Patent ID: 12203023

EXAMPLES

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

dist. distilledDABCO 1,4-Diazabicyclo[2.2.2]octaneTHE TetrahydrofuranMTB ether Methyl-tert-butyl etherdist. distilledXPhos 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenylXPhos Pd G2 Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)palladium (II)Pd(amphos)Cl2Bis(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

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

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.

Phase sequence: K 82 N 180 I (decomp)Δε=8.42Δn=0.2701γ1=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

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

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.

Phase sequence K 48 N (23) I.Δε=8.92Δn=0.3776γ1=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

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

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.

Phase sequence: K 58 SmA 164 N 226 I.Δε=10.51Δn=0.5021γ1=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

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

Pd(amphos)Cl2(6.0 mg, 9 μmol) 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

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.

Phase sequence: K 65 SmA 123 N 199 I.Δε=9.72Δn=0.4573γ1=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

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

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.

Phase sequence K 109 N 165 I.Δε=1.92Δn=0.3329γ1=522 mPas

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

physicalNo.Compoundproperties67891011121314151617K 52 I Δε = 9.92 Δn = 0.4079 γ1= 70 mPas18K 52 N (44) I Δε = 9.14 Δn = 0.3863 γ1= 89 mPas192021222324K 41 I  Δε = 7.52 Δn = 0.3252 γ1= 106 mPas2526272829303132333435363738394041424344454647484950515253545556575859606162636465666768K 55 SmA 123 N 191 I Δε = 9.43 Δn = 0.4827697071727374757677787980818283848586

MIXTURE EXAMPLES

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

Comparative Example C1

ST-3b-10.12Clp. [° C.]:155.5PTU-3-S9.988Δn [589 nm, 20° C.]:0.3688PTU-5-S10.9868ne[589 nm, 20° C.]:1.8739PPTU-4-S5.9928no[589 nm, 20° C.]:1.5051PPTU-5-S9.988Δε [1 kHz, 20° C.]:18.8PGTU-4-S5.9928ε||[1 kHz, 20° C.]:22.8PGU-3-S11.9856ε⊥[1 kHz, 20° C.]:4.0PPU-TO-S22.9724γ1[mPa s, 20° C.]:464CPTU-5-S21.9736K1[pN, 20° C.]:17.2Σ100.0K3[pN, 20° C.]:24.9K3/K1[pN, 20° C.]:1.44V0[V, 20° C.]:1.02LTS bulk [h, −30° C.]:1000LTS bulk [h, −40° C.]:1000εr, ||[20° C., 19 GHz]:3.70tan δε r, ||[20° C., 19 GHz]:0.0061εr, ⊥[20° C., 19 GHz]:2.45tan δε r, ⊥[20° C., 19 GHz]:0.0110τ [20° C., 19 GHz]:0.338η [20° C., 19 GHz]:30.9

Mixture Example M1

PPTU-4-S6.0Clp. [° C.]:160.5PPTU-5-S10.0Δε [1 kHz, 20° C.]:16.1PGTU-4-S6.0ε||[1 kHz, 20° C.]:19.8PGU-3-S12.0ε⊥[1 kHz, 20° C.]:3.7PPU-TO-S23.0γ1[mPa s, 20° C.]:466CPTU-5-S22.0K1[pN, 20° C.]:19.0PTG(F)-3-S11.0K3[pN, 20° C.]:25.8PTG(F)-4-S10.0K3/K1[pN, 20° C.]:1.36Σ100.0V0[V, 20° C.]:1.15LTS bulk [h, −30° C.]:1000εr, ||[20° C., 19 GHz]:3.76tan δε r, ||[20° C., 19 GHz]:0.0060εr, ⊥[20° C., 19 GHz]:2.46tan δε r, ⊥[20° C., 19 GHz]:0.0102τ [20° C., 19 GHz]:0.346η [20° C., 19 GHz]:34.0

