】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, (O) represents a single bond or -O-; alkyl represents an alkyl group having 1 to 6 C atoms. 【Chemistry 47】 (In the formula, alkyl * represents an alkyl group having 1 to 6 C atoms.

5. comprising at least one compound of formula I, may comprise at least one compound selected from the group of compounds represented by formulae IIA-13 to IIA-31, IIA-44 to IIA-52, IIB-7 to IIB-10, L-1 to L-11, T-1 to T-12, T14 to T-21, BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1, BS-2, O-6, P-1 to P-4, Z-1 to Z-9 and B-1a; However, it may contain at least one compound selected from the group of compounds represented by formulae IIA-13, IIA-14, IIA-19 to IIA-23, IIA-26 to IIA-31, IIA-44 to IIA-52, L-1 to L-11, BF-1, BF-2, BS-1, BS-2, O-6, P-1 to P-4, Z-1 to Z-9, and B-1a, provided that the compound contains at least one compound selected from the group consisting of compounds represented by formulas L-4, BF-1, BS-1, IIA-50, or O-6, However, the compound represented by the acronym CC-3-V in the formula [Chemical Formula 71] is included. A liquid crystal medium comprising: 【Chemistry 48】 (In the formula, R 1 and R 1* each independently of the other represents alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH 2 The groups are -C≡C-, -CF so that the O atoms are not directly linked to each other. 2 O-, -CH=CH-, 【Chemistry 49】 may be replaced by -O-, -CO-O-, or -O-CO-, provided that in addition, one or more H atoms may be replaced by halogen; Z 1 and Z 2 are each independently a single bond, -CH 2 CH 2 -, -CH=CH-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -COO-, -OCO-, -C 2 F 4 -, -C≡C-, -CF=CF-, or -CH=CHCHO-; L 1~3 are each independently F, Cl, CF 3 , O.C.F. 3 or CHF 2 Represents.) 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 (In the formula, alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, Alkenyl and alkenyl * each independently represent a straight-chain alkenyl group having 2 to 6 C atoms, p represents 0, 1 or 2, and (O) represents a single bond or -O-.) 【Chemistry 56】 【Chemistry 57】 (In the formula, R, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 58】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, (O) represents a single bond or -O-; alkyl represents an alkyl group having 1 to 6 C atoms, and s represents 1 or 2. 【Chemistry 59】 【Chemistry 60】 【Chemistry 61】 (In the formula, R represents a straight-chain alkyl or alkoxy group having 1 to 7 C atoms or an alkenyl group having 2 to 6 C atoms, (O) represents a single bond or -O-; m represents 0, 1, 2, 3, 4, 5 or 6; n represents 0, 1, 2, 3 or 4. 【Chemistry 62】 (In the formula, R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 63】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, c represents 0, 1 or 2; d represents 1 or 2. 【Chemistry 64】 (In the formula, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 65】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by --, --OC--O-- or --O--CO--.) 【Chemistry 66】 (In the formula, R represents straight-chain alkyl, alkoxy or alkenyl, each having up to 6 C atoms, X is F, Cl, CF 3 , O.C.F. 3 , OCHFCF 3 or CCF 2 CHFCF 3 Represents.) 【Chemistry 67】 【Chemistry 68】 (In the formula, R is H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 69】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, (O) represents a single bond or -O-; alkyl represents an alkyl group having 1 to 6 C atoms. 【Chemistry 70】 (In the formula, alkyl * represents an alkyl group having 1 to 6 C atoms. 【Chemistry 71】 6. The liquid-crystalline medium according to claim 1, comprising as compound of the formula I at least one compound of the formulae I-a to I-h. 【Chemical Formula 72】 (In the formula, R 1 and R 1* has the meaning given in claim 1.

7. The liquid-crystalline medium according to claim 1, comprising as compound of the formula I at least one compound of the formulae I-a-1 to I-a-36. 【Chemical Formula 73】 【Chemical 74】 【Chemistry 75】 【Chemical 76】

8. 8. Liquid-crystalline medium according to claim 1, characterized in that the proportion of compounds of the formula I in the overall mixture is from 1 to 30% by weight.

9. additionally comprising one or more compounds selected from the group of compounds of formula IIA, IIB, and IIC, with the proviso that one or more of the compounds of formula IIA, IIB, and IIC are not compounds IIA-13 to IIA-31, IIA-44 to IIA-52, and IIB-7 to IIB-10 9. The liquid-crystalline medium according to claim 1 . 【Chemical 77】 (In the formula, R 2A , R 2B and R 2C are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemical 78】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, L 1~4 are each independently F, Cl, CF 3 or CHF 2 represents Z 2 and Z 2’ are each independently a single bond, -CH 2 CH 2 -, -CH=CH-, -CF 2 O-, -OCF 2 --, --CH 2 O-, -OCH 2 -, -COO-, -OCO-, -C 2 F 4 -, -CF=CF-, -C≡C-, -CH=CHCH 2 represents O-, p represents 0, 1 or 2; q represents 0 or 1, and v represents 1 to 6.

