专利摘要:
ZHDKKRISTASHCHSKY DIELECTRIC for electro-optical devices, content. 3-8 liquid crystal components, including liquid crystal compounds selected from the classes of azoxybenzenes, bife-. NSH10B, phenylcyclohexanes, cyclohexylcyclohexanes, benzoic acid esters, cyclohexanecarboxylic acid esters, phenyldioxanes, Schiff and diketone base, and liquid crystal compounds with a high transition temperature in an isotropic liquid, which is used to increase the flow rate, in order to improve the temperature, due to the case, it is not necessary to apply a, отлич,, с 1-3 compounds of the general formula (1) Ft R - trans-4-n-pentylcyclohexyl or tr are used for liquid crystal compounds with a high transition temperature to an isotropic liquid ns-4-n-propylcyclohexyl, or R - trans-4-n-pentiltsiklogeko. R is trans-4-methylcyclohexyl, trans-4-n-propylcyclohexy forces, trans-4-n-hexylcyclohexyl when, CO or RR - trns-4-n-propylcyclohexyl, trans-4-n-propylcyclohexen-1 -yl, -trans-4-n-penti.gggicyclohexyl: en-1-yl R-trans-4-n-propylcyclohexen-1-yl was added with the following corre sponding gi mono, May,%: Liquid crystal chesky compounds 67-90 ni (In Compounds of formula M1 (1) The rest is up to 100
公开号:SU1055336A3
申请号:SU803223405
申请日:1980-12-04
公开日:1983-11-15
发明作者:Айденшинк Рудольф;Поль Людвиг;Ремер Михаэль;Дель Пино Фернандо
申请人:Мерк Патент Гмбх (Фирма);
IPC主号:
专利说明:

The invention relates to liquid crystal dielectrics intended for use in electrical information display and information processing systems, in particular S in display panels of automobiles.  Liquid crystal dielectrics for electro-optical devices are known, including liquid crystal compounds selected from the class of azoxy compounds, Schiff bases, bc phenyls, benzoic acid esters, and derivatives of phenylcyclohexanes.  The mentioned crystal-crystalline dielectrics possess a temperature range of the nematic mesophase (-10) (+71) ° C and a viscosity of 24-55 cP at 20 ° C 1.  The disadvantages of these materials are the rather narrow temperature range of the nematic mesophase and, in particular, the temperature of transition to an isotropic liquid is not high enough.  Closest to the invention is a liquid crystal dielectric for electro-optical devices including liquid crystal compounds, for example, from the classes of azoxy benzenes, biphenyls, phenyl cyclohexanes, cyclohexyl cyclohexanes, esters of benzoic acids, etc. , and crystalline compounds with a high transition temperature into an isotropic liquid, in which 4-cyano-4- (trans-4-n-apkylcyclohexyl) biphenyls are used in an amount of 12-26 wt.% as liquid-crystalline substances with a high transition temperature to isotropic liquid. %  These liquid crystal dielectrics.  ki have a temperature range of the nematic mesophase (-10) - (+ 100) C and a viscosity of 21-37 cP at 2.  The specified materials. characterize, but the tacles are not wide enough, the temporal range of nematic mesophases. The chain of the invention is an extension of the temperature range of the existence of the nematic mesophase.  This goal is achieved by the fact that in a liquid crystal dielectric for electro-optical devices containing 3-8 liquid crystal components, including liquid crystal compounds selected from the class.  