CN114787318A - Liquid crystal composition capable of adapting to wider working temperature and application thereof in device - Google Patents

Liquid crystal composition capable of adapting to wider working temperature and application thereof in device Download PDF

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CN114787318A
CN114787318A CN201980102835.9A CN201980102835A CN114787318A CN 114787318 A CN114787318 A CN 114787318A CN 201980102835 A CN201980102835 A CN 201980102835A CN 114787318 A CN114787318 A CN 114787318A
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compound
general formula
parts
weight
liquid crystal
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李承贺
储士红
陈卯先
王杰
陈海光
姜天孟
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Beijing Bayi Space LCD Technology Co Ltd
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Beijing Bayi Space LCD Technology Co Ltd
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    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/46Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters

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Abstract

The invention relates to a liquid crystal composition capable of adapting to a wider working temperature and a preparation method thereof. The liquid crystal composition can be applied to various display devices, especially to PDLC devices.

Description

Liquid crystal composition capable of adapting to wider working temperature and application thereof in device Technical Field
The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal composition capable of adapting to a wider working temperature and application thereof in a liquid crystal display device.
Background
A liquid crystal display is a display using liquid crystal as a material. Liquid crystals are organic compounds that are intermediate between solid and liquid states. It becomes a transparent liquid when heated and becomes a crystalline turbid solid when cooled. Under the action of the electric field, the liquid crystal molecules change in arrangement, thereby affecting the change of light passing through the liquid crystal molecules, and the change of light can be expressed as light and shade change through the action of the polarizer. Therefore, people finally control the light and shade change of the light through controlling the electric field, thereby achieving the purpose of displaying images.
In recent years, the application fields of liquid crystal compounds have been remarkably widened to various display devices, electro-optical devices, electronic components, sensors, and the like. For this reason, many different structures have been proposed, particularly in the field of nematic liquid crystals, nematic liquid crystal compounds having hitherto been widely used in flat panel displays and in the field of dimming. The demand for display technology is also increasing, especially in achieving wide operating temperatures, fast response, and reduced drive voltages to reduce power consumption. The liquid crystal composition provided by the invention has the characteristics of large optical anisotropy and high clearing point, and the effect of effectively enlarging the working temperature range is realized.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a liquid crystal composition having a large optical anisotropy and a wide temperature range, and its application in a liquid crystal display device. The liquid crystal composition is a nematic liquid crystal composition, has high optical anisotropy and high clearing point, and realizes the effect of effectively enlarging the working temperature range.
The technical scheme adopted by the invention is as follows:
a liquid crystal composition capable of adapting to a wide working temperature comprises the following raw material components in parts by weight:
1-20 parts by weight of a compound with a general formula I;
15-70 parts by weight of a compound of general formula II;
0-15 parts by weight of a compound of formula III;
0-20 parts by weight of a compound of formula IV;
1-40 parts by weight of a compound with a general formula V;
1-40 parts of a compound shown as a general formula VI;
1-20 parts by weight of a compound with a general formula VII;
1-20 parts by weight of a compound with a general formula VIII;
the structures of the above 8 compounds are as follows:
the structure of the compound with the general formula I is as follows:
Figure PCTCN2019127697-APPB-000001
R 1、R 2each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
the structure of the compound with the general formula II is as follows:
Figure PCTCN2019127697-APPB-000002
R 3、R 4each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
the structure of the compound with the general formula III is as follows:
Figure PCTCN2019127697-APPB-000003
R 5represents an alkoxy group of 1 to 7 carbon atoms; r6Represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
the structure of the compound with the general formula IV is as follows:
Figure PCTCN2019127697-APPB-000004
R 7represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
the structure of the compound with the general formula V is as follows:
Figure PCTCN2019127697-APPB-000005
R 8represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
the compound with the general formula VI has the structure:
Figure PCTCN2019127697-APPB-000006
R 9、R 10each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
the structure of the compound with the general formula VII is as follows:
Figure PCTCN2019127697-APPB-000007
R 11represents an alkoxy group of 1 to 7 carbon atoms; r12Representing 1 to 7 carbon atomsAlkyl or alkenyl of 2 to 7 carbon atoms;
the structure of the compound with the general formula VIII is as follows:
Figure PCTCN2019127697-APPB-000008
R 13、R 14each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms.
