Liquid crystal media and compounds

Abstract

We provide liquid crystal media and compounds. [Solution] The present invention relates to a liquid crystal medium (also called a liquid crystal material) having a nematic phase comprising one or more compounds having a 5,6-difluorobenzo[b]furan ring at the terminal represented by the formula, its use in electro-optical displays, particularly active matrix displays based on IPS or FFS effects, and displays comprising this type of liquid crystal material, particularly energy-saving LC displays or low-power LC displays.

Description

[Technical Field]

[0001] The present invention relates to a liquid crystal medium (also called a liquid crystal material) having a nematic phase containing one or more benzofuran compounds of formula I, novel compounds according to formula I, their use in electro-optical displays, particularly in active matrix displays based on IPS or FFS (fringe-field switching) effects using dielectrically positive liquid crystals, and displays of the same kind containing such liquid crystal media.

[0002] [ka]

[0003] In the formula, the parameters have the meanings given in the following text. [Background technology]

[0004] IPS and FFS displays, which use liquid crystals with a positive dielectric constant, are well-known in this field and are widely used not only in various displays such as desktop monitors and televisions, but also in gaming, mobile, and automotive applications.

[0005] However, in recent years, IPS displays, particularly FFS displays, that use liquid crystals with a negative dielectric constant have become widely adopted. The latter is also called UB-FFS (ultra-high brightness FFS). Such displays are disclosed, for example, in U.S. Patent Application Publication No. 2013 / 0207038 (Patent Document 1). These displays are characterized by significantly improved transmittance compared to conventional IPS and FFS displays that use liquid crystals with a positive dielectric constant. However, conventional displays using liquid crystals with a negative dielectric constant have a major drawback: they require a higher operating voltage than displays using liquid crystals with a positive dielectric constant. The liquid crystal medium used in UB-FFS has a dielectric anisotropy of -0.5 or less, preferably -1.5 or less.

[0006] The liquid crystal media used in high-brightness FFS (HB-FFS) have a dielectric anisotropy of 0.5 or higher, preferably 1.5 or higher. For example, U.S. Patent Application Publication No. 2013 / 0207038 (Patent Document 1) discloses a liquid crystal media for HB-FFS that includes both dielectrically negative liquid crystal compounds and dielectrically positive liquid crystal compounds, i.e., mesogenic compounds. These media are ε ⊥ and ε avg Although the value of (ε) is already quite large, ⊥ The ratio of / Δε) is relatively small.

[0007] However, in this application, an IPS effect or FFS effect using a uniformly oriented dielectrically positive liquid crystal medium is preferred.

[0008] To industrially apply this effect to electro-optical display elements, a liquid crystal phase that meets diverse requirements is necessary. Particularly important is resistance to physical influences such as moisture, air, heat, radiation in the infrared, visible light, and ultraviolet regions, and direct current (DC) and alternating current (AC) electric fields.

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

[0010] Among the previously disclosed compounds having a liquid crystal mesophase, there is no single compound that satisfies all of these requirements. Therefore, in order to obtain a substance that can be used as a liquid crystal phase, a mixture of 2 to 25 types, preferably 3 to 18 types of compounds, is generally prepared.

[0011] Development in the field of liquid crystal materials is still ongoing. Constant efforts are being made to develop novel compounds that will enable the optimization of displays in order to improve the characteristics of liquid crystal display elements. [Prior art documents] [Patent Documents]

[0012] [Patent Document 1] U.S. Patent Application Publication No. 2013 / 0207038 [Patent Document 2] Chinese Patent Application Publication No. 108018049 Specification [Patent Document 3] Chinese Patent Application Publication No. 108003895 Specification [Overview of the project] [Problems that the invention aims to solve]

[0013] The object of the present invention is to provide a liquid crystal medium with advantageous properties. In addition to the physical properties required of the material, sustainability, such as environmentally related properties (e.g., perfluoroalkyl content), is becoming increasingly important.

[0014] Considering the diverse application fields of such compounds with high Δε, compounds with properties that precisely suit each application, preferably having a high transparency point and low viscosity, are desirable.

[0015] Therefore, the present invention aims to find novel and stable compounds that are particularly suitable as components of liquid crystal media such as TN, STN, IPS, FFS, and TN TFT displays.

[0016] Furthermore, the compounds according to the present invention should be thermally and photochemically stable under the conditions of application. As mesogens, they should enable a broad nematic phase in mixtures with liquid crystal co-components and have excellent miscibility with nematic base mixtures, especially at low temperatures. Substances with low melting points and enthalpies of melting are preferred, as these values ​​are indicators of the desirable properties mentioned above, such as high solubility, a broad liquid crystal phase, and a low tendency for spontaneous crystallization of the mixture at low temperatures. Solubility at low temperatures, i.e., avoidance of crystallization, is particularly important for the safe operation and transport of displays in and out of aircraft.

[0017] Liquid crystal media with positive dielectric anisotropy for IPS and FFS displays have already been disclosed.

[0018] Benzofurans as liquid crystal materials and their synthesis methods are disclosed in Chinese Patent Application Publication No. 108018049 (Patent Document 2). The uses of the mixture are disclosed in Chinese Patent Application Publication No. 108003895 (Patent Document 3).

[0019] The phase range of a liquid crystal mixture must be sufficiently broad depending on the display application. The response time of the liquid crystal medium in a display must be as short as possible, especially for video, animation simulation, and gaming applications. This is particularly important for television and multimedia displays. To improve response time, optimizing the rotational viscosity (γ1) of the liquid crystal medium, i.e., achieving a medium with the lowest possible rotational viscosity, has been repeatedly proposed. However, the results to date have been insufficient for many applications, and it is desirable to find further optimization methods.

[0020] It is extremely important that the medium has sufficient stability against extreme loads, especially ultraviolet irradiation and heating. This can be particularly crucial for display applications in mobile devices such as cell phones.

[0021] Active-matrix displays that have been released to date have several drawbacks in addition to relatively low transmittance and relatively long response times. For example, they have relatively low contrast, relatively high viewing angle dependence, difficulty in reproducing grayscale, especially when viewed from an oblique angle, and insufficient VHR (Variable Life Cycle) and their lifespan. Optimizing transmission characteristics and response time is essential to improve the energy efficiency of displays and, consequently, their high-speed video display capabilities.

[0022] Therefore, there remains a high demand for displays with a wide operating temperature range, short response time, relatively low threshold voltage, and very high resistivity, capable of displaying a wide range of gray tones, and especially for displays with good and stable VHR.

[0023] The present invention aims to provide displays based on ECB, IPS, or FFS effects that are suitable not only for monitor and television applications but also for mobile applications such as telephones and navigation systems. These displays overcome or mitigate the aforementioned drawbacks while simultaneously possessing very high resistivity. In particular, mobile phones and navigation systems are required to operate in extremely high and extremely low temperature environments. [Means for solving the problem]

[0024] Remarkably, it has been found that environmentally friendly liquid crystal displays can be realized, particularly in IPS and FFS displays, that have a low threshold voltage and short response time, a sufficiently wide nematic phase, good birefringence (Δn), and at the same time high transmittance, high contrast, excellent stability against decomposition by heating and UV irradiation, and a stable high VHR. This is achieved by using a nematic liquid crystal medium in these display elements that contains at least one, preferably two or more, compounds of formula I, preferably one or more, preferably two or more, compounds selected from the group of compounds of formulas T, II, and III, and / or one or more, preferably two or more, compounds selected from the group of compounds of formula IV and / or V.

[0025] This type of medium can be used in electro-optical displays, particularly those with active matrix addressing for IPS or FFS displays.

[0026] The contrast of an LCD display can be improved, on the one hand, by increasing the transmittance, which is due to the ε in the FFS cell layout. ⊥ This can be achieved by increasing the elastic constant (K). On the other hand, it can be improved by improving the dark state. The latter, i.e., the dark state, is greatly influenced in particular by the scattering parameter. Here, a high elastic constant (K 11 , K 33A liquid crystal medium having ) reduces scattering and thereby improves the contrast of LCDs. This also leads to excellent performance in the display according to the present invention.

[0027] These media are characterized by particularly high transmittance and particularly excellent black state representation, which is mainly caused by very low scattering and reduced response time in each display. This is due to particularly high elastic constants, in particular high K 11 , high K avg values, and the rotational viscosity (γ₁) and elastic constant (K 11 ) ratio (γ₁ / K 11 ) has an excellent low value, which is achieved by a unique combination of physical properties. Thereby, excellent performance is obtained in the display according to the present invention.

[0028] The medium according to the present invention preferably further comprises one or more compounds selected from the group of compounds of formulae T, II and III, preferably one or more compounds of formula II, more preferably one or more compounds of formula III, even more preferably one or more compounds selected from the group of compounds of formulae IV and V, and still more preferably one or more compounds selected from the group of compounds of formulae VI to IX, wherein all formulae are as defined below.