co-azoxybenzenes, biphenyls, phenyl cyclohexanes, cyclohexylcyclohexanes, benzoic esters, cyclohexanecarboxylic esters,. phenyldioxanes, Schiff bases and diketones, and liquid crystal compounds with a high transition temperature into an isotropic liquid, as liquid crystal compounds with a high transition temperature into an isotropic liquid 1Л: use 1-3 compounds of the general formula (t): where R trans-4-n- pentylcyclohexyl or trans-4-n-propylcyclohexyl, trans-4-n-pentylcyclohexyl, trans-4-methylcyclohexyl, trans-4-n-propylcyclohexyl, trans-4-n-hexylcycj 2 logex, with n 2, or - trans-4 -n-propylcyclohexyl, trans-4-n-propylcyclohexen-1-yl, trans-4-n- pentylcyclohexy R sen-1-yl, R2trans-4-n-propSh1Ciclog of exen-1-sh1 with n 1, with the following ratio of components, weight. %: Liquid-crystalline compounds 67-90 Compounds of formula (I) Else to yr Examples A to G illustrate the preparation of partially hydrogenated oligo-1,4-phenyls of formula (1), where m.  square  - melting point, t. etc. - the temperature at which the P liquid crystal compound enters an isotropic liquid, and so on. kip  - boiling point i. PRI me R A.  a) To a solution of 230 g of (trans-4-n-propylcyclohexyl) benzene in 750 ml of carbon tetrachloride is added dropwise in the presence of 15 g of iron shavings and with stirring 160 g of bromine at such a rate that the temperature of the mixture does not rise above .  The reaction mixture is then boiled for 10 minutes, filtered and subjected to fractional distillation.  After distilling off the solvent under reduced pressure, 163 g of 4- (trans-A-i-pro-11-cyclohexyl) bromobenzene are recovered, T. kip  130135 ° C at 0.1 Torr.  b) To a solution of the Grignard reagent prepared from 31 g of 4- (trans-4-n propylcyclohexyl) -bromobenzene and 3 g of magnesium shavings in 100 ml of tetrahydrofuran is added dropwise at room temperature and stirring a solution of 18 g 4-n-propylcyclohexanone in 30 m of tetrahydrofuran. Then hydrolysis is carried out with a 10% aqueous solution of ammonium chloride, the organic phase is separated, washed twice with 50 ml of water, and dried. over sodium sulfate and evaporated.  The residue was diluted with 300 MP of ethanol and the resulting solution was subjected to hydrogenation in the presence of 4 g of palladium on carbon (5% Pd) for 48 hours at room temperature.  After completion of the hydrogenation, the catalyst is filtered off, the solvent is distilled off, the residue is dissolved in 50 ml of dimethyl sulfoxide and solidified to obtain a 1 st solution for 16 hours with no access of moisture and in the presence of 7 g of tert. -butyl potassium.  After cooling, the reaction mixture was poured into 300 ml of ice-water, and extraction was carried out twice with 100 ml portions of dichloromethane.  the extracts are washed with 100 ml of water, dried on calcium chloride and evaporated.  The resulting 1,4-bis- (trans-4-n-propylcyclohexyl) benzene is recrystallized (from ethanol.  Yield 19 g, t. square  t. etc.  .  PRI me R B.  a) Following Example A (and conducting bromination of 4- (trans-4-n-pentylcyclohexnl) -biphenyl.  After carbon tetrachloride is distilled off, the portions of the crystals are crystallized as 4- (trans-4-n-pentocyclohexyl) -4-bromophenyl as a crystalline mass are recrystallized from ethanol.  T.  square  , t etc.  .  .  b) According to Example A (b), the reaction between 4-methylcyclohexane and the Grignard reagent solution was obtained, from 38.5 g of 4-trans-4-n-pentyl-letexyl) -4-bromobiphenyl and 3 g of magnesium in 200 MP tetrahydrofuran.  After hydrolysis, hydrogenation and isomerization, carried out by the method of Example A (b), after recrystallization from ethanol, 4- {trans-4-n-pentyl 64 pz clohexyl) {trans-4-methylcyclohexyl) -biphenyl is obtained.  T, pl.  , t  etc.  ,, The following method of preparation of the compound is obtained in a very convenient way; 4- (trans-4-n-pentylcyclohexyl) -j- (trans-4-n-propylcyclohexyl) -biphenyl; 4- (trans-4-npentylcyclohexyl) -4- (trans-4-n-hexylcyclohexyl) 7bifekil, t. square  , | t.  etc.  240 C; 4,4-bis- (trans-4-n-prop-1-cyclohexyl) -bifeiil, m. square  , t  etc.  308 ° C; 4,4-bis- (trans-4-n-pen or cyclohexyl) -biphenyl, t. square  43 ° C, t.  etc.  300 ° C.  Example B.  