WO2020034759A1

WO2020034759A1 - Liquid crystal composition having high dielectric constant and application thereof

Info

Publication number: WO2020034759A1
Application number: PCT/CN2019/092471
Authority: WO
Inventors: 李珊珊; 陆嘉文; 陈新华
Original assignee: 晶美晟光电材料（南京）有限公司
Priority date: 2018-08-13
Filing date: 2019-06-24
Publication date: 2020-02-20
Also published as: CN108865178A

Abstract

A liquid crystal composition having a negative dielectric constant, comprising liquid crystal compounds represented by general formulas I, II, and III. The general formula I is, the general formula II is, and the general formula III is. The liquid crystal composition has a relatively high vertical dielectric constant value, a nematic phase of a relatively wide temperature range, and a relatively high elastic coefficient K, and is beneficial to the manufacturing of a quick-response liquid crystal display device and to energy conservation.

Description

Liquid crystal composition with high dielectric constant and application thereof

Technical field

The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition and application thereof.

Background technique

In the 1960s, RCA first discovered that electrical stimulation would change the transmission mode of liquid crystals, and then released the liquid crystal display technology using this property. Liquid crystals gradually attracted people's attention and quickly developed into various fields. In 1966, after Kevlar fiber was synthesized from aramid liquid crystal by DuPont, the liquid crystal material began industrialization. After decades of rapid development, liquid crystal materials have been widely used in many fields such as display technology, optical storage equipment and solar cells due to their special properties. The research scope has covered many fields such as chemistry, biology and information science, and has become a society today. One of the most popular and indispensable new materials.

The liquid crystal display can be divided into two driving modes: a passive matrix (also called a passive matrix or a simple matrix) and an active matrix (also called an active matrix). Among them, the active matrix liquid crystal display changes the arrangement of liquid crystal compounds by applying a voltage, thereby changing the light emission intensity of the backlight source to form an image. It has high resolution, high contrast, low power, thin surface, and light weight. The characteristics are more and more popular. Active matrix liquid crystal displays can be divided into two types according to active devices: MOS (metal oxide semiconductor) or other diodes on a silicon chip as a substrate; thin film transistors (ThinFilm) on a glass plate as a substrate Transistor-TFT), of which the most rapidly developing is the thin film transistor liquid crystal display (TFT-LCD), which has been well applied in display devices such as mobile phones, computers, LCD TVs and cameras, and has become the mainstream of the current LCD market product.

With the continuous development of TFT-LCD, the wide viewing angle mode has become the goal pursued in the industry. At present, the mainstream wide viewing angle technologies mainly include VA vertical orientation technology, IPS in-plane switching technology and FFS fringe field switching technology. Both require higher light transmission and less color cast. Among them, for the IPS in-plane switching technology and the FFS fringe field switching technology, because an in-plane electric field is generated between the electrodes when a voltage is applied, the light penetration in this area is restricted, which will increase energy consumption and affect the display effect. Liquid crystal compounds perform better in color misregistration and are affected by vertical electric fields. Compared with positive materials, liquid crystal compounds exhibit higher light transmittance and are therefore widely used. However, the general-purpose negative liquid crystal materials on the market generally have high viscosity and are not conducive to the improvement of response speed. Therefore, the development of liquid crystal materials with low viscosity and high negative dielectric constant has become the main research direction of negative liquid crystal materials.

With the wide application of liquid crystal displays, the requirements for their performance are constantly increasing, requiring a wider operating temperature, faster response speed and higher contrast, while at the same time requiring lower and lower power consumption, reducing power consumption This means that liquid crystal displays need lower driving voltage and higher light transmittance. These performance improvements are inseparable from the improvement of liquid crystal materials.

Summary of the Invention

The object of the present invention is to provide a negative liquid crystal composition having a high dielectric constant, so as to improve the problems of high viscosity and high driving voltage of the negative liquid crystal material in the prior art, thereby improving response speed and reducing power consumption.

Another object of the present invention is to provide an application of the above-mentioned liquid crystal composition.

Technical solution: In order to achieve the above object, according to an aspect of the present invention, a liquid crystal composition is provided, the liquid crystal composition includes at least one liquid crystal compound having the general formula I, at least one liquid crystal compound having the general formula II, and At least one liquid crystal compound having the general formula III,

The general formula I is:

among them,

Y and Y 'are independently selected from H, C1 ~ C7 alkyl, C1 ~ C7 alkoxy group, an alkenyl group of C2 ~ C7 alkenyl or C2 ~ C7 alkoxy, wherein H or CH ₂ may be a ring Substituted with pentyl, cyclopentenyl or F; or, each of said Y and Y 'is independently selected from cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, Y and Y 'are each independently selected from cyclopentenyl, oxycyclopentenyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethyl cyclopentenyl;

m is selected from 0 or 1; n is selected from 0, 1 or 2;

Z is selected from a single bond, O,

CH ₂ , CH ₂ O, C ₂ H ₄ , C ₂ H ₄ O, C ₃ H ₆ , C ₃ H ₆ O, C ₄ H ₈ , OC ₄ H ₈ , C ₂ H ₂ , C ₂ H ₂ O, Any of C ₃ H ₄ O, OCH ₂ O, OC ₂ H ₄ O, OC ₃ H ₆ O, or OC ₄ H ₈ O, wherein H may be replaced by F;

When n is 1,

From

Any one of the group.

When n is 2, two are included in the formula

which is

Occurs twice in the general formula, at each occurrence

Each independently selected

Any one of the group.

The general formula II is:

Among them, Y ₁ and Y ₁ ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH ₂ may be substituted with cyclopentyl, cyclopentenyl or F; or, Y ₁ and Y ₁ ′ are each independently selected from cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, Y ₁ and Y ₁ ′ are each independently selected from cyclopentenyl, oxycyclopentenyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

k is selected from 0, 1 or 2;

From

Any one of the group.

The general formula III is:

Among them, Y ₂ and Y ₂ ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH ₂ may be substituted with cyclopentyl, cyclopentenyl or F; or, each of Y ₂ and Y ₂ ′ is independently selected from cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, Y ₂ and Y ₂ ′ are each independently selected from cyclopentenyl, oxycyclopentenyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

Each independently selected

Any one of the group.

According to another aspect of the present invention, an application of the above-mentioned liquid crystal composition in a liquid crystal display material or a liquid crystal display device is provided.

