CN112391171B - Liquid crystal composition having positive dielectric anisotropy and liquid crystal display device thereof - Google Patents

Liquid crystal composition having positive dielectric anisotropy and liquid crystal display device thereof Download PDF

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CN112391171B
CN112391171B CN201910749190.XA CN201910749190A CN112391171B CN 112391171 B CN112391171 B CN 112391171B CN 201910749190 A CN201910749190 A CN 201910749190A CN 112391171 B CN112391171 B CN 112391171B
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CN112391171A (en
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姚利芳
丁文全
徐海彬
贺笛
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Jiangsu Hecheng Display Technology Co Ltd
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/46Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
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    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0474Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CHFO- chain
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

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Abstract

The present invention discloses a liquid crystal composition having positive dielectric anisotropy, the liquid crystal composition comprising: at least one compound of the formula I, at least one compound of the formula N and at least one compound of the formula M. The invention also discloses a liquid crystal display device comprising the liquid crystal composition. The liquid crystal composition of the invention has higher optical anisotropy, higher absolute value of dielectric anisotropy and larger epsilon Greater average elastic constant, greater transmittance, a wider operating temperature range (i.e., higher clearing point and lower nematic lower limit temperature), and better low temperature miscibility; in particular, when the Δε level is improved by about 50%, the liquid crystal molecular ordering is good, and the K value can be maintained at a significantly high level, thereby achieving higher transmittance.

Description

Liquid crystal composition having positive dielectric anisotropy and liquid crystal display device thereof
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition with positive dielectric anisotropy and a liquid crystal display device thereof.
Background
Liquid crystal displays (Liquid Crystal Display, LCD) have been rapidly developed due to their small size, light weight, low power consumption and excellent display quality, and have been widely used, particularly, in portable electronic information products. With the increase in the size of liquid crystal screens for portable computers, office applications, video applications, in order to enable the liquid crystal display to be used for large-screen display and eventually replace Cathode Ray Tubes (CRTs), there are still some problems to be solved, such as improvement of viewing angle characteristics, improvement of response speed, increase of contrast ratio, improvement of transmittance, and the like. The narrower viewing angle of the LCD means that the contrast ratio is significantly reduced when the LCD is viewed away from the normal direction perpendicular to the liquid crystal cell, and the gray scale and color inversion phenomenon occurs when the viewing angle is large, which seriously affects the display quality of the LCD, so that the problem of viewing angle becomes a big obstacle for the LCD to replace CRT technology.
The viewing angle problem of the LCD is determined by the operating principle of the liquid crystal. The liquid crystal molecules themselves are rod-shaped, and different molecular arrangements correspond to different optical anisotropies. The smaller the angle between the incident light and the liquid crystal molecules, the smaller the birefringence; conversely, the greater the birefringence. Light rays entering the liquid crystal box at different angles from the normal direction of the display screen have different included angles with directors of liquid crystal molecules, so that the effective optical path difference delta n is different under different viewing angles. However, the optimum optical path difference of the liquid crystal cell is designed in a direction perpendicular to the normal line of the liquid crystal cell, and for obliquely incident light rays, the minimum transmittance increases with increasing angle, and at the same time, the contrast ratio decreases, and when the angle is sufficiently large, even contrast ratio reversal occurs.
Currently, a variety of approaches to solve the viewing angle problem have been proposed, such as: optically compensated bend (optically compensated bend, OCB) mode, in-plane switching (IPS) mode, fringe field switching (fringe field switching, FFS) mode, and multi-domain homeotropic alignment (MVA) mode, among others. They all have respective advantages and disadvantages: the MVA mode has the characteristics of high contrast and quick response, but it requires one biaxial compensation film and two elliptical polarizers, and thus is costly; in the OCB mode, it is difficult to maintain stable control by using ac voltage, the transmittance of three kinds of monochromatic light for R, G, B is different, in addition, in the field-free condition, the molecules in the liquid crystal cell are arranged in a direction parallel to the substrate, in order to implement bending arrangement, a voltage of several seconds is required to be applied to the cell for presetting, and then the arrangement mode can be maintained under a lower voltage, which is inconvenient to use; the IPS mode requires only a linear polarizer and no compensation film, but its response speed is too slow to display a fast moving picture. Since the IPS mode and FFS mode are simple to manufacture and have a wide viewing angle, they are the most attractive methods capable of improving viewing angle characteristics and realizing a large-area display.
In the beginning of the last 70 th century, experimental studies have been made on the basic electro-optical characteristics of the uniformly aligned and twisted nematic liquid crystal IPS mode, which is characterized in that a pair of electrodes are formed on the same substrate and the other substrate has no electrode, and the alignment of liquid crystal molecules is controlled by a transverse electric field applied between the pair of electrodes, so that this mode is also called a transverse field mode. In the IPS mode, nematic liquid crystal molecules are aligned uniformly and parallel between two substrates, and two polarizers are placed orthogonally. In the IPS mode, when no electric field is applied, incident light is blocked by two orthogonal polarizers to be in a dark state, and when an electric field is applied, liquid crystal molecules are rotated to cause retardation, so that light leaks from the two orthogonal polarizers.
The IPS mode may use a positive liquid crystal or a negative liquid crystal. Since the driving voltage required for the transmittance to reach 100% decreases with an increase in the absolute value of Δε, the driving voltage required for the transmittance of positive liquid crystal to reach 100% is lower than that of negative liquid crystal, and the response speed is faster. However, the transmittance of the negative liquid crystal is better than that of the positive liquid crystal, mainly because the alignment of liquid crystal molecules in a liquid crystal cell is different in the positive and negative IPS modes, and the alignment and rotation of the liquid crystal molecules are different when power is applied. The positive liquid crystal molecules are affected by the fringe vertical electric field, and the effective Δn×d is reduced, so that the transmittance of the positive IPS mode is lower than that of the negative IPS mode under the power-up condition. In view of the slow response speed in the case of using a negative liquid crystal, it is highly desirable to maximize the transmittance in the positive IPS mode.
