LCD Media

Abstract

To provide a liquid-crystalline medium suitable for an active matrix display.SOLUTION: The present invention relates to a liquid-crystalline medium which comprise at least one compound of the formula I and to the use thereof for an active matrix display, in particular for an active matrix display based on the VA, PSA, PS-VA, PALC, FFS, PS-FFS, PS-IPS, or IPS effect. (In the formula, R1 and R1* each, independently of one another, denote an alkyl or alkoxy radical having 1 to 15 C atoms; Z1 and Z2 each, independently of one another, denote a single bond, -CH2CH2-, -CH=CH-, etc.; and L1-3 each, independently of one another, represent F, Cl, CF3, etc.)SELECTED DRAWING: None

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, provided that in addition, one or more CH groups in these groups are each independently selected from -C≡C-, -CF2O-, -CH=CH-, ...

[0003] [ka] -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, -CH2CH2-, -CH=CH-, -C2O-, -OCH2-, -CF2O-, -OCF2-, -COO-, -OCO-, -C2F4-, -C≡C-, -CF=CF-, or -CH=CHCHO-; L 1~3 each independently represent 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 IPS (in-plane switching) or FFS (fringe field switching) 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 described in 1971 (M.F.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)), followed by papers by J.F.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, a liquid-crystalline phase must have a high value of the ratio of the elastic constants K3 / K1, a high value of the optical anisotropy Δn, and a value of the dielectric anisotropy Δε of less than or equal to −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, C.T. 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. 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 15.2: "Development of High Quality LCDTV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 754-757 (Non-Patent Document 11)) are currently one of the three most important types of LCD displays, particularly for television applications.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 technologies have been compared in a general way, for example, in the SID Seminar at 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 a video-compatible response time, especially in switching grayscales (gray-shading), remains a problem that has yet to be satisfactorily solved.

[0008] The industrial application of this effect in electro-optical display elements requires LC phases that 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, commercially usable LC phases are required to have a liquid crystal mesophase within a suitable temperature range and low viscosity.

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

[0011] Matrix liquid-crystal displays (MLC displays) are known. Non-linear elements that can be used to switch each individual pixel are, for example, active elements (i.e. transistors). The term "active matrix" is 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 preferred and more promising 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. This 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 switchable pixel.

[0016] The term MLC display is used herein to cover any matrix display with integrated non-linear elements, i.e. displays that, in addition to the active matrix, also include 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 time, MLC displays also suffer from problems due to the insufficient resistivity of the liquid crystal mixture [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. Because the resistivity of the liquid crystal mixture generally decreases over the lifetime of an MLC display due to interactions with the display's internal surfaces, a high (initial) resistance is crucial for the display to have acceptable resistance values ​​over long periods of operation.

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

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

[0020] VA displays have a significantly better viewing angle dependence and are therefore primarily used for televisions and monitors. However, there is a continuing demand for improved response times. 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., vol. 19 (1971), pp. 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, C.T. 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 Applications," 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., Proc. Eurodisplay, Vol. 84, September 1984, A210-288, "Matrix LCD Controlled by Double Stage Diode Rings", 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, pp. 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 based on the ECB effect or the IPS or FFS effect, in particular for use in monitors and televisions, which do not have the above-mentioned defects or only have them to a reduced extent, and 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 improved reliability behavior, in particular that image sticking does not occur or is significantly reduced 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 in 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 characteristics and good low-temperature behavior.The liquid crystal mixtures according to the invention are particularly characterized by a very good ratio of rotational viscosity to elastic constant, preferably K3.

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

[0025] The mixtures according to the invention exhibit 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, relatively high values ​​for retention, and at the same time very good low-temperature stability at −20° C. and −30° C., as well as very low rotational viscosity and short response times. The mixtures according to the invention furthermore exhibit, in addition to an improved rotational viscosity γ1, a low elastic constant K for improved response times. 33 The compounds of formula I are particularly suitable for the preparation of liquid-crystal mixtures with negative Δε. DETAILED DESCRIPTION OF THE INVENTION

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

[0027] In 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 also alkenyl and alkoxy.

[0028] In 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 represent a single bond.

