FLUORINATED AROMATIC COMPOUNDS

Abstract

The present invention relates to aromatic isothiocyanates of formula U

##STR00001##

as defined in claim 1, to liquid-crystalline media comprising one or more compounds of formula U and to 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 U ##STR00439## in which R.sup.U denotes H, alkyl or alkoxy having 1 to 12 C atoms, or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12 C atoms, in which one or more CH.sub.2-groups may be replaced by ##STR00440## or a group R.sup.P, R.sup.P denotes halogen, CN, NCS, R.sup.F, R.sup.F—O— or R.sup.F—S—, wherein R.sup.F denotes fluorinated alkyl or fluorinated alkenyl having up to 9 C atoms, Z.sup.U1, Z.sup.U2, Z.sup.U3 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C— or a single bond, X.sup.1, X.sup.2 identically or differently, denote H, Cl, F, CH.sub.3 or C.sub.2H.sub.5, Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 identically or differently, denote H, F, Cl, or straight chain or branched or cyclic alkyl, alkenyl, alkoxy or alkenyloxy, each having up to 12 C atoms, where at least one of Y.sup.1, Y.sup.2, Y.sup.3 and Y.sup.4 is different from F, s is 0, 1 or 2, t is 0, 1 or 2, and s+t iso, 1 or 2, ##STR00441## identically or differently, denote a radical selected from the following groups: a) the group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by L, b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]pentane-1,3-diyl, 4,4″-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, in which one or more non-adjacent CH.sub.2 groups may be replaced by —O— and/or —S— and in which one or more H atoms may be replaced by F, and c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl, selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L, L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF.sub.5 or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms.

2. The compound according to claim 1, wherein ##STR00442## on each occurrence, independently of one another, denote ##STR00443## in which one or two CH-groups may be replaced by N, and wherein ##STR00444## alternatively denotes ##STR00445## and L.sup.1 and L.sup.2 identically or differently, denote F, Cl or straight chain or branched or cyclic alkyl or alkenyl each having up to 12 C atoms.

3. The compound according to claim 1, wherein Z.sup.U1 and Z.sup.U2, identically or differently, denote —C≡C— or a single bond.

4. The compound according to claim 1, wherein the compound is selected from the compounds of the formulae U-1 to U-20 ##STR00446## ##STR00447## ##STR00448## in which L.sup.1, L.sup.2 identically or differently, denote H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl, and R.sup.U, X.sup.1, X.sup.2, Y.sup.1, Y.sup.2, Y.sup.3 and Y.sup.4 have the meanings given for formula U.

5. The compound according to claim 1, wherein the radicals X.sup.1 and X.sup.2 denote H or F.

6. The compound according to claim 1, wherein the radicals Y.sup.1, Y.sup.2, Y.sup.3, and Y.sup.4, identically or differently, denote H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl.

7. The compound according to claim 1, wherein R.sup.U denotes alkyl having 1 to 12 C atoms.

8. The compound according to claim 1, wherein the group R.sup.U denotes R.sup.P.

9. A liquid crystal medium comprising one or more compounds according to claim 1.

10. The liquid crystal medium according to claim 9, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae I, II and III, ##STR00449## 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 may be replaced by ##STR00450## n is 0, 1 or 2, ##STR00451## to ##STR00452## on each occurrence, independently of one another, denote ##STR00453## in which R.sup.L, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms, and wherein ##STR00454## alternatively denotes ##STR00455## 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 may be replaced by ##STR00456## Z.sup.21 denotes trans-CH═CH—, trans-CF═CF— or —C≡C—, and ##STR00457## independently of one another, denote ##STR00458## 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 may be replaced by ##STR00459## one of Z.sup.31 and Z.sup.32, denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other one, independently thereof, denotes —C≡C—, trans-CH═CH—, trans-CF═CF— or a single bond, and ##STR00460## to ##STR00461## independently of one another, denote ##STR00462## in which R.sup.L, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms, and wherein ##STR00463## alternatively denotes ##STR00464## alternatively denotes ##STR00465##

11. The liquid crystal medium according to claim 10, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae I-1 to I-5 ##STR00466## 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, ##STR00467## have the meanings given for formula I.