[0029] The mixture according to the present invention exhibits a very broad nematic phase range with a clearing point of 70°C or higher, a very favorable capacitance threshold, a relatively high holding ratio, simultaneously good low-temperature stability at 20°C and -30°C, and very low rotational viscosity. The mixture according to the present invention is further characterized by a good ratio of clearing point to rotational viscosity, and relatively high positive dielectric anisotropy.

[0030] The medium of the present invention is characterized by a combination of specific physical properties. Most importantly among these is the high value of the elastic constant, and in particular, the ratio (γ₁ / k 11 ) of rotational viscosity (γ₁) to elastic constant (k 11 ) is very low. Furthermore, it exhibits high ε ⊥ and achieves good transmittance.

[0031] A first embodiment of the present invention is a liquid crystal medium comprising the following:

[0032] a) One or more compounds of formula I are used, 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%.

[0033] [ka]

[0034] During the ceremony, R 1 represents an alkyl group having 1 to 15 carbon atoms, where one or more CH2 groups containing terminal carbon atoms in this group are independently linked to each other in such a way that O or S atoms are not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] Substitutions may be made with -O-, -S-, -(CO)-O-, and -O-(CO)-, provided that one or more H atoms are replaced with F or Cl. A 0 Each instance independently represents phenylene-1,4-diyl (wherein one or two CH groups may be replaced by N, and one or more H atoms may be replaced by halogens, CN, CH3, CHF2, CH2F, OCH3, OCHF2, or OCF3), cyclohexane-1,4-diyl (wherein one or two non-adjacent CH2 groups may be independently 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. A 0 Preferably, [ka] more, [ka] This represents, During the ceremony, L 1 , L 2 Each of these independently represents F, Cl, CH3 or OCH3, preferably F, and Y represents CH3 or CH2CH3, Z 0 These represent, independently of each other, identical or different single bonds, -CH2O-, -(CO)O-, -CF2O-, -CH2CH2CF2O-, -CF2CF2-, -CH2CF2-, -CH2CH2-, -(CH2)4-, -OCH2-, -OCF2-, -CH=CH-, -CH=CF-, -CF=CF- or -C≡C-, and n represents 1, 2, or 3, preferably 1 or 2.

[0035] Further embodiments of the present invention include compounds of formula I and their use in liquid crystal displays, particularly in liquid crystal media in positive dielectric media (preferably IPS, FFS). [Modes for carrying out the invention]

[0036] The medium according to the present invention preferably further comprises one or more additional compounds selected from the group of compounds according to the following conditions b) to f).

[0037] b) One or more preferably dielectrically neutral compounds of formula T.

[0038] [ka]

[0039] During the ceremony R 1 and R 2represents a linear or branched alkyl group having H, F, Cl, Br, -CN, or 1 to 12 C atoms, provided that in addition, one or more CH2 groups containing terminal C atoms are each independently linked to each other in such a way that O or S atoms are not directly linked to each other, 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. L 1 This represents H, F, or CH3, preferably H. A 0 teeth, [ka] This represents the (fluoro)phenylene ring, which may be substituted with one or two methyl and / or ethyl groups. A 1 These independently represent phenylene-1,4-diyl (wherein 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, OCH3, OCHF2, or OCF3), cyclohexane-1,4-diyl (wherein one or two non-adjacent CH2 groups may independently be 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. m represents 0, 1, or 2, preferably 1, independently of each other in each case.

[0040] c) One or more preferably dielectrically positive compounds selected from the group of compounds of formula II and III, preferably compounds having a dielectric anisotropy greater than 3, preferably one or more compounds of formula II.

[0041] [ka]

[0042] During the ceremony R 2 This is an alkyl group having 1 to 15 carbon atoms (however, one or more CH2 groups containing terminal carbon atoms in this group are each independently connected to each other in such a way that O or S atoms are not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] -O-, -S-, -(CO)-O-, -O-(CO)- may be substituted, however, one or more H atoms may be substituted with F or Cl. ) or represents H, preferably an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, an alkenyl, alkenyloxy, alkoxyalkyl, fluorinated alkenyl, cycloalkyl (having 3 to 5 C atoms), cycloalkylalkyl, cycloalkylalkoxy, most preferably alkyl, cyclopropyl, cyclopentyl or alkenyl, [ka] Each of them appeared independently of the others. [ka] However, the (fluoro)phenylene ring may be substituted with one or two methyl and / or ethyl groups. Preferably, [ka] This represents, L 21 and L 22 This represents H or F, L 2a represents H or CH3, preferably H. X2 This represents a halogen, an alkyl or alkoxy halide having 1 to 3 carbon atoms, or an alkenyl or alkenyloxy halide having 2 or 3 carbon atoms, preferably F, Cl, -OCF3, -OCHF2, -OCH2F, -O-CH2CF3, -O-CH=CH2, -O-CH=CF2 or -CF3, very preferably F, Cl, -O-CH=CF2 or -OCF3. m represents 0, 1, 2, or 3, preferably 1 or 2, and particularly preferably 2.

[0043] R 3 This is an alkyl group having 1 to 15 carbon atoms (however, one or more CH2 groups containing terminal carbon atoms in this group are each independently connected to each other in such a way that O or S atoms are not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] -O-, -S-, -(CO)-O-, -O-(CO)- may be substituted, however, one or more H atoms may be substituted with F or Cl. ) or represents H, preferably an alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, an alkenyl, alkenyloxy, alkoxyalkyl, fluorinated alkenyl, cycloalkyl (having 3 to 5 C atoms), cycloalkylalkyl, cycloalkylalkoxy, most preferably alkyl, cyclopropyl, cyclopentyl or alkenyl, [ka] Each of them appeared independently of the others. [ka] However, the (fluoro)phenylene ring may be substituted with one or two methyl and / or ethyl groups. Preferably, [ka] This represents, L 31 and L 32 These represent H or F independently of each other, preferably L 31 This represents F, L 3a represents H or CH3, preferably H. X 3 This represents a halogen, 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, -OCH2F, -O-CH2CF3, -O-CH=CH2, -O-CH=CF2, or -CF3, preferably F, Cl, -O-CH=CF2, -OCHF2, -OCH2F, or -OCF3. Z 3 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, and n represents 0, 1, 2, or 3, preferably 1, 2, or 3, and particularly preferably 1.

[0044] d) One or more dielectrically neutral compounds selected from the groups of formulas IV and V.

[0045] [ka]

[0046] During the ceremony, R 41 and R 42 In equation III, R is independent of each other. 3 It has the meaning shown above, preferably R 41 represents alkyl, R 42 R represents alkyl, cyclopropyl, cyclopentyl, or alkoxy, or R 41 represents alkenil, R 42 represents alkyl, [ka] Each of them appeared independently of the others. [ka] However, the (fluoro)phenylene ring may be substituted with one or two methyl and / or ethyl groups. Preferably, one or more [ka] teeth, [ka] This represents, Z 41 and Z 42 They are independent 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, and

[0047] R 51 and R 52 R is independent of each other 41 and R 42 It has one of the meanings given to it, 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, an alkoxy having 1 to 7 carbon atoms, preferably an n-alkoxy, particularly preferably an n-alkoxy having 2 to 5 carbon atoms, 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] Each of them appeared independently of the others. [ka] However, the (fluoro)phenylene ring may be substituted with one or two methyl and / or ethyl groups. Preferably, [ka] This represents, 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.

[0048] e) One or more dielectrically negative compounds selected from the group of formulas VI to IX.

[0049] [ka]

[0050] 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, an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably a linear alkenyl group, particularly preferably an unsubstituted alkoxy group having 2 to 5 carbon atoms and 1 to 6 carbon atoms, 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, and L 61 , L 62 is independently H or methyl, preferably H. l represents 0 or 1,

[0051] 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 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, and L 71 , L 72 is independently H or methyl, preferably H. [ka] Independently [ka] This represents,

[0052] 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 unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably a linear alkenyl group, particularly preferably having 2 to 5 carbon atoms, or C 3~5 -Cycloalkyl-(CH2) 0~1 This represents, R82 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] teeth, [ka] Preferably [ka] comfortably [ka] This represents, Z 8 This represents -(C=O)-O-, -CH2-O-, -CF2-O- or -CH2-CH2-, preferably -(C=O)-O- or -CH2-O-, and o represents 0 or 1,

[0053] R 91 and R 92 They are independent of each other, R 72 It has the meaning given above, R 91 This represents an alkyl group having preferably 2 to 5 carbon atoms, 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] This represents, p and q each independently represent either 0 or 1, and (p+q) preferably represents 0 or 1. [ka] When representing, Preferably, p=q=1.

[0054] f) One or more compounds of formula X are used, preferably in a concentration of 1% to 30%, more preferably in a concentration of 2% to 20%, and particularly preferably in a concentration of 3% to 10%.

