Thiophene compound, liquid-crystalline medium and liquid-crystal display comprising the same

Abstract

The invention relates to a liquid-crystalline medium, preferably having a nematic phase and dielectric anisotropy of 0.5 or more, which comprises one or more compounds of formula T ##STR00001## in which ##STR00002##
and the other parameters have the meanings 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 compounds of formula T and their use for the improvement of the transmission and/or response times of a liquid-crystalline medium which comprises one or more additional mesogenic compounds.

Claims

1. A liquid-crystalline medium comprising one or more compounds of formula T ##STR00286## in which ##STR00287## denotes ##STR00288## one of ##STR00289## which is present, denotes ##STR00290## and the other ##STR00291## if present, denotes ##STR00292## wherein each ##STR00293## are optionally substituted by one or two alkyl groups, n denotes 1 or 2, R.sup.S denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, or denotes alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, and X.sup.s denotes F, Cl, CN, NCS or fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy having 1 to 4 C atoms, and one or more compounds of formula II ##STR00294## in which R.sup.2 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, ##STR00295## on each appearance, independently of one another, denote ##STR00296## 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 2.

2. The medium according to claim 1, wherein the one or more compounds of formula T are of formulae T-1 to T-4 ##STR00297## in which R.sup.S denotes alkyl, alkoxy, fluorinated alkyl, fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, X.sup.s denotes F, Cl, CN, NCS, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy, and ##STR00298## wherein ##STR00299## is optionally substituted by one or two alkyl groups, and wherein the compounds of formulae T-1 and T-2 are excluded from formulae T-3 and T-4.

3. The medium according to claim 2, comprising one or more compounds of formula formulae T-1 and/or one or more compounds of formula T-3.

4. The medium according to claim 1, further comprising one or more compounds of formula III ##STR00300## in which R.sup.3 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms ##STR00301## on each appearance, independently of one another, are ##STR00302## 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.2CHd—, —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. The liquid-crystalline medium according to claim 1, further comprising one or more compounds selected from the group consisting of compounds of formulae IV and V: ##STR00303## 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, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, ##STR00304## independently of one another and, if ##STR00305##  occurs twice, also these independently of one another, denote ##STR00306## 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, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, ##STR00307## if present, each, independently of one another, denote ##STR00308## 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. The liquid-crystalline medium according to claim 5, further comprising one or more compounds selected from the group consisting of compounds of formulae VI to IX: ##STR00309## 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, ##STR00310## 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, ##STR00311## Z.sup.8 denotes —(C═O)—O—, —CH.sub.2—O—, —CF.sub.2—O— or —CH.sub.2—CH.sub.2—, o denotes 0 or 1, R.sup.91 and R.sup.92 each, independently of one another 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, ##STR00312## p and q independently of each other denote 0 or 1.

7. The medium according to claim 1, further comprising one or more compounds of formula I ##STR00313## in which ##STR00314## n denotes 0 or 1, R.sup.11 and R.sup.12 independently of each other denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, having 1 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, or denotes alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclo-propylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, 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 having 1 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclo-propylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, or denotes alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclo-propylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, and X.sup.1 denotes F, Cl, fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyoxy.

8. The medium according to claim 7, wherein the total concentration of the compounds of formula T in the medium as a whole is 1% to 60%.

9. The medium according to claim 1, additionally comprising one or more chiral compounds.

10. An electro-optical display or electro-optical component, comprising a liquid-crystalline medium according to claim 1.

11. The display according to claim 10, which is based on the IPS-, FFS, HB-FFS and XB-FFS mode.

12. The display according to claim 10, which contains an active-matrix addressing device.

13. The display according to claim 10, which is a mobile display.

14. A process for preparing the liquid-crystalline medium according to claim 1, comprising mixing one or more compounds of formula T with one or more compounds of formula II.

15. A process for preparing a compound of formula T ##STR00315## in which ##STR00316## one of ##STR00317## which is present, denotes ##STR00318## and the other ##STR00319## if present, denotes ##STR00320## wherein each ##STR00321## are optionally substituted by one or two alkyl groups, n denotes 1 or 2, R.sup.S denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, or denotes alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, in which one —CH.sub.2— group may be replaced by cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene or 1,3-cyclo-pentenylene, and X.sup.S denotes F, Cl, CN, NCS or fluorinated alkyl, fluorinated alkenyl, fluorinated alkoxy or fluorinated alkenyloxy having 1 to 4 C atoms, comprising coupling a cyclohexenyl-aryl-bromide with a thiophene boronic acid, which is substituted by a polar group, or coupling a cyclohexenyl-aryl-bromide with a thiophene boronic acid.

Description

EXAMPLES

(1) 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.

(2) The following abbreviations are used in the synthetic examples of the present application:

(3) BuLi n-Butyllithium

(4) MTB ether tert-Butyl methyl ether

(5) THE Tetrahydrofuran

(6) dist. distilled

Synthesis Example 1

Synthesis of 2-[4-(4-propylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene (CLS-3-T)

(7) ##STR00223##

Step 1.1: 4-(4-Propylcyclohexyl)-1-[5-(trifluoromethyl)-2-thienyl]cyclohexanol

(8) ##STR00224##

(9) BuLi (59.0 ml, 15% in n-hexane, 93 mmol) is slowly added to a solution of 2-bromo-5-(trifluoromethyl)thiophene (1, CAS 143469-22-1) (20.0 g, 86 mmol) in diethylether (250 mL) at −70° C. under nitrogen atmosphere. The mixture is allowed to warm up to −50° C. after 1 h. Then it is cooled again to −70° C., and a solution of 4-(4-propylcyclohexyl)-cyclohexanone (2, CAS 82832-73-3) (22.0 g, 98 mmol) in diethylether (100 mL) is added dropwise. The reaction mixture is stirred for 1 h, then it is allowed to warm up to room temperature and quenched with dist. water and hydrochloric acid (2 M). 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 to give 4-(4-propylcyclohexyl)-1-[5-(trifluoromethyl)-2-thienyl]cyclohexanol (3) as a brown solid.

Step 1.2: 2-[4-(4-Propylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene (CLS-3-T)

(10) ##STR00225##

(11) A mixture of 4-(4-propylcyclohexyl)-1-[5-(trifluoromethyl)-2-thienyl]cyclohexanol (3) (37.8 g, 86 mmol) and toluene-4-sulfonic acid monohydrate (1.5 g, 7.9 mmol) in toluene (400 mL) is heated in a Dean Stark trap at reflux temperature for 2 h. Then it is cooled to room temperature and the mixture is quenched with aqueous sodium hydroxide. The aqueous phase is separated and extracted with toluene. 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). Subsequent recrystallization of the crude product from isopropyl alcohol results in colorless crystals of 2-[4-(4-butylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene (4).

(12) Compound (4) has the following phase characteristics: K 76 N 104 I.

Synthesis Example 2

Synthesis of 2-[4-(4-propylcyclohexyl)cyclohexyl]-5-(trifluoromethyl)thiophene (CCS-3-T)

(13) ##STR00226##

Step 2.1: 2-[4-(4-Propylcyclohexyl)cyclohexyl]-5-(trifluoromethyl)thiophene

(14) ##STR00227##

(15) 2-[4-(4-Propylcyclohexyl)cyclohexen-1-yl]-5-(trifluoromethyl)thiophene (1) (23.5 g, 65 mmol) in toluene (300 mL) is reacted with hydrogen in the presence of a catalytic amount of Palladium on activated charcoal for 24 h. The reaction mixture is concentrated in vacuo, and the residue is purified by silica gel chromatography (solvent n-heptane) to give the trans-isomer of the desired product. Subsequent recrystallization of the crude product from a mixture of isopropyl alcohol and methylcyclohexane results in colorless crystals of 2-[4-(4-propylcyclohexyl)cyclohexyl]-5-(trifluoromethyl)thiophene (2).

(16) Compound (2) has the following phase characteristics: K 41 S.sub.X 45 S.sub.B 52 N 95 I.

Synthesis Example 3

Synthesis of 2-[2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-5-(trifluoromethyl)thiophene (LGS-3-T)

(17) ##STR00228##

Step 3.1: 1-(4-Bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol

(18) ##STR00229##

(19) A solution of isopropylmagnesium chloride (2.0 M) in THE (260 mL, 0.52 mol, diluted in 200 mL THF) is slowly added to a solution of 1-bromo-2-fluoro-4-iodo-benzene (1, CAS 136434-77-0) (150 g, 0.50 mol) in THE (1 L) at −10° C. under nitrogen atmosphere. The reaction mixture is stirred at this temperature for 3 h. Then a solution of 4-propylcyclohexanone (2, CAS 40649-36-3) (73.0 g, 0.52 mol) in THE (200 mL) is added at −10° C. The mixture is allowed to warm up to room temperature and stirred overnight.

(20) Then it is quenched with dist. water and hydrochloric acid (10%) 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 to give 1-(4-bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol (3) as a brown oil.

Step 3.2: 1-Bromo-2-fluoro-4-(4-propylcyclohexen-1-yl)benzene

(21) ##STR00230##

(22) A mixture of 1-(4-bromo-3-fluoro-phenyl)-4-propyl-cyclohexanol (3) (194.0 g, 0.44 mol) and toluene-4-sulfonic acid monohydrate (5.0 g, 26.3 mmol) in toluene (1.3 L) is heated in a Dean Stark trap at reflux temperature for 3 h. Then it is cooled to room temperature 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 (4) as a light yellow oil.

Step 3.3: 2-[2-Fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-5-(trifluoromethyl)thiophene

(23) ##STR00231##

(24) A mixture of 1-bromo-2-fluoro-4-(4-propylcyclohexen-1-yl)benzene (4) (7.2 g, 24.2 mmol), potassium carbonate (5.5 g, 39.8 mmol), tris(dibenzylideneacetone)-dipalladium(0) (100 mg, 0.11 mmol) and CataCXium A (70 mg, 0.19 mmol) in THE (100 mL) and dist. water (25 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of [5-(trifluoromethyl)-2-thienyl]boronic acid (5, CAS 958451-91-7) (5.0 g, 25.5 mmol) in THE (30 mL). The reaction mixture is heated at reflux temperature for 3 h. 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 distilled water and brine, dried (sodium sulfate) and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent heptane). Subsequent recrystallization of the crude product from isopropyl alcohol and heptane results in colorless crystals of 2-[2-fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-5-(trifluoromethyl)thiophene (6).

(25) Compound (6) has the following phase characteristics: K 72 SmA 123 I.

