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CN103205265B - Liquid crystal composition and liquid crystal display device - Google Patents

Liquid crystal composition and liquid crystal display device Download PDF

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CN103205265B
CN103205265B CN201310082451.XA CN201310082451A CN103205265B CN 103205265 B CN103205265 B CN 103205265B CN 201310082451 A CN201310082451 A CN 201310082451A CN 103205265 B CN103205265 B CN 103205265B
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liquid crystal
crystal composition
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CN103205265A (en
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韩文明
严加洁
胡娟
谭玉东
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Jiangsu Hecheng Display Technology Co Ltd
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Jiangsu Hecheng Display Technology Co Ltd
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Abstract

The invention provides a positive dielectric anisotropic liquid crystal composition and applications thereof. The liquid crystal composition comprises at least one compound of the general formular (I) as a first component and at least one compound of the general formula (II) as a second component. The content of the first component is not more than 30% of the total mass of the liquid crystal composition. The liquid crystal composition has low rotary viscosity and high response speed. Besides, the invention further provides a liquid crystal display with the liquid crystal composition.

Description

Liquid crystal composition and display device thereof
Technical Field
The invention relates to a liquid crystal composition, in particular to a liquid crystal composition with low rotational viscosity and high response speed and application thereof.
Background
The liquid crystal material is a mixture of organic rod-shaped small molecular compounds which have liquid fluidity and crystal anisotropy at a certain temperature. Liquid crystal materials are mainly used as dielectrics in displays, since the optical properties of such substances can be changed by an applied voltage. The liquid crystal composition is classified into twisted nematic (TN type), super twisted nematic (STN type), thin film transistor type (TFT type), guest-host type (GH type), dynamic scattering type (DS type), and the like, in which the most common display element is based on the Schadt-hellrich effect and has a twisted phase column structure. Furthermore, there are also liquid crystal cells for electric field operation parallel to the substrate and liquid crystal plane, such as IPS (in-plane switching) liquid crystal cells.
For liquid crystal displays, liquid crystal compounds and liquid crystal media having good chemical and thermal stability, suitable optical anisotropy, fast response speed and good stability to electric fields and electromagnetic radiation are in line with the current demand. In order to expand the operating range of liquid crystal displays, liquid crystal display materials also need to have a wide nematic temperature range to meet the requirement of maintaining good display in various environments.
In order to meet the process requirements of liquid crystal display devices, liquid crystal materials are required to have wide and various performance parameters, and the currently practical liquid crystal materials are all mixed liquid crystal materials, but the optimization of various performance parameters of the mixed liquid crystal materials is contradictory, restricted and influenced, and certain difficulty exists in meeting the process performance requirements. In liquid crystal compositions as described in EP0667555, EP0673986, DE19528106, DE19528107, WO962851, a significant disadvantage is the long response time.
Thus, there is a need for new liquid crystal compositions with improved properties, and liquid crystal compositions with low rotational viscosity, fast response times, are particularly important for many types of applications.
Disclosure of Invention
The object of the present invention is to provide, by optimal combination and preferred formulation of various liquid crystal compositions, a liquid crystal composition having a low rotational viscosity and a fast response speed, which liquid crystal composition can exhibit none or at least to a significantly lesser extent the disadvantages of the prior art materials.
