CN1329481C - Liquid crystal compound containing monofluoro ethylene bridge and its preparing method - Google Patents
Liquid crystal compound containing monofluoro ethylene bridge and its preparing method Download PDFInfo
- Publication number
- CN1329481C CN1329481C CNB2005101090699A CN200510109069A CN1329481C CN 1329481 C CN1329481 C CN 1329481C CN B2005101090699 A CNB2005101090699 A CN B2005101090699A CN 200510109069 A CN200510109069 A CN 200510109069A CN 1329481 C CN1329481 C CN 1329481C
- Authority
- CN
- China
- Prior art keywords
- trans
- cyclohexyl
- ethane
- formula
- fluoro
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 14
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 21
- 238000000034 method Methods 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 82
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 13
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000007810 chemical reaction solvent Substances 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 5
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 238000003747 Grignard reaction Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BJLUKSIUZZJFHF-UHFFFAOYSA-N 1-(1-bromoethyl)-4-ethylbenzene Chemical compound CCC1=CC=C(C(C)Br)C=C1 BJLUKSIUZZJFHF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a liquid crystal compound containing monofluoro ethylene bridge bond and a preparing method thereof, the liquid crystal compound containing monofluoro ethylene bridge bond provided by the present invention has a general formula I structure, wherein n shows the positive integers of 1 to 7, and m shows the positive integers of 1 to 5. fluorin atoms apperar on a center bridge bond of the liquid crystal compound of the present invnetion. The present invention has the characteristics of simple preparation method, low fusing point, wide temperature range of liquid crystal phase, low viscosity, etc., and has wide application foreground in the liquid crystal display field.
Description
Technical field
The present invention relates to liquid crystalline cpd and preparation method thereof, particularly relate to liquid crystalline cpd that contains monofluoro ethylene bridge and preparation method thereof.
Background technology
Entered since 21 century, thin film transistor (Thin Solid Film:TFT) liquid-crystal display has covered the demonstration field of large, medium and small each size comprehensively, be widely used in various terminal displays such as TV, portable computer, desktop computer, pick up camera, mobile phone, become the main flow of flat pannel display.High speed development along with the TFT lcd technology, requirement to the high-performance liquid crystal material is more and more urgent, and therefore development is to heat, chemistry, electricity, good light stability, electric charge conservation rate height, viscosity is low, and the high-performance liquid crystal material that resistivity is high is from now on the research direction of TFT with liquid crystal material.
Because any monomer liquid crystal all can not satisfy all properties requirement on showing, so on showing, all adopt the mixed liquid crystal material of forming in proportion by multiple monomer liquid crystal.Ethane class liquid crystal is because its structural singularity, when its a certain component as mixed liquid crystal exists, can reduce the viscosity and the optical anisotropy of mixed liquid crystal, widen the use temperature scope of mesomorphic phase, also having good light stability and chemical stability simultaneously, is a kind of well behaved liquid crystal material therefore.The Yasuyuki Goto of Japan Chisso company etc. synthesized various containing-ethane class liquid crystal monomer (the US Patent 4797228 of CH2CH2-center bridged bond, US Patent 4820443), Shuichi Matsui etc. is also doing a lot of researchs (US Patent 5468421) aspect the research of ethane class liquid crystal monomer.
Summary of the invention
The purpose of this invention is to provide a kind of liquid crystalline cpd that contains monofluoro ethylene bridge and preparation method thereof.
The liquid crystalline cpd that contains monofluoro ethylene bridge provided by the present invention, its structural formula be suc as formula I,
Wherein, n is the positive integer of 1-7; M is the positive integer of 1-5.
Concrete, above-mentioned liquid crystalline cpd is a kind of in the following compound:
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane.
This preparation method of this liquid crystalline cpd comprises the steps:
1) the preparation structure is suc as formula the 1-of II (4 '-trans-(4 "-trans-alkyl-cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -alkyl phenyl) ethane: the 4-alkyl phenyl monobromethane of formula III structure is generated Grignard reagent with the MAGNESIUM METAL reaction earlier; again with the 4-of formula IV structure trans-(4 '-trans-alkyl-cyclohexyl) hexahydrobenzaldehyde carries out reduction reaction, obtains formula II compound;
Wherein, n is the positive integer of 1-7; M is the positive integer of 1-5;
2) preparation formula I liquid crystalline cpd: the diethylamino sulfur trifluoride reaction with formula II compound and formula V structure obtains described formula I liquid crystalline cpd.