Synthesis Example 4

Synthesis of 2-[2-fluoro-4-(4-propylcyclohexyl)phenyl]-5-(trifluoromethyl)thiophene (CGS-3-T)

(26) ##STR00232##

Step 4.1:2-[2-Fluoro-4-(4-propylcyclohexyl)phenyl]-5-(trifluoromethyl)thiophene

(27) ##STR00233##

(28) 2-[2-Fluoro-4-(4-propylcyclohexen-1-yl)phenyl]-5-(trifluoromethyl)thiophene (1) (3.5 g, 9.5 mmol) in toluene (30 mL) is reacted with hydrogen in the presence of a catalytic amount of Palladium on activated charcoal for 24 h. The reaction mixture is concentrated in vacuo, and the residue is purified by silica gel chromatography (solvent n-heptane) to give the trans-isomer of the desired product. Subsequent recrystallization of the crude product from a mixture of isopropyl alcohol and methylcyclohexane results in colorless crystals of 2-[2-fluoro-4-(4-propylcyclohexyl)phenyl]-5-(trifluoromethyl)thiophene (2).

(29) Compound (2) has the following phase characteristics:

(30) K 70 N, 77 I.

Synthesis Example C-1 (LB(S)-3-OT)

Synthesis of 4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethoxy-dibenzothiophene

(31) ##STR00234##

Step C-1.1: 3,2′,3′-Trifluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol

(32) ##STR00235##

(33) A mixture of 6-bromo-2-fluoro-3-trifluoromethoxyphenol (2, CAS 1805580-01-1) (68.0 g, 0.25 mol), potassium carbonate (50.0 g, 0.36 mol), tris(dibenzylideneacetone)-dipalladium(0) (1.2 g, 1.25 mmol) and CataCXium A (1.4 g, 3.71 mmol) in THE (500 mL) and distilled water (100 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of 2,3-difluoro-4-(4-propyl-cyclohex-1-enyl)-phenylboronic acid (1, CAS 947607-78-5) (70.6 g, 0.25 mol) in THE (200 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. Throughout this application, unless explicitly stated otherwise, room temperature and ambient temperature are used synonymously and signify a temperature of about 20° C., typically (20±1°) C. 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/heptane 1:1). 3,2′,3′-Trifluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol (3) is isolated as a brown solid.

Step C-1.2: Trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl ester

(34) ##STR00236##

(35) Trifluoromethanesulfonic anhydride (31 mL, 0.19 mol) is slowly added to a solution of 3,2′,3′-trifluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-ol (3) (66 g, 0.15 mol), TEA (32 mL, 0.23 mol) and DMAP (560 mg, 4.58 mmol) in dichloromethane (500 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 dichlormethane) to give trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl ester (4) as a brown oil.

Step C-1.3:4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethoxy-dibenzothiophene

(36) ##STR00237##

(37) This reaction is performed as a one-pot reaction. In the first step, a solution of trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohex-1-enyl)-4-trifluoromethoxy-biphenyl-2-yl ester (4) (87 g, 0.15 mol), 3-mercapto-propionic acid 2-ethylhexyl ester (45 mL, 0.19 mol), N-ethyldiisopropylamine (40 mL, 0.24 mol) and toluene (350 mL) is degassed with Argon for 1 h. Tris(dibenzylideneacetone)dipalladium(0) (1.5 g, 1.56 mmol) and (oxydi-2,1-phenylene)bis(diphenylphosphine) (1.6 g, 2.91 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 (22 g, 0.20 mol) in THE (200 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 (11 g, 0.1 mol) in THE (100 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 4,6-difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethoxy-dibenzothiophene (6) as white crystals.

(38) Compound (6) has the following phase characteristics: K 66° C. SmA 181° C. 1.

Synthesis Example C-2 (LB(S)-3-T)

Synthesis of 4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzothiophene

(39) ##STR00238##

Step C-2.1: 3,2′,3′-Trifluoro-4-trifluoromethyl-biphenyl-2-ol

(40) ##STR00239##

(41) A mixture of 6-bromo-2-fluoro-3-trifluoromethylphenol (2, CAS 1804908-52-8) (100 g, 0.38 mol), potassium carbonate (80 g, 0.58 mol), tris(dibenzylideneacetone)-dipalladium(0) (1.9 g, 2.0 mmol) and CataCXium A (2.2 g, 5.8 mmol) in THE (500 mL) and distilled water (200 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of 2,3-difluoro-4-phenylboronic acid (1, CAS 121219-16-7) (70 g, 0.43 mol) in THE (300 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. Throughout this application, unless explicitly stated otherwise, room temperature and ambient temperature are used synonymously and signify a temperature of about 20° C., typically (20±1°) C. 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 dichloromethane). 3,2′,3′-Trifluoro-4-trifluoromethyl-biphenyl-2-ol (3) is isolated as a brown solid.

Step C-2.2: Trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4-trifluoromethyl-biphenyl-2-yl ester

(42) ##STR00240##

(43) Trifluoromethanesulfonic anhydride (30.0 mL, 0.18 mol) is slowly added to a solution of 3,2′,3′-trifluoro-4-trifluoromethyl-biphenyl-2-ol (3) (46.8 g, 0.15 mol), TEA (32 mL, 0.23 mol) and DMAP (600 mg, 4.9 mmol) in dichloromethane (300 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 dichlormethane) to give trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4-trifluoromethyl-biphenyl-2-yl ester (4) as a yellow oil.

Step C-2.3: 4,6-Difluoro-3-trifluoromethyl-dibenzothiophene

(44) ##STR00241##

(45) This reaction is performed as a one-pot reaction. In the first step, a solution of trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4-trifluoromethyl-biphenyl-2-yl ester (4) (66 g, 0.15 mol) and ethyl 3-mercaptopropionate (24 mL, 0.18 mol) in toluene (500 mL) is heated under nitrogen atmosphere to 80° C. Potassium carbonate (50 g, 0.36 mol), tris(dibenzylideneacetone)dipalladium(0) (7.0 g, 7.3 mmol) and (oxydi-2,1-phenylene)bis(diphenylphosphine) (8.0 g, 14.6 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 (18 g, 0.16 mol) in THE (150 mL) is added to the reaction mixture containing intermediate (5) in situ. The reaction mixture is heated 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 4,6-difluoro-3-trifluoromethyl-dibenzothiophene (6) as yellow crystals.

Step C-2.4:1-(4,6-Difluoro-7-trifluoromethyl-dibenzothiophen-3-yl)-4-propyl-cyclohexanol

(46) ##STR00242##

(47) Lithiumdiisopropylamide (6 mL, 2 M in cyclohexane/ethylbenzene/THF, 12 mmol) is added to a solution of 4,6-difluoro-3-trifluoromethyl-dibenzothiophene (6) (3.2 g, 10 mmol) in THE (100 mL) at −70° C. under nitrogen atmosphere. A solution of 4-propylcyclohexanone (1.7 g, 12 mmol) in THE (10 mL) is added after 1 h, and the reaction mixture is stirred for 2 h at −70° C. Then it is allowed to warm to room temperature and is stirred overnight. The reaction is 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 dichlormethane) to give 1-(4,6-difluoro-7-trifluoromethyl-dibenzothiophen-3-yl)-4-propyl-cyclohexanol (7) as yellow crystals.

Step C-2.5:4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzothiophene

(48) ##STR00243##

(49) A mixture of 1-(4,6-difluoro-7-trifluoromethyl-dibenzothiophen-3-yl)-4-propyl-cyclohexanol (7) (1.2 g, 2.5 mmol) and toluene-4-sulfonic acid monohydrate (50 mg, 0.3 mmol) in toluene (50 mL) is heated in a Dean Stark trap 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). Subsequent recrystallization of the crude product from heptane results in colorless crystals of 4,6-difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzothiophene.

(50) Compound (7) has the following phase characteristics: K 121° C. SmA 162° C. I.

Synthesis Example C-3 (CB(S)-3-T)

Synthesis of 4,6-Difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl-dibenzothiophene

(51) ##STR00244##

Step 3.1: 3,2′,3′-Trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-ol

(52) ##STR00245##

(53) A mixture of 6-bromo-2-fluoro-3-trifluoromethylphenol (2, CAS 1804908-52-8) (7.1 g, 26.9 mmol), potassium carbonate (5.6 g, 40.5 mmol), tris(dibenzylideneacetone)-dipalladium(0) (130 mg, 0.14 mmol) and CataCXium A (150 mg, 0.40 mmol) in THE (50 mL) and distilled water (15 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of 2,3-difluoro-4-(4-propyl-cyclohexyl)-phenylboronic acid (1, CAS 183438-45-1) (7.8 g, 27.2 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 distilled water. Throughout this application, unless explicitly stated otherwise, room temperature and ambient temperature are used synonymously and signify a temperature of about 20° C., typically (20±1°) C. 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/heptane 1:1). 3,2′,3′-Trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-ol (3) is isolated as a yellow solid.

Step C-3.2: Trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-yl ester

(54) ##STR00246##

(55) Trifluoromethanesulfonic anhydride (2.8 mL, 17.0 mmol) is slowly added to a solution of 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-ol (3) (5.5 g, 13.2 mmol), TEA (2.8 mL, 20.2 mmol) and DMAP (50 mg, 0.41 mmol) in dichloromethane (50 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 dichlormethane) to give trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-yl ester (4) as a yellow oil.

Step C-3.3: 4,6-Difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl-dibenzothiophene

(56) ##STR00247##

(57) This reaction is performed as a one-pot reaction. In the first step, a solution of trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethyl-biphenyl-2-yl ester (4) (7.3 g, 13.1 mmol) and ethyl 3-mercaptopropionate (2.2 mL, 16.7 mmol) in toluene (70 mL) is quickly heated under nitrogen atmosphere to 80° C. Potassium carbonate (5.0 g, 36.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.7 g, 0.73 mmol) and (oxydi-2,1-phenylene)bis(diphenylphosphine) (0.8 g, 1.46 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 (1.8 g, 16.0 mmol) in THE (20 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 (1.8 g, 16.0 mmol) in THE (20 mL). The reaction mixture is heated 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 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl-dibenzothiophene (6) as yellowish crystals.

