CN112080284A - Liquid crystal compound, liquid crystal composition, liquid crystal display element or liquid crystal display - Google Patents

Liquid crystal compound, liquid crystal composition, liquid crystal display element or liquid crystal display Download PDF

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CN112080284A
CN112080284A CN201910511413.9A CN201910511413A CN112080284A CN 112080284 A CN112080284 A CN 112080284A CN 201910511413 A CN201910511413 A CN 201910511413A CN 112080284 A CN112080284 A CN 112080284A
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姜军
李佳明
李明
孟劲松
张虎波
王晓娜
梁志安
员国良
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

The invention discloses a liquid crystal compound, the structural formula of which is shown as the following formula I,
Figure DDA0002093620060000011
the liquid crystal compound has better reliability, good low-temperature intersolubility and faster response speed. The invention also discloses a liquid crystal composition containing the liquid crystal compound and a liquid crystal display element or a liquid crystal display.

Description

Liquid crystal compound, liquid crystal composition, liquid crystal display element or liquid crystal display
Technical Field
The invention relates to the technical field of liquid crystal display. And more particularly, to a liquid crystal compound, a liquid crystal composition comprising the liquid crystal compound, a liquid crystal display device or a liquid crystal display.
Background
With the development of Display technology, flat panel Display devices such as Liquid Crystal Display (LCD) devices have advantages of high image quality, power saving, thin body, and wide application range, and thus are widely used in various consumer electronics products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, and desktop computers, and are becoming the mainstream of Display devices.
In order to satisfy the requirements of various consumer electronic products, liquid crystal materials used for display elements and display devices in IPS display mode, FFS display mode, VA display mode, and the like are required to have (i) a low driving voltage: the liquid crystal material has proper negative dielectric anisotropy; quick response: the liquid crystal material has low rotational viscosity; high reliability: high charge retention rate, high specific resistance value, excellent high-temperature stability, strict requirements on the stability of UV light or irradiation by conventional backlight illumination and the like; good low-temperature intersolubility: the solubility of the liquid crystal material is relatively good. However, when the basic characteristics (low driving voltage, fast response) required by the above displays are achieved, the reliability problem is revealed. In the dynamic display process of the liquid crystal display, in order to ensure that the previous display frame is not displayed any more in the next frame, which causes the phenomenon of ghost or tailing in the frame switching process, the liquid crystal display is required to have a fast response speed, and further the rotational viscosity of the liquid crystal material is required to be low. Meanwhile, in many cases, the liquid crystal mixture is required to work at a very low temperature, especially in an outdoor environment, and the liquid crystal mixture is required to work at-30 ℃ for a long time, so that the liquid crystal composition is required to have good low-temperature performance, that is, the liquid crystal composition is stored at a low temperature for a long time without monomer precipitation, and therefore, the development of a liquid crystal composition with good intersolubility at a low temperature is still necessary.
Disclosure of Invention
In order to solve the problems in the prior art, a first object of the present invention is to provide a liquid crystal compound having better reliability, good low-temperature mutual solubility and faster response speed.
In addition, a second object of the present disclosure is to provide a liquid crystal composition that has improved low-temperature compatibility, improved reliability, and improved response speed while maintaining good rotational viscosity.
A third object of the present disclosure is to provide a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition of the present disclosure, which has a fast response speed.
In order to achieve the purpose, the following technical scheme is adopted in the disclosure:
the disclosure provides a liquid crystal compound, the structural formula of which is shown as the following formula I,
Figure BDA0002093620040000011
Figure BDA0002093620040000021
wherein R represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms, or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, any of which is-CH not bonded to-O-2-optionally substituted by-O-;
any one or more of the groups represented by R being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Figure BDA0002093620040000022
represents 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene or fluoro-1, 4-phenylene;
p represents 0, 1,2, 3.
The present disclosure also provides a liquid crystal display element comprising the liquid crystal composition of the present disclosure, the liquid crystal display element being an active matrix addressing display element or a passive matrix addressing display element.
The present disclosure also provides a liquid crystal display comprising the liquid crystal composition of the present disclosure, the liquid crystal display being an active matrix addressed display or a passive matrix addressed display.
The introduction of alkenyl groups into liquid crystal molecules can increase the elastic constant K of the liquid crystal molecules, so that a liquid crystal composition containing the liquid crystal compound has a higher response speed; however, the naked terminal olefinic bond on the one hand and the direct bond between the olefinic bond and the aromatic system on the other hand are very likely to cause poor reliability of the monomers. The reliability of the liquid crystal monomer is greatly improved after the end position of the olefinic bond is added with the dimethyl substituent. Due to the fact that the regularity of the liquid crystal molecules is damaged to a certain extent by adding the dimethyl substituent group at the end position of the olefinic bond, the liquid crystal monomer has good low-temperature intersolubility, and meanwhile, the original large negative dielectric anisotropy can be kept. The liquid crystal display element or the liquid crystal display comprising the liquid crystal composition also has the characteristics of the liquid crystal composition, and the details are not repeated herein.
