NEMATIC LIQUID-CRYSTAL COMPOSITION

Abstract: The invention relates to a nematic liquid-crystal composition especially for active matrix displays with high voltage holding ratio, good low temperature stability and without reversed domains. The nematic liquid-crystal composition is based on terminally and laterally fluorinated compounds, characterized in that it comprises about 8 to 70 % by weight of one or more compounds from group (1) wherein R<1> denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E<1> is (a), (b) or (c), L is H or F and Q is OCF2, OCFH, OCFCl, CF2 or a single bond, about 8 to 60 % by weight of one or more compounds from group (2) wherein R<2> denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E<2> is (d), (e) or (f) and each L is H or F, and/or about 8 to 40 % by weight of one or more compounds from group (3) wherein R<3> denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E<3> is (a), (g) or (h) and Q and L are as defined above, with the proviso that both L are F if E<3> is trans-1,4-cyclohexylene.

Description: Nematic liquid-Crystal composition The invention relates to nematic liquid-crystal compositions based on terminally and laterally fluorinated compounds. These compositions are useful for active and passive matrix application. Active matrix displays (AMD) are highly favored for commer¬ cially interesting displays with a high information content. Such AMDs are used for TV application and also for displays with high information content for automobiles and aeroplanes. AMDs have non-linear electrical switching elements which are integrated at each picture element. As non-linear driving elements thin film transistors (TFT) [Okubo, U., et al., 1982, SID 82 Digest, pp. 40-41] or diodes (e.g.: metal insu¬ lator metal: MIM) [Niwa, K., et al., 1984, SID 84, Digest, pp. 304-307] can be applied. These non-linear driving ele¬ ments allow to use an electro-optical effect with a rather flat electro-optical characteristic if a good viewing angle characteristic can be obtained. So a TN-type LC cell [Schadt, M. and Helfrich, W., 1971, Appl. Phys. Lett., 18, 127] with a twist angle of 90° can be used. To provide the good contrast over a wide viewing angle, operation in the first minimum of transmission [Pohl, L., Eidenschink, R., Pino, F. del., and Weber, G., 1980, German Pat., DBP 30 22 818, and 1981, US Pat. 4 398 803; Pohl, L., Weber, G., Eidenschink, R., Baur, G., and Fehrenbach, W., 1981, Appl. Phys. Lett., 38, 497; Weber, G., Finkenzeller, U., Geelhaar, T., Plach, H.J., Rieger, B., and Pohl, L., 1988, Int. Symp. on Liq. Cryst., Freiburg, to be published in Liq. Crys.] is required. These AMDs are very well suited for TV applications and conse¬ quently are of high commercial interest. For these applica¬ tions some physical properties of the liquid crystals become more important than for passive TN displays. Some of the decisive properties for the performance of an AMD are resis¬ tivity and stability of the liquid crystal [Togashi, S., Sekiguchi, K., Tanabe, H., Yamamoto, E., Sorimachi, K., Kajima, E., Watanabe, H., Shimuzu, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, p. 144 ff, Paris; Stromer, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for Matrix Addressing of Television Liquid Crystal Displays, p. 145 ff, Paris] . In an AMD the non-linear switching elements are addressed in a multiplex scheme. So they charge the electrodes of a pixel in the limited time they are active. Then they become inac¬ tive until they are addressed again in the next cycle. Conse¬ quently the change of the voltage on an activated (charged) pixel is a nondesired but a very decisive feature of such a display. The discharge of a pixel is determined by two fac¬ tors. They are the capacity of the electrodes of the pixel and resistivity of the dielectric material between the elec¬ trodes, namely the liquid crystal. The characteristic time constant of the decay of the voltage at a pixel (RC-time) has to be significantly bigger than the time between two adress- ing cycles (tadr.) . A parameter frequently used to describe the performance of an AMD is the voltage holding ratio HR of a picture element: V (to) + V (to + tadr . ) HR = 2 V (to) As the voltage at a pixie decays exponentially an increase of the holding ratio necessitates liquid crystal materials with exceptionally high resistivities. There are several points of importance for the resistivity of the liquid crystal inside a display, e.g. orientation layers, curing condition of the orientation material. But by no means less important are the electrical properties of the liquid crystal used. Especially the resistivitiy of the liquid crystal in the display determines the magnitude of the volt¬ age drop at the pixel. Recently LC compositions with very good HR values could be obtained by using exclusively fluorinated compounds instead of the conventional LC compositions which are based on cyano compounds. Unfortunately, however, such LC compositions based on fluorinated compounds still pose severe problems. In many cases they tend to have lower pretilt angles than cyano based mixtures and they tend to show smectic phases and/or crystal¬ lization problems at low temperatures and it is also very difficult to realize very low threshold voltages without using cyano compounds. Finally the compositions based on fluorinated compounds show reverse domain phenomena (reverse tilt disclination) in many cases. One reason for this problem may reside in the relatively small surface tilt angle of the compositions compared to cyano LC based compositions. Another reason may also be the influence of the elastic constants and especially the K 22 value. There is thus still a great need for liquid-crystal composi¬ tion having a high resistivity and other suitable material properties for use in AMDs such as a broad nematic mesophase range with an extremely low transition temperature smectic- nematic, no crystallization at low temperatures and being completely free of reverse domain phenomena (reverse tilt disclination) . The invention has for its object to provide a liquid-crystal composition with a very high resistivity which meets also the other demands. Fluorinated compounds generally show a tendency towards lower pretilt angles than cyano compounds. Nevertheless, the present inventors found big differences of pretilt angles between different structures of fluorinated compounds. Some examples are given in the following table 1 which shows that fluorinated LCs can come close to the pretilt angles of cyano LCs. Tablβ 1 Tilt Angles of Various Mixtures *ι Each compound, L-P, is mixed with Mix.X in the ratio of 25:75. *2 This compound is mixed with ZLI-3086 (a sales item of E. Merck Darmstadt, Germany in the ratio of 25:75). *3 Low temp, baking type polyimides from Japan Synthetic Rubbers were used as alignment reagents. *4 Does not contain cyano components and consists of 15 % of PCH-32. 15 % of PCH-53. 20 % of PCH-301, 15 % cf PCH-302, 15 % of PCH-304, 6 % of BCH-32, 6 % of BCH-52, 4 % of CBC-33F and 4 % of CBC-53F. 800 - 6 The structures of fluorinated compounds used in Table 1 It has now been found that a nematic liquid-crystal composi¬ tion based on terminally and laterally fluorinated compounds, characterized in that it comprises about 8 to 70 % by weight of one or more compounds from group 1: group 1: wherein R 1 denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E* is -/H V, -CH 2 CH 2 - H V or -/ H VcH 2 CH 2 -, L is H or F and Q is OCF 2 , OCFH, OCFCl, CF 2 or a single bond, about 8 to 60 % by weight of one or more compounds from group 2: L group 2: R 2 - E2-( >-F L wherein R 2 denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E 2 is and each L is H or F, and/or about 8 to 40 % by weight of one or more compounds from group 3: / group 3: K?-( H -E 3 ** o VQ-I wherein R 3 denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E 3 is - f H V, - H V-COO- or -( 0 /-COO- and Q and L are as defined above, with the proviso that both L are F if E 3 is trans-l,4-cyclohexylene, is highly suited for AMD application. Very high RC time values can be obtained in AMDs. These compositions also show a reduced viscosity, allow operation in AMDs in the first minimum of transmission, do not exhibit any crystallization at —30 °C and are free of reverse domain problems (reverse tilt disclination) . The latter being due to the very specific selection of fluorinated compounds which makes it possible to achieve fairly high pretilt angles. Such compositions preferably contain two, three or four compounds from group 1. Preferred compositions comprise more than 12 % by weight of one or more compounds from group 1. The compounds from groups 1 to 3 are known from the European Patent Applns. 