Transmission rate formula according to IPS mode Transmitttance (T) +|Deltaε|/ε (wherein ". Alpha." represents an "inverse proportion" relationship, and Δε represents dielectric anisotropy, ε) For a dielectric constant perpendicular to the molecular axis), attempts may be made to reduce the Δεof the liquid crystal medium, but one to increase the transmittance of positive liquid crystalsThe driving voltage of the same product has a limited adjustment range. In addition, the liquid crystal molecules are inclined to the Z-axis direction under the action of the vertical component of the fringe electric field, so that the optical anisotropy delta n of the liquid crystal molecules is changed according to the formula(wherein χ is the angle between the optical axis of the liquid crystal layer and the optical axis of the polarizer, Δn is the optical anisotropy, d is the cell spacing, λ is the wavelength), it is known that the effective Δn×d affects T, and increasing Δn×d is also considered to increase the transmittance of positive liquid crystals, but the retardation design of each product is fixed.
In view of the above, a common way to increase the transmittance of the liquid crystal material in the positive IPS mode can be considered as follows: (1) The dielectric anisotropy delta epsilon of the liquid crystal composition is kept unchanged by increasing epsilon The penetration rate can be effectively improved; (2) The value of the elastic constant K of the liquid crystal composition is improved, so that the order degree of liquid crystal molecules is better, light leakage is less, and the transmittance is improved. In order to maintain a sufficiently high transmittance, the absolute value of dielectric anisotropy of most of the liquid crystal compositions in the prior art is low, so that the threshold voltage of a liquid crystal display device including such a liquid crystal composition is high, and as a result, the energy saving and environmental protection properties of the liquid crystal display device are affected. However, since the liquid crystal molecules of the liquid crystal composition having a low threshold voltage generally contain a large dielectric polar group, the order of the liquid crystal molecules is reduced, and the value of the elastic constant K is also reduced, thereby affecting the light leakage and contrast of the liquid crystal material, which are generally difficult to be compatible. In the currently known liquid crystal materials with smaller power consumption, the value of the elastic constant K is not large enough, epsilon The penetration rate is not high enough due to low, and when other performances are similar, the working temperature range is small, so that the high-contrast-ratio high-performance vehicle-mounted product cannot be applied to some vehicle-mounted products requiring high contrast ratio.
Disclosure of Invention
The invention aims to: in view of the drawbacks of the prior art, an object of the present invention is to provide a dielectric material having a higher optical anisotropy, a higher absolute value of dielectric anisotropy,Greater epsilon A larger average elastic constant, a larger transmittance, a wider working temperature range (i.e., a higher clearing point and a lower nematic phase lower limit temperature), and a better low temperature miscibility. The invention also aims to provide a liquid crystal display device comprising the liquid crystal composition.
The technical scheme of the invention is as follows:
in order to achieve the above object, the present invention provides a liquid crystal composition having positive dielectric anisotropy, the liquid crystal composition comprising:
at least one compound of the formula I
At least one compound of the formula N
And
At least one compound of the formula M
Wherein,,
R 1 represents a linear or branched alkyl group having 1 to 12 carbon atoms,1 or non-adjacent more than 2-CH in the straight-chain or branched alkyl group containing 1-12 carbon atoms 2 -can be replaced independently of one another by-ch=ch-, -c≡c-, -O-, -CO-O-or-O-CO-, and the straight-chain or branched alkyl radical having 1 to 12 carbon atoms, -or>Wherein one or more of-H's may be independently replaced by-F or-Cl;
R x represents-O-or-CH 2 -;
R N1 And R is N2 Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or non-adjacent more than 2-CH in the straight-chain or branched alkyl group containing 1-12 carbon atoms 2 -may each be independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
R M1 and R is M2 Each independently represents-H, a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or non-adjacent more than 2-CH in the straight-chain or branched alkyl group containing 1-12 carbon atoms 2 -may each be independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
ring(s)And (C) a ring->Each independently represents->Wherein,,one or more of-CH 2 Can be replaced by-O-, single bonds in one or more rings can be replaced by double bonds,in which one or more of-H may be substituted by-CN, -F or-Cl and one or more of-ch=may be substituted by-n=in the ring;
ring(s)Ring->And (C) a ring->Each independently represents-> Wherein (1)>One or more of-CH 2 -can be replaced by-O->At most one-H of (c) may be substituted by halogen;
Z N1 and Z N2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH=CH-、-C≡C-、-CH 2 CH 2 -、-(CH 2 ) 4 -、-CF 2 O-、-OCF 2 -or-CF 2 CF 2 -;
Z M1 And Z M2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH=CH-、-C≡C-、-CH 2 CH 2 -or- (CH) 2 ) 4 -;
n N1 Represents 0, 1, 2 or 3, n N2 Represents 0 or 1, and 0.ltoreq.n N1 +n N2 Not more than 3, and when n N1 When=2 or 3, the ringZ, which may be the same or different N1 May be the same or different;
n M1 represents 0, 1, 2 or 3, and when n M1 When=2 or 3, the ringZ, which may be the same or different M2 May be the same or different;
at least one of the compounds of formula N satisfies any one of the following conditions:
a:Z N1 and Z N2 At least one of which is not a single bond;
b: when n is N1 Represents 2 and n N2 When 0 is represented, the ringAll are not +.>
In some embodiments of the invention, the absolute value of the dielectric anisotropy of the compound of formula M does not exceed 3.
In some embodiments of the invention, the compounds of formula I comprise from 0.1 to 40% by weight of the total liquid crystal composition.
Regarding the preferred content of the compounds of formula I: the preferred lower limit of the content of the compounds of the formula I is 0.1%,0.5%,1%,2%,3%,4%,5%,7%,8%,9%,10%,11%,12%,13%,14% or 15% relative to the total weight of the liquid-crystalline composition according to the invention; the preferred upper limit of the content of the compounds of the formula I is 40%,35%,30%,28%,27%,26%,25.5%,25%,24.5%,24%,22% or 20% relative to the total weight of the liquid-crystalline composition according to the invention.
