Liquid crystalline medium

Abstract

The invention relates to a liquid-crystalline medium which comprises at least one compound of the formula I, ##STR00001##
and to the use thereof for an active-matrix display, in particular based on the VA, PSA, PS-VA, PALC, FFS or IPS effect.

Claims

1. A liquid-crystalline medium comprising a mixture of polar compounds, said mixture comprises at least one compound of the formula I, ##STR00258## in which R.sup.1 and R.sup.1* each, independently of one another, denote an alkyl or alkoxy Radical having 1 to 15 C atoms, wherein one or more CH.sub.2 groups in these radicals is optionally replaced, independently of one another, by —C≡C—, —CF.sub.2O—, —CH═CH—, ##STR00259##  —O—, —CO—O—, —O—CO— in such a way that O atoms are not linked directly to one another, and wherein one or more H atoms may be replaced by halogen, and L.sup.1 and L.sup.2 each, independently of one another, denote F, Cl, CF.sub.3 or CHF.sub.2.

2. The liquid-crystalline medium according to claim 1, further comprising one or more compounds of formulae IIA, IIB and IIC, ##STR00260## in which R.sup.2A, R.sup.2B and R.sup.2C each, independently of one another, denote H, an alkyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF.sub.3 or at least monosubstituted by halogen, wherein one or more CH.sub.2 groups in these radicals is optionally replaced by —O—, —S—, ##STR00261##  —CH═CH—, —C≡C—, —CF.sub.2O—, —OCF.sub.2—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another, L.sup.1-4 each, independently of one another, denote F or Cl, Z.sup.2 and Z.sup.2′ each, independently of one another, denote a single bond, —CH.sub.2CH.sub.2—, —CH═CH—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2O—, —OCH.sub.2—, —COO—, —OCO—, —C.sub.2F.sub.4—, —CF═CF—, —CH═CHCH.sub.2O—, n denotes 0 or 1, p denotes 1 or 2, q denotes 0 or 1, and v denotes 1 to 6.

3. The liquid-crystalline medium according to claim 1, further comprising one or more compounds of the formula III, ##STR00262## in which R.sup.31 and R.sup.32 each, independently of one another, denote a straight-chain alkyl, alkoxyalkyl or alkoxy radical having up to 12 C atoms, and ##STR00263##  denotes ##STR00264## Z.sup.3 denotes a single bond, —CH.sub.2CH.sub.2—, —CH═CH—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2O—, —OCH.sub.2—, —COO—, —OCO—, —C.sub.2F.sub.4—, —C.sub.4H.sub.9—, —CF═CF—.

4. The liquid-crystalline medium according to claim 1, comprising at least compound of the formulae I-1 to I-10, ##STR00265## in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms, alkoxy and alkoxy* each, independently of one another, denote a straight-chain alkoxy radical having 1-6 C atoms, and L.sup.1 and L.sup.2 each, independently of one another, denote F or Cl.

5. The liquid-crystalline medium according to claim 1, further comprising at least one compound of the formulae L-1 to L-11, ##STR00266## ##STR00267## in which R, R.sup.1 and R.sup.2 each, independently of one another, denote H, an alkyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF.sub.3 or at least monosubstituted by halogen, wherein one or more CH.sub.2 groups in these radicals is optionally replaced by —O—, —S—, ##STR00268##  —C≡C—, —CF.sub.2O—, —OCF.sub.2—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another, alkyl denotes an alkyl radical having 1-6 C atoms, n denotes 0 or 1, and s denotes 1 or 2.

6. The liquid-crystalline medium according to claim 1, further comprising one or more terphenyls of the formulae T-1 to T-21, ##STR00269## ##STR00270## ##STR00271## in which R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms, x denotes 0-4, n denotes 0 or 1, m denotes 1-6.

7. The liquid-crystalline medium according to claim 1, further comprising one or more compounds of the formulae O-1 to O-16, ##STR00272## ##STR00273## in which R.sup.1 and R.sup.2 each, independently of one another, denote H, an alkyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF.sub.3 or at least monosubstituted by halogen, wherein one or more CH.sub.2 groups in these radicals is optionally replaced by —O—, —S—, ##STR00274##  —C≡C—, —CF.sub.2O—, —OCF.sub.2—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another.

8. The liquid-crystalline medium according to claim 1, further comprising one or more indane compounds of the formula In, ##STR00275## in which R.sup.11, R.sup.12, R.sup.13 denote a straight-chain alkyl, alkoxy, alkoxyalkyl or alkenyl radical having 1-5 C atoms, R.sup.12 and R.sup.13 can also denote halogen, ##STR00276##  denotes ##STR00277## i denotes 0, 1 or 2.

9. The liquid-crystalline medium according to claim 1, having a proportion of compounds of the formula I in the mixture as a whole is ≧1% by weight.

10. A process for the preparation of a liquid-crystalline medium according to claim 1, comprising mixing at least one compound of the formula I with at least one further liquid-crystalline compound, and additives are optionally added.

11. An electro-optical display, comprising a liquid-crystalline medium according to claim 1.

12. An electro-optical display having active-matrix addressing, comprising, as dielectric, a liquid-crystalline medium according to claim 1.

