CN102827614A - Negative liquid crystal containing 2, 3, 5, 6-tetra-fluorine phenylene, as well as synthesis method and application of negative liquid crystal - Google Patents
Negative liquid crystal containing 2, 3, 5, 6-tetra-fluorine phenylene, as well as synthesis method and application of negative liquid crystal Download PDFInfo
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Abstract
The invention relates to a negative liquid crystal containing 2, 3, 5, 6-tetra-fluorine phenylene and with the following structural formula, as well as a synthesis method and application of the negative liquid crystal, wherein R equals to C1-C8 positive alkyl. The synthesis method comprises the following steps of: introducing 2, 3, 5, 6-tetra-fluorine phenylene groups into a negative liquid crystal molecules, and connecting the groups with the molecules by ethylidene bridged bonds, thereby forming the negative liquid crystal containing the 2, 3, 5, 6-tetra-fluorine phenylene. The introduced nonpolar tetra-fluorine phenylene is beneficial to improving response speed, electrical resistivity and chemical stability of the negative liquid crystal. The series of liquid crystals are monotropic nematic-phase liquid crystals, and free from smectic phase. The negative liquid crystal can be used for preparing negative liquid crystal compound materials.
Description
Technical field
The present invention relates to a kind ofly contain 2,3,5, negative liquid crystal, compound method and the application of 6-tetrafluoro phenylene.
Background of invention
The development that shows along with liquid crystal flat-panel in order to improve liquid-crystal display (LCDs) display speed and to widen the visual angle of device, has been developed the indicating meter of various different characteristics display formats.In the AMLCD of practicability (AM-LCD), majority adopts the positivity liquid crystal, and promptly the difference Δ ε of the axial specific inductivity of molecular axis direction and perpendicular molecules is a positive number.Some AM-LCD are also arranged in contrast, and for example, VA-TFT LCD (Thin Film Transistor-LCD of molecule arranged vertical) uses the mixed liquid crystal of Δ ε as negative, and the display image quality that can produce is outstanding, and not only response speed is fast, and wide visual angle is arranged.Wide visual angle is the outstanding advantage of VA-TFT LCD pattern.Characteristics of the present invention are in the negative liquid crystal molecule, to import 2,3,5, and 6-tetrafluoro phenylene group utilizes the ethylidene bridged bond to connect, and forms new negative liquid crystal.Help improving response speed, resistivity and chemicalstability owing to import nonpolar tetrafluoro phenylene.This series liquid crystal all is monotropic nematic liquid crystal, does not have smectic phase.Can be used to prepare the negative liquid crystal compound-material.
Summary of the invention
The object of the invention provides a kind of and contains 2,3,5, the negative liquid crystal compound of 6-tetrafluoro phenylene.
The object of the invention also provides a kind of compound method of above-mentioned negativity liquefaction compound;
Another object of the present invention provides above-mentioned negative liquid crystal application of compound.
Of the present inventionly contain 2,3,5, the negative liquid crystal of 6-tetrafluoro phenylene has following molecular formula:
Wherein, the positive alkyl of the alkyl of R=C1-C8, especially C2-C5.
Of the present invention 2,3,5, the synthetic reaction formula of the negative liquid crystal compound of 6-tetrafluoro phenylene is following:
Wherein, the positive alkyl of R=C1-C8, the positive alkyl of preferred C2-C5.
Concrete synthesis step is following:
1), aligns the synthetic of C1-C8 alkoxyl group perfluor phenylacetylene E
At normal temperatures with organic solvent in perfluorophenyl trimethylsilyl acetylene D, salt of wormwood, positive C1-C8 alcohol mol ratio is followed successively by 1:1 ~ 2:1 ~ 5 o'clock reaction 72h.The preferred positive C2-C5 alcohol of wherein positive C1-C8 alcohol.
2), 2,3-two fluoro-4-thanatol A's is synthetic
In organic solvent with 0 ~ 40 ℃ under, 2,3-two fluoro-4-phenetole boric acid react 5 ~ 20h when Glacial acetic acid min. 99.5 and ydrogen peroxide 50 mol ratio are followed successively by 1:1 ~ 3:1:20.