(58) Compound (6) has the following phase characteristics: K 150° C. N (139° C.) I

Synthesis Example C-3a (CB(S)-3-T)

(59) Alternatively, 4,6-Difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethyl-dibenzothiophene is obtained by hydrogenation of 4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethyl-dibenzothiophene:

(60) ##STR00248##

Synthesis Example C-4 (CB(S)-3-OT)

Synthesis of 4,6-Difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethoxy-dibenzothiophene

(61) ##STR00249##

Step C-4.1: 3,2′,3′-Trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-ol

(62) ##STR00250##

(63) A mixture of 6-bromo-2-fluoro-3-trifluoromethoxyphenol (2, CAS 1805580-01-1) (33.0 g, 0.12 mol), potassium carbonate (25.0 g, 0.18 mol), tris(dibenzylideneacetone)-dipalladium(0) (600 mg, 0.6 mmol) and CataCXium A (700 mg, 1.9 mmol) in THE (250 mL) and distilled water (75 mL) is heated to reflux under nitrogen atmosphere, followed by dropwise addition of a solution of 2,3-difluoro-4-(4-propyl-cyclohexyl)-phenylboronic acid (1, CAS 183438-45-1) (34.4 g, 0.12 mol) in THE (100 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. Throughout this application, unless explicitly stated otherwise, room temperature and ambient temperature are used synonymously and signify a temperature of about 20° C., typically (20±1°) C. 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/heptane 1:1). 3,2′,3′-Trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-ol (3) is isolated as a yellow solid.

Step C-4.2: Trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-yl ester

(64) ##STR00251##

(65) Trifluoromethanesulfonic anhydride (6.0 mL, 36.4 mmol) is slowly added to a solution of 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-ol (3) (12.6 g, 29.0 mmol), TEA (6.3 mL, 45.4 mmol) and DMAP (110 mg, 0.9 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 dichlormethane) to give trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-yl ester (4) as a yellow oil.

Step C-4.3: 4,6-Difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethoxy-dibenzothiophene

(66) ##STR00252##

(67) This reaction is performed as a one-pot reaction. In the first step, a solution of trifluoromethanesulfonic acid 3,2′,3′-trifluoro-4′-(4-propyl-cyclohexyl)-4-trifluoromethoxy-biphenyl-2-yl ester (4) (16.3 g, 28.1 mmol) and ethyl 3-mercaptopropionate (5.0 mL, 37.9 mmol) in toluene (150 mL) is quickly heated under nitrogen atmosphere to 80° C. Potassium carbonate (10 g, 72.4 mmol), tris(dibenzylidene-acetone)dipalladium(0) (1.4 g, 1.5 mmol) and (oxydi-2,1-phenylene)bis(diphenylphosphine) (1.6 g, 2.9 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, 31.2 mmol) in THE (50 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 (3.5 g, 31.2 mmol) in THE (50 mL). The reaction mixture is heated 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.

(68) The residue is purified by silica gel chromatography (solvent heptane) to give 4,6-difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethoxy-dibenzothiophene (6) as colorless crystals.

(69) Compound (6) has the following phase characteristics:

(70) K 108° C. SmA 141° C. N, 169° C. I

Synthesis Example C-4a (CB(S)-3-OT)

(71) Alternatively, 4,6-Difluoro-3-(4-propyl-cyclohexyl)-7-trifluoromethoxy-dibenzothiophene is obtained by hydrogenation of 4,6-Difluoro-3-(4-propyl-cyclohex-1-enyl)-7-trifluoromethoxy-dibenzothiophene:

(72) ##STR00253##

COMPOUND EXAMPLES

(73) Exemplary compounds having a high dielectric constant perpendicular to the director (ε.sub.⊥) and a high average dielectric constant (ε.sub.av.) are exemplified in the following compound examples.

Compound Examples 1 to 10

(74) Compounds of formula T are e.g.

(75) ##STR00254##

(76) This compound (CCS-3-T) has a melting point of 41° C., a clearing point of 95° C., a phase range of K 41° C. S.sub.X 45° C. S.sub.A 52° C. N, 95° C. I and a Δε of +7.4.

(77) ##STR00255##

(78) This compound (CLS-3-T) has a melting point of 76° C., a clearing point of 104° C., a phase range with only a nematic phase as a mesophase, i.e. K 76° C. N, 104° C. I and a Δε of +8.4.

(79) ##STR00256##

(80) This compound (CGS-3-T) has a melting point of 70° C., a clearing point of 77° C., a phase range of K 70° C. N, 77° C. I and a Δε of +11.1.

(81) ##STR00257##

(82) This compound (CYS-3-T) has a melting point of 68° C., a monotropic clearing point of 66° C., a phase range of K 68° C. S.sub.A (40° C.) N (66° C.) I and a Δε of +5.7.

(83) ##STR00258##

(84) This compound (CUS-3-T) has a melting point of 61° C., a clearing point of 172° C., a phase range of K 61° C. S.sub.B 98° C. S.sub.A 172° C. I and a Δε of +14.4.

(85) ##STR00259##

(86) This compound (LGS-3-T) has a melting point of 72° C., a clearing point of 123° C., a phase range of K 72° C. S.sub.A 123° C. I and a Δε of +13.3.

(87) ##STR00260##

(88) This compound (PS-3-T) has a melting point (T(K.fwdarw.I)) of 69° C. and a Δε of +9.1.

(89) ##STR00261##

(90) This compound (YS-20-T) has a melting point (T(K.fwdarw.I)) of 68° C. and a Δε of +5.5.

(91) Analogously the following compounds of formula T-1-1 are prepared

(92) ##STR00262##

(93) TABLE-US-00007 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 (see above) CF.sub.3 K 41 S.sub.X 45 S.sub.A 52 +7.4 N 95 I C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(94) Analogously the following compounds of formula T-2-1 are prepared

(95) ##STR00263##

(96) TABLE-US-00008 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 (see above) CF.sub.3 K 76 N 104 I. +8.4 C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(97) Analogously the following compounds of formula T-3-1 are prepared

(98) ##STR00264##

(99) TABLE-US-00009 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 CF.sub.3 C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(100) Analogously the following compounds of formula T-3-2 are prepared

(101) ##STR00265##

(102) TABLE-US-00010 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 (see above) CF.sub.3 K 70 N 77 I +11.1 C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(103) Analogously the following compounds of formula T-3-3 are prepared

(104) ##STR00266##

(105) TABLE-US-00011 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 (see above) CF.sub.3 K 68 S.sub.A (40) N +5.7 (66) I C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(106) Analogously the following compounds of formula T-3-4 are prepared

(107) ##STR00267##

(108) TABLE-US-00012 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 (see above) CF.sub.3 K 61 S.sub.B 98 S.sub.A +14.4 172 I C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(109) Analogously the following compounds of formula T-4-1 are prepared

(110) ##STR00268##

(111) TABLE-US-00013 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 CF.sub.3 C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(112) Analogously the following compounds of formula T-4-2 are prepared

(113) ##STR00269##

(114) TABLE-US-00014 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 (see above) CF.sub.3 K 72 SmA 123 I +13.3 C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(115) Analogously the following compounds of formula T-4-3 are prepared

(116) ##STR00270##

(117) TABLE-US-00015 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 CF.sub.3 C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(118) Analogously the following compounds of formula T-4-4 are prepared

(119) ##STR00271##

(120) TABLE-US-00016 R.sup.S X.sup.S Phase range Δε CH.sub.3 F C.sub.2H.sub.5 F C.sub.3H.sub.7 F C.sub.4H.sub.9 F C.sub.5H.sub.11 F C.sub.6H.sub.13 F C.sub.7H.sub.15 F CH.sub.2═CH F CH.sub.2═CH—CH.sub.2 F CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3—CH.sub.2═CH F CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 F CH.sub.3 OCF.sub.3 C.sub.2H.sub.5 OCF.sub.3 C.sub.3H.sub.7 OCF.sub.3 C.sub.4H.sub.9 OCF.sub.3 C.sub.5H.sub.11 OCF.sub.3 C.sub.6H.sub.13 OCF.sub.3 C.sub.7H.sub.15 OCF.sub.3 CH.sub.2═CH OCF.sub.3 CH.sub.2═CH—CH.sub.2 OCF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3—CH.sub.2═CH OCF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 OCF.sub.3 CH.sub.3 CF.sub.3 C.sub.2H.sub.5 CF.sub.3 C.sub.3H.sub.7 CF.sub.3 C.sub.4H.sub.9 CF.sub.3 C.sub.5H.sub.11 CF.sub.3 C.sub.6H.sub.13 CF.sub.3 C.sub.7H.sub.15 CF.sub.3 CH.sub.2═CH CF.sub.3 CH.sub.2═CH—CH.sub.2 CF.sub.3 CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3 CH.sub.3—CH.sub.2═CH CF.sub.3 CH.sub.3—CH.sub.2═CH—[CH.sub.2].sub.2 CF.sub.3

(121) Further compound examples

(122) ##STR00272## ##STR00273##

Comparative, Additional Compounds 1 to 6

(123) Compounds of formula I-S-1 are e.g.

(124) ##STR00274##

(125) This compound (LB(S)-3-F) has a melting point of 133° C., a clearing point of 155.3° C., a phase range of K 133° C. N, 155.3° C. I and a Δε of +1.3.

(126) ##STR00275##

(127) This compound (LB(S)-3-OT), the compound of synthesis example 2, has a melting point of 66° C., a clearing point of 181° C., a phase range of K 66° C. S.sub.A 181° C. I and a Δε of +4.7.

(128) ##STR00276##

(129) Compounds of formula I-S-2 are e.g.

(130) This compound (LB(S)-3-T) has a melting point of 121° C., a clearing point of 162° C., a phase range of 121° C. S.sub.A 162° C. I and a Δε of +7.8.

(131) ##STR00277##

(132) This compound (CB(S)-3-F) has a melting point of 157° C., a clearing point of 170.3° C., a phase range of K 157° C. N, 170.3 I.

(133) ##STR00278##

(134) This compound (CB(S)-3-OT), the compound of synthesis example 2, has a melting point of 108° C., a clearing point of 168.5° C., a phase range of K 108° C. S.sub.A 141° C. N, 168.5° C. I and a Δε of +4.5.

(135) ##STR00279##

(136) This compound (CB(S)-3-T) has a melting point of 150° C., a (monotropic) clearing point of 138.8° C., a phase range of K 150° C. N (138.8° C.) I and a Δε of +8.1.

(137) Analogously the following compounds of formula I comprising a dibenzothophene moiety are prepared

(138) ##STR00280##

(139) This compound (DB(S)-3-OT) has a melting point of 153° C., a clearing point of 174.1° C. and a phase range of K 153° C. S.sub.A 165° C. N, 174.1° C. 1.

(140) ##STR00281##

(141) This compound (DB(S)-3-OT) has a melting point of 146° C., a clearing point of 168° C. and a phase range of K 146° C. S.sub.A 168° C. 1.

(142) Further comparative, additional compound examples

(143) ##STR00282## ##STR00283## ##STR00284##

MIXTURE EXAMPLES

(144) In the following are exemplary mixtures disclosed.

Example 1

(145) The following mixture (M-1) is prepared and investigated.

