Liquid-crystalline medium

Abstract

To provide a liquid-crystalline medium.SOLUTION: The present invention relates to a liquid-crystal material (LC medium) comprising thiophene derivatives which are stabilised by sterically hindered amines or amine derivatives (HALS, hindered amine light stabilisers), and to liquid-crystal displays (LC displays) which contain these LC materials.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a liquid crystal material (LC (liquid crystal) medium) containing a thiophene derivative stabilized with a sterically hindered amine or amine derivative (HALS, hindered amine light stabilizer), and a liquid crystal display (LC (liquid crystal) display) containing these liquid crystal materials. [Background technology]

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

[0003] The principle of electrically controlled birefringence, namely the ECB (electrically controlled birefringence) effect or DAP (deformation of aligned phases) effect, was first described in 1971 (MFS. Chieckel and K. Fahrenschon, "Deformation of nematic liquid crystals with vertical orientation in electrical fields," Appl. Phys. Lett. Vol. 19 (1971), p. 3912 (Non-Patent Literature 1)). This was followed by reports by J.F. Kahn (Appl. Phys. Lett. Vol. 20 (1972), p. 1193 (Non-Patent Literature 2)) and G. Labrunie and J. Robert (J. Appl. Phys. Vol. 44 (1973), p. 4869 (Non-Patent Literature 3)).

[0004] In a report by J. Robert and F. Clerc (SID 80 Digest Techn. Papers (1980), p. 30 (Non-Patent Literature 4)), J. Duchene (Displays Vol. 7 (1986), p. 3 (Non-Patent Literature 5)), and H. Schad (SID 82 Digest Techn. Papers (1982), p. 244 (Non-Patent Literature 6)), it was shown that in order to be suitable for use in advanced information display elements based on the ECB effect, the liquid crystal phase must have a high ratio of elastic constants K3 / K1, a high optical anisotropy Δn, and a dielectric anisotropy Δε of -0.5 or less. Electro-optical display elements based on the ECB effect have homeotropic edge orientation (VA technology, i.e., vertically aligned). Dielectrically negative liquid crystal media can also be used in displays using IPS or FFS effects.

[0005] In particular, TN, VA, IPS, and FFS cells are currently areas of commercial interest for media according to the present invention.

[0006] The liquid crystal material must have good chemical and thermal stability, as well as good stability against electric fields and electromagnetic radiation. Furthermore, the liquid crystal material must have low viscosity, resulting in a short address time, low threshold voltage, and high contrast in the cell.

[0007] These materials must also possess an intermediate phase, such as a nematic intermediate phase, suitable for the aforementioned cells over the widest possible range above and below normal operating temperatures, i.e., room temperature. Since liquid crystals are generally used as mixtures of multiple components, it is important that the components mix easily with each other. Further properties such as electrical conductivity, dielectric anisotropy, and optical anisotropy must meet various requirements depending on the type of cell and application field. For example, cell materials with a twisted nematic structure must have positive dielectric anisotropy and low electrical conductivity.

[0008] For example, a matrix liquid crystal display (MLC) with integrated nonlinear elements for switching individual pixels is desirable for a medium having high positive dielectric anisotropy, a broad nematic phase, relatively low birefringence, very high resistivity, good UV and temperature stability, and low vapor pressure.

[0009] This type of matrix liquid crystal display is known. An example of a nonlinear element that can be used to switch individual pixels individually is an active element (i.e., a transistor). Thus the term “active matrix” is used and can be distinguished into two types: 1. MOS (metal oxide semiconductor) or other diodes on a silicon wafer as a substrate, 2. Thin-film transistors (TFTs) on a glass plate as a substrate.

[0010] The TFT matrix is ​​applied to the inner surface of one glass plate of the display, while the other glass plate has transparent counter electrodes on its inner surface. Compared to the size of the pixel electrodes, the TFT is very small and has virtually no adverse effect on the image. Furthermore, this technology can be extended to full-color displays, in which a mosaic of red, green, and blue filters is arranged so that the filter elements face each of the switchable pixels.

[0011] TFT displays typically operate as TN cells, which are transmissive polarizers crossed together, and incorporate a backlight.

[0012] The term MLC display, as used herein, also encompasses any matrix display having integrated nonlinear elements, i.e., displays that include passive elements such as varistors or diodes (MIM, i.e., metal-insulator-metal) in addition to the active matrix.

[0013] This type of MLC display is particularly suitable as a high-information display for television applications (e.g., pocket televisions), computer applications (laptops), and in the structure of automobiles or aircraft. In addition to problems related to the angular dependence of contrast and response time, MLC displays also have 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 Literature 7); STROMER, M., Proc. Eurodisplay, Vol. 84, September 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, p. 145ff, Paris (Non-Patent Literature 8)]. When the resistance decreases, problems such as reduced contrast and the disappearance of afterimages can occur in MLC displays. Since the resistivity of liquid crystal mixtures generally decreases with the lifespan of the MLC display due to interaction with the internal surface of the display, high (initial) resistance is crucial for achieving an acceptable lifespan. Especially for low-voltage mixtures, achieving very high resistivity values ​​has been impossible until now. Furthermore, it is important that the resistivity shows the smallest possible increase in temperature and after heating and / or UV exposure. Therefore, prior art MLC displays do not meet today's requirements.

[0014] Television and video applications require MLC displays with short response times. Such short response times can be achieved, in particular, by using liquid crystal media with low viscosity, especially low rotational viscosity γ1. However, diluting additives generally lowers the transparency point, thus narrowing the operating temperature range of the media.

[0015] Therefore, there remains a great demand for MLC displays that offer a wide operating temperature range, short response time even at low temperatures, a low threshold voltage, and very high resistivity, while also exhibiting no or only reduced levels of these drawbacks.

[0016] For TN (Schadt-Helfrich) cells, a medium that promotes the following advantages in the cell is desirable: • Expanded nematic phase range (especially down to low temperatures) • Switching capability at extremely low temperatures (outdoor use, automotive, avionics) • Improved resistance to UV radiation (longer lifespan) • Low threshold voltage.

[0017] Achieving these advantages while simultaneously maintaining other parameters using media available from prior art is impossible with backlights.

[0018] Prior art, such as International Publication No. 2010 / 099853 (Patent Document 1) and German Patent Application Publication No. 10 2010 027 099 (Patent Document 2), discloses thiophene-containing LC media. International Publication No. 2010 / 099853 (Patent Document 1) discloses a compound containing a thiophene-2,5-diyl unit directly linked to a 2- and / or 6-substituted 1,4-phenylene unit. The objective of International Publication No. 2010 / 099853 (Patent Document 1) was the development of novel materials for use in liquid crystal displays. This objective was achieved by providing a compound of the following general formula.

[0019] [ka] In the formula, A 0 represents the 2,6-difluoro-1,4-phenylene unit, A 1 and A 2 Besides other meanings, it represents the 1,4-phenylene or 1,4-cyclohexylene unit, Z 1 and Z 2 This represents a bridging element or a single bond.

[0020] The specific examples described are, for example, the following compounds (see International Publication No. 2010 / 099853 (Patent Document 1)).

[0021] [Chemical formula]

[0022] In many practical applications of liquid crystal displays, known liquid crystal media containing thiophene compounds are not sufficiently stable. In particular, exposure to irradiation not only by UV radiation but also by normal backlighting results in a decrease in electrical properties, especially an increase in conductivity.

[0023] German Patent Application Publication No. 10 2010 027 099 (Patent Document 2) describes an LC medium containing a compound disclosed in International Publication No. 2010 / 099853 (Patent Document 1) and a bithienyl derivative of the following formula as a stabilizer.

[0024] [Chemical formula] Here, these bithienyl derivatives are preferably employed in combination with a thiophene 1,1-dioxide derivative of the following formula.

[0025] [Chemical formula]

[0026] In both of the above formulas, A 1 and A 2 represent, for example, 1,4-phenylene or 1,4-cyclohexylene, and Z 1 and Z 2 represent, among other meanings, for example, a single bond. The specific examples described are the following compounds (see German Patent Application Publication No. 10 2010 027 099 (Patent Document 2)).

[0027] [Chemical formula]

[0028] The use of so-called "hindered amine light stabilizers," or HALS for short, to stabilize liquid crystal mixtures has already been proposed.

[0029] Ohkatsu, Y., J. of Japan, Petroleum Institute, Vol. 51, 2008, pp. 191-204 (Non-Patent Literature 9), states that HALS with various substituents on the nitrogen atom are pK B The values ​​are being compared. The following types of structural formulas are disclosed.

[0030] [ka]

[0031] The compound TEMPOL, given the following formula, is known.

[0032] [ka] This is described, for example, in Mieville, P. et al., Angew. Chem. 2010, Vol. 122, pp. 6318-6321 (Non-Patent Literature 10). It is commercially available and used by various manufacturers as a photo or UV protectant in combination with UV absorbers, for example, as a polymerization inhibitor and in formulations for polyolefins, polystyrene, polyamides, coatings and PVC precursors.

[0033] German Patent Application No. 102011117937.6 (Patent Document 3) describes a liquid crystal mixture having negative dielectric anisotropy, comprising TINUVIN® 770, i.e., the compound shown below, for stabilization.

[0034] [ka]

[0035] German Patent Application No. 102011119144.9 (Patent Document 4) and International Patent Application No. PCT / EP2011 / 005692 (Patent Document 5) describe liquid crystal mixtures containing HALS N-oxide in particular for stabilization.

[0036] A nematic liquid crystal mixture containing a small amount of TINUVIN® 770 as a stabilizer and the compound shown below, exhibiting negative dielectric anisotropy, has been proposed, for example, in International Publication No. 2009 / 129911 (Patent Document 6). However, the corresponding liquid crystal mixture does not possess sufficient properties for some practical applications. In particular, they may not be sufficiently stable against irradiation by typical CCFL (cold cathode fluorescent lamp) backlights, or they may exhibit LTS (low-temperature stability) problems.

[0037] The use of various stabilizers in liquid crystal media is described, for example, in Japanese Patent Publication No. 55-023169 (Patent Document 7), Japanese Patent Publication No. 05-117324 (Patent Document 8), International Publication No. 02 / 18515 (Patent Document 9), and Japanese Patent Publication No. 09-291282 (Patent Document 10).

[0038] Furthermore, TINUVIN(registered trademark) 123, that is, the compound shown below, has also been proposed for stabilization purposes.

[0039] [ka]

[0040] Mesogenic compounds containing one or two HALS units are disclosed in European Patent Application Publication No. 1784442 (Patent Document 11).

[0041] European Patent Application Publication No. 3 271 440 (Patent Document 12) discloses a mesogenic compound of the following formula together with a HALS stabilizer of the following formula.

[0042] [ka] In the formula, A 0 represents the 2,6-difluoro-1,4-phenylene unit, A 1 and A 2 Besides other meanings, it represents the 1,4-phenylene or 1,4-cyclohexylene unit, Z 1 and Z 2 For example, this represents a bridging element or a single bond.

[0043] [ka] In the formula, q represents either 1 or 2. However, despite the significant improvements in the stabilization of thiophene compounds, as demonstrated by comparisons between mixtures containing the compound of formula II and those without such compounds, there is still a demand for a higher level of stabilization, particularly in terms of VHR.

[0044] Due to the complexity of the mechanism of action and the fact that LC media are composed of up to 10 or more individual substances that are chemically distinct from one another, selecting a suitable light stabilizer is extremely difficult even for those skilled in the art in terms of the diversity of available materials. [Prior art documents] [Patent Documents]

[0045] [Patent Document 1] International Publication No. 2010 / 099853 [Patent Document 2] German Patent Application Publication No. 10 2010 027 099 Specification [Patent Document 3] German Patent Application No. 102011117937.6 Specification [Patent Document 4] Unique Country License for Issuance No. 102011119144.9 [Patent Document 5] International Declaration No. PCT / EP2011 / 005692 [License 6] International Publication No. 2009 / 129911 [License 7] Special Announcement No. 55-023169 [License 8] Special Announcement No. 05-117324 [License 9] International Publication No. 02 / 18515 [License 10] Special Announcement No. 09-291282 [License 11] European Patent Publication No. 11784442 [License 12] European Patent Publication No. 3271440 [Non-licensed literature]

[0046] [Non-licensed Document 1] MFSchieckel K.Fahrenschon, "Deformation of nematic liquid crystals with vertical orientation in electrical fields", Appl.Phys.Lett.19 volume (1971), 3912 pages [Non-licensed Document 2] J.F. Kahn (Appl. Phys. Lett. 20 (1972), p. 1193) [Non-licensed Document 3] G.Labrunie J.Robert (J.Appl.Phys.44 volume (1973), 4869 pages [Non-licensed Document 4] J. Robert F. Clerc (SID 80 Digest Techn. Papers (1980), 30 pages [Non-licensed 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] 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 8] 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 9] Ohkatsu, Y., J. of Japan. Petroleum Institute, Vol. 51, 2008, pp. 191-204. [Non-Patent Document 10] Mieville, P. et al., Angew. Chem. 2010, Vol. 122, pp. 6318-6321. [Disclosure of the Invention] [Problems that the invention aims to solve]

[0047] In particular, an object of the present invention was to provide a medium for this type of TN, VA, or IPS display that has the desired characteristics shown above and does not exhibit, or exhibits to a lesser extent, the drawbacks shown above. In particular, the LC medium must have high dielectric anisotropy and high birefringence, as well as fast response time and low rotational viscosity. In addition, the LC medium must have a high transparency point, a wide nematic phase range, and a low threshold voltage.

