• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Compounds of the formula (I) <IMAGE> wherein X is -R, -OR or -O-CO-R and R is alkyl of 1-12 C-atoms, are useful as liquid crystals or as solvents for measuring n.m.r., u.v. or visible spectra in anisotropic media.
    公开号:SU938745A3
    申请号:SU782569100
    申请日:1978-01-20
    公开日:1982-06-23
    发明作者:Айденшинк Рудольф；КРАУЗЕ Йоахим；Поль Людвиг
    申请人:Мерк Патент Гмбх(Фирма)；
    IPC主号:
    专利说明:

    The invention relates to liquid crystal dielectrics based on nematic liquid crystals with positive dielectric anisotropy, containing, in particular, 5 derivatives of cyclohexycyclohexanes, and can be used in electro-optical indicator devices.
    Known liquid crystal dielectric (ZhD-1) based on I-substituted cyanobiphenyls, which has a wide temperature range for the existence of the nematic phase, chemical stability, relatively low viscosity (40-70 cP) fl J. ts
    Also known is a liquid crystal dielectric (ZhD-2) based on # 1-substituted phenylcyclohexanes, which has improved properties compared to ZhD-1, in particular low viscosity - 20-40 cP G2].
    Odyako-known railway trains have a significant drawback - the magnitude of their optical anisotropy (Ap) is relatively large, for example, for railway-1
    Dp is not less than (+) 0.22, for ZhD-2 Ap it is about (+) 0.13, which does not provide the required angular correlation of contraplaces of indicator elements.
    The aim of the invention is to reduce the optical anisotropy of a liquid crystal dielectric.
    This goal is achieved by using a liquid crystal dielectric, including a nematic liquid crystal with positive dielectric anisotropy, in which from one to four compounds of cyclohexylcyclohexanes of the general formula k —sk are additionally introduced, where R is alkyl, in the following ratio, wt.%:
    Compound of the general formula ’I-83.3
    Nematic liquid crystal with positive dielectric anisotropy
    Rest
    Cyclohexylcyclohexanes of the general formula 1 are characterized by positive values of dielectric anisotropy from (+) 3 to (+) 12, have a low viscosity and have lower than 1 optical anisotropy compared to, for example, L-substituted cyanobiphenidamine and phenylcyclohexanes. Cyclohexylcyclohexanes of general formula J can be used as a valuable component of a liquid crystal dielectric for indicator elements, which reduces the optical anisotropy of the railway, since the low optical anisotropy of the railway provides an extremely small angular dependence of the contrast of the indicator element, and also improves the contrast of indicator elements operating on the guest and nemato effect -cholesteric phase transition.
    In addition to cyclohexanes of the general formula 1, other components of the railway may include the known nematic liquid crystals of the series or cyanobiphenyls, or cyanophenylcyclohexanes, or azoxy compounds, or phenylbenzoates.
    Example 1. A liquid crystal dielectric consisting of 33% by weight of tran-trans-4-n-pentylcyclohexylcyclohexan-4-carbonitrile and 67% by weight of trans-4-n-propyl- (4 * cyanophenyl) cyclohexane is nematic in the temperature range 25 ~ 57 ° C, has a dielectric anisotropy A £ = (+) 8.2 and optical • anisotropy Δ n = (+) 0, Vol.
    In FIG. 1 shows the angular dependence of the contrast K of liquid crystal dielectrics with optical * anisotropy Δη = 0.06; 0.12 and 0.24 for K = 3, where K is the ratio of the intensity of the indicator element under tension and without tension; in FIG. 2 - determination of the angle of view of Phi and c.
    For comparison, the well-known liquid crystal dielectric E-7 of the British company BDH Chemisa2s, consisting of alkyl and alkoxycyanobiphenyls, Δπ of which (+) 0.24, is given. As can be seen from FIG. 1 offered at 50
    938 745 4
    Railway SDP = (+) 0,0b is characterized by a small angular dependence of contrast and corresponds to it .. the largest section of the surface, inside of which the contrast ratio K almost does not change. The worst angular contrast ratio is shown by the well-known railway E-7 with Ln = (+) 0.24.
    From FIG. 1 by extrapolation, the angular contrast dependences can be obtained for the given examples of liquid crystal dielectrics.