12. The liquid crystal medium according to claim 10, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae II-1 to II-3 ##STR00468## in which R.sup.2, ##STR00469## have the meanings given for formula II.

13. Liquid crystal medium according to claim 2, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae III-1 to III-6 ##STR00470## in which R.sup.3, ##STR00471## have the meanings given 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—.

14. The liquid crystal medium according to claim 9, wherein the medium comprises one or more compounds of formula T ##STR00472## 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 or fluorinated alkenyl having up to 12 C atoms, ##STR00473## on each occurrence, independently of one another, denote ##STR00474## L.sup.4 and L.sup.5 identically or differently, denote F, Cl or straight chain or branched or cyclic alkyl or alkenyl each having up to 12 C atoms; Z.sup.T3, Z.sup.T4 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C— or a single bond, and t is 0 or 1.

15. A component for high-frequency technology, characterized in that it comprises the liquid crystal medium according to claim 9.

16. The component according to claim 15, 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.

17. A microwave antenna array, characterized in that it comprises one or more components according to claim 15.

Description

EXAMPLES

[0579] The following examples illustrate the present invention without limiting it in any way. 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

Abbreviations

[0580] RT room temperature (typically 20° C.±1° C.)

[0581] THF tetrahydrofuran

[0582] MTB ether methyl-tert-butyl ether

[0583] DCM dichloromethane

[0584] dist. distilled

Example 1: 2-Butyl-5-[2-[4-(3,5-difluoro-4-isothiocyanato-phenyl)phenyl]ethynyl]-1,3-difluoro-benzene

Step 1.1: 2-(4-Butyl-3,5-difluoro-phenyl)ethynyl-trimethyl-silane

[0585] ##STR00409##

[0586] A mixture of 5-bromo-2-butyl-1,3-difluoro-benzene (CAS-no. 160976-00-1, 15.1 g, 61 mmol), trimethylsilyl acetylene (17.6 ml, 124 mmol), diisopropylamine (70 ml), copper(I)iodide (277 mg, 1.5 mmol) and bis(triphenylphosphine)-palladium(II)chloride (1.7 g, 2.4 mmol) is heated at reflux temperature overnight. Then the reaction mixture is cooled to RT, and MTB ether and dist. water are added. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane) to give 2-(4-butyl-3,5-difluoro-phenyl)ethynyl-trimethyl-silane as a yellow oil.

Step 1.2: 2-Butyl-5-ethynyl-1,3-difluoro-benzene

[0587] ##STR00410##

[0588] Tetra-n-butylammonium fluoride (1 M in THF, 60 ml) is added dropwise to a solution of 2-(4-butyl-3,5-difluoro-phenyl)ethynyl-trimethyl-silane (15.9 g, 60 mmol) in THF (350 ml) at RT, and the reaction mixture is stirred overnight. Then it is hydrolyzed by addition of HCl (1 A and dist. water, and MBT ether is added. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue is purified by silica gel chromatography (heptane) to give 2-butyl-5-ethynyl-1,3-difluoro-benzene as a light yellow oil.

Step 1.3: 4-[4-[2-(4-Butyl-3,5-difluoro-phenyl)ethynyl]phenyl]-2,6-difluoro-aniline

[0589] ##STR00411##

[0590] A solution of 2-butyl-5-ethynyl-1,3-difluoro-benzene (4.6 g, 24 mmol), 4-(4-bromophenyl)-2,6-difluoro-aniline (CAS-no. 2244281-20-5, 7.0 g, 23 mmol) and diisopropylamine (55 ml) in THF (60 ml) is heated at reflux temperature. Copper(I)iodide (4.4 mg), 2-dicyclohexylphosphino-2′4′6′-triisopropyl-1,1′-biphenyl (22 mg) and chloro(2-dicyclohexylphosphino-2′4′6′-triisopropyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)palladium(II) (37 mg) are added, and the reaction mixture is stirred at reflux temperature overnight. Then it is cooled to RT, filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (heptane/MTB ether 5/1) and crystallization (heptane) to give 4-[4-[2-(4-butyl-3,5-difluoro-phenyl)ethynyl]phenyl]-2,6-difluoro-aniline as brown crystals.