(C
2H
5)
2NSF
3(formula V)
Wherein, step 1) grignard reaction solvent for use is a tetrahydrofuran (THF), and temperature of reaction is 20-30 ℃; The reduction reaction solvent for use is a tetrahydrofuran (THF), and temperature of reaction is-10～5 ℃.
Step 2) reaction solvent is a methylene dichloride, and temperature of reaction is-80～-70 ℃.
Fluorine atom occurs on the center bridged bond of liquid crystalline cpd of the present invention, the preparation method is simple, and it is low to have a fusing point, and characteristics such as wide liquid crystal phase temperature range and low viscosity will have broad application prospects in field of liquid crystal display.
Embodiment
The preparation of embodiment 1,1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane
1, preparation 1-(4 '-trans-(4 "-trans-third cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -ethylphenyl) ethane
In the 500ml there-necked flask, add 19.9g (0.1mol) 4-ethylphenyl monobromethane, the 100ml tetrahydrofuran (THF), 2.43g (0.1mol) MAGNESIUM METAL and 1～2 iodine at room temperature stir after (20～30 ℃) initiation reaction and made Grignard reagent in 1 hour.With frozen water this solution is cooled off 0 ℃, slowly drip in this solution contain 23.6g (0.1mol) 4-trans-mixing solutions of (4 '-trans-propyl group cyclohexyl) hexahydrobenzaldehyde and 200ml tetrahydrofuran (THF), dropwise the back and stirred 12 hours, obtain lurid turbid solution.The hydrochloric acid of Dropwise 5 0ml0.1mol obtains yellow settled solution in this solution.Divide with the 750ml ether and to extract this solution, combining extraction liquid then three times.With the 100ml mass concentration is 2%NaHCO
3Behind twice of this diethyl ether solution of solution washing, use anhydrous Na
2SO
4Dry ether solution 4 hours steams and removes ether, obtains lurid solid 28g.With 200ml dehydrated alcohol recrystallization, obtain white solid 1-(4 '-trans-(4 "-trans-third cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -ethylphenyl) ethane-(4 '-trans-(4 "-trans-third cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -ethylphenyl) ethane 21.5g, gas chromatographic purity is 99.1%, and yield is 60.4%.
IR：3300，2962，2920，2846，1520，1444，1425，1370，1320，1265，1223，1100，1065，1020，975，850，810，670；
MS：356(M+)，355，339，296，237，220，207，132，119，117，91，83，69?55，43；
2, the preparation of 1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane
The methylene dichloride mixing solutions that adds 7.2g (0.02mol) 1-(4 '-trans-(4 "-trans-third cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -ethylphenyl) ethane and 180ml in the 500ml there-necked flask; solution is cooled to-70 ℃ with liquid nitrogen and alcoholic acid mixture then; agitation condition drips the solution of diethylamino sulfur trifluoride (DAST) and 50ml methylene dichloride down; the maintenance temperature of reaction is not higher than-70 ℃, stirring reaction 10 hours.Be warming up to-45 ℃, add the 100ml saturated sodium bicarbonate aqueous solution, rise to room temperature.Leave standstill separatory, the water dichloromethane extraction merges organic phase, is washed to neutrality, uses anhydrous sodium sulfate drying again 5 hours.Revolve steaming behind the suction filtration, obtain white crude product 4.8g, separate crude product with silicagel column, be spin-dried for solution after the sherwood oil drip washing, obtain white solid 3.5g, use the dehydrated alcohol recrystallization again, obtain white crystal 1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane 2.8g; gas chromatographic purity is 99.5%, and yield is 39.1%.
DSC：Cr?38.7℃N?160.7℃I
IR：2980，2920，2846，1516，1444，1429，1375，1261，1223，1097，1050，1020，972，940，854，810，687
MS：358(M+)，339，253，239，220，149，132，119，103，91，83，69，55，43，41
Viscosity (η): 20mm
2S
Show that the gained compound structure is correct.
Its DSC and viscosity data show that this compound is a kind of liquid crystalline cpd of excellent property.