(146) TABLE-US-00017 Mixture 1 Composition Compound Concentration/ No. Abbreviation % by weight  1 CCS-3-T 7.0  2 CC-3-V 27.0  3 CC-3-V1 7.0  4 CC-3-2V1 8.0  5 CCP-V-1 8.0  6 CCP-V2-1 4.5  7 CLP-V-1 6.0  8 PP-1-2V1 4.0  9 CCVC-3-V 5.0 10 CCP-3-OT 5.0 11 CLP-3-T 2.0 12 CCGU-3-F 4.0 13 CDUQU-3-F 8.0 14 DGUQU-2-F 1.5 15 DGUQU-4-F 3.0 Σ 100.0 Physical properties T(N, I) = 106.5° C. n.sub.e(20° C., 589 nm) = 1.5725 Δn(20° C., 589 nm) = 0.0900 ε.sub.∥(20° C., 1 kHz) = 8.0 ε.sub.⊥(20° C., 1 kHz) = 2.8 Δε(20° C., 1 kHz) = 5.1 ε.sub.av.(20° C., 1 kHz) = 4.5 γ.sub.1(20° C.) = 91 mPa .Math. s k.sub.11(20° C.) = 19.8 pN k.sub.33(20° C.) = 21.7 pN V.sub.0(20° C.) = 2.07 V ε.sub.⊥/Δε(20° C.) = 0.55 γ.sub.1/k.sub.11 (20° C.) = 4.60 * Remark: * [mPa .Math. s/pN].

(147) This mixture, mixture M-1, is characterized by a good transmission in an FFS display and shows a short response time.

Example 2

(148) The following mixture (M-2) is prepared and investigated.

(149) TABLE-US-00018 Mixture M-2 Composition Compound Concentration/ No. Abbreviation % by weight  1 CCS-3-T 8.0  2 LB(S)-3-OT 5.5  3 CC-3-V 29.5  4 CC-3-V1 8.0  5 CC-3-2V1 8.0  6 CCP-V-1 10.5  7 CLP-V-1 6.0  8 CCVC-3-V 1.5  9 CCP-3-OT 3.5 10 CLP-3-T 5.0 11 CCGU-3-F 3.5 12 CDUQU-3-F 5.5 13 DGUQU-2-F 1.5 14 DGUQU-4-F 4.0 Σ 100.0 Physical properties T(N, I) = 103.0° C. n.sub.e(20° C., 589 nm) = 1.5719 Δn(20° C., 589 nm) = 0.0903 ε.sub.∥(20° C., 1 kHz) = 8.3 ε.sub.⊥(20° C., 1 kHz) = 3.2 Δε(20° C., 1 kHz) = 5.1 ε.sub.av.(20° C., 1 kHz) = 4.9 γ.sub.1(20° C.) = 92 mPa .Math. s k.sub.11(20° C.) = 19.6 pN k.sub.33(20° C.) = 20.7 pN V.sub.0(20° C.) = 2.05 V ε.sub.⊥/Δε(20° C.) = 0.63 γ.sub.1/k.sub.11 (20° C.) = 4.70 * Remark: * [mPa .Math. s/pN].

(150) This mixture, mixture M-2, is characterized by a good transmission in an FFS display and shows a short response time.

Example 3

(151) The following mixture (M-3) is prepared and investigated

(152) TABLE-US-00019 Mixture M-3 Composition Compound Concentration/ No. Abbreviation % by weight  1 CCS-3-T 10.0  2 LB(S)-3-OT 6.5  3 CC-3-V 32.0  4 CC-3-V1 7.5  5 CC-3-2V1 1.5  6 CCP-V-1 8.0  7 CLP-V-1 7.0  8 CCVC-3-V 3.5  9 CCP-3-OT 5.0 10 CLP-3-T 7.0 11 CCGU-3-F 2.0 12 CDUQU-3-F 4.5 13 DGUQU-2-F 1.5 14 DGUQU-4-F 4.0 Σ 100.0 Physical properties T(N, I) = 104.5° C. n.sub.e(20° C., 589 nm) = 1.5732 Δn(20° C., 589 nm) = 0.0916 ε.sub.∥(20° C., 1 kHz) = 8.4 ε.sub.⊥(20° C., 1 kHz) = 3.2 Δε(20° C., 1 kHz) = 5.2 ε.sub.av.(20° C., 1 kHz) = 4.9 γ.sub.1(20° C.) = 92 mPa .Math. s k.sub.11(20° C.) = 19.8 pN k.sub.33(20° C.) = 20.6 pN V.sub.0(20° C.) = 2.06 V ε.sub.⊥/Δε(20° C.) = 0.62 γ.sub.1/k.sub.11 (20° C.) = 4.65 * Remark: * [mPa .Math. s/pN].

(153) This mixture, mixture M-3, is characterized by a good transmission in an FFS display and shows a short response time.

Example 4

(154) The following mixture (M-4) is prepared and investigated

(155) TABLE-US-00020 Mixture M-4 Composition Compound Concentration/ No. Abbreviation % by weight  1 CCS-3-T 7.0  2 CC-3-V 29.5  3 CC-3-V1 7.0  4 CC-3-2V1 8.0  5 CCP-V-1 8.0  6 CCP-V2-1 4.5  7 CLP-V-1 6.0  8 CCVC-3-V 5.0  9 PP-1-2V1 3.5 10 CCP-3-OT 4.0 11 CLP-3-T 2.0 12 CCGU-3-F 3.0 13 CDUQU-3-F 8.0 14 DGUQU-2-F 1.5 15 DGUQU-4-F 3.0 Σ 100.0 Physical properties T(N, I) = 104.0° C. n.sub.e(20° C., 589 nm) = 1.5729 Δn(20° C., 589 nm) = 0.0900 ε.sub.∥(20° C., 1 kHz) = 7.8 ε.sub.⊥(20° C., 1 kHz) = 2.8 Δε(20° C., 1 kHz) = 4.9 ε.sub.av.(20° C., 1 kHz) = 4.4 γ.sub.1(20° C.) = 90 mPa .Math. s k.sub.11(20° C.) = 19.6 pN k.sub.33(20° C.) = 21.7 pN V.sub.0(20° C.) = 2.11 V ε.sub.⊥/Δε(20° C.) = 0.57 γ.sub.1/k.sub.11 (20° C.) = 4.60 * Remark: * [mPa .Math. s/pN].

(156) This mixture, mixture M-4 is characterized by a good transmission in an FFS display and shows a short response time.

Example 5

(157) The following mixture (M-5) is prepared and investigated.

(158) TABLE-US-00021 Mixture M-5 Composition Compound Concentration/ No. Abbreviation % by weight 1 CLS-3-T 8.0 2 LB(S)-3-OT 5.5 3 CC-3-V 30.5 4 CC-3-V1 8.0 5 CC-3-2V1 8.0 6 CCP-V-1 10.5 7 CLP-V-1 6.0 8 CCVC-3-V 1.5 9 CCP-3-OT 3.5 10 CLP-3-T 5.0 11 CCGU-3-F 3.0 12 CDUQU-3-F 5.5 13 DGUQU-2-F 1.5 14 DGUQU-4-F 3.5 Σ 100.0 Physical properties T(N, I) = 102.5° C. n.sub.e(20° C., 589 nm) = 1.5742 Δn(20° C., 589 nm) = 0.0918 ε.sub.∥(20° C., 1 kHz) = 8.0 ε.sub.⊥(20° C., 1 kHz) = 3.1 Δε(20° C., 1 kHz) = 4.9 ε.sub.av.(20° C., 1 kHz) = 4.7 γ.sub.1(20° C.) = 93 mPa .Math. s k.sub.11(20° C.) = 19.9 pN k.sub.33(20° C.) = 20.3 pN V.sub.0(20° C.) = 2.13 V ε.sub.⊥/Δε(20° C.) = 0.66 γ.sub.1 /k.sub.11(20° C.) = 4.67 * Remark: *: [mPa .Math. s/pN].

(159) This mixture, mixture M-5, is characterized by a good transmission in an FFS display and shows a short response time.

Example 6

(160) The following mixture (M-6) is prepared and investigated.

(161) TABLE-US-00022 Mixture M-6 Composition Compound Concentration/ No. Abbreviation % by weight 1 CLS-3-T 10.0 2 LB(S)-3-OT 5.5 3 CC-3-V 34.0 4 CC-3-V1 8.0 5 CC-3-2V1 3.5 6 CCP-V-1 6.0 7 CLP-V-1 7.0 8 CCVC-3-V 5.0 9 CCP-3-OT 3.0 10 CLP-3-T 5.5 11 CCGU-3-F 2.0 12 CDUQU-3-F 4.0 13 DGUQU-2-F 1.5 14 DGUQU-4-F 5.0 Σ 100.0 Physical properties T(N, I) = 102.5° C. n.sub.e(20° C., 589 nm) = 1.5732 Δn(20° C., 589 nm) = 0.0915 ε.sub.∥(20° C., 1 kHz) = 8.2 ε.sub.⊥(20° C., 1 kHz) = 3.2 Δε(20° C., 1 kHz) = 5.0 ε.sub.av.(20° C., 1 kHz) = 4.9 γ.sub.1(20° C.) = 92 mPa .Math. s k.sub.11(20° C.) = 19.7 pN k.sub.33(20° C.) = 20.6 pN V.sub.0(20° C.) = 2.09 V ε.sub.⊥/Δε(20° C.) = 0.64 γ.sub.1/k.sub.11(20° C.) = 4.67 * Remark: *: [mPa .Math. s/pN].

(162) This mixture, mixture M-6, is characterized by a good transmission in an FFS display and shows a short response time.

Example 7

(163) The following mixture (M-7) is prepared and investigated.

(164) TABLE-US-00023 Mixture M-7 Composition Compound Concentration/ No. Abbreviation % by weight 1 CLS-3-T 15.0 2 LB(S)-3-OT 6.0 3 CC-3-V 36.0 4 CC-3-V1 8.0 5 CCP-V-1 6.0 6 CLP-V-1 7.0 7 CCVC-3-V 5.0 8 CCP-3-OT 2.0 9 CLP-3-T 4.0 10 CCGU-3-F 2.0 11 CDUQU-3-F 2.5 12 DGUQU-2-F 1.5 13 DGUQU-4-F 5.0 Σ 100.0 Physical properties T(N, I) = 100.5° C. n.sub.e(20° C., 589 nm) = 1.5746 Δn(20° C., 589 nm) = 0.0924 ε.sub.∥(20° C., 1 kHz) = 8.0 ε.sub.⊥(20° C., 1 kHz) = 3.3 Δε(20° C., 1 kHz) = 4.8 ε.sub.av.(20° C., 1 kHz) = 4.9 γ.sub.1(20° C.) = 90 mPa .Math. s k.sub.11(20° C.) = 19.5 pN k.sub.33(20° C.) = 19.5 pN V.sub.0(20° C.) = 2.13 V ε.sub.⊥/Δε(20° C.) = 0.69 γ.sub.1/k.sub.11(20° C.) = 4.62 * Remark: *: [mPa .Math. s/pN].