Step 1.4: 2-Butyl-5-[2-[4-(3,5-difluoro-4-isothiocyanato-phenyl)phenyl]ethynyl]-1,3-difluoro-benzene

[0591] ##STR00412##

[0592] A solution of 4-[4-[2-(4-butyl-3,5-difluoro-phenyl)ethynyl]phenyl]-2,6-difluoro-aniline (7.4 g, 19 mmol) and 1,4-diazabicyclo[2.2.2]octane (5.2 g, 47 mmol) in DCM (70 ml) is cooled to 0° C. and treated dropwise with thiophosgene (1.6 ml, 20 mmol). The reaction mixture is stirred at RT for 60 min. Then it is hydrolyzed with brine, and the aqueous phase is separated and extracted with DCM. The combined organic phases are washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue is purified by silica gel chromatography (heptane) and crystallization (heptane) to give 2-butyl-5-[2-[4-(3,5-difluoro-4-isothiocyanato-phenyl)phenyl]ethynyl]-1,3-difluoro-benzene as light orange crystals.

[0593] Phase sequence: K 84 N 174 I. K 84 N 174.0 I

[0594] Δε=7.40

[0595] Δn=0.4180

[0596] γ.sub.1=735 mPas

[0597] In analogy to Synthesis Example 1 the following compounds are obtained:

TABLE-US-00007 physical No. Compound parameters  2 [00413] K 80 I Δε = 5.50 Δn = 0.3090 γ.sub.1 = 126 mPas  3 [00414] K 63 I Δε = 4.90 Δn = 0.2722 γ.sub.1 = 86 mPas  4 [00415] K 64 I Δε = 4.70 Δn = 0.2870 γ.sub.1 = 94 mPas  5 [00416] K 79 I Δε = 5.43 Δn = 0.2690 γ.sub.1 = 104 mPas  6 [00417] K 111 N 151.0 I Δε = 7.40 Δn = 0.3430 γ.sub.1 = 878 mPas  7 [00418] K 88 I Δε = 3.89 Δn = 0.2376 γ.sub.1 = 915 mPas  8 [00419] K 113 N 172.2 I Δε = 6.90 Δn = 0.4250 γ.sub.1 = 707 mPas  9 [00420] K 84 N 165.5 I Δε = 7.60 Δn = 0.4213 γ.sub.1 = 701 mPas 10 [00421] K 73 N 170.0 I Δε = 7.60 Δn = 0.4180 γ.sub.1 = 753 mPas 11 [00422] 12 [00423] K 114 I Δε = 4.70 Δn = 0.3770 γ.sub.1 = 947 mPas 13 [00424] 14 [00425] K 107 SmB 110 SmA 168 N 217.6 Δε = 9.90 Δn = 0.4390 γ.sub.1 = 472 mPas 15 [00426] 16 [00427] 17 [00428] 18 [00429] 19 [00430] 20 [00431] K 92 I Δε = −0.3 Δn = 0.2570 γ.sub.1 = 62 mPas 21 [00432] K 140 I 22 [00433] K 127 N 164.1 I 23 [00434] Tg −23 K 78 I Δε = −1.49 Δn = 0.1908 γ.sub.1 = 607 mPas 24 [00435] K 149 I Δε = 0.10 Δn = 0.3070 25 [00436] K 115 N 182.9 I Δε = 1.31 Δn = 0.3744 γ.sub.1 = 489 mPas 26 [00437] K 139 N (115) I 27 [00438] K 116 N 184.4 I Δε = 0.52 Δn = 0.3829 γ.sub.1 = 603 mPas

Mixture Examples

[0598] Liquid-crystal mixtures N1 to N19 and comparative mixture C1 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 20° C.