Adopt with last identical method 4-alkyl phenyl monobromethane and MAGNESIUM METAL reacted the generation Grignard reagent, again with 4-trans-(4 '-trans-alkyl-cyclohexyl) hexahydrobenzaldehyde carries out reduction reaction and makes 1-(4 '-trans-(4 "-trans-alkyl-cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -alkyl base phenyl) ethane.1-(4 '-trans-(4 "-trans-alkyl-cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -alkyl base phenyl) ethane and diethylamino sulfur trifluoride (DAST) are reacted again and can obtain following compound, these compounds equally all are liquid crystalline cpds of excellent property:
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -aminomethyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -propyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -butyl phenyl) ethane,
1-(4 '-trans-(4 "-trans-methylcyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-ethyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-butyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-amyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-hexyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane,
1-(4 '-trans-(4 "-trans-heptyl cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -amyl group phenyl) ethane.
Claims (5)
1, the liquid crystalline cpd that contains monofluoro ethylene bridge, its structural formula be suc as formula I,
(formula I)
Wherein, n is the positive integer of 1-7; M is the positive integer of 1-5.
2, liquid crystalline cpd according to claim 1 is characterized in that: described compound is 1-(4 '-trans-(4 "-trans-propyl group cyclohexyl) cyclohexyl)-1-fluoro-2-(4 -ethylphenyl) ethane.
3, the preparation method of the described liquid crystalline cpd of claim 1 comprises the steps:
1) the preparation structure is suc as formula the 1-of II (4 '-trans-(4 "-trans-alkyl-cyclohexyl) cyclohexyl)-1-hydroxyl-2-(4 -alkyl phenyl) ethane: the 4-alkyl phenyl monobromethane of formula III structure is generated Grignard reagent with the MAGNESIUM METAL reaction earlier; again with the 4-of formula IV structure trans-(4 '-trans-alkyl-cyclohexyl) hexahydrobenzaldehyde carries out reduction reaction, obtains formula II compound;
Wherein, n is the positive integer of 1-7; M is the positive integer of 1-5;
2) preparation formula I liquid crystalline cpd: the diethylamino sulfur trifluoride reaction with formula II compound and formula V structure obtains described formula I liquid crystalline cpd
(C
2H
5)
2NSF
3(formula V).
4, preparation method according to claim 3 is characterized in that: step 1) grignard reaction solvent for use is a tetrahydrofuran (THF), and temperature of reaction is 20-30 ℃; The reduction reaction solvent for use is a tetrahydrofuran (THF), and temperature of reaction is-10～5 ℃.
5, preparation method according to claim 3 is characterized in that: step 2) reaction solvent is methylene dichloride, temperature of reaction is-80～-70 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101090699A CN1329481C (en) | 2005-10-17 | 2005-10-17 | Liquid crystal compound containing monofluoro ethylene bridge and its preparing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101090699A CN1329481C (en) | 2005-10-17 | 2005-10-17 | Liquid crystal compound containing monofluoro ethylene bridge and its preparing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1743414A CN1743414A (en) | 2006-03-08 |
| CN1329481C true CN1329481C (en) | 2007-08-01 |
Family
ID=36138940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005101090699A Expired - Fee Related CN1329481C (en) | 2005-10-17 | 2005-10-17 | Liquid crystal compound containing monofluoro ethylene bridge and its preparing method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1329481C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103242859B (en) * | 2013-04-16 | 2014-08-06 | 西安彩晶光电科技股份有限公司 | Liquid crystal composition with wide nematic phase and high response speed |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405488A (en) * | 1980-10-09 | 1983-09-20 | Chisso Corporation | Liquid-crystalline halogenobenzene derivatives |
| US5064565A (en) * | 1989-07-26 | 1991-11-12 | Chisso Corporation | Cyclohexenylethane compound |
| CN1087664A (en) * | 1992-05-28 | 1994-06-08 | 窒素株式会社 | The liquid crystal display of liquid-crystal composition and use liquid crystal composition |
| US5536442A (en) * | 1987-09-25 | 1996-07-16 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Fluorinated liquid crystal compounds and liquid crystal medium containing same |
| CN1130670A (en) * | 1994-12-22 | 1996-09-11 | 智索股份有限公司 | Liquid crystalline compound containing fluorine atom substituted alkyl group(s) and a liquid crystal composition |
| US5641432A (en) * | 1993-03-10 | 1997-06-24 | Chisso Corporation | Dicyclohexylethylene derivative |