Beneficial effect: The liquid crystal composition of the present invention can effectively improve the viscosity and dielectric constant value of the liquid crystal material, thereby improving the response speed of the liquid crystal material and reducing energy consumption.

detailed description

It should be noted that, in the case of no conflict, the embodiments in the present application and the features in the embodiments can be combined with each other. The present invention will be described in detail with reference to the following embodiments.

In a typical embodiment of the present invention, a liquid crystal composition is provided. The liquid crystal composition includes at least one liquid crystal compound having the general formula I, at least one liquid crystal compound having the general formula II, and at least one having Liquid crystal compound of general formula III.

The general formula I is:

among them,

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

m is selected from 0 or 1; n is selected from 0, 1 or 2;

Z is selected from a single bond, O,

When n is 1,

From

Any one of the group.

When n is 2, two are included in the formula

which is

Occurs twice in the general formula, at each occurrence

Each independently selected

Any one of the group.

The general formula II is:

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

k is selected from 0, 1 or 2;

From

Any one of the group.

The general formula III is:

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

Each independently selected

Any one of the group.

A liquid crystal compound having the general formula I is white in a pure state, and is a liquid crystal compound having negative dielectric anisotropy. The liquid crystal compound having a negative dielectric constant is characterized by having a large Dipole effect, so the corresponding component of the relative dielectric constant in the vertical direction is relatively large, that is, has a high vertical dielectric constant ε _⊥ , so the dielectric anisotropy Δε = ε _// -ε _⊥ appears negative value. Especially for the liquid crystal compound represented by the general formula I, due to the repulsive action of the lone pair of electrons carried by the O atom to the electrons carried by the F atom, the electrons carried by the F atom tend to be aligned more perpendicular to the long axis, and the central oxygen Atoms also contribute to the dielectric constant perpendicular to the long axis, and therefore have a higher vertical dielectric constant ε _⊥ . According to the driving voltage formula

The driving voltage is inversely proportional to the dielectric constant, so the higher the dielectric constant, the lower the driving voltage, that is, the lower the energy consumption. Due to the higher vertical dielectric constant ε _，, liquid crystal molecules tend to be distributed perpendicular to the electric field, and the negative liquid crystal materials are aligned on the horizontal plane under the fringe electric field. The pretilt angle distribution is more uniform than that of the positive material. Shows high light transmittance and wide viewing angle, especially suitable for preparing VA, PSVA, IPS and FFS liquid crystal materials with high transmission and wide viewing angle. In addition, the addition of a liquid crystal compound with a negative dielectric constant can increase the bending elastic coefficient K _{33 of} the system, which can improve the transmittance and contrast of light throughout the system, is conducive to energy saving, and can improve the image display quality, which can better meet Performance requirements for liquid crystal displays. According to the off-state response time formula

The off-state response time is inversely proportional to k ₃₃ , so the larger k ₃₃ and the shorter the response time, the faster the response speed.

The liquid crystal compound having the general formula II is white in a pure substance state, and is a liquid crystal compound having negative dielectric anisotropy. Compared with the negative liquid crystal compound of the general formula I, the dielectric constant of the liquid crystal compound of the general formula II Slightly smaller, but it has a lower rotational viscosity and a lower melting point. According to the on-state response time formula

A low rotational viscosity γ ₁ can further improve the response speed of the liquid crystal composition. The lower melting point can improve the low-temperature reliability of the liquid crystal composition and increase the operating temperature range of the liquid crystal material.

The liquid crystal compound having the general formula III is white in a pure substance state, and is a liquid crystal compound having weak polarity or non-polarity. The liquid crystal compound having the general formula III is characterized by a lower rotational viscosity and a lower melting point. Therefore, when mixed with other types of liquid crystal compounds, it has better mutual solubility and improved viscosity and low temperature reliability of liquid crystal materials.

Therefore, combining the liquid crystal compound of the general formula I with the liquid crystal compounds of the general formula II and the general formula III can not only retain the advantages of the negative dielectric constant of the negative liquid crystal material, but also improve its viscosity and low-temperature reliability. Insufficient liquid crystal materials can be obtained, so that lower driving voltage, wider operating temperature and faster response speed can be obtained.

In addition, it should be clear to those skilled in the art that the above-mentioned alkyl groups include not only straight-chain alkyl groups but also corresponding branched-chain alkyl groups.

In order to obtain a more suitable liquid crystal width, a higher dielectric anisotropy value, a smaller rotational viscosity, and a suitable elastic coefficient K, it is more conducive to improving the response speed of the liquid crystal material, reducing the threshold voltage, and improving the interaction of the liquid crystal material. Solubility, in a preferred embodiment of the present application, the liquid crystal compound having the negative dielectric constant of the general formula I is a negative-polarity liquid crystal compound having the formulae I1 to I37, and the highly optically anisotropic liquid crystal compound of the general formula II is The liquid crystal compounds having Formulae II1 to II35, and the liquid crystal compounds having a low rotational viscosity of Formula III are preferably liquid crystal compounds having Formulae III1 to III3.

The above compounds having the general formulae I1 to I37 have the general formula:

Among them, R ₁ and R ₁ ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH ₂ may be substituted with cyclopentyl, cyclopentenyl, or F; or, R ₁ and R ₁ ′ are each independently selected from cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethyl cyclopentyl; or, R ₁ and R ₁ ′ are each independently selected from cyclopentenyl, oxycyclopentenyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl.

The above compounds having the general formulae II1 to II35 have the general formula:

Among them, R ₂ and R ₂ ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH ₂ may be substituted by cyclopentyl, cyclopentenyl or F; or, R ₂ and R ₂ ′ are each independently selected from cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, R ₂ and R ₂ ′ are each independently selected from cyclopentenyl, oxycyclopentenyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

The above compounds having the general formulae III1 to III3 have the general formula:

Among them, Y ₃ and Y ₃ ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenoxy, wherein H or CH ₂ may be substituted by cyclopentyl, cyclopentenyl or F; or, each of Y ₃ and Y ₃ ′ is independently selected from cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, each of Y ₃ and Y ₃ ′ is independently selected from cyclopentenyl, oxycyclopentenyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

When the liquid crystal composition of the present invention is combined with other types of liquid crystal compounds to form a liquid crystal mixture having a negative dielectric constant, the characteristics of the liquid crystal composition having the negative dielectric constant can be adjusted in a wide range, thereby satisfying the requirements of more liquid crystal materials. Performance requirements. In addition, the liquid crystal composition of the present invention has good mutual solubility when mixed with other types of liquid crystal compounds, and has less restrictions on the types of other liquid crystal compounds and the like used in combination. It can be applied to various liquid crystal materials according to the purpose, and is particularly advantageous. Improve the comprehensive properties of liquid crystal materials. In addition, the liquid crystal composition has good UV, light, and thermal stability.