3), 4-Iodobenzoic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester B's is synthetic
In organic solvent and under the room temperature, 4-Iodobenzoic acid, 2,3-two fluoro-4-thanatols, NSC 57182 and 4-Dimethylamino pyridine mol ratio are followed successively by 1.5:1:1 ~ 2:0.5 ~ 1 o'clock reaction 10 ~ 30h.
4), 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F's is synthetic
Align C1-C8 alkoxyl group perfluor phenylacetylene E (preferential positive C2-C5 alkoxyl group perfluor phenylacetylene E), 4-Iodobenzoic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester B, Pd (PPh
3)
2Cl
2, CuI and triethylamine react 1 ~ 5h under reflux temperature, above-mentioned C1-C8 alkoxyl group perfluor phenylacetylene E, 4-Iodobenzoic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester B, the Pd (PPh of aligning
3)
2Cl
2, CuI mol ratio be 1 ~ 1.5:1:0.01 ~ 0.10:0.01 ~ 0.10.
5), 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester G's is synthetic
In organic solvent, in room temperature ~ 45 ℃ and the excess hydrogen atmosphere, still internal pressure 3MPa, 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F, the Pd/C reaction 6h of catalytic amount.Usually the weight ratio of 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F and Pd/C is 1:0.01-0.10.The mol ratio of described 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F and hydrogen is 1:1-100.Recommending the mol ratio of 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F and hydrogen is 1:10-100..
Described organic solvent can be N (DMF), THF, triethylamine or toluene.
Above-mentioned step 3) and 4) is recommended under nitrogen protection and reacts.
The product of above-mentioned steps can adopt filtration, organic solvent extraction separate, dry, concentrate, method purifying such as column chromatography or recrystallization.
Of the present inventionly contain 2,3,5, the negative liquid crystal compound of 6-tetrafluoro phenylene helps improving response speed, resistivity and chemicalstability owing to import nonpolar tetrafluoro phenylene.This series liquid crystal all is monotropic nematic liquid crystal, does not have smectic phase.Can be used to prepare the negative liquid crystal compound-material.
Embodiment
The present invention can be further understood through following embodiment, but content of the present invention can not be limited.Any within the technical scheme that those skilled in that art all belong to the present invention to the simple replacement done of invention or improvement etc. and protected
Embodiment 1: with the example that synthesizes of 4-[(4-n-pentyloxy-2,3,5,6-tetrafluoro phenyl) ethyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester:
Synthesizing of five fluorine iodobenzenes
The THF (THF) that under nitrogen protection, in the there-necked flask of 250ml, adds 3.30g (0.14mol) magnesium and 100ml behind the logical nitrogen 5min, adds the mixed solution of 30.90g (0.125mol) five bromofluorobenzenes and 50mlTHF; Solution flavescence behind the 15min; And exothermic heat of reaction, this moment, cryosel was bathed controlled temperature about 0 ℃, dripped off behind the 30min; Continue reaction 1h, it is brown to darken.Take by weighing iodine 36.00g (0.14mol) and be dissolved in 60mlTHF, drip, about 0 ℃ of controlled temperature, 1h drips off, and continues reaction 50min.Stopped reaction adds the solution that 30ml concentrated hydrochloric acid and 48ml water are made into, and stirs; The solid dissolving is washed repeatedly with the aqueous solution of Sulfothiorine (10%), merges organic phase; Use anhydrous sodium sulfate drying, water pump pressure reducing and steaming solvent, oil pump underpressure distillation again; Collect 52-56 ℃/14mmHg, get brown liquid product 22.00g, yield y:64%.
Synthesizing of perfluorophenyl trimethylsilyl acetylene
Under nitrogen protection, in the there-necked flask of 250ml, add Pd (PPh3) 2Cl2 and the 0.18g cuprous iodide of 0.18g, add 100ml exsiccant triethylamine, logical nitrogen 5min; Add the five fluorine iodobenzenes of 10.00g (34mmol) and the trimethylsilyl acetylene of 5.00g (50mmol), magnetic agitation, temperature are controlled between 25-40 ℃; TCL follows the tracks of and reacts completely behind the 40h, in reaction solution, adds the MTBE of 100ml, suction filtration; Wash solid with MTBE, get sorrel liquid, repeatedly remove a certain amount of triethylamine with washing; Drying, water pump pressure reducing and steaming solvent, oil pump underpressure distillation again; Collect 56-58 ℃/2mmHg cut, get colorless liquid product 6.84g, yield y:82%.