In some embodiments of the invention, in the compounds of formula I, R 1 Preferably a straight chain containing 1 to 8 carbon atomsOr branched alkyl or alkoxy, straight or branched alkenyl or alkenyloxy containing 2 to 8 carbon atoms; further preferred are straight or branched alkyl or alkoxy groups having 1 to 5 carbon atoms, straight or branched alkenyl or alkenyloxy groups having 2 to 5 carbon atoms.
In some embodiments of the invention, the compound of formula i is selected from the group consisting of:
and
Wherein,,
R 1 represents a linear alkyl group having 2 to 5 carbon atoms,
In some embodiments of the present invention, the liquid crystal composition of the present invention preferably contains at least one compound of formula I-1, and more preferably contains at least two compounds of formula I-1.
In some embodiments of the present invention, the liquid crystal composition of the present invention preferably contains at least one compound of formula I-2, and more preferably contains at least two compounds of formula I-2.
In some embodiments of the present invention, the liquid crystal composition of the present invention preferably contains at least one compound of formula I-1 and at least one compound of formula I-2.
In some embodiments of the invention, in the compound of formula N, R N1 And R is N2 Each independently is preferably a linear or branched alkyl or alkoxy group containing 1 to 8 carbon atoms, a linear or branched alkenyl or alkenyloxy group containing 2 to 8 carbon atoms; further preferred are straight-chain or branched alkyl or alkoxy groups having 1 to 5 carbon atoms, straight-chain or branched alkenyl or alkene groups having 2 to 5 carbon atomsAn oxy group;
R N1 further preferably a linear or branched alkyl group having 1 to 5 carbon atoms, or a linear or branched alkenyl group having 2 to 5 carbon atoms, still further preferably a linear or branched alkyl group having 2 to 5 carbon atoms, or a linear or branched alkenyl group having 2 to 3 carbon atoms;
R N2 further preferred are straight or branched chain alkoxy groups containing 1 to 4 carbon atoms;
ring(s)And (C) a ring->Preferably +.>
In some embodiments of the invention, the compound of formula N is selected from the group consisting of:
and
In some embodiments of the invention, in order to obtain a relatively higher ε And wider workerAs the temperature range, the liquid crystal composition of the present invention preferably contains at least one compound selected from the group consisting of compounds of the general formulae N3 to N4, the general formulae N6 to N9, the general formulae N12, the general formulae N17 and the general formulae N19; it is further preferable to contain at least one compound selected from the group consisting of compounds of the general formulae N3 to N4, the general formulae N6 to N7, the general formulae N12, the general formulae N17 and the general formulae N19.
In some embodiments of the invention, in order to reduce ε The liquid crystal composition of the present invention preferably contains at least one compound selected from the group consisting of compounds of the general formula N12 and the general formula N17, while maintaining properties such as K value, power consumption, operating temperature range, transmittance, low-temperature miscibility, etc. at a high level and also having significantly high optical anisotropy.
In some embodiments of the present invention, the liquid crystal composition of the present invention contains at least one compound selected from the group consisting of compounds of the general formulae N3 to N4, the general formulae N6 to N7, and the general formula N19, and at least one compound selected from the group consisting of compounds of the general formulae N12 and N17.
In some embodiments of the invention, the compound of formula N comprises 0.1 to 50% by weight of the total liquid crystal composition.
Regarding the preferred content of the compounds of formula N: the preferred lower limit of the content of the compound of the formula N is 0.1%,0.5%,1%,3%,5%,10%,13%,14%,15%,18% or 20% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the preferred content of the compound of the formula N is 50%,40%,38%,35%,33%,30%,28%,25%,23%,20%,18%,15% or 10% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, the lower limit of the content of the compounds of the group consisting of the compounds of the general formulae N3 to N4, N6 to N9, N12, N17 and N19 is 1%,3%,5% or 10% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of the group consisting of the compounds of the general formulae N3 to N4, N6 to N9, N12, N17 and N19 is 50%,30%,28%,25%,23%,20%,18%,15% or 10% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, when it is desired to keep the viscosity of the liquid crystal composition of the present invention low and the response time short, it is preferable that the lower limit value and the upper limit value of the content of the compound of formula N be low. Further, when it is necessary to keep the clearing point of the liquid crystal composition of the present invention high and the temperature stability is good, it is preferable that the lower limit value and the upper limit value of the content of the compound of the formula N be low. In order to keep the drive voltage low and to increase the absolute value of the dielectric anisotropy, it is preferable that the lower limit value and the upper limit value of the content of the compound of the formula N be high.
In some embodiments of the invention, in the compound of formula M, R M1 And R is M2 Each independently is preferably a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 9 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms; further preferred are straight-chain alkyl groups having 1 to 8 carbon atoms, straight-chain alkoxy groups having 1 to 7 carbon atoms, or straight-chain alkenyl groups having 2 to 8 carbon atoms; still more preferred are straight chain alkyl groups having 1 to 5 carbon atoms, straight chain alkoxy groups having 1 to 4 carbon atoms, or straight chain alkenyl groups having 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, R M1 And R is M2 One or both of which are straight chain alkenyl groups containing 2 to 8 carbon atoms; further preferably, R M1 And R is M2 One or both of which are straight chain alkenyl groups containing 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, R M1 And R is M2 One of which is a linear alkenyl group having 2 to 5 carbon atoms and the other is a linear alkyl group having 1 to 5 carbon atoms.
In some embodiments of the invention, R M1 And R is M2 Both are independently preferably a linear alkyl group having 1 to 8 carbon atoms or a linear alkoxy group having 1 to 7 carbon atoms; advancing oneThe step is preferably a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms.
In some embodiments of the invention, preferably, R M1 And R is M2 One of which is a linear alkyl group having 1 to 5 carbon atoms, and the other of which is a linear alkyl group having 1 to 5 carbon atoms, or a linear alkoxy group having 1 to 4 carbon atoms; further preferably, R M1 And R is M2 Both are straight chain alkyl groups containing 1 to 5 carbon atoms.
The alkenyl group in the present invention is preferably selected from the group represented by any one of the formulas (V1) to (V9), and particularly preferably is formula (V1), formula (V2), formula (V8) or formula (V9). The groups represented by the formulas (V1) to (V9) are as follows:
wherein represents a carbon atom in the bonded ring structure.
