GB2229722A - Liquid crystalline chiral compounds - Google Patents
Liquid crystalline chiral compounds Download PDFInfo
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- GB2229722A GB2229722A GB9006368A GB9006368A GB2229722A GB 2229722 A GB2229722 A GB 2229722A GB 9006368 A GB9006368 A GB 9006368A GB 9006368 A GB9006368 A GB 9006368A GB 2229722 A GB2229722 A GB 2229722A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
- C09K19/2028—Compounds containing at least one asymmetric carbon atom containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Description
1 Mesogenic and promesogenic non-racemic chiral compounds This invention
relates to mesogenic and promesogenic non-racemic chiral compounds for crystalline liquid mixtures, a method of producing and the application of the above-mentioned compounds in optoelectronics and thermography.
Liquid crystals are already known for a relatively large number of applications. A particular role is thereby played by those types of liquid crystals which have a twisted structure. and particularly the twisted nematic phases (cholesterinic liquid crystals) and twisted smectic C-phases (C phases), both of which occur in chiral compounds. Both twisted nematic and also C phases can be used in optoelectronic displays (E. Kaneko: Liquid Crystal TV Displays: Principles and Applications of Liquid Crystal Displays, M Scientific Publ. Tokyo 1987).
Furthermore, twisted nematic compounds (cholesterinic compounds) are used for thermography (H. Kelker, R. Hatz: Handbook of Liquid Crystals, Verlag Chemie Weinheim 1980).
According to the desired field of application, so compounds are required which have quite specific properties. There are no individual substances which come even close to fulfilling the practical demands in terms of temperature range of the mesophases. optical, electro-optical, dielectric or rheological properties. Therefore, in practice, the only mixtures used are those which may consist of up to about 15 different components. The properties of the mixtures depend upon the properties of the components used. In order to achieve optimum adaptation of the mixtures to specific demands, a large number of individual components are required which have the most widely diverse properties. In order to be able to find compounds with altered properties, new classes of substances are constantly being incorporated into liquid crystal chemistry. Particularly in the field of chiral substances, there is still a great need for mesogenic and promesogenic compounds of differing molecular structure.
It is already known (D.M. Walba, H A. Razawi US 4 695 650) to react 4formyl benzoic acid- (4-alkyloxy-phenyl ester) with 2-alkyl ethyn-llithium to produce a prochiral ketone which by means of stoichiometric quantities of alpine borane is reduced to the corresponding chiral hydroxy compounds which then have to be further hydrated in a further synthesizing stage. This method has only very limited application. The enantio selective reduction of prochiral aryl alkyl ketones II with BH3. THF in the presence of the catalyst IIIa was described by Corey et al (J. Am.Chem.Soc. 109, 7925 (1987). However, by reason their low solubility, the prochiral ketones cannot effectively reduced in THF by the method described Corey.
of be by The aim of the invention resides in new mesogenic and promesogenic non- racemic chiral compounds for mixtures for application in optoelectronic components and for thermography.
According to the invention, mesogenic and promesogenic nonracemic chiral compounds to the general formula 1 R 3 Z 2 A3) 4 4) 4 R 11 J -If in which pp q, r, s, t, u 0 or 1 p + q + r + r + s 1 to 3 and t + u = 1 or 2 1 RRCOO- o ROOC- s Halogen, Na- j Sem- j r 3c- 3 3 -Cl, -OH, -OR', -(-Q _1,4-plionyleile-) q_00C -C-IRII CH 3 GLA L j :p 1 (wi.th2:1 rlii.-ist 9) 2 R4 = alkyl chain with 1 to 18 carbon atoms.
C 1 A1 1 A2 1 A3 9 A4 (identical or different) - 1,4-phenylene, 1,4cyclohexylene, one of the rings Al, A2y A3, or A4 also being a benzene ring in which one or more CH groups are replaced by N; Z3 substituted 1,4phenylene; thiadiazol2,5-diyl; 1,4-bicyclo(2,2,2)-octylene; piperidine-1, 4-diyl and Qly Q 2 Y Q 3 9 Q 4 (identical or different) - single bond, -CH20-Y -OCH2-Y -COO-y -OOC-, -CH2CH2-, -C 5 C,, subst. ethylene, CH2CH2C00-1 -OOCCH2CH2- Z1 1 Z3 (identical or different) - halogen, -OCH3, -CH3, -OC2H5y 11 Z2 = halogen, H, -CNy -OCDH2n+11 -CnH2n+l in which n = 3 to 18 and i R2 R' 5 R' ' (identical or different) = straight chain or simply branched alkyl chain with 1 to 18 carbon atoms in which any CH2 group may be substituted by -CH2-phenyl-X- or cyclohexylene-Y-, in R or M' also a CH2 group which may be separated by at least 2 C-atoms from an 0-atom, may be substituted by 0, S -COO-, -HC=CH- R' ' = straight chain or branched alkyl chain with 2 to 5 carbon atoms with X, Y = -COO-, -OOC-2 02 S and C = non-racemic asymmetrical carbon atom.
