AROMATIC ISOTHIOCYANATES

Abstract

The present invention relates to a compound of formula GF

##STR00001##

in which the occurring groups and parameters have the meanings defined in claim 1, to a liquid crystal medium comprising a compound of formula GF 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 GF ##STR00608## in which R.sup.G denotes H, straight-chain or branched, non-fluorinated alkyl or alkoxy, each having 1 to 12 C atoms or straight-chain or branched non-fluorinated alkenyl having 2 to 12 C atoms, in each of which one or more CH.sub.2-groups may be replaced by ##STR00609## or a group R.sup.P, R.sup.P denotes halogen, CN, NCS, R.sup.F, R.sup.F-G- or R.sup.FS, wherein R.sup.F denotes fluorinated alkyl having 1 to 9 C atoms, Z.sup.G1, Z.sup.G2 identically or differently, denote CH?CH, CF?CF, CH?CF, CF?CH, C?C, C?CC?C or a single bond, X.sup.G1, X.sup.G2, identically or differently, denote Cl or F, ##STR00610## 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, tetralin-2,6-diyl, tetralin-5,8-diyl, decalin-2,6-diyl, bicyclo[1.1.1]pentane-1,3-diyl, 4,4-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, and spiro[3.3]-heptane-2,6-diyl, in which one or two CH groups may be replaced by N, 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 L, and c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl, and 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 each having 1 to 12 C atoms, and u is 0, 1 or 2, wherein at least one of ##STR00611## is not trans-1,4-cyclohexylene.

2. The compound according to claim 1, wherein the compound is selected from the group of compounds of the formulae GF-1 to GF-5: ##STR00612## in which and R.sup.G, X.sup.G1 and X.sup.G2, ##STR00613## and have the meanings given in claim 1.

3. The compound according to claim 1, in which X.sup.G1 and X.sup.G2 denote F.

4. The compound according to claim 1, wherein the group ##STR00614## denotes 1,4-phenylene, in which one or two CH groups may each be replaced by N and in which one or more H atoms may each be replaced by L, and L denotes F, optionally fluorinated alkyl or optionally fluorinated alkoxy each having 1 to 6 C atoms.

5. The compound according to claim 1, wherein R.sup.G denotes straight chain alkyl having 1 to 7 C atoms or branched alkyl having 3 to 9 C atoms.

6. The compound according to claim 1, wherein R.sup.G denotes straight chain fluorinated alkyl or straight chain fluorinated alkoxy having 1 to 7 C atoms.

7. A liquid-crystal medium comprising one or more compounds of formula GF according to claim 1.

8. The medium according to claim 7, wherein the medium additionally comprises one or more compounds selected from the group of compounds of the formulae I, II and III: ##STR00615## in which R.sup.1 denotes H, non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17 C atoms, or non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH.sub.2-groups may each be replaced by ##STR00616## n is 0, 1 or 2, ##STR00617## to ##STR00618## on each occurrence, independently of one another, denote ##STR00619## in which R.sup.L, on each occurrence, identically or differently, denotes H or alkyl having 1 to 6 C atoms, ##STR00620## in which one or more H or atoms may each be replaced by alkyl having 1 to 6 C atoms or F, and wherein ##STR00621## alternatively denotes ##STR00622## R.sup.2 denotes H, non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17 C atoms, or non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH.sub.2-groups may each be replaced by ##STR00623## Z.sup.21 denotes trans-CH?CH, trans-CF?CF or C?C, and ##STR00624## independently of one another, denote ##STR00625## in which R.sup.L, on each occurrence, identically or differently, denotes H or alkyl having 1 to 6 C atoms, or ##STR00626## in which one or more H atoms may each be replaced by alkyl having 1 to 6 C atoms or F, R.sup.3 denotes H, non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17 C atoms, or non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH.sub.2-groups may each be replaced by ##STR00627## 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 ##STR00628## to ##STR00629## independently of one another, denote ##STR00630## in which R.sup.L, on each occurrence, identically or differently, denotes H or alkyl having 1 to 6 C atoms, or ##STR00631## in which one or more H atoms may each be replaced by alkyl having 1 to 6 C atoms or F, and wherein ##STR00632## alternatively denotes, or ##STR00633## and where the compounds of the formula GF are excluded from the compounds of the formulae I, II, and III.

9. The liquid crystal medium according to claim 7, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae I-1 to I-5 ##STR00634## 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, ##STR00635## and have the meanings given for formula I in claim 8.

10. The liquid crystal medium according to claim 8, wherein the medium comprises one or more compounds selected from the group of compounds of the formulae II-1 to II-3 ##STR00636## in which R.sup.2, ##STR00637## and have the meanings given in claim 8 for formula II.

11. The medium according to claim 8, wherein the medium comprises one or more compounds of formula III selected from the group consisting of the compounds of the formulae III-1 to III-6 ##STR00638## in which 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 and the other groups have the meaning given in claim 8 under formula III, R.sup.3 denotes non-fluorinated alkyl or alkoxy having 1 to 7 C atoms or non-fluorinated alkenyl having 2 to 7 C atoms, and one of ##STR00639## to ##STR00640## denotes ##STR00641## and the others, independently of one another, denote ##STR00642## where ##STR00643## alternatively denotes ##STR00644##

12. The medium according to claim 7, wherein the medium further comprises one or more compounds of formula T ##STR00645## in which R.sup.T denotes halogen, CN, NCS, R.sup.F, R.sup.FO or R.sup.FS, wherein R.sup.F denotes fluorinated alkyl or fluorinated alkenyl having up to 12 C atoms, ##STR00646## on each occurrence, independently of one another, denote ##STR00647## 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.

