CN108239538B - Liquid crystal composition with negative dielectric anisotropy and application thereof - Google Patents

Liquid crystal composition with negative dielectric anisotropy and application thereof Download PDF

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CN108239538B
CN108239538B CN201611203621.5A CN201611203621A CN108239538B CN 108239538 B CN108239538 B CN 108239538B CN 201611203621 A CN201611203621 A CN 201611203621A CN 108239538 B CN108239538 B CN 108239538B
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liquid crystal
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crystal composition
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CN108239538A (en
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徐海彬
韩文明
陈昭远
徐爽
俞燕蕾
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Jiangsu Hecheng Display Technology Co Ltd
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Abstract

The invention discloses a liquid crystal composition with negative dielectric anisotropy, which comprises one or more compounds with a general formula I and one or more compounds with a general formula II. The invention also discloses a liquid crystal display device comprising the liquid crystal composition. The liquid crystal composition with negative dielectric anisotropy provided by the invention can meet the requirements of a proper large refractive index, has the characteristics of a large absolute value of dielectric anisotropy and lower rotational viscosity, has excellent performance, and can realize the balance of the performance of all aspects.

Description

Liquid crystal composition with negative dielectric anisotropy and application thereof
Technical Field
The invention belongs to the field of liquid crystal materials, and particularly relates to a liquid crystal composition with negative dielectric anisotropy and application thereof.
Background
Liquid crystal display elements are used in various household electric appliances such as watches and calculators, measuring instruments, automobile panels, word processors, computers, printers, televisions, and the like. The display mode is classified into PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), and the like, according to the type of the display mode. The driving method of the element is classified into a PM (passive matrix) type and an AM (active matrix) type. PM is classified into static (static) and multiplex (multiplex) types. AM is classified into a TFT (thin film transistor), an MIM (metal insulator metal), and the like. The types of TFTs are amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to a manufacturing process. Liquid crystal display elements are classified into a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both light sources of natural light and backlight, depending on the type of light source.
Among these display modes, IPS mode, ECB mode, VA mode, CSH mode, and the like are different from TN mode or STN mode which are currently used in general in that the former uses a liquid crystal material having negative dielectric anisotropy. Among these display systems, VA display by AM driving is particularly applied to display elements requiring high speed and wide viewing angle, and among them, liquid crystal elements such as televisions are most expected.
The liquid crystal material used in any display mode is required to have a low driving voltage, a high response speed, a wide operating temperature range, a large absolute value of negative dielectric anisotropy, a high phase transition temperature, and good miscibility. However, it has been difficult to obtain a liquid crystal composition having both large refraction and large negative dielectric constant and having a rapid response. A liquid crystal composition having a large absolute value of dielectric anisotropy has a high critical voltage, consumes a high power, and has a relatively slow response speed. Therefore, in order to meet the increasing application demands, there is a continuing need in the art for improved liquid crystal compounds of negative dielectric anisotropy.
Disclosure of Invention
The purpose of the invention is as follows:
in view of the drawbacks of the prior art, an object of the present invention is to provide a liquid crystal composition having a large absolute value of negative dielectric anisotropy, a rapid response, and a large refractive index, and a liquid crystal display element including the same.
The technical scheme of the invention is as follows:
one aspect of the present invention provides a liquid crystal composition having a negative dielectric anisotropy, comprising:
one or more compounds of formula (I)
Figure BDA0001189553950000021
And
one or more compounds of the general formula II
Figure BDA0001189553950000022
Wherein the content of the first and second substances,
R1、R2、R3and R4Each independently represents H, alkyl or alkoxy of 1 to 12 carbon atoms, alkenyl or alkenyloxy of 2 to 12 carbon atoms, wherein one or more H of the alkyl or alkoxy and the alkenyl or alkenyloxy may be substituted by F;
Z1represents a single bond, CH2CH2Or CH2O；
Ring (C)
Figure BDA0001189553950000023
To represent
Figure BDA0001189553950000024
n represents 1 or 2, and when n is 2, the ring