Detailed Description
The disclosure provides a liquid crystal compound, the structural formula of which is shown as the following formula I,
Figure BDA0002093620040000023
wherein R represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted carbon atomAn alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms, or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, any of which is-CH not bonded to-O-2-optionally substituted by-O-;
any one or more of the groups represented by R being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, and the like.
Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, and a decyloxy group.
Examples of the alkenyl group having 2 to 10 carbon atoms include a vinyl group, a 1-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, and a 3-hexenyl group.
The "fluoro-substituted" in the above-mentioned fluoro-substituted alkyl group having 1 to 10 carbon atoms, fluoro-substituted alkoxy group having 1 to 10 carbon atoms, fluoro-substituted alkenyl group having 2 to 10 carbon atoms, and fluoro-substituted alkenyloxy group having 3 to 8 carbon atoms may be a monofluoro-substituted, or a polyfluoro-substituted, such as a difluoro-substituted, trifluoro-substituted, or a perfluoro-substituted group, and the number of fluoro-substituted groups is not particularly limited. Examples of the fluorine-substituted alkyl group having 1 to 10 carbon atoms include, but are not limited to, fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1, 2-difluoroethyl, 1,1, 2-trifluoroethyl, and 1,1,1,2, 2-pentafluoro-substituted ethyl.
Figure BDA0002093620040000031
Represents a 1, 4-cyclohexylene group, a 1, 4-cyclohexenylene group, a 1,4-phenylene or fluoro-1, 4-phenylene;
p represents 0, 1,2, 3.
In the liquid crystal compound of the present disclosure, preferably, the compound represented by the aforementioned formula I is selected from the group consisting of the following compounds represented by formulae I-1 to I-14:
Figure BDA0002093620040000032
Figure BDA0002093620040000041
wherein R represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms, or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, any of which is-CH not bonded to-O-2-optionally substituted by-O-;
any one or more of the groups represented by R being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene.
Preferably, the liquid crystal compound has a structural formula as shown in the following formulas I-1-1 to I-14-2,
Figure BDA0002093620040000042
Figure BDA0002093620040000051
the compound shown in the formula I has large negative dielectric anisotropy, good low-temperature intersolubility and large elastic constant K value, and the driving voltage of the liquid crystal composition is adjusted and the low-temperature intersolubility is solved by the compound shown in the formula I.
It is understood that the technical scheme of the liquid crystal composition of the invention includes but is not limited to the specific forms listed.
According to a second object of the present invention, there is provided a liquid crystal composition comprising the liquid crystal compound provided in the first object.
Preferably, the liquid crystal composition further comprises one or more compounds represented by the following formula II,
Figure BDA0002093620040000061
in the formula II, R1、R2Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms,
Figure BDA0002093620040000062
each independently represent
Figure BDA0002093620040000063
Or
Figure BDA0002093620040000064
Preferably, the one or more compounds of formula II are selected from the group consisting of compounds of formula II-1 through formula II-17,
Figure BDA0002093620040000065
Figure BDA0002093620040000071
the compound shown in the formula II has the characteristics of low rotational viscosity and good intersolubility with other compounds. The lower rotational viscosity is more favorable for improving the response speed of the liquid crystal composition.
Preferably, the liquid crystal composition further comprises one or more compounds represented by the following formula III,
Figure BDA0002093620040000072
in the formula III, R3、R4Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, a linear alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted linear alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R3、R4Any one or more non-adjacent-CH2-may be optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z1、Z2each independently represents a single bond, -CH2CH2-or-CH2O-；
Figure BDA0002093620040000073
Each independently represent
Figure BDA0002093620040000074
Or
m represents 1 or 2;
n represents 0, 1 or 2.
As R in the aforementioned formula III3、R4One or more non-adjacent-CH in the alkyl with 1-10 carbon atoms2Substituted by cyclopropylene, cyclobutylene or cyclopentyleneExamples of the group include cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopropylidene, ethylcyclopropylidene, propylcyclopropylidene, isopropylcyclopropylidene, n-butylcyclopropylidene, isobutylcyclopropylidene, tert-butylcyclopropylidene, methylcyclobutyl, ethylcyclobutyl, propylcyclobutyl, isopropylcyclobutyl, n-butylcyclobutyl, isobutylcyclobutyl, tert-butylcyclobutyl, methylcyclopentyl, ethylcyclopentylidene, propylcyclopentylidene, isopropylcyclopentylidene, n-butylidene, isopropylcyclopentylidene, n-butylcyclopentylidene, isobutylcyclopentylidene, and the like. R3、R4Among the groups shown, preferred is cyclopropylene, cyclobutylene or cyclopentylene from the viewpoint of the rotational viscosity, solubility and clearing point of the liquid crystal compound.
Preferably, the one or more compounds of formula III are selected from compounds of formulae III-1 to III-15,
Figure BDA0002093620040000081
Figure BDA0002093620040000091
wherein R is3、R4Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, a linear alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted linear alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R3、R4Any one or more non-adjacent-CH2-may be optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene.
The compound shown in the formula III has negative dielectric anisotropy, and the driving voltage of the liquid crystal composition is adjusted by the compound shown in the formula III.
