Liquid-crystalline medium

Abstract

The invention relates to a liquid-crystalline medium, characterised in that it comprises one or more compounds of the formula IA, ##STR00001##
and
one or more compounds of the formula IB, ##STR00002##
in which R.sup.A, R.sup.B, X.sup.A, X.sup.B and Y.sup.1-13 have the meanings indicated in Claim 1, and to the use thereof for electro-optical purposes, in particular for shutter glasses, 3D applications, in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS and PS-VA-IPS displays.

Claims

1. A liquid crystalline medium, which comprises one or more compounds of the formula IA, ##STR00226## and one or more compounds of the formula IB, ##STR00227## wherein the total amount of compounds of formula IA and formula IB is ≥20% by weight, based on the weight of the liquid crystal medium, in which R.sup.A and R.sup.B each, independently of one another, denote a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF.sub.2O—, —CH═CH—, ##STR00228## —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, X.sup.A denotes SF.sub.5, SCN or NCS and X.sup.B denotes SCN or NCS, and Y.sup.1-13 each, independently of one another, denote H or F.

2. A liquid crystalline medium according to claim 1, which additionally comprises one or more stabilisers.

3. A liquid-crystalline medium according to claim 2, which comprises one or more compounds selected from the compounds of the formulae IB-a to IB-h ##STR00229##

4. A liquid-crystalline medium according to claim 2, which additionally comprises one or more compounds selected from the formulae II and/or III, ##STR00230## in which R.sup.0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF.sub.2O—, —CH═CH—, ##STR00231## —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, X.sup.0 denotes F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms, and Y.sup.1-5 each, independently of one another, denote H or F, ##STR00232## each, independently of one another, denote ##STR00233##

5. A liquid crystalline medium according to claim 2, which additionally comprises one or more compounds selected from the formulae IV to VIII, ##STR00234## in which Y.sup.1-4 have the meanings indicated in claim 1, R.sup.0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF.sub.2O—, —CH═CH—, ##STR00235## —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another and X° denotes F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms, Z.sup.0 denotes —C.sub.2H.sub.4—, —(CH.sub.2).sub.4—, —CH═CH—, —CF═CF—, —C.sub.2F.sub.4—, —CH.sub.2CF.sub.2—, —CF.sub.2CH.sub.2—, —CH.sub.2O—, —OCH.sub.2—, —COO— or —OCF.sub.2—, in formulae V and VI also a single bond, in formulae V and VIII also —CF.sub.2O—, r denotes 0 or 1, and s denotes 0 or 1.

6. A liquid crystalline medium according to claim 2, which additionally comprises one or more compounds selected from the formulae IX to XII, ##STR00236## in which X.sup.0 denotes F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms and L denotes H or F, “alkyl” denotes C.sub.1-6-alkyl, R′ denotes C.sub.1-6-alkyl, C.sub.1-6-alkoxy or C.sub.2-6-alkenyl, and “alkenyl” and “alkenyl*” each, independently of one another, denote C.sub.2-6-alkenyl.

7. A liquid crystalline medium according to claim 2, which additionally comprises one or more compounds of the formula XIII, ##STR00237## in which R.sup.1 and R.sup.2 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms, where at least one of the radicals R.sup.1 and R.sup.2 denotes alkenyl having 2 to 6 C atoms.

8. A liquid crystalline medium according to claim 2, which additionally comprises one or more compounds of the formula XVII, ##STR00238## in which R.sup.1 and R.sup.2 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 8 C atoms, and L denotes H or F.

9. A liquid crystalline medium according to claim 2, which comprises one or more compounds selected from the group of the compounds of the formulae XXVII, XXVIII and XXIX, ##STR00239## in which R.sup.1 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF.sub.2O—, —CH═CH—, ##STR00240## —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another and X.sup.0 denotes F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms.

10. A liquid crystalline medium according to claim 2, which comprises one or more compounds selected from the group of the compounds of the formulae XIX, XX, XXI, XXII, XXIII and XXIV, ##STR00241## in which R.sup.0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF.sub.2O—, —CH═CH—, ##STR00242## —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another and X.sup.0 denotes F, Cl, CN, SF.sub.5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms, and Y.sup.1-4 each, independently of one another, denote H or F.

11. A liquid crystalline medium according to claim 2, which comprises ≥20% by weight of the compound of the formula IXb, ##STR00243## in which alkyl denotes C.sub.1-6-alkyl.

12. A liquid crystalline medium according to claim 2, which comprises at least two compounds of the formula IA and at least two compounds of the formula IB.

13. A liquid-crystalline medium according to claim 2, which comprises in total ≥30% by weight of compounds of the formula IA and compounds of the formula IB, based on the mixture.

14. A liquid-crystalline medium according to claim 2, which comprises one or more compounds selected from the compounds of the formulae IA-a to IA-f, ##STR00244##

15. A liquid-crystalline medium according to claim 2, which additionally comprises one or more polymerisable compounds.

16. A process for the preparation of a liquid-crystalline according to claim 2, where one or more compounds of the formula IA and one or more compounds of the formula IB, are mixed with one or more stabilizers.

