LIQUID-CRYSTALLINE MEDIUM AND LIQUID-CRYSTAL DISPLAY COMPRISING THE SAME AND COMPOUNDS

Abstract

The invention relates to a liquid-crystalline medium having a nematic phase comprising one or more compounds of formula X

##STR00001##

wherein the parameters have the meaning given in the text,
to the use thereof in an electro-optical display, particularly in an active-matrix display based on the IPS or FFS effect, to displays of this type which contain a liquid-crystalline medium of this type and to the use of the compounds of formula X for improvement of the transmission and/or response times of a liquid-crystalline medium which comprises one or more additional mesogenic compounds, as well as to certain compounds of formula X, as specified in the text.

Claims

1. Liquid-crystalline medium having a nematic phase and a dielectric anisotropy (Δε) of 0.5 or more, characterized in that it comprises one or more compounds of formula X ##STR00437## in which W denotes O or S R.sup.1X and R.sup.2X independently of each other denote H, an alkyl radical having 1 to 15 C atoms, wherein one or more CH.sub.2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF.sub.2O—, —OCF.sub.2—, —CH═CH—, ##STR00438## —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, and R.sup.2X alternatively denotes X.sup.X, A on each occurrence, identically or differently, denotes a radical selected from the following groups: a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, and decaline-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, b) the group consisting of 1,4-phenylene and 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which, in addition, one or more H atoms may be replaced by L, c) the group consisting of 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, thiophene-2,5-diyl, selenophene-2,5-diyl, and 1,2,3,4-tetrahydronanaphthaline-2,6-diyl, each of which may be mono- or polysubstituted by L, d) the group consisting of bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, and spiro[3.3]heptane-2,6-diyl, in which one or more H atoms may be replaced by F, L each, identically or differently, denote halogen, cyano, alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl group with 1 to 7 C atoms, wherein one or more H atoms may be substituted by F or Cl, Z on each occurrence, identically or differently, denotes a single bond, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2CH.sub.2—, —CF.sub.2CF.sub.2—, —C(O)O—, —OC(O)—, —CH.sub.2O—, —OCH.sub.2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C□C—, n denotes 0, 1, or 2, Y.sup.1, Y.sup.2 and Y.sup.3 identically or differently, denote H, F, Cl, CF.sub.3, or CHF.sub.2, wherein one of Y.sup.1 and Y.sup.2 is not H or Y.sup.3 is F, and, in case both Y.sup.1 and Y.sup.3 are both F, Y.sup.2 is not H, and X.sup.X denotes F, Cl, CN, NCS, SF.sub.5, fluorinated alkyl, alkoxy, alkenyl or alkenyloxy each having up to 5 C atoms, preferably F, CF.sub.3, OCF.sub.3 or NCS and one or more additional compounds.

2. Medium according to claim 1, characterized in that it comprises one or more compounds of formula B, ##STR00439## in which ##STR00440## denotes ##STR00441## denotes ##STR00442## n denotes 1 or 2, R.sup.1 denotes alkyl, alkoxy, fluorinated alkyl, fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl and X.sup.1 denotes F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenlyoxy.

3. Medium according to claim 1, characterized in that it additionally comprises one or more compounds of formula I: ##STR00443## in which ##STR00444## denotes ##STR00445## denotes ##STR00446## n denotes 0 or 1, R.sup.11 and R.sup.12 independently of each other denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms and R.sup.11 alternatively denotes R.sup.1 and R.sup.12 alternatively denotes X.sup.1, R.sup.1 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, preferably having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms and preferably alkyl or alkenyl, and X.sup.1 denotes F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, from which the compounds of formula B are excluded.

4. Medium according to claim 1, characterized in that it comprises one or more compounds selected from the group of compounds of formulae II and III. ##STR00447## in which R.sup.2 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, ##STR00448## on each appearance, independently of one another, denote ##STR00449## L.sup.21 and L.sup.22 denote H or F, X.sup.2 denotes halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, m denotes 0, 1, 2 or 3, R.sup.3 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms ##STR00450## on each appearance, independently of one another, are ##STR00451## L.sup.31 and L.sup.32, independently of one another, denote H or F, X.sup.3 denotes halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, F, Cl, —OCF.sub.3, —OCHF.sub.2, —O—CH.sub.2CF.sub.3, —O—CH═CF.sub.2, —O—CH═CH.sub.2 or —CF.sub.3, Z.sup.3 denotes —CH.sub.2CH.sub.2—, —CF.sub.2CF.sub.2—, —COO—, trans-CH═CH—, trans-CF═CF—, —CH.sub.2O— or a single bond, and n denotes 0, 1, 2 or 3.

5. Liquid-crystalline medium according to claim 1, characterized in that it comprises one or more dielectrically neutral compounds selected from the group of formulae IV and V: ##STR00452## in which R.sup.41 and R.sup.42, independently of one another, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, ##STR00453## independently of one another and, if ##STR00454## A occurs twice, also these independently of one another, denote ##STR00455## Z.sup.41 and Z.sup.42, independently of one another and, if Z.sup.41 occurs twice, also these independently of one another, denote —CH.sub.2CH.sub.2—, —COO—, trans-CH═CH—, trans-CF═CF—, —CH.sub.2O—, —CF.sub.2O—, —C≡C— or a single bond, p denotes 0, 1 or 2, R.sup.51 and R.sup.52, independently of one another, have one of the meanings given for R.sup.41 and R.sup.42, ##STR00456## if present, each, independently of one another, denote ##STR00457## Z.sup.51 to Z.sup.53 each, independently of one another, denote —CH.sub.2—CH.sub.2—, —CH.sub.2—O—, —CH═CH—, —C≡C—, —COO— or a single bond, and i and j each, independently of one another, denote 0 or 1.