(165) This mixture, mixture M-7, is characterized by a good transmission in an FFS display and shows a short response time.

Example 8

(166) The following mixture (M-8) is prepared and investigated.

(167) TABLE-US-00024 Mixture M-8 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 12.0 2 LB-3-T 1.5 3 LB(S)-3-OT 7.0 4 CC-3-V 42.5 5 CCP-V-1 5.0 6 PGP-1-2V 8.0 7 PGP-2-2V 6.0 8 PGU-2-F 4.0 9 PGU-3-F 2.0 10 PPGU-3-F 0.5 11 APUQU-2-F 2.0 12 APUQU-3-F 2.0 13 PGUQU-3-F 3.5 14 PGUQU-4-F 2.0 15 PGUQU-5-F 2.0 Σ 100.0 Physical properties T(N, I) = 85.5° C. n.sub.e(20° C., 589 nm) = 1.6156 Δn(20° C., 589 nm) = 0.1256 ε.sub.∥(20° C., 1 kHz) = 9.2 ε.sub.⊥(20° C., 1 kHz) = 3.7 Δε(20° C., 1 kHz) = 5.5 ε.sub.av.(20° C., 1 kHz) = 5.5 γ.sub.1(20° C.) = 67 mPa .Math. s k.sub.11(20° C.) = 16.1 pN k.sub.33(20° C.) = 14.3 pN V.sub.0(20° C.) = 1.80 V ε.sub.⊥/Δε(20° C.) = 0.67 γ.sub.1/k.sub.11(20° C.) = 4.16 * Remark: *: [mPa .Math. s/pN].

(168) This mixture, mixture M-8, is characterized by a good transmission in an FFS display and shows a short response time.

Example 9

(169) The following mixture (M-9) is prepared and investigated

(170) TABLE-US-00025 Mixture M-9 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 7.0 2 LB(S)-3-OT 7.0 3 CC-3-V 49.5 4 PGP-1-2V 8.0 5 PGP-2-2V 8.0 6 PGP-3-2V 2.0 7 PPGU-3-F 0.5 8 APUQU-2-F 4.0 9 APUQU-3-F 4.0 10 PGUQU-3-F 4.0 11 PGUQU-4-F 2.0 12 PGUQU-5-F 4.0 Σ 100.0 Physical properties T(N, I) = 84.0° C. n.sub.e(20° C., 589 nm) = 1.6136 Δn(20° C., 589 nm) = 0.1249 ε.sub.∥(20° C., 1 kHz) = 9.2 ε.sub.⊥(20° C., 1 kHz) = 3.5 Δε(20° C., 1 kHz ) = 5.7 ε.sub.av.(20° C., 1 kHz) = 5.4 γ.sub.1(20° C.) = 63 mPa .Math. s k.sub.11(20° C.) = 15.2 pN k.sub.33(20° C.) = 14.2 pN V.sub.0(20° C.) = 1.72 V ε.sub.⊥/Δε(20° C.) = 0.61 γ.sub.1/k.sub.11(20° C.) = 4.14 * Remark: *: [mPa .Math. s/pN].

(171) This mixture, mixture M-9, is characterized by a good transmission in an FFS display and shows a short response time.

Example 10

(172) The following mixture (M-10) is prepared and investigated.

(173) TABLE-US-00026 Mixture M-10 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 4.0 2 LB(S)-3-OT 7.0 3 CC-3-V 45.0 4 CC-3-V1 2.5 5 CCP-V-1 5.0 6 PP-1-2V1 2.5 7 PGP-1-2V 7.0 8 PGP-2-2V 3.0 9 PGP-3-2V 4.0 10 PPGU-3-F 0.5 11 APUQU-2-F 4.5 12 APUQU-3-F 4.5 13 PGUQU-3-F 4.0 14 PGUQU-4-F 2.5 15 PGUQU-5-F 4.0 Σ 100.0 Physical properties T(N, I) = 85.5° C. n.sub.e(20° C., 589 nm) = 1.6132 Δn(20° C., 589 nm) = 0.1240 ε.sub.∥(20° C., 1 kHz) = 9.4 ε.sub.⊥(20° C., 1 kHz) = 3.4 Δε(20° C., 1 kHz) = 5.9 ε.sub.av.(20° C., 1 kHz) = 5.4 γ.sub.1(20° C.) = 67 mPa .Math. s k.sub.11(20° C.) = 15.2 pN k.sub.33(20° C.) = 14.9 pN V.sub.0(20° C.) = 1.69 V ε.sub.⊥/Δε(20° C.) = 0.58 γ.sub.1/k.sub.11(20° C.) = 4.41* Remark: *: [mPa .Math. s/pN].

(174) This mixture, mixture M-10, is characterized by a good transmission in an FFS display and shows a short response time.

Example 11

(175) The following mixture (M-11) is prepared and investigated.

(176) TABLE-US-00027 Mixture M-11 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 8.0 2 LB-3-T 3.0 3 CC-3-V 46.5 4 CCP-V-1 5.0 5 PGP-1-2V 7.0 6 PGP-2-2V 8.0 7 PGP-3-2V 4.0 8 PPGU-3-F 0.5 9 APUQU-2-F 4.5 10 APUQU-3-F 4.5 11 PGUQU-3-F 3.0 12 PGUQU-4-F 3.0 13 PGUQU-5-F 3.0 Σ 100.0 Physical properties T(N, I) = 85.5° C. n.sub.e(20° C., 589 nm) = 1.6129 Δn(20° C., 589 nm) = 0.1234 ε.sub.∥(20° C., 1 kHz) = 9.0 ε.sub.⊥(20° C., 1 kHz) = 3.4 Δε(20° C., 1 kHz) = 5.6 ε.sub.av.(20° C., 1 kHz) = 5.3 γ.sub.1(20° C.) = 66 mPa .Math. s k.sub.11(20° C.) = 15.1 pN k.sub.33(20° C.) = 14.5 pN V.sub.0(20° C.) = 1.73 V ε.sub.⊥/Δε(20° C.) = 0.61 γ.sub.1/k.sub.11(20° C.) = 4.37 * Remark: *: [mPa .Math. s/pN].

(177) This mixture, mixture M-11, is characterized by a good transmission in an FFS display and shows a short response time.

Example 12

(178) The following mixture (M-12) is prepared and investigated.

(179) TABLE-US-00028 Mixture M-12 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 5.5 2 B(S)-2O-O4 2.0 3 B(S)-2O-O5 2.0 4 CC-3-V 48.5 5 CCVC-3-V 3.0 6 PP-1-2V1 3.0 7 PGP-1-2V 7.0 8 PGP-2-2V 7.0 9 PGP-3-2V 4.0 10 PPGU-3-F 0.5 11 DPGU-4-F 4.0 12 DGUQU-2-F 1.5 13 DGUQU-4-F 4.0 14 PGUQU-3-F 3.0 15 PGUQU-4-F 3.0 16 PGUQU-5-F 2.0 Σ 100.0 Physical properties T(N, I) = 84.0° C. n.sub.e(20° C., 589 nm) = 1.6146 Δn(20° C., 589 nm) = 0.1245 ε.sub.∥(20° C., 1 kHz) = 9.0 ε.sub.⊥(20° C., 1 kHz) = 3.6 Δε(20° C., 1 kHz ) = 5.4 ε.sub.av.(20° C., 1 kHz) = 5.4 γ.sub.1(20° C.) = 64 mPa .Math. s k.sub.11(20° C.) = 15.0 pN k.sub.33(20° C.) = 14.2 pN V.sub.0(20° C.) = 1.76 V ε.sub.⊥/Δε(20° C.) = 0.67 γ.sub.1/k.sub.11(20° C.) = 4.27 * Remark: *: [mPa .Math. s/pN].

(180) This mixture, mixture M-12, is characterized by a good transmission in an FFS display and shows a short response time.

Example 13

(181) The following mixture (M-13) is prepared and investigated.

(182) TABLE-US-00029 Mixture M-13 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 5.5 2 LB(S)-3-OT 5.0 3 CC-3-V 49.5 4 CCVC-3-V 2.0 5 PP-1-2V1 3.5 6 PGP-1-2V 7.0 7 PGP-2-2V 7.0 8 PGP-3-2V 3.5 9 PPGU-3-F 0.5 10 DPGU-4-F 4.0 11 DGUQU-2-F 1.5 12 DGUQU-4-F 3.0 13 PGUQU-3-F 3.0 14 PGUQU-4-F 3.0 15 PGUQU-5-F 2.0 Σ 100.0 Physical properties T(N, I) = 84.0° C. n.sub.e(20° C., 589 nm) = 1.6143 Δn(20° C., 589 nm) = 0.1247 ε.sub.∥(20° C., 1 kHz) = 8.7 ε.sub.⊥(20° C., 1 kHz) = 3.3 Δε(20° C., 1 kHz) = 5.4 ε.sub.av.(20° C., 1 kHz) = 5.1 γ.sub.1(20° C.) = 62 mPa .Math. s k.sub.11(20° C.) = 15.2 pN k.sub.33(20° C.) = 14.3 pN V.sub.0(20° C.) = 1.77 V ε.sub.⊥/Δε(20° C.) = 0.61 γ.sub.1/k.sub.11(20° C.) = 4.08 * Remark: *: [mPa .Math. s/pN].

(183) This mixture, mixture M-13, is characterized by a good transmission in an FFS display and shows a short response time.

Example 14

(184) The following mixture (M-14) is prepared and investigated.

(185) TABLE-US-00030 Mixture M-14 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 7.0 2 LB(S)-3-OT 3.5 3 CC-3-V 47.0 4 CCP-V-1 4.0 5 PP-1-2V1 1.5 6 PGP-1-2V 7.0 7 PGP-2-2V 7.5 8 PGP-3-2V 4.0 9 PPGU-3-F 0.5 10 APUQU-2-F 4.5 11 APUQU-3-F 4.5 12 PGUQU-3-F 3.0 13 PGUQU-4-F 3.0 14 PGUQU-5-F 3.0 Σ 100.0 Physical properties T(N, I) = 85.0° C. n.sub.e(20° C., 589 nm) = 1.6148 Δn(20° C., 589 nm) = 0.1249 ε.sub.∥(20° C., 1 kHz) = 8.9 ε.sub.⊥(20° C., 1 kHz) = 3.3 Δε(20° C., 1 kHz) = 5.6 ε.sub.av.(20° C., 1 kHz) = 5.2 γ.sub.1(20° C.) = 64 mPa .Math. s k.sub.11(20° C.) = 15.2 pN k.sub.33(20° C.) = 14.7 pN V.sub.0(20° C.) = 1.73 V ε.sub.⊥/Δε(20° C.) = 0.59 γ.sub.1/k.sub.11(20° C.) = 4.21 * Remark: *: [mPa .Math. s/pN].