13. An electro-optical display according to claim 12, that is a VA, PSA, PS-VA, PALC, FFS or IPS display.

14. A compound, which is one of the following compounds ##STR00278## ##STR00279## ##STR00280##

Description

WORKING EXAMPLES

(1) The following examples are intended to explain the invention without restricting it. In the examples, m.p. denotes the melting point and C denotes the clearing point of a liquid-crystalline substance in degrees Celsius; boiling points are denoted by b.p. Furthermore:

(2) C denotes crystalline solid state, S denotes smectic phase (the index denotes the phase type), N denotes nematic state, Ch denotes cholesteric phase, I denotes isotropic phase, T.sub.g denotes glass transition temperature. The number between two symbols indicates the conversion temperature in degrees Celsius.

(3) The host mixture used for determination of the optical anisotropy Δn of the compounds of the formula I is the commercial mixture ZLI-4792 (Merck KGaA). The dielectric anisotropy Δ∈ is determined using commercial mixture ZLI-2857. The physical data of the compound to be investigated are obtained from the change in the dielectric constants of the host mixture after addition of the compound to be investigated and extrapolation to 100% of the compound employed. In general, 10% of the compound to be investigated are dissolved in the host mixture, depending on the solubility.

(4) Unless indicated otherwise, parts or percent data denote parts by weight or percent by weight.

(5) Conventional work-up means: water is added, the mixture is extracted with methylene chloride, the phases are separated, the organic phase is dried and evaporated, and the product is purified by crystallisation and/or chromatography.

Example 1

(6) ##STR00250##

(7) 100 g (0.54 mol) of 2,3-difluorobutoxybenzene are initially introduced in 750 ml of THF and cooled to −70° C. 360 ml of a 1.6 M solution (0.57 mol) of n-butyllithium in hexane are then added dropwise. The mixture is stirred at −70° C. for a one further hour, and 66 ml (0.59 mol) of trimethyl borate in 100 ml of THF are subsequently added dropwise. The batch is warmed to 0° C., and 46 ml of glacial acetic acid and 100 ml of water are added. 140 ml of hydrogen peroxide (30%) are then added dropwise at 30° C. During this addition, the reaction mixture warms to about 45° C. The mixture is allowed to cool to room temperature and is stirred for a further 1 h, before being subjected to conventional work-up. This gives 78 g of crude product, which, without further purification, is dissolved in 200 ml of ethyl methyl ketone, and 0.4 mol of n-butyl bromide and 0.5 mol of potassium carbonate are added. The mixture is boiled under reflux overnight and subjected to conventional work-up. The final purification is carried out by distillation at 0.5 mbar and a boiling point of 107-110° C.

(8) C −8 I; Δn=0.0832; Δ∈=−8.6

(9) The following compounds of the formula

(10) ##STR00251##
are prepared analogously:

(11) TABLE-US-00005 R.sup.1 R.sup.1* L.sup.1 L.sup.2 C.sub.2H.sub.5O OC.sub.3H.sub.7 F F T.sub.g −77 I; Δn = 0.0802; Δε = −8.7 C.sub.2H.sub.5O OC.sub.4H.sub.9 F F T.sub.g −80 C −19 I; Δn = 0.0876; Δε = −9.4 C.sub.2H.sub.5O OC.sub.5H.sub.11 F F T.sub.g −81 C −8 I; Δn = 0.0838; Δε = −8.2 C.sub.2H.sub.5O OC.sub.6H.sub.13 F F C 8 I; Δn = 0.0880; Δε = −8.4 C.sub.2H.sub.5O OC.sub.3H.sub.7 F Cl C.sub.2H.sub.5O OC.sub.4H.sub.9 F Cl C.sub.2H.sub.5O OC.sub.5H.sub.11 F Cl C.sub.2H.sub.5O OC.sub.6H.sub.13 F Cl C.sub.2H.sub.5O OC.sub.3H.sub.7 Cl F C.sub.2H.sub.5O OC.sub.4H.sub.9 Cl F C.sub.2H.sub.5O OC.sub.5H.sub.11 Cl F C.sub.2H.sub.5O OC.sub.6H.sub.13 Cl F C.sub.3H.sub.7O OC.sub.3H.sub.7 F F C 0 I; Δn = 0.0785; Δε = −7.8 C.sub.3H.sub.7O OC.sub.4H.sub.9 F F C −12 I; Δn = 0.0797; Δε = −8.3 C.sub.3H.sub.7O OC.sub.5H.sub.11 F F C 4 I; Δn = 0.0776; Δε = −7.7 C.sub.3H.sub.7O OC.sub.6H.sub.13 F F C 4 I; Δn = 0.0787; Δε = −7.2 C.sub.3H.sub.7O OC.sub.3H.sub.7 F Cl C.sub.3H.sub.7O OC.sub.4H.sub.9 F Cl C.sub.3H.sub.7O OC.sub.5H.sub.11 F Cl C.sub.3H.sub.7O OC.sub.6H.sub.13 F Cl C.sub.3H.sub.7O OC.sub.3H.sub.7 Cl F C.sub.3H.sub.7O OC.sub.4H.sub.9 Cl F C.sub.3H.sub.7O OC.sub.5H.sub.11 Cl F C.sub.3H.sub.7O OC.sub.6H.sub.13 Cl F C.sub.4H.sub.9O OC.sub.5H.sub.11 F F C −6 I; Δn = 0.0783; Δε = −8.1 C.sub.4H.sub.9O OC.sub.6H.sub.13 F F C 1 I; Δn = 0.0859; Δε = −8.0 C.sub.4H.sub.9O OC.sub.4H.sub.9 F Cl C.sub.4H.sub.9O OC.sub.5H.sub.11 F Cl C.sub.4H.sub.9O OC.sub.6H.sub.13 F Cl C.sub.4H.sub.9O OC.sub.4H.sub.9 Cl F C.sub.4H.sub.9O OC.sub.5H.sub.11 Cl F C.sub.4H.sub.9O OC.sub.6H.sub.13 Cl F C.sub.5H.sub.11O OC.sub.5H.sub.11 F F C 21 I; Δn = 0.0755; Δε = −7.8 C.sub.5H.sub.11O OC.sub.6H.sub.13 F F C −1 I; Δn = 0.0771 ;Δε = −7.7 C.sub.5H.sub.11O OC.sub.5H.sub.11 F Cl C.sub.5H.sub.11O OC.sub.6H.sub.13 F Cl C.sub.5H.sub.11O OC.sub.5H.sub.11 Cl F C.sub.5H.sub.11O OC.sub.6H.sub.13 Cl F C.sub.6H.sub.13O OC.sub.6H.sub.13 F F C 17 I; Δn = 0.0853; Δε = −7.8 C.sub.6H.sub.13O OC.sub.6H.sub.13 F Cl C.sub.6H.sub.13O OC.sub.6H.sub.13 Cl F

