CN117070229A - Liquid crystal mixture and application thereof - Google Patents

Liquid crystal mixture and application thereof Download PDF

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Publication number
CN117070229A
CN117070229A CN202310981516.8A CN202310981516A CN117070229A CN 117070229 A CN117070229 A CN 117070229A CN 202310981516 A CN202310981516 A CN 202310981516A CN 117070229 A CN117070229 A CN 117070229A
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liquid crystal
crystal compound
mass
carbon atoms
compound
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陈新华
李珊珊
陈海舟
吴成胜
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VVI Bright China Ltd
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VVI Bright China Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1343—Electrodes
    • G02F1/134309—Electrodes characterised by their geometrical arrangement
    • G02F1/134372—Electrodes characterised by their geometrical arrangement for fringe field switching [FFS] where the common electrode is not patterned
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
    • G02F1/13712—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having negative dielectric anisotropy

Abstract

The application provides a negative liquid crystal mixture with higher clearing point, which is prepared from the following componentsLiquid crystal compound having structure and havingLiquid crystal compound having structure and havingA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofA liquid crystal compound of structure; has the following characteristics ofLiquid crystal compound having structure and method for producing the same

Description

Liquid crystal mixture and application thereof
The application is a division of the prior application patent with the application number of 2017110555753 and the application date of 2017.10.31.
Technical Field
The application relates to the field of liquid crystal materials, in particular to a liquid crystal compound, a liquid crystal mixture containing the liquid crystal compound and application thereof.
Background
In the 60 s of the 20 th century, RCA corporation discovered for the first time that the light transmission mode of liquid crystals was changed by electric stimulation, and then after the liquid crystal display technology was released by applying this property, liquid crystals gradually attracted high attention and rapidly developed to various fields. In 1966, duPont had synthesized Kevlar fibers using aramid liquid crystals, and the liquid crystal materials began the industrialization process. Through rapid development for decades, the liquid crystal material has been widely applied to various fields such as display technology, optical storage equipment, solar cells and the like by virtue of the special properties, and the research scope is more over the fields such as chemistry, biology, information science and the like, so that the liquid crystal material becomes one of the favored and indispensable novel materials in the current society.
With the recent trend of science and technology, the requirements of liquid crystal materials are also increasing. The development of liquid crystal materials is expected to mainly have the following aspects in the future: (1) The new process for preparing the existing liquid crystal material is explored, the generation of byproducts and harmful substances is reduced, and the production cost is reduced; (2) The performance of the existing liquid crystal material is modified, such as reducing the requirement on the environmental temperature, improving the color richness and diversity of the liquid crystal material for display, etc.; (3) The novel functional liquid crystal material is prepared to meet the high standard use requirements of multiple fields, such as novel liquid crystal material for display, novel photoelectric liquid crystal storage material in the field of information engineering, novel medicinal liquid crystal material in the field of bioengineering and the like.
Liquid crystal displays can be divided into passive matrix (also called passive matrix or simple matrix) and active matrix (also called active matrix) driving methods. Among them, the active matrix lcd is to change the arrangement of liquid crystal compounds by applying a voltage, so as to change the light emission intensity of the backlight source to form an image, and is increasingly popular due to its characteristics of high resolution, high contrast, low power, thin surface and light weight. Active matrix liquid crystal displays can be classified into two types according to active devices: a MOS (metal oxide semiconductor) or other diode on a silicon chip as a substrate; among them, thin film transistor (TFT-LCD) is the most rapidly developed one, which has been well applied to display devices such as mobile phones, computers, liquid crystal televisions, and cameras, and has become the mainstream product of the liquid crystal market. With the continuous development of TFT-LCDs, a wide viewing angle mode has become a target pursued in the industry, and currently, the main wide viewing angle technologies mainly include VA vertical alignment technology, IPS in-plane switching technology, FFS fringe field switching technology, and the like, which all require higher light transmittance and smaller color shift. Negative type liquid crystal compounds are excellent in color shift and are affected by a vertical electric field, and exhibit higher light transmittance than positive type materials, and thus are widely used.
