DE19528107A1 - In-plane-switching electro=optical LCD with short switching times - Google Patents

Abstract

An electrooptical LCD has an orientation film, the field of which has a significant component parallel to the liquid crystal (LC) layer, and an LC medium with positive dielectric anisotropy, which contains mesogenic cpd(s). with a 3,4,5-trifluorophenyl gp. (Ph.3F) and/or mesogenic cpd(s). contg. a unit of formula T<1> - Z - T<2>-CN (A); T<1> = a gp. of formula (B); and T<2> = a gp. of formula (C); A = O or CH; Z = -COO- or a single bond; L<1> = F or, if A = O, may also = H; L<2> = H or F. Also claimed is a liquid crystal medium with positive dielectric anisotropy.

Description

The invention relates to an electro-optical liquid crystal display with a Reorientation layer for reorientation of the liquid crystals whose Field a significant component parallel to the liquid crystal layer comprising a liquid-crystalline medium having a positive dielectric Anisotropy, wherein the medium comprises at least one mesogenic compound containing a group of the formula I:

wherein
L₁ and L₂ each independently represent H or F.

In conventional liquid crystal displays (TN, STN, OMI, AMD-TN) For example, the electric fields for reorientation become substantially generated perpendicular to the liquid crystal layer.

International Patent Application WO 91/10936 discloses a liquid crystal display disclosed in which the electrical signals are generated so who that the electric fields are a significant component parallel to Liquid crystal layer have (IPS, in-plane switching). The principles, to operate such a display, z. As described by R.A. Soref in Journal of Applied Physics, Vol. 45, No. 12, p. 5466-5468 (1974).

In EP 0 588 568 various possibilities for driving are provided such a display.

These IPS displays can work with liquid crystalline materials either with a positive or a negative dielectric anisotropy (Δε ≠ 0) are operated. With the hitherto known materials are in  However, IPS displays have relatively high threshold voltages and long switching achieved times. It was therefore the object of liquid-crystalline materials which are suitable for IPS displays relatively low threshold to achieve voltages and short switching times.

This problem has surprisingly been solved by the use of liquid crystalline materials which ent at least one compound ent which have a 4- (dioxanyl) benzonitrile group.

Such compounds are for. B. known from US 4,332,354, US 4,704,227 and EP 0 090 183.

There is no indication, however, that with the help of these substances the threshold voltages and switching times of IPS displays verbes can.

The invention thus relates to an electro-optical liquid crystal Display with a reorientation layer for reorientation of the liquid crystals whose field is a significant component parallel to the liquid crystal having stable layer containing a liquid crystalline medium with positive dielectric anisotropy, wherein the medium is at least one mesogenic Contains compound having a group of the formula I:

wherein
L₁ and L₂ each independently represent H or F.