The liquid crystal composition having a negative dielectric constant of the present invention can be prepared according to a conventional method. Generally, the required amount of the component is dissolved in the component constituting the main component at a relatively low temperature; the solution of each component can also be mixed into an organic solvent, such as acetone, chloroform, or methanol, and thoroughly mixed and removed again. The solvent is removed, for example, by distillation.

The type of the existing liquid crystal compound contained in the liquid crystal composition having a negative dielectric constant of the present invention is not limited, and any kind of liquid crystal compound can be selected according to the purpose to form a liquid crystal mixture together with the liquid crystal compound of the present invention, and can also be used as required Add other additives in the technical field. For example, a polymerizable compound, an optically active component, and / or a stabilizer may be added in a mass content of 0 to 20%.

The general formula of the above polymerizable compound is as follows:

among them,

—T ₁ and —T ₂ are each independently represented

Or epoxy

—W ₁ — and —W ₂ — each independently represent a single bond or an alkyl group having 1 to 8 carbon atoms;

—X ₁ —and —X ₂ — each independently represent a single bond, —O—, —CO—, —COO— or —OCO—;

—Z ₁ —Single bond, —O—, —CO—, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —C ₂ H ₄ —, —CF ₂ O—, — OCF ₂ —,

—CH = CH—,

One or two of the group consisting of;

i is 0, 1 or 2;

When i is 1, —Z ₁ — represents a single bond, —O—, —CO—, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —C ₂ H ₄ —, —CF ₂ O—, —OCF ₂ —,

—CH = CH—,

When i is 2, —Z ₁ — appears twice in the general formula, —Z ₁ — each represents a single bond, —O—, —CO—, —COO—, —OCO—, — CH ₂ O—, —OCH ₂ —, —C ₂ H ₄ —, —CF ₂ O—, —OCF ₂ —,

—CH = CH—,

Express

Where —CH ₂ — on cyclohexyl can be substituted by O, or

Where = CH— on the benzene ring can be replaced by N, and H on the benzene ring can be replaced by F, or

When i is 1,

Express

Where —CH ₂ — on cyclohexyl can be substituted by O, or

When i is 2, two are included in the formula

which is

Appears twice in the formula,

Independently for each occurrence

Where —CH ₂ — on cyclohexyl can be substituted by O, or

The optically active component is preferably:

Wherein R is a halogenated or unsubstituted alkyl, alkoxy or alkenyl group having 1 to 7 carbon atoms.

The stabilizer is preferably one or more of compounds having the general formulae VI1 to VI5.

In formulae VI1 to VI5, R ₉ is an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, and 1 to 7 carbon atoms Halogenated alkyl, halogenated alkoxy having 1 to 7 carbon atoms, or halogenated alkenyl having 2 to 7 carbon atoms; the alkyl group, the alkoxy group, and the alkenyl group are linear or branched Chain alkyl, alkoxy and alkenyl;

From

Any one of the group.

In a preferred embodiment of the present application, the liquid crystal composition further includes at least one polar compound and / or at least one non-polar compound. The polar compound is a positive polar compound and / or a negative polar compound, and is preferably a negative polar compound. The positive polar compound is selected from one or more of the compounds represented by the formulae X1 to X105. The negative polar compound is selected From one or more of the compounds represented by formulae IV1 to IV52, the non-polar compound is selected from one or more of the compounds represented by formulae V1 to V33.

Wherein, the positive-polarity compounds having X1 to X105 are:

In the formulae X1 to X105, R ₇ is H, an alkyl group, an alkoxy group, an alkenyl group, or an alkenyloxy group having 1 to 7 carbon atoms, wherein H or CH ₂ may be cyclopentyl, cyclopentene Or F substitution; R ₇ may be cyclopentyl or cyclopentyl substituted with alkyl, alkoxy or alkenyl of 1 to 7 carbon atoms; R ₈ is H, F, CN, NCS, Cl, OCF _3. Alkyl, alkoxy, alkenyl or alkenyloxy group having 1 to 7 carbon atoms, in which H or CH ₂ may be substituted by cyclopentyl or F; R ₈ may also be cyclopentyl or oxygen ring Amyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or selected from cyclopentenyl, oxycyclopentenyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl; the alkyl group having 1 to 7 carbon atoms is preferably: -CH ₃ , -C ₂ H ₅ , -C ₃ H ₇ , -C ₄ H ₉ , -C ₅ H ₁₁ , -C ₆ H ₁₃ or -C ₇ H ₁₅ ; the alkenyl group having 1 to 7 carbon atoms is preferably: -CH = CH ₂ , -CH = CHCH ₃ , -CH = CHC ₂ H ₅ , -CH = CHC ₃ H ₇ , -C ₂ H ₄ CH = CH ₂ , -C ₂ H ₄ CH = CHCH ₃ , -C ₃ H ₆ CH = CH ₂ or -C ₃ H ₆ CH = CHCH ₃ ; said An alkoxy group having 1 to 7 carbon atoms is preferably: -OCH ₃ , -OC ₂ H ₅ , -OC ₃ H ₇ , -OC ₄ H ₉ , -OC ₅ H ₁₁ , -OC ₆ H ₁₃ or -OC ₇ H ₁₅ ; The alkenyloxy group having 1 to 7 carbon atoms is preferably: -OCH = CH ₂ , -OCH ₂ CH = CH ₂ , -OCH ₂ CH = CHCH _3, or -OCH ₂ CH = CHC ₂ H ₅ ; X ₉ and X ₁₀ are each independently selected from H or F,

The polar liquid crystal compounds X1 to X105 have positive dielectric anisotropy, and can be combined with the liquid crystal composition to form a positive dielectric liquid crystal mixture or a negative dielectric liquid crystal mixture, which can be used to adjust the dielectric constant of the system. , Refractive index, rotational viscosity, elastic coefficient, and clearing point temperature. In addition, the addition of a positive dielectric liquid crystal compound with a large structural difference on the basis of the above composition is beneficial to lower the melting point and improve the low-temperature reliability of the liquid crystal mixture, thereby reducing the lower limit temperature of the liquid crystal medium and widening the operating temperature range of the liquid crystal medium.