Further preferably, the raw material components of the liquid crystal composition comprise the following compounds in parts by weight:
3-15 parts of a compound with a general formula I;
25-60 parts of a compound shown as a general formula II;
1-15 parts by weight of a compound of formula III;
1-15 parts by weight of a compound of formula IV;
5-30 parts by weight of a compound shown as a general formula V;
5-30 parts by weight of a compound with a general formula VI;
3-18 parts by weight of a compound with a general formula VII;
2-15 parts of a compound with a general formula VIII.
Further preferably, the raw material components of the liquid crystal composition comprise the following compounds in parts by weight:
4-10 parts by weight of a compound with a general formula I;
35-50 parts by weight of a compound of formula II;
2-10 parts by weight of a compound of formula III;
2-10 parts by weight of a compound with a general formula IV;
10-20 parts by weight of a compound shown as a general formula V;
8-25 parts by weight of a compound with a general formula VI;
8-15 parts of a compound with a general formula VII;
3-10 parts of a compound with a general formula VIII.
Further preferably, the raw material components of the liquid crystal composition comprise the following compounds in parts by weight:
6 parts by weight of a compound of formula I;
40 parts by weight of a compound represented by the general formula II;
3 parts by weight of a compound of formula III;
8 parts by weight of a compound of the general formula IV;
16 parts by weight of a compound of formula V;
12 parts by weight of a compound of the general formula VI;
12 parts by weight of a compound shown as a general formula VII;
3 parts by weight of a compound having a general formula VIII.
The compound with the general formula I is a compound containing alkynyl, and has a high response speed; the compound with the general formula I is selected from one or more compounds represented by the following formulas IA-ID:
Figure PCTCN2019127697-APPB-000009
the compound with the general formula II is a compound containing alkynyl and fluorine, and has high response speed. The compound with the general formula II is selected from one or more compounds represented by the following formula IIA-formula IIC:
Figure PCTCN2019127697-APPB-000010
the compound with the general formula III is a compound containing two ring structures, and the compound has better low-temperature intersolubility; the compound with the general formula III is selected from one or more compounds represented by the following formulas IIIA-IIIE:
Figure PCTCN2019127697-APPB-000011
the compound with the general formula IV is a compound containing two ring structures, and has large positive dielectric anisotropy; the compound with the general formula IV is selected from one or more compounds represented by the following formula IVA-IVD:
Figure PCTCN2019127697-APPB-000012
the compound with the general formula V is a compound containing a tricyclic cyano structure, and the compound has a high clearing point and large positive dielectric anisotropy; the compound with the general formula V is selected from one or more compounds represented by the following formula VA-formula VD:
Figure PCTCN2019127697-APPB-000013
the compound with the general formula VI is a compound containing a bicyclic ester group structure, and has good low-temperature intersolubility. The compound with the general formula VI is selected from one or more compounds represented by the following formula VIA-formula VIC:
Figure PCTCN2019127697-APPB-000014
the compound with the general formula VII is a compound containing a bicyclic ester group structure, and has good low-temperature intersolubility. The compound with the general formula VII is selected from one or more compounds represented by the following formula VIIA-formula VIIE:
Figure PCTCN2019127697-APPB-000015
the compound with the general formula VIII is a compound containing a tetracyclic structure, and has a high clearing point. The compound with the general formula VIII is selected from one or more compounds represented by the following formulas VIII A-VIII F:
Figure PCTCN2019127697-APPB-000016
further preferably, the raw material components of the liquid crystal composition further include 0.1 to 0.5 parts by mass of an ultraviolet absorber.
The ultraviolet absorbent is one or a mixture of a plurality of benzotriazoles, benzophenones, triazines and benzoates.
Further preferably, the raw material components of the liquid crystal composition further include 0.01 to 0.05 parts by mass of an antioxidant.
The antioxidant is one or more of hindered phenols, phosphites and a compound of hindered phenols and phosphites.
The preparation method of the liquid crystal composition comprises the following steps: and taking the raw material components, sequentially adding the raw material components according to the sequence from high melting point to low melting point, dissolving under the heating and stirring conditions, fully and uniformly mixing, and filtering and removing impurities to obtain the liquid crystal composition.
The heating temperature is 60-100 ℃.