To synthesizing of n-pentyloxy perfluor phenylacetylene
With the perfluorophenyl trimethylsilyl acetylene of 2.45 (10.0mmol), 2.45g (17.8mmol) salt of wormwood, the Pentyl alcohol of 3.5g (39.8mmol) and the dimethyl-formyl of 40ml add in the there-necked flask of 50ml magnetic agitation successively by (DMF); TCL followed the tracks of after normal temperature reacted 72h down, reacted completely, and added the water of 30ml; With MTBE (40*3) extraction, use anhydrous sodium sulfate drying, the pressure reducing and steaming solvent; Cross post with sherwood oil, get yellow liquid product 1.98g, yield y:76%.
2,3-two fluoro-4-thanatols synthetic
With 2 of 18.4g (0.091mol); 3-two fluoro-4-phenetole boric acid, the Glacial acetic acid min. 99.5 of 10.9g (0.182mol) and 70ml exsiccant THF add in the there-necked flask of 250ml, under ice-water bath, from the normal pressure tap funnel, drip 40.8g (11.2mol) ydrogen peroxide 50; The control reacting liquid temperature is below 40 ℃ in the dropping process; 10min dropwises, and continues to react at normal temperatures 20h, and TCL follows the tracks of and reacts completely.In reaction solution, add sodium sulfate (15%) aqueous solution of 100ml and stir 5min, with the MTBE extraction, get organic phase and use anhydrous magnesium sulfate drying, the pressure reducing and steaming solvent gets white solid product 15.80g, yield y:99.7% again.
Synthesizing of 4-Iodobenzoic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester
4-Iodobenzoic acid with 2.5g (10.1mmol); 2.1g (10.0mmol) 2,3-two fluoro-4-thanatols, the 4-Dimethylamino pyridine of the NSC 57182 of 2.3g (11.1mmol) and 90mg (0.74mmol) adds in the there-necked flask of 100ml under nitrogen protection; The THF dissolving that adds 60ml; Magnetic agitation is reacted 30h at normal temperatures, and TCL follows the tracks of and reacts completely.The reaction solution suction filtration, solid is washed with methylene dichloride, and the lower floor's mother liquor that obtains is used 5% acetic acid respectively; Salt solution and water are respectively given a baby a bath on the third day after its birth time, organic phase used anhydrous sodium sulfate drying, the pressure reducing and steaming solvent; The solid that obtains is used sherwood oil: the eluent of methylene dichloride=1:1 is crossed post; The crude product that obtains is used the proportioning recrystallization of sherwood oil: methylene dichloride=20:1 again, gets white solid product 2.70g, yield y:67%.Synthesizing of 4-[(4-n-pentyloxy-2,3,5,6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester
With 280mg (1.1mmol) to n-pentyloxy perfluor phenylacetylene, the 4-Iodobenzoic acid of 400mg (1.0mmol) (2,3-two fluoro-4-oxyethyl groups) phenyl ester, the Pd (PPh of 80mg
3)
2Cl
2, the CuI of 80mg and the triethylamine of 70ml add under nitrogen protection in the there-necked flask of 100ml, magnetic agitation, reaction under refluxing; TCL follows the tracks of behind the 5h, reacts completely cooling; Suction filtration is washed solid with MTBE, lower floor mother liquor water (50*5) extract yellow organic phase; Use anhydrous sodium sulfate drying, the pressure reducing and steaming solvent uses eluent to be the post of crossing of sherwood oil: ETHYLE ACETATE=40:1; Obtain the white solid crude product and use the sherwood oil recrystallization, obtain white solid product 0.48g, yield y:88.7%.