0 387 032 and 0 280 902, the European Patents 0 051 738 and 0 125 653, the International Patent Application WO 89/02884 and USP 4,302,352, USP 4,710,315 and USP 4,419,264 or can be prepared in analogy to known compounds. Preferred compositions comprise simultaneously one or more compounds from each of groups la and lb: group la: group lb: Preferably the compositions comprise one or more compounds from group 2 which are selected from the following formulae: Preferably the compositions comprise one or more compounds from group 3 which are selective from the formula 3a to 3f: 3e Preferred compounds from group 1 are those wherein L = F and Q = single bond (= subgroup 1') . However, compositions are especially preferred which contain also compounds from group 1 wherein Q is 0CF 2 , OCFH, OCFCl or CF 2 and L is H or F (= subgroup 1") . In subgroup 1" Q is preferably OCF 2 or CF 2 , OCF 2 being especially preferred. The weight ratio of components from subgroup 1' and subgroup 1" is preferably > 1. Espe¬ cially preferred are compositions with subgroup 1'/sub¬ group 1" > 2:1. Of course also compositions are of particular importance which are mainly or even exclusively based on subgroup 1' components. Also preferred are compositions being based on subgroup 1' components which comprise simultaneously one or more compounds from each of groups la and lb. Preferred compositions also comprise one or more compounds from group 0 having two rings: group 0: R° -<E> *E0-< 0 >-Q-Ξ where R° denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E° is -(CH 2 ) 4 -, -(CH 2 ) 2 -, -CO-O- or a single bond an L and Q are as defined in group 1. Preferably E° is -(CH 2 ) 2 or a single bond, Q is a single bond and one of L is H and the other L is H or F. The compositions according to this invention preferably comprise 30 to 60 % by weight and especially 35 to 55 % by weight of components from group 1. The preferred weight percent ranges for the other groups (if present) are as follows: group 0 5 to 30 %, especially 10 to 25 % group 2 12 to 40 %, especially 15 to 25 % group 3 12 to 30 %, especially 15 to 25 % Preferably the components from groups 1, 2 and 3 from the basis of the claimed compositions and constitute at least 60 % (preferably at least 75 %) by weigh of the compositions. It is, however, also possible to use besides components from groups 0 to 3 also other LC components in smaller percentages for fine-tuning the claimed compositions. From many experimental investigations it also resulted that the most efficient compounds from group 2 are those of the formula These components are preferably used in an amount of 18 to 30 % by weight. Higher amounts are possible but do not fur¬ ther improve the "reverse domain" behavior. The preparation of the compositions according to the inven¬ tion is effected in the conventional manner. In general, the desired amount of the components which is used in the smaller amount is dissolved in the componentns which constitutes the main constituent, preferably at elevated temperature. If this temperature is chosen to be above the clear point of the main constituent, the completeness of the process of dissolving can be observed particularly easily. However, it is also possible to mix solutions of the compo¬ nents in a suitable organic solvent, for example acetone, chloroform or methanol, and to remove the solvent after thorough mixing, for example by distillation under reduced pressure. It is self-evident that with this method it must be ensured that the solvent does not introduce any contaminants or undesirable dopants. By means of suitable additives the liquid crystal phases according to the invention can be modified in such a way that they can be used in any hitherto disclosed kind of AMD. For the