Isothiocyanato compounds, including tolanes

Abstract

Liquid-crystalline media comprising one or more compounds of formula T ##STR00001##
as defined in claim 1, and high-frequency components comprising these media, especially microwave components for high-frequency devices, such as devices for shifting the phase of microwaves, tunable filters, tunable metamaterial structures, and electronic beam steering antennas, e.g. phased array antennas.

Claims

1. A compound of formula T ##STR00420## in which R.sup.T denotes halogen, CN, NCS, R.sup.F, R.sup.F—O— or R.sup.F—S—, wherein R.sup.F denotes fluorinated alkyl having 1 to 12 C atoms or fluorinated alkenyl having 2 to 12 C atoms, ##STR00421## on each occurrence, independently of one another, denote ##STR00422## where ##STR00423## alternatively denote ##STR00424## in which one or two H atoms, identically or differently, are optionally replaced by a radical L.sup.1; L.sup.1 and L.sup.2 identically or differently, denote F, Cl straight chain alkyl having 1 to 12 C atoms, branched or cyclic alkyl having 3 to 12 C atoms or alkenyl having 2 to 12 C atoms; Z.sup.T1, Z.sup.T2 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C— or a single bond, wherein at least one of Z.sup.T1 and Z.sup.T2 denotes —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH— or —C≡C—, and t is 0 or 1.

2. The compound according to claim 1, wherein Z.sup.T1 and Z.sup.T2 denote a single bond or —C≡C— and wherein at least one of Z.sup.T1 and Z.sup.T2 denotes —C≡C—.

3. The compound according to claim 1, wherein the compound is selected from the compounds of the formulae T-1 to T-4 ##STR00425## in which L.sup.11 and L.sup.12 identically or differently, denote H, F, Cl, methyl or ethyl, L.sup.13, L.sup.14 and L.sup.15 identically or differently, denote H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl, R.sup.T denotes halogen, CN, NCS, R.sup.F, R.sup.F—O— or R.sup.F—S—, wherein R.sup.F denotes fluorinated alkyl having 1 to 12 C atoms or fluorinated alkenyl having 2 to 12 carbon atoms.

4. The compound according to claim 1, wherein R.sup.T denotes CF.sub.3 or CF.sub.3O.

5. A liquid crystal medium comprising one or more compounds of formula T according to claim 1.

6. The liquid crystal medium according to claim 5, wherein the medium further comprises one or more compounds selected from the group of compounds of the formulae I, II and III, ##STR00426## in which R.sup.1 denotes 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, in which one or more CH.sub.2-groups are optionally replaced by ##STR00427## n is 0, 1 or 2, ##STR00428## on each occurrence, independently of one another, denote ##STR00429## in which R.sup.L, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms, and wherein ##STR00430## alternatively denotes ##STR00431## R.sup.2 denotes 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, in which one or more CH.sub.2-groups are optionally replaced by ##STR00432## Z.sup.21 denotes trans-CH═CH—, trans-CF═CF— or and ##STR00433## independently of one another, denote ##STR00434## in which R.sup.L, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms; R.sup.3 denotes 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, in which one or more CH.sub.2-groups are optionally replaced by ##STR00435## one of Z.sup.3′ and Z.sup.32, denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other one, independently thereof, denotes trans-CH═CH—, trans-CF═CF— or a single bond, and ##STR00436## independently of one another, denote ##STR00437## in which R.sup.L, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms, and wherein ##STR00438## alternatively denotes ##STR00439##

7. The liquid-crystal medium according to claim 6, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae I-1 to I-5: ##STR00440## in which L.sup.1, L.sup.2 and L.sup.3 on each occurrence, identically or differently, denote H or F, and R.sup.1, ##STR00441## have the meanings given for formula I in claim 6.

8. The liquid-crystal medium according to claim 6, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae II-1 to II-3: ##STR00442## in which R.sup.2, ##STR00443## have the meanings given in claim 6 for formula II.