To the exclusion of the alternative embodiment: pp q, t = OP Q 32 Q4 single bond, A3, A4 = phenylene, R1 = alkyl or alkyloxy, R2 = methyl, R3 OH or ester group.
According to the invention, the compounds to the general formula I are produced by enantio selective reduction of the prochiral ketones to the general formula II with BH3.THF in the presence of 0.2 to 10 parts by quantity as a percentage of one of the chiral catalysts III in THF with the addition of 5 to 90 parts by mass percent of a solutizer such as, for example, toluene. benzene, diglymes, at temperatures of between -10C and +80' and preferably at 200C.
At this stage, the non-racemic chiral benzyl alcohols IV are obtained in virtually quantitative chemical yield and in high optical purity (.66 to 98%). Consequently. these can without further purification operations be converted by known methods (Houben-Weylt Methods of Organic Chemistry) to obtain or to reverse the relative configuration into the compounds to the general formula I.
1 1 (C0) 2' U- R CC) 13 R 11.1 b -CIA (C11.3) 2 11:1 c -CA4,-phenyl R4 CW -GH(C)2 21 'S.
311a 0 4 0 11 Cli, 1-, 1 1,1 (A2,11) 4U-R 2 1-1-C -DH 5 0 11 The compounds according to the invention are chemically and thermally stable and have favourable conversion temperatures. Many of the compounds are themselves crystalline-liquid, all are readily miscible with other liquid crystals and their mixturesand can be added in high concentrations without the clarification point of the liquid crystal being substantially reduced. The addition of even small quantities of the compounds produces the induction of twisted crys ta lline- liquid phases such as N or smectic C.
11 IV r ; k.
Tables 1, 2 3 and 3 show examples of substances according to the invention, together with their conversion temperatures. In the tables: N nematic, N' = cholesterinic phase cr crystalline solid, is - isotropic liquid SA2 SC - smectic phases types A, C (the star denotes a chiral variation) liquid crystalline phase exists liquid crystalline phase does not exist numbers shown between two dots: conversion temperature between these phase numbers in brackets denote monotropic conversions Table 1
Compound 1/3. HO-G 1 1 0 H 17 C0), - G 4 lit 1 -W 11,3 110-cl, H_ 000 OC 10 H 21 1 &J -C)-& G1gi 1 1.9 C r 105 0 C 162 S A 167, 5 in cr 82is cr 56 is or 142 is T 1 1 Table 2
Compound No.
ti 00-C cr 40 is Zj/,Z S 0 C7 9 7 i4-ID) ' Doe 0)-OC8H t) 19 17 CH1 1 214c c-' if 00C CICH 21 L crtg (565) i's cr 24 S 29 Is cr 23 is I'S c liiCOO-C W 40 is CH-A . 1, 1 if. _--- _\ 1 H7 --cfi 2 cox 44-&0w- 0 OC or 2 /7 -, a 1 I-N - r9- H-, 0 %,.ocldw 1.7 -4 I-J cl -&Ol DH21 cal 9 93 5 ar 60 5 c; t119 is 2 /9 /--DOG DCb cl ot 107 5 130 2/10 c 1 Oc p- 1.
c 1 a r 73 5 154-.1.5 ; - Wi 'i 1 - -, - cr 44 is if 2/11 cl] O-C 11 0 00c 00c c11.1 3 -C7- GO 10 21 cr 159 (N 56) is 0 2/12 cl 1 3_ c H or 110,5 G A 128,5 N 134 Is H 19C H -&-OOC -&Doe-&C 10 bl 21 1 c 3.
cr tr33.5c63) 9 A 112 Is 7 H 15 L %,W-G Wc-&ClOH21 r-C )1115) cr 63 ic 11 2/1j G 1.oll 21 U-C 14 00C.1 Ocic c 10H21 1 -&.-& -G- GA 1 cl' 60 ( N 64) is - 2/1(3 2/17 cr 70 10 H-CH(CH 3)2 UH er 3C is Table 3
1 13 141 UOU- 0 OUG Compound E.' VI. HO p V4 3/7 IA 0 cli.
c 3.
