CN102660295A - Fluorine-containing azacyclic liquid crystal compound, synthetic method thereof and application thereof - Google Patents
Fluorine-containing azacyclic liquid crystal compound, synthetic method thereof and application thereof Download PDFInfo
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Abstract
The invention discloses a fluorine-containing azacyclic liquid crystal compound. The compound has a structure represented by formula I. A method for preparing the compound comprises the following steps: 1, mixing 2,2,3,3-tetrafluoro-1,4-butylene glycol with pyridine, adding trifluoromethanesulfonic anhydride, and reacting to obtain 2,2,3,3-tetrafluoro-1,4-butylene trifluoromethanesulfonate; 2, reacting a compound with the structure represented by formula V with 2,2,3,3-tetrafluoro-1,4-butylene trifluoromethanesulfonate to obtain a compound with the structure represented by formula III; 3, reacting the compound with the structure represented by the formula III with sodium t-butoxide to obtain a compound with the structure represented by formula IV; and 4, reacting a compound with the structure represented by formula II with the compound with the structure represented by the formula IV to obtain the fluorine-containing azacyclic liquid crystal compound with the structure represented by the formula I. The synthetic method of the fluorine-containing azacyclic liquid crystal compound of the invention has the advantages of simplicity, easy implementation, and high yield; the obtained fluorine-containing azacyclic liquid crystal compound has a wide mesomorphic phase temperature and a low melting point; and the mesomorphic phase transition temperature can be adjusted through adjusting the alkyl chain length and the fluorine content.
Description
Technical field
The invention belongs to the liquid crystal material field, be specifically related to a kind of fluorine-containing nitrogen heterocyclic liquid crystalline cpd compound method and application.
Background technology
In recent decades, the fast development in liquid crystal material field has brought the great change of liquid-crystal display industry, and liquid-crystal display because its light weight, volume and power consumption are little, becomes one of leading product of modern displays as important information electronic product.And fluoro liquid crystals has that viscosity is low, resistivity is high, response speed is very fast, specific inductivity is than advantages such as height, is fit to very much the liquid-crystal display that TFT drives.The fluorine liquid crystalline cpd can reduce fusing point, suppresses or the elimination smectic phase, can widen nematic temperature range, increases specific inductivity.Fluorinated liquid crystal has high voltage retention, and not with temperature variation, is the liquid crystal material that is applicable to the TFT mode.
Liquid-crystal display requirement driving voltage is low, energy input is little, thus need to use the liquid crystal material of low threshold voltage, and such liquid crystal material necessarily requires high dielectric anisotropy.In recent years; People pass through molecule design method; In liquid crystal molecule, introduce the dielectric anisotropy that a plurality of polarity fluorine atoms improve molecule; The liquid crystal monomer of the high dielectric anisotropy of institute's synthetic mainly can be divided into to phenyl ring side direction, end and bridge chain introduces fluorine atom, through increasing molecular polarity, thereby effectively increases the dielectric anisotropy of molecule.
Liquid crystal is widely used in liquid-crystal display from being found to, and has experienced the course in more than 100 year.Liquid crystal material plays crucial effect in the evolution of liquid crystal display device, along with the raising of lcd technology level, to the demands for higher performance of liquid crystal material.Fluorinated liquid crystal is low with its good properties such as viscosity, response speed is fast, proper dielectric constant etc., occupies the critical role of liquid crystal display material, has vast potential for future development.
Summary of the invention
For the shortcoming and deficiency that overcome prior art, primary and foremost purpose of the present invention is to provide a kind of fluorine-containing nitrogen heterocyclic liquid crystalline cpd.
Another object of the present invention is to provide the preparation method of above-mentioned fluorine-containing nitrogen heterocyclic liquid crystalline cpd.
A purpose more of the present invention is to provide the purposes of above-mentioned fluorine-containing nitrogen heterocyclic liquid crystalline cpd.