MS(m/z,%):536(M+,148),363(100.00);
1H?NMR(400MHz,CDCl3):δ0.94(t,J=7.0Hz,3H),1.34-1.49(m,7H),1.77-1.84(m,2H),4.14(q,J=6.8Hz,2H),4.29(t,J=6.6Hz,2H),6.74-6.79(m,1H),6.93-6.98(m,1H),7.71(d,J=8.0Hz,2H),8.20(d,J=8.0Hz,2H)
IR(KBr,
max,cm
-1):3451,2961,2933,2867,1738,1606,1514,1494,1440,1394,1272,1244,1119,1072,1018,982,858,762
52 ℃ of Cr of 188 ℃ of N of 189.5 ℃ of I of 76 ℃ of N of polarized light microscope observing: Cr
DSC detects 54.15 ℃ of Cr of 189.02 ℃ of N of 190.04 ℃ of I of 87.62 ℃ of N of data: Cr.
Synthesizing of 4-[(4-n-pentyloxy-2,3,5,6-tetrafluoro phenyl) ethyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester
4-[(4-n-pentyloxy-2,3,5,6-tetrafluoro phenyl) ethynyl] phenylformic acid (2 with 0.30g; 3-two fluoro-4-oxyethyl groups) phenyl ester, the Pd/C of catalytic amount and the toluene of 200ml add in the reaction kettle, add excessive hydrogen, and controlled temperature is about 40 ℃; The 6h afterreaction is complete, uses sherwood oil: the eluent of ETHYLE ACETATE=5:1 is crossed post, gets white solid crude product 0.3g; Use the sherwood oil recrystallization, obtain white solid product 0.27g, yield y:89%.
MS(m/z,%):540(M+,0.69),367(100.00);
1H?NMR(400MHz,CDCl3):δ0.93(t,J=7.0Hz,3H),1.35-1.49(m,7H),1.74-1.81(m,2H),2.96-3.03(m,4H),4.11-4.20(m,4H),6.73-6.78(m,1H),6.92-6.97(m,1H),7.32(d,J=8.4Hz,2H),8.12(d,J=8.0Hz,2H)
IR(KBr,
max,cm
-1):3448,2935,2872,1747,1654,1610,1495,1417,1392,1277,1245,1136,1116,1081,1068,1024,982,942,856,700
57.5 ℃ of Cr of 77 ℃ of N of 83 ℃ of I of polarized light microscope observing: Cr
DSC detects 60.46 ℃ of Cr of 76.17 ℃ of N of 85.40 ℃ of I of data: Cr.
The same embodiment of compound method of embodiment 2 similar target compounds:
Wherein, at normal temperatures with the DMF solvent in perfluorophenyl trimethylsilyl acetylene D, salt of wormwood is followed successively by 1:1 ~ 2:1 ~ 5 o'clock reaction 72h with the mol ratio of positive alkyl (C1-C8) alcohol respectively.Continue reaction with embodiment 1 then, it is following to obtain the result:
4-[(4-oxyethyl group-2,3,5,6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester MS (m/z, %): 494.1 (M+, 1.25), 321.1 (100.00);
1H?NMR(400MHz,CDCl3):δ1.36-1.42(m,6H),4.07(q,J=7.0Hz,2H),4.31(q,J=7.0Hz,2H),6.67-6.72(m,1H),6.86-6.91(m,1H),7.64(d,J=8.4Hz,2H),8.13(d,J=8.4Hz,2H)
DSC detects 90.01 ℃ of Cr of 217.94 ℃ of N of 218.41 ℃ of I of 125.99 ℃ of N of data: Cr
4-[(4-positive propoxy-2,3,5,6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester MS m/z, %): 508.2 (M+, 27.80), 335.1 (100.00);
1H?NMR(400MHz,CDCl3):δ0.99(t,J=7.4Hz,3H),1.40(t,J=7.0Hz,3H),1.71-1.80(m,2H),4.07(q,J=7.0Hz,2H),4.20(t,J=6.4Hz,2H),6.67-6.72(m,1H),6.86-6.91(m,1H),7.63(d,J=8.0Hz,2H),8.13(d,J=8.0Hz,2H)
DSC detects 65.64 ℃ of Cr of 206.44 ℃ of N of 206.86 ℃ of I of 109.86 ℃ of N of data: Cr
4-[(4-n-butoxy-2,3,5,6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester MS (m/z, %): 522.1 (M+, 1.96), 349.1 (100.00);
1H?NMR(400MHz,CDCl3):δ0.92(t,J=7.4Hz,3H),1.39-1.47(m,5H),1.68-1.75(m,2H),4.07(q,J=7.0Hz,2H),4.23(t,J=6.4Hz,2H),6.67-6.72(m,1H),6.86-6.91(m,1H),7.64(d,J=8.4Hz,2H),8.13(d,J=8.4Hz,2H)
DSC detects 57.67 ℃ of Cr of 202.35 ℃ of N of 203.32 ℃ of I of 102.14 ℃ of N of data: Cr
4-[(4-oxyethyl group-2,3,5,6-tetrafluoro phenyl) ethyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester
MS(m/z,%):498.1(M+,0.69),325.1(100.00);