The alkenyloxy group in the present invention is preferably selected from the group represented by any one of the formulae (OV 1) to (OV 9), and particularly preferably is the formula (OV 1), the formula (OV 2), the formula (OV 8) or the formula (OV 9). The groups represented by the formulas (OV 1) to (OV 9) are as follows:
wherein represents a carbon atom in the bonded ring structure.
In some embodiments of the invention, the compound of formula M is selected from the group consisting of:
and
In some embodiments of the present invention, the content of the compound of formula M must be appropriately adjusted depending on the desired properties of solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop marks, burn-in, dielectric anisotropy, and the like.
In some embodiments of the invention, the compound of formula M comprises 20-95% by weight of the total liquid crystal composition.
Regarding the preferred content of the compounds of the general formula M: the preferred lower limit of the content of the compound of formula M is 20%,25%,30%,35%,40%,45% or 50% relative to the total weight of the liquid-crystalline composition of the invention; the preferred upper limit of the content of the compound of the formula M is 95%,85%,75%,65%,60%,55%,45%,35% or 25% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the invention, where reliability is important, R is preferred M1 And R is M2 Are all alkyl groups; in the case where importance is attached to reducing the volatility of the compound, R is preferably M1 And R is M2 Are all alkoxy groups; and R is preferable in the case where importance is attached to the reduction of viscosity M1 And R is M2 At least one of which is alkenyl.
In some embodiments of the present invention, the liquid crystal composition contains at least one R M1 And/or R M2 A compound of formula M which is alkenyl; preferably, the liquid crystal composition contains at least two kinds of R M1 And/or R M2 A compound of formula M which is alkenyl; further preferably, the liquid crystal composition contains at least three kinds of R M1 And/or R M2 A compound of formula M which is alkenyl.
In some embodiments of the invention, the compounds of formula M are particularly preferably selected from the group consisting of compounds of formula M1, formula M2, formula M3, formula M7, formula M8 and formula M9.
In some embodiments of the invention, the compound of formula M1 is preferably selected from the group consisting of:
and
Wherein,,
R M11 and R is M21 Each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkoxy group having 1 to 7 carbon atoms.
Regarding the content of the compound of formula M1: the lower limit of the content of the compound of the formula M1 is 1%,2%,3%,5%,7%,10%,15%,20%,25%,30%,35%,40%,45%,50% or 55% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of the formula M1 is 70%,65%,60%,55%,50%,45%,40%,35%,30% or 25% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, the compounds of formula M1 are preferably selected from the group consisting of compounds of formula M1-a and compounds of formula M1-b.
In some embodiments of the invention, R in the compounds of formula M1-a, formula M1-b, formula M1-d and formula M1-e M11 Preferably a straight chain alkyl group containing 1 to 5 carbon atoms; more preferred are straight chain alkyl groups containing 2 to 5 carbon atoms.
In some embodiments of the inventionIn order to improve the response time in particular, preference is given to compounds of the formula M1-a in which R M11 A compound which is n-propyl.
R in the compounds of the formula M1-a relative to the total weight of the liquid-crystalline composition according to the invention M11 The lower limit of the content of the compound representing n-propyl group is 0%,1%,5%,10%,15%,17%,20%,23%,25%,27%,30% or 35%; r in the compounds of the formula M1-a relative to the total weight of the liquid-crystalline composition according to the invention M11 The upper limit of the content of the compound representing n-propyl group is 60%,55%,50%,45%,42%,40%,38%,35%,33% or 30%.
In some embodiments of the invention, R in the compounds of formula M1-a is preferred when a higher clearing point is desired in terms of response time M11 A compound which is n-butyl or n-pentyl.
R in the compounds of the formula M1-b relative to the total weight of the liquid-crystalline composition according to the invention M11 The lower limit of the content of the compound representing n-propyl group is 0%,1%,2%,3%,5%,7% or 10%; r in the compounds of the formula M1-b relative to the total weight of the liquid-crystalline composition according to the invention M11 The upper limit of the content of the compound representing n-propyl group was 20%,15%,13%,10%,8%,7%,6%,5% or 3%.
In some embodiments of the invention, R in the compounds of the formula M1-c M11 And R is M21 Each independently represents a linear alkyl group having 1 to 8 carbon atoms, or a linear alkoxy group having 1 to 7 carbon atoms; further preferred is a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms.
The lower limit of the content of the compounds of the general formulae M1 to c is 0%,1%,5%,10%,13%,15%,17%,20%,23%,25% or 30% relative to the total weight of the liquid-crystalline composition of the invention; the upper limit of the content of the compounds of the general formulae M1 to c is 60%,55%,50%,45%,40%,37%,35%,33%,30%,27%,25%,23%,20%,17%,15%,13% or 10% relative to the total weight of the liquid-crystal composition of the invention.
In some embodiments of the invention, in order to improve in particular the response time of the liquid-crystalline compositions according to the invention, particular preference is given to R in the compounds of the formula M1-c M11 Is n-propyl, and R M21 Is C 2 H 5 -a compound.
The compounds of the general formula M1-c have R, relative to the total weight of the liquid-crystalline composition according to the invention M11 Is n-propyl, and R M21 Is C 2 H 5 -the lower limit of the content of compounds is 0%,1%,2%,3%,5%,7%,10%,13%,15%,18% or 20%; the compounds of the general formula M1-c have R, relative to the total weight of the liquid-crystalline composition according to the invention M11 Is n-propyl, and R M21 Is C 2 H 5 The upper limit of the content of the compounds is 20%,17%,15%,13%,10%,8%,7% or 6%.
The lower limit of the content of the compounds of the general formulae M1 to d is 0%,1%,5%,10%,13%,15%,17% or 20% relative to the total weight of the liquid-crystal composition of the invention; the upper limit of the content of the compounds of the general formulae M1 to d is 25%,23%,20%,17%,15%,13% or 10% relative to the total weight of the liquid-crystal composition of the invention.
The lower limit of the content of the compounds of the general formulae M1 to e is 0%,1%,5%,10%,13%,15%,17% or 20% relative to the total weight of the liquid-crystalline composition according to the invention; the upper limit of the content of the compounds of the formula M1-e is 25%,23%,20%,17%,15%,13% or 10% relative to the total weight of the liquid-crystal composition of the invention.