[0048] A further object of the present invention was to provide a thiophene-containing LC medium that does not exhibit the above-mentioned drawbacks, or exhibits them to a lesser extent. [Means for solving the problem]

[0049] Surprisingly, it has been found that the objectives described above can be achieved by using thiophene derivatives in combination with HALS in LC media, particularly in active-address LC displays and in LC media in TN, VA, IPS, or FFS displays. As a result of combining HALS and thiophene derivatives as shown below, the LC media has the desired properties described above.

[0050] Based on the prior art, those skilled in the art would not expect improvements in properties, namely, particularly in fast response time and low rotational viscosity, as a result of using the thiophene derivatives of the present invention with HALS added as a light stabilizer in nematic LC media having essentially non-twisted phases, especially in LC media having positive dielectric anisotropy, and in TN, VA, IPS, or FFS displays. [Modes for carrying out the invention]

[0051] Therefore, the present invention relates to an LC medium characterized by containing one or more compounds of formula I and one or more compounds of formula H.

[0052] [ka]

[0053] In the formula, each base has the following meaning: R 1 and R 2 represents a linear or branched alkyl group having H, F, Cl, Br, -CN, -NCS, or 1 to 12 C atoms, provided that one or more CH2 groups also contain terminal C atoms, and each group is independently configured such that O or S atoms are not directly linked to each other, such as -CH=CH-, -C≡C-, [ka] Substitutions may include -O-, -S-, -CO-, -CO-O-, and -O-CO-, provided that one or more H atoms are replaced with F or Cl. A 0 , A 1 and A 2 Each of these independently represents phenylene-1,4-diyl (in which one or two additional CH groups may be replaced with N, and one or more H atoms may be replaced with halogens, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2, or OCF3), cyclohexane-1,4-diyl (in which one or two additional non-adjacent CH2 groups may be independently replaced with O and / or S, and one or more H atoms may be replaced with F), cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, where A 0 preferably represents 2,6-difluoro-1,4-phenylene, A 1 is preferably 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, and particularly preferably 1,4-phenylene. Z 1 and Z 2These each independently represent -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2H4-, -C2F4-, -CF2CH2-, -CH2CF2-, -CFHCFH-, -CFHCH2-, -CH2CFH-, -CF2CFH-, -CFHCF2-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C- or a single bond, and m and n each independently represent 0, 1, 2, or 3, where m+n is preferably 1, 2, or 3, and especially preferably 1.

[0054] [ka]

[0055] During the ceremony, R H H, O ● , CH3, OH or OR S Preferably H or O ● This represents, R S This represents H, an alkyl group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms. R 11 Each instance independently represents a linear or branched alkyl chain having H, F, and 1 to 20 C atoms, where one -CH2- group or multiple -CH2- groups if present may be replaced by -O- or -(C=O)-, but two adjacent -CH2- groups cannot be replaced by -O-, and one or multiple -CH2- groups if present may be replaced by -CH=CH- or -C≡C-, where one or more H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 It can be replaced with, R 11 This preferably represents H or alkyl, particularly preferably alkyl, particularly preferably n-alkyl, and very particularly preferably n-butyl. R 12This represents a linear or branched alkyl chain having 1 to 20 C atoms independently in each occurrence (in the chain, one or more -CH2- groups may be replaced with -O- or -(C=O)-, but two adjacent -CH2- groups cannot be replaced with -O-), or a hydrocarbon group containing a cycloalkyl or alkylcycloalkyl unit (in the group, one or more -CH2- groups may be replaced with -O- or -(C=O)-, but two adjacent -CH2- groups cannot be replaced with -O-, and in the group, one or more H atoms may be F, OR 13 , N(R 13 )(R 14 ) or R 15 It may be replaced by: ) representing an aromatic or heteroaromatic hydrocarbon group (in which one or more H atoms are F, OR 13 , N(R 13 )(R 14 ) or R 15 It may be replaced with ). R 12 This preferably represents H, an unbranched alkyl group, or a branched alkyl group, and particularly preferably H or an unbranched alkyl group. R 13 Each instance independently represents a linear or branched alkyl or acyl group having 1 to 10 carbon atoms, preferably an n-alkyl group having 6 to 12 carbon atoms, or an aromatic hydrocarbon or carboxylic acid group. R 14 Each instance independently represents a linear or branched alkyl or acyl group having 1 to 10 carbon atoms, preferably an n-alkyl group, or an aromatic hydrocarbon or carboxylic acid group having 6 to 12 carbon atoms. R 15 Each instance represents a linear or branched alkyl group having 1 to 10 C atoms independently of each other, where one or more -CH2- groups may be replaced by -O- or -(C=O)-, but two adjacent -CH2- groups cannot be replaced by -O-. S 11 and S 12 Each instance represents an alkylene group having 1 to 20 carbon atoms independently of each other, and the group is branched or preferably linear and preferably has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and particularly preferably 1 to 8 carbon atoms -(CH2-) n However, one -CH2- group or multiple -CH2- groups if present may be replaced with -O- or -(C=O)-, but two adjacent -CH2- groups cannot be replaced with -O-, one or multiple -CH2- groups if present may be replaced with -CH=CH- or -C≡C-, however, one H atom or multiple H atoms may be replaced with F, OR 13 , N(R 13 )(R 14 ) or R 15 It can be replaced with, X 11 This represents C, Y 11 ~Y 14 Each represents either methyl or ethyl independently of the other, and most preferably all represent either methyl or ethyl, and most preferably all represent methyl. Z 11 ~Z 14 In each occurrence, -O-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -O-(C=O)-O-, -(NR 13 )-, -NR 13 -(C=O)- or represents a single bond, but S 11 If it is a single bond, Z 11 and Z 12 Neither of them simultaneously represents -O-, however S 12 If it is a single bond, Z 13 and Z 14 Neither of them simultaneously represents -O-, and however -X 11 [-R 11 ] o - If it is a single bond, Z 12 and Z 13 Neither of them simultaneously represents -O-, Z 11Preferably, represents -O-, Z 13 Preferably, represents a single bond, n×p represents an integer from 3 to 10, preferably up to 8. p represents either 1 or 2. o represents (3-p), If p is 1, n represents 3, 4, 5, 6 or 8, particularly preferably 4, 6 or 8, very particularly preferably 4 or 6, and m represents (10-n), and If p is 2, n represents an integer between 2 and 4, preferably 2 or 3, and particularly preferably 3. m represents (4-n), [ka] This refers to an organic group having (m+n) bonding sites, preferably up to 4 bonding sites, and preferably an alkanediyl, alkanetriyl, or alkanetetrayl unit having 1 to 30 C atoms (where m groups R are present in the molecule). 12 In addition, however, R present in the molecule 12 Independently from that, another H atom is R 12 It may be replaced by R 12 ) may be replaced by ), preferably alkanetetrayl units having monovalent or divalent valencies on each terminal C atom (wherein one or more -CH2- groups may be replaced by -O- or -(C=O)- such that two O atoms are not directly bonded to each other), or substituted or unsubstituted aromatic or heteroaromatic hydrocarbon groups having up to 10 valencies (wherein m groups R present in the molecule) 12 In addition, however, R present in the molecule 12 Independently from that, one further H atom is R 12 It may be replaced by R 12 It may be replaced with ). If p=1, or -X 11[-R 11 o - may also represent a single bond.

[0056] The present invention further relates to the use of the medium according to the invention in an electro-optical device, in particular in an LC display.

[0057] The present invention more particularly relates to an LC display containing an LC medium according to the invention in a TN, VA, IPS or FFS display.

[0058] A 0 represents a compound of formula I in which phenylene-1,4-diyl (in which in addition one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH3, CHF2, CH2F, OCH3, OCHF2, CF3 or OCF3). A medium containing such a compound is preferred, particularly preferably,

[0059]

Chemical formula

Chemical formula

[0061] Preferred compounds of formula I result in a medium having particularly high clearing points, low rotational viscosities, broad nematic phases, high birefringences and good stabilities.

[0062] In another preferred embodiment, one or more of R 0 , R 1 or R 2 are

Chemical formula

Chemical formula

[0063] Furthermore, compounds of formula I in which m and n represent 0, 1 or 2, particularly preferably 0 or 1, are preferred. Compounds of formula I in which n represents 0, i.e., the thiophene ring is the terminal ring, are particularly preferred. Furthermore, compounds of formula I in which m represents 0, 1 or 2, preferably 1 or 2, very particularly preferably 1, are preferred.

[0064] A in formula I 1 and A 2 are particularly preferably phenylene-1,4-diyl (and the group may be mono- or polysubstituted by F). Furthermore, it represents cyclohexane-1,4-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl.

[0065] Z in formula I 1 and Z 2 are particularly preferably -CF2O-, -OCF2- or a single bond, particularly a single bond.

[0066] A in formula I 1 and A 2 are particularly preferably

[0067]

Chemical formula

[0068] Furthermore, R 1 and R 2 However, compounds of formula I are preferred, each independently representing H, F, Cl, Br, -CN, -SCN, -NCS, SF5, halogen, or alkyl, alkenyl, or alkynyl groups having 1 to 8, preferably 1 to 5, carbon atoms (each of these groups may be substituted with a halogen, particularly F).

[0069] In formula I, the base R is particularly preferred. 1 and R 2 is H, halogen, or alkyl, alkenyl, alkynyl, or alkoxy having 1 to 12, preferably 1 to 8 C atoms (each of the groups may be substituted with a halogen, particularly F), particularly preferably H, F, or alkyl, alkenyl, or alkynyl having 1 to 8 C atoms. Preferably at least one group is not H, and particularly preferably both groups R 1 and R 2 It is not H. 1 It is very preferably equal to alkyl. 2 More preferably, is H, alkyl, or fluorine. Very preferably, R 1 is alkyl, R 2 R is H or alkyl. 1 , R 2 Each of these independently represents an unbranched alkyl group having, very preferably, 1 to 5 carbon atoms. 1 and R 2 When representing an alkyl, alkoxy, alkenyl, or alkynyl that has been substituted, the two groups R 1 and R 2 The total number of C atoms in is preferably less than 10.

[0070] Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl.

[0071] Preferred alkenyl groups include, for example, ethenyl, propenyl, butenyl, and pentenyl.

[0072] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, and octinyl.

[0073] Preferred alkoxy groups include, for example, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, and n-octoxy.

[0074] The halogen preferably represents F or Cl.

[0075] Particularly preferred compounds of formula I are selected from the following sub-formulas.

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] In the formula, R 1 and R 2 The above and below have meanings, L 1 ~L 6R independently represents H or F. 1 and R 2 L preferably represents a fluorinated alkyl, alkenyl, alkynyl, or alkoxy having 1 to 12 carbon atoms, and particularly preferably a fluorinated alkyl, alkenyl, or alkynyl having 1 to 5 carbon atoms. 2 preferably represents F. In formulas I3 to I11, L 3 and L 4 preferably represents H. In formulas I12 to I16, L 3 and L 4 preferably represents F. The preferred medium according to the present invention comprises a compound selected from formulas I3 and I5.

[0081] In equation I and the more defining equations above and below it, base R 1 Preferably, linear or branched alkyl groups having 1 to 12 carbon atoms (however, one or more CH2 groups also contain terminal carbon atoms, and each group is configured such that the oxygen or sulfur atoms are not directly linked to each other, such as -CH=CH-, -C≡C-, [ka] It may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, and in addition, one or more H atoms may be replaced with F or Cl. More preferably, it is an alkyl having 1 to 7 C atoms or an alkenyl, cyclopentylmethyl or cyclopentyl having 2 to 7 C atoms.

[0082] In equation I and the more defining equations above and below it, base R 2 Preferably, linear or branched alkyl groups having 1 to 12 carbon atoms (however, one or more CH2 groups also contain terminal carbon atoms, and each group is configured such that the oxygen or sulfur atoms are not directly linked to each other, such as -CH=CH-, -C≡C-, [ka] It may be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO-, ), the group -CF3, -OCF3 or F, more preferably methyl, ethyl, n-propyl, n-butyl, CF3 or F, most preferably methyl, ethyl or propyl.

[0083] In addition, an LC medium containing the compound of formula I below is particularly preferred.

[0084] [ka]

[0085] [ka]

[0086] The most preferred compounds of formula I are, in particular, one or more of the following:

[0087] [ka]

[0088] As a further possibility, the compound of formula I below may be used.

[0089] [ka]

[0090] [ka]

[0091] The compound of formula I is known to those skilled in the art and can be prepared in a manner similar to that described in, for example, Houben-Weyl's *Methoden der organischen Chemie* (Methods of Organic Chemistry), Thieme-Verlag, Stuttgart, and other standard works in organic chemistry.

