CN105131973B - A kind of liquid-crystal compounds contained to Trifluoromethoxyphen-l, composition and its preparation method and application - Google Patents
A kind of liquid-crystal compounds contained to Trifluoromethoxyphen-l, composition and its preparation method and application Download PDFInfo
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- CN105131973B CN105131973B CN201510438631.6A CN201510438631A CN105131973B CN 105131973 B CN105131973 B CN 105131973B CN 201510438631 A CN201510438631 A CN 201510438631A CN 105131973 B CN105131973 B CN 105131973B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 130
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims description 8
- -1 p-trifluoromethoxyphenyl Chemical group 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 0 CCCc1ccc-2c3c1cccc3C(C)(CC1OC1)c1cc(-c3ccc(*)cc3)ccc-21 Chemical compound CCCc1ccc-2c3c1cccc3C(C)(CC1OC1)c1cc(-c3ccc(*)cc3)ccc-21 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 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 description 2
- NHNOUJCAHMXIGR-UHFFFAOYSA-N 7h-benzo[a]phenalene Chemical compound C1=CC(CC=2C3=CC=CC=2)=C2C3=CC=CC2=C1 NHNOUJCAHMXIGR-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of liquid-crystal compounds contained to Trifluoromethoxyphen-l.The structural formula of the liquid-crystal compounds is
Description
Technical Field
The invention relates to a liquid crystal compound containing p-trifluoromethoxyphenyl, a composition containing the liquid crystal compound, and a preparation method and application of the liquid crystal compound.
Background
Liquid crystal displays are now widely used in various aspects of social life, and liquid crystal display technologies have been developed so far, and various liquid crystal compounds have been practically used. Some common requirements for liquid crystal compounds, including phase transition temperature, optical anisotropy, dielectric anisotropy, viscosity, resistivity, etc., of the liquid crystal compounds, have a great influence on the final application of the liquid crystal material. The development of new liquid crystal compounds and compositions comprising the same are extremely important for improving various properties of liquid crystals and improving the application effects of liquid crystal displays.
Disclosure of Invention
The invention provides a novel liquid crystal compound which has liquid crystal characteristics and can be used in a liquid crystal composition for a liquid crystal display. The compound has a high clearing point.
The structural formula of the liquid crystal compound provided by the invention is shown as a formula I:
the invention also provides a method for preparing the liquid crystal compound, which comprises the following steps:
step a) reacting the compound shown in the formula I-1 with N-bromosuccinimide in tetrahydrofuran to obtain a compound shown in the formula I-2,
step b) reacting the compound shown in the formula I-2 with propyl magnesium bromide under the catalysis of tetrakis (triphenylphosphine) palladium to obtain a compound shown in the formula I-3,
step c) reacting the compound represented by the formula I-3 with bromine in dichloromethane to obtain a compound represented by the formula I-4,
step d) reacting the compound shown as the formula I-4 with tetrakis (triphenylphosphine) palladium under the action of potassium carbonate
The compound shown in the formula I is obtained through reaction,
preferably, the reaction of step d) is carried out in a mixed solvent of toluene, ethanol and water.
The invention also provides a composition containing the liquid crystal compound.
In one embodiment of the invention, the composition of the invention comprises a compound of formula I, a compound of formula II, a compound of formula III, a compound of formula IV, a compound of formula V, a compound of formula VI, a compound of formula VII, and a compound of formula VIII; wherein,
formula II:
formula III:
formula IV:
formula V:
formula VI:
formula VII:
formula VIII:
wherein the weight percentage of each component is as follows:
5-10% of a compound shown as a formula I;
4-8% of a compound shown in a formula II;
7-20% of a compound shown in formula III;
7-30% of a compound shown as a formula IV;
8-15% of a compound shown as a formula V;
3-6% of a compound shown as a formula VI;
8-60% of a compound represented by the formula VII and
5-10% of a compound represented by formula VIII.
In one technical scheme of the invention, the composition comprises the following components in percentage by weight:
6-8% of a compound shown as a formula I;
4-8% of a compound shown in a formula II;
10-16% of a compound shown in a formula III;
10-25% of a compound shown as a formula IV;
8-15% of a compound shown as a formula V;
4-5% of a compound shown as a formula VI;
30-60% of a compound represented by the formula VII
6-8% of a compound represented by formula VIII.
Preferably, the weight percentage of each component is as follows:
7% of a compound of formula I;
6% of a compound represented by formula II;
14% of a compound represented by formula III;
15% of a compound of formula IV;
10% of a compound represented by formula V;
5% of a compound represented by formula VI;
36% of a compound of the formula VII and
a compound of formula VIII 7%.
The application of the liquid crystal compound or the composition in the preparation of a liquid crystal display device also belongs to the protection scope of the invention.