(186) This mixture, mixture M-14, is characterized by a good transmission in an FFS display and shows a short response time.

Example 15

(187) The following mixture (M-15) is prepared and investigated.

(188) TABLE-US-00031 Mixture M-15 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 7.5 2 B(S)-2O-O4 2.5 3 B(S)-2O-O5 2.0 4 CC-3-V 48.0 5 CCVC-3-V 2.5 6 PP-1-2V1 1.5 7 PGP-1-2V 7.5 8 PGP-2-2V 7.5 9 PGP-3-2V 3.0 10 PPGU-3-F 0.5 11 DPGU-4-F 3.0 12 DGUQU-2-F 1.5 13 DGUQU-4-F 4.0 14 PGUQU-3-F 3.5 15 PGUQU-4-F 3.5 16 PGUQU-5-F 2.0 Σ 100.0 Physical properties T(N, I) = 84.5° C. n.sub.e(20° C., 589 nm) = 1.6138 Δn(20° C., 589 nm) = 0.1241 ε.sub.∥(20° C., 1 kHz) = 9.3 ε.sub.⊥(20° C., 1 kHz) = 3.7 Δε(20° C., 1 kHz) = 5.5 ε.sub.av.(20° C., 1 kHz) = 5.6 γ.sub.1(20° C.) = 65 mPa .Math. s k.sub.11(20° C.) = 15.2 pN k.sub.33(20° C.) = 14.1 pN V.sub.0(20° C.) = 1.74 V ε.sub.⊥/Δε(20° C.) = 0.67 γ.sub.1/k.sub.11(20° C.) = 4.28 * Remark: *: [mPa .Math. s/pN].

(189) This mixture, mixture M-15, is characterized by a good transmission in an FFS display and shows a short response time.

Example 16

(190) The following mixture (M-16) is prepared and investigated.

(191) TABLE-US-00032 Mixture M-16 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 8.0 2 B(S)-2O-O4 2.5 3 B(S)-2O-O5 2.0 4 CC-3-V 47.0 5 CC-3-V1 1.5 6 CCVC-3-V 1.5 7 PGP-1-2V 8.0 8 PGP-2-2V 8.0 9 PGP-3-2V 3.0 10 PPGU-3-F 0.5 11 DPGU-4-F 3.0 12 DGUQU-2-F 1.5 13 DGUQU-4-F 4.0 14 PGUQU-3-F 3.5 15 PGUQU-4-F 4.0 16 PGUQU-5-F 2.0 Σ 100.0 Physical properties T(N, I) = 85.0° C. n.sub.e(20° C., 589 nm) = 1.6147 Δn(20° C., 589 nm) = 0.1253 ε.sub.∥(20° C., 1 kHz) = 9.6 ε.sub.⊥(20° C., 1 kHz) = 3.8 Δε(20° C., 1 kHz) = 5.8 ε.sub.av.(20° C., 1 kHz) = 5.7 γ.sub.1(20° C.) = 66 mPa .Math. s k.sub.11(20° C.) = 15.3 pN k.sub.33(20° C.) = 14.2 pN V.sub.0(20° C.) = 1.71 V ε.sub.⊥/Δε(20° C.) = 0.66 γ.sub.1/k.sub.11(20° C.) = 4.31 * Remark: *: [mPa .Math. s/pN].

(192) This mixture, mixture M-16, is characterized by a good transmission in an FFS display and shows a short response time.

Example 17

(193) The following mixture (M-17) is prepared and investigated

(194) TABLE-US-00033 Mixture M-17 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 10.0 2 CCS-4-T 3.5 3 LB-3-T 12.0 4 LB(S)-3-OT 10.0 5 CLY-3-OT 7.0 6 CC-3-V 41.0 7 CCP-V-1 10.0 8 PP-1-2V1 1.5 9 PUQU-3-F 5.0 Σ 100.0 Physical properties T(N, I) = 77.5° C. n.sub.e(20° C., 589 nm) = 1.5801 Δn(20° C., 589 nm) = 0.0994 ε.sub.∥(20° C., 1 kHz) = 7.4 ε.sub.⊥(20° C., 1 kHz) = 4.8 Δε(20° C., 1 kHz) = 2.6 ε.sub.av.(20° C., 1 kHz) = 5.7 γ.sub.1(20° C.) = 67 mPa .Math. s k.sub.11(20° C.) = 15.3 pN k.sub.33(20° C.) = 13.9 pN V.sub.0(20° C.) = 2.54 V ε.sub.⊥/Δε(20° C.) = 1.85 γ.sub.1/k.sub.11(20° C.) = 4.38 * Remark: *: [mPa .Math. s/pN].

(195) This mixture, mixture M-17, is characterized by a good transmission in an FFS display and shows a short response time.

Example 18

(196) The following mixture (M-18) is prepared and investigated.

(197) TABLE-US-00034 Mixture M-18 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 8.0 2 LB-3-T 6.0 3 CLY-3-OT 8.0 4 CC-3-V 34.0 5 CCP-V-1 9.0 6 CCP-V2-1 3.0 7 CCVC-3-V 4.0 8 PGP-1-2V 1.5 9 PGP-2-2V 5.0 10 CPPC-3-3 3.0 11 CGPC-3-3 3.0 12 CPGP-5-2 3.0 13 CPGP-5-3 3.0 14 PUQU-3-F 2.5 15 PGUQU-3-F 3.5 16 PGUQU-4-F 3.5 Σ 100.0 Physical properties T(N, I) = 116.0° C. n.sub.e(20° C., 589 nm) = 1.6080 Δn(20° C., 589 nm) = 0.1203 ε.sub.∥(20° C., 1 kHz) = 7.2 ε.sub.⊥(20° C., 1 kHz ) = 3.6 Δε(20° C., 1 kHz ) = 3.7 ε.sub.av.(20° C., 1 kHz) = 4.8 γ.sub.1(20° C.) = 113 mPa .Math. s k.sub.11(20° C.) = 19.2 pN k.sub.33(20° C.) = 19.3 pN V.sub.0(20° C.) = 2.39 V ε.sub.⊥/Δε(20° C.) = 0.96 γ.sub.1/k.sub.11(20° C.) = 5.88 * Remark: *: [mPa .Math. s/pN].

(198) This mixture, mixture M-18, is characterized by a good transmission in an FFS display and shows a short response time.

Example 19

(199) The following mixture (M-19) is prepared and investigated.

(200) TABLE-US-00035 Mixture M-19 Composition Compound Concentration/ No. Abbreviation % by weight 1 CCS-3-T 5.0 2 LB-3-T 2.5 3 LB(S)-3-OT 2.5 4 CC-3-V 25.0 5 CC-3-V1 8.0 6 CCP-V-1 14.0 7 CCP-V2-1 8.0 8 CCVC-3-V 5.0 9 PP-1-2V1 6.0 10 PGP-1-2V 7.0 11 PGP-2-2V 5.5 12 PPGU-3-F 0.5 13 CDUQU-3-F 7.0 14 DGUQU-4-F 2.0 15 PGUQU-3-F 2.0 Σ 100.0 Physical properties T(N, I) = 107.5° C. n.sub.e(20° C., 589 nm) = 1.6130 Δn(20° C., 589 nm) = 0.1220 ε.sub.∥(20° C., 1 kHz) = 6.9 ε.sub.⊥(20° C., 1 kHz) = 3.2 Δε(20° C., 1 kHz) = 3.8 ε.sub.av.(20° C., 1 kHz) = 4.4 γ.sub.1(20° C.) = t.b.d. mPa .Math. s k.sub.11(20° C.) = 19.5 pN k.sub.33(20° C.) = 19.5 pN V.sub.0(20° C.) = 2.40 V ε.sub.⊥/Δε(20° C.) = 0.84 γ.sub.1/k.sub.11(20° C.) = t.b.d * Remark: t.b.d.: to be determined and *: [mPa .Math. s/pN].

(201) This mixture, mixture M-19, is characterized by a good transmission in an FFS display and shows a short response time.

Example 20

(202) The following mixture (M-20) is prepared and investigated.

(203) TABLE-US-00036 Mixture M-20 Composition No. Abbreviation /% by weight Physical properties  1 CCS-3-T 8.0 n.sub.e(20° C., 589 nm) = 1.6133  2 LB-3-T 3.5 Δn(20° C., 589 nm) = 0.1216  3 LB(S)-3-OT 3.5 ε.sub.||(20° C., 1 kHz) = 7.2  4 CC-3-V 25.0 ε.sub.⊥(20° C., 1 kHz) = 3.4  5 CC-3-V1 7.0 Δε(20° C., 1 kHz) = 3.8  6 CCP-V-1 14.0 ε.sub.av.(20° C., 1 kHz) = 4.7  7 CCP-V2-1 6.0 γ.sub.1(20° C.) = t.b.d. mPa .Math. s  8 CCVC-3-V 4.0 k.sub.11(20° C.) = 20.1 pN  9 PP-1-2V1 6.0 k.sub.33(20° C.) = 19.1 pN 10 PGP-1-2V 7.0 V.sub.0(20° C.) = 2.44 V 11 PGP-2-2V 5.5 ε.sub.⊥/Δε(20° C.) = 0.89 12 PPGU-3-F 0.5 γ.sub.1/k.sub.11(20° C.) = t.b.d. * 13 CDUQU-3-F 7.0 14 DGUQU-4-F 3.0 Σ 100.0 Remark: t.b.d.: to be determined and * [mPa .Math. s/pN].

(204) This mixture, mixture M-20, is characterized by a good transmission in an FFS display and shows a short response time.

Example 21

(205) The following mixture (M-21) is prepared and investigated.

(206) TABLE-US-00037 Mixture M-21 Composition Compound Concentration/ No. Abbreviation % by weight Physical properties 1 CCS-3-T 10.0 T(N, I) = 80.1° C. 2 LB-3-T 10.0 3 LB(S)-3-OT 10.0 4 CC-3-V 46.5 5 CCP-V-1 13.0 6 PP-1-2V1 4.0 7 PPGU-3-F 0.5 8 CDUQU-3-F 2.0 9 PGUQU-3-F 4.0 Σ 100.0 γ.sub.1/k.sub.11(20° C.) = * Remark: * [mPa .Math. s/pN].

(207) This mixture, mixture M-21, is characterized by a good transmission in an FFS display and shows a short response time.