[0092] The synthesis of suitable thiophenes of formula I is known, for example, from WO 2009 / 129915, WO 2010 / 099853 and WO 2010 / 094455.

[0093] In formula H, aryl represents an aromatic or heteroaromatic hydrocarbon group having 4 to 40 C atoms, and may contain 1, 2, 3 or 4 aromatic rings including a condensed ring which may be linked directly or via an alkylene linking group having 1 to 12 C atoms, provided that one or more H atoms may be replaced by alkyl or alkoxy having 1 to 6 C atoms or alkenyl having 2 to 6 C atoms, or by CN, CF3 or halogen, provided that one or more CH2 groups may each independently be replaced by -O-, -S-, -NH-, -N(C1-C4-alkyl)-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH- or -C≡C- such that O or S atoms are not directly linked to each other.

[0094] Preferred aryl groups are benzene, naphthalene, anthracene, biphenyl, m-terphenyl, p-terphenyl and (phenylalkyl)benzene, where alkyl is a straight-chain alkyl having 1 to 12 C atoms.

[0095] Also in the compounds of formula H, the group N(R 13 )(R 14 ) may preferably be amines.

[0096] The compounds of the following formula H are more preferred.

[0097] p is 2.

[0098]

Chemical formula

[0099] [ka] teeth, [ka] It represents.

[0100] [ka] teeth, [ka] It represents.

[0101] [ka] is -CH2-[CH2] r -CH2- (where r is 0, 1, 2, 3, 4, 5~18), octane-1,8-diyl, heptane-1,7-diyl, hexane-1,6-diyl, pentane-1,5-diyl, butane-1,4-diyl, propane-1,3-diyl, ethane-1,2-diyl or [Chem.] represents.

[0102] In a preferred embodiment of the present invention, in the compound of formula H, it is as follows.

[0103] [Chem.] is [Chem.] <e represents. <00009e3>

[0104] <00z00966> [Chem.] is <00z00971> [Chem.] represents.

[0105] [Chem.] is -(CH2-)2, -(CH2-)3, -(CH2-)4, -(CH2-)5, -(CH2-)6, -(CH2-)7, -(CH2-)8, that is, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, [Chem.] represents.

[0106] and / or -Z 12 -S 11 -Z 11 - is, independently of each other in each occurrence, -O-, -S 11 -O-, -O-S 11 -O-, -(C=O)-O-S 11 It should be noted that there may be some inaccuracies in the translation due to the lack of clear context for some chemical notations. It is recommended to double-check with relevant chemical knowledge and specific context for more accurate understanding.-O-, -O-(C=O)-S 11 -O-, -O-(C=O)-S 11 -(C=O)-O-, -OS 11 -(C=O)-O-, -(C=O)-OS 11 -(C=O)-O-, or -(NR 13 )-S 11 -O-, -NR 13 -(C=O)-S 11 -(C=O)-O- or a single bond, preferably -O-, -S 11 -O-, -OS 11 -O-, -(C=O)-OS 11 -O-, -O-(C=O)-S 11 -O- or -OS 11 -(C=O)-O- represents and / or R 11 If present, represents alkyl, alkoxy or H, preferably H or alkyl, and / or R 12 H represents methyl, ethyl, propyl, isopropyl, or 3-heptyl, or cyclohexyl.

[0107] In a preferred embodiment of the present invention, the compound of formula H is as follows:

[0108] [ka] The following formula [ka] This represents a group selected from the group.

[0109] In a preferred embodiment of the present invention, the compound of formula H is as follows:

[0110] [ka] The following formula [ka] This represents a group selected from the group.

[0111] In a preferred embodiment of this application, in a compound of formula I in which p preferably represents 1,

[0112] [ka] teeth, [ka] Preferably -OS 11 -O-, -S 11 -O- or -OS 11 -, especially preferably -OS 11 Represents -O-

[0113] In a preferred embodiment of this application, in a compound of formula H, the group

[0114] [ka] Preferably, the formula [ka] This represents a base selected from the group.

[0115] In a further preferred embodiment of this application, which may be identical or different from the above, a compound of formula I,

[0116] [ka] Preferably, the formula [ka] This represents a base selected from the group.

[0117] In a further preferred embodiment of this application, which may be identical or different from the above, in a compound of formula H,

[0118] [ka] Each of them appeared independently of the others. [ka] Preferably, [ka] It represents.

[0119] In a particularly preferred embodiment of the present invention, all groups present in the compound of formula H

[0120] [ka] These have the same meaning.

[0121] In each preferred embodiment of the present invention, the medium according to the present invention is selected from the following group of compounds of formula H-1 to H-13, preferably selected from the group of compounds of formula H-3, H-5, H-6, H-7, H-8, H-9, H-10, H-12 and H-13, particularly preferably selected from the group of compounds of formula H-6 to H-9, and very particularly preferably H-9, comprising one or more compounds of formula H.

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] [ka]

[0126] [ka]

[0127] [ka]

[0128] In a more preferred embodiment of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula H selected from the group of compounds of formula H-1 and / or H-3 to H-7 and / or H-8 and / or H-9.

[0129] In a more preferred embodiment of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula H selected from the group of compounds of formula H-8 and / or H-9.

[0130] The medium according to the present invention comprises at least one compound of formula H in each case, wherein p represents 1, n represents 3, 4, 5, or 6, preferably 4, and the group Z 11 -S 11 -Z 12 - is ω-bisoxyalkylene, i.e., -OS 11 In a more preferred embodiment of the present invention, these media have excellent stability.

[0131] Compounds of formula H can be advantageously and preferably prepared according to the disclosures given in U.S. Patent Application No. 15 / 883,976.

[0132] The medium contains a compound of formula H in a total of preferably 10 ppm to 3000 ppm, preferably 50 ppm to 2000 ppm, and very preferably 100 to 1000 ppm.

[0133] Preferably, the medium according to the present invention comprises a compound selected from the group of compounds of formula ST-1 to ST-18.

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] During the ceremony, R ST -CH=CH- represents an alkyl or alkoxy group having H and 1 to 15 C atoms, provided that in addition, one or more CH2 groups in these groups are arranged such that the O atoms are not directly bonded to each other, such as -C≡C-, -CF2O-, -OCF2-, and -CH=CH-. [ka] Substitutions may be made with -O-, -CO-O-, and -O-CO-, and in addition, one or more H atoms may be replaced with halogens. [ka] In each appearance, they are the same or different. [ka] This represents, Z ST These each independently represent -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-, -CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond. L 1 and L 2Each of these independently represents F, Cl, CH3, CF3, or CHF2. p represents 0, 1, or 2. q represents 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0138] Among the compounds of formula ST, formula ST-3 and the compound shown below are particularly preferred.

[0139] [ka]

[0140] [ka]

[0141] [ka]

[0142] In the compounds of formulas ST-3a and ST-3b, n preferably represents 3. In the compound of formula ST-2a, n preferably represents 7.

[0143] A particularly preferred mixture according to the present invention comprises one or more stabilizers from the group of compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1, and ST-12.

[0144] [ka]

[0145] [ka]

[0146] The compounds of formulas ST-1 to ST-19 are preferably present in the liquid crystal mixture according to the present invention in an amount of 0.005 to 0.5% based on the mixture.

[0147] When the mixture according to the present invention contains two or more compounds from the group of compounds of formula ST-1 to ST-15, the concentration increases accordingly, based on the mixture, to 0.01 to 1% in the case of two compounds.

[0148] However, the total proportion of compounds of formulas ST-1 to ST-15 based on the mixture according to the present invention shall not exceed 3%.

[0149] Particularly preferred LC media according to the present invention are shown below.

[0150] An LC medium comprising one or more preferably dielectrically positive compounds selected from the group of compounds of formula II and III, preferably each having a dielectric anisotropy greater than 3, preferably one or more compounds of formula II.

[0151] [ka]

[0152] [ka]

[0153] During the ceremony, R 2 This refers to alkyl groups having 1 to 15 carbon atoms (where one or more CH2 groups include terminal carbon atoms, and in these groups, O or S atoms are independently not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] It may be replaced by -O-, -S-, -(CO)-O-, -O-(CO)-, and in addition, one or more H atoms may be replaced by F or Cl. ) or H, Preferably, the terms represent alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, alkenyl, alkenyloxy, alkoxyalkyl, fluorinated alkenyl, cycloalkyl (having 3 to 5 carbon atoms), cycloalkylalkyl, cycloalkylalkoxy, most preferably alkyl, cyclopropyl, cyclopentyl or alkenyl. [ka] Preferably [ka] This represents, L 21 and L 22 This represents H or F, L 23 is H or CH3, preferably H. X 2 This represents a halogen, a halogenated alkyl or alkoxy having 1 to 3 carbon atoms, or a halogenated alkenyl or alkenyloxy having 2 or 3 carbon atoms, preferably F, Cl, -OCF3, -O-CH2CF3, -O-CH=CH2, -O-CH=CF2 or -CF3, and very preferably F, Cl, -O-CH=CF2 or -OCF3. m represents 0, 1, 2, or 3, preferably 1 or 2, and particularly preferably 2. R 3 This refers to alkyl groups having 1 to 15 carbon atoms (where one or more CH2 groups include terminal carbon atoms, and in these groups, O or S atoms are independently not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] It may be replaced by -O-, -S-, -(CO)-O-, -O-(CO)-, and in addition, one or more H atoms may be replaced by F or Cl. ) or H, Preferably, the terms represent alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, alkenyl, alkenyloxy, alkoxyalkyl, fluorinated alkenyl, cycloalkyl (having 3 to 5 carbon atoms), cycloalkylalkyl, cycloalkylalkoxy, most preferably alkyl, cyclopropyl, cyclopentyl or alkenyl. [ka] Preferably [ka] And, L 31 and L 32 These represent H or F independently of each other, preferably L 31 This represents F, L 33 is H or CH3, preferably H. X 3 This represents a halogen, a halogenated alkyl or alkoxy having 1 to 3 carbon atoms, or a halogenated alkenyl or alkenyloxy having 2 or 3 carbon atoms, and is very preferably F, Cl, -OCF3, -OCHF2, -O-CH2CF3, -O-CH=CF2, -O-CH=CH2 or -CF3. Z 3 This represents -CH2CH2-, -CF2CF2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O- or a single bond, preferably -CH2CH2-, -COO-, trans-CH=CH- or a single bond, very preferably -COO-, trans-CH=CH- or a single bond. n represents 0, 1, 2, or 3, preferably 1, 2, or 3, and particularly preferably 1.

[0154] d) As an optional component, preferably as an essential component, one or more dielectrically neutral compounds selected from the group of compounds of formulas IV and V.

[0155] [ka]

[0156] During the ceremony, R 41 and R 42 These are, independently of each other, R in Equation III. 3 The above has the meanings shown above, and preferably, R 41 R represents alkyl, 42 R represents alkyl, cyclopropyl, cyclopentyl, or alkoxy, or R 41 This represents Alkenil, R 42 This represents alkyl, [ka] Z 41 and Z 42 They are, independently of each other, and Z 41 If it appears twice, these also independently represent -CH2CH2-, -COO-, trans-CH=CH-, trans-CF=CF-, -CH2O-, -CF2O-, -C≡C-, or a single bond, preferably one or more of them representing a single bond. p represents 0, 1, or 2, preferably 0 or 1. R 51 and R 52 R 41 and R 42 It has one of the meanings given for, and preferably represents an alkyl having 1 to 7 carbon atoms, preferably an n-alkyl, particularly preferably an n-alkyl having 1 to 5 carbon atoms, or an alkoxy having 1 to 7 carbon atoms, preferably an n-alkoxy, particularly preferably an n-alkoxy having 2 to 5 carbon atoms, or an alkoxyalkyl having 2 to 7 carbon atoms, preferably an alkoxyalkyl having 2 to 4 carbon atoms, an alkenyl or alkenyloxy, preferably an alkenyloxy. [ka] Preferably [ka] Z 51 ~Z 53 Each of these independently represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond, preferably -CH2-CH2-, -CH2-O-, or a single bond, particularly preferably a single bond. i and j each represent either 0 or 1, independently of each other. (i+j) preferably represents 0, 1, or 2, more preferably 0 or 1. However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0157] e) Also, as an optional component, may be substituted or added one or more dielectrically negative compounds selected from the group of compounds of formulas VI to IX.