The object of the invention is realized through following technical proposals:
A kind of fluorine-containing nitrogen heterocyclic liquid crystalline cpd has suc as formula the structure shown in the I:
Wherein, n is the natural number between the 0-10, and m is 1 or 2, R
1Be H, Cl, F, Br or CN, R
2Be H, Cl, F, Br or CN, X does
Preferably, n is 3 or 5, R
1=R
2=H.
The compound method of above-mentioned fluorine-containing nitrogen heterocyclic liquid crystalline cpd may further comprise the steps:
(1) get 2,2,3,3-tetrafluoro-1,4-butyleneglycol and pyridine are with mol ratio 1: (1.5-2.5) mix, add CH
2Cl
2And stir, adding trifluoromethanesulfanhydride anhydride again, stirring reaction 10 hours obtains product trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester after reaction finishes; Following reaction takes place in this process:
(2) compound shown in the modus ponens V and trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester mixes with mol ratio at 1: 1, adds dissolve with ethanol, and oil bath reflux 12 hours obtains the compound shown in the formula III after reaction finishes; Following reaction takes place in this process:
(3) compound shown in the modus ponens III and sodium tert-butoxide are with mol ratio 1: (4-8) mix, add DMSO 99.8MIN. as solvent, 60-100 ℃ of reaction 12 hours down obtains the compound shown in the formula IV after reaction finishes; Following reaction takes place in this process:
(4) compound shown in the formula II is mixed with mol ratio with the compound shown in formula III or the formula IV at 1: 1; Add N again; N '-NSC 57182 (DCC) and 4-Dimethylamino pyridine (DMAP); As solvent, reflux 12 hours obtains suc as formula the fluorine-containing nitrogen heterocyclic liquid crystalline cpd shown in the I after reaction finishes with trichloromethane; Following reaction takes place in this process:
Among the described formula II, n is the natural number between the 0-10, and n preferred 3 or 5; M is 1 or 2.
Among described formula III-V, R
1Be H, Cl, F, Br or CN, R
2Be H, Cl, F, Br or CN, X does
Preferably, R
1=R
2=H.
The described trifluoromethanesulfanhydride anhydride of step (1) and 2,2,3,3-tetrafluoro-1, the mol ratio of 4-butyleneglycol is 2: 1;
After the said reaction of step (1) finishes,, remove CH with organic layer washing, drying
2Cl
2, obtain the product trifluoromethanesulfonic acid 2,2,3 of white powder, 3-tetrafluoro-1,4-fourth diester solid; Described is water, saturated common salt water washing successively with the organic layer washing; Described drying is to use anhydrous Na
2SO
4Dry;
After the said reaction of step (2) finishes, remove ethanol, add CH
2Cl
2, the washing organic layer, drying obtains the compound shown in the formula III with petrol ether/ethyl acetate mixed solvent column chromatography at last; Described washing organic layer is water, saturated common salt water washing successively; Described drying is to use anhydrous MgSO
4Dry; In the described petrol ether/ethyl acetate mixed solvent, the volume ratio of sherwood oil and ETHYLE ACETATE is 20: 1;
After the said reaction of step (3) finishes, add CH
2Cl
2, the washing organic layer, drying obtains the compound shown in the formula IV with petrol ether/ethyl acetate mixed solvent column chromatography then; Described washing organic layer is water, saturated common salt water washing successively; Described drying is to use anhydrous MgSO
4Dry; In the described petrol ether/ethyl acetate mixed solvent, the volume ratio of sherwood oil and ETHYLE ACETATE is 30: 1;
The mol ratio of compound shown in the said formula II of step (4) and DCC, DMAP is 1: 1: 0.05;
After the said reaction of step (4) finishes, obtain fluorine-containing nitrogen heterocyclic liquid crystalline cpd with sherwood oil/trichloromethane mixed solvent column chromatography; Described N, N '-NSC 57182 (DCC) is as dewatering agent; Described 4-Dimethylamino pyridine (DMAP) is as catalyzer; In described sherwood oil/trichloromethane mixed solvent, the volume ratio of sherwood oil and trichloromethane is 5: (2-3).
Above-mentioned fluorine-containing nitrogen heterocyclic liquid crystalline cpd can be used as liquid crystal display material.