6. Liquid-crystalline medium according to claim 5, characterized in that it comprises one or more compounds selected from the group of formulae VI to IX: ##STR00458## wherein R.sup.61 denotes an unsubstituted alkyl radical having 1 to 7 C atoms, an unsubstituted alkenyl radical having 2 to 7 C atoms, an unsubstituted alkoxy radical having 1 to 6 C atoms or an unsubstituted alkenyloxy radical having 2 to 6 C atoms, R.sup.62 denotes an unsubstituted alkyl radical having 1 to 7 C atoms, an unsubstituted alkoxy radical having 1 to 6 C atoms or an unsubstituted alkenyloxy radical having 2 to 6 C atoms, and I denotes 0 or 1, R.sup.71 denotes an unsubstituted alkyl radical having 1 to 7 C atoms, or an unsubstituted alkenyl radical having 2 to 7 C atoms, R.sup.72 denotes an unsubstituted alkyl radical having 1 to 7 C atoms, an unsubstituted alkoxy radical having 1 to 6 C atoms or an unsubstituted alkenyloxy radical having 2 to 6 C atoms, ##STR00459## denotes ##STR00460## R.sup.81 denotes an unsubstituted alkyl radical having 1 to 7 C atoms, or an unsubstituted alkenyl radical having 2 to 7 C atoms, R.sup.82 denotes an unsubstituted alkyl radical having 1 to 7 C atoms, an unsubstituted alkoxy radical having 1 to 6 C atoms or an unsubstituted alkenyloxy radical having 2 to 6 C atoms, preferably having 2, 3 or 4 C atoms, ##STR00461## denotes ##STR00462## Z.sup.8 denotes —(C═O)—O—, —CH.sub.2—O—, —CF.sub.2—O— or —CH.sub.2—CH.sub.2—, denotes 0 or 1, R.sup.91 and R.sup.92 independently of one another have the meaning given for R.sup.72 above, ##STR00463## denotes ##STR00464## p and q independently of each other denote 0 or 1, and

7. Medium according to claim 1, characterized in that the total concentration of the compounds of formula B in the medium as a whole is 1% or more to 60% or less.

8. Medium according to claim 1, characterized in that it additionally comprises one or more chiral compounds and/or stabilizers.

9. Electro-optical display or electro-optical component, characterized in that it comprises a liquid-crystalline medium according to claim 1.

10. Display according to claim 9, characterized in that it is based on the IPS- or FFS mode.

11. Display according to claim 9, characterized in that it contains an active-matrix addressing device.

12. An electro-optical display or an electro-optical component comprising medium according to claim 1.

13. Process for the preparation of a liquid-crystalline medium according to claim 1, characterized in that one or more compounds of formula X are mixed with one or more additional mesogenic compounds and optionally one or more additives.

14. Compound selected from the group of compounds of formulae X-4 to X-6 ##STR00465## in which the parameters R, denotes R.sup.1X, X denotes X.sup.X, and R.sup.1X, X.sup.X, Y.sup.1, Y.sup.2, Y.sup.3 and the other parameters have the respective meanings given in claim 1.

15. Process for the preparation of a compound selected from the group of compounds of formulae X-4 to X-6 as given in claim 14, characterized in that a phenol of formula P or of formula P.sup.I ##STR00466## or a compound of formula S or of formula S.sup.I ##STR00467## wherein R of the ester group is alkyl, preferably with one to 3 C atoms and the other parameters have the respective meanings given in claim 14, is treated with a base.

Description

EXAMPLES

[0400] The following examples explain the present invention without restricting it in any way. However, the physical properties make it clear to the person skilled in the art 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: Synthesis of 2,4-Difluoro-7-(4-n-propylcyclohexen-1-yl)-3-(trifluoro-methyl)dibenzofuran (1)

[0401] ##STR00389##

Step 1.1: 1-(4-Bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol

[0402] ##STR00390##

[0403] A solution of 1-bromo-2-fluoro-4-iodo-benzene (CAS-no.136434-77-0, 40.2 g, 134 mmol) in THE (250 mL) is cooled to −5° C., followed by dropwise addition of a solution of isopropyl magnesium chloride (2 mol/L in THF, 68 mL, 136 mmol) and THE (100 mL). The reaction mixture is stirred for 90 min at 0° C.

[0404] Then a solution of 4-propylcyclohexanone (CAS-no.40649-36-3, 19.1 g, 136 mmol) in THE (50 mL) is added dropwise at 0° C., and the reaction mixture is slowly warmed up to room temperature and stirred for 3 h. The reaction mixture is hydrolyzed with ice water, diluted with MTB ether and acidified with hydrochloride acid (2 N). 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. 1-(4-bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol is isolated as a yellow oil.

Step 1.2: 1-Bromo-2-fluoro-4-(4-propylcyclohexen-1-yl)benzene

[0405] ##STR00391##

[0406] A mixture of 1-(4-bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol (44 g, 97 mmol) and toluene-4-sulfonic acid monohydrate (1.5 g, 8 mmol) in toluene (400 mL) is heated at reflux temperature for 2 h. Then it is cooled to room temperature, neutralized with sodium hydroxide solution (2 N) and diluted with water. The aqueous phase is separated and extracted with toluene. The combined organic phases are dried (sodium sulfate) and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent n-heptane) to give 1-bromo-2-fluoro-4-(4-propylcyclohexen-1-yl)benzene as a colorless oil.

Step 1.3: [2-Fluoro-4-(4-propylcyclohexen-1-yl)phenyl]boronic Acid

[0407] ##STR00392##

[0408] A solution of 1-bromo-2-fluoro-4-(4-propylcyclohexen-1-yl)benzene (80 g, 245 mmol) in THE (650 mL) is cooled to −65° C., followed by dropwise addition of butyl lithium solution (175 mL, 279 mmol) at −60° C. and stirred for 1 h. A solution of trimethyl borate (31 mL, 273 mmol) in THE (100 mL) is added dropwise at −65° C. and stirred for further 60 minutes. Then the reaction mixture is slowly allowed to warm up and hydrolyzed at 5° C. with water, diluted with MTB ether and acidified with hydrochloride solution (2 N). 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 extracted with n-heptane to give [2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]boronic acid as a light yellow solid.