10. 10. Liquid-crystalline medium according to claim 1, additionally comprising one or more compounds of the formula III. 【Chemical Formula 79】 (In the formula, R 31 and R 32 each independently of one another represents a straight-chain alkyl, alkenyl, alkoxy, alkoxyalkyl or alkenyloxy group having up to 12 C atoms, and 【Chemistry 80】 Z 3 is a single bond, -CH 2 CH 2 -, -CH=CH-, -CF 2 O-, -OCF 2 --, --CH 2 O-, -OCH 2 -, -COO-, -OCO-, -C 2 F 4 -, -C 4 H 8 -, -C≡C-, -CF=CF-.)

11. 11. The liquid-crystalline medium according to claim 1, additionally comprising one or more compounds of the formulae O-1 to O-5 and O-7 to O-17. 【Chemistry 81】 【Chemistry 82】 (In the formula, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 83】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by --, --OC--O-- or --O--CO--.)

12. 12. The liquid-crystalline medium according to claim 1, additionally comprising one or more compounds of the following formulae: 【Chemistry 84】 【Chemistry 85】 【Chemistry 86】 【Chemistry 87】 【Chemistry 88】

13. 13. The liquid-crystalline medium according to claim 1, comprising one or more compounds selected from the group consisting of compounds of the following formulae: 【Chemistry 89】 【Chemistry 90】 (In the formula, R, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 91】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 C atoms, Alkenyl and alkenyl * each independently represent a straight-chain alkenyl group having 2 to 6 C atoms, (O)alkyl, (O)-alkyl and (O)alkyl * each independently represents alkyl or O-alkyl, (O)alkenyl * each independently represents alkenyl or O-alkenyl, m represents 0, 1, 2, 3, 4, 5 or 6; n represents 0, 1, 2, 3 or 4; x represents 1 to 6; c represents 0, 1 or 2.

14. 14. The liquid-crystalline medium according to claim 1, which comprises at least one polymerizable compound.

15. 15. The liquid-crystalline medium according to claim 1, further comprising one or more additives.

16. 16. Liquid-crystalline medium according to claim 1, characterized in that the additives are selected from the group consisting of free-radical scavengers, antioxidants and / or UV stabilizers.

17. 2. A process for the preparation of a liquid-crystalline medium according to claim 1, characterized in that at least one compound of formula I is mixed with a compound of the acronym CC-3-V and, optionally, one or more additives and one or more polymerizable compounds.

18. 5. A process for the preparation of a liquid-crystalline medium according to claim 4, characterized in that at least one compound of the formula I is mixed with at least one compound selected from the group of the compounds of the formulae L-4, BF-1, BS-1, IIA-50 or O-6, and optionally one or more additives and one or more polymerizable compounds are added.

19. 6. Process for the preparation of a liquid-crystalline medium according to claim 5, characterized in that at least one compound of the formula I is mixed with at least one compound selected from the group of the compounds of the acronym CC-3-V and of the formulae L-4, BF-1, BS-1, IIA-50 or O-6, and optionally with one or more additives and one or more polymerizable compounds.

20. Use of a liquid-crystalline medium according to any one of claims 1 to 16 in an electro-optical display.

21. Electro-optical display with active matrix address, characterized in that it contains as dielectric a liquid-crystalline medium according to any one of claims 1 to 16.

22. 22. An electro-optical display according to claim 21, characterized in that it is a VA, PSA, PA-VA, PS-VA, PALC, IPS, PS-IPS, FFS, PS-FFS display.

23. 23. An electro-optic display according to claim 22 which is an IPS, PS-IPS, FFS or PS-FFS display with a planar alignment layer.

24. 17. The liquid-crystalline medium according to claim 1, further comprising at least one compound of the formula IIC-1. 【Chemistry 92】 (In the formula, alkyl and alkyl * each independently represents a linear alkyl group having 1 to 6 C atoms.

25. 17. The liquid-crystalline medium according to claim 1, further comprising one or more biphenyls of the formulae B-1 to B-3. 【Chemistry 93】 (In the formula, alkyl and alkyl * each independently of one another represents a straight-chain alkyl group having 1 to 6 C atoms, and Alkenyl and alkenyl * each independently represents a straight-chain alkenyl group having 2 to 6 C atoms.