The liquid crystal composition of the present invention is preferably a negative dielectric anisotropic liquid crystal composition.
Preferably, in the liquid crystal composition of the present invention, the compound represented by formula i is added in an amount (mass ratio) of 1 to 20%, preferably 5 to 10%; the addition amount (mass ratio) of the compound shown in the formula II in the liquid crystal composition is 10-60%, and preferably 20-45%; the amount (mass ratio) of the compound represented by the formula III added to the liquid crystal composition is 15 to 60%, preferably 25 to 50%.
Preferably, the liquid crystal composition further comprises one or more compounds shown as a formula IV,
Figure BDA0002093620040000092
wherein R is5、R6Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R5、R6Any one or more non-adjacent-CH2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene; w represents-O-, -S-or-CH2O-。
By containing the compound shown in the formula IV in the liquid crystal composition, the liquid crystal composition has larger negative dielectric anisotropy, and is favorable for reducing the driving voltage of a device. When the liquid crystal composition of the present invention contains the compound represented by the formula IV, the amount (mass ratio) of the compound represented by the formula IV added to the liquid crystal composition may be 1 to 20%, preferably 2 to 15%.
Preferably, the one or more compounds of formula IV are selected from the group consisting of compounds of formulae IV-1 to IV-10,
Figure BDA0002093620040000093
Figure BDA0002093620040000101
wherein R is51、R61Represents an alkyl group having 2 to 6 carbon atoms.
Preferably, the liquid crystal composition further comprises one or more compounds represented by formula V,
Figure BDA0002093620040000102
wherein R is7、R8Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure BDA0002093620040000103
each independently represent
Figure BDA0002093620040000104
Or
Figure BDA0002093620040000105
Preferably, the one or more compounds of formula V are selected from the group consisting of compounds of formula V-1 to formula V-4,
Figure BDA0002093620040000106
wherein R is71、R81Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; wherein, the foregoingExamples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group, a 2-propenyl group and a 3-pentenyl group. R82Represents an alkoxy group having 1 to 5 carbon atoms;
the amount (mass ratio) of the compound represented by the formula V added to the liquid crystal composition may be 1 to 30%, preferably 3 to 25%.
The compounds of the formula V have a high clearing point and elastic constant, in particular the bending elastic constant K33And is beneficial to improving the parameter performance of the liquid crystal composition.
Preferably, the liquid crystal composition further comprises one or more compounds shown as a formula VI
Figure BDA0002093620040000111
Wherein R is9、R10Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure BDA0002093620040000112
to represent
Figure BDA0002093620040000113
Or
Figure BDA0002093620040000114
F1、F2、F3Each independently represents H or F, and F2、F3Not simultaneously F.
Preferably, the one or more compounds of formula VI are selected from the group consisting of compounds of formulae VI-1 to VI-3,
Figure BDA0002093620040000115
wherein R is9、R10Each independently preferably represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms.
The compounds shown in the formulas VI-1 to VI-3 have high clearing points which are generally higher than 200 ℃, and can more remarkably improve the clearing points of the liquid crystal composition.
The compound of formula VI may be added to the liquid crystal composition in an amount (mass ratio) of 1 to 10%, preferably 2 to 7%.
In order to achieve the third object, the present invention provides a liquid crystal display element or a liquid crystal display, which comprises the liquid crystal composition provided in the second object, wherein the liquid crystal display element or the liquid crystal display is an active matrix display element or a display or a passive matrix display element or a display.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 shows a mass spectrum of a liquid crystal compound obtained in example 2.
Examples
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method if no special description is provided, the used raw materials can be obtained from a public commercial way if no special description is provided, the percentages refer to mass percentage, the temperature is centigrade (DEG C), the liquid crystal compound also becomes a liquid crystal monomer, and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
Δ n represents optical anisotropy, and Δ n ═ ne-noWherein n isoRefractive index of ordinary light, neThe refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
Δ represents dielectric anisotropy, Δ ═/-, where/is the dielectric constant parallel to the molecular axis,/-is the dielectric constant perpendicular to the molecular axis, the test conditions were 25 ± 0.5 ℃,20 micron parallel cells, INSTEC: ALCT-IR1 test;
VHR represents the voltage holding ratio (%), and the test conditions are 20 +/-2 ℃, voltage +/-5V, pulse width 10ms and voltage holding time 16.7 ms. The testing equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
γ 1 represents rotational viscosity (mPa. multidot.s) at 25. + -. 0.5 ℃ in a 20 μm parallel cell INSTEC: ALCT-IR1 test;
K11is the splay elastic constant, K33For the flexural elastic constant, the test conditions were: 25 ℃ INSTEC, ALCT-IR1, 18 micron vertical cell.
The preparation method of the liquid crystal composition comprises the following steps: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The liquid crystal monomer structure used in the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables 1 and 2.