Preferred embodiments are IPS displays where

• a) the medium contains at least one compound of the formula I; wherein
  R₁ is H, an unsubstituted, an alkyl or alkenyl radical having from 1 to 15 carbon atoms, which is monosubstituted by CN or CF₃ or at least monosubstituted by halogen, in which radicals one or more CH₂ groups are each independently denoted by -O- , -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- may be replaced so that O atoms are not directly linked to one another,
  Q is a radical of the formula - (O) _q - (CH₂) _r - (CF₂) _s -worin
  q is 0 or 1
  r is 0, or an integer between 1 and 6 is and
  s is an integer between 0 and 6,
  XF or Cl, in case = 1-6 also H, and
  p 0, 1 or 2,
  A₁ and A₂ each independently
  • (a) 1,4-cyclohexenylene or trans-1,4-cyclohexylene radical, in which also one or more non-adjacent CH₂ groups may be replaced by -O- and / or -S-,
  • (b) 1,4-phenylene radical, in which also one or two CH groups may be replaced by N,
  • (c) radical from the group consisting of 1,4-bicyclo (2,2,2) octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, deca-hydronaphthalene-2,6-diyl and 1,2 , 3,4-tetrahydro-naphthalene-2,6-diyl,
• where the radicals (a) and (b) can be substituted by one or two fluorine,
  L₃ and L₄ H or F,
  Z₁ and Z₂ are each independently -CO-O-, -O-CO-, -CH₂O-, -OCH₂-, -CH₂CH₂-, -CH = CH-, -C≡C- or a single bond, one of the radicals Z₁ and Z₂ also - (CH₂) ₄- or -CH = CH-CH₂CH₂-, and
  m 0, 1 or 2
  means;
• b) the medium contains at least one compound of formula II wherein
  L₁ and L₂ have the meaning indicated,
  R₂ has the meaning given for R₁,
  A₃ and A₄ each independently have the meaning given for A₁ and A₂,
  Z₃ and Z₄ each independently have the meaning given for Z₁ and Z₂, and
  n is 0, 1 or 2;
• c) the medium has a dielectric anisotropy Δε <8.5, before preferably between 8, 6 and 14, in particular between 8.7 and 13.5;
• d) the medium contains at least one compound of formula III, R₃- (A₅-Z₅) _o -A₆-R₄ (III) wherein
  R₃ and R₄ each independently of one another have the meaning given for R₁,
  A₅ and A₆ each independently have the meaning given for A₁ and A₂,
  Each independently of one another has the meaning given to Z₁ and Z₂, and
  o is 1, 2 or 3;
• e) the medium contains at least one compound of formula IV wherein
  R₅ has the meaning given for R₆, means
  Z represents a single bond or -COO-, and
  L₅ and L₆ are each F or H.

Further preferred is an IPS display, wherein the picture elements by means of Active matrix to be controlled.

Another object of the invention is a liquid-crystalline medium with positive dielectric anisotropy, which has at least one verbin of formula I and at least one compound having a group of Contains formula II, in particular which

• - 60 to 95, preferably 75 to 90 wt .-% of at least one Compound of the formula I,
• - 5 to 25, preferably 7 to 20 wt .-% of at least one Compound of the formula II,
• - 0 to 10, preferably 25 to 50 wt .-% of at least one Compound of formula III, and  
• - 1 to 10, preferably 2 to 8 wt .-% of a compound of Formula IV,

contains.

Preferably, the medium contains

• - contains at least one compound selected from the formulas Ia, Ib and Ic
• contains at least one compound selected from the formulas IIa to IIc,
• optionally containing at least one compound selected from the formulas IIIa, IIIb and IIIc, such as
• contains at least one compound selected from the formulas IVa to IVd, wherein Z₂-COO-, -CH₂CH₂- or a single bond
  mean, and R₁, R₂, R₃, R₄, R₅, L₁ to L₆ have the meaning given.

The liquid-crystalline media according to the invention generally have a birefringence (Δn) <0.12, preferably Δn is between 0.07 and 0.1, in particular between 0.075 and 0.09.

The flow viscosity (at 20 ° C.) of the materials according to the invention is generally less than 30 mm 2 s ^-1 , in particular between 15 and 25 mm 2 s ^-1 . The rotational viscosity of the media according to the invention is generally none of 200 mPa · s, preferably less than 150 mPa · s, in particular between 80 and 120 mPa · s. The specific resistance of the materials according to the invention is usually between 5 × 10¹⁰ and 5 × 10¹³ Ω · cm at 20 ° C.

It has been found that even a relatively low proportion of Verbindun gene of the dioxane derivatives in admixture with conventional Flüssigkristallmateria but in particular with one or more compounds of the Formula I, III and / or IV to a considerable lowering of the threshold voltage and leads to fast switching times, while at the same time wide nematic phases with low transition temperatures smectic-nema be observed. The compounds of formulas I to IV are colorless, stable and with each other and with other Flüssigkristallmate good miscible.