The negative-polarity compounds having IV1 to IV52 are:

In the formulae IV1 to IV52, R ₃ and R ₄ are each independently H, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, and an alkenyl group having 2 to 7 carbon atoms. Or an alkenyloxy group having 2 to 7 carbon atoms, or an alkyl group having 1 to 7 carbon atoms and 1 to 7 carbon atoms in which H or CH ₂ is substituted with cyclopentyl, cyclopentenyl, or F 7 alkoxy, alkenyl having 2 to 7 carbon atoms or alkenyloxy having 2 to 7 carbon atoms, or cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl; the alkyl group having 1 to 7 carbon atoms is -CH ₃ , -C ₂ H ₅ , -C ₃ H ₇ , -C ₄ H ₉ , -C ₅ H ₁₁ , -C ₆ H ₁₃ or -C ₇ H ₁₅ ; the alkenyl group having 2 to 7 carbon atoms is preferably -CH = CH ₂ , -CH = CHCH ₃ , -CH = CHC ₂ H ₅ , -CH = CHC ₃ H ₇ , -C ₂ H ₄ CH = CH ₂ , -C ₂ H ₄ CH = CHCH ₃ , -C ₃ H ₆ CH = CH ₂ or -C ₃ H ₆ CH = CHCH ₃ ; the carbon atom The alkoxy group having a number of 1 to 7 is preferably -OCH ₃ , -OC ₂ H ₅ , -OC ₃ H ₇ , -OC ₄ H ₉ , -OC ₅ H ₁₁ , -OC ₆ H ₁₃ or -OC ₇ H ₁₅ ; The alkenyloxy group having 2 to 7 carbon atoms is preferably -OCH = CH ₂ , -OCH ₂ CH = CH ₂ , -OCH ₂ CH = CHCH _3, or -OCH ₂ CH = CHC ₂ H ₅ .

The above-mentioned polar liquid crystal compounds IV1 to IV52 have negative dielectric anisotropy. The negative dielectric constant liquid crystal compound is characterized by a large dipole effect in a direction perpendicular to the long axis of the molecule, and the corresponding dielectric constant is vertical. The component of the direction is relatively large, that is, it has a high vertical dielectric constant ε _{，, the} liquid crystal molecules tend to be distributed along the direction perpendicular to the electric field, and the negative liquid crystal material is arranged on the horizontal plane under the fringe electric field, and the pretilt angle distribution The positive material is more uniform, so it shows higher light transmittance and wide viewing angle. In addition, the addition of a liquid crystal compound with a negative dielectric constant can increase the bending elastic coefficient K _{33 of} the system, thereby improving the light transmittance in the entire system. , It is conducive to energy saving, and is helpful to improve the contrast. In addition, the addition of different types of liquid crystal compounds is also beneficial to improve the low temperature reliability of the liquid crystal medium, reduce the lower limit temperature of the liquid crystal medium, and widen the operating temperature range of the liquid crystal medium.

The non-polar liquid crystal compound is selected from one or more of the compounds represented by the formulae V1 to V33; wherein the formulae V1 to V33 are as follows:

In the formulae V1 to V33, R ₅ and R ₆ are each independently selected from H, F, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, and 2 carbon atoms. Alkenyl to 7 or alkenyloxy having 2 to 7 carbon atoms, or alkyl or carbon having 1 to 7 carbon atoms in which H or CH ₂ is substituted with cyclopentyl, cyclopentenyl, or F Alkoxy having 1 to 7 atoms, alkenyl having 2 to 7 carbon atoms or alkenyloxy having 2 to 7 carbon atoms; or cyclopentyl, oxycyclopentyl

Oxymethylcyclopentyl

Oxyethyl cyclopentyl

Oxymethylcyclopentenyl

Oxyethyl cyclopentenyl

The above non-polar liquid crystal compounds V1 to V6 have lower rotational viscosity γ ₁ , and the response time is proportional to the rotational viscosity γ ₁ , which means that the lower the rotational viscosity γ ₁ value, the lower the response time, the faster the response speed, and Liquid crystal mixtures having the above-mentioned non-polar liquid crystal compounds V1 to V6 are used to manufacture a fast-response liquid crystal medium. The above-mentioned non-polar liquid crystal compounds V7 to V17 have a relatively high clearing point temperature, and are mainly used to adjust the T _NI value of the system, so that the liquid crystal mixture having the above-mentioned non-polar liquid crystal compounds V7 to V17 is beneficial to increase the upper limit temperature of the liquid crystal medium. , Widen the operating temperature range of the liquid crystal medium. The above non-polar liquid crystal compounds V18 to V23 have an alkynylbenzene structure, and V27 to V33 have terphenyl structures, all of which are compounds of a large conjugate system, which is beneficial to increase the optical anisotropy Δn value of the system, and usually the optical path difference d · The value of Δn is predetermined. The higher the value of Δn, the lower the value of d, and the response speed is inversely proportional to the value of d. Therefore, the response speed of the liquid crystal mixtures having the above non-polar liquid crystal compounds V18 to V23 is more ideal. Value. The above non-polar liquid crystal compounds V24 to V26 have a large elastic coefficient K, and the response time is inversely proportional to the elastic coefficient K. It means that the higher the elastic coefficient K value, the lower the response time, the faster the response speed, so the above non-polar The liquid crystal mixture of the liquid crystal compounds V24 to V26 has a relatively ideal response speed.

The outstanding characteristics of the liquid crystal composition in the present invention are that the general formula I and the general formula II are added in small amounts to obtain appropriate optical characteristics, so the overall viscosity of the liquid crystal mixture can be reduced, and the response speed can be increased. Preferably, at least one low-viscosity non-polar liquid crystal compound having a structural formula III1 is added to the liquid crystal mixture to obtain a low-viscosity liquid crystal mixture and improve response speed. III1 is more preferably a compound in which R ₃ is propyl and R ₃ ′ is vinyl. The liquid crystal mixture is preferably applied to a liquid crystal display mode of vertical alignment display (VA), polymer stable vertical alignment (PSVA), or fringe field switch (FFS) type.

