CN104342168B - There is liquid-crystal composition and the liquid crystal display device of good low temperature storage stability - Google Patents
There is liquid-crystal composition and the liquid crystal display device of good low temperature storage stability Download PDFInfo
- Publication number
- CN104342168B CN104342168B CN201310339363.3A CN201310339363A CN104342168B CN 104342168 B CN104342168 B CN 104342168B CN 201310339363 A CN201310339363 A CN 201310339363A CN 104342168 B CN104342168 B CN 104342168B
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- crystal composition
- compound
- weight
- total weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 189
- 239000000203 mixture Substances 0.000 title claims abstract description 167
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 239000011159 matrix material Substances 0.000 claims abstract description 5
- 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 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004991 fluoroalkenyl group Chemical group 0.000 claims description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 229940126214 compound 3 Drugs 0.000 claims 9
- 229940125782 compound 2 Drugs 0.000 claims 4
- 230000004044 response Effects 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QOIWHSKYUNIFCV-UHFFFAOYSA-N (2-fluoro-4-propylphenyl)boronic acid Chemical compound CCCC1=CC=C(B(O)O)C(F)=C1 QOIWHSKYUNIFCV-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- ZRTWIJKGTUGZJY-UHFFFAOYSA-N 3,4,5-trifluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1 ZRTWIJKGTUGZJY-UHFFFAOYSA-N 0.000 description 1
- HWQNWWGSYSISNO-UHFFFAOYSA-N 4-bromo-2,3,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(Br)C(F)=C1F HWQNWWGSYSISNO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 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
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- -1 hydrogen trifluoride Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 description 1
- IPGCWJZKTTZTSB-UHFFFAOYSA-K trisodium;trifluoride Chemical compound [F-].[F-].[F-].[Na+].[Na+].[Na+] IPGCWJZKTTZTSB-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
The present invention provides a kind of liquid-crystal composition and application thereof, and this liquid-crystal composition comprises in terms of described liquid-crystal composition gross weight: one or more of 5-40% are selected from compounds of formula I；One or more of 30-60% are selected from the compound of formula II；The compound of one or more choosing free general formula III-1, general formula III-2 and combinations thereof compositions of 5-45%.The liquid-crystal composition of the present invention has big dielectric anisotropy, the highest refractive anisotrop, faster response speed and good low temperature storage stability.The present invention also provides for comprising the active matrix liquid crystal display device of this liquid-crystal composition.
Description
Technical Field
The present invention relates to a liquid crystal composition, and more particularly, to a liquid crystal composition having appropriate optical anisotropy and dielectric anisotropy, a fast response speed, and good low-temperature storage stability, and an application thereof in an active matrix liquid crystal display device.
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 display devices operate by utilizing optical anisotropy and dielectric anisotropy of liquid crystal materials themselves, and are now widely used. The device can be designed into various operation modes by utilizing different characteristics and operation modes of the liquid crystal material, wherein the conventional display commonly uses a TN mode (twisted nematic mode, a liquid crystal mixture has a nematic structure with a twist degree of about 90 degrees), an STN mode (super twisted nematic mode), an SBE mode (super twisted birefringence), an ECB mode (electrically controlled birefringence), a VA mode (vertical alignment), IPS (in-plane switching), and the like, and a plurality of improvement modes are made according to the above various modes.
For liquid crystal displays, liquid crystal compounds and liquid crystal media having good chemical and thermal stability, good stability to electric fields and electromagnetic radiation, suitable optical anisotropy, faster response speed, and lower threshold voltage are in line with the current demand. For active matrix addressed liquid crystal displays, the liquid crystal medium also has 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 very wide nematic temperature range.
However, the properties of liquid crystal media are contradictory, and the existing liquid crystal media cannot have the properties at the same time. Therefore, in the field of liquid crystal materials, there is a need for novel liquid crystal compositions having improved properties. In particular, for many types of applications, the liquid crystal composition must have a suitable nematic phase range, a suitable refractive index, dielectric anisotropy and low temperature storage stability.
Disclosure of Invention
The invention aims to provide a liquid crystal composition which has the characteristics of proper optical anisotropy and dielectric anisotropy, higher response speed, good low-temperature storage stability and the like. The liquid crystal composition can be applied to an AM element, and the AM element has the characteristics of short response time, high voltage holding ratio, high contrast, long service life and the like.