Step 1.4: 6-Bromo-2,4-difluoro-3-(trifluoromethyl)phenol

[0409] ##STR00393##

[0410] A solution of 5-bromo-1,3-difluoro-2-(trifluoromethyl) benzene (CAS-no. 156243-64-0, 86 g, 321 mmol) in THE (400 mL) is cooled to −75° C., followed by dropwise addition of lithium diisopropyl amide solution (200 mL, 400 mmol) and stirring at −75° C. for 1 h. Then trimethyl borate (75 mL, 660 mmol) is added dropwise at −75° C., and the reaction mixture is stirred for further 60 minutes. Then it is warmed up to 0° C. and a mixture of hydrochloride acid (10%, 500 mL) and THE (100 mL) is added. After phase separation, the organic phase is cooled to 0° C. Hydrogen peroxide (210 mL, 2.68 mol) is added at 0° C. to the reaction mixture, which is stirred for 1 h and then heated up to 40° C. and stirred overnight. It is cooled to room temperature, diluted with MTB ether, and the phases are separated. The organic phase is washed with dist. water, brine and sodium sulfite solution until peroxide-free. The organic phase is dried (sodium sulfate) and concentrated in vacuo. The residue is washed with sodium hydroxide solution and hydrochloride acid and purified by silica gel chromatography (solvent dichloromethane) to give 6-bromo-2,4-difluoro-3-(trifluoromethyl) phenol as a brown oil.

Step 1.5: 2,4-Difluoro-6-[2-fluoro-4-(4-propylcyclohexen-1-yl) phenyl]-3-(trifluoromethyl)phenol

[0411] ##STR00394##

[0412] A mixture of 6-bromo-2,4-difluoro-3-(trifluoromethyl) phenol (9.5 g, 30 mmol), potassium carbonate (6.1 g, 44 mol), tris(dibenzylideneacetone)-dipalladium(0) (57 mg, 0.1 mmol) and CataCXium A (33 mg, 0.1 mmol) in THE (50 mL) and dist. water (25 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of [2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]boronic acid 5 (7.8 g, 30 mmol) in THE (25 mL). The reaction mixture is heated at reflux temperature overnight. Then it is cooled to room temperature and diluted with MTB ether and dist. water. 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 1-chlorobutane). 2,4-difluoro-6-[2-fluoro-4-(4-propylcyclohexen-1-yl) phenyl]-3-(trifluoromethyl)phenol 8 is isolated as a light brown solid.

Step 1.6: 2,4-Difluoro-7-(4-n-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzofuran

[0413] ##STR00395##

[0414] A mixture of 2,4-difluoro-6-[2-fluoro-4-(4-propylcyclohexen-1-yl) phenyl]-3-(trifluoromethyl) phenol 8 (3.2 g, 8 mmol), potassium phosphate monohydrate (2.4 g, 10 mmol) and 1,3-dimethyltetrahydro-2(1H)-pyrimidinone (30 mL, 248 mmol) is stirred at 110° C. overnight. The reaction mixture is purified by silica gel chromatography (solvent n-heptane) and crystallization (ethanol) to give 2,4-difluoro-7-(4-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzofuran as a colorless solid.

[0415] Phase Sequence: T.sub.g −35° C. K 67° C. S.sub.X (33° C.) S.sub.A (40° C.) I; Δε=18.5; Δn=0.2036.

Synthesis Example 2: Synthesis of 2,4-Difluoro-7-(4-n-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzothiophene (2)

[0416] ##STR00396##

Step 2.1: [2,4-Difluoro-6-[2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-3-(trifluoromethyl)phenyl]trifluoromethanesulfonate

[0417] ##STR00397##

[0418] Trifluoromethanesulfonic anhydride (3 mL, 18 mmol) is slowly added to a solution of 2,4-difluoro-6-[2-fluoro-4-(4-propylcyclohexen-1-yl) phenyl]-3-(trifluoromethyl)phenol (6 g, 14 mmol), triethylamine (3 mL, 21 mmol) and 4-(dimethylamino)-pyridine (52 mg, 0.4 mmol) in dichloromethane (65 mL) at 5° C. under nitrogen atmosphere. The solution is stirred at room temperature overnight. The reaction mixture is purified by silica gel chromatography (solvent 1-chlorobutane) to give [2,4-difluoro-6-[2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-3-(trifluoromethyl)phenyl]trifluoromethanesulfonate as a yellow oil.

Step 2.2: 2,4-Difluoro-7-(4-n-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzothiophene

[0419] ##STR00398##

[0420] A solution of [2,4-difluoro-6-[2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-3-(trifluoromethyl)phenyl] trifluoromethanesulfonate (8.2 g, 15 mmol), 3-mercapto-propionic acid 2-ethylhexyl ester (4.3 mL, 18 mmol) and N-ethyl diisopropyl amine (3.7 mL, 22 mmol) in toluene (40 mL) is degassed with Argon. Tris(dibenzylideneacetone)dipalladium(0) (140 mg, 0.2 mmol) and (oxydi-2,1-phenylene)bis(diphenylphosphine) (160 mg, 0.3 mmol) are quickly added to the solution, and the reaction mixture is heated at reflux overnight. Then it is cooled to room temperature, and a solution of potassium tert-butylate (2.0 g, 18 mmol) in THE (12 mL) is added to the reaction mixture containing intermediate in situ. The reaction mixture is heated at reflux overnight, followed by addition of a second portion of a solution of potassium tert-butylate (1.0 g, 9 mmol) in THE (6 mL). The reaction mixture is heated again at reflux overnight. Then it is cooled to room temperature, quenched with water, acidified with hydrochloric acid (25%) at 0° C. and diluted with MTB ether. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with dist. water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent n-heptane) and crystallization (ethanol) to give 2,4-difluoro-7-(4-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzothiophene 12 as colourless crystals.