Example 2

(12) ##STR00252##

(13) 10 g of 4-propoxy-2,3-difluorophenol (53 mmol) are boiled under reflux overnight with 8.4 g of 3-bromo-1-propene (69 mmol) and 8.1 g of potassium carbonate. The mixture is subjected to conventional work-up, and the residue is distilled at 0.5 mbar and a boiling point of 88-90° C.

(14) T.sub.g −86 C −38 I; Δn=0.0873; Δ∈=−7.7

(15) The following compounds of the formula

(16) ##STR00253##
are prepared analogously:

(17) TABLE-US-00006 R.sup.1 L.sup.1 L.sup.2 C.sub.3H.sub.7O F F C.sub.3H.sub.7O F Cl C.sub.3H.sub.7O Cl F C.sub.4H.sub.9O F F C.sub.4H.sub.9O F Cl C.sub.4H.sub.9O Cl F C.sub.5H.sub.11O F F C.sub.5H.sub.11O F Cl C.sub.5H.sub.11O Cl F C.sub.6H.sub.13O F F C.sub.6H.sub.13O F Cl C.sub.6H.sub.13O Cl F

(18) Above and below, V.sub.0 denotes the threshold voltage, capacitive [V] at 20° C. Δn denotes the optical anisotropy measured at 20° C. and 589 nm Δ∈ denotes the dielectric anisotropy at 20° C. and 1 kHz cl.p. denotes the clearing point [° C.] K.sub.1 denotes the elastic constant, “splay” deformation at 20° C. [pN] K.sub.3 denotes the elastic constant, “bend” deformation at 20° C. [pN] γ.sub.1 denotes the rotational viscosity measured at 20° C. [mPa.Math.s], determined by the rotation method in a magnetic field LTS denotes the low-temperature stability (nematic phase), determined in test cells

(19) The display used for measurement of the threshold voltage has two plane-parallel outer plates at a separation of 20 μm and electrode layers with overlying alignment layers of SE-1211 (Nissan Chemicals) on the insides of the outer plates, which effect a homeotropic alignment of the liquid crystals.

(20) All concentrations in this application relate to the corresponding mixture or mixture component, unless explicitly indicated otherwise. All physical properties are determined as described in “Merck Liquid Crystals, Physical Properties of Liquid Crystals”, status November 1997, Merck KGaA, Germany, and apply for a temperature of 20° C., unless explicitly indicated otherwise.

MIXTURE EXAMPLES

Example M1

(21) TABLE-US-00007 CY-3-O2 16.00% Clearing point [° C.]: 80.5 CCY-3-O2 7.00% Δn [589 nm, 20° C.]: 0.0950 CCY-4-O2 3.00% Δε [1 kHz, 20° C.]: −2.8 CPY-2-O2 8.00% ε.sub.∥ [1 kHz, 20° C.]: 3.4 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.2 CCH-34 6.00% K.sub.3 [pN, 20° C.]: 14.9 CCH-23 22.00% K.sub.3/K.sub.1 [20° C.]: 1.03 CCP-3-3 7.00% γ.sub.1 [mPa .Math. s, 20° C.]: 104 CCP-3-1 8.00% V.sub.0 [20° C., V]: 2.45 BCH-32 6.00% PCH-301 3.00% Y-2O-O4 4.00%