With the wide application of liquid crystal displays, the performance requirements of the liquid crystal displays are continuously increasing. The liquid crystal display requires a wider operating temperature, a faster response speed, and a higher contrast ratio in terms of high image quality, and requires lower and lower power consumption, which means that the liquid crystal display has a lower driving voltage and higher light transmittance. These improvements in properties are all kept away from the improvement of the liquid crystal material.
Disclosure of Invention
The application aims to provide a liquid crystal compound with negative dielectric constant, which is used for improving the rotation viscosity and the elastic coefficient characteristics of a liquid crystal material in the prior art, so as to improve the response speed, the light transmittance and the contrast of the liquid crystal material and reduce the driving voltage.
It is another object of the present application to provide a liquid crystal mixture comprising the above liquid crystal compound.
It is a further object of the present application to provide the use of the above liquid crystalline compounds and liquid crystalline mixtures.
The technical scheme is as follows: in order to achieve the above object, according to one aspect of the present application, there is provided a liquid crystal compound having the general formula I:
wherein the method comprises the steps of
R is C1-C7 alkyl, C1-C7 alkoxy, C1-C7 alkenyl, C1-C7 alkenylalkoxy, cyclopentyl, or cyclopentyl substituted by C1-C7 alkyl, C1-C7 alkoxy, C1-C7 alkenyl, or C1-C7 alkenylalkoxy;
n is 0, 1 or 2;
selected from-> One or more of the group consisting of; when n is 1, ">One selected from the group consisting of the above groups; when n is 2, two +.>Two->Is the same group or two different groups selected from the group consisting of the above groups.
According to another aspect of the present application, there is provided a liquid crystal mixture having negative dielectric anisotropy, the liquid crystal compound comprising at least one of the liquid crystal compounds described above.
According to a further aspect of the present application there is provided the use of a liquid crystal compound as described above in a liquid crystal display material or a liquid crystal display device.
According to a further aspect of the present application there is provided the use of a liquid crystal mixture as described above in a liquid crystal display material or a liquid crystal display device.
The beneficial effects are that: the liquid crystal compound can effectively improve the rotation viscosity and the elasticity coefficient characteristics of the liquid crystal material, so that the response speed, the light transmittance and the contrast ratio of the liquid crystal display are improved, and the driving voltage of the liquid crystal display is reduced.
Detailed Description
It should be noted that, without conflict, the embodiments of the present application and features of the embodiments may be combined with each other. The present application will be described in detail with reference to examples.
In one exemplary embodiment of the present application, a liquid crystal compound is provided having the general formula I
In the general formula I
R is an alkyl, alkoxy, alkenyl or alkenylalkoxy group having 1 to 7 carbon atoms, or is a cyclopentyl group, or is an alkyl, alkoxy, alkenyl or alkenylalkoxy-substituted cyclopentyl group having 1 to 7 carbon atoms;
n is 0, 1 or 2;
when n is a number of times 1,selected from-> Any one of the group consisting of;
when n is 2, in formula ITwo occurrences, two->Can be selected from-> Either the same group or two different groups in the group consisting.
The liquid-crystalline compounds having a negative dielectric constant of the formula I are white in the pure state. The liquid crystal compound with negative dielectric constant is characterized by larger dipole action in the direction perpendicular to the long axis of the molecule, and thus the corresponding dielectric constant is in the vertical directionThe directional component is relatively large, i.e. has a high vertical dielectric constant epsilon ⊥ Thus dielectric anisotropy Δε=ε // -ε ⊥ Exhibiting negative values. Due to the higher vertical dielectric constant epsilon ⊥ The liquid crystal molecules tend to be distributed along the direction perpendicular to the electric field, so that the liquid crystal molecules show a lower pretilt angle, and the negative liquid crystal material is arranged on a horizontal plane under the fringe electric field, and the pretilt angle distribution is more uniform than that of the positive material, so that the liquid crystal molecules show higher light transmittance and wide viewing angle, and are particularly suitable for preparing VA, PSVA and FFS type liquid crystal materials with high transmittance and wide viewing angle; in addition, the addition of the liquid crystal compound with negative dielectric constant can improve the bending elastic coefficient K of the system 33 Therefore, the light transmittance and contrast ratio of the whole system can be improved, the energy conservation is facilitated, the image display quality can be improved, and the performance requirement of liquid crystal display can be better met.
