Components for high-frequency technology, and liquid-crystalline media

Abstract

A component for high-frequency technology or for the microwave range and millimeter wave range of the electromagnetic spectrum. The component contains a liquid-crystal compound of the formula I ##STR00001##
in which the parameters have the respective meanings given in the claims or in the text, or a liquid-crystal medium which itself comprises one or more compounds of this formula I. Also, the corresponding, novel liquid-crystal media, the use and preparation thereof, and the production and use of the components. The components are particularly suitable as phase shifters in the microwave and millimeter wave range, for microwave and millimeter wave array antennae and very particularly for so-called tuneable reflectarrays.

Claims

1. Component which operates in the microwave range or millimeter wave range of the electromagnetic spectrum, wherein the component is selected from the group consisting of the following components: wireless and radiowave antenna arrays; microwave antenna arrays; and devices selected from the group consisting of the following devices: phase shifters; varactors; and matching circuit adaptive filters; and wherein the component comprises a liquid-crystal medium, wherein the medium comprises two or more compounds of the formula I, wherein the concentration of all of the compounds of formula I is 30 to 95% by weight, based on the total weight of the medium, ##STR00210## in which R.sup.11 and R.sup.12, independently of one another, denote unfluorinated alkyl having 1 to 15 C atoms, or unfluorinated alkenyl having 2 to 15 C atoms, R.sup.13 denotes ethyl or cycloalkyl having 3 to 6 carbon atoms, provided that: the liquid-crystal medium contains one or more compounds of the formula I-2 ##STR00211## and contains one or more compounds of the formula I-3 ##STR00212## wherein A.sup.1 denotes cycloalkyl having 3 to 6 C atoms; and wherein the liquid-crystal medium additionally comprises one or more components selected from the group of the following components, components B and D to E, a strongly dielectrically positive component, component B, which has a dielectric anisotropy of 10 or more, a component, component D, which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and comprises one or more compounds of the following formula IV: ##STR00213## in which R.sup.41 and R.sup.42, independently of one another, denote unfluorinated alkyl or unfluorinated alkoxy, each having 1 to 15 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms, L.sup.41 to L.sup.44 on each appearance, in each case independently of one another, denote H, alkyl having 1 to 5 C atoms, F or Cl, provided that at least two of the substituents L.sup.41 to L.sup.44 are not H, and P denotes an integer in the range from 7 to 14; and a component, component E, which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and comprises one or more compounds of the formulae V to IX: ##STR00214## in which L.sup.51 denotes R.sup.51 or X.sup.51, L.sup.52 denotes R.sup.52 or X.sup.52, R.sup.51 and R.sup.52, independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, X.sup.51 and X.sup.52, independently of one another, denote H, F, Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms, and ##STR00215##  independently of one another, denote ##STR00216## L.sup.61 denotes R.sup.21 and, in the case where Z.sup.61 and/or Z.sup.62 denote trans-CH═CH— or trans-CF═CF—, alternatively denotes X.sup.21, L.sup.62 denotes R.sup.62 and, in the case where Z.sup.61 and/or Z.sup.62 denote trans-CH═CH— or trans-CF═CF—, alternatively denotes X.sup.62, R.sup.61 and R.sup.62, independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, X.sup.61 and X.sup.62, independently of one another, denote F or Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or alkoxy having 1 to 7 C atoms or fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 7 C atoms, one of Z.sup.61 and Z.sup.62 denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other, independently thereof, denotes trans-CH═CH—, trans-CF═CF— or a single bond, and ##STR00217##  independently of one another, denote ##STR00218## L.sup.71 denotes R.sup.71 or X.sup.71, L.sup.72 denotes R.sup.72 or X.sup.72, R.sup.71 and R.sup.72, independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, X.sup.71 and X.sup.72, independently of one another, denote H, F, Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms, and Z.sup.71 to Z.sup.73, independently of one another, denote trans-CH═CH—, trans-CF═CF—, —C≡C— or a single bond, and ##STR00219##  independently of one another, denote ##STR00220## R.sup.81and R.sup.82, independently of one another, denote H, unfluorinated alkyl or alkoxy having 1 to 15 C atoms or unfluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 15 C atoms, one of Z.sup.81and Z.sup.82 denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other, independently thereof, denotes trans-CH═CH—, trans-CF═CF— or a single bond, and ##STR00221##  independently of one another, denote ##STR00222## L.sup.91 denotes R.sup.91 or X.sup.91, L.sup.92 denotes R.sup.92 or X.sup.92, R.sup.91 and R.sup.92, independently of one another, denote H, unfluorinated alkyl or alkoxy having 1 to 15 C atoms or unfluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 15 C atoms, X.sup.91 and X.sup.92, independently of one another, denote H, F, Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms, and Z.sup.91 to Z.sup.93, independently of one another, denote trans-CH═CH—, trans-CF═CF—, —C≡C— or a single bond, ##STR00223##  independently of one another, denote ##STR00224## and where compounds of the formula IIIA ##STR00225## where R.sup.31 and R.sup.32 denote unfluorinated alkyl or unfluorinated alkoxy, each having 1 to 15 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, are excluded from the compounds of the formula VI.