13. The medium according to claim 7, wherein the medium further comprises one or more compounds of formula U ##STR00648## 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 each be replaced by ##STR00649## or denotes a group R.sup.P, R.sup.P denotes halogen, CN, NCS, R.sup.F, R.sup.FO or R.sup.FS, wherein R.sup.F denotes fluorinated alkyl or fluorinated alkenyl having up to 9 C atoms, Z.sup.U1, Z.sup.U2 identically or differently, denote CH?CH, CF?CF, CH?CF, CF?CH, C?C or a single bond, X.sup.1, X.sup.2, X.sup.3 and X.sup.4 identically or differently, denote Cl or F, t is 0 or 1, and ##STR00650## 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 each be replaced by N and in which one or more H atoms may each be replaced by L, wherein tetrafluoro-1,4-phenylene is excluded, 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 and spiro[3.3]heptane-2,6-diyl, in which one or more non-adjacent CH.sub.2 groups may each be replaced by O and/or S and in which one or more H atoms may each 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, wherein 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.

14. The medium according to claim 13, wherein the medium comprises one or more compounds selected from the group consisting of the compounds of the formulae U-1 to U-11 ##STR00651## ##STR00652## in which L.sup.1, L.sup.2 and L.sup.3 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, X.sup.3 and X.sup.4 have the meanings given in claim 13.

15. An electronic component comprising a first substrate and a second substrate facing each other, an electrode provided on each substrate or two electrodes provided on only one of the substrates, wherein the component comprises the liquid crystal medium according to claim 7 sandwiched between said first and second substrate.

16. The component according to claim 15, wherein the liquid crystal medium in the component is arranged as a tunable dielectric configured for use in high-frequency technology.

17. The component according to claim 16, 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.

18. A microwave antenna array, wherein said array comprises one or more components according to claim 15.

19. The component according to claim 15, wherein the component is a transmissive or a reflective spatial light modulator.

Description

EXAMPLES

[0844] 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:

[0845] dist. distilled [0846] DABCO 1,4-Diazabicyclo[2.2.2]octane [0847] THE Tetrahydrofuran [0848] MTB ether Methyl-tert-butyl ether [0849] dist. distilled [0850] XPhos 2-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl [0851] XPhos Pd G2 Chloro(2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl)[2-(2-amino-1,1-biphenyl)palladium (II) [0852] Pd(amphos)Cl.sub.2 Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)

Synthesis Example 1: 1-[4-(4-Butylcyclohexyl)phenyl]-2,5-difluoro-4-isothiocyanatobenzene

Step 1.1: 4-[4-(4-Butylcyclohexyl)phenyl]-2,5-difluoro-aniline

[0853] ##STR00516##

[0854] Bis(di-tert-butyl-(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.8 mg, 0.001 mmol) is added to a mixture of [4-(4-butylcyclohexyl)phenyl]boronic acid (CAS 516510-90-0) (5.0 g, 19 mmol) and 4-bromo-2,5-difluoro-aniline (4.0 g, 19 mmol) in THE (30 ml) under argon atmosphere at 50? C. Aqueous sodium hydroxide (2 N) (14.0 ml, 29 mmol) is slowly added at reflux temperature, and the reaction mixture is heated at reflux temperature overnight. Then the reaction mixture is allowed to cool to room temperature, quenched with dist. water and hydrochloric acid (2 N) and diluted with MTB ether. 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 (solvent heptane/MTB ether) to give 4-[4-(4-butylcyclohexyl)phenyl]-2,5-difluoro-aniline as a brown solid.

Step 1.2: 1-[4-(4-Butylcyclohexyl)phenyl]-2,5-difluoro-4-isothiocyanato-benzene

[0855] ##STR00517##

[0856] Thiophosgene (1.5 ml, 19 mmol) is slowly added to a solution of 4-[4-(4-butylcyclohexyl)phenyl]-2,5-difluoro-aniline (6.0 g, 17 mmol) and DABCO (4.9 g, 44 mmol) in dichloromethane (70 ml) at 0? C. under argon atmosphere. The reaction mixture is stirred at room temperature for 1 h. Then it is quenched with dist. water and brine. The aqueous phase is separated and extracted with dichloromethane. The combined organic phases are washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane) and crystallization (heptane) to give white crystals of 1-[4-(4-butylcyclohexyl)phenyl]-2,5-difluoro-4-isothiocyanato-benzene.

[0857] Phase sequence: K 82 N 180 I (decomp) [0858] ??=8.42 [0859] ?n=0.2701 [0860] ?.sub.1=565 mPas

Synthesis Example 2: 1-[2-(4-Butylphenyl)ethynyl]-2,5-difluoro-4-isothiocyanatobenzene

Step 2.1: 4-[2-(4-Butylphenyl)ethynyl]-2,5-difluoro-aniline

[0861] ##STR00518##

[0862] XPhos Pd G2 (40 mg, 0.05 mmol), XPhos (24 mg, 0.05 mmol) and copper(I) iodide (4.8 mg, 0.03 mmol) are added to a mixture of 1-butyl-4-ethynylbenzene (4.0 g, 25 mmol), 4-bromo-2,5-difluoro-aniline (5.0 g, 24 mmol) and diisopropylamine (60 ml) in THE (60 ml) under argon atmosphere slightly below the boiling point. The reaction mixture is heated at reflux temperature for 4 h. Then it is allowed to cool to room temperature, and the precipitate is filtered, washed with THF, and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane/MTB ether) to give 4-[2-(4-butylphenyl)ethynyl]-2,5-difluoro-aniline as a brown oil.

Step 2.2: 1-[2-(4-Butylphenyl)ethynyl]-2,5-difluoro-4-isothiocyanato-benzene

[0863] ##STR00519##

[0864] Thiophosgene (2.2 ml, 28 mmol) is slowly added to a solution of 4-[2-(4-butylphenyl)ethynyl]-2,5-difluoro-aniline (7.2 g, 25 mmol) and DABCO (7.1 g, 63 mmol) in dichloromethane (120 ml) at 0? C. under argon atmosphere. The reaction mixture is stirred at room temperature for 1 h. Then it is quenched with dist. water and brine. The aqueous phase is separated and extracted with dichloromethane. The combined organic phases are washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane/MTB ether) and crystallization (heptane) to give white crystals of 1-[2-(4-butylphenyl)ethynyl]-2,5-difluoro-4-isothiocyanato-benzene.