The method for producing the liquid crystal composition of the present invention is not particularly limited, and it can be produced by mixing two or more compounds by a conventional method, such as a method of mixing different components at a high temperature of 60 to 100 ℃ and dissolving each other, wherein the liquid crystal composition is dissolved in a solvent for the compounds and mixed, and then the solvent is distilled off under reduced pressure; alternatively, the liquid crystal composition of the present invention can be prepared by a conventional method, for example, by dissolving the component having a smaller content in the main component having a larger content at a higher temperature, or by dissolving the respective components in an organic solvent, for example, acetone, chloroform, methanol, etc., and then mixing the solutions to remove the solvent.
The liquid crystal composition is applied to a liquid crystal display.
The invention has the beneficial effects that:
the liquid crystal composition is prepared by adopting a compound with a general formula I, a compound with a general formula II, a compound with a general formula III, a compound with a general formula IV, a compound with a general formula V, a compound with a general formula VI, a compound with a general formula VII and a compound with a general formula VIII as raw materials and carrying out proper proportioning, and the liquid crystal composition contains polycyclic compounds, alkynyl cyano compounds and ester-based compounds, has the characteristics of high bright point and large optical anisotropy, has a wide working temperature range and can adapt to high-temperature environmental conditions. The liquid crystal composition can be suitable for various display devices, and is particularly suitable for PDLC devices.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples are intended to illustrate the invention, but are not intended to limit the scope of the invention.
Unless otherwise indicated, percentages in the present invention are weight percentages; the temperature units are centigrade; Δ n represents optical anisotropy (25 ℃); Δ ∈ (∈ ═ epsilon/∈ j) represents dielectric anisotropy (25 ℃, 1000Hz), and ∈/,) and ∈ respectively represent parallel and perpendicular dielectric constants (25 ℃, 1000 Hz); η represents the bulk viscosity (mPas, 25 ℃); cp represents the clearing point (. degree. C.) of the liquid crystal composition.
In each of the following examples, the group structure of the liquid crystal compound is represented by a code shown in Table 1.
TABLE 1 group Structure code of liquid Crystal Compounds
Figure PCTCN2019127697-APPB-000017
Figure PCTCN2019127697-APPB-000018
Take the following compound structure as an example:
Figure PCTCN2019127697-APPB-000019
expressed as: 3 PGUQUF.
Figure PCTCN2019127697-APPB-000020
Expressed as: v2 PZUCN.
In the following examples, the weight percentages of the raw material components in the liquid crystal composition and the performance parameters of the liquid crystal composition are shown in the following tables.
In the following examples, the liquid crystal composition was prepared by a thermal dissolution method, comprising the steps of: weighing the liquid crystal compound by a balance according to the weight percentage, wherein the weighing and adding sequence has no specific requirement, generally weighing and mixing the liquid crystal compound in sequence from high melting point to low melting point, heating and stirring at 60-100 ℃ to uniformly dissolve all components, filtering, rotatably steaming, and finally packaging to obtain the target sample.
Example 1
TABLE 2 weight percents of the components in the liquid crystal composition and the performance parameters of the liquid crystal compounds
Figure PCTCN2019127697-APPB-000021
Example 2
TABLE 3 weight percents of the components in the liquid crystal composition and the performance parameters of the liquid crystal compounds
Figure PCTCN2019127697-APPB-000022
Example 3
TABLE 4 weight percents of the components in the liquid crystal composition and the performance parameters of the liquid crystal compounds
Figure PCTCN2019127697-APPB-000023
Figure PCTCN2019127697-APPB-000024
Example 4
TABLE 5 weight percents of the components in the liquid crystal composition and the performance parameters of the liquid crystal compounds
Figure PCTCN2019127697-APPB-000025
The liquid crystal compound of this example was prepared in the same manner as in example 1.
Example 5
TABLE 6 weight percents of the components in the liquid crystal composition and the Properties of the liquid crystal Compounds
Figure PCTCN2019127697-APPB-000026
Figure PCTCN2019127697-APPB-000027
The liquid crystal compound of this example was prepared in the same manner as in example 1.
Example 6
TABLE 7 weight percents of the components in the liquid crystal composition and the Properties of the liquid crystal Compounds
Figure PCTCN2019127697-APPB-000028
Figure PCTCN2019127697-APPB-000029
The liquid crystal compound of this example was prepared in the same manner as in example 1.
Example 7
TABLE 8 weight percent of the components in the liquid crystal composition and the liquid crystal compound Performance parameters
Figure PCTCN2019127697-APPB-000030
The liquid crystal compound of this example was prepared in the same manner as in example 1.
