CN103361076A - Liquid crystal composition with negative dielectric anisotropy and application thereof - Google Patents
Liquid crystal composition with negative dielectric anisotropy and application thereof Download PDFInfo
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- CN103361076A CN103361076A CN2013102557960A CN201310255796A CN103361076A CN 103361076 A CN103361076 A CN 103361076A CN 2013102557960 A CN2013102557960 A CN 2013102557960A CN 201310255796 A CN201310255796 A CN 201310255796A CN 103361076 A CN103361076 A CN 103361076A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 102
- 239000000203 mixture Substances 0.000 title claims abstract description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 9
- 239000011159 matrix material Substances 0.000 abstract description 5
- 239000010409 thin film Substances 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 0 CCC(*)C(CC1)(CCC1C1CCC(C)CC1)C#N Chemical compound CCC(*)C(CC1)(CCC1C1CCC(C)CC1)C#N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 description 1
- KKCMUGXMFHRQRO-UHFFFAOYSA-N CCC(CC1)(CCC1C1CCC(C)CC1)C#N Chemical compound CCC(CC1)(CCC1C1CCC(C)CC1)C#N KKCMUGXMFHRQRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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Abstract
The invention provides a liquid crystal composition. The liquid crystal composition has negative dielectric anisotropy and comprises at least one compound ith a general formula I (shown in the description), at least one compound with a general formula II (shown in the description) and at least one compound with a general formula III (shown in the description). The liquid crystal composition has proper negative dielectric anisotropy, proper optical anisotropy, low viscosity and wide nematic phase temperature range. The liquid crystal composition provided by the invention is suitable for an active matrix addressing liquid crystal display in a VA (Vertical Alignment), PSVA (Polymer Stabilize Vertical Align), IPS (In Plane Switching) or TFT (Thin Film Transistor) mode. The invention further provides a liquid crystal display device containing the liquid crystal composition.
Description
Technical Field
The invention relates to a liquid crystal composition, in particular to a liquid crystal composition with proper negative dielectric anisotropy, proper optical anisotropy, lower viscosity and wider nematic phase range and application thereof in VA, PSVA, IPS or TFT mode liquid crystal displays.
Background
In the liquid crystal display device, there are classifications based on the operation mode of liquid crystal: phase change (hereinafter, abbreviated as PC), twisted nematic (hereinafter, abbreviated as TN), super twisted nematic (hereinafter, abbreviated as STN), electrically controlled birefringence (hereinafter, abbreviated as ECB), optically compensated bend (hereinafter, abbreviated as OCB), transverse electric field switching (IPS), vertical transverse (VA), and the like. The device-based driving method is classified into: passive Matrix (PM) and AM. The PM is classified into static (static) and multiplex (multiplex), and the AM is classified into a Thin Film Transistor (TFT), a metal insulator metal (MTM), and the like. The TFT is classified into amorphous silicon (amorphous silicon) and polycrystalline silicon (polycrystalline silicon). The latter may be classified into a high temperature type and a low temperature type according to manufacturing steps. The light source-based classification includes a reflection type using natural light, a transmission type using backlight (black light), and a semi-transmission type using both natural light and backlight.
Currently, Vertical Alignment (VA) displays are increasingly well known and widely used in TVs, monitors, and vehicle-mounted displays, and the liquid crystal medium used in conjunction with the VA displays needs to be specially customized. For example, the liquid-crystalline medium should have a suitable negative dielectric anisotropy, a suitable optical anisotropy, a wide nematic temperature range, a low viscosity and a fast response. For active matrix addressed liquid crystal displays, the liquid crystal medium also needs to have a high voltage holding ratio, and good optical and thermal stability. In particular, for displays used in the on-board category and other outdoor uses, it is particularly desirable to have a wide nematic temperature range and a fast response time.
However, the properties of liquid crystal media are contradictory, and the existing liquid crystal media cannot have the properties at the same time. For displays used in on-vehicle type and other outdoor applications, while securing a very wide nematic phase temperature range, appropriate negative dielectric anisotropy, appropriate optical anisotropy, as small a viscosity as possible, and good light and heat stability are required. The liquid crystal composition disclosed in chinese patent application publication No. CN101679867A has a sufficiently wide upper limit of nematic phase temperature, but has a relatively large viscosity and a relatively slow response.
Disclosure of Invention
The invention aims to provide a liquid crystal medium which has proper negative dielectric anisotropy, proper optical anisotropy, lower viscosity, wider nematic phase range and higher response speed and can be suitable for active matrix addressing liquid crystal displays of VA, PSVA, IPS or TFT modes.