[0865] Phase sequence K 48 N (23) I. [0866] ??=8.92 [0867] ?n=0.3776 [0868] ?.sub.1=74 mPas

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

Step 3.1: 4-[2-[4-(4-Butylphenyl)phenyl]ethynyl]-2,5-difluoro-aniline

[0869] ##STR00520##

[0870] XPhos Pd G2 (26 mg, 0.03 mmol), XPhos (16 mg, 0.03 mmol) and copper(I) iodide (3.2 mg, 0.02 mmol) are added to a mixture of 1-butyl-4-(4-ethynylphenyl)benzene (CAS 136723-70-1) (3.9 g, 17 mmol), 4-bromo-2,5-difluoro-aniline (3.3 g, 16 mmol) and diisopropylamine (40 ml) in THE (40 ml) under argon atmosphere slightly below the boiling point. The reaction mixture is heated at reflux temperature overnight. Then it is allowed to cool to room temperature, and the precipitate is filtered, washed with THF, and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane/MTB ether) to give 4-[2-[4-(4-butylphenyl)phenyl]ethynyl]-2,5-difluoro-aniline as a brown solid.

Step 3.2: 1-[2-[4-(4-Butylphenyl)phenyl]ethynyl]-2,5-difluoro-4-isothiocyanato-benzene

[0871] ##STR00521##

[0872] Thiophosgene (0.9 ml, 11 mmol) is slowly added to a solution of 4-[2-[4-(4-butylphenyl)phenyl]ethynyl]-2,5-difluoro-aniline (3.6 g, 10 mmol) and DABCO (2.8 g, 25 mmol) in dichloromethane (50 ml) at 0? C. under argon atmosphere. The reaction mixture is stirred at room temperature for 1 h. Then it is quenched with dist. water and brine. The aqueous phase is separated and extracted with dichloromethane. The combined organic phases are washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane/MTB ether) and crystallization (heptane) to give yellow crystals of 1-[2-[4-(4-butylphenyl)phenyl]ethynyl]-2,5-difluoro-4-isothiocyanato-benzene.

[0873] Phase sequence: K 58 SmA 164 N 226 I. [0874] ??=10.51 [0875] ?n=0.5021 [0876] ?.sub.1=472 mPas

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

Step 4.1: 2-[4-[2-(4-Butylphenyl)ethynyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0877] ##STR00522##

[0878] XPhos Pd G2 (170 mg, 0.2 mmol), XPhos (100 mg, 0.2 mmol) and copper(I) iodide (20 mg, 0.1 mmol) are added to a mixture of 1-butyl-4-ethynylbenzene (18.0 g, 0.1 mol), 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30.0 g, 0.1 mol) and diisopropylamine (250 ml) in THE (30 ml) under argon atmosphere at 55? C. The reaction mixture is heated at reflux temperature overnight. Then it is allowed to cool to room temperature, filtered and concentrated in vacuo. The residue is dissolved in toluene, washed with dist. water, dried (sodium sulfate), filtered and concentrated in vacuo. The crude product is purified by silica gel chromatography (solvent toluene) and crystallization (heptane) to give yellow crystals of 2-[4-[2-(4-butylphenyl)ethynyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Step 4.2: 4-[4-[2-(4-Butylphenyl)ethynyl]phenyl]-2,5-difluoro-aniline

[0879] ##STR00523##

[0880] Pd(amphos)Cl.sub.2 (6.0 mg, 9 ?mol) is added to a mixture of 2-[4-[2-(4-butylphenyl)ethynyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.2 g, 9 mmol) and 4-bromo-2,5-difluoro-aniline (1.8 g, 9 mmol) in ethylene glycol (20 ml) and THE (20 ml) under argon atmosphere at 60? C. Aqueous sodium hydroxide (2 N) (6.7 ml, 13 mmol) is slowly added at reflux temperature, and the reaction mixture is heated at reflux temperature overnight. Then it is allowed to cool to room temperature and quenched with acetic acid (0.8 ml) and dist. water. MTB ether is added, and the aqueous phase is separated and again extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane/MTB ether) to give 4-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,5-difluoro-aniline as a yellow solid.

Step 4.3: 1-[4-[2-(4-Butylphenyl)ethynyl]phenyl]-2,5-difluoro-4-isothiocyanato-benzene

[0881] ##STR00524##

[0882] Thiophosgene (0.6 ml, 8 mmol) is slowly added to a solution of 4-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,5-difluoro-aniline (2.5 g, 7 mmol) and DABCO (1.9 g, 17 mmol) in dichloromethane (30 ml) at 0? C. under argon atmosphere. The reaction mixture is stirred for 1 h at room temperature. Then it is quenched with dist. water and brine. The aqueous phase is separated and extracted with dichloromethane. The combined organic phases are washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane) and crystallization (heptane) to give white crystals of 1-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,5-difluoro-4-isothiocyanato-benzene.

[0883] Phase sequence: K 65 SmA 123 N 199 I. [0884] ??=9.72 [0885] ?n=0.4573 [0886] ?.sub.1=732 mPas

Synthesis Example 5:1,4-Difluoro-2-isothiocyanato-5-[4-[4-(trifluoromethoxy)phenyl]-phenyl]benzene

Step 5.1: 2,5-Difluoro-4-[4-[4-(trifluoromethoxy)phenyl]phenyl]aniline

[0887] ##STR00525##

[0888] Bis(dibenzylidene-acetone)palladium(0) (10 mg, 0.02 mmol) and tris-(o-tolyl)phosphine (5.4 mg, 0.02 mmol) are added to a mixture of [4-(4-(trifluoromethoxy)phenyl]phenyl]boronic acid (CAS 501944-50-9) (5.0 g, 18 mmol) and 4-bromo-2,5-difluoro-aniline (3.7 g, 18 mmol) in acetone (35 ml) under argon atmosphere at 50? C. Aqueous sodium hydroxide (2 N) (17.7 ml, 35 mmol) is slowly added at reflux temperature, and the reaction mixture is heated at reflux temperature overnight. Then it is quenched with water and hydrochloric acid (2 N) and diluted with MTB ether. 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 (solvent heptane/MTB ether) to give 2,5-difluoro-4-[4-[4-(trifluoromethoxy)phenyl]phenyl]aniline as a white solid.