9. The liquid-crystal medium according to claim 6, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae III-1 to III-6: ##STR00444## in which R.sup.3, ##STR00445## have the meanings given in claim 6 for formula III, and Z.sup.31 and Z.sup.32 independently of one another, denote trans-CH═CH— or trans-CF═CF—, and in formula III-6 alternatively one of Z.sup.31 and Z.sup.32 may denote —C≡C—.

10. The liquid-crystal medium according to claim 5, wherein the medium further comprises one or more compounds of formula TA: ##STR00446## in which t is 0 or 1 and R.sup.T ##STR00447## have the meanings given for formula T.

11. The liquid-crystal medium according to claim 5, wherein the medium further comprises one or more chiral compounds.

12. The liquid-crystal medium according to claim 5, wherein the clearing temperature of the medium is 90° C. or more.

13. A component for high-frequency technology, which comprises the liquid crystal medium according to claim 5.

14. The component according to claim 13, wherein the component is a liquid-crystal based antenna element, a phase shifter, a tunable filter, a tunable metamaterial structure, a matching network or a varactor.

15. A microwave antenna array, which comprises one or more components according to claim 13.

Description

EXAMPLES

(1) The following examples illustrate the present invention without limiting it in any way.

(2) It is 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.

SYNTHESIS EXAMPLES

Synthesis Example 1: 1,3-difluoro-2-isothiocyanato-5-[2-methyl-4-[4-(trifluoromethoxy)phenyl]phenylethynyl]benzene

Step 1: 1-Bromo-2-methyl-4-[4-(trifluoromethoxy)phenyl]benzene

(3) ##STR00379##

(4) Tetrakis-(triphenylphosphin)-palladium-(0) (2.0 g; 1.7 mmol) is added to a mixture of 1-bromo-4-iodo-2-methyl-benzene (50.5 g, 170 mmol) and sodium carbonate (43.2 g, 408 mmol) in toluene (250 mL) and water (150 mL) at 80° C., followed by dropwise addition of a solution of [4-(trifluoromethoxy)phenyl]boronic acid (35.0 g, 170 mmol) in ethanol (40 mL). The reaction mixture is heated at reflux temperature overnight. Then it is quenched with water and MTB-ether. The aqueous phase is separated and extracted with MTB-ether, and the combined organic phases are washed with water, dried (sodium sulphate) and concentrated i. vac. The residue is purified by flash chromatography (heptane) to give 1-bromo-2-methyl-4-[4-(trifluoromethoxy)phenyl]benzene as a colourless oil.

Step 2: 2,6-Difluoro-4-[2-methyl-4-[4-(trifluoromethoxy)phenyl]-phenylethynyl]aniline

(5) ##STR00380##

(6) 1-Bromo-2-methyl-4-[4-(trifluoromethoxy)phenyl]benzene (52.2 g, 158 mmol), 4-ethynyl-2,6-difluoro-aniline (23.0 g, 150 mmol) and diisopropylamine (360 mL) are dissolved in THE (400 mL) and heated to 70° C. under nitrogen. XPhos PD G2 (236 mg, 0.30 mmol), XPhos (143 mg, 0.30 mmol) and copper(I)-iodide (29 mg, 0.15 mmol) are added, and the reaction mixture is stirred at 70° C. overnight. It is filtered, and the filtrate is concentrated in vacuo. The residue is purified by flash chromatography (heptane/MTB-ether 5/1) to give 2,6-difluoro-4-[2-methyl-4-[4-(trifluoromethoxy)phenyl]phenylethynyl]aniline, which is crystallized (heptane/ethanol 3/1) to give the pure product as beige crystals.