[0158] [ka]

[0159] During the ceremony, R 61 This includes an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, or an alkenyl group having 2 to 7 carbon atoms, preferably a linear alkenyl group, particularly preferably a group having 2 to 5 carbon atoms, or an unsubstituted alkoxy group having 1 to 6 carbon atoms, or an unsubstituted alkenyloxy group having 2 to 6 carbon atoms or C 3~5 -Cycloalkyl-(CH2) 0~1 This represents, R 62 This includes an unsubstituted alkyl group having 1 to 7 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, and C 3~5 - Represents a cycloalkyloxy or an unsubstituted alkenyloxy group having 2 to 6 C atoms. L 61 , L 62 is independently H or methyl, preferably H. l represents 0 or 1, R 71 This includes an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably a linear alkenyl group, particularly preferably a group having 2 to 5 carbon atoms or C 3~5 -Cycloalkyl-(CH2) 0~1 This represents, R 72 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms; an unsubstituted alkoxy group having 1 to 6 carbon atoms, preferably 1, 2, 3, or 4 carbon atoms; or an unsubstituted alkenyloxy group having 2 to 6 carbon atoms, preferably 2, 3, or 4 carbon atoms. L 71 , L 72 is independently H or methyl, preferably H. [ka] This represents, R 81 This includes an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably propyl or pentyl, an alkenyl group having 2 to 7 carbon atoms, preferably a linear alkenyl group, particularly preferably a group having 2 to 5 carbon atoms or C 3~5 -Cycloalkyl-(CH2) 0~1 This represents, R 82 This includes an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms; an unsubstituted alkoxy group having 1 to 6 carbon atoms, preferably 1, 2, 3, or 4 carbon atoms; an unsubstituted alkenyloxy group having 2 to 6 carbon atoms, preferably 2, 3, or 4 carbon atoms; or C 3~5- Represents cycloalkyloxy, L 81 , L 82 is independently H or methyl, preferably H. [ka] Z 8 This represents -(C=O)-O-, -CH2-O-, -CF2-O-, or -CH2-CH2-, preferably -(C=O)-O- or -CH2-O-, o represents 0 or 1, R 91 and R 92 These are, independently of each other, on R 72 It has meaning given to it, R 91 This preferably represents an alkyl group having 2 to 5 carbon atoms, and more preferably 3 to 5 carbon atoms. R 92 This preferably represents an alkyl or alkoxy group having 2 to 5 carbon atoms, more preferably an alkoxy group having 2 to 4 carbon atoms, or an alkenyloxy group having 2 to 4 carbon atoms. [ka] p and q represent either 0 or 1 independently of each other. (p+q) preferably represents 0 or 1, [ka] In cases where this is the case, alternatively, and preferably, p=q=1 is used.

[0160] f) Preferably in the range of 1% to 30%, more preferably in the range of 2% to 20%, and particularly preferably in the range of 3% to 10%, one or more compounds of formula X again as optional components, preferably as essential components.

[0161] [ka]

[0162] During the ceremony [ka] [ka] n represents 1 or 2, preferably 1. R 1 Preferably, alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, C 3~5 -Cycloalkyl, C 3~5 -Cycloalkylalkyl, C 3~5 - Represents cycloalkylalkoxy, preferably alkyl, alkoxy, alkenyl or alkenyloxy, more preferably alkyl, alkenyl, alkoxy or alkenyloxy, most preferably alkyl, X 1 This represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy, or fluorinated alkenyloxy (the latter four groups preferably have 1 to 4 C atoms), more preferably F, Cl, CF3, or OCF3. However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0163] g) Again, as an optional component, preferably as an essential component, one or more compounds of formula XI, either as a substitute or as an addition.

[0164] [ka]

[0165] During the ceremony [ka] [ka] [ka] Preferably, [ka] n represents 0 or 1, R 11 and R 12 Each of these independently preferably represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms (wherein one CH2 group may be replaced by a 1,2-cyclopropyl group, a 1,3-cyclopentyl group, or a 1,3-cyclopentenylene group), an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms, preferably an alkyl, alkoxy, alkenyl or alkenyloxy, most preferably an alkyl, alkoxy or alkenyloxy, or R 11 is R 1 Represents, or R 12 is X 1 This represents, R 1 This preferably represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms (wherein one CH2 group may be replaced by a 1,2-cyclopropyl group, a 1,3-cyclopentyl group, or a 1,3-cyclopentenylene group), preferably an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably an alkyl or alkenyl. X 1 This represents F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy, or fluorinated alkenyloxy (the latter four groups preferably have 1 to 4 C atoms), more preferably F, Cl, CF3, or OCF3. However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group. Compounds of formula X are excluded.

[0166] The medium according to this application optionally contains one or more compounds of more compounds of formula L, preferably in a concentration of 1% to 40%, more preferably in a concentration of 2% to 30%, and particularly preferably in a concentration of 3% to 20%.

[0167] [ka]

[0168] During the ceremony, R L1 and R L2 These are alkyl groups having 1 to 15 carbon atoms independently of each other (however, in these groups, one or more CH2 groups, preferably one CH2 group, may be independently replaced by -C≡C-, -CF2O-, -OCF2-, -O-, -(CO)-O-, -O-(C=O)-, cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, preferably cyclopropylene or 1,3-cyclopentylene, and preferably one CH2 group may be replaced by a 1,2-cyclopropyl group, a 1,3-cyclopentyl group, or a 1,3-cyclopentenylene group). Represents an alkenyl, alkenyloxy, alkoxyalkyl, or fluorinated alkenyl having 2 to 7 C atoms, preferably alkyl or alkenyl (wherein one or more CH2 groups may be replaced with cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, or 1,3-cyclopentenylene, preferably cyclopropylene or 1,3-cyclopentenylene, such that the O atoms are not directly linked to each other, and where one or more H atoms may be replaced with halogens). Y L1 and Y L2 These are the same or different, representing H, F, or Cl, preferably Y L1 and Y L2 At least one of them is H, preferably Y L2 H is most preferably Y L1 and YL2 H is H.

[0169] The liquid crystal medium according to this application preferably has a nematic phase.

[0170] Through this application, especially R 1 , R 2 , R 3 , R 41 , R 51 , R L1 etc., and R L2 Regarding the definition of alkyl, alkyl means an alkyl group which may be linear or branched. Each of these groups is preferably linear and preferably has 1, 2, 3, 4, 5, 6, 7 or 8 C atoms, and is therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0171] When alkyl refers to a branched alkyl group, it preferably means 2-alkyl, 2-methylalkyl, or 2-(2-ethyl)-alkyl, preferably 2-butyl (=1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, especially 2-methylbutyl, 2-methylbutoxy-4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl, and 2-dodecyl. Of these groups, 2-hexyl and 2-octyl are preferred.

[0172] In this application, each branched group leading to a chiral compound is also referred to as a chiral group. Particularly preferred chiral groups are 2-alkyl, 2-alkoxy, 2-methylalkyl, 2-methylalkoxy, 2-fluoroalkyl, 2-fluoroalkoxy, 2-(2-ethyn)alkyl, 2-(2-ethyn)alkoxy, 1,1,1-trifluoro-2-alkyl, and 1,1,1-trifluoro-2-alkoxy.

[0173] Particularly preferred chiral groups include, for example, 2-butyl (=1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, especially 2-methylbutyl, 2-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 2-ethylhexoxy, 1-methylhexoxy, 2-octyloxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpentyl, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl, 2-dodecyl, 6-methoxyoctoxy, 6-methyloctoxy, 6-methyloctanoyloxy, and 5-methylheptyloxycarbonyl. These are 2-methylbutyryloxy, 3-methylvaleroyloxy, 4-methylhexanoyloxy, 2-chloropropionyloxy, 2-chloro-3-methylbutyryloxy, 2-chloro-4-methylvaleroyloxy, 2-chloro-3-methylvaleroyloxy, 2-methyl-3-oxapentyl, 2-methyl-3-oxahexyl, 1-methoxypropyl-2-oxy, 1-ethoxypropyl-2-oxy, 1-propoxypropyl-2-oxy, 1-butoxypropyl-2-oxy, 2-fluorooctyloxy, 2-fluorodecyloxy, 1,1,1-trifluoro-2-octyloxy, 1,1,1-trifluoro-2-octyl, and 2-fluoromethyloctyloxy. Highly preferred are 2-hexyl, 2-octyl, 2-octyloxy, 1,1,1-trifluoro-2-hexyl, 1,1,1-trifluoro-2-octyl, and 1,1,1-trifluoro-2-octyloxy.

[0174] Through this application, especially R D Regarding the definition of alkenyl, an alkenyl may be linear or branched, preferably linear, and preferably an alkenyl group having 2, 3, 4, 5, 6 or 7 or 8 carbon atoms. It is preferably vinyl, 1-E-alkenyl, or 3-E-alkenyl, and most preferably vinyl, 1-E-propenyl, 1-E-butenyl, 1-E-pentenyl, 3-butenyl, or 3-E-pentenyl.

[0175] Compounds of general formulas PY, T and II-IX are prepared by methods known in themselves, precisely known, and under reaction conditions suitable for the aforementioned reactions, as described in the literature (e.g., standard works such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, and Stuttgart). Variants known in themselves but not described in more detail here may be used.

[0176] Compounds of general formula Py can be synthesized as disclosed in European Patent Application Publication No. 2137154 and as shown in the synthesis examples.

[0177] Compounds of general formula T are preferably synthesized as disclosed in International Publication No. 2012 / 013281.

[0178] The present invention further relates to a liquid crystal display containing a liquid crystal medium according to the present invention, particularly an IPS or FFS display, and especially preferably an FFS or SG-FFS display.

[0179] The present invention further relates to an IPS or FFS type liquid crystal display comprising a liquid crystal cell consisting of two substrates (where at least one substrate is transparent to light and at least one substrate has an electrode layer) and a liquid crystal medium layer disposed between the substrates and containing polymerized components and low molecular weight components, wherein the polymerized components can be obtained by polymerizing one or more polymerizable compounds between the substrates of the liquid crystal cell in a liquid crystal medium, preferably while applying a voltage, and the low molecular weight components are the liquid crystal mixture according to the present invention as described above and below.

[0180] The display according to the present invention is preferably addressed by an active matrix LCD (AMD), preferably by a matrix of thin-film transistors (TFTs). However, the liquid crystal according to the present invention can also be used in advantageous manner with displays having other known addressing methods.

[0181] The present invention further relates to a method for preparing a liquid crystal medium by mixing one or more compounds of formula Py or its subformulas with one or more low molecular weight liquid crystal compounds or liquid crystal mixtures, and as an optional component, further liquid crystal compounds and / or additives.

[0182] The following meanings apply to "above" and "below."

[0183] Unless otherwise indicated, the term "FFS" is used to refer to FFS and SG-FFS displays.

[0184] The term "mesogenic group" is known to those skilled in the art and is documented in the literature. It refers to a group that, due to the anisotropy of its attractive and repulsive interactions, essentially contributes to the formation of a liquid-crystalline (LC) phase in low-molecular-weight or high-molecular-weight materials. Compounds containing mesogenic groups (mesogenic compounds) do not necessarily have an LC phase themselves. It is also possible for mesogenic compounds to exhibit liquid-crystalline phase behavior only after mixing with other compounds and / or polymerization. Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units. An overview of the terms and definitions used with respect to mesogens or liquid-crystalline compounds is given in Pure Appl. Chem. Vol. 73 (No. 5), p. 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368.

[0185] The term “spacer group” or simply “spacer,” also known above and below as “Sp,” is known to those skilled in the art and is documented in the literature, see, for example, Pure Appl. Chem., Vol. 73 (No. 5), p. 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368. Unless otherwise indicated above, the term “spacer group” or simply “spacer” above and below refers to a flexible group linking a mesogenic group and one or more polymerizable groups in a polymerizable mesogenic compound.

[0186] For the purposes of this invention, the term "liquid crystal medium" is intended to represent a medium comprising a liquid crystal mixture and one or more polymerizable compounds (e.g., a reactive mesogen). The term "liquid crystal mixture" (or "host mixture") is intended to represent a liquid crystal mixture consisting only of non-polymerizable low molecular weight compounds, preferably two or more liquid crystal compounds and optionally further additives (e.g., a chiral dopant or stabilizer).

[0187] Liquid crystal mixtures or liquid crystal media having a nematic phase at room temperature are particularly preferred.

[0188] In a preferred embodiment of the present invention, the liquid crystal medium is selected from the group of compounds of formula Py-A, more preferably from the group of compounds of formulas Py-1 to Py-5, and preferably comprises one or more compounds having more than 20 dielectric anisotropies.

[0189] [ka]

[0190] During the ceremony, R 1 This refers to alkyl groups having 1 to 15 carbon atoms (where one or more CH2 groups include terminal carbon atoms, and in these groups, O or S atoms are independently not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] It may be replaced by -O-, -S-, -(CO)-O-, -O-(CO)-, and in addition, one or more H atoms may be replaced by F or Cl. ) or H, A 1 Each of them appeared independently of the others. [ka] Preferably [ka] This represents, Z 1 These are independently identical or different, and are single bonds, -CH2O-, -(CO)O-, -CF2O-, -CH2CH2CF2O-, -CF2CF2-, -CH2CF2-, -CH2CH2-, -(CH2)4-, -CH=CH-, -CH=CF-, -CF=CF-, or -CH≡CH-, provided that asymmetric bridges may face both sides. L 1 , L 2 , L 3 , L 4 These are independently H, F, or Cl. L 5 is H, CH3 or CH2CH3, preferably H. X is F, Cl, -CF3, -OCF3, -CN, or -SCN. a represents 0, 1, or 2, preferably 1. b represents 0, 1 or 2, preferably 1, and However, a+b is 3 or less, preferably 1, 2, or 3, and particularly preferably equal to 1 or 2.

[0191] In this specification, compounds of the formula Py or Py-A, in which a+b is 1, 2, or 3, are particularly preferred. In particular, b is 1 and a is 1. In this specification, group A 1 Preferably, [ka] It represents.