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

ST-3b-10.12Clp. [° C.]:158PPTU-4-S5.9928Δn [589 nm, 20° C.]:0.4015PPTU-5-S14.982ne[589 nm, 20° C.]:1.9286PPU-TO-S15.9808no[589 nm, 20° C.]:1.5271CPTU-5-S24.97Δε [1 kHz, 20° C.]:15.0PTU-3-S9.988ε||[1 kHz, 20° C.]:18.6PTU-5-S9.988ε⊥[1 kHz, 20° C.]:3.6CPU(F.F)-3-S17.9784γ1[mPa s, 20° C.]:492Σ100.0K1[pN, 20° C.]:17.6K3[pN, 20° C.]:24.4K3/K1[pN, 20° C.]:1.39V0[V, 20° C.]:1.14LTS bulk [h, −30° C.]:1000LTS bulk [h, −40° C.]:960εr, ||[20° C., 19 GHz]:3.59tan δε r, ||[20° C., 19 GHz]:0.0052εr, ⊥[20° C., 19 GHz]:2.42tan δε r, ⊥[20° C., 19 GHz]:0.0084τ [20° C., 19 GHz]:0.328η [20° C., 19 GHz]:39.0

Mixture Example M2

PPTU-4-S6.0Clp. [° C.]:159.5PPTU-5-S15.0Δε [1 kHz, 20° C.]:13.0PPU-TO-S14.0ε||[1 kHz, 20° C.]:16.4CPTU-5-S25.0ε⊥[1 kHz, 20° C.]:3.4CPU(F.F)-3-S18.0γ1[mPa s, 20° C.]:472PTG(F)-3-S11.0K1[pN, 20° C.]:19.1PTG(F)-4-S11.0K3[pN, 20° C.]:24.3Σ100.0K3/K1[pN, 20° C.]:1.27V0[V, 20° C.]:1.28LTS bulk [h, −30° C.]:1000εr, ||[20° C., 19 GHz]:3.62tan δε r, ||[20° C., 19 GHz]:0.0050εr, ⊥[20° C., 19 GHz]:2.41tan δε r, ⊥[20° C., 19 GHz]:0.0075τ [20° C., 19 GHz]:0.334η [20° C., 19 GHz]:44.9

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 η due to both a higher tunability and a lower dielectric loss.

Mixture Example M3

PTU-5-S9.0Clp. [° C.]:156.5PPTU-4-S6.0Δε [1 kHz, 20° C.]:14.1PPTU-5-S12.0ε||[1 kHz, 20° C.]:17.5CPTU-5-S21.0ε⊥[1 kHz, 20° C.]:3.4CPU(F.F)-3-S18.0γ1[mPa s, 20° C.]:458CPG(F)-4-S4.0K1[pN, 20° C.]:19.9PTPG(F)-4-S6.0K3[pN, 20° C.]:22.7PTG(F)-4-S14.0K3/K1[pN, 20° C.]:1.14PPG(F)-TO-S2.0V0[V, 20° C.]:1.25PPTG(F)-4-S8.0LTS bulk [h, −20° C.]:144Σ100.0τ [20° C., 19 GHz]:0.330εr, ||[20° C., 19 GHz]:3.58εr, ⊥[20° C., 19 GHz]:2.39tan δε r, ||[20° C., 19 GHz]:0.0047tan δε r, ⊥[20° C., 19 GHz]:0.0069η [20° C., 19 GHz]:47.9

Mixture Example M4

PTU-3-S10.0Clp. [° C.]:153PPTU-4-S6.0Δε [1 kHz, 20° C.]:16.6PPTU-5-S10.0ε||[1 kHz, 20° C.]:20.3PGTU-4-S6.0ε⊥[1 kHz, 20° C.]:3.8PGU-3-S6.0γ1[mPa s, 20° C.]:417PPU-TO-S16.0K1[pN, 20° C.]:19.0CPTU-5-S18.0K3[pN, 20° C.]:22.4PTPG(F)-4-S4.0K3/K1[pN, 20° C.]:1.18PTG(F)-4-S16.0V0[V, 20° C.]:1.13PPTG(F)-4-S8.0LTS bulk [h, −20° C.]:144Σ100.0τ [20° C., 19 GHz]:0.344εr, ||[20° C., 19 GHz]:3.73εr, ⊥[20° C., 19 GHz]:2.45tan δε r, ||[20° C., 19 GHz]:0.0059tan δε r, ⊥[20° C., 19 GHz]:0.0098η [20° C., 19 GHz]:35.1