2. Component according to claim 1, wherein the liquid-crystal medium additionally comprises: a strongly dielectrically negative component, component C, which has a dielectric anisotropy having a value of −5.0 or less.

3. Component according to claim 1, characterised in that the liquid-crystal medium comprises a component B.

4. Component according to claim 1, characterised in that the liquid-crystal medium comprises a component D.

5. Liquid-crystal medium, characterised in that it comprises a component A comprising two or more compounds of the formula I wherein the concentration of all of the compounds of formula I is 30 to 95% by weight, based on the total weight of the medium, ##STR00226## in which R.sup.11 and R.sup.12, independently of one another, denote unfluorinated alkyl having 1 to 15 C atoms, or unfluorinated alkenyl having 2 to 15 C atoms, R.sup.13 denotes ethyl or cycloalkyl having 3 to 6 carbon atoms, provided that: the liquid-crystal medium contains one or more compounds of the formula I-2 ##STR00227## and contains one or more compounds of the formula I-3 ##STR00228## wherein A.sup.1 denotes cycloalkyl having 3 to 6 C atoms, and additionally comprises one or more components selected from the group of the following components B, D and E: a strongly dielectrically positive component, component B, which has a dielectric anisotropy of 10 or more, a component, component D, which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and comprises one or more compounds of the following formula IV: ##STR00229## in which R.sup.41 and R.sup.42, independently of one another, denote unfluorinated alkyl or unfluorinated alkoxy, each having 1 to 15 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms, L.sup.41 to L.sup.44 on each appearance, in each case independently of one another, denote H, alkyl having 1 to 5 C atoms, F or Cl, provided that at least two of the substituents L.sup.41 to L.sup.44 are not H, and P denotes an integer in the range from 7 to 14; and a component, component E, which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and comprises one or more compounds of the formulae V to IX: ##STR00230## in which L.sup.51 denotes R.sup.51 or X.sup.51, L.sup.52 denotes R.sup.52 or X.sup.52, R.sup.51 and R.sup.52, independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, X.sup.51 and X.sup.52, independently of one another, denote H, F, Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms, provided that X.sup.51 is not —CN, and ##STR00231##  independently of one another, denote ##STR00232## L.sup.61 denotes R.sup.21 and, in the case where Z.sup.61 and/or Z.sup.62 denote trans-CH═CH— or trans-CF═CF—, alternatively denotes X.sup.21, L.sup.62 denotes R.sup.62 and, in the case where Z.sup.61 and/or Z.sup.62 denote trans-CH═CH— or trans-CF═CF—, alternatively denotes X.sup.62, R.sup.61 and R.sup.62, independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, X.sup.61 and X.sup.62, independently of one another, denote F or Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or alkoxy having 1 to 7 C atoms or fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 7 C atoms, one of Z.sup.61 and Z.sup.62 denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other, independently thereof, denotes trans-CH═CH—, trans-CF═CF— or a single bond, and ##STR00233##  independently of one another, denote ##STR00234## L.sup.71 denotes R.sup.71 or X.sup.71, L.sup.72 denotes R.sup.72 or X.sup.72, R.sup.71 and R.sup.72, independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, X.sup.71 and X.sup.72, independently of one another, denote H, F, Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms, provided that X.sup.71 is not —CN, and Z.sup.71 to Z.sup.73 , independently of one another, denote trans-CH═CH—, trans-CF═CF—, —C≡C— or a single bond, and ##STR00235##  independently of one another, denote ##STR00236## R.sup.81 and R.sup.82, independently of one another, denote H, unfluorinated alkyl or alkoxy having 1 to 15 C atoms or unfluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 15 C atoms, one of Z.sup.81 and Z.sup.82 denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other, independently thereof, denotes trans-CH═CH—, trans-CF═CF— or a single bond, and ##STR00237##  independently of one another, denote ##STR00238## L.sup.91 denotes R.sup.91 or X.sup.91, L.sup.92 denotes R.sup.92 or X.sup.92, R.sup.91 and R.sup.92, independently of one another, denote H, unfluorinated alkyl or alkoxy having 1 to 15 C atoms or unfluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 15 C atoms, X.sup.91 and X.sup.92, independently of one another, denote H, F, Cl, —CN, —NCS, —SF.sub.5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms, and Z.sup.91 to Z.sup.93, independently of one another, denote trans-CH═CH—, trans-CF═CF—, —C≡C— or a single bond, ##STR00239##  independently of one another, denote ##STR00240## and where compounds of the formula IIIA ##STR00241## where R.sup.31 and R.sup.32 denote unfluorinated alkyl or unfluorinated alkoxy, each having 1 to 15 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, are excluded from the compounds of the formula VI.