CH 3 0 G W 3 Ow- i) - 1.3 0 C 1 1:
1-) 18 212 n-G H rt-C H 13- n-C 8 H 17 on - C, (S H 1.3 0.. n G f.I [1 17 0n-C H 11 17 0- c 11 S 6@. 74- 0 - N is 1.1 4 84 9 96 62 - 57 - 70 - 52 - 66,5 56 melting enthalpy in kJ/mol 43el E30 0 as 9 66 41.3).
0 37,9 - to- Examples of procedures to produce the compounds according to the invention Example 1 (R)-4-(4-n-decylbenzoyloxy)-benzoic decyl)-phenyl ester/ 1/5 acid-/4-(1-hydroxy-n- 2.0 mmol(l.2 g) 4-(4-n-decylbenzoyloxy)-benzoic acid-4-ndecanoyl phenyl ester are dissolved in an Erlenmeyer flask in a mixture of 10 ml absolute toluene. Under agitation and barrier gas, at approx. 0% 0.1 mmol (27.6 g) of the catalyst IIIa was added in 2 ml absolute THF. At 00C2 2.0 mmol BG3. THF dissolved in 10 ml absolute THF, were added to the resultant solution dropwise over a period of 10 mins. After heating to room temperature, agitation continued for one hour and then hydrolysis followed, carried out carefully with 2 ml cold 2 N HCl. After dilution with 50 ml ether, the organic phase is separated off and washed three times with in each case 10 ml 2 N HCl$ with 10 ml saturated NaHC03 solution and with 10 ml water. The ether solution is dried over Na2S04 and the solvent distilled off in a rotary evaporator. Recrystallisation from ethanol delivers the chiral alcohol 1/5 in a chemical yield of 90%.
/,X /22 =+8.9 (c = 2.64; THF) 85% oo 3 79 Phase behaviour: cr 105 Se 119 S 127 is A Example 2 (R)-4-n-oetyloxybenzoic ester 2/1 acid-/4-(1-methoxyethyl)-phenyl 1.0 mmol (0.37 g) (R)-4-n-oetyloxybenzoic acid-/4-(lhydroxy-ethyl) - phenyl ester/ is in 15 ml absolute dioxane blended with 3.0 mmol (0.7 g) freshly precipitated dried A920 and 5.0 mmol (0.71 g) CH3, and shaken at room temperature for 24 hours while light and humidity are excluded. Then the mixture is heated to WC for 8 hours. After the solution has been diluted with 50 ml ether, the residue is extracted and washed twice, each time with 10 ml ether. The solutions are purified and the solvent distilled off in a rotary evaporator. By recrystallising the raw product from methanol, compound 2/1 is obtained with a yield of 80%.
Melting point WC.
Example 3 (R)-4-(4-n-decylbenzoyloxy)-benzoic acid-/4(1-octanoyloxyn-decyl)- phenylester/ 2/14 5.0 mmol (3.07 g) (R)-4-(4-n-decylbenzoyloxy)-benzoic acid/-4- (1-hydroxy- n-decyl) -phenyl ester/ are placed in 20 ml absolute CH2C12. After the addition of 15 mmol (1.52 g) triethyl amine and approx. 20 mg DMAP, 5.0 mmol- (0.81 g) octanoyl chloride are added dropwise over a period of 5 mins. at room temperature, accompanied by agitation. After 6 hours, dilution is carried out with 100 ml ether, followed by three washes with in each case 20 ml 2N HC19 20 ml NaHe03 solution and 10 ml water. The organic phase is dried over Na2S04, the solvent is removed at a rotary evaporator and the raw product obtained is recrystallised from methanol, the pure ester 2/14 being obtained in a yield of 85%.
Melting point: 63'C.
1.