Table 1: corresponding code of ring structure
Figure BDA0002093620040000121
Figure BDA0002093620040000131
Table 2: corresponding codes for end groups and linking groups
Figure BDA0002093620040000132
Examples are:
Figure BDA0002093620040000133
the code is CC-Cp-V1;
Figure BDA0002093620040000134
the code is PGP-Cpr 1-2;
Figure BDA0002093620040000135
the code is CPY-2-O2;
Figure BDA0002093620040000141
the code is CCY-3-O2;
Figure BDA0002093620040000142
the code is COY-3-O2;
Figure BDA0002093620040000143
the code is CCOY-3-O2;
Figure BDA0002093620040000144
the code is Sb-CpO-O4;
Figure BDA0002093620040000145
the code is Sc-CpO-O4;
Figure BDA0002093620040000146
the code is CY-Ib-O2;
Figure BDA0002093620040000147
the code is PY-Ib-O2;
Figure BDA0002093620040000148
the code is YY-Ib-O2;
Figure BDA0002093620040000149
the code is CPY-Ib-O2;
Figure BDA00020936200400001410
the code is CYY-Ib-O2;
Figure BDA00020936200400001411
the code is CCY-Ib-O2;
Figure BDA0002093620040000151
the code is CLY-Ib-O2;
Figure BDA0002093620040000152
the code is PY-1V-O2.
[ liquid Crystal Compound ]
The method for preparing the compound shown in the formula I can be synthesized according to the following scheme:
1) when R represents a substituted or unsubstituted alkyl, alkoxy, alkenyl,
Figure BDA0002093620040000153
in the case of a cyclohexyl ring, the reaction process is as follows:
Figure BDA0002093620040000154
the preparation method comprises the following steps:
a. to and with
Figure BDA0002093620040000155
The raw materials are subjected to addition reaction in the presence of butyl lithium to obtain
Figure BDA0002093620040000156
b. To be provided with
Figure BDA0002093620040000157
Is taken as a raw material and is respectively subjected to p-toluenesulfonic acid dehydration and Pd/C catalytic hydrogenation to obtain
Figure BDA0002093620040000158
c. To be provided with
Figure BDA0002093620040000159
As raw material, hydrolyzed under acidic condition to compound
Figure BDA00020936200400001510
d. To be provided with
Figure BDA0002093620040000161
Is prepared from raw materials through wittig reaction under alkaline condition
Figure BDA0002093620040000162
e. To be provided with
Figure BDA0002093620040000163
As raw material, hydrolyzed under acidic condition to compound
Figure BDA0002093620040000164
f. To be provided with
Figure BDA0002093620040000165
Is prepared from raw materials through wittig reaction under alkaline condition
Figure BDA0002093620040000166
To be provided with
Figure BDA0002093620040000167
As a substitute for raw materials
Figure BDA0002093620040000168
Can be synthesized by the above general formula
Figure BDA0002093620040000169
2) When R represents a substituted or unsubstituted alkoxy group, an alkenyl group,
Figure BDA00020936200400001610
when representing a benzene ring, the reaction process is as follows:
Figure BDA00020936200400001611
the preparation method comprises the following steps:
(ii) above
Figure BDA00020936200400001612
Takes a coupling reaction as raw material under the condition of catalyst,
Figure BDA00020936200400001613
② by
Figure BDA0002093620040000171
Taking the raw material, and carrying out wittig reaction in the presence of potassium tert-butoxide to obtain the product
Figure BDA0002093620040000172
The 2, 3-difluoro-4-bromobenzaldehyde is used as a raw material to replace p-bromobenzaldehyde for synthesis
Figure BDA0002093620040000173
To be provided with
Figure BDA0002093620040000174
Can be synthesized by replacing bromobenzaldehyde with raw material
Figure BDA0002093620040000175
The raw materials and reagents in the general formula of the synthesis can be purchased from commercial sources, the method principle, the operation process, the conventional post treatment, the silica gel column passing, the recrystallization purification and other means are well known by synthesizers in the field, and the synthesis process can be completely realized to obtain the target product.
The reactions of all the steps of all the above processes are carried out in a solvent; the solvent is at least one selected from tetrahydrofuran, N-dimethylformamide, ethanol, methanol, dichloromethane, acetone, toluene and deionized water.
Example 1
The structural formula of the compound is shown as the following formula I-1-3:
Figure BDA0002093620040000176
the preparation route is as follows:
Figure BDA0002093620040000177
the specific operation flow of the preparation is as follows:
step 1: intermediate 1-a
Adding 0.5mol of 2, 3-difluorophenetole into a 5L three-necked bottle, cooling to-78 ℃, carrying out nitrogen protection, dropwise adding 0.6mol of butyl lithium, keeping the temperature to-78 ℃, stirring for 1 hour, dropwise adding 0.5mol of monoethylene glycol cyclohexanedione, after the reaction is finished, adding 1.0L of water and regulating the pH to be less than 7, stirring and standing by 0.5L of ethyl acetate for liquid separation, washing an organic phase by 0.5L of multiplied by 2 water, drying anhydrous sodium sulfate, then carrying out liquid spin-drying,
adding 2L of toluene and 0.02mol of p-toluenesulfonic acid, heating, refluxing and dehydrating for 2 hours, separating liquid after the reaction is finished, washing an organic phase once by using 0.5L of water, adding 10g of Pd/C and 50psi of hydrogen, and reacting for 2 hours. After the reaction was completed, the catalyst was filtered, the solvent was concentrated, and the residue was recrystallized to obtain 100g of intermediate 1-a as a white solid, 98% by GC, and 67% by yield Y.