tilt angle measurement, we used crystal rotation method. Cell gap of all test cells used in this work was around 50 μm. Test cells were cells made of Soda lime + ITO by DNT with Polyimide orientation layer (Nissan Chemicals SE-150) . Before tilt angle measurement, all test cells were heated up 20 minutes at 120 °C after filling LC mixtures as the isotropic treatment. The examples below serve to illustrate the invention without limiting it. In the examples, the melting point and clear point of a liquid crystal substance are given in degrees Celsius. The percentages are by weight. Example 1 . A liquid-crystal composition consisting of 11 % of trans-l-p-fluorophenyl-4-n-pentylcyclohexane, 11 % of trans-l-p-fluorophenyl-4-n-hexylcyclohexane, 14 % of l-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane, 14 % of l-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane, 7 % of l-[trans-4-(trans-4-n-propylcyclohexyl)-cyclohexyl]- 2-(p-fluorophenyl)-ethane, 7 % of l-[trans-4-(trans-4-n-pentylcyclohexyl)-cyclohexyl]- 2-(p-fluorophenyl)-ethane, 10 % of 4'-(trans-4-n-propylcyclohexyl)-3,4-difluoro- biphenyl, 10 % of 4'-(trans-4-n-pentylcyclohexyl)-3,4-difluoro- bipheny1, 8 % of p-fluorophenyl trans-4-(trans-4-propylcyclohexyl)- cyclohexane carboxylate and 8 % of p-fluorophenyl trans-4-(trans-4-pentylcyclohexyl)- cyclohexane carboxylate shows a clearing point of 91° and a birefringence Δn of 0.0871. This composition can be stored at -30° without crys¬ tallization, shows a high resistivity in the order of 10 13 Ω-cm or more and is well suited for AMDs without reverse domain phenomena (tilt angle 4.7°) . Example 2 A liquid crystal composition consisting of 8 % of trans-l-p-fluorophenyl-4-n-pentylcyclohexane, 8 % of trans-l-p-fluorophenyl-4-n-hexylcyclohexane, 5 % of p-fluorophenyl-trans-4-(trans-4-propylcyclohexyl)- cyclohexane carboxylate, 5 % of p-fluorophenyl-trans-4-(trans-4-pentylcyclohexyl)- cyclohexane carboxylate, 1 % of 4'-(trans-4-propylcyclohexyl)-3,4-difluorobiphenyl, 1 % of 4'-(trans-4-pentylcyclohexyl)-3,4-difluorobiphenyl, 6 % of p-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 5 % of p-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 5 % of p-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 5 % of p-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 3 % of l-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane, 2 % of l-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane, 3 % of l-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-2- (p-fluorophenyl)-ethane and 3 % of l-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-2- (p-fluorophenyl)-ethane shows a clearing point of 98° and a birefringence of 0.0917. This composition can be stored at -30° without crystalliza¬ tion, shows a high resistivity in the order of 10 13 Ω-cm and is well suited for AMD's without reverse domain phenomena (tilt angle 4.2°) . Example 3 A liquid crystal composition consisting of 11 % of trans-l-p-fluorophenyl-4-n-pentylcyclohexane, 10 % of trans-l-p-fluorophenyl-4-n-hexylcyclohexane, 10 % of p-fluorophenyl-trans-4-(trans-4-propylcyclohexyl)- cyclohexane carboxylate, 10 % of p-fluorophenyl-trans-4-(trans-4-pentylcyclohexyl)- cyclohexane carboxylate, 11 % of 4'-(trans-4-propylcyclohexyl)-3,4-difluorobiphenyl, li % of 4'-(trans-4-pentylcyclohexyl)-3,4-difluorobiphenyl, 3 % of p-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 3 % of p-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 3 % of p-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 3 % of p-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 13 % of l-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane and 12 % of l-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane shows a clearing point of 93° and a birefringence of 0.0899. This composition can be stored at -30° without crystalliza¬ tion, shows a high resistivity in the order of 10 13 Ω-cm and is well suited for AMD's without reverse domain phenomena (tilt angle 4.2°) . Example 4 A liquid crystal composition consisting of 6 % of trans-1-p-fluorophenyl-4-n-pentylcyclohexane, 8 % of trans-l-p-fluorophenyl-4-n-hexylcyclohexane, 4 % of trans-l-p-fluorophenyl-4-n-heptylcyclohexane, 