In order to accomplish the above object, the present invention provides a positive dielectric anisotropic liquid crystal composition comprising:
at least one compound of the general formula (I) as a first component
And
at least one compound of the general formula (II) as a second component
Wherein:
the content of the first component does not exceed 30 percent of the total weight of the liquid crystal composition;
R1、R2may be the same or different and are independently selected from the group consisting of C1~C7Alkyl of (C)1~C7Alkoxy and C2~C7Wherein said C is1~C7One or more CH in the alkyl group of (2)2May be replaced independently of one another by O, S, -CH = CH-, -C ≡ C-or-COO-, and each two O or S are not linked to one another; when said R is2Is selected from the group consisting of2~C7When said alkenyl is (C), said2~C7One or more H in the alkenyl group of (a) may be substituted independently of each other by F;
z is selected from the group consisting of a single bond, -CH = CH-, -C.ident.C-, -O-, -COO-, -OCO-, -OCH2-、-C2H4-、-CH2O-、-OCF2-and-CF2O-;
x is selected from halogen, CN, C1~C7Alkyl and C1~C7Wherein said C is1~C7Alkyl and C1~C7One or more H in the alkoxy group of (a) may be substituted independently of each other by F;
L1、L2may be the same or different and are each independently H or F, wherein L is1、L2At least one of which is F;
may be the same or different and are independently selected fromAnda group of components selected from the group consisting of,is selected from the group consisting ofWherein, theOne or more CH in2Can be replaced independently of one another by O or SMay be substituted independently of one another by F;
a. b may be the same or different and are independently 0 or 1.
In the embodiment of the present invention, preferably, the compound of formula (I) accounts for 5% to 25% of the total weight of the liquid crystal composition.
The R is1、R2May be the same or different and are independently selected from the group consisting of C1~C5Alkyl of (C)1~C5Alkoxy and C2~C5Wherein said C is1~C5One or more CH in the alkyl group of (2)2Can be replaced by O or S independently of each other, and every two of O or S are not connected to each other; when said R is2Is selected from the group consisting of2~C5When said alkenyl is (C), said2~C5One or more H in the alkenyl group of (a) may be substituted independently of each other by F;
z is selected from single bond, -COO-, -OCF2-and-CF2O-;
said X is selected from the group consisting of F, CN, C1~C5And C is fluoroalkyl and1~C5fluoro alkoxy group of (a);
the above-mentionedMay be the same or different and are independently selected from Wherein, in addition to the above definitions, said Can also be
In an embodiment of the present invention, more preferably, the compound of the general formula (I) is a compound selected from one or more of the group consisting of;
the compound of the general formula (II) is a compound selected from one or more of the group consisting of:
the liquid crystal composition provided by the invention can also comprise one or more compounds selected from compounds conforming to the general formula (III):
wherein:
R3、R4may be the same or different and are independently selected from the group consisting of C1~C7Alkyl of (C)1~C7Alkoxy and C2~C7Wherein said C is1~C7One or more CH in the alkyl group of (2)2Can be O, S or-OCF independently of each other2-substituted, and each two O or S are not linked to each other; wherein, in addition to the above definitions, said R4May also be-OCF3
Independently of each other selected fromA group consisting of, wherein,one or more CH in2May be replaced independently of one another by O or S; when saidIs composed ofWhen is in use, theMay be substituted independently of one another by F;
c is 0 or 1.
In an embodiment of the present invention, preferably, said R is3、R4May be the same or different and are independently selected from the group consisting of C1~C5Alkyl of (C)1~C5Alkoxy and C2~C5Alkenyl groups of (a); wherein, in addition to the above definitions, said R4May also be-OCF3
In an embodiment of the present invention, more preferably, the compound of the general formula (III) is a compound selected from one or more of the group consisting of:
another aspect of the invention provides the use of a liquid crystal composition of the invention in the manufacture of an electro-optical device.
In a further aspect of the invention there is provided an electro-optical liquid crystal display comprising the liquid crystal composition of the invention.
The liquid crystal medium comprising the liquid crystal composition is determined to have low rotational viscosity and shorter response time by comparing with a control example through a combination experiment of the compounds.
In the present invention, unless otherwise specified, the proportions are weight ratios, all temperatures are in degrees centigrade, and the thickness of the box selected for the response time data test is 7 μm.
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.
The liquid crystal displays used in the following embodiments are all TN-TFT liquid crystal display devices, have a cell thickness d =7 μm, and are composed of a polarizer (polarizer), an electrode substrate, and the like. The display device is in a normally white mode, i.e. when no voltage difference is applied between the row and column electrodes, a viewer perceives a pixel color that is white. The upper and lower polarizer axes on the substrate are at a 90 degree angle to each other. The space between the two substrates is filled with an optical liquid crystal material.