Figure BDA0001189553950000025
The same or different.
Further, the compound of the general formula I accounts for at least 10% of the total weight of the liquid crystal composition.
Furthermore, the compound of the general formula I accounts for 10-30% of the total weight of the liquid crystal composition.
Still further, the compound of the general formula I accounts for 10-20% of the total weight of the liquid crystal composition.
Preferably, the compound of formula i is selected from the group consisting of:
Figure BDA0001189553950000026
Figure BDA0001189553950000031
preferably, the compound of formula ii is selected from the group consisting of:
Figure BDA0001189553950000041
wherein the content of the first and second substances,
R31represents H, an alkyl or alkoxy group of 1 to 7 carbon atoms;
R41represents an alkoxy group of 1 to 7 carbon atoms.
More preferably, the compound of formula II-1 is selected from the group consisting of:
Figure BDA0001189553950000042
Figure BDA0001189553950000051
the compound of formula II-2 is selected from the group consisting of:
Figure BDA0001189553950000052
Figure BDA0001189553950000061
the compound of formula II-3 is selected from the group consisting of:
Figure BDA0001189553950000062
Figure BDA0001189553950000071
the compound of formula II-4 is selected from the group consisting of:
Figure BDA0001189553950000072
the compound of formula II-5 is selected from the group consisting of:
Figure BDA0001189553950000073
Figure BDA0001189553950000081
the compound of formula II-6 is selected from the group consisting of:
Figure BDA0001189553950000082
Figure BDA0001189553950000091
further, the liquid crystal composition also comprises one or more compounds of a general formula III
Figure BDA0001189553950000092
And/or one or more compounds of the formula IV
Figure BDA0001189553950000093
Wherein the content of the first and second substances,
R5、R6、R7and R8Each independently represents H, F, an alkyl or alkoxy group of 1 to 12 carbon atoms, an alkenyl or alkenyloxy group of 2 to 12 carbon atoms, wherein one or more H of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may be substituted by F;
ring (C)
Figure BDA0001189553950000094
Each independently represent
Figure BDA0001189553950000095
Figure BDA0001189553950000096
Ring (C)
Figure BDA0001189553950000097
To represent
Figure BDA0001189553950000098
Further, the compound of the general formula III and/or the general formula IV accounts for 0-70% of the total weight of the liquid crystal composition.
Still further, the compound of the general formula III and/or the general formula IV accounts for 0-50% of the total weight of the liquid crystal composition.
Preferably, the compound of formula iii is selected from the group consisting of:
Figure BDA0001189553950000099
the compound of formula iv is selected from the group consisting of:
Figure BDA00011895539500000910
Figure BDA0001189553950000101
wherein the content of the first and second substances,
R51、R61、R71and R81Each independently represents H, F, an alkyl or alkoxy group of 1 to 7 carbon atoms, an alkenyl or alkenyloxy group of 2 to 7 carbon atoms.
More preferably, the compound of formula III-1 is selected from the group consisting of:
Figure BDA0001189553950000102
the compound of formula III-2 is selected from the group consisting of:
Figure BDA0001189553950000111
the compound of formula III-3 is selected from the group consisting of:
Figure BDA0001189553950000112
Figure BDA0001189553950000121
Figure BDA0001189553950000131
the compound of the general formula IV-1 is selected from the group consisting of:
Figure BDA0001189553950000132
Figure BDA0001189553950000141
the compound of formula IV-2 is selected from the group consisting of:
Figure BDA0001189553950000142
the compound of the general formula IV-3 is selected from the group consisting of:
Figure BDA0001189553950000143
Figure BDA0001189553950000151
the compound of formula IV-4 is selected from the group consisting of:
Figure BDA0001189553950000152
further, the liquid crystal composition also comprises one or more compounds of the general formula V
Figure BDA0001189553950000161
Wherein the content of the first and second substances,
R9and R10Each independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms;
ring (C)
Figure BDA0001189553950000162
Each independently represent
Figure BDA0001189553950000163
Figure BDA0001189553950000164
Z2Represents a single bond, -CH2O-or-COO-.
Furthermore, the compound of the general formula V accounts for 0-10% of the total weight of the liquid crystal composition.
Still further, the compound of the general formula V accounts for 0-5% of the total weight of the liquid crystal composition.
Preferably, said compound of formula v is selected from the group consisting of:
Figure BDA0001189553950000165
wherein the content of the first and second substances,
R91and R101Each independently represents an alkyl or alkoxy group of 1 to 7 carbon atoms.
More preferably, said compound of formula V-1 is selected from the group consisting of:
Figure BDA0001189553950000166
Figure BDA0001189553950000171
the compound of formula V-2 is selected from the group consisting of:
Figure BDA0001189553950000172
Figure BDA0001189553950000181
