• 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:

    公开号:SU1056907A3
    申请号:SU802948200
    申请日:1980-07-04
    公开日:1983-11-23
    发明作者:Айденшинк Рудольф；Эрдманн Дитрих；КРАУЗЕ Йоахим；Поль Людвиг
    申请人:Мерк Патент Гмбх (Фирма)；
    IPC主号:
    专利说明:

    yp
    : :about
    about
    h

    The invention relates to liquid crystal dielectrics that are used in various electro-optical display and information processing devices.
    Known liquid-crystal dielectric, comprising 35 wt.% .. 4,4-pentylcidobiphenyl, 11 wt.% 4.4-hexyloxycyanobiphenyl, 32 wt.% Throne -4-pentyl- (4-cyanophenyl) -cyclohexane and 22 wt.% Trans -4-hexyl- (4-cyanophenyl) -cyclohexane. The temperature range of the nematic mesophase for it is from -10 to + 50 ° C, the viscosity is 38 cP at 20 ° C 1.
    The disadvantages of this material are the narrow temperature range of the nematic mesophase and high viscosity.
    Also known liquid-crystal dielectric, comprising 31 wt.% P; -methoxy-p-b tylazoxybenzene, 19 wt.% P -butyl-p-methoxyazoxybenzene and 50 wt.% P, p-dibutylazoxybenzene. The temperature range of the nematic mesophase for it is from -14, 8 to +52 ,, viscosity 31 сП at 20 ° С 2 ..
    The disadvantages of this material are also the narrow temperature range of the nematic mesophase and the rather high viscosity.
    The closest to the invention according to the technical essence is a liquid crystal dielectric for electro-optical purposes, consisting of the known nematic liquid crystal substances - azoxybenzenes of biphenyls, phenylcyclohexanes, esters and substances that broaden the temperature range of the nematic mesophase. As a substance that broadens the temperature range of the nematic mesophase, it contains a hexahydroterphenyl derivative of the general formula
    where one of the cycles A and B is a phenyl i second is a trans -1,4-disubstituted cyclohexane ring, R is an alkyl or alkoxy group containing 1-9 carbon of native atoms.
    Thus, a liquid-crystal dielectric containing 36 wt.% Of the throne of -4-propyl- (4-cyanophenyl) -cyclohexane,
    31 wt.% Trans-4-alkyl- (4-cyanophenyl) -cyclohexane, 21 wt.% To the throne-4-heptyl- (4-cyanophenyl) -cyclohexane and 12 wt.% 4-cyano-4 Chtrans-4-pentylcyclohexyl ) -biphenyl, has a temperature range of nematic mesophase from -6 to + 72 ° С and viscosity
    29 SP at 20 ° C.
    A disadvantage of the known material is a relatively narrow interval of the nematic mesophase.
    The aim of the invention is to expand the temperature range of the nematic mesophase.
    This goal is achieved by using a liquid crystal dielectric for electro-optical devices consisting of 1-6 nematic liquid-crystalline substances and a substance that broadens the temperature interval of the nematic mesophase, which, as a substance that broadens the temperature range of the nematic mesophase, contains a compound of the general formula
    0)
    where R is n-alkyl with 2-6 carbon atoms;
    R is n-alkyl with 2-7 carbon atoms or n-alkoxy group with 2-6 carbon atoms, with the following ratio of components, wt.%:
    The compound of formula (I) 5-26 Nematicheskie liquid crystal substances Rest
    up to 100
    Example. In a suspension of anhydrous aluminum chloride in 2000 m of dichloromethane at 10 ° C and with stirring, 306 g of 4- (4-g1-pentylcyclohexyl) -biphenyl are dissolved and a solution of 79 g of acetyl chloride in a mixture is added to the solution with stirring over 2 hours 250 mts dichloromethane. The reaction mixture is stirred for another 16 hours and poured into a solution of 300 ml of concentrated hydrochloric acid in 2.5 liters of ice water. The organic phase is separated, washed with water and sodium bicarbonate solution, dried over calcium chloride and evaporated. The remaining P: - (4-P-pentylcyclohexyl-p - acetyl biphenyl is recrystallized from ethanol. 315 g. Mp. 125 ° C. 125 ° C.