Mixture Example M5

PTU-3-S11.0Clp. [° C.]:155PTU-5-S11.0Δε [1 kHz, 20° C.]:20.0PPTU-4-S6.0ε||[1 kHz, 20° C.]:24.0PPTU-5-S10.0ε⊥[1 kHz, 20° C.]:4.0PGTU-4-S6.0γ1[mPa s, 20° C.]:471PGU-3-S12.0K1[pN, 20° C.]:18.8PPU-TO-S12.0K3[pN, 20° C.]:23.3CPTU-5-S22.0K3/K1[pN, 20° C.]:1.24PTPG(F)-4-S10.0V0[V, 20° C.]:1.03Σ100.0LTS bulk [h, −40° C.]:1000εr, ||[20° C., 19 GHz]:3.70tan δε r, ||[20° C., 19 GHz]:0.0058εr, ⊥[20° C., 19 GHz]:2.45tan δε r, ⊥[20° C., 19 GHz]:0.0105τ [20° C., 19 GHz]:0.338η [20° C., 19 GHz]:32.3

Mixture Example M6

PTU-3-S10.0Clp. [° C.]:150.5PTU-5-S10.0Δε [1 kHz, 20° C.]:18.4PPTU-4-S6.0ε||[1 kHz, 20° C.]:22.3PPTU-5-S15.0ε⊥[1 kHz, 20° C.]:3.9PGTU-4-S6.0γ1[mPa s, 20° C.]:655PTPG(F)-4-S8.0K1[pN, 20° C.]:18.5PP(1)TU-TO-S14.0K3[pN, 20° C.]:22.2PTPU-TO-S6.0K3/K1[pN, 20° C.]:1.20PPTU-4(1[2])-S25.0V0[V, 20° C.]:1.06Σ100.00εr, ||[20° C., 19 GHz]:3.81tan δε r, ||[20° C., 19 GHz]:0.0050εr, ⊥[20° C., 19 GHz]:2.45tan δε r, ⊥[20° C., 19 GHz]:0.0085τ [20° C., 19 GHz]:0.357η [20° C., 19 GHz]:42.3

Mixture Example M7

PTU-3-S10.0Clp. [° C.]:160.5PTU-5-S5.0Δε [1 kHz, 20° C.]:17.7PPTU-4-S6.0ε||[1 kHz, 20° C.]:21.4PPTU-5-S15.0ε⊥[1 kHz, 20° C.]:3.8PGTU-4-S6.0γ1[mPa s, 20° C.]:768PTPG(F)-4-S8.0K1[pN, 20° C.]:19.0PP(1)TU-TO-S16.0K3[pN, 20° C.]:23.4PTPU-TO-S8.0K3/K1[pN, 20° C.]:1.23PPTU-4(1[2])-S26.0V0[V, 20° C.]:1.09Σ100.0εr, ||[20° C., 19 GHz]:3.86tan δε r, ||[20° C., 19 GHz]:0.0048εr, ⊥[20° C., 19 GHz]:2.48tan δε r, ⊥[20° C., 19 GHz]:0.0084τ [20° C., 19 GHz]:0.357η [20° C., 19 GHz]:42.8

Mixture Example M8

PPTU-4-S6.0Clp. [° C.]:165PPTU-5-S14.0LTS bulk [h, −30° C.]:480PPU-TO-S22.0LTS bulk [h, −40° C.]:1000CPTU-5-S22.0εr, ||[20° C., 19 GHz]:3.61PTU-3-S8.0tan δε r, ||[20° C., 19 GHz]:0.0053PTU-5-S8.0εr, ⊥[20° C., 19 GHz]:2.45CPG(F)-4-S20.0tan δε r, ⊥[20° C., 19 GHz]:0.0084Σ100.0τ [20° C., 19 GHz]:0.322η [20° C., 19 GHz]:38.3