the compound of formula V-3 is selected from the group consisting of:
Figure BDA0001189553950000182
Figure BDA0001189553950000191
the compound of formula V-4 is selected from the group consisting of:
Figure BDA0001189553950000192
Figure BDA0001189553950000201
the compound of formula V-5 is selected from the group consisting of:
Figure BDA0001189553950000202
Figure BDA0001189553950000211
the compound of formula V-6 is selected from the group consisting of:
Figure BDA0001189553950000212
Figure BDA0001189553950000221
another aspect of the present invention provides a liquid crystal display device comprising the liquid crystal composition having a negative dielectric anisotropy of the present invention.
Has the advantages that:
the liquid crystal composition with negative dielectric anisotropy provided by the invention can meet the requirements of proper large refractive index, has the characteristics of large absolute value of negative dielectric anisotropy and quick response, has excellent performance, and can realize the balance of performances of all aspects.
In some embodiments of the invention, there are provided liquid crystal compositions of the invention having a clearing point Tni between 70 and 90 deg.C, a viscosity γ 1 between 85 and 125mpa.s (20 deg.C), an optical anisotropy Δ n between 0.09 and 0.115, and an absolute value of dielectric anisotropy | Δ ε | between 4.0 and 5.0(25 deg.C).
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Figure BDA0001189553950000231
Compounds of the following formula are exemplified:
Figure BDA0001189553950000232
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane, G represents 2-fluoro-1, 4-phenylene and F represents fluorine.
The abbreviated codes of the test items in the following examples are as follows:
tni (. degree. C.) clearing Point (nematic-isotropic phase transition temperature)
Δ n refractive index anisotropy (589nm, 20 ℃ C.)
Delta epsilon dielectric anisotropy (1KHz, 25 ℃ C.)
Eta flow viscosity (mm)2·s-125 ℃ unless otherwise stated)
Gamma 1 rotational viscosity (mPas at 20 ℃ C.)
Wherein the content of the first and second substances,
the refractive index anisotropy was measured using an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃.
Δε＝ε‖-ε⊥Wherein, epsilon‖Is a dielectric constant parallel to the molecular axis,. epsilon⊥For the dielectric constant perpendicular to the molecular axis, test conditions: the test box is TN90 type at 25 deg.C and 1KHz, and has a thickness of 7 μm.
Gamma 1 is obtained by testing a TOYO6254 type liquid crystal physical property evaluation system; the test temperature was 25 ℃ and the test voltage was 90V.
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Example 1
The liquid crystal composition of example 1 was prepared according to the compounds and weight percentages listed in table 2, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 2 liquid crystal composition formulations and their test properties
Figure BDA0001189553950000241
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 3, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
Figure BDA0001189553950000251
Example 3
The liquid crystal composition of example 3 was prepared according to the compounds and weight percentages listed in table 4, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Figure BDA0001189553950000261
Example 4
The liquid crystal composition of example 4 was prepared according to the compounds and weight percentages listed in table 5, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Figure BDA0001189553950000262
Example 5
The liquid crystal composition of example 5 was prepared according to the compounds and weight percentages listed in table 6, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Figure BDA0001189553950000271
Example 6
The liquid crystal composition of example 6 was prepared according to the compounds and weight percentages listed in table 7, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
Figure BDA0001189553950000281
Example 7
The liquid crystal composition of example 7 was prepared according to the compounds and weight percentages listed in table 8, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 8 liquid crystal composition formulations and their test properties
Figure BDA0001189553950000282
Example 8
The liquid crystal composition of example 8 was prepared according to the compounds and weight percentages listed in table 9, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 9 liquid crystal composition formulations and their test properties
Figure BDA0001189553950000291
From the data of the above examples, it can be seen that the liquid crystal composition provided by the present invention has a high absolute value of negative dielectric anisotropy, a suitably high refractive index anisotropy, a relatively low rotational viscosity, and a suitably wide nematic phase temperature range, and a liquid crystal display including the liquid crystal composition of the present invention can satisfy the requirements of low voltage driving and fast response.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the present invention is not limited thereto, and equivalent changes and modifications made according to the spirit of the present invention should be covered thereby.