A solution of 24 g of I, 4-dibromobenzene in 30 ml of tetrahydrofuran is slowly added dropwise with stirring to 48 g of magnesium shavings in 50 ml of tetrahydrofuran.  Then the reaction mixture was boiled for 2 hours and, after cooling, it was added dropwise with stirring with a solution of 28 g of 4-n-proshschikloheksanon in 40 ml of tetrahydrofuran.  Stirring is continued for another 2 hours at 60 ° C, after which hydrolysis is carried out by adding 1 l of 5% hydrochloric acid to the mixture dropwise.  At the end of the hydrolysis from the reaction mixture, extraction was carried out three times with diethyl ether, the total amount of which was 600 ml.  Extracts with water and evaporated (at the end under reduced pressure). The syrupy residue is dissolved in 90 ml of acetone, the resulting solution is mixed with 5 g of p-toluenesulfonic acid and refluxed for 4 hours. Then, the reaction mixture is cooled to -5 ° C, and the 1,4-bis (4-n-proprocyclohexene-1-yl) -benzene crystalline precipitate is filtered off and recrystallized from isoproxy alcohol.  Yield 17.6 g, t. square  42 ° C, t.  etc.  .  PRI me R G.  A solution of 31 g of 4- (AI: pentylcyclohexen-1-yl) -bromobenzene in 50 ml of tetrahydrofuran is slowly added dropwise with stirring to 24 g of magnesium shavings in 50 ml of tetrahydrofuran.  The reaction mixture is then boiled for 2 hours and, after cooling, is mixed, added dropwise, with a solution of 14 g of 4-n-propylcyclohexanone in 20 ml of tetrahydrofuran.  Stirring is continued for another 2 hours at 60 ° C, after which hydrolysis is carried out by adding 500 ml of a 5% aqueous solution of hydrochloric acid to the reaction mixture.  After completion of hydrolysis from the reaction mixture, extraction is carried out four times with diethyl ether.  The total amount of ether added is 800 ml. The extracts are washed with water and evaporated (by the end under reduced pressure). The syrupy residue is dissolved in 90 ml of acetone and the resulting solution is boiled with 5 g of p-toluenesulfonic acid for 4 hours under reflux.  Then the reaction mixture is cooled to -5 ° C. A precipitating crystalline precipitate of 1- (4-n-pentylcyclohexen-1-yl) (4N-propanecyclohexen-1-W1) -benzene is filtered off and recrystallized from isopropyl alcohol.  Output 23.6 g.  The final product is a colorless crystals with a t. square  35 ° C and t. etc.  141 ° C.  Examples 1-17 illustrate the production of dielectrics according to the invention by known methods.  Usually, the components taken in a predetermined ratio are placed in a vessel, heated to a temperature 5-10 ° C above the transition temperature to an isotropic liquid, mixed and cooled.  In this case, a ready-to-use liquid crystal dielectric is obtained.  In another embodiment, the solutions are first mixed in a suitable organic solvent, for example acetone, chorophore or methanol, taken in an appropriate amount of components, and then, after thorough mixing, the solvent is removed, for example, from.  they are chased under reduced pressure and get ready for use; liquid crystal dielectric.  Example 1, a) Limestone dielectric, consisting of, weight. %: 4-n-butyl-4-methoxy-azoxybenzene 33.3; 4-ethyl-methoxy-azoxybenzene 16.7; 4- (trans-4-n-pentylcyclohexyl) 50.0, has a temperature at which it is clear, 64 G, threshold voltage in a twisted nematic cell at 40 s 1.7 V.  Temperature dependence of threshold voltage 10.5 mV / ° C.  b) A dielectric consisting of an 86% mixture of Example 1a and 14% 1 4- (trans 4-n-pentylcyclohexyl) -V- {trans 4-nhexylcyclohexyl) -biphenyl has a temperature at which it becomes transparent, the threshold eg In a twisted nematic cell of 1.9 V at 40 ° C, the dependence of the threshold voltage on temperature for it is only 4.7 MB / OC.  