[0421] Phase sequence: K 150° C. S.sub.X 116° C. I; Δε=22.9; Δn=0.2101.

Synthesis Example 3: Synthesis of 4-Fluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzofuran

[0422] ##STR00399##

Step 3.1: 2′,3′-Difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethyl-biphenyl-2-ol

[0423] ##STR00400##

[0424] A mixture of 2-bromo-5-trifluoromethyl-phenol (2) (CAS 402-05-1) (10 g, 41 mmol), potassium carbonate (8.4 g, 61.0 mmol), Tris(dibenzylideneacetone)-dipalladium(0) (80 mg, 0.08 mmol) and CataCXium A (50 mg, 0.13 mmol) in THE (50 mL) and distilled water (33 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of 2,3-difluoro-4-(4-propylcyclohexen-1-yl)-phenylboronic acid (1) (11.6 g, 41 mmol) in THE (50 mL). The reaction mixture is heated at reflux temperature overnight. Then it is cooled to room temperature and diluted with MTB-ether and distilled water. The aqueous phase is separated and extracted with MTB-ether. The combined organic phases are washed with distilled water and brine, dried (sodium sulphate) and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent 1-chlorobutane). 2′,3′-Difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethyl-biphenyl-2-ol (3) is isolated as a yellow solid.

Step 3.2: 4-Fluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzofuran

[0425] ##STR00401##

[0426] A mixture of 2′,3′-difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethyl-biphenyl-2-ol (3) (5.9 g, 15 mmol), potassium phosphate monohydrate (4.5 g, 18.7 mmol) and 1,3-dimethyltetrahydro-2(1H)-pyrimidinone (60 mL, 0.5 mol) is stirred at 110° C. overnight. The reaction mixture is purified by silica gel chromatography (solvent n-heptane) and crystallization (ethanol) to give 4-fluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenozofuran (4) as white crystals.

[0427] Compound (4) has the following phase characteristics: [0428] K 92° C. SmA 110° C. I and the properties: [0429] Δn=0.1994; Δε=5.0; γ.sub.1=397.

Synthesis Example 4: Synthesis of 4-Fluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzothiophene (4)

[0430] ##STR00402##

Synthesis Example 5: Synthesis of 4-Fluoro-7-(4-propyl-cyclohex-1-enyl)-3-trifluoromethoxy-dibenzo furan (5)

[0431] ##STR00403##

Synthesis Example 6: Synthesis of 4-Fluoro-7-(4-propyl-cyclohex-1-enyl)-3-trifluoromethoxy-dibenzothiophene

[0432] ##STR00404##

Step 6.1: 3,2′-Difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol

[0433] ##STR00405##

[0434] A mixture of 6-Bromo-2-fluoro-3-trifluoromethoxyphenol (2, CAS 1805580-01-1) (15 g, 50 mmol), potassium carbonate (10.4 g, 75 mmol), tris(dibenzylideneacetone)-dipalladium(0) (100 mg, 0.1 mmol) and CataCXium A (60 mg, 0.16 mmol) in THE (100 mL) and distilled water (50 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of 2-fluoro-4-(4-propylcyclohexen-1-yl)-phenylboronic acid (1) (13.2 g, 50 mmol) in THE (50 mL). The reaction mixture is heated at reflux temperature overnight. Then it is cooled to room temperature and diluted with MTB ether and distilled water. The aqueous phase is separated and extracted with MTB-Ether. The combined organic phases are washed with distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent 1-chlorobutane). 3,2′-Difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol (3) is isolated as a brown solid.

Step 6.2: Trifluoro-methanesulfonic acid 3,2′-difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl ester

[0435] ##STR00406##

[0436] Trifluoromethanesulfonic anhydride (5 mL, 30 mmol) is slowly added to a solution of 3,2′-difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol (3) (10 g, 24 mmol), TEA (5 mL, 36 mmol) and DMAP (90 mg, 0.74 mmol) in dichloromethane (100 mL) at 5° C. under nitrogen atmosphere. The solution is stirred at room temperature overnight. The reaction mixture is purified by silica gel chromatography (solvent 1-chlorbutane) to give trifluoro-methanesulfonic acid 3,2′-difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl ester (4) as a brown oil.

Step 6.3: 4-Fluoro-7-(4-propyl-cyclohex-1-enyl)-3-trifluoromethoxy-dibenzothiophene

[0437] ##STR00407##

[0438] This reaction is performed as a one-pot reaction. In the first step, a solution of trifluoro-methanesulfonic acid 3,2′-difluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl ester (4) (13.3 g, 23 mmol), 3-mercapto-propionic acid 2-ethylhexyl ester (7 mL, 30 mol), N-ethyldiisopropylamine (6.5 mL, 38 mmol) and toluene (60 mL) is degassed with Argon for 1 h. Tris(dibenzylideneacetone)dipalladium(0) (240 mg, 0.25 mmol) and (oxydi-2,1-phenylene)bis(diphenylphosphine) (270 mg, 0.49 mmol) are quickly added to the solution, and the reaction mixture is heated at reflux temperature overnight. Then it is allowed to cool to room temperature. In the second step, a solution of potassium tert-butylate (3.5 g, 31 mmol) in THE (30 mL) is added to the reaction mixture containing intermediate (5) in situ. The reaction mixture is heated at reflux temperature overnight, followed by addition of a second portion of a solution of potassium tert-butylate (1.75 g, 16 mmol) in THE (15 mL). The reaction mixture is heated again at reflux temperature overnight. Then it is cooled to room temperature, quenched with distilled water and hydrochloric acid (25%) at 0° C. and diluted with MTB-ether. The aqueous phase is separated and extracted with MTB-ether. The combined organic phases are washed with distilled water and brine, dried (sodium sulphate) and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane) to give 4-fluoro-7-(4-propyl-cyclohex-1-enyl)-3-trifluoromethoxy-dibenzothiophene (6) as white crystals.