[0055] [ka]

[0056] During the ceremony, [ka] teeth, [ka] This represents, L independently represents H, CH3, or CH2CH3, preferably H. [ka] Each of them appeared independently of the others. [ka] Preferably [ka] This represents, n represents 1 or 2, preferably 1. R 1Preferably, 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 -Cycloalkyl-alkyl, C 3~5 - Represents cycloalkyl-alkoxy, alkyl, alkoxy, alkenyl or alkenyloxy, more preferably alkyl, alkenyl, alkoxy or alkenyloxy, most preferably alkyl, and X 1 These are F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy, or fluorinated alkenyloxy, where the latter four groups preferably have 1 to 4 C atoms and preferably represent F, Cl, CF3, or OCF3. However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, and preferably one methyl group.

[0057] g) Again optionally, preferably essentially, one or more compounds of formula XI, either as substitutes or additions.

[0058] [ka]

[0059] During the ceremony, [ka] teeth, [ka] This represents, L independently represents H, CH3, or CH2CH3, preferably H. [ka] teeth, [ka] Preferably [ka] This represents, n represents 0 or 1, 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 with 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. However, each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group. Therefore, compounds of formula X are excluded from those.

[0060] The compound of formula I is characterized by a remarkably large positive dielectric anisotropy (Δε), making it particularly suitable for use in TN-TFT displays, as well as IPS and FFS displays. The compound has a relatively low melting point and a very high transparency point, exhibiting excellent compatibility with conventional materials used in liquid crystal mixtures for displays, and dissolving readily in such media. Furthermore, the compound contains no perfluoroalkyl groups in its structure, making it environmentally harmless in terms of the accumulation of perfluoroalkyl structural materials.

[0061] The compounds according to the present invention preferably have a Δε greater than 9, preferably greater than 15, and particularly preferably greater than 17.

[0062] Optionally, the medium according to the present application comprises one or more compounds of formula L in a concentration preferably in the range of 1% to 40%, more preferably in the range of 2% to 30%, particularly preferably in the range of 3% to 20%.

[0063]

Chemical Formula

[0064] In the formula, R L1 and R L2 each, independently of each other, represent an alkyl group having 1 to 15 carbon atoms, provided that one or more CH₂ groups in these groups, preferably one CH₂ group, are each, independently of one another, replaced such that no two oxygen atoms are directly connected to each other, 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, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms, provided that one or more hydrogen atoms may be replaced by halogen, and Y L1 and Y L2 , which are the same or different, represent H, F or Cl, preferably at least one of Y L1 and Y L2 is H, preferably Y L2 is H, and most preferably Y L1 and Y L2 are both H.

[0065] The liquid-crystal medium according to the present application preferably has a nematic phase.

[0066] Throughout the present application, in particular R 1 , R 2 , R 3 , R 41 , R 51 , R 61 , R 71 , R81 , R 91 , 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 carbon atoms, and is therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0067] Throughout this application, the alkenyl may be linear or branched, preferably linear, and more 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.

[0068] Compounds of general formulas I, L, T and II-XI are prepared by methods known in themselves and under precise 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). Modifications known in themselves but not described in more detail herein may be used.

[0069] The compound of formula I can be synthesized as shown in the example synthesis or according to the following reaction scheme.

[0070] [ka]

[0071] <Scheme 1>A 0 benzene (L 1~3A general synthetic scheme for preparing benzofuran compounds of formula I, which may be substituted with ). The variable group is defined according to formula I, L 1~3 The group is independently H, F, or CH3. Reaction details: a) Cyclization with a strong base (BuLi, ZnCl2), b) Heteroaryl Heck reaction.

[0072] The present invention further relates to a liquid crystal display, particularly an IPS or FFS display, and especially preferably an FFS or SG-FFS display, that includes a liquid crystal medium according to the present invention.

[0073] The display according to the present invention is preferably addressed by an active matrix LCD (AMD), preferably a matrix of thin-film transistors (TFTs). However, the liquid crystal according to the present invention can also be used advantageously in displays having other known addressing methods.

[0074] The present invention further relates to a method for preparing a liquid crystal medium by mixing one or more compounds of formula I or its subformulas with one or more low molecular weight liquid crystal compounds or liquid crystal mixtures and optionally additional mesogenic compounds and / or additives.

[0075] The following meanings apply to "above" and "below."

[0076] Liquid crystal mixtures or liquid crystal media having a nematic phase at room temperature (20°C) are particularly preferred.

[0077] In a preferred embodiment of the present invention, the liquid crystal medium comprises one or more compounds selected from the group of compounds of formula Ia and Ib.

[0078] [ka]

[0079] In the formula, variable group A 0 and A1 Independently, in formula I, base A 0 Defined as follows, and m is 0, 1, or 2.

[0080] Here, compounds of formula I where n is 1 or 2, preferably 2, and compounds of formula Ia / Ib where n is 0 or 1, preferably 1, are particularly preferred. Group A 1 Preferably, phenylene may be fluorinated, and particularly preferably [ka] It represents.

[0081] Base A in formulas I and Ia / Ib 0 Preferably [ka] It represents.

[0082] A 0 but [ka] Compounds of formula Ia representing the above are preferred.

[0083] In Equation I, and independently in the more specific related equations above and below n is either 1 or 2, or in equations Ia and Ib, m is either 0 or 1, respectively. R 1 This is an alkyl group having 1 to 7 carbon atoms (however, one or more CH2 groups containing terminal carbon atoms in this group are independently linked to each other in such a way that the oxygen atoms are not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] Alternatively, it may be replaced with -O-, and in addition, one or more H atoms may be replaced with F. ), more preferably, it is an alkyl group having 2 to 7 C atoms. Compounds are preferred.

[0084] In a preferred embodiment of the present invention, the liquid crystal medium comprises one or more compounds selected from the group of compounds of the following formulas.

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] In the formula, R 1 , X 1 The terms are defined above and below as shown in Formula I, and include preferred definitions. Compounds of Formula I-10 and I-11 are particularly preferred.

[0089] The preferred compound of formula T is selected from the compounds of the following formula.

[0090] [ka]

[0091] In the formula, the base is defined as above, L 1 It is preferably H.

[0092] In formula T and its more restrictive formulas above and below, the base R 1 Preferably, linear or branched alkyl groups having 1 to 12 carbon atoms (however, one or more CH2 groups including terminal carbon atoms are arranged 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 an alkyl group having 1 to 7 C atoms or an alkenyl, cyclopentylmethyl, or cyclopentyl group having 2 to 7 C atoms.

[0093] In formula T and its more restrictive formulas above and below, the base R 2 Preferably, linear or branched alkyl groups having 1 to 12 carbon atoms (however, one or more CH2 groups including terminal carbon atoms are arranged 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.

[0094] In a preferred embodiment of the present invention, the liquid crystal medium comprises one or more compounds selected from the group of compounds of formula T-1 to T-4.

[0095] [ka]

[0096] In the formula, R 2 is CH3, CH2CH3, CF3 or F, preferably CH3 or CF3, and R 1 is defined above as in equation T, preferably R 1 This is an alkyl group having 1 to 7 carbon atoms (however, in this group, one or more CH2 groups containing terminal carbon atoms are each independently such that O or S atoms are not directly bonded to each other, such as -C≡C-, -CH=CH-, [ka] may be replaced by -O-, -S-, -(CO)-O- or -O-(CO)-, with the proviso that additionally one or more H atoms may be replaced by F.) 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, cycloalkyl (having 3 to 5 C atoms), cycloalkylalkyl or cycloalkylalkoxy, most preferably alkyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl or alkenyl.

[0097] In a preferred embodiment of the present invention, the liquid-crystal medium is preferably dielectrically positive, preferably has a dielectric anisotropy greater than 3, and comprises one or more compounds selected from the group of compounds of formulae II-1 and II-2.

[0098]

Chemical Formula

[0099] in which the parameters each have the meanings given above for formula II, L 23 and L 24 each independently represent H or F, preferably L 23 represents F, and

Chemical Formula

Chemical Formula

Chemical Formula

[0100] [ka]

[0101] In the equation, the parameter has the meaning given by equation III.

[0102] The medium according to the present invention may contain, in addition to or substitute for, one or more compounds of formula III-3 for the compounds of formula III-1 and / or III-2.

[0103] [ka]

[0104] 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.

[0105] The liquid crystal medium preferably comprises a compound selected from the group of compounds of formulas II-1 and II-2, where L 21 and L 22 Furthermore / or L 24 and L 25 Both of them represent F.

[0106] In a preferred embodiment, the liquid crystal medium comprises a compound selected from the group of compounds of formula II-2, where L 21 , L 22 , L 24 and L 25 All of these represent F.

[0107] 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 formulas II-1a to II-1e, preferably one or more compounds of formula II-1a and / or II-1b and / or II-1d, more preferably compounds of formula II-1a and / or II-1e or II-1c and / or II-1e, and most preferably compounds of formula II-1e.