Mixture Example M9

PPTU-4-S10.0Clp. [° C.]:164PPTU-5-S20.0Δε [1 kHz, 20° C.]:12.3CPTU-5-S15.0ε||[1 kHz, 20° C.]:15.5CPU(F.F)-3-S18.0ε⊥[1 kHz, 20° C.]:3.2CPG(F)-4-S12.0γ1[mPa s, 20° C.]:475CPG(F)-4-S10.0K1[pN, 20° C.]:19.9PTG(F)-4-S15.0K3[pN, 20° C.]:22.0Σ100.0K3/K1[pN, 20° C.]:1.11V0[V, 20° C.]:1.34εr, ||[20° C., 19 GHz]:3.53tan δε r, ||[20° C., 19 GHz]:0.0044εr, ⊥[20° C., 19 GHz]:2.40tan δε r, ⊥[20° C., 19 GHz]:0.0058τ [20° C., 19 GHz]:0.322η [20° C., 19 GHz]:55.9
Host Mixture H1

ST-3b-10.12Clp. [° C.]:151PTU-3-S15.98Δn [589 nm, 20° C.]:0.3779PGU-3-S13.98ne[589 nm, 20° C.]:1.9169PPTU-5-S19.98no[589 nm, 20° C.]:1.5390CPU-2-S34.96Δε [1 kHz, 20° C.]:22.7CPU-4-S14.98ε∥[1 kHz, 20° C.]:27.0Σ95.00ε⊥[1 kHz, 20° C.]:4.4γ1[mPa s, 20° C.]:384K1[pN, 20° C.]:16.8K3[pN, 20° C.]:21.6K3/K1[pN, 20° C.]:1.29V0[V, 20° C.]:0.91LTS bulk [h, −20° C.]:1000LTS bulk [h, −30° C.]:216εr, ∥[20° C., 19 GHz]:3.59tan δε r, ∥[20° C., 19 GHz]:0.0059εr, ⊥[20° C., 19 GHz]:2.47tan δε r, ⊥[20° C., 19 GHz]:0.0106τ [20° C., 19 GHz]:0.311η [20° C., 19 GHz]:29.3

Comparative Example C3

PTU-3-S10.0er, ∥[20° C., 19 GHz]:3.53H190.0tan de r, ∥[20° C., 19 GHz]:0.00620.0er,{circumflex over ( )} [20° C., 19 GHz]:2.44S100.0tan de r,{circumflex over ( )} [20° C., 19 GHz]:0.0111t [20° C., 19 GHz]:0.310h [20° C., 19 GHz]:27.9

Mixture Example M10

PTG(F)-3-S10.0εr, ∥[20° C., 19 GHz]:3.59H190.0tan δε r, ∥[20° C., 19 GHz]:0.0063Σ100.0εr, ⊥[20° C., 19 GHz]:2.47tan δε r, ⊥[20° C., 19 GHz]:0.0109τ [20° C., 19 GHz]:0.313η [20° C., 19 GHz]:28.9

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

PTG(F)-5-S10.0εr, ∥[20° C., 19 GHz]:3.58H190.0tan δε r, ∥[20° C., 19 GHz]:0.0063Σ100.0εr, ⊥[20° C., 19 GHz]:2.46tan δε r, ⊥[20° C., 19 GHz]:0.0109τ [20° C., 19 GHz]:0.313η [20° C., 19 GHz]:28.9

Comparative Example C4

PPTU-4-S10.0er, ∥[20° C., 19 GHz]:3.61H190.0tan δe r, ∥[20° C., 19 GHz]:0.00590.0er,{circumflex over ( )} [20° C., 19 GHz]:2.49Σ100.0tan de r,{circumflex over ( )} [20° C., 19 GHz]:0.0104t [20° C., 19 GHz]:0.312h [20° C., 19 GHz]:30.0

Mixture Example M12

PPTG(F)-4-S10.0εr, ∥[20° C., 19 GHz]:3.63H190.0tan δε r, ∥[20° C., 19 GHz]:0.0057Σ100.0εr, ⊥[20° C., 19 GHz]:2.47tan δε r, ⊥[20° C., 19 GHz]:0.0102τ [20° C., 19 GHz]:0.318η [20° C., 19 GHz]:31.4

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

PPTG(F)-4(1[2])-S10.0εr, ∥[20° C., 19 GHz]:3.59H190.0tan δε r, ∥[20° C., 19 GHz]:0.0055Σ100.0εr, ⊥[20° C., 19 GHz]:2.45tan δε r, ⊥[20° C., 19 GHz]:0.0096τ [20° C., 19 GHz]:0.318η [20° C., 19 GHz]33.1

