CN109575948B - Liquid crystal composition and liquid crystal display device thereof - Google Patents
Liquid crystal composition and liquid crystal display device thereof Download PDFInfo
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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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
- C09K19/46—Mixtures 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 discloses a liquid crystal composition and a liquid crystal display device thereof, wherein the liquid crystal composition comprises: at least one compound of formula I, and at least one compound of formula II. The liquid crystal composition provided by the invention has proper optical anisotropy, a high clearing point, a large absolute value of dielectric anisotropy and good low-temperature storage performance, when the liquid crystal composition is applied to a liquid crystal display, the driving voltage of the liquid crystal display can be reduced, the power consumption is reduced, and meanwhile, the liquid crystal display has good weather resistance and can be used in a severe external environment.
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition and a liquid crystal display device thereof.
Background
Liquid Crystal Displays (LCDs) have been rapidly developed due to their small size, light weight, low power consumption and excellent Display quality, and are widely used particularly in portable electronic information products. As the size of liquid crystal screens for portable computers, office applications, and video applications increases, liquid crystal displays can be used for large screen displays and eventually replace Cathode Ray Tube (CRT) displays.
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 liquid crystal material must have good low temperature miscibility and thermal stability. Furthermore, the liquid crystal material should have low viscosity and short response time, low threshold voltage and high contrast. In order to obtain a liquid crystal display device having good characteristics and to improve various performance indexes of the liquid crystal composition, the following table 1 summarizes the relationship between one performance of the liquid crystal composition and one corresponding performance of the liquid crystal display device. The performance indexes of the composition are further described based on commercially available liquid crystal display elements. The temperature range of the nematic phase is associated with the operating temperature range of the element. The upper limit temperature of the nematic phase is preferably 70 ℃ or higher, and the lower limit temperature of the nematic phase is preferably-10 ℃ or lower. The viscosity of the composition correlates to the response time of the element. In order to display animation in the element, it is preferable that the response time of the element is short. Therefore, it is preferable that the viscosity of the composition is small, and it is more preferable that the viscosity of the composition is small at a low temperature.
TABLE 1 general characteristics of the compositions and liquid crystal display elements
| NO. | General characteristics of the composition | General characteristics of liquid crystal display elements |
| 1 | Wide temperature range of nematic phase | Wide temperature range |
| 2 | Low viscosity | Short response time |
| 3 | Appropriate optical anisotropy | High contrast |
| 4 | Large positive or negative dielectric constant anisotropy | Low critical voltage, low power consumption and high contrast |
| 5 | High resistivity | High voltage holding ratio and high contrast |
| 6 | UV and heat stabilization | Long service life |
It is generally difficult for a single liquid crystal compound to exert its properties, and it is generally mixed with a plurality of other liquid crystal compounds to prepare a composition. In the existing liquid crystal composition, the better characteristics can be obtained, but the composition has the disadvantages of lower clearing point, higher viscosity, insufficient optical anisotropy, lower absolute value of dielectric anisotropy, low voltage holding ratio, and low contribution to the composition mixed to have larger optical anisotropy, absolute value of suitable dielectric anisotropy, better stability and better contrast, and directly causes the adverse effects of low contrast, slow response speed, poor display effect of devices and the like, for example, foreign patent documents WO9202597, WO9116398, WO9302153, WO9116399, chinese patent document CN1157005A and the like, and the disadvantages are caused to different degrees.
Therefore, there is a need for a liquid crystal composition having characteristics of large optical anisotropy, high absolute value of dielectric anisotropy, high clearing point, low driving voltage, good stability, good steepness, good gray scale display effect, and the like.
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 optical anisotropy, a large absolute value of dielectric anisotropy, a wide nematic phase, a high low-temperature storage stability, and a low driving voltage, and a liquid crystal display element including the liquid crystal composition.
