TW201928024A - Liquid-crystalline medium and liquid-crystal display comprising the same - Google Patents

Abstract

The invention relates to a liquid-crystalline medium having a nematic phase comprising one or more compounds of formula B wherein the parameters have the meaning given in the text, to the use thereof in an electro-optical display, particularly in an active-matrix display based on the IPS or FFS effect, to displays of this type which contain a liquid-crystalline medium of this type and to the use of the compounds of formula B for improvement of the transmission and/or response times of a liquid-crystalline medium which comprises one or more additional mesogenic compounds.

Description

Liquid crystal medium and liquid crystal display containing same

The present invention relates to novel liquid crystal media, specifically, those used in liquid crystal displays, and to these liquid crystal displays, and specifically to the use of IPS (In- Plane Switching ) using dielectric positive liquid crystals or, LCD with FFS ( Frequency Field Switching ) effect. The latter is occasionally referred to as the SG-FFS ( Super Grip FFS) effect. In response to this effect, a dielectric positive liquid crystal is used, which contains one or more compounds having a high dielectric constant parallel to the molecular director and perpendicular to the molecular director, which results in a large average dielectric Constant and high dielectric ratio. The liquid crystal medium optionally further contains a dielectric negative, a dielectric neutral compound, or both. Liquid crystal media are used with a horizontal (ie, planar) initial alignment. The liquid crystal medium according to the present invention has a positive dielectric anisotropy and contains a compound having a large dielectric constant that is both parallel and perpendicular to the molecular director.

The medium is characterized by a particularly high transmittance and reduced response time in the respective display, which is a combination of its unique physical properties, especially its dielectric properties and, in particular, its high dielectric ratio (ε _^ / Δε) values are brought about by their high (ε _^ / ε _av. ) Ratio. This also leads to its excellent performance in the display according to the invention.

IPS and FFS displays using dielectric positive liquid crystals are well known in the art and have been widely adopted for various types of displays such as, for example, desktop monitors and televisions, and for mobile applications.

Recently, however, IPS and specifically FFS displays using dielectric negative liquid crystals have been widely used. The latter is sometimes referred to as UB-FFS ( Super Bright FFS). Such displays are disclosed, for example, in US 2013/0207038 A1. These displays are characterized by a marked increase in transmittance compared to previously used IPS- and FFS displays, which are dielectric positive liquid crystals. However, these displays using conventional dielectric negative liquid crystals have the serious disadvantage of requiring higher operating voltages than the respective displays using dielectric positive liquid crystals. The liquid crystal medium used for UB-FFS has a dielectric anisotropy of -0.5 or less and preferably -1.5 or less.

The liquid crystal medium used for HB-FFS (High Brightness FFS) has a dielectric anisotropy of 0.5 or more and preferably 1.5 or more. A liquid crystal medium system for HB-FFS including both dielectric negative and dielectric positive liquid crystal compounds, and respective mesogen compounds is disclosed in, for example, US 2013/0207038 A1. These media are characterized by considerable ε _^ and ε _av. Values, however, their (ε _^ / Δε) ratio is relatively small.

However, according to the present application, the IPS or FFS effect using a dielectrically-positive liquid crystal medium with horizontal alignment is preferred.

Industrial applications of this effect in electro-optical display elements require LC phases that must meet the required diversity. Of particular importance here is the chemical resistance to moisture, air, and physical influences such as radiation in the thermal, infrared, visible, and ultraviolet regions and direct current (DC) and alternating current (AC) electric fields.

In addition, the LC phase that can be used industrially is required to have a liquid crystal mesophase in a suitable temperature range and low viscosity.

None of the series of compounds having a liquid crystal mesophase disclosed so far includes a single compound that meets all of these requirements. Therefore, a mixture of 2 to 25, preferably 3 to 18 compounds is generally prepared to obtain a substance that can be used as an LC phase.

A matrix liquid crystal display (MLC display) is known. Non-linear elements that can be used for individual switching of individual primitives are, for example, active elements (ie, transistors). In the case where thin film transistors (TFTs) are generally used, and such thin film transistors are generally arranged on a glass plate as a substrate, the term "active matrix" is used.

A distinction is made between two technologies: TFTs including compound semiconductors (such as, for example, CdSe) or metal oxides (such as ZnO) or TFTs based on polycrystalline silicon and especially amorphous silicon. The latter technology currently has the most commercial importance throughout the world.

A TFT matrix is applied to the inside of one glass plate of a display, and the other glass plate carries a transparent counter electrode on its inside. Compared to the pixel electrode size, the TFT is very small and does not actually have an adverse effect on the image. This technology can also be extended to full-color displays, in which red, green, and blue filter mosaics are arranged in such a way that the filter elements are located opposite to each switchable element.

The most commonly used TFT displays to date are usually operated in transmissive mode with orthogonal polarizers and are backlit. For TV applications, ECB (or VAN) units or FFS units are used, while monitors usually use IPS units or TN ( Twisted Nematic ) units and laptops, laptops, and mobile applications often use TN, VA or FFS unit.

As used herein, the term MLC display covers any matrix display with integrated non-linear elements (i.e., in addition to the active matrix). It also includes displays with passive elements such as rheostats or diodes (MIM = Metal-Insulator-Metal). .

This type of MLC display is particularly suitable for TV applications, monitors and notebook computers or for displays with high information density, for example, in automobile manufacturing or aircraft construction. In addition to the issues of angular dependence of the contrast and response time, difficulties arise due to the insufficient specific resistance of the liquid crystal mixture in MLC displays [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, September 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, p. 141 and Later, Paris; STROMER, M., Proc. Eurodisplay 84, September 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, p. 145 and later, Paris]. As the resistance decreases, the contrast of the MLC display deteriorates. Because the specific resistance of liquid crystal mixtures generally decreases with the lifetime of MLC displays due to interaction with the inner surface of the display, high (initial) resistance is very important for displays that must have acceptable resistance values over long operating cycles important.

Except for IPS displays (eg Yeo, SD, Paper 15.3: "An LC Display for the TV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pages 758 and 759) and earlier known TN displays It has been established using the display on the ECB effect of the so-called VAN (vertical alignment of nematic) display, as the most important of the three kinds of new types of liquid crystal displays in one of those specific words used in TV applications.

This article can mention the most important design: MVA ( Multi-domain Vertical Alignment , for example: Yoshide, H. et al., Paper 3.1: "MVA LCD for Notebook or Mobile PCs ...", SID 2004 International Symposium, Digest of Technical Papers , XXXV, Book I, pages 6-9, and Liu, CT et al., Thesis 15.1: "A 46-inch TFT-LCD HDTV Technology ...", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pages 750 to 753), PVA ( patterned vertical alignment, for example: Kim, Sang Soo, Paper 15.4: "Super PVA Sets New State-of-the-Art for LCD-TV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pages 760 to 763) and ASV ( advanced large perspective , for example: Shigeta, Mitzuhiro and Fukuoka, Hirofumi, Paper 15.2: "Development of High Quality LCDTV", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 754-757). More modern versions of the VA effect are the so-called PAVA (photo-alignment VA) and PSVA (polymer-stabilized VA).

These technologies are compared in general, for example, in the following comparisons: Souk, Jun, SID Seminar 2004, Seminar M-6: "Recent Advances in LCD Technology", Seminar Lecture Notes, M-6 / 1 to M-6 / 26, and Miller, Ian, SID Seminar 2004, Seminar M-7: "LCD-Television", Seminar Lecture Notes, M-7 / 1 to M-7 / 32. Although the response time of modern ECB displays has been significantly improved by using super-driven addressing methods, for example: Kim, Hyeon Kyeong et al., Paper 9.1: "A 57-in. Wide UXGA TFT-LCD for HDTV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pages 106 to 109, but the achievement of video compatible response time (especially in grayscale switching) is still an unsolved issue to a satisfactory level.

ECB displays (such as ASV displays) use liquid crystal media with negative dielectric anisotropy (Δε), while TN and all conventional IPS displays have used liquid crystal media with positive dielectric anisotropy. However, there is an increasing demand for IPS and FFS displays using dielectric negative liquid crystal media.

In this type of liquid crystal display, these liquid crystals are used as dielectrics, and their optical properties change reversibly with the application of voltage.

Because in general displays, that is, also in displays based on these mentioned effects, the operating voltage should be as low as possible, using a liquid crystal medium usually composed mainly of liquid crystal compounds, all of which have the same sign of dielectric anisotropy Anisotropy with the highest possible dielectric anisotropy value. Generally speaking, at most a relatively small ratio of neutral compounds is used, and if possible, no compound having a sign of dielectric anisotropy opposite to the dielectric anisotropy of the medium. In the case of a liquid crystal medium having a negative dielectric anisotropy (for example, for an ECB or UB-FFS display), a compound mainly having a negative dielectric anisotropy is used. The respective liquid crystal media used are generally composed, and usually even consist essentially of, liquid crystal compounds having negative dielectric anisotropy.

In the medium used according to this application, a significant amount of a dielectric positive liquid crystal compound and generally only a very small amount of a dielectric negative compound or even no dielectric compound are generally used, because in general, a liquid crystal display is intended to have a minimum Possible addressing voltage. In some cases, it may be beneficial to use a small amount of a dielectric neutral compound at the same time.

US 2013/0207038 A1 discloses a liquid crystal medium for HB-FFS displays, which proposes to improve the performance of FFS displays using liquid crystals with positive dielectric anisotropy by additionally incorporating a dielectric negative liquid crystal. However, this leads to the need to compensate for the negative contribution of these compounds to the overall dielectric anisotropy of the resulting medium. For this reason, the concentration of the dielectric positive material must be increased, which in turn leaves less space to use a dielectric neutral compound as a diluent in the mixture, or alternatively, a compound with stronger positive dielectric anisotropy must be used . Both of these alternatives have the powerful disadvantage of increasing the response time of liquid crystals in displays.

Liquid crystal media with positive dielectric anisotropy have been disclosed for IPS and FFS displays. Some examples are given below.

CN 104232105 A, WO 2014/192390 and WO 2015/007131 disclose liquid crystal media with positive dielectric anisotropy, some of which have a relatively high dielectric constant perpendicular to the director.

Obviously, the phase range of the liquid crystal mixture must be wide enough for the intended application of the display.

It is also necessary to improve (ie, reduce) the response time of the liquid crystal medium in the display. This is particularly important for displays used in television or multimedia applications. In order to improve the response time, it has been repeatedly suggested in the past to optimize the rotational viscosity (γ ₁ ) of the liquid crystal medium, that is, to achieve a medium with the lowest possible rotational viscosity. However, the results achieved in this paper are not sufficient for many applications and therefore other optimization methods need to be found.

US 2016-0298033 (A) specifically discloses the following compounds for use in LCDs

and

US 2016-0298034 (A) particularly discloses compounds of the formula
,

and

It is recommended to use the respective compounds for the same purpose.

Sufficient stability of the medium to extreme loads (specifically, to UV exposure and heating) is very important. In particular, this may be crucial in the case of displays applied to mobile devices such as, for example, mobile phones.

In addition to the relatively poor transmittance and relatively long response time, the MLC displays disclosed so far have other disadvantages. These are, for example, their relatively low contrast, their relatively high viewing angle dependence, and the difficulty of grayscale reproduction in these displays, especially when viewed from an oblique viewing angle, and their insufficient VHR and their insufficient life. The required improvements in the transmittance and response time of these displays are needed to improve their energy efficiency, their respective capabilities for moving pictures quickly.

Therefore, there is still a great demand for MLC displays with very high specific resistance and a large operating temperature range, short response time, and low threshold voltage. With the help of these MLC displays, various grayscales and their (specifically) good And stable VHR.

The object of the present invention is to provide MLC displays, not only for monitors and TV applications, but also for mobile applications (such as, for example, telephone and navigation systems), which are based on the ECB, IPS or FFS effect and do not have the disadvantages indicated above , Or has only a small degree of disadvantages, and at the same time has a very high specific resistance value. In particular, it must be ensured that mobile phones and navigation systems can also operate at extremely high and low temperatures.

Surprisingly, it has been found (specifically, in IPS and FFS displays) that a low threshold voltage and short response time, a sufficiently nematic phase, a favorable birefringence (Δn), and at the same time a high transmittance can be achieved For liquid crystal displays with good stability and stability, which are decomposed by heating and UV exposure, and high VHR, if used in these display elements of nematic liquid crystal mixtures, these liquid crystal mixtures contain at least one compound. Preferably two or more compounds of formula B, preferably selected from the group of compounds of formulae B-1 and B-2, particularly preferably formulae B-1 and / or B-2, more preferably formula B -1 and both compounds of formula B-2, and further preferably one or more compounds of formula I, preferably selected from the group of compounds of formulae I-1 and I-2, particularly preferably of formulae I-1 and / Or I-2, preferably both compounds of formula I-2 and most preferably compounds of formula I-1 and formula I-2, and further preferably at least one compound, preferably two or more compounds Compounds from the group of compounds of formulae II and III, the former preferably compounds of formula II-1 and / or II-2, and / or at least one compound, preferably two or more selected from Compounds of the group of formulae IV and / or V, and preferably one or more compounds selected from the group of formulae VII to IX (all formulae are as defined below).