Step 5.2: 1,4-Difluoro-2-isothiocyanato-5-[4-[4-(trifluoromethoxy)phenyl]phenyl]benzene

[0889] ##STR00526##

[0890] Thiophosgene (1.3 ml, 16 mmol) is slowly added to a solution of 2,5-difluoro-4-[4-[4-(trifluoromethoxy)phenyl]phenyl]aniline (5.4 g, 15 mmol) and DABCO (4.2 g, 37 mmol) in dichloromethane (70 ml) at 0? C. under argon atmosphere. The mixture is stirred at room temperature for 1 h. Then the reaction mixture is quenched with dist. water and brine. The aqueous phase is separated and extracted with dichloromethane. The combined organic phases are washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane/MTB ether) and crystallization (heptane) to give white crystals of 1,4-difluoro-2-isothiocyanato-5-[4-[4-(trifluoromethoxy)phenyl]phenyl]benzene.

[0891] Phase sequence K 109 N 165 I. [0892] ??=1.92 [0893] ?n=0.3329 [0894] ?.sub.1=522 mPas

[0895] In analogy to Synthesis Examples 1 to 5 the following compounds are obtained:

TABLE-US-00007 physical No. Compound properties 6 [00527] 7 [00528] 8 [00529] 9 [00530] 10 [00531] 11 [00532] 12 [00533] 13 [00534] 14 [00535] 15 [00536] 16 [00537] 17 [00538] K 52 I ?? = 9.92 ?n = 0.4079 ?.sub.1 = 70 mPas 18 [00539] K 52 N (44) I ?? = 9.14 ?n = 0.3863 ?.sub.1 = 89 mPas 19 [00540] 20 [00541] 21 [00542] 22 [00543] 23 [00544] 24 [00545] K 41 I ?? = 7.52 ?n = 0.3252 ?.sub.1 = 106 mPas 25 [00546] 26 [00547] 27 [00548] 28 [00549] 29 [00550] 30 [00551] 31 [00552] 32 [00553] 33 [00554] 34 [00555] 35 [00556] 36 [00557] 37 [00558] 38 [00559] 39 [00560] 40 [00561] 41 [00562] 42 [00563] 43 [00564] 44 [00565] 45 [00566] 46 [00567] 47 [00568] 48 [00569] 49 [00570] 50 [00571] 51 [00572] 52 [00573] 53 [00574] 54 [00575] 55 [00576] 56 [00577] 57 [00578] 58 [00579] 59 [00580] 60 [00581] 61 [00582] 62 [00583] 63 [00584] 64 [00585] 65 [00586] 66 [00587] 67 [00588] 68 [00589] K 55 SmA 123 N 191 I ?? = 9.43 ?n = 0.4827 69 [00590] 70 [00591] 71 [00592] 72 [00593] 73 [00594] 74 [00595] 75 [00596] 76 [00597] 77 [00598] 78 [00599] 79 [00600] 80 [00601] 81 [00602] 82 [00603] 83 [00604] 84 [00605] 85 [00606] 86 [00607]

MIXTURE EXAMPLES

[0896] Comparative examples C1 to C4 and Mixture Examples M1 to M19 are prepared and investigated as described below.

Comparative Example C1

[0897]

TABLE-US-00008 ST-3b-1 0.12 Clp. [? C.]: 155.5 PTU-3-S 9.988 ?n [589 nm, 20? C.]: 0.3688 PTU-5-S 10.9868 n.sub.e [589 nm, 20? C.]: 1.8739 PPTU-4-S 5.9928 n.sub.o [589 nm, 20? C.]: 1.5051 PPTU-5-S 9.988 ?? [1 kHz, 20? C.]: 18.8 PGTU-4-S 5.9928 ?.sub.|| [1 kHz, 20? C.]: 22.8 PGU-3-S 11.9856 ?.sub.? [1 kHz, 20? C.]: 4.0 PPU-TO-S 22.9724 ?.sub.1 [mPa s, 20? C.]: 464 CPTU-5-S 21.9736 K.sub.1 [pN, 20? C.]: 17.2 ? 100.0 K.sub.3 [pN, 20? C.]: 24.9 K.sub.3/K.sub.1 [pN, 20? C.]: 1.44 V.sub.0 [V, 20? C.]: 1.02 LTS bulk [h, ?30? C.]: 1000 LTS bulk [h, ?40? C.]: 1000 ?.sub.r, || [20? C., 19 GHz]: 3.70 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0061 ?.sub.r, ? [20? C., 19 GHz]: 2.45 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0110 ? [20? C., 19 GHz]: 0.338 ? [20? C., 19 GHz]: 30.9

Mixture Example M1

[0898]

TABLE-US-00009 PPTU-4-S 6.0 Clp. [? C.]: 160.5 PPTU-5-S 10.0 ?? [1 kHz, 20? C.]: 16.1 PGTU-4-S 6.0 ?.sub.|| [1 kHz, 20? C.]: 19.8 PGU-3-S 12.0 ?.sub.? [1 kHz, 20? C.]: 3.7 PPU-TO-S 23.0 ?.sub.1 [mPa s, 20? C.]: 466 CPTU-5-S 22.0 K.sub.1 [pN, 20? C.]: 19.0 PTG(F)-3-S 11.0 K.sub.3 [pN, 20? C.]: 25.8 PTG(F)-4-S 10.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.36 ? 100.0 V.sub.0 [V, 20? C.]: 1.15 LTS bulk [h, ?30? C.]: 1000 ?.sub.r, || [20? C., 19 GHz]: 3.76 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0060 ?.sub.r, ? [20? C., 19 GHz]: 2.46 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0102 ? [20? C., 19 GHz]: 0.346 ? [20? C., 19 GHz]: 34.0

[0899] Mixture Example M1 shows that replacement of the compounds PTU-3-S and PTU-5-S of Comparative Example C1 with the compounds PTG(F)-3-S and PTG(F)-4-S according to the invention results in a significant increase of the material quality 11 from 30.9 to 34.0 due to a higher tunability.