The technical scheme of the invention is as follows:
one aspect of the present invention provides a liquid crystal composition comprising:
at least one compound of the formula I
At least one compound of the general formula II
Wherein the content of the first and second substances,
R1represents an alkyl group having 1 to 7 carbon atoms;
R2represents-H, -F, alkyl or alkoxy containing 1-7 carbon atoms, alkenyl or alkenyloxy containing 2-7 carbon atoms,
Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
X1and X2Each independently represents-F, -CF3、-OCF3-CN or-SCN;
Z1and Z2Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-、-CF2O-、-OCF2-or-CH2CH2-；
L1And L4Each independently represents-H or-CH3；
L2、L3、L5And L6Each independently represents-H or-F;
ring (C)
And ring
Each independently represent
Wherein
In one or more-CH2-can be replaced by-O-,
wherein one or more H may be substituted by halogen, wherein the ring is
And ring
One or more of the single bonds in (a) may be replaced by a double bond, and one or more-CH-may be replaced by-N;
a represents an integer of 1 to 12;
n and m each independently represent 1, 2, 3 or 4, and when n is 2, 3 or 4, a ring
May be the same or different, Z1May be the same or different; when m is 2, 3, 4, the ring
May be the same or different, Z2May be the same or different.
Preferably, the compound of formula i is selected from the group consisting of:
wherein the content of the first and second substances,
ring (C)
And ring
Each independently represent
Z11Represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
n1 represents 0, 1, 2 or 2, and when n1 is 2 or 3, the ring
May be the same or different, Z1May be the same or different.
Further preferably, the compound of formula I-1 is selected from the group consisting of:
the compound of formula I-2 is selected from the group consisting of:
in some embodiments of the invention, a is preferably 2, 3 or 4.
In some embodiments of the present invention, the compound of formula I comprises 5-80% of the total weight of the liquid crystal composition; preferably, the compound of the general formula I accounts for 5-65% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula I accounts for 10-50% of the total weight of the liquid crystal composition; still more preferably, the compound of formula i accounts for 10-30% of the total weight of the liquid crystal composition.
Preferably, the compound of formula ii is selected from the group consisting of:
wherein the content of the first and second substances,
ring (C)
And a ring
Each independently represent
Z21Represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
m1 represents 0, 1 or 2, and when m1 is 2, the ring
May be the same or different, Z2May be the same or different.
Further preferably, the compound of formula II-1 is selected from the group consisting of:
the compound of formula II-2 is selected from the group consisting of:
further, the liquid crystal composition also comprises at least one compound of a general formula III
Wherein the content of the first and second substances,
R3and R4Each independently represents-H, an alkyl or alkoxy group having 1 to 12 carbon atoms, an alkenyl or alkenyloxy group having 2 to 12 carbon atoms,
Ring (C)
Ring (C)
And ring
Each independently represent
Z3Represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
r represents 0, 1 or 2, and when r is 2, a ring
May be the same or different, Z3May be the same or different.
In some embodiments of the invention, the compound of formula II comprises 10 to 80% of the total weight of the liquid crystal composition; preferably, the compound of the general formula II accounts for 10-70% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula II accounts for 10-60% of the total weight of the liquid crystal composition; still further preferably, the compound of formula II accounts for 10-50% of the total weight of the liquid crystal composition.
Preferably, the compound of formula iii is selected from the group consisting of:
wherein, the first and the second end of the pipe are connected with each other,
R31and R41Each independently represents-H, an alkyl or alkoxy group having 1 to 7 carbon atoms, an alkenyl or alkenyloxy group having 2 to 7 carbon atoms,
In some embodiments of the present invention, preferably, the compound of formula III-1 is selected from the group consisting of:
the compound of formula III-2 is selected from the group consisting of:
the compound of formula III-3 is selected from the group consisting of:
the compound of formula III-4 is selected from the group consisting of:
the compound of formula III-5 is selected from the group consisting of:
the compound of formula III-6 is selected from the group consisting of:
the compound of formula III-7 is selected from the group consisting of:
the compound of formula III-8 is selected from the group consisting of:
the compounds of formula III-9 are selected from the group consisting of:
the compounds of formula III-10 are selected from the group consisting of:
the compounds of formula III-11 are selected from the group consisting of:
the compounds of formula III-12 are selected from the group consisting of:
the compounds of formulae III-13 are selected from the group consisting of:
the compounds of formulas III-14 are selected from the group consisting of:
the compounds of formulas III-15 are selected from the group consisting of:
the compounds of formulas III-16 are selected from the group consisting of:
in some embodiments of the invention, R31And R41At least one of which is an alkenyl or alkenyloxy group containing 2 to 7 carbon atoms.