- P1 - Example 4 (S)-4-octyloxybenzoic ester/ 2/7 acid-/4-(1-chloropentyl)-phenyl 2.0 mmol (0.74 g) (R)-4-n-octyloxybenzoic acid-/4-(lhydroxypentyl)-phenyl ester/ are dissolved in 10 mI absolute CC14 and, accompanied by agitation and cooling, added dropwise to a suspension of 2.0 mmol (0.42 g) PC1s in 5 ml absolute CC14 within a period of 10 mins. After 12 hours agitation at 0 to 5'C to the exclusion of atmospheric humidity. the solution is diluted with 10 ml CC14 and filtered to remove -any minimal PC15 residues. At the rotary evaporator, the solvent and the resultant P0C13 are distilled off at about 3CC. Recrystallising the raw product from hexane delivers the compound 2/7 in a yield of 82%.
Melting point: WC.
Example 5 (R)-1-hydroxy ethyl hydrochinone-bis-(4-n-octyloxybenzoate) 3/1 In an Erlenmeyer flask, 2.0 mmol (1.23 g) acetyl hydrochinone-bis-4-noctyloxybenzoate are dissolved in 15 ml absolute THF. With agitation and under barrier gas, at 0% 0.1 mmol (27.6 mg) in (S)-tetrahydro-3,3diphenyl-lmethyl-1H, M-pyrrolo (1.2c) (1,3,2) oxazaborol was added in 2m1 absolute THF. To the resultant solution and accompanied by agitation at 0% 2.0 mmol BH3MF dissolved in 10 ml absolute THF were added dropwise over 10 mins. After heating to room temperature, agitation was continued for 1 hour followed by careful hydrolysis with 2 mI cold 2 N HCl. After dilution with 50 mI ether, the organic 1 A A 1 0 l 4 - js - phase is separated off and washed three times with in each case 10 ml 2 N HCl, with 10 ml saturated Na HC03 solution and with 10 ml water. The ether solution is dried over Na2S04 and the solvent distilled off in a rotary evaporator. Recrystallisation from benzine (clarification point 60 - 85'C supplies compound 3/1 in a yield of 95% of the theory.
/ v /22 578 m +2.53 (c - 3.16; acetone) enantiomeric purity:
1% 71% ep, conversion behaviour: cr 58 N' 84 is Example 6 (S)-i-chloroethyl hydrochinone-bis-(4n-hexyloxybenzoate) 3/5 2.0 mmol (1.12 g) of compound 1/2 are dissolved in 10 ml absolute CC14 and, accompanied by agitation and cooling at 0% added dropwise to a suspension of 2.0 mmol (0.42 g) PC15 in 5 ml absolute CC14 in a period of 10 mins. After 12 hours agitation at 0 to 5'C to the exclusion of atmospheric humidity, the solution is diluted with 10 ml CC14 and filtered to remove any minimal residues of PC15. In the rotary evaporator, the solvent and the resultant P0C13 are distilled off at 30'C. Recrystallising the raw product from benzine (clarification point 60 to 85C) supplies the compound 3/5 in a yield of 80% of the theory.
Conversion behaviour: cr 57 N 88 is Example 7 (R)-1-methoxy ethyl hydrochinone-bis-(4-n-octyloxybenzoate) 3/6 4 f a - i - 1.0 mmol (0.1 g) of compound 1/1 are blended in 15 ml absolute dioxane with 3.0 mmol (0.7 g) freshly precipitated dried A920 and 5.0 mmol (0.71 g) CH31 and, to the exclusion of light and humidity. shaken for 24 hours at room temperature. Then, the mixture is heated to 50C for 8 hours. After the solution has been diluted with 50 ml ether, it is extracted from the residue and the latter is washed twice with in each case 10 ml ether. The solutions are cleansed and the solvent distilled off at the rotary evaporator. By recrystallising the raw product from nhexane, the ether 3/6 is obtained in a yield of 75%.
Conversion behaviour: cr 70 N 86 is e a _Of - Is - Examples by application Example 1 way of more detailed explanation of the By means of a DSC calorimeter, enthalpies W/Pol) were determined:
Compound No. Fusion enthalpy 2/13 34.6 2/16 30.6 2/17 24.2 Example 2 the following fusion For displays based on ferroelectrical 'smectic C-phases (N.A.Clark, S.T. Lagerwall: Appl. Phys. Lett. 36, 899 (1980), mixtures with smectic C- phases are required which can be obtained by chiral induction by means of substances according to the invention from substances which contain non- chiral C-phases. This is demonstrated by the following mixtures.