Comparative Example C2

[0900]

TABLE-US-00010 ST-3b-1 0.12 Clp. [? C.]: 158 PPTU-4-S 5.9928 ?n [589 nm, 20? C.]: 0.4015 PPTU-5-S 14.982 n.sub.e [589 nm, 20? C.]: 1.9286 PPU-TO-S 15.9808 n.sub.o [589 nm, 20? C.]: 1.5271 CPTU-5-S 24.97 ?? [1 kHz, 20? C.]: 15.0 PTU-3-S 9.988 ?.sub.|| [1 kHz, 20? C.]: 18.6 PTU-5-S 9.988 ?.sub.? [1 kHz, 20? C.]: 3.6 CPU(F.F)-3-S 17.9784 ?.sub.1 [mPa s, 20? C.]: 492 ? 100.0 K.sub.1 [pN, 20? C.]: 17.6 K.sub.3 [pN, 20? C.]: 24.4 K.sub.3/K.sub.1 [pN, 20? C.]: 1.39 V.sub.0 [V, 20? C.]: 1.14 LTS bulk [h, ?30? C.]: 1000 LTS bulk [h, ?40? C.]: 960 ?.sub.r, || [20? C., 19 GHz]: 3.59 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0052 ?.sub.r, ? [20? C., 19 GHz]: 2.42 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0084 ? [20? C., 19 GHz]: 0.328 ? [20? C., 19 GHz]: 39.0

Mixture Example M2

[0901]

TABLE-US-00011 PPTU-4-S 6.0 Clp. [? C.]: 159.5 PPTU-5-S 15.0 ?? [1 kHz, 20? C.]: 13.0 PPU-TO-S 14.0 ?.sub.|| [1 kHz, 20? C.]: 16.4 CPTU-5-S 25.0 ?.sub.? [1 kHz, 20? C.]: 3.4 CPU(F.F)-3-S 18.0 ?.sub.1 [mPa s, 20? C.]: 472 PTG(F)-3-S 11.0 K.sub.1 [pN, 20? C.]: 19.1 PTG(F)-4-S 11.0 K.sub.3 [pN, 20? C.]: 24.3 ? 100.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.27 V.sub.0 [V, 20? C.]: 1.28 LTS bulk [h, ?30? C.]: 1000 ?.sub.r, || [20? C., 19 GHz]: 3.62 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0050 ?.sub.r, ? [20? C., 19 GHz]: 2.41 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0075 ? [20? C., 19 GHz]: 0.334 ? [20? C., 19 GHz]: 44.9

[0902] Mixture Example M2 shows that replacement of the compounds PTU-3-S and PTU-5-S in Comparative Example C2 with the compounds PTG(F)-3-S and PTG(F)-4-S according to the invention results in a significant increase of the material quality ? due to both a higher tunability and a lower dielectric loss.

Mixture Example M3

[0903]

TABLE-US-00012 PTU-5-S 9.0 Clp. [? C.]: 156.5 PPTU-4-S 6.0 ?? [1 kHz, 20? C.]: 14.1 PPTU-5-S 12.0 ?.sub.|| [1 kHz, 20? C.]: 17.5 CPTU-5-S 21.0 ?.sub.? [1 kHz, 20? C.]: 3.4 CPU(F.F)-3-S 18.0 ?.sub.1 [mPa s, 20? C.]: 458 CPG(F)-4-S 4.0 K.sub.1 [pN, 20? C.]: 19.9 PTPG(F)-4-S 6.0 K.sub.3 [pN, 20? C.]: 22.7 PTG(F)-4-S 14.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.14 PPG(F)-TO-S 2.0 V.sub.0 [V, 20? C.]: 1.25 PPTG(F)-4-S 8.0 LTS bulk [h, ?20? C.]: 144 ? 100.0 ? [20? C., 19 GHz]: 0.330 ?.sub.r, || [20? C., 19 GHz]: 3.58 ?.sub.r, ? [20? C., 19 GHz]: 2.39 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0047 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0069 ? [20? C., 19 GHz]: 47.9

Mixture Example M4

[0904]

TABLE-US-00013 PTU-3-S 10.0 Clp. [? C.]: 153 PPTU-4-S 6.0 ?? [1 kHz, 20? C.]: 16.6 PPTU-5-S 10.0 ?.sub.|| [1 kHz, 20? C.]: 20.3 PGTU-4-S 6.0 ?.sub.? [1 kHz, 20? C.]: 3.8 PGU-3-S 6.0 ?.sub.1 [mPa s, 20? C.]: 417 PPU-TO-S 16.0 K.sub.1 [pN, 20? C.]: 19.0 CPTU-5-S 18.0 K.sub.3 [pN, 20? C.]: 22.4 PTPG(F)-4-S 4.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.18 PTG(F)-4-S 16.0 V.sub.0 [V, 20? C.]: 1.13 PPTG(F)-4-S 8.0 LTS bulk [h, ?20? C.]: 144 ? 100.0 ? [20? C., 19 GHz]: 0.344 ?.sub.r, || [20? C., 19 GHz]: 3.73 ?.sub.r, ? [20? C., 19 GHz]: 2.45 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0059 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0098 ? [20? C., 19 GHz]: 35.1

Mixture Example M5

[0905]

TABLE-US-00014 PTU-3-S 11.0 Clp. [? C.]: 155 PTU-5-S 11.0 ?? [1 kHz, 20? C.]: 20.0 PPTU-4-S 6.0 ?.sub.|| [1 kHz, 20? C.]: 24.0 PPTU-5-S 10.0 ?.sub.? [1 kHz, 20? C.]: 4.0 PGTU-4-S 6.0 ?.sub.1 [mPa s, 20? C.]: 471 PGU-3-S 12.0 K.sub.1 [pN, 20? C.]: 18.8 PPU-TO-S 12.0 K.sub.3 [pN, 20? C.]: 23.3 CPTU-5-S 22.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.24 PTPG(F)-4-S 10.0 V.sub.0 [V, 20? C.]: 1.03 ? 100.0 LTS bulk [h, ?40? C.]: 1000 ?.sub.r, || [20? C., 19 GHz]: 3.70 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0058 ?.sub.r, ? [20? C., 19 GHz]: 2.45 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0105 ? [20? C., 19 GHz]: 0.338 ? [20? C., 19 GHz]: 32.3