Example 2  a) Dielectric consisting of, weight. %: 4- (trans-4-ethylcyclohexyl) -benzonitrile 12; 4 (trans-4-n-butsh1cyclohexyl) -benzonitrile 23; 4-ethyl-4-cyano-biphenyl 14} 4-n-propyloxy-4-cyano-bfeiyl 10; trans-4-n-propylcyclohexyl ester, 4- (trans-4-ethylcyclohexn1) benzoic acid 20; trans-4-n-pro-cyclo-cyclohexyl ester 4- (trans-4-n-butylcyclohexyl) -benzoic acid 21 has t. square  -5 ° C, t. etc.  68 ° C, the threshold voltage in a twisted nematic cell is 1.52 Vcr 40 ° C, and the temperature dependence of the threshold voltage is 6.0.  b) A dielectric consisting of 90% of the mixture of Example 2a and 10% of 4- (trans-4-n-pentylcyclohexyl) (trans-4-n-hexg silcyclohexyl) -biphenyl, has m.  square  , t etc.  threshold the voltage in the swirling nematic cell I, 74 V at 40 ° C and the temperature dependence of the threshold voltage 3.0 mV / ° C.  Example  a) Dielectric, composed of, weight. %: 4- (trans-4-n-propylcyclohexyl) -benzonitrile 24; 4 (trans-4-n-pentylcyclohexyl) -benzonitrile 36; 4- (trans-4-n-heptylcyclohexyl) -benzonitrile 25; 4- (trans-4-npentylcyclohexyl) - -cyan-biphenyl 15, has T. Ш1.  -6 ° С, t.  etc.  72 ° C, the threshold voltage in a swirling nematic cell of 1.7 V at and the temperature dependence of the threshold voltage of 10.0 mV / ° C.  b) A dielectric consisting of a 90% mixture of the example of Pro and 10%. 4,4-bis-. trans4-n-pentylcyclohexyl) -biphenyl, has t. square  -7C, t. etc.  88 ° C, the threshold voltage in a twisted nematic cell is 2.0 V at 40 ° C, and the temperature dependence of the threshold voltage is only 7.5.  PRI me R 4.  The dielectric consisting of, weight. %: 4-n-pentylethylamine anisic acid ester 28; 4-n-pro; 4-n-gexanoyloxybenzoic acid sylphenyl ester 22; 4- (trans-4-nbutylcyclohexyl) benzoic acid 20; 4-n-propylcyclohexyl ester; 4- (trans-4-n-shshccyclohexyl) ethylbenzene 19; 4- (trans-4-n-pentylcyclohexyl) (trans-4-n-propylcyclohexyl) -biphenyl 11, has t. gsh  -7C, t.  etc.  70 ° C, a viscosity of 35–10 P with a dielectric anisotropy of –0.2.  It can be successfully used for the manufacture of indicator elements operating in a dynamic scattering circuit.  PRI m e r 5.  The dielectric consisting of, weight. %: 4- {trans-4-n-penti-cyclohexyl) -benzonitrile 23; 4 (trans-4-n-prop1 Cyclohexyl) -benzonitrile 17; 4- (trans-4-n-propylcyclohexyl) phenetol 16; 4- (trans4-n-propylcyclohexyl) -I-n-butyloxybenzene 12; 4- (trans-4-n-pentylcycpohexyl) - -ethylbiferal 22; 4 (trans-4-n-propylcyclohexyl) -l (trais-4-n-pentylcyclohexyl) -biphenyl 10, has t. square  -20s, tons, etc.  85 ° С, viscosity 1910lIaC with dielectric and schzotropy + 6.0, according to I, the horn voltage in a swirled nonmatical cell is 2.3 V - and the temperature dependence of the threshold voltage is only 8 mV / ®С.  For account of its viscosity and wide temperature range of the existence of the nematic phase, it can be successfully used for the indicator elements of trucks.  EXAMPLE 6, Dielectric consisting of, weight. %: 4- (trans-4-n-propyl-cyclohexyl) -1 -n-butyryloxybenzene 4- (trans-4-n-propyl-cyclohexyl) -phenetol 21; 4- (trans-4-n-propyncycyclohexyl) -1-n-butyloxybenzene 18; 4 (trans-4-n-propylcyclohexyl) (trais-4-n-pentylcyclohexyl) -biphenyl 12, is able to exist in the nematic phase in the temperature range (-10) - (+59) s, has a Pas viscosity at and dielectric anisotropy –0.59.  It can be used with particular success to produce indicator elements with short switching times and relatively low threshold voltages operating on the principle of dynamic dissipation.  Example 7  The dielectric consisting of, weight. %: 4- (trais-4-i-and-mild) clohexyl) -benzonitrile 21; 4 (trans-4t-sh oxycyclohexyl) -ben-, zonitrile 14; 4- (trans-4-n-propylcyclohexyl) - phenetol 16; 4- (trans-A propshiklogeloksil) -Gnn-butyloxybey sol 12; 4- (trans-4-n-pentylcyclohexyl) - -ethylbiphenyl 22; 4- (trans-4-npentylcyclohexyl) - -cyaiobiphenyl 5; 4- (trans-A-n-pentylcyclohexyl) (trans-4-n-propylcyclohexyl) -biphenyl. 