In some embodiments of the present invention, the compound of formula I is present in an amount of 5 to 80% by weight, the compound of formula II is present in an amount of 10 to 80% by weight, and the compound of formula III is present in an amount of 5 to 80% by weight of the total liquid crystal composition.
Further, in some embodiments of the present invention, the compound of formula I is present in an amount of 10 to 50% by weight, the compound of formula II is present in an amount of 10 to 70% by weight, and the compound of formula III is present in an amount of 10 to 60% by weight of the total liquid crystal composition.
In some embodiments of the invention, the compound of formula i is preferably selected from the following compounds: i-1-1, I-1-2, I-1-3, I-1-4, I-1-10, I-1-20 and I-2-1.
In some embodiments of the invention, the compound of formula ii is preferably selected from the following compounds: II-1-1, II-1-2, II-1-4, II-1-7, II-1-17, II-2-1, II-2-7, II-2-28, II-2-2, II-2-30 and II-2-49.
In some embodiments of the invention, the compound of formula iii is preferably selected from the following compounds: III-1-10, III-1-15, III-5-4, III-8-4, III-14-6 and III-16-10.
In another aspect, the present invention provides a liquid crystal composition further comprising one or more additives known to those skilled in the art and described in the literature. For example, pleochroic dyes and/or chiral dopants may be added in an amount of 0 to 15 wt% based on the total weight of the liquid crystal composition.
The following shows possible dopants which are preferably added to the mixtures according to the invention.
In the embodiment of the present invention, it is preferable that the dopant is 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the dopant is present in an amount of 0 to 1 wt% based on the total weight of the liquid crystal composition.
The stabilizers which may be added to the mixtures according to the invention are mentioned below, for example.
Preferably, the stabilizer is selected from the group consisting of the stabilizers shown below.
In the embodiment of the present invention, it is preferable that the stabilizer accounts for 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the stabilizer accounts for 0-1 wt% of the total weight of the liquid crystal composition; as a particularly preferred embodiment, the stabilizer is 0 to 0.1 wt% of the total weight of the liquid crystal composition.
In another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
Has the advantages that:
the liquid crystal composition provided by the invention has proper optical anisotropy, a high clearing point, a large absolute value of dielectric anisotropy and good low-temperature storage performance, when the liquid crystal composition is applied to a liquid crystal display, the driving voltage of the liquid crystal display can be reduced, the power consumption is reduced, and meanwhile, the liquid crystal display has good weather resistance and can be used in a severe external environment.
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 2:
TABLE 2 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
the structural formula is represented by the code listed in Table 2, 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-F.
The abbreviated codes of the test items in the following examples are as follows:
wherein the content of the first and second substances,
the optical anisotropy is obtained by testing 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.
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 are tested for compliance with electronic compound standards.
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
The liquid crystal composition of comparative example 1 was prepared with 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
Example 1
The liquid crystal composition of example 1 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, the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Example 2
The liquid crystal composition of example 2 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, the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
As can be seen from comparison of comparative example 1 with examples 1 and 2, the introduction of the component of the general formula I of the present invention can significantly improve the clearing point, the absolute value of dielectric anisotropy, and the low-temperature storage property of the liquid crystal composition.
Comparative example 2
The liquid crystal composition of comparative example 2 was prepared with 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
Example 3
The liquid crystal composition of example 3 was prepared with the compounds and weight percentages listed in table 7, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
As can be seen from comparison of comparative example 2 and example 3, the introduction of the component of the general formula I of the present invention can significantly improve the clearing point, the absolute value of the dielectric anisotropy, and the low-temperature storage property of the liquid crystal composition.