This type of media can be used, specifically for electro-optic displays with active matrix addressing for IPS- or FFS displays.

The invention therefore relates to a liquid crystal medium based on a mixture of polar compounds, the mixture comprising one or more dielectric ratios (ε _^ / Δε) having a dielectric constant perpendicular to the director to dielectric anisotropy of 2.0 or less And preferably 3.8 or more, preferably 4.5 or more, and most preferably a compound having a dielectric constant (ε _^ ) perpendicular to the director of 6.0 or more.

The ratio of the dielectric constant perpendicular to the director to the dielectric anisotropy (ε _^ / Δε) of 1.0 or more corresponds to a dielectric constant (ε _|| ) parallel to the director that is 2.0 or less versus the director The ratio of the dielectric constant (ε _^ ), that is, the ratio of (ε _|| / ε _^ ).

The medium according to the invention preferably further comprises one or more compounds selected from the group of compounds of the formulae II and III, preferably one or more compounds of the formula II, more preferably one or more compounds of the formula III, and most preferably In addition, one or more compounds selected from the group of compounds of the formulae IV and V, and still more preferably, one or more compounds selected from the group of compounds of the formulae VI to IX (all formulae are defined below).

The mixture according to the invention exhibits a very wide nematic phase range with a clarification point of ≥70 ° C, a very advantageous value for the threshold value of the capacitance, a relatively high value for maintaining the ratio and at the same time has a temperature of -20 ° C And good low temperature stability at -30 ℃, and very low rotational viscosity. Furthermore, the mixture according to the invention is characterized by a good ratio of clearing point to rotational viscosity and a relatively high positive dielectric anisotropy.

Now, it has been unexpectedly discovered that an FFS type LC using a liquid crystal with positive dielectric anisotropy can be realized using a specifically selected liquid crystal medium. These media are characterized by specific combinations of physical properties. Among them, the most decisive are its dielectric properties and high average dielectric constant (ε _av. ), High dielectric constant (ε _^ ) perpendicular to the director of the liquid crystal molecules, and, in particular, Relatively high ratio of these latter two values: (ε _^ / Δε).

Preferably, the liquid crystal medium according to the present invention has a dielectric anisotropy value of 1.5 or more, preferably 3.5 or more, and preferably 4.5 or more in one aspect. In another aspect, it preferably has a dielectric anisotropy of 26 or less.

Preferably, the liquid crystal medium according to the present invention has a dielectric constant value perpendicular to the director on the one hand, 2 or more, more preferably 6 or more, and preferably 20 or less, on the other hand.

Preferably, the liquid crystal medium according to the present invention preferably has a dielectric ratio (ε _^ / Δε) of 2.0 or less, more preferably 1.5 or less, and most preferably 1.0 or less.

In a preferred embodiment, the liquid crystal medium according to the present invention preferably has a range of 1.5 or more to 20.0 or less, more preferably a range of 3.0 or more to 8.0 or less, and most preferably 4.0 or more. Positive dielectric anisotropy in the range of 7.0 or below.

In a preferred embodiment (which may be the same as the preferred embodiment described above), the liquid crystal medium according to the present invention has 5.0 or more, more preferably 6.0 or more, more preferably 7.0 or more, more preferably 8.0 or more , More preferably 9 or more, and most preferably 10.0 or more, the dielectric constant (ε _^ ) of the director perpendicular to the liquid crystal molecules.

The liquid crystal medium of the present invention has a dielectric anisotropy of 0.5 or more, preferably 1.5 or more, and a dielectric ratio (ε _^ / Δε) of 2.0 or less and includes
a) one or more compounds of formula B, preferably selected from the group of compounds of formulas B-1 and B-2, preferably in the range of 1% to 60%, more preferably in the range of 5% to 40% , Particularly preferably in the range of 8% to 35%,

among them
Express
,
Represents each other independently of each other


Better
n represents 1 or 2, preferably 1,
R ¹ represents an alkyl group, an alkoxy group, a fluorinated alkyl group or a fluorinated alkoxy group preferably having 1 to 7 C atoms, and an alkenyl group, alkenyl group, or alkoxy group having 2 to 7 C atoms Alkyl or fluorinated alkenyl, preferably alkyl, alkoxy, alkenyl or alkenyloxy, more preferably alkyl, alkenyl, alkoxy or alkenyloxy, and most preferably alkyl, and
X ¹ represents F, Cl, a fluorinated alkyl group, a fluorinated alkenyl group, a fluorinated alkoxy group, or a fluorinated alkenyloxy group, and the latter four groups preferably have 1 to 4 C atoms, more preferably F, Cl, CF ₃ or OCF ₃ , and
b) one or more dielectrically positive compounds selected from the group of compounds of formulae II and III, preferably from compounds each having a dielectric anisotropy greater than 3:


among them
R ² represents an alkyl group, alkoxy group, fluorinated alkyl group or fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl group, alkenyl group, alkoxyalkyl group or alkoxy group having 2 to 7 C atoms Fluorinated alkenyl, and preferably alkyl or alkenyl,
and
Represented independently of each other

, Preferably

L ²¹ and L ²² represent H or F, preferably L ²¹ represents F,
X ² represents halogen, a halogenated alkyl or alkoxy group having 1 to 3 C atoms, or a halogenated alkenyl or alkenyl group having 2 or 3 C atoms, preferably F, Cl, -OCF ₃ , -O -CH ₂ CF ₃ , -O-CH = CH ₂ , -O-CH = CF ₂ or -CF ₃ , preferably F, Cl, -O-CH = CF ₂ or -OCF ₃ ,
m represents 0, 1, 2 or 3, preferably 1 or 2 and particularly preferably 1,
R ³ represents an alkyl group, alkoxy group, fluorinated alkyl group or fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl group, alkenyl group, alkoxyalkyl group, or Fluorinated alkenyl and preferably alkyl or alkenyl,
and
At each occurrence, independently of each other


, Preferably

L ³¹ and L ³² independently represent H or F, preferably L ³¹ represents F,
X ³ represents a halogen, a halogenated alkyl or alkoxy group having 1 to 3 C atoms, or a halogenated alkenyl or alkenyl group having 2 or 3 C atoms, F, Cl, -OCF ₃ , -OCHF ₂ ,- O-CH ₂ CF ₃ , -O-CH = CF ₂ , -O-CH = CH ₂ or -CF ₃ , excellently F, Cl, -O-CH = CF ₂ , -OCHF ₂ or -OCF ₃ ,
Z ³ represents _{-CH 2 CH 2 -, - CF} 2 CF 2 -, - COO-, trans -CH = CH-, trans - CF = CF -, - CH 2 O- or a single bond, preferably - CH ₂ CH _2- , -COO-, trans-CH = CH- or a single bond and 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, and
c) optionally one or more dielectric neutral compounds selected from the group of formulae IV and V:

among them
R ⁴¹ and R ⁴² independently have the meanings indicated above for R ² under Formula II, preferably R ⁴¹ represents an alkyl group and R ⁴² represents an alkyl or alkoxy group or R ⁴¹ represents an alkenyl group and R ⁴² represents an alkane base,
and
Independently of each other Appears twice, these are also shown independently of each other


Better and One or more of

Z ⁴¹ and Z ⁴² independently of one another and, if Z ⁴¹ occurs twice, also these independently of one another denote _{-CH 2 CH 2 -, - COO-} , trans -CH = CH-, trans - CF = CF- , -CH ₂ O-, -CF ₂ O-, -C≡C- or a single bond, preferably one or more of them represents a single bond, and
p represents 0, 1 or 2, preferably 0 or 1, and
R ⁵¹ and R ⁵² independently of each other have one of the meanings given by R ⁴¹ and R ⁴² and preferably represent an alkyl group having 1 to 7 C atoms, preferably an n-alkyl group, particularly preferably having 1 to N-alkyl with 5 C atoms; alkoxy with 1 to 7 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy with 2 to 5 C atoms; C atom, preferably alkoxyalkyl, alkenyl or alkenyl, preferably alkenyl, having 2 to 4 C atoms,
to
If present, each represents each other independently

Better

Better
Express ,
And, if it exists,
then Better represent ,
Z ⁵¹ to Z ⁵³ each independently represent -CH ₂ -CH _2- , -CH ₂ -O-, -CH = CH-, -C≡C-, -COO-, or a single bond, preferably -CH ₂ CH _2- , -CH ₂ -O- or single bond and particularly preferably single bond,
i and j each independently represent 0 or 1,
(i + j) preferably represents 0, 1 or 2, more preferably 0 or 1, and most preferably 1,
d) optionally, or alternatively, or in addition, one or more dielectric negative compounds selected from the group of formulae VI to IX:


among them
R ⁶¹ represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably a propyl or pentyl group; Unsubstituted alkenyl, preferably straight-chain alkenyl, particularly preferably having 2 to 5 C atoms; unsubstituted alkoxy having 1 to 6 C atoms or having 2 to 6 C atoms Unsubstituted alkenyloxy,
R ⁶² represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or an unsubstituted alkenyloxy group having 2 to 6 C atoms, And
l means 0 or 1,
R ⁷¹ represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably a propyl or pentyl group; or having 2 to 7 C atoms Unsubstituted alkenyl, preferably straight-chain alkenyl, particularly preferably having 2 to 5 C atoms,
R ⁷² represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms; having 1 to 6 C atoms, preferably having 1, 2, 3 or 4 C atoms An unsubstituted alkoxy group of an atom; or an unsubstituted alkoxy group having 2 to 6 C atoms, preferably having 2, 3 or 4 C atoms, and
Express

R ⁸¹ represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably a linear alkyl group, more preferably an n-alkyl group, most preferably a propyl or pentyl group or an alkyl group having 2 to 7 C atoms Unsubstituted alkenyl, preferably straight-chain alkenyl, particularly preferably having 2 to 5 C atoms,
R ⁸² represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms; having 1 to 6 C atoms, preferably having 1, 2, 3, or 4 C atoms An unsubstituted alkoxy group of atoms or an unsubstituted alkenyloxy group having 2 to 6 C atoms, preferably 2, 3 or 4 C atoms,
Express

Better
or ,
Better
,
Z ⁸ represents-(C = O) -O-, -CH ₂ -O-, -CF ₂ -O- or -CH ₂ -CH _2- , preferably-(C = O) -O- or -CH ₂ -O-, and
o means 0 or 1,
R ⁹¹ and R ⁹² independently of each other have the meanings given above for R ⁷² ,
R ⁹¹ preferably represents an alkyl group having 2 to 5 C atoms, preferably 3 to 5 C atoms,
R ⁹² preferably represents an alkyl or alkoxy group having 2 to 5 C atoms, more preferably an alkoxy group having 2 to 4 C atoms or an alkenyl group having 2 to 4 C atoms,
Express or ,
p and q independently represent 0 or 1 and
(p + q) preferably represents 0 or 1,
in Express or In the case,
Or, preferably, p = q = 1,
e) optionally, or alternatively, or in addition, one or more compounds of formula I:

among them
Express


Express

Better

n means 0 or 1,
R ¹¹ and R ¹² each independently represent an alkyl group, an alkoxy group, a fluorinated alkyl group, or a fluorinated alkoxy group preferably having 1 to 7 C atoms; an alkenyl group or olefin group having 2 to 7 C atoms Alkoxy, alkoxyalkyl or fluorinated alkenyl and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkyl, alkoxy or alkenyloxy, and R ¹¹ or represents R ¹ and R ¹² or X ¹ ,
R ¹ represents an alkyl group, an alkoxy group, a fluorinated alkyl group, or a fluorinated alkoxy group preferably having 1 to 7 C atoms; an alkenyl group, an alkenyl group, preferably having 2 to 7 C atoms, Alkoxyalkyl or fluorinated alkenyl and preferably alkyl or alkenyl, and
X ¹ represents F, Cl, a fluorinated alkyl group, a fluorinated alkenyl group, a fluorinated alkoxy group, or a fluorinated alkenyloxy group, and the latter four groups preferably have 1 to 4 C atoms, more preferably F, Cl, CF ₃ or OCF ₃ ,
This does not include compounds of formula B.

The liquid crystal medium according to the present application preferably has a nematic phase.

Throughout this application and in particular the definition of R ¹ alkyl means an alkyl group, which may be straight or branched. Each of these groups is preferably straight chain and preferably has 1, 2, 3, 4, 5, 6, 7, or 8 C atoms and is therefore preferably methyl, ethyl, n-propyl , N-butyl, n-pentyl, n-hexyl or n-heptyl.

If alkyl means branched chain alkyl, it preferably means 2-alkyl, 2-methylalkyl or 2- (2-ethyl) -alkyl, preferably 2-butyl (= 1 -Methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, and specifically, 2-methylbutyl Group, 2-methylbutoxy-4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl and 2-dodecyl. Most preferably these groups are 2-hexyl and 2-octyl.