1 % of 4'-(trans-4-propylcyclohexyl)-3,4-difluorobiphenyi, 1 % of 4'-(trans-4-pentylcyclohexyl)-3,4-difluorobiphenyl, 6 % of p-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 6 % of p-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 6 % of p-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 6 % of p-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 3 % of l-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane. 13 % of l-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-2- (3,4-difluorophenyl)-ethane, 5 % of l-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-2- (p-fluorophenyl)-ethane and 5 % of l-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-2- (p-fluorophenyl)-ethane shows a clearing point of 90° and a birefringence of 0.0900. This composition can be stored at -30° without crystalliza¬ tion, shows a high resistivity in the order of 10 13 Ω-cm and is well suited for AMD's without reverse domain phenomena (tilt angle 3.9°) . Example 5 A liquid crystal composition consisting of 10 % of trans-l-p-fluorophenyl-4-n-pentylcyclohexane, 8 % of trans-l-p-fluorophenyl-4-n-hexylcyclohexane, 6 % of trans-l-p-fluorophenyl-4-n-heptylcyclohexane, 5 % of p-trifluoromethoxyphenyl-trans-4-(trans-4-propyl- cyclohexyl)-cyclohexane carboxylate, 5 % of p-trifluoromethoxyphenyl-trans-4-(trans-4-pentyl- cyclohexyl)-cyclohexane carboxylate, 12 % of 4'-(trans-4-propylcyclohexyl)-3,4-difluorobiphenyl, 10 % of 4'-(trans-4-pentylcyclohexyl)-3,4-difluorobiphenyl, 8 % of p-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 2 % of ρ-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 7 % of p-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene. 11 % of p-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 2 % of 4,4'-bis-(trans-4-propylcyclohexyl)-2-fluorobiphenyl, 2 % of 4,4'-bis-(trans-4-pentylcyclohexyl)-2-fluorobiphenyl and 2 % of 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propylcyclo- hexyl)2-fluorobiphenyl shows a clearing point of 96° and a birefringence of 0.094. This composition can be stored at -30° without crystalliza¬ tion, shows a high resistivity in the order of 10 13 Ω-cm and is well suited for AMD's without reverse domain phenomena (tilt angle 4.2°) . Example 6 A liquid crystal composition consisting of 10 % of trans-l-p-fluorophenyl-4-n-pentylcyclohexane, 8 % of trans-l-p-fluorophenyl-4-n-hexylcyclohexane, 6 % of trans-l-p-fluorophenyl-4-n-heptylcyclohexane, 5 % of 3,4-difluorophenyl-(trans-4-propylcyclohexyl- ethyl)-benzoate, 5 % of 3,4-difluorophenyl-(trans-4-pent lcyclohexyl- ethyl)-benzoate, 2 % of 4'-(trans-4-propylcyclohexyl)-3, -difluorobiphenyl, 0 % of 4'-(trans-4-pentylcyclohexyl)-3,4-difluorobiphenyl, 8 % of p-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-tri- fluoromethoxybenzene, 12 % of p-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 7 % of p-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-tri fluoromethoxybenzene, 11 % of p-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]- trifluoromethoxybenzene, 2 % of 4,4'-bis-(trans-4-propylcyclohexyl)-2-fluorobiphenyl 2 % of 4,4'-bis-(trans-4-pentylcyclohexyl)-2-fluorobiphenyl and 2 % of 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propylcyclo hexyl)2-fluorobiphenyl shows a clearing point of 98° and a birefringence of 0.101. This composition can be stored at -30° without crystalliza¬ tion, shows a high resistivity in the order of 10 13 Ω-cm and is well suited for AMD's without reverse domain phenomena. In the present application and in the examples below, the structures of the liquid-crystal compounds are indicated by acronyms, with the transformation into chemical formulae taking place in accordance with Tables A and B below. All radicals C n H 2n+ ι are straight-chain alkyl radicals containing or m carbon atoms. The coding in Table B is self-evident. In Table A, only the acronym for the base structure is given. I individual cases, the acronym for the base structure is followed, separated by a hyphen, by a code for the substi- tutents Ri, R 2 , L 1 . L 2 and L 3 : TableA: L i L 2 V- L 2 PYP PYRP H L 2 R1_, ( _°) ~ (° " R2 RI -( H ) ** ^- O ) ** -<2) V - R2 ^ BCH CBC CCH CCP CP CPTP CEPTP R1-(H)- H -C 2 H 4 ECCP CECP EPCH HP L L i1 L IP 2 L-* _ L 2 R1 - )-coo- o}-R2 Ri -d ό/- -R E 2 ME PCH IΛ L2 L i L PDX P P R1-(H -C 2 H 4 BECH EBCH CPC CCEB CCB CCB-n.FX Li L2 ]__ R1 ~(θ)-{0-R 2 B C n H;2n + l-(0)-(θ>- B-n.PX Table B: T15 K3n M3n BCH-n.FX C n H 2n+1 - H -@ ) OC-C m H2 B* Inm C-nm CH 3 CH-* C 2 H 5 -CH-CH 2 -0-(θV O -CN C 2 H 5 -CH-CH 2 - θ -<2-CN C15 CB15 Example 7 S →N [°C] < 40 Clearing point [°C] +103 Viscosity [mπ^s- 1 ] 20 °C 21 Δn (589 nm, 20 °C) e (589 nm, 20 °C) '(10,0,20) [V] V (50,0,20) [V] '(90,0,20) [V] Composition [%] Example 8 S →N [°C] < -40 Clearing point [°C] +99 Viscosity [mm2s-i] 20 °C 23 Δn (589 nm, 20 °C) ^ (589 nm, 20 °C) V (10,0,20) [V] V (50,0,20) [V] (90,0,20) [V] Composition [%] Example 9 S →N [°C] Clearing point [°C] +93 Viscosity [mm 2 s-i] 20 °C 21 Δn (589 nm, 20 °C) +0.0772 ^ (589 nm, 20 °C) 1.5478 V (10,0,20) [ ] 1.82 V(50, 0,20) [ ] 2.16 V (90,0,20) [V] 2.78 Composition [%] : PCH-5F 6.0 CCH-301 6.0 CCH-303 5.0 CCH-501 6.0 CCP-20CF3 6.0 CCP-30CF3 7.0 CCP-40CF3 6.0 CCP-50CF3 7-0 ECCP-3F.F 7.0 ECCP-5F.F 8.0 CUP-3F.F 3.0 CUP-5F.F 4.0 CCP-30CF2.F.F 11.0 CCP-50CF2.F.F 12.0 CP-30CF3 7.0 Example 10 Clearing point [°C] +102 Viscosity [mm 2 s-i] 20 °C - 14.00 5.00 5.00 5.00 5.00 5.00 5.00 14.00 14.00 5.00 5.00 9.00 9.00 0 -30- Example 11 Clearing point [°C] +102 Viscosity tmm 2 s-i] 20 °C 20 Example 12 Clearing point [°C] +73 Viscosity [mm 2 s-i ] 20 °C - 8.00 8.00 5.00 6.00 6.00 6.00 5.00 5.00 14 .00 13.00 9.00 9.00 0 - 32 - Example 13 Clearing point [°C] 95 Viscosity [mm 2 s-i ] 20 °C - Composition [%] CP-30CF3 10.00 CP-50CF3 10.00 PCH-5F 8.00 PCH-6F 7.00 PCH-7F 6.00 CCP-20CF3 7.00 CCP-30CF3 7 .00 CCP-40CF3 7.00 CCP-50CF3 7.00 ECCP-3F .F 5.00 ECCP-5F.F 5.00 BCH-3F.F 11.00 BCH-5F.F 10.00 Example 14 Clearing point [°C] +93 Viscosity [ m∑s- 1 ] 20 °C - 11.00 10.00 10.00 10.00 11.00 11.00 3.00 3.00 3.00 3.00 13.00 12.00 0 34- Example 15 Clearing point [°C] +100 Viscosity [mm 2 s-i] 20 °C - SUBSTITUTE SHEET -35 Example 16 S ->N [°C] < -40 Clearing point [°C] +100 Viscosity firings- 1 ] 20 °C 19 Viscosity [mπ^s- 1 ] 0 °C 55 Viscosity [ ms~i] -20 °C 276 Viscosity [ιran?s-i] -30 °C 767 Viscosity [mm 2 s- 1 ] -40 °C 2609 6.00 3.00 5.00 9.00 6.00 8.00 9.00 5.00 8.50 8.50 8.50 2.50 SUBSTITUTE SHEET Example 17 S →N [°C] Clearing point [°C] 83 Viscosity [mm 2 s- 1 ] 20 °C - Example 18 S →N [°C] Clearing point [°C] +83 Viscosity [mm2s- 1 ] 20 °C - Examole 19 S →N [°C] Clearing point [°C] +83 Viscosity [mm 2 s-i] 20 °C 18 Viscosity [mm 2 s-i] 0 °C 51 Viscosity [mm 2 s-i] -20 °C 248 Viscosity [mm 2 s-i] -30 °C 693 Viscosity [mm 2 s-^] -40 °C 2515 00 -40 Example 20 S →N [°C] Clearing point [°C] +76 Viscosity [imtfs-i] 20 °C 21 Viscosity [mm2s-ιj 0 °C 64 Δn (589 nm, 20 °C) ri e (589 nm, 20 °C) V{io,0,20) [V] V(50,0,20, [V] V (90,0,20) tV] Composition [%] : SUBSTITUTE SHEET Example 21 S →N [°C] Clearing point [°C] +92 Δn (589 nm, 20 °C) +0.0928 i -e (589 nm, 20 °C) 1.5736 v <5o,o,2θ. [V] 2.02 v (90,o,20) [V] 2.53 Composition [%] : PCH-5F 4.00 PCH-7F 4.00 CCP-20CF3 7.00 CCP-30CF3 7.00 CCP-40CF3 7.00 CCP-50CF3 8.00 ECCP-3F.F 8.00 ECCP-5F.F 8.00 BCH-3F.F.F 14.00 BCH-5F.F.F 13.00 CCP-3F.F.F 9.00 CCP-5F.F.F 9.00 CBC-33F 2.00 0 -42- Exam le 22 8.00 6.00 6.00 7.00 6.00 6.00 8.00 8.00 14.00 13.00 9.00 9.00 Example 24 S →N [°C] Clearing point [°C] +81 Viscosity [mm2s-i] 20 °C 23 Example 25 S →N [°C] Clearing point [°C] +92 +0.0969 1.5684 1.69 2.06 2.55 Composition [%] : 0 - 4*5 Example 26 S →N [°C] Clearing point [°C] +92 Δn (589 nm, 20 °C) +0.0929 n e (589 nm, 20 °C) 1.5694 V (10, 0, 20) [V] 1.80 V (5O, 0,2O) [V] 2.18 V(90, 0,20) [V] 2.66 Composition [%] HP-30CF3 5.00 HP-50CF3 5.00 CP-30CF3 8.00 CP-50CF3 8.00 PCH-5F 8.00 PCH-6F 8.00 PCH-7F 8.00 CCP-20CF3 8.00 CCP-30CF3 8.00 CCP-40CF3 8.00 CCP-50CF3 8 .00 BCH-3F .F 9.00 BCH-5F.F 9.00 SUBSTITUTE SHEET Example 27 S →N [°C] < -40 Clearing point [°C] +105 Viscosity [mπ^s- 1 20 °C 19 Viscosity [mm 2 s- 1 0 °C 57 Viscosity [mπ^s- 1 -20 °C 312 Viscosity [mm 2 s-ι -30 °C 941 Viscosity [mm 2 s- 1 -40 °C 3828 Δn (589 nm, 20 °C) +0.0914 (10,0,20) [V] 2.10 V (50,0,20) [V] 2.55 (90,0,20) [V] 3.15 Composition [%] PCH-5F 7.00 