10 is able to exist in the imatic phase in the temperature range (-: 20) - (+93) ° C, has a viscosity of 2210 PaS at, dielectric anisotropy - "- 5.7 and a threshold voltage of 2.3 V.  It can be used with particular success in the indicator elements of trucks.  PRI me R 8.  The dielectric is a weight. %: 4- (trans-4-n-butylcyclohexyl) -benzonitrile 20; 4- (trans4-n-pentilcyclohexane) -benzonitril 18; 4-n-butyl-4-cyanbiphenyl 17; 4-ethyl-4 cyanbiphenyl 13; 4-n-yl) 4- {trans-4-n-propyl-cyclohexyl) benzoic acid 12; 4- (trans-4-n-pen.  tylcyclohexyl) (trans-4-n-propylschlohexyl) -biphenyl 10; 4- (trans-4n-n eHfjtn cycle of oh ek forces) - 4-3 tyl biphenyl 10, is able to exist in the chemical phase in the temperature range (r) j- (+84) s, has a viscosity of 3 x 10 , the dielectric anisotropy is +10, the threshold voltage is I, 5 V at 20 ° C, and the temperature dependence of the threshold voltage is only 4.  It can be successfully used for the manufacture of indicator elements with a large information density based on nematic swirling cells, which act as matrix indicator elements in multiplexed mode.  Example 9.  The dielectric consisting of, weight. %: 4- (trans-4-n-propanoxy-cyclohexyl) -benzonitrile 20; 4- (trans-n-butylcyclohexyl) -benzonitrile 46; 4- (trans-4-n-pentylcyclohexyl) -beisonitrile 22; 4- (trans-4-n-pentylcyclohexyl) -4 ethylbiphenyl 25; 4- (trans4 n-propylcyclohexyl) ethylbenzene 7; 4- (trans-4-n-peitylcyclohexn1) (trans-4-1g-propy1cyclohexy) -biphenyl 10, is able to exist in the nematic phase in the temperature range (-15) - (+85) ° С, has a viscosity of 21 -10 Pa.  with at 20 ° C, dizlektriches-; This anisotropy is +7.5 and the threshold voltage B at 20 s with a temperature dependence of approximately 7.0 MVA.  Example 10  A dielectric consisting of %: 4- (trans-4-ethylcyl1-hexyl) -benzonitrile 16; 4- (trans-4-n-.  propylcyclohexyl) -benzonitrile 22 j - (trans-4-n-butylcyclohexyl} -ben zonitrile 17; 4-. (trans-4-n-pentylnc lehexyl) -benzonitrile 27; 4- (trans4-n-peitylcyclohexyl) -ethylbiphenyl 8; 4- (trans-4-n-peitylcyclohexyl) -4- (trans-4-n-propylcyclohexyl) -biphenyl 10, is able to exist in the nematic phase in the temperature range.  (-10) - (+ 66) ° С, has a viscosity of 2310 Pa s at 20 ° С and a dielectric aimsoTporotro +9.7 and a threshold voltage in a twisted nematic cell of 1.6 V.  Indicator elements with such a dielectric can, for example, be used in portable computing devices.  .  Example P.  Dielectric sos TOYASH1IY of, weight. %: trans-2 - (- cyanophenyl) -5 p-propyl-1, 3-dioxane 13; Trans-2- (4-cyanophenyl) -5-n-butyl-1,3 dioxane 18; 4-ethoxyphenyl trans-4-n-propylcyclohexanecarboxylic cyblot 17; transt - (4-ethoxyphenyl) 1-4-n-propellant Clohexane 23; 4- (trans-A-n-pentylcyclohexyl) (trans-4-methylcyclohexyl) -biphenyl 13; 4- (tryns-4-n-pentylcyclohexyl) L- (trans-4-n-propyl 1 Cyclohexyl) -beeffel 11; 4,4-bis- (trans-4-n-benzyl cloxyl) -biphenyl 5, forms a non-mathematical phase in the temperature range (-6) - (+105) ° С, has a viscosity of 22-10 Pas and dielectric Which anisotropy is +9.2.  Example 12  Dielectric, consisting of, weight. %: 4- (trans-4-n-propylcyclohexyl) -benzonitrile 23; 4 (trans-4-n-butylcyclohexyl) -benzonitrile 18; 4- (trans-4-n-propylcyclohexyl) phenetol 24; 4,4-bis- (trans 4-n-propylcyclohexyl) -biphenyl 6; 4 (trans-4-n-pentylcyclohexyl) -4 (trans-4-methylcyclohexyl) -biphenyl 12; 4- (trans-4-n-pentylcyclohexyl) 4- (trans-4-n-propylcyclohexyl) -biphenyl 12; 4,4-bis- (trans-4-n-pentyl cyclohexyl) -biphenyl 5 forms non-mathematical. the phase in the temperature range () - (+ 112) С, has a viscosity of 21.3. “Yu Pa-s at. and dielectric anisotropy +4.8.  