The respective branched chain groups (especially for R ¹ ) leading to the palmitic compound in this application are also referred to as palmitic groups. Particularly good palm groups are 2-alkyl, 2-alkoxy, 2-methylalkyl, 2-methylalkoxy, 2-fluoroalkyl, 2-fluoroalkoxy, 2- ( 2-acetylene) -alkyl, 2- (2-acetylene) -alkoxy, 1,1,1-trifluoro-2-alkyl and 1,1,1-trifluoro-2-alkoxy.

Particularly good palm groups are, for example, 2-butyl (= 1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethyl Hexyl, 2-propylpentyl, specifically 2-methylbutyl, 2-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 2-ethylhexyloxy Methyl, 1-methylhexyloxy, 2-octyloxy, 2-oxo-3-methylbutyl, 3-oxo-4-methylpentyl, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2-decyl, 2-dodecyl, 6-methoxyoctyloxy, 6-methyloctyloxy, 6-methyloctyloxy, 5- Methylheptyloxycarbonyl, 2-methylbutyryloxy, 3-methylpentyloxy, 4-methylhexyloxy, 2-chloropropanyloxy, 2-chloro-3-methyl Butanyloxy, 2-chloro-4-methylpentamyloxy, 2-chloro-3-methylpentamyloxy, 2-methyl-3-oxopentyl, 2-methyl-3- Oxahexyl, 1-methoxypropyl-2-oxy, 1-ethoxypropyl-2-oxy, 1-propoxypropyl-2-oxy, 1-butoxypropyl -2-oxy, 2-fluorooctyloxy, 2-fluorodecyloxy, 1,1,1-trifluoro-2-octyloxy, 1,1,1-trifluoro-2-octyl, 2 -Fluoromethyloctyloxy. Excellently 2-hexyl, 2-octyl, 2-octyloxy, 1,1,1-trifluoro-2-hexyl, 1,1,1-trifluoro-2-octyl and 1,1, 1-trifluoro-2-octyloxy.

Preferably, the compound of formula B is selected from the group of compounds of formula B-1 and B-2:

among them
R ¹ represents an alkyl group, an alkoxy group, a fluorinated alkyl group or a fluorinated alkoxy group preferably having 1 to 7 C atoms; an alkenyl group, alkenyl group, alkoxy group having 2 to 7 C atoms Alkyl or fluorinated alkenyl and preferably alkyl or alkenyl, and
X ¹ represents F, Cl, CN, NCS, a fluorinated alkyl group, a fluorinated alkenyl group, a fluorinated alkoxy group, or a fluorinated alkenyl group. good to F, Cl, CF ₃ or OCF _3, more preferably F, CF ₃ or OCF _3, or OCF ₃ and most preferably CF _3.

Preferably, the compound of formula I is selected from the group of compounds of formulas I-1 and I-2:

among them
R ¹¹ and R ¹² each independently represent an alkyl group, an alkoxy group, a fluorinated alkyl group, or a fluorinated alkoxy group preferably having 1 to 7 C atoms; an alkenyl group or olefin group having 2 to 7 C atoms Alkoxy, alkoxyalkyl or fluorinated alkenyl and preferably alkyl, alkoxy, alkenyl or alkenyloxy, most preferably alkoxy or alkenyloxy,
R ¹ represents an alkyl group, an alkoxy group, a fluorinated alkyl group or a fluorinated alkoxy group preferably having 1 to 7 C atoms; an alkenyl group, alkenyl group, alkoxy group having 2 to 7 C atoms Alkyl or fluorinated alkenyl and preferably alkyl or alkenyl, and
X ¹ represents F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, and the latter four groups preferably have 1 to 4 C atoms, more than Preferably F, Cl, CF ₃ or OCF ₃ , more preferably F, CF ₃ or OCF ₃ , and most preferably CF ₃ or OCF ₃ .

Compound of formula B (Scheme 1) according to the following reaction scheme.

These parameters have their respective meanings given under formula B above.

Separation of the stereoisomer of B-1 (if any) by or without seed crystals by conventional methods, such as flash chromatography and / or recrystallization, can be performed as a single, separate step or repeat and / Or in combination with each other. Basically, it can be used as batch reaction or continuous reaction to process and process the reaction mixture. The continuous reaction mode includes, for example, a reaction in a continuous stirred tank reactor, a stirred reactor cascade, a loop or cross flow reactor, a flow tube, or a microreactor. Process the reaction mixtures as appropriate, by filtering through the solid phase, chromatography, separation (e.g., extraction) between immiscible phases, adsorption on a solid support, distilling off the solvent, and / Either azeotropic mixtures, selective distillation, sublimation, crystallization, co-crystallization or filtration through nanometers on membranes.

The compound of formula I is prepared according to WO 02/055463 and preferably according to the following reaction scheme: ( Reaction scheme 2 ) Starting from the basic compound dibenzofuran, the preparation contains two alkoxy groups (R ¹¹ => R ¹ -O; R ¹² => R ² -O).

-Reaction diagram 2 continued-

-Reaction diagram 2 continued-

Scheme 2. Synthesis of compounds having the formula I-1 of the two alkoxy end groups

Preferably according to the following reaction diagram: ( Reaction Diagram 3 ) Starting from the basic compound dibenzofuran, the preparation contains an alkoxy group (R ¹ -O) and an alkyl group (R ² ) (R ¹¹ => R ¹ -O R ¹² => R ² ) a compound of formula I-1.

Reaction Figure 3. Synthesis of a compound of formula I-1 with one alkyl and one alkoxy end group. The group R corresponds to a group such as R ^{2 which} is correspondingly shortened by one carbon atom.

The following reaction scheme is preferred: ( Reaction Scheme 4 ) Starting from the basic compound dibenzofuran, a compound of formula I-1 containing two alkyl groups (R ¹¹ => R ¹ ; R ¹² => R ² ) is prepared.

4. Synthesis of compound of Formula I-1 Reaction of FIG. The group R of the aldehyde used corresponds to a group such as R ^{2 which} is correspondingly shortened by one carbon atom.

Preferably, for example, the compound of formula I-2 is prepared according to the following reaction scheme.

5 Synthesis of Compound I-2 of the reaction scheme.

The invention further relates to the use of a liquid crystal mixture and a liquid crystal medium according to the invention in IPS and FFS displays, in particular to a use in a SG-FFS display containing a liquid crystal medium for improving response time and / or transmission rate.

The invention further relates to a liquid crystal display containing a liquid crystal medium according to the invention, in particular an IPS or FFS display, particularly preferably an FFS or SG-FFS display.

The present invention further relates to an IPS or FFS type liquid crystal display including a liquid crystal cell composed of two substrates, wherein at least one substrate is transparent and at least one substrate has an electrode layer, and the polymerized component and A layer of a liquid crystal medium with a low molecular weight component, wherein the polymerizable component can be obtained by polymerizing one or more polymerizable compounds in a liquid crystal medium between substrates of the liquid crystal cell, preferably applying a voltage and the low molecular weight thereof. The components are the liquid crystal mixtures according to the invention as described above and below.

The display according to the present invention is preferably addressed by an active matrix (referred to as an active matrix LCD , AMD), and preferably by a matrix of a thin film transistor (TFT). However, the liquid crystal according to the invention can also be used in an advantageous manner in displays with other known addressing methods.

The invention further relates to a method for preparing a liquid crystal medium according to the invention by using one or more compounds of formula B and one or more low molecular weight liquid crystal compounds preferably selected from the group of compounds of formulas B-1 and B-2. Or liquid crystal mixtures and optionally with other liquid crystal compounds and / or additives.

The following meanings apply above and below:

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

The term "liquid crystalline group" is known to those skilled in the art and is described in the literature, and indicates the anisotropy due to its attractive and repulsive interactions, which essentially contributes to low-molecular-weight or polymeric liquid crystals ( LC) group. The compound containing a mesogen group (the mesogen) need not necessarily have a liquid crystal phase in itself. The mesogen compound may also exhibit liquid crystal phase behavior only after being mixed with other compounds and / or after polymerization. Typical mesogen groups are, for example, rigid rods or disc-shaped cells. Uses related to mesogens or liquid crystal compounds are given in Pure Appl. Chem. 73 (5), 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368 Overview of terms and definitions.

The term "spacer" or "spacer", also referred to as "Sp" above and below, is known to those skilled in the art and is described in the literature. See, for example, Pure Appl. Chem. 73 (5 ), 888 (2001) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. Unless otherwise indicated, the term "spacer" or "spacer" above and below means a flexible group that connects the mesogen and the polymerizable group in the polymerizable mesogen compound to each other.

For the purposes of the present invention, the term "liquid crystal medium" is intended to mean a medium comprising a liquid crystal mixture and one or more polymerizable compounds such as, for example, a reactive mesogen. The term "liquid crystal mixture" (or "host mixture") is intended to mean completely composed of a non-polymerizable low molecular weight compound, preferably two or more liquid crystal compounds, and optionally other additives such as, for example, palmitic blending Miscellaneous agent or stabilizer).

Particularly preferred are liquid crystal mixtures and liquid crystal media having a nematic phase at room temperature.

In a preferred embodiment of the present invention, the liquid crystal medium includes one or more dielectric positive compounds having a dielectric anisotropy greater than 3, which are selected from the group of compounds of formulas II-1 and II-2:

Wherein these parameters have their respective meanings indicated under formula II above, and L ²³ and L ²⁴ independently represent H or F, preferably L ²³ represents F, and
With One of the given meanings,
And in the case of formulas II-1 and II-2, X ² preferably represents F or OCF ₃ , particularly preferably F, and, in the case of formula II-2,
and
Independent of each other, preferably represented
or ,
And / or selected from the group of compounds of formulas III-1 and III-2:

These parameters have the meanings given in Formula III,
And the medium according to the invention may comprise or in addition to compounds of formula III-1 and / or III-2, one or more compounds of formula III-3

Among them, these parameters have their respective meanings indicated above, and the parameters L ³¹ and L ³² represent H or F independently of each other and independently of other parameters.

The liquid crystal medium preferably comprises a compound selected from the group of compounds of formulae II-1 and II-2, wherein L ²¹ and L ²² and / or L ²³ and L ²⁴ each represent F.

In a preferred embodiment, the liquid crystal medium comprises a compound selected from the group of compounds of formulae II-1 and II-2, wherein L ²¹ , L ²² , L ²³ and L ²⁴ all represent F.

The liquid crystal medium preferably comprises one or more compounds of formula II-1. The compounds of formula II-1 are preferably selected from the group of compounds of formula II-1a to II-1e, preferably one or more compounds of formula II-1a and / or II-1b and / or II-1d, more preferably Compounds of formula II-1a and / or II-1d or II-1b and / or II-1d, most preferably compounds of formula II-1d:


Wherein these parameters have their respective meanings indicated above, and L ²⁵ and L ²⁶ represent H or F independently of each other and independently of other parameters, and preferably, in Formula II-1a and II-1b, L ²¹ And L ²² both represent F, and in formulas II-1c and II-1d, L ²¹ and L ²² each represent F and / or L ²³ and L ²⁴ each represent F, and in formula II-1e, L ²¹ and L ²² indicates F.

The liquid crystal medium preferably comprises one or more compounds of formula II-2, which is preferably selected from the group of compounds of formula II-2a to II-2k, preferably one or more of formula II-2a and / or II- Compounds of 2h and / or II-2j:


Wherein these parameters have their respective meanings indicated above, and L ²⁵ to L ²⁸ represent H or F independently of each other, preferably L ²⁷ and L ²⁸ both represent H, and particularly preferably L ²⁶ represents H.

The liquid crystal medium preferably comprises a compound selected from the group of compounds of the formulae II-2a to II-2k, wherein L ²¹ and L ²² each represent F and / or L ²³ and L ²⁴ each represent F.

In a preferred embodiment, the liquid crystal medium comprises a compound selected from the group of compounds of formulae II-2a to II-2k, wherein L ²¹ , L ²² , L ²³ and L ²⁴ all represent F.

Particularly preferably, the compound of formula II-2 is a compound of the following formula, particularly preferably a compound of formula II-2a-1 and / or II-2h-1 and / or II-2k-2:



Wherein R ² and X ² have the meanings indicated above, and X ² preferably represents F.

The liquid crystal medium preferably comprises one or more compounds of formula III-1. The compounds of the formula III-1 are preferably selected from the group of compounds of the formulae III-1a to III-1j, preferably from the compounds of the formulae III-1c, III-1f, III-1g and III-1j:


Wherein these parameters have the meanings given above and preferably among them, these parameters have their respective meanings indicated above, the parameters L ³³ and L ³⁴ represent H or F independently of each other and independently of other parameters and the parameter L ³⁵ And L ³⁶ represent H or F independently of each other and independently of other parameters.

The liquid crystal medium preferably comprises one or more compounds of formula III-1c, which are preferably selected from the group of compounds of formula III-1c-1 to III-1c-5, preferably formula III-1c-1 and / Or III-1c-2 compounds, most preferably compounds of formula III-1c-1:

Wherein R ³ has the meaning indicated above.

The liquid crystal medium preferably comprises one or more compounds of formula III-1f, which is preferably selected from the group of compounds of formula III-1f-1 to III-1f-6, preferably formula III-1f-1 and / Or a compound of III-1f-2 and / or III-1f-3 and / or III-1f-6, more preferably a compound of formula III-1f-3 and / or III-1f-6, more preferably formula III-1f -6 compounds:

Wherein R ³ has the meaning indicated above.