[0439] Compound (6) has the following phase characteristics: [0440] K 101° C. SmA 194° C. I and the properties: [0441] Δn=0.2143; Δε=10.8; γ.sub.1=556.

[0442] In the following table the following abbreviations for the end groups are used

##STR00408##

[0443] The physical properties are given at a temperature of 20° C. and γ.sub.1 is given in mPa.Math.s.

TABLE-US-00007 XA-1-1 [00409] No: 1- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 K 86° C. I; Δn = 0.1512; Δε = 12.1; γ.sub.1 = 134 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 K 63° C. I 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00008 XA-1-2 [00410] No: 2- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.3 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.3 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00009 XA-1-3 [00411] No: 3- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.3 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F K 109° C. I 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F K 81° C. I; Δn = 0.1411 Δε = 11.9; γ.sub.1 = 58 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F K 48° C. I; Δn = 0.1351 Δε = 9.9; γ.sub.1 = 69 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 K 74° C. I; Δn = 0.1450 Δε = 19.1; γ.sub.1 = 121 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 K 82° C. I 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00010 XA-1-4 [00412] No: 4- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.3 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.7 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F K 73° C. I; Δn = 0.1270; Δε = 5.1; γ.sub.1 = 87 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 K 111° C. I 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3 K 89° C. I; Δn = 0.1210; Δε = 9.9; γ.sub.1 = 173

TABLE-US-00011 XB-1-1 [00413] No: 5- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 K 105° C. S.sub.A 113° C. I; Δn = 0.1591; Δε = 17.7; γ.sub.1 = 217 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 K 113° C. S.sub.A 125° C. I 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00012 XB-1-2 [00414] No: 6- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.3 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.3 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00013 XB-1-3 [00415] No: 7- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.3 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F K 146° C. I 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 K 97° C. S.sub.A (77° C.) I; Δn = 0.1571, Δε = 23.3; γ.sub.1 = 287 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 K 110° C. S.sub.A (95° C.) I; Δn = 0.1450, Δε = 17.3; γ.sub.1 = 240 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00014 XB-1-4 [00416] No: 8- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.3 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F K 74° C. I; Δn = 0.1351; Δε = 7.0; γ.sub.1 = 96 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 K 81° C. S.sub.A (69° C.) I; Δn = 0.1489; Δε = 15.3; γ.sub.1 = 1407 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3 K 108° C. I

TABLE-US-00015 XA-2-1 [00417] No: 9- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 C-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 85° C. S.sub.A 108° C. I; Δn = 0.2168; Δε = 9.5; γ.sub.1 = 462 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 K 83° C. S.sub.A 132° C. I; Δn = 0.2068; Δε = 6.2; γ.sub.1 = 338 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 K 63° C. I 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00016 XA-2-2 [00418] No: 10- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00017 XA-2-3 [00419] No: 11- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F K 85° C. N 94.° C. I; Δn = 0.2090; Δε = 9.7; γ.sub.1 = 366  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 T.sub.g −35° C. K 67° C. X.sub.X (33° C.) S.sub.A (40° C.) I; Δn = 0.2036; Δε = 18.5; γ.sub.1 = 457 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 K 75° C. S.sub.A 75° C. N 86° C. I; Δn = 0.1341; Δε = 13.3; γ.sub.1 = 424 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00018 XA-2-4 [00420] No: 12- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F K 112° C. I, Δn = 0.1992; Δε = 5.5; γ.sub.1 = 447  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 63° C. S.sub.A (54° C. ) I; Δn = 0.1928; Δε = 12.7; γ.sub.1 = 446 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 K 83° C. S.sub.A (82° C.) I; Δn = 0.1690; Δε = 8.3; γ.sub.1 = 574 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00019 XA-2-5 [00421] No: 13- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 92 C S.sub.A 110° C. I; Δn = 0.1994; Δε = 5.0; γ.sub.1 = 397 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 T.sub.g −58° C. K 61 S.sub.A 124° C. I; Δn = 0.1966; Δε = 2.7; γ.sub.1 = 283 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00020 XB-2-1 [00422] No: 14- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 142° C. S.sub.A 181° C. I; Δn = 0.2251; Δε = 16.1; γ.sub.1 = 750 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 K 101° C. S.sub.A 194° C. I; Δn = 0.2143; Δε = 10.8; γ.sub.1 = 556 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00021 XB-2-2 [00423] No: 15- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00022 XB-2-3 [00424] No: 16- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F K 143° C. S.sub.A (125° C.) N (133° C.) I; Δn = 0.2050; Δε = 14.1; γ.sub.1 = 429  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 150° C. S.sub.X 116° C. I; Δn = 0.2101; Δε = 22.9; γ.sub.1 = 635 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 K 137° C. S.sub.A 147° C. I; Δn = 0.1957; Δε = 20.9; γ.sub.1 = 831 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00023 XB-2-4 [00425] No: 17- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F K 127° C. N 133° C. I; Δn = 0.2210; Δε = 7.9; γ.sub.1 = 574  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 117° C. S.sub.A (110° C.) I; Δn = 0.2004; Δε = 15.6; γ.sub.1 = 526 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 K 116° C. S.sub.A 140° C. I; Δn = 0.1850; Δε = 10.7; γ.sub.1 = 722 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00024 XB-2-5 [00426] No: 18- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 101 C S.sub.A 169° C. I; Δn = 0.2081; Δε = 7.0; γ.sub.1 = 686 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 T.sub.g −66° C. K 86 C S.sub.A 180° C. I; Δn = 0.2084; Δε = 4.0; γ.sub.1 = 439 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00025 XA-3-1 [00427] No: 19- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 112° C. I; Δn = 0.1672 Δε = 8.1; γ.sub.1 = 451 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 K 62° C. S.sub.A 78° C. N 85.5° C. I; Δn = 0.1630; Δε = 4.7; γ.sub.1 = 366 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00026 XA-3-2 [00428] No: 20- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00027 XA-3-3 [00429] No: 21- R.sup.1X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00028 XA-3-4 [00430] No: 22- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00029 XA-3-5 [00431] No: 23- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00030 XB-3-1 [00432] No: 24- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 K 143° C. I; Δn = 0.1862; Δε = 13.7; γ.sub.1 = 885 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00031 XB-3-2 [00433] No: 25- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00032 XB-3-3 [00434] No: 26- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00033 XB-3-4 [00435] No: 27- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