6. Liquid-crystal medium according to claim 5, characterised in that the liquid-crystal medium comprises a component B.

7. Liquid-crystal medium according to claim 5, characterised in that the liquid-crystal medium further comprises a component C which is a strongly dielectrically negative component which has a dielectric anisotropy having a value of −5.0 or less.

8. Process for the preparation of a liquid-crystal medium according to claim 5, characterised in that compounds of the formula I, are mixed with one or more further compounds and/or with one or more additives, including one or more components selected from components B, D and E.

9. Process for the production of a component according to claim 1, comprising adding the liquid crystal medium to the component.

10. Microwave antenna array, characterised in that it comprises one or more components according to claim 1.

11. Component according to claim 1, wherein the liquid-crystal medium comprises a component E and wherein X.sup.51 and X.sup.71 are not —CN.

12. Liquid-crystal medium according to claim 5, wherein the liquid-crystal medium comprises a component D.

13. Liquid-crystal medium according to claim 8, wherein the liquid-crystal medium comprises a component E.

14. Component according to claim 1, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.20 or more.

15. Liquid-crystal medium according to claim 5, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.20 or more.

16. Component according to claim 1, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.30 or more.

17. Liquid-crystal medium according to claim 5, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.30 or more.

18. Component according to claim 1, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.40 or more.

19. Liquid-crystal medium according to claim 5, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.40 or more.

20. Component according to claim 14, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.80 or less.

21. Liquid-crystal medium according to claim 15, wherein the liquid-crystal medium has a birefringence at a wavelength of 589 nm of 0.80 or less.

22. Component according to claim 1, wherein the medium comprises the two or more compounds of the formula I, wherein the concentration of all of the compounds of formula I is 40 to 90% by weight, based on the total weight of the medium.

23. Liquid-crystal medium according to claim 5, wherein the medium comprises the two or more compounds of the formula I, wherein the concentration of all of the compounds of formula I is 40 to 90% by weight, based on the total weight of the medium.

24. Component according to claim 4, wherein the medium consists essentially of the two or more compounds of the formula I and the component D.