Example 13  The dielectric consisting of, weight. (trans-4-n-propylcyclohexyl) phenetol 10; 4-methoxybenzoic acid 4-npropylphenyl ester 10 ;.  4-n-pentylphenyl ester with 4-methoxybenzoic acid 20; N (p-methoxybenzylidene) - "- nbutylaniline 23; N- (p-ethoxybenzylidene) -4-n-butyl1 Ilin 12; 4- (trans-4-npropylcyclohexyl) benzoic acid 10; 4-n-butyl2-cyanophenyl ester; 4- (trans-4-n-pentylcyclohexane strength) -V- (trans-4-n-propylcyclohexyl) -fefcil 10; 4- (trans-4-n-pentylcyclohexyl) -4-ethylphenyl 5,.  forms a nematic phase in the temperature range (-25) - (+ 84) С, has a viscosity of 4610 Pa s with and a dielectric anisotropy of -0.6.  Example 14  The dielectric consisting of, weight. %: 4- (trans-4-n-propylcyclohexyl) -benzonitrile 13; trans1- (4-fluorophenyl) -n-propylcyclohexane 10; trap-G - (4-ethylphenyl) -npropylcyclohexane 20; 4- (trans 4-npropylcyclohexyl) -phenetol- 10; 4 (trans-4-n-pentylcyclohexyl) -t-ipi ananbiphenyl 9 ;.  4- (trans-4-n-pentylcyclohexyl) - -ethylbiphenyl 20; 5- (trans-4-n-propylcyclohexyl) -biphenyl 10; 4- (4-trans-n-Shhiscyclohexyl) -phenyl ester 4- (trans-n-pentylcyclohexane) -carboxylic acid 9 forms a nematic phase in the temperature range (-10) - (+84) C, has a viscosity of 10 Pa- c and d} r electric anisotropy + 4.4.  Example 15  Dielectric consisting of, weight. %: trans-1- (4-ethoxyphosl) -4-y-propylcyclohexane 15; trans-4-n-propylcyclohexane 10 ;; 4- (trans4 n pentylcyclohexyl) -4-ethylbiphenyl 20; 4- (trans-4-n-pentilcyclohexyl) 4- (trans-4-n-propyl cyclohexn1) -biphenyl 5; 4methoxybenzoic acid 4-n-pentylphenyl ester 18; 4-n-butyl-2-cyano-phenyl ester, 4- (trans4-n-propylcyclohexyl) benzoic acid 22; 1- 4-ran-4-n-pentyl-1CHl-1 | -phenyl -pentane-1,3-dione IO, forms a nematic phase in the temperature range t-ZO) (+89) C, has a viscosity of 45- with and a dielectric anisotr -0.6 opium.  Example 16  The dielectric consisting of, weight. %: 4- (trans-4-propylcyclohexyl) -benzonitrile 19; 4- (trans4-n-pentylcyclohexyl) -benzonitrile 18; trans-1- (trans-4-n-butycrylcyclohexyl) 4-cg1oxyclohexane 23; 4- (trans-4-n-pentylcyclohexyl) -4-Gyrc-4-n-ylcyccyclohexyl) -biphenyl 5; Trans-4-n-pentylcyclohexane) carboxylic acid 4-n-pentylphenyl ester;
Trans-4-n-propylcyclohexane carboxylic acid 16-ethoxyphenyl ester 16; forms a nematic phase in the temperature range (-10) -. + 60 ° C, has a viscosity of 2410 5 Pa-s with and a dielectric anisotropy of +9.8.
Example 17. A dielectric consisting of, in wt.%: 4- (trans-4-n-propylcyclohexyl) -benzonitr1 17; 4- (trans-3-n-pentshchik Logeksil) benzonitrile 23; 4-cyan-4-n-pentylbiphenyl 28 J, 4-bis- (4-n-prop1-tcyclohexen-1-yl) -benzene 9i 1- (4-n-pentylcycpohexen-1-yl) -4- (4-n -propylcyclohexen-1-yl) -benzene 8; 1 "4bis- (grains-4-n-propylcyclohexane 1) benzene 15., forms the nematic phase in the temperature range (-8) - (+ 68) С and has a viscosity of 2210 Pa s at,
npe; uiaraehaae liquid crystal dielectrics have a wider temperature range of the nematic mesophase (-20) - (+ 112) C at the same time low viscosity values (19-23 cP) and a low temperature dependence of the threshold voltage of the twist effect (up to 3).
权利要求:
Claims (2)
[1]
LIQUID CRYSTAL DIELECTRIC for electro-optical devices containing 3-8 liquid crystalline components, including liquid crystalline compounds selected from the classes of azoxybenzenes, biphenyls, phenylcyclohexanes, cyclohexylcyclohexanes, benzoic acid esters, high temperature cyclohexanecarboxylic esters, phenyldioxydioxides, transition phenoxydioxanes, dicycloxydioxanes into an isotropic liquid, characterized in that, in order to expand the temperature range of the existence of non-mother mesophase, as liquid crystal compounds with a high transition temperature c. isotropic liquid using 1-3 compounds of General formula (1)
1 b where R = R d
[2]