The term "alkyl" includes straight-chain and branched alkyl groups with 1-7 carbon atoms, in particular the straight-chain groups methyl, Ethyl, propyl, butyl, pentyl, hexyl and heptyl. Group with 2-5 carbon Atoms are generally preferred.

The term "alkenyl" includes straight and branched alkenyl groups with 2-7 carbon atoms, in particular the straight-chain Groups. Especially alkenyl groups are C₂-C₇-1E-alkenyl, C₄-C₇- 3E-alkenyl, C₅-C₇-4-alkenyl, C₆-C₇-5-alkenyl and C₇-alkenyl, esp in particular C₂-C₇-1E-alkenyl, C₄-C₇-3E-alkenyl and C₅-C₇-4-alkenyl. Examples of preferred alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl, 6-heptenyl and the like. Groups of up to 5 carbon atoms are generally preferred.

The term "fluoroalkyl" preferably includes straight-chain groups terminal fluorine, d. H. Fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl. Other Positions of the fluorine are not excluded.

The term "oxaalkyl" preferably includes straight-chain radicals of the formula C _n H _{2n + 1} -O- (CH₂) _m , wherein n and m are each independently 1 to 6. Preferably, n = 1 and m is 1 to 6.

By a suitable choice of the meanings of R₁ and R₅ An Speech times, the threshold voltage, the steepness of the transmissions characteristics, etc. are modified in the desired manner. For example lead 1E-alkenyl, 3E-alkenyl, 2E-Alkenyloxyreste and the like, usually to shorter response times, improved nematic tendencies and a higher ratio of elastic Constants k₃₃ (bend) and k₁₁ (splay) compared to alkyl or alkoxy residues. 4-alkenyl radicals, 3-alkenyl radicals and the like result in general lower threshold voltages and smaller values of k₃₃ / k₁₁ in comparison to alkyl and alkoxy radicals.

A group -CH₂CH₂- in Z₁ or Z₂ generally leads to higher Values of k₃₃ / k₁₁ compared to a simple covalent bond. Higher values of k₃₃ / k₁₁ allow z. B. flatter transmission Kennenn lines in TN cells with 90 ° twist (to obtain shades of gray) and steeper transmission characteristics in STN, SBE and OMI cells (higher Multiplexability) and vice versa.

The optimum ratio of the compounds of the formulas I and II + III + IV depends largely on the desired properties, from the Choice of the components of the formulas I, II, III and / or IV and of the choice further optionally present components. suitable Quantity ratios within the range specified above can be easily determined on a case-by-case basis.

The total amount of compounds of formulas 1 to IV in the inventions The mixtures according to the invention are not critical. The mixtures can therefore one or more other components included for optimization different properties. The observed effect on the response times and the threshold voltage, however, is generally greater higher is the total concentration of compounds of formulas 1 and II.  

In a particularly preferred embodiment, the inventions contain According to the invention media compounds of formula IV (preferably II and / or III), in which Q-X represents OCF₃ or OCHF₂. A cheap one synergistic action with the compounds of formula I leads to particularly advantageous properties.

The liquid-crystalline media of the invention preferably contain in addition to one or more compounds of the formulas I, II, II and IV as further constituents 2 to 40, in particular 4 to 30 components. All more preferably, these media contain one or more besides Compounds of the invention 7 to 25 components. These others Ingredients are preferably selected from nematic or nematogenic (monotropic or isotropic) substances, in particular Substances from the classes of the azoxybenzenes, Benzylidenaniline, Biphenyls, terphenyls, phenyl or cyclohexyl benzoates, cyclohexane carboxylic acid phenyl or cyclohexyl esters, phenyl or cyclohexyl esters cyclohexylbenzoic acid, phenyl or cyclohexyl esters of cyclo hexylcyclohexanecarboxylic acid, cyclohexyl-phenylester of benzoic acid, cyclohexanecarboxylic acid or cyclohexylcyclohexanecarboxylic acid, Phenylcyclohexanes, cyclohexylbiphenyls, phenylcyclohexylcyclohexanes, Cyclohexylcyclohexanes, cyclohexylcyclohexylcyclohexenes, 1,4-bis-cyclo hexylbenzenes, 4,4'-bis-cyclohexylbiphenyls, phenyl or cyclohexyl pyrimidines, phenyl or cyclohexylpyridines, phenyl or cyclohexyl dioxanes, phenyl or cyclohexyl-1,3-dithiane, 1,2-diphenylethane, 1,2-dicyclohexylethane, 1-phenyl-2-cyclohexylethane, 1-cyclohexyl 2- (4-phenylcyclohexyl) ethanes, 1-cyclohexyl-2-biphenylylethanes, 1-phenyl-2-cyclohexyl-phenylethane, optionally halogenated Stilbenes, benzylphenyl ethers, tolans and substituted cinnamic acids. The 1,4-phenylene groups in these compounds may also be fluorinated.