Step 2: intermediate 1-b
Adding 0.33mol of intermediate 1-a and 500mL of tetrahydrofuran into a 2L three-necked flask, starting stirring, dropwise adding 340mL of 20% hydrochloric acid aqueous solution for half an hour, keeping the temperature at 50-60 ℃, reacting and stirring for 1 hour. After the reaction is finished, pouring the mixture into 500ml of deionized water for hydrolysis, separating liquid, extracting the water phase once by using 1000ml of ethyl acetate, combining organic layers, evaporating the solvent to dryness, and distilling under reduced pressure to obtain 60g of colorless solid 1-b, wherein the GC is 97.5 percent, and the yield Y is 70.5 percent. A
And step 3: intermediate 1-c
Adding 0.28mol of chloromethyl ether triphenylphosphine salt and 500mL of tetrahydrofuran into a 2L three-necked flask, starting stirring, carrying out nitrogen protection, cooling to-10 ℃, adding 0.28mol of potassium tert-butoxide in batches, stirring for half an hour after adding, dropwise adding a mixed solution of 0.23mol of intermediate 1-b and 200mL of tetrahydrofuran, and reacting and stirring for 1 hour after dropwise adding. After the reaction is finished, pouring the mixture into 500ml of deionized water for hydrolysis, extracting by ethyl acetate, separating liquid, combining organic layers, evaporating the solvent to dryness, and recrystallizing to obtain 50g of colorless solid 1-c, wherein the GC rate is 97.5 percent, and the yield Y is 75 percent.
And 4, step 4: intermediates 1-d
Adding 0.17mol of intermediate 1-c and 300mL of tetrahydrofuran into a 1L three-necked flask, starting stirring, dropwise adding 170mL of 20% hydrochloric acid aqueous solution for half an hour, keeping the temperature at 50-60 ℃, reacting and stirring for 1 hour. After the reaction is finished, pouring the mixture into 500ml of deionized water for hydrolysis, separating liquid, extracting the water phase once by using 1000ml of ethyl acetate, combining organic layers, evaporating the solvent to dryness, and recrystallizing to obtain 35g of colorless solid 1-d totally, wherein GC is 98 percent, and the yield Y is 77 percent.
And 5: object Compound I-1-3
Adding 0.15mol of 2-bromopropane triphenylphosphine salt and 200mL of tetrahydrofuran into a 1L three-necked flask, starting stirring, reducing the temperature to-10 ℃ under the protection of nitrogen, adding 0.15mol of potassium tert-butoxide in batches, stirring for half an hour after the addition, dropwise adding a mixed solution of 0.13mol of intermediate 1-d and 200mL of tetrahydrofuran, and reacting and stirring for 1 hour after the dropwise addition. After the reaction is finished, pouring the mixture into 500ml of deionized water for hydrolysis, extracting by ethyl acetate, separating liquid, combining organic layers, evaporating the solvent to dryness, and recrystallizing to obtain 20g of the target compound I-1-3, wherein the GC content is 99.5%, and the yield Y is 51%.
The liquid crystal compound (I-1-3) was tested as follows:
Δn[589nm,25℃]：0.1121；
Cp：26℃；
K33：9.2；
Δ[1KHz,25℃]：-6.7。
example 2
The structural formula of the compound is shown as the following formula I-2-1:
Figure BDA0002093620040000181
the preparation route is as follows:
Figure BDA0002093620040000191
the specific operation flow of the preparation is as follows:
step 1: intermediate 2-a
0.1mol of 2, 3-difluoro-4-ethoxyphenylboronic acid, 0.2mol of p-bromobenzaldehyde and 0.3mol of potassium carbonate are added to a 1L three-necked flask, 500ml of toluene and 100ml of water are added, nitrogen is used for protection, and 100mg of palladium tetratriphenylphosphine are added. The temperature is raised to 80 ℃ and the reaction is carried out for 3 hours. After the reaction is finished, 500ml of deionized water is poured, ethyl acetate is used for extraction, liquid separation is carried out, organic layers are combined, the solvent is evaporated to dryness, and recrystallization is carried out to obtain 41g of the target compound 2-a, the GC content is 99%, and the yield Y is 78%.
Step 2: object Compound I-2-1
Referring to the procedure for synthesizing the objective compound 1-e in step 5 of example 1, the objective compound i-2-1 was synthesized using 2-a as a starting material to obtain 21g of a white solid, 99.5% by GC and 46% by yield Y.
The liquid crystal compound (I-2-1) was tested as follows:
Δn[589nm,25℃]：0.1877；
Cp：23℃；
K33：8.5；
Δ[1KHz,25℃]：-6.5。
example 3
The structural formula of the compound is shown as the following formula I-3-1:
Figure BDA0002093620040000192
the preparation route is as follows:
Figure BDA0002093620040000193
the specific operation flow of the preparation is as follows:
step 1: intermediate 3-a
The target compound 3-a was synthesized from 2, 3-difluoro-4-bromobenzaldehyde and 2, 3-difluoro-4-ethoxyphenylboronic acid in the same manner as in step 1 of example 2, to obtain 10g of a white solid, 98% of GC and 95% of yield Y.