2 SSh1 '. .
R is trans-4-methylcyclohexyl ; trans-4-n-propylcyclohexyl, trans-4-n-hexylcyclo-B * loghexyl at n = 2, or R = R - trans-4-n-propylcyclohexyl, trans-4-n-propylcyclo-
1 loghexen-1-yl, or R is trans-4-n-pentylcyclohexen-1-yl ^ r2 _ trans-4-n-propylcyclohexen-1-yl at n = 1 in the following ratio of components, May. 7 „:
Liquid Crystal Compounds 67-90
The compounds of formula (1)
The rest is up to 100
SU <„, 1055336
类似技术:
公开号 | 公开日 | 专利标题
SU1055336A3|1983-11-15|Liquid-crystal dielectrical material
US4545922A|1985-10-08|Liquid crystalline fluorine-containing cyclohexylbiphenyls and dielectrics and electro-optical display elements based thereon
US4620938A|1986-11-04|Hydroterphenyls
US4797228A|1989-01-10|Cyclohexane derivative and liquid crystal composition containing same
DE3237367C2|1991-11-28|
DE3335550C2|1992-02-27|
US4505837A|1985-03-19|Liquid crystalline phenylcyclohexene derivatives
EP0062470B1|1984-08-15|Liquid crystal benzene derivatives
EP0316715B1|1992-06-03|Cyclohexane derivatives
US4439340A|1984-03-27|Cyano-mono-or diphenylbicyclohexane derivatives
US4820443A|1989-04-11|Cyclohexane derivative and liquid crystal composition containing the same
US4477369A|1984-10-16|New high temperature liquid-crystalline substances consisting of 4 or 5 six-member-rings and liquid-crystalline compositions containing same
US4325830A|1982-04-20|Three ring dioxane liquid crystalline compounds
EP0099099B1|1987-04-08|High temperature liquid crystal substances having four rings and liquid crystal compositions containing the same
US4548731A|1985-10-22|2,4-Difluorobenzene derivatives
DE3150312A1|1982-07-22|DECALINE, METHOD FOR THE PRODUCTION AND USE THEREOF
EP0458176B1|1995-08-02|Bicyclohexyl derivatives
US4434073A|1984-02-28|Perhydrophenanthrene derivatives, their preparation, and their use in liquid-crystalline dielectrics and electro-optical display elements
WO1991016291A1|1991-10-31|Phenyl cyclohexanes and liquid crystalline medium
US5468421A|1995-11-21|Cyclohexane derivative and liquid crystal composition containing the same
EP0588291B1|1996-03-27|2-Fluorobenzonitrile derivative
JP3772351B2|2006-05-10|Bicyclohexane-4-one derivative
JPH1143450A|1999-02-16|New alkenylbiphenyl derivative
JP2829438B2|1998-11-25|3-halogeno-4-bicyclohexylbenzotrifluoride derivative
KR840000444B1|1984-04-07|Composition of liquid crystal of partially hydrogenated oligo-1,4-phenylenes containing
同族专利:
公开号 | 公开日
SG72483G|1984-08-03|
CA1148981A|1983-06-28|
DE2948836A1|1981-06-11|
DE3064444D1|1983-09-01|
EP0030277B1|1983-07-27|
AT4309T|1983-08-15|
JPS6246527B2|1987-10-02|
HK37184A|1984-05-11|
US4331552A|1982-05-25|
DD155002A5|1982-05-05|
JPS56103120A|1981-08-18|
EP0030277A1|1981-06-17|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题

US2263448A|1938-09-15|1941-11-18|Dow Chemical Co|Poly-cyclohexyl-diphenyls|
FR2207758B1|1972-11-09|1977-09-09|United Kingdom Government|
GB1433130A|1972-11-09|1976-04-22|Secr Defence|Substituted biphenyl and polyphenyl compounds and liquid crystalmaterials and devices containing them|
DE2548360C2|1975-10-29|1983-12-08|Merck Patent Gmbh, 6100 Darmstadt|Liquid crystalline materials with reduced viscosity|
NL7701750A|1976-02-26|1977-08-30|Hoffmann La Roche|MIXTURES OF LIQUID CRYSTALS.|
DE2636684C3|1976-08-14|1980-06-19|Merck Patent Gmbh, 6100 Darmstadt|Phenylcyclohexane derivatives and their use in liquid-crystalline dielectrics|
DE2701591C3|1977-01-15|1979-12-20|Merck Patent Gmbh, 6100 Darmstadt|Hexahydroterphenyl derivatives and their use in liquid crystalline dielectrics|
DE2702598C2|1977-01-22|1984-10-25|Merck Patent Gmbh, 6100 Darmstadt|Cyclohexylcyclohexanes and dielectrics containing them|
US4198130A|1977-06-03|1980-04-15|Hoffmann-La Roche Inc.|Liquid crystal mixtures|
CA1106406A|1977-11-21|1981-08-04|Takashi Inukai|Liquid crystal compounds|
AT364000B|1978-01-30|1981-09-10|Bbc Brown Boveri & Cie|LIQUID CRYSTAL SUBSTANCE|DE2949080A1|1979-12-06|1981-06-11|Merck Patent Gmbh, 6100 Darmstadt|NAPHTHALINE DERIVATIVES, THESE DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT|
DE3006666A1|1980-02-22|1981-09-17|Merck Patent Gmbh, 6100 Darmstadt|PHENYLCYCLOHEXEN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THE LIQUID CRYSTALINE CONTAINING THEM AND ELECTRO-OPTICAL DISPLAY ELEMENT|