Mixture Example M6

[0906]

TABLE-US-00015 PTU-3-S 10.0 Clp. [? C.]: 150.5 PTU-5-S 10.0 ?? [1 kHz, 20? C.]: 18.4 PPTU-4-S 6.0 ?.sub.|| [1 kHz, 20? C.]: 22.3 PPTU-5-S 15.0 ?.sub.? [1 kHz, 20? C.]: 3.9 PGTU-4-S 6.0 ?.sub.1 [mPa s, 20? C.]: 655 PTPG(F)-4-S 8.0 K.sub.1 [pN, 20? C.]: 18.5 PP(1)TU-TO-S 14.0 K.sub.3 [pN, 20? C.]: 22.2 PTPU-TO-S 6.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.20 PPTU-4(1.sup.[2])-S 25.0 V.sub.0 [V, 20? C.]: 1.06 ? 100.00 ?.sub.r, || [20? C., 19 GHz]: 3.81 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0050 ?.sub.r, ? [20? C., 19 GHz]: 2.45 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0085 ? [20? C., 19 GHz]: 0.357 ? [20? C., 19 GHz]: 42.3

Mixture Example M7

[0907]

TABLE-US-00016 PTU-3-S 10.0 Clp. [? C.]: 160.5 PTU-5-S 5.0 ?? [1 kHz, 20? C.]: 17.7 PPTU-4-S 6.0 ?.sub.|| [1 kHz, 20? C.]: 21.4 PPTU-5-S 15.0 ?.sub.? [1 kHz, 20? C.]: 3.8 PGTU-4-S 6.0 ?.sub.1 [mPa s, 20? C.]: 768 PTPG(F)-4-S 8.0 K.sub.1 [pN, 20? C.]: 19.0 PP(1)TU-TO-S 16.0 K.sub.3 [pN, 20? C.]: 23.4 PTPU-TO-S 8.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.23 PPTU-4(1.sup.[2])-S 26.0 V.sub.0 [V, 20? C.]: 1.09 ? 100.0 ?.sub.r, || [20? C., 19 GHz]: 3.86 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0048 ?.sub.r, ? [20? C., 19 GHz]: 2.48 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0084 ? [20? C., 19 GHz]: 0.357 ? [20? C., 19 GHz]: 42.8

Mixture Example M8

[0908]

TABLE-US-00017 PPTU-4-S 6.0 Clp. [? C.]: 165 PPTU-5-S 14.0 LTS bulk [h, ?30? C.]: 480 PPU-TO-S 22.0 LTS bulk [h, ?40? C.]: 1000 CPTU-5-S 22.0 ?.sub.r, || [20? C., 19 GHz]: 3.61 PTU-3-S 8.0 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0053 PTU-5-S 8.0 ?.sub.r, ? [20? C., 19 GHz]: 2.45 CPG(F)-4-S 20.0 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0084 ? 100.0 ? [20? C., 19 GHz]: 0.322 ? [20? C., 19 GHz]: 38.3

Mixture Example M9

[0909]

TABLE-US-00018 PPTU-4-S 10.0 Clp. [? C.]: 164 PPTU-5-S 20.0 ?? [1 kHz, 20? C.]: 12.3 CPTU-5-S 15.0 ?.sub.|| [1 kHz, 20? C.]: 15.5 CPU(F.F)-3-S 18.0 ?.sub.? [1 kHz, 20? C.]: 3.2 CPG(F)-4-S 12.0 ?.sub.1 [mPa s, 20? C.]: 475 CPG(F)-4-S 10.0 K.sub.1 [pN, 20? C.]: 19.9 PTG(F)-4-S 15.0 K.sub.3 [pN, 20? C.]: 22.0 ? 100.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.11 V.sub.0 [V, 20? C.]: 1.34 ?.sub.r, || [20? C., 19 GHz]: 3.53 tan ?.sub.? r, || [20? C., 19 GHz]: 0.0044 ?.sub.r, ? [20? C., 19 GHz]: 2.40 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0058 ? [20? C., 19 GHz]: 0.322 ? [20? C., 19 GHz]: 55.9

Host Mixture H1

[0910]

TABLE-US-00019 ST-3b-1 0.12 Clp. [? C.]: 151 PTU-3-S 15.98 ?n [589 nm, 20? C.]: 0.3779 PGU-3-S 13.98 n.sub.e [589 nm, 20? C.]: 1.9169 PPTU-5-S 19.98 n.sub.o [589 nm, 20? C.]: 1.5390 CPU-2-S 34.96 ?? [1 kHz, 20? C.]: 22.7 CPU-4-S 14.98 ?.sub.? [1 kHz, 20? C.]: 27.0 ? 95.00 ?.sub.? [1 kHz, 20? C.]: 4.4 ?.sub.1 [mPa s, 20? C.]: 384 K.sub.1 [pN, 20? C.]: 16.8 K.sub.3 [pN, 20? C.]: 21.6 K.sub.3/K.sub.1 [pN, 20? C.]: 1.29 V.sub.0 [V, 20? C.]: 0.91 LTS bulk [h, ?20? C.]: 1000 LTS bulk [h, ?30? C.]: 216 ?.sub.r, ? [20? C., 19 GHz]: 3.59 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0059 ?.sub.r, ? [20? C., 19 GHz]: 2.47 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0106 ? [20? C., 19 GHz]: 0.311 ? [20? C., 19 GHz]: 29.3

Comparative Example C3

[0911]

TABLE-US-00020 PTU-3-S 10.0 e.sub.r, ? [20? C., 19 GHz]: 3.53 H1 90.0 tan d.sub.e r, ? [20? C., 19 GHz]: 0.0062 0.0 e.sub.r, {circumflex over ()} [20? C., 19 GHz]: 2.44 S 100.0 tan d.sub.e r, {circumflex over ()} [20? C., 19 GHz]: 0.0111 t [20? C., 19 GHz]: 0.310 h [20? C., 19 GHz]: 27.9

Mixture Example M10

[0912]

TABLE-US-00021 PTG(F)-3-S 10.0 ?.sub.r, ? [20? C., 19 GHz]: 3.59 H1 90.0 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0063 ? 100.0 ?.sub.r, ? [20? C., 19 GHz]: 2.47 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0109 ? [20? C., 19 GHz]: 0.313 ? [20? C., 19 GHz]: 28.9

[0913] The addition of 10% of the compound PTG(F)-3-S to the host mixture H1 (Mixture Example 10) results in a significantly higher figure-of-merit than when using the isomer PTU-3-S(Comparative Example C3).