One aspect of the present invention provides a liquid crystal composition comprising, based on the total weight of the liquid crystal composition:
5-40% of one or more compounds selected from formula I
30-60% of one or more compounds selected from the group consisting of compounds of formula II
And
5-45% of one or more compounds selected from the group consisting of formula III-1, formula III-2, and combinations thereof
Wherein,
R1、R2、R3、R4、R5and R6The same or different, each is independently selected from H, alkyl or alkoxy with 1-7 carbon atoms,A fluoroalkyl group or fluoroalkoxy group having 1 to 7 carbon atoms, an alkenyl group or alkenyloxy group having 2 to 7 carbon atoms, or a fluoroalkenyl group or fluoroalkenyloxy group having 2 to 7 carbon atoms;
X1selected from the group consisting of H, F, Cl, -OCF3An alkyl group or an alkoxy group having 1 to 7 carbon atoms, a fluoroalkyl group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms, a fluoroalkenyl group having 2 to 5 carbon atoms or a fluoroalkenyloxy group having 2 to 5 carbon atoms;
andare the same or different and are each independently selected from the group consisting of Anda group of (a);
L1、L2and L3The same or different, each independently represents H or F.
The liquid crystal composition further comprises:
1-25% by weight of the total liquid crystal composition of a compound selected from the group consisting of compounds of formula IV-1, compounds of formula IV-2 and combinations thereof
Wherein,
R7、R8and R9The same or differentEach independently selected from the group consisting of an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms;
L4、L5、L6、L7and L8The same or different, each independently represents H or F.
In some embodiments of the present invention, it is preferred that the compound of formula I comprises 10 to 35% by weight of the total liquid crystal composition; the compound of the general formula II accounts for 35-55% of the total weight of the liquid crystal composition; the compound composed of the general formula III-1, the general formula III-2 and the combination accounts for 10-40% of the total weight of the liquid crystal composition; and the compound formed by the general formula IV-1, the general formula IV-2 and the combination thereof accounts for 2-20% of the total weight of the liquid crystal composition.
In some embodiments of the invention, the compound of formula i is selected from one or more of the group consisting of:
and
wherein,
the R is1Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
In some embodiments of the invention, the compound of formula ii is selected from one or more compounds in the group consisting of:
and
wherein,
the R is2Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
In some embodiments of the invention, the compound of formula III-1 is selected from one or more compounds from the group consisting of:
and
wherein,
the R is4Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
Said X1Selected from the group consisting of F or an alkyl or alkoxy group having 1 to 5 carbon atoms.
In some embodiments of the invention, the compound of formula III-2 is selected from one or more compounds of the group consisting of:
and
in some embodiments of the invention, the compound of formula IV-1 is selected from one or more compounds in the group consisting of:
and
wherein,
R7selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms;
in some embodiments of the invention, the compound of formula IV-2 is selected from one or more compounds of the group consisting of:
and
wherein,
R8and R9The same or different, each is independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms;
another aspect of the present invention provides a liquid crystal display device comprising the liquid crystal composition of the present invention.
A further aspect of the invention provides an active matrix liquid crystal display device comprising a liquid crystal composition of the invention.
The liquid crystal medium comprising the liquid crystal composition is determined to have the characteristics of small viscosity, good low-temperature stability, large dielectric anisotropy and high thermal stability by performing a combination experiment on the compounds and comparing the compounds with a control.
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.
Drawings
FIG. 1 is a drawing of Compound B1H NMR chart;
FIG. 2 is a drawing of Compound D1H NMR chart;
FIG. 3 is of Compound E1H NMR chart;
FIG. 4 is a drawing of Compound F1H NMR chart;
FIG. 5 is a drawing of Compound G1H NMR chart;
FIG. 6 is of Compound H1H NMR chart.
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: 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.
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: dielectric anisotropy (1 KHz, 25 ℃ C.)
γ 1: torsional viscosity (mPas at 20 ℃ C.)
LTS: low temperature storage time (at-20 ℃ C.)
Wherein, the refractive index anisotropy is obtained by testing an Abbe refractometer under a sodium lamp (589 nm) light source at 25 ℃; the dielectric test cell was of the type TN90, the cell thickness being 7 μm.
The components used in the examples below, except for the compound of formula I, can be synthesized by known methods or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Preparation example 1
The synthetic route for formula B is represented as follows:
the specific process comprises the following steps:
among them, compound B1 is commercially available.