Example 4
The liquid crystal composition of example 4 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, the test data are shown in the following table:
TABLE 8 liquid crystal composition formulations and their test properties
Example 5
The liquid crystal composition of example 5 was prepared with 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
Example 6
The liquid crystal composition of example 6 was prepared according to the compounds and weight percentages listed in table 10, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 10 liquid crystal composition formulations and their test properties
It can be seen from the above comparative examples and examples that the liquid crystal composition provided by the present invention has suitable optical anisotropy, a high clearing point, a large absolute value of dielectric anisotropy, and also has good low-temperature storage property, and when the liquid crystal composition is applied to a liquid crystal display, the liquid crystal composition can reduce driving voltage, reduce power consumption, and also has good weather resistance, and can be used in a severe external environment.
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 (7)
1. A liquid crystal composition, comprising:
5-80% by weight of the total liquid crystal composition of at least one compound of formula I selected from the group consisting of:
10-80% by weight of the total liquid crystal composition of at least one compound of formula II:
at least one compound of the general formula III accounting for 5-80% of the total weight of the liquid crystal composition
Wherein, the first and the second end of the pipe are connected with each other,
R1represents an alkyl group having 1 to 7 carbon atoms;
R2represents-H, -F, alkyl or alkoxy containing 1-7 carbon atoms, alkenyl or alkenyloxy containing 2-7 carbon atoms,
Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
R3and R4Each independently represents-H, an alkyl or alkoxy group having 1 to 12 carbon atoms, an alkenyl or alkenyloxy group having 2 to 12 carbon atoms,
X1And X2Each independently represents-F, -CF3or-OCF3；
Z1And Z2Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-、-CF2O-、-OCF2-or-CH2CH2-；
Z3And Z11Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；L1And L4Each independently represents-H or-CH3；
L2、L3、L5And L6Each independently represents-H or-F;
ring (C)
And ring
Each independently represent
Ring (C)
To represent
Wherein
In one or more-CH2-can be replaced by-O-,
wherein one or more H may be substituted by halogen, wherein the ring is
One or more of the single bonds in (a) may be replaced by a double bond, one or more-CH-may be replaced by-N;
ring (C)
Ring (C)
And ring
Each independently represent
a represents an integer of 1 to 12;
m represents 1, 2, 3 or 4, n represents 2, 3, 4, n1 represents 0, 1, 2 or 3; and when n is 2, 3, 4, the ring
May be the same or different, Z1May be the same or different; when n1 is 2 or 3, the ring
May be the same or different, Z1May be the same or different; when m is 2, 3, 4, the ring
May be the same or different, Z2May be the same or different;
r represents 0, 1 or 2, and when r is 2, a ring
May be the same or different, Z3May be the same or different.
2. The liquid crystal composition of claim 1, wherein the compound of formula i-1 is selected from the group consisting of:
the compound of formula I-2 is selected from the group consisting of:
3. the liquid crystal composition of claim 1, wherein the compound of formula ii is selected from the group consisting of:
wherein the content of the first and second substances,
ring (C)
And ring
Each independently represent
Z21Represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
m1 represents 0, 1 or 2, and when m1 is 2, the ring
May be the same or different, Z2May be the same or different.
4. The liquid crystal composition of claim 3, wherein the compound of formula ii-1 is selected from the group consisting of:
the compound of formula II-2 is selected from the group consisting of:
5. the liquid crystal composition of claim 1, wherein the compound of formula iii is selected from the group consisting of:
wherein the content of the first and second substances,
R31and R41Each independently represents-H, an alkyl or alkoxy group having 1 to 7 carbon atoms, an alkenyl or alkenyloxy group having 2 to 7 carbon atoms,
6. The liquid crystal composition of claim 1, wherein the compound of formula i is present in an amount of 10 to 50% by weight, the compound of formula ii is present in an amount of 10 to 70% by weight, and the compound of formula iii is present in an amount of 10 to 60% by weight, based on the total weight of the liquid crystal composition.
7. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 6.
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Address after: 2/F, Sino Japan Cooperation Innovation Park, No. 16 Zidan Road, Qinhuai District, Nanjing, Jiangsu Province, 210014 Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Address before: 212212 East Side of Yangzhong Yangtze River Bridge, Zhenjiang City, Jiangsu Province Patentee before: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. |