    PRI me R 2. Railway, consisting of
    40 wt.% Trans-trans-4-H-pentylcyclohexylcyclohexane-4'-carbonitrile and 60 wt.% 4-n-octyloxy-4 / cyanobiphenyl, has a nematic phase in the range 34-75 ° C, Ab = (+) 9 and dn = = (+) 0.16.
    Example 3 · Railway, consisting of wt.% Trans-trans-4-H-pentylcyclohexylcyclohexane-4 * -carbonitrile, 60 wt.% 4-H ~ butyl-4 / methoxyisoxybenzene and 30 wt.% 4-ethyl-4 '- methaxiazoxybenzene, has a nematic phase in the range of 5 _ 47 ° C, aE = (+) 1.3 and An = (+) 0.0b.
    Π PRI me R 4. Railway, consisting of 44 wt.% 4-I-pentyl-1 - (4-cyanophenyl) -cyclohexane, 33 wt.% 4-h-heptyl-T- (4-cyanophenyl) - cyclohexane, wt.% trans-heptyl-1- (4-cyanophenyl) cyclohexane, 11 wt.% trans, -trans-4-H-pentylcyclohexylcyclohexane-4 / -carbonitrile and 12 wt.% trans-trans-4-Η -heptylcyclohexylcyclohexane-4'-carbonitrile, has a nematic phase in the range of O-62 ° C, d £ = (+) 8.6, viscosity 27 cP at 20 ° C and
    An = (+) 0.11.
    Example 5 · railway, consisting of 15 wt.% Trans-trans-4-M-propylcyclohexylcyclohexane-4-carbonitrile, 16 wt.% Trans-trans-4-I-pentylcyclohexylcyclohexane-4′-carbonitrile and 69 wt.% 4 -k-pentyl-4 * -cyanobiphenyl, has a nematic phase in the range of 6-50 ° C, AE = (+) 9.7, viscosity'33 cP at 20 ° C, ip = (+) 0.18.
    PRI me R 6. The dielectric consisting of 12 wt.% Trans-trans-4-H-propylcyclohexylcyclohexane-4-carbonitrile, 12 wt.% Trans-trans-4-H-pentylcyclohexylcyclohexane-4 | -carbonitrile, 13 wt.% trans-trans-4-Η-heptylcyclohexylcyclohexane-4 '-carbonitrile and 63 wt.% 4-H-pentylphenyl ether of anisic acid, has a nematic phase in the range of 4 ~ 58 ° C, viscosity 40 cP at 20 ° C, ΔΕ = (+) 2.5 and Dp = (+) 0.12. This dielectric is particularly suitable for field effect indicator cells operating in a sealed mode.
    The data of examples 1-6 demonstrate a decrease in the optical anisotropy of iron based on nematic liquid crystals belonging to different classes of organic compounds (biphenyls, phenylbenzates, phenylcyclohexanes, azoxy compounds) when cyclohexylcyclohexanes of the general formula I are introduced into them.
    The data of the following examples show a decrease in the optical anisotropy of the railway with an increase in the content of the cyclohexylcyclohexanes of the general formula I in the railway, but it does not matter to achieve this, add one or more compounds of the general formula I.
    PRI me R 7. Known mixture consisting of 29 wt. 4-M-propyl-4 * cyanophenylcyclohexane, 41 wt. 4-pentyl-‘4 '-dicyanophenylcyclohexane and 30 wt. 4-n-heptyl-4 * -cyanophenylcyclohexane, has an optical anisotropy dn = () 0.12. When cycloIS derivatives are added to this mixture
    938 745 6
    -heptylcyclohexylcyclohexane-4 * -carbonitrile, equal to 0.07. Since the derivatives of cyclohexylcyclohexane of the general formula I have negative diamagnetic anisotropy (DMA), it is possible to fabricate liquid crystal dielectrics with a negative value of DMA, when used in the field-effect indicator elements Significantly reduces the time the indicator element turns off, and also improves the contrast by eliminating cross-modulation by magnetic fields. Such railways consist solely of a compound of general formula I.
    Example 10. Railway, consisting of 36 wt. trans-trans-4-n-propylcyclohexylcyclohexane-4'-carbonitrile, 34 wt. trans-trans-4-y-pentylcyclohexylcyclohexane-4'-carbonitrile and 30 wt. trans-trans-4-n-heptylcyclohexylcyclohexane-4-carbonitrile, has a nematic phase in the range 32-83 ° C, d £ = (+) 3.9, viscosity 30 cP at 35 ° C and optical anisotropy dn = (+) 0, about This dielectric has a negative DMA and for this reason it can be used for the manufacture of indicator elements, hexylcyclohexane dp decreases to (+) 0.10 in the railway, consisting of 19.3 wt. 4-H-propyl-4 / cyanophenylcyclohexane, 27.3 wt. 4-n-pentyl-4 * -cyanophenylcyclohexane, 20 wt. 4-n-heptyl-4 1 -cyanophenylcyclohexane and 33.4 wt. trans-trans-4-H-pentylcyclohexyl cyclohexane-4-carbonitrile.
    PRI me R 8. Optical anisotropy of a mixture consisting of 14.5 wt. 4-H-propyl-4 '-cyanophenylcyclohexane, 20.5 wt. 4-H-pentyl-4'-cyanophenylcyclohexane, 15 wt. 4-heptyl-4 1 -cyanophenylcyclohexane, 27 wt. trans-trans-4-n-pentylcyclohexylcyclohexane-4-carbonitrile and 23 wt. trans-trans-4-H-heptylcyclohexylcyclohexane-4-carbonitrile, equal to 0.09
    PRI me R 9 · Optical anisotropy of a mixture consisting of 16.7 wt. 4-I-pentyl-4 * cyanophenylcyclohexane, 30 wt. trans-trans-4-n-propylcyclohexylcyclohexane-4'-carbonitrile, 28.3 wt. TRANS-TRANS-4-4-pentyl cyclohexylcyclohexane-4 * -carbonitrile and 25 weight trans-trans-4-H in which, through an additional magnetic field of the order of 8 KG, the shutdown time is reduced by approximately 35 2 times.
    PRI me R 11. Railway, consisting of 23 wt. trans-trans-4-n-procylcyclohexylcyclohexane-4'-carbonitrile, wt. trans-trans-4-n-butylcyclohexylcyclohexane-4 / -carbonitrile, wt. trans-trans-4-pentylcyclohexylcyclohexane-4 1 -carbonitrile, 20 wt. trans-trans-4-Η-hexylcyclohexylcyclohexane-4 '-
    -carbonitrile and 18 wt. trans-trans-4-H-heptylcyclohexylcyclohexane-4 * -carbonitrile, has a nematic phase in the range of 10 ~ 75 ° С, Δ f = (+) 3,7, viscosity 27 cP and optical anisotropy 50 tpn = (+) 0 0b. In addition, it has a negative DMA and can be used in indicator elements of the field effect operating in the compressed mode, in which cross modulation is eliminated by means of additional magnetic fields.
    Example 12. If the ID composition as described in Example 11, additionally, 3% optically active 4- (2-methylbutyl) -4 x -cyanobiphenyl and % dichroic azo dye GF-3 (commercial product of the American company General. Electric , are added ), then. get an indicator element with a contrast ratio of K = 10.2. If in a similar way to displace the known railway E-7, then K will be equal to only 6.4.
    As can be seen from the above examples, a liquid crystal dielectric containing cyclohexylcyclohexanes of the general formula I has improved electro-optical characteristics in comparison with the known railway.
    权利要求:
    Claims (2)
    [1]
    Nematic liquid crystal with a positive dielectric. Still anisotropy of cyclohexyl cyclohexanes of general formula 1 is characterized by positive dielectric anisotropy values (from) (+) 3 to (+) 12, have low viscosity and have lower values of optical anisotropy compared to, for example, L, -substituted cyanobiphenylamine and phenylcyclohexanes. Cyclohexylcyclohexanes of general formula 1 can be used as a valuable component of liquid crystal dielectric for indicator elements, reducing the optical anisotropy of railways, because low optical anisotropy of railways provides an extremely small angle dependence of the contrast of the indicator element, and also provides an improvement in the contrast of indicator elements that work on the effect of the guest farm and the nemato-cholesteric phase of the transition. In addition to cyclohexanes of general formula 1, other components of the railway would be known nematic liquid crystals of a series of either cyanobiphenyls, or cyanophenylcyclohexanes, or azoxy compounds, or phenyl benzoates. Example 1 A liquid dielectric consisting of 33% by weight trans-trans-n-pentylcyclohexylcyclohexan-a-carbonitrile and 67% by weight trans-n-propyl- (4-cyano-phenyl) -cyclohexane is nematic in temperature range 25-57 ° С, has dielectric anisotropy Л (+) 8,2 and optical anisotropy Д п (+) О, О. FIG. 1 shows the angular 3aBki contrast of K liquid-crystal dielectrics with optical anisotropy, О; 0.12 and 0.2 d, where K is the ratio of the intensity of the indicator element under voltage and without voltage; in fig. 2 - Determination of the angle of view F For comparison, the well-known E-7 liquid-crystal dielectric of the British firm VON ChemicaZs, consisting of alkyl- and alkoxycyanobiphenyls, Lp of which (+) 0.2, is given As can be seen from FIG. 1, the proposed 4 HDD sdn (+) 0.0b is characterized by a small angular dependence of contrast and corresponds to it. The largest surface area within which the contrast ratio K is almost unchanged. The worst angular contrast ratio shows the well-known E-7 railways with dp (+) 0.24. From FIG. In Fig. 1, the angle dependences of the contrast can be obtained by extrapolation for the given examples of liquid crystal dielectrics. PRI mme R 2. Railway consisting of tO weight. The trans-trans-H-pentylcyclohexylcyclohexane-β-carbonitrile and 60 wt D a-H-octyloxy-cyanobiphenyl have a nematic phase in the range of 3t-75 ° C, (+) 9 and &amp; p (+) 0.1b. Example Railway consisting of 10% by weight of trans-trans-4-H-pentylcyclohexylcyclohexane-4 -carbonitrile, 60 wt. 4-N-butyl-4-methoxy-isobenzene and 30 wt. 4-ethyl-4-metaxyazoxybenzene, has a nematic phase in the range of C, l (+) 1,3 idp (+) 0.0b. PRI me R 4. Railway consisting of kk wt.% -I-pentyl- - (- cyanophenyl) -cyclohexane, 33 wt.% 4-H-heptyl-T- (4-cyanophenyl) -cyclohexane, 11 wt.% Trans-heptyl-1 - (- cyanophenyl) -cyclohexane, 11 wt.% Trans, -trans- -H-peitylcyclohexylcyclohexane -carbonitrile and 12 wt. trans-trans-n-heptylcyclohexylcyclohexane -carbonitrile, has a nematic phase in the range of 0-62 C, A ((-) 8.6, viscosity 27 cP at 20 ° C and Dp (+) 0.11. When measure 5-HD, consisting of 15 wt.% trans-trans-M-propylcyclohexylcyclohexane-4 -carbonitrile, 16 wt .- trans-trans-4-I-pentylcyclohexylcyclohexane-V -carbonitrile and b9 wt.% 4-H -pentyl-4-cyanobiphenyl, has a nematic phase in the range of 6–50 ° C, A (h) 9.7i, viscosity33 cP at Ilp (+) 0.18. EXAMPLE 6 A dielectric consisting of 12 wt.% Trans-trans-4-H-propylcyclohexylcyclohexane-A -carbonitrile, 12 wt.% Trans-trans-H-Penti lcyclohexylcyclohexane -carbonitrile, 13 wt.% trans-trans-H-heptylcyclohexylcyclohexane -carbonitrile and 63 wt.% -I-pentylphenyl ether of anisic acid, has a non-magic phase in the range of t-SS C, the viscosity of CO cP at 20 C, (+) 2.5 IDP (+) 0.12. This dielectric is especially suitable for field effect indicator elements operating in a compressed mode. The data of examples 1-6 demonstrate a decrease in the optical anisotropy of railway on the basis of nematic fluids to sources related to various classes of organic compounds (biphenyls, phenylbenzates, Phenylcyclohexanes, azoxy compounds), when cyclohexylcyclohexanes are introduced into them, are general formulas I, The following examples show a decrease in the optical anisotropy of railways with an increase in the cyclohexylcyclohexanes content of general formula I, while achieving this goal does not matter, add one or more compounds Formula I, Example 7, A mixture of 29% by weight, 4-H-propyl-4-cyanophenylcyclohexane, 1% by weight of pentyl-A-dicyanophenylcyclohexane and 30% by weight of t-H- heptyl-cyano phenylcyclohexane, has an opt cic anisotropy of lp () 0.12. When cyclohexylcyclohexane derivatives are introduced into this mixture, the dp is reduced to (+) 0.10 in the HDD, consisting of 19.3%, -H-propyl-cyanophenylcyclohexane, 27.3 wt. α-i-pentyl-β-cyanophenylcyclohexane, 20 wt.% tH-rentil-β-cyanophenylcyclohexane and 33, i wt.% trans-trans-β-H-pentylcyclohexylcyclohexane-β-carbonitrile, Pr m and me 8 from 1.5 weight, -H-propyl-cyanophenylcyclohexane, 20.5 wt., 4-H-pentyl-β-cyanophenylcyclohexane, 15 wt.% C -heptyl-cyanophenylcyclohexane, 27 wt.% trans-trans-n- pentylcyclohexylcyclohexane -carbonitrile and 23 wt.% trans-trans, -I-heptylcyclohexylcyclohexane--carbonitrile, equal to 0.09P and measure 9. Optical anisotropy mixture consisting of 1b, 7weight, C -p entip-C-cyanophenylcyclohexane, 30 wt. L trans-trans-A-n-propyl cyclohexylcyclohexane -carbonitril, 28.3 wt.% trans-trans- - -penta cyclohexylcyclohexane -carbonitrile and 25 wt., trans-trans- H 5 -heptylcyclohexylcyclohexane -carbonitrile, equal to 0.07 Since the derivatives of cyclohexylcyclohexane of general formula I have negative diamagnetic anisotropy (DND), it is possible to produce liquid-crystal dielectrics with a negative DMA value, which are used in radiation-sensitive elements that are applied to a surface with a surface dielectric, using DMA, when using surface diameters that work with a surface, they are used with negative diameters, and they are used with negative diameters. ety shortened off time of the display element, and uluchshits contrast by eliminating cross modulation magnetic fields. Such HDDs consist solely of a compound of general formula I. Example 10. A HDD consisting of 36 wt. trans-trans-n-propylcyclohexylcyclohexane-carbonitrile, 3 weight. trans-trans-i-pentylcyclohexylcyclohexane -carbonitrile and 30 wt. trans-trans-n-heptylcyclohexylcyclohexane -carbonitrile, has a nematic phase in the range of 32-83 ° C, ye (h-) 3.9. viscosity 30 cP at 35 ° C and optical anisotropy dp (+) 0.06. This dielectric has a negative DMA and for this reason it can be used to manufacture indicator elements in which, by means of an additional magnetic field of the order of 8 KG, the cut-off time is reduced by about 2 times, EXAMPLE 11 , trans-trans-n-procylcyclohexylcyclohexane-4 -carbonitrile, 19 wt.% trans-trans-4-n-butylcyclohexylcyclohexane -carbonitrile, 20 weight,% trans-trans- - pentylcyclohexylcyclohexane-A -carbonitrile, 20 wt. trans-N-hexylcyclohexylcyclohexane-4-carbonitrile and 18 wt, tr ns trans - "- H-carbonitrile geptiltsiklogeksiltsiklogeksan- has a nematic phase in the range 1 0-75 ° C, R f (+) 3, 7, 27 cps viscosity and optical anisotropy dn (+) 0,0b. In addition, it possesses negative DMA and can be used in field effect indicator elements operating in compressed mode, in which cross-modulation is eliminated by means of additional magnetic fields, Example 12, If 6 of the HDD composition of example 11, additionally 3% optically active 4- (2-methylbutyl) - "- cyanobiphenyl and% dichroic azo dye GF-3 (commercial product of the American company General. Electric) are introduced, then. receive an indicator element with a contrast ratio, 2. If in a similar way to mix the known railways E - then K will be equal to only 6 ,. As can be seen from the examples given above, a liquid crystal dielectric containing cyclohexylcyclohexanes of general formula 1 has improved electro-optical characteristics as compared with the known railways. DETAILED DESCRIPTION A liquid dielectric dielectric for electro-optical purposes based on nematic liquid crystals with positive dielectric anisotropy is distinguished by the fact that, in order to reduce the opF90 and anisotropy, it is additionally introduced from one to four compounds of general formula J: where is alkyl, in the following ratio of components, wt.%: Compound of general formula I 10-83,3 Nematic liquid crystal with positive dielectric anisotropy Remaining Sources of information taken into account when 1.bgau examination 6.W. The liquid crystal properties of some neu / mesogenes.J. Phys (Paris), 36, (C1 / 3 /, 339-7, 1975.
    [2]
    2.Patent of the USSR according to application f No. 2510803 / 23-04, cl. From 09 to Z / Z, 1976 (prototype).
    t
    FIG. 2
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19772702598|DE2702598C2|1977-01-22|1977-01-22|Cyclohexylcyclohexanes and dielectrics containing them|
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