The most important as further constituents of inventive media in Questioning compounds can be represented by the formulas 1, 2, 3, 4 and 5 characterize:

R'-L-E-R '' (1)

R'-L-COO-E-R '' (2)

R'-L-OOC-E-R '' (3)

R'-L-CH₂CH₂-E-R '' (4)

R'-L-C≡C-E-R "(5).

In the formulas 1, 2, 3, 4 and 5, L and E denote the same or ver can be separate, each independently a bivalent The residue of -Phe-, -Cyc-, -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -Pyr-, -Dio, -G-Phe and -G-Cyc and their mirror images formed group, where Phe is unsubstituted or fluorine-substituted 1,4-phenylene, Cyc trans-1,4-cyclohexylene or 1,4-cyclohexylene, Pyr pyrimidine-2,5-diyl or pyridine-2,5-diyl, dio-1,3-dioxane-2,5-diyl and G 2- (trans-1,4-cyclo hexyl) -ethyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl or 1,3-dioxane-2,5-diyl mean.

Preferably, one of L and E is Cyc, Phe or Pyr. E is present preferably Cyc, Phe or Phe-Cyc. Preferably, the inventions contain According to the media one or more components selected from the compounds of formulas 1, 2, 3, 4 and 5 wherein L and E are selected are from the group Cyc, Phe and Pyr and at the same time one or more Components selected from the compounds of the formulas 1, 2, 3, 4 and 5, wherein one of the radicals L and E is selected from the group Cyc, Phe and Pyr and the other rest is selected from the group -Phe-Phe, -Phe-Cyc, -Cyc-Cyc, -G-Phe and -G-Cyc-, and given if one or more components selected from the compounds of the formulas 1, 2, 3, 4 and 5, wherein the radicals L and E are selected from the group -Phe-Cyc, -Cyc-Cyc, -G-Phe and -G-Cyc-.

R 'and R "in a smaller subgroup of the compounds mean Formulas 1, 2, 3, 4 and 5 are each independently alkyl, alkenyl, Alkoxy, alkoxyalkyl, alkenyloxy or alkanoyloxy of up to 8 carbon atoms. In the following, this smaller subgroup is called group A.  and the compounds are described with sub-formulas 1a, 2a, 3a, 4a and 5a designated. For most of these compounds, R 'and R "are of one different, one of these radicals usually alkyl, alkenyl, alkoxy or alkoxyalkyl.

In a smaller subgroup of compounds of formulas 1, 2, 3, 4 and 5, other than group B, R '' is -F, -Cl, -NCS or - (O) _i CH ₃ - _{(k + 1)} F _k Cl₁, where i is 0 or 1 and k + 1 is 1, 2 or 3; the compounds in which R "has this meaning are designated by sub-formulas 1 b, 2 b, 3 b, 4 b and 5 c. Particularly preferred are those connec tions of the sub-formulas 1b, 2b, 3b, 4b and 5b, in which R '' has the meaning -F, -Cl, NCS, -CF₃, -OCHF₂ or -OCF₃.