25. Liquid-crystal medium according to claim 12, wherein the medium consists essentially of the two or more compounds of the formula I and the component D.

26. Component according to claim 4, wherein the medium comprises 80% by weight or more of the two or more compounds of the formula I, the component D and the optional components B and E.

27. Liquid-crystal medium according to claim 12, wherein the medium comprises 80% by weight or more of the two or more compounds of the formula I, the component D and the optional components B and E.

28. Component according to claim 1, wherein the component operates in the frequency range of from 5 GHz to 150 GHz.

29. Component according to claim 4, wherein the medium consists essentially of the two or more compounds of the formula I, the component D, and the component B.

30. Liquid-crystal medium according to claim 12, wherein the medium consists essentially of the two or more compounds of the formula I, the component D, and the component B.

31. Component according to claim 4, wherein the medium consists essentially of the two or more compounds of the formula I, the component D, and the component E.

32. Liquid-crystal medium according to claim 12, wherein the medium consists essentially of the two or more compounds of the formula I, the component D, and the component E.

Description

EXAMPLES

(1) The following examples illustrate the present invention without limiting it in any way. However, it becomes clear to the person skilled in the art from the physical properties what properties can be achieved and in what ranges they can be modified. In particular, the combination of the various properties which can preferably be achieved is thus well defined for the person skilled in the art.

Example 1

(2) A liquid-crystalline substance having the abbreviated name PTP(2)TP-6-3 is prepared by the method of Hsu, C. S., Shyu, K. F., Chuang, Y. Y. and Wu, S.-T., Liq. Cryst., 27 (2), (2000), pp. 283-287 and investigated with respect to its physical properties, in particular in the microwave range. The compound has a nematic phase and a clearing point (T(N,I)) of 114.5° C. Further physical properties at 20° C. are: n.sub.e(589.3 nm)=1.8563; Δn(589.3 nm)=0.3250; ε.sub.∥(1 kHz)=; Δε(1 kHz) and γ.sub.1=2.100 mPa.Math.s. The compound is suitable for applications in the microwave range, in particular for phase shifters. For comparison, the following values are obtained with the compound 4′-pentyl-4-cyanobiphenyl (also known as 5CB or K15, Merck KGaA) at 20° C.

(3) TABLE-US-00007 TABLE 1a Properties of the compound PTP(2)TP-6-3 at 30 GHz T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ tan δ.sub.ε,r,⊥ η 20 3.22 2.44 0.242 0.0018 0.0064 37.9

(4) TABLE-US-00008 TABLE 1b Properties of the compound K15 at 30 GHz tan T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ δ.sub.ε,r,⊥ η 20 2.87 2.55 0.110 0.0114 0.026 4.3

(5) TABLE-US-00009 TABLE 2 Comparison of the properties of the various examples at 30 GHz and at 20° C. Liquid Example crystal ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.εr,max. η Comparison K15 2.87 2.55 0.110 0.0262  4.3 1 P2-6-3* 3.22 2.44 0.242 0.0064 37.9 2 M-1 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 3 M-2 3.21 2.39 0.256 0.0070 35.5 4 M-3 3.20 2.45 0.234 0.0068 34.5 5 M-4 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 6 M-5 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 7 M-6 3.26 2.46 0.245 0.0069 35.6 8 M-7 3.20 2.42 0.244 0.0082 30.0 9 M-8 3.24 2.45 0.244 0.0083 29.4 10 M-9 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 11 M-10 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 12 M-11 3.19 2.42 0.241 0.0075 33.0 13 M-12 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 14 M-13 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 15 M-14 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 16 M-15 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 17 M-16 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 18 M-17 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 19 M-18 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 20 M-19 0.224 18.3 21 M-20 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 22 M-21 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. 23 M-22 t.b.d. t.b.d. t.b.d. t.b.d. t.b.d. Notes: *P2-6-3: PTP(2)TP-6-3 and t.b.d.: to be determined.

Example 2

(6) A liquid-crystal mixture M-1 having the composition and properties as indicated in the following table is prepared.