[0192] In formulas Py, Py-A, and Py-1 to Py-5, independently b is 1, L 2 is F, L 3 is H or F, preferably F, and L 4 is F, L 5 H is H, R 1 This refers to alkyl groups having 1 to 7 carbon atoms (where one or more CH2 groups include terminal carbon atoms, and in these groups, the oxygen atoms are independently separated from each other so as not to be directly bonded to one another, such as -C≡C-, -CH=CH-, [ka] It may be replaced by -O-, and in addition, one or more H atoms may be replaced by F. ) Preferably, it is an alkyl group having 2 to 7 C atoms. Compounds are preferred.

[0193] In a preferred embodiment of the present invention, the liquid crystal medium is preferably one or more compounds having a dielectrically positive dielectric anisotropy of 3 or more, and includes compounds selected from the group of compounds of formula II-1 and II-2, and / or compounds selected from the group of compounds of formula III-1 and III-2.

[0194] [ka]

[0195] [ka]

[0196] In the formula, the parameter has the respective meanings shown above in formula II, L 24 and L 25 These independently represent H or F, preferably L 24 This represents F, [ka] In the case of equations II-1 and II-2, X 2 is preferably F or OCF3, particularly preferably F, and in the case of formula II-2, [ka]

[0197] [ka]

[0198] [ka]

[0199] In the equation, the parameter has the meaning given in Equation III.

[0200] The medium according to the present invention may contain, in place of or in addition to, one or more compounds of formula III-3, in addition to the compounds of formula III-1 and / or III-2.

[0201] [ka]

[0202] In the formula, the parameters have the respective meanings shown above, and parameter L 31 and L 32 These represent H or F, independently of each other and other parameters.

[0203] The liquid crystal medium is preferably L 21 and L 22 Furthermore / or L 24 and L 25 This includes compounds selected from the group of compounds represented by formulas II-1 and II-2, where both represent F.

[0204] In a preferred embodiment, the liquid crystal medium is L21 , L 22 , L 24 and L 25 This includes compounds selected from the group of compounds represented by formulas II-1 and II-2, where all of them represent F.

[0205] The liquid crystal medium preferably contains one or more compounds of formula II-1. The compounds of formula II-1 are preferably selected from the group of compounds of formula II-1a to II-1e, preferably one or more compounds of formula II-1a and / or II-1b and / or II-1d, preferably II-1a and / or II-1d or II-1b and / or II-1d, and most preferably the compound of formula II-1d.

[0206] [ka]

[0207] In the formula, the parameters have the respective meanings shown above, L 25 and L 26 These represent H or F, independently of each other and other parameters, preferably In equations II-1a and II-1b, L 21 and L 22 Both of them represent F, In equations II-1c and II-1d, L 21 and L 22 Both of them represent F, and / or L 23 and L 24 Both of them represent F, In equation II-1e, L 21 , L 22 and L 25 This represents F, However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0208] The liquid crystal medium preferably comprises one or more compounds of formula II-2, preferably selected from the group of compounds of formula II-2a to II-2k, and preferably containing one or more compounds each of formula II-2a and / or II-2h and / or II-2j.

[0209] [ka]

[0210] [ka]

[0211] [ka]

[0212] In the formula, the parameters have the respective meanings shown above, and L 25 ~L 28 These represent H or F independently of each other, preferably L 27 and L 28 Both of these represent H, and particularly preferably L 26 This represents H, However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0213] The liquid crystal medium is preferably L 21 and L 22 Both of them represent F, and / or L 23 and L 24 The compound includes compounds selected from the group of compounds represented by formulas II-2a to II-2k, where both represent F.

[0214] In a preferred embodiment, the liquid crystal medium is L 21 , L 22 , L 23 and L 24All of these include compounds selected from the group of compounds represented by formulas II-2a to II-2k, where all of them represent F.

[0215] Particularly preferred compounds of formula II-2 are those of the following formulas, and particularly preferred compounds are those of formula II-2a-1 and / or II-2h-1 and / or II-2k-2.

[0216] [ka]

[0217] [ka]

[0218] [ka]

[0219] In the formula, R 2 and X 2 The above has the meaning, and X 2 This preferably represents F.

[0220] The liquid crystal medium preferably contains one or more compounds of formula III-1. The compounds of formula III-1 are preferably selected from the group consisting of compounds of formulas III-1a to III-1j, and more preferably from formulas III-1d, III-1g, III-1h, III-1j, III-1k and III-1m.

[0221] [ka]

[0222] [ka]

[0223] [ka]

[0224] In the formula, the parameter has the meaning given above, preferably in the formula, X 3 This represents F, Cl, an alkyl or alkoxy halide having 1 to 3 carbon atoms, or an alkenyl or alkenyloxy halide having 2 or 3 carbon atoms, F, Cl, -OCF3, -OCHF2, -O-CH2CF3, -O-CH=CF2, -O-CH=CH2, or -CF3, preferably representing F, -OCF3, or -CF3. L 33 and L 34 These represent H or F independently of each other. L 35 and L 36 These independently represent H or F, preferably H.

[0225] The liquid crystal medium is preferably one or more compounds of formula III-1c, preferably selected from the group of compounds of formula III-1c-1 to III-1c-5, preferably from the group of compounds of formula III-1c-1 and / or III-1c-2, and most preferably from the group of compounds of formula III-1c-1.

[0226] [ka]

[0227] In the formula, R 3 It has the meaning shown above, However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0228] The liquid crystal medium preferably contains one or more compounds of formula III-1d, and the compounds are preferably selected from the group of compounds of formula III-1d-1 to III-1d-2, and preferably from the group of compounds of formula III-1d-1.

[0229] [ka]

[0230] During the ceremony, R 3 X is defined as above, 3 This is CF3, F, or OCF3, preferably CF3.

[0231] The liquid crystal medium preferably comprises one or more compounds of formula III-1f, and the compounds are preferably selected from the group of compounds of formula III-1g-1 to III-1g-6, preferably from the group of compounds of formula III-1f-1 and / or III-1g-2 and / or III-1g-3 and / or III-1g-6, more preferably from the group of compounds of formula III-1g-3 and / or III-1g-6, and more preferably from the group of compounds of formula III-1g-6.

[0232] [ka]

[0233] In the formula, R 3 It has the meaning shown above, However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0234] The liquid crystal medium preferably contains one or more compounds of formula III-1g, and the compounds are preferably selected from the group of compounds of formula III-1h-1 to III-1h-5, and more preferably from the group of compounds of formula III-1h-3.

[0235] [ka]

[0236] In the formula, R 3 It has the meaning shown above, However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0237] The liquid crystal medium preferably comprises one or more compounds selected from formulas III-1j, III-1k, and III-1m, and the compound is preferably selected from the group of compounds of formulas III-1j-1, III-1k-1, III-1m-1, and preferably III-1i-1.

[0238] [ka]

[0239] In the formula, the parameter has the meaning given above, X 3 preferably represents F or -OCF3.

[0240] The liquid crystal medium preferably comprises one or more compounds of formula III-1k, and the compounds are preferably selected from the group of compounds of formula III-1m-1 and III-1m-2, preferably from the group of compounds of formula III-1m-1.

[0241] [ka]

[0242] In the formula, the parameters have the meaning given above. However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0243] The liquid crystal medium according to the present invention preferably comprises one or more dielectrically neutral compounds preferably selected from the group of compounds of formulas VI, VII, VIII, and IX, having a dielectric anisotropy in the range of -1.5 to 3.

[0244] In this application, all elements include their respective isotopes. In particular, one or more H atoms in the compound may be replaced with D, which is especially preferred depending on the embodiment. By correspondingly highly deuterating the corresponding compound, for example, detection and recognition of the compound becomes possible.

[0245] In this application, The alkyl is particularly preferably a linear alkyl, especially CH3-, C2H5-, n-C3H7-, n-C4H9- or n-C5H 11 - represents, The alkenyl is particularly preferably CH2=CH-, E-CH3-CH=CH-, CH2=CH-CH2-CH2-, E-CH3-CH=CH-CH2-CH2-, or E-(n-C3H7)-CH=CH-.

[0246] In a preferred embodiment of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula VI selected from the group of compounds of formula VI-1 to VI-4, preferably one or more compounds of formula VI-2.

[0247] [ka]

[0248] In the formula, the parameters have the respective meanings given above in formula VI, preferably, In formula VI-1, R 61 and R 62 Each of these independently represents methoxy, ethoxy, propoxy, butoxy, or pentoxy, preferably ethoxy, butoxy, or pentoxy, more preferably ethoxy or butoxy, and most preferably butoxy. In Equation VI-2, R 61 Preferably, represents vinyl, 1-E-propenyl, buta-4-en-1-yl, penta-1-en-1-yl or penta-3-en-1-yl and n-propyl or n-pentyl. R62 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms, or an unsubstituted alkoxy group having 1 to 6 carbon atoms, particularly preferably 2 or 4 carbon atoms, most preferably an ethoxy group.

[0249] In a preferred embodiment of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula VII selected from the group of compounds of formula VII-1 to VII-3, preferably one or more compounds of formula VII-1 and one or more compounds of formula VII-2.

[0250] [ka]

[0251] In the formula, the parameters have the respective meanings given above in formula VII, preferably, R 71 This represents vinyl, 1-E-propenyl, buta-4-en-1-yl, penta-1-en-1-yl or penta-3-en-1-yl, n-propyl or n-pentyl, R 72 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms, or an unsubstituted alkoxy group having 1 to 6 carbon atoms, particularly preferably 2 or 4 carbon atoms, most preferably an ethoxy group. However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably a methyl group and / or an ethyl group, preferably one methyl group.

[0252] In preferred embodiments of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula VI-1 selected from the group of compounds of the following formula.

[0253] [ka]

[0254] In preferred embodiments of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula VI-2 selected from the group of compounds of the following formula.

[0255] [ka]

[0256] In preferred embodiments of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula VII-1 selected from the group of compounds of the following formula.

[0257] [ka]

[0258] In preferred embodiments of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula VII-2 selected from the group of compounds of the following formula.

[0259] [ka]

[0260] In addition to compounds of formula Py or its preferred subformulas, the medium according to the present invention may contain one or more dielectrically negative compounds selected from the group of compounds of formulas VI and VII, preferably in a total concentration within the range of 5% to 90%, preferably 10% to 80%, and particularly preferably 20% to 70%.

[0261] In preferred embodiments of the present invention, the medium according to the present invention comprises, in each case, one or more compounds of formula VIII selected from the group of compounds of formula VIII-1 to VIII-3, preferably one or more compounds of each of formula VIII-1 and / or one or more compounds of formula VIII-3.

[0262] [ka]

[0263] In the formula, the parameters have the respective meanings given above in formula VIII, preferably, R 81 This represents a vinyl group, 1-E-propenyl, buta-4-en-1-yl, penta-1-en-1-yl or penta-3-en-1-yl, ethyl, n-propyl or n-pentyl, alkyl, preferably ethyl, n-propyl or n-pentyl. R 82 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, preferably 1 to 5 carbon atoms, or an unsubstituted alkoxy group having 1 to 6 carbon atoms.

[0264] In equations VIII-1 and VIII-2, R 82 Preferably, represents an alkoxy having two or four C atoms, most preferably ethoxy, and in formula VIII-3, preferably an alkyl, preferably methyl, ethyl or n-propyl, most preferably methyl.

[0265] In a more preferred embodiment, the medium comprises one or more compounds of formula IV, preferably formula IVa.

[0266] [ka] During the ceremony, R 41 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably an n-alkyl group, and particularly preferably a group having 2, 3, 4, or 5 carbon atoms. R 42This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, an unsubstituted alkenyl group having 2 to 7 carbon atoms, or an unsubstituted alkoxy group having 1 to 6 carbon atoms, both of which preferably have 2 to 5 carbon atoms, and the unsubstituted alkenyl group preferably has 2, 3, or 4 carbon atoms, more preferably a vinyl group or a 1-propenyl group, particularly a vinyl group.

[0267] In a particularly preferred embodiment, the medium comprises one or more compounds of formula IV selected from the group of compounds of formula IV-1 to IV-4, preferably formula IV-1.

[0268] [ka]

[0269] During the ceremony, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. Alkenyl and alkenyl' independently represent alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms. 'alkenyl' preferably represents an alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms. alkoxy represents an alkoxy having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0270] In a particularly preferred embodiment, the medium according to the present invention comprises one or more compounds of formula IV-1 and / or one or more compounds of formula IV-2.

[0271] In a more preferred embodiment, the medium comprises one or more compounds of formula V.

[0272] In a more preferred embodiment, the medium comprises one or more compounds of formula XI, selected from the group of compounds of formula XI-1 and XI-2.