1H?NMR(400MHz,CDCl3):δ1.34(t,J=7.2Hz,3H),1.40(t,J=7.0Hz,3H),2.88-2.97(m,4H),4.07(q,J=7.0Hz,2H),4.20(q,J=7.2Hz,2H),6.60-6.71(m,1H),6.85-6.90(m,1H),7.25(d,J=8.0Hz,2H),8.05(d,J=8.0Hz,2H)
19F?NMR(400MHz,CDCl3):δ-157.65~-157.57(m,2F),-155.84(d,J=16.4Hz,1F),-149.21(d,J=21.6Hz,1F),-146.10~-146.02(m,2F)
DSC detects 77.09 ℃ of Cr of 81.69 ℃ of N of 123.20 ℃ of I of data: Cr.
4-[(4-positive propoxy-2,3,5,6-tetrafluoro phenyl) ethyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester?
4-[(4-n-butoxy-2,3,5,6-tetrafluoro phenyl) ethyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester 1H NMR (400MHz, CDCl3): δ 0.90 (t, J=7.4Hz; 3H), and 1.35-1.46 (m, 5H), 1.65-1.72 (m, 2H), 2.89-2.96 (m, 4H); 4.04-4.14 (m, 4H), 6.66-6.71 (m, 1H), 6.85-6.90 (m, 1H); 7.25 (d, J=8.0Hz, 2H), 8.04 (d, J=8.4Hz, 2H)
19F?NMR(400MHz,CDCl3):δ-157.70~-157.62(m,2F),-155.84(d,J=16.8Hz,1F),-149.21(d,J=22.8Hz,1F),-146.16~-146.08(m,2F)
DSC detects 73.70 ℃ of Cr of 84.63 ℃ of N of 92.99 ℃ of I of data: Cr.
Claims (8)
1. one kind contains 2,3,5, and the negative liquid crystal of 6-tetrafluoro phenylene has following molecular formula:
Wherein, the positive alkyl of R=C1-C8.
2. as claimed in claim 1ly contain 2,3,5, the negative liquid crystal of 6-tetrafluoro phenylene is characterized in that the positive alkyl of described R=C2-C5.
3. as claimed in claim 12,3,5, the compound method of the negative liquid crystal compound of 6-tetrafluoro phenylene is characterized in that obtaining through following step:
1), aligns the synthetic of C1-C8 alkoxyl group perfluor phenylacetylene E
At normal temperatures with organic solvent in perfluorophenyl trimethylsilyl acetylene D, salt of wormwood, positive C1-C8 alcohol mol ratio is followed successively by 1:1 ~ 2:1 ~ 5 o'clock reaction 72h;
2), 2,3-two fluoro-4-thanatol A's is synthetic
In organic solvent with 0 ~ 40 ℃ under, 2,3-two fluoro-4-phenetole boric acid react 5 ~ 20h when Glacial acetic acid min. 99.5 and ydrogen peroxide 50 mol ratio are followed successively by 1:1 ~ 3:1:20;
3), 4-Iodobenzoic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester B's is synthetic
In organic solvent and under the room temperature, 4-Iodobenzoic acid, 2,3-two fluoro-4-thanatols, NSC 57182 and 4-Dimethylamino pyridine mol ratio are followed successively by 1.5:1:1 ~ 2:0.5 ~ 1 o'clock reaction 10 ~ 30h;
4), 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F's is synthetic
Align C1-C8 alkoxyl group perfluor phenylacetylene E, 4-Iodobenzoic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester B, Pd (PPh
3)
2Cl
2, CuI and triethylamine react 1 ~ 5h under reflux temperature, above-mentioned C1-C8 alkoxyl group perfluor phenylacetylene E, 4-Iodobenzoic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester B, the Pd (PPh of aligning
3)
2Cl
2, CuI and triethylamine mol ratio be 1 ~ 1.5:1:0.01 ~ 0.10:0.01 ~ 0.10:1 ~ 20; 5), 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester G's is synthetic
In organic solvent, in room temperature ~ 45 ℃ and the excess hydrogen atmosphere, still internal pressure 3MPa, 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F, the Pd/C reaction 6h of catalytic amount; The weight ratio of 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F and Pd/C is 1:0.01-0.10; The mol ratio of described 4-[(the positive C1-C8 alkoxyl group-2,3,5 of 4-, 6-tetrafluoro phenyl) ethynyl] phenylformic acid (2,3-two fluoro-4-oxyethyl groups) phenyl ester F and hydrogen is 1:10-100.