Step 3:1,3-Difluoro-2-isothiocyanato-5-[2-methyl-4-[4-(trifluoromethoxy)phenyl]phenylethynyl]benzene

(7) ##STR00381##

(8) Alternative 1: A solution of 2,6-difluoro-4-[2-methyl-4-[4-(trifluoromethoxy)phenyl]phenylethynyl]aniline (3.2 g, 8 mmol) in dichloromethane (35 mL) and DMF (1.2 mL, 16 mmol) is treated with 1,1-thiocarbonyldiimidazole (3.0 g, 16 mmol) at room temperature. The reaction mixture is stirred overnight at 28° C., then a second portion of 1,1-thiocarbonyldiimidazole (1.5 g, 8 mmol) is added, and the reaction mixture is stirred overnight. It is concentrated i. vac. and purified by flash chromatography (heptane/MTB 5/1) followed by crystallization from heptane to give 1,3-difluoro-2-isothiocyanato-5-[2-methyl-4-[4-(trifluoromethoxy)-phenyl]phenylethynyl]benzene.

(9) Alternative 2:

(10) To a mixture of 2,6-difluoro-4-[2-methyl-4-[4-(trifluoromethoxy)phenyl]phenylethynyl]aniline (48.0 g, 119 mmol) and 1,4-diazabicyclo[2.2.2]octane (33.4 g, 298 mmol) in dichloromethane (450 mL) thiophosgene (10.3 mL, 131 mmol) is added dropwise at 0° C. The reaction mixture is stirred for 1 h at room temperature. It is hydrolyzed with saturated NaC-solution. The aqueous phase is separated and extracted with dichloromethane, and the combined organic phases are washed with water, dried (sodium sulphate) and concentrated in vacuo. The residue is purified by flash chromatography (heptane) to give 1,3-difluoro-2-isothiocyanato-5-[2-methyl-4-[4-(trifluoromethoxy)phenyl]phenylethynyl]benzene as a yellow solid. Final crystallization (heptane) gives colourless crystals.

(11) Phase sequence K79 N185 I

(12) Δε=3.60

(13) Δn=0.4300

(14) γ.sub.1=862 mPa s

(15) In analogy to Synthesis Example 1 the following compounds are obtained:

(16) TABLE-US-00006 No. Compound 2 Phase sequence K 72 I Δε = 2.67 Δn = 0.3021 γ.sub.1 = 50 mPa s 3 Phase sequence K 82 I Δε = 1.35 Δn = 0.3179 4 Phase sequence K 62 I Δε = 2.51 Δn = 0.2584 γ.sub.1 = 62 mPa s 5 6 7 8 9 Phase sequence K 102 N 217 I Δε = 4.10 Δn = 0.4390 γ.sub.1 = 749 mPa s 10 0 11 12 13 14 Phase sequence K 99 N 168 I Δε = 1.72 Δn = 0.4209 γ.sub.1 = 593 mPa s 15 Phase sequence K 130 N 168 I Δε = 1.52 Δn = 0.4249 γ.sub.1 = 978 mPa s 16 17 18 19 Phase sequence K 102 N 217 I Δε = 4.10 Δn = 0.4390 γ.sub.1 = 749 mPa s 20 00 Phase sequence K 84 I Δε = 2.10 Δn = 0.3270 γ.sub.1 = 437 mPa s 21 01 Phase sequence K 85 N 130 I Δε = 4.70 Δn = 0.3890 γ.sub.1 = 1070 mPa s 22 02 Phase sequence K 118 N (114) I Δε = 4.70 Δn = 0.3890 γ.sub.1 = 1070 mPa s 23 03 24 04 25 05 26 06 27 07 28 08 29 09 30 0 31 Phase sequence K 97 N 212 I Δε = 2.50 Δn = 0.4250 γ.sub.1 = 454 mPa s 32 Phase sequence K 106 N 176 I Δε = 3.52 Δn = 0.4049 γ.sub.1 = 832 mPa s 33 34 35 Phase sequence K 65 N 172 I Δε = 3.09 Δn = 0.4086 γ.sub.1 = 623 mPa s 36 Phase sequence K 143 I Δε = 2.12 Δn = 0.3589 37 Phase sequence K 140 N 297 (decomp.) Δε = 4.52 Δn = 0.4889 γ.sub.1 = 2133 mPa s

MIXTURE EXAMPLES

(17) Liquid-crystal mixtures N1 to N51 having the compositions and properties as indicated in the following tables are prepared and characterized with respect to their general physical properties and their applicability in microwave components at 19 GHz and 2000. The mixture components are given as acronyms according to Tables A to C above. The individual proportions are % by weight.