[0108] Chemical structure

[0109] wherein the parameters have the respective meanings indicated above, and the parameter L 25 and L 26 each represent H or F independently of each other and of the other parameters, and preferably in formulas II-1a and II-1b, L 21 and L 22 both represent F, in formulas II-1d and II-1e, L 21 and L 22 both represent F, and / or L 23 and L 24 both represent F, and in formula II-1f, L 21 and L 22 represent F, and, with the proviso that each ring, preferably phenylene ring, may be optionally substituted by one or two alkyl groups, preferably methyl and / or ethyl groups, most preferably one methyl group, respectively.

[0110] The liquid crystal medium preferably contains one or more compounds of formula II-2, which are preferably selected from the group of compounds of formulas II-2a to II-2k, and preferably contains one or more compounds of formula II-2a and / or II-2h and / or II-2j and / or II-2k.

[0111] [ka]

[0112] [ka]

[0113] [ka]

[0114] 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 L is particularly preferred. 26 This represents H.

[0115] The liquid crystal medium preferably contains a compound selected from the group of compounds of formulas II-2a to II-2k, where L 21 and L 22 Both of these represent F, and / or L 23 and L 24 Both of them represent F.

[0116] In a preferred embodiment, the liquid crystal medium comprises a compound selected from the group of compounds of formulas II-2a to II-2k, where L 21 , L 22 , L 23 and L 24 All of these represent F.

[0117] Particularly preferred compounds of formula II-2 are those of the following formulas, with formula II-2a-1 and / or II-2h-1 and / or II-2k-2 being particularly preferred.

[0118] [ka]

[0119] [ka]

[0120] [ka]

[0121] [ka]

[0122] In the formula, R 2 and X 2 The above has the meanings shown, and X 2 This preferably represents F.

[0123] 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 of compounds of formula III-1a to III-1j, preferably from formulas III-1d, III-1e, III-1g, III-1h, III-1j, III-1k, III-1m and III-1n, and more preferably from formulas III-1j, III-1k, III-1m and III-1n.

[0124] [ka]

[0125] [ka]

[0126] [ka]

[0127] In the formula, the parameter has the meaning given above, and preferably in the formula, X 3This 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.

[0128] The liquid crystal medium preferably comprises 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 III-1c-1 and / or III-1c-2, and most preferably III-1c-1.

[0129] [ka]

[0130] In the formula, R 3 The above has the meaning, and each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0131] The liquid crystal medium preferably contains one or more compounds of formula III-1d, 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.

[0132] [ka]

[0133] During the ceremony, R 3 X is defined as above, and X 3The elements are CF3, F, OCF3, -OCF2H, or -OCH2F, preferably F or CF3.

[0134] The liquid crystal medium preferably comprises one or more compounds of formula III-1g, preferably selected from the group of compounds of formula III-1g-1 to III-1g-6, preferably III-1g-1 and / or III-1g-2 and / or III-1g-3 and / or III-1g-6, more preferably III-1g-3 and / or III-1g-6, and more preferably III-1g-6.

[0135] [ka]

[0136] In the formula, R 3 The above has the meaning, and each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0137] The liquid crystal medium preferably contains one or more compounds of formula III-1g, preferably selected from the group of compounds of formula III-1h-1 to III-1h-6, and preferably from the group of compounds of formula III-1h-3.

[0138] [ka]

[0139] In the formula, R 3 The above has the meaning, and each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0140] The liquid crystal medium preferably contains one or more compounds selected from formulas III-1j, III-1k, III-1m, and III-1n, and is preferably selected from the group of compounds of formulas III-1j-1, III-1k-1, III-1m-1, and III-1n-1, preferably from the group of compounds of formula III-1j-1.

[0141] [ka]

[0142] In the formula, the parameter has the meaning given above, X 3 preferably represents F, -OCF3, -OCHF2, or -OCH2F.

[0143] The liquid crystal medium preferably contains one or more compounds of formula III-1k, and is preferably selected from the group of compounds of formula III-1n-1 and III-1n-2, and preferably from the group of compounds of formula III-1n-1.

[0144] [ka]

[0145] In the formula, the parameters have the meanings given above, and each ring, preferably a phenylene ring, may be substituted with one or two alkyl groups, preferably methyl and / or ethyl groups, preferably one methyl group.

[0146] The liquid crystal medium according to the present invention preferably comprises a dielectrically neutral compound having a dielectric anisotropy in the range of -1.5 to 3, and is preferably selected from the group of compounds of formulas VI, VII, VIII, and IX.

[0147] In this application, all elements include their respective isotopes. In particular, one or more H atoms in a compound may be replaced with D, which is especially preferred in some embodiments. Increasing the degree of deuteration of the corresponding compound enables, for example, detection and identification of the compound.

[0148] In this application, The alkyl (alkyl) is particularly preferably a linear alkyl, especially CH3-, C2H5-, n-C3H7-, n-C4H9- or n-C5H 11 - represents, and Alkenyl is particularly preferred to represent CH2=CH-, E-CH3-CH=CH-, CH2=CH-CH2-CH2-, E-CH3-CH=CH-CH2-CH2-, or E-(n-C3H7)-CH=CH-.

[0149] In a more preferred embodiment, the medium comprises one or more compounds of formula IV, preferably formula IVa or IVb.

[0150] [ka]

[0151] During the ceremony, R 41 This refers to an unsubstituted alkyl group having 1 to 7 C atoms (however, in addition, one or more CH2 groups are present). [ka] (This can be replaced with...) Or an unsubstituted alkenyl group having 2 to 7 carbon atoms, preferably an n-alkyl group, and particularly preferably having 2, 3, 4 or 5 carbon atoms, and R 42 This represents an unsubstituted alkyl group having 1 to 7 carbon atoms or an unsubstituted alkoxy group having 1 to 6 carbon atoms (preferably having 2 to 5 carbon atoms), or an unsubstituted alkenyl group having 2 to 7 carbon atoms (preferably having 2, 3, or 4 carbon atoms), more preferably a vinyl group or a 1-propenyl group.

[0152] In a particularly preferred embodiment, the medium comprises one or more compounds of formula IV, preferably formula IV-1, selected from the group of compounds of formula IV-1 to IV-11.

[0153] [ka]

[0154] During the ceremony, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. Alkenyl represents an alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms. 'alkenyl' represents an alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms. Cycloalkyl represents a partially or completely cyclic alkyl group having 3 to 12 carbon atoms, preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylalkyl, cyclobutylalkyl, or cyclopentylalkyl, and very preferably [ka] A selection from the group consisting of, most preferably cyclopropyl, and alkoxy represents an alkoxy having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0155] In a 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.

[0156] In another preferred embodiment, the medium according to the present invention comprises two or more compounds of formula IV-1, and formula

[0157] [ka] Selected from, in particular, the combination of compounds IV-1-1 and IV-1-4.

[0158] 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.

[0159] [ka]

[0160] 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.

[0161] In a more preferred embodiment, the medium comprises one or more compounds of formula V. In this more preferred embodiment, the medium comprises one or more compounds of formula V selected from the group of compounds of formula V-1 to V-5, preferably one or more of formulas V-1, V-3, V-4, and V-5.

[0162] [ka]

[0163] [ka]

[0164] In the formula, the parameter has the meaning given in formula V above, and preferably q is 0 or 1, preferably 0. R 51 This represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms, and 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.

[0165] In a more preferred embodiment, the medium comprises one or more compounds of formula V-1 selected from the following formulas.

[0166] [ka]

[0167] In the formula, "alkyl" has the definition given above and is preferably methyl, ethyl, propyl, or butyl. Compounds of formulas V-1a, V-1b, and V-1c are particularly preferred.

[0168] In a more preferred embodiment, the medium comprises one or more compounds of formula V-2, R 51 and R 52 At least one of the groups is an alkenyl having 2 to 6 carbon atoms, preferably selected from the following formulas.

[0169] [ka]

[0170] In the formula, preferably alkenyl has 2 to 5 C atoms, preferably 2 to 4 C atoms, and is particularly preferably vinyl or 3-buten-1-yl, R 52 It is defined as above, and is preferably methyl or ethyl.

[0171] In a more preferred embodiment, the medium comprises one or more compounds of formula V-4, R 51 and R 52 One or both of the groups are alkenyls having 2 to 6 carbon atoms, preferably selected from the following formulas.

[0172] [ka]

[0173] During the ceremony, Alkyl refers to a linear alkyl group having 1 to 6 carbon atoms, particularly methyl, ethyl, or n-propyl, and Alkenyl represents an alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably vinyl.

[0174] Compounds of formula V-4d are particularly preferred.

[0175] In a more preferred embodiment, the medium comprises one or more compounds of formula V-8, selected from the group of compounds of formula V-8a to V-8c, and preferably V-8a.

[0176] [ka]

[0177] During the ceremony, Alkyl and alkyl * These are linear alkyl groups having 1 to 6 carbon atoms, particularly methyl, ethyl, or n-propyl, and alkenyl and alkenyl * Preferably, it represents an alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably vinyl.