The present invention has following advantage and effect with respect to prior art:
1, the compound method of fluorine-containing nitrogen heterocyclic liquid crystalline cpd of the present invention is simple, and yield is high.
2, fluorine-containing nitrogen heterocyclic liquid crystalline cpd of the present invention has wide mesomorphous phase temperature, and lower fusing point is arranged.
3, fluorine-containing nitrogen heterocyclic liquid crystalline cpd of the present invention can be regulated the mesomorphous phase transition temperature through length and the fluorine content of regulating alkyl chain.
Description of drawings
Fig. 1 is that the poor formula scanning calorimeter of the embodiment of the invention 1 product 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1-hydrogen-2,3-difluoro pyrroles) phenyl ester is analyzed collection of illustrative plates (DSC collection of illustrative plates).
Fig. 2 is the polarizing microscope collection of illustrative plates (POM collection of illustrative plates) of the embodiment of the invention 1 product 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1-hydrogen-2,3-difluoro pyrroles) phenyl ester; Wherein, a is this compound at 164 ℃ POM collection of illustrative plates, and b is this compound at 265 ℃ POM collection of illustrative plates, and c is this compound at 280 ℃ POM collection of illustrative plates.
Embodiment
Below in conjunction with embodiment and accompanying drawing the present invention is described in further detail, but embodiment of the present invention is not limited thereto.
Embodiment 1
Synthesizing of 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1-H-2,3-difluoro pyrroles) phenyl ester, may further comprise the steps:
(1) trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester synthetic
With 2,2,3,3-tetrafluoro-1, the 4-butyleneglycol (3.24g, 20mmol) and pyridine (3.96g 50mmol) places round-bottomed flask, adds 100ml CH
2Cl
2And after stirring 10 minutes, add then trifluoromethanesulfanhydride anhydride (11g, 40mmol).Add the back and stirred 10 hours, water, saturated common salt water washing organic layer successively then, anhydrous Na
2SO
4Drying is removed CH
2Cl
2, obtain white powder trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester, productive rate 90%.
(2) 4-(3,3,4,4-tetrafluoro tetramethyleneimine) phenol is synthetic
Get PARA AMINOPHENOL (0.55g 5mmol) in round-bottomed flask, adds trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1, (2.13g 5mmol), adds dissolve with ethanol to 4-fourth diester, loads onto reflux condensing tube reflux 12 hours in oil bath.Remove ethanol after reaction finishes, add CH
2Cl
2, water, saturated common salt water washing organic layer successively then, anhydrous MgSO
4Drying, (V: V=20: 1) the mixed solvent column chromatography obtains lurid product 4-(3,3,4,4-tetrafluoro tetramethyleneimine) phenol, productive rate 72% to use petrol ether/ethyl acetate at last.
Structural characterization data to product are:
1H NMR (CDCl
3) δ (ppm): 6.81 (d, J=8.6Hz, 2H), 6.44 (d, J=8.8Hz, 2H), 3.74 (t, J=10.4Hz, 4H).
19F NMR (CDCl
3) δ: (ppm) :-121.90-121.97 (m, 4F) .MS (ESI) m/z:234.91 (M
+) .Anal.Calcd (%) for:C10H9F4NO (235.18): C, 51.07; H, 3.86; N, 5.96.Found:C, 51.06; H, 3.83; N, 5.97. infer that in view of the above the structure of product is following, are 4-(3,3,4,4-tetrafluoro tetramethyleneimine) phenol.
(3) 4-(1H-3,4-difluoro pyrroles) phenol is synthetic
(0.47g, 2mmol) in round-bottomed flask, (0.64g 16mmol), makes solvent with DMSO 99.8MIN., and 100 ℃ were reacted 12 hours down to add sodium tert-butoxide to get 4-(2,2,3,3-tetrafluoro tetramethyleneimine) phenol.After finishing, reaction adds CH
2Cl
2, water, saturated common salt water washing organic layer successively then, anhydrous MgSO
4Drying, (V: V=30: 1) the mixed solvent column chromatography obtains lurid product 4-(1H-3,4-difluoro pyrroles) phenol, productive rate 85% to use petrol ether/ethyl acetate at last.