Mixture Example M11

[0914]

TABLE-US-00022 PTG(F)-5-S 10.0 ?.sub.r, ? [20? C., 19 GHz]: 3.58 H1 90.0 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0063 ? 100.0 ?.sub.r, ? [20? C., 19 GHz]: 2.46 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0109 ? [20? C., 19 GHz]: 0.313 ? [20? C., 19 GHz]: 28.9

Comparative Example C4

[0915]

TABLE-US-00023 PPTU-4-S 10.0 e.sub.r, ? [20? C., 19 GHz]: 3.61 H1 90.0 tan ?.sub.e r, ? [20? C., 19 GHz]: 0.0059 0.0 e.sub.r, {circumflex over ()} [20? C., 19 GHz]: 2.49 ? 100.0 tan d.sub.e r, {circumflex over ()} [20? C., 19 GHz]: 0.0104 t [20? C., 19 GHz]: 0.312 h [20? C., 19 GHz]: 30.0

Mixture Example M12

[0916]

TABLE-US-00024 PPTG(F)-4-S 10.0 ?.sub.r, ? [20? C., 19 GHz]: 3.63 H1 90.0 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0057 ? 100.0 ?.sub.r, ? [20? C., 19 GHz]: 2.47 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0102 ? [20? C., 19 GHz]: 0.318 ? [20? C., 19 GHz]: 31.4

[0917] The addition of 10% of the compound PPTG(F)-3-S to the host mixture H1 (Mixture Example 12) results in a significantly higher figure-of-merit than when using the isomer PPTU-3-S(Comparative Example C3).

Mixture Example M13

[0918]

TABLE-US-00025 PPTG(F)-4(1[2])-S 10.0 ?.sub.r, ? [20? C., 19 GHz]: 3.59 H1 90.0 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0055 ? 100.0 ?.sub.r, ? [20? C., 19 GHz]: 2.45 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0096 ? [20? C., 19 GHz]: 0.318 ? [20? C., 19 GHz] 33.1

Mixture Example M14

[0919]

TABLE-US-00026 PPTU-4-S 6.0 Clp. [? C.]: 151 PPTU-5-S 12.0 ?? [1 kHz, 20? C.]: 16.1 PGTU-4-S 6.0 ?.sub.? [1 kHz, 20? C.]: 19.9 PGU-3-S 16.0 ?.sub.? [1 kHz, 20? C.]: 3.8 PPU-TO-S 26.0 ?.sub.1 [mPa s, 20? C.]: 419 CPTU-5-S 10.0 K.sub.1 [pN, 20? C.]: 18.6 PTG(F)-3-S 14.0 K.sub.3 [pN, 20? C.]: 24.3 PTG(F)-4-S 10.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.31 ? 100.0 V.sub.0 [V, 20? C.]: 1.13 ?.sub.r, ? [20? C., 19 GHz]: 3.78 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0064 ?.sub.r, ? [20? C., 19 GHz]: 2.47 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0109 ? [20? C., 19 GHz]: 0.348 ? [20? C., 19 GHz]: 32.1

Mixture Example M15

[0920]

TABLE-US-00027 PPTU-4-S 6.0 Clp. [? C.]: 155 PPTU-5-S 12.0 ?? [1 kHz, 20? C.]: 16.6 PGTU-4-S 6.0 ?.sub.? [1 kHz, 20? C.]: 20.3 PGU-3-S 16.0 ?.sub.? [1 kHz, 20? C.]: 3.8 PPU-TO-S 24.0 ?.sub.1 [mPa s, 20? C.]: 445 CPTU-5-S 14.0 K.sub.1 [pN, 20? C.]: 19.3 PTG(F)-3-S 12.0 K.sub.3 [pN, 20? C.]: 24.8 PTG(F)-4-S 10.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.28 ? 100.0 V.sub.0 [V, 20? C.]: 1.14 LTS bulk [h, ?30? C.]: 72 ?.sub.r, ? [20? C., 19 GHz]: 3.75 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0062 ?.sub.r, ? [20? C., 19 GHz]: 2.46 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0106 ? [20? C., 19 GHz]: 0.343 ? [20? C., 19 GHz]: 32.6

Mixture Example M16

[0921]

TABLE-US-00028 PPTU-4-S 6.0 Clp. [? C.]: 151 PPTU-5-S 12.0 ?? [1 kHz, 20? C.]: 12.4 PPU-TO-S 16.0 ?.sub.? [1 kHz, 20? C.]: 15.8 CPTU-5-S 22.0 ?.sub.? [1 kHz, 20? C.]: 3.4 CPU(F.F)-3-S 18.0 ?.sub.1 [mPa s, 20? C.]: 440 PTG(F)-3-S 14.0 K.sub.1 [pN, 20? C.]: 17.9 PTG(F)-4-S 12.0 K.sub.3 [pN, 20? C.]: 24.7 ? 100.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.38 V.sub.0 [V, 20? C.]: 1.27 LTS bulk [h, ?30? C.]: 456 ?.sub.r, ? [20? C., 19 GHz]: 3.59 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0052 ?.sub.r, ? [20? C., 19 GHz]: 2.40 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0076 ? [20? C., 19 GHz]: 0.332 ? [20? C., 19 GHz]: 43.7

Mixture Example M17

[0922]