[0030] Base L 1 , L 2 and L 3 Preferably, each independently 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, 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 represent 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 as follows: a) Liquid-crystalline medium which additionally 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 represent H, an alkyl or alkenyl group having up to 15 C atoms which is unsubstituted or monosubstituted by CN or CF3 or at least monosubstituted by halogen, provided that in addition, one or more CH2 groups in these groups are not joined together by -O-, -S-, ...

[0049] [ka] may be replaced by -C≡C-, -CF2O-, -OCF2-, -OC-O- or -O-CO-; L 1~4 each independently represent 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-, -CF4-, -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 compounds 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 also alkenyl, in particular CH2=CH, CH3CH=CH, C2H5CH=CH, 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 represents F. 2 and Z 2’ preferably each independently of one another represents a single bond or also 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 represent 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 carbon atoms.

[0062] Particularly preferred mixtures according to the invention comprise one or more compounds of formula 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 formula IIA and / or IIB in the mixture as a whole is preferably at least 20% by weight.

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

[0071] alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 carbon 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 denotes an alkyl or alkoxy group having 1 to 6 C atoms; z and m each independently of one another denotes 1 to 6; x denotes 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 the formulae T-1, T-2, T-19 and T-20. In these compounds, R preferably represents alkyl, furthermore alkoxy, each having 1 to 6 carbon atoms. In compounds of the formula T-19, R preferably represents alkyl or alkenyl, in particular alkyl. In compounds of the 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 carbon 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 formulae B-1 to B-3, the compounds of 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 formula B-1a are in particular compounds 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 containing a non-terminal double bond in the alkenyl side chain:

[0109] [ka]

[0110] The proportion of compounds of formula O-17 in the mixture as a whole 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% by weight or more, in particular 10% by weight or more:

[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 group consisting of the following 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 formula 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 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 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] A very particularly preferred mixture comprises 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 an amount 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 containing 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 of each other, R 2A and preferably denotes straight-chain alkyl, straight-chain alkoxy or straight-chain alkenyl, and Z 1 and Z 2 represent, independently of one another, -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 formula 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 of each other, R 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 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 carbon atoms.

[0142] Very particular preference is given to mixtures comprising one, two or three compounds of the formulae BC-2, BF-1 and / or BF-2.

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

[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 concentrations of 5% by weight or more, in particular 5 to 30% by weight, very particularly preferably 5 to 25% by weight.

[0150] n) Preferred mixtures additionally comprise 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 carbon atoms. s represents 1 or 2.

[0153] Compounds of formulae L-1 and L-4, especially L-4, are particularly preferred.

[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 total 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 total 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 to 30%, based on the total 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 to 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 total mixture, include.

[0157] Furthermore, the mixtures according to the invention are preferred, which include the following mixture concepts (n and m each independently represent 1 to 6): CPY-n-Om and CY-n-Om, preferably in a concentration of 10 to 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 to 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 of each other, R 2A It means Alkyl and alkyl * each independently represent a linear alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl * each independently represents a linear alkenyl group having 2 to 6 carbon 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 further 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-crystalline media according to the invention preferably have a nematic phase from -20°C or lower to 70°C or higher, particularly preferably from -30°C or lower to 80°C or higher, very particularly preferably from -40°C or lower to 90°C or higher.

[0163] In this document, the expression "having a nematic phase" means, on the one hand, that no smectic phase or crystallization is observed at low temperatures at the corresponding temperatures, and, on the other hand, that heating from the nematic phase does not result in clearing. Low-temperature studies are carried out in a flow viscometer at the corresponding temperatures and are confirmed by storage for at least 100 hours in test cells with a layer thickness corresponding to the electro-optical use. A medium is considered stable at this temperature if its storage stability at a temperature of -20°C in the corresponding test cell is 1000 hours or more. At temperatures of -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At higher temperatures, the clearing point is measured conventionally in capillary tubes.

[0164] The liquid crystal mixture preferably has a nematic phase range of at least 60 K and a maximum of 30 mm 2 ·s -1 Flow viscosity ν 20 It 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 or less, in particular 120 mPa·s or less.

[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 2.5 V or less, very particularly preferably 2.3 V or less.