(7) TABLE-US-00010 Composition Compound No. Abbreviation 1 PTP(2)TP-3-3 25.0 2 PTP(2)TP-4-3 25.0 3 PTP(2)TP-6-3 50.0 Σ 100.0 Physical properties T(N, I) = 123.0° C. ε.sub.∥ (20° C., 1 kHz) = 3.4 Δε (20° C., 1 kHz) = 0.8 Note: The compounds PTP(2)TP-3-3 and PTP(2)TP-4-3 are prepared analogously to the compound of Example 1.

(8) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 3

(9) A liquid-crystal mixture M-2 having the composition and properties as indicated in the following table is prepared.

(10) TABLE-US-00011 Composition Compound No. Abbreviation 1 PTP(1)TP-3-6 11.0 2 PTP(1)TP-3-O5 5.0 3 PTP(2)TP-3-6 15.0 4 PTP(2)TP-6-3 63.0 5 PTP(2)TP-3-O5 6.0 Σ 100.0 Physical properties T(N, I) = 129.5° C. n.sub.e (20° C., 589.3 nm) = 1.8721 Δn (20° C., 589.3 nm) = 0.3430 ε.sub.∥ (20° C., 1 kHz) = 3.3 Δε (20° C., 1 kHz) = 0.7

(11) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

(12) TABLE-US-00012 TABLE 3 Properties of mixture M-2 at 30 GHz T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ tan δ.sub.ε,r,⊥ η 20 3.21 2.39 0.256 0.0020 0.0070 35.5

Example 4

(13) A liquid-crystal mixture M-3 having the composition and properties as indicated in the following table is prepared.

(14) TABLE-US-00013 Composition Compound No. Abbreviation 1 PTP(2)TP-3-3 40.0 2 PTP(2)TP-6-3 20.0 3 PTP(2)TP-3-O5 20.0 4 PTP(c6)TP-3-6 20.0 Σ 100.0 Physical properties T(N, I) = 112.5° C. ε.sub.∥ (20° C., 1 kHz) = 3.5 Δε (20° C., 1 kHz) = 0.8 Note: The compounds are all prepared analogously to the compound of Example 1. The compound PTP(c6)TP-3-6 has a glass transition temperature (T.sub.g) of −23° C.

(15) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

(16) TABLE-US-00014 TABLE 4 Properties of mixture M-3 at 30 GHz T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ tan δ.sub.ε,r,⊥ η 20 3.20 2.45 0.234 0.0023 0.0068 34.5

Example 5

(17) A liquid-crystal mixture M-4 having the composition and properties as indicated in the following table is prepared.

(18) TABLE-US-00015 Composition Compound No. Abbreviation 1 PTP(2)TP-3-3 40.0 2 PTP(2)TP-6-3 20.0 3 PTP(2)TP-3-O5 20.0 4 PTP(c3)TP-4-4 20.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Notes: t.b.d.: to be determined. The compounds are all prepared analogously to the compound of Example 1. The compound PTP(c3)TP-4-4 has a nematic phase and a clearing point of 84.5° C.

(19) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 6

(20) A liquid-crystal mixture M-5 having the composition and properties as indicated in the following table is prepared.

(21) TABLE-US-00016 Composition Compound No. Abbreviation 1 PTP(2)TP-3-3 40.0 2 PTP(2)TP-6-3 20.0 3 PTP(2)TP-3-O5 20.0 4 PTP(c4)TP-4-4 20.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Notes: t.b.d.: to be determined. The compounds are all prepared analogously to the compound of Example 1. The compound PTP(c4)TP-4-4 has a nematic phase and a clearing point of 70.1° C.

(22) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 7

(23) A liquid-crystal mixture M-6 having the composition and properties as indicated in the following table is prepared.