[0273] [ka]

[0274] [ka]

[0275] During the ceremony, R 11 and R 12 Each of these independently represents, preferably, an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms (wherein one CH2 group may be replaced by a 1,2-cyclopropyl group, a 1,3-cyclopentyl group or a 1,3-cyclopentenylene group), an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms, preferably an alkyl, alkoxy, alkenyl or alkenyloxy, most preferably an alkoxy or alkenyloxy. R 1 This preferably represents an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms (wherein one CH2 group may be replaced by a 1,2-cyclopropyl group, a 1,3-cyclopentyl group or a 1,3-cyclopentenylene group), an alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, preferably an alkyl or alkenyl. X 1 This represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy, or fluorinated alkenyloxy (the latter four groups preferably have 1 to 4 C atoms), preferably F, Cl, CF3, or OCF3, more preferably F, CF3, or OCF3, and most preferably CF3 or OCF3.

[0276] The medium according to the present invention preferably contains the following compounds in the total concentrations shown below: One or more compounds of formula H, especially formula H-1, especially H-1-1, Any one or more compounds of formula ST, particularly compounds of formula ST-15 and / or ST-18 and One or more compounds selected from the group of compounds of formula Py, in an amount of 0-30% by weight, and One or more compounds selected from the group of compounds of formula II, preferably formulas II-1 and II-2, in an amount of 0 to 60% by weight, and / or One or more compounds of formula III in an amount of 0-60% by weight, and / or One or more compounds of formula IV in an amount of 0-80% by weight, and / or One or more compounds of formula V in an amount of 0-50% by weight, and / or 0 to 20% by weight of one or more compounds of formula VI, and / or 0 to 20% by weight of one or more compounds of formula VII, and / or Preferably, 0 to 20% by weight of one or more compounds of formula VIII selected from the group of compounds of formula VIII-1 and VIII-2, and / or 0 to 20% by weight of one or more compounds of formula IX, and / or One or more compounds selected from the group of compounds of formula X, in an amount of 0-30% by weight.

[0277] The latter condition applies to all media covered by this application.

[0278] In a particularly preferred embodiment, the medium according to the present invention is One or more compounds of formula I, in a total concentration within the range of 1% to 40%, preferably within the range of 5% to 25%, and One or more compounds of formula H, particularly formula H-1, especially H-1-1, in a total concentration of the compounds of formula H in the range of 10 ppm to 3000 ppm, preferably 50 ppm to 2000 ppm, and very preferably 100 to 1000 ppm, and One or more compounds of formula ST, particularly formula ST-15 and / or ST-18, of formula H, in a total concentration ranging from 10 ppm to 3000 ppm, preferably 50 ppm to 2000 ppm, and very preferably 100 ppm to 1000 ppm, and / or One or more compounds of formula II, in a total concentration in the range of 5% to 50%, preferably in the range of 10% to 40%, and / or One or more compounds of formula VII-1 in a total concentration ranging from 5% to 30%, and / or One or more compounds of formula VII-2 in a total concentration ranging from 3% to 30%, and / or One or more compounds of formula XI, in a total concentration in the range of 3% to 50%, preferably 5% to 30%, and / or The mixture contains one or more compounds of formula X in a total concentration ranging from 3% to 50%, preferably from 5% to 30%.

[0279] Preferably, the concentration of the compound of formula Py in the medium according to the present invention is within the range of 1% to 20%, more preferably 1.5% to 20%, and most preferably 2% to 10%.

[0280] In a preferred embodiment of the present invention, the concentration of the compound of formula II in the medium is in the range of 3% to 60%, more preferably 5% to 55%, more preferably 10% to 50%, and most preferably 15% to 45%.

[0281] In a preferred embodiment of the present invention, the concentration of the compound of formula VII in the medium is in the range of 2% to 50%, more preferably 5% to 40%, more preferably 10% to 35%, and most preferably 15% to 30%.

[0282] The present invention also relates to an electro-optical display or electro-optical component containing a liquid crystal medium according to the present invention. An electro-optical display based on an FFS, IPS, VA, or ECB effect, preferably based on an IPS or FFS effect, and in particular preferably addressed by an active-matrix addressing device.

[0283] Similarly, the present invention relates to the use of a liquid crystal medium according to the present invention in an electro-optical display or electro-optical component, and is characterized by a method for preparing a liquid crystal medium according to the present invention, which is characterized by mixing one or more compounds of formula I with one or more compounds of formula H.

[0284] In a more preferred embodiment, the medium comprises one or more compounds of formula IV selected from the group of compounds of formula IV-2 and IV-3.

[0285] [ka]

[0286] [ka]

[0287] During the ceremony, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. alkoxy represents an alkoxy having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0288] In a more preferred embodiment, the medium comprises one or more compounds of formula V selected from the group of one or more compounds of formulas V-1 to V-5, preferably one or more compounds of formulas V-3, V-4, and V-5.

[0289] [ka]

[0290] In the formula, the parameter has the meaning given above in formula V, preferably, R 51 This represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms. R 52 This represents an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, preferably an alkyl group or an alkenyl group.

[0291] In a further preferred embodiment, the medium is R 51 and R 52 The compound comprises one or more compounds of formula V-3, preferably selected from the following formulas, in which at least one of the groups is an alkenyl having 2 to 6 carbon atoms.

[0292] [ka]

[0293] In the formula, "Alkyl" has the definition given above and is preferably methyl or ethyl. Compounds of formula V-3d are particularly preferred.

[0294] In a further preferred embodiment, the medium comprises one or more compounds of formula V-4 selected from the group of compounds of formula V-4a to V-4c.

[0295] [ka]

[0296] In the formula, alkyl and alkyl * These are linear alkyl groups, each independently having 1 to 6 carbon atoms, particularly methyl, ethyl, n-propyl, and pentyl.

[0297] The liquid crystal medium preferably comprises two or more compounds selected from the group of compounds of formulas V-4a, V-4b, and V-4c.

[0298] In a further preferred embodiment, the medium comprises one or more compounds of formula V-5 selected from the group of compounds of formula V-5a to V-5c, preferably formula V-5a.

[0299] [ka]

[0300] During the ceremony, Alkyl and alkyl * These are linear alkyl groups having 1 to 6 carbon atoms independently of each other, particularly methyl, ethyl, or n-propyl. Alkenyl preferably represents an alkenyl having 2 to 5 carbon atoms, more preferably 2 to 4 carbon atoms, and particularly preferably vinyl.

[0301] In addition to the compounds of formulas I, H, II-IX, L, and X, other components may also be present, for example, in amounts up to 45%, but preferably up to 35%, and particularly up to 10% of the total mixture.

[0302] The medium according to the present invention may also contain dielectrically negative compounds, the total concentration of which is preferably 20% or less, more preferably 10% or less, based on the total medium.

[0303] In a preferred embodiment, the liquid crystal medium according to the present invention is, in total amount based on the whole mixture, A compound of formula H in a total concentration in the range of 10 ppm to 3000 ppm, preferably 50 ppm to 2000 ppm and very preferably 100 to 1000 ppm, and A compound of formula I in an amount of 1% to 35%, preferably 2% to 30%, and particularly preferably 5% to 25%, and A compound of formula ST in total concentration of 10 ppm to 3000 ppm, preferably 50 ppm to 2000 ppm, and very preferably 100 to 1000 ppm, and / or A compound of formula II and / or III in an amount of 3% to 50%, preferably 4% to 45%, and particularly preferably 5% to 40%, and / or A compound of formula IV and / or V in an amount of 40% to 70%, preferably 50% to 65%, and particularly preferably 55% to 65%, and / or The mixture contains compounds of formula VI and / or VII and / or VIII and / or IX in amounts of 0% to 30%, 0% to 20%, and preferably 0% to 15%.

[0304] The liquid crystal medium according to the present invention may contain one or more chiral compounds.

[0305] Particularly preferred embodiments of the present invention satisfy one or more of the following conditions: However, acronyms (abbreviations) are explained in Tables A to C.

[0306] Preferably, the medium according to the present invention comprises one or more compounds of formula I and one or more compounds of formula H, and satisfies one or more of the following conditions.

[0307] i) The liquid crystal medium has a birefringence of 0.060 or higher, and more preferably 0.070 or higher.

[0308] ii) The liquid crystal medium has a birefringence of 0.200 or less, and particularly preferably 0.180 or less.

[0309] iii) The liquid crystal medium has a birefringence in the range of 0.090 or more and 0.180 or less.

[0310] iv) The total concentration of the compound of formula II in the whole mixture is 0.5% or more, preferably 1% or more, preferably 14% or less, particularly preferably 9% or less, and very particularly preferably 1% or more to 6% or less.

[0311] v) The liquid crystal medium contains one or more compounds of formula IV selected from the group of compounds CC-nV and / or CC-n-Vm and / or CC-VV and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably a compound of CC-3-V, at a concentration of preferably 60% or less, and particularly preferably 50% or less. Optionally, in addition to CC-3-V, it may also contain CC-3-V1 at a concentration of preferably 15% or less, and / or CC-3-2V1 at a concentration of preferably 15% or less, and / or CC-4-V at a concentration of preferably 40% or less, and particularly preferably 30% or less.

[0312] vi) The medium contains a compound of formula CC-nV, preferably CC-3-V, at a concentration of preferably 1% to 60%, more preferably 20% to 55%.

[0313] vii) The liquid crystal medium contains one or more compounds of formula IV, preferably formula IV-1 and / or IV-2, in an amount of preferably 20% or more, particularly 30% or more, very particularly preferably 40% or more, and preferably in the range of 46% to 55%.

[0314] viii) The total concentration of the compound of formula V in the whole mixture is 15% or more, preferably 20% or more, preferably in the range of 15% to 40%, and particularly preferably in the range of 20% to 30%.

[0315] ix) The total concentration of the compound of formula V-3 in the whole mixture is preferably 5% to 25%, and preferably 5% to 15%.

[0316] x) The total concentration of the compound of formula V-4, preferably V-4a to V-4c, in the entire mixture is preferably 3% to 30%, and preferably 10% to 25%.

[0317] xi) The total concentration of the compound selected from formula V-5, preferably V-5-a, and III-1d, preferably III-1d-1, in the whole mixture is preferably 2% to 20%, and preferably 4% to 15%.

[0318] The present invention further relates to an electro-optical display having an active matrix address based on an IPS, FFS, or UB-FFS effect, characterized in that it contains the liquid crystal medium according to the present invention as a dielectric.

[0319] The liquid crystal mixture preferably has a nematic phase range with a temperature range of at least 70°C.

[0320] The rotational viscosity γ1 is preferably 350 mPa·s or less, preferably 250 mPa·s or less, and particularly 150 mPa·s or less.

[0321] The mixture according to the present invention is suitable for all IPS and FFS-TFT applications using dielectrically positive liquid crystal media such as XB-FFS.

[0322] The liquid crystal medium according to the present invention preferably consists substantially entirely of 4 to 15 types, particularly 5 to 12 types, and especially preferably 10 types or less of compounds. These are preferably selected from the group of compounds of formulas Py, T, II, III, IV, V, VI, VII, VIII, and IX.

[0323] The liquid crystal medium according to the present invention may contain more than 18 types of compounds. In this case, the medium preferably contains 18 to 25 types of compounds.

[0324] In a preferred embodiment, the liquid crystal medium according to the present invention comprises a compound that does not contain a cyano group, preferably essentially, and most preferably substantially entirely.

[0325] In preferred embodiments, the liquid crystal media according to the present invention are selected from the group of compounds of formulas I, H, II, III, and IV and V, and preferably include compounds selected from the group of compounds of formulas I, H, II-1, II-2, III-1, III-2, IV and V; they preferably consist mostly, particularly preferably essentially, of compounds of the said formulas.

[0326] The liquid crystal medium according to the present invention preferably has a nematic phase in each case that is at least -10°C to 70°C or higher, particularly preferably -20°C to 80°C or higher, very particularly preferably -30°C to 85°C or higher, and most preferably -40°C to 90°C or higher.

[0327] In this specification, 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 temperature, and on the other hand, that no transparency occurs even when heated from the nematic phase. Low-temperature studies are performed in a fluid viscometer at the corresponding temperature and confirmed by storage for at least 100 hours in a test cell with a layer thickness suitable for electro-optical applications. If the storage stability at -20°C in the corresponding test cell is 1,000 hours or more, the medium is considered stable at this temperature. At -30°C and -40°C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the transparency point is measured in a capillary tube using conventional methods.

[0328] In a preferred embodiment, the liquid crystal medium according to the present invention is characterized by an optical anisotropy value in the moderate to low range. The birefringence value is preferably in the range of 0.075 or more to 0.130 or less, particularly preferably in the range of 0.085 or more to 0.120 or less, and very particularly preferably in the range of 0.090 or more to 0.115 or less.

[0329] In this embodiment, the liquid crystal medium according to the present invention has a positive dielectric anisotropy Δε, which is in the range of 2.0 to 20, more preferably 15, more preferably 2.0 to 10, particularly preferably 2.0 to 9.0, and very particularly preferably 2.5 to 8.0.

[0330] The liquid crystal medium according to the present invention preferably has a relatively low threshold voltage (V0) in the range of 1.0V to 5.0V, preferably to 2.5V, preferably 1.2V to 2.2V, and particularly preferably 1.3V to 2.0V.

[0331] In addition, the liquid crystal medium according to the present invention has a high VHR value in the liquid crystal cell.