The liquid crystal medium preferably comprises one or more compounds of formula III-1g, which are preferably selected from the group of compounds of formula III-1g-1 to III-1g-5, preferably compounds of formula III-1g-3:

Wherein R ³ has the meaning indicated above.

The liquid crystal medium preferably comprises one or more compounds of formula III-1h, which are preferably selected from the group of compounds of formula III-1h-1 to III-1h-3, preferably compounds of formula III-1h-3:

Wherein these parameters have the meanings given above, and X ³ preferably represents F.

The liquid crystal medium preferably comprises one or more compounds of formula III-1i, which are preferably selected from the group of compounds of formula III-1i-1 and III-1i-2, preferably compounds of formula III-1i-2:


Wherein these parameters have the meanings given above, and X ³ preferably represents F.

The liquid crystal medium preferably comprises one or more compounds of formula III-1j, which are preferably selected from the group of compounds of formula III-1j-1 and III-1j-2, preferably compounds of formula III-1j-1:

These parameters have the meanings given above.

The liquid crystal medium preferably comprises one or more compounds of formula III-2. The compounds of the formula III-2 are preferably selected from the group of compounds of the formulae III-2a and III-2b, more preferably the compounds of the formula III-2b:

Wherein these parameters have their respective meanings indicated above, and the parameters L ³³ and L ³⁴ represent H or F independently of each other and independently of other parameters.

The liquid crystal medium preferably comprises one or more compounds of formula III-2a, which are preferably selected from the group of compounds of formula III-2a-1 to III-2a-6:


Wherein R ³ has the meaning indicated above.

The liquid crystal medium preferably comprises one or more compounds of formula III-2b, which are preferably selected from the group of compounds of formula III-2b-1 to III-2b-4, preferably III-2b-4 compounds:

Wherein R ³ has the meaning indicated above.

Alternatively or in addition to compounds of formula III-1 and / or III-2, the medium according to the invention may comprise one or more compounds of formula III-3

These parameters have their respective meanings indicated under formula III above.

These compounds are preferably selected from the group of formulae III-3a and III-3b:

Wherein R ³ has the meaning indicated above.

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

In this application, all elements include their respective isotopes. In particular, one or more H in the compound may be replaced by D, and this is particularly preferred in some embodiments. The corresponding high degree of deuteration of the corresponding compounds enables, for example, detection and identification of the compounds. In some cases, this is particularly useful in the case of compounds of formula I.

In this application,
The alkyl group particularly preferably represents a linear alkyl group, specifically, CH _3- , C ₂ H _5- , n -C ₃ H _7- , n -C ₄ H _9- , or n -C ₅ H _11- , and Alkenyl particularly preferably represents CH ₂ = CH-, E- CH ₃ -CH = CH-, CH ₂ = CH-CH ₂ -CH _2- , E- CH ₃ -CH = CH-CH ₂ -CH ₂ -or E- ( n -C ₃ H ₇ ) -CH = CH-.

In a preferred embodiment of the invention, the medium according to the invention comprises in each case one or more compounds of the formula VI selected from the group of compounds of the formulae VI-1 and VI-2, preferably one or more formulae Compounds of each of VI-1 and one or more compounds of formula VI-2,

Wherein these parameters have their respective meanings given under formula VI above, and are preferably in formula VI-1
R ⁶¹ and R ⁶² independently of each other represent methoxy, ethoxy, propoxy, butoxy (or pentoxy), preferably ethoxy, butoxy or pentoxy, more preferably Ethoxy or butoxy and optimally butoxy.
In Formula VI-2
R ⁶¹ preferably represents vinyl, 1- E -propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl and n-propyl or N-pentyl, and
R ⁶² represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, or, preferably, 1 to 6 C atoms, particularly preferably 2 or 4 Unsubstituted alkoxy and preferably ethoxy.

In a preferred embodiment of the invention, the medium according to the invention comprises in each case one or more compounds of the formula VII selected from the group of compounds of the formulae VII-1 to VII-3, preferably one or more formulas Compounds of each of VII-1 and one or more compounds of formula VII-2,

Wherein these parameters have their respective meanings given under formula VII above, and preferably
R ⁷¹ represents vinyl, 1- E -propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, n-propyl or n-pentyl , And
R ⁷² represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, or, preferably, 1 to 6 C atoms, particularly preferably 2 or 4 Unsubstituted alkoxy and preferably ethoxy.

In a preferred embodiment of the invention, the medium according to the invention comprises in each case one or more compounds of the formula VI-1 selected from the group of compounds of the following:

In a preferred embodiment of the invention, the medium according to the invention comprises in each case one or more compounds of the formula VI-2 selected from the group of the following compounds:

In a preferred embodiment of the invention, the medium according to the invention comprises, in each case, one or more compounds of the formula VII-1 selected from the group of compounds:

In a preferred embodiment of the invention, the medium according to the invention comprises, in each case, one or more compounds of the formula VII-2 selected from the group of the following compounds:

In addition to the compound of formula B or a preferred sub-formula thereof, the medium according to the present invention preferably contains one or more dielectric negative compounds selected from the group of compounds of formula VI and VII, preferably from 5% or more to 90 % Or less, preferably 10% or more to 80% or less, and particularly preferably a total concentration in the range of 20% or more to 70% or less.

In a preferred embodiment of the invention, the medium according to the invention comprises in each case one or more compounds of the formula VIII selected from the group of compounds of the formulae VIII-1 to VIII-3, preferably one or more compounds of the formula Compounds of each of VIII-1 and / or one or more compounds of formula VIII-3,

Wherein these parameters have their respective meanings given under formula VIII above, and preferably
R ⁸¹ represents vinyl, 1- E -propenyl, but-4-en-1-yl, pent-1-en-1-yl or pent-3-en-1-yl, ethyl, n-propyl or N-pentyl, alkyl, preferably ethyl, n-propyl or n-pentyl, and
R ⁸² represents an unsubstituted alkyl group having 1 to 7 C atoms, preferably 1 to 5 C atoms or an unsubstituted alkoxy group having 1 to 6 C atoms.

In formulae VIII-1 and VIII-2, R ⁸² preferably represents an alkoxy group having 2 or 4 C atoms, and most preferably ethoxy group and in formula VIII-3, R ⁸² preferably represents Alkyl, preferably methyl, ethyl or n-propyl, most preferably methyl.

In another preferred embodiment, the medium comprises one or more compounds of formula IV, preferably compounds of formula IVa

among them
R ⁴¹ represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, preferably an n-alkyl group, particularly preferably having 2, 3, 4 or 5 C atoms, and
R ⁴² represents an unsubstituted alkyl group having 1 to 7 C atoms; an unsubstituted alkenyl group having 2 to 7 C atoms or an unsubstituted alkoxy group having 1 to 6 C atoms (all It preferably has 2 to 5 C atoms); preferably an unsubstituted alkenyl group having 2, 3 or 4 C atoms, more preferably vinyl or 1-propenyl and, in particular, vinyl.

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

Wherein the alkyl group and the alkyl group independently represent an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms,
Alkenyl and alkenyl 'independently of each other represent alkenyl groups having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 C atoms,
Alkenyl 'preferably means an alkenyl group having 2 to 5 C atoms, preferably 2 to 4 C atoms, particularly preferably 2 to 3 C atoms, and an alkoxy group having 1 to 5 C atom, preferably an alkoxy group having 2 to 4 C atoms.

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

In another preferred embodiment, the medium comprises one or more compounds of formula V.

The medium according to the invention preferably comprises the following compounds at the indicated total concentration:
1 to 60% by weight of one or more compounds selected from the group of compounds of formula B and
0 to 60% by weight of one or more compounds of formula I, preferably selected from the group of compounds of formulas I-1 and I-2, most preferably compounds of formula I-2 and / or
5 to 60% by weight of one or more compounds of the formula II preferably selected from the group of compounds of the formulae II-1 and II-2 and / or
5 to 25% by weight of one or more compounds of formula III, and / or
5 to 45% by weight of one or more compounds of formula IV, and / or
5 to 25% by weight of one or more compounds of formula V, and / or
5 to 25% by weight of one or more compounds of formula VI, and / or
5 to 20% by weight of one or more compounds of formula VII, and / or
5 to 30% by weight of one or more compounds of the formula VIII, preferably selected from the group of compounds of the formulae VIII-1 and VIII-2, and / or
0 to 60% by weight of one or more compounds of formula IX in which the total content of all compounds of formula B and formulae I to IX present in the medium is preferably 95% or more, more preferably 97% or more, and most Best 100%.

The latter condition applies to all media under this application.

In another preferred embodiment, in addition to a compound of formula B or a preferred sub-formula thereof and a compound of formula VI and / or VII and / or VIII and / or IX and / or I, the medium according to the present invention preferably comprises a Or more dielectrically neutral compounds selected from the group of compounds of formulae IV and V, preferably from 5% or more to 90% or less, preferably from 10% or more to 80% or less, particularly preferably 20 Total concentration in the range of% or more to 70% or less.

In a particularly preferred embodiment, the medium according to the present invention comprises one of a total concentration in a range of 3% or more to 50% or less, preferably in a range of 5% or more to 30% or less, or A plurality of compounds of formula B, and one or more compounds of formula I at a total concentration in the range of 3% or more to 50% or less, preferably 5% or more to 30% or less, and / or One or more compounds of formula II at a total concentration in the range of 5% or more to 50% or less, preferably in the range of 10% or more to 40% or less, and / or at 5% or more One or more compounds of formula VII-1 at a total concentration in the range of 30% or less, and / or one or more compounds of formula VII-2 at a total concentration in the range of 3% or more to 30% or less .

Preferably, the concentration of the compound of formula B in the medium according to the invention is from 1% or more to 60% or less, more preferably 5% or more to 40% or less, most preferably 8% or more to 35 % Or less.

In a preferred embodiment of the present invention, the concentration of the compound of formula I in the medium according to the present invention is 1% or more to 60% or less, more preferably 5% or more to 40% or less, most preferably 8% or more to 35% or less.

In a preferred embodiment of the present invention, the concentration of the compound of formula II in the medium is 3% or more to 60% or less, more preferably 5% or more to 55% or less, more preferably 10%. Or more to 50% or less, and optimally in the range of 15% or more to 45% or less.

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

In a preferred embodiment of the present invention, the concentration of the compound of formula VII-1 in the medium is 1% or more to 40% or less, more preferably 2% or more to 35% or less, or, or , 15% or more to 25% or less.

In a preferred embodiment of the present invention, the concentration of the compound of formula VII-2 in the medium (if present) is 1% or more to 40% or less, more preferably 5% or more to 35% or less , And preferably within a range of 10% or more to 30% or less.

The present invention also relates to an electro-optical display or an electro-optical component containing a liquid crystal medium according to the present invention. Electro-optic displays based on VA, ECB, IPS, or FFS effects, preferably based on VA, IPS, or FFS effects, and in particular, addressing by means of an active matrix addressing device, and the like.

Therefore, the present invention also relates to the use of a liquid crystal medium according to the present invention in an electro-optical display or to an electro-optical component, and to a method for preparing a liquid crystal medium according to the present invention, which is characterized by mixing the following: one or more formulas B Compounds with one or more compounds of formula I, preferably with one or more compounds of formula I-1 and / or I-2, preferably compounds of formula I-2 and / or one or more compounds of formula II, preferably With one or more compounds of formula II-1 and / or II-2, with one or more compounds of formula VII, preferably with one or more compounds of formula VII-1 and / or VII-2, particularly preferably one or Multiple from two or more, preferably from three or more different formulae, and very particularly preferably from all of formulae II-1, II-2, VII-1 and VII-2 The four compounds and one or more other compounds preferably selected from the group of compounds of the formulae IV and V, more preferably with one or more of the compounds of the formulae IV and V.

In another 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,

Wherein the alkyl group and the alkyl group independently represent an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms,
An alkoxy group means an alkoxy group having 1 to 5 C atoms, preferably 2 to 4 C atoms.

In another preferred embodiment, the medium comprises one or more compounds of formula V selected from the group of compounds of formula V-1 and V-2, preferably compounds of formula V-1,

Wherein these parameters have the meanings given under the formula V above, and preferably
R ⁵¹ represents an alkyl group having 1 to 7 C atoms or an alkenyl group having 2 to 7 C atoms, and
R ⁵² represents an alkyl group having 1 to 7 C atoms, an alkenyl group having 2 to 7 C atoms, or an alkoxy group having 1 to 6 C atoms, preferably an alkyl group or an alkenyl group, and particularly preferably an alkyl group base.

In another preferred embodiment, the medium comprises one or more compounds of formula V-1 selected from the group of compounds of formula V-1a and V-1b,


Wherein the alkyl group and the alkyl group independently represent an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, and the alkenyl group represents 2 to 7 C atoms, preferably 2 Alkenyl to 5 C atoms.