In some embodiments of the invention, preference is given to compounds of the formula M1-d and of the formula M1-e in which R M11 A compound which is n-propyl.
Compounds of the general formula M1-d in which R is relative to the total weight of the liquid-crystalline composition according to the invention M11 The lower limit of the content of the compound which is n-propyl is 0%,1%,2%,3%,5%,7%,10%,13%,15%,18% or 20%; compounds of the general formula M1-d in which R is relative to the total weight of the liquid-crystalline composition according to the invention M11 Containing compounds which are n-propylThe upper limit of the amount is 20%,17%,15%,13%,10%,8%,7% or 6%.
Regarding the content of the compound of formula M2: the lower limit of the content of the compound of the formula M2 is 0%,1%,2%,3%,5%,7% or 10% relative to the total weight of the liquid-crystalline composition of the invention; the upper limit of the content of the compound of the formula M2 is 20%,15%,13%,10%,8%,7%,6%,5% or 3% relative to the total weight of the liquid crystal composition of the present invention.
Regarding the content of the compound of formula M3: the lower limit of the content of the compound of the formula M3 is 0%,1%,2%,3%,5%,7% or 10% relative to the total weight of the liquid-crystalline composition of the invention; the upper limit of the content of the compound of the formula M3 is 20%,15%,13%,10%,8%,7%,6%,5% or 3% relative to the total weight of the liquid crystal composition of the present invention.
Regarding the compound content of formula M7: the lower limit of the content of the compound of the formula M7 is 0%,1%,2%,3%,5%,7%,10%,14%,16%,20%,23%,26%,30%,35% or 40% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of the formula M7 is 50%,40%,35%,30%,20%,15%,10% or 5% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, R in the compound containing formula M7 is preferred in view of the required properties of solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc M1 Is a straight-chain alkenyl group having 2 to 4 carbon atoms, and R M2 Is CH 3 -compounds, said alkenyl groups containing 2-4 carbon atoms in a straight chain, further preferred are
R in the compound of the formula M7 is, relative to the total weight of the liquid-crystalline composition according to the invention M1 Is thatAnd R is M2 Is CH 3 -the lower limit of the content of the compound is 0%,3%,5%,7%,9%,11%,12%,13%,18% or 21%, and the upper limit of the content is 45%,40%,35%,30%,25%,23%,20%,18%,15%,13%,10% or 8%. When both of the two compounds are contained, the lower limit value of the content of the two compounds is 9%,15%,19%,24% or 30%, and the upper limit value of the content is 45%,40%,35%,30%,25%,23%,20%,18%,15% or 13% with respect to the total weight of the liquid crystal composition of the present invention.
Regarding the content of the compound of formula M8: the lower limit of the content of the compound of the formula M8 is 0%,1%,2%,3%,4%,5%,7%,10%,14%,16% or 20% relative to the total weight of the liquid-crystal composition of the invention; the upper limit of the content of the compound of the formula M8 is 45%,40%,35%,30%,20%,15%,10% or 5% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, R in the compound containing formula M8 is preferred in view of the desired properties of solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc M1 Is a straight-chain alkenyl group having 2 to 4 carbon atoms, and R M2 Is CH 3 -compounds, said alkenyl groups containing 2-4 carbon atoms in a straight chain, further preferred are
The compounds of the general formula M8 have R, relative to the total weight of the liquid-crystalline composition according to the invention M1 Is thatAnd R is M2 Is CH 3 The lower limit of the content of compounds is 0%,3%,4%,5%,7%,9%,11%,12%,13%,18% or 20% and the upper limit value of the content is 40%,35%,30%,25%,23%,20%,18%,15%,13%,10% or 8%. When both the compounds are contained, the lower limit value of the content of the two compounds is 15%,19%,24% or 30% and the upper limit value of the content is 45%,40%,35%,30%,25%,23%,20%,18%,15% or 13% with respect to the total weight of the liquid crystal composition of the present invention.
Regarding the compound content of formula M9: the lower limit of the content of the compound of the formula M9 is 0%,1%,2%,3%,5%,7%,10%,14%,16%,20%,23%,26%,30%,35% or 40% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of the formula M9 is 50%,40%,35%,30%,20%,15%,10% or 5% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the invention, the compound of formula M9 is preferably R M1 Is n-propyl or n-pentyl, and R M2 Is C 2 H 5 -a compound, or preferably R M1 Is thatAnd R is M2 Compounds which are n-propyl, or preferably R M1 Is n-propyl, n-butyl or n-pentyl, and R M2 Is CH 3 O-compounds; r is particularly preferred M1 Is n-propyl, and R M2 Is C 2 H 5 -a compound.
In some embodiments of the invention, the compound of formula M9 is preferably R M1 And R is M2 At least one of isA compound of (a); r is particularly preferred M2 Is->Is a compound of (a).
In some embodiments of the invention, a compound of formula M9R in the compound M2 Is thatThe lower limit of the content of the compound of (a) is 0%,1%,2%,3%,4%,5%,7%,9% or 10%, and the upper limit of the content is 25%,23%,20%,18%,15%,13%,10% or 8%. When both the compounds are contained, the lower limit value of the content of the two compounds is 2%,3%,4% or 5% and the upper limit value of the content is 30%,25%,20%,15% or 10% with respect to the total weight of the liquid crystal composition of the present invention.
Regarding the compound content of formula M11: the lower limit of the content of the compound of the formula M11 is 0%,1%,2%,3%,5%,7%,10%,14%,16%,20%,23%,26%,30%,35% or 40% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of the formula M11 is 50%,40%,35%,30%,20%,15%,10% or 5% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the invention, the compound of formula M11 is preferably R M1 And R is M2 Compounds each independently representing a straight-chain alkyl radical having 2 to 5 carbon atoms, or preferably R M1 And R is M2 One of them is And the other is CH 3 -or C 2 H 5 -a compound.