One aspect of the present invention provides a liquid crystal composition having negative dielectric anisotropy, the liquid crystal composition comprising:
at least one compound of the general formula I
At least one compound of the general formula II
at least one compound of the formula III
Wherein,
R1、R2、R3、R4、R5and R6The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms, in which one or more hydrogen atoms may be substituted by fluorine.
In some embodiments, the liquid crystal composition of the present invention further comprises one or more of the compounds according to formula iv:
wherein,
R7and R8The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
z represents-CH2O-or a single bond, Z is a single bond when n = 0;
and
same or different, selected from the group consisting of
And
group of wherein
One or more of H may be substituted by F;
m and n are the same or different and each independently represents 0 or 1.
In some embodiments of the present invention, it is preferred that the compound of formula I comprises 5 to 30% by weight of the total liquid crystal composition; the compound of the general formula II accounts for 20-60% of the total weight of the liquid crystal composition; the compound of the general formula III accounts for 1-15% of the total weight of the liquid crystal composition; and the compound of the general formula IV accounts for 15-50% of the total weight of the liquid crystal composition.
In some embodiments of the invention, it is preferred that R is1、R2、R3、R4、R5And R6Is an alkyl or alkoxy group having 1 to 7 carbon atoms, wherein one or more hydrogen atoms may be substituted by fluorine.
More preferably, the compound of the general formula I accounts for 10-25% of the total weight of the liquid crystal composition; the compound of the general formula II accounts for 30-60% of the total weight of the liquid crystal composition; the compound of the general formula III accounts for 1-10% of the total weight of the liquid crystal composition; and the compound of the general formula IV accounts for 20-45% of the total weight of the liquid crystal composition.
In some embodiments, the compound of formula I is preferably one or more of the following compounds:
the compound of formula ii is preferably one or more of the following compounds:
the compound of formula iii is preferably one or more of the compounds:
the compound of formula iv is preferably one or more of the following compounds:
another aspect of the present invention is to provide a liquid crystal display comprising the liquid crystal composition of the present invention.
It is a further aspect of the present invention to provide a liquid crystal display for VA, PSVA, IPS or TFT mode comprising the liquid crystal composition of the present invention.
The liquid crystal medium comprising the liquid crystal composition is determined by performing combination experiments on the compounds and comparing with a control, has proper dielectric anisotropy, proper optical anisotropy, lower viscosity and wider nematic phase range, and can be suitable for active matrix addressing liquid crystal displays of VA, PSVA, IPS or TFT modes.
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.
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
Compounds of the following formula are exemplified:
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCC1OWm, wherein n and m in the code represent the number of C atoms in the alkyl group at the left end and the right end respectively, for example, n is 3, that is, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane; 1O represents a methyleneoxy group; w represents 2, 3-difluoro-1, 4-phenylene.
The abbreviated codes of the test items in the following examples are as follows:
cp (. degree. C.): clearing points (nematic-isotropic phase transition temperature)
Δ n: optical anisotropy (589 nm, 25 ℃ C.)
Δ ε: dielectric anisotropy (1 KHz, 25 ℃ C.)
Eta: flow viscosity (mm)2·s-125 ℃ unless otherwise stated)
τ on: time until reaching a transmittance of 90% (ms)
τ off: time (ms) until cut at which transmittance 10% is reached
τ Ton + Toff (response time) (ms)
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.
Table 2 shows the components and ratios of the liquid crystal composition of the comparative example and the results of the performance test conducted on the liquid crystal composition filled between two substrates of the liquid crystal display device, so as to compare the performance of the liquid crystal composition of the present invention.
Comparative example 1
The liquid crystal composition of comparative example 1, 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 2, 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 example 1 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
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 the weight percentages listed in table 4, and 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, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Comparative example 3
The liquid crystal composition of comparative example 3, 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 6, 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 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
Comparative example 4
The liquid crystal composition of comparative example 4, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared according to the compounds and the weight percentages listed in table 8, and the test data are shown in the following table:
TABLE 8 liquid crystal composition formulations and their test properties
Example 4
The liquid crystal composition of example 4 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, and the test data are shown in the following table:
TABLE 9 liquid crystal composition formulations and their test properties
Referring to comparative examples 1, 2,3 and 4, it can be seen from the test data of examples 1, 2,3 and 4 above that the liquid crystal composition provided by the present invention has a suitable negative dielectric anisotropy, a suitable optical anisotropy, a lower viscosity and a higher clearing point. When the refractive index anisotropy, clearing point and dielectric anisotropy data are similar, the liquid crystal composition provided by the invention has smaller viscosity and higher response speed, and can be suitable for VA, PSVA, IPS or TFT mode liquid crystal displays.