Comparative Mixture C1

[0599]

TABLE-US-00008 PPTU-4-S 6.0% T(N,l) [° C.]: 158 PPTU-5-S 10.0% Δn [589 nm, 20° C.]: 0.3797 PPU-TO-S 22.0% n.sub.e [589 nm, 20° C.]: 1.9144 CPU-2-S 26.0% n.sub.o [589 nm, 20° C.]: 1.5347 CPTU-4-S 10.0% Δε [1 kHz, 20° C.]: 15.4 CPTU-5-S 14.0% ε.sub.∥ [1 kHz, 20° C.]: 19.4 P(2)TU-5-S 12.0% ε.sub.⊥ [1 kHz, 20° C.]: 4.0 Σ 100.0% γ.sub.1 [mPa s, 20° C.]: 528 K.sub.1 [pN, 20° C.]: 14.2 K.sub.3 [pN, 20° C.]: 24.8 K.sub.3/K.sub.1 [pN, 20° C.]: 1.74 V.sub.0 [V, 20° C.]: 1.01 LTS bulk [h, −30° C.]: 1000 LTS bulk [h, −40° C.]: 600 τ [20° C., 19 GHz]: 0.314 ε.sub.r,∥ [20° C., 19 GHz]: 3.56 ε.sub.r,⊥ [20° C., 19 GHz]: 2.45 tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0056 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0091 η [20° C., 19 GHz]: 34.5

Example N1

[0600]

TABLE-US-00009 PPTU-4-S 6.0% Δε [589 nm, 20° C.]: 14.0 PPTU-5-S 12.0% ε.sub.∥ [1 kHz, 20° C.]: 17.7 PPU-TO-S 23.0% ε.sub.⊥ [1 kHz, 20° C.]: 3.7 CPTU-5-S 25.0% γ.sub.1 [mPa s, 20° C.]: 631 P(2)TU-5-S 14.0% K.sub.1 [pN, 20° C.]: 16.0 CPU-2-S 10.0% K.sub.3 [pN, 20° C.]: 23.6 UITPU-4-S 10.0% K.sub.3/K.sub.1 [pN, 20° C.]: 1.47 Σ 100.0% V.sub.0 [V, 20° C.]: 1.13 τ [20° C., 19 GHz]: 0.324 ε.sub.r,∥ [20° C., 19 GHz]: 3.62 ε.sub.r,⊥ [20° C., 19 GHz]: 2.45 tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0051 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0082 η [20° C., 19 GHz]: 39.7

[0601] Example N1 corresponds to Comparative mixture C1 and additionally comprises a compound of formula U according to the invention. An improvement of the material quality η from 34.5 to 39.7 is observed.

Example N2

[0602]

TABLE-US-00010 PPTU-4-S 6.0% T(N,l) [° C.]: 159 PPTU-5-S 12.0% Δε [589 nm, 20° C.]: 15.0 PPU-TO-S 25.0% ε.sub.∥ [1 kHz, 20° C.]: 18.7 CPTU-5-S 25.0% ε.sub.⊥ [1 kHz, 20° C.]: 3.7 PTU-3-S 10.0% γ.sub.1 [mPa s, 20° C.]: 530 PTU-5-S 10.0% K.sub.1 [pN, 20° C.]: 17.0 UITPU-4-S 12.0% K.sub.3 [pN, 20° C.]: 26.2 Σ 100.0% K.sub.3/K.sub.1 [pN, 20° C.]: 1.54 V.sub.0 [V, 20° C.]: 1.13 τ [20° C., 19 GHz]: 0.338 ε.sub.r,∥ [20° C., 19 GHz]: 3.69 ε.sub.r,⊥ [20° C., 19 GHz]: 2.44 tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0055 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0089 η [20° C., 19 GHz]: 38.2

Example N3

[0603]

TABLE-US-00011 PGU-3-S 13.0% τ [20° C., 19 GHz]: 159.9 PPTU-4-S 6.0% ε.sub.r,∥ [20° C., 19 GHz]: 0.323 PPTU-5-S 10.0% ε.sub.r,⊥ [20° C., 19 GHz]: 3.6339 PPU-TO-S 22.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 2.4589 CPTU-4-S 8.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0050 CPTU-5-S 12.0% η [20° C., 19 GHz]: 0.0082 UITU-3-S 7.0% τ [20° C., 19 GHz]: 39.3 UITU-5-S 7.0% CPU(F,F)-3-S 15.0% Σ 100.0%

Example N4

[0604]