(1) Synthesis of Compound B2
Adding 25.5g of 2,3, 5-trifluoro-4-bromobenzoic acid (B1), 100mL of toluene, 14.0g of 1, 3-propanedithiol and 19.5g of trifluoromethanesulfonic acid into a 250mL three-necked flask in sequence, heating and refluxing, dividing water for 3 hours, evaporating to remove about 50mL of toluene, cooling to room temperature under the protection of nitrogen, adding 100mL of dichloromethane into the reaction flask, cooling to-78 ℃, adding a mixture of 15g of triethylamine, 19g of 3,4, 5-trifluorophenol and 50mL of dichloromethane dropwise into the reaction flask, stirring for 1 hour under the protection of nitrogen, adding 24g of triethylamine composite hydrogen trifluoride solution dropwise into the reaction flask, adding 24g of bromine into the reaction flask after 5 minutes, continuously controlling the temperature to-78 ℃, stirring for 1 hour, naturally heating to-30 ℃, pouring the reaction solution into a mixture of 8g of sodium hydroxide and 300g of sodium trifluoride, post-treatment and purification by column chromatography gave a white solid, b216.5g, GC: 99.2, yield: 40.5 percent.
(2) Synthesis of Compound B4
14.2g of p-bromoiodobenzene (B3), 9.0g of 4-n-propyl-2-fluorobenzeneboronic acid, 60mL of toluene, 30mL of ethanol, 30mL of water and 11g of sodium carbonate are sequentially added into a 250mL three-necked flask, stirred for 5min, added with 0.2g of 4-triphenylphosphine palladium under the protection of nitrogen, heated and refluxed for 5 hours, subjected to aftertreatment, and purified by column chromatography to obtain a white-like solid B4, 13.1g of GC: 98.3%, yield: 89.4 percent.
(3) Synthesis of Compound B5
Adding 13.1g B4 and 100mL of anhydrous tetrahydrofuran into a 250mL three-neck flask, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 21mL of n-butyl lithium n-hexane solution (2.4 mol/L), continuously controlling the temperature to-78 ℃, stirring for 1 hour, then dropwise adding a mixture of 12g of triisobutyl borate and 40mL of anhydrous tetrahydrofuran into the reaction flask, continuously controlling the temperature to-78 ℃, stirring for 1 hour, post-treating, and evaporating the solvent to obtain an off-white solid B59.9g, HPLC: 95%, yield: 85.8 percent.
(4) Synthesis of Compound B
5.2g B5, 8.2g B2, 50mL toluene, 25mL ethanol, 25mL water and 4.3g sodium carbonate are added into a 250mL three-necked bottle in sequence, stirred for 5min, then added with 0.1g 4-triphenylphosphine palladium under the protection of nitrogen, heated and refluxed for 6 hours, and then subjected to aftertreatment and purification by column chromatography to obtain a white solid B, 8.1g, GC: 99.8%, yield: 75 percent.
In the same manner, compound D, E, F, G, H of the following formula can be prepared:
TABLE 2 liquid Crystal Properties of Compound B, D, E, F, G, H
| Compound (I) | DSC | Δε | Δn |
| B | C111.7I | 18 | 0.181 |
| C | C148.6I | 20.2 | 0.17 |
| D | C81.8N118.1I | 19.7 | 0.126 |
| E | C81.7N87.9I | 20 | 0.127 |
| F | C99N113.4I | 22 | 0.18 |
| G | C109.3N144.1I | 17.8 | 0.225 |
Compound (I)Of B1FIG. 1 shows an H-NMR chart;
of compound C1FIG. 2 shows an H-NMR chart;
of Compound D1FIG. 3 shows an H-NMR chart;
of the Compound E1The H-NMR chart is shown in FIG. 4;
of compound F1FIG. 5 shows an H-NMR chart;
of compound G1The H-NMR chart is shown in FIG. 6.
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 4 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 3, 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, 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
Example 3
The liquid crystal composition of example 3 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
Example 4
The liquid crystal composition of example 4 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
Example 5
The liquid crystal composition of example 5 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
Example 6
The liquid crystal composition of example 6 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 example 1, as can be seen from the test data of examples 1, 2,3, 4,5 and 6 above, the liquid crystal composition provided by the present invention has a smaller viscosity, a larger dielectric anisotropy, a suitably high refractive index anisotropy and a higher clearing point.
The display device has the advantages of high response speed, good display effect and low-temperature storage stability, and is suitable for AM display devices.