Structural characterization data to product are:
1H NMR (CDCl
3) δ (ppm): 7.14 (d, J=8.7Hz, 2H), 6.87 (d, J=8.7Hz, 2H), 6.61 (s, 2H), 4.89 (s, 1H).
19F NMR (CDCl
3) δ (ppm) :-178.29 (s, 2F) .MS (ESI) m/z:194.27 (M
++ 1) .Anal.Calcd (%) for:C10H7F2NO (195.17): C, 61.54; H, 3.62; N, 7.18.Found:C, 61.55; H, 3.64; N, 7.16. infer that in view of the above the structure of product is following, are 4-(1H-3,4-difluoro pyrroles) phenol.
(4) fluorine-containing nitrogen heterocyclic liquid crystalline cpd 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester is synthetic
(structure is
(0.25g in round-bottomed flask, to add 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid; 1mmol) and 4-(1H-3,4-difluoro pyrroles) phenol (0.2g, 1mmol); N; N '-NSC 57182 (DCC) (0.21g, 1mmol) and 4-Dimethylamino pyridine (DMAP) (0.006g, 0.05mmol); With trichloromethane as solvent, reflux 12 hours.After reaction finished, (V: V=5: 2) the mixed solvent column chromatography obtained fluorine-containing nitrogen heterocyclic liquid crystalline cpd 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester, productive rate 83% with sherwood oil/trichloromethane.
Structural characterization data to product are:
1H NMR (CDCl
3) δ (ppm): 7.24 (d, J=8.7Hz, 2H), 7.10 (d, J=8.7Hz, 2H), 6.68 (s, 2H), 2.49-1.28 (m, 27H).
19F NMR (CDCl
3) δ (ppm) :-177.34 (s, 2F) .MS (ESI) m/z:452.10 (M
++ 23) .Anal.Calcd (%) for:C26H33F2NO2 (429.54): C, 72.70; H, 7.74; N, 3.26.Found:C, 72.34; H, 7.73; N, 3.29. infer that in view of the above the structure of product is following, are 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester.
Embodiment 2
Synthesizing of 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(3,3,4,4-tetrafluoro pyrroles) phenyl ester, may further comprise the steps:
(1) trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester synthetic
With embodiment 1 step (1);
(2) 4-(3,3,4,4-tetrafluoro pyrroles) phenol is synthetic
With embodiment 1 step (2);
(3) fluorine-containing nitrogen heterocyclic liquid crystalline cpd 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(3,3,4,4-tetrafluoro pyrroles) phenyl ester is synthetic
In round-bottomed flask, add 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid
(0.25g, 1mmol) and 4-(3,3; 4,4-tetrafluoro pyrroles) phenol (0.24g, 1mmol); N; N '-NSC 57182 (DCC) (0.21g, 1mmol) and 4-Dimethylamino pyridine (DMAP) (0.006g, 0.05mmol); With trichloromethane as solvent, reflux 12 hours.After reaction finished, (V: V=5: 3) the mixed solvent column chromatography obtained fluorine-containing nitrogen heterocyclic liquid crystalline cpd 4-(anti--4 '-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(3,3,4,4-tetrafluoro pyrroles) phenyl ester, productive rate 85% with sherwood oil/trichloromethane.
Structural characterization data to product are:
1H NMR (CDCl
3) δ (ppm): 6.99 (d, J=8.7Hz, 2H), 6.51 (d, J=8.8Hz, 2H), 3.86-3.75 (m, 4H), 2.46-0.85 (m, 27H).
19F NMR (CDCl
3) δ (ppm) :-122.65-122.72 (m, 4F) .MS (ESI) m/z:469.50 (M
+) .Anal.Calcd (%) for:C26H35F4NO2 (469.56): C, 66.51; H, 7.51; N, 2.98.Found:C, 66.47; H, 7.46; N, 3.00. infer that in view of the above the structure of product is following, are 4-(anti--4 '-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(3,3,4,4-tetrafluoro pyrroles) phenyl ester.