In the compounds of sub-formulas 1b, 2b, 3b, 4b and 5b R 'has the at the meaning of the compounds of sub-formulas 1a-5a and is preferably alkyl, alkenyl, alkoxy or alkoxyalkyl.

In a further smaller subgroup of the compounds of the formulas 1, 2, 3, 4 and 5 are R "-CN; this subgroup is hereafter referred to as Group C and become the compounds of this subgroup according to sub-formulas 1c, 2c, 3c, 4c and 5c described. In the Compounds of sub-formulas 1c, 2c, 3c, 4c and 5c have R 'in the Compounds of the subformulae 1a-5a given meaning and is present preferably alkyl, alkoxy or alkenyl.

In addition to the preferred compounds of groups A, B and C are also other compounds of formulas 1, 2, 3, 4 and 5 with other variants the proposed substituents in use. All these substances are by literature methods or in analogy available.

The media according to the invention contain, in addition to inventive Ver compounds of the formula I preferably one or more compounds, which are selected from group A and / or group B. and / or group C. The mass fractions of the compounds from these Groups on the media according to the invention are preferably

Group A:
0 to 90%, preferably 20 to 90%, in particular 30 to 90%
Group B:
0 to 80%, preferably 10 to 80%, especially 10 to 65%
Group C:
0 to 80%, preferably 5 to 80%, especially 5 to 50%

wherein the sum of the mass fractions of the fiction in the respective Compounds contained in the media from groups A and / or B and / or C preferably 5% to 90% and especially 10% to 90%.

The media according to the invention preferably contain 1 to 40%, ins particular preferably 5 to 30% of the invention verbin fertilize. Further preferred are media containing more than 40%, in particular 45 to 90% of compounds according to the invention. The Media preferably contain three, four or five inventive Links.

The structure of the IPS display according to the invention corresponds to that for Such ads usual construction, such. B. described in the WO 91/10936 or EP 0 588 568. The term is the usual Construction here broad and includes all modifications and Modifications of the IPS display, in particular z. B. also matrix display elements based on poly-Si TFT or MIM.

A significant difference of the displays according to the invention to the hitherto usual, however, consists in the choice of liquid crystal parameters the liquid crystal layer.

The preparation of the liquid crystal which can be used according to the invention Mixtures takes place in a conventional manner. In general, the ge desired amount of components used in lesser amount the components constituting the main component are solved, purpose moderately at elevated temperature. It is also possible solutions of  Components in an organic solvent, eg. In acetone, Chloroform or methanol, and the solvent after Remove again mixing, for example by distillation.

The dielectrics may also other, known in the art and in the Literature described additives contain. For example, 0-15% pleochroic dyes or chiral dopants are added.

C is a crystalline, S is a smectic, S _{B is} a smectic B, N is a nematic and I is the isotropic phase.

V₁₀ denotes the voltage for 10% transmission (view perpendicular right to the disk surface). t _on denotes the switch-on time and t _off the switch-off time at an operating voltage corresponding to 2.5 times the value of V₁₀. Δn denotes the optical anisotropy and n _o the refractive index (in each case at 589 nm). Δε denotes the dielectric anisotropy (Δε = ε _{∥ -ε ⟂} , where ε _{∥ denotes} the dielectric constant parallel to the _longitudinal molecular _axes and ε _⟂ the dielectric constant perpendicular to this The electro-optical data were measured in an IPS cell at 20 ° C., if not The optical data were measured at 20 ° C, unless expressly stated otherwise.

It became an IPS test cell according to WO 91/10936 with a comb structure used, wherein the electrodes and the electrode interspaces a Thickness of 20 pm.

The layer thickness d of the liquid crystal material is 5 pm. The cell also states:

Output twist angle: 0 °
Alignment angle: 5 °
Tilt angle: 3 °

The cells are dark in the "off" state.  