Claims (9)
1. A liquid crystal composition having a negative dielectric anisotropy, comprising:
at least one compound of the general formula I
At least one compound of the general formula II
at least one compound of the formula III
Wherein,
R1、R2、R3、R4、R5and R6The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms, in which one or more hydrogen atoms may be substituted by fluorine.
2. The liquid crystal composition of claim 1, further comprising one or more compounds of formula iv:
wherein,
R7and R8The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
z represents-CH2O-or a single bond, Z is a single bond when n = 0;
m and n are the same or different and each independently represents 0 or 1.
3. The liquid crystal composition of claim 2, wherein the compound of formula i comprises 5-30% by weight of the total liquid crystal composition; the compound of the general formula II accounts for 20-60% of the total weight of the liquid crystal composition; the compound of the general formula III accounts for 1-15% of the total weight of the liquid crystal composition; and the compound of the general formula IV accounts for 15-50% of the total weight of the liquid crystal composition.
4. The liquid crystal composition of claim 3, wherein R is1、R2、R3、R4、R5And R6The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms in which one or more hydrogen atoms may be substituted by fluorine.
5. The liquid crystal composition of claim 4, wherein the compound of formula I comprises 10-25% by weight of the total liquid crystal composition; the compound of the general formula II accounts for 30-60% of the total weight of the liquid crystal composition; the compound of the general formula III accounts for 1-10% of the total weight of the liquid crystal composition; and the compound of the general formula IV accounts for 20-45% of the total weight of the liquid crystal composition.
6. The liquid crystal composition of claim 5, wherein the compound of formula I is selected from one or more compounds of the group consisting of:
the compound of formula ii is selected from one or more compounds of the group consisting of:
the compound of formula iii is selected from one or more compounds of the group consisting of:
the compound of the general formula IV is selected from one or more compounds in the group consisting of:
7. the liquid crystal composition of claim 6, wherein the liquid crystal composition comprises:
2% by weight of a compound of formula (IV-16);
8% by weight of a compound of formula (I-7);
12% by weight of a compound of formula (II-2);
11% by weight of a compound of formula (II-5);
11% by weight of a compound of formula (II-6);
8% by weight of a compound of formula (I-6);
4% by weight of a compound of the formula (III-4);
8% by weight of a compound of the formula (IV-2);
7% by weight of a compound of formula (IV-4);
7% by weight of a compound of formula (IV-6);
11% by weight of a compound of formula (II-8);
6% by weight of a compound of formula (IV-13); and
5% by weight of a compound of the formula (IV-12),
alternatively, the liquid crystal composition comprises:
2% by weight of a compound of formula (IV-20);
2% by weight of a compound of formula (IV-24);
2% by weight of a compound of formula (IV-16);
7% by weight of a compound of formula (I-7);
10% by weight of a compound of formula (II-2);
10% by weight of a compound of formula (II-5);
10% by weight of a compound of formula (II-6);
8% by weight of a compound of formula (I-6);
3% by weight of a compound of formula (III-5);
3% by weight of a compound of the formula (III-4);
5% by weight of a compound of formula (IV-2);
5% by weight of a compound of formula (IV-6);
10% by weight of a compound of formula (II-8);
8% by weight of a compound of the formula (IV-7);
5% by weight of a compound of formula (IV-8);
5% by weight of a compound of formula (IV-13); and
5% by weight of a compound of the formula (IV-12),
alternatively, the liquid crystal composition comprises:
7% by weight of a compound of formula (I-7);
12% by weight of a compound of formula (II-2);
12% by weight of a compound of formula (II-5);
12% by weight of a compound of formula (II-6);
8% by weight of a compound of formula (I-6);
4% by weight of a compound of the formula (III-4);
5% by weight of a compound of formula (IV-2);
5% by weight of a compound of formula (IV-6);
12% by weight of a compound of formula (II-8);
8% by weight of a compound of the formula (IV-7);
5% by weight of a compound of formula (IV-8);
5% by weight of a compound of formula (IV-13); and
5% by weight of a compound of the formula (IV-12),
alternatively, the liquid crystal composition comprises:
2% by weight of a compound of formula (IV-20);
2% by weight of a compound of formula (IV-24);
2% by weight of a compound of formula (IV-16);
6% by weight of a compound of formula (I-7);
12% by weight of a compound of formula (II-2);
12% by weight of a compound of formula (II-5);
12% by weight of a compound of formula (II-6);
7% by weight of a compound of formula (I-6);
6% by weight of a compound of the formula (III-5);
7% by weight of a compound of the formula (III-4);
15% by weight of a compound of formula (IV-7);
5% by weight of a compound of formula (IV-10);
6% by weight of a compound of formula (IV-13); and
6% by weight of a compound of the formula (IV-12).