Example M2

(22) TABLE-US-00008 CY-3-O2 13.00% Clearing point [° C.]: 80.5 CCY-3-O2 7.00% Δn [589 nm, 20° C.]: 0.0932 CCY-4-O2 3.00% Δε [1 kHz, 20° C.]: −2.9 CPY-2-O2 8.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.5 CCH-34 6.00% K.sub.3 [pN, 20° C.]: 14.8 CCH-23 22.00% K.sub.3/K.sub.1 [20° C.]: 1.02 CCP-3-3 9.00% γ.sub.1 [mPa .Math. s, 20° C.]: 103 CCP-3-1 9.00% V.sub.0 [20° C., V]: 2.40 BCH-32 6.00% Y-2O-O4 7.00%

Example M3

(23) TABLE-US-00009 CY-3-O2 8.50% Clearing point [° C.]: 80.5 CCY-3-O2 9.50% Δn [589 nm, 20° C.]: 0.0950 CPY-2-O2 8.00% Δε [1 kHz, 20° C.]: −2.8 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 CCH-34 6.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.5 CCH-23 21.00% K.sub.3 [pN, 20° C.]: 14.7 CCP-3-3 9.00% K.sub.3/K.sub.1 [20° C.]: 1.01 CCP-3-1 11.00% γ.sub.1 [mPa .Math. s, 20° C.]: 98 BCH-32 7.00% V.sub.0 [20° C., V]: 2.43 Y-2O-O4 10.00%

Example M4

(24) TABLE-US-00010 CY-3-O2 3.50% Clearing point [° C.]: 74.5 CCY-3-O2 5.00% Δn [589 nm, 20° C.]: 0.0943 CLY-3-O2 7.00% Δε [1 kHz, 20° C.]: −2.6 CPY-2-O2 9.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.2 PYP-2-3 3.00% K.sub.3 [pN, 20° C.]: 14.5 CC-3-V 40.00% K.sub.3/K.sub.1 [20° C.]: 1.16 CCP-V-1 14.00% γ.sub.1 [mPa .Math. s, 20° C.]: 68 Y-2O-O4 8.50% V.sub.0 [20° C., V]: 2.52

Example M5

(25) TABLE-US-00011 CY-3-O2 14.50% Clearing point [° C.]: 79.5 CCY-3-O2 11.00% Δn [589 nm, 20° C.]: 0.0946 CPY-2-O2 8.50% Δε [1 kHz, 20° C.]: −3.0 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-34 5.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.7 CCP-3-3 8.00% K.sub.3/K.sub.1 [20° C.]: 1.01 CCP-3-1 8.00% γ.sub.1 [mPa .Math. s, 20° C.]: 109 BCH-32 6.00% V.sub.0 [20° C., V]: 2.33 Y-4O-O5 7.00%

Example M6

(26) TABLE-US-00012 CY-3-O2 11.00% Clearing point [° C.]: 79.5 CCY-3-O2 11.00% Δn [589 nm, 20° C.]: 0.0941 CCY-4-O2 4.00% Δε [1 kHz, 20° C.]: −3.0 CPY-2-O2 2.00% ε.sub.∥ [1 kHz, 20° C.]: 3.8 CPY-3-O2 11.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.8 CCH-34 6.00% K.sub.3 [pN, 20° C.]: 14.8 CCH-23 22.00% K.sub.3/K.sub.1 [20° C.]: 1.03 CCP-3-3 6.00% γ.sub.1 [mPa .Math. s, 20° C.]: 102 CCP-3-1 8.00% V.sub.0 [20° C., V]: 2.34 BCH-32 6.00% Y-2O-O4 10.00% CPGP-4-3 3.00%

Example M7

(27) TABLE-US-00013 CY-3-O2 16.00% Clearing point [° C.]: 80.0 CCY-3-O2 5.00% Δn [589 nm, 20° C.]: 0.0941 CPY-2-O2 10.00% Δε [1 kHz, 20° C.]: −2.9 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-34 6.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.5 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.5 CCP-3-1 9.00% K.sub.3/K.sub.1 [20° C.]: 1.04 BCH-32 7.00% γ.sub.1 [mPa .Math. s, 20° C.]: 96 Y-2O-O4 7.00% V.sub.0 [20° C., V]: 2.39 CCVC-3-V 8.00%

Example M8

(28) TABLE-US-00014 CY-3-O2 6.00% Clearing point [° C.]: 76.0 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0964 CLY-3-O2 9.00% Δε [1 kHz, 20° C.]: −3.1 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.8 PYP-2-3 2.00% K.sub.3 [pN, 20° C.]: 14.8 CC-3-V 44.00% K.sub.3/K.sub.1 [20° C.]: 1.14 Y-2O-O4 7.00% γ.sub.1 [mPa .Math. s, 20° C.]: 78 CPGP-4-3 3.00% V.sub.0 [20° C., V]: 2.32

Example M9

(29) TABLE-US-00015 CY-3-O2 13.00% Clearing point [° C.]: 79.5 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0946 CPY-2-O2 9.00% Δε [1 kHz, 20° C.]: −2.8 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 CCH-34 6.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.5 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.6 CCP-3-3 9.00% K.sub.3/K.sub.1 [20° C.]: 1.02 CCP-3-1 8.00% γ.sub.1 [mPa .Math. s, 20° C.]: 100 BCH-32 7.00% V.sub.0 [20° C., V]: 2.39 Y-2O-O3 7.00%