    175 g of AND - {4-n-pentylcyclohexyl) - P-acetylbiphenyl is dissolved in 1.5 l of tetrahydrofuran and in the presence of 10 g palladium on coal (5% palladium) is hydrogenated at room temperature and normal pressure for 80 hours. Then the catalyst is filtered off, the filtrate is evaporated and the remaining P- {4-n-methyl-cyclohexyl) -n-ethylbiphenyl is recrystallized from ethanol. Exit 149 g. 34 ° C, etc. 164s
    Similarly, other H- (4-C-alkylcyclohexyl) -n-alkylbiphenyls are obtained.
    PRI mme R 2. A suspension of 35 g of P- (4-H-pentylcyclohexyl) -p-acetylbifenyl in 200 ml of 98% formic acid is mixed with a mixture of 20 ml of 33% hydrogen peroxide and 50 ml of 98% - formic acid and stirred at room temperature for 72 hours. The reaction mixture is poured onto 1000 g of ice and extracted twice with 500 ml portions of dichloromethane. After evaporation of the solvent, the remaining p- (4-n-pentylcyclohexyl) - M-acetoxy Syphenyl is recrystallized from ethanol (mp.).
    46 g of p- (4-n-pentylcyclohexyl) -P-acetoxybiphenyl with 20 g of sodium hydroxide are suspended in 250 ml of water and 85 ml of ethanol. The suspension is heated at boiling for 2 hours and then acidified with hydrochloric acid. After precipitating the n - (4 - "- pentylcyclohexyl) - -hydroxybiphenyl, the filter is filtered and washed with water (mp. 202 ° q).
    A solution of 32 gp - (4-n-pentylcyclo-: hexyl) -P-hydroxybiphenyl in 250 ml of acetone is heated to boiling with 31 g-pentyl bromide in the presence of 70 g of anhydrous potassium carbonate for 24 hours under reflux. After cooling, the reaction mixture is filtered, the filtrate is evaporated and the remaining p - (4-n-pentylcyclohexyl) -p-pentyloxybiphenyl is recrystallized from ethanol. Exit 37 g. 42 ° С, tpr 183 ° С.
    Similarly, other P- (4-n-alkylcyclohexyl) -n-alkyl oxo-biphenyls are prepared.
    To prepare a liquid crystal dielectric according to examples 3-11, components taken in an appropriate amount are placed in a glass vessel, heated to a temperature 5-10 ° C above the point of clarification, stirred and cooled to room temperature. Get ready to use liquid crystal dielectric.
    Example 3. A dielectric made up of 67% 4-n-butyl-4-methoxyazoxybenzene and 33% 4-ethyl-4-methoxyazoxybenzene has a nematic phase in the temperature range from -15 to + 73 ° С and a viscosity of 31 SP at 20 ° C.
    According to the invention, a dielectric of 95.% of this two-component mixture and 5% of P - (4-H-pentylcyclohexyl) -P-ethoxybiphenyl has a nematic phase in the temperature range from -79 to + 79 ° С and a viscosity of 28 cP at 20 C. .
    For comparison, an electrician of 95%
    the aforementioned two-component mixture and 5% 4-cyano-4 (Trans-4-c-pentyl-cyclohexyl) -bifenyl has a nematic phase in the temperature range from -7 to + 78 ° C and a viscosity of 28 cP at 20 ° C.
    PRI me R 4. Dielectric of 67%, 4-H-pentylphenyl ether of anise J
    acid and 33% 4-c-pentylphenyl ester of 4-n-hexyloxybenzoic acid has a nematic phase in the temperature range from 15 to and viscosity of 58 cP at 20 ° C.