In addition, the present invention relates to a method for reducing the wavelength dispersion of the birefringence of a liquid crystal medium. The liquid crystal medium contains one or more compounds of formula II, and optionally one or more compounds selected from formulas VII-1 and VII-2. A compound of the group of compounds and / or one or more compounds of formula IV and / or one or more compounds of formula V, the method is characterized by using one or more compounds of formula B in the medium.

In addition to the compounds of the formulae I to V, other components may be present, for example, in an amount of up to 45% of the overall mixture, but preferably up to 35%, in particular up to 10%.

The medium according to the present invention may optionally contain a dielectric positive component, and its total concentration is preferably 20% or less, more preferably 10% or less based on the entire medium.

In a preferred embodiment, the liquid crystal medium according to the present invention contains a total of
1% or more to 20% or less, preferably 2% or more to 15% or less, particularly preferably 3% or more to 12% or less, a compound of formula B,
1% or more to 20% or less, preferably 2% or more to 15% or less, particularly preferably 3% or more to 12% or less, a compound of formula I,
20% or more to 50% or less, preferably 25% or more to 45% or less, particularly preferably 30% or more to 40% or less of a compound of formula II and / or III, and
0% or more to 35% or less, preferably 2% or more to 30% or less, particularly preferably 3% or more to 25% or less of a compound of formula IV and / or V, and
5% or more to 50% or less, 10% or more to 45% or less, preferably 15% or more to 40% or less of a compound of formula VI and / or VII and / or VIII and / or IX.

The liquid crystal medium according to the present invention may contain one or more palmitic compounds.

A particularly preferred embodiment of the present invention satisfies one or more of the following conditions,
The acronyms (abbreviations) are illustrated in Tables A to C and illustrated in Table D by way of example.

Preferably the medium according to the invention satisfies one or more of the following conditions.
i. The liquid crystal medium has a birefringence of 0.060 or more, particularly preferably 0.070 or more.
ii. The liquid crystal medium has a birefringence of 0.200 or less, particularly preferably 0.180 or less.
iii. The liquid crystal medium has a birefringence in a range of 0.090 or more to 0.160 or less.
iv. The liquid crystal medium comprises one or more particularly preferred compounds of formula BI, preferably selected from (sub) formulas B-1 and B-2, most preferably (sub) formula B-2 compounds.
v. The liquid crystal medium comprises one or more particularly preferred compounds of formula I, preferably selected from (sub) formulas I-1 and I-2, most preferably (sub) compounds of formula I-2.
vi. The total concentration of the compound of formula II in the overall mixture is 25% or more, preferably 30% or more, and preferably in a range of 25% or more to 49% or less, particularly preferably 29% or more Within the range of from above to 47% or below, and very particularly preferably within the range of from 37% or above to 44% or below.
vii. the liquid crystal medium comprises one or more compounds of formula IV selected from the group of compounds of the formula: CC-nV and / or CC-n-Vm and / or CC-VV and / or CC-V-Vn and / or CC-nV-Vn, particularly preferably CC-3-V, preferably at a concentration of up to 60% or less, particularly preferably at a concentration of up to 50% or less, and optionally CC-3-V1, preferably Concentrations of at most 15% or less, and / or CC-4-V, preferably of at most 40% or less, particularly preferably of at most 30% or less.
viii. The medium comprises a compound of formula CC-nV, preferably a CC-3-V compound, preferably at a concentration of 1% or more to 60% or less, more preferably 3% or more to 35% or less concentration.
ix. The total concentration of the compound of formula CC-3-V in the overall mixture is preferably 15% or less, preferably 10% or less or 20% or more, and preferably 25% or more.
x. The total concentration of the compound of formula Y-nO-Om in the overall mixture is 2% or more to 30% or less, preferably 5% or more to 15% or less.
xi. The total concentration of the compound of formula CY-n-Om in the overall mixture is 5% or more to 60% or less, preferably 15% or more to 45% or less.
xii. The total concentration of the compound of the formula CCY-n-Om and / or CCY-nm in the overall mixture is preferably 5% or more to 40% or less, preferably 1% or more to 25 % Or below.
xiii. The total concentration of the compound of formula CLY-n-Om in the overall mixture is 5% or more to 40% or less, preferably 10% or more to 30% or less.
xiv. the liquid crystal medium comprises one or more compounds of formula IV, preferably compounds of formula IV-1 and / or IV-2, preferably 1% or more, specifically 2% or more, and very particularly preferably A total concentration of 3% or more to 50% or less, preferably 35% or less.
xv. the liquid crystal medium comprises one or more compounds of formula V, preferably compounds of formula V-1 and / or V-2, preferably 1% or more, specifically 2% or more, and very particularly preferably A total concentration of 15% or more to 35% or less, preferably 30% or less.
xvi. The total concentration of the compound of formula CCP-Vn, preferably CCP-V-1 in the overall mixture is preferably 5% or more to 30% or less, preferably 15% or more to 25% or less.
xvii. The total concentration of the compound of formula CCP-V2-n, preferably CCP-V2-1 in the overall mixture is preferably 1% or more to 15% or less, preferably 2% or more to 10% or less .

The invention further relates to an electro-optic display with active matrix addressing based on the VA, ECB, IPS, FFS or UB-FFS effect, which is characterized in that it comprises a liquid crystal medium according to the invention as a dielectric.

The liquid crystal mixture preferably has a nematic phase range with a width of at least 70 degrees.

The rotational viscosity γ _{1 is} preferably 350 mPa × s or less, preferably 250 mPa × s or less and, specifically, 150 mPa × s or less.

The mixture according to the invention is suitable for all IPS and FFS-TFT applications using dielectric positive liquid crystal media, such as, for example, SG-FFS.

The liquid crystal medium according to the present invention preferably consists entirely of 4 to 15 species, specifically 5 to 12 species, and particularly preferably 10 or less compounds. These are preferably selected from the group of compounds of the formulae B, I, II, III, IV, V, VI, VII, VIII and IX.

The liquid crystal medium according to the present invention may optionally contain more than 18 compounds. In this case, it preferably contains 18 to 25 compounds.

In a preferred embodiment, the liquid crystal medium according to the present invention mainly comprises a cyano-free compound, preferably consisting essentially of it, and most preferably consisting entirely of it.

In a preferred embodiment, the liquid crystal medium according to the present invention comprises a group selected from the compounds of formulae I, II, III, IV, V and VI to IX, preferably selected from the formulae I-1, I-2, II -1, II-2, III-1, III-2, IV, V, VII-1, VII-2, VIII, and IX; a group of compounds; it is preferably composed mainly of compounds of the formula, particularly preferably The ground consists essentially of it and very, very preferably, actually consists entirely of it.

The liquid crystal medium according to the present invention preferably has at least -10 ° C or below to 70 ° C or above in each case, particularly preferably -20 ° C or below to 80 ° C or above, very particularly preferably -30 ° C or below Nematic phases to 85 ° C or above and optimally -40 ° C or below to 90 ° C or above.

The expression "having a nematic phase" herein means that, on the one hand, no smectic phase and crystals are observed at a low temperature at the corresponding temperature, and on the other hand, no clarification occurs upon heating beyond the nematic phase. Research at low temperatures was performed in a flow viscometer at the corresponding temperature and checked by storing in a test unit with a unit thickness corresponding to an electro-optical application for at least 100 hours. If the storage stability in the corresponding test unit at a temperature of -20 ° C is 1000 hours or more, the medium is considered to be stable at this temperature. At temperatures of -30 ° C and -40 ° C, the corresponding times are 500 hours and 250 hours, respectively. At high temperatures, the clearing point is measured in a capillary tube by conventional methods.

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

In this embodiment, the liquid crystal medium according to the present invention has a positive dielectric anisotropy and a relatively high absolute value of the dielectric anisotropy Δε, which is preferably from 2.0 or more to 20 or less, more preferably to 15 or less, more preferably 3.0 or more to 10 or less, particularly preferably 4.0 or more to 9.0 or less and very particularly preferably 4.5 or more to 8.0 or less.

The liquid crystal medium according to the present invention preferably has a voltage of 1.0 V or higher to 5.0 V or lower, preferably 2.5 V or lower, preferably 1.2 or higher to 2.2 V or lower, particularly preferably 1.3 V or higher to A relatively low threshold voltage (V ₀ ) value in the range of 2.0 V or below.

In another preferred embodiment, the liquid crystal medium according to the present invention preferably has a relatively high average dielectric constant (ε _av. ≡ (ε _êê + 2ε _^ / 3) / 3) value, which is preferably at 8.0. Or more to 25.0 or less, preferably 8.5 or more to 20.0 or less, still more preferably 9.0 or more to 19.0 or less, particularly preferably 10.0 or more to 18.0 or less and very particularly preferably 11.0 or more to 16.5 Or below.

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

In units newly filled at 20 ° C, the VHR of these media is greater than or equal to 95%, preferably greater than or equal to 97%, particularly preferably greater than or equal to 98%, and very special Preferably greater than or equal to 99%, and after 5 minutes in an oven at 100 ° C, in these units, the VHR value is greater than or equal to 90%, preferably greater than or equal to 93%, particularly preferably greater than or Equal to 96% and very particularly preferably greater than or equal to 98%.

Generally speaking, a liquid crystal medium having a low addressing voltage or a threshold voltage herein has a lower VHR than those having a higher addressing voltage or a threshold voltage, and vice versa.

These preferred values of the individual physical properties are also preferably maintained in each case by combining the media according to the invention with each other.

In this application, the term "compounds", also written as "compound (s)", means one compound and also means a plurality of compounds, unless expressly indicated otherwise.

In a preferred embodiment, the liquid crystal medium according to the present invention comprises one or more compounds of formula B, preferably selected from the formulas CB-nF, CB-n-OT, CB-nT, LB-nF, LB-n- The group of OT and LB-nT is more preferably selected from the group of formulas CB-n-OT, CB-nT, LB-n-OT and LB-nT, and is preferably selected from the group of formulas CB-n-OT, CB- a group of nT, and one or more compounds of formula I, preferably selected from the group consisting of formulas B-nO-Om, B (S) -nO-Om, B-nO-OT, B-nO-T, Bn-OT and BnF A group, preferably selected from the group of formulas B-nO-OT, B-nO-T, Bn-OT, and BnF, and / or one or more compounds of formula II, preferably selected from the formulas PUQU-nF, CDUQU -nF, APUQU-nF and PGUQU-nF, and / or one or more compounds of formula III, preferably selected from the group of formulas CCP-n-OT, CGG-nF and CGG-n-OD, and / or One or more compounds of formula IV and / or V, preferably selected from the group of formulas CC-nV, CCP-nm, CCP-Vn, CCP-V2-n and CGP-nn, and / or one or more compounds of formula VI , Preferably selected from the group of formulas Yn-Om, Y-nO-Om and / or CY-n-Om, preferably selected from formulas Y-3-O1, Y-4O-O4, CY-3-O2 , CY-3-O4, CY-5-O2 and CY-5-O4 compounds, and / or optionally, preferably necessarily, one or more compounds of formula VII-1 , Preferably selected from the group of compounds of formula CCY-nm and CCY-n-Om, preferably compound of formula CCY-n-Om, preferably selected from formula CCY-3-O2, CCY-2-O2, CCY A group of -3-O1, CCY-3-O3, CCY-4-O2, CCY-3-O2, and CCY-5-O2 compounds, and / or optionally, preferably necessarily, one or more formulas VII -2 compounds, preferably compounds of formula CLY-n-Om, preferably selected from the group of compounds of formula CLY-2-O4, CLY-3-O2, CLY-3-O3, and / or one or more formula VIII Compounds, preferably selected from the group of formulas CZY-n-On and CCOY-nm, and / or one or more compounds of formula IX, preferably selected from formulas PYP-nm, PYP-n-Vl and PYP-n- The group of mVl is preferably selected from the group of formulas PYP-2-3, PYP-2-4, PYP-2-5, PYP-2-V and PYP-2-2V1, and / or one or more selected from Compounds of the group of formulas PGP-nm, PGP-nV, PGP-n-Vm, PGP-n-mV and PGP-n-mVl, preferably selected from the formulas PGP-2-3, PGP-2-4, PGP A group of -2-5, PGP-1-V, PGP-2-V and PGP-2-2V1, and / or optionally, preferably necessarily, one or more compounds of formula IV, preferably selected from Groups of compounds of formula CC-nV, CC-n-Vm, CC-n-mVl and CC-nV-Vm, preferably CC-3-V, CC-3-V1, CC-4-V, CC-5 -V, C The C-3-2V1 and CC-VV compounds are particularly preferably selected from the group of the compounds CC-3-V, CC-3-V1, CC-4-V, CC-3-2V1, and CC-VV, and are very particularly preferred. Compound CC-3-V, and optionally additional compounds CC-4-V and / or CC-3-V1 and / or CC-3-2V1 and / or CC-VV, and / or Preferably, one or more compounds of formula V are preferably selected from the group of formulas CCP-V-1 and / or CCP-V2-1.

In a specific preferred embodiment of the invention, the medium according to the invention comprises one or more compounds of formula IX.

The compounds of formula IX are also very suitable as stabilizers in liquid crystal mixtures, especially in the case of p = q = 1 and ring A ⁹ = 1,4-phenylene. In particular, it stabilizes the VHR of the mixture against UV exposure.