Mixture Example M14

PPTU-4-S6.0Clp. [° C.]:151PPTU-5-S12.0Δε [1 kHz, 20° C.]:16.1PGTU-4-S6.0ε∥[1 kHz, 20° C.]:19.9PGU-3-S16.0ε⊥[1 kHz, 20° C.]:3.8PPU-TO-S26.0γ1[mPa s, 20° C.]:419CPTU-5-S10.0K1[pN, 20° C.]:18.6PTG(F)-3-S14.0K3[pN, 20° C.]:24.3PTG(F)-4-S10.0K3/K1[pN, 20° C.]:1.31Σ100.0V0[V, 20° C.]:1.13εr, ∥[20° C., 19 GHz]:3.78tan δε r, ∥[20° C., 19 GHz]:0.0064εr, ⊥[20° C., 19 GHz]:2.47tan δε r, ⊥[20° C., 19 GHz]:0.0109τ [20° C., 19 GHz]:0.348η [20° C., 19 GHz]:32.1

Mixture Example M15

PPTU-4-S6.0Clp. [° C.]:155PPTU-5-S12.0Δε [1 kHz, 20° C.]:16.6PGTU-4-S6.0ε∥[1 kHz, 20° C.]:20.3PGU-3-S16.0ε⊥[1 kHz, 20° C.]:3.8PPU-TO-S24.0γ1[mPa s, 20° C.]:445CPTU-5-S14.0K1[pN, 20° C.]:19.3PTG(F)-3-S12.0K3[pN, 20° C.]:24.8PTG(F)-4-S10.0K3/K1[pN, 20° C.]:1.28Σ100.0V0[V, 20° C.]:1.14LTS bulk [h, −30° C.]:72εr, ∥[20° C., 19 GHz]:3.75tan δε r, ∥[20° C., 19 GHz]:0.0062εr, ⊥[20° C., 19 GHz]:2.46tan δε r, ⊥[20° C., 19 GHz]:0.0106τ [20° C., 19 GHz]:0.343η [20° C., 19 GHz]:32.6

Mixture Example M16

PPTU-4-S6.0Clp. [° C.]:151PPTU-5-S12.0Δε [1 kHz, 20° C.]:12.4PPU-TO-S16.0ε∥[1 kHz, 20° C.]:15.8CPTU-5-S22.0ε⊥[1 kHz, 20° C.]:3.4CPU(F.F)-3-S18.0γ1[mPa s, 20° C.]:440PTG(F)-3-S14.0K1[pN, 20° C.]:17.9PTG(F)-4-S12.0K3[pN, 20° C.]:24.7Σ100.0K3/K1[pN, 20° C.]:1.38V0[V, 20° C.]:1.27LTS bulk [h, −30° C.]:456εr, ∥[20° C., 19 GHz]:3.59tan δε r, ∥[20° C., 19 GHz]:0.0052εr, ⊥[20° C., 19 GHz]:2.40tan δε r, ⊥[20° C., 19 GHz]:0.0076τ [20° C., 19 GHz]:0.332η [20° C., 19 GHz]:43.7

Mixture Example M17

PTU-3-S10.0Clp. [° C]:156PPTU-4-S6.0Δε [1 kHz, 20° C.]:13.9PPTU-5-S12.0ε∥[1 kHz, 20° C.]:17.5PPU-TO-S16.0ε⊥[1 kHz, 20° C.]:3.5CPTU-5-S25.0γ1[mPa s, 20° C.]:459CPU(F.F)-3-S18.0K1[pN, 20° C.]:18.1PTG(F)-3-S13.0K3[pN, 20° C.]:24.7Σ100.0K3/K1[pN, 20° C.]:1.36V0[V, 20° C.]:1.21LTS bulk [h, −30° C.]:168εr, ∥[20° C., 19 GHz]:3.62tan δε r, ∥[20° C., 19 GHz]:0.0052εr, ⊥[20° C., 19 GHz]:2.43tan δε r, ⊥[20° C., 19 GHz]:0.0080τ [20° C., 19 GHz]:0.329η [20° C., 19 GHz]:41.2