Claims (9)
1. A liquid crystal composition comprising, based on the total weight of the liquid crystal composition:
5-40% of one or more compounds selected from formula I
30-60% of one or more compounds selected from the group consisting of compounds of formula II
5-45% of one or more compounds selected from the group consisting of formula III-1, formula III-2, and combinations thereof
1-25% by weight of the total liquid crystal composition of a compound selected from the group consisting of compounds of formula IV-1, compounds of formula IV-2 and combinations thereof
Wherein,
R1、R2、R3、R4、R5and R6The same or different, each independently selected from the group consisting of H, alkyl or alkoxy group having 1 to 7 carbon atoms, fluoroalkyl or fluoroalkoxy group having 1 to 7 carbon atoms, alkenyl or alkenyloxy group having 2 to 7 carbon atoms, or fluoroalkenyl or fluoroalkenyloxy group having 2 to 7 carbon atoms;
R7、R8and R9The same or different, each independently selected from the group consisting of an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms, and R8And R9An alkyl group having not 3 carbon atoms; x1Selected from the group consisting of H, F, Cl, -OCF3An alkyl group or an alkoxy group having 1 to 7 carbon atoms, a fluoroalkyl group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms, a fluoroalkenyl group having 2 to 5 carbon atoms or a fluoroalkenyloxy group having 2 to 5 carbon atoms;
are the same or different and are each independently selected from the group consisting of A group of (a);
L1、L2、L3、L4、L5、L6、L7and L8The same or different, each independently represents H or F.
2. The liquid crystal composition of claim 1, wherein the compound of formula i comprises 10-35% by weight of the total liquid crystal composition; the compound of the general formula II accounts for 35-55% of the total weight of the liquid crystal composition; the compound composed of the general formula III-1, the general formula III-2 and the combination accounts for 10-40% of the total weight of the liquid crystal composition; and the compound formed by the general formula IV-1, the general formula IV-2 and the combination thereof accounts for 2-20% of the total weight of the liquid crystal composition.
3. The liquid crystal composition of claim 2, wherein the compound of formula i is selected from one or more compounds of the group consisting of:
wherein,
the R is1Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
4. The liquid crystal composition of claim 2, wherein the compound of formula ii is selected from one or more compounds of the group consisting of:
wherein,
the R is2Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
5. The liquid crystal composition of claim 2, wherein the compound of formula iii-1 is selected from one or more compounds of the group consisting of:
and is
The compound of the general formula III-2 is selected from one or more compounds of the group consisting of:
wherein,
the R is4Selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms;
said X1Selected from the group consisting of F or an alkyl or alkoxy group having 1 to 5 carbon atoms.
6. The liquid crystal composition of claim 2, wherein the compound of formula iv-1 is selected from one or more compounds of the group consisting of:
and is
The compound of the general formula IV-2 is selected from one or more compounds in the group consisting of:
wherein,
R7selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms;
R8and R9The same or different, each independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, and wherein R is8And R9Not an alkyl group having 3 carbon atoms.
7. A liquid crystal composition, comprising:
3CPPC3 compound accounting for 3 percent of the total weight of the liquid crystal composition
Compound 2CPGF accounting for 3 percent of the total weight of the liquid crystal composition
3CPGF compound accounting for 3 percent of the total weight of the liquid crystal composition
54% by weight of the total liquid crystal composition of compound 3CCV
7 percent of compound 2PGP3 in the total weight of the liquid crystal composition
Compound 3PGP4 accounting for 6 percent of the total weight of the liquid crystal composition
Compound 3PGP2 accounting for 6 percent of the total weight of the liquid crystal composition
2% by weight of compound 2PPU (F) QUF based on the total weight of said liquid crystal composition
2% by weight of the total weight of the liquid crystal composition of the compound 3PPU (F) QUF
Compound 2PGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
3PGU (F) QUF compound in an amount of 3% by weight based on the total weight of said liquid crystal composition
Compound 4PGU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
Compound 5PGU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
compound 3CPUF at 8% of the total weight of the liquid crystal composition
Compound 5CPUF in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3 CCUF accounting for 2% of the total weight of the liquid crystal composition
2% by weight of the total liquid crystal composition of compound 2 CCUF
49% by weight of compound 3CCV based on the total weight of the liquid crystal composition
Compound 2PGP3 accounting for 6 percent of the total weight of the liquid crystal composition
7% by weight of the total liquid crystal composition of compound 3PGP4