(24) TABLE-US-00017 Composition Compound No. Abbreviation 1 PTP(2)TP-2-2 15.0 2 PTP(2)TP-3-3 20.0 3 PTP(2)TP-6-3 30.0 4 PTP(2)TP-3-O5 15.0 5 PTP(c6)TP-3-6 20.0 Σ 100.0 Physical properties T(N, I) = 105.0° C. ε.sub.∥ (20° C., 1 kHz) = 3.5 Δε (20° C., 1 kHz) = 0.8

(25) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

(26) TABLE-US-00018 TABLE 5 Properties of mixture M-6 at 30 GHz T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ tan δ.sub.ε,r,⊥ η 20 3.26 2.46 0.245 0.0020 0.0069 35.6

Example 8

(27) A liquid-crystal mixture M-7 having the composition and properties as indicated in the following table is prepared.

(28) TABLE-US-00019 Composition Compound No. Abbreviation 1 PTP(1)TP-3-6 15.0 2 PTP(2)TP-3-6 10.0 3 PTP(2)TP-6-3 55.0 4 PTP(2)TP-3-O5 5.0 5 PGUQU-3-F 5.0 6 PGUQU-4-F 5.0 7 PGUQU-5-F 5.0 Σ 100.0 Physical properties T(N, I) = 124.5° C. ε.sub.∥ (20° C., 1 kHz) = 7.4 Δε (20° C., 1 kHz) = 4.5 γ.sub.1 (20° C.) = 1.637 mPa .Math. s

(29) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

(30) TABLE-US-00020 TABLE 6 Properties of mixture M-7 at 30 GHz T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ tan δ.sub.ε,r,⊥ η 10.0 3.21 2.41 0.248 0.0021 0.0070 35.3 20.0 3.20 2.42 0.244 0.0024 0.0082 30.0 30.0 3.19 2.42 0.240 0.0027 0.0093 26.0 40.0 3.17 2.42 0.236 0.0030 0.0104 22.6 50.0 3.15 2.42 0.231 0.0035 0.0115 20.1

Example 9

(31) A liquid-crystal mixture M-8 having the composition and properties as indicated in the following table is prepared.

(32) TABLE-US-00021 Composition Compound No. Abbreviation 1 PTP(1)TP-6-3 17.2 2 PTP(2)TP-3-3 34.4 3 PTP(2)TP-3-O5 17.2 4 PTP(c6)TP-3-6 17.2 5 PGUQU-3-F 7.0 6 PGUQU-5-F 7.0 Σ 100.0 Physical properties T(N, I) = 108.5° C. ε.sub.∥ (20° C., 1 kHz) = 7.0 Δε (20° C., 1 kHz) = 4.0 γ.sub.1 (20° C.) = 1.126 mPa .Math. s

(33) TABLE-US-00022 TABLE 7 Properties of mixture M-8 at 30 GHz T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ tan δ.sub.ε,r,⊥ η 20 3.24 2.45 0.244 0.0024 0.0083 29.4

Example 10

(34) A liquid-crystal mixture M-9 having the composition and properties as indicated in the following table is prepared.

(35) TABLE-US-00023 Composition Compound No. Abbreviation 1 PTP(1)TP-6-3 17.2 2 PTP(2)TP-3-3 34.4 3 PTP(2)TP-3-O5 17.2 4 PTP(c3)TP-4-4 17.2 5 PGUQU-3-F 7.0 6 PGUQU-5-F 7.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Note: t.b.d.: to be determined.

Example 11

(36) A liquid-crystal mixture M-10 having the composition and properties as indicated in the following table is prepared.

(37) TABLE-US-00024 Composition Compound No. Abbreviation 1 PTP(1)TP-6-3 17.2 2 PTP(2)TP-3-3 34.4 3 PTP(2)TP-3-O5 17.2 4 PTP(c4)TP-4-4 17.2 5 PGUQU-3-F 7.0 6 PGUQU-5-F 7.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Note: t.b.d.: to be determined.

Example 12

(38) A liquid-crystal mixture M-11 having the composition and properties as indicated in the following table is prepared.