Based on the technical scheme, the liquid crystal compound is a novel 7-hydrogen benzo [ de ] anthracene liquid crystal compound, and has a high clearing point. The liquid crystal composition containing the compound provided by the invention has a wider nematic phase range, and the application field is greatly widened.
Drawings
FIG. 1 is a 1H-NMR spectrum of a liquid crystal compound of the present invention of formula I.
FIG. 2 is a 1H-NMR spectrum of a liquid crystal compound represented by the formula VIII according to the present invention.
Detailed Description
The preferred embodiments of the present invention will be described in conjunction with the accompanying drawings, and it will be understood that they are described herein for the purpose of illustration and explanation and not limitation.
Based on the invention, the liquid crystal compound is provided, and the structural formula of the liquid crystal compound is shown as the formula I:
the synthetic route for the compounds of formula I is as follows:
the invention also provides a composition containing the liquid crystal compound.
In one embodiment of the invention, the composition of the invention comprises a compound of formula I, a compound of formula II, a compound of formula III, a compound of formula IV, a compound of formula V, a compound of formula VI, a compound of formula VII, and a compound of formula VIII; wherein,
formula II:
formula III:
formula IV:
formula V:
formula VI:
formula VII:
formula VIII:
examples
In the liquid crystal compositions referred to in the following examples, the starting materials or components of the present invention are commercially available unless otherwise specified.
Example 1 preparation of liquid Crystal Compound of formula I
Step a. in a 250mL three-necked flask, 2.5 g of a compound of formula I-1 (7, 7-dimethyl-7H-benzo [ de ] anthracene, prepared according to patent WO 2011/115378) was dissolved in 50mL of tetrahydrofuran, 1.8 g of N-bromosuccinimide was added with stirring, the temperature was raised to 35 ℃ to react for 1 hour, then 80 mL of water was added to precipitate a yellow solid, which was filtered and dried to give 3.15 g of a compound of formula I-2, yield 93.6%, product mass spectrum (m/e):322,
the reaction formula is as follows:
step b. in a 250mL three-necked flask, 2.9 g of the compound having the formula I-2 obtained in step a was dissolved in 50mL of toluene, and then a catalytic amount (about 0.1g) of tetrakis (triphenylphosphine) palladium catalyst was added, and 27 g of a 15 wt% solution of propylmagnesium bromide in tetrahydrofuran was added dropwise at 30 ℃ with stirring, followed by incubation for 3 hours, addition of water, liquid separation, washing of the organic layer with water, drying with magnesium sulfate, silica gel column chromatography, petroleum ether: dichloromethane 10: 1 to give 2.28 g of the compound of formula I-3 in 88.7% yield, 286 by mass spectrometry (m/e) of the product, wherein the reaction is as follows:
step c, dissolving 2.08 g of the compound having the formula I-3 obtained in step b in 50mL of dichloromethane in a 250mL three-necked flask, controlling the system temperature to be kept at 25 ℃, dropwise adding 5 mL of a dichloromethane solution of bromine (1.6g), keeping the temperature at 25 ℃ after the addition is finished, reacting for 2 hours, adding water, separating, sequentially washing an organic layer with a sodium bisulfite aqueous solution, water, drying magnesium sulfate, performing silica gel column chromatography, and performing petroleum ether: dichloromethane 10: 1 to give 2.55 g of compound of formula I-4 in 96.1% yield, 364, product Mass Spectrum (m/e) to give the compound of formula I-4, which is represented by the following reaction scheme:
step d.in a 500 ml three-necked flask, 100 ml of toluene, 100 ml of ethanol and 60 ml of water are added under nitrogen protection, 3.6 g of the compound represented by the formula I-4 obtained in step c are added, and then 2.1 g of the compound is added3.8 g of potassium carbonate and 0.5 g of tetrakis (triphenylphosphine) palladium, heating, refluxing, reacting for 4 hours, cooling, washing, separating liquid, drying an organic layer with magnesium sulfate, performing silica gel column chromatography, and performing petroleum ether: dichloromethane ═ 2: 1 to give 3.35 g of compound of formula-I in 76.1% yield, product mass spectrum: (m/e): 446, the product hydrogen nuclear magnetic spectrum is shown in FIG. 1, and the reaction formula is as follows:
the clearing point of the compound shown in the formula I is 138 ℃ through detection, and the compound has good physical and chemical stability.