Another outstanding feature of the liquid-crystalline compounds of the general formula I with a negative dielectric constant is that, when combined with other liquid-crystalline compounds, suitable optical properties and dielectric constants can be obtained with a small addition. Therefore, the liquid crystal mixture obtained by combining the liquid crystal compound with the negative dielectric constant in the general formula I with other liquid crystal compounds has lower overall viscosity, and the reduced viscosity can effectively reduce the response time of the liquid crystal material and increase the response speed.
Furthermore, it should be clear to a person skilled in the art that the above 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 advantageous to increase the response speed of the liquid crystal material, decrease the threshold voltage, and improve the intersolubility of the liquid crystal material, in a preferred embodiment of the present application, the liquid crystal compound having a negative dielectric constant of the general formula I is a negative polarity liquid crystal compound having the formulas I1 to I13.
The above compounds of the general formulae I1 to I13 are of the formula:
wherein R is 1 Is an alkyl, alkoxy, alkenyl or alkenylalkoxy group having 1 to 7 carbon atoms, or is a cyclopentyl group, or is an alkyl, alkoxy, alkenyl or alkenylalkoxy-substituted cyclopentyl group having 1 to 7 carbon atoms.
Because the liquid crystal compound with the negative dielectric constant of the general formula I has lower rotational viscosity and higher elastic coefficient K, when the liquid crystal compound with the general formula I is combined with other liquid crystal compounds to form a liquid crystal mixture with the negative dielectric constant, the characteristics of the liquid crystal mixture with the negative dielectric constant can be adjusted in a wider range, so that the performance requirements of more liquid crystal materials are met; the liquid crystal compound with the negative dielectric constant of the general formula I has better intersolubility when being mixed with other liquid crystal compounds, has less limitation on the types of other liquid crystal compounds used in combination, can be suitable for various liquid crystal mixtures corresponding to purposes, and is particularly beneficial to improving the comprehensive properties of the liquid crystal mixture; in addition, the liquid crystal mixture has good UV, light and heat stability.
The liquid-crystal mixtures according to the application having a negative dielectric constant can be prepared in a conventional manner. The desired amount of the components is dissolved in the components constituting the main ingredient in a relatively low amount, usually at high temperature; the solutions of the components may also be mixed with an organic solvent, for example, acetone, chloroform or methanol, and after thorough mixing, the solvent is removed again, for example, by distillation.
The type of the conventional liquid crystal compound contained in the liquid crystal mixture having a negative dielectric constant of the present application is not limited, and any type of liquid crystal compound may be selected according to the purpose to constitute the liquid crystal mixture together with the liquid crystal compound of the present application, and other additives in the art may be added as required. For example, a polymerizable compound and/or a stabilizer may be added in an amount of 0 to 20% by mass.
The above polymerizable compound has the following general formula:
wherein the method comprises the steps of
—T 1 and-T 2 Each independently representsOr an epoxy group;
—Y 1 -and-Y 2 -each independently represents a single bond or an alkyl group having 1 to 8 carbon atoms;
—X 1 -and-X 2 -each independently represents a single bond, -O- (CO), -COO-, or-OCO-;
m is 0, 1 or 2;
when m 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 —、-C≡C-、—CH＝CH—、
When m is 2, -Z 1 -appear twice in the general formula, -Z 1 -each occurrence independently represents a single bond, -O, -CO, -COO, -OCO, -CH 2 O—、—OCH 2 —、—C 2 H 4 —、—CF 2 O—、—OCF 2 —、-C≡C-、—CH＝CH—、
Representation->wherein-CH 2-on the cyclohexyl group may be replaced by O, or represents +.>Wherein =ch-on the benzene ring may be substituted by N, H on the benzene ring may be substituted by F, or +.>
When m is 1, the number of the groups,representation->wherein-CH 2-on the cyclohexyl group may be replaced by O, or representsWherein =ch-on the benzene ring may be substituted by N, H on the benzene ring may be substituted by F, or +.>
When m is 2, two are included in the formulaI.e. < ->Two occurrences of +_in the general formula>Each occurrence is independently +.>wherein-CH 2-on the cyclohexyl radical may be replaced by O, or is +.>Wherein =ch-on the benzene ring may be substituted by N, H on the benzene ring may be substituted by F, or +.>
The stabilizer is preferably one or more of the compounds represented by the general formulae IV1 to IV 5.