Step 2: object Compound I-3-1
Referring to the procedure of step 2 of example 2, the synthesis of the objective compound I-3-1 was carried out starting from 3-a to give 5g of a white solid, GC: 99.8%, yield Y was 75%.
The liquid crystal compound (I-3-1) was tested as follows:
Δn[589nm,25℃]：0.1823；
Cp：11℃；
K33：4.5；
Δ[1KHz,25℃]：-7.1。
example 4
The structural formula of the compound is shown as the following formula I-7-1:
Figure BDA0002093620040000201
the preparation route is as follows:
Figure BDA0002093620040000202
the specific operation flow of the preparation is as follows:
step 1: intermediate 4-a
The intermediate 4-a was synthesized by using p-bromoiodobenzene as a raw material instead of p-bromobenzaldehyde with reference to step 1 in example 2.
Step 2: intermediate 4-b
Intermediate 4-b was synthesized in step 1 of reference example 1 using 4-a instead of 2, 3-difluorophenetole as a starting material.
And step 3: intermediate 4-c
Starting from 4-b instead of 1-a, intermediate 4-c was synthesized according to step 2 of example 1.
And 4, step 4: intermediate 4-d
Starting from 4-c instead of 1-b, intermediate 4-d was synthesized according to step 3 of example 1.
And 5: intermediate 4-e
Starting from 4-d instead of 1-c, intermediate 4-e was synthesized according to step 4 of example 1.
Step 6: object Compound I-5-1
Starting from 4-e instead of 1-d, the target compound I-7-1 was synthesized in step 5 of reference example 1.
The liquid crystal compound (I-7-1) was tested as follows:
Δn[589nm,25℃]：0.2215；
Cp：181℃；
K33：42.1；
Δ[1KHz,25℃]：-6.1。
example 5
The structural formula of the compound is shown as the following formula I-8-1:
Figure BDA0002093620040000211
the preparation route is as follows:
Figure BDA0002093620040000212
the specific operation flow of the preparation is as follows:
step 1: intermediate 5-a
Intermediate 5-a was synthesized in step 1 of reference example 4 starting from 2, 3-difluorobromobenzene instead of p-bromobenzene iodide.
Step 2: intermediate 5-b
Intermediate 5-b was synthesized in step 2 of reference example 4, starting from intermediate 5-a.
And step 3: intermediate 5-c
Intermediate 5-c was synthesized in step 3 of reference example 4, starting from intermediate 5-b.
And 4, step 4: intermediate 5-d
Intermediate 5-d was synthesized in step 4 of reference example 4, starting from intermediate 5-c.
And 5: intermediate 5-e
Intermediate 5-e was synthesized in step 5 of reference example 4, starting from intermediate 5-d.
Step 6: object Compound I-8-1
The target compound I-8-1 was synthesized in step 6 of reference example 4, starting from intermediate 5-e.
The liquid crystal compound (I-8-1) was tested as follows:
Δn[589nm,25℃]：0.2103；
Cp：139℃；
K33：31.5；
Δ[1KHz,25℃]：-8.1。
example 6
The structural formula of the compound is shown as the following formula I-9-2:
Figure BDA0002093620040000221
the preparation route is as follows:
Figure BDA0002093620040000222
the specific operation flow of the preparation is as follows:
step 1: intermediate 6-a
Synthesizing a target compound 6-a by using monoethylene glycol condensed 1, 4-dicyclohexyl dione instead of monoethylene glycol condensed cyclohexanedione as a raw material according to the step 1 in the reference example 1;
step 2: intermediate 6-b
Synthesizing a target compound 6-b by using 6-a instead of 1-a as a raw material according to the step 2 in the example 1;
and step 3: intermediate 6-c
Synthesizing an intermediate 6-c by using 6-b instead of 1-b as a raw material according to step 3 in example 1;
and 4, step 4: intermediate 6-d
Synthesizing an intermediate 6-d by using 6-c instead of 1-c as a raw material according to the step 4 in the example 1;
and 5: target Compound I-7-2
The target compound I-9-2 was synthesized by using 6-d instead of 1-d as the starting material in reference to step 5 in example 1.