Example 8
TABLE 9 weight percents of the components in the liquid crystal composition and the Properties of the liquid crystal Compounds
Figure PCTCN2019127697-APPB-000031
Figure PCTCN2019127697-APPB-000032
The liquid crystal compound of this example was prepared in the same manner as in example 1.
Example 9
TABLE 10 weight percent of the components in the liquid crystal composition and the liquid crystal compound Performance parameters
Figure PCTCN2019127697-APPB-000033
Figure PCTCN2019127697-APPB-000034
The liquid crystal compound of this example was prepared in the same manner as in example 1.
Example 10
TABLE 11 weight percents of the components in the liquid crystal composition and the Performance parameters
Figure PCTCN2019127697-APPB-000035
The liquid crystal compound of this example was prepared in the same manner as in example 1.
Example 11
This example only differs from example 1 in that: the raw material components further include an ultraviolet absorber V001, and the other raw material components and the liquid crystal compound were prepared in the same manner as in example 1.
The liquid crystal composition of this example had the raw material components shown in Table 12.
TABLE 12 amounts of the respective raw material components in the liquid-crystalline compounds
Components Compound code Weights (g)
3CPTP2 6
3PPTU2 20
3PPTU4 10
3PPTU5 10
3CPO1 3
3PZGCN 8
2CPZGCN 4
3CPZGCN 4
4CPZGCN 4
5CPZGCN 4
3PZP5 12
5CZPO2 12
3CCZPC3 3
—— Ultraviolet absorber V001 0.3
Example 12
This example differs from example 1 only in that: the raw material composition further included a hindered phenol antioxidant 0001, and the preparation methods of the other raw material compositions and the liquid crystal compound were the same as in example 1.
The liquid crystal composition of this example had the following raw material composition as shown in Table 13.
TABLE 13 amount of raw Material Components in liquid Crystal Compounds
Components Compound code Weights (g)
3CPTP2 6
3PPTU2 20
3PPTU4 10
3PPTU5 10
3CPO1 3
3PZGCN 8
2CPZGCN 4
3CPZGCN 4
4CPZGCN 4
5CPZGCN 4
3PZP5 12
5CZPO2 12
3CCZPC3 3
—— Hindered phenol antioxidant 0001 0.03
Comparative example 1
TABLE 14 weight percents of the components in the liquid crystal composition and the Performance parameters of the liquid crystal composition
Figure PCTCN2019127697-APPB-000036
Figure PCTCN2019127697-APPB-000037
The liquid crystal compound described in this comparative example was prepared in the same manner as in example 1.
The liquid crystal compositions obtained in example 1 and comparative example 1 were compared together for each of their performance parameter values, see table 15.
TABLE 15 comparison of the Performance parameters of the liquid crystal compositions obtained in example 1 and comparative example 1
Liquid crystal compounds Cp △n Δε η
Example 1 129 0.241 11.8 67
Comparative example 1 100 0.242 12.0 66
As can be seen from table 15, compared with comparative example 1, the optical anisotropy Δ n, the dielectric anisotropy Δ ∈, and the bulk viscosity η of the liquid crystal mixture provided in example 1 are substantially the same, but the clearing point Cp of the liquid crystal mixture provided in example 1 is higher, which means that the liquid crystal compound provided by the present invention has a wider temperature working range and can adapt to high temperature environment conditions under similar conditions such as driving voltage.
The present invention is not limited to the above preferred embodiments, and any other various products can be obtained by anyone in light of the present invention, but any changes in shape or structure thereof, which are similar or identical to the technical solution of the present invention, fall within the protection scope of the present invention.

