Dibenzofuran and dibenzothiophene derivatives

Abstract

The present invention relates to a compound of the general formula I ##STR00001##
in which the occurring groups and parameters have the meanings indicated in claim 1, to the use thereof in liquid-crystalline or mesogenic media and to liquid-crystalline or mesogenic media comprising these derivatives.

Claims

1. A compound of formula I ##STR00169## in which W denotes O or S R denotes 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—, ##STR00170##  —O—, —CO—O— or —O—CO— in such a way that 0 atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, 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 on each occurrence, identically or differently, denotes 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—, Y.sup.1 and Y.sup.2 denote F and Y.sup.3 denotes H, X denotes OCF.sub.3 or CF.sub.3 and n is 0, 1 or 2, wherein the compound has positive dielectric anosotropy.

2. The compound according to claim 1 selected from the following sub-formulae: ##STR00171## in which R, A, Z, X and n have the meanings given in claim 1.

3. The compound according to claim 1, wherein Z denotes a single bond.

4. The compound according to claim 1, wherein n is 1 and A denotes trans-1,4-cyclohexylene or 1,4-cyclohexenylene.

5. A compound of formula P or P′ ##STR00172## in which R denotes 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—, ##STR00173##  —O—, —CO—O— or —O—CO— in such a way that 0 atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, 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 on each occurrence, identically or differently, denotes 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—, Y.sup.1 and Y.sup.2 denote F and Y.sup.3 denotes H, X denotes OCF.sub.3 or CF.sub.3, n is 0, 1 or 2.

6. A process for the preparation of a compound of formula I of claim 1, treating a compound of formula P or P′ ##STR00174## wherein R, A, Z, n, X, Y.sup.1, Y.sup.2 and Y.sup.3 are defined as in formula I with a base.

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

8. The liquid-crystalline medium according to claim 7, wherein the medium comprises one or more compounds selected from the group of compounds of formulae II and III ##STR00175## 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, ##STR00176## on each appearance, independently of one another, denote ##STR00177## 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 ##STR00178## on each appearance, independently of one another, are ##STR00179## 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, 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 is 0, 1, 2 or 3.

9. Electro-optical display element containing a liquid-crystalline medium according to claim 7.

10. The display element according to claim 9, wherein the display element is a TN-TFT, IPS or FFS display.

Description

SYNTHESIS EXAMPLES

Example 1: 2,4-Difluoro-7-(4-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzofuran (1)

(1) ##STR00135##

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

(2) ##STR00136##

(3) 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. 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

(4) ##STR00137##

(5) 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

(6) ##STR00138##

(7) 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

(8) ##STR00139##

(9) 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

(10) ##STR00140##

(11) 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-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzofuran

(12) ##STR00141##

(13) 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.

(14) Phase Sequence: Tg−35 Cr 67 Sx (33) SmA (40) 1.

(15) Δε=18.5

(16) Δn=0.2036

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

(17) ##STR00142##

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

(18) ##STR00143##

(19) 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-propylcyclohexen-1-yl)-3-(trifluoromethyl)dibenzothiophene

(20) ##STR00144##

(21) 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.

(22) Phase sequence: Cr 150 Sx 1161.

(23) Δε=22.9

(24) Δn=0.2101

Example 3

(25) In analogy to example 1 is obtained:

(26) ##STR00145##

(27) Phase Sequence: Cr 85 I

(28) Δε=12.3

(29) Δn=0.1742

(30) In analogy to the above described examples the following exemplary compounds of formula I and its respective sub-formulae are obtained:

(31) In the following table the following abbreviations for the end groups are used

(32) TABLE-US-00007 c-C.sub.3H.sub.5 c-C.sub.3H.sub.5CH.sub.2 c-C.sub.4H.sub.7 c-C.sub.5H.sub.7 c-C.sub.5H.sub.9 0

(33) The physical properties are given at a temperature of 20° C. and γ.sub.1 is given in mPa.Math.s. Phase transition temperatures are given in ° C.

(34) ##STR00151##

(35) TABLE-US-00008 No: 4- R 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 Cr 109 I 18 C.sub.2H.sub.5O F 19 n-C.sub.3H.sub.7O F Cr 81 I; Δn = 0.1411 Δε = 11.9; γ1 = 58 20 n-C.sub.4H.sub.9O F 21 n-C.sub.5H.sub.11O F Cr 48 I; Δn = 0.1351 Δε = 9.9; γ1 = 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 Cr 74 I; Δn = 0.1450 Δε = 19.1; γ1 = 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 Cr 82 I 63 n-C.sub.5H.sub.11O OCF.sub.3

(36) ##STR00152##

(37) TABLE-US-00009 No: 5- R 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 Cr 146 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 Cr 97 SA (77) I; Δn =0.1571, Δε = 23.3; γ1 = 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 Cr 110 SA (95) I; Δn =0.1450, Δε = 17.3; γ1 = 240 63 n-C.sub.5H.sub.11O OCF.sub.3