Example 22

(208) The following mixture (M-22) is prepared and investigated.

(209) TABLE-US-00038 Mixture M-22 Composition Compound Concentration/ No. Abbreviation % by weight Physical properties  1 CCS-3-T 10.0 T(N, I) = 99.5° C.  2 LB-3-T 7.0 n.sub.e(20° C., 589 nm) = 1.5942  3 LB(S)-3-OT 9.0 Δn(20° C., 589 nm) = 0.1100  4 CC-3-V 24.0 ε.sub.||(20° C., 1 kHz) = 10.1  5 CC-3-V1 9.0 ε.sub.⊥(20° C., 1 kHz) = 4.2  6 CC-3-2V1 6.0 Δε(20° C., 1 kHz) = 5.9  7 CCP-V-1 13.5 ε.sub.av.(20° C., 1 kHz) = 6.2  8 CCP-V2-1 5.0 γ.sub.1(20° C.) = 102 mPa .Math. s  9 CDUQU-3-F 2.5 k.sub.11(20° C.) = 18.8 pN 10 DGUQU-4-F 4.0 k.sub.33(20° C.) = 18.2 pN 11 PGUQU-3-F 3.5 V.sub.0(20° C.) = 1.88 V 12 PGUQU-4-F 6.5 ε.sub.⊥/Δε(20° C.) = 0.71 Σ 100.0 γ.sub.1/k.sub.11(20° C.) = 5.43 * Remark: t.b.d.: to be determined and * [mPa .Math. s/pN].

(210) This mixture, mixture M-22, is characterized by a good transmission in an FFS display and shows a short response time.

Example 23

(211) The following mixture (M-23) is prepared and investigated.

(212) TABLE-US-00039 Mixture M-23 Composition Compound Concentration/ No. Abbreviation % by weight Physical properties  1 CCS-3-T 10.0 T(N, I) = 99.0° C.  2 LB-3-T 8.5 n.sub.e(20° C., 589 nm) = 1.5927  3 LB(S)-3-OT 10.0 Δn(20° C., 589 nm) = 0.1095  4 CC-3-V 24.0 ε.sub.||(20° C., 1 kHz) = 10.3  5 CC-3-V1 9.0 ε.sub.⊥(20° C., 1 kHz) = 4.5  6 CC-3-2V1 5.5 Δε(20° C., 1 kHz) = 5.9  7 CCP-V-1 11.5 ε.sub.av.(20° C., 1 kHz) = 6.4  8 CCP-V2-1 5.0 γ.sub.1(20° C.) = 106 mPa .Math. s  9 CDUQU-3-F 5.5 k.sub.11(20° C.) = 19.1 pN 10 DGUQU-4-F 4.0 k.sub.33(20° C.) = 18.2 pN 11 PGUQU-3-F 3.5 V.sub.0(20° C.) = 1.90 V 12 PGUQU-4-F 3.5 ε.sub.⊥/Δε(20° C.) = 0.76 Σ 100.0 γ.sub.1/k.sub.11(20° C.) = 5.55 * Remark: * [mPa .Math. s/pN].

(213) This mixture, mixture M-23, is characterized by a good transmission in an FFS display and shows a short response time.

Example 24

(214) The following mixture (M-24) is prepared and investigated.

(215) TABLE-US-00040 Mixture M-24 Composition Compound Concentration/ No. Abbreviation % by weight Physical properties  1 CPS-3-T 5.0 T(N, I) = 79.0° C.  2 CC-3-V 44.0 n.sub.e(20° C., 589 nm) = 1.5903  3 CC-3-V1 12.0 Δn(20° C., 589 nm) = 0.1021  4 CCP-V-1 6.0 ε.sub.||(20° C., 1 kHz) = 5.5  5 CCP-V2-1 9.0 ε.sub.⊥(20° C., 1 kHz) = 2.6  6 PP-1-2V1 7.0 Δε(20° C., 1 kHz) = 2.8  7 PGP-2-3 6.0 ε.sub.av.(20° C., 1 kHz) = 3.6  8 PPGU-3-F 0.5 γ.sub.1(20° C.) = 55 mPa .Math. s  9 APUQU-3-F 4.5 k.sub.11(20° C.) = 14.8 pN 10 PGUQU-3-F 6.0 k.sub.33(20° C.) = 16.3 pN Σ 100.0 V.sub.0(20° C.) = 2.41 V ε.sub.⊥/Δε(20° C.) = 0.93 γ.sub.1/k.sub.11(20° C.) = 3.72 * Remark: * [mPa .Math. s/pN].

(216) This mixture, mixture M-24, is characterized by a good transmission in an FFS display and shows a short response time.

Example 25

(217) The following mixture (M-25) is prepared and investigated.

(218) TABLE-US-00041 Mixture M-25 Composition Compound Concentration/ No. Abbreviation % by weight Physical properties  1 PS-3-T 10.0 T(N, I) = 62.0° C.  2 CC-3-V 28.4 n.sub.e(20° C., 589 nm) = 1.5895  3 CC-3-V1 5.8 Δn(20° C., 589 nm) = 0.1003  4 CCP-3-3 5.4 ε.sub.||(20° C., 1 kHz) = 9.4  5 CCP-V-1 10.8 ε.sub.⊥(20° C., 1 kHz) = 3.3  6 CCP-V2-1 10.8 Δε(20° C., 1 kHz) = 6.1  7 PP-1-2V1 4.5 ε.sub.av.(20° C., 1 kHz) = 5.3  8 CPGP-5-2 1.8 γ.sub.1(20° C.) = 55 mPa .Math. s  9 PUQU-3-F 18.0 k.sub.11(20° C.) = 11.6 pN 10 APUQU-2-F 4.5 k.sub.33(20° C.) = 12.3 pN Σ 100.0 V.sub.0(20° C.) = 1.46 V ε.sub.⊥/Δε(20° C.) = 0.54 γ.sub.1/k.sub.11(20° C.) = 4.74 * Remark: t.b.d.: to be determined and * [mPa .Math. s/pN].

(219) This mixture, mixture M-25, is characterized by a good transmission in an FFS display and shows a short response time.

Example 26

(220) The following mixture (M-26) is prepared and investigated.

(221) TABLE-US-00042 Mixture M-26 Composition Compound Concentration/ No. Abbreviation % by weight Physical properties  1 YS-2O-T 10.0 T(N, I) = 67.5° C.  2 CC-3-V 28.4 n.sub.e(20° C., 589 nm) = 1.5897  3 CC-3-V1 5.8 Δn(20° C., 589 nm) = 0.1027  4 CCP-3-3 5.4 ε.sub.||(20° C., 1 kHz) = 9.7  5 CCP-V-1 10.8 ε.sub.⊥(20° C., 1 kHz) = 3.8  6 CCP-V2-1 10.8 Δε(20° C., 1 kHz) = 5.9  7 PP-1-2V1 4.5 ε.sub.av.(20° C., 1 kHz) = 5.8  8 CPGP-5-2 1.8 γ.sub.1(20° C.) = 59 mPa .Math. s  9 PUQU-3-F 18.0 k.sub.11(20° C.) = 12.2 pN 10 APUQU-2-F 4.5 k.sub.33(20° C.) = 12.9 pN Σ 100.0 V.sub.0(20° C.) = 1.53 V ε.sub.⊥/Δε(20° C.) = 0.66 γ.sub.1/k.sub.11(20° C.) = 4.84 * Remark: t.b.d.: to be determined and * [mPa .Math. s/pN].

(222) This mixture, mixture M-26, is characterized by a good transmission in an FFS display and shows a short response time.

Comparative Example A

(223) The following mixture (CE-A) is prepared and investigated.

(224) TABLE-US-00043 Mixture CE-A Composition Compound Concentration/ No. Abbreviation % by weight Physical properties 1 CC-3-V 31.5 T(N, I) = 78.5° C. 2 CC-3-V1 6.5 n.sub.e(20° C., 589 nm) = 1.5877 3 CCP-3-3 6.0 Δn(20° C., 589 nm) = 0.1001 4 CCP-V-1 12.0 ε.sub.⊥(20° C., 1 kHz) = 3.0 5 CCP-V2-1 12.0 Δε(20° C., 1 kHz) = 6.0 6 PP-1-2V1 5.0 ε.sub.av.(20° C., 1 kHz) = 5.0 7 CPGP-5-2 2.0 γ.sub.1 (20° C.) = 64 mPa .Math. s 8 PUQU-3-F 20.0 k.sub.11(20° C.) = 13.3 pN 9 APUQU-2-F 5.0 k.sub.33(20° C.) = 15.5 pN Σ 100.0 V.sub.0(20° C.) = 1.58 V V.sub.10(20° C.) = 2.13 V ε.sub.⊥/Δε = 0.50 γ.sub.1/ k.sub.11 = 4.81 * Remark: *) γ.sub.1/ k.sub.11 in mPa .Math. s / pN,

(225) This comparative mixture, mixture A, has a dielectric ratio (ε.sub.⊥/Δε) of 0.50, a ratio of (γ.sub.1/k.sub.11) of 4.81 mPa.Math.s/pN and is characterized a moderately good transmission in an FFS display and shows an at best acceptable short response time.

(226) To this mixture, used as a host mixture, several compounds of interest are added and the resultant mixtures are subsequently investigated.