In the present application and in the following examples, the structures of the liquid crystal compounds are indicated by acronyms, wherein the transformation into chemical formulas according to following Tables A and B takes place. All radicals C _n H _{2n + 1} are straight-chain alkyl radicals with n or m C atoms. The coding according to Table B is self-evident. In Table A, only the acronym for the main body is given. In individual cases, separated from the acronym for the main body followed by a line a code for the substituents R₁, R₂, L₁ and L₂:

Table A

Table B

Example 1

An IPS display contains a nematic mixture with

Clearing point | + 68 ° C .DELTA.n 0.0789 n _o 1.4725 Δε 12.7 ε _⟂ 5.1   Viscosity (20 ° C) 18 mm² s ^-1 K₁ [10 ^-12 N] (20 ° C) 7.4 K₃ [10 ^-12 N] (20 ° C) 15.6

consisting of

PCH-3 6.00 CCP 2OCF₂.F.F 12,00 CCP 2F.F.F 17.00 CCP 3F.F.F 14.00 CCP 5F.F.F 13,00 CCP 2OCF₃ 15.00 CCP 3OCF₃ 13,00 PDX-3N.F.F 5.00 PDX-5N.F.F 5.00

and has high contrast and low switching times.

example 2

An IPS display contains a nematic mixture with

clearing point 75 .DELTA.n 0.0800 n _o 1.4735 AE 11.7 ε _⟂ 4.8 Viscosity (20 ° C) 24 mm² s ^-1

consisting of

PCH-3 6.00 CCP 2OCF₂.F.F 12,00 CCP 2F.F.F 17.00 CCP 3F.F.F 14.00 CCP 5F.F.F 13,00 CCP 2OCF₃ 15.00 CCP 3OCF₃ 13,00 PDX-3N.F 5.00 PDX-5N.F 5.00

and has high contrast and low switching times.

example 3

An IPS display contains a nematic mixture consisting of

PCH-3 10.00 PDX-3N.F 14.00 PDX-3N.F.F 9.00 CCP 3OCF2.F.F 11.00 CCP 5OCF2.F.F 10.00 CCP 3F.F.F 11.00 CCP 5F.F.F 11.00 CH-33 4.00 CH-35 3.00 CCH 501 7.00

and has high contrast and low switching times.  

example 4

An IPS display contains a nematic mixture with

PCH-3 7.00 PCH-7F 2.00 CCP 2F.F.F 16.00 CCP 3F.F.F 10.00 CCP 5F.F.F 9.00 CCP 2OCF₃ 16.00 CCP 3OCF₃ 15.00 CCP 4OCF₃ 5.00 PDX-2N.F 5.00 PDX-3N.F 5.00 PDX-5N.F 4.00 PDX-3 6.00

Clearing point | + 60 ° C .DELTA.n .0798 Δε .0798 ε _⟂ 5.6 e 18.2 Rotational viscosity (20 ° C) 97 mPa · s V₁₀ 0.77 V Specific resistance 4.9 10¹⁰ cm K₁ 6.6 x 10 ^-12 N K₃ 14.7 · 10 ^-12 N

and has high contrast and low switching times.

example 5

An IPS display contains a nematic mixture with

PCH-3 11.00 CCP 2F.F.F 16.00 CCP 3F.F.F 10.00 CCP 5F.F.F 7.00 CCP 2OCF₃ 16.00 CCP 3OCF₃ 15.00 CCP 5OCF₃ 11.00 PDX-2N.F 5.00 CCH-34 6.00

Clearing point | + 83 ° C .DELTA.n .0809 Δε +10.3 ε _⟂ +4.0 Rotational viscosity (20 ° C) 105 mPa · s V₁₀ 1.05 V Specific resistance 3.4 10 11 cm

and has high contrast and low switching times.  