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

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

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

[0171] In the present invention, the term "dielectrically positive compound" refers to a compound with Δε > 1.5, the term "dielectrically neutral compound" refers to one with -1.5 ≦ Δε ≦ 1.5, and the term "dielectrically negative compound" refers to one with Δε < -1.5. Herein, the dielectric anisotropy of a compound is determined by dissolving 10% of the compound 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 measurement 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 VAN, MVA, (S)-PVA, ASV, PSA (polymer sustained VA) and PS-VA (polymer stabilized VA), etc. They are also 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, imparting 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 of 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 with a flow viscosity of

[0181] Component B is a monotropic or enantiotropic nematic, does not have a smectic phase, and can prevent the occurrence of a smectic phase in a liquid crystal mixture down 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 smectic phase suppression achieved.

[0182] The mixture may also contain a component C containing compounds with 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 total mixture.

[0183] If the mixture according to the invention comprises one or more compounds having a dielectric anisotropy Δε of 1.5 or more, these are preferably one type of compound 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 2 to 15%, in particular in a concentration of 2 to 10%.

[0186] Compounds of the following formulae are particularly preferred and are preferably used in amounts of 2 to 15% in the mixtures according to the invention:

[0187] [ka]

[0188] Additionally, 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 formula IIA, IIB and / or IIC, and optionally one or more compounds of formula O-17.

[0190] In addition to the compounds of formula I and the compounds of formulae 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 other constituents are preferably selected from known substances that fall into the classes of nematic or nematogenic substances, in particular 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 constituents of liquid crystal phases of this type can be characterized by formula IV.

[0193] [ka] wherein L and E represent, respectively, a carbon or heterocyclic ring structure 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, NO, NCS, CF, SF, OCF, F, Cl or Br.

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

[0195] It will also be apparent to 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 (RMs), as disclosed, for example, in U.S. 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 contain initiators, as described, for example, in U.S. Pat. No. 6,781,665. Initiators, such as Irganox-1076 from BASF, are preferably added to the mixtures containing the polymerizable compounds in an amount of 0 to 1%. Mixtures of this type can be used for so-called polymer-stabilized VA (PS-VA) or PSA (polymer-sustained VA) modes, in which polymerization of the reactive mesogen is intended to occur in the liquid crystal mixture. A prerequisite for this is that the liquid crystal mixture does not contain any polymerizable components that would also polymerize under the conditions in which the RMs polymerize. Polymerization is preferably carried out under the following conditions:

[0197] A UV-A lamp of a predetermined intensity is used for a predetermined period of time, and the polymerizable component is polymerized in the cell while applying a voltage (typically 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 is typically 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 represent P, P-Sp-, H, halogen, SF5, NO2, an alkyl, alkenyl or alkynyl group, 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 each independently represent an aromatic, heteroaromatic, alicyclic or heterocyclic group which preferably has 4 to 25 ring atoms, preferably C atoms, and 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 straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms (provided that 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 O and / or S atoms are not directly linked to one another, 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 may each independently be -C(R 0 )=C(R 00 )-, -C≡C-, -N(R 00 )-, -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 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 (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 ... 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, provided that all of these groups 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 (provided that 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 (provided 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 O and / or S atoms are not directly linked to each other, and 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 denotes P or P-Sp-.

[0204] Suitable and preferred RMs or monomers or comonomers for use in the liquid-crystalline media according to the invention and in PS-VA or PSA displays are selected, for example, 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—, wherein p1 is an integer of 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 independently be 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 in 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-, -CHO-, -OCH-, -CFO-, -OCF- or -(CH) n -, where n is 2, 3 or 4; L is, identically or differently in each occurrence, F, Cl, CN, SCN, SF5 or linear or branched, optionally monofluorinated or polyfluorinated, alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 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] wherein L, identically or differently, in each occurrence has one of the above meanings and preferably represents F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, particularly preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, very particularly preferably F, Cl, CH3, OCH3, COCH3 or OCF3, in particular F or CH3.

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

[0214] The liquid-crystalline 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] Particularly preferred are polymerizable compounds of formula M and formulae RM-1 to RM98.

[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-A-0 240 379.

[0218] The following examples are intended to illustrate the invention without limiting it: Above and below, 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 transformation of the chemical formulas is carried out according to Tables 1 to 3. In each case, 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 abbreviates 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 ingredients 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 of the other, 1, 2, 3, 4, 5 or 6; (O)C m H 2m+1 OC m H 2m+1 or C m H 2m+1 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 can be 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, preferably at elevated temperature.It is also possible to mix the solution of components in organic solvent, such as 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 so far.