26. 17. The liquid-crystalline medium according to claim 1, which comprises one or more compounds of the formulae Z-1 to Z-9. 【Chemistry 94】 【Chemistry 95】 (In the formula, R is H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 96】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by -, -OC-O- or -O-CO-, (O) represents a single bond or -O-; alkyl represents an alkyl group having 1 to 6 C atoms.

27. 17. The liquid-crystalline medium according to claim 1, further comprising one or more of the following compounds: 【Chemistry 97】

28. 17. The liquid-crystalline medium according to claim 1, additionally comprising a compound of the formula CC-3-V1. 【Chemistry 98】

29. 29. The liquid-crystalline medium according to claim 28, wherein the total concentration of compounds of the formula CC-3-V1 is from 10 to 65% by weight.

30. 17. The liquid-crystalline medium according to claim 1, further comprising at least one compound selected from the formulae O-10a and O-10b and at least one compound selected from the formulae O-17a to O-17d. 【Chemistry 99】

31. 31. The liquid-crystalline medium according to claim 30, wherein the total amount of compounds of the formulae O-10a and / or O-10b and of the formulae O-17a to O-17d is 5 to 40% by weight.

32. 31. Liquid-crystalline medium according to claim 30, characterized in that it comprises at least one compound of the formula O-10a and at least one compound of the formula O-17a.

33. 33. The liquid-crystalline medium according to claim 32, wherein the total amount of compounds of the formulae O-10a and O-17a is from 15 to 35% by weight.

34. 31. Liquid-crystalline medium according to claim 30, characterized in that it comprises at least one compound of the formula O-10b and at least one compound of the formula O-17a.

35. 35. The liquid-crystalline medium according to claim 34, wherein the total amount of compounds of the formulae O-10b and O-17a is from 15 to 35% by weight.

36. 31. Liquid-crystalline medium according to claim 30, comprising at least one compound of the formulae O-10a, at least one compound of the formulae O-10b and at least one compound of the formulae O-17a.

37. 37. The liquid-crystalline medium according to claim 36, wherein the total amount of compounds of the formulae O-10a, O-10b and O-17a is 15 to 35% by weight.

38. 17. The liquid-crystalline medium according to claim 1, further comprising at least one compound selected from the formulae O-7, O-10 and O-17. 【Chemistry 100】 (In the formula, R, R 1 and R 2 are each independently H, unsubstituted, CN or CF 3 or at least one halogen, provided that in addition, one or more CH 2 The groups are arranged in such a way that the O atoms are not directly linked to each other, such as -O-, -S-, 【Chemistry 101】 -C≡C-, -CF 2 O-, -OCF 2 may be replaced by --, --OC--O-- or --O--CO--.)

39. In the compounds of formulae O-7 and O-17, R 1 is alkyl having 1 to 6 C atoms or alkenyl having 2 to 6 C atoms, R 2 is alkenyl having 2 to 6 C atoms, In the compound of formula O-10, R 1 is alkyl having 1 to 6 C atoms or alkenyl having 2 to 6 C atoms, R 2 is alkyl having 1 to 6 C atoms 39. The liquid-crystalline medium according to claim 38.

40. 17. The liquid-crystalline medium according to claim 1, wherein the total amount of compounds of the formulae BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1 and BS-2 is from 3 to 20% by weight.

41. 17. The liquid-crystalline medium according to claim 1, comprising at least one compound of the formulae BC, CR, BF-1 and BS-1, wherein the compounds of the formulae BC, CR, BF-1 and BS-1 are selected from the compounds of the formulae BC-1 to BC-7, CR-1 to CR-5, BF-1a to BF-1c, BS-1a to BS-1c. 【Chemistry 102】 【Chemistry 103】 【Chemistry 104】 (In the formula, alkyl and alkyl * each independently of one another represents a straight-chain alkyl group having 1 to 6 C atoms, and Alkenyl and alkenyl * each independently represents a straight-chain alkenyl group having 2 to 6 C atoms.

42. 17. The liquid-crystalline medium according to claim 1, which comprises one, two or three compounds selected from the formulae BC-2, BF-1 and BF-2.

43. 17. A liquid-crystalline medium according to claim 1, further comprising one or more compounds of the formula In. 【Chemistry 105】 (In the formula, R 11 , R 12 , R 13 each independently represent a straight-chain alkyl, alkoxy, alkoxyalkyl or alkenyl group having 1 to 6 C atoms, R 12 and R 13 represents additionally a halogen, preferably F, 【Chemistry 106】 represents i represents 0, 1 or 2.