Example M10

(30) TABLE-US-00016 CY-3-O2 13.00% Clearing point [° C.]: 79.0 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0943 CPY-2-O2 9.00% Δε [1 kHz, 20° C.]: −2.8 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-34 6.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.4 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.3 CCP-3-3 9.00% K.sub.3/K.sub.1 [20° C.]: 1.01 CCP-3-1 8.00% γ.sub.1 [mPa .Math. s, 20° C.]: 101 BCH-32 7.00% V.sub.0 [20° C., V]: 2.39 Y-3O-O3 7.00%

Example M11

(31) TABLE-US-00017 CY-3-O2 4.00% Clearing point [° C.]: 74.5 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0967 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −3.0 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.8 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.8 PYP-2-3 5.00% K.sub.3 [pN, 20° C.]: 14.3 CC-3-V 43.00% K.sub.3/K.sub.1 [20° C.]: 1.13 CCP-V-1 2.00% γ.sub.1 [mPa .Math. s, 20° C.]: 85 Y-3O-O3 7.00% V.sub.0 [20° C., V]: 2.29

Example M12

(32) TABLE-US-00018 CY-3-O2 4.00% Clearing point [° C.]: 75.0 CCY-3-O2 10.00% Δn [589 nm, 20° C.]: 0.0958 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −3.1 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.7 PYP-2-3 5.00% K.sub.3 [pN, 20° C.]: 15.2 CC-3-V 44.00% K.sub.3/K.sub.1 [20° C.]: 1.12 Y-3O-O5 7.00% γ.sub.1 [mPa .Math. s, 20° C.]: 77 V.sub.0 [20° C., V]: 2.28

Example M13

(33) TABLE-US-00019 CY-3-O2 14.50% Clearing point [° C.]: 80.0 CCY-3-O2 11.00% Δn [589 nm, 20° C.]: 0.0952 CPY-2-O2 8.50% Δε [1 kHz, 20° C.]: −3.1 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.5 CCH-34 5.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 15.1 CCP-3-3 8.00% K.sub.3/K.sub.1 [20° C.]: 1.01 CCP-3-1 8.00% γ.sub.1 [mPa .Math. s, 20° C.]: 111 BCH-32 6.00% V.sub.0 [20° C., V]: 2.35 Y-4O-O6 7.00%

Example M14

(34) TABLE-US-00020 CY-3-O2 15.00% Clearing point [° C.]: 80.0 CCY-3-O2 11.00% Δn [589 nm, 20° C.]: 0.0948 CPY-2-O2 8.00% Δε [1 kHz, 20° C.]: −3.0 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.4 CCH-34 5.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.4 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.8 CCP-3-3 8.00% K.sub.3/K.sub.1 [20° C.]: 1.00 CCP-3-1 8.00% γ.sub.1 [mPa .Math. s, 20° C.]: 113 BCH-32 6.00% V.sub.0 [20° C., V]: 2.36 Y-6O-O6 7.00% LTS [bulk, −30° C.]: >1000 h

Example M15

(35) TABLE-US-00021 CCY-3-O2 10.00% Clearing point [° C.]: 61.0 CLY-3-O2 10.00% Δn [589 nm, 20° C.]: 0.0915 CPY-2-O2 4.00% Δε [1 kHz, 20° C.]: −3.1 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 4.0 PYP-2-3 8.00% ε.sub.⊥ [1 kHz, 20° C.]: 7.1 CC-3-V 45.00% K.sub.3 [pN, 20° C.]: 12.1 Y-2O-O4 13.00% K.sub.3/K.sub.1 [20° C.]: 1.11 γ.sub.1 [mPa .Math. s, 20° C.]: 58 V.sub.0 [20° C., V]: 2.10

Example M16

(36) TABLE-US-00022 CLY-3-O2 10.00% Clearing point [° C.]: 80.0 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0948 CPY-2-O2 6.00% Δε [1 kHz, 20° C.]: −2.9 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 CCH-34 3.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 CCH-23 30.00% K.sub.3 [pN, 20° C.]: 14.4 CCP-3-1 10.00% K.sub.3/K.sub.1 [20° C.]: 0.96 CCP-3-3 2.00% γ.sub.1 [mPa .Math. s, 20° C.]: 94 PYP-2-3 2.00% V.sub.0 [20° C., V]: 2.36 BCH-32 6.00% Y-2O-O5 12.00%

Example M17

(37) TABLE-US-00023 CY-3-O2 4.00% Clearing point [° C.]: 75.5 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0972 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −3.1 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.5 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 PYP-2-3 5.00% K.sub.3 [pN, 20° C.]: 14.7 CC-3-V 43.50% K.sub.3/K.sub.1 [20° C.]: 1.11 CCP-V-1 1.50% γ.sub.1 [mPa .Math. s, 20° C.]: 76 Y-4O-O4 7.00% V.sub.0 [20° C., V]: 2.32