(227) TABLE-US-00044 TABLE 1 Example CE-A A-1 A-2 A-3 Composition Cpd. None CCS-3-T CCS-4-T CLS-3-T c(Cpd.)/% 0.0 10.0 10.0 10.0 c(CE-A)/% 100.0 90.0 90.0 90.0 Properties T(N, I)/° C. 78.5 81.0 80.5 82.0 n.sub.e(589 nm) 1.5875 1.5848 1.5843 1.5895 Δn(589 nm) 0.1001 0.0987 0.0981 0.1020 ε.sub.||(1 kHz) 9.0 9.3 9.15 9.3 ε.sub.⊥(1 kHz) 3.0 3.3 3.12 3.1 Δε(1 kHz) 6.0 6.0 6.0 6.2 ε.sub.av.(1 kHz) 5.0 5.3 5.1 5.2 γ.sub.1/mPa .Math. s 64 67 68 73 k.sub.11/pN 13.3 14.4 14.2 14.9 k.sub.33/pN 15.5 15.2 15.2 16.2 ε.sub.⊥/Δε 0.50 0.55 0.52 0.50 γ.sub.1/k.sub.11* 4.81 4.72 4.79 4.90 V.sub.0/V 1.77 1.62 1.61 1.63 Example A-4 A-5 A-6 A-7 Composition Cpd. CGS-3-T CYS-3-T CUS-3-T LGS-3-T c(Cpd.)/% 10.0 10.0 10.0 10.0 c(CE-A)/% 90.0 90.0 90.0 90.0 Properties T(N, I)/° C. 79.0 78.0 77.0 81.0 n.sub.e(589 nm) 1.5942 1.5926 1.5917 1.6001 Δn(589 nm) 0.1063 0.1054 0.1047 0.1114 ε.sub.| |(1 kHz) 9.7 9.3 10.0 10.0 ε.sub.⊥(1 kHz) 3.2 3.3 3.2 3.2 Δε(1 kHz) 6.5 5.9 6.8 6.8 ε.sub.av.(1 kHz) 5.4 5.3 5.5 5.4 γ.sub.1/mPa .Math. s 70 70 69 70 k.sub.11/pN 13.9 13.5 13.4 15.4 k.sub.33/pN) 15.0 14.7 15.0 15.1 ε.sub.⊥/Δε 0.49 0.56 0.47 0.46 γ.sub.1/k.sub.11* 5.04 5.19 5.15 4.55 V.sub.0/V 1.64 1.59 1.48 1.59 Example A-8 A-9 A-10 A-11 Composition Cpd. CLS-4-T CLS-3-F CCS-5-T CPS-3-F c(Cpd.)/% 10.0 10.0 20.0 10.0 c(CE-A)/% 90.0 90.0 80.0 90.0 Properties T(N, I)/° C. 82.0 85.0 77.0 83.5 n.sub.e(589 nm) 1.5886 1.5923 1.5821 1.5976 Δn(589 nm) 0.1010 0.1029 0.0966 0.1073 ε.sub.||(1 kHz) 9.2 8.8 9.3 8.8 ε.sub.⊥(1 kHz) 3.1 3.0 3.2 3.0 Δε(1 kHz) 6.1 5.7 6.1 5.8 ε.sub.av.(1 kHz) 5.1 4.9 5.2 4.9 γ.sub.1/mPa .Math. s 73 73 t.b.d. 70 k.sub.11/pN 14.6 14.9 15.8 14.6 k.sub.33/pN) 15.1 17.1 15.9 16.3 ε.sub.⊥/Δε 0.51 0.53 0.52 0.52 γ.sub.1/k.sub.11* 5.00 4.90 t.b.d. t.bd. V.sub.0/V 1.62 1.70 1.69 1.67 Example A-12 Composition Cpd. CPS-3-T c(Cpd.)/% 10.0 c(CE-A)/% 90.0 Properties T(N, I)/° C. 81.0 n.sub.e(589 nm) 1.5951 Δn(589 nm) 0.1065 ε.sub.||(1 kHz) 9.4 ε.sub.⊥(1 kHz) 3.1 Δε(1 kHz) 6.3 ε.sub.av.(1 kHz) 5.2 γ.sub.1/mPa .Math. s 70 k.sub.11/pN 14.6 k.sub.33/pN) 15.1 ε.sub.⊥/Δε 0.49 γ.sub.1/k.sub.11* 4.79 V.sub.0/V 1.62 Remarks: all values (except clearing point) at 20° C., *[mPa .Math. s/pN] and t.b.d.: to be determined.

Comparative Example B

(228) The following mixture (CE-B) is prepared and investigated.

(229) TABLE-US-00045 Mixture CE-B Composition Compound Concentration/ No. Abbreviation % by weight Physical properties 1 CC-3-5 10.0 T(N, I) = 74.0° C. 2 CP-5-3 20.0 n.sub.e(20° C., 589 nm) = 1.5484 3 CCG-3-OT 10.0 Δn(20° C., 589 nm) = 0.0730 4 CCG-5-OT 10.0 ε.sub.||(20° C., 1 kHz) = 8.6 5 CCU-2-F 12.0 ε.sub.⊥(20° C., 1 kHz) = 3.2 6 CCU-3-F 10.0 Δε(20° C., 1 kHz) = 5.4 7 CCU-5-F 8.0 ε.sub.av.(20° C., 1 kHz) = 5.0 8 CCEP-3-F 10.0 γ.sub.1(20° C.) = 114 mPa .Math. s 9 CCEP-5-F 10.0 k.sub.11(20° C.) = 12.6 pN Σ 100.0 k.sub.33(20° C.) = 15.6 pN V.sub.0(20° C.) = 1.62 V ε.sub.⊥/Δε = 0.59 γ.sub.1/ k.sub.11 = 9.04 * Remark: * γ.sub.1/ k.sub.11 in mPa .Math. s / pN,

(230) This comparative mixture, mixture B, has a dielectric ratio (ε.sub.⊥/Δε) of 0.59 a ratio of (γ.sub.1/k.sub.11) of 9.04 mPa.Math.s/pN and is characterized a moderately good transmission in an FFS display and shows an at best acceptable short response time.

(231) Also to this mixture, used as another host mixture, several compounds of interest are added and the resultant mixtures are subsequently inveigated.

(232) TABLE-US-00046 TABLE 2 Example CE-B B-1 B-2 B-3 Composition Cpd. None CCS-3-T CCS-4-T CLS-3-T c(Cpd.)/% 0.0 10.0 10.0 10.0 c(CE-A)/% 100.0 90.0 90.0 90.0 Properties T(N, I)/° C. 74.0 75.5 75.5 76.0 Example B-4 B-5 B-6 B-7 Composition Cpd. CLS-4-T CLS-3-CI CPS-3-F CPS-3-T c(Cpd.)/% 10.0 10.0 10.0 10.0 c(CE-B)/% 90.0 90.0 90.0 90.0 Properties T(N, I)/° C. 76.0 84.0 78.5 74.0

Comparative Example C

(233) The following mixture (CE-C) is prepared and investigated.

(234) TABLE-US-00047 Mixture CE-A Composition Compound Concentration/ No. Abbreviation % by weight Physical properties  1 CC-3-V 30.0 T(N, I) = 96.9° C.  2 CC-3-V1 6.0 n.sub.e(20° C., 589 nm) = 1.6126  3 CC-4-V 5.5 Δn(20° C., 589 nm) = 0.1201  4 CCP-V-1 12.0 ε.sub.||(20° C., 1 kHz) = 6.1  5 CCP-V2-1 8.5 ε.sub.⊥(20° C., 1 kHz) = 2.8  6 PGP-2-3 5.0 Δε(20° C., 1 kHz) = 3.3  7 PGP-2-4 5.0 ε.sub.av.(20° C., 1 kHz) = 3.9  8 PGP-2-5 5.0 γ.sub.1(20° C.) = 93 mPa .Math. s  9 CPGC-3-3 1.5 k.sub.11(20° C.) = 15.6 pN 10 CPGP-5-2 3.0 k.sub.33(20° C.) = 16.5 pN 11 CPGP-5-3 3.0 V.sub.0(20° C.) = 2.29 V 12 CPG-3-F 2.0 V.sub.10(20° C.) = t.b.d. V 13 PPGU-3-F 0.5 ε.sub.⊥/Δε = 0.84 14 PUQU-3-f 10.0 γ.sub.1/ k.sub.11 = 5.96 * 15 APUQU-3-F 2.0 16 PGUQU-2-F 1.0 Σ 100.0 Remark: * γ.sub.1/ k.sub.11 in mPa .Math. s / pN,

(235) This comparative mixture, mixture C, has a dielectric ratio (ε.sub.⊥/Δε) of 0.84, a ratio of (γ.sub.1/k.sub.11) of 5.96 mPa.Math.s/pN and is characterized a moderately good transmission in an FFS display and shows an at best acceptable short response time.

(236) TABLE-US-00048 TABLE 3 Example CE-C C-1 Composition Cpd. None CCS-4-T c(Cpd.)/% 0.0 10.0 c(CE-C)/% 100.0 90.0 Properties T(N, I)/° C. 96.9 98.0 n.sub.e(589 nm) 1.6126 1.6084 Δn(589 nm) 0.1201 0.1168 ε.sub.||(1 kHz) 6.1 6.6 ε.sub.⊥(1 kHz) 2.8 2.9 Δε(1 kHz) 3.3 3.7 ε.sub.av.(1 kHz) 3.9 4.3 γ.sub.1/mPa .Math. s 93 t.b.d. k.sub.11/pN 15.6 t.b.d. k.sub.33/pN 16.5 t.b.d. ε.sub.⊥/Δε 0.84 t.b.d. γ.sub.1/k.sub.11* 5.96 t.b.d. V.sub.0/V 2.29 t.b.d. Remarks: all values (except clearing point) at 20° C., *[mPa .Math. s/pN] and t.b.d.: to be determined.

Comparative Example D-0

(237) The following mixture (CE-D-0) is prepared and investigated.

(238) TABLE-US-00049 Mixture CE-D-0 Composition Compound Concentration/ No. Abbreviation % by weight Physical properties  1 CC-3-V 28.0 T(N, I) = 105.0° C.  2 CC-3-V1 7.0 n.sub.e(20° C., 589 nm) = t.b.d.  3 CCP-V-1 14.0 Δn(20° C., 589 nm) = t.b.d.  4 CCP-V2-1 9.0 ε.sub.||(20° C., 1 kHz) = t.b.d.  5 CCVC-3-V 6.0 ε.sub.⊥(20° C., 1 kHz) = t.b.d.  6 PP-1-2V1 8.0 Δε(20° C., 1 kHz) = t.b.d.  7 PGP-1-2V 5.0 ε.sub.av.(20° C., 1 kHz) = t.b.d.  8 PGP-2-2V 8.0 γ.sub.1(20° C.) = t.b.d. mPa .Math. s  9 PPGU-3-F 0.5 k.sub.11(20° C.) = t.b.d. pN 10 CDUQU-3-F 7.5 k.sub.33(20° C.) = t.b.d. pN 11 DGUQU-4-F 2.5 V.sub.0(20° C.) = t.b.d. V 12 PGUQU-3-F 4.0 V.sub.10(20° C.) = t.b.d. V Σ 100.0 ε.sub.⊥/Δε = t.b.d. γ.sub.1/ k.sub.11 = t.b.d. *

(239) This comparative mixture, mixture D-0, has a high clearing point and is characterized a moderately good transmission in an FFS display and shows an at best acceptable short response time.

(240) To this mixture, mixture D-0, 0.04% of the compound of the formula

(241) ##STR00285##
wherein n is 3, are added. The resultant mixture is called mixture D. It has a clearing point of 105° C., just like the host mixture D-0.

(242) TABLE-US-00050 TABLE 2 Example CE-D D-1 D-2 Composition Cpd. None CCS-4-T CCS-4-T c(Cpd.)/% 0.0 5.0 10.0 c(CE-D)/% 100.0 95.0 90.0 Properties T(N, I)/° C. 105.0 105.0 105.5