(18) Mixture N1

(19) TABLE-US-00007 PTU-3-S 9.0 T.sub.(N,l) [° C.]: 161.5 PTU-5-S 9.0 τ [20° C., 19 GHz]: 0.347 PPTU-4-S 8.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7237 PPTU-5-S 8.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4320 PGTU-4-S 8.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0058 PGU-3-S 6.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0105 PPU-TO-S 15.0 η [20° C., 19 GHz]: 33.0 CPTU-4-S 8.0 CPTU-5-S 12.0 PPTU-TO-S 7.0 PP(1)TU-TO-S 10.0 Σ 100.0
Mixture N2

(20) TABLE-US-00008 PTU-3-S 9.0 T(N, l) [° C.]: 155 PTU-5-S 9.0 τ [20° C., 19 GHz]: 0.342 PPTU-4-S 8.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7961 PPTU-5-S 8.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4997 PGTU-4-S 8.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0059 PGU-3-S 6.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0107 PPU-TO-S 15.0 η [20° C., 19 GHz]: 32.0 CPTU-4-S 8.0 CPTU-5-S 12.0 PPTU-TO-S 7.0 ThTU-5-S 10.0 Σ 100.0
Mixture N3

(21) TABLE-US-00009 PTU-3-S 10.0 T(N, l) [° C.]: 158.5 PTU-5-S 10.0 τ [20° C., 19 GHz]: 0.346 PPTU-4-S 8.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7593 PPTU-5-S 11.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4601 PGTU-4-S 8.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0061 PGU-3-S 10.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0113 PPU-TO-S 20.0 η [20° C., 19 GHz]: 30.6 CPTU-5-S 13.0 PPTU-TO-S 10.0 Σ 100.0
Mixture N4

(22) TABLE-US-00010 PTU-3-S 10.0 T(N, l) [° C.]: 162.5 PTU-5-S 10.0 τ [20° C., 19 GHz]: 0.343 PPTU-4-S 8.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7299 PPTU-5-S 10.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4499 PGTU-4-S 6.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0060 PPU-TO-S 24.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0104 CPTU-4-S 8.0 η [20° C., 19 GHz]: 33.0 CPTU-5-S 14.0 PPTU-TO-S 10.0 Σ 100.0
Mixture N5

(23) TABLE-US-00011 PTU-3-S 10.0 PTU-5-S 10.0 PPTU-4-S 6.0 PPTU-5-S 12.0 PGU-3-S 14.0 PPU-TO-S 20.0 CPTU-4-S 20.0 PPTU-TO-S 8.0 Σ 100.0
Mixture N6

(24) TABLE-US-00012 PTU-3-S 10.0 PTU-5-S 10.0 PPTU-4-S 6.0 PPTU-5-S 12.0 PGU-3-S 14.0 PPU-TO-S 24.0 CPTU-4-S 12.0 PGTU-4-S 6.0 PPTU-TO-S 6.0 Σ 100.0
Mixture N7

(25) TABLE-US-00013 PTU-3-S 10.0 PTU-5-S 10.0 PPTU-4-S 6.0 PPTU-5-S 12.0 PGU-3-S 14.0 PPU-TO-S 20.0 PGTU-4-S 5.0 PGTU-5-S 5.0 PPTU-TO-S 5.0 PTPU-4-S 13.0 Σ 100.0
Mixture N8

