CN110372480B - Liquid crystal compound with trifluoroethoxy and composition thereof - Google Patents

Liquid crystal compound with trifluoroethoxy and composition thereof Download PDF

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CN110372480B
CN110372480B CN201910724320.4A CN201910724320A CN110372480B CN 110372480 B CN110372480 B CN 110372480B CN 201910724320 A CN201910724320 A CN 201910724320A CN 110372480 B CN110372480 B CN 110372480B
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liquid crystal
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crystal compound
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trifluoroethoxy
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CN110372480A (en
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李建
杜渭松
杨晓哲
莫玲超
万丹阳
高嫒嫒
邓登
李娟利
车昭毅
杨诚
胡明刚
张璐
别国军
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XI'AN CAIJING OPTO-ELECTRICAL SCIENCE & TECHNOLOGY Co.,Ltd.
Xian Modern Chemistry Research Institute
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Xi'an Caijing Opto Electrical Science & Technology Co ltd
Xian Modern Chemistry Research Institute
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    • C09K19/3001—Cyclohexane rings
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3016—Cy-Ph-Ph

Abstract

The invention discloses a liquid crystal compound with high average dielectric constant, which is characterized in that the structure is shown as a general formula (1):
Figure DDA0002158383990000011
wherein R is a linear alkyl or alkoxy group with a carbon number of 1-9 or an alkenyl group with a carbon number of 2-7; ring A is trans-cyclohexane, cyclohexenyl, and the hydrogen atoms on the phenyl ring may be substituted by 1 or more fluorine atoms; n, m is 0, 1, 2; x1、X2Is a hydrogen atom or a fluorine atom; and a liquid crystal composition comprising the general formula (1). The liquid crystal composition has the characteristics of wide liquid crystal phase region, higher average dielectric constant and lower rotational viscosity, and is suitable for TFT liquid crystal display, particularly liquid crystal display modes such as IPS (in-plane switching) mode, FFS (fringe field switching) mode and the like.

Description

Liquid crystal compound with trifluoroethoxy and composition thereof
Technical Field
The invention belongs to the technical field of liquid crystal materials, and particularly relates to a fluorine-containing liquid crystal compound and a composition containing the liquid crystal compound, which are mainly used for a liquid crystal display.
Background
The liquid crystal display has the advantages of flat panel, low power consumption, light weight, no radiation and the like, and is rapidly developed in the field of information display. The liquid crystal display uses the characteristics of optical anisotropy and dielectric anisotropy of a liquid crystal material to realize a display function. The display modes are classified into Twisted Nematic (TN), Super Twisted Nematic (STN), dynamic scattering mode (DSP), thin film transistor driving mode (TFT), and the like. The TFT liquid crystal display can realize full color, high resolution, wide viewing angle, fast response, etc., has been widely used, and is the most important display technology in the current market.
The liquid crystal material for liquid crystal display has a nematic phase within a temperature range of the use environment, generally within a temperature range of-20 ℃ to +70 ℃ or more; meanwhile, the liquid crystal material must have high chemical stability, low viscosity, and suitable application of liquid crystal physical properties such as birefringence, dielectric anisotropy, resistivity and the like. One liquid crystal compound cannot meet all use conditions, and several or even more than ten liquid crystal compounds are compounded to form a mixed liquid crystal material, so that the practical use requirements of a display device can be met.
In the TFT liquid crystal display technology, depending on the liquid crystal alignment method, the liquid crystal display technology can be divided into several modes such as Twisted Nematic (TN), in-plane switching (IPS), Fringe Field Switching (FFS), and vertical alignment VA. The TN mode uses a dielectric anisotropy Δ ε (Δ ε ═ ε)∥－ε⊥) A liquid crystal material that is positive; use of VA modeA liquid crystal material having a negative dielectric anisotropy Δ ∈; in the IPS and FFS modes, a liquid crystal material having a positive dielectric anisotropy Δ ∈ or a liquid crystal material having a negative dielectric anisotropy Δ ∈ may be used. For the FFS mode, a liquid crystal material with negative anisotropy delta epsilon is used, and compared with a liquid crystal material with positive anisotropy delta epsilon, higher light transmittance can be obtained; however, the negative liquid crystal has a large viscosity, and thus the response time is slow and a problem such as an afterimage is likely to occur. With the continuous improvement of the resolution of the display panel, the integral light transmittance of the liquid crystal device is reduced; therefore, the development of a positive liquid crystal material (delta epsilon > 0) with high average dielectric constant is urgently needed to improve the light transmittance of the device; meanwhile, the optimization of the response speed of the liquid crystal display device is also a technical problem, and the development of a liquid crystal material having low rotational viscosity is required.