Of the formulae IV1 to IV5
R 7 Is a halogenated or unsubstituted alkyl, alkoxy or alkenyl group having 1 to 7 carbon atoms, the alkyl, alkoxy or alkenyl group being a straight or branched alkyl, alkoxy or alkenyl group;
is-> Any one of the group consisting of.
In a preferred embodiment of the present application, the liquid-crystal mixture further comprises at least one polar compound and/or at least one non-polar compound. The polar compound is preferably a negative polar compound, and the negative polar compound is preferably one or more selected from compounds represented by formulas II1 to II77, wherein formulas II1 to II77 are respectively:
wherein R is 3 And R is 4 Each independently represents H, 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 or an alkenylalkoxy group having 2 to 7 carbon atoms, H or CH in the above alkyl, alkoxy, alkenyl and alkenylalkoxy groups 2 Can be substituted by cyclopentyl; r is R 3 And R is 4 Or can be cyclopentyl or an alkyl, alkoxy or alkenyl substituted cyclopentyl of 1 to 7 carbon atoms; alkyl groups having 1 to 7 carbon atoms are: -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 method comprises the steps of carrying out a first treatment on the surface of the Alkenyl 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 The method comprises the steps of carrying out a first treatment on the surface of the Alkoxy 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 method comprises the steps of carrying out a first treatment on the surface of the Alkenylalkoxy having 1 to 7 carbon atoms is preferably-OCH 2 CH＝CH 2 、-OCH 2 CH＝CHCH 3 or-OCH 2 CH＝CHC 2 H 5 。
The polar liquid crystal compounds II1 to II77 have negative dielectric anisotropy, and can be combined with a compound having the general formula I to form a negative dielectric liquid crystal mixtureFor adjusting the dielectric constant, refractive index, rotational viscosity gamma of the system 1 Parameters such as elasticity coefficient, clearing point temperature and the like, and the collocation with the general formula I is beneficial to improving the low-temperature reliability of the liquid crystal mixture, reducing the lower limit temperature of the use of the liquid crystal medium and widening the working temperature range of the liquid crystal medium.
The nonpolar liquid crystal compound is selected from one or more of compounds shown in formulas III 1-III 29; wherein, the formulas III1 to III29 are as follows:
/>
in the formulae III1 to III29, R 5 、R 6 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 or an alkenylalkoxy group having 2 to 7 carbon atoms, H or CH in the above alkyl, alkoxy, alkenyl and alkenylalkoxy groups 2 Can be substituted by cyclopentyl; r is R 5 、R 6 Or can be cyclopentyl or an alkyl, alkoxy or alkenyl substituted cyclopentyl of 1 to 7 carbon atoms; the above 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 method comprises the steps of carrying out a first treatment on the surface of the The alkenyl group having 2 to 7 carbon atoms mentioned above 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 method comprises the steps of carrying out a first treatment on the surface of the The above 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 method comprises the steps of carrying out a first treatment on the surface of the The above alkenylalkoxy groups having 2 to 7 carbon atoms are preferably-OCH 2 CH＝CH 2 、-OCH 2 CH＝CHCH 3 or-OCH 2 CH＝CHC 2 H 5 . It will be clear to the person skilled in the art that the above alkyl, alkoxy, alkenyl, alkenylalkoxy groups may be straight chain alkyl, straight chain alkoxy, straight chain alkenyl, straight chain alkenylalkoxy groups, or branched alkyl, alkoxy, alkenyl and alkenylalkoxy groups.