Example M18

(38) TABLE-US-00024 CY-3-O2 14.00% Clearing point [° C.]: 79.5 CCY-3-O2 11.00% Δn [589 nm, 20° C.]: 0.0949 CPY-2-O2 10.00% Δε [1 kHz, 20° C.]: −3.0 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 CCH-34 6.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.7 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.7 CCP-3-3 6.50% K.sub.3/K.sub.1 [20° C.]: 1.03 CCP-3-1 9.00% γ.sub.1 [mPa .Math. s, 20° C.]: 104 BCH-32 5.00% V.sub.0 [20° C., V]: 2.32 Y-3O-O1V 6.50%

Example M19

(39) TABLE-US-00025 CY-3-O2 4.00% Clearing point [° C.]: 76.0 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0973 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −3.0 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.7 PYP-2-3 5.00% K.sub.3 [pN, 20° C.]: 14.7 CC-3-V 43.00% K.sub.3/K.sub.1 [20° C.]: 1.12 CCP-V-1 2.00% γ.sub.1 [mPa .Math. s, 20° C.]: 76 Y-2O-O5 7.00% V.sub.0 [20° C., V]: 2.32

Example M20

(40) TABLE-US-00026 CY-3-O2 4.00% Clearing point [° C.]: 75.5 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0970 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −3.1 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.7 PYP-2-3 5.00% K.sub.3 [pN, 20° C.]: 14.6 CC-3-V 43.00% K.sub.3/K.sub.1 [20° C.]: 1.12 CCP-V-1 2.00% γ.sub.1 [mPa .Math. s, 20° C.]: 77 Y-3O-O4 7.00%

Example M21

(41) TABLE-US-00027 CY-3-O2 4.50% Clearing point [° C.]: 76.0 CCY-3-O2 10.00% Δn [589 nm, 20° C.]: 0.0963 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −3.0 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 PYP-2-3 5.00% K.sub.3 [pN, 20° C.]: 14.5 CC-3-V 44.00% K.sub.3/K.sub.1 [20° C.]: 1.10 Y-5O-O5 6.50% γ.sub.1 [mPa .Math. s, 20° C.]: 79 V.sub.0 [20° C., V]: 2.32

Example M22

(42) TABLE-US-00028 CLY-3-O2 10.00% Clearing point [° C.]: 80.5 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.0949 CPY-2-O2 6.00% Δε [1 kHz, 20° C.]: −2.9 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-34 3.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.5 CCH-23 30.00% K.sub.3 [pN, 20° C.]: 14.8 CCP-3-1 10.00% K.sub.3/K.sub.1 [20° C.]: 0.95 CCP-3-3 2.00% γ.sub.1 [mPa .Math. s, 20° C.]: 95 PYP-2-3 2.00% V.sub.0 [20° C., V]: 2.37 BCH-32 6.00% Y-4O-O4 12.00%

Example M23

(43) TABLE-US-00029 CLY-3-O2 10.00% Clearing point [° C.]: 80.5 CCY-3-O2 10.00% Δn [589 nm, 20° C.]: 0.0931 CPY-2-O2 6.50% Δε [1 kHz, 20° C.]: −3.1 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-34 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.7 CCH-23 20.00% K.sub.3 [pN, 20° C.]: 15.0 CCP-3-1 10.00% K.sub.3/K.sub.1 [20° C.]: 0.98 CCP-3-3 3.00% γ.sub.1 [mPa .Math. s, 20° C.]: 98 BCH-32 4.00% V.sub.0 [20° C., V]: 2.33 Y-4O-O4 12.50% PCH-301 4.00%

Example M24

(44) TABLE-US-00030 CLY-3-O2 10.00% Clearing point [° C.]: 79.0 CCY-3-O2 10.00% Δn [589 nm, 20° C.]: 0.0932 CPY-2-O2 4.00% Δε [1 kHz, 20° C.]: −3.0 CPY-3-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-23 30.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 CCP-3-1 10.00% K.sub.3 [pN, 20° C.]: 15.1 CCP-3-3 4.00% K.sub.3/K.sub.1 [20° C.]: 1.02 BCH-32 3.00% γ.sub.1 [mPa .Math. s, 20° C.]: 99 Y-4O-O4 13.00% V.sub.0 [20° C., V]: 2.36 PCH-301 3.00% CPYP-3-2 3.00%

Example M25

(45) TABLE-US-00031 PCH-302 11.00% Clearing point [° C.]: 75.5 CCH-34 18.00% Δn [589 nm, 20° C.]: 0.0914 CCH-25 5.00% Δε [1 kHz, 20° C.]: −2.7 CCH-35 5.00% γ.sub.1 [mPa .Math. s, 20° C.]: 102 CEY-3-O2 14.00% CCP-3-1 9.00% CCP-3-O1 5.00% CPY-2-O2 6.00% CCP-3-3 2.00% CPY-3-O2 10.00% CPY-5-O2 4.00% CCY(F,Cl)-3-O2 4.00% Y-4O-O4 7.00%

Example M26

(46) TABLE-US-00032 CY-3-O2 7.00% Clearing point [° C.]: 84.0 CCY-3-O2 12.00% Δn [589 nm, 20° C.]: 0.1170 CPY-2-O2 8.00% Δε [1 kHz, 20° C.]: −2.5 CPY-3-O2 11.00% γ.sub.1 [mPa .Math. s, 20° C.]: 102 CCH-34 6.00% CCH-23 22.00% CCP-3-3 10.00% CCP-3-1 10.00% BCH-32 2.00% PCH-301 5.00% Y-4O-O4 4.00% Y-2O-O5 3.00%