Patent US20130207038a1 proposes to disclose liquid crystal compositions having high light transmittance characteristics. The composition is prepared by adding a certain amount of liquid crystal compound with negative dielectric anisotropy into a liquid crystal composition with positive dielectric anisotropy, wherein the dielectric anisotropy delta epsilon of the composition is more than 0, and the composition has larger dielectric constant (epsilon) vertical to liquid crystal director⊥) And a larger average dielectric constant (. epsilon.)ave). The liquid crystal compound disclosed therein, which has a negative dielectric anisotropy, has a 2, 3-difluoro-4-alkoxybenzene unit, and a typical molecular structure is as follows:
Figure BDA0002158383980000021
although the liquid crystal compound based on 2, 3-difluoro-4-ethoxybenzene has a large epsilon⊥Value, however ε∥The value is small; and rotational viscosity value (. gamma.)1) Relatively large, adversely affecting the response speed.
Disclosure of Invention
In response to the demand of the FFS mode liquid crystal display technology for a liquid crystal composition with high light transmittance, the invention aims to provide a novel liquid crystal compound with high average dielectric anisotropy and low rotational viscosity and a composition thereof.
In order to realize the task, the invention adopts the following technical solution:
a liquid crystal compound is characterized by the structural formula (1):
Figure BDA0002158383980000022
wherein R is a linear alkyl or alkoxy group with a carbon number of 1-9 or an alkenyl group with a carbon number of 2-7; ring A is trans-cyclohexane, cyclohexenyl, and the hydrogen atoms on the phenyl ring may be substituted by 1 or more fluorine atoms; n, m is 0, 1, 2; x1、X2Is a hydrogen atom or a fluorine atom.
The liquid crystal compound of the invention adopts 2, 3-difluoro-4- (2,2, 2-trifluoroethoxy) benzene to construct a liquid crystal molecular framework, and is characterized in that the dielectric anisotropy delta epsilon is a positive value. The structure not only has high epsilon⊥Value, higher epsilon∥And εaveAnd has the advantages of lower rotational viscosity and wider liquid crystal phase region.
The synthetic route for the compounds of the invention is shown below:
Figure BDA0002158383980000023
the preparation method specifically comprises the following steps:
(1) the compound containing 2, 3-difluoro-4-methoxybenzene or 2, 3-difluoro-4-ethoxybenzene is used as the starting material (the preparation method of the compound is shown in the literature: Angew. chem. int. Ed.,2000,39, 4216-substituted benzene 4235), and alkyl is eliminated under the action of a demethylating/ethyl reagent (R is1A group); said demethylating/ethyl reagent, such as boron tribromide, is reacted at low or room temperature; or heating and refluxing a hydrobromic acid/acetic acid solution with the mass concentration of more than 40% to react to obtain a phenol intermediate.
(2) Reacting the obtained phenol intermediate with trifluoroethanol methane sulfonate, or trifluoroethanol p-toluene sulfonic acid value, or trifluoroethanol trifluoromethane sulfonate to form ether under an alkaline condition to obtain a target product; the alkali can be sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.
The invention can also be prepared according to the following route:
Figure BDA0002158383980000031
the phenol intermediate obtained is reacted with trifluoroethanol, diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD), triphenylphosphine to prepare the compound by Mitsunobu reaction.
The liquid crystal compounds of the general formula (1) according to the invention are preferably selected from the following structures:
Figure BDA0002158383980000032
Figure BDA0002158383980000041
Figure BDA0002158383980000051
Figure BDA0002158383980000061
another object of the present invention is to provide a liquid crystal composition characterized in that the composition comprises at least one liquid crystal compound selected from the group consisting of the liquid crystal compounds represented by the general structural formula (1) as a first component in a mass ratio of 1 to 70% by weight, preferably 3 to 40% by weight, more preferably 5 to 30% by weight.
The second feature of the liquid crystal composition of the present invention is that the composition contains at least one liquid crystal compound selected from the group consisting of liquid crystal compounds represented by the general structural formula (2) as a second component:
Figure BDA0002158383980000062
wherein R is1，R2F, Cl, ring B, ring C, and ring D are benzene rings or cyclohexane, tetrahydropyran, dioxane, etc., wherein the benzene rings may be substituted with 1 or more fluorine atoms, and n is 0, 1. The second component of the composition of the invention is a liquid crystal compound having a smaller or close to 0. DELTA.. epsilon.in a mass proportion of 5 to 80%, preferably 15 to 75%, more preferably 30 to 70% by weight.