The content of the liquid crystal compound in the liquid crystal mixture can be adjusted according to the performance requirements of the liquid crystal material. In order to obtain a more suitable liquid crystal width, a higher dielectric anisotropy value, a smaller rotational viscosity, and a suitable elastic coefficient K, it is more conducive to improving the response speed of the liquid crystal material, reducing the threshold voltage, and improving the interaction of the liquid crystal material. Solubility, in a preferred embodiment of the present invention, the liquid crystal compound having the general formula I in the liquid crystal composition has a weight content of 0.1 to 75%, preferably 1 to 50%, and more preferably 1 to 30%; The liquid crystal compound II has a weight content of 0.1 to 75%, preferably 1 to 50%, and more preferably 1 to 30%; the liquid crystal compound having the general formula III has a weight content of 0.1 to 75%, and more preferably 0.1 to 50%. The remaining ingredients can be added in accordance with the above teachings of the present invention. The mass fraction of the polar liquid crystal compound is preferably 0 to 80%, and the mass fraction of the non-polar liquid crystal compound is preferably 0 to 80%. In short, the sum of the percentage content of each component is 100%.

In a typical embodiment of the present application, an application of the above liquid crystal composition in a liquid crystal display device is provided. Applying the liquid crystal composition of the present invention to the preparation of a liquid crystal display material or a liquid crystal display device can significantly improve the performance of the liquid crystal display material or the liquid crystal display device.

The beneficial effects of the present invention will be further described below in combination with the examples and comparative examples.

The following examples are intended to explain the invention without limiting it. The percentages involved in the examples are all mass percentages, and the temperature is expressed in degrees Celsius. The physical and chemical parameters measured is expressed as follows: T _NI represents clearing point; △ n denotes optical anisotropy _{_{(△ n = n e -n o}} , 589nm, measured temperature 25 ℃); ε _⊥ denotes the dielectric constant perpendicular (measuring temperature 25 ℃ ); △ ε represents the dielectric anisotropy (△ ε = ε _∥ -ε _⊥ , 25 ° C); k ₁₁ represents the coefficient of elasticity at expansion (measurement temperature 25 ° C); k ₃₃ represents the coefficient of bending elasticity (measurement temperature 25 ° C) ; Γ ₁ represents rotational viscosity (measured at 25 ° C.), and T _{NI is} measured using DSC; Δn is measured using an abbe refractometer; ε _⊥ , Δε, k ₁₁ , k _33, and γ _{1 are} measured using CV.

In the embodiments of the present invention, the main chain of the liquid crystal molecule is named: cyclohexyl

Represented by the letter C; benzene ring

Represented by the letter P; cyclohexenyl

Expressed as A; positive dielectric difluorobenzene

Expressed as Y; tetrahydropyran

Represented by Py; methoxy bridge -CH ₂ O- represented by B; difluoromethoxy bridge -CF ₂ O- represented by Q; alkynyl

Expressed as G, monofluorobenzene

Represented by the letter PF, negative dielectric difluorobenzene

Expressed as Z, difluorodibenzofuran

Represented by the letter X1.

The corresponding codes for specific group structures are shown in Table 1.

Table 1

The branch of each compound is converted into a chemical formula according to Table 2 below. The left branch is represented by R1 and the right branch is represented by R2. Wherein, the groups C _n H _{2n + 1} and C _m H _{2m + 1} are linear alkyl groups having n and m carbon atoms, respectively, and C _p represents cyclopentyl

C _n H _{2n + 1} C _p represents a cyclopentyl group with a linear alkyl group having n carbon atoms. When naming, the main chain is at the front and the branch chain is at the back. The main chain and the branch chain are separated by "-", such as

Expressed as WGX1-3O2;

Expressed as WW-2OO2;

Expressed as CCBW-3O2;

Expressed as PW-3O2;

Expressed as X1-2OO2;

Expressed as X1-CpOO2;

Expressed as Z-CpOO4;

Expressed in PHP-2Cp;

Expressed as PWP-3Cp3;

Expressed as PGW-3O2;

Expressed as X1-2OH.

Table 2

代码Code	R1R1	R2R2
nmnm	C _nH _2n+1 C _n H _{2n + 1}	C _mH _2m+1 C _m H _{2m + 1}
nHnH	C _nH _2n+1 C _n H _{2n + 1}	HH
nOHnOH	OC _nH _2n+1 OC _n H _{2n + 1}	HH
nOmnOm	C _nH _2n+1 C _n H _{2n + 1}	OC _mH _2m+1 OC _m H _{2m + 1}
nOOmnOOm	OC _nH _2n+1 OC _n H _{2n + 1}	OC _mH _2m+1 OC _m H _{2m + 1}
nCpnCp	C _nH _2n+1 C _n H _{2n + 1}	CpCp
nmCpnmCp	C _nH _2n+1 C _n H _{2n + 1}	C _mH _2m+1Cp C _m H _{2m + 1} Cp
nFnF	C _nH _2n+1 C _n H _{2n + 1}	FF
nOTFnOTF	C _nH _2n+1 C _n H _{2n + 1}	OCF ₃ OCF ₃
CpmCpm	CpCp	C _mH _2m+1 C _m H _{2m + 1}
CpHCpH	CpCp	HH
CpOHCpOH	OCpOCp	HH
CpOmCpOm	CpCp	OC _mH _2m+1 OC _m H _{2m + 1}
CpOOmCpOOm	OCpOCp	OC _mH _2m+1 OC _m H _{2m + 1}

CpFCpF	CpCp	FF
nCpmnCpm	C _nH _2n+1Cp C _n H _{2n + 1} Cp	C _mH _2m+1 C _m H _{2m + 1}
nCpHnCpH	C _nH _2n+1Cp C _n H _{2n + 1} Cp	HH
nCpOmnCpOm	C _nH _2n+1Cp C _n H _{2n + 1} Cp	OC _mH _2m+1 OC _m H _{2m + 1}
nCpOOmnCpOOm	OC _nH _2n+1Cp OC _n H _{2n + 1} Cp	OC _mH _2m+1 OC _m H _{2m + 1}
nCpFnCpF	C _nH _2n+1Cp C _n H _{2n + 1} Cp	FF

In addition, liquid crystal compounds

Expressed as 3HHV; liquid crystal compound

Expressed as 4HHV;

Expressed as VHHP1;

Represented by CC31D1;

Expressed as PPFP-F3;

Expressed as WW-2OO5V1.