The above nonpolar liquid crystal compounds III1 to III20 have low rotational viscosity gamma 1 Its response time and rotational viscosity gamma 1 Proportional, illustrative of rotational viscosity gamma 1 The lower the value, the lower the response time, the faster the response speed, and the liquid-crystal mixtures with the above-mentioned nonpolar liquid-crystal compounds III1 to III20 can be used for producing fast-responding liquid-crystal media. The above-mentioned nonpolar liquid crystal compounds III21 to III27 have a terphenyl structure, which is advantageous in increasing the optical anisotropy Δn value of the system, and in general, the higher the Δn value, the lower the d value, and the response speed is inversely proportional to the d value, so that the response speed of the liquid crystal mixture having the above-mentioned nonpolar liquid crystal compounds III21 to III27 has a more desirable value. The nonpolar liquid crystal compounds III28 to III29 have higher clearing point temperature and are mainly used for regulating T of a system NI The values, and thus the liquid-crystalline mixtures having the above-mentioned nonpolar liquid-crystalline compounds III28 to III29, advantageously lead to an increase in the upper temperature of the liquid-crystalline medium used and a broadening of the operating temperature range of the liquid-crystalline medium.
The liquid crystal compound shown in the general formula I has the outstanding characteristics that when the liquid crystal compound is combined with a low-viscosity liquid crystal compound, the liquid crystal compound can obtain proper optical characteristics by adding a small amount of the liquid crystal compound, so that the overall viscosity of a liquid crystal mixture can be reduced, and the response speed is increased. Preferably, at least one low-viscosity nonpolar liquid crystal compound having the structural formula III1 to III20 is added to the liquid crystal mixture to obtain a low-viscosity liquid crystal mixture, thereby improving the response speed. It is particularly preferred to add at least one low-viscosity nonpolar liquid-crystalline compound of the formula III5 to the liquid-crystalline mixture. The liquid crystal mixture is preferably used in a vertical alignment display (VA), a Polymer Stabilized Vertical Alignment (PSVA) or Fringe Field Switching (FFS) type liquid crystal display mode.
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 advantageous to increase the response speed of the liquid crystal material, decrease the threshold voltage, and improve the intersolubility of the liquid crystal material, and in a preferred embodiment of the present application, the weight content of the liquid crystal compound having the general formula I in the liquid crystal mixture is 0.1 to 75%, preferably 1 to 50%, and more preferably 1 to 30%. The remaining ingredients may be added in accordance with the teachings of the present application as set forth above. In general, the sum of the percentages of the components is 100%.
In one exemplary embodiment of the present application, there is provided a use of the liquid crystal compound represented by the above formula I in a liquid crystal display device. In yet another exemplary embodiment of the present application, there is provided a use of a liquid crystal mixture comprising a liquid crystal compound represented by formula I in a liquid crystal display device. The liquid crystal compound can be applied to the preparation of liquid crystal display materials or liquid crystal display equipment, and can obviously improve the performance of the liquid crystal display materials or the liquid crystal display equipment.
The advantageous effects of the present application will be further described below with reference to examples and comparative examples.
The following examples are intended to illustrate the application without limiting it. All percentages referred to in the examples are mass percentages and temperatures are expressed in degrees celsius. The measured physicochemical parameters are expressed as follows: t (T) NI Indicating a clearing point; Δn represents optical anisotropy (Δn=n) e -n o 589nm, measurement temperature 25 ℃); epsilon ⊥ Represents the vertical dielectric constant (measured temperature 25 ℃); Δεrepresents dielectric anisotropy (Δε=ε) ∥ -ε ⊥ ，25℃)；k 33 The bending modulus of elasticity (measured temperature 25 ℃ C.); gamma ray 1 The rotational viscosity was expressed (measurement temperature 25 ℃ C.), and T was measured by DSC NI The method comprises the steps of carrying out a first treatment on the surface of the Measuring delta n by using an abbe refractometer; measurement of ε using CV ⊥ 、△ε、k 33 And gamma 1 。
In various embodiments of the present application, each compound in the liquid crystal mixture has the general structural formula:
wherein a, b, c, d, e, f, g and h are each independently selected from 0, 1, 2,3 or 4.
Naming of the main chain of the liquid crystal molecule: cyclohexyl groupIndicated by the initial letter C; benzene ring->Denoted by the initial letter P; cyclohexenyl->Represented by A; difluorobenzene->Expressed as PFF; tetrahydropyran->Represented by Py; -CH 2O-is represented by-CH 2O-.
In addition, liquid crystal compoundExpressed in 3 HHV; />Expressed as VHHP 1; />Denoted by CC31D 1.
The corresponding codes for specific group structures are shown in table 1.