[0332] Generally speaking, liquid crystal media with a lower address voltage or threshold voltage have a lower VHR than liquid crystal media with a higher address voltage or threshold voltage, and vice versa.

[0333] Furthermore, these preferred values ​​of individual physical properties are preferably maintained in combination with each other by the medium according to the present invention in each respective case.

[0334] In this application, the term "compound" is also written as "compound (one type or multiple types)," and unless otherwise specified, it refers to both one type of compound and multiple types of compounds.

[0335] In the present invention, unless otherwise specified in individual cases, the following definitions apply in relation to the identification of the constituent components of a composition.

[0336] • "Contains": The concentration of the target component in the composition is preferably 5% or more, particularly preferably 10% or more, and very particularly preferably 20% or more.

[0337] • "Constitutes the majority": The concentration of the target component in the composition is preferably 50% or more, particularly preferably 55% or more, and very particularly preferably 60% or more.

[0338] • "Essentially constitutes": The concentration of the target component in the composition is preferably 80% or more, particularly preferably 90% or more, and very particularly preferably 95% or more.

[0339] • "Substantially complete": The concentration of the component in question in the composition is preferably 98% or higher, particularly preferably 99% or higher, and very particularly preferably 100.0%.

[0340] This applies to both a medium as a composition having a group of compounds and components that may be individual compounds, and to a group of compounds having each of those components and compounds. As far as the concentration of individual compounds in the medium as a whole, the term "contains" means that the concentration of the compound (one type) or compound (multiple types) in question is preferably 1% or more, particularly preferably 2% or more, and very particularly preferably 4% or more.

[0341] In this invention, "≦" means less than or equal to, preferably less than, and "≧" means greater than or equal to, preferably greater than.

[0342] In the present invention, [ka] This represents trans-1,4-cyclohexylene, [ka] This represents a mixture of both cis- and trans-1,4-cyclohexylene. [ka] This represents 1,4-phenylene.

[0343] Throughout this application, 1,3-cyclopentenylene is a substructure selected from the group shown below. [ka] Preferably [ka] Most preferably [ka]

[0344] In this invention, the expression "dielectrically positive compound" means a compound having Δε > 1.5, the expression "dielectrically neutral compound" means a compound having -1.5 ≤ Δε ≤ 1.5, and the expression "dielectrically negative compound" means a compound having Δε < -1.5. The dielectric anisotropy of a compound is determined herein by dissolving 10% of the compound in a liquid crystal host and, in each case, determining the capacitance of the mixture obtained at 1 kHz in at least one test cell having a cell thickness of 20 μm and homeotropic and homogeneous surface orientations. The measurement voltage is typically 0.5 V to 1.0 V, but is always kept lower than the capacitance threshold of each liquid crystal mixture under consideration.

[0345] The host mixture used for dielectrically positive and dielectrically neutral compounds is ZLI-4792, and the host mixture used for dielectrically negative compounds is ZLI-2857; both are manufactured by Merck AG in Germany. The values ​​for each compound under consideration are obtained from the change in the dielectric constant of the host mixture after the addition of the compound under consideration, and the compound used is extrapolated to 100%. The compound under consideration is dissolved in the host mixture at a concentration of 10%. If the solubility of the substance is too low for this purpose, the concentration is gradually halved until the study can be conducted at the desired temperature.

[0346] The liquid crystal medium according to the present invention may also contain, if necessary, in typical amounts, further additives such as stabilizers and / or polychromatic, for example, dichroic dyes and / or chiral dopants. The amount of these additives used is preferably 0% to 10%, and particularly preferably 0.1% to 6%, based on the total amount of the mixture. The concentration of the individual compounds used is preferably 0.1% to 3%. The concentrations of these and similar additives are generally not considered when specifying the concentration and concentration range of the liquid crystal compounds in the liquid crystal medium.

[0347] In a preferred embodiment, the liquid crystal medium according to the present invention comprises a polymer precursor, which comprises, in a typical amount, one or more reactive compounds, preferably reactive mesogens, and, optionally, further additives such as polymerization initiators and / or polymerization moderators. The amount of these additives used is preferably 0% to 10%, and particularly preferably 0.1% to 2%, based on the total amount of the mixture. The concentrations of these and similar additives are generally not considered when specifying the concentration and concentration range of the liquid crystal compounds in the liquid crystal medium.

[0348] The composition consists of several types of compounds, preferably 3 to 30 types, particularly preferably 6 to 20 types, and very particularly preferably 10 to 16 types, and these compounds are mixed by conventional methods. Generally, a desired amount of a compound used in smaller quantities is dissolved in the compound constituting the main component of the mixture. This is advantageously carried out by raising the temperature. If the selected temperature is above the transparency point of the main component, it is particularly easy to observe the completion of the dissolution operation. However, liquid crystal mixtures can also be prepared by other conventional methods, for example, using a pre-mixture or from a so-called "multi-bottle system".

[0349] The mixture according to the present invention exhibits a very broad nematic phase range with a transparency point above 65°C, a very favorable volume threshold, and a relatively high retention rate, while simultaneously demonstrating very good low-temperature stability at -30°C and -40°C. Furthermore, the mixture according to the present invention is distinguished by its low rotational viscosity γ1.

[0350] Those skilled in the art will not need to mention that the media according to the present invention for use in VA, IPS, FFS, or PALC displays may also include, for example, compounds in which H, N, O, Cl, or F are replaced with corresponding isotopes.

[0351] The structure of the liquid crystal display according to the present invention corresponds to a conventional configuration, for example, as described in U.S. Patent Application Publication No. 2002 / 0041354.

[0352] The liquid crystal phase according to the present invention can be modified by appropriate additives to be used in any type of display disclosed to date, such as IPS and FFS LCD displays.

[0353] In the context of this invention, all concentrations are expressed in weight percent unless otherwise clearly stated, and unless otherwise clearly stated, they refer to the entire mixture or the entire component of the mixture. In this sense, the term "mixture" refers to a liquid crystal medium.

[0354] Unless otherwise clearly indicated, all temperature values ​​expressed in this application, such as the melting point T(C,N), the transition T(S,N) from the smectic (S) phase to the nematic (N) phase, and the transparency point T(N,I), are expressed in degrees Celsius (°C), and all temperature differences are expressed in degrees difference (° or degrees).

[0355] In this invention, unless otherwise explicitly stated, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Fredericks threshold.

[0356] Unless otherwise explicitly stated in each case, all physical properties are determined or have been determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals," published November 1997, Merck AG, Germany, with a temperature of 20°C applied, Δn determined at 436 nm, 589 nm, and 633 nm, and Δε determined at 1 kHz.

[0357] Electro-optical properties, such as threshold voltage (V0) (capacitive measurement), are determined in a test cell manufactured by Merck Japan, as well as the switch behavior. The measurement cell has a soda-lime glass substrate and a polyimide orientation layer (SE-1211 and diluent). ** It is constructed with an ECB or VA configuration containing 26 (mixing ratio 1:1, both manufactured by Nissan Chemical Corporation, Japan), and the alignment layers are rubbed orthogonally to each other, producing the effect of homeotropic alignment of the liquid crystal. The surface area of ​​the substantially square ITO electrode for transmission is 1 cm² 2 That is the case.

[0358] Unless otherwise indicated, chiral dopants are not added to the liquid crystal mixture used; however, this liquid crystal mixture is particularly suitable for applications where this type of doping is required.

[0359] Rotational viscosity was determined using the rotating permanent magnet method, and fluid viscosity was determined in a modified Ubbelohde viscometer. The liquid crystal mixtures ZLI-2293, ZLI-4792, and MLC-6608 are all products of Merck AG of Germany. The rotational viscosity values ​​determined at 20°C were 161 mPa·s, 133 mPa·s, and 186 mPa·s, respectively, and the fluid viscosity (ν) was 21 mm². 2 ·s -1 , 14mm 2 ·s -1 and 27mm 2 ·s -1 That is the case.

[0360] For practical purposes, the dispersion of materials has conventionally been characterized as follows, and will be used throughout this application unless otherwise explicitly stated. The birefringence value is determined at a temperature of 20°C at several fixed wavelengths using a modified Abbe refractometer having a homeotropically oriented surface on the side of the prism that contacts the material. The birefringence value is determined at specific wavelengths of 436 nm (selected spectral lines of a low-pressure mercury lamp), 589 nm (sodium D line), and 633 nm (He-Ne laser), using a combination of attenuators / diffusers to prevent damage to the observer's eyes. In the table below, Δn is given at 589 nm, and Δ(Δn) is given by Δ(Δn) = Δn(436 nm) - Δn(633 nm).

[0361] Unless otherwise specified, use the following symbols: Capacitive threshold voltage at 20°C [V] n e Anomalous refractive index at 20°C and 589nm Typical refractive index at 020°C and 589nm Δn Optical anisotropy at 20℃ and 589nm λ Wavelength λ [nm] Δn(λ) Optical anisotropy measured at 20°C and wavelength λ Δ(Δn) is the change in optical anisotropy, defined as follows. Δn(20℃, 436nm)-Δn(20℃, 633nm) Δ(Δn * ) The "relative change in optical anisotropy" is defined as follows: Δ(Δn) / Δn(20℃, 589nm) ε ⊥ Dielectric constant perpendicular to the director at 20°C and 1kHz ε ∥ Dielectric constant parallel to the director at 20°C and 1kHz Δε Dielectric anisotropy at 20℃ and 1kHz T(N,I) or clp. Point of transparency [°C] ν is the fluid viscosity measured at 20°C [mm²] 2 ·s -1 ] γ Rotational viscosity [mPa·s] measured at 120℃ K 11 Elastic constant [pN] for "spray" deformation at 20°C K 22 Elastic constant [pN] for "twist" deformation at 20°C

number

number

[0362] The following examples illustrate the present invention without limiting it. However, the following examples will be helpful to those skilled in the art in illustrating preferred compounds, their respective concentrations, and preferred combinations thereof, along with the concept of preferred mixtures. In addition, the following examples illustrate feasible properties and combinations of properties.

[0363] In this invention and the following examples, the structure of the liquid crystal compound is indicated by its initial letter, and the conversion to a chemical formula is performed according to Tables A to C below. All groups C n H 2n+1 , C m H 2m+1 and C l H 2l+1 or C n H 2n , C m H 2m and C l H 2lThese are linear alkyl or alkenyl groups having n, m, and l carbon atoms, respectively. Preferably, n, m, and l are independently 1, 2, 3, 4, 5, 6, or 7. Table A shows the codes for the ring elements of the compound's core structure, Table B lists the bridging groups, and Table C lists the meanings of the codes for the left or right terminal groups of the molecule. The initials consist of the code for the ring element along with any present linking groups, followed by a first hyphen and the code for the left terminal group, and a second hyphen and the code for the right terminal group.

[0364] <Table A: Ring elements>

[0365] [Table 1]

[0366] [Table 2]

[0367] [Table 3]

[0368] <Table B: Bridge Units>

[0369] [Table 4]

[0370] <Table C: Terminal group>

[0371] [Table 5]

[0372] In the formulas, n and m represent integers, respectively, and the three dots "..." are spaces for other abbreviations from this table.

[0373] In addition to the compound of formula B, the mixture according to the present invention preferably includes one or more compounds as described below.

[0374] Use the following abbreviations: (n, m, k, and l are each an integer, preferably 1 to 9, preferably 1 to 7, and k and l may also be 0, preferably 0 to 4, more preferably 0 or 2, most preferably 2; n is preferably 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, more preferably 2 or 4 in combination "-nO-"; m is preferably 1, 2, 3, 4, or 5, preferably 1, 2, 3, or 4, more preferably 2 or 4 in combination "-Om"; the combination "-lVm" is preferably "2V1".) [Examples]

[0375] <Stabilizers to be used>

[0376] [Table 6]

[0377] <Mixture example>

[0378] To measure VHR, a mixture corresponding to an electro-optic test cell consisting of two AF glass substrates with an ITO layer approximately 20 nm thick and a polyimide layer 100 nm thick is filled. VHR is measured before and after a predetermined time by applying a voltage of 1 V / 60 Hz at 60°C. The difference in VHR before and after stress is:

number

[0379] Typically, thermal stress causes a decrease in VHR in LC mixtures; therefore, the smaller the absolute value of the decrease in VHR after stress, the better the performance for display applications.

[0380] <Host mixture - H-1> The following mixtures are prepared according to the table below.

[0381] [Table 7]

[0382] Then, 10% by weight of PUS-3-2 according to the acronym table given above is added, resulting in host mixture H-1.

[0383] [Table 8]

[0384] <Host mixture - H-2> The following mixtures are prepared according to the table below.

[0385] [Table 9]

[0386] Then, 10% by weight of PUS-2-2 according to the acronym table given above is added, resulting in the acquisition of host mixture H-2.

[0387] <Mixture M-1> Mixture H-1 is mixed with stabilizer S-1 at a concentration of 0.03% by weight, resulting in mixture M-1.

[0388] [Table 10]

[0389] <Comparative mixture CM-1> 0.03% by weight of Tinuvin® 770 is added to mixture H-1, resulting in a comparative mixture CM-1, which is a comparison with mixture M-1.