For convenience of expression, in the following examples, the group structures of the liquid crystal compounds are represented by the codes listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Take the following structure as an example:
the structure is represented by the code in table 1: it can be represented as 3PTGQP3, again as:
it can be expressed as nCPTPm, where n in the code represents the number of C atoms of the left alkyl group, e.g., n is "3", i.e., the alkyl group is-C3H7(ii) a C in the code represents cyclohexane; p in the code represents phenylene; t in the code represents alkynyl; in the code, m represents the number of C atoms in the alkyl group at the right end, for example, m is "1", that is, the alkyl group at the right end is-CH3
The shorthand codes of the test items in the embodiments are respectively expressed as:
the components used in the examples which follow are synthesized by the inventors according to known methods, as described in the literature (for example in standard works such as Houben-Weyl, Methoden der organischen Chemie (methods of organic chemistry), Georg-Thieme-Verlag, Stuttgart). These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds. Methods for introducing a target end group, ring structure and binding group into a starting material are described in publications such as Organic synthesis (John Wiley & Sons, Inc), Organic Reactions (John Wiley & Sons, Inc), Comprehensive Organic synthesis (Pergamon Press), and New laboratory chemistry lecture (Bolus). Among them, the preparation method of the indene ring compounds used in the examples is disclosed in CN 102477305A. The compounds mentioned in the examples are known conventional compounds, the preparation of which is known to the person skilled in the art.
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.
Comparative example 1
Comparative liquid crystal compositions were prepared according to the compounds and weight percentages listed in table 2, and were 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
Example 1
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 3, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
Example 2
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 4, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
The liquid crystal compositions of examples 1 and 2 have suitable refractive index anisotropy and dielectric anisotropy, low rotational viscosity, faster response speed, and good display effect, compared to the comparative examples, and are suitable for use in display devices.
Comparative example 2
The liquid crystal composition of comparative example 2, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared according to the compounds and weight percentages listed in table 5, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Example 3
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 6, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Example 4
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 7, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
The liquid crystal compositions of examples 3 and 4 have suitable refractive index anisotropy and dielectric anisotropy, low rotational viscosity, faster response speed, good display effect, and suitability for use in display devices, as compared with comparative example 2 (please confirm, it has been confirmed).

Claims (10)

1. A positive dielectric anisotropic liquid crystal composition comprising:
at least one compound of the general formula (I) as a first component
And
at least one compound of the general formula (II) as a second component
Wherein:
the content of the first component does not exceed 30 percent of the total weight of the liquid crystal composition;
R1、R2may be the same or different and are independently selected from the group consisting of C1~C7Alkyl of (C)1~C7Alkoxy and C2~C7Wherein said C is1~C7One or more CH in the alkyl group of (2)2May be replaced independently of one another by O, S, -CH = CH-, -C ≡ C-or-COO-, and each two O or S are not linked to one another; when said R is2Is selected from the group consisting of2~C7When said alkenyl is (C), said2~C7One or more H in the alkenyl group of (a) may be substituted independently of each other by F;
z is selected from the group consisting of a single bond, -CH = CH-, -C.ident.C-, -O-, -COO-, -OCO-, -OCH2-、-C2H4-、-CH2O-、-OCF2-and-CF2O-;
x is selected from halogen, CN, C1~C7Alkyl and C1~C7Wherein said C is1~C7Alkyl and C1~C7One or more H in the alkoxy group of (a) may be substituted independently of each other by F;
L1、L2may be the same or different and are each independently H or F, wherein L is1、L2At least one of which is F;
may be the same or different and are independently selected from A group of components selected from the group consisting of,is selected from the group consisting ofA group consisting of, wherein,one or more CH in2Can be replaced independently of one another by O or S,may be substituted independently of one another by F;
a. b may be the same or different and are independently 0 or 1.