Wherein the preferred specific structure of formula (2) is as follows:
Figure BDA0002158383980000063
Figure BDA0002158383980000064
wherein (2) -1 is more preferably of the structure:
Figure BDA0002158383980000071
among them, (2) -2 are more preferably the following specific compounds:
Figure BDA0002158383980000072
among them, (2) -3 are more preferably the following specific compounds:
Figure BDA0002158383980000073
Figure BDA0002158383980000074
among them, (2) to 4 are more preferably the following specific compounds:
Figure BDA0002158383980000075
among them, (2) to 5 are more preferably the following specific compounds:
Figure BDA0002158383980000081
among them, (2) to 6 are more preferably the following specific compounds:
Figure BDA0002158383980000082
the liquid crystal composition of the present invention is characterized in that the composition comprises at least one liquid crystal compound selected from the group consisting of liquid crystal compounds represented by the general structural formula (3) as a third component:
Figure BDA0002158383980000083
wherein R is a straight-chain alkyl group, an alkenyl group, or an alkyl group containing an ethylenic bond, and ring B, ring C, and ring D are a benzene ring, a cyclohexane ring, a tetrahydropyran ring, a dioxane ring, wherein the benzene ring may be substituted with 1 or more fluorine atoms; x1，X2＝H，F；Y＝F，Cl，OCF3，OCF2H, straight-chain alkyl groups or alkyl groups containing an ethylenic bond, etc.; z ═ CF2O，CH2CH2COO, single bond, etc.; n is 0, 1. The third component of the invention is characterized in that the liquid crystal compound with a larger delta epsilon value has a mass proportion of 1-50%, preferably 5-45% by weight, more preferably 10-40%.
Wherein the general formula (3) is preferably of the following specific structure:
Figure BDA0002158383980000091
among them, (3) -1 is preferably a compound:
Figure BDA0002158383980000101
Figure BDA0002158383980000111
among them, (3) -2 is preferably a compound:
Figure BDA0002158383980000112
Figure BDA0002158383980000121
among them, (3) -3 are preferably compounds:
Figure BDA0002158383980000122
among them, (3) -4 are preferred compounds:
Figure BDA0002158383980000123
among them, (3) -5 are preferred compounds:
Figure BDA0002158383980000124
Figure BDA0002158383980000131
among them, (3) -6 are preferred compounds:
Figure BDA0002158383980000132
among them, (3) -7 are preferred compounds:
Figure BDA0002158383980000133
among them, (3) -8 are preferred compounds:
Figure BDA0002158383980000134
among them, (3) to 9 are preferred compounds:
Figure BDA0002158383980000141
among them, (3) -10 are preferred compounds:
Figure BDA0002158383980000142
among them, (3) -11 are preferred compounds:
Figure BDA0002158383980000143
among them, (3) -12 are preferred compounds:
Figure BDA0002158383980000144
among them, (3) -13 are preferred compounds:
Figure BDA0002158383980000151
among them, (3) to 14 are preferred compounds:
Figure BDA0002158383980000152
the liquid crystal composition is characterized by also comprising one or more liquid crystal compounds selected from the liquid crystal compounds shown in the structural general formula (4) as a fourth component:
Figure BDA0002158383980000153
wherein R is1、R2Is a C1-7 linear alkyl or alkoxy group, a C2-7 linear alkenyl or alkenyloxy group, and the ring B, the ring C and the ring D are benzene rings, cyclohexane and tetrahydropyrane rings, wherein the benzene rings can be substituted by 1 or more fluorine atoms; x1，X2H, F; z being a single bond, CH2CH2，CH2O; n is 0, 1. The fourth component of the invention is a liquid crystal material with negative delta epsilon, and the mass proportion of the liquid crystal material is 0-30%, preferably 2-20% by weight, and more preferably 3-15%.