[0178] Among the compounds of formula V-8b, the following structure is preferred.

[0179] [ka]

[0180] In a more preferred embodiment, the medium comprises one or more compounds of formula V-6, selected from the group of compounds of formulas V-4a to V-6c.

[0181] [ka]

[0182] During the ceremony, Alkyl and alkyl * These are linear alkyl groups, each independently having 1 to 6 carbon atoms, particularly methyl, ethyl, n-propyl, and pentyl.

[0183] The liquid crystal medium preferably comprises two or more compounds selected from the group of compounds of formulas V-6a, V-6b, and V-6c.

[0184] In a more preferred embodiment, the medium comprises one or more compounds of formula V-7, selected from the group of formulas below.

[0185] [ka]

[0186] During the ceremony, Alkyl refers to a linear alkyl group having 1 to 6 carbon atoms, particularly methyl, ethyl, or n-propyl, and Alkenyl represents an alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, particularly preferably vinyl or 3-buten-1-yl, and R 52 The above definition is used, and is preferably alkyl or alkoxy, more preferably methyl or ethyl, and more preferably ethyl.

[0187] The medium according to the present invention preferably contains the following compounds in the total concentrations shown below: One or more compounds selected from the group of compounds of formula I, in an amount of 1 to 20% by weight, Preferably, 2 to 60% by weight of one or more compounds of formula II selected from the group of compounds of formula II-1 and II-2, and / or One or more compounds of formula III in an amount of 1 to 60% by weight, and / or 5 to 80% by weight of one or more compounds of formula IV, and / or One or more compounds of formula T in 0-20% 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. However, the total content of all compounds of formulas I, T, II-IX, and X present in the medium is preferably 95% or more, more preferably 97% or more, and most preferably 100%, but is always 100% or less.

[0188] The latter condition applies to all media covered by this application.

[0189] In a more preferred embodiment, the medium according to the present invention preferably contains, in addition to compounds of formula I or its preferred subformulas, one or more dielectrically neutral compounds selected from the group of compounds of formulas IV and V, in a total concentration preferably within the range of 5% to 90% by weight, preferably 10% to 80%, and particularly preferably 20% to 70%.

[0190] In a particularly preferred embodiment, the medium according to the present invention is independently One or more compounds of formula I, in a total concentration in the range of 3% to 30%, preferably 5% to 25%, and / or One or more compounds of formula T, in a total concentration within the range of 1% to 40%, preferably within the range of 5% to 25%, and / or One or more compounds of formula II, in a total concentration in the range of 5% to 50%, preferably 10% to 40%, and / or One or more compounds of formula III, 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 IV, in a total concentration within the range of 5% to 55%, preferably within the range of 25% to 50%, and / or One or more compounds of formula V, in a total concentration in the range of 3% to 30%, preferably 5% to 30%, and / or The compound contains one or more compounds of formula VI and / or VII and / or VIII and / or IX in a total concentration within the range of 0% to 30%, preferably 0% to 20%, and more preferably 0% to 15% of the formula.

[0191] All percentages (%) of the mixture components in this disclosure are understood to be weight percent.

[0192] Preferably, the concentration of the compound of formula I in the medium according to the present invention is 1% or more to 20%, more preferably 1.5% or more to 20%, and most preferably 2% or more to 12%.

[0193] In preferred embodiments of the present invention, the concentration of the compound of formula II in the medium is 3% to 60%, more preferably 5% to 45%, more preferably 5% to 20%, and most preferably 7% to 16%.

[0194] In a preferred embodiment of the present invention, the combined concentrations of compounds I, T, and V in the medium are in the range of 30% to 70%, more preferably 35% to 65%.

[0195] In a preferred embodiment of the present invention, the combined concentrations of the compounds of formulas IV-1, IV-2, IV-3, and V-1 in the medium are in the range of 45% to 75%, more preferably 50% to 70%.

[0196] In a preferred embodiment of the present invention, the combined concentrations of the compounds of formula III-1d and V-5 in the medium are in the range of 4% to 25%, more preferably 8% to 20%.

[0197] In a preferred embodiment of the present invention, the combined concentration of compounds V-1a and V-5, preferably V-5a, in the medium is within the range of 12% to 30%, more preferably 18% to 28%.

[0198] 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 FFS, IPS, VA, or ECB effects, preferably based on IPS or FFS effects, and in particular preferably addressed by an active matrix addressing device.

[0199] 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 to a method for preparing a liquid crystal medium according to the present invention, characterized by mixing one or more compounds of formula I with one or more additional mesogenic compounds and optionally one or more additives.

[0200] In addition to the compounds of formulas I, T, II-X, and L, 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.

[0201] Furthermore, 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, relative to the entire medium.

[0202] The liquid crystal medium according to the present invention may contain one or more chiral compounds.

[0203] Particularly preferred embodiments of the present invention satisfy one or more of the following conditions: However, acronyms (abbreviations) are explained in Tables A-C and illustrated in the examples in Table D.

[0204] Preferably, the medium according to the present invention satisfies one or more of the following conditions.

[0205] i. The liquid crystal medium has a birefringence of 0.060 or higher, and particularly preferably 0.070 or higher.

[0206] ii. The liquid crystal medium has a birefringence of 0.200 or less, and particularly preferably 0.180 or less.

[0207] iii. The liquid crystal medium has a birefringence within the range of 0.090 to 0.180.

[0208] iv. The liquid crystal medium preferably comprises one or more particularly preferred compounds of formula I, selected from (sub)formula Ia or Ib.

[0209] v. The liquid crystal medium contains one or more preferred compounds of formula T.

[0210] vi. The total concentration of the compound of formula II in the whole mixture is 0.5% or more, preferably 1% or more, preferably 7% or less, particularly preferably 8% or less, and very particularly preferably within the range of 1% to 40%.

[0211] vii. The liquid crystal medium contains one or more compounds of formula IV selected from the group of compounds of formula CC-nV and / or CC-n-Vm and / or CC-n-nVm and / or CC-VV and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably CC3-V, in a concentration of up to 60%, particularly preferably 50%, and in addition to CC-3-V, it may contain one or more compounds CC-3-V1 in a concentration of up to 15%, and / or CC-3-2V1 in a concentration of up to 15%, and / or CC-4-V1 in a concentration of up to 20%, particularly preferably 15%, and / or CC-5-V in a concentration of up to 20%.

[0212] viii. 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%.

[0213] ix. The liquid crystal medium contains one or more compounds of formula IV, preferably IV-1 and / or IV-2, in a total concentration of preferably 20% or more, particularly 30% or more, and very preferably 40% or more, and preferably 46% to 56% of the compounds of formula IV-1.

[0214] x. The total concentration of the compound of formula V in the whole mixture is 5% or more, preferably 7% or more, preferably in the range of 5% to 40%, and particularly preferably in the range of 5% to 30%.

[0215] xi. The total concentration of the compound of formula V-4 in the whole mixture is preferably 5% to 25%, and preferably 5% to 15%.

[0216] xii. The total concentration of the compound of formula V-6, preferably V-6a to V-6c, in the whole mixture is preferably 3% or more and 30% or less, preferably 10% or more and 25% or less.

[0217] xiii. The total concentration of the compound selected from formula V-8, preferably V-8-a and III-1d, preferably III-1d-1, in the whole mixture is preferably 2% to 20%, and preferably 4% to 15%.

[0218] The present invention further relates to an electro-optical display having an active matrix address that addresses based on IPS, FFS, or UB-FFS effects, and containing the liquid crystal medium according to the present invention as a dielectric.

[0219] The liquid crystal mixture preferably has a nematic phase range with a temperature range of at least 70°C.

[0220] The rotational viscosity γ1 is preferably 350 mPa·s or less, preferably 250 mPa·s or less, and particularly 150 mPa·s or less.

[0221] 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.

[0222] 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 I, T, II, III, IV, V, VI, VII, VIII, and IX.

[0223] The liquid crystal medium according to the present invention may contain more than 18 types of compounds. In this case, they preferably contain 18 to 25 types of compounds.

[0224] 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.

[0225] In a preferred embodiment, the liquid crystal medium according to the present invention is selected from the group of compounds of formulas I, T, II, III, and IV and V, and preferably comprises compounds selected from the group of compounds of formulas Ia, T, II-1, II-2, III-1, III-2, IV, and V, which preferably consist mostly, particularly preferably essentially, of the compounds of said formula.

[0226] The liquid crystal medium according to the present invention preferably has a nematic phase at a temperature of at least -10°C to 70°C, particularly preferably -20°C to 80°C, very preferably -30°C to 85°C, and most preferably -40°C to 90°C in each case.

[0227] 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 transparency does not occur 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.