The mixtures were produced by using the following comparative substance:
N v 1 (11 0 11 2 P-C N' 'JCJ.2"25 3ttbt3t. No. xvi Phase sequence 0,95 er Aa s 17 's /is 0,90 er 418 6 51 S 96,5 is C A 6. c r 40 8 79 S 97 is 0,95 A 0j90 er 50 3 70 S 94.1s c A ,7 0,05 c r A.9 G (11 79 S A 93 is 0,90 er 50 Gj' 64 S 95 Is c A - mola fraction 1 -- er 50 -S---06 - ib Example 3
For displays with twisted nematic coatings and for thermography with liquid crystals, twisted nematic phases are required which can be obtained by chiral induction using substances according to the invention from non-chiral nematic phases. This will be demonstrated from the following mixtures.
The nematic basic mixture Mi 5 has the following composition:
30.2% 4-n-pentyl oxybenzoic acid-4-n-octyl oxyphenyl ester 13.3% 4-nhexyl oxybenzoic acid-4-n-heptyl oxyphenyl ester 34.5% hexyl benzoic acid4-n-butyl oxyphenyl ester 22.0% mathoxy benzoic acid-4-n-hexyl oxyphenyl ester At room temperature, the mixture is nematic and has a clarification point of 71'C.
Substances according to the invention were added to this Mi 5. The basic nematic mixture became cholesterinic and the depressions of the clarification temperature shown in the following Table resulted.
Added compound % 5 10 20 30 No.
1/1 2 3 7 10 2/1 3 6 12 18 2/5 5 9 19 28 2/6 2 5 11 17 2/17 5 10 21 32 1 1 1 & f Example 4
BY admixing the substances according to the invention to other liquid crystalline substances, chiral liquid crystal phases with a twisted structure are obtained. This is demonstrated by the following juxtaposition in which a nonchiral substance A is provided with additives of various substances according to the invention.
Comparative substance A:
lN c 0 H 17 o-(()) N OC 12 11 25 4 SW = 50 2 WA /00 1 Conversions or 50 S c a 6 ES A 93 Is v A or 5 L GI 11 is c A 314- 95 3/1 95 3 /S 95 96 f3185 95 78 95 -49 49 0 3/4 90 S /0 47,5. 71 03 4 9 49 91 0 D 6 1 9 95 - - 0 a 1 4
Claims (5)
1 C.B 1 1 4 19 R4 = alkyl chain with 1 to 18 carbon atoms Alq A29 A3p A4 (equal or different) - 1,4-phenylene; 1,4cyclohexylene in which one of the rings A1 p A2t A3, or A4 may also be a benzene ring in which one or more CH groups are substituted by N; Z3 subst. 1,4- phenylene: thiadiazol2,5-diyl; 1,4-bicylo(2,2,2)-oetylene; piperidin-1,4- diyl and Q 1 t Q 2p Q3p Q4 (identical or different) - single bond, - CH -OCH -COO-t -OOC-, -CH CH subst.
20-9 21 2 2-9 -C2--C-o ethylene, -CH2CH2COO-Y -OOCCH2CH2- Z1 $ Z3 (identical or different) - halogen, -OCH3, -CH3, -CN, -OC2H5, H Z2 = halogen, H, -Wp.-OCnH2n+ly -CnH2n+l in which n - 3 to 18 and R$ Re$ M' (identical or different) = straight chain or simply branched alkyl chain with 1 to 18 carbon atoms in which any desired CH2 group may be substituted by -CH2phenyl-X- or cyclohexylene-Y-, in R or M' also a CH2 group which is separated by at least two carbon atoms from an 0 atom, may be replaced by 02 S2 -COO-, -HC=CH- R... = straight chain or branched alkyl chain with 2 to 5 carbon atoms with X$ Y = -COO-p -OOC-1 Ot S and C = non-racemic asymmetric carbon atom, to the exclusion of the variation.
pp q, r = 0 Q37 Q4 - single bond, A3, A4 - phenylene R1 = alkyl or alkoxy, R2 = methyl, R3 - OH or ester group.
2. Compounds to formula I which contain crystalline liquid mixtures, in accordance with claim 1.
3. A method of producing the compounds to the general formula I according to claim 1, characterised in that prochiral ketones to the general formula III 0 f.
l-- 2-0 2 2 3 3 4 A ú0 -) t -(Q A a p- (A cl 1,) r_ (Q A C0 with BH3.THF in suitable mixtures of solvents in the presence of 0.2 to 10 paAs as a percentage of one of the chiral catalysts III T S. T Q 01 11113 II1C P,4 = -co(cnz)2.