    According to the invention, the dielectric. of 80% of this two-component mixture and 20% of P- (4-n-pentylcyclohexyl) -n -ethylbiphenyl has a nematic phase in the temperature range from O to
    + 71 ° С and viscosity 49 сP at 20 ° С.
    For comparison, a dielectric of 80% of the aforementioned two-component mixture and 20% 4-cyano-4T | and "C-4-n-pentylcyclohexyl) biphenyl has a nematic phase in the temperature range from 20 to 82 ° C, and a viscosity of 56 cP at 20 ° C.
    Example 5: According to the invention, a dielectric of 77% of a two-component mixture according to example 3 and 23% of P- (4-H-pentylcyclohexyl) -n-ethylbiphenyl has a nematic | phase from -15 to and a viscosity of 30 JV at 20 ° WITH.
    For comparison, a dielectric of 77% two-component mixture according to example 3 and 23% of 4-cyano-4 - (tpOHC-4-H-pentylcyclohexyl) -bifenyl has a nematic phase in the temperature range from 22 to 104 ° C and
    viscosity 35 SP at 20 ° C.
    Example 6: According to the invention, a dielectric from an 80% two-component mixture according to example 4 and 20% P - (4-H-hexylcyclohexyl) -p-ethylbiphenyl has a nematic phase from 6 to, viscosity 52 cP at 20 ° WITH.
    For comparison, the dielectric of the 80% two-component mixture according to size 4 and 20% of 4-cyano-4- (trans-4-H -heptylcyclohexyl) -biphenyl has a nematic phase in the temperature range from 24 to 78 ° C and viscosity 59 SP at.
    Example7. The dielectric of 29% 4- (4-n-propylcyclohexyl) -benzonitrile, 41% 4- (4-n-pentylcyclohexyl) -benzonitrile and 30% of 4- (4-n-heptylcyclohexyl) -benzonitrile has a nematic phase in the temperature range from -3 to + 52s and viscosity 24 SP at 20 ° С.
    According to the invention, a dielectric of 74% of this three-component mixture and 26% of P- (4-m-pentylcyclohexyl) -biphenyl has a nematic phase in the temperature range from –10 to + 740 s and a viscosity of 23 cP at 20 ° C.
    To compare, a dielectric of 74% of the mentioned three-component mixture and 26% of 4-cyano-4- (trans-4-n-heptylcyclohexyl) -bifenyl has a nematic phase in the temperature range from 24 to 90 ° C and a viscosity of 33 cP at 20 ° C. Example Liquid-crystalline compound P -H-pentyl-p-cyanobiphenyl has a nematic phase in the temperature range from 22.5 to 350 ° C and a viscosity of 29.5 cP at (supercooled state). According to the invention, a mixture of 90% PH-pentyl-P-cyanobiphenyl and 10% P- (4-c-pentylcyclohexyl) -n -h-butylbiphenyl has a nematic phase in the temperature range from 18.5 to 49.2 ° C and viscosity 29 cps at. To compare, a dielectric of 90% of the mentioned PH-pentyl-p-cyanobiphenyl and 10% of 4-cyano-4- (trpc-4-H-heptylcyclohexyl) -biphenyl has a nematic phase between 20 and 50 ° C and a viscosity of 29 SP at 20 ° C. Example 9. Liquid dielectric dielectric from 20% 4- (tro1ns -4-p-pentyl-cyclohexyl) -benzonitrile, 22% 4- (trans -4-H-propylcyclohexyl) -phenetol, 14% 4- ethyl 4-cyanobifen, 13% 4-n-butyl-4-cyanobiphenyl, 11% 4- {trans-4-n-pentylcyclohexyl) -4 - (trois-4-n-propylcyclohexyl) biphenyl, and 15% 4 -n-propylphenyl 4-tTpoiHc-4-H-propylcyclohexyl-benzoic acid ester has a nematic phase in the temperature range from -2 to and viscosity 23 cP at 20 C. According to the invention, a dielectric of 92% of this six-component mixture . and 8% 