Wherein the general formula (4) is preferably of the following specific structure:
Figure BDA0002158383980000154
among them, (4) -1 is preferably a compound:
Figure BDA0002158383980000155
among them, (4) -2 are preferred compounds:
Figure BDA0002158383980000161
among them, (4) -3 are preferred compounds:
Figure BDA0002158383980000162
among them, (4) -4 are preferred compounds:
Figure BDA0002158383980000163
among them, (4) -5 are preferably the following compounds:
Figure BDA0002158383980000164
the liquid crystal composition can also comprise one or more chiral additives, and the content is 0.01-1%; preferably 0.1% to 0.5%. The chiral additive is preferably selected from the following structures:
Figure BDA0002158383980000171
the liquid crystal composition also comprises a plurality of hindered phenols as antioxidant stabilizers, and the content of the hindered phenols is 1ppm-10000 ppm; preferably from 10ppm to 1000 ppm. The antioxidant stabilizer is preferably selected from the following structures:
Figure BDA0002158383980000172
the liquid crystal composition also comprises one or more ultraviolet light stabilizers with the content of 1ppm to 10000 ppm; preferably from 10ppm to 1000 ppm. The ultraviolet light stabilizer is preferably selected from the following structures:
Figure BDA0002158383980000173
the invention may further comprise one or more liquid crystal components having a polymerizable group in an amount of 1ppm to 10000 ppm; preferably 100ppm to 1000 ppm. The polymerizable liquid crystal component is preferably selected from the following structures:
Figure BDA0002158383980000174
the liquid crystal composition has larger average dielectric constant, lower rotational viscosity and faster response speed, and is suitable for TFT liquid crystal display technology, especially FFS and IPS modes.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
The preparation method of the liquid crystal formula comprises the following steps: a thermal dissolution method is used. Firstly, weighing monomer liquid crystals with different weight proportions by using a precision balance, heating to 60-100 ℃, and stirring and mixing for 1-2 hours to uniformly dissolve all components. Cooling, filtering, degassing the filtered liquid in high vacuum (less than or equal to 100Pa), and packaging with high-purity nitrogen to obtain the target mixed liquid crystal.
Unless otherwise specified, the liquid crystal compositions according to the invention are prepared according to this process.
And testing the physical property and the photoelectric property of the mixed liquid crystal. The detailed test method of the physical property and the photoelectric property comprises the following steps:
(1) clearing point (Tni):
the polarizing hot stage method: the liquid crystal sample was coated on a glass slide and placed in an orthogonal polarization microscope hot stage with a temperature rise rate of 2 ℃/min. And observing the temperature at which the liquid crystal sample turns black from a bright state in a polarizing microscope, namely the clearing point.
Or by differential scanning calorimetry: the heating rate was set at 2 ℃/min under nitrogen atmosphere.
(2) Low temperature storage temperature (LTS): about 1mL of the mixed liquid crystal was put into a transparent glass bottle and placed in a low-temperature refrigerator. The temperature is set to-20 ℃, 30 ℃ and 40 ℃, and the mixture is stored for 10 days respectively, and whether crystal precipitation or smectic phase exists is observed. If no crystal is precipitated at the temperature of minus 30 ℃, LTS is less than or equal to minus 30 ℃.
(3) Birefringence (Δ n): respectively measuring ordinary rays (n) by using Abbe refractometer at constant temperature of 25 DEG Co) And extraordinary ray (n)e) Refractive index of (1), birefringence (Δ n) being equal to ne－no。
(4) Dielectric constant (Δ ∈): and (3) testing by using an LCR (liquid crystal resistance) meter at the constant temperature of 25 ℃. Δ ε ═ ε∥-ε⊥I.e. the dielectric constant (. epsilon.) in the direction of the molecular long axis∥) Dielectric constant (. epsilon.) with respect to the minor axis of the molecule⊥) The difference of (a).
(5) Spring constant (K)11，K33): under the constant temperature condition of 25 ℃, K is obtained by testing a liquid crystal capacitance-voltage (C-V) curve and fitting11And K33。
(6) Rotational viscosity (. gamma.)1): under the constant temperature condition of 25 ℃, the transient current value Ip of the liquid crystal molecules deflected along with the movement of the electric field is tested by applying voltage to the liquid crystal test box, and the rotational viscosity gamma is calculated1。
The performance of the monomer liquid crystal was tested by dissolving it in the following basic formulation (Host). The property parameters of the monomers, e.g. clearing point, Δ ε, Δ n, γ1Calculated by extrapolation. The basic formula (Host) is prepared from the following three liquid crystal compounds according to the mass ratio of 1:1: 1.
Figure BDA0002158383980000181
Code number and description:
(1) physical parameters
Figure BDA0002158383980000182
Figure BDA0002158383980000191
(2) Structural abbreviations
Figure BDA0002158383980000192
For example:
Figure BDA0002158383980000193
Figure BDA0002158383980000201
liquid crystal phase transition temperature: c represents melting point, S represents smectic phase, N represents nematic phase, and Iso represents liquid state.
Abbreviation of reagents:
DMF N, N-dimethylformamide
CF3CH2OMs trifluoroethanol methanesulfonate
DEAD azodicarboxylic acid diethyl ester
Example 1:
synthesis of 2, 3-difluoro-1- (4-propylcyclohexyl) -4- (2,2, 2-trifluoroethoxy) benzene
The reaction equation is as follows:
Figure BDA0002158383980000202
the specific synthesis steps are as follows:
(1) synthesis of 2, 3-difluoro-1- (4-propylcyclohexyl) -phenol
In a 500mL three-necked flask, 2, 3-difluoro-1- (4-propylcyclohexyl) -4-ethoxybenzene (14.0g, 0.05mol) and 80mL of methylene chloride were added, the temperature was lowered to-10 ℃ and BBr was added dropwise3After the solution is dripped, the temperature is naturally raised to the room temperature, and after the reaction is carried out for 3 hours, water is slowly dripped to quench the reaction. Standing, separating, washing the organic phase to neutrality, drying with anhydrous sodium sulfate, filtering, and spin-drying to obtain light yellow solid. 1g of n-heptane: 2ml of the solution was recrystallized to obtain 12g of white crystals. The GC content was 99.9% and the yield was 95.4%.