TABLE-US-00012 PPTU-4-S 6.0% τ [20° C., 19 GHz]: 160.7 PPTU-5-S 10.0% ε.sub.r,∥ [20° C., 19 GHz]: 0.318 PPU-TO-S 22.0% ε.sub.r,⊥ [20° C., 19 GHz]: 3.6235 CPU-2-S 22.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 2.4719 CPTU-4-S 8.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0054 CPTU-5-S 12.0% η [20° C., 19 GHz]: 0.0085 UITU-3-S 7.0% τ [20° C., 19 GHz]: 37.2 UITU-5-S 7.0% PPTU-TO-S 6.0% Σ 100.0%

Example N5

[0605]

TABLE-US-00013 PPTU-4-S 6.0% τ [20° C., 19 GHz]: 158.5 PPTU-5-S 10.0% ε.sub.r,∥ [20° C., 19 GHz]: 0.322 PPU-TO-S 22.0% ε.sub.r,⊥ [20° C., 19 GHz]: 3.6162 CPU-2-S 22.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 2.4511 CPTU-4-S 8.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0053 CPTU-5-S 12.0% η [20° C., 19 GHz]: 0.0084 UITU-3-S 7.0% τ [20° C., 19 GHz]: 38.4 UITU-5-S 7.0% PP(1)TU-TO-S 6.0% Σ 100.0%

Example N6

[0606]

TABLE-US-00014 PPTU-4-S 6.0% τ [20° C., 19 GHz]: 157.2 PPTU-5-S 10.0% LTS bulk [h, −30° C.]: 144 PPU-TO-S 22.0% τ [20° C., 19 GHz]: 0.323 CPU-2-S 22.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.6535 CPTU-4-S 8.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4726 CPTU-5-S 12.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0053 UITU-3-S 6.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0084 UITU-5-S 6.0% η [20° C., 19 GHz]: 38.4 ThTU-5-S 8.0% Σ 100.0%

Example N7

[0607]

TABLE-US-00015 PPTU-4-S 6.0% τ [20° C., 19 GHz]: 151.4 PPTU-5-S 10.0% LTS bulk [h, −30° C.]: 120 PPU-TO-S 20.0% τ [20° C., 19 GHz]: 0.326 CPU-2-S 20.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.6117 CPTU-4-S 8.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4338 CPTU-5-S 12.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0053 UITU-3-S 7.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0082 UITU-5-S 7.0% η [20° C., 19 GHz]: 39.8 ThTU-n-S 10.0% Σ 100.0%

Example N8

[0608]

TABLE-US-00016 PTU-3-S 6.0% τ [20° C., 19 GHz]: 160 PTU-5-S 6.0% ε.sub.r,∥ [20° C., 19 GHz]: 0.345 PPTU-4-S 8.0% ε.sub.r,⊥ [20° C., 19 GHz]: 3.7673 PPTU-5-S 10.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 2.4678 PGTU-4-S 6.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0057 PPU-TO-S 24.0% η [20° C., 19 GHz]: 0.0097 CPTU-4-S 8.0% τ [20° C., 19 GHz]: 35.6 CPTU-5-S 14.0% PPTU-TO-S 10.0% UITU-3-S 4.0% UITU-5-S 4.0% Σ 100.0%

Example N9

[0609]

TABLE-US-00017 PPTU-4-S 6.0% T(N,l) [° C.]: 148.5 PPTU-5-S 12.0% Δε [589 nm, 20° C.]: 14.0 PGU-3-S 14.0% ε.sub.∥ [1 kHz, 20° C.]: 17.8 PPU-TO-S 28.0% ε.sub.⊥ [1 kHz, 20° C.]: 3.8 CPTU-4-S 20.0% K.sub.1 [pN, 20° C.]: 15.6 UITU-3-S 10.0% K.sub.3 [pN, 20° C.]: 24.0 UITU-5-S 10.0% K.sub.3/K.sub.1 [pN, 20° C.]: 1.54 Σ 100.0% V.sub.0 [V, 20° C.]: 1.07 τ [20° C., 19 GHz]: 0.330 ε.sub.r,∥ [20° C., 19 GHz]: 3.6647 ε.sub.r,⊥ [20° C., 19 GHz]: 2.4566 tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0055 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0091 η [20° C., 19 GHz]: 36.3

Example N10

[0610]