2. The liquid crystal composition of claim 1, wherein the compound of formula (I) comprises 5% to 25% by weight of the total liquid crystal composition.
3. The liquid crystal composition of claim 1, wherein R is1、R2May be the same or different and are independently selected from the group consisting of C1~C5Alkyl and C2~C5Wherein said C is1~C5One or more CH in the alkyl group of (2)2Can be replaced by O or S independently of each other, and every two of O or S are not connected to each other; when said R is2Is selected from the group consisting of2~C5When said alkenyl is (C), said2~C5One or more H in the alkenyl group of (a) may be substituted independently of each other by F;
z is selected from single bond, -COO-, -OCF2-and-CF2O-;
said X is selected from the group consisting of F, CN, C1~C5And C is fluoroalkyl and1~C5fluoro alkoxy group of (a);
the above-mentionedMay be the same or different and are independently selected from A group of (a); wherein, in addition to the above definitions, said Can also be
4. The liquid crystal composition according to claim 3, wherein the compound of formula (I) is one or more compounds selected from the group consisting of;
the compound of the general formula (II) is a compound selected from one or more of the group consisting of:
5. liquid crystal composition according to claim 1, characterized in that it may also comprise one or more compounds chosen from the compounds corresponding to general formula (III):
wherein:
R3、R4may be the same or different and are independently selected from the group consisting of C1~C7Alkyl of (C)1~C7Alkoxy and C2~C7Wherein said C is1~C7One or more CH in the alkyl group of (2)2Can be replaced by O or S independently of each other, and every two of O or S are not connected to each other; wherein, in addition to the above definitions, said R4May also be-OCF3
Independently of each other selected fromA group of (a); wherein,one or more CH in2May be replaced independently of one another by O or S; when saidIs composed ofWhen is in use, theMay be substituted independently of one another by F;
c is 0 or 1.
6. The liquid crystal composition of claim 5, wherein R is3、R4May be the same or different and are independently selected from the group consisting of C1~C5Alkyl of (C)1~C5Alkoxy and C2~C5Alkenyl groups of (a); wherein, in addition to the above definitions, said R4May also be-OCF3
7. The liquid crystal composition according to claim 6, wherein the compound of formula (III) is selected from one or more compounds selected from the group consisting of;
8. the liquid crystal composition according to any one of claims 4 to 7, wherein the liquid crystal composition comprises:
compound III-6 in an amount of 10% by weight based on the total weight of the liquid crystal composition;
compound I-1 accounting for 6 percent of the total weight of the liquid crystal composition;
compound I-3 accounting for 6 percent of the total weight of the liquid crystal composition;
38% by weight of compound III-12, based on the total weight of the liquid crystal composition;
compound III-13 in an amount of 4% by weight based on the total weight of the liquid crystal composition;
compound II-3 accounting for 4 percent of the total weight of the liquid crystal composition;
7% by weight of compound III-14, based on the total weight of the liquid crystal composition;
7% by weight of compound III-17 relative to the total weight of the liquid crystal composition;
5% by weight of compound III-9 relative to the total weight of the liquid crystal composition;
compound II-18 in an amount of 5% by weight based on the total weight of the liquid crystal composition;
compound II-20 accounting for 4 percent of the total weight of the liquid crystal composition; and
compound II-21 in an amount of 4% by weight based on the total weight of the liquid crystal composition,
alternatively, the liquid crystal composition comprises:
compound III-6 in an amount of 10% by weight based on the total weight of the liquid crystal composition;
compound I-1 accounting for 6 percent of the total weight of the liquid crystal composition;
6 percent of compound I-9 in the total weight of the liquid crystal composition;
38% by weight of compound III-12, based on the total weight of the liquid crystal composition;
compound III-13 in an amount of 4% by weight based on the total weight of the liquid crystal composition;
compound II-3 accounting for 4 percent of the total weight of the liquid crystal composition;
7% by weight of compound III-14, based on the total weight of the liquid crystal composition;