Regarding the content of the compounds of the general formulae M17 to M21: the lower limit value of the total content of the compounds of the general formulae M17 to M21 is 0%,1%,2%,3%,5%,7%,10%,14%,16% or 20% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the total content of the compounds of the general formulae M17 to M21 is 30%,25%,23%,20%,18%,15%,10% or 5% relative to the total weight of the liquid-crystal composition of the invention.
In some embodiments of the invention, the liquid crystal composition further comprises at least one compound of formula A-1 and/or at least one compound of formula A-2, said compound of formula A-1 and/or compound of formula A-2 having positive dielectric anisotropy:
wherein,,
R A1 and R is A2 Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms, Said straight or branched alkyl group having 1 to 12 carbon atoms, < >>Of 1 or non-adjacent 2 or more-CH' s 2 -can be replaced independently of one another by-ch=ch-, -c≡c-, -O-, -CO-O-or-O-CO-, and the straight-chain or branched alkyl radical having 1 to 12 carbon atoms, -or> Wherein one or more of-H's may each be independently substituted with-F or-Cl;
ring(s)And (C) a ring->Each independently represents-> Wherein (1)>In which one or more of-H may be substituted by-CN, -F or-Cl and one or more of-ch=may be substituted by-n=in the ring;
ring(s)And (C) a ring->Each independently represents-> Wherein (1)>At most 1-CH 2 The group may be replaced by an-O-group,in which one or more of-H may be substituted by-CN, -F or-Cl and one or more of-ch=may be substituted by-n=in the ring;
Z A11 、Z A21 and Z A22 Each independently represents a single bond, -CH 2 CH 2 -、-CF 2 CF 2 -、-CO-O-、-O-CO-、-O-CO-O-、-CH=CH-、-CF=CF-、-CH 2 O-or-OCH 2 -;
L A11 、L A12 、L A13 、L A21 And L A22 Each independently represents-H, -F or-CH 3
X A1 And X A2 Each independently represents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, haloalkenyl or haloalkenoxy having 2 to 5 carbon atoms; and is also provided with
n A1 And n A2 Each independently represents 0, 1, 2 or 3, and when n A1 When=2 or 3, the ringZ, which may be the same or different A11 May be the same or different, when n A2 When=2 or 3, the ring->Z, which may be the same or different A21 May be the same or different.
In some embodiments of the invention, the compound of formula A-1 and/or the compound of formula A-2 is preferably a compound having an absolute value of dielectric anisotropy greater than 3.
In some embodiments of the invention, the compound of formula a-1 is selected from the group consisting of:
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and
The compound of formula a-2 is selected from the group consisting of:
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/>
/>
/>
and
Wherein,,
R A11 and R is A21 Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or not adjacent more than 2-CH of the linear or branched alkyl groups having 1 to 12 carbon atoms 2 Can be independently and individually represented by-ch=ch-, C.ident.C-, -O-, -CO-,)CO-O-or-O-CO-.
Regarding the content of the compound of the formula A-1 and/or the compound of the formula A-2: the lower limit of the content of the compound of the formula A-1 and/or the compound of the formula A-2 is 0%,1%,5%,10% or 20% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of the formula A-1 and/or the compound of the formula A-2 is 45%,40%,35%,30%,25% or 20% relative to the total weight of the liquid crystal composition of the present invention.
In addition to the above-mentioned compounds, the liquid crystal composition of the present invention may contain a usual nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, infrared absorber, polymerizable monomer, light stabilizer, or the like.
Possible dopants which are preferably added to the liquid crystal composition according to the invention are shown below.
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And
In some embodiments of the invention, preferably, the dopant comprises 0 to 5wt% of the total weight of the liquid crystal composition; more preferably, the dopant comprises 0 to 1wt% of the total weight of the liquid crystal composition.
The additives such as antioxidants and light stabilizers used in the liquid crystal composition of the present invention are preferably the following:
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/>
/>
wherein n represents a positive integer of 1 to 12.
Preferably, the light stabilizer is selected from the group consisting of the light stabilizers shown below:
in some embodiments of the present invention, preferably, the light stabilizer comprises 0 to 5wt% of the total weight of the liquid crystal composition; more preferably, the light stabilizer comprises 0 to 1wt% of the total weight of the liquid crystal composition; particularly preferably, the light stabilizer comprises 0 to 0.1% by weight of the total weight of the liquid crystal composition.
In another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
The beneficial effects are that:
the liquid crystal composition of the invention has higher optical anisotropy, higher absolute value of dielectric anisotropy and larger epsilon Greater average elastic constant, greater transmittance, a wider operating temperature range (i.e., higher clearing point and lower nematic lower limit temperature), and better low temperature miscibility; in particular, when the Δε level is improved by about 50%, the liquid crystal molecular ordering is good, and the K value can be maintained at a significantly high level, thereby achieving higher transmittance.
Detailed Description
The invention will be described below in connection with specific embodiments. The following examples are illustrative of the present invention and are not intended to limit the present invention. Other combinations and various modifications within the spirit of the invention may be made without departing from the spirit or scope of the invention.
The liquid crystal displays used in the following embodiments are TFT liquid crystal display devices, and the cell thickness d=7μm (unless otherwise specified).
For ease of expression, in the following examples, the group structures of the liquid crystal compositions are represented by the codes listed in Table 1:
TABLE 1 group Structure codes for liquid Crystal Compounds
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Take as an example a compound of the formula:
the structural formula is expressed by codes listed in table 1, and can be expressed as follows: nCCGF, where n in the code represents the number of C atoms in the left-hand alkyl group, e.g., n is "3", i.e., the alkyl group is-C 3 H 7 The method comprises the steps of carrying out a first treatment on the surface of the C in the code represents 1, 4-cyclohexylene, G represents 2-fluoro-1, 4-phenylene and F represents a fluorine substituent.
The shorthand designations for the test items in the following examples are as follows:
cp clearing point (nematic phase-isotropic phase transition temperature, DEG C)
Delta n optical anisotropy (589 nm,25 ℃ C.)
Delta epsilon dielectric anisotropy (1 KHz,25 ℃ C.)