example 6

An IPS display contains a nematic mixture with

PCH-3 6.00 CCP 2OCF2.F.F 12,00 CCP 2F.F.F 17.0 CCP 3F.F.F 14.00 CCP 2OCF₃ 15.00 CCP 3OCF₃ 13,00 DU-3-N 5.00 CU-5-N 5.00

Clearing point | + 68 ° C .DELTA.n 0.0789 Δε 12.7 ε _⟂ 5.1 V₁₀ 0.81V K₁ 7.4 × 10 ^-12 N K₃ 15.6 ± 10 ^-12 N

and has high contrast and low switching times.

example 7

An IPS display contains a nematic mixture with

CCP 2F.F.F 16.00 CCP 3F.F.F 14.00 CCP 5F.F.F 11.00 CCP 2OCF₃ 17.00 CCP 3OCF₃ 14.00 PDX-2N.F 3.00 PDX-3N.F 6.00 PDX-5N.F 11.00 CDU-3-F 8.00

Clearing point | + 60 ° C .DELTA.n 0.0756 Δε +13.7 ε _⟂ +6.1 Rotational viscosity (20 ° C) 109 mPa · s V₁₀ 0,70V K₁ 6.0 · 10 ^-12 N K₃ 14.5 x 10 ^-12 N

and has high contrast and low switching times.  

example 8

An IPS display contains a nematic mixture with

PCH-3 7.00 CCP 2F.F.F 16.00 CCP 3F.F.F 7.00 CCP 5F.F.F 9.00 CCP 2OCF₃ 16.00 CCP 3OCF₃ 15.00 CCP 5OCF₃ 4.00 PDX-2N.F 5.00 PDX-3N.F 5.00 PDX-5N.F 3.00 CCH-34 8.00 CCH-35 5.00

Clearing point | + 71 ° C .DELTA.n 0.0777 Δε +10.6 ε _⟂ 4.7 Rotational viscosity (20 ° C) 88 mPa · s V₁₀ 0,94 v K₁ 8.5 · 10 ^-12 N K₃ 15.2 × 10 ^-12 N

and has high contrast and low switching times.

example 9

An IPS display contains a nematic mixture with

CCP 2F.F.F 16.00 CCP 3F.F.F 13,00 CCP 5F.F.F 9.00 CCP 2OCF₃ 16.00 CCP 3OCF₃ 15.00 CCP 5OCF₃ 5.00 PDX-3 11.00 CCH-34 10.00 PCH-7F 5.00

Clearing point | + 76 ° C Δε +9.0 ε _⟂ +3.9 .DELTA.n 0.0768 V₁₀ 1.16 V Rotational viscosity (20 ° C) 93 mPa · s Specific resistance 2.3 10¹² cm

The IPS displays of Examples 1 to 9 are characterized by a low Drive voltage and lead in cells according to Embodient 1 of EP 0 58 568 for good "Voltage Holding Ratio" values.

Comparative example

An IPS display contains a nematic mixture with

Clearing point | 64 ° C .DELTA.n 0.0813 Δε +12.0

consisting of

ME2N.F 4.00 ME3N.F 4.00 MESN.F 10.00 ME7N.F 6.00 CCH 2 12,00 CCH 3 12,00 CCH-4 12,00 CCP 3OCF₃ 6.00 CCP 5OCF₃ 6.00 CH-33 3.00 CH-35 3.00 CCH-34 10.00 CCH-35 4.00 CCH 303 4.00 CCH 501 4.00

and has a lower contrast and a higher switching time than the Display example 1.

Claims (12)

1. Electro-optical liquid crystal display

• with a reorientation layer for reorienting the liquid crystals whose field has a significant component parallel to the liquid crystal layer,
• containing a liquid-crystalline medium having positive dielectric anisotropy, characterized in that the medium contains a mesogenic compound which has a group of the formula I: wherein
  L₁ and L₂ each independently represent H or F.