Example M27

(47) TABLE-US-00033 CCY-3-O2 10.00% Clearing point [° C.]: 95.0 CCY-4-O2 7.00% Δn [589 nm, 20° C.]: 0.0996 CCY-3-O3 6.00% Δε [1 kHz, 20° C.]: −3.2 CPY-2-O2 6.00% γ.sub.1 [mPa .Math. s, 20° C.]: 127 CPY-3-O2 9.00% CCP-V-1 11.00% CC-5-V 10.00% CC-3-V1 10.00% CC-4-V 10.00% PYP-2-4 4.00% CCH-35 5.00% C-Naph-5-02 5.00% Y-4O-O4 7.00%

Example M28

(48) TABLE-US-00034 PY-3-O2 9.50% Clearing point [° C.]: 75.0 CCY-3-O2 4.50% Δn [589 nm, 20° C.]: 0.1181 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −2.9 CPY-3-O2 11.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 CCH-34 8.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 13.7 PYP-2-3 10.00% K.sub.3/K.sub.1 [20° C.]: 0.94 PYP-2-4 5.00% γ.sub.1 [mPa .Math. s, 20° C.]: 101 CCP-3-1 7.00% V.sub.0 [20° C., V]: 2.28 BCH-32 5.00% Y-4O-O4 8.00%

Example M29

(49) TABLE-US-00035 BCH-32 6.00% Clearing point [° C.]: 75.0 CC-3-V 30.00% Δn [589 nm, 20° C.]: 0.0922 CC-3-V1 8.00% Δε [1 kHz, 20° C.]: −3.4 CCY-3-O2 10.00% γ.sub.1 [mPa .Math. s, 20° C.]: 91 CCY-3-O3 8.00% CK-3-F 3.00% CK-4-F 3.00% CK-5-F 2.00% CPY-2-O2 8.00% CPY-3-O2 10.00% CY-3-O4 4.00% Y-4O-O4 8.00%

Example M30

(50) TABLE-US-00036 CC-3-V 27.00% Clearing point [° C.]: 75.0 CC-3-V1 8.00% Δn [589 nm, 20° C.]: 0.0929 CCP-V-1 11.00% Δε [1 kHz, 20° C.]: −3.4 CCY-3-O2 10.00% γ.sub.1 [mPa .Math. s, 20° C.]: 88 CK-3-F 4.00% CK-4-F 4.00% CK-5-F 4.00% CLY-3-O2 8.00% CPY-3-O2 9.00% PYP-2-3 5.00% Y-4O-O4 10.00%

Example M31

(51) TABLE-US-00037 CCY-3-O2 10.00% Clearing point [° C.]: 79.0 CCY-3-O3 9.00% Δn [589 nm, 20° C.]: 0.0911 CCY-4-O2 9.00% Δε [1 kHz, 20° C.]: −3.7 CPY-2-O2 10.00% ε.sub.∥ [1 kHz, 20° C.]: 3.8 CPY-3-O2 10.00% ε.sub.⊥ [1 kHz, 20° C.]: 7.5 PYP-2-3 3.00% K.sub.3 [pN, 20° C.]: 14.0 CCH-23 14.00% K.sub.3/K.sub.1 [20° C.]: 1.04 CCH-34 8.00% V.sub.0 [20° C., V]: 2.0 CCH-35 7.00% CCH-301 75.00% PCH-301 3.00% Y-4O-O4 10.00%

(52) For the preparation of a PS-VA mixture, 0.2% of the polymerisable compound of the formula

(53) ##STR00254##
is added to 99.8% of the mixture from Example M31.

(54) The PS-VA mixture is introduced into a cell with homeotropic alignment. After application of a voltage of 24 V, the cell is irradiated with UV light with a power of 100 mW/cm.sup.2. The following tilt angles then arise:

(55) TABLE-US-00038 Irradiation duration Tilt angle 0 min 89° 1 min 83° 4 min 66° 6 min 65°

Example M32

(56) TABLE-US-00039 PY-3-O2 9.50% Clearing point [° C.]: 75.0 CPTP-302FF 7.00% Δn [589 nm, 20° C.]: 0.1194 CLY-3-O2 10.00% Δε [1 kHz, 20° C.]: −2.9 CPY-3-O2 11.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-34 8.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.5 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.2 PYP-2-3 8.00% K.sub.3/K.sub.1 [20° C.]: 1.02 CCP-3-1 6.50% γ.sub.1 [mPa .Math. s, 20° C.]: 100 BCH-32 5.00% V.sub.0 [20° C., V]: 2.35 Y-4O-O4 8.00% PCH-301 5.00%