TABLE-US-00018 PPTU-4-S 6.0% T(N,l) [° C.]: 155 PPTU-5-S 12.0% τ [20° C., 19 GHz]: 0.327 PPU-TO-S 28.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.6644 CPTU-4-S 14.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4661 CPTU-5-S 20.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0052 UITU-3-S 10.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0080 UITU-5-S 10.0% η [20° C., 19 GHz]: 40.9 Σ 100.0%

Example N11

[0611]

TABLE-US-00019 PPTU-4-S 6.0% T(N,l) [° C.]: 160 PPTU-5-S 12.0% LTS bulk [h, −20° C.]: 268 PPU-TO-S 20.0% τ [20° C., 19 GHz]: 0.325 CPU-2-S 16.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.5874 CPTU-4-S 12.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4224 CPTU-5-S 18.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0051 UITU-3-S 8.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0079 UITU-5-S 8.0% η [20° C., 19 GHz]: 41.1 Σ 100.0%

Example N12

[0612]

TABLE-US-00020 PPTU-4-S 6.0% T(N,l) [° C.]: 160 PPTU-5-S 10.0% τ [20° C., 19 GHz]: 0.324 PPU-TO-S 22.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.5821 CPU-2-S 24.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4228 CPTU-4-S 10.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0054 CPTU-5-S 14.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0085 UITU-3-S 7.0% η [20° C., 19 GHz]: 38.1 UITU-5-S 7.0% Σ 100.0%

Example N13

[0613]

TABLE-US-00021 PPTU-4-S 6.0% T(N,l) [° C.]: 162 PPTU-5-S 10.0% τ [20° C., 19 GHz]: 0.302 CPU-2-S 28.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.5488 CPU-4-S 22.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4763 PPU-TO-S 24.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0057 UITU-3-S 5.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0090 UITU-5-S 5.0% η [20° C., 19 GHz]: 33.6 Σ 100.0%

Example N14

[0614]

TABLE-US-00022 PPTU-4-S 6.0% T(N,l) [° C.]: 160.5 PPTU-5-S 10.0% LTS bulk [h, -20° C.]: 168 PPU-TO-S 22.0% τ [20° C., 19 GHz]: 0.321 CPU-2-S 24.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.5871 CPTU-5-S 24.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4362 UITU-3-S 7.0% tan δ.sub.ε .sub.r,∥ [20° C., 19 GHz]: 0.0052 UITU-5-S 7.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0082 Σ 100.0% η [20° C., 19 GHz]: 39.1

Example N15

[0615]

TABLE-US-00023 PPTU-4-S 6.0% LTS bulk [h, −20° C.]: 96 PPTU-5-S 10.0% τ [20° C., 19 GHz]: 0.318 PPU-TO-S 22.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.5865 CPU-2-S 24.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.4446 CPTU-4-S 24.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0055 UITU-3-S 7.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0086 UITU-5-S 7.0% η [20° C., 19 GHz]: 37.0 Σ 100.0%

Example N16

[0616]

TABLE-US-00024 PPTU-4-S 6.0% PPTU-5-S 10.0% PPU-TO-S 20.0% CPU-2-S 20.0% CPTU-4-S 10.0% CPTU-5-S 20.0% UITU-3-S 7.0% UITU-5-S 7.0% Σ 100.0%

Example N17

[0617]

TABLE-US-00025 PPTU-4-S 6.0% PPTU-5-S 10.0% PPU-TO-S 20.0% CPU-2-S 18.0% CPTU-4-S 10.0% CPTU-5-S 20.0% UITU-3-S 8.0% UITU-5-S 8.0% Σ 100.0%

Example N18

[0618]

TABLE-US-00026 PPTU-4-S 6.0% T(N,I) [° C.]: 157 PPTU-5-S 14.0% τ [20° C., 19 GHz]: 0.322 CPTU-5-S 25.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.60 PTU-3-S 9.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.44 PTU-5-S 9.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0049 UITPU-4-S 12.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0085 CPU-2-S 25.0% η [20° C., 19 GHz]: 38.1 Σ 100.0%

Example N19

[0619]