The liquid crystal compound (I-9-2) was tested as follows:
Δn[589nm,25℃]：0.1687；
Cp：187℃；
K33：44.6；
Δ[1KHz,25℃]：-6.8。
example 7
The structural formula of the compound is shown as the following formula I-10-1:
Figure BDA0002093620040000231
the preparation route is as follows:
Figure BDA0002093620040000232
the specific operation flow of the preparation is as follows:
step 1: intermediate 7-a
Adding 0.1mol of 2, 3-difluoroether and 500ml of THF into a 1L three-necked bottle, cooling to-78 ℃, carrying out nitrogen protection, dropwise adding 0.15mol of butyl lithium, keeping the temperature to-78 ℃, stirring for 1 hour, dropwise adding 0.1mol of monoethylene glycol to condense 1, 4-dicyclo cyclohexanedione, after the reaction is finished, adding 1.0L of water and regulating the pH to be less than 7, stirring with 0.5L of ethyl acetate, standing for liquid separation, washing an organic phase with 0.5L of multiplied by 2 water, drying anhydrous sodium sulfate, carrying out liquid spin drying,
adding 1L of toluene and 0.02mol of p-toluenesulfonic acid, heating, refluxing and dehydrating for 2 hours, separating liquid after the reaction is finished, washing an organic phase once by using 0.5L of water, concentrating a solvent, and recrystallizing a residue to obtain a white solid, namely an intermediate 7-a30g, wherein GC is 98% and the yield Y is 79.3%.
Step 2: intermediate 7-b
Synthesizing an intermediate 7-b by using 7-a instead of 1-a as a raw material according to the step 2 in the example 1;
and step 3: intermediate 7-c
Synthesizing an intermediate 7-c by using 7-b instead of 1-b as a raw material according to step 3 in example 1;
and 4, step 4: intermediate 7-d
Synthesizing an intermediate 7-d by using 7-c instead of 1-c as a raw material according to the step 4 in the example 1;
and 5: object Compound I-8-1
Synthesizing a target compound I-10-1 by using 7-d instead of 1-d as a raw material according to the step 5 in the reference example 1;
the liquid crystal compound (I-10-1) was tested as follows:
Δn[589nm,25℃]：0.1958；
Cp：204℃；
K33：45.7；
Δ[1KHz,25℃]：-7.2。
[ liquid Crystal composition ]
Example 8
The formulation and corresponding properties of the liquid crystal compositions are shown in table 3 below.
Table 3: formulation and corresponding Properties of the liquid Crystal composition of example 8
Figure BDA0002093620040000241
Example 9
The formulation and corresponding properties of the liquid crystal compositions are shown in table 4 below.
Table 4: formulation and corresponding Properties of the liquid Crystal composition of example 9
Figure BDA0002093620040000242
Figure BDA0002093620040000251
Example 10
The formulation and corresponding properties of the liquid crystal compositions are shown in table 5 below.
Table 5: formulation and corresponding Properties of the liquid Crystal composition of example 10
Figure BDA0002093620040000252
Example 11
The formulation and corresponding properties of the liquid crystal compositions are shown in table 6 below.
Table 6: formulation and corresponding Properties of the liquid Crystal composition of example 11
Figure BDA0002093620040000261
Example 12
The formulation and corresponding properties of the liquid crystal compositions are shown in table 7 below.
Table 7: formulation and corresponding Properties of the liquid Crystal composition of example 12
Figure BDA0002093620040000271
Example 13
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 8 below.
TABLE 8 formulation and corresponding Properties of the liquid crystal composition of example 13
Figure BDA0002093620040000272
Figure BDA0002093620040000281
Example 14
The formulation and corresponding properties of the liquid crystal compositions are shown in table 9 below.
TABLE 9 formulation and corresponding Properties of the liquid crystal composition of example 14
Figure BDA0002093620040000282
Comparative example 1
Replacement of I in example 14 with the existing Compound of formula comparative Structure 1
Figure BDA0002093620040000291
The formulation and corresponding properties of the liquid crystal composition are shown in table 10 below.
TABLE 10 formulation and corresponding Properties of the liquid crystal composition of comparative example 1
Figure BDA0002093620040000292
Compare example 14 to comparative example 1, compareClearing Point Cp, refractive indices Δ n, K of example 133With only slight variations. When the liquid crystal compositions of the example 14 and the comparative example 1 are respectively placed in a 10ml glass bottle and stored at-30 ℃ for 120 hours, the liquid crystal composition of the example 14 has no crystal precipitation, and the liquid crystal composition of the comparative example 1 has crystal precipitation, so that the composition of the scheme has good low-temperature intersolubility and can realize a wider working temperature range.
Comparative example 2
Replacement of I in example 12 with the existing Compound of formula comparative Structure 2
Figure BDA0002093620040000293
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 11 below.
TABLE 11 formulation and corresponding Properties of the liquid crystal composition of comparative example 2
Figure BDA0002093620040000301
TABLE 12 reliability data for examples and comparative examples
Numbering VHR/％ VHR(UV)/％ VHR(Heat)/％
Example 12 99.75 98.52 98.55
Comparative example 2 99.70 73.50 83.55
The reliability of the liquid crystal composition was measured by ultraviolet, high temperature aging test and VHR test.
The smaller the VHR data change before and after the ultraviolet and high temperature test of the liquid crystal composition, the stronger the ultraviolet and high temperature resistance. Therefore, the ultraviolet and high temperature resistance was judged by comparing the difference between the VHR data before and after the test in each of examples and comparative examples.
First, before the ultraviolet and high-temperature aging test, VHR data of the liquid crystal composition was measured as initial VHR data, and then, the ultraviolet and high-temperature aging test was performed on the liquid crystal composition, and after the test, VHR data of the liquid crystal composition was measured again.