[0390] [Table 11]

[0391] <Mixture M-2> Mixture H-1 is mixed with 0.1% by weight of S-1 to obtain mixture M-2.

[0392] [Table 12]

[0393] <Mixture M-3> Mixture H-1 is mixed with 0.1% by weight of S-2 to obtain mixture M-4.

[0394] [Table 13]

[0395] <Comparative mixture CM-2> 0.1% by weight of Tinuvin® 770 was added to mixture H-1, resulting in comparative mixture CM-2, which is a comparison with mixtures M-2 and M-3.

[0396] [Table 14]

[0397] <Mixture M-4> Mixture H-1 is mixed with 10% by weight of M-2 to obtain mixture M-4.

[0398] <Mixture M-5> Mixture H-1 is mixed with 10% by weight of M-3 to obtain mixture M-5.

[0399] <Comparative mixture CM-3> Mixture CM-2 is added at a concentration of 10% by weight to mixture H-1, resulting in comparative mixture CM-3, which is a comparison with mixtures M-4 and M-5.

[0400] <Mixture M-6> Mixture H-2 is mixed with 0.1% by weight of S-1 to obtain mixture M-6.

[0401] <Mixture M-7> The following mixtures are prepared according to the table below, resulting in mixture M-7.

[0402] [Table 15]

[0403] <Mixture M-8> The following mixtures are prepared according to the table below, resulting in mixture M-8.

[0404] [Table 16]

Claims

1. An LC medium characterized by containing one or more compounds of formula I and one or more compounds of formula H. 【Chemistry 1】 (In the formula, each base has the following meaning: R １ and R ２ H, F, Cl, Br, -CN, -SCN, -NCS, SF ５ Alternatively, it represents a linear or branched alkyl group having 1 to 12 carbon atoms, in addition to one or more non-adjacent CH groups. ２ The groups may be replaced with -CH=CH-, -C≡C-, -O-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, where each group is independent of the others and the oxygen atoms are not directly bonded to each other, and one or more hydrogen atoms may be replaced with F, Cl or Br. A ０ 、 A １ and A ２ are each, independently of one another, phenylene-1,4-diyl (in which in addition one or two CH groups may be replaced by N and one or more H atoms are halogen, CN, CH ３ , CHF ２ , CH ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ and may be replaced. ), cyclohexane-1,4-diyl (in which in addition one or two non-adjacent CH ２ groups may each, independently of one another, be replaced by O and / or S and one or more H atoms may be replaced by F. ), cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, Z １ and Z ２ Each of them is independent of the other, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -CO-O-, -O-CO-, -C ２ H ４ -, -C ２ F ４ -, -CF ２ CH ２ -ien-CH ２ CF ２ -, -CFHCFH-, -CFHCH ２ -ien-CH ２ CFH-, -CF ２ CFH-, -CFHCF ２ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C- or single bond, m and n each independently represent 0, 1, 2, or 3. 【Chemistry 2】 (In the formula, R Ｈ H, O ● ,CH ３ , OH or OR Ｓ This represents, R Ｓ This represents an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms. R １１ Each instance independently represents a linear or branched alkyl chain having H, F, and 1 to 20 C atoms, except for one -CH ２ - One or more -CH groups, if present. ２ The - group may be replaced with -O- or -(C=O)-, but two adjacent -CH groups may be replaced. ２ - A - group cannot be replaced with -O-; one or multiple -CH groups if present. ２ The - group may be replaced with -CH=CH- or -C≡C-, where one or more H atoms are replaced with F, OR １３ , N(R １３ ) (Caution １４ ) or R １５ It can be replaced with, R １２ Each instance independently comprises a linear or branched alkyl chain having 1 to 20 carbon atoms (in the chain, one -CH ２ - group or multiple -CH groups ２ The - group may be replaced with -O- or -(C=O)-, but two adjacent -CH groups may be replaced. ２ - The - group cannot be replaced with -O-. ), a hydrocarbon group containing a cycloalkyl or alkylcycloalkyl unit (in the group, one -CH ２ - group or multiple -CH groups ２ The - group may be replaced with -O- or -(C=O)-, but two adjacent -CH groups may be replaced. ２ - The group cannot be replaced with -O-, and in the group, one or more H atoms are F, OR １３ , N(R １３ ) (Caution １４ ) or R １５ It may be replaced by: ) or an aromatic or heteroaromatic hydrocarbon group (in the group, one or more H atoms are F, OR １３ , N(R １３ ) (Caution １４ ) or R １５ It can be replaced with this.) R １３ Each instance represents a linear or branched alkyl or acyl group having 1 to 10 carbon atoms independently of each other. R １４ Each instance represents a linear or branched alkyl or acyl group having 1 to 10 carbon atoms independently of each other. R １５ Each instance represents a linear or branched alkyl group having 1 to 10 C atoms independently of each other, and the group contains 1 -CH ２ - group or multiple -CH groups ２ The - group may be replaced with -O- or -(C=O)-, but two adjacent -CH groups may be replaced. ２ -It is not possible to replace the - group with -O-. S １１ and S １２ Each instance represents an alkylene group having 1 to 20 C atoms independently of each other, and the group is branched or linear, except for one -CH group. ２ - One or more -CH groups, if present. ２ The - group may be replaced with -O- or -(C=O)-, but two adjacent -CH groups may be replaced. ２ - A - group cannot be replaced with -O-; one or multiple -CH groups if present. ２ The - group may be replaced with -CH=CH- or -C≡C-, where one or more H atoms are replaced with F, OR １３ , N(R １３ ) (Caution １４ ) or R １５ It can be replaced by, or it represents a single bond. X １１ This represents C, Y １１ ~Y １４ Each of these independently represents either methyl or ethyl. Z １１ ~Z １４ independently of each other at each occurrence, represents -O-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -O-(C=O)-O-, -(N-R １３ ), -N-R １３ -(C=O)- or a single bond, provided that when S １１ is a single bond, Z １１ and Z １２ do not both represent -O- at the same time, however when S １２ is a single bond, Z １３ and Z １４ do not both represent -O- at the same time, and however when -X １１ [-R １１ ｏ - is a single bond, Z １２ and Z １３ do not both represent -O- at the same time,​ n × p represents an integer between 3 and 10. p represents 1 or 2, o represents (3-p), If p is 1, n represents 3, 4, 5, 6 or 8, and m represents (10-n), and If p is 2, n represents an integer between 2 and 4, and m represents (4-n), 【Transformation 3】 is an organic group having (m + n) bonding sites (where m groups R present in the molecule １２ In addition to, but independently of them, one additional H atom may be replaced by R １２ or a plurality of additional H atoms may be replaced by R １２ where, however, one —CH ２ — group or a plurality of —CH ２ — groups may be replaced by —O— or —(C═O)— so that two O atoms are not directly bonded to each other).) or a substituted or unsubstituted aromatic or heteroaromatic hydrocarbon group having up to 10 valences (where m groups R present in the molecule １２ In addition to, but independently of them, one additional H atom may be replaced by R １２ or a plurality of additional H atoms may be replaced by R １２ ).), And when p = 1, or -X １１ [-R １１ ] ｏ (The dash can also represent a single bond.)

2. The LC medium according to claim 1, characterized by containing one or more compounds of formula I selected from the group of compounds I1 to I16. 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 (In the formula, R １ , R ２ and L １ ~L ６ (This has the meaning set forth in claim 1.)

3. The LC medium according to claim 1, characterized in that the compound of formula H is selected from the following group of compounds of formula H-1 to H-13. 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】

4. The LC medium according to claim 1, characterized by further comprising one or more compounds of formula II and / or III. 【Chemistry 14】 (In the formula, R ２ This is an alkyl group having 1 to 15 C atoms (provided that it has 1 or more CH ２ The group contains a terminal carbon atom, and in this group, the oxygen or sulfur atoms are arranged such that they are not directly bonded to each other, such as -C≡C-, -CH=CH-, 【Chemistry 15】 It may be replaced with -O-, -S-, -(CO)-O-, -O-(CO)-, and in addition, one or more H atoms may be replaced with F or Cl. ) or H, 【Chemistry 16】 This represents, L ２１ and L ２２ This represents H or F, L ２３ is H or CH ３ And, X ２ This represents a halogen, a halogenated alkyl or alkoxy having 1 to 3 carbon atoms, or a halogenated alkenyl or alkenyloxy having 2 or 3 carbon atoms. m represents 0, 1, 2, or 3. R ３ This is an alkyl group having 1 to 15 C atoms (provided that it has 1 or more CH ２ The group contains a terminal carbon atom, and in this group, the oxygen or sulfur atoms are arranged such that they are not directly bonded to each other, such as -C≡C-, -CH=CH-, 【Chemistry 17】 It may be replaced with -O-, -S-, -(CO)-O-, -O-(CO)-, and in addition, one or more H atoms may be replaced with F or Cl. ) or H, [Chemistry 18] And, L ３１ and L ３２ These represent H or F independently of each other. L ３３ is H or CH ３ And, X ３ This represents a halogen, a halogenated alkyl or alkoxy having 1 to 3 carbon atoms, or a halogenated alkenyl or alkenyloxy having 2 or 3 carbon atoms. Z ３ is, -CH ２ CH ２ -, -CF ２ CF ２ -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH ２ O- or single bond is represented, n represents 0, 1, 2, or 3.

5. The LC medium according to claim 1, characterized by further comprising one or more compounds selected from the group consisting of the following formulas. 【Chemistry 19】 (In the formula, R ４１ and R ４２ These are alkyl groups having 1 to 15 carbon atoms independently of each other (where one or more CH₂ groups include terminal carbon atoms, and in these groups, O or S atoms are not directly bonded to each other independently, such as -C≡C-, -CH=CH-, 【Chemistry 20】 It may be replaced with -O-, -S-, -(CO)-O-, -O-(CO)-, and in addition, one or more H atoms may be replaced with F or Cl. ) or H, 【Chemistry 21】 Z ４１ and Z ４２ They are independent of each other, and Z ４１ If it appears twice, these also appear independently of each other, -CH ２ CH ２ -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH ２ O-, -CF ２ O-, -C≡C-, or single bond are represented. p represents 0, 1, or 2. R ５１ and R ５２ They are independent of each other, R ４１ and R ４２ It has one of the meanings that can be given about it, 【Chemistry 22】 Z ５１ ~Z ５３ Each of them is independent of the other, -CH ２ -CH ２ -ien-CH ２ -O-, -CH=CH-, -C≡C-, -COO-, or single bond are represented. i and j each represent either 0 or 1 independently of each other. (i + j) represents 0, 1, or 2. However, each ring may be substituted with one or two alkyl groups.

6. The LC medium according to claim 1, characterized by further comprising one or more compounds selected from the group consisting of the following formulas. 【Chemistry 23】 (In the formula, R ６１ This represents an unsubstituted alkyl group having 1 to 7 carbon atoms. R ６２ This includes an unsubstituted alkyl group having 1 to 7 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, and C ３～５ - Represents a cycloalkyloxy or an unsubstituted alkenyloxy group having 2 to 6 carbon atoms. L ６１ , L ６２ is independently H or methyl, l represents 0 or 1, R ７１ This represents an unsubstituted alkyl group having 1 to 7 carbon atoms. R ７２ This represents an unsubstituted alkyl group having 1 to 7 carbon atoms. L ７１ , L ７２ is independently H or methyl, 【Chemistry 24】 This represents, R ８１ This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, and an unsubstituted alkoxy group having 1 to 6 carbon atoms. R ８２ This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, and an unsubstituted alkoxy group having 1 to 6 carbon atoms. L ８１ , L ８２ is independently H or methyl, 【Chemistry 25】 This represents, Z ８ is -(C=O)-O-, -CH ２ -O-, -CF ２ -O- or -CH ２ -CH ２ - represents, o represents 0 or 1, R ９１ and R ９２ They are independent of each other, on R ７２ It has meaning given to it, R ９１ This represents an alkyl group having 2 to 5 carbon atoms. R ９２ This represents an alkyl or alkoxy group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms. 【Chemistry 26】 This represents, p and q independently represent 0 or 1, and (p + q) represents either 0 or 1. 【Chemistry 27】 (If this is the case, then p = q = 1 is an alternative.)

7. The LC medium according to claim 1, characterized by containing one or more compounds of formula IVa. 【Chemistry 28】 (In the formula, R ４１ This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkenyl group having 2 to 7 carbon atoms. R ４２ (This represents an unsubstituted alkyl group having 1 to 7 carbon atoms, an unsubstituted alkenyl group having 2 to 7 carbon atoms, or an unsubstituted alkoxy group having 1 to 6 carbon atoms.)

8. The LC medium according to claim 1, characterized in that the total concentration of the compound of formula I in the entire medium is 1% to 25%.

9. The LC medium according to claim 1, characterized in that the total concentration of the compound of formula H in the LC medium is in the range of 10 ppm to 10,000 ppm.

10. Use of the LC medium according to claim 1 in an electro-optical device.

11. An LC display comprising the LC medium described in claim 1.

12. The display according to claim 11, characterized by being based on IPS or FFS effects.

13. A method for preparing the LC medium according to claim 1, characterized in that one or more compounds of formula I are mixed with one or more compounds of formula H.

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