[0228] In a preferred embodiment, the liquid crystal medium according to the present invention is characterized by a moderate to low range of optical anisotropy values. The birefringence value is preferably in the range of 0.075 to 0.130, particularly preferably in the range of 0.085 to 0.120, and very particularly preferably in the range of 0.090 to 0.115.

[0229] Preferably, the liquid crystal medium according to the present invention has a dielectric anisotropy value of 1.5 or more, preferably 2.5 or more. On the other hand, it has a dielectric anisotropy of 26 or less, preferably 15 or less, and most preferably 10 or less.

[0230] 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 to 15, more preferably 2.0 to 10, particularly preferably 2.0 to 9.0, and very particularly preferably 2.5 to 8.0.

[0231] The liquid crystal medium according to the present invention preferably has a relatively low threshold voltage (V0) in the range of 1.1V to 5.0V, preferably to 2.7V, preferably 1.3V to 2.6V, and particularly preferably 1.4V to 2.5V.

[0232] In addition, the liquid crystal medium according to the present invention has a high VHR value in the liquid crystal cell.

[0233] Generally speaking, liquid crystal media with a lower address voltage or threshold voltage have a lower VHR than those with a higher address voltage or threshold voltage, and vice versa.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] • "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.

[0238] • "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.

[0239] • "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.

[0240] • "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%.

[0241] 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.

[0242] In this invention, "≦" means less than or equal to, preferably less than, and "≧" means greater than or equal to, preferably greater than.

[0243] 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.

[0244] Throughout this application, 1,3-cyclopentenylene is a substructure selected from the group shown below. [ka] Preferably [ka] Most preferably [ka]

[0245] 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.

[0246] 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.

[0247] 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% by weight, 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.

[0248] In other embodiments, the liquid crystal medium according to the present invention comprises a polymer precursor, which comprises, in typical amounts, 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% by weight, and particularly preferably 0.1% to 2% by weight, 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.

[0249] 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".

[0250] 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 excellent 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.

[0251] 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.

[0252] The structure of the FFS 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.

[0253] 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.

[0254] Table E below shows the dopants that may be added to the mixture according to the present invention. When the mixture contains one or more dopants, the dopant(s) (one or more) are used in an amount of 0.01% to 4% by weight, preferably 0.1% to 1.0%.

[0255] For example, the stabilizers that can be added to the mixture according to the present invention are preferably in an amount of 0.01% to 6% by weight, and particularly 0.1% to 3%, as shown below in Table F.

[0256] 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.

[0257] 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).

[0258] Unless otherwise clearly indicated in this invention, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Fredericks threshold.

[0259] Unless otherwise clearly indicated in each case, all physical properties are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals," published November 1997, Merck, Germany, with a temperature of 20°C applied, Δn determined at 436 nm, 589 nm, and 633 nm, and Δε determined at 1 kHz.

[0260] 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 transmission surface area is substantially square with ITO electrodes, 1 cm 2 That is the case.

[0261] Unless otherwise indicated, chiral dopants are not added to the liquid crystal mixtures used; however, the liquid crystal mixtures used in this invention are also suitable for applications requiring this type of doping.

[0262] 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.

[0263] For practical purposes, the dispersion of the refractive index of a material has conventionally been characterized as follows, and will be used throughout this invention unless otherwise specified. 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 (helium-neon 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).

[0264] Unless otherwise clearly indicated, use the following symbols: Capacitive threshold voltage at 20°C [V] n e Anomalous refractive index measured at 20°C and 589nm Typical refractive index measured at 20°C and 589nm Δn Optical anisotropy measured at 20℃ and 589nm λ Wavelength λ [nm] Δn(λ) Optical anisotropy measured at 20°C and wavelength λ Δn(Δn) Δn(20℃, 436nm)-Δn(20℃, 633nm) The change in optical anisotropy as defined above. Δn(Δn * ) Δ(Δn) / Δn(20℃, 589nm) The "relative change in optical anisotropy" is defined as follows. 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 cl.p. (Clearness point) [°C] ν is the fluid viscosity (mm²) measured at 20°C. 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

[0265] 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 examples illustrate achievable properties and combinations of properties.

[0266] In the present invention and the following examples, the structure of the liquid crystal compound is indicated by an acronym, 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 H2 n , C m H2 m and C l H2l These are linear alkyl or alkylene groups, each having n, m, and l carbon atoms, respectively. Preferably, n, m, and l are 1, 2, 3, 4, 5, 6, or 7, independently of each other. Table A shows the codes of the core ring elements of the compound, Table B lists the bridging units, and Table C lists the meanings of the symbols of the left- and right-end groups of the molecule. The acronym consists of the code of the ring element having any linking group, followed by a first hyphen and the code of the left-end group, and a second hyphen and the code of the right-end group. Table D shows exemplary structures of the compound with their respective abbreviations.

[0267] <Table A: Ring elements>

[0268] [Table 1]

[0269] [Table 2]

[0270] <Table B: Bridge Units>

[0271] [Table 3]

[0272] <Table C: Terminal group>

[0273] [Table 4]

[0274] In the table, n and m are integers, and the three dots "..." are spaces for other abbreviations from this table.

[0275] In addition to the compound of formula B, the mixture according to the present invention preferably includes one or more compounds as described below.

[0276] Use the following abbreviations: (n, m, k, and l are each independent integers, 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, and in the combination "-nO-", preferably 1, 2, 3, or 4, more preferably 2 or 4; m is preferably 1, 2, 3, 4, or 5, and in the combination "-Om", preferably 1, 2, 3, or 4, more preferably 2 or 4; the combination "-lVm" is preferably "2V1".)

[0277] Exemplary and preferred dielectrically positive compounds

[0278] [Table 5]

[0279] [Table 6]

[0280] [Table 7]

[0281] [Table 8]

[0282] [Table 9]

[0283] [Table 10]

[0284] [Table 11]

[0285] [Table 12]

[0286] [Table 13]

[0287] Exemplary and preferred dielectrically neutral compounds

[0288] [Table 14]

[0289] [Table 15]

[0290] [Table 16]

[0291] [Table 17]

[0292] [Table 18]

[0293] [Table 19]

[0294] [Table 20]

[0295] [Table 21]

[0296] high ε ⊥ Exemplary compounds having

[0297] [Table 22]

[0298] [Table 23]

[0299] Exemplary and preferred dielectrically negative compounds

[0300] [Table 24]

[0301] [Table 25]

[0302] [Table 26]

[0303] [Table 27]

[0304] [Table 28]

[0305] [Table 29]

[0306] [Table 30]

[0307] [Table 31]

[0308] [Table 32]

[0309] Table E shows the chiral dopants that are preferably used in the mixture according to the present invention.

[0310]

[0311] [Table 33]

[0312] [Table 34]

[0313] In a preferred embodiment of the present invention, the medium according to the present invention comprises one or more compounds selected from the group of compounds in Table E.

[0314] Table F shows stabilizers that can be optionally added to the mixture according to the present invention. In this specification, the parameter n represents an integer in the range of 1 to 12. In particular, the phenol derivatives shown below can be used as additional stabilizers because they act as antioxidants.

[0315]

[0316] [Table 35]

[0317] [Table 36]

[0318] [Table 37]

[0319] [Table 38]

[0320] [Table 39]

[0321] [Table 40]

[0322] In a preferred embodiment of the present invention, the medium according to the present invention comprises one or more compounds selected from the group of compounds from Table F, particularly one or more compounds selected from the group of compounds of the following two formulas.

[0323] [Table 41] [Examples]

[0324] The following examples illustrate the present invention without limiting it in any way. However, the physical properties will clarify to those skilled in the art the achievable properties and the extent to which they can be modified. Thus, the various combinations of properties that can be preferably achieved are well defined for those skilled in the art.

[0325] <Example of synthesis>

[0326] <Synthesis Example 1>

[0327] [ka]

[0328] Compound 1 is prepared as follows.

[0329] Under a nitrogen atmosphere, 600 ml of anhydrous tetrahydrofuran is placed in a 2000 ml four-necked flask, 50.5 g (0.13 mol) of alkyne A is added, and the mixture is cooled to 18°C ​​while stirring well in an ice salt bath. 50.0 ml (0.13 mol) of n-butyllithium (in 2.7 m heptane) is slowly added over 60 minutes at a temperature below -15°C, followed by stirring for 20 minutes. Next, 55.0 ml (0.04 mol) of zinc chloride (in 0.7 m THF) and 18.0 g (0.08 mol) of anhydrous zinc bromide are added, and the mixture is raised to room temperature over 30 minutes. 1000 ml of anhydrous toluene is added, and the mixture is heated to 120°C to remove the tetrahydrofuran by distillation, followed by stirring well for another 90 minutes. After confirming that a considerable amount of conversion has occurred at this point by TLC check, the mixture is cooled to room temperature. The mixture was completely evaporated at 35°C using a rotary evaporator, and 81.9 g of the residue was dissolved in 500 ml of petroleum ether and filtered through 1200 ml of silica gel. Since low solubility was observed, further washing was performed with warm petroleum ether. 50.4 g of clean whole fraction was obtained, which was mostly dissolved in 2800 ml of petroleum ether and slowly concentrated to 1000 ml. After cooling, it was left overnight at 4°C, filtered, and air-dried, leaving 47.9 g of white crystals. This was recrystallized using the method described. After filtration and air-drying, 47.0 g (93%) of white crystals remained, and high purity was confirmed by DC and GC-MS analysis.