PCH-6F 7.00 PCH-30CF3 8.00 PCH-50CF3 8.00 ECCP-3F 12.00 ECCP-5F 12.00 BCH-3F.F 11.00 BCH-5F.F 11.00 ECCP-3F.F 12.00 ECCP-5F.F 12.00 SUBSTITUTE SHEET 0 Exam le 28 5.00 13.00 7.00 10.00 11.00 10.00 12.00 12.00 12.00 4.00 4.00 Ex m 7.00 7.00 6.00 6.00 4.00 7.00 6.00 6.00 4.00 13.00 11.00 12.00 11.00 0 -50- Example 30 S -→N [°C] Clearing point [°C] +103 Δn (589 nm, 20 °C) +0.0928 ri e (589 nm, 20 °C) 1.5752 V(io,o,20) [V] 2.30 V (50,0,20) [V] 2.70 V (90,0,20) [V] 3.30 Composition [%] : PCH-5F 7.00 PCH-6F 7.00 CP-30CF3 6.00 CP-50CF3 6.00 BCH-3F.F 11.00 BCH-5F.F 11.00 CCP-20CF3 6.00 CCP-30CF3 6.00 CCP-40CF3 4.00 CCP-50CF3 5.00 ECCP-3F.F 10.00 ECCP-5F.F 10.00 ECCP-3F 6.00 ECCP-5F 5.00 51 Example 31 S -→N [°C] Clearing point [°C] +93 +0.0955 1 .5845 2.52 3.08 Composition [%] : PCH-5F 10.00 PCH-6F 9.00 CP-30CF3 5.00 CP-50CF3 5.00 BCH-3F.F 13.00 BCH-5F.F 14.00 HP-30CF3 2.00 BCH-32 2.00 ECCP-3F.F 10.00 ECCP-5F.F 10.00 ECCP-3F 10.00 ECCP-5F 10.00 Example 32 S →N [°C] < -40 Clearing point [°C] 96 Viscosity [mm 2 s-i] 20 °C 15 Viscosity m 2s-i] 0 °C 41 Viscosity [mm s--*] -20 °C 189 Viscosity [mm s-i ] -30 °C 581 Viscosity [mm 2 s-i] -40 °C 1882 10.00 8.00 6.00 CCP-20CF3 8.00 CCP-30CF3 12.00 CCP-40CF3 7.00 CCP-50CF3 11.00 BCH-3F.F 12.00 BCH-5F.F 10.00 CCP-30CF3 5.00 CCP-50CF3 5.00 CBC-33F 2.00 CBC-53F 2.00 CBC-53F 2.00 Example 33 S →N [°C] Clearing point [°C] 96 0.0923 1.5656 1.52 2.33 Composition [%] SUBSTITUTE SHEET Example 34 S →N [°C] Clearing point [°C] +106 Δn (589 nm, 20 °C) +0.0928 He (589 nm, 20 °C) 1.5752 V (10, 0, 20) [V] 2.42 V(50, 0, 20) -V] 2.89 V (90, 0, 20) [V] Composition [%] PCH-5F 7.00 PCH-6F 7.00 CP-30CF3 10.00 CP-50CF3 10.00 BCH-3F.F 11.00 BCH-5F.F 11 .00 CCP-20CF3 3.00 CCP-30CF3 3.00 CCP-40CF3 3.00 CCP-50CF3 3.00 ECCP-3F 6.00 ECCP-5F 6.00 ECCP-3F.F 10.00 ECCP-5F.F 10.00 Example 35 S →N [°C] Clearing point [°C] +103 Δn (589 nm, 20 °C) +0.0932 ^ (589 nm, 20 °C) 1.5731 (10,0,20) [V] 2.11 (50,0,20) [V] 2.52 V (90,0,20) [V] 3.07 Composition [%] PCH-6F 7.00 PCH-7F 6.00 CCP-20CF3 7.00 CCP-30CF3 7.00 CCP-40CF3 7.00 CCP-50CF3 7.00 CP-30CF3 6.00 CP-50CF3 6.00 ECCP-3F.F 13.00 ECCP-5F.F 11.00 BCH-3F.F 12.00 BCH-5F.F 11.00 Example 36 S →N [°C] Clearing point [°C] +100 Δn (589 nm, 20 °C) +0.0924 V (10, 0, 20) [V] 2.06 ' (50, 0, 20) [V] 2.45 V (90, 0,20) [V] 2.96 Composition [%] PCH-6F 7.00 PCH-7F 8.00 CCP-20CF3 7.00 CCP-30CF3 7.00 CCP-40CF3 7.00 CCP-50CF3 7.00 ECCP-3F 5.00 ECCP-5F 3.00 ECCP-3F.F 13.00 ECCP-5F.F 11.00 BCH-3F.F 10.00 BCH-5F.F 4.00 HP-30CF3 6.00 HP-50CF3 5.00 57- Example 37 S →N [°C] < -40 Clearing point [°C] 96 Viscosity [mrr_ 2 s- i ] 20 °C 15 Viscosity [mms- i ] 0 °C 41 Viscosity [mi s- i ] -20 °C 189 Viscosity [mm 2 s-i] -30 °C 581 Viscosity [mm2 S -i] -40 °C 1882 10.00 8.00 6.00 8.00 12.00 7.00 11.00 12.00 10.00 5.00 5.00 2.00 2.00 2.00 Example 38 11.00 11.00 8.00 8.00 8.00 8.00 3.00 3.00 10.00 10.00 10.00 10.00 E 10.00 9.00 4.00 4 .00 13.00 14.00 3.00 11.00 11.00 11.00 10.00 SUBSTITUTE SHEET - 60 - Example 40 S →N [°C] Clearing point [°C] +91 Example 41 S →N [°C] Clearing point [°C] +88 SUBSTITUTE SHEET Example 42 Composition [%] : CP-30CF3 10.00 PCH-5F 9.00 PCH-6F 7.20 PCH-7F 7.20 CCP-20CF3 8.10 CCP-30CF3 8.10 CCP-40CF3 8.10 CCP-50CF3 8.10 ECCP-3F.F 5.40 ECCP-5F.F 5.40 BCH-3F.F 11.70 BCH-5F.F 11.70 - 63 Example 43 S →N [°C] Clearing point [°C] +107 Viscosity [mm2s-i ] 20 °C 18 Viscosity [mm2s-i ] 0 °C 53 Viscosity [mn s-i ] -20 °C 268 Viscosity [mm∑s-i] -30 °C 782 Viscosity [mm2 S -i] -40 °C 3174 Δn (589 nm, 20 °C) +0.0956 (589 nm, 20 °C) 1.5758 (10, 0.20) [V] 2.00 ' (50, 0.20) [V] 2.42 . (90.0.20) [V] 2.97 Composition [%] PCH-5F 6.00 PCH-6F 6.00 CCP-20CF3 5.00 CCP-30CF3 6.00 CCP-40CF3 4.00 CCP-50CF3 5.00 BCH-3F.F 12.00 BCH-5F.F 12.00 ECCP-3F.F 12.00 ECCP-5F.F 12.00 CP-30CF3 10.00 CP-50CF3 10.00 SUBSTITUTESHEET - 64 - Example 44 S →N [°C] Clearing point [°C] +104 Viscosity [mm s-i] 20 °C 18 Viscosity [mm∑s-i] 0 °C 53 Viscosity [inmzs- i ] -20 °C 272 Viscosity [mm 2 s-i] -30 °C 789 Viscosity [mm 2 s-i] -40 °C 3010 6.00 6.00 6.00 5.00 4.00 5.00 12.00 12.00 12.00 12.00 5.00 5.00 5.00 5.00 Example 45 S →N [°C] Clearing point [°C] 109 Δn (589 nm, 20 °C) 0.094 , (589 nm, 20 °C) 1.571 V (10,0,20) [V] 2.18 