4. as claimed in claim 32,3,5, the compound method of the negative liquid crystal compound of 6-tetrafluoro phenylene is characterized in that the alcohol described in the described step 1) adopts positive C2-C5 alcohol.
5. as claimed in claim 32,3,5, the compound method of the negative liquid crystal compound of 6-tetrafluoro phenylene is characterized in that described step 3) or 4) be under nitrogen protection, to react.
6. as claimed in claim 32,3,5, the compound method of the negative liquid crystal compound of 6-tetrafluoro phenylene is characterized in that described organic solvent can be N, THF, triethylamine or toluene.
7. as claimed in claim 32,3,5, the compound method of the negative liquid crystal compound of 6-tetrafluoro phenylene, the product that it is characterized in that every step adopts and filters, organic solvent extraction separates, dry, concentrate, column chromatography or recrystallization method purifying.
One kind as claimed in claim 12,3,5, the application of the negative liquid crystal compound of 6-tetrafluoro phenylene in the preparation liquid crystal material.
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| CN107699253A (en) * | 2017-10-18 | 2018-02-16 | 上海天问化学有限公司 | Super fluorine negative liquid crystal compound and constituent, the preparation and application in liquid crystal display device |
| CN110903832A (en) * | 2019-12-20 | 2020-03-24 | 上海瓜呱科技有限公司 | Negative liquid crystal compound, liquid crystal composition containing negative liquid crystal compound and application of negative liquid crystal compound |
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| CN103333697A (en) * | 2013-07-16 | 2013-10-02 | 上海天问化学有限公司 | Nematic negative liquid crystal containing 2,3,5,6-tetrafluorotolane, synthetic method and application |
| CN103333697B (en) * | 2013-07-16 | 2015-06-03 | 福建省邵武市永晶化工有限公司 | Nematic negative liquid crystal containing 2,3,5,6-tetrafluorotolane, synthetic method and application |
| CN104610975B (en) * | 2013-11-05 | 2017-03-01 | 财团法人工业技术研究院 | Negative dielectric anisotropy liquid crystal compound, liquid crystal display, and electro-optical device |
| CN105295947A (en) * | 2014-07-25 | 2016-02-03 | Dic株式会社 | Manufacturing method by contacting hydrogen reduction |
| JP2016030754A (en) * | 2014-07-25 | 2016-03-07 | Dic株式会社 | Production method by catalytic hydrogen reduction |
| CN106365950A (en) * | 2016-08-26 | 2017-02-01 | 大连奇凯医药科技有限公司 | Preparation method of pentafluoroiodobenzene |
| CN106365950B (en) * | 2016-08-26 | 2018-10-30 | 大连奇凯医药科技有限公司 | A kind of preparation method of five fluorine iodobenzene |
| CN107699253A (en) * | 2017-10-18 | 2018-02-16 | 上海天问化学有限公司 | Super fluorine negative liquid crystal compound and constituent, the preparation and application in liquid crystal display device |
| CN110903832A (en) * | 2019-12-20 | 2020-03-24 | 上海瓜呱科技有限公司 | Negative liquid crystal compound, liquid crystal composition containing negative liquid crystal compound and application of negative liquid crystal compound |
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