TABLE-US-00027 PPTU-4-S 6.0% T(N,I) [° C.]: 156 PPTU-5-S 12.0% τ [20° C., 19 GHz]: 0.331 PPU-TO-S 20.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.65 CPTU-5-S 22.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.44 PTU-3-S 10.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0052 PTU-5-S 10.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0085 IS-8706 10.0% η [20° C., 19 GHz]: 39.2 UITPU-4-S 10.0% Σ 100.0%

Example N20

[0620]

TABLE-US-00028 PPTU-4-S 6.0% T(N,I) [° C.]: 165 PPTU-5-S 12.0% Δε [1 kHz, 20° C.]: 17.4 PPU-TO-S 11.0% ε.sub.∥ [1 kHz, 20° C.]: 21.2 CPTU-5-S 25.0% ε.sub.⊥ [1 kHz, 20° C.]: 3.8 CPU-2-S 22.0% γ.sub.1 [mPa s, 20° C.]: 532 PTU-3-S 7.0% K.sub.3 [pN, 20° C.]: 17.0 PTU-5-S 7.0% K.sub.1 [pN, 20° C.]: 24.0 UITPU-4-S 10.0% K.sub.3/K.sub.1 [pN, 20° C.]: 1.42 Σ 100.0% V.sub.0 [V, 20° C.]: 1.04 LTS bulk [h, -40°C]: 192 τ [20° C., 19 GHz]: 0.328 ε.sub.r,∥ [20° C., 19 GHz]: 3.60 ε.sub.r,⊥ [20° C., 19 GHz]: 2.42 tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0051 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0084 η [20° C., 19 GHz]: 39.0

Example N21

[0621]

TABLE-US-00029 PPTU-4-S 6.0% T(N,I) [° C.]: 165 PPTU-5-S 12.0% τ [20° C., 19 GHz]: 0.325 PPU-TO-S 11.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.56 CPTU-5-S 25.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.41 CPU-2-S 20.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0050 PTU-3-S 7.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0081 PTU-5-S 7.0% η [20° C., 19 GHz]: 40.1 UITPU-5-S 12.0% Σ 100.0%

Example N22

[0622]

TABLE-US-00030 PPTU-4-S 6.0% T(N,I) [° C.]: 165 PPTU-5-S 12.0% Δε [1 kHz, 20° C.]: 17.1 PPU-TO-S 11.0% ε.sub.∥ [1 kHz, 20° C.]: 20.8 CPTU-5-S 25.0% ε.sub.⊥ [1 kHz, 20° C.]: 3.8 CPU-2-S 20.0% γ.sub.1 [mPa s, 20° C.]: 548 PTU-3-S 7.0% K.sub.3 [pN, 20° C.]: 17.0 PTU-5-S 7.0% K.sub.1 [pN, 20° C.]: 24.9 UITPU-5-S 12.0% K.sub.3/K.sub.1 [pN, 20° C.]: 1.47 Σ 100.0% V.sub.0 [V, 20° C.]: 1.07 LTS bulk [h, -40°C]: 336 τ [20° C., 19 GHz]: 0.328 ε.sub.r,∥ [20° C., 19 GHz]: 3.60 ε.sub.r,⊥ [20° C., 19 GHz]: 2.42 tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0050 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0083 η [20° C., 19 GHz]: 39.5

Example N23

[0623]

TABLE-US-00031 PPTU-4-S 6.0% T(N,I) [° C.]: 163 PPTU-5-S 12.0% τ [20° C., 19 GHz]: 0.332 PPU-TO-S 15.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.60 CPTU-5-S 25.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.40 CPU-2-S 14.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0051 PTU-3-S 8.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0084 PTU-5-S 8.0% η [20° C., 19 GHz]: 39.5 UITPU-4-S 7.35 UITPU-5-S 4.65 Σ 100.0%

Example N24

[0624]