(2) Synthesis of 2, 3-difluoro-1- (4-propylcyclohexyl) -4- (2,2, 2-trifluoroethoxy) benzene
Into a 250mL three-necked flask, 2, 3-difluoro-1- (4-propylcyclohexyl) -phenol (8.9g, 0.035mol), anhydrous potassium carbonate (9.66g, 0.07mol), CF were added3CH2OSO2CH3(6.54g, 0.037mol) and DMF (50mL) were heated to 130 ℃ with stirring for 8 h. The temperature was lowered to room temperature, and 100ml of water and 50ml of toluene were added thereto, followed by extraction with 2. Washing the organic phase twice, drying the organic phase by anhydrous sodium sulfate, filtering the organic phase, and spin-drying the filtrate to obtain light yellow oily liquid. Dissolving the crude product with n-heptane, passing through silica gel column, and subjecting to n-heptaneAnd (5) eluting with alkane, and spin-drying to obtain colorless oily liquid. Ethanol was added for recrystallization to give 8.8g of white crystalline product. GC content 99.9% and yield 75%.
The structure identification data is as follows:
1HNMR(CDCl3，500MHz)δ：6.904～6.867(m，1H)，6.760～6.724(m，1H)，4.418～4.369(m，2H)，2.797～2.735(m，1H)，1.868～1.831(m，4H)，1.477～1.393(m，2H)，1.366～1.254(m，3H)，1.235～1.189(m，2H)，1.108～1.026(m，2H)，0.914～0.885(t，3H，J＝7.5Hz)。
MS(70eV)m/z(％)：238.1(100)，225.1(50.78)，336.2(M+，49.91)，251.1(35.48)，252.1(19.53)，239.1(14.26)，155.1(10.96)，43.2(10.48)。
physical property test data are as follows:
melting point by DSC: c43.53 Iso.
Dissolving the compound into a basic formula by the mass ratio of 15% for physical property test, and extrapolating to obtain the following performance parameters: t isni＝-67.2℃；Δn＝0.0564；ε⊥＝9.152，ε∥＝13.137，εave＝10.48，Δε＝3.985；γ1＝-55.3mPa·s。
Example 2: the synthesis reaction equation of 2, 3-difluoro-1- (4-pentylcyclohexyl) -4- (2,2, 2-trifluoroethoxy) benzene is shown as follows:
Figure BDA0002158383980000211
in the same manner as in example 1, 2, 3-difluoro-1- (4-pentylcyclohexyl) -4- (2,2, 2-trifluoroethoxy) benzene was obtained.
The structure identification data is as follows:
1H NMR(δ，CDCl3)：6.904～6.867(m，1H)，6.760～6.724(m，1H)，4.419～4.371(dd，2H，J1＝16Hz，J2＝8Hz)，2.796～2.735(m，1H)，1.872～1.824(m，4H)，1.474～1.390(m，2H)，1.348～1.198(m，9H)，1.107～1.025(m，2H)，0.907～0.879(t，3H，J＝7.5Hz)；
MS(70eV)m/z(％)：238.1(100)，364.3(M+，61.78)，225.1(58.18)，251.1(22.78)，252.1(17.73)，239.1(14.29)，365.3(14.26)，71.1(11.48)。
physical property test data are as follows:
melting point by DSC: c48.53 Iso.
Dissolving the compound into a basic formula by the mass ratio of 10% for physical property test, and extrapolating to obtain the following performance parameters: t isni＝-52.4℃；Δn＝0.0601；ε⊥＝8.882，ε∥＝11.524，εave＝9.763，Δε＝2.632；γ1＝-12mPa·s。
Example 3: synthesis of 2, 3-difluoro-4' -propyl-4- (2,2, 2-trifluoroethoxy) biphenyl
2,3-difluoro-4'-propyl-4-(2,2,2-trifluoroethoxy)biphenyl
Figure BDA0002158383980000221
In the same manner as in example 1, 2, 3-difluoro-4' -propyl-4- (2,2, 2-trifluoroethoxy) biphenyl was obtained.