TABLE 1
In contrast to the general structural formula of each compound in the above liquid crystal mixtures, each compound branch is converted into a chemical formula according to Table 2 below, wherein the group C n H 2n+1 And C m H 2m+1 Is a straight-chain alkyl group having n and m carbon atoms, C p Represents cyclopentylC n H 2n+1 C p Represents a cyclopentyl group having a linear alkyl group of n carbon atoms. When named, the main chain is at the front and the branched chain is at the rear, e.gC- (CH 2O) -PFF3H,>expressed as CC-CH2O-PFF3H,expressed as PPFFCpO2, ">Expressed as CC-CH2O-PFF3O2,>represented by PPFP2 Cp.
TABLE 2
Example 1
The synthesis method of CC-CH2O-PFF3H comprises the following steps:
1) Preparation of sulfonic acid esters of propyldicyclohexyl methanol
A thermometer, a mechanical stirring and constant pressure dropping funnel are arranged in a 2000ml four-port bottle, nitrogen is introduced, 75g of propyldicyclohexyl methanol, 101.6g of triethylamine and 600ml of dichloromethane are added into a reaction system, stirring and cooling are carried out by using an ice salt bath, a mixed solution of 115g of methylbenzenesulfonyl chloride and 200ml of dichloromethane is dropwise added into the reaction system at 0-10 ℃, after the dropwise addition is finished, stirring and reaction are continued for 1 hour at 0-10 ℃, sampling analysis is carried out, after the reaction is finished, the system is poured into water, dichloromethane is added for dilution, standing and layering are carried out, a lower organic phase is separated out, water washing is carried out to be neutral, and after anhydrous magnesium sulfate is used for drying, ethanol is used for crystallization, and a product with the content of more than 99.5% is obtained.
2) Preparation of CC-CH2O-PFF3H
A low-temperature thermometer, mechanical stirring and a constant-pressure dropping funnel are arranged in a 250ml three-port bottle, nitrogen is introduced, 10g of 2, 3-difluorophenol, 13.8g of anhydrous potassium carbonate and 50ml of DMF are added into the system, after stirring and dissolution, the mixed solution of the sulfonate of propyl dicyclohexyl methanol and DMF prepared in the step 1) is added into the reaction system dropwise at 65 ℃, after finishing the dripping, the temperature is kept at 80 ℃ for 4 hours, the post-treatment is carried out, after pouring into the separating funnel, tap water is added into the separating funnel, the mixture is stood for layering, water is washed to be neutral, the solvent is removed by concentration, and then 9.8g of trans CC-CH2O-PFF3H with the purity of more than 99.8% can be obtained by ethanol recrystallization. The liquid crystal mixture composition and the measurement parameters of example 1 are shown in Table 3.
TABLE 3 Table 3
Note that: the liquid crystal compound with the sequence number of 5 is a liquid crystal compound with the general formula I.
Example 2
The liquid crystal mixture composition and the measurement parameters of example 2 are shown in Table 4.
TABLE 4 Table 4
/>
Note that: 7 is a liquid crystal compound having the general formula I.
Example 3
The liquid crystal mixture composition and the measurement parameters of example 3 are shown in Table 5.
TABLE 5
Note that: 7 is a liquid crystal compound having the general formula I.
Example 4
The liquid crystal mixture composition and the measurement parameters of example 4 are shown in Table 6.
TABLE 6
/>
Note that: 7 is a liquid crystal compound having the general formula I.
Example 5
The liquid crystal mixture composition and the measurement parameters of example 5 are shown in Table 7.
TABLE 7
Note that: 7 is a liquid crystal compound having the general formula I.
Example 6
The liquid crystal mixture composition and the measurement parameters of example 6 are shown in Table 8.
TABLE 8
Note that: 5 is a liquid crystal compound having the general formula I.
Example 7
The liquid crystal mixture composition and the measurement parameters of example 7 are shown in Table 9.
TABLE 9
/>
Note that: 7 is a liquid crystal compound having the general formula I.