TABLE-US-00029 PTU-3-S 10.0 Clp. [? C]: 156 PPTU-4-S 6.0 ?? [1 kHz, 20? C.]: 13.9 PPTU-5-S 12.0 ?.sub.? [1 kHz, 20? C.]: 17.5 PPU-TO-S 16.0 ?.sub.? [1 kHz, 20? C.]: 3.5 CPTU-5-S 25.0 ?.sub.1 [mPa s, 20? C.]: 459 CPU(F.F)-3-S 18.0 K.sub.1 [pN, 20? C.]: 18.1 PTG(F)-3-S 13.0 K.sub.3 [pN, 20? C.]: 24.7 ? 100.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.36 V.sub.0 [V, 20? C.]: 1.21 LTS bulk [h, ?30? C.]: 168 ?.sub.r, ? [20? C., 19 GHz]: 3.62 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0052 ?.sub.r, ? [20? C., 19 GHz]: 2.43 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0080 ? [20? C., 19 GHz]: 0.329 ? [20? C., 19 GHz]: 41.2

Mixture Example M18

[0923]

TABLE-US-00030 PPTU-4-S 6.0 Clp. [? C.]: 161 PPTU-5-S 15.0 ?? [1 kHz, 20? C.]: 15.7 PGU-3-S 12.0 ?.sub.? [1 kHz, 20? C.]: 19.3 PPU-TO-S 23.0 ?.sub.? [1 kHz, 20? C.]: 3.6 CPTU-5-S 23.0 ?.sub.1 [mPa s, 20? C.]: 466 PTG(F)-3-S 11.0 K.sub.1 [pN, 20? C.]: 19.2 PTG(F)-4-S 10.0 K.sub.3 [pN, 20? C.]: 26.7 ? 100.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.39 V.sub.0 [V, 20? C.]: 1.17 ?.sub.r, ? [20? C., 19 GHz]: 3.75 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0058 ?.sub.r, ? [20? C., 19 GHz]: 2.46 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0096 ? [20? C., 19 GHz]: 0.343 ? [20? C., 19 GHz]: 35.9

Mixture Example M19

[0924]

TABLE-US-00031 PGU-3-S 6.0 Clp. [? C]: 155.5 PPTU-4-S 6.0 ?? [1 kHz, 20? C.]: 13.8 PPTU-5-S 12.0 ?.sub.? [1 kHz, 20? C.]: 17.3 PPU-TO-S 22.0 ?.sub.? [1 kHz, 20? C.]: 3.5 CPTU-5-S 23.0 ?.sub.1 [mPa s, 20? C.]: 448 CPU(F.F)-3-S 7.0 K.sub.1 [pN, 20? C.]: 18.1 PTG(F)-3-S 13.0 K.sub.3 [pN, 20? C.]: 26.0 PTG(F)-4-S 11.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.43 ? 100.0 V.sub.0 [V, 20? C.]: 1.21 LTS bulk [h, ?30? C.]: 648 ?.sub.r, ? [20? C., 19 GHz]: 3.65 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0056 ?.sub.r, ? [20? C., 19 GHz]: 2.40 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0086 ? [20? C., 19 GHz]: 0.343 ? [20? C., 19 GHz]: 39.9

Mixture Example M20

[0925]

TABLE-US-00032 PTG(F)-3-S 12.0 PTG(F)-4-S 12.0 PPTG(F)-4-S 12.0 PPTU-4(1.sup.[2])-S 20.0 PTPG(F)-4-S 8.0 PPG(F)-TO-S 6.0 CPG(F)-4-S 30.0 ? 100.0

Mixture Example M20

[0926]

TABLE-US-00033 PTG(F)-3-S 10.0 Clp. [? C.]: 155.5 PTU-3-S 10.0 ?? [1 kHz, 20? C.]: 17.3 PTU-5-S 10.0 ?.sub.? [1 kHz, 20? C.]: 21.3 PPTU-5-S 15.0 ?.sub.? [1 kHz, 20? C.]: 4.0 CPTU-5-S 15.0 ?.sub.1 [mPa s, 20? C.]: 800 PPI(1)GU-5-S 7.0 K.sub.1 [pN, 20? C.]: 17.2 PPI(2)PU-5-S 10.0 K.sub.3 [pN, 20? C.]: 26.2 PGPU-5-S 5.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.53 PP(1)PU-5-S 6.0 V.sub.0 [V, 20? C.]: 1.06 PPI(1)PU-5-S 7.0 ?.sub.r, ? [20? C., 19 GHz]: 3.81 CTUIU-5-S 5.0 tan ?? .sub.r, ? [20? C., 19 GHz]: 0.0043 ? 100.0 ?.sub.r, ? [20? C., 19 GHz]: 2.60 tan ?? .sub.r, ? [20? C., 19 GHz]: 0.0070 ? [20? C., 19 GHz]: 0.317 ? [20? C., 19 GHz]: 45.3

Mixture Example M21

[0927]

TABLE-US-00034 PPTU-4-S 6.0 Clp. [? C.]: 160.5 PPTU-5-S 15.0 ?? [1 kHz, 20? C.]: 13.0 CPTU-5-S 24.0 ?.sub.? [1 kHz, 20? C.]: 16.2 CPU(F.F)-3-S 18.0 ?.sub.? [1 kHz, 20? C.]: 3.3 PTUI-2-S 12.0 ?.sub.1 [mPa s, 20? C.]: 477 PTUI-4-S 10.0 K.sub.1 [pN, 20? C.]: 20.3 PPTU-4(1[2])-S 10.0 K.sub.3 [pN, 20? C.]: 22.0 PPTG(F)-4-S 5.0 K.sub.3/K.sub.1 [pN, 20? C.]: 1.08 ? 100.0 V.sub.0 [V, 20? C.]: 1.32 ?.sub.r, ? [20? C., 19 GHz]: 3.76 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0046 ?.sub.r, ? [20? C., 19 GHz]: 2.48 tan ?.sub.? r, ? [20? C., 19 GHz]: 0.0057 ? [20? C., 19 GHz]: 0.341 ? [20? C., 19 GHz]: 60.3