Example 1

The composition and measurement parameters of the liquid crystal mixture of Example 1 are shown in Table 3.

table 3

Note: The liquid crystal compounds with the numbers 1 to 2 are liquid crystal compounds with the general formula I, the liquid crystal compounds with numbers 3 to 5 are the liquid crystal compounds with the general formula II, and the liquid crystal compounds with the numbers 6 to 7 are the liquid crystal compounds with the general formula III Liquid crystal compound.

Example 2

The composition and measurement parameters of the liquid crystal mixture of Example 2 are shown in Table 4.

Table 4

Note: The liquid crystal compound with the number 1 is a liquid crystal compound with the general formula I, the liquid crystal compound with the number 2 to 7 is a liquid crystal compound with the general formula II, and the liquid crystal compound with the number 8 to 10 is a liquid crystal compound with general formula III .

Example 3

The composition and measurement parameters of the liquid crystal mixture of Example 3 are shown in Table 5.

table 5

Note: The liquid crystal compound with the number 1 is a liquid crystal compound with the general formula I, the liquid crystal compound with the numbers 2-9 is a liquid crystal compound with the general formula II, and the liquid crystal compound with the number 10-10 is a liquid crystal compound with general formula III .

Example 4

The composition and measurement parameters of the liquid crystal mixture of Example 4 are shown in Table 6.

Table 6

Note: The liquid crystal compound with the number 1 is a liquid crystal compound with the general formula I, the liquid crystal compound with the number 2 to 8 is a liquid crystal compound with the general formula II, and the liquid crystal compound with the number 9 to 10 is a liquid crystal compound with general formula III .

Example 5

The composition and measurement parameters of the liquid crystal mixture of Example 5 are shown in Table 7.

Table 7

Example 6

The composition and measurement parameters of the liquid crystal mixture of Example 6 are shown in Table 8.

Table 8

Note: The liquid crystal compounds with the numbers 1 to 2 are liquid crystal compounds with the general formula I, the liquid crystal compounds with numbers 3 to 7 are the liquid crystal compounds with the general formula II, and the liquid crystal compounds with the numbers 8 to 9 are the liquid crystal compounds with the general formula III Liquid crystal compound.

Example 7

The composition and measurement parameters of the liquid crystal mixture of Example 7 are shown in Table 9.

Table 9

Note: The liquid crystal compound with the number 1 is a liquid crystal compound with the general formula I, the liquid crystal compound with the number 2 to 8 is a liquid crystal compound with the general formula II, and the liquid crystal compound with the number 9 to 11 is a liquid crystal compound with general formula III .

Example 8

The composition and measurement parameters of the liquid crystal mixture of Example 8 are shown in Table 10.

Table 10

Note: The liquid crystal compound having the number 1 is a liquid crystal compound having the general formula I, the liquid crystal compound having the number 2 to 8 is a liquid crystal compound having the general formula II, and the liquid crystal compound having the number 9 is a liquid crystal compound having general formula III.

Example 9

The composition and measurement parameters of the liquid crystal mixture of Example 9 are shown in Table 11.

Table 11

Example 10

The composition and measurement parameters of the liquid crystal mixture of Example 10 are shown in Table 12.

Table 12

Example 11

The composition and measurement parameters of the liquid crystal mixture of Example 11 are shown in Table 13.

Table 13

Note: The liquid crystal compound with the number 1 is a liquid crystal compound with the general formula I, the liquid crystal compound with the number 2 to 6 is a liquid crystal compound with the general formula II, and the liquid crystal compound with the number 7 to 8 is a liquid crystal compound with general formula III .

Example 12

The composition and measurement parameters of the liquid crystal mixture of Example 12 are shown in Table 14.

Table 14

Note: The liquid crystal compounds with serial numbers 1 to 2 are liquid crystal compounds with general formula I, the liquid crystal compounds with serial numbers 3 to 8 are liquid crystal compounds with general formula II, and the liquid crystal compounds with serial numbers 9 to 11 are Liquid crystal compound.

Example 13

The composition and measurement parameters of the liquid crystal mixture of Example 13 are shown in Table 15.

Table 15

Note: The liquid crystal compound with the number 1 is a liquid crystal compound with the general formula I, the liquid crystal compound with the number 2 to 7 is a liquid crystal compound with the general formula II, and the liquid crystal compound with the number 8 to 9 is a liquid crystal compound with general formula III .

Example 14

The composition and measurement parameters of the liquid crystal mixture of Example 14 are shown in Table 16.

Table 16

Note: The liquid crystal compound having the number 1 is a liquid crystal compound having the general formula I, the liquid crystal compound having the number 2 to 6 is a liquid crystal compound having the general formula II, and the liquid crystal compound having the number 7 is a liquid crystal compound having general formula III.

Example 15

The composition and measurement parameters of the liquid crystal mixture of Example 15 are shown in Table 17.

Table 17

Note: The liquid crystal compounds with serial numbers 1 to 2 are liquid crystal compounds with general formula I, the liquid crystal compounds with serial numbers 3 to 10 are liquid crystal compounds with general formula II, the liquid crystal compounds with serial number 11 are liquid crystal compounds with general formula III .

Comparative Example 1

The composition and measurement parameters of the liquid crystal mixture of Comparative Example 1 are shown in Table 18.

Table 18

Comparative Example 2

The composition and measurement parameters of the liquid crystal mixture of Comparative Example 2 are shown in Table 19.

Table 19

The composition and measurement parameters of the liquid crystal mixture of Comparative Example 3 are shown in Table 20.

Table 20

Among them, in Comparative Example 1, a general-purpose negative liquid crystal compound was used instead of the compound of the general formula I in Example 14, and in Comparative Example 2 was replaced by a compound of the general formula I in Example 14 of the CW-type compound of the general formula II. In Comparative Example 3, the compound of the general formula II in Example 14 was replaced by the compound of the general formula I.