7% by weight of compound III-17 relative to the total weight of the liquid crystal composition;
5% by weight of compound III-9 relative to the total weight of the liquid crystal composition;
compound II-18 in an amount of 5% by weight based on the total weight of the liquid crystal composition;
compound II-20 accounting for 4 percent of the total weight of the liquid crystal composition; and
compound II-21 in an amount of 4% by weight based on the total weight of the liquid crystal composition,
alternatively, the liquid crystal composition comprises:
compound III-1 in an amount of 8% by weight based on the total weight of the liquid crystal composition;
compound I-1 accounting for 5 percent of the total weight of the liquid crystal composition;
compound I-3 accounting for 5 percent of the total weight of the liquid crystal composition;
37% by weight of compound III-12 based on the total weight of the liquid crystal composition;
compound III-13 in an amount of 6% by weight based on the total weight of the liquid crystal composition;
compound II-12 accounting for 3 percent of the total weight of the liquid crystal composition;
7% by weight of compound III-14, based on the total weight of the liquid crystal composition;
7% by weight of compound III-17 relative to the total weight of the liquid crystal composition;
compound II-6 accounting for 6 percent of the total weight of the liquid crystal composition;
compound II-9 accounting for 8 percent of the total weight of the liquid crystal composition;
compound II-14 in an amount of 4% by weight based on the total weight of the liquid crystal composition; and
compound II-15 accounting for 4 percent of the total weight of the liquid crystal composition,
alternatively, the liquid crystal composition comprises:
compound III-1 in an amount of 8% by weight based on the total weight of the liquid crystal composition;
compound I-1 accounting for 5 percent of the total weight of the liquid crystal composition;
5% of compound I-9 by weight of the total liquid crystal composition;
37% by weight of compound III-12 based on the total weight of the liquid crystal composition;
compound III-13 in an amount of 6% by weight based on the total weight of the liquid crystal composition;
compound II-12 accounting for 3 percent of the total weight of the liquid crystal composition;
7% by weight of compound III-14, based on the total weight of the liquid crystal composition;
7% by weight of compound III-17 relative to the total weight of the liquid crystal composition;
compound II-6 accounting for 6 percent of the total weight of the liquid crystal composition;
compound II-9 accounting for 8 percent of the total weight of the liquid crystal composition;
compound II-14 in an amount of 4% by weight based on the total weight of the liquid crystal composition; and
compound II-15 in an amount of 4% by weight based on the total weight of the liquid crystal composition.
9. Use of a liquid crystal composition according to any one of claims 1 to 8 in the manufacture of an electro-optical device.
10. An electro-optical liquid crystal display comprising the liquid crystal composition according to any one of claims 1 to 8.
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CN103409146B (en) * 2013-04-01 2015-10-28 石家庄诚志永华显示材料有限公司 For the liquid-crystal composition of driven with active matrix liquid-crystal display
CN104371746B (en) * 2013-08-16 2016-05-25 江苏和成显示科技股份有限公司 Liquid-crystal composition and liquid crystal display device
CN104513140B (en) * 2013-09-30 2016-04-13 江苏和成新材料有限公司 Contain the liquid crystalline cpd and preparation method and application of holding position difluoroethylene group
CN104513129B (en) * 2013-09-30 2016-06-08 江苏和成新材料有限公司 Preparation is containing the intermediate and the preparation method that hold position two vinyl fluoride group liquid crystalline cpd
WO2016115719A1 (en) * 2015-01-23 2016-07-28 北京欣奕华科技有限公司 Liquid crystal compound and preparation method therefor, liquid crystal composition and liquid crystal display panel

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EP0325796A1 (en) * 1987-12-28 1989-08-02 Chisso Corporation A liquid crystal compound and a mixture containing the same
CN1214036A (en) * 1996-03-18 1999-04-14 智索股份有限公司 Bisalkenyl derivatives, liquid crystalline compounds and liquid crystal compsns.
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EP0325796A1 (en) * 1987-12-28 1989-08-02 Chisso Corporation A liquid crystal compound and a mixture containing the same
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