ε Dielectric constant perpendicular to the molecular axis
K ave Average spring constant
T penetration (%)
t -40℃ Low temperature storage time (-40 ℃ C., tian)
Wherein,,
the optical anisotropy was measured at 25℃using an Abbe refractometer under a sodium light (589 nm) source.
Δε=ε Wherein ε is For dielectric constant parallel to the molecular axis ε For dielectric constants perpendicular to the molecular axis, test conditions: the test box is TN90 type at 25 ℃ and 1KHz, and the thickness of the box is 7 mu m.
Wherein K is 11 、K 22 、K 33 The C-V curve of the liquid crystal is tested by using an LCR instrument and an antiparallel friction box, and the test conditions are as follows: 7 μm antiparallel friction cassette, v=0.1 to 20V.
Test conditions for penetration T: the transmittance of the light modulation device was measured by using a DMS 505 tester, and the thickness of the light modulation device was 5.2 μm.
The components used in the examples below were synthesized by known methods or obtained commercially. These synthetic techniques are conventional and the resulting liquid crystal compounds are tested to meet the electronic class of compound standards.
Liquid crystal compositions were prepared in accordance with the proportions of the respective liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared by mixing the components according to a specified proportion by adopting a mode of heating, ultrasonic wave, suspension and the like according to a conventional method in the field.
Liquid crystal compositions as given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1 was prepared according to the respective compounds and weight percentages listed in table 2, and was filled between two substrates of a liquid crystal display for performance test.
Table 2 liquid crystal composition formulation and performance parameter testing
Comparative example 2
The liquid crystal composition of comparative example 2 was prepared according to the respective compounds and weight percentages listed in table 3, and was filled between two substrates of a liquid crystal display for performance test.
Table 3 liquid crystal composition formulation and performance parameter testing
Example 1
The liquid crystal composition of example 1 was prepared according to the respective compounds and weight percentages listed in table 4, and was filled between two substrates of a liquid crystal display for performance test.
Table 4 liquid crystal composition formulation and performance parameter testing
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Example 2
The liquid crystal composition of example 2 was prepared according to the respective compounds and weight percentages listed in table 5, and was filled between two substrates of a liquid crystal display for performance test.
Table 5 liquid crystal composition formulation and performance parameter testing
Example 3
The liquid crystal composition of example 3 was prepared according to the respective compounds and weight percentages listed in table 6, and was filled between two substrates of a liquid crystal display for performance test.
Table 6 liquid crystal composition formulation and performance parameter testing
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Example 4
The liquid crystal composition of example 4 was prepared according to the respective compounds and weight percentages listed in table 7, and was filled between two substrates of a liquid crystal display for performance test.
Table 7 liquid crystal composition formulation and performance parameter testing
Example 5
The liquid crystal composition of example 5 was prepared according to the respective compounds and weight percentages listed in table 8, and was filled between two substrates of a liquid crystal display for performance test.
Table 8 liquid crystal composition formulation and performance parameter testing
Example 6
The liquid crystal composition of example 6 was prepared according to the respective compounds and weight percentages listed in table 9, and was filled between two substrates of a liquid crystal display for performance test.
Table 9 liquid crystal composition formulation and performance parameter testing
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Example 7
The liquid crystal composition of example 7 was prepared by the respective compounds and weight percentages listed in table 10, and was filled between two substrates of a liquid crystal display for performance test.
Table 10 liquid crystal composition formulation and performance parameter testing
Example 8
The liquid crystal composition of example 8 was prepared by the respective compounds and weight percentages listed in table 11, and was filled between two substrates of a liquid crystal display for performance test.
Table 11 liquid crystal composition formulation and performance parameter testing
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Example 9
The liquid crystal composition of example 9 was prepared by the respective compounds and weight percentages listed in table 12, and was filled between two substrates of a liquid crystal display for performance test.
Table 12 liquid crystal composition formulation and performance parameter testing
/>
Example 10
The liquid crystal composition of example 10 was prepared by the respective compounds and weight percentages listed in table 13, and was filled between two substrates of a liquid crystal display for performance test.
Table 13 liquid crystal composition formulation and performance parameter testing
Example 11
The liquid crystal composition of example 11 was prepared by the respective compounds and weight percentages listed in table 14, and was filled between two substrates of a liquid crystal display for performance test.
Table 14 liquid crystal composition formulation and performance parameter testing
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As is apparent from the above comparative examples 1 to 2 and examples 1 to 11, the liquid crystal composition of the present invention has higher optical anisotropy, higher absolute value of dielectric anisotropy, larger ε Greater average elastic constant, greater transmittance, a wider operating temperature range (i.e., higher clearing point and lower nematic lower limit temperature), and better low temperature miscibility; in particular, when the Δε level is improved by about 50%, the liquid crystal molecular ordering is good, and the K value can be maintained at a significantly high level, thereby achieving higher transmittance.
The above embodiments are only for illustrating the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the present invention and to implement it, but not limit the scope of the present invention, and all equivalent changes or modifications made according to the spirit of the present invention should be included in the scope of the present invention.