It can be found from the above examples that the liquid crystal mixture composed of general formula I, general formula II and general formula III is particularly beneficial to increase the dielectric constant value of the system, and can improve the viscosity of the system, adjust the optical anisotropy value of the system, and increase the bending of the system The coefficient of elasticity K ₃₃ improves the response speed and the light transmittance in the whole system, which is conducive to energy saving and to improve contrast. When liquid crystal mixtures of general formula I, general formula II and general formula III are mixed with other liquid crystal compounds of different types, appropriate optical anisotropy, dielectric anisotropy, high-definition highlights, lower viscosity and higher elasticity can be obtained. Coefficient liquid crystal mixtures, especially III1, are more preferably compounds in which Y ₃ is propyl and Y ₃ ′ is vinyl. A low-viscosity liquid crystal mixture can be obtained, which can be used to produce a fast-response liquid crystal medium. The above measurement parameters are related to the physical and chemical properties of all liquid crystal compounds constituting the liquid crystal medium. The liquid crystal mixture of the present invention is mainly used to adjust the liquid crystal parameters of the system.

By comparing Example 14 and Comparative Example 1, it can be found that when a liquid crystal compound of the general formula I is combined with the general formula II and the general formula III, a relatively high optical anisotropy and a high vertical dielectric constant can be obtained. The liquid crystal mixture of ε _⊥ and bending elastic coefficient K ₃₃ , that is, the combination of the liquid crystal compound of the general formula I with the general formula II and the general formula III can obtain a liquid crystal compound with faster response speed, lower power consumption, higher transmittance and contrast Liquid crystal mixture.

By comparing Example 14 and Comparative Example 2, it can be found that when the compound of the general formula II in Example 14 is replaced by the compound of the general formula I, the liquid crystal mixture has a high rotational viscosity, which is not conducive to the response of the liquid crystal display. Increase in speed; it can be found by comparing Example 14 and Comparative Example 3 that when the CCW compound of Formula II in Example 14 is replaced by the compound of Formula I, the liquid crystal mixture has a very low clearing point. Conducive to increasing the display width of the liquid crystal display.

To sum up, the liquid crystal mixture composed of general formula I, general formula II and general formula III is particularly beneficial to adjust the dielectric constant value of the system, and can improve the viscosity of the system, adjust the optical anisotropy value of the system, and increase the bending elastic coefficient K _{33 of the} system. , Improve the liquid crystal use temperature width, which is conducive to the manufacture of fast response, low energy consumption, high contrast liquid crystal display devices.

Although the present invention does not exhaust all the liquid crystal mixtures claimed, those skilled in the art can foresee that on the basis of the above-disclosed embodiments, only similar professional methods can be used to obtain other similar liquid crystal materials. No creative work is required. Due to the limited space here, only representative embodiments are listed.

The above descriptions are merely preferred embodiments of the present invention and are not intended to limit the present invention. For those skilled in the art, the present invention may have various modifications and changes. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

A liquid crystal composition having a negative dielectric constant, wherein the liquid crystal composition includes at least one liquid crystal compound having the general formula I, at least one liquid crystal compound having the general formula II, and at least one liquid crystal III liquid crystal compounds,

The general formula I is:

among them,

Y and Y 'are independently selected from H, C1 ~ C7 alkyl, C1 ~ C7 alkoxy group, an alkenyl group of C2 ~ C7 alkenyl or C2 ~ C7 alkoxy, wherein H or CH 2 may be a ring Substituted with pentyl, cyclopentenyl or F; or, each of said Y and Y 'is independently selected from
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, Y and Y 'are each independently selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethyl cyclopentenyl;

m is selected from 0 or 1; n is selected from 0, 1 or 2;

Z is selected from a single bond, O,
CH 2 , CH 2 O, C 2 H 4 , C 2 H 4 O, C 3 H 6 , C 3 H 6 O, C 4 H 8 , OC 4 H 8 , C 2 H 2 , C 2 H 2 O, Any of C 3 H 4 O, OCH 2 O, OC 2 H 4 O, OC 3 H 6 O, or OC 4 H 8 O, wherein H may be replaced by F;

When n is 1,
From

Any one of the group.

When n is 2, two are included in the formula
which is
Occurs twice in the general formula, at each occurrence
Each independently selected

Any one of the group.

The general formula II is:

Among them, Y 1 and Y 1 ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH 2 may be substituted with cyclopentyl, cyclopentenyl or F; or, Y 1 and Y 1 ′ are each independently selected from cyclopentyl, oxycyclopentyl
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, Y 1 and Y 1 ′ are each independently selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethyl cyclopentenyl;

k is selected from 0, 1 or 2;

From

Any one of the group.

The general formula III is:

Among them, Y 2 and Y 2 ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH 2 may be substituted with cyclopentyl, cyclopentenyl or F; or, each of Y 2 and Y 2 ′ is independently selected from cyclopentyl, oxycyclopentyl
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, Y 2 and Y 2 ′ are each independently selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethyl cyclopentenyl;

Each independently selected

Any one of the group.
The liquid crystal composition according to claim 1, wherein the general formula I is

Among them, R 1 and R 1 ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH 2 may be substituted with cyclopentyl, cyclopentenyl, or F; or, R 1 and R 1 ′ are each independently selected from cyclopentyl, oxycyclopentyl
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethyl cyclopentyl; or, R 1 and R 1 ′ are each independently selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl.
The liquid crystal composition according to claim 1, wherein the general formula II is:

Among them, R 2 and R 2 ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenyloxy, wherein H or CH 2 may be substituted by cyclopentyl, cyclopentenyl or F; or, R 2 and R 2 ′ are each independently selected from cyclopentyl, oxycyclopentyl
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, R 2 and R 2 ′ are each independently selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl.
The liquid crystal composition according to claim 1, wherein the general formula III is:

Among them, Y 3 and Y 3 ′ are each independently selected from H, C1 to C7 alkyl, C1 to C7 alkoxy, C2 to C7 alkenyl, or C2 to C7 alkenoxy, wherein H or CH 2 may be substituted by cyclopentyl, cyclopentenyl or F; or, each of Y 3 and Y 3 ′ is independently selected from cyclopentyl, oxycyclopentyl
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or, each of Y 3 and Y 3 ′ is independently selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl.
The liquid crystal composition according to any one of claims 1 to 4, wherein the liquid crystal composition further comprises at least one polar compound and / or at least one non-polar compound.
The liquid crystal composition according to claim 1, wherein a weight content of the liquid crystal compound having the general formula I in the liquid crystal composition is 0.1 to 75%, preferably 0.1 to 50%, and more preferably 0.1. -30%; the weight content of the liquid crystal compound having the general formula II is 0.1 to 75%, preferably 0.1 to 50%, and still more preferably 0.1 to 30%; the weight content of the liquid crystal compound having the general formula III is 0.1 to 75%, and more preferably 0.1 to 50%.
The liquid crystal composition according to claim 5, wherein the polar compound is a positive electrode compound and / or a negative electrode compound, preferably a negative electrode compound, and the negative electrode compound is selected from the group consisting of formulae IV1 to IV52. One or more of the compounds, the non-polar compound is selected from one or more of the compounds represented by formulas V1 to V33,