Ultraviolet aging test: the liquid crystal composition was irradiated with 5000mJ energy under an ultraviolet lamp having a wavelength of 365 nm.
High-temperature aging test: the liquid crystal composition was placed in an oven at 100 ℃ for one hour.
The smaller the change of the VHR data after the aging test relative to the initial VHR data, the stronger the ultraviolet and high temperature resistance of the liquid crystal composition is, so that the stronger the resistance of the liquid crystal composition to the external environment during the working process can be judged, and therefore, the higher the reliability of the liquid crystal composition is.
Comparing example 12 with comparative example 2, comparative example 2 has approximately the same rotational viscosity γ 1 and a lower VHR, and the UV and high temperature resistance of the liquid crystal composition of the present invention is very significant. Therefore, the liquid crystal composition has good reliability and higher response speed.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (10)

1. A liquid crystal compound is characterized in that the liquid crystal compound is shown as the following formula I,
Figure FDA0002093620030000011
wherein R represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms, or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, any of which is-CH not bonded to-O-2-optionally substituted by-O-;
any one or more of the groups represented by R being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Figure FDA0002093620030000012
represents 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene or fluoro-1, 4-phenylene;
p represents 0, 1,2, 3.
2. The liquid crystal compound according to claim 1, wherein the liquid crystal compound is represented by the following formulae I-1 to I-14,
Figure FDA0002093620030000013
Figure FDA0002093620030000021
wherein R represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms, or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, any of which is-CH not bonded to-O-2-optionally substituted by-O-;
any one or more of the groups represented by R being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene.
3. The liquid crystal compound according to claim 1 or 2, wherein the liquid crystal compound is represented by the following formulae I-1-1 to I-14-2,
Figure FDA0002093620030000022
Figure FDA0002093620030000031
4. a liquid crystal composition comprising one or more liquid crystal compounds according to any one of claims 1 to 3.
5. The liquid crystal composition of claim 4, further comprising one or more compounds of formula II,
Figure FDA0002093620030000041
in the formula II, R1、R2Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms,
Figure FDA0002093620030000042
each independently represent
Figure FDA0002093620030000043
6. The liquid crystal composition of claim 4, further comprising one or more compounds of formula III,
Figure FDA0002093620030000044
in the formula III, R3、R4Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, a linear alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted linear alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R3、R4Any one or more non-adjacent-CH2-may be optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z1、Z2each independently represents a single bond, -CH2CH2-or-CH2O-；
Figure FDA0002093620030000045
Each independently represent
Figure FDA0002093620030000046
m represents 1 or 2;
n represents 0, 1 or 2.
7. The liquid crystal composition of any of claims 4 to 6, further comprising one or more compounds of formula IV,
Figure FDA0002093620030000047
wherein R is5、R6Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R5、R6Any one or more non-adjacent-CH2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene; w represents-O-, -S-or-CH2O-。
8. The liquid crystal composition of any one of claims 4 to 7, further comprising one or more compounds of formula V,
Figure FDA0002093620030000051
wherein R is7、R8Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0002093620030000052
each independently represent
Figure FDA0002093620030000053
9. The liquid crystal composition of any one of claims 4 to 8, further comprising one or more compounds of formula VI
Figure FDA0002093620030000054
Wherein R is9、R10Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0002093620030000055
to represent
Figure FDA0002093620030000056
F1、F2、F3Each independently represents H or F, and F2、F3Not simultaneously F.
10. A liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 4 to 9, which is an active matrix display element or a display or a passive matrix display element or a display.
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US5798058A (en) * 1994-07-01 1998-08-25 Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Gt. Britain & N. Ireland Of Defence Evaluation And Research Agency Liquid crystal compounds, mixtures and devices
JP2004217552A (en) * 2003-01-14 2004-08-05 Chisso Corp Compound containing bis(trifluoromethyl)vinyl group, liquid crystal composition and liquid crystal display element
CN107189792A (en) * 2016-03-15 2017-09-22 北京八亿时空液晶科技股份有限公司 A kind of positive and negative mixed liquid crystal composition and its application
CN109722255A (en) * 2017-10-27 2019-05-07 北京八亿时空液晶科技股份有限公司 Containing 2- methyl -3,4, the liquid-crystal composition of 5- trifluoro-benzene structural compounds and its application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5798058A (en) * 1994-07-01 1998-08-25 Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Gt. Britain & N. Ireland Of Defence Evaluation And Research Agency Liquid crystal compounds, mixtures and devices
JP2004217552A (en) * 2003-01-14 2004-08-05 Chisso Corp Compound containing bis(trifluoromethyl)vinyl group, liquid crystal composition and liquid crystal display element
CN107189792A (en) * 2016-03-15 2017-09-22 北京八亿时空液晶科技股份有限公司 A kind of positive and negative mixed liquid crystal composition and its application
CN109722255A (en) * 2017-10-27 2019-05-07 北京八亿时空液晶科技股份有限公司 Containing 2- methyl -3,4, the liquid-crystal composition of 5- trifluoro-benzene structural compounds and its application

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