8. A liquid crystal display comprising a liquid crystal composition according to at least one of claims 1 to 7.
9. Liquid crystal display of the VA, PSVA, IPS and TFT mode comprising a liquid crystal composition according to at least one of claims 1 to 7.
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Cited By (9)
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| CN103666485A (en) * | 2013-12-04 | 2014-03-26 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropic liquid crystal composition |
| CN104152155A (en) * | 2014-07-17 | 2014-11-19 | 北京大学 | High negative dielectric anisotropy liquid crystal mixture with high birefringence and low viscosity and application thereof |
| CN104974766A (en) * | 2014-04-09 | 2015-10-14 | 江苏和成显示科技股份有限公司 | High-clearing-point and high-refractive-index anisotropic negative liquid crystal composition and application thereof |
| CN105368464A (en) * | 2014-09-02 | 2016-03-02 | 江苏和成显示科技股份有限公司 | Liquid crystal composition with negative dielectric anisotropy and display device thereof |
| CN105441085A (en) * | 2014-08-26 | 2016-03-30 | 江苏和成显示科技股份有限公司 | A liquid crystal composition and a liquid crystal display element containing the same |
| CN106635054A (en) * | 2015-10-28 | 2017-05-10 | 江苏和成显示科技股份有限公司 | Liquid crystal composition having negative dielectric anisotropy, and applications thereof |
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| CN108315019A (en) * | 2018-02-01 | 2018-07-24 | 烟台显华化工科技有限公司 | A kind of negative dielectric anisotropy liquid crystal composition and its application |
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| CN103666485B (en) * | 2013-12-04 | 2015-12-09 | 石家庄诚志永华显示材料有限公司 | A kind of negative dielectric anisotropy liquid crystal composition |
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| CN106662784B (en) * | 2014-07-29 | 2020-06-05 | Dic株式会社 | Liquid crystal display element |
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| CN105441085A (en) * | 2014-08-26 | 2016-03-30 | 江苏和成显示科技股份有限公司 | A liquid crystal composition and a liquid crystal display element containing the same |
| CN105368464A (en) * | 2014-09-02 | 2016-03-02 | 江苏和成显示科技股份有限公司 | Liquid crystal composition with negative dielectric anisotropy and display device thereof |
| CN105368464B (en) * | 2014-09-02 | 2020-09-08 | 江苏和成显示科技有限公司 | Liquid crystal composition having negative dielectric anisotropy and display device thereof |
| CN106635054A (en) * | 2015-10-28 | 2017-05-10 | 江苏和成显示科技股份有限公司 | Liquid crystal composition having negative dielectric anisotropy, and applications thereof |
| US20180312757A1 (en) * | 2015-11-19 | 2018-11-01 | Jiangsu Hecheng Display Technology Co., Ltd. | Liquid crystal composition and display device thereof |
| JP2019501239A (en) * | 2015-11-19 | 2019-01-17 | ジアンスー ヘチェン ディスプレイ テクノロジー カンパニー リミテッド | Liquid crystal composition and display device thereof |
| CN106753422A (en) * | 2015-11-19 | 2017-05-31 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and its display device |
| WO2017084568A1 (en) * | 2015-11-19 | 2017-05-26 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and display device thereof |
| US10920146B2 (en) * | 2015-11-19 | 2021-02-16 | Jiangsu Hecheng Display Technology Co., Ltd. | Liquid crystal composition and display device thereof |
| CN106753422B (en) * | 2015-11-19 | 2021-04-20 | 江苏和成显示科技有限公司 | Liquid crystal composition and display device thereof |
| CN108315019A (en) * | 2018-02-01 | 2018-07-24 | 烟台显华化工科技有限公司 | A kind of negative dielectric anisotropy liquid crystal composition and its application |
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