The structure identification data is as follows:
1H NMR(δ，CDCl3)：7.420～7.401(m，2H)，7.267～7.251(m，2H)，7.146～7.108(m，1H)，6.879～6.843(m，1H)，4.490～4.442(dd，2H，J1＝16Hz，J2＝8Hz)，2.648～2.617(m，2H)，1.719～1.645(m，2H)，0.989～0.960(t，3H，J＝7.5Hz)；
MS(70eV)m/z(％)：301.2(100)，330.2(M+，47.84)，218.1(21.36)，302.2(20.02)，190.1(14.58)。
physical property test data are as follows:
melting point by DSC: c59.81 Iso.
Dissolving the compound into a basic formula by the mass ratio of 10% for physical property test, and extrapolating to obtain the following performance parameters:Tni＝-73.6℃；Δn＝0.1202；ε⊥＝10.938，ε∥＝14.25，εave＝9.763，Δε＝3.312；γ1＝-101mPa·s。
example 4: synthesis of 4- (2, 3-difluoro-4- (2,2, 2-trifluoroethoxy) phenyl) -4' -propylbicyclohexane
4-(2,3-difluoro-4-(2,2,2-trifluoroethoxy)phenyl)-4'-propylbi(cyclohexane)
Figure BDA0002158383980000222
In the same manner as in example 1, 4- (2, 3-difluoro-4- (2,2, 2-trifluoroethoxy) phenyl) -4' -propylbicyclohexane was obtained.
The structure identification data is as follows:
1H NMR(δ，CDCl3)：6.898～6.862(m，1H)，6.758～6.721(m，1H)，4.418～4.369(dd，2H，J1＝16.5Hz，J2＝8.5Hz)，2.771～2.717(m，1H)，1.877～1.826(t，4H，J＝13.5Hz)，1.775～1.719(t，4H，J＝13.5Hz)，1.447～1.379(m，2H)，1.346～1.274(m，2H)，1.206～1.136(m，6H)，1.098～0.957(m，3H)，0.890～0.826(m，5H)；
MS(70eV)m/z(％)：418.4(M+，100)，225.1(79.86)，238.1(79.02)，69.1(46.18)，83.1(35.02)，55.1(17.4)，125.1(13.96)，81.1(12.6)，239.1(10.97)，251.1(10.27)。
physical property test data are as follows:
melting point by DSC: C106.4N 142.56 Iso.
The compound is dissolved into a basic formula by the mass ratio of 5% for physical property test, and performance parameters are obtained by extrapolation: t isni＝120.3℃；Δn＝0.0971；ε⊥＝9.142，ε∥＝11.754，εave＝10.013，Δε＝2.612；γ1＝296mPa·s。
Example 5: synthesis of 4' -propylcyclohexyl-2, 3-difluoro-4- (2,2, 2-trifluoroethoxy) biphenyl
Figure BDA0002158383980000231
In the same manner as in example 1, 4' -propylcyclohexyl-2, 3-difluoro-4- (2,2, 2-trifluoroethoxy) biphenyl was obtained.
The structure identification data is as follows:
1H NMR(δ，CDCl3)：6.887～6.850(m，1H)，6.716～6.679(m，1H)，6.207～5.970(m，1H)，4.254～4.194(m，2H)，2.762～2.708(m，1H)，1.876～1.823(t，4H，J＝14Hz)，1.775～1.718(t，4H，J＝13.5Hz)，1.444～1.377(m，2H)，1.346～1.273(m，2H)，1.205～1.148(m，6H)，1.097～0.957(m，3H)，0.890～0.826(m，5H)；
MS(70eV)m/z(％)：412.3(M+，100)，314.1(51.39)，327.2(45.71)，301.1(29.92)，231.1(21.4)，328.2(16.23)，228.1(11.01)，315.1(10.39)。
physical property test data are as follows:
melting point by DSC: C90.59SA 123.66 N 128.0 Iso。
Dissolving the compound into a basic formula by the mass ratio of 10% for physical property test, and extrapolating to obtain the following performance parameters: t isni＝102.4℃；Δn＝0.1362；ε⊥＝9.291，ε∥＝13.576，εave＝10.719，Δε＝4.276；γ1＝192mPa·s。
Example 6: synthesis of 4 '-propylcyclohexyl-2, 2', 3-trifluoro-4- (2,2, 2-trifluoroethoxy) biphenyl
Figure BDA0002158383980000241
In the same manner as in example 1, 4 '-propylcyclohexyl-2, 2', 3-trifluoro-4- (2,2, 2-trifluoroethoxy) biphenyl was obtained.