(39) TABLE-US-00025 Composition Compound No. Abbreviation 1 PTP(1)TP-3-6 15.0 2 PTP(2)TP-3-6 20.0 3 PTP(2)TP-6-3 45.0 4 PTP(2)TP-3-O5 10.0 5 CPWZG-3-N 10.0 Σ 100.0 Physical properties T(N, I) = 139.5° C. ε.sub.∥ (20° C., 1 kHz) = 5.0 Δε (20° C., 1 kHz) = 2.0 Notes: CPWZG-3-N: (phases: C 104 SA (79) N 169.4 I)

(40) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

(41) TABLE-US-00026 TABLE 8 Properties of mixture M-11 at 30 GHz T/° C. ε.sub.r,∥ ε.sub.r,⊥ τ tan δ.sub.ε,r,∥ tan δ.sub.ε,r,⊥ η 20 3.19 2.42 0.241 0.0020 0.0075 33.0

Example 13

(42) A liquid-crystal mixture M-12 having the composition and properties as indicated in the following table is prepared.

(43) TABLE-US-00027 Composition Compound No. Abbreviation 1 PTP(2)TP-6-3 60.0 2 PTYY-3-O2 10.0 3 PTYY-3-O3 15.0 4 PTYY-3-O4 15.0 Σ 100.0 Physical properties T(N, I) = 141.5° C. ε.sub.∥ (20° C., 1 kHz) = 6.0 Δε (20° C., 1 kHz) = −0.5

(44) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 14

(45) A liquid-crystal mixture M-13 having the composition and properties as indicated in the following table is prepared.

(46) TABLE-US-00028 Composition Compound No. Abbreviation 1 PTP(2)TP-6-3 75.0 2 PfX-5-O4 25.0 Σ 100.0 Physical properties T(N, I) = 137.5° C. ε.sub.∥ (20° C., 1 kHz) = 5.2 Δε (20° C., 1 kHz) = −0.5

(47) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 15

(48) A liquid-crystal mixture M-14 having the composition and properties as indicated in the following table is prepared.

(49) TABLE-US-00029 Composition Compound No. Abbreviation 1 PTP(1)TP-3-6 10.0 2 PTP(2)TP-3-6 15.0 3 PTP(2)TP-6-3 35.0 4 PTYY-3-O2 5.0 5 PTYY-3-O3 10.0 6 PTYY-3-O4 10.0 7 PfX-5-O4 15.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Note: t.b.d.: to be determined.

(50) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 16

(51) A liquid-crystal mixture M-15 having the composition and properties as indicated in the following table is prepared.

(52) TABLE-US-00030 Composition Compound No. Abbreviation 1 PTP(2)TP-3-1 10.0 2 PTP(2)TP-6-3 63.0 3 PTP(2)TP-3-O5 10.0 4 PGUQU-3-F 5.0 5 PU[QGU].sub.2-3-F 5.0 6 PU[QGU].sub.2-5-F 7.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Notes: PU[QGU].sub.2-5-F: PUQGUQGU-5-F (phases: C 86 N 236.4 I) PU[QGU].sub.2.sup.(3)-5-F: PUQGU(3)QGU-5-F (phases: C 80° C. S.sub.A (39) N 100.6 I) and t.b.d.: to be determined.

Example 17

(53) A liquid-crystal mixture M-16 having the composition and properties as indicated in the following table is prepared.

(54) TABLE-US-00031 Composition Compound No. Abbreviation 1 PTP(2)TP-6-3 85.0 2 PU[QGU].sub.2-5-F 10.0 3 PU[QGU].sub.2.sup.(3)-5-F 5.0 Σ 100.0 Physical properties T(N, I) = 118.5° C. ε.sub.∥ (20° C., 1 kHz) = 5.7 Δε (20° C., 1 kHz) = 2.8 k.sub.1 (20° C.) = 13.9 k.sub.3 (20° C.) = 35.7 Notes: PU[QGU].sub.2-3-F: PUQGUQGU-3-F, PU[QGU].sub.2-5-F: PUQGUQGU-5-F.

Example 18

(55) A liquid-crystal mixture M-17 having the composition and properties as indicated in the following table is prepared.

