CN1827572A - Cyclohexyl biphenyls liquid crystal compounds - Google Patents
Cyclohexyl biphenyls liquid crystal compounds Download PDFInfo
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- CN1827572A CN1827572A CN 200610072804 CN200610072804A CN1827572A CN 1827572 A CN1827572 A CN 1827572A CN 200610072804 CN200610072804 CN 200610072804 CN 200610072804 A CN200610072804 A CN 200610072804A CN 1827572 A CN1827572 A CN 1827572A
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- cyclohexyl
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Abstract
The invention discloses a liquid crystal compound of cyclohexyl diphenyl with a constitutional general formula (I) on the right, in which R standing for linear alkyl with the number of 1-9 of the carbon atom, and R'standing for alkyl with the number of 1-5 of the carbon atom. In order to solve the problem of small negative anisotropic dielectric value of the liquid crystal compound, three fluorin atoms introduced upwards into the benzene ring of the liquid crystal compound of cyclohexyl diphenyl in order to provide a liquid crystal compound not only with a big negative anisotropic dielectric value but also with a high electrical resistivity. The invention is mainly used in the liquid crystal display.
Description
Technical field
The present invention relates to a kind of cyclohexyl biphenyls liquid crystal compounds, belong to liquid crystal material, be mainly used in liquid-crystal display.
Technical background
Liquid-crystal display has panelized, advantage such as low in energy consumption, in light weight, radiationless, in the field of information display development rapidly.Along with the continuous reduction of continuous improvement such as saturated colourity, response speed, contrast gradient, brightness and cost, LCD TV obtains popularizing rapidly.LCD TV has TN-TFT, IPS and three kinds of display formats of VA-TFT at present.The TN-TFT pattern is a kind of display format of being used widely the earliest, and the visual angle is little, response speed waits problem slowly but exist.IPS pattern and VA-TFT pattern have wide visual angle, the fast characteristics of response speed, are the main display formats of LCD TV.
Utilize the liquid-crystal display dielectric anisotropy of liquid crystal material and optically anisotropic characteristic realize Presentation Function.At present also there is not a kind of single liquid crystalline cpd can satisfy every physicals requirement of liquid-crystal display.Several liquid crystalline cpds or the tens of kinds of liquid crystalline cpds that will have different qualities in the practical application are mixed by proper proportion, learn from other's strong points to offset one's weaknesses on every performance, to obtain optimal display result.
Dielectric radio in the liquid crystal molecule on the long axis direction is ε
∥, the dielectric radio of short-axis direction is ε
⊥, the difference of the two is dielectric anisotropy value Δ ε:
Δε＝ε
∥-ε
⊥
Traditional TN-TFT and IPS pattern all adopt the liquid crystal material of positive dielectric anisotropy, i.e. Δ ε＞0.In order to satisfy the requirement of Δ ε＞0, generally take on the long axis direction of liquid crystal molecule to introduce and have strong polar group, as cyano group, fluorine atom, trifluoromethoxy, trifluoromethyl etc.And the liquid crystal material that the VA-TFT pattern requires to be adopted has negative dielectric anisotropic (Δ ε＜0), need promptly introduce groups such as strong polar fluorine atom or cyano group on the side direction of molecule at the short-axis direction of molecule.Though it is bigger to contain the liquid crystalline cpd negative dielectric anisotropic value of side direction cyano group replacement, its resistivity is low, and application is restricted.The liquid crystalline cpd that the side direction fluorine atom replaces has the resistivity height, and the characteristics that polarity is bigger satisfy the requirement of VA-TFT pattern.DE3906058 discloses a class and has had 2, and 3-difluorophenol esters liquid crystal compound is introduced 2 fluorine atoms in the molecule side direction, obtains bigger dielectric anisotropy.But esters liquid crystal compound resistivity is lower, and application is restricted.
DE4444813 discloses has 2, the liquid crystalline cpd of 3-difluorophenyl hexanaphthene:
This compounds resistivity height is stablized.But the dielectric anisotropy value is less.
Summary of the invention
The objective of the invention is to design a kind of big negative dielectric anisotropic value that both had, have the liquid crystalline cpd of high resistivity again in order to solve the little deficiency of known liquid crystalline cpd dielectric anisotropy value.
In order to realize purpose of the present invention, the present invention introduces three fluorine atoms on the side direction of cyclohexyl biphenyls liquid crystal compounds molecule, makes the bigger dielectricity ε of acquisition on the short-axis direction of molecule
⊥Thereby, increase Δ ε value.
(I) is as follows for compound structure of the present invention:
Wherein R is the straight chained alkyl of carbon number 1～9, ethyl for example, n-propyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl.Preferably has carbon number and is 2～7 straight chained alkyl, ethyl for example, n-propyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl.More preferably has carbon number and is 2～5 straight chained alkyl, ethyl for example, n-propyl, normal-butyl, n-pentyl.
Wherein R ' is the alkyl of carbon number 1～5, methyl for example, ethyl, n-propyl, normal-butyl, n-pentyl, sec.-propyl, isobutyl-, the tertiary butyl, isopentyl.The straight chained alkyl that preferably has carbon number 1～5, methyl for example, ethyl, n-propyl, normal-butyl, n-pentyl.More preferably has carbon number and is 1～3 straight chained alkyl, methyl for example, ethyl, n-propyl.
The present invention adopts following synthetic route:
In the invention described above synthetic route
The 1st, intermediate 4-(trans-the 4-alkyl-cyclohexyl)-2,3-two fluorobenzoic boric acids;
The 2nd, intermediate 4-bromo-2-fluorophenyl alkyl oxide.
The present invention adopts following steps synthetic:
1. intermediate 4-(trans-the 4-alkyl-cyclohexyl)-2, the preparation of 3-two fluorobenzoic boric acids
1) adopting 1,2-Difluorobenzene is raw material, sloughs the ortho-hydrogens atom and lithiumation with the n-Butyl Lithium reaction down at-70 ℃, reacts with the 4-alkyl cyclohexanone to obtain 1-(4-alkyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
2) at tosic acid, or under the Catalyzed by Potassium Bisulfate, in toluene, or reflux dewatering obtains 1-(4-alkyl-1-cyclohexenyl)-2,3-two fluorobenzene in the dimethylbenzene;
3) palladium/carbon, or skeleton nickel catalyzed hydrogenation obtains 1-(4-alkyl-cