• 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:
    The invention relates to liquid crystal dielectrics, in particular, for an electro-optical indicator device, which as components are used in displays based on guest-host effect, twist effect and on dynamic scattering effect. The dielectric contains 62-94 wt.% A derivative of cyclohexane of the general formula 4Rr4-C H -CH- (CH2) j-CRj (CN) - (CHj), where K C2-C is alkyl; Rj kil., And the rest are nematic liquid crystals selected from the group of biphenyl derivatives, cyclohexyl or phenyl 4-substituted esters. benzoic acids. This composition ensures the achievement of a greater negative dielectric anisotropy from; (-) 5.4 to (-) 8.7 and optical anisotropy 0.03-0.07. and S 00 SP O5 with O5 SP cm
    公开号:SU1356965A3
    申请号:SU833633978
    申请日:1983-08-24
    公开日:1987-11-30
    发明作者:Айденшинк Рудольф；Хаас Гюнтер；Поль Лудвиг；Ремер Михаэль；Шойбле Бернхард；Вебер Георг
    申请人:Мерк Патент Гмбх (Фирма)；
    IPC主号:
    专利说明:

    one
    1356965
    This invention relates to a liquid crystal dielectric for electro-optical indicator devices that may be used as components of liquid-crystal dielectrics used in displays based on the twist effect, guest-host effect or dynamic scattering effect.
    This dielectric consists of nematic liquid crystals and 2–5 compounds derived from cyclohexane of the general formula I
    I.
    ate / /.
    where R is alkyl;
    R is alkyl when defined
    the ratio of components The aim of the invention is to achieve greater negative dielectric anisotropy,
    Example 1 illustrates the method for producing these cyclohexane derivatives of general formula I, and examples 2-12 illustrate the use of cyclohexane derivatives in dielectrics for electro-optical devices.
    Example 1: Dissolve 23.3 trans, trans-4-cyano-4-propylcyclohexyl diclohexane and 45.g pentylbromide in 70 ml of toluene, mix with 4.3 g of NaNHj (50% in toluene) and boil for 5 h After the usual treatment, 1-cyano-1-pentyl-cis-4- (trans-4-propyl-cyclohexyl) -cyclohexane is obtained, T д d. 39.5% t.pr. 48.5% yield 66%.
    Similarly, the following compounds are obtained (in brackets the output in% is indicated):
    1.-Cyan-1-ethyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane, Т, „4ГС, т, пр, 100%. (60);
    1-cyano-1-ethyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane, T 41 ° T.c., 30% (56);
    1-cyan-1-propyl-cis-4- (trans-4-- ppctcyclohexyl) -cyclohexane T ,,. 32% t, pr, 13 (62);
    1-cyano-1-propyl-cis-4- (trans-4-buts1 cyclohexyl) -cyclohexane,
     Submarine
    31% t, Ave, 27 ° (65);
    1-cyano-l-propyl-cis-4- (trans-4-pentilcyclohexyl) -cyclohexane, T „,. 32% t, vol, 42% (71);
    0
    1-cyan-1-propyl-cis-4- (trans-4-heptyl cyclohexyl-Jr) -cyclohexane, T „,. 38% m. Ex. 49 ° (61);
    1-cyano-1-isoprog Il-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane, T ,, ,, 73% t, ex, 30 (55);
    1-cyan-1-butyl-cis-4- (trans-4-propyl cyclohexyl) -cyclohexane, 28, t, ex, 28.5 (61);
    1-cyano-I-butyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane, T ,, 9%, etc., 36, (74);
    1-cyan-1-pentyl-cis-4- (trans-5 4-butylcyclohexyl) -cyclohexane, T, d. 8 °, t, ex. 56 (72);
    1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, Tll. 28% t, sp, 63 (74); Q1-cyan-1-pentyl-cis-4- (trans4-heptylcyclohexyl) -cyclic ore xan, m.p., 56 (60);
    1-cyan-1-hexyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 5 TPd. 17% t, sp, 55 (58);
    1-cyano-1-hexyl-cis-4- (trans-4-butylcyclohexn1) -cyclohexane, T „. 30% t, pr, 55 (58);
    1-cyano-1-heptyl cis-4- (trans-Q 4-propylcyclohexyl) -cyclohexane, T „. 22% t, sp, 56 (63);
    1-cyano-1-heptyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane, T ,,. 28% t, pr, 6 G (60);
    1-cyano-1-heptyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, t, ex. 50 ° (56);
    1-cyano-1-octyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, Q t, ol, 50% (70);
    1-cyano-1-nonyl-qi with-4- (tr an with-4-propylcyclohexyl) -cyclohexane, t, ave, 49 (55);
    1-cyan-1-decyl-cis-4- (trans-5 4-propylcyclohexyl) -cyclohexane, T „,. 48% t, ex, 46 ° (56) .;
    Example 2 A mixture of the following constituents (mixture A),%: 1-cyano-1-pentyl-cis-4- (trans-4-Q. propyl cyclohexyl) -cyclohexane 11; 1-cyano-1-heptyl-cis-4- (trans-4-proxy cyclohexyl) -cyclohexane 24; 1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 21; c 1-cyano-1-pentyl-cis-4- (trans-4-pentylcycpohexyl) -cyclohexane 2 1; 1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane 13; 4- (trans-4-pentylcyclohexyl) -4 1 1 C, K. 75 ° C, viscosity
    (trans-4-propylcyclohexyl) -biphenyl 10.
    T. pl.
    67CT, dielectric anisotropy - 7.7, optical anisotropy 0.05,
    Example 3. In 98, parts of mixture A, 2 weight, parts of blue dye 4,8-diamino-1,5-dioxy-2-p-methoxyphenyl-anthraxinone, are dissolved
    Viscosity 67 cSt, dielectric anisotropy 7.7, optical anisotropy 0.05.
    Example 4, Preparing a mixture of
    The following components,%: 1-cy-g 67 CCT, dielectric anisotropy an-1-pentyl-cis-4- (trans-4-propyl- 7.9, optical anisotropy 0.04.
    cyclohexyl) -cyclohexane, 9; 1-cyan Example 8. Prepared
    1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 19; 1-cyan mixture of the following composition,%: 1-cyano-1 - -heptyl-cis-4- (trans-4-propyl cyclogene
    1-propyl-cis-4- (trans-4-pentylcyclo-JQ forces) -cyclohexane, 18; 1-cyan-1-prohex1) cyclohexane, 17; 1-cyano-1 pentyl-cis-4- (trans-4-pentylcyclo-.
    hexyl) -cyclohexane, 17; 1-dian-1propyl-cis-4- (trans-4-heptylcyclohexyl) -diclohexane, 10; 4-ethyl-2 fluoro-4 - (trans-4-pentylcycpohexyl) biphenyl, 28.g
    T..PD. le C, K66 ° C, viscosity 55 cST, dielectric anisotropy - 6.3, optical anisotropy 0.07.
    Example 5. 98 weight. parts of the mixture according to example 4 dissolve 2 wt. portions of the red dye: 1-p-dimethyl amino benzylidene amine o-4-p-cyanophenyl naphthalene. The viscosity is 55 cSt, the dielectric anisotropy is 6.8, the optical anisotropy is 0.07.
    Example 6. A mixture of the following constituents is prepared,%:
    1-cyano-1-pentyl-cis-4- (trans-4-shimcyclohexyl) -cyclohexane, 12;
    1-cyano-1-heptsh-1-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 25;
    1-cyano-1-PROPSH1-CIS-4- (trans-pentil-cyclohexyl) -cyclohexane, 22;
    1-cyano-1-pentsh1-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 22;
    1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane, 13;
    trans- (4-propyl-dichexyl ester a) tr anc-tr an c-4-propylcyclohexylcyclohexane-4-carboxylic acid, 6.
    T. Sh1. -10 ° C. K. 59 ° C, viscosity 69 cST, dielectric anisotropy -8.1, optical anisotropy Oj03.
    Example 7, Preparing a mixture of ingredients,%: 1-cyano-1-pentylpyl-cis-4- (trans-4-pentylcyclohexyl.) -Cyclohexane, 17; 1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 17; 1-cyan-1-pro25 pil-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane, 10; P- (trans-4-propylcyclohexyl) benzoic acid 4-butyl-2-cyanophenyl ester, 24; trans-1- (p-ethoxyphenyl) -4-propyl
    „Cyclohexane, 14.
    T, rd. -16 ° C, K., viscosity 83 cCT, dielectric anisotropy - 6.3, optical anisotropy 0.07.
    Example 9. The mixture is prepared
     of the following composition,%: 1-cyano-1-pentyl-cis-4- (trans-4-propyl cyclohexyl) -cyclohexane, 19; 1-cyan-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cycloxane, 31; 1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 33; 4- (trans-4-pentylcyclohexyl) -4 - (trans-4-propyclohexyl) -biphenyl, 17.
    40
    45
    T, pa.
    -2 ° C, K. 91 ° C, viscosity
    50
    63 cst, dielectric anisotropy - 6.8, optical anisotropy 0.06 ..
    Example 10. A mixture of the following composition was prepared,%: 1-cyan-1-pentyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 11; 1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 25; 1-cyano-1-propyl-cis-4- (trans-4-pentylcyclo-55 hexyl) -cyclohexane, 21; 1-cyan-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 22; 1-cyan-1-propyl-cis-4- (trans-4-heptylcyclo-.
    cis-4- (trans-4-propylcyclohexyl) - cyclohexane, 12; 1-cyano-1-heptyl-cis- (4-trans-4-propylcyclohexylX cyclohexane, 24; 1-cyanopropyl-cis-4- (trans-4-pentylcyclohexyl) cyclohexane, 21; 1-cyano- 1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 21; 1-cyano-1-propyl-cis-4- (trax-4-heptylcyclohexyl) -cyclohexane, 13; p- trans-4-butylcyclohexylphenyl ester trans-4-pentylcyclohexyncarboxylic acid, 9. So pl, K, 63 ° Cf viscosity
    Example 8. Preparing
    a mixture of the following composition,%: 1-cyan-1 - -heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 18; 1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohex. Sil) -cyclohexane, 17; 1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 17; 1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane, 10; P- (trans-4-propylcyclohexyl) benzoic acid 4-butyl-2-cyanophenyl ester, 24; trans-1- (p-ethoxyphenyl) -4-propylcyclohexane, 14.
    T, rd. -16 ° C, K., viscosity 83 cCT, dielectric anisotropy - 6.3, optical anisotropy 0.07.
    Example 9. The mixture is prepared
    of the following composition,%: 1-cyano-1-pentyl-cis-4- (trans-4-propyl cyclohexyl) -cyclohexane, 19; 1-cyan-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cycloxane, 31; 1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 33; 4- (trans-4-pentylcyclohexyl) -4 - (trans-4-propyclohexyl) -biphenyl, 17.
    T, pa.
    -2 ° C, K. 91 ° C, viscosity
    63 cst, dielectric anisotropy - 6.8, optical anisotropy 0.06 ..
    Example 10. A mixture of the following composition was prepared,%: 1-cyan-1-pentyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 11; 1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, 25; 1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 21; 1-cyan-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 22; 1-cyan-1-propyl-cis-4- (trans-4-heptylcyclo-.
    five
    ten
    15
    , 51356965
    hexyl) -cyclohexane, 13; trans-4-propylcyclohexyl ester of p (trans-4-propylcyclohexyl) -benzoic acid, 8,
    T. „d. -PC, K., viscosity 74 cST, dielectric anisotropy 8.0, optical anisotropy 0.04,
    Example 11 A mixture of the following composition is prepared,%: trans, trans-4-propylcyclohexylcyclohexane-4-carbonitrile, 9; trans, trans-4-pentilcyclohexylcyclohexan-4 -carbonitrile, 9; trans, trans-4-g. heptyl-cyclohexylcyclohexan-4 -carbonitrile, 5; g-1-cyano- -heptyl-cis- (trans-4-butylcyclohexyl) -cyclohexane, 38,
    Example 12. A mixture of the following composition is prepared,%: g-1-cyano-1-heptyl-cis-4 (trans-4-butyl-cyclohexyl) -cyclohexane, 34.0; g-1-cyano-1-pentyl-tdis-4- (trans-4-pentylcyclohexyl) -cyclohexane, 29.0; trans, trans-4-methylcyclohexyl-4-propylcyclohexane, 10.0; trans, trans-4-ethoxycyclohexyl-4-propylcyclohexane, 9.7; 4-propyl-cyclohexyl ester of trans, trlns-4- (4 propylcyclohexyl) -11, iclohexane-carboxylic acid, 4.8; 4-pentylcyclohexyl trans, trans-4- (4-propylcyclohexyl} -cyclohexanecarboxylic acid, 3.9; 4-propyl cyclohexyl ester trans, trans-4- (4-butylcyclohexyl) -cyclohexane carboxylic acid, 3 , 9; 4-pentyl-cyclohexyl ester of trans, trans-4- (4-butyl-cyclohexyl) -cyclohexane-carboxylic acid, 3.9,
    20
    thirty
    25 o
    35
    40
     t, PA, -10 °, t. ex. +70, viscosity 45 сСТ, ui -5,4dn + 0,037.
    As can be seen from the above examples, the use of cyclohexane derivatives of general formula I in the amount of 62-94% of the total mixture with nematic liquid crystals allows to obtain a dielectric for an electro-optical indicator device with a dielectric anisotropy value from (-) 5.4 to (-) 8.7 and optical anisotropy from 0.03 to 0.07.
    Local Diethyl -: Tric has dielectric anisotropy (-) 1.5 - (-) 5.1 s
    Invention Formula
    A dielectric for an electro-optical indicator device containing nematic liquid crystals selected from the group of biphenyl derivatives, cyclohexyl or phenyl 4-substitution esters; benzoic acids and cyclohexane derivatives, in order to achieve greater negative dielectric anisotropy, as derivatives of cyclohexane use 2-5 compounds of General formula I
    SI R,
    where R, - Cj-C 7-apkil; 35 Rj - C-C-alkyl
    in the following ratio tov, wt,%:
    Derivatives of cyclohexane of general formula I. Nematic liquid crystals.
    40
    Editor Y. Sereda
    Compiled by M. Merkulova
    Tehred L. Serdyukova Proofreader G. Reshetnik
    Order 5816/58 Circulation 634Subscription
    VNIIPI USSR State Committee
    . for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab, 4/5
    Production of the printing company, Uzhgorod, ud. Project, 4
    权利要求:
    Claims (1)
    [1]
    Claim
    A dielectric for an electro-optical indicator device containing nematic liquid crystals selected from the group of biphenyl derivatives, cyclohexyl or phenyl ethers of 4-substituted benzoic acids and cyclohexane derivatives, characterized in that, in order to achieve greater negative dielectric anisotropy, 2- 5 compounds of the general formula I where R, - 'C -C 7 alkyl;
    Rj - C 2 -C f -alkyl in the following ratio of components, wt.%: ·
    Derivatives of cyclohexane of the general formula I 62-94 Nematic liquid crystals Up to 100
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    同族专利:
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    JPH0432803B2|1992-06-01|
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    CH471124A|1965-09-29|1969-04-15|Ciba Geigy|Process for the preparation of new cyclohexane derivatives|
    US3932148A|1975-01-21|1976-01-13|Criterion Manufacturing Company, Inc.|Method and apparatus for making complex aspheric optical surfaces|
    JPS6353177B2|1980-10-21|1988-10-21|Chisso Corp|
    JPS6136744B2|1980-11-18|1986-08-20|Asahi Glass Co Ltd|
    JPS6332051B2|1981-01-07|1988-06-28|Chisso Corp|
    JPH0210810B2|1981-01-14|1990-03-09|Dainippon Ink & Chemicals|JPS629278B2|1980-10-03|1987-02-27|Mitsui Toatsu Chemicals|
    US4502974A|1982-03-31|1985-03-05|Chisso Corporation|High temperature liquid-crystalline ester compounds|
    US4550981A|1982-09-30|1985-11-05|Hoffmann-La Roche Inc.|Liquid crystalline esters and mixtures|
    US4565425A|1983-03-16|1986-01-21|Hoffmann-La Roche Inc.|Liquid crystals|
    JPS60112739A|1983-11-02|1985-06-19|Hoffmann La Roche|Cyclohexylbenzene derivative and cyclohexylbiphenyl derivative|
    EP0158252B1|1984-04-07|1988-12-21|MERCK PATENT GmbH|Liquid crystal phase|
    US4629581A|1984-06-29|1986-12-16|Hoffmann-La Roche Inc.|Cyclohexanecarbonitriles|
    DE3437935A1|1984-10-17|1986-04-24|Merck Patent Gmbh, 6100 Darmstadt|HETEROCYCLIC COMPOUNDS|
    JPH0372119B2|1985-05-27|1991-11-15|Dainippon Ink & Chemicals|
    GB2248059A|1990-09-20|1992-03-25|Merck Patent Gmbh|Fluorocyclohexane derivatives and liquid-crystalline medium|
    US8858829B2|2010-07-17|2014-10-14|Organo Science Co., Ltd.|Cyclohexane compound and liquid crystal composition containing the same|
    DE102017010487A1|2016-12-02|2018-06-07|Merck Patent Gmbh|MONOFLUORIZED CYCLOHEXANES|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19823231707|DE3231707A1|1982-08-26|1982-08-26|Cyclohexane derivatives|
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