4- (trans-4-n-propylcyclohexyl 4 -ethylbiphenyl has a nematic phase in the temperature range from -5 to + 85 ° C and a viscosity of 23 cP at 20 ° C. Comparing the dielectric of 95% of the six-component mixture and 8% of 4-cyano-4- (trans-4-n-propyl lekeksyl) -biphenyl has a nematic phase in the temperature range from 23 to 85 ° C and a viscosity of 25 cP at 20 EXAMPLE. A liquid dielectric from 28% 4- (trans -4-n-proT1ylcyclohexyl) ethylbenzene, 19% 4- (trO | HC -4-n-propylcyclohexyl) phenetol, 16% 4- (trans-4-n-propyl., Cyclohexyl) -benzonitrile, 9% 4 - (trans-4-I-pentylcyclohex Il) -4 gtsyanobifenil and 15% 4- n-propylphenyl ether 4- (trans-4-n-propylcyclohexyl) -benzoic acid has a nematic phase in the temperature range from -1 to + 68s and a viscosity of 16 cP when, according to the invention, the dielectric of 78% of this five-component mixture and 22% of 4- (tra (HC-4-ethylcyclohexyl) -4-H-hexyl hydroxybiphenyl) has a nematic phase in the temperature range from -8 to + 101 ° C and a viscosity of 16 cP at 20 ° C . For comparison, a dielectric of 78% of the mentioned five-component mixture and 22% of 4-cyano-4- (trans-4-heptylcyclohexyl) -biphenyl has a nematic phase in the temperature range from 23 to 90 ° C and a viscosity of 24 cP at 20 ° C . Example. Liquid crystal dielectric of 29% 4- (trans-4-N-propylcyclohexyl) -phenetol, 24% 4- (Trans-4-n-propylcyclohexyl) -H-butyloxybenzene, 18% 4-M-butyl-2-cI-phenyl ether 4 - (trans-4-H-propylcyclohexyl) -benzoic acid and 29% 4-H-pentylphenyl 4-methylbenoic acid ester has a nematic mesophase in the temperature range from 0 to 42 ° C and a viscosity of 21 cP at 20 ° C. According to the invention, a dielectric of 85% of this four-component mixture and 15% of 4- (TpaiHC-4-H-butylcyclohexyl) -4-H-hectylbiphenyl has a nematic phase in the temperature range from -5 to + 62 ° С and viscosity 20 сP at 20 ° С. To compare, a dielectric of 85% of the mentioned four-component mixture and 15% 4-cyano-4 - (tro1Hc-4-n-pentylcyclohexyl) -biphenyl has a nematic phase in the temperature range from +7 to + 65 ° C and a viscosity of 26 cP at . Thus, the use of the invention allows obtaining liquid crystal dielectrics for electro-optical devices with a wider range of nematic mesophases from Th-15 to + 95 ° C), while the dielectric viscosity remains unchanged or decreases (16-23 cP at 20 s).
    权利要求:
    Claims (1)
    [1]
    (54) LIQUID CRYSTAL DIELECTRIC for electro-optical devices, consisting of 1-6 nematic liquid crystalline substances and a substance that extends the temperature range of the nematic mesophase, characterized in that, in order to expand the temperature range of the nematic meeophase, it contains a substance that extends the interval of the nematic mesophase, the compound of General formula. (I) ( where R r '
    - n-alkyl with 2-6 carbon atoms;
    - n-alkyl with 2-7 carbon atoms or n-alkoxy group with 2-6 carbon atoms, in the following ratio, weight
    The compound of formula (I) Nematic liquid crystal substances komponent5-26
    The rest is up to 100
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19792927277|DE2927277A1|1979-07-06|1979-07-06|CYCLOHEXYLBIPHENYLE, METHOD FOR THE PRODUCTION THEREOF, THESE DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT|
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