[0252] The dielectric may also contain further additives known to those skilled in the art and described in the literature, such as UV absorbers, antioxidants, nanoparticles, and free radical scavengers. For example, 0-15% of pleochroic dyes, stabilizers such as phenols, HALS (hindered amine light stabilizers), e.g., Tinuvin 770 (=bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate), or chiral dopants can be added. Suitable stabilizers 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 conductive salts, preferably ethyldimethyldodecylammonium 4-hydroxybenzoate, tetrabutylammonium tetraphenylboronate, or complex salts of crown ethers (see, for example, Haller et al., Mol. Cryst. Liq. Cryst. 24, 249-258 (1973)), can be added to improve the electrical conductivity, or substances can be added to modify the dielectric anisotropy, viscosity, and / or alignment of the nematic phase. Substances of this type are described, for example, in German Patent Application Publication Nos. 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 that 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] Stabilisers which can be added to the mixtures according to the invention, for example in amounts of 0 to 10% by weight, are listed below.

[0258] [Table 24]

[0259] [Table 25]

[0260] [Table 26]

[0261] [Table 27]

[0262] [Table 28]

[0263] Table E lists exemplary compounds that 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. [Example]

[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 as 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 investigated is obtained from the change in the dielectric constant of the host mixture after adding the compound to be investigated and extrapolating to 100% of the compound used. Depending on the solubility, generally 10% of the compound to be investigated 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 [°C], 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 [pN] at 20°C, K2 represents the elastic constant for "twist" deformation at 20°C [pN], K3 represents the elastic constant for "bend" deformation [pN] at 20°C, LTS stands for low temperature stability (nematic phase) determined in a test cell.

[0281] Unless otherwise expressly stated, 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 denotes the melting point, cl.p. 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 stated otherwise, all physical properties are determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals", November 1997, Merck KGaA, Germany, and apply to a temperature of 20°C, Δn being determined at 589 nm and Δε being determined at 1 kHz.

[0283] In the present invention, the term "threshold voltage" refers to the capacitive threshold (V), also known as the Freederickss threshold, unless otherwise specified. In an embodiment, as is common and usual, the optical threshold is the voltage 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 plates separated by a gap of 20 μm, each with an inner electrode layer and a polyimide alignment layer on top, which produces 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 separated by a gap of 4 μm, each with an electrode layer on the inside 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 (usually 365 nm) of a given intensity for a predetermined time, together with a voltage applied to the display (usually 10 V to 30 V AC, 1 kHz). In the examples, unless otherwise stated, the intensity is 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 band pass filter.

[0287] The tilt angle is measured by a rotational crystal test (Autronic Melchers TBA-105). A low value (i.e., a large deviation from the 90° angle) corresponds to a large tilt in this context.

[0288] The VHR value is 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 (90° rubbed, TN polyimide alignment layer, layer thickness d approximately 6 μm). The HR value is determined before and after 2 hours of UV exposure (sunlight test) at 100 °C for 5 minutes at 1 V, 60 Hz, 64 μs pulse (measuring device: Autronic-Melchers VHRM-105).

[0289] To determine 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 is placed in storage at -10°C and periodically checked for crystallization and precipitation of the mixture.

[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 expressly stated otherwise.

[0292] The following exemplary 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, especially 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> To prepare the 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 to 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> To prepare the 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 to 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> To prepare the 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 to 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 and one or more compounds selected from the group of compounds of formulas BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1 and BS-2, with the proviso that the compound of formula BC is selected from compounds of formula DFDBC-n(O)-(O)m; wherein the compound of formula CR is selected from compounds of formula COChrom-n-Om to CCOChrom-n-m; with the proviso that the compounds of formulae BF-1 to BS-2 are selected from compounds of formulae B-nO-Om to B(S)-n-Om or compounds of formulae CB(S)-n-(O)m to PB-n-Om A liquid crystal medium characterized by: 【Chemistry 1】 (In the formula, R １ and R １＊ each independently represent alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH ２ The group is formed by forming a -C≡C-, -CF group such 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 , OCF ３ or CHF ２ Represents.) 【Transformation 3】 (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 monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 4】 -C≡C-, -CF ２ O-, -OCF ２ optionally replaced by —, —OC—O— or —O—CO—; c represents 0, 1 or 2; d represents 1 or 2. 【Transformation 5】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6; (O) represents an oxygen atom or a single bond. 【Transformation 6】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6. 【Transformation 7】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6. 【Transformation 8】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6; (O) represents an oxygen atom or a single bond.