The structure identification data is as follows:
1H NMR(δ，CDCl3)：7.264～7.234(m，1H)，7.100～7.056(m，2H)，7.032～7.006(m，1H)，6.884～6.848(m，1H)，4.500～4.452(dd，2H，J1＝16Hz，J2＝8Hz)，2.543～2.482(m，1H)，1.941～1.876(m，4H)，1.495～1.414(m，2H)，1.392～1.270(m，3H)，1.245～1.199(m，2H)，1.100～1.020(m，2H)，0.923～0.894(t，3H，J＝7Hz)；
MS(70eV)m/z(％)：430.3(100)，332.1(57.27)，319.1(31.22)，431.3(28.16)，249.1(18.69)，345.1(15.41)，333.1(12.39)，346.1(11.34)。
physical property test data are as follows:
melting point by DSC: C75.55N 77.40 Iso.
Dissolving the compound into a basic formula by the mass ratio of 10% for physical property test, and extrapolating to obtain the following performance parameters: t isni＝74.2℃；Δn＝0.1301；ε⊥＝9.342，ε∥＝14.414，εave＝10.719，Δε＝5.072；γ1＝237mPa·s。
Example 7: synthesis of 2, 3-difluoro-1- (4- (4-propylcyclohexyl) cyclohex-1-enyl) -4- (2,2, 2-trifluoroethoxy) benzene
Figure BDA0002158383980000242
The intermediate 2, 3-difluoro-1- (4- (4-propylcyclohexyl) cyclohex-1-enyl) -4-phenol was prepared by the same procedure as in example 1.
3.3g of 2, 3-difluoro-1- (4- (4-propylcyclohexyl) cyclohex-1-enyl) -4-phenol, 2.1g of diethyl azodicarboxylate and 3.1g of triphenylphosphine were dissolved in 30ml of tetrahydrofuran, and the temperature was reduced to 0 ℃ and a solution of 1.4g of trifluoroethanol in 20ml of tetrahydrofuran was added dropwise. After the dropwise addition, the mixture was slowly warmed to room temperature and stirred for 4 hr. The reaction mixture was poured into water, and 50ml of toluene was added thereto for extraction. The organic phase was dried and the solvent was removed under reduced pressure. Dissolving the crude product with n-heptane, passing through silica gel column, eluting with n-heptane, and spin drying to obtain white solid. Ethanol was added thereto for recrystallization to obtain 3.4g of white crystals. GC content 99.9% and yield 82%.
The structure identification data is as follows:
1HNMR(δ，CDCl3)：6.93–6.89(m,1H),6.75–6.71(m,1H),5.93(t,J＝2.5Hz,1H),4.41(q,J＝8.0Hz,2H),2.40–2.22(m,3H),1.98–1.89(m,2H),1.83–1.75(m,4H),1.44–1.28(m,4H),1.20–1.11(m,4H),1.07–0.96(m,2H),0.91–0.84(m,5H).
MS(70eV)m/z(％)：416.1(M+,54.5),276.9(100),224.9(73.9),69.0(68.3),273.9(67.3),180.9(48.0),55.1(40.9)。
physical property test data are as follows:
melting point by DSC: C102.41S 121.70N 138.49 Iso.
Dissolving the compound into a basic formula by the mass ratio of 10% for physical property test, and extrapolating to obtain the following performance parameters: t isni＝117.4℃；Δn＝0.0732；ε⊥＝8.188，ε∥＝10.65，εave＝9.01，Δε＝2.532；γ1＝251mPa·s。
Example 8 (composition)
Figure BDA0002158383980000251
Example 9 (composition)
Figure BDA0002158383980000261
Example 10 (composition)
Figure BDA0002158383980000262
Example 11 (composition)
Figure BDA0002158383980000271
Comparative example 1:
a 2, 3-difluoro-4-ethoxybenzene-containing liquid crystal compound represented by the following formula:
Figure BDA0002158383980000272
adding the mixture into a basic formula HOST according to a mass ratio of 15%, carrying out physical property test, and extrapolating to obtain the following performance parameters: t isni＝-27.2℃；Δn＝0.0771；ε⊥＝11.782，ε∥＝7.461，εave＝10.34，Δε＝-4.321；γ1＝25mPa·s。
Example 1 of the present invention had a significantly increased ε as compared to comparative example 1∥Δ ε is a positive value, the polarity is reversed, εaveIncreasing; and gamma1And (4) greatly reducing.
Comparative example 2:
a 2, 3-difluoro-4-ethoxybenzene-containing liquid crystal compound represented by the following formula:
Figure BDA0002158383980000273
adding the mixture into a basic formula HOST according to the mass ratio of 10%, carrying out physical property test, and extrapolating to obtain the following performance parameters: t isni＝176.0℃；Δn＝0.1683；ε⊥＝9.991，ε∥＝6.887，εave＝8.956，Δε＝-2.935；γ1＝255.9mPa·s。
Example 5 of the present invention has a significantly increased ε compared to comparative example 2∥Δ ε is a positive value, the polarity is reversed, εaveIncreasing; and gamma1And (4) greatly reducing.