Example 8
The synthesis method of the C-CH2O-PFF3H comprises the following steps:
1) Preparation of sulfonic acid esters of propylcyclohexylmethoxy
A thermometer, a mechanical stirring and constant pressure dropping funnel are arranged in a 1000ml four-port bottle, 78g of propylcyclohexyl methanol, 101.2g of triethylamine and 400ml of dichloromethane are added into a reaction system, stirring and cooling are carried out by using an ice salt bath, a mixed solution of 114g of methylbenzenesulfonyl chloride and 200ml of dichloromethane is dropwise added into the reaction system at 0-10 ℃, after the dropwise addition is finished, stirring and reaction are carried out for 1 hour at 0-10 ℃ continuously, sampling analysis is carried out, after the reaction is finished, the system is poured into water, dichloromethane is added for dilution, standing and layering are carried out, a lower organic phase is separated out, water washing is carried out until the lower organic phase is neutral, anhydrous magnesium sulfate is used for drying, and ethanol is used for crystallization after the solvent is removed, thus obtaining a product with the content of more than 99.5%.
2) Preparation of C-CH2O-PFF3H
A low-temperature thermometer, mechanical stirring and a constant-pressure dropping funnel are arranged in a 250ml three-port bottle, nitrogen is introduced, 10g of 2, 3-difluorophenol, 13.8g of anhydrous potassium carbonate and 50ml of DMF are added into the system, after stirring and dissolution, the mixed solution of the propylcyclohexyl methoxy sulfonate prepared in the step 1) and DMF is added into the reaction system dropwise at 65 ℃, after finishing the dripping, the temperature is kept at 80 ℃ for 4 hours, after post treatment, pouring into a separating funnel, adding tap water into the separating funnel, standing for layering, washing to be neutral, concentrating and desolventizing, and then 10g of trans-C-CH 2O-PFF3H with the purity of more than 99.9% can be obtained by ethanol recrystallization.
The liquid crystal mixture composition and the measurement parameters of example 8 are shown in Table 10.
Table 10
/>
Note that: 7 is a liquid crystal compound having the general formula I.
Example 9
The liquid crystal mixture composition and the measurement parameters of example 9 are shown in Table 11.
TABLE 11
/>
Note that: 7 is a liquid crystal compound having the general formula I.
Example 10
The liquid crystal mixture composition and the measurement parameters of example 10 are shown in Table 12.
Table 12
Note that: 7 is a liquid crystal compound having the general formula I.
Example 11
The liquid crystal mixture composition and the measurement parameters of example 11 are shown in Table 13.
TABLE 13
/>
Note that: 8 is a liquid crystal compound having the general formula I.
Example 12
The liquid crystal mixture composition and the measurement parameters of example 12 are shown in Table 14.
TABLE 14
Note that: 8 is a liquid crystal compound having the general formula I.
Example 13
The liquid crystal mixture composition and the measurement parameters of example 13 are shown in Table 15.
TABLE 15
Note that: 7 is a liquid crystal compound having the general formula I.
Example 14
The liquid crystal mixture composition and the measurement parameters of example 14 are shown in Table 16.
Table 16
/>
Note that: 7 is a liquid crystal compound having the general formula I.
Example 15
The liquid crystal mixture composition and the measurement parameters of example 15 are shown in Table 17.
TABLE 17
Note that: 6 is a liquid crystal compound having the general formula I.
Comparative example 1
The liquid crystal mixture composition and the measurement parameters of comparative example 1 are shown in Table 18.
TABLE 18
/>
Comparative example 2
The liquid crystal mixture composition and the measurement parameters of comparative example 2 are shown in Table 19.
TABLE 19
/>
Wherein, in comparative example 1 and comparative example 2, liquid crystal compounds were used(CC-CH 2O-PFF3O 2) in place of +.sup.in example 14 and example 15, respectively>(CC-CH2O-PFF3H)。
As can be seen from the above examples, the liquid crystal compound having the formula I can reduce the viscosity of the system and increase the flexural modulus K of the system 33 Vertical dielectric constant ε ⊥ Thereby improving the response speed, improving the light transmittance in the whole system, being beneficial to energy saving and improving the contrast ratio. When the liquid crystal compound of the formula I is mixed with other liquid crystal compounds of different kinds, a liquid crystal mixture with high clearing point, lower viscosity and higher elasticity coefficient can be obtained, and especially when the liquid crystal mixture is mixed with a nonpolar liquid crystal compound of the formula III5 (such as a nonpolar liquid crystal compound with the code of 3 HHV), a liquid crystal mixture with low viscosity can be obtained, and the liquid crystal mixture can be used for manufacturing a liquid crystal medium with quick response. The above-mentioned measurement parameters relate to the physicochemical properties of all the liquid-crystalline compounds constituting the liquid-crystalline medium, the liquid-crystalline mixtures according to the application being used mainly for adjusting the liquid-crystalline parameters of the system.