2. comprising at least one compound of formula I and one or more compounds selected from the group of compounds of formulas BC, CR, PH-1, PH-2, BF-1, BF-2, BS-1 and BS-2, with the proviso that the compound of formula BC is selected from compounds of formula DFDBC-n(O)-(O)m; wherein the compound of formula CR is selected from compounds of formula COChrom-n-Om to CCOChrom-n-m; with the proviso that the compounds of formulae BF-1 to BS-2 are selected from compounds of formulae B-nO-Om to B(S)-n-Om or compounds of formulae CB(S)-n-(O)m to PB-n-Om; However, the proportion of the compound of formula I in the entire mixture is 1 to 30% by weight. A liquid crystal medium characterized by: 【Chemistry 9】 (In the formula, R １ and R １＊ each independently represent alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH ２ The group is formed by forming a -C≡C-, -CF group such that the O atoms are not directly linked to each other. ２ O-, -CH=CH-, 【Chemistry 10】 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 , OCF ３ or CHF ２ Represents.) 【Chemistry 11】 (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 monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 12】 -C≡C-, -CF ２ O-, -OCF ２ optionally replaced by —, —OC—O— or —O—CO—; c represents 0, 1 or 2; d represents 1 or 2. 【Chemistry 13】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6; (O) represents an oxygen atom or a single bond. 【Chemistry 14】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6. 【Chemistry 15】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6. 【Chemistry 16】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6; (O) represents an oxygen atom or a single bond.

3. at least one compound of formula I and one or more compounds selected from the group of compounds of formulas BF-1, BF-2, BS-1 and BS-2, with the proviso that the compounds of formulae BF-1 to BS-2 are selected from compounds of formulae B-nO-Om to B(S)-n-Om or compounds of formulae CB(S)-n-(O)m to PB-n-Om A liquid crystal medium characterized by: 【Chemistry 17】 (In the formula, R １ and R １＊ each independently represent alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH ２ The group is formed by forming a -C≡C-, -CF group such that the O atoms are not directly linked to each other. ２ O-, -CH=CH-, [Chemistry 18] 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 , OCF ３ or CHF ２ Represents.) 【Chemistry 19】 (In the formula, R １ , R ２ are each independently H, unsubstituted, CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 20】 -C≡C-, -CF ２ O-, -OCF ２ optionally replaced by —, —OC—O— or —O—CO—; c represents 0, 1 or 2; d represents 1 or 2. 【Chemistry 21】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6. 【Chemistry 22】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6; (O) represents an oxygen atom or a single bond.

4. at least one compound of formula I and one or more compounds selected from the group of compounds of formulas BF-1, BF-2, BS-1 and BS-2, with the proviso that the compounds of formulae BF-1 to BS-2 are selected from compounds of formulae B-nO-Om to B(S)-n-Om or compounds of formulae CB(S)-n-(O)m to PB-n-Om; However, the proportion of the compound of formula I in the entire mixture is 1 to 30% by weight. A liquid crystal medium characterized by: 【Chemistry 23】 (In the formula, R １ and R １＊ each independently represent alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH ２ The group is formed by forming a -C≡C-, -CF group such that the O atoms are not directly linked to each other. ２ O-, -CH=CH-, 【Chemistry 24】 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 , OCF ３ or CHF ２ Represents.) 【Chemistry 25】 (In the formula, R １ , R ２ are each independently H, unsubstituted, CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 26】 -C≡C-, -CF ２ O-, -OCF ２ optionally replaced by —, —OC—O— or —O—CO—; c represents 0, 1 or 2; d represents 1 or 2. 【Chemistry 27】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6. 【Chemistry 28】 (In the formula, n and m are each independently 1, 2, 3, 4, 5, or 6; (O) represents an oxygen atom or a single bond.