TABLE-US-00034 XB-3-5 [00436] No: 28- R.sup.X X.sup.X Phase Range; properties  1 CH.sub.3 F  2 C.sub.2H.sub.5 F  3 n-C.sub.3H.sub.7 F  4 n-C.sub.4H.sub.9 F  5 n-C.sub.5H.sub.11 F  6 n-C.sub.6H.sub.13 F  7 n-C.sub.7H.sub.15 F  8 n-C.sub.8H.sub.17 F  9 c-C.sub.3H.sub.5 F 10 c-C.sub.3H.sub.5CH.sub.2 F 11 c-C.sub.4H.sub.7 F 12 c-C.sub.5H.sub.7 F 13 c-C.sub.5H.sub.9 F 14 CH.sub.2═CH F 15 CH.sub.3CH═CH F 16 CH.sub.2═CH(CH.sub.2).sub.2 F 17 CH.sub.3O F 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F 22 CH.sub.3 CF.sub.3 23 C.sub.2H.sub.5 CF.sub.3 24 n-C.sub.3H.sub.7 CF.sub.3 25 n-C.sub.4H.sub.9 CF.sub.3 26 n-C.sub.5H.sub.11 CF.sub.3 27 n-C.sub.6H.sub.13 CF.sub.3 28 n-C.sub.7H.sub.15 CF.sub.3 29 n-C.sub.8H.sub.17 CF.sub.3 30 c-C.sub.3H.sub.5 CF.sub.3 31 c-C.sub.3H.sub.5CH.sub.2 CF.sub.3 32 c-C.sub.4H.sub.7 CF.sub.3 33 c-C.sub.5H.sub.7 CF.sub.3 34 c-C.sub.5H.sub.9 CF.sub.3 35 CH.sub.2═CH CF.sub.3 36 CH.sub.3CH═CH CF.sub.3 37 CH.sub.2═CH(CH.sub.2).sub.2 CF.sub.3 38 CH.sub.3O CF.sub.3 39 C.sub.2H.sub.5O CF.sub.3 40 n-C.sub.3H.sub.7O CF.sub.3 41 n-C.sub.4H.sub.9O CF.sub.3 42 n-C.sub.5H.sub.11O CF.sub.3 43 CH.sub.3 OCF.sub.3 44 C.sub.2H.sub.5 OCF.sub.3 45 n-C.sub.3H.sub.7 OCF.sub.3 46 n-C.sub.4H.sub.9 OCF.sub.3 47 n-C.sub.5H.sub.11 OCF.sub.3 48 n-C.sub.6H.sub.13 OCF.sub.3 49 n-C.sub.7H.sub.15 OCF.sub.3 50 n-C.sub.8H.sub.17 OCF.sub.3 51 c-C.sub.3H.sub.5 OCF.sub.3 52 c-C.sub.3H.sub.5CH.sub.2 OCF.sub.3 53 c-C.sub.4H.sub.7 OCF.sub.3 54 c-C.sub.5H.sub.7 OCF.sub.3 55 c-C.sub.5H.sub.9 OCF.sub.3 56 CH.sub.2═CH OCF.sub.3 57 CH.sub.3CH═CH OCF.sub.3 58 CH.sub.2═CH(CH.sub.2).sub.2 OCF.sub.3 59 CH.sub.3O OCF.sub.3 60 C.sub.2H.sub.5O OCF.sub.3 61 n-C.sub.3H.sub.7O OCF.sub.3 62 n-C.sub.4H.sub.9O OCF.sub.3 63 n-C.sub.5H.sub.11O OCF.sub.3

MIXTURE EXAMPLES

[0444] In the following exemplary mixtures are disclosed.

Comparative Example A

[0445] The following mixture (CE-A) is prepared and investigated.

TABLE-US-00035 Mixture CE-A Composition Compound Concentration No. Abbreviation /% by weight 1 CC-3-V 31.5 2 CC-3-V1 6.5 3 CCP-3-3 6.0 4 CCP-V-1 12.0 5 CCP-V2-1 12.0 6 PP-1-2V1 5.0 7 CPGP-5-2 2.0 8 PUQU-3-F 20.0 9 APUQU-2-F 5.0 Σ 100.0 Physical properties T(N, I)= 78.5° C. n.sub.e(20° C., 589 nm)= 1.5876 Δn(20° C., 589 nm)= 0.1001 ε.sub.⊥(20° C., 1 kHz)= 3.0 Δε(20° C., 1 kHz)= 6.0 ε.sub.av.(20° C., 1 kHz)= 5.0 γ.sub.1(20° C.)= 64 mPa .Math. s k.sub.11(20° C.)= 13.3 pN k.sub.22(20° C.)= t.b.d. pN k.sub.33(20° C.)= 15.5 pN V.sub.0(20° C.)= 1.58 V V.sub.10(20° C.)= 2.13 V Remark: t.b.d.: to be determined