Example M33

(57) TABLE-US-00040 CY-3-O2 3.50% Clearing point [° C.]: 79.0 CCY-3-O2 8.00% Δn [589 nm, 20° C.]: 0.1063 CPY-3-O2 8.00% Δε [1 kHz, 20° C.]: −3.0 PYP-2-3 8.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 PYP-2-4 3.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.7 CLY-3-O2 7.00% K.sub.3 [pN, 20° C.]: 14.6 CCY-3-O1 4.00% K.sub.3/K.sub.1 [20° C.]: 0.99 CCP-3-3 5.00% γ.sub.1 [mPa .Math. s, 20° C.]: 106 CCP-3-1 9.00% V.sub.0 [20° C., V]: 2.32 CCH-23 16.00% LTS [Zelle, −30° C.]: >1000 h CCH-34 5.00% LTS [bulk, −20° C.]: >1000 h CCH-35 3.00% BCH-32 6.00% PCH-301 2.00% Y-4O-O4 12.50%

Example M34

(58) TABLE-US-00041 CY-3-O2 3.00% Clearing point [° C.]: 80.0 CCY-3-O2 8.00% Δn [589 nm, 20° C.]: 0.1052 CPY-3-O2 8.00% Δε [1 kHz, 20° C.]: −3.0 PYP-2-3 8.00% ε.sub.∥ [1 kHz, 20° C.]: 3.7 PYP-2-4 3.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.7 CLY-3-O2 7.00% K.sub.3 [pN, 20° C.]: 14.5 CCY-3-O1 4.00% K.sub.3/K.sub.1 [20° C.]: 0.95 CCP-3-3 5.00% γ.sub.1 [mPa .Math. s, 20° C.]: 105 CCP-3-1 9.00% V.sub.0 [20° C., V]: 2.32 CCH-23 16.00% LTS [bulk, −30° C.]: >1000 h CCH-34 8.00% CCH-35 2.00% BCH-32 6.00% Y-4O-O4 13.00%

Example M35

(59) TABLE-US-00042 CY-3-O2 3.00% Clearing point [° C.]: 73.0 CCY-3-O2 9.00% Δn [589 nm, 20° C.]: 0.1050 CLY-3-O2 9.00% Δε [1 kHz, 20° C.]: −3.3 CCY-3-O1 3.00% ε.sub.∥ [1 kHz, 20° C.]: 3.8 CPY-2-O2 2.00% ε.sub.⊥ [1 kHz, 20° C.]: 7.1 CPY-3-O2 9.00% K.sub.3 [pN, 20° C.]: 14.9 PYP-2-3 8.00% K.sub.3/K.sub.1 [20° C.]: 1.12 CC-3-V 31.00% γ.sub.1 [mPa .Math. s, 20° C.]: 88 CC-3-V1 10.00% V.sub.0 [20° C., V]: 2.23 Y-4O-O4 11.00% PPYY-5-3 5.00%

Example M36

(60) TABLE-US-00043 PY-3-O2 8.00% Clearing point [° C.]: 78.0 CPTP-302FF 7.00% Δn [589 nm, 20° C.]: 0.1286 CLY-3-O2 8.00% Δε [1 kHz, 20° C.]: −2.9 CPY-3-O2 11.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CCH-34 8.00% ε.sub.⊥ [1 kHz, 20° C.]: 6.6 CCH-23 22.00% K.sub.3 [pN, 20° C.]: 14.8 PYP-2-3 5.50% K.sub.3/K.sub.1 [20° C.]: 1.01 PTP-302FF 6.00% γ.sub.1 [mPa .Math. s, 20° C.]: 107 CCP-3-1 7.00% V.sub.0 [20° C., V]: 2.39 BCH-32 8.00% Y-4O-O4 8.00% PCH-301 1.50%

Example M37

(61) TABLE-US-00044 CY-3-O2 4.00% Clearing point [° C.]: 75.0 Y-4O-O4 6.00% Δn [589 nm, 20° C.]: 0.1002 CCY-3-O3 11.00% Δε [1 kHz, 20° C.]: −3.1 CCY-4-O2 12.00% ε.sub.∥ [1 kHz, 20° C.]: 3.6 CPY-2-O2 5.00% K.sub.3 [pN, 20° C.]: 12.7 CPY-3-O2 10.00% K.sub.3/K.sub.1 [20° C.]: 0.98 CCH-34 10.00% V.sub.0 [20° C., V]: 2.15 CCH-23 22.00% PYP-2-3 12.00% PCH-301 8.00%

Example M38

(62) For the preparation of a PS-VA mixture, 0.3% of the polymerisable compound of the formula

(63) ##STR00255##
is added to 99.7% of the mixture from Example M37.

(64) The PS-VA mixture is introduced into a cell with homeotropic alignment. After application of a voltage of 24 V, the cell is irradiated with UV light with a power of 100 mW/cm.sup.2.

Example M39

(65) For the preparation of a PS-VA mixture, 0.3% of the polymerisable compound of the formula

(66) ##STR00256##
is added to 99.7% of the mixture from Example M37.

(67) The PS-VA mixture is introduced into a cell with homeotropic alignment. After application of a voltage of 24 V, the cell is irradiated with UV light with a power of 100 mW/cm.sup.2.

Example M40

(68) For the preparation of a PS-VA mixture, 0.3% of the polymerisable compound of the formula

(69) ##STR00257##
is added to 99.7% of the mixture from Example M37.

(70) The PS-VA mixture is introduced into a cell with homeotropic alignment. After application of a voltage of 24 V, the cell is irradiated with UV light with a power of 100 mW/cm.sup.2.