| CN1218451A (en) * | 1996-04-02 | 1999-06-02 | 智索公司 | Liquid crystal compounds, liquid crystal compositions containing the compounds, and liquid crystal display devices made by using the compositions |
| CN1403535A (en) * | 2002-10-24 | 2003-03-19 | 李文惠 | Fluoric liquid crystal compound with pyrimidine ring and its application |
-
2005
- 2005-10-17 CN CNB2005101090699A patent/CN1329481C/en not_active Expired - Fee Related
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405488A (en) * | 1980-10-09 | 1983-09-20 | Chisso Corporation | Liquid-crystalline halogenobenzene derivatives |
| US5536442A (en) * | 1987-09-25 | 1996-07-16 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Fluorinated liquid crystal compounds and liquid crystal medium containing same |
| US5064565A (en) * | 1989-07-26 | 1991-11-12 | Chisso Corporation | Cyclohexenylethane compound |
| CN1087664A (en) * | 1992-05-28 | 1994-06-08 | 窒素株式会社 | The liquid crystal display of liquid-crystal composition and use liquid crystal composition |
| US5641432A (en) * | 1993-03-10 | 1997-06-24 | Chisso Corporation | Dicyclohexylethylene derivative |
| CN1130670A (en) * | 1994-12-22 | 1996-09-11 | 智索股份有限公司 | Liquid crystalline compound containing fluorine atom substituted alkyl group(s) and a liquid crystal composition |
| CN1218451A (en) * | 1996-04-02 | 1999-06-02 | 智索公司 | Liquid crystal compounds, liquid crystal compositions containing the compounds, and liquid crystal display devices made by using the compositions |
| CN1403535A (en) * | 2002-10-24 | 2003-03-19 | 李文惠 | Fluoric liquid crystal compound with pyrimidine ring and its application |
Non-Patent Citations (1)
| Title |
|---|
| 1,2-双取代的乙烷类液晶 郑远洋等，液晶与显示，第12卷第4期 1997 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1743414A (en) | 2006-03-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6306271B2 (en) | Liquid crystal compound having difluoromethoxy crosslink, composition and application thereof | |
| CN106318402B (en) | A kind of negative liquid crystal compound, composition and its application | |
| CN104087312A (en) | Liquid crystal composition and its application | |
| JP4776279B2 (en) | Novel compound and liquid crystal composition | |
| CN109423296B (en) | Dibenzothiophene negative dielectric anisotropy compound and preparation method and application thereof | |
| CN104610975B (en) | Negative dielectric anisotropy liquid crystal compound, liquid crystal display, and electro-optical device | |
| CN100509724C (en) | Multifluoro substituted diphenyl acetylene derivative, composition containing multifluoro substituted diphenyl acetylene derivatire, preparation method and use thereof | |
| CN109423297A (en) | A kind of dibenzothiophenes liquid-crystal compounds and its preparation method and application | |
| CN103773390B (en) | Liquid-crystal composition containing pentafluoropropenyl ether type monomers and application thereof | |
| KR20060082821A (en) | Liquid crystal composition comprising novel silicon containing compounds and liquid crystal display device using the same | |
| CN111778040B (en) | Liquid crystal compound and preparation method and application thereof | |
| CN1329481C (en) | Liquid crystal compound containing monofluoro ethylene bridge and its preparing method | |
| CN103756688A (en) | Pentafluoropropylene ether liquid crystal compound as well as preparation method and application thereof | |
| JP2003342219A (en) | Optically active compound and liquid crystal composition containing the compound | |
| CN106398717B (en) | A kind of epoxypentyl class liquid-crystal compounds and preparation method and application | |
| CN104212461A (en) | Symmetric triazole rod-like liquid crystal compound and preparation method thereof | |
| CN103788039B (en) | Liquid-crystal compounds containing oxinane difluoromethylenedioconnecting linking group and preparation method and application | |
| CN114702967A (en) | Novel liquid crystal compound and preparation method and application thereof | |
| CN111484475B (en) | Liquid crystal compound and preparation method and application thereof | |
| CN114105919A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN114105966A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN104496767A (en) | Ether liquid crystal compound and preparation method and applications thereof | |
| CN110938439A (en) | High-polarity large-optical birefringence liquid crystal composition | |
| CN114958390B (en) | Negative liquid crystal compound and preparation method and application thereof | |
| KR20050029523A (en) | Liquid crystalline compound having negative dielectric anisotropy and liquid crystalline composition comprising the same |
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 | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070801 Termination date: 20141017 |
|
| EXPY | Termination of patent right or utility model |