TABLE-US-00036 TABLE 1 Example CE-A A-1 A-2 A-3 Composition Cpd. None LBh-3-T LBh(S)-3-T LBfi-3-T Synth.Ex. None (1) (2) (3) c(Cpd.)/% 0 10.0 10.0 10.0 c(Host A)/% 100 90.0 90.0 90.0 Properties T(N, I)/° C. 78.5 77.5 81.0 79.5 n.sub.e(589 nm) 1.5876 t.b.d. t.b.d. 1.5988 Δn(589 nm) 0.1001 t.b.d. t.b.d. 0.1105 ε.sub.⊥(1 kHz) 3.0 t.b.d. t.b.d. 3.4 Δε(1 kHz) 6.0 t.b.d. t.b.d. 5.8 ε.sub.av.(1 kHz) 5.0 t.b.d. t.b.d. 5.3 ε.sub.⊥/Δε(1 kHz) 0.50 t.b.d. t.b.d. 0.59 γ.sub.1/mPa .Math. s 64 t.b.d. t.b.d. 67 k.sub.11/pN 13.3 t.b.d. t.b.d. 14.7 k.sub.22/pN t.b.d. t.b.d. t.b.d. t.b.d. k.sub.33/pN 15.5 t.b.d. t.b.d. 14.6 γ.sub.1/k.sub.11 * 4.81 t.b.d. t.b.d. 4.55 V.sub.0/V 1.58 t.b.d. t.b.d. 1.65 V.sub.10/V 2.13 t.b.d. t.b.d. t.b.d. Example CE-A A-4 A-5 A-6 Composition Cpd. None LBfi(S)-3-T LBf-3-OT LBf(S)-3-OT Synth.Ex. None (4) (5) (6) c(Cpd.)/% 0 10.0 5.0 10.0 c(Host A)/% 100 90.0 95.0 90.0 Properties T(N, I)/° C. 78.5 t.b.d. 75.0 78.0 n.sub.e(589 nm) 1.5876 t.b.d. t.b.d. 1.5942 Δn(589 nm) 0.1001 t.b.d. t.b.d. 0.1072 ε.sub.⊥(1 kHz) 3.0 t.b.d. t.b.d. 3.4 Δε(1 kHz) 6.0 t.b.d. t.b.d. 5.5 ε.sub.av.(1 kHz) 5.0 t.b.d. t.b.d. 5.2 ε.sub.⊥/Δε(1 kHz) 0.50 t.b.d. t.b.d. 0.62 γ.sub.1/mPa .Math. s 64 t.b.d. t.b.d. t.b.d. k.sub.11/pN 13.3 t.b.d. t.b.d. 13.2 k.sub.22/pN t.b.d. t.b.d. t.b.d. t.b.d. k.sub.33/pN 15.5 t.b.d. t.b.d. 15.6 γ.sub.1/k.sub.11 * 4.81 t.b.d. t.b.d. t.b.d. V.sub.0/V 1.58 t.b.d. t.b.d. 1.63 V.sub.10/V 2.13 t.b.d. t.b.d. t.b.d. Remarks: all extrapolated values at 20° C., * [mPa .Math. s/pN] and t.b.d.: to be determined.

[0446] These mixtures, mixtures A-1 to A-6, have good dielectric ratios (ε.sub.⊥/Δε), good ratios of (γ.sub.1/k.sub.11) and are characterized by very good transmissions in an FFS display and show very short response time. Moreover, they show excellent deep temperature stability at least up to a temperature of −20° C.

Example 1

[0447] The following mixture (M-1) is prepared and investigated.

TABLE-US-00037 Mixture M-1 Composition Compound Concentration No. Abbreviation /% by weight 1 LBfi-3-T 6.0 2 LB-3-OT 10.0 3 LB-3-T 5.0 4 LB(S)-3-OT 10.0 5 Y-4O-O4 5.5 6 CY-3-O2 6.5 7 CC-3-V 20.0 8 CCP-3-1 3.0 9 CCVC-3-V 5.0 10 PPGU-3-F 0.5 11 CCQU-3-F 8.0 12 CCQU-5-F 8.0 13 CDUQU-3-F 1.5 14 APUQU-3-F 5.5 15 DGUQU-4-F 5.5 Σ 100.0 Physical properties T(N, I)= 79.0° C. n.sub.e(20° C., 589 nm)= 1.5935 Δn(20° C., 589 nm)= 0.1169 ε.sub.⊥(20° C., 1 kHz)= 7.8 Δε(20° C., 1 kHz)= 5.6 ε.sub.av.(20° C., 1 kHz)= 9.7 γ.sub.1(20° C.)= t.b.d. mPa .Math. s k.sub.11(20° C.)= 16.8 pN k.sub.33(20° C.)= 15.4 pN V.sub.0(20° C.)= 1.77 V

[0448] This mixture, mixture M-1, has a dielectric ratio (ε.sub.⊥/Δε) of 1.39, is characterized by a very good transmission in an FFS display and has a very good low temperature stability.

Example 2

[0449] The following mixture (M-2) is prepared and investigated.

TABLE-US-00038 Mixture M-2 Composition Compound Concentration No. Abbreviation /% by weight 1 LBfi-3-T 5.0 2 LB-3-OT 9.0 3 LB-3-T 5.0 4 LB(S)-3-OT 8.0 5 CB-3-OT 10.0 6 Y-4O-O4 6.5 7 CCY-3-O2 3.5 8 CC-3-V 21.0 9 CCVC-3-V 3.5 10 PPGU-3-F 0.5 11 CCQU-3-F 8.0 12 CCQU-5-F 8.0 13 CDUQU-3-F 6.0 14 DGUQU-4-F 6.0 Σ 100.0 Physical properties T(N, I)= 79.5° C. n.sub.e(20° C., 589 nm)= 1.5910 Δn(20° C., 589 nm)= 0.1171 ε.sub.⊥(20° C., 1 kHz)= 8.6 Δε(20° C., 1 kHz)= 5.1 ε.sub.av.(20° C., 1 kHz)= 10.3 γ.sub.1(20° C.)= t.b.d. mPa .Math. s k.sub.11(20° C.)= 15.6 pN k.sub.33(20° C.)= 15.1 pN V.sub.0(20° C.)= 1.85 V

[0450] This mixture, mixture M-2, has a dielectric ratio (ε.sub.⊥/Δε) of 1.69, is characterized by a very good transmission in an FFS display and has a very good low temperature stability.

