New chiral oxazolidinone cpds. with mesogenic side chain

    公开(公告)号:DE4023493A1

    公开(公告)日:1992-04-30

    申请号:DE4023493

    申请日:1990-07-24

    Applicant: HOECHST AG

    Abstract: New chiral oxazolidin-2-one cpds. with a mesogenic side chain in the 3- or 4-position are of formula (IA) and (IB): where "star" = a chiral centre; (star) = opt. a chiral centre; R1 = opt. branched 1-16C alkyl or 3-16C alkenyl, opt. contg. asymmetrical C atoms, in which one or more non-adjacent -CH2- gps. may be replaced by -O-, -S-, -CO-, -O-CO- and/or -CO-O and one or more H may be replaced by F, Cl, Br or CN; R1-3 R2-3 = H, 1-12C alkyl (in which one -CH2- gp. may be replaced by -O- or -S- and the terminal CH3 gp. may be replaced by CH2OR4, CH2SR4 or CH2CONH2), phenyl or cyclohexyl (opt. substd. by ORT4, F or I); R4 = 1-10C alkyl; j, l and n = O, 1 or 2; k and m = O or 1; k = O if j and/or 1 = O; m = O if n = O, K + 1 + n = 1,2 or 3; A1-3 = phenyl, cyclohexyl, pyrimidin-5-yl,pyrimidin-2-yl, pyrid-2-yl, pyrid-3-yl, pyridazin-3-yl; and A1-2 = also pyazin-2-yl, 1,3,4-thiadiazol-2-yl, 1,3-dioxan-2-yl, 1,3-dioxan-5-yl, 1,3-dithian-2-yl, 1,3-dithian-5-yl, thiazol-5-yl, thien-2-yl, piperazin-2-piperazin-1-yl or thiazol-2-yl; M1-2 = -CO-O-, -O-CO-, -CH2CH2-, -CH=CH-, -CH2O- or -OCH2-; X = -O-CH2-, -CH2-, -CO-O-, -O-CO-, -CH2-O- or -C2H4-. They are prepd. by multistage synthesis, using standard techniques described in the literature.

    Discotic liquid crystals
    5.
    发明专利

    公开(公告)号:DE4307049A1

    公开(公告)日:1994-09-15

    申请号:DE4307049

    申请日:1993-03-08

    Applicant: HOECHST AG

    Abstract: Discotic liquid crystals in which the radicals R to R , independently of one another, can have the following meanings: a) H b) a branched or unbranched alkyl group having 1 to 24 or 3 to 24 carbon atoms respectively, which may also be optically active, in which one or more CH2 groups may be replaced by -O-, -S-, -NH-, -COO-, -CO-, 1,4-cyclohexylene, 1,4-phenylene, which may be mono- or di-fluorine-substituted, -CH=CH-, 2,3-oxiranediyl, -COS-, -CH=N-, -O-N=N-, -N=N- or -C IDENTICAL C-, and in which one or more H atoms may be replaced by fluorine, or a cycloalkyl group having 3 to 6 carbon atoms, c) -OH, -NR2 , -NO2, -F, -Cl, -Br, -CN, -NCO, -OCN or -SCN, where R is an alkyl group having 1 to 6 carbon atoms, with the proviso that 3 to 8 of the substituents R must come from group b and 0 to 4 substituents R must come from group c, are suitable as constituents of displays which utilise the effect of helix deformation.

    7.
    发明专利
    未知

    公开(公告)号:DE3620049A1

    公开(公告)日:1987-12-17

    申请号:DE3620049

    申请日:1986-06-14

    Applicant: HOECHST AG

    Abstract: The novel compounds are chiral esters of alpha -substituted phenylalkanoic acids and mesogenic hydroxy compounds, the symbols in the general formula (I) (I) being defined as follows: MO=molecular radical of a mesogenic hydroxy compound MOH after removal of one H, the radical MO being expressed by the general formula (II) R2-(A1)n1-(B-)n2(A2)n3-O (II) where R2=straight-chain or branched (C1-C12)-alkyl, it being possible for one or two non-adjacent CH2 groups to be replaced by O and/or S atoms, or, if n1=1, also F, Cl, Br, CN or CF3, A1, A2=independently of one another 1,4-phenylene, diazine-2,5-diyl, diazine-3,6-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)octylene, it being possible for these groups also to be at least monosubstituted by F, Cl, Br, CN, CF3 and/or (C1-C12)-alkyl (one or two non-adjacent CH2 groups may be replaced by O and/or S atoms), B=CO-O, O-CO, CH2-CH2, OCH2, CH2O, CH=N, N=CH, N=N, N(O)=N, n1, n2, n3=independently of one another 0, 1 or 2, n1 and n3 not being 0 simultaneously, Y=an electron-attracting substituent, Z=H or an electron-attracting substituent, but not identical with Y, and R1=benzyl or phenyl, it being possible for these groups to be substituted in the aromatic moiety in the same way as A1 and A2, with the exception of the compounds with Z=H, Y=F, Cl or Br, R2=(C1-C11)-alkoxy, A1 and A2=phenyl, n1, and n3=1 and n2=0. The compounds are preferably used in tilted smectic liquid crystal phases, which are converted into ferroelectric liquid crystal phases by these compounds; they show high values of spontaneous polarization.

    Alkyl-oxiranyl-alkyl ester(s) of mesogenic carboxylic acids useful in liquid crystal mixts.

    公开(公告)号:DE4423044A1

    公开(公告)日:1996-01-04

    申请号:DE4423044

    申请日:1994-07-01

    Applicant: HOECHST AG

    Abstract: 1-(3-Alkyloxiran-2-yl)alkyl esters (I) of mesogenic carboxylic acids are new. Pref. (I) are of formula (IA): R = (a) H, CN, F, Cl, -CF3, -CHF2, -CH2F, -OCF3, -OCHF2 or -OCH2F; (b) 1-20C alkyl (opt. with asymmetrical C atom), in which CH2 gp(s). may be replaced by -O-, -S-, -CO-, -CS-, -CH=CH-, -C?=C-, cyclopropan-1,2-diyl, -SiMe2-, 1,4-phenylene (Phe), trans-1,4-cyclohexylene (Cyc) or trans-1,3-cyclopentylene and/r with F, Cl, Br, -OR , -SCN, -OCN or -N3 substit(s).; or (c) (optically active or racemic) gps. of formula (IIA-R): R = linear 1-12 alkyl, in which CH2 gp(s). may be replaced by -O- and/or -CH=CH- without directly linked O atoms; R = H; 1-16C alkyl (opt. with an asymmetrical C atoms), in which 1 or more CH2 gps. may be replaced by -O- and/or -CH=CH-, without directly linked O atoms, and/or with 1 or more F or Cl substit(s).; or R + R = -(CH2)4- or -(CH2)5-; Y = Cl, F or CN; Z = -CO- or -CH2-; M = -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-S-, -S-CO-, -CS-O-, -O-CS-, -S-CS-S-, -O-CS-O-, -S-CO-S-, -CS-, -CH2-O-, -O-CH2-, -CH2-S-, -S-CH2-, -CH=CH- or -C?=C-; A = Phe, pyridin-2,5-diyl (Pyd), naphthalen-2,6-diyl or bicyclo(2.2.2)octan-1,4-diyl, opt. with 1 or more F, Cl and/or CN substit(s).; pyrazin-2,5-diyl (Pyr), pyridazin-3,6-diyl, pyrimidin-2,5-diyl or thiophen-2,5-diyl or thiophen-2,4-diyl, opt. with one F, Cl and/or CN substit.; Cyc, opt. with 1 or 2 CN and/or Me substits.; (1,3,4)-thiadiazol-2,5-diyl; 1,3-dioxan-2,5-diyl (Dio); 1,3-dithian-2,5-diyl; piperazin-1,4- or -2,5-diyl; 1,3-dioxaborinan-2,5-diyl; or a B gp. (sic); a, b, c, d, e, f, g, h, i, k = 0 or 1 but b + d+ f+ h must = at least 2. Also claimed are liquid crystal (LC) mixts. contg. (I), esp. ferroelectric and antiferroelectric LC mixts.

    9.
    发明专利
    未知

    公开(公告)号:DE4001965A1

    公开(公告)日:1991-07-25

    申请号:DE4001965

    申请日:1990-01-24

    Applicant: HOECHST AG

    Abstract: Esters of 2-methylalkanecarboxylic acids which are substituted in the 3-position and of mesogenic alcohols, of the general formula (I) in which: R is, for example, straight-chain or branched alkyl having 1 to 14 C atoms (with or without asymmetric C atom), A , A and A are identical or different and are, for example, 1,4-phenylene in which one or two H atoms can be replaced by F, Cl and/or CN, or trans-1,4-cyclohexylene or pyrimidine-2,5-diyl, M and M are identical or different and are CO-O, O-CO, CH2-O, O-CH2, C IDENTICAL C, CH=CH or CH2-CH2, X is F, Cl or CN, R is straight-chain or branched alkyl having from 1 to 10 C atoms or cycloalkyl having 5 to 8 C atoms, and a is 1, and b, c, d and e are zero or 1 with the proviso that c + e equals 1 or 2, are distinguished by a high stability of their mesophases to UV irradiation and heating. They can be employed advantageously as doping agents in liquid-crystalline mixtures.

    10.
    发明专利
    未知

    公开(公告)号:DE3675136D1

    公开(公告)日:1990-11-29

    申请号:DE3675136

    申请日:1986-09-18

    Applicant: HOECHST AG

    Abstract: The new esters derived from a chiral compound containing two OH groups and at least one mesogenic carboxylic acid which have the general formula (I) (I) in which X1=O-H or O-CO-(C1 to C12)alkyl and X2=O-MC or X1 and X2 denote O-MC independently of each other, where MC is the molecular radical of a mesogenic monocarboxylic acid after splitting off an OH group. The esters or esters substituted in the aromatic part of the phenolic part preferably find application as an admixture intwistable liquid crystal phases in which they produce a temperature compensation and a high degree of twisting.

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