TABLE-US-00032 PTU-3-S 10.0% T(N,I) [° C.]: 156 PTU-5-S 10.0% Δε [1 kHz, 20° C.]: 19.3 PPTU-4-S 6.0% ε.sub.∥ [1 kHz, 20° C.]: 23.4 PPTU-5-S 11.0% ε.sub.⊥ [1 kHz, 20° C.]: 4.0 PGTU-4-S 6.0% K.sub.1 [pN, 20° C.]: 18.4 PGU-3-S 12.0% K.sub.3 [pN, 20° C.]: 24.4 PPU-TO-S 13.0% K.sub.3/K.sub.1 [pN, 20° C.]: 1.33 CPTU-5-S 22.0% V.sub.0 [V, 20° C.]: 1.03 UIPTU-5-S 10.0% τ [20° C., 19 GHz]: 0.338 Σ 100.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.71 ε.sub.r,⊥ [20° C., 19 GHz]: 2.46 tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0056 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0102 η [20° C., 19 GHz]: 33.1

Example N25

[0625]

TABLE-US-00033 PPTU-4-S 10.0% T(N,I) [° C.]: 166 PPTU-5-S 20.0% Δε [1 kHz, 20° C.]: 14.5 CPTU-5-S 13.0% ε.sub.∥ [1 kHz, 20° C.]: 17.9 PGTU-4-S 10.0% ε.sub.⊥ [1 kHz, 20° C.]: 3.4 PPTU-TO-S 10.0% K.sub.1 [pN, 20° C.]: 21.5 PTUI-4-S 17.0% K.sub.3 [pN, 20° C.]: 22.5 UIPTU-5-S 20.0 % K.sub.3/K.sub.1 [pN, 20° C.]: 1.05 Σ 100.0% V.sub.0 [V, 20° C.]: 1.29 τ [20° C., 19 GHz]: 0.357 ε.sub.r,∥ [20° C., 19 GHz]: 3.82 ε.sub.r,⊥ [20° C., 19 GHz]: 2.46 tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0049 tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0079 η [20° C., 19 GHz]: 45.5

Example N26

[0626]

TABLE-US-00034 CPTU-5-S 23.5% T(N,I) [° C.]: 173.5 CPU(F,F)-3-S 19.0% τ [20° C., 19 GHz]: 0.299 CPUI-4-S 12.5% ε.sub.r,∥ [20° C., 19 GHz]: 3.46 PTUI-4-S 10.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.43 UIPTU-5-S 15.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0043 PPTUI-4-S 20.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0048 Σ 100.0% η [20° C., 19 GHz]: 62.9

Example N27

[0627]

TABLE-US-00035 PPTU-4-S 6.0% T(N,I) [° C.]: 172.2 PPTU-5-S 12.0% LTS bulk [h, −20° C.]: 24 PPU-TO-S 23.0% LTS bulk [h, −30° C.]: 120 CPTU-5-S 25.0% τ [20° C., 19 GHz]: 0.323 CPU(F,F)-3-S 18.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.52 CPU(F,F)-4-S 6.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.38 UITU-4-S 5.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0045 UITU-5-S 5.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0067 Σ 100.0% η [20° C., 19 GHz]: 48.2

Example N28

[0628]

TABLE-US-00036 PTU-3-S 5.0% T(N,I) [° C.]: 158.7 PTU-5-S 5.0% LTS bulk [h, −30° C.]: 72 PPTU-4-S 6.0% τ [20° C., 19 GHz]: 0.322 PPTU-5-S 12.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.58 PPU-TO-S 23.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.43 CPTU-5-S 23.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0050 CPU(F,F)-3-S 18.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0078 UITU-4-S 4.0% η [20° C., 19 GHz]: 41.3 UITU-5-S 4.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: Σ 100.0%

Example N29

[0629]

TABLE-US-00037 PPTU-4-S 6.0% T(N,I) [° C.]: 156 PPTU-5-S 12.0% τ [20° C., 19 GHz]: 0.331 PPU-TO-S 20.0% ε.sub.r,∥ [20° C., 19 GHz]: 3.65 CPTU-5-S 22.0% ε.sub.r,⊥ [20° C., 19 GHz]: 2.44 PTU-3-S 10.0% tan δ.sub.ε r,∥ [20° C., 19 GHz]: 0.0052 PTU-5-S 10.0% tan δ.sub.ε r,⊥ [20° C., 19 GHz]: 0.0085 CPU(F,F)-3-S 10.0% η [20° C., 19 GHz]: 39.2 UITPU-4-S 10.0% Σ 100.0%