V (50,0,20) [V] V (90,0,20) [V] Composition [%] CP-30CF3 10.00 CP-50CF3 10.00 PCH-5F 8.00 PCH-6F 6.40 PCH-7F 4.80 CCP-20CF3 6.40 CCP-30CF3 9.60 CCP-40CF3 5.60 CCP-50CF3 8.80 BCH-3F.F 9.60 BCH-5F.F 8.00 ECCP-30CF3 4.00 ECCP-50CF3 4.00 CBC-33F 1.60 CBC-53F 1.60 CBC-55F 1.60 SUBSTITUTE SHEET Example 46 S →N [°C] Clearing point [°C] +100 Δn (589 nm, 20 °C) li e (589 nm, 20 °C) V (10, 0,20) [V] V (50, 0, 20) [V] V, (90,0,20) [V] Composition [%] Example 47 S →N [°C] Clearing point [°C] +101 Δn (589 nm, 20 °C) +0.0942 V (10, 0, 20) [V] 2.15 V (50, 0, 20) [V] 2.56 V (90, 0, 20) [V] 3 .11 Composition [%] PCH-5F 7.00 PCH-6F 7.00 CUP-3F.F 2.00 CCP-20CF3 6.00 CCP-30CF3 6.00 CCP-40CF3 5.00 CCP-50CF3 6.00 BCH-3F.F 10.00 BCH-5F.F 9.00 ECCP-3F.F 11.00 ECCP-5F.F 11.00 CCP-30CF2.F.F 4.00 CCP-50CF2.F.F 3.00 CP-30CF3 5.00 CP-50CF3 5.00 CBC-33F 3.00 Example 48 S →N [°C] Clearing point [°C] 83 Δn (589 nm, 20 °C) 0.093 H e (589 nm, 20 °C) 1.574 V (10,0,20) [V] 1.81 (50,0,20) [V] (90,0,20) [V] Composition [ % ] HP-30CF3 5.00 HP-50CF3 5.00 PCH-5F 9.00 PCH-6F 7.20 PCH-7F 7.20 CCP-20CF3 8.10 CCP-30CF3 8.10 CCP-40CF3 8.10 CCP-50CF3 8.10 ECCP-3F.F 5.40 ECCP-5F.F 5.40 BCH-3F.F 11.70 BCH-5F.F 11.70 Example 49 S →N [°C] Clearing point [°C] 101 Δn (589 nm, 20 °C) (10,0,20) [V] V (50,0,20) [V] V (90,0,20) [V] Composition [%] 0 - 70 - Example 50 S →N [°C] Clearing point [°C] +101 Viscosity [mm2 S -i] 20 °C 17 Viscosity [mm2s-i] 0 °C 50 Viscosity [inm Z s- i ] -20 °C 230 Viscosity [mms-i] -30 °C Smectic Viscosity [m 2s-i] -40 °C - Δn (589 nm, 20 °C) n e (589 nm, 20 °C) V(10,0,20) [V] V (50,0,20) V] V (90,0,20) [V] Composition [%] : - 71 - Example 51 S →N [°C] Clearing point [°C] +102 Viscosity [mm 2 s-i] 20 °C 16 Viscosity [mm∑s- 1 ] 0 °C 47 Viscosity [mm 2 s-i] -20 °C 222 Viscosity [mm 2 s-i] -30 °C 634 Viscosity [mm 2 s- 1 ] -40 °C Sm Δn (589 nm, 20 °C) +0.0876 n* (589 nm, 20 °C) 1.5631 V (10,0,20) [V] 2.10 (1st) V (50,0,20) [V] 2.54 V (90,0,20) [V] 3.11 Composition [%] PCH-5F 8.00 PCH-6F 8.00 CP-3F 5.00 CP-5F 5.00 BCH-3F.F 7.00 BCH-5F.F 7.00 CCP-20CF3 8.00 CCP-30CF3 7.00 CCP-40CF3 7.00 CCP-50CF3 7.00 ECCP-3F.F 9.00 ECCP-5F.F 8.00 CCP-30CF2.F.F 7.00 CCP-50CF2.F.F 7.00 0 - 72 - T„ι 92 °C Δn 0 ,091 Vio 1.50 V tilt angle θ 3.7° T NI 85 °C Δn 0.086 V 10 1.45 V tilt angle θ 3.8° SUBSTITUTE SHEET T KI 88 °C Δn 0.083 tilt angle θ 4 .3° SUBSTITUTE SHEET

Claims: Claim 1. A nematic liquid-crystal composition based on terminally and laterally fluorinated compounds, characterized in that it comprises about 8 to 70 % by weight of one or more compounds from group 1: wherein Ri denotes a straight-chain alkyl group of 2 to 5 carbon atoms, Ei - H VcH 2 CH 2 -, L i H or F and Q is OCF 2 , OCFH, OCFCl, CF 2 or a single bond, about 8 to 60 % by weight of one or more compounds from group 2: group 2: wherein R 2 denotes a straight -chain alkyl group of 2 to and each L is H or F, and/or about 8 to 40 % by weight of one or more compounds from group 3: group 3: wherein R 3 denotes a straight-chain alkyl group of 2 to 5 carbon atoms, E 3 is -( H V*, -( H V-COO- or - 0 V* COO- and Q and L are as defined above, with the proviso that both L are F if E 3 is trans-l,4-cyclohexylene. A nematic liquid-crystal composition according to claim 1, characterized in that it comprises simulta¬ neously one or more compounds from each of groups la and lb: group la: group lb: 800 76 - A nematic liquid-crystal composition according to claim 1 or 2, characterized in that it comprises one or more compounds from group 2 which are of the following formula: A nematic liquid-crystal composition according to one of claims 1 to 3, characterized in that it comprises one or more compounds from group 3 which are selected from the following formulae 3a to 3e: 5. A nematic liquid-crystal composition according to claim 2, characterized in that Q is a single bond and L is F.

Inventors: PLACH HERBERT, RIEGER BERNHARD, SAWADA ATSUSHI, WEBER GEORG, YOSHITAKE HIROKI, PLACH, HERBERT, RIEGER, BERNHARD, SAWADA, ATSUSHI, WEBER, GEORG, YOSHITAKE, HIROKI
Applicants: MERCK PATENT GMBH, MERCK PATENT GESELLSCHAFT MIT BESCHRAENKTER HAFTUNG
Application year: 1992
Main classification: C09K19
IPC codes: C09K19, G02F1