44. 17. The liquid-crystalline medium according to claim 1, further comprising one or more polymerizable compounds selected from compounds of the formula M 【Chemistry 107】 (wherein each group has the following meaning: R Ma and R Mb are each independently P, P-Sp-, H, a halogen, or SF 5 , NO 2 , alkyl, alkenyl or alkynyl groups, provided that at least one group R Ma and R Mb preferably represents or contains the group P or P-Sp-, P represents a polymerizable group; Sp represents a spacer group or a single bond; A M1 and A M2 denote, each independently of one another, an aromatic, heteroaromatic, alicyclic or heterocyclic group which preferably has 4 to 25 ring atoms, preferably C atoms, which may also include or contain fused rings and which may be mono- or polysubstituted by L, L is P, P-Sp-, OH, CH 2 OH, F, Cl, Br, I, -CN, -NO 2 , -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x ) 2 , -C(=O)Y 1 , -C(=O)R x , -N(R x ) 2 , optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms (in addition, one or more H atoms in these groups may be replaced by F, Cl, P or P-Sp-), preferably P, P-Sp-, H, OH, CH 2 OH, halogen, SF 5 , NO 2 , an alkyl, alkenyl or alkynyl group; Y 1 represents a halogen, Z M1 is -O-, -S-, -CO-, -CO-O-, -OCO-, -O-CO-O-, -OCH 2 --, --CH 2 O-, -SCH 2 --, --CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -(CH 2 ) n1 -, -CF 2 CH 2 --, --CH 2 CF 2 -, - (CF 2 ) n1 -, -CH=CH-, -CF=CF-, -C≡C-, -CH=CH-, -COO-, -OCO-CH=CH-, CR 0 R 00 or a single bond, R 0 and R 00 each independently of one another denotes H or alkyl having 1 to 12 C atoms, R x is P, P-Sp-, H, halogen, linear, branched or cyclic alkyl having 1 to 25 C atoms (but in addition, one or more non-adjacent CH 2 The group 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 linked to one another, with the proviso that in addition one or more H atoms may be replaced by F, Cl, P or P-Sp-), an optionally substituted aryl or aryloxy group having 6 to 40 C atoms or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms, m1 represents 0, 1, 2, 3 or 4, and n1 represents 1, 2, 3 or 4; However, the group R Ma , R Mb and at least one, preferably one, two or three, particularly preferably one or two of the substituents L present represents or contains at least one of the groups P or P-Sp-.

45. 17. The liquid-crystalline medium according to claim 1, further comprising one or more polymerizable compounds selected from the compounds of the formulae M1 to M44. 【Chemistry 108】 【Chemistry 109】 【Chemistry 110】 【Chemistry 111】 【Chemistry 112】 【Chemistry 113】 (wherein each group has the following meaning: P 1 , P 2 and P 3 are the same or different and each represents a polymerizable group, Sp 1 , Sp 2 and Sp 3 are each independently a single bond or, preferably, Sp a represents a spacer group having one of the meanings given above and below for However, the present group P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 At least one of - is R aa one or more groups P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - is R aa may also represent R aa represents H, F, Cl, CN, or a linear or branched alkyl having 1 to 25 C atoms, provided that in addition thereto one or more non-adjacent CH 2 The groups are each independently of one another C(R 0 ) = C(R 00 )-, -C≡C-, -N(R 0 ) -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, provided that in addition, one or more H atoms are replaced by F, Cl, CN or P 1 -Sp 1 may be replaced by -, R 0 , R 00 each, independently of one another, identically or differently at each occurrence, represents H or alkyl having 1 to 12 C atoms, R y and R z are each independently H, F, or CH 3 or CF 3 represents X 1 , X 2 and X 3 each independently represents -CO-O-, -O-CO- or a single bond, Z 1 -O-, -CO-, -C(R y R z ) - or -CF 2 CF 2 - represents Z 2 and Z 3 are each independently -CO-O-, -O-CO-, or -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 - or - (CH 2 ) n -, where n is 2, 3 or 4; L is the same or different in each occurrence and is selected from the group consisting of F, Cl, CN, SCN, SF 5 or an alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, which may be linear or branched, monofluorinated or polyfluorinated, and has 1 to 12 C atoms, L′ and L″ each independently represent H, F or Cl; r represents 0, 1, 2, 3 or 4; s represents 0, 1, 2 or 3; t represents 0, 1 or 2; x represents 0 or 1.

46. 17. The liquid-crystalline medium according to claim 1, further comprising one or more stabilizers selected from the following compounds in an amount of up to 10% by weight: 【Table 1】 【Table 2】 【Table 3】 【Table 4】 【Table 5】

47. 17. The liquid-crystalline medium according to claim 1, further comprising one or more reactive mesogens selected from the following compounds: 【Table 6】 【Table 7】 【Table 8】 【Table 9】 【Table 10】 【Table 11】 【Table 12】 【Table 13】 【Table 14】 【Table 15】 【Table 16】 【Table 17】

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