[0330] [Table 42]

[0331] Compound (1) has the following phase characteristics.

[0332] [Table 43]

[0333] <Synthesis Example 2>

[0334] [ka]

[0335] Compound (2) is prepared in a manner similar to that of Synthesis Example 1.

[0336] Compound (2) has the following phase characteristics.

[0337] [Table 44]

[0338] Here are some further examples of compounds.

[0339] [Table 45]

[0340] [Table 46]

[0341] [Table 47]

[0342] In the table below, the following abbreviations are used for terminal groups.

[0343] [Table 48]

[0344] Further exemplary compounds.

[0345] [ka]

[0346] [Table 49]

[0347] [Table 50]

[0348] [Table 51]

[0349] <Mixture example> Exemplary mixtures are disclosed below. All percentage values ​​are by weight.

[0350] <Mixture example 1> The following mixture (M-1) will be prepared and investigated.

[0351] [Table 52]

[0352] This mixture has an advantageously high mean elastic constant K avg It has a (17.6pN) and moderate optical anisotropy Δn. Furthermore, the response time parameter γ1 / K 11 It's also low.

[0353] <Mixture examples 1.1~1.4> Alternatively, 0.05% of any of the compounds in the following formulas may be added to mixture M-1.

[0354] [ka]

[0355] In the formula, the two O atoms bonded to the N atom represent radicals, and

[0356] [ka] and

[0357] [ka]

[0358] The resulting mixtures M-1.1, M-1.2, M-1.3, and M-1.4 are characterized by improved stability under harsh conditions, particularly against exposure to light.

[0359] <Mixture example 2> The following mixture (M-2) will be prepared and investigated.

[0360] [Table 53]

[0361] This mixture has an advantageously high mean elastic constant K avg It has a (17.6pN) and moderate optical anisotropy Δn. Furthermore, the response time parameter γ1 / K 11 It's also low.

[0362] <Mixture example 3> The following mixture (M-3) will be prepared and investigated.

[0363] [Table 54]

[0364] This mixture has an advantageously high mean elastic constant K avg It has a (16.9 pN) and moderate optical anisotropy Δn. Furthermore, the response time parameter γ1 / K 11 It's also low.

[0365] <Mixture example 4> The following mixture (M-4) will be prepared and investigated.

[0366] [Table 55]

[0367] This mixture has an advantageously high mean elastic constant K avg It has a (17.3pN) and moderate optical anisotropy Δn. Furthermore, the response time parameter γ1 / K 11 It's also low.

[0368] <Mixture example 5> The following mixture (M-5) will be prepared and investigated.

[0369] [Table 56]

[0370] <Comparative mixture example 1> The following mixture (C-1) will be prepared and investigated.

[0371] [Table 57]

[0372] <Comparative mixture example 2> The following mixture (C-2) will be prepared and investigated.

[0373] [Table 58]

[0374] <Mixture example 6> The following mixture (M-6) will be prepared and investigated.

[0375] [Table 59]

[0376] Table 1: Average elastic constant K of mixtures M-1 and M-6 avg (Scattering parameter) and response time parameter γ1 / K 11Comparison of these with their corresponding C-1 and C-2 >

[0377] [Table 60]

[0378] Scattering parameter K avg A higher value indicates better contrast due to improved dark levels. Response time parameter γ1 / K 11 A lower value indicates faster switching.

[0379] Table 2: Average elastic constant K of several mixtures avg and response time parameter γ1 / K 11 >

[0380] [Table 61]

[0381] <Mixture example 7> The following mixture (M-7) will be prepared and investigated.

[0382] [Table 62]

[0383] <Mixture example 8> The following mixtures will be prepared and investigated.

[0384] [Table 63]

[0385] <Mixture example 9> The following mixtures will be prepared and investigated.

[0386] [Table 64]

[0387] <Mixture example 10> The following mixtures will be prepared and investigated.

[0388] [Table 65]

[0389] <Mixture example 11> The following mixtures will be prepared and investigated.

[0390] [Table 66]

[0391] <Mixture example 12> The following mixtures will be prepared and investigated.

[0392] [Table 67]

[0393] <Mixture example 13> The following mixtures will be prepared and investigated.

[0394] [Table 68]

[0395] <Mixture example 14> The following mixtures will be prepared and investigated.

[0396] [Table 69]

[0397] <Mixture example 15> The following mixtures will be prepared and investigated.

[0398] [Table 70]

[0399] <Mixture example 16> The following mixtures will be prepared and investigated.

[0400] [Table 71]

[0401] <Mixture example 17> The following mixtures will be prepared and investigated.

[0402] [Table 72]

[0403] <Mixture example 18> The following mixtures will be prepared and investigated.

[0404] [Table 73]

[0405] <Mixture example 19> The following mixtures will be prepared and investigated.

[0406] [Table 74]

[0407] <Mixture example 20> The following mixtures will be prepared and investigated.

[0408] [Table 75]

[0409] <Mixture example 21> The following mixtures will be prepared and investigated.

[0410] [Table 76]

[0411] <Mixture example 22> The following mixtures will be prepared and investigated.

[0412] [Table 77]

[0413] <Mixture example 23> The following mixtures will be prepared and investigated.

[0414] [Table 78]

[0415] <Mixture example 24> The following mixtures will be prepared and investigated.

[0416] [Table 79]

[0417] <Mixture example 25> The following mixtures will be prepared and investigated.

[0418] [Table 80]

[0419] <Mixture example 26> The following mixtures will be prepared and investigated.

[0420] [Table 81]

[0421] <Mixture example 27> The following mixtures will be prepared and investigated.

[0422] [Table 82]

[0423] <Mixture example 28> The following mixtures will be prepared and investigated.

[0424] [Table 83]

[0425] <Mixture example 29> The following mixtures will be prepared and investigated.

[0426] [Table 84]

[0427] <Mixture example 30> The following mixtures will be prepared and investigated.

[0428] [Table 85]

[0429] <Mixture example 31> The following mixtures will be prepared and investigated.

[0430] [Table 86]

[0431] <Mixture example 32> The following mixtures will be prepared and investigated.

[0432] [Table 87]

[0433] <Mixture example 33> The following mixtures will be prepared and investigated.

[0434] [Table 88]

[0435] <Mixture example 34> The following mixtures will be prepared and investigated.

[0436] [Table 89]

[0437] <Mixture example 35> The following mixtures will be prepared and investigated.

[0438] [Table 90]

[0439] <Mixture example 36> The following mixtures will be prepared and investigated.

[0440] [Table 91]

[0441] <Mixture example 37> The following mixtures will be prepared and investigated.

[0442] [Table 92]

[0443] <Mixture example 38> The following mixtures will be prepared and investigated.

[0444] [Table 93]

[0445] <Mixture example 39> The following mixtures will be prepared and investigated.

[0446] [Table 94]

[0447] <Mixture example 40> The following mixtures will be prepared and investigated.

[0448] [Table 95]

[0449] <Mixture example 41> The following mixtures will be prepared and investigated.

[0450] [Table 96]

[0451] <Mixture example 42> The following mixtures will be prepared and investigated.

[0452] [Table 97]

[0453] <Mixture example 43> The following mixtures will be prepared and investigated.

[0454] [Table 98]

[0455] <Mixture example 44> The following mixtures will be prepared and investigated.

[0456] [Table 99]

[0457] <Mixture example 45> The following mixtures will be prepared and investigated.

[0458] [Table 100]

[0459] <Mixture example 46> The following mixtures will be prepared and investigated.

[0460] [Table 101]

[0461] <Mixture example 47> The following mixtures will be prepared and investigated.

[0462] [Table 102]

Claims

1. A liquid crystal medium having a nematic phase, characterized by containing one or more compounds of formula I and one or more additional compounds. 【Chemistry 1】 (In the formula, R １ This is an alkyl group having 1 to 15 carbon atoms, provided that this group contains one or more CH groups including the terminal carbon atoms. ２ The groups are arranged independently of each other, such that the O or S atoms are not directly bonded to one another, with -C≡C-, -CH=CH-, 【Chemistry 2】 -O-, -S-, -(CO)-O-, -O-(CO)- may be substituted, and in addition, one or more H atoms may be substituted with F or Cl. A ０ each occurrence is independently phenylene-1,4-diyl, provided that additionally one or two CH groups may be replaced by N, and one or more H atoms may be replaced by halogen, CN, CH ３ , CHF ２ , CH ２ F, OCH ３ , OCHF ２ or OCF ３ may be substituted. ), cyclohexane-1,4-diyl, provided that additionally one or two non-adjacent CH ２ groups may be replaced independently of each other 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 ０ These are independently, single-bonded, -CH ２ O-, -(CO)O-, -CF ２ O-, -CH ２ CH ２ CF ２ O-, -CF ２ CF ２ -ien-CH ２ CF ２ -ien-CH ２ CH ２ -, - (CH ２ ) ４ -, -OCH ２ -, -OCF ２ -, -CH=CH-, -CH=CF-, -CF=CF-, or -C≡C-, provided that asymmetric bridges may be inserted in any direction. n represents 1, 2, or 3.