7% by weight of the total liquid crystal composition of compound 3PGP2
Compound 4PGU (F) QUF at 2% by weight of the total weight of the liquid crystal composition
3PGU (F) QUF compound in an amount of 3% by weight based on the total weight of said liquid crystal composition
Compound 2CGU (F) QUF at 2% by weight of the total weight of the liquid crystal composition
Compound 3CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 4CGU (F) QUF at 2% by weight of the total weight of the liquid crystal composition
Compound 5CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
compound 3CPUF at 8% of the total weight of the liquid crystal composition
Compound 5CPUF in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3 CCUF accounting for 4% of the total weight of the liquid crystal composition
49% by weight of compound 3CCV based on the total weight of the liquid crystal composition
7 percent of compound 2PGP3 in the total weight of the liquid crystal composition
7% by weight of the total liquid crystal composition of compound 3PGP4
7% by weight of the total liquid crystal composition of compound 3PGP2
2% by weight, based on the total weight of said liquid-crystal composition, of compound 3GPU (F) QUF
Compound 4GPU (F) QUF at 2% by weight of the total weight of the liquid-crystal composition
Compound 2CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 3CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 4CGU (F) QUF at 2% by weight of the total weight of the liquid crystal composition
Compound 5CGU (F) QUF at 2% by weight of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
3CPUF compound 3% of total weight of said liquid crystal composition
Compound 5CPUF in an amount of 2% by weight based on the total weight of the liquid crystal composition
Compound 3CPPC3 accounting for 4 percent of the total weight of the liquid crystal composition
Compound 2PGP3 in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3PGP4 in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3PGP2 in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3CCV accounting for 48 percent of the total weight of the liquid crystal composition
Compound VCCGF accounting for 4 percent of the total weight of the liquid crystal composition
2% by weight of the total liquid crystal composition of compound 2 CCPCCF 3
2% by weight of the total liquid crystal composition of compound 3 CCPCF 3
Compound 2PGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 3PGU (F) QUF in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 2CGU (F) QUF at 2% by weight of the total weight of the liquid crystal composition
Compound 3CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 4CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 2PPU (F) QUF at 4% by weight of the total weight of the liquid-crystal composition
Compound 3PPU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
3CPUF compound 3% of total weight of said liquid crystal composition
Compound 5CPUF at 3% by weight of the total liquid crystal composition
Compound 3 CCUF accounting for 2% of the total weight of the liquid crystal composition
Compound 2PGP3 in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3PGP4 in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3PGP2 in an amount of 4% by weight based on the total weight of the liquid crystal composition
46 percent of compound 3CCV based on the total weight of the liquid crystal composition
Compound VCCGF accounting for 4 percent of the total weight of the liquid crystal composition
3% by weight of the total liquid crystal composition of compound 2 CCPCCF 3
3% by weight of the total liquid crystal composition of compound 3 CCPCF 3
Compound 2CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 3CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 4CGU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
Compound 3PPU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
Compound 4PPU (F) QUF at 5% by weight of the total weight of the liquid crystal composition
5PPU (F) QUF compound in an amount of 5% by weight of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
compound 5CPUF in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound 3 CCUF accounting for 2% of the total weight of the liquid crystal composition
Compound 4 CCPF 2% by weight of the total liquid crystal composition
Compound 2PGP3 accounting for 5 percent of the total weight of the liquid crystal composition
Compound 3PGP4 accounting for 5 percent of the total weight of the liquid crystal composition
Compound 3PGP2 accounting for 5 percent of the total weight of the liquid crystal composition
46 percent of compound 3CCV based on the total weight of the liquid crystal composition
3% by weight of the total liquid crystal composition of compound 2 CCPCCF 3
3% by weight of the total liquid crystal composition of compound 3 CCPCF 3
Compound 2PGU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
Compound 3PGU (F) QUF at 5% by weight of the total weight of the liquid crystal composition
Compound 4PGU (F) QUF at 5% by weight of the total weight of the liquid crystal composition
Compound 2CGU (F) QUF at 3% by weight of the total weight of the liquid crystal composition
Compound 3CGU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
Compound 4CGU (F) QUF at 4% by weight of the total weight of the liquid crystal composition