2. A liquid crystal display according to claim 1, characterized in that the medium contains at least one compound of formula I: wherein
R₁ is H, an unsubstituted, an alkyl or alkenyl radical having from 1 to 15 carbon atoms, which is monosubstituted by CN or CF₃ or at least monosubstituted by halogen, in which radicals one or more CH₂ groups are each independently denoted by -O- , -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- may be replaced so that O atoms are not directly linked to one another,
Q is a radical of the formula - (O) _q - (CH₂) _r - (CF₂) _s -worin
q is 0 or 1
r is 0, or an integer between 1 and 6 is and
s is an integer between 0 and 6
XF or Cl, in case = 1-6 also H, and
p is 0.1 or 2,
A₁ and A₂ each independently

• (A) 1,4-cyclohexenylene or trans-1,4-cyclo hexylene, wherein one or more non-adjacent CH₂ groups may be replaced by -O- and / or -S-
• (b) 1,4-phenylene radical, in which also one or two CH groups may be replaced by N,
• (c) radical from the group consisting of 1,4-bicyclo (2,2,2) octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydro naphthalene-2,6-diyl and 1,2 , 3,4-tetrahydro-naphthalene-2,6-diyl,

where the radicals (a) and (b) can be substituted by one or two fluorine,
L₃ and L₄ H or F,
Z₁ and Z₂ are each independently -CO-O-, -O-CO-, -CH₂O-, -OCH₂-, -CH₂CH₂-, -CH = CH-, -C≡C- or a single bond, one of the radicals Z₁ and Z₂ also - (CH₂) ₄- or -CH = CH-CH₂C H₂-, and
m 0, 1 or 2
means. 3. Liquid crystal display according to one of claims 1 to 3, characterized in that the medium contains at least one compound of formula II wherein
L₁ and L₂ have the meaning indicated,
R₂ has the meaning given for R₁,
A₃ and A₄ each independently have the meaning given for A₁ and A₂,
Z₃ and Z₄ each independently have the meaning given for Z₁ and Z₂, and
n is 0, 1 or 2. 4. Liquid crystal display according to one of claims 1 to 3, characterized characterized in that the medium has a dielectric anisotropy Δε <8.5. 5. Liquid crystal display according to one of claims 1 to 4, characterized in that the medium contains at least one compound of formula III, R₃- (A₅-Z₅) _o -A₆-R₄ (III) wherein
R₃ and R₄ each independently of one another have the meaning given for R₁,
A₅ and A₆ each independently have the meaning given for A₁ and A₂,
each independently of one another has the meaning given for Z₁ and Z₂ given, and
o is 1, 2 or 3. 6. Liquid crystal display according to one of claims 1 to 5, characterized in that the medium contains at least one compound of formula IV wherein
R₅ has the meaning given for R₁, means
Z represents a single bond or -COO-, and
L₅ and L₆ are each F or H. 7. Display according to one of claims 1 to 6, characterized gekennzeich net, that the picture elements are controlled by means of active matrix. 8. Liquid-crystalline medium with positive dielectric anisotropy, which is a composition according to claims 2 to 7 having. 9. Liquid-crystalline medium according to claim 8, characterized in that it

• From 60 to 95, preferably from 75 to 90,% by weight of at least one compound of the formula I,
• From 5 to 25, preferably from 7 to 20,% by weight of at least one compound of the formula II,
• - 0 to 10, preferably 25 to 50 wt .-% of at least one compound of formula III, and
• From 1 to 10, preferably from 2 to 8,% by weight of a compound of the formula IV,

contains. 10. Liquid-crystalline medium according to claim 8 or 9, characterized in that it comprises:

• - contains at least one compound selected from the formulas Ia, Ib and Ic
• contains at least one compound selected from the formulas IIa, IIb and IIc,
• optionally containing at least one compound selected from the formulas IIIa, IIIb and IIIc, such as
• contains at least one compound selected from the formulas IVa and IVb, wherein and
  Z₂-COO-, -CH₂CH₂- or a single bond
  means, and R₁, R₂, R₃, R₄, R₅, L₁ to L₆ have the meaning given in each case.