Claims (5)

1. A liquid crystal composition having positive dielectric anisotropy, the liquid crystal composition comprising:
at least one compound of formula i selected from the group consisting of:
and
At least one compound of the formula N
And is also provided with
The at least one compound of formula N comprises at least one compound selected from the group consisting of:
and
And
At least one compound of the formula M
Wherein,,
R 1 represents a linear alkyl group having 2 to 5 carbon atoms,
R N1 And R is N2 Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or non-adjacent more than 2-CH in the straight-chain or branched alkyl group containing 1-12 carbon atoms 2 -may each be independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
R M1 and R is M2 Each independently represents-H, a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or non-adjacent more than 2-CH in the straight-chain or branched alkyl group containing 1-12 carbon atoms 2 -may each be independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
ring(s)And (C) a ring->Each independently represents->Wherein,,one or more of-CH 2 Can be replaced by-O-, single bonds in one or more rings can be replaced by double bonds,in which one or more of-H may be substituted by-CN, -F or-Cl and one or more of-ch=may be substituted by-n=in the ring;
ring(s)Ring->And (C) a ring->Each independently represents-> Wherein (1)>One or more of-CH 2 -can be replaced by-O->At most one-H of (c) may be substituted by halogen;
Z N1 and Z N2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH=CH-、-C≡C-、-CH 2 CH 2 -、-(CH 2 ) 4 -、-CF 2 O-、-OCF 2 -or-CF 2 CF 2 -and Z N1 And Z N2 At least one of which is not a single bond;
Z M1 and Z M2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH=CH-、-C≡C-、-CH 2 CH 2 -or- (CH) 2 ) 4 -;
n N1 Represents 0, 1, 2 or 3, n N2 Represents 0 or 1, and 0.ltoreq.n N1 +n N2 Not more than 3, and when n N1 When=2 or 3, the ringZ, which may be the same or different N1 May be the same or different;
n M1 represents 0, 1, 2 or 3, and when n M1 When=2 or 3, the ringZ, which may be the same or different M2 May be the same or different;
the compound of the general formula N accounts for 0.1-20% of the total weight of the liquid crystal composition;
the compound of the general formula M accounts for 20-75% of the total weight of the liquid crystal composition;
the liquid crystal composition contains at least two compounds of the general formula I-2
2. The liquid crystal composition having positive dielectric anisotropy according to claim 1, wherein the compound of formula N further comprises a compound selected from the group consisting of:
and
3. The liquid crystal composition with positive dielectric anisotropy according to claim 2, wherein the liquid crystal composition comprises at least one compound selected from the group consisting of compounds of the general formula N3-N4, the general formula N6-N9, the general formula N12, the general formula N17 and the general formula N19.
4. The liquid crystal composition with positive dielectric anisotropy according to claim 1, wherein the compound of the general formula M is selected from the group consisting of:
and
5. A liquid crystal display device comprising the liquid crystal composition having positive dielectric anisotropy of any one of claims 1 to 4.
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Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103320142A (en) * 2012-02-15 2013-09-25 默克专利股份有限公司 Liquid-crystalline medium
CN103740377A (en) * 2013-12-27 2014-04-23 北京八亿时空液晶科技股份有限公司 Liquid crystal composition and application thereof
CN104371745A (en) * 2014-10-24 2015-02-25 石家庄诚志永华显示材料有限公司 Liquid crystal composite
CN104498055A (en) * 2014-12-31 2015-04-08 石家庄诚志永华显示材料有限公司 Liquid crystal composition
CN105199745A (en) * 2015-09-30 2015-12-30 石家庄诚志永华显示材料有限公司 Positive-negative-mixed liquid crystal composition
CN105295955A (en) * 2015-09-30 2016-02-03 石家庄诚志永华显示材料有限公司 Positive and negative mixed liquid crystal composition
CN105722950A (en) * 2013-11-18 2016-06-29 捷恩智株式会社 Liquid crystal composition and liquid crystal display element
CN107118782A (en) * 2017-06-29 2017-09-01 石家庄诚志永华显示材料有限公司 A kind of liquid-crystal composition
CN107236549A (en) * 2017-06-29 2017-10-10 石家庄诚志永华显示材料有限公司 Liquid-crystal composition and the liquid crystal display cells comprising the liquid-crystal composition
CN107779201A (en) * 2016-08-29 2018-03-09 石家庄诚志永华显示材料有限公司 Liquid-crystal composition and liquid crystal display cells
CN108659858A (en) * 2017-03-30 2018-10-16 江苏和成显示科技有限公司 Liquid-crystal composition with positive dielectric anisotropy and its display device
CN109134423A (en) * 2017-11-23 2019-01-04 江苏和成显示科技有限公司 A kind of compound and its liquid-crystal composition and photoelectric display device
CN109796990A (en) * 2017-11-16 2019-05-24 石家庄诚志永华显示材料有限公司 Liquid-crystal compounds and liquid crystal compound and its display device containing lateral trifluoromethyl
CN109988583A (en) * 2018-01-03 2019-07-09 石家庄诚志永华显示材料有限公司 A kind of liquid-crystal composition and liquid crystal display device

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103320142A (en) * 2012-02-15 2013-09-25 默克专利股份有限公司 Liquid-crystalline medium
CN105722950A (en) * 2013-11-18 2016-06-29 捷恩智株式会社 Liquid crystal composition and liquid crystal display element
CN103740377A (en) * 2013-12-27 2014-04-23 北京八亿时空液晶科技股份有限公司 Liquid crystal composition and application thereof
CN104371745A (en) * 2014-10-24 2015-02-25 石家庄诚志永华显示材料有限公司 Liquid crystal composite
CN104498055A (en) * 2014-12-31 2015-04-08 石家庄诚志永华显示材料有限公司 Liquid crystal composition
CN105295955A (en) * 2015-09-30 2016-02-03 石家庄诚志永华显示材料有限公司 Positive and negative mixed liquid crystal composition
CN105199745A (en) * 2015-09-30 2015-12-30 石家庄诚志永华显示材料有限公司 Positive-negative-mixed liquid crystal composition
CN107779201A (en) * 2016-08-29 2018-03-09 石家庄诚志永华显示材料有限公司 Liquid-crystal composition and liquid crystal display cells
CN108659858A (en) * 2017-03-30 2018-10-16 江苏和成显示科技有限公司 Liquid-crystal composition with positive dielectric anisotropy and its display device
CN107118782A (en) * 2017-06-29 2017-09-01 石家庄诚志永华显示材料有限公司 A kind of liquid-crystal composition
CN107236549A (en) * 2017-06-29 2017-10-10 石家庄诚志永华显示材料有限公司 Liquid-crystal composition and the liquid crystal display cells comprising the liquid-crystal composition
CN109796990A (en) * 2017-11-16 2019-05-24 石家庄诚志永华显示材料有限公司 Liquid-crystal compounds and liquid crystal compound and its display device containing lateral trifluoromethyl
CN109134423A (en) * 2017-11-23 2019-01-04 江苏和成显示科技有限公司 A kind of compound and its liquid-crystal composition and photoelectric display device
CN109988583A (en) * 2018-01-03 2019-07-09 石家庄诚志永华显示材料有限公司 A kind of liquid-crystal composition and liquid crystal display device

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