R 4- = 11.1A P,4 ---- -cti 2 -CH (CH 3)2_ 111 cl 0 It 9 W < 0 0 1 N=- B C H 3 and of a solutizer such as. for example toluene. benzene, diglymes, at temperatures between -100C and +800C and preferably at 20% are reduced to the chiral non-racemic benzyl alcohols IV l- 1. 1 2 2 a) - (QA4 R, (A 0) p - (A a) q_ _( H-C -OR 13 P.
OH 1 -132 J(C),, 1 44 IV t Z( these being then converted to the chiral non-racemic compounds.
4. The application of the compounds to general formula I according to claim 1 in crystalline liquid mixtures in optoelectronic components, particularly displays based on liquid crystals, and in thermography.
5. Compounds obtained by the process of claim 3.
Published 1990atThePatentC)Mce. State House.8871 High Holborn. IoondonWC1R4TP.Purther copies maybe obtained from The Patent Office Sales Branch, St Mary Cray. Oiptiron, Kent BM 3RD. Printed by MWtlplex techniques It& St Mary Cray, Rent, Con 1187
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD32710589A DD280962A1 (en) | 1989-03-31 | 1989-03-31 | METHOD FOR PRODUCING MESOGENIC AND PROMESOGENIC NONTRACEMIC CHIRAL COMPOUNDS |
| DD32710489A DD280974A1 (en) | 1989-03-31 | 1989-03-31 | APPLICATION OF MESOGENIC AND PROMESOGENIC NONTRACEMIC CHIRAL COMPOUNDS |
| DD32710389A DD282237A5 (en) | 1989-03-31 | 1989-03-31 | MIXTURES OF LATERAL BRANCHED MESOGENIC AND PROMESOGENIC CHIRAL NON-TRACEMIC SUBSTANCES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9006368D0 GB9006368D0 (en) | 1990-05-16 |
| GB2229722A true GB2229722A (en) | 1990-10-03 |
Family
ID=27179929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9006368A Withdrawn GB2229722A (en) | 1989-03-31 | 1990-03-21 | Liquid crystalline chiral compounds |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH02289528A (en) |
| DE (1) | DE4004281A1 (en) |
| FR (1) | FR2645166B3 (en) |
| GB (1) | GB2229722A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0603786A2 (en) * | 1992-12-23 | 1994-06-29 | Hoechst Aktiengesellschaft | Alkyl-substituted hydroquinone derivatives for use in ferro-electric liquid crystal mixtures |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0284371A2 (en) * | 1987-03-23 | 1988-09-28 | Sumitomo Chemical Company, Limited | Novel optically active benzene derivatives, process for producing the same and liquid-crystalline substances containing said derivatives as active ingredient and optical switching elements |
| EP0297745A1 (en) * | 1987-06-10 | 1989-01-04 | Sumitomo Chemical Company, Limited | Optically active ether derivatives, preparation processes therefor, liquid crystal materials and an optical switching element |
-
1990
- 1990-02-13 DE DE19904004281 patent/DE4004281A1/en not_active Withdrawn
- 1990-03-06 FR FR9002785A patent/FR2645166B3/en not_active Expired - Fee Related
- 1990-03-21 GB GB9006368A patent/GB2229722A/en not_active Withdrawn
- 1990-03-30 JP JP8147990A patent/JPH02289528A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0284371A2 (en) * | 1987-03-23 | 1988-09-28 | Sumitomo Chemical Company, Limited | Novel optically active benzene derivatives, process for producing the same and liquid-crystalline substances containing said derivatives as active ingredient and optical switching elements |
| EP0297745A1 (en) * | 1987-06-10 | 1989-01-04 | Sumitomo Chemical Company, Limited | Optically active ether derivatives, preparation processes therefor, liquid crystal materials and an optical switching element |
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts 111 ( * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0603786A2 (en) * | 1992-12-23 | 1994-06-29 | Hoechst Aktiengesellschaft | Alkyl-substituted hydroquinone derivatives for use in ferro-electric liquid crystal mixtures |
| EP0603786A3 (en) * | 1992-12-23 | 1994-08-17 | Hoechst Ag | Alkyl-substituted hydroquinone derivatives for use in ferro-electric liquid crystal mixtures. |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9006368D0 (en) | 1990-05-16 |
| JPH02289528A (en) | 1990-11-29 |
| DE4004281A1 (en) | 1990-10-04 |
| FR2645166A1 (en) | 1990-10-05 |
| FR2645166B3 (en) | 1991-07-12 |
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