Example 3

[0451] The following mixture (M-3) is prepared and investigated.

TABLE-US-00039 Mixture M-3 Composition Compound Concentration No. Abbreviation /% by weight 1 LBfi-3-T 5.0 2 LB-3-OT 10.0 3 LB-3-T 5.5 4 LB(S)-3-OT 8.5 5 CCS-3-T 10.0 6 B(S)-2O-O5 4.0 7 Y-4O-O4 6.0 8 CCY-3-O2 2.0 9 CC-3-V 21.5 10 CCVC-3-V 4.0 11 PPGU-3-F 0.5 12 CCQU-3-F 9.0 13 CDUQU-3-F 8.0 14 DGUQU-4-F 6.0 Σ 100.0 Physical properties T(N, I)= 81.5° C. n.sub.e(20° C., 589 nm)= 1.5951 Δn(20° C., 589 nm)= 0.1196

[0452] This mixture, mixture M-3, has a a very good low temperature stability.

Example 4

[0453] The following mixture (M-4) is prepared and investigated.

TABLE-US-00040 Mixture M-4 Composition Compound Concentration No. Abbreviation /% by weight 1 LBfi-3-T 5.0 2 LB-3-OT 10.0 3 LB-3-T 5.5 4 LB(S)-3-OT 8.5 5 CLY-3-OT 10.0 6 B(S)-2O-O5 2.0 7 Y-4O-O4 7.0 8 CCY-3-O2 3.5 9 CC-3-V 20.5 10 CCVC-3-V 4.0 11 PPGU-3-F 0.5 12 CCQU-3-F 9.5 13 CDUQU-3-F 8.0 14 DGUQU-4-F 6.0 Σ 100.0 Physical properties T(N, I)= 81.5° C. n.sub.e(20° C., 589 nm)= 1.5933 Δn(20° C., 589 nm)= 0.1193 ε.sub.⊥(20° C., 1 kHz)= 8.7 Δε(20° C., 1 kHz)= 5.1 ε.sub.av.(20° C., 1 kHz)= 10.4 γ.sub.1(20° C.)= t.b.d. mPa .Math. s k.sub.11(20° C.)= 18.8 pN k.sub.33(20° C.)= 35.2 pN V.sub.0(20° C.)= 2.01 V

[0454] This mixture, mixture M-4, has a dielectric ratio (ε.sub.⊥/Δε) of 1.70, is characterized by a very good transmission in an FFS display and has a very good low temperature stability.

Example 5

[0455] The following mixture (M-5) is prepared and investigated.

TABLE-US-00041 Mixture M-5 Composition Compound Concentration No. Abbreviation /% by weight 1 LBh-3-T 5.0 2 B(S)-2O-O4 4.0 3 B(S)-2O-O5 4.0 4 CPY-3-O2 9.0 5 CC-3-V 49.5 6 CCP-V-1 14.0 7 PGP-2-2V 2.0 8 CCGU-3-F 6.0 9 PPGU-3-F 0.5 10 PUQU-3-F 6.0 Σ 100.0 Physical properties T(N, I)= 83.5° C. n.sub.e(20° C., 589 nm)= 1.5896 Δn(20° C., 589 nm)= 0.1036 ε.sub.⊥(20° C., 1 kHz)= 4.4 Δε(20° C., 1 kHz)= 2.0 ε.sub.av.(20° C., 1 kHz)= 5.1 γ.sub.1(20° C.)= 65 mPa .Math. s k.sub.11(20° C.)= 14.6 pN k.sub.33(20° C.)= 15.2 pN V.sub.0(20° C.)= 2.84 V

[0456] This mixture, mixture M-5, has a dielectric ratio (ε⊥/Δε) of 2.2, a ratio of (γ.sub.1/k.sub.11) of 4.45, is characterized by a very good transmission in an FFS display and fast switching time and has a very good low temperature stability.

Example 6

[0457] The following mixture (M-6) is prepared and investigated.

TABLE-US-00042 Mixture M-6 Composition Compound Concentration No. Abbreviation /% by weight 1 LBh-3-T 5.0 2 B(S)-2O-O4 4.0 3 B(S)-2O-O5 4.0 4 CPY-3-O2 8.0 5 CC-3-V 49.5 6 CCP-V-1 15.5 7 CCGU-3-F 6.5 8 PPGU-3-F 0.5 9 PUQU-3-F 7.0 Σ 100.0 Physical properties T(N, I)= 83.0° C. n.sub.e(20° C., 589 nm)= 1.5858 Δn(20° C., 589 nm)= 0.1002 ε.sub.⊥(20° C., 1 kHz)= 4.3 Δε(20° C., 1 kHz)= 2.3 ε.sub.av.(20° C., 1 kHz)= 5.1 γ.sub.1(20° C.)= 65 mPa .Math. s k.sub.11(20° C.)= 14.3 pN k.sub.33(20° C.)= 15.2 pN V.sub.0(20° C.)= 2.61 V

[0458] This mixture, mixture M-6, has a dielectric ratio (ε.sub.⊥/Δε) of 1.87, a ratio of (γ.sub.1/k.sub.11) of 4.55, is characterized by a very good transmission in an FFS display and fast switching times and has a very good low temperature stability.