Claims (10)

  1. A liquid crystal composition capable of adapting to a wide working temperature is characterized in that raw material components comprise the following compounds in parts by weight:
    1-20 parts by weight of a compound with a general formula I;
    15-70 parts of a compound shown as a general formula II;
    0-15 parts by weight of a compound of formula III;
    0-20 parts by weight of a compound of formula IV;
    1-40 parts by weight of a compound with a general formula V;
    1-40 parts of a compound shown as a general formula VI;
    1-20 parts by weight of a compound with a general formula VII;
    1-20 parts by weight of a compound with a general formula VIII;
    the structures of the above 8 compounds are as follows:
    the structure of the compound with the general formula I is as follows:
    Figure PCTCN2019127697-APPB-100001
    R 1、R 2each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
    the structure of the compound with the general formula II is as follows:
    Figure PCTCN2019127697-APPB-100002
    R 3、R 4each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
    the structure of the compound with the general formula III is as follows:
    Figure PCTCN2019127697-APPB-100003
    R 5represents an alkoxy group of 1 to 7 carbon atoms; r is6Represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
    the structure of the compound with the general formula IV is as follows:
    Figure PCTCN2019127697-APPB-100004
    R 7represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
    the structure of the compound with the general formula V is as follows:
    Figure PCTCN2019127697-APPB-100005
    R 8represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
    the compound with the general formula VI has the structure:
    Figure PCTCN2019127697-APPB-100006
    R 9、R 10each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
    the structure of the compound with the general formula VII is as follows:
    Figure PCTCN2019127697-APPB-100007
    R 11represents an alkoxy group of 1 to 7 carbon atoms; r is12Represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms;
    the structure of the compound with the general formula VIII is as follows:
    Figure PCTCN2019127697-APPB-100008
    R 13、R 14each independently represents an alkyl group of 1 to 7 carbon atoms or an alkenyl group of 2 to 7 carbon atoms.
  2. The liquid crystal composition of claim 1, wherein the raw material components comprise the following compounds in parts by weight:
    3-15 parts by weight of a compound with a general formula I;
    25-60 parts by weight of a compound shown as a general formula II;
    1-15 parts by weight of a compound of formula III;
    1-15 parts by weight of a compound of formula IV;
    5-30 parts by weight of a compound with a general formula V;
    5-30 parts by weight of a compound with a general formula VI;
    3-18 parts by weight of a compound with a general formula VII;
    2-15 parts of a compound with a general formula VIII.
  3. The liquid crystal composition of claim 1, wherein the raw material components comprise the following compounds in parts by weight:
    4-10 parts by weight of a compound with a general formula I;
    35-50 parts by weight of a compound of formula II;
    2-10 parts by weight of a compound of formula III;
    2-10 parts by weight of a compound of formula IV;
    10-20 parts by weight of a compound with a general formula V;
    8-25 parts of a compound shown as a general formula VI;
    8-15 parts by weight of a compound with a general formula VII;
    3-10 parts by weight of a compound with a general formula VIII.
  4. The liquid crystal composition according to claim 1, wherein the raw material components comprise the following compounds in parts by weight:
    6 parts by weight of a compound of formula I;
    40 parts by weight of a compound of formula II;
    3 parts by weight of a compound of the general formula III;
    8 parts by weight of a compound of the general formula IV;
    16 parts by weight of a compound of formula V;
    12 parts by weight of a compound of the general formula VI;
    12 parts by weight of a compound of the general formula VII;
    3 parts by weight of a compound having a general formula VIII.
  5. The liquid crystal composition according to claim 1, wherein the compound of formula I is an alkynyl-containing compound selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100009
    the compound with the general formula II is a compound containing alkynyl and fluorine, and is selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100010
    the compound with the general formula III is a compound containing a two-ring structure, and is selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100011
    the compound with the general formula IV is a compound containing a two-ring structure, and is selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100012
    the compound with the general formula V is a compound containing a tricyclic cyano structure, and is selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100013
    the compound with the general formula VI is a compound containing a bicyclic ester group structure, and is selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100014
    the compound with the general formula VII is a compound containing a bicyclic ester group structure, and is selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100015
    the compound with the general formula VIII is a compound containing a tetracyclic structure, and is selected from one or more of the following compounds:
    Figure PCTCN2019127697-APPB-100016
  6. the liquid crystal composition according to any one of claims 1 to 5, wherein the raw material composition further comprises 0.1 to 0.5 parts by weight of an ultraviolet absorber;
    the ultraviolet absorbent is one or a mixture of more of benzotriazoles, benzophenones, triazines and benzoates.
  7. The liquid crystal composition of any one of claims 1 to 5, wherein the raw material components further comprise 0.01 to 0.05 parts by weight of an antioxidant.
    The antioxidant is one or more of hindered phenols, phosphites and compound antioxidants.
  8. A method for producing a liquid crystal composition according to any one of claims 1 to 7, comprising the steps of: and taking the raw material components, sequentially adding the raw material components according to the sequence from high melting point to low melting point, dissolving under the heating and stirring conditions, fully and uniformly mixing, and filtering and removing impurities to obtain the liquid crystal composition.
  9. The method of claim 8, wherein the heating is at a temperature of 60-100 ℃.
  10. Use of a liquid crystal composition according to any one of claims 1 to 7 in a liquid crystal display.
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