(56) TABLE-US-00032 Composition Compound No. Abbreviation 1 PTP(c3)TP-4-4 15.0 2 GGP-3-CL 10.0 3 GGP-5-CL 20.0 4 PPTUI-3-2 20.0 5 PPTUI-3-4 20.0 6 PPTUI-4-4 5.0 7 CPGP-5-2 5.0 8 CPGP-5-2 5.0 Σ 100.0 Physical properties T(N, I) = 152.0° C. T(S, N) < −20° C. ε.sub.∥ (20° C., 1 kHz) = 7.6 Δε (20° C., 1 kHz) = 4.1

(57) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 19

(58) A liquid-crystal mixture M-18 having the composition and properties as indicated in the following table is prepared.

(59) TABLE-US-00033 Composition Compound No. Abbreviation 1 PTP(c3)TP-4-4 20.0 2 GGP-3-CL 10.0 3 GGP-5-CL 20.0 4 PPTUI-3-4 20.0 5 PPTUI-4-4 20.0 6 CPGP-5-2 5.0 7 CPGP-5-2 5.0 Σ 100.0 Physical properties T(N, I) = 145.5° C. T(C, I) = −10° C. ε.sub.∥ (20° C., 1 kHz) = 7.0 Δε (20° C., 1 kHz) = 4.0 γ.sub.1 (20° C.) = 1.237 mPa .Math. s k.sub.1 (20° C.) = 15.9 k.sub.3 (20° C.) = 27.5 V.sub.0 (20° C.) = 2.11 V

(60) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

(61) TABLE-US-00034 TABLE 9 Properties of mixture M-18 at 30 GHz T/° C. τ η 10.0 0.227 22.0 20.0 0.224 18.3 30.0 0.220 15.2 40.0 0.215 13.4 50.0 0.211 11.7 60.0 0.207 10.4 70.0 0.202 9.1 80.0 0.196 8.0 90.0 0.190 7.2 92.3 0.188 7.0

Example 20

(62) A liquid-crystal mixture M-19 having the composition and properties as indicated in the following table is prepared.

(63) TABLE-US-00035 Composition Compound No. Abbreviation 1 PTP(2)TP-6-3 20.0 2 PTP(c3)TP-4-4 5.0 Σ 100.0 Physical properties T(N, I) = 113.5° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Note: t.b.d.: to be determined.

(64) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 21

(65) A liquid-crystal mixture M-20 having the composition and properties as indicated in the following table is prepared.

(66) TABLE-US-00036 Composition Compound No. Abbreviation 1 PTP(2)TP-2-2 20.0 2 PTP(2)TP-3-3 30.0 3 PTP(2)TP-6-3 10.0 4 PTP(c6)TP-3-6 20.0 5 PTP(2)TP-3-O5 20.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Note: t.b.d.: to be determined.

(67) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 22

(68) A liquid-crystal mixture M-21 having the composition and properties as indicated in the following table is prepared.

(69) TABLE-US-00037 Composition Compound No. Abbreviation 1 PTP(2)TP-3-3 10.0 2 PTP(2)TP-3-6 10.0 3 PTP(2)TP-4-3 10.0 4 PTP(2)TP-6-3 70.0 Σ 100.0 Physical properties T(N, I) = t.b.d. ° C. ε.sub.∥ (20° C., 1 kHz) = t.b.d. Δε (20° C., 1 kHz) = t.b.d. Note: t.b.d.: to be determined.

(70) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.

Example 23

(71) A liquid-crystal mixture M-22 having the composition and properties as indicated in the following table is prepared.

(72) TABLE-US-00038 Composition Compound No. Abbreviation 1 PTP(2)TP-3-3 25.0 2 PTP(2)TP-4-3 25.0 3 PTP(2)TP-6-3 50.0 Σ 100.0 Physical properties T(N, I) = 123.0° C. ε.sub.∥ (20° C., 1 kHz) = 3.4 Δε (20° C., 1 kHz) = 0.8

(73) This mixture is very suitable for applications in the microwave range, in particular for phase shifters.