Claims (8)

1. A liquid crystal composition having negative dielectric anisotropy, comprising:
one or more compounds of formula (I)
Figure FDF0000014876390000011
One or more compounds of the general formula II
Figure FDF0000014876390000012
One or more compounds of the formula III
Figure FDF0000014876390000013
And
one or more compounds of formula IV
Figure FDF0000014876390000014
Wherein the content of the first and second substances,
R1represents an alkyl group of 1 to 12 carbon atoms;
R2、R3and R4Each independently represents H, 1-12An alkyl or alkoxy group of carbon atoms, an alkenyl or alkenyloxy group of 2 to 12 carbon atoms, wherein one or more H of said alkyl or alkoxy group and said alkenyl or alkenyloxy group may be substituted by F;
R5、R6、R7and R8Each independently represents H, F, an alkyl or alkoxy group of 1 to 12 carbon atoms, an alkenyl or alkenyloxy group of 2 to 12 carbon atoms, wherein one or more H of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may be substituted by F;
Z1represents a single bond, CH2CH2Or CH2O；
Ring (C)
Figure FDF0000014876390000015
To represent
Figure FDF0000014876390000016
Ring (C)
Figure FDF0000014876390000017
Each independently represent
Figure FDF0000014876390000018
Figure FDF0000014876390000019
Ring (C)
Figure FDF00000148763900000110
To represent
Figure FDF00000148763900000111
n represents 1 or 2, and when n is 2, the ring
Figure FDF00000148763900000112
The same or different, and the same or different,
wherein the compound of the general formula I accounts for 10-30% of the total weight of the liquid crystal composition;
the compounds of the general formula III and the general formula IV account for 28-70% of the total weight of the liquid crystal composition.
2. The liquid crystal composition having negative dielectric anisotropy according to claim 1, wherein the compound of formula i is selected from the group consisting of:
Figure FDF0000014876390000021
Figure FDF0000014876390000031
the compound of formula ii is selected from the group consisting of:
Figure FDF0000014876390000032
wherein the content of the first and second substances,
R31represents H, an alkyl or alkoxy group of 1 to 7 carbon atoms;
R41represents an alkoxy group of 1 to 7 carbon atoms.
3. The liquid crystal composition having negative dielectric anisotropy according to claim 2, wherein the compound of the formula ii-1 is selected from the group consisting of:
Figure FDF0000014876390000033
Figure FDF0000014876390000041
the compound of formula II-2 is selected from the group consisting of:
Figure FDF0000014876390000042
Figure FDF0000014876390000051
the compound of formula II-3 is selected from the group consisting of:
Figure FDF0000014876390000052
Figure FDF0000014876390000061
the compound of formula II-4 is selected from the group consisting of:
Figure FDF0000014876390000062
Figure FDF0000014876390000071
the compound of formula II-5 is selected from the group consisting of:
Figure FDF0000014876390000072
the compound of formula II-6 is selected from the group consisting of:
Figure FDF0000014876390000073
Figure FDF0000014876390000081
4. the liquid crystal composition having negative dielectric anisotropy according to claim 1, wherein the compound of formula iii is selected from the group consisting of:
Figure FDF0000014876390000082
the compound of formula iv is selected from the group consisting of:
Figure FDF0000014876390000083
wherein the content of the first and second substances,
R51、R61、R71and R81Each independently represents H, F, an alkyl or alkoxy group of 1 to 7 carbon atoms, an alkenyl or alkenyloxy group of 2 to 7 carbon atoms.
5. The liquid crystal composition having negative dielectric anisotropy according to claim 4, wherein the compound of the general formula III-1 is selected from the group consisting of:
Figure FDF0000014876390000084
Figure FDF0000014876390000091
the compound of formula III-2 is selected from the group consisting of:
Figure FDF0000014876390000092
Figure FDF0000014876390000101
the compound of formula III-3 is selected from the group consisting of:
Figure FDF0000014876390000102
Figure FDF0000014876390000111
Figure FDF0000014876390000121
the compound of the general formula IV-1 is selected from the group consisting of:
Figure FDF0000014876390000122
the compound of formula IV-2 is selected from the group consisting of:
Figure FDF0000014876390000131
the compound of the general formula IV-3 is selected from the group consisting of:
Figure FDF0000014876390000132
Figure FDF0000014876390000141
the compound of formula IV-4 is selected from the group consisting of:
Figure FDF0000014876390000142
6. the liquid crystal composition with negative dielectric anisotropy according to claim 1, further comprising one or more compounds of formula V
Figure FDF0000014876390000143
Wherein the content of the first and second substances,
R9and R10Each independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms;
ring (C)
Figure FDF0000014876390000144
Each independently represent
Figure FDF0000014876390000145
Figure FDF0000014876390000146
Z2Represents a single bond, -CH2O-or-COO-.
7. The liquid crystal composition having negative dielectric anisotropy according to claim 6, wherein the compound of formula V is selected from the group consisting of:
Figure FDF0000014876390000151
wherein the content of the first and second substances,
R91and R101Each independently represents an alkyl or alkoxy group of 1 to 7 carbon atoms.
8. A liquid crystal display device comprising the liquid crystal composition having a negative dielectric anisotropy according to any one of claims 1 to 7.
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