US4405488A|1980-10-09|1983-09-20|Chisso Corporation|Liquid-crystalline halogenobenzene derivatives|
GB2085910B|1980-10-13|1985-05-22|Secr Defence|A liquid crystal composition comprising a mixture of diester and cyclohexane derivative|
DE3042391A1|1980-11-10|1982-06-16|Merck Patent Gmbh, 6100 Darmstadt|FLUORINE CYCLOHEXYLBIPHENYL DERIVATIVES, THESE DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT|
DE3266741D1|1981-03-13|1985-11-14|Secr Defence Brit|Liquid crystal compositions|
US4422951A|1981-04-02|1983-12-27|Chisso Corporation|Liquid crystal benzene derivatives|
DE3117152A1|1981-04-30|1982-11-18|Merck Patent Gmbh, 6100 Darmstadt|"FLUORINE 4,4'-BISBIPHENYL DERIVATIVES, THESE DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT"|
JPS588780A|1981-07-08|1983-01-18|Hitachi Ltd|Liquid crystal composition|
JPS588778A|1981-07-08|1983-01-18|Hitachi Ltd|Liquid crystal composition|
DE3136624A1|1981-09-15|1983-03-31|Merck Patent Gmbh, 6100 Darmstadt|LIQUID CRYSTALLINE HALOGEN COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF, THESE DIELECTRICS CONTAINING THEM AND ELECTRO-OPTICAL DISPLAY ELEMENT|
US4583826A|1981-10-14|1986-04-22|Hoffmann-La Roche Inc.|Phenylethanes|
JPS5896673A|1981-12-04|1983-06-08|Seiko Epson Corp|Liquid crystal composition|
US4528114A|1981-12-18|1985-07-09|Hoffmann-La Roche Inc.|Acetylenes|
JPS58118884A|1982-01-08|1983-07-15|Toshiba Corp|Liquid crystal display element|
US4477369A|1982-01-22|1984-10-16|Chisso Corporation|New high temperature liquid-crystalline substances consisting of 4 or 5 six-member-rings and liquid-crystalline compositions containing same|
DE3211601C2|1982-03-30|1990-04-19|Merck Patent Gmbh, 6100 Darmstadt, De|
JPS58191782A|1982-04-30|1983-11-09|Sharp Corp|Liquid crystal composition|
JPS58208241A|1982-05-28|1983-12-03|Hamasawa Kogyo:Kk|Preparation of 4,4'-bis--biphenyl compound|
JPH0316331B2|1982-06-12|1991-03-05|Chisso Corp|
JPS6124430B2|1982-06-21|1986-06-11|Sharp Kk|
EP0099099B1|1982-07-16|1987-04-08|Chisso Corporation|High temperature liquid crystal substances having four rings and liquid crystal compositions containing the same|
EP0107759B1|1982-08-26|1992-12-16|MERCK PATENT GmbH|Cyclohexane derivatives and their use as components for liquid crystals|
JPS625434B2|1982-08-26|1987-02-04|Chisso Corp|
GB2130231A|1982-10-18|1984-05-31|Tektronix Inc|Liquid crystal materials for use in electro-optical display devices|
JPS6218592B2|1982-12-24|1987-04-23|Fujitsu Ltd|
GB2134110B|1983-01-26|1987-01-14|Secr Defence|Liquid crystal 1-fluorophenyl-2-cyclohexyl-ethanes|
JPH0246027B2|1983-03-02|1990-10-12|Chisso Corp|
EP0122389B1|1983-03-16|1987-08-05|F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft|Liquid crystal components having an alkenyl chain|
JPH0349959B2|1983-05-31|1991-07-31|Sharp Kk|
DE3321373C2|1983-06-14|1990-08-09|Merck Patent Gmbh, 6100 Darmstadt, De|
JPH0359952B2|1983-08-30|1991-09-12|Shaapu Kk|
GB2155465B|1984-01-23|1987-12-31|Dainippon Ink & Chemicals|Tolan-type nematic liquid crystalline compounds|
EP0158252B1|1984-04-07|1988-12-21|MERCK PATENT GmbH|Liquid crystal phase|
EP0168701B1|1984-07-14|1988-11-02|MERCK PATENT GmbH|Tercyclohexyles|
DE3703145A1|1986-03-14|1988-08-18|Merck Patent Gmbh|METHOD FOR PRODUCING TERTIAL ALCOHOLS WITH METAL ORGANIC COMPOUNDS|
US4879061A|1986-09-29|1989-11-07|Crystaloid Electronics Co.|Liquid crystalline materials and method of making same|
US5180519A|1989-03-13|1993-01-19|Chisso Corporation|Alkenyl ether derivative and liquid crystal composition containing the same|
US6117361A|1996-02-29|2000-09-12|Chisso Corp.|Liquid crystal compound having fluorine-substituted 1,4-phenylene moiety, liquid crystal composition and liquid crystal display element|
DE10032346A1|2000-07-04|2002-01-17|Merck Patent Gmbh|Liquid crystal medium, useful for electro-optical purposes, is based on a mixture of polar compounds having positive dielectric anisotropy and contains at least one aryl-cyclohexyl compound|
JPWO2016152405A1|2015-03-26|2017-04-27|Dic株式会社|Liquid crystal compound, liquid crystal composition and display element|
法律状态:
优先权:
申请号 | 申请日 | 专利标题
DE19792948836|DE2948836A1|1979-12-05|1979-12-05|PARTLY HYDRATED OLIGO-1,4-PHENYLENE, ITS CONTAINING DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT|
[返回顶部]