In a preferred embodiment, the medium according to the invention comprises one or more compounds of formula IX selected from one or more of the group of compounds of formula IX-1 to IX-4, very particularly preferably formula IX-1 To IX-3 compounds,

These parameters have the meanings given in Formula IX.

In another preferred embodiment, the medium comprises one or more compounds of formula IX-3, preferably compounds of formula IX-3-a,

Wherein alkyl and alkyl 'independently represent an alkyl group having 1 to 7 C atoms, preferably 2 to 5 C atoms, from each other.

If the compound of formula IX is used in a liquid crystal medium according to the present application, it is preferably present at a concentration of 20% or less, more preferably 10% or less, and most preferably 5% or less, and for individual (ie Compounds are preferably present at a concentration of 10% or less and more preferably 5% or less.

For the present invention, unless otherwise indicated in individual cases, the following definitions apply in conjunction with the specifications of the ingredients of the composition:
-"Comprising": the concentration of the ingredient in question in the composition is preferably 5% or more, particularly preferably 10% or more, very particularly preferably 20% or more,
-"Consisting mainly of": the concentration of the ingredient in question in the composition is preferably 50% or more, particularly preferably 55% or more and very particularly preferably 60% or more,
-"Consisting essentially of": the concentration of the ingredient in question in the composition is preferably 80% or more, particularly preferably 90% or more and very particularly preferably 95% or more, and
-"Consistently composed entirely of": The concentration of the ingredient in question in the composition is preferably 98% or more, particularly preferably 99% or more and very particularly preferably 100.0%.

This applies to the medium and its components in the form of a composition, which can be components and compounds, and also to components and their components (the compounds). When referring only to the concentration of an individual compound relative to the medium as a whole, the term does include the following meaning: The concentration of the compound in question is preferably 1% or more, particularly preferably 2% or more, and very particularly preferably 4% or above.

For the present invention, "≤" means less than or equal to, preferably less than, and "≥" means greater than or equal to, preferably greater than.

Against the invention

For trans-1,4-cyclohexyl,

Represents a mixture of cis- and trans-1,4-cyclohexyl,
and

Represents 1,4-phenylene.

For the purposes of the present invention, the expression "dielectrically positive compound" means a compound having Δε of> 1.5, the expression "dielectrically neutral compound" means one of which -1.5 £ Δε £ 1.5 and the expression "dielectric negative compound" "Means those in which Δε <-1.5. The capacitance of the resulting mixture is determined here by dissolving 10% of these compounds in the liquid crystal body and in each case at least one test cell with a cell thickness of 20 µm and vertical and parallel surface alignment at 1 kHz. To determine the dielectric anisotropy of these compounds. The measurement voltage is usually 0.5 V to 1.0 V, but it is always lower than the capacitance threshold of the respective liquid crystal mixture under study.

The host mixture for dielectric positive and dielectric neutral compounds is ZLI-4792 and the host mixture for dielectric negative compounds is ZLI-2875, both from Merck KGaA in Germany. The change in the dielectric constant of the host mixture after addition of the compound to be studied and extrapolated to 100% of the compound used, the values for the respective compounds to be studied are obtained. The compound to be studied is dissolved in the host mixture in an amount of 10%. If the solubility of the substance is too low for this purpose, the concentration is gradually halved until the study can be carried out at the required temperature.

The liquid crystal medium according to the present invention (if necessary) may also contain other additives in conventional amounts such as, for example, stabilizers and / or polychromatic (eg, dichroic) dyes and / or palmar dopants. The amount of these additives employed is preferably a total of 0% or more to 10% or less, particularly preferably 0.1% or more to 6% or less, based on the amount of the entire mixture. The concentration of the individual compound used is preferably 0.1 or more to 3% or less. When specifying the concentration and concentration range of liquid crystal compounds in a liquid crystal medium, the concentrations of these and similar additives are generally not considered.

In a preferred embodiment, the liquid crystal medium according to the present invention comprises a polymer precursor, the polymer precursor comprising one or more reactive compounds, preferably a reactive mesogen, and, if necessary, commonly used The amount includes other additives such as, for example, a polymerization initiator and / or a polymerization moderator. The amount of these additives employed is a total of 0% or more to 10% or less, preferably 0.1% or more to 2% or less, based on the amount of the entire mixture. When specifying the concentration and concentration range of the liquid crystal compound in the liquid crystal medium, the concentrations of these and similar additives are not considered.

These compositions are composed of a plurality of compounds, preferably 3 or more to 30 or less, particularly preferably 6 or more to 20 or less and very particularly preferably 10 or more to 16 or less compounds , Which is mixed in a conventional manner. Generally, the required amount of the components used in a smaller amount is dissolved in the components constituting the main ingredients of the mixture. This should be done at high temperatures. If the selected temperature is above the clearing point of the main component, it is particularly easy to observe the completion of the dissolution operation. However, other liquid crystal mixtures can also be prepared in other conventional ways, for example, using a premix or from a so-called "multi-bottle system".

The mixture according to the present invention exhibits a very wide nematic phase range with a clear point of 65 ° C or above, a very favorable capacitance threshold, a relatively high retention ratio value, and is excellent at both -30 ° C and -40 ° C. Low temperature stability. Furthermore, the mixture according to the invention is characterized by a low rotational viscosity γ ₁ .

It is self-evident to those skilled in the art that the medium according to the present invention for VA, IPS, FFS or PALC displays may also include compounds in which, for example, H, N, O, Cl, F have been replaced by corresponding isotopes .

The structure of a liquid crystal display according to the invention corresponds to a common geometric structure, as described, for example, in EP-A 0 240 379.

The liquid crystal phase according to the present invention can be modified by means of suitable additives so that it can be modified in the manner adopted in any type of (for example) IPS and FFS LCD displays that have been disclosed so far.

Table E below indicates possible dopants that can be added to the mixture according to the invention. If the mixtures contain one or more dopants, the (equal) dopants are used in an amount of 0.01% to 4%, preferably 0.1% to 1.0%.

It is shown in Table F below that stabilizers can preferably be added to the mixture according to the invention, for example, in an amount of 0.01% to 6%, in particular 0.1% to 3%.

For the purposes of the present invention, all concentrations are indicated in% by weight, unless explicitly stated otherwise, and with respect to the corresponding mixture as a whole or the components of the mixture as a whole, unless otherwise explicitly indicated. In this context, the term "mixture" describes a liquid crystal medium.

All temperature values indicated in this application, such as, for example, melting point T (C, N), smectic (S) to nematic (N) phase transition T (S, N), and clarification point T (N, I) are All temperature differences are indicated in degrees (° or degrees), respectively, indicated in degrees Celsius (° C) and unless explicitly indicated otherwise.

For the present invention, the term “threshold voltage” refers to a capacitance threshold (V ₀ ), and is also referred to as a Freedericks threshold unless otherwise explicitly indicated.

Unless otherwise explicitly indicated, all physical properties have been measured and measured in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals" (status November 1997, Merck KGaA, Germany) and a temperature of 20 ° C has been applied, And Δn was measured at 436 nm, 589 nm and 633 nm, and De was measured at 1 kHz.

As with switching behavior, electro-optic properties (for example, threshold voltage (V ₀ ) (capacitance measurement)) are measured in a test unit produced by Merck, Japan. The measurement unit has a soda-lime glass substrate and a polyimide alignment layer (SE-1211, dilution ** 26 (mixing ratio 1: 1), all from Japan's Nissan Chemicals) is constructed according to the ECB or VA configuration. The vertical alignment of the liquid crystals has been rubbed perpendicularly to each other. The surface area of the transparent, practically square ITO electrode is 1 cm ² .

Unless otherwise indicated, palm dopants are not added to the liquid crystal mixture used, but the latter are also particularly suitable for applications where this type of doping is necessary.

Rotary permanent magnet method was used to measure the rotational viscosity and the flow viscosity was measured in a modified Ubbelohde viscometer. For liquid crystal mixtures ZLI-2293, ZLI-4792 and MLC-6608 (all products from Merck KGaA, Darmstadtz, Germany), the rotational viscosity values measured at 20 ° C were 161 mPa · s, 133 mPa · s, and 186 mPa · s, and the flow viscosity values (ν) are 21 mm ² · s ^-1 , 14 mm ² · s ^-1, and 27 mm ² · s ^{-1, respectively} .

Unless explicitly stated otherwise, for practical purposes, the dispersion of materials may be conveniently characterized in the following manner used throughout this application. At a temperature of 20 ° C, the birefringence value was measured using a modified Abbé refractometer using a vertically aligned surface of the side of the prism in contact with the material at several fixed wavelengths. At specific wavelength values of 436 nm (spectrum line of the low pressure mercury lamp selected individually), 589 nm (sodium `` D '' line) and 633 nm (wavelength of HE-Ne laser) (used in combination with an attenuator / diffuser to (To prevent damage to the eyes of the observer) measuring the birefringence value. Δn is given at 589 nm and Δ (Δn) is given as Δ (Δn) = Δn (436 nm)-Δn (633 nm) in the following table.

Unless expressly indicated otherwise, the following symbols are used:
V ₀ threshold voltage, capacitance [V], at 20 ° C,
n _e extraordinary refractive index measured at 20 ℃ and 589 nm,
n _o ordinary refractive index measured at 20 ℃ and 589 nm,
Δn Optical anisotropy measured at 20 ° C and 589 nm,
λ wavelength λ [nm],
Δn (λ) Optical anisotropy measured at 20 ℃ and wavelength λ,
Δ (Δn) changes in optical anisotropy as defined below:
Δn (20 ° C, 436 nm)-Δn (20 ° C, 633 nm),
Δ (Δn *) "relative change in optical anisotropy" as defined below: Δ (Δn) / Δn (20 ° C, 589 nm),
ε _^ At 20 ° C and 1 kHz, the electromagnetic induction rate perpendicular to the director,
ε _÷÷ at 20 ° C and 1 kHz, the electromagnetic induction rate parallel to the director,
Δε dielectric anisotropy at 20 ° C and 1 kHz,
T (N, I) or clp. Clarification point [℃],
ν Flow viscosity [mm ² · s ^-1 ] measured at 20 ℃,
Rotational viscosity [mPa × s] of γ ₁ measured at 20 ℃,
k ₁₁ elastic constant, "unrolled" deformation [pN] at 20 ° C,
k ₂₂ elastic constant, "torsional" deformation [pN] at 20 ° C,
k ₃₃ elastic constant, "bending" deformation [pN] at 20 ° C,
Low-temperature stability of the phase determined by LTS in the test unit,
VHR voltage retention ratio ,
A decrease in the ΔVHR voltage retention ratio, and
Relative stability of S _rel VHR.

The following examples illustrate the invention without limiting it. However, the examples show those skilled in the art the concept of better mixtures, among which the compounds to be used and their respective concentrations and combinations thereof are preferred. In addition, these examples illustrate the available properties and combinations of properties.

For the present invention and in the following examples, the structure of the liquid crystal compound is indicated by an acronym, wherein the conversion to the chemical formula is performed according to the following tables A to C. All groups C _n H _{2n + 1} , C _m H _{2m + 1,} and C _l H _{2l + 1} or C _n H _2n , C _m H _2m, and C _l H _2l are straight-chain alkyl or alkenyl groups. In this case, each has n, m, and l C atoms. Preferably, n, m and l are independently 1, 2, 3, 4, 5, 6, or 7. Table A shows the codes of the ring elements used in the nucleus of the compound, Table B lists the bridging units, and Table C lists the meanings of the symbols used for the left-hand and right-hand end groups of the molecule. The acronyms consist of a code for the ring element and optionally a linking group, followed by a first hyphen and a code for the left-hand end group and a second hyphen and a right-hand end group. Code composition. Table D shows illustrative compound structures along with their respective abbreviations.

Table A : Ring Elements
Table B : Bridge unit


Table C : End groups
Among them, each of n and m is an integer, and the three dots "..." are reserved places of other abbreviations from this table.

In addition to the compound of formula B, the mixture according to the invention preferably comprises one or more of the compounds mentioned below.

Use the following abbreviations:
(n, m, k, and l are each an integer independently of each other, preferably 1 to 9, preferably 1 to 7, k and l may also be 0 and preferably 0 to 4, more preferably 0 or 2 and optimally 2, n is preferably 1, 2, 3, 4 or 5, and in the combination "-nO-", n is preferably 1, 2, 3 or 4, preferably 2 Or 4, m is preferably 1, 2, 3, 4 or 5, and in the combination "-Om", m is preferably 1, 2, 3, or 4, more preferably 2 or 4. The combination "-lVm "Preferably" 2V1 ".)