Mixture Example M18

PPTU-4-S6.0Clp. [° C.]:161PPTU-5-S15.0Δε [1 kHz, 20° C.]:15.7PGU-3-S12.0ε∥[1 kHz, 20° C.]:19.3PPU-TO-S23.0ε⊥[1 kHz, 20° C.]:3.6CPTU-5-S23.0γ1[mPa s, 20° C.]:466PTG(F)-3-S11.0K1[pN, 20° C.]:19.2PTG(F)-4-S10.0K3[pN, 20° C.]:26.7Σ100.0K3/K1[pN, 20° C.]:1.39V0[V, 20° C.]:1.17εr, ∥[20° C., 19 GHz]:3.75tan δε r, ∥[20° C., 19 GHz]:0.0058εr, ⊥[20° C., 19 GHz]:2.46tan δε r, ⊥[20° C., 19 GHz]:0.0096τ [20° C., 19 GHz]:0.343η [20° C., 19 GHz]:35.9

Mixture Example M19

PGU-3-S6.0Clp. [° C]:155.5PPTU-4-S6.0Δε [1 kHz, 20° C.]:13.8PPTU-5-S12.0ε∥[1 kHz, 20° C.]:17.3PPU-TO-S22.0ε⊥[1 kHz, 20° C.]:3.5CPTU-5-S23.0γ1[mPa s, 20° C.]:448CPU(F.F)-3-S7.0K1[pN, 20° C.]:18.1PTG(F)-3-S13.0K3[pN, 20° C.]:26.0PTG(F)-4-S11.0K3/K1[pN, 20° C.]:1.43Σ100.0V0[V, 20° C.]:1.21LTS bulk [h, −30° C.]:648εr, ∥[20° C., 19 GHz]:3.65tan δε r, ∥[20° C., 19 GHz]:0.0056εr, ⊥[20° C., 19 GHz]:2.40tan δε r, ⊥[20° C., 19 GHz]:0.0086τ [20° C., 19 GHz]:0.343η [20° C., 19 GHz]:39.9

Mixture Example M20

PTG(F)-3-S12.0PTG(F)-4-S12.0PPTG(F)-4-S12.0PPTU-4(1[2])-S20.0PTPG(F)-4-S8.0PPG(F)-TO-S6.0CPG(F)-4-S30.0Σ100.0

Mixture Example M20

PTG(F)-3-S10.0Clp. [° C.]:155.5PTU-3-S10.0Δε [1 kHz, 20° C.]:17.3PTU-5-S10.0ε∥[1 kHz, 20° C.]:21.3PPTU-5-S15.0ε⊥[1 kHz, 20° C.]:4.0CPTU-5-S15.0γ1[mPa s, 20° C.]:800PPI(1)GU-5-S7.0K1[pN, 20° C.]:17.2PPI(2)PU-5-S10.0K3[pN, 20° C.]:26.2PGPU-5-S5.0K3/K1[pN, 20° C.]:1.53PP(1)PU-5-S6.0V0[V, 20° C.]:1.06PPI(1)PU-5-S7.0εr, ∥[20° C., 19 GHz]:3.81CTUIU-5-S5.0tan δεr, ∥[20° C., 19 GHz]:0.0043Σ100.0εr, ⊥[20° C., 19 GHz]:2.60tan δεr, ⊥[20° C., 19 GHz]:0.0070τ [20° C., 19 GHz]:0.317η [20° C., 19 GHz]:45.3

Mixture Example M21

PPTU-4-S6.0Clp. [° C.]:160.5PPTU-5-S15.0Δε [1 kHz, 20° C.]:13.0CPTU-5-S24.0ε∥[1 kHz, 20° C.]:16.2CPU(F.F)-3-S18.0ε⊥[1 kHz, 20° C.]:3.3PTUI-2-S12.0γ1[mPa s, 20° C.]:477PTUI-4-S10.0K1[pN, 20° C.]:20.3PPTU-4(1[2])-S10.0K3[pN, 20° C.]:22.0PPTG(F)-4-S5.0K3/K1[pN, 20° C.]:1.08Σ100.0V0[V, 20° C.]:1.32εr, ∥[20° C., 19 GHz]:3.76tan δε r, ∥[20° C., 19 GHz]:0.0046εr, ⊥[20° C., 19 GHz]:2.48tan δε r, ⊥[20° C., 19 GHz]:0.0057τ [20° C., 19 GHz]:0.341η [20° C., 19 GHz]:60.3