As is evident from the comparison of example 14 with comparative example 1 and the comparison of example 15 with comparative example 2, when the liquid-crystalline compound of the formula I is contained in a liquid-crystalline mixture, it has a relatively low rotational viscosity, which is particularly advantageous for the production of a liquid-crystalline medium with a rapid response and for the adjustment of the appropriate clearing point T of the system NI Coefficient of flexural elasticity K 33 Vertical dielectric constant ε ⊥ And dielectric anisotropy Δε values, which are lower for a broader operating temperature, faster response speed, higher contrast and transmittancePower consumption is helpful.
Although not exhaustive, it is anticipated by those skilled in the art that, based on the examples disclosed above, other similar compounds can be obtained in a similar reaction scheme without the need for inventive effort, with only professional attempts per se. Representative embodiments are only exemplified herein for limited space.
The above description is only of the preferred embodiments of the present application and is not intended to limit the present application, but various modifications and variations can be made to the present application by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the protection scope of the present application.

Claims (4)

1. A liquid crystal mixture comprising 5.5% by mass of a liquid crystal materialA liquid crystal compound of structure; has a mass fraction of 5.0%A liquid crystal compound of structure; 8.0% by mass of the composition havingA liquid crystal compound of structure; 11.0% by mass of a composition havingA liquid crystal compound of structure; 3.7% by mass of the composition havingA liquid crystal compound of structure; 7.4% by mass of the composition havingA liquid crystal compound of structure; 7.4% by mass of the composition havingA liquid crystal compound of structure; has a mass fraction of 2.5%A liquid crystal compound of structure; 30.3% by mass of the composition havingA liquid crystal compound of structure; has a mass fraction of 5.1%A liquid crystal compound of structure; 4.0% by mass of the composition havingA liquid crystal compound of structure; has a mass fraction of 6.1%Liquid crystal compound having structure and mass fraction of 4.0%A liquid crystal compound of a structure.
2. The liquid crystal mixture according to claim 1, further comprising 0-20% by mass of a polymerizable compound having the formula:
wherein the method comprises the steps of
—T 1 and-T 2 Each independently representsOr an epoxy group;
—Y 1 -and-Y 2 -each independently represents a single bond or an alkyl group having 1 to 8 carbon atoms;
—X 1 -and-X 2 -each independently represents a single bond, -O- (CO), -COO-, or-OCO-;
—Z 1 -selected from the group consisting of single bonds, -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;
m is 0, 1 or 2;
each occurrence independently represents-CH 2-on unsubstituted or cyclohexylene being replaced by O +.>Unsubstituted or phenylene ring =ch-substituted by N->H in the ring being substituted by F
3. The liquid crystal mixture according to claim 1, further comprising 0-20% by mass of a stabilizer, preferably one or more of the compounds represented by the general formulae IV 1-IV 5:
IV1、IV2、/>
IV3、IV4、/>
IV5、
wherein the method comprises the steps of
R 7 Alkyl having 1 to 7 carbon atoms, alkoxy having 1 to 7 carbon atoms, alkenyl having 2 to 7 carbon atoms, halogenated alkyl having 1 to 7 carbon atoms, halogenated alkoxy having 1 to 7 carbon atoms or halogenated alkenyl having 2 to 7 carbon atoms; the alkyl, alkoxy and alkenyl groups are straight or branched alkyl, alkoxy and alkenyl groups;
is-> Any one of the group consisting ofA kind of module is assembled in the module and the module is assembled in the module.
4. Use of a liquid crystal mixture according to any of claims 1 to 3 in a liquid crystal display material or a liquid crystal display device, preferably in a negative display mode, preferably VA, PSVA or FFS display mode.
CN202310981516.8A 2017-10-31 2017-10-31 Liquid crystal mixture and application thereof Pending CN117070229A (en)

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