17. A method which comprises using a liquid-crystalline according to claim 2 in an electro-optical device.

18. An electro-optical liquid-crystal display containing a liquid-crystalline medium according to claim 2.

19. A liquid crystalline medium according to claim 2, wherein the one or more stabilizers is selected from the group consisting of ##STR00245## ##STR00246## ##STR00247## ##STR00248##

20. A liquid crystalline medium according to claim 2, wherein the one or more stabilizers is ##STR00249##

21. A liquid-crystalline medium according to claim 1, which comprises one or more compounds selected from the group of the compounds of the formulae ##STR00250## in which n and m each, independently of one another, denote 1, 2, 3, 4, 5, 6, or 7.

22. A liquid-crystalline medium according to claim 21, wherein n denotes 3, 4 or 5 and m denotes 1.

23. A liquid-crystalline medium according to claim 21, wherein the compound of the formula CC-n-Vm is selected from the group consisting of ##STR00251##

24. A liquid-crystalline medium according to claim 1, which comprises two or more compounds of the formula IA.

Description

EXAMPLES

(1) TABLE-US-00008 Example M1 CC-3-V 28.0% Clearing point [° C.]: 90.5 CC-3-V1 5.5% Δn [589 nm, 20° C.]: 0.0991 CCP-V2-1 5.0% Δε [1 kHz, 20° C.]: 12.5 CCP-30CF.sub.3 7.0% γ.sub.1 [mPa .Math. s, 20° C.]: 100 CCP-50CF.sub.3 5.0% V.sub.0 [V]: 1.10 ACQU-3-F 2.5% CCQU-3-F 8.0% CCQU-5-F 6.0% CCGU-3-F 4.0% PUQU-3-F 7.5% APUQU-2-F 5.0% APUQU-3-F 7.0% PGUQU-3-F 2.0% PGUQU-4-F 5.0% PGUQU-5-F 2.5% Example M2 CC-3-V 24.5% Clearing point [° C.]: 95 CC-3-V1 7.0% Δn [589 nm, 20° C.]: 0.0996 CCP-V2-1 6.0% Δε [1 kHz, 20° C.]: 11.0 CCP-V-1 8.0% γ.sub.1 [mPa .Math. s, 20° C.]: 98 CCP-30CF.sub.3 7.0% V.sub.0 [V]: 1.21 CCP-50CF.sub.3 5.0% CCQU-3-F 8.0% CCQU-5-F 6.0% PUQU-3-F 7.0% APUQU-2-F 5.0% APUQU-3-F 8.0% PGUQU-3-F 1.5% PGUQU-4-F 7.0% Example M3 CC-3-V 32.0% Clearing point [° C.]: 75.9 CC-3-V1 9.0% Δn [589 nm, 20° C.]: 0.1258 CCP-V-1 5.0% Δε [1 kHz, 20° C.]: 16.5 PGP-2-2V 3.0% γ.sub.1 [mPa .Math. s, 20° C.]: 87 PGU-2-F 4.0% V.sub.0 [V]: 0.90 PGU-3-F 3.5% PUQU-3-F 6.5% APUQU-2-F 5.0% APUQU-3-F 12.0% PGUQU-3-F 5.0% PGUQU-4-F 7.0% PGUQU-5-F 8.0% Example M4 CC-3-V 27.0% Clearing point [° C.]: 74.8 CC-3-V1 9.0% Δn [589 nm, 20° C.]: 0.1255 CCP-V-1 8.5% Δε [1 kHz, 20° C.]: 18.6 PGU-2-F 4.5% γ.sub.1 [mPa .Math. s, 20° C.]: 95 PGU-3-F 3.0% V.sub.0 [V]: 0.83 PUQU-3-F 11.0% APUQU-2-F 5.0% APUQU-3-F 12.0% PGUQU-3-F 5.0% PGUQU-4-F 7.0% PGUQU-5-F 8.0% Example M5 CC-3-V 30.0% Clearing point [° C.]: 94.5 CC-3-V1 8.0% Δn [589 nm, 20° C.]: 0.0990 CCP-V2-1 4.0% Δε [1 kHz, 20° C.]: 11.0 CCP-V-1 8.0% γ.sub.1 [mPa .Math. s, 20° C.]: 92 CCP-30CF.sub.3 7.0% LTS [bulk, −25° C.]: >1000 h CCQU-3-F 4.0% V.sub.0 [V]: 1.22 PUQU-3-F 5.0% APUQU-2-F 5.0% APUQU-3-F 