Embodiment 3
Instead-and 4-n-propyl hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester synthetic, may further comprise the steps:
(1) trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester synthetic
With embodiment 1 step (1);
(2) 4-(3,3,4,4-tetrafluoro pyrroles) phenol is synthetic
With embodiment 1 step (2);
(3) 4-(1H-3,4-difluoro pyrroles) phenol is synthetic
With embodiment 1 step (3);
(4) fluorine-containing nitrogen heterocyclic liquid crystalline cpd anti--4-n-propyl hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester synthetic
In round-bottomed flask, add anti--4-n-propyl hexahydrobenzoic acid
(0.17g; 1mmol) and 4-(1H-3,4-difluoro pyrroles) phenol (0.24g, 1mmol); N; N '-NSC 57182 (DCC) (0.21g, 1mmol) and 4-Dimethylamino pyridine (DMAP) (0.006g, 0.05mmol); With trichloromethane as solvent, reflux 12 hours.After reaction finishes, with sherwood oil/trichloromethane (V: V=5: 2) the mixed solvent column chromatography obtain fluorine-containing nitrogen heterocyclic liquid crystalline cpd instead-4-n-propyl hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester, productive rate 86%.
Structural characterization data to product are:
1H NMR (CDCl
3) δ (ppm): 7.24 (d, J=8.7Hz, 2H), 7.11 (d, J=8.8Hz, 2H), 6.68 (s, 2H), 2.48-0.90 (m, 17H).
19F NMR (CDCl
3) δ (ppm) :-177.34 (s, 2F) .MS (ESI) m/z:347.85 (M
+) .Anal.Calcd (%) for:C20H23F2NO2 (347.4): C, 69.15; H, 6.67; N, 4.03.Found:C, 69.12; H, 6.65; N, 4.04. infer that in view of the above the structure of product is following, for instead-4-n-propyl hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester.
Embodiment 4
Product 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester of embodiment 1 is tested its phase transition temperature with differential scanning calorimetric analysis appearance (DSC).
The result is as shown in Figure 1, and the temperature that is changed into mesomorphic phase by crystallization phases is 157.5 ℃, is 290.5 ℃ by liquid crystal phase transition for each temperature to phasic property liquid.
Embodiment 5
Product 4-(anti--4-n-propyl cyclohexyl) hexahydrobenzoic acid 4 '-(1H-3,4-difluoro pyrroles) phenyl ester of embodiment 1 is carried out the polarizing microscope sign.
The result is as shown in Figure 2, figure a, and b, c are respectively 164 ℃, 265 ℃, the polarizing microscope collection of illustrative plates under 280 ℃, collection of illustrative plates demonstrates the typical schlieren texture that nematic liquid crystal has.
The result of comprehensive embodiment 4-5 can find out that the product of embodiment 1 has wide mesomorphous phase TR.
Its DSC test result of the product of embodiment 2-3 and polarizing microscope characterization result and embodiment's 1 is approximate, shows that the product of embodiment 2-3 also has wide mesomorphous phase TR.
The foregoing description is a preferred implementation of the present invention; But embodiment of the present invention is not restricted to the described embodiments; Other any do not deviate from change, the modification done under spirit of the present invention and the principle, substitutes, combination, simplify; All should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (10)
1. fluorine-containing nitrogen heterocyclic liquid crystalline cpd is characterized in that: have suc as formula the structure shown in the I:
Wherein, n is the natural number between the 0-10, and m is 1 or 2, R
1Be H, Cl, F, Br or CN, R
2Be H, Cl, F, Br or CN, X does
2. fluorine-containing nitrogen heterocyclic liquid crystalline cpd according to claim 1 is characterized in that: described n is 3 or 5, R
1=R
2=H.