Formulas IV1 to IV52 are as follows:

In the formulae IV1 to IV52, R 3 and R 4 are each independently H, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, and an alkenyl group having 2 to 7 carbon atoms. Or an alkenyloxy group having 2 to 7 carbon atoms, or an alkyl group having 1 to 7 carbon atoms and 1 to 7 carbon atoms in which H or CH 2 is substituted with cyclopentyl, cyclopentenyl, or F 7 alkoxy, alkenyl having 2 to 7 carbon atoms or alkenyloxy having 2 to 7 carbon atoms, or cyclopentyl, oxycyclopentyl
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl; the alkyl group having 1 to 7 carbon atoms is -CH 3 , -C 2 H 5 , -C 3 H 7 , -C 4 H 9 , -C 5 H 11 , -C 6 H 13 or -C 7 H 15 ; the alkenyl group having 2 to 7 carbon atoms is preferably -CH = CH 2 , -CH = CHCH 3 , -CH = CHC 2 H 5 , -CH = CHC 3 H 7 , -C 2 H 4 CH = CH 2 , -C 2 H 4 CH = CHCH 3 , -C 3 H 6 CH = CH 2 or -C 3 H 6 CH = CHCH 3 ; the carbon atom The alkoxy group having a number of 1 to 7 is preferably -OCH 3 , -OC 2 H 5 , -OC 3 H 7 , -OC 4 H 9 , -OC 5 H 11 , -OC 6 H 13 or -OC 7 H 15 ; The alkenyloxy group having 2 to 7 carbon atoms is preferably -OCH = CH 2 , -OCH 2 CH = CH 2 , -OCH 2 CH = CHCH 3, or -OCH 2 CH = CHC 2 H 5 .

The formulas V1 to V33 are:

In the formulae V1 to V33, R 5 and R 6 are each independently selected from H, F, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, and 2 carbon atoms. Alkenyl to 7 or alkenyloxy having 2 to 7 carbon atoms, or alkyl or carbon having 1 to 7 carbon atoms in which H or CH 2 is substituted with cyclopentyl, cyclopentenyl or F An alkoxy group having 1 to 7 atoms, an alkenyl group having 2 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms, or a cyclopentyl group or an oxycyclopentyl group
Oxymethylcyclopentyl
Oxyethyl cyclopentyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentyl, oxycyclopentyl, oxymethylcyclopentyl, Oxyethylcyclopentyl; or selected from cyclopentenyl, oxycyclopentenyl
Oxymethylcyclopentenyl
Oxyethyl cyclopentenyl
Or C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl or C2-C7 alkoxy substituted cyclopentenyl, oxycyclopentenyl, oxymethyl cyclopentyl Alkenyl, oxyethylcyclopentenyl; the alkyl group having 1 to 7 carbon atoms is -CH 3 , -C 2 H 5 , -C 3 H 7 , -C 4 H 9 , -C 5 H 11 , -C 6 H 13 or -C 7 H 15 ; the alkenyl group having 2 to 7 carbon atoms is preferably -CH = CH 2 , -CH = CHCH 3 , -CH = CHC 2 H 5 , -CH = CHC 3 H 7 , -C 2 H 4 CH = CH 2 , -C 2 H 4 CH = CHCH 3 , -C 3 H 6 CH = CH 2 or -C 3 H 6 CH = CHCH 3 ; the carbon atom The alkoxy group having a number of 1 to 7 is preferably -OCH 3 , -OC 2 H 5 , -OC 3 H 7 , -OC 4 H 9 , -OC 5 H 11 , -OC 6 H 13 or -OC 7 H 15 ; The alkenyloxy group having 2 to 7 carbon atoms is preferably -OCH = CH 2 , -OCH 2 CH = CH 2 , -OCH 2 CH = CHCH 3, or -OCH 2 CH = CHC 2 H 5 .

Preferably, the mass fraction of the polar liquid crystal compound in the liquid crystal composition is 0 to 80%, and the mass fraction of the non-polar liquid crystal compound is 0 to 80%.
The liquid crystal composition according to any one of claims 1 to 7, wherein the liquid crystal mixture further comprises a polymerizable compound having a mass fraction of 0 to 20%, and the general formula of the polymerizable compound is as follows:

among them

—T 1 and —T 2 are each independently represented
Or epoxy

—W 1 — and —W 2 — each independently represent a single bond or an alkyl group having 1 to 8 carbon atoms;

—X 1 —and —X 2 — each independently represent a single bond, —O—, —CO—, —COO— or —OCO—;

—Z 1 —Single bond, —O—, —CO—, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —C 2 H 4 —, —CF 2 O—, — OCF 2 —, -C≡C-, —CH = CH—,

One or two of the group consisting of;

i is 0, 1 or 2;

Each occurrence independently represents an unsubstituted or -CH 2 -on cyclohexylene group substituted with O
= CH on unsubstituted or phenylene ring-substituted by N
H on the ring is replaced by F
The liquid crystal composition having a positive dielectric constant according to any one of claims 1 to 7, wherein the liquid crystal composition further comprises a stabilizer with a mass fraction of 0 to 20%. The stabilizer is one or more of the compounds represented by the general formulae VI1 to VI5:

R 9 is an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, and a halogenated alkyl group having 1 to 7 carbon atoms , A halogenated alkoxy group having 1 to 7 carbon atoms, or a halogenated alkenyl group having 2 to 7 carbon atoms; the alkyl group, the alkoxy group, and the alkenyl group are linear or branched alkyl groups , Alkoxy and alkenyl;

From

Any one of the group.
The use of the liquid crystal composition according to any one of claims 1 to 9 in a liquid crystal display material or a liquid crystal display device is preferably an application in a negative display mode, and the negative display mode is preferably VA, PSVA, or FFS and other display modes.