8. A liquid crystal display device comprising the liquid crystal composition of any one of claims 1 to 7.
9. An active matrix liquid crystal display device comprising the liquid crystal composition of any one of claims 1 to 7.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310339363.3A CN104342168B (en) | 2013-08-06 | 2013-08-06 | There is liquid-crystal composition and the liquid crystal display device of good low temperature storage stability |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310339363.3A CN104342168B (en) | 2013-08-06 | 2013-08-06 | There is liquid-crystal composition and the liquid crystal display device of good low temperature storage stability |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104342168A CN104342168A (en) | 2015-02-11 |
| CN104342168B true CN104342168B (en) | 2016-08-10 |
Family
ID=52498639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310339363.3A Active CN104342168B (en) | 2013-08-06 | 2013-08-06 | There is liquid-crystal composition and the liquid crystal display device of good low temperature storage stability |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104342168B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107723000B (en) * | 2017-09-28 | 2021-03-16 | 江苏和成显示科技有限公司 | Liquid crystal composition and application thereof |
| CN107955631B (en) * | 2017-11-22 | 2019-11-29 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
| CN108659851A (en) * | 2018-06-22 | 2018-10-16 | 烟台显华化工科技有限公司 | A kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond |
| CN108690639A (en) * | 2018-06-22 | 2018-10-23 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200902687A (en) * | 2007-02-02 | 2009-01-16 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN102076821A (en) * | 2008-06-27 | 2011-05-25 | 默克专利股份有限公司 | Liquid-crystalline medium |
| CN103242860A (en) * | 2013-05-15 | 2013-08-14 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101031631B (en) * | 2004-10-04 | 2013-02-13 | Jnc株式会社 | Liquid crystal composition and liquid crystal display element |
| JP5359478B2 (en) * | 2008-04-11 | 2013-12-04 | Ｊｎｃ株式会社 | Liquid crystal composition and liquid crystal display element |
-
2013
- 2013-08-06 CN CN201310339363.3A patent/CN104342168B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200902687A (en) * | 2007-02-02 | 2009-01-16 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN102076821A (en) * | 2008-06-27 | 2011-05-25 | 默克专利股份有限公司 | Liquid-crystalline medium |
| CN103242860A (en) * | 2013-05-15 | 2013-08-14 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104342168A (en) | 2015-02-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103242860B (en) | Liquid crystal composition and liquid crystal display device | |
| KR102080953B1 (en) | Liquid Crystal Compound And Liquid Crystal Mixture Containing Cyclopropyl | |
| CN108865175B (en) | Liquid crystal composition containing dibenzofuran and application thereof | |
| CN109796991B (en) | Liquid crystal compound containing lateral trifluoromethyl, liquid crystal mixture and display device thereof | |
| WO2022073400A1 (en) | Liquid crystal compound having negative dielectric anisotropy, liquid crystal composition, and liquid crystal display device | |
| KR102190145B1 (en) | Liquid crystal composition and liquid crystal display | |
| CN108203583B (en) | Liquid crystal compound with negative dielectric anisotropy and application thereof | |
| CN108203584B (en) | Compound, liquid crystal composition and application thereof | |
| KR20140043838A (en) | Liquid crystal composition and liquid crystal display device comprising the liquid crystal composition | |
| CN106318403B (en) | Liquid-crystal compounds and its synthetic method with negative dielectric anisotropic and application | |
| CN104371743B (en) | Liquid crystal composition and liquid crystal display device | |
| CN103242856B (en) | Liquid crystal composition and liquid crystal display device | |
| CN109880635B (en) | Liquid crystal compound containing dibenzofuran-oxygen-containing heterocyclic ring, composition and application | |
| CN102492430A (en) | Liquid crystal composition and liquid crystal display element containing the same | |
| CN104342168B (en) | There is liquid-crystal composition and the liquid crystal display device of good low temperature storage stability | |
| CN104371746B (en) | Liquid-crystal composition and liquid crystal display device | |
| CN109207163A (en) | A kind of liquid-crystal composition and its application | |
| CN103242862B (en) | Liquid crystal composition with low-temperature storage stability and liquid crystal display device | |
| CN102994100B (en) | Liquid crystal composition and liquid crystal display device containing liquid crystal composition | |
| CN104629773A (en) | Liquid crystal composition and display device thereof | |
| CN105586050B (en) | Liquid-crystal composition and liquid crystal display device | |
| CN103351876B (en) | Liquid crystal composition and liquid crystal display device thereof | |
| CN106635051B (en) | Liquid-crystal compounds with negative dielectric anisotropic and its application | |
| CN105505404B (en) | Liquid-crystal composition and its display device | |
| CN104610980B (en) | Liquid-crystal composition and its display device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Patentee before: Jiangsu Hecheng Display Technology Co.,Ltd. |
|
| CP02 | Change in the address of a patent holder | ||
| CP02 | Change in the address of a patent holder |
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. |