2. In equation I, A ０ teeth, 【Transformation 3】 This represents, L １ , L ２ These are F, Cl, and CH, respectively, independently of each other. ３ or OCH ３ and Y is CH ３ or CH ２ CH ３ Representing, The liquid crystal medium according to claim 1.

3. The liquid crystal medium according to claim 1, comprising one or more compounds of formula T. 【Chemistry 4】 (In the formula, each base has the following meaning: R １ and R ２ This is a linear or branched alkyl group having H, F, Cl, Br, -CN, or 1 to 12 C atoms, in addition to one or more CH groups containing terminal C atoms. ２ The groups are arranged independently of each other, such that the O or S atoms are not directly bonded to one another, as in -CH=CH-, -C≡C-, 【Transformation 5】 -O-, -S-, -CO-, -CO-O-, -O-CO- may be substituted, and in addition, one or more H atoms may be substituted with F or Cl. L １ is H, F, or CH ３ And, A ０ teeth, 【Transformation 6】 This represents the (fluoro)phenylene ring, which may be substituted with one or two methyl and / or ethyl groups. A １ Each instance independently comprises phenylene-1,4-diyl (wherein addition, one or two CH groups may be replaced by N, and one or more H atoms may be halogens, CN, or CH). ３ CHF ２ ,CH ２ F, OCH ３ , OCHF ２ or OCF ３ It may be replaced with ), cyclohexane-1,4-diyl (in addition, one or two non-adjacent CH ２ The groups may be independently replaced by O and / or S, and one or more H atoms may be replaced by F. ), representing 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, (In each case, m represents 0, 1, or 2, independently of each other.)

4. A liquid crystal medium according to claim 1 or 2, characterized by comprising one or more compounds selected from the group of compounds of formula II and III. 【Transformation 7】 (In the formula, R ２ This is an alkyl group having 1 to 15 carbon atoms (however, one or more CH groups including the terminal carbon atoms in this group). ２ The groups are arranged independently of each other, such that the O or S atoms are not directly bonded to one another, with -C≡C-, -CH=CH-, 【Transformation 8】 -O-, -S-, -(CO)-O-, -O-(CO)- may be substituted, but one or more H atoms may be replaced with F or Cl. ) or represents H, 【Chemistry 9】 Each of them appeared independently 【Chemistry 10】 The (fluoro)phenylene ring may be substituted with one or two methyl and / or ethyl groups. L ２１ and L ２２ This represents H or F, L ２ａ is H or CH ３ This represents, X ２ This represents a halogen, an alkyl or alkoxy halide having 1 to 3 carbon atoms, or an alkenyl or alkenyloxy halide having 2 or 3 carbon atoms. m represents 0, 1, 2, or 3. R ３ represents an alkyl group having 1 to 15 carbon atoms, provided that this group includes one or more CH groups containing terminal carbon atoms. ２ The groups are arranged independently of each other, such that the O or S atoms are not directly bonded to one another, with -C≡C-, -CH=CH-, 【Chemistry 11】 -O-, -S-, -(CO)-O-, -O-(CO)- may be substituted, and in addition, one or more H atoms may be substituted with F or Cl. 【Chemistry 12】 Each of them appeared independently of the others. 【Chemistry 13】 The (fluoro)phenylene ring may be substituted with one or two methyl and / or ethyl groups. L ３１ and L ３２ These represent H or F independently of each other. L ３ａ is H or CH ３ This represents, X ３ This includes halogens, alkyl or alkoxy halides having 1 to 3 carbon atoms, or alkenyl or alkenyloxy halides having 2 or 3 carbon atoms, F, Cl, and -OCF. ３ , -OCHF ２ , -O-CH ２ CF ３ -O-CH=CF ２ -O-CH=CH ２ or -CF ３ This represents, Z ３ is, -CH ２ CH ２ -, -CF ２ CF ２ -, -COO-, trans-CH=CH-, trans-CF=CF-, -CH ２ O- or single bond, and n represents 0, 1, 2, or 3.

5. A liquid crystal medium according to any one of claims 1 to 3, characterized by containing one or more dielectrically neutral compounds selected from the group of formulas IV and V. 【Chemistry 14】 (In the formula, R ４１ and R ４２ Each group is an alkyl group having 1 to 15 carbon atoms independently of the others, provided that each group contains one or more CH groups including the terminal carbon atoms. ２ The groups are arranged independently of each other, such that the O or S atoms are not directly bonded to one another, with -C≡C-, -CH=CH-, 【Chemistry 15】 -O-, -S-, -(CO)-O-, -O-(CO)- may be substituted, and in addition, one or more H atoms may be substituted with F or Cl. 【Chemistry 16】 Each of them appeared independently of the others. 【Chemistry 17】 This represents the (fluoro)phenylene ring, which may be substituted with one or two methyl and / or ethyl groups. Z ４１ and Z ４２ In each appearance, -CH is independent of each other. 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 R ４１ and R ４２ It has one of the meanings that can be given to it, [Chemistry 18] Each of them appeared independently of the others. 【Chemistry 19】 This represents the (fluoro)phenylene ring, which may be substituted with one or two methyl and / or ethyl groups. Z ５１ ~Z ５３ each independently represent -CH ２ -CH ２ -, -CH ２ -O-, -CH=CH-, -C≡C-, -COO- or a single bond, and i and j each represent either 0 or 1, independently of each other.

6. A liquid crystal medium according to any one of claims 1 to 4, characterized by comprising one or more compounds selected from formula I-10 or I-11. 【Chemistry 20】 (In the formula, R １ (This has the meaning set forth in claim 1.)

7. A liquid crystal medium according to any one of claims 1 to 5, characterized by further comprising one or more compounds selected from formulas III-1j, III-1k, III-1m, and III-1n. 【Chemistry 21】 (In the formula, R ３ This represents alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, and alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms. X ３ represents F, Cl, halogenated alkyl or alkoxy having 1 to 3 carbon atoms, or halogenated alkenyl or alkenyloxy having 2 or 3 carbon atoms, F, Cl, -OCF ３ , -OCHF ２ , -OCH ２ F, -O-CH ２ CF ３ , -O-CH=CF ２ , -O-CH=CH ２ or -CF ３ , L ３３ and L ３４ These represent H or F independently of each other, and L ３５ and L ３６ These represent H or F, preferably H, independently of each other.

8. A liquid crystal medium according to any one of claims 1 to 6, characterized by further comprising one or more compounds selected from the group of compounds of formula IV-1 to IV-8. 【Chemistry 22】 (In the formula, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms. Alkenyl refers to an alkenyl having 2 to 5 carbon atoms. 'alkenyl' represents an alkenyl having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms. cycloalkyl represents a cyclic alkyl group having 3 to 12 carbon atoms, preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylalkyl, cyclobutylalkyl, or cyclopentylalkyl. Alkoxy represents an alkoxy molecule containing 1 to 5 carbon atoms.

9. A liquid crystal medium according to any one of claims 1 to 7, characterized in that the total concentration of the compound of formula I in the entire medium is 1% or more but less than 30%.

10. A liquid crystal medium according to any one of claims 1 to 8, characterized by further comprising one or more chiral compounds and / or stabilizers.

11. A liquid crystal compound of formula I, preferably formula I-a, as described in claim 1. 【Chemistry 23】 (In the formula, R １ It is defined as in formula I of claim 1, A １ teeth, 【Chemistry 24】 And, L １ , L ２ These are F, Cl, and CH, respectively, independently of each other. ３ or OCH ３ Represents, and Y is CH ３ or CH ２ CH ３ This represents, m is 0, 1 or 2, and A ０ teeth, 【Chemistry 25】 (This represents...)

12. An electro-optical display or electro-optical component characterized by including a liquid crystal medium as described in any one of claims 1 to 9.

13. The display according to claim 11, characterized in that it is based on IPS mode or FFS mode.

14. The display according to claim 11 or 12, characterized by including an active matrix addressing device.

15. Use of the medium according to any one of claims 1 to 9 in electro-optical displays, electro-optical components, or energy-saving applications.

16. A method for preparing a liquid crystal medium according to any one of claims 1 to 9, characterized by mixing one or more compounds of formula I with one or more additional mesogenic compounds and optionally one or more additives.

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