Comparative example 3:
patent DE4222371 discloses liquid-crystalline compounds of the following structure:
Figure BDA0002158383980000281
the liquid crystal compounds are different from the present invention in the substitution position of fluorine atom on benzene ring.
The compound was prepared according to the method described in patent DE4222371, the structural identification data being as follows:
1H NMR(δ，CDCl3)：6.781～6.741(m，2H)，4.428～4.378(dd，2H，J1＝16.5H

Claims (5)

1. a liquid crystal compound having a high average dielectric constant, characterized by having a structure represented by general formula (1):
Figure 95806DEST_PATH_IMAGE002
（1）
wherein R is a linear alkyl or alkoxy group with a carbon number of 1-9 or an alkenyl group with a carbon number of 2-7; ring A is trans-cyclohexane or cyclohexenyl; n, m =0, 1, 2; x1、X2Is a hydrogen atom or a fluorine atom; and when m =0, R is alkenyl, ring a is not cyclohexenyl.
2. The liquid crystal compound according to claim 1, characterized in that n =1 and m = 0.
3. The liquid crystal compound according to claim 1, characterized in that n =1 and m = 1.
4. A nematic liquid crystal composition is characterized by comprising a liquid crystal compound as a first component, wherein the liquid crystal compound has a structural general formula (1) and is contained in an amount of 1-70%:
Figure DEST_PATH_IMAGE003
（1）
wherein R, ring A, n, m, X1、X2Is as defined in claim 1.
5. A liquid crystal display element comprising the liquid crystal composition according to claim 4.
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Citations (8)

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DE4142519A1 (en) * 1991-01-31 1992-08-06 Merck Patent Gmbh New fluoro-benzene derivs. - useful as components of liq. crystal media for LC and electro=optical display elements
EP1903090A2 (en) * 2006-09-06 2008-03-26 Chisso Corporation Cyclohexene derivative having alkenyl, liquid crystal composition and liquid crystal display device
CN101868439A (en) * 2007-09-06 2010-10-20 智索株式会社 Tetra- or penta-cyclic liquid crystalline compound having lateral fluorine, liquid crystal composition, and liquid crystal display element
CN104004527A (en) * 2014-05-07 2014-08-27 北京八亿时空液晶科技股份有限公司 Liquid crystal compound and its preparation method and use
CN104086376A (en) * 2014-07-21 2014-10-08 西安近代化学研究所 Liquid crystal midbody containing difluoro methyl ether bridged bond and synthesis method thereof
CN108003895A (en) * 2016-10-28 2018-05-08 西安近代化学研究所 A kind of nematic phase liquid crystal composition and its display element
CN108949190A (en) * 2017-05-17 2018-12-07 北京八亿时空液晶科技股份有限公司 A kind of liquid-crystal composition containing cyclohexene compound and its application
CN109401758A (en) * 2017-08-16 2019-03-01 石家庄诚志永华显示材料有限公司 A kind of liquid-crystal compounds and liquid-crystal composition

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4142519A1 (en) * 1991-01-31 1992-08-06 Merck Patent Gmbh New fluoro-benzene derivs. - useful as components of liq. crystal media for LC and electro=optical display elements
EP1903090A2 (en) * 2006-09-06 2008-03-26 Chisso Corporation Cyclohexene derivative having alkenyl, liquid crystal composition and liquid crystal display device
CN101868439A (en) * 2007-09-06 2010-10-20 智索株式会社 Tetra- or penta-cyclic liquid crystalline compound having lateral fluorine, liquid crystal composition, and liquid crystal display element
CN104004527A (en) * 2014-05-07 2014-08-27 北京八亿时空液晶科技股份有限公司 Liquid crystal compound and its preparation method and use
CN104086376A (en) * 2014-07-21 2014-10-08 西安近代化学研究所 Liquid crystal midbody containing difluoro methyl ether bridged bond and synthesis method thereof
CN108003895A (en) * 2016-10-28 2018-05-08 西安近代化学研究所 A kind of nematic phase liquid crystal composition and its display element
CN108949190A (en) * 2017-05-17 2018-12-07 北京八亿时空液晶科技股份有限公司 A kind of liquid-crystal composition containing cyclohexene compound and its application
CN109401758A (en) * 2017-08-16 2019-03-01 石家庄诚志永华显示材料有限公司 A kind of liquid-crystal compounds and liquid-crystal composition

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