(26) TABLE-US-00014 PTU-3-S 10.0 T(N, l) [° C.]: 157 PTU-5-S 10.0 LTS bulk [h, −30° C.]: 816 PPTU-4-S 6.0 τ [20° C., 19 GHz]: 0.342 PPTU-5-S 10.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7408 PGU-3-S 14.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4605 PPU-TO-S 22.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0061 CPTU-4-S 8.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0110 CPTU-5-S 12.0 η [20° C., 19 GHz]: 31.1 PPTU-TO-S 8.0 Σ 100.0
Mixture N9

(27) TABLE-US-00015 PTU-3-S 8.0 T(N, l) [° C.]: 159 PTU-5-S 8.0 τ [20° C., 19 GHz]: 0.346 PPTU-4-S 6.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7178 PPTU-5-S 10.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4300 PGTU-4-S 6.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0057 PGU-3-S 8.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0102 PPU-TO-S 15.0 η [20° C., 19 GHz]: 33.9 CPTU-4-S 8.0 CPTU-5-S 15.0 ThTU-5-S 10.0 PPTU-TO-S 6.0 Σ 100.0
Mixture N10

(28) TABLE-US-00016 PTU-3-S 9.0 T(N, l) [° C.]: 162 PTU-5-S 9.0 τ [20° C., 19 GHz]: 0.347 PPTU-4-S 6.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7249 PPTU-5-S 12.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4309 PGTU-4-S 7.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0058 PGU-3-S 6.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0104 PPU-TO-S 15.0 η [20° C., 19 GHz]: 33.4 CPTU-4-S 8.0 CPTU-5-S 12.0 PPTU-TO-S 6.0 PP(1)TU-TO-S 10.0 Σ 100.0
Mixture N11

(29) TABLE-US-00017 PTU-3-S 9.0 τ [20° C., 19 GHz]: 0.350 PTU-5-S 9.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7285 PPTU-4-S 6.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4236 PPTU-5-S 12.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0058 PGTU-4-S 7.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0104 PGU-3-S 6.0 η [20° C., 19 GHz]: 33.7 PPU-TO-S 15.0 CPTU-4-S 9.0 CPTU-5-S 9.0 PPTU-TO-S 6.0 PP(1)TU-TO-S 12.0 Σ 100.0
Mixture N12

(30) TABLE-US-00018 PTU-3-S 9.0 τ [20° C., 19 GHz]: 0.351 PTU-5-S 9.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7247 PPTU-4-S 6.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4157 PPTU-5-S 12.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0058 PGTU-4-S 7.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0104 PGU-3-S 6.0 η [20° C., 19 GHz]: 33.8 PPU-TO-S 15.0 CPTU-4-S 8.0 CPTU-5-S 8.0 PPTU-TO-S 6.0 PP(1)TU-TO-S 14.0 Σ 100.0
Mixture N13

(31) TABLE-US-00019 PTU-3-S 9.0 T(N, l) [° C.]: 160 PTU-5-S 9.0 τ [20° C., 19 GHz]: 0.348 PPTU-4-S 6.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7894 PPTU-5-S 12.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4700 PGTU-4-S 7.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0059 PGU-3-S 6.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0108 PPU-TO-S 15.0 η [20° C., 19 GHz]: 32.2 CPTU-4-S 7.0 CPTU-5-S 7.0 PPTU-TO-S 6.0 PP(1)TU-TO-S 16.0 Σ 100.0
Mixture N14

(32) TABLE-US-00020 PTU-3-S 9.0 PTU-5-S 9.0 PPTU-4-S 6.0 PPTU-5-S 12.0 PGTU-4-S 7.0 PGU-3-S 6.0 PPU-TO-S 11.0 CPTU-4-S 8.0 CPTU-5-S 12.0 PPTU-TO-S 8.0 PP(1)TU-TO-S 12.0 Σ 100.0
Mixture N15