Table D
Exemplary preferred compounds of formula B with high ε _^ :


Exemplary preferred compounds of formula I with high ε _^ :





Exemplary preferred dielectric positive compounds:








Exemplary preferred dielectric neutral compounds:






Exemplary preferred dielectric negative compounds:

Table E shows the palmitic dopants which are preferably used in the mixtures according to the invention.
Table E

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

Table F shows that in addition to the compound of formula B, stabilizers which can be preferably used in the mixtures according to the invention. The parameter n herein represents an integer in the range of 1 to 12. In particular, the phenol derivative shown can be used as an additional stabilizer because it acts as an antioxidant.
Table F

In a preferred embodiment of the invention, the medium according to the invention comprises one or more compounds selected from the group of compounds from Table F, in particular, one or more compounds selected from the group of compounds of the following two formulas

Examples The following examples illustrate the invention without limiting it in any way. However, these physical properties make clear to those skilled in the art the achievable properties and the range in which these properties can be modified. In particular, it is therefore sufficient for those skilled in the art to define combinations of various properties that can be better achieved.

Synthesis Example <br/> Synthesis of an exemplary compound of Formula B (with a high dielectric constant (ε _^ ) perpendicular to the director).

Synthesis Example 1
Synthesis of 4,6-difluoro-3- (4-propyl-cyclohex-1-enyl) -7-trifluoromethoxy-dibenzofuran:

Step 1.1: 3,2 ', 3'-trifluoro-4-trifluoromethoxy-biphenyl-2-phenol

Under a nitrogen atmosphere, 6-bromo-2-fluoro-3-trifluoromethoxyphenol ( 2 ) (100 g, 0.36 mol), potassium carbonate in THF (500 mL) and distilled water (250 mL) (75 g, 0.54 mol), a mixture of ginseng (dibenzylideneacetone) -dipalladium (0) (1.6 g, 1.7 mmol) and CataCXium A (2.0 g, 5.3 mmol) was heated to reflux, followed by the dropwise addition of A solution of 2,3-difluoro-4-phenyldihydroxyboronic acid ( 1 ) (63 g, 0.38 mol) in THF (250 mL). The reaction mixture was heated at reflux temperature overnight. It was then cooled to room temperature and diluted with MTB ether and distilled water. Throughout this application, unless otherwise specified, room temperature and ambient temperature are used synonymously and represent a temperature of about 20 ° C, typically (20 ± 1) ° C. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent methylene chloride, followed by 1-chlorobutane). 3,2 ', 3'-trifluoro-4-trifluoromethoxy-biphenyl-2-phenol ( 3 ) isolated as a brown solid.

Step 1.2: 4,6-Difluoro-3-trifluoromethoxy-dibenzofuran

3,2 ', 3'-trifluoro-4-trifluoromethoxy-biphenyl-2-phenol ( 3 ) (11.0 g, 35 mmol) and potassium phosphate in DMPU (300 mL) monohydrate A mixture of the substances (10.0 g, 44 mmol) was stirred at 110 ° C for 16 hours. It was then cooled to room temperature and diluted with MTB ether and distilled water. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent 1-chlorobutane) to obtain 4,6-difluoro-3-trifluoromethoxy-dibenzofuran ( 4 ) as slightly yellow crystals.

Step 1.3: 1- (4,6-difluoro-7-trifluoromethoxy-dibenzofuran-3-yl) -4-propyl-cyclohexanol

Under a nitrogen atmosphere at -70 ° C, add n-butyllithium (27 mL, 15% in hexane, 43 mmol) to 4,6-difluoro-3-trifluoromethoxy-di A solution of benzofuran ( 4 ) (10.3 g, 34 mmol) in THF (100 mL). After 1 hour, a solution of 4-propylcyclohexanone (6.0 g, 43 mmol) in THF (100 mL) was added, and the reaction mixture was stirred at -70 ° C for 2 hours. It was then allowed to warm to room temperature and stirred for another 72 hours. The reaction was stopped at 0 ° C with distilled water and hydrochloric acid (2 N ) and diluted with MTB ether. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent 1-chlorobutane) to obtain 1- (4,6-difluoro-7-trifluoromethoxy-dibenzofuran-3-yl)-as yellow crystals. 4-propyl-cyclohexanol ( 5 ).

Step 1.4: 4,6-Difluoro-3- (4-propyl-cyclohex-1-enyl) -7-trifluoromethoxy-dibenzofuran

1- (4,6-difluoro-7-trifluoromethoxy-dibenzofuran-3-yl) -4-propyl-cyclohexanol ( 5 ) in toluene (100 mL) ( A mixture of 7.9 g, 15 mmol) and toluene-4-sulfonic acid monohydrate (300 mg, 1.7 mmol) was heated in a Dean Stark trap at reflux temperature overnight. It was then cooled to room temperature and diluted with MTB ether and distilled water. The aqueous phase was separated and extracted with MTB ether. The combined organic phases were washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (solvent 1-chlorobutane). The crude product was subsequently recrystallized from methanol / heptane and ethanol to produce 4,6-difluoro-3- (4-propyl-cyclohex-1-enyl) -7-trifluoromethoxy-dibenzofuran ( B-2-A ) is a colorless crystal. This compound has the following phase characteristics:
K 62 ° C S _A 121 ° C I.

Synthesis Example 2
Synthesis of 4,6-difluoro-3- (4-propyl-cyclohexyl) -7-trifluoromethoxy-dibenzofuran:

Step 2.1: 4,6-difluoro-3- (4-propyl-cyclohexyl) -7-trifluoromethoxy-dibenzofuran

and

4,6-difluoro-3- (4-propyl-cyclohex-1-enyl) -7-trifluoro in toluene (30 mL) in the presence of a catalytic amount of activated carbon on palladium Methoxy-dibenzofuran ( B-2-A ) (2.4 g, 6 mmol) was reacted with hydrogen for 24 hours. The reaction mixture was concentrated in vacuo and the residue was purified by silica chromatography (solvent 1-chlorobutane) to give the trans isomer of the desired product. After subsequent recrystallization from ethanol and heptane, 4,6-difluoro-3- (4-propyl-cyclohexyl) -7-trifluoromethoxy-dibenzofuran ( B -1-A ).
This compound has the following phase characteristics:
T _g -49 ℃ K 69 ℃ S _A 86 ℃ N 98 ℃ I.

Synthesis Example 3
Synthesis of 4,6-difluoro-3- (4-propyl-cyclohex-1-enyl) -7-trifluoromethyl-dibenzofuran:

Similar to 4,6-difluoro-3- (4-propyl-cyclohex-1-enyl) -7-trifluoromethoxy-dibenzofuran ( B-2-A ), from 6-bromo Began synthesis of 2,6-difluoro-3- (4-propyl-cyclohexyl-2-fluoro-3-trifluoromethylphenol and 2,3-difluoro-4-phenyldihydroxyboronic acid ( 1 ) 1-alkenyl) -7-trifluoromethyl-dibenzofuran ( B-2-B ). The crude product was recrystallized from heptane to obtain 4,6-difluoro-3- (4-propyl-cyclohex-1-enyl) -7-trifluoromethyl-dibenzofuran ( B-2-B ) Of colorless crystals. This compound has the following phase characteristics:
K 89 ° C S _A 108 ° C I.

Synthesis Example 4
Synthesis of 4,6-difluoro-3- (4-propyl-cyclohexyl) -7-trifluoromethyl-dibenzofuran:

This compound was prepared similarly to the compound of Synthesis Example 2. It has the following phase characteristics:
K 116 ° C S _A (64 ° C) N (84.4 ° C) I.

Synthesis Example 5
Synthesis of 4,6,7-trifluoro-3- (4-propyl-cyclohex-1-enyl) dibenzofuran:

This compound was prepared similar to the compounds of Synthesis Examples 1 and 3. It has the following phase characteristics:
K 103 ° C N (93.0 ° C) I.

Synthesis Example 6
Synthesis of 4,6,7-trifluoro-3- (4-propyl-cyclohexyl) dibenzofuran:

This compound was prepared similar to the compounds of Synthesis Examples 2 and 4. It has the following phase characteristics:
K 123 ° C N (106.4 ° C) I.

Compounds of formula B-1 are similarly prepared

among them

Compounds of formula B-2 are similarly prepared

among them

Compound Examples <br/> Exemplary compounds having a high dielectric constant (ε _^ ) perpendicular to the director and a high average dielectric constant (ε _av. ) _Are exemplified in the following compound examples.

Compound Examples B1.1 to B1.3
Compounds of formula B-1 are for example
.
This compound (CB-3-OT) has a glass transition temperature of -49 ° C, a melting point of 69 ° C, a clearing point extrapolated from 102 ° C (5% in ZLI-4792), T _g -49 ° C K 69 ° C Phase sequence of S _A 86 ℃ N 98 ℃ I, Δε of 1.7 and ε _{^ of} 10.5.

Compound Examples B1.4 to B1.6

This compound (LB-3-OT) has a melting point of 62 ° C, a clearing point extrapolated from 97 ° C (5% in ZLI-4792), a phase sequence of K 62 ° C S _A 121 ° C I, Δε of 2.5, and 10.5 Of ε _^ .

This compound (LB-3-T) has a melting point of 89 ° C, a phase sequence of K 89 ° S _A 108 ° C I, a clearing point extrapolated from 83 ° C (10% in ZLI-4792), a Δε of 3.5, and 12.5 Of ε _^ .

Examples of additional compounds 1.1 and 1.2 <br/> The compounds of formula I-1 are for example

This compound (B-2O-O5) having a melting point of 57 ℃, Δε -13.7 17.9 of the even and ε _av.

This compound (B-4O-O5) has better similar properties.

Examples of additional compounds 2.1 and 2.2 <br/> Two compounds of formula I-2 are, for example, the following:

This compound (B-5O-OT) having a melting point of 68 deg.] C, Δε of -3.7 and even only of ε 18.6 _av..

This compound (B-6O-OT) had a melting point of 72 ° C.

Examples of additional compounds 3.1 to 3.6 <br/> Other compounds of formula I-1 are for example

This compound (B-4-4) had a melting point of 38 ° C.

This compound (B-5-2V) has a melting point of 35 ° C.

This compound (B-V2-2V) has a melting point of 60 ° C.

This compound (B-2-O2) has a melting point of 60 ° C.

This compound (B-3-O3) had a melting point of 54 ° C.

This compound (B-3-O2V) has a melting point of 50 ° C.

Examples of additional compounds 4.1 to 4.11 <br/> Other compounds of formula I-2 are for example

This compound (B-3-F) had a melting point of 76 ° C.

This compound (B-5-F) had a melting point of 42 ° C.

This compound (B-5-T) has a melting point of 46 ° C.

This compound (B-5-OT) has a melting point of 46 ° C.

This compound (B-2O-F) had a melting point of 114 ° C.

This compound (B-5O-F) has a melting point of 65 ° C.

This compound (B-5O-Cl) has a melting point of 51 ° C.

This compound (B-4O-T) had a melting point of 81 ° C.

This compound (B-5O-T) had a melting point of 74 ° C.

This compound (B-6O-T) had a melting point of 76 ° C.

This compound (B-V2O-OT) has a melting point of 87 ° C.

Examples of additional compounds 5.1 to 5.3 <br/> The compound of formula I (where n is 1) is for example

This compound (CB-3-O4) has a phase range of K 76 ° C N 145.6 ° C I.

This compound (PB-3-O4) has a phase range of K 122 ° N (121.6 ° C) I.

This compound (GB-4-O2) has a phase range of K 69 ° C N (34.5 ° C) I.

Examples of mixtures <br/> Exemplary mixtures are disclosed below.

Comparative Example A
The following mixtures (CE-A) were prepared and studied.
Note: tbd: To be determined


Table 1
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and
tbd: To be determined
Table 1 ( continued )
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and tbd: To be determined.

These mixtures (mixtures A-1 to A-6) have good dielectric ratios (ε _^ / Δε), good (γ ₁ / k ₁₁ ) ratios and are characterized by excellent transmittance and display in FFS displays Very short response time. In addition, it shows excellent deep temperature stability up to a temperature of at least -20 ° C.
Table 1 ( continued )
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and tbd: To be determined.


Table 1 ( continued )
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and tbd: To be determined.


Table 1 ( continued )
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and tbd: To be determined.


Table 1 ( continued )
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and tbd: To be determined.

Comparative Example B
The following mixtures (CE-B) were prepared and studied.
Note: tbd: To be determined


Table 2
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and
tbd: To be determined.


Table 2 ( continued )
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and tbd: To be determined.

These mixtures (mixtures B-1 to B-6) have good dielectric ratio (ε _^ / Δε), good (γ ₁ / k ₁₁ ) ratio and are characterized by excellent transmittance and display in FFS displays Very short response time. In addition, it shows excellent deep temperature stability up to a temperature of at least -20 ° C.

Comparative Example C
The following mixtures (CE-C) were prepared and studied.
Note: tbd: To be determined.


Table 3
Note: All extrapolated values are at 20 ° C.
*: [MPa × s / pN] and
tbd: To be determined.