Example 2 preparation of liquid Crystal Compound of formula VIII
In a 500 ml three-necked flask, 100 ml of toluene, 100 ml of ethanol and 60 ml of water are added under nitrogen protection, 2.4 g of the compound represented by the formula I-4 are added, and then 1.6g of the compound is added2.5 g of potassium carbonate and 0.3 g of tetrakis (triphenylphosphine) palladium, heating, refluxing, reacting for 4 hours, cooling, washing, separating liquid, drying an organic layer with magnesium sulfate, performing silica gel column chromatography, and performing petroleum ether: dichloromethane ═ 2: 1 to obtain 2.48 g of the compound of the formula VIII with the yield of 80%; product mass spectrum: (m/e): 472, the nuclear magnetic spectrum of the product hydrogen is shown in figure 2, and the reaction formula is as follows:
the clearing point of the compound shown in the formula VIII is 151 ℃ through detection, and the compound has good physical and chemical stability.
Example 3 preparation of liquid Crystal composition and verification of Effect thereof
The liquid crystal composition of this example contains the compound shown in formula I, the specific components and the ratio are shown in tables 1 to 4, and the liquid crystal composition having the formula shown in table 1 is prepared by mixing these components uniformly. And carrying out performance test, wherein the abbreviations of the performance test parameters are as follows:
Δ n is optical anisotropy;
V10the threshold voltage is a characteristic voltage (V,20 ℃) when the transmittance is changed by 10%, and the liquid crystal comprehensive parameter tester EOT-5016. A polarizing plate having a polarization axis orthogonal to the polarization axis was set, and the polarizing plate was attached to the upper and lower surfaces of a cell (4.0 μm) filled with liquid crystal. The liquid crystal cell is applied with a voltage, and the voltage when the light is reduced from the initial state of full transmittance to 10% transmittance is a saturation voltage. The light source was halogen light and the cells were driven with a 64HZ square wave.
Cp is the clearing point (. degree. C.) of the liquid crystal composition;
table 1:
table 2:
table 3:
table 4:
finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. A liquid crystal compound containing p-trifluoromethoxyphenyl has a structural formula shown in formula I:
(formula I).
2. A composition comprising the liquid crystal compound according to claim 1.
3. The composition of claim 2, wherein: comprises a compound shown as a formula I, a compound shown as a formula II, a compound shown as a formula III, a compound shown as a formula IV, a compound shown as a formula V, a compound shown as a formula VI, a compound shown as a formula VII and a compound shown as a formula VIII; wherein,
formula II:
formula III:
formula IV:
formula V:
formula VI:
formula VII:
formula VIII:。
4. the composition of claim 3, wherein: the weight percentage of each component is as follows:
5-10% of a compound shown as a formula I;
4-8% of a compound shown in a formula II;
7-20% of a compound shown in formula III;
7-30% of a compound shown as a formula IV;
8-15% of a compound shown as a formula V;
3-6% of a compound shown as a formula VI;
8-60% of a compound represented by the formula VII and
5-10% of a compound represented by formula VIII.
5. The composition of claim 4, wherein: the weight percentage of each component is as follows:
6-8% of a compound shown as a formula I;
4-8% of a compound shown in a formula II;
10-16% of a compound shown in a formula III;
10-25% of a compound shown as a formula IV;
8-15% of a compound shown as a formula V;
4-5% of a compound shown as a formula VI;
30-60% of a compound represented by the formula VII
6-8% of a compound represented by formula VIII.
6. The composition of claim 5, wherein: the weight percentage of each component is as follows:
7% of a compound of formula I;
6% of a compound represented by formula II;
14% of a compound represented by formula III;
15% of a compound of formula IV;
10% of a compound represented by formula V;
5% of a compound represented by formula VI;
36% of a compound of the formula VII and
a compound of formula VIII 7%.
7. Use of the liquid crystal compound of claim 1 or the composition of any one of claims 2 to 6 for the preparation of a liquid crystal display device.
8. A liquid crystal display device comprising the liquid crystal compound according to claim 1 or the composition according to any one of claims 2 to 6.
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| KR20080039763A (en) * | 2006-11-01 | 2008-05-07 | 삼성전자주식회사 | Organic light emitting compound and organic light emitting device comprising the same |
| CN103992801B (en) * | 2014-05-23 | 2015-07-08 | 京东方科技集团股份有限公司 | 7-hydrobenzo (de) anthracene liquid crystal compound and liquid crystal composition thereof |
| CN104017586B (en) * | 2014-05-29 | 2015-07-15 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| CN104017585B (en) * | 2014-05-29 | 2015-07-15 | 京东方科技集团股份有限公司 | Liquid crystal compound, liquid crystal composition, preparation methods thereof and liquid crystal display panel |
| CN104045504B (en) * | 2014-05-30 | 2015-07-08 | 京东方科技集团股份有限公司 | Compound, preparation method of compound, liquid crystal composition and preparation method of composition |
| CN104496742B (en) * | 2014-12-30 | 2016-03-30 | 京东方科技集团股份有限公司 | A kind of liquid crystalline cpd, composition and application thereof |
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