(33) TABLE-US-00021 PTU-3-S 10.0 T(N, l) [° C.]: 160.6 PTU-5-S 10.0 τ [20° C., 19 GHz]: 0.346 PPTU-4-S 8.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7603 PPTU-5-S 10.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4585 PGTU-4-S 10.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0057 PPU-TO-S 10.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0104 CPTU-4-S 8.0 η [20° C., 19 GHz]: 33.3 CPTU-5-S 12.0 PPTU-TO-S 10.0 PP(1)TU-TO-S 12.0 Σ 100.0
Mixture N16

(34) TABLE-US-00022 PTU-3-S 10.0 T(N, l) [° C.]: 161 PTU-5-S 10.0 τ [20° C., 19 GHz]: 0.350 PPTU-4-S 10.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7728 PPTU-5-S 10.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4528 PGTU-4-S 10.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0057 PPU-TO-S 10.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0104 CPTU-4-S 10.0 η [20° C., 19 GHz]: 33.7 CPTU-5-S 10.0 PPTU-TO-S 10.0 PP(1)TU-TO-S 10.0 Σ 100.0
Mixture N17

(35) TABLE-US-00023 PTU-3-S 10.0 T(N, l) [° C.]: 153 PTU-5-S 10.0 τ [20° C., 19 GHz]: 0.340 PPTU-4-S 6.0 ε.sub.r,∥ [20° C., 19 GHz]: 3.7400 PPTU-5-S 10.0 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4679 PGU-3-S 6.0 tan δ.sub.εr,∥ [20° C., 19 GHz]: 0.0060 PPU-TO-S 22.0 tan δ.sub.εr,⊥ [20° C., 19 GHz]: 0.0106 CPTU-4-S 8.0 η [20° C., 19 GHz]: 32.1 CPTU-5-S 12.0 PPTU-TO-S 8.0 PP(2)TU-TO-S 8.0 Σ 100.0

(36) The liquid-crystalline media according to the invention exhibit high clearing temperatures in combination with very good LTS and excellent microwave application relevant properties.

(37) In a preferred embodiment the media according to the present invention comprise a stabiliser.

(38) The following Mixtures N18 to N34 are obtained from the mixtures N1 to 10 N17 using the stabiliser ST-3b-1 in the amounts given in Table 2.

(39) ##STR00418##

(40) TABLE-US-00024 TABLE 2 Mixture Example Host Mixture c(ST-3b-1) [%] N18 N1  0.12 N19 N2  0.90 N20 N3  0.10 N21 N4  0.11 N22 N5  0.12 N23 N6  0.13 N24 N7  0.12 N25 N8  0.12 N26 N9  0.12 N27 N10 0.12 N28 N11 0.13 N29 N12 0.14 N30 N13 0.15 N31 N14 0.17 N32 N15 0.10 N33 N16 0.10 N34 N17 0.10

(41) The following Mixtures N29 to N42 are obtained from the mixtures N1 to N14 using the stabiliser ST-3a-1 in the amounts given in Table 3.

(42) ##STR00419##

(43) TABLE-US-00025 TABLE 3 Mixture Example Host Mixture c(ST-3b-1) [%] N35 N1  0.12 N36 N2  0.90 N37 N3  0.10 N38 N4  0.11 N39 N5  0.12 N40 N6  0.13 N41 N7  0.12 N42 N8  0.12 N43 N9  0.12 N44 N10 0.12 N45 N11 0.13 N46 N12 0.14 N47 N13 0.15 N48 N14 0.17 N49 N15 0.12 N50 N16 0.12 N51 N17 0.12

(44) Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. The preceding preferred specific embodiments are, therefore, to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.

(45) The entire disclosure[s] of all applications, patents and publications, cited herein and of corresponding EP Patent Application No. 19171815, filed Apr. 30, 2019, is [are] incorporated by reference herein.

(46) The preceding examples can be repeated with similar success by substituting the generically or specifically described reactants and/or operating conditions of this invention for those used in the preceding examples.

(47) From the foregoing description, one skilled in the art can easily ascertain the essential characteristics of this invention and, without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.