3. the compound method of claim 1 or 2 described fluorine-containing nitrogen heterocyclic liquid crystalline cpds is characterized in that may further comprise the steps:
(1) get 2,2,3,3-tetrafluoro-1,4-butyleneglycol and pyridine are with mol ratio 1: (1.5-2.5) mix, add CH
2Cl
2And stir, adding trifluoromethanesulfanhydride anhydride again, stirring reaction 10 hours obtains product trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester after reaction finishes;
(2) compound shown in the modus ponens V and trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester mixes with mol ratio at 1: 1, adds dissolve with ethanol, and oil bath reflux 12 hours obtains the compound shown in the formula III after reaction finishes;
(3) compound shown in the modus ponens III and sodium tert-butoxide are with mol ratio 1: (4-8) mix, add DMSO 99.8MIN. as solvent, 60-100 ℃ of reaction 12 hours down obtains the compound shown in the formula IV after reaction finishes;
(4) compound shown in the formula II is mixed with mol ratio with the compound shown in formula III or the formula IV at 1: 1; Add N again; N '-NSC 57182 and 4-Dimethylamino pyridine; As solvent, reflux 12 hours obtains suc as formula the fluorine-containing nitrogen heterocyclic liquid crystalline cpd shown in the I after reaction finishes with trichloromethane;
The described trifluoromethanesulfanhydride anhydride of step (1) and 2,2,3,3-tetrafluoro-1, the mol ratio of 4-butyleneglycol is 2: 1;
Among the described formula II, n is the natural number between the 0-10, and m is 1 or 2;
4. the compound method of fluorine-containing nitrogen heterocyclic liquid crystalline cpd according to claim 3 is characterized in that:
Among the described formula II, n is 3 or 5;
Among described formula III-V, R
1=R
2=H.
5. the compound method of fluorine-containing nitrogen heterocyclic liquid crystalline cpd according to claim 3 is characterized in that: after the said reaction of step (1) finishes, with organic layer washing, drying, remove CH
2Cl
2, obtain trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro-1,4-fourth diester.
6. the compound method of fluorine-containing nitrogen heterocyclic liquid crystalline cpd according to claim 3 is characterized in that: after the said reaction of step (2) finishes, remove ethanol, add CH
2Cl
2, the washing organic layer, drying obtains the compound shown in the formula III with petrol ether/ethyl acetate mixed solvent column chromatography at last.
7. the compound method of fluorine-containing nitrogen heterocyclic liquid crystalline cpd according to claim 3 is characterized in that: after the said reaction of step (3) finishes, add CH
2Cl
2, the washing organic layer, drying obtains the compound shown in the formula IV with petrol ether/ethyl acetate mixed solvent column chromatography then.
8. the compound method of fluorine-containing nitrogen heterocyclic liquid crystalline cpd according to claim 3 is characterized in that: compound and the N shown in the said formula II of step (4), the mol ratio of N '-NSC 57182,4-Dimethylamino pyridine is 1: 1: 0.05.
9. the compound method of fluorine-containing nitrogen heterocyclic liquid crystalline cpd according to claim 3 is characterized in that: after the said reaction of step (4) finishes, obtain fluorine-containing nitrogen heterocyclic liquid crystalline cpd with sherwood oil/trichloromethane mixed solvent column chromatography.
10. claim 1 or 2 application of described fluorine-containing nitrogen heterocyclic liquid crystalline cpd in liquid crystal display material.
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CN105062502A (en) * | 2015-08-07 | 2015-11-18 | 华南师范大学 | Liquid crystal compound containing five membered nitrogen-containing heterocycles, as well as synthesizing method and application thereof |
CN108774536A (en) * | 2018-05-22 | 2018-11-09 | 王红 | A kind of preparation method of flexure type liquid crystal new material |
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US20050224756A1 (en) * | 2002-06-24 | 2005-10-13 | Volker Reiffenrath | 3,3,4,4-Tetrafluorocyclopentane compounds, used as components of liquid crystal media |
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CN105062502A (en) * | 2015-08-07 | 2015-11-18 | 华南师范大学 | Liquid crystal compound containing five membered nitrogen-containing heterocycles, as well as synthesizing method and application thereof |
CN108774536A (en) * | 2018-05-22 | 2018-11-09 | 王红 | A kind of preparation method of flexure type liquid crystal new material |
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