2.0% PGUQU-3-F 2.0% PGUQU-4-F 5.0% PGUQU-5-F 5.0% CDUQU-3-F 10.0% ECCP-31 5.0% Example M6 CC-3-V 37.0% Clearing point [° C.]: 80.0 CCP-V-1 5.0% Δn [589 nm, 20° C.]: 0.1287 PGU-2-F 3.0% Δε [1 kHz, 20° C.]: 17.3 PGU-3-F 8.0% γ.sub.1 [mPa .Math. s, 20° C.]: 99 BCH-3F.F.F 8.0% LTS [bulk, −25° C.]: >1000 h APUQU-2-F 7.0% V.sub.10 [V]: 1.05 APUQU-3-F 8.0% PGUQU-3-F 4.0% PGUQU-4-F 6.0% PGUQU-5-F 6.0% DPGU-4-F 8.0% Example M7 APUQU-2-F 5.0% Clearing point [° C.]: 74.5 APUQU-3-F 6.0% Δn [589 nm, 20° C.]: 0.1345 BCH-3F.F.F 2.0% Δε [1 kHz, 20° C.]: 13.8 CC-3-V 31.5% CC-3-V1 5.0% CCP-3-3 1.0% CCP-V-1 3.0% CPU-3-OXF 5.0% PGP-2-2V 10.5% PGU-2-F 6.0% PGUQU-3-F 7.0% PGUQU-4-F 3.0% PGUQU-5-F 3.0% PPGU-3-F 1.0% PUQU-3-F 11.0% Example M8 CC-3-V 22.0% Clearing point [° C.]: 79.5 CCP-1F.F.F 3.0% Δn [589 nm, 20° C.]: 0.1294 CCP-2F.F.F 9.0% Δε [1 kHz, 20° C.]: 20.2 CCP-3F.F.F 9.0% γ.sub.1 [mPa .Math. s, 20° C.]: 129 CPU-3-OXF 12.0% LTS [bulk, −25° C.]: >1000 h PGU-2-F 3.0% V.sub.10 [V]: 1.05 PGU-3-F 6.0% APUQU-2-F 7.0% APUQU-3-F 7.0% PGUQU-3-F 4.0% PGUQU-4-F 5.0% PGUQU-5-F 6.0% DPGU-4-F 7.0% Example M9 CC-3-V 37.0% Clearing point [° C.]: 77.5 PUQU-3-F 14.0% Δn [589 nm, 20° C.]: 0.1372 APUQU-2-F 4.0% Δε [1 kHz, 20° C.]: 12.8 APUQU-3-F 5.0% γ.sub.1 [mPa .Math. s, 20° C.]: 82 PGP-1-2V 6.0% LTS [bulk, −25° C.]: >1000 h PGP-2-2V 6.0% V.sub.10 [V]: 1.24 PGP-3-2V 6.0% CCP-V2-1 5.0% PGUQU-3-F 7.0% PGUQU-4-F 5.0% PGUQU-5-F 5.0% Example M10 APUQU-2-F 6.0% Clearing point [° C.]: 75.0 APUQU-3-F 12.0% Δn [589 nm, 20° C.]: 0.1268 PGUQU-3-F 8.0% Δε [1 kHz, 20° C.]: 14.4 PGUQU-4-F 10.0% γ.sub.1 [mPa .Math. s, 20° C.]: 78 PGUQU-5-F 8.0% V.sub.0 [V]: 0.99 PGP-2-2V 5.0% CC-3-V 42.0% CC-3-V1 3.0% PP-1-2V1 6.0% Example M11 APUQU-2-F 10.0% Clearing point [° C.]: 76.5 APUQU-3-F 10.0% Δn [589 nm, 20° C.]: 0.1183 PGUQU-3-F 8.0% Δε [1 kHz, 20° C.]: 14.0 PGUQU-4-F 8.0% V.sub.0 [V]: 0.95 PGUQU-5-F 8.0% CC-3-V 50.0% PGP-2-2V 6.0% Example M12 CC-3-V 33.0% Clearing point [° C.]: 93.5 CC-3-V1 12.0% Δn [589 nm, 20° C.]: 0.1086 CCP-V2-1 6.0% Δε [1 kHz, 20° C.]: 13.7 CCP-30CF3 6.0% γ.sub.1 [mPa .Math. s, 20° C.]: 92 CCQU-3-F 4.0% V.sub.0 [V]: 1.09 APUQU-2-F 10.0% APUQU-3-F 10.0% PGUQU-3-F 5.0% PGUQU-4-F 8.0% DPGU-4-F 6.0% Example M13 CC-3-V 32.0% Clearing point [° C.]: 96.0 CC-3-V1 12.0% Δn [589 nm, 20° C.]: 0.1092 CCP-V2-1 9.0% Δε [1 kHz, 20° C.]: 15.0 CCGU-3-F 4.0% γ.sub.1 [mPa .Math. s, 20° C.]: 108 APUQU-2-F 9.0% V.sub.0 [V]: 1.03 APUQU-3-F 9.0% PGUQU-3-F 6.0% PGUQU-4-F 6.0% PGUQU-5-F 4.0% CDUQU-3-F 9.0% Example M14 CC-3-V 31.0% Clearing point [° C.]: 96.0 CC-3-V1 12.0% Δn [589 nm, 20° C.]: 0.1087 CCP-V2-1 5.0% Δε [1 kHz, 20° C.]: 15.2 CCGU-3-F 3.0% γ.sub.1 [mPa .Math. s, 20° C.]: 106 CCQU-3-F 11.0% V.sub.0 [V]: 1.03 APUQU-2-F 10.0% APUQU-3-F 10.0% PGUQU-3-F 5.0% PGUQU-4-F 6.0% DPGU-4-F 7.0%