(38) ##STR00153##

(39) TABLE-US-00010 No: 6- R 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 Cr 86 I; Δn = 0.1512; Δε = 12.1; γ1 = 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 Cr 63 I 63 n-C.sub.5H.sub.11O OCF.sub.3

(40) ##STR00154##

(41) TABLE-US-00011 No: 7- R 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 Cr 105 SA 113 I; Δn = 0.1591; Δε = 17.7; γ1 = 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 Cr 63 I 63 n-C.sub.5H.sub.11O OCF.sub.3

(42) ##STR00155##

(43) TABLE-US-00012 No: 8- R 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

(44) ##STR00156##

(45) TABLE-US-00013 No: 9- R 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

(46) ##STR00157##

(47) TABLE-US-00014 No: 10- R X Phase Range; properties 1 CH.sub.3 F 2 C.sub.2H.sub.5 F 3 n-C.sub.3H.sub.7 F Cr 85 N 94.3 I; Δn = 0.2090; Δε = 9.7; γ1 =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 Tg −35 Cr 67 SX (33) SA (40) I; Δn = 0.2036; Δε = 18.5 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 Cr 75 SA 75 N 86 I; Δn = 0.1341; Δε = 13.3; γ1 =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

(48) ##STR00158##

(49) TABLE-US-00015 No: 11- R 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 Cr 150 S.sub.X 116 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 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

(50) ##STR00159##

(51) TABLE-US-00016 No:12- R 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 Cr 85 S.sub.A 108 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 Cr 83 S.sub.A 132 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 Cr 63 I 63 n-C.sub.5H.sub.11O OCF.sub.3

(52) ##STR00160##

(53) TABLE-US-00017 No: 13- R 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 Cr 142 S.sub.A 181 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 Cr 101 S.sub.A 194 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

(54) ##STR00161##

(55) TABLE-US-00018 No: 14- R 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

(56) ##STR00162##

(57) TABLE-US-00019 No: 15- R 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

(58) ##STR00163##

(59) TABLE-US-00020 No: 16- R.sup.1X 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 T.sub.g −35 Cr 67 S.sub.X (33 S.sub.A 40) I; Δn = 0.2036; Δε = 18.5; γ.sub.1 = 518 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

(60) ##STR00164##

(61) TABLE-US-00021 No: 17- R 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

(62) ##STR00165##

(63) TABLE-US-00022 No: 18- R 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 Cr 112 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 Cr 62 S.sub.A 78 N 85.5 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

(64) ##STR00166##

(65) TABLE-US-00023 No: 19- R 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 Cr 143 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

(66) ##STR00167##

(67) TABLE-US-00024 No: 20- R 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

(68) ##STR00168##

(69) TABLE-US-00025 No: 21- R 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

Use Examples

(70) A nematic liquid-crystal mixture N-1 having the composition and properties as indicated in the following table is prepared.

(71) TABLE-US-00026 Mixture N-1 BCH-3F.F 12.0% T(N, I) = 92 ° C. BCH-5F.F 10.0% Δn (20° C., 589.3 nm) = 0.0969 ECCP-30CF3 5.0% Δε (20° C., 1 kHz) = 5.2 ECCP-50CF3 5.0% γ.sub.1 (20° C.) = 134 mPa .Math. s CBC-33F 2.0% CBC-53F 2.0% CBC-55F 2.0% PCH-6F 8.0% PCH-7F 6.0% CCP-20CF3 8.0% CCP-30CF3 12.0% CCP-40CF3 7.0% CCP-50CF3 11.0% PCH-5F 10.0% Σ 100.0%

(72) A nematic liquid-crystal medium M-1 consisting of 90% of the medium N-1 and 10% of the compound of Synthesis Example 1 (compound (1)) has the following properties:

(73) TABLE-US-00027 N-1 90.0% T(N, I) = 90 ° C. (1) 10.0% Δn (20° C., 589.3 nm) = 0.1075 Σ 100.0% Δε (20° C., 1 kHz) = 6.6 γ.sub.1 (20° C.) = 150 mPa .Math. s

(74) The compound (1) is well soluble in the medium N-1. The addition of the compound (1) according to the invention to the medium N-1 has the effect that the dielectric anisotropy is advantageously increased.

(75) A nematic liquid-crystal medium M-2 consisting of 95% of the medium N-1 and 5% of the compound of Synthesis Example (2) (compound (2)) has the following properties:

(76) TABLE-US-00028 N-1 95.0% T(N, I) = 92.8 ° C. (2) 5.0% Δn (20° C., 589.3 nm) = 0.1026 Σ 100.0% Δε (20° C., 1 kHz) = 6.2 γ.sub.1 (20° C.) = 143 mPa .Math. s

(77) The compound (2) is well soluble in the medium N-1. The addition of the compound (2) according to the invention to the medium N-1 has the effect that the dielectric anisotropy is advantageously increased.