5. 5. Liquid-crystalline medium according to claim 1, which comprises at least one compound of the formulae Ia to Ih. 【Chemistry 29】 (In the formula, R １ and R １＊ each independently represent alkyl or alkoxy having 1 to 15 C atoms, provided that in addition, one or more CH ２ The group is formed by forming a -C≡C-, -CF group such that the O atoms are not directly linked to each other. ２ O-, -CH=CH-, 【Transformation 30】 may be replaced by —O—, —CO—O—, or —O—CO—, and in addition, one or more H atoms may be replaced by halogen.

6. 6. Liquid-crystalline medium according to claim 1, which comprises at least one compound of the formulae Ia-1 to Ia-36. 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】

7. 7. Liquid-crystalline medium according to claim 1, additionally comprising one or more compounds selected from the group of the compounds of the formulae IIA, IIB and IIC 【Transformation 36】 (In the formula, R ２Ａ , R ２Ｂ and R ２Ｃ are each independently H, unsubstituted, CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 37】 -C≡C-, -CF ２ O-, -OCF ２ optionally 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.

8. 8. Liquid-crystalline medium according to claim 1, further comprising one or more compounds of the formula III. 【Transformation 38】 (In the formula, R ３１ and R ３２ each independently represent a straight-chain alkyl, alkenyl, alkoxy, alkoxyalkyl or alkenyloxy group having up to 12 C atoms, and 【Chemistry 39】 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-.)

9. 9. Liquid-crystalline medium according to claim 1, further comprising one or more compounds of the formulae L1 to L11. 【Chemistry 40】 【Chemistry 41】 (In the formula, R, R １ and R ２ are each independently H, unsubstituted, CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 42】 -C≡C-, -CF ２ O-, -OCF ２ optionally replaced by —, —OC—O— or —O—CO—; alkyl represents an alkyl group having 1 to 6 C atoms, and s represents 1 or 2.

10. 10. Liquid-crystalline medium according to claim 1, which additionally contains one or more terphenyls of the formulae T1 to T21. 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 (In the formula, R represents a linear alkyl or alkoxy group having 1 to 7 C atoms, m represents 0, 1, 2, 3, 4, 5 or 6; n represents 0, 1, 2, 3 or 4.

11. 11. Liquid-crystalline medium according to claim 1, further comprising one or more compounds of the formulae O-1 to O-17. 【Chemistry 46】 【Chemistry 47】 (In the formula, R １ and R ２ are each independently H, unsubstituted, CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 48】 -C≡C-, -CF ２ O-, -OCF ２ may be replaced by —, —OC—O—, or —O—CO—.)

12. 12. Liquid-crystalline medium according to claim 1, which additionally comprises one or more compounds of the following formulae: 【Chemistry 49】 [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】

13. 13. Liquid-crystalline medium according to claim 1, comprising from 5 to 60% of compounds of the following formula (acronym: CC-3-V): 【Chemistry 54】

14. 14. The liquid-crystalline medium according to claim 1, further comprising one or more compounds selected from the group consisting of the compounds of the formulae P-1 to P-4: 【Transformation 55】 (In the formula, R represents a straight-chain alkyl, alkoxy or alkenyl, each having 1 or 2 to 6 C atoms, X is F, Cl, CF ３ , OCF ３ , OCHFCF ３ or CCF ２ CHFCF ３ Represents.)

15. 15. The liquid-crystalline medium according to claim 1, further comprising one or more compounds selected from the group consisting of compounds of the following formulae: 【Transformation 56】 【Chemistry 57】 (In the formula, R, R １ , R ２ and R １０ are each independently H, unsubstituted, CN or CF ３ or at least monosubstituted with halogen, provided that in addition, one or more CH ２ The group is formed by combining -O-, -S-, and -O- groups so that the O atoms are not directly linked to each other. 【Chemistry 58】 -C≡C-, -CF ２ O-, -OCF ２ optionally 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, 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.

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

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

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

19. 19. A process for the preparation of a liquid-crystalline medium according to any one of the preceding claims, characterized in that at least one compound of formula I is mixed with at least one further mesogenic compound and, optionally, 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 18 in an electro-optical display.

21. Electro-optical display with active matrix addressing, characterized in that it contains as dielectric a liquid-crystalline medium according to any one of claims 1 to 18.

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.

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