Example 3
The following mixtures (M-3) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-3) has a dielectric ratio (ε _{^ /} Δε) of 0.87, a ratio of (γ ₁ / k ₁₁ ) of 4.28 mPa × s / pN and is characterized by excellent transmission in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 4
The following mixtures (M-4) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-4) has a dielectric ratio (ε _{^ /} Δε) of 1.02, a ratio of (γ ₁ / k ₁₁ ) of 4.48 mPa × s / pN and is characterized by excellent transmittance in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 5
The following mixtures (M-5) were prepared and studied.
Note: tbd: To be determined

This mixture (mixture M-5) has a dielectric ratio (ε _{^ /} Δε) of 0.73, a ratio of (γ ₁ / k ₁₁ ) of 4.44 mPa × s / pN and is characterized by excellent transmission in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 6
The following mixtures (M-6) were prepared and studied.
Note: tbd: To be determined

Example 7
The following mixtures (M-7) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-7) has a dielectric ratio (ε _{^ /} Δε) of 0.80, a ratio of (γ ₁ / k ₁₁ ) of 4.32 mPa × s / pN and is characterized by excellent transmission in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 8
The following mixtures (M-8) were prepared and studied.
Note: tbd: to be determined and *: [mPa × s / pN]. This mixture (Mixture M-8) is characterized by good transmittance in FFS displays, shows short response time, and has excellent low temperature stability.

Example 9
The following mixtures (M-9) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-9) is characterized by excellent transmittance in FFS displays, shows very short response time, and has excellent low temperature stability.

Example 10
The following mixtures (M-10) were prepared and studied.
Note: tbd: To be determined

This mixture (mixture M-10) has a dielectric ratio (ε _{^ /} Δε) of 0.86, a ratio of (γ ₁ / k ₁₁ ) of 4.11 mPa × s / pN and is characterized by excellent transmission in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 11
The following mixtures (M-11) were prepared and studied.
Note: tbd: To be determined

This mixture (mixture M-11) has a dielectric ratio (ε _{^ /} Δε) of 0.77, a ratio of (γ ₁ / k ₁₁ ) of 4.17 mPa × s / pN and is characterized by excellent transmittance in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 12
The following mixtures (M-12) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-12) has a dielectric ratio (ε _{^ /} Δε) of 1.26, a ratio of (γ ₁ / k ₁₁ ) of 4.97 mPa × s / pN and is characterized by excellent transmission in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 13
The following mixtures (M-13) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-13) has a dielectric ratio (ε _{^ /} Δε) of 1.09, a ratio of (γ ₁ / k ₁₁ ) of 5.0 mPa × s / pN and is characterized by excellent transmittance in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 14
The following mixtures (M-14) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-14) has a good dielectric ratio (ε _^ / Δε), a good (γ ₁ / k ₁₁ ) ratio and is characterized by excellent transmission in an FFS display, showing a very short response time , And has excellent low temperature stability.

Example 15
The following mixtures (M-15) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-15) has a dielectric ratio (ε _{^ /} Δε) of 0.89, a ratio of (γ ₁ / k ₁₁ ) of 4.31 mPa × s / pN and is characterized by excellent transmission in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 16
The following mixtures (M-16) were prepared and studied.
Note: tbd: To be determined

This mixture (Mixture M-16) has a dielectric ratio (ε _{^ /} Δε) of 0.93, a ratio of (γ ₁ / k ₁₁ ) of 4.36 mPa × s / pN and is characterized by excellent transmission in an FFS display , Shows very short response time, and has excellent low temperature stability.

Example 17
The following mixtures (M-17) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-17) is characterized by excellent transmission in FFS displays, shows very short response times, and has good low temperature stability.

Example 18
The following mixtures (M-18) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-18) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 19
The following mixtures (M-19) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-19) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 20
The following mixtures (M-20) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-20) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 21
The following mixtures (M-21) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-21) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 22
The following mixtures (M-22) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-22) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 23
The following mixtures (M-23) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-23) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 24
The following mixtures (M-24) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-24) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 25
The following mixtures (M-25) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-25) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 26
The following mixtures (M-26) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-26) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 27
The following mixtures (M-27) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-27) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 28
The following mixtures (M-28) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-28) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 29
The following mixtures (M-29) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-29) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 30
The following mixtures (M-30) were prepared and studied.
Note: tbd: to be measured and *: [mPa × s / pN] This mixture (Mixture M-30) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 31
The following mixtures (M-31) were prepared and studied.
Remarks: tbd: to be measured and *: [mPa × s / pN] This mixture (Mixture M-31) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 32
The following mixtures (M-32) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-32) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 33
The following mixtures (M-33) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-33) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 34
The following mixtures (M-34) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-34) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 35
The following mixtures (M-35) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-35) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 36
The following mixtures (M-36) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-36) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 37
The following mixtures (M-37) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-37) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 38
The following mixtures (M-38) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-38) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 39
The following mixtures (M-39) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-39) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 40
The following mixtures (M-40) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-40) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 41
The following mixtures (M-41) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-41) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 42
The following mixtures (M-42) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-42) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 43
The following mixtures (M-43) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-43) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 44
The following mixtures (M-44) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-44) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 45
The following mixtures (M-45) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-45) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 46
The following mixtures (M-46) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-46) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 47
The following mixtures (M-47) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-47) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 48
The following mixtures (M-48) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-48) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 49
The following mixtures (M-49) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-49) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 50
The following mixtures (M-50) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-50) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 51 (MDA-17-2436)
The following mixtures (M-51) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-51) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 52
The following mixtures (M-52) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-52) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 53
The following mixtures (M-53) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-53) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 54
The following mixtures (M-54) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-54) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 55
The following mixtures (M-55) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-55) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 56
The following mixtures (M-56) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-56) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 57
The following mixtures (M-57) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-57) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 58
The following mixtures were prepared and studied (M-58).
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-58) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 59
The following mixtures (M-59) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-59) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 60
The following mixtures (M-60) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-60) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 61
The following mixtures (M-61) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-61) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 62
The following mixtures (M-62) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-62) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 63
The following mixtures (M-63) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-63) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 64
The following mixtures (M-64) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-64) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 65
The following mixtures (M-65) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-65) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 66
The following mixtures (M-66) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-66) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 67
The following mixtures (M-67) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-67) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 68
The following mixtures were prepared and studied (M-68).
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-68) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 69
The following mixtures (M-69) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-69) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 70
The following mixtures (M-70) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-70) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 71
The following mixtures (M-71) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-71) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 72
The following mixtures (M-72) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-72) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 73
The following mixtures (M-73) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-73) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 74
The following mixtures were prepared and studied (M-74).
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-74) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 75
The following mixtures (M-75) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-75) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 76
The following mixtures (M-76) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-76) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 77
The following mixtures (M-77) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-77) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 78
The following mixtures were prepared and studied (M-78).
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-78) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 79
The following mixtures (M-79) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-79) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 80
The following mixtures (M-80) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-80) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 81
The following mixtures (M-81) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-81) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 82
The following mixtures (M-82) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-82) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 83
The following mixtures (M-83) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-83) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Example 84
The following mixtures were prepared and studied (M-84).
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-84) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 85
The following mixtures (M-85) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-85) is characterized by excellent transmission in FFS displays and good low temperature stability.

Example 86
The following mixtures (M-86) were prepared and studied.
Remarks: tbd: to be determined and *: [mPa × s / pN]

This mixture (Mixture M-86) is characterized by excellent transmittance in FFS displays and good low temperature stability.

Claims (15)

A liquid crystal medium having a nematic phase and a dielectric anisotropy (De) of 0.5 or more, characterized in that it contains one or more compounds of formula B among them Express Express , N represents 1 or 2, R ¹ represents alkyl, alkoxy, fluorinated alkyl, fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl, or fluorinated alkenyl and X ¹ represents F , Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy. If the medium of claim 1, which contains one or more compounds of formula B, these compounds are selected from the group of compounds of formula B-1 and B-2 Among them, these parameters have their respective meanings as given in claim 1. The medium of claim 1 or 2 which further comprises one or more compounds of formula I: among them Express , Express n represents 0 or 1, and R ¹¹ and R ¹² independently of each other represent an alkyl group, alkoxy group, fluorinated alkyl group or fluorinated alkoxy group, alkenyl group, alkenyl group, alkoxy group having 2 to 7 C atoms Alkyl or fluorinated alkenyl, and either R ¹¹ represents R ¹ and or R ¹² represents X ¹ , R ¹ represents an alkyl, alkoxy, fluorinated alkyl or Fluorinated alkoxy; alkenyl, alkenyl, alkoxyalkyl or fluorinated alkenyl and preferably alkyl or alkenyl having 2 to 7 C atoms, and X ¹ represents F, Cl, fluorine Alkylated, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, excluding compounds of formula B. If the medium of any one of claims 1 to 3, which comprises one or more compounds selected from the group of compounds of formulae II and III, Wherein R ² represents an alkyl group, alkoxy group, fluorinated alkyl group or fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl group, alkenyl group, alkoxyalkyl group having 2 to 7 C atoms Or fluorinated alkenyl, and Represents each other independently of each other L ²¹ and L ²² represent H or F, X ² represents halogen, a halogenated alkyl or alkoxy group having 1 to 3 C atoms, or a halogenated alkenyl or alkenyl group having 2 or 3 C atoms, and m represents 0 , 1, 2 or 3, R ³ represents an alkyl group, alkoxy group, fluorinated alkyl group or fluorinated alkoxy group having 1 to 7 C atoms; an alkenyl group or alkenyl group having 2 to 7 C atoms , Alkoxyalkyl or fluorinated alkenyl, and Independently of each other for L ³¹ and L ³² independently represent H or F, X ³ represents halogen, a halogenated alkyl or alkoxy group having 1 to 3 C atoms, or a halogenated alkenyl or alkenyl group having 2 or 3 C atoms, F, Cl, -OCF ₃ , -OCHF ₂ , -O-CH ₂ CF ₃ , -O-CH = CF ₂ , -O-CH = CH ₂ or -CF ₃ , Z ³ represents -CH ₂ CH _2- , _{-CF 2 CF 2 -, - COO-} , trans -CH = CH-, trans - CF = CF -, - CH 2 O- or a single bond, and n represents 0, 1 or 3. The liquid crystal medium of any one of claims 1 to 4, which comprises one or more dielectric neutral compounds selected from the group of formulae IV and V: Wherein R ⁴¹ and R ⁴² independently have the meanings as indicated in claim 4 for R ² under formula II, and Independently of each other Appears twice, these are also shown independently of each other Z ⁴¹ and Z ⁴² independently of one another and, if Z ⁴¹ occurs twice, also these independently of one another denote _{-CH 2 CH 2 -, - COO-} , trans -CH = CH-, trans - CF = CF- , -CH ₂ O-, -CF ₂ O-, -C≡C- or a single bond, p represents 0, 1 or 2, R ⁵¹ and R ⁵² independently of each other have the meanings given for R ⁴¹ and R ⁴² One of them, to , If present, each represents each other independently Z ⁵¹ to 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 These represent 0 or 1 independently of each other. The liquid crystal medium of claim 5, wherein it comprises one or more compounds selected from the group of formulae VI to IX: Wherein R ⁶¹ represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkenyl group having 2 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or An unsubstituted alkenyloxy group having 2 to 6 C atoms, R ⁶² represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or Unsubstituted alkenyloxy group having 2 to 6 C atoms, and l represents 0 or 1, R ⁷¹ represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkyl group having 2 to 7 C atoms A substituted alkenyl group, R ⁷² represents an unsubstituted alkyl group having 1 to 7 C atoms, an unsubstituted alkoxy group having 1 to 6 C atoms, or an unsubstituted alkyl group having 2 to 6 C atoms. Substituted alkenyloxy, Express , or R ⁸¹ represents an unsubstituted alkyl group having 1 to 7 C atoms or an unsubstituted alkenyl group having 2 to 7 C atoms, and R ⁸² represents an unsubstituted alkyl group having 1 to 7 C atoms An unsubstituted alkoxy group having 1 to 6 C atoms or an unsubstituted alkoxy group having 2 to 6 C atoms, preferably 2, 3 or 4 C atoms, Express , or , Z ⁸ represents-(C = O) -O-, -CH ₂ -O-, -CF ₂ -O- or -CH ₂ -CH _2- , o represents 0 or 1, R ⁹¹ and R ⁹² are independent of each other Has the meaning given above for R ⁷² , Express or , P and q independently represent 0 or 1 and (p + q) preferably represents 0 or 1. If the medium of any one of claims 1 to 6, wherein the total concentration of the compound of formula B in the medium as a whole is 1% or more to 60% or less. The medium of any one of claims 1 to 7, which further comprises one or more palmitic compounds and / or stabilizers. An electro-optical display or an electro-optical component, characterized in that it comprises a liquid crystal medium as in any one of claims 1 to 8. The display as claimed in claim 9, wherein it is based on the IPS- or FFS mode. The display of claim 9 or 10, which comprises an active matrix addressing device. A use of a medium according to any one of claims 1 to 8 in an electro-optical display or in an electro-optical module. A method for preparing a liquid crystal medium according to any one of claims 1 to 8, characterized in that one or more compounds of formula B are mixed with one or more additional mesogen compounds and optionally one or more additives. A compound of formula B These other parameters have their respective meanings as given under claim B in claim 1. A method for preparing a compound of formula B as given in claim 14, characterized in that it comprises converting a fluorinated biphenol compound (e.g. compound 3 of the synthetic reaction diagram 1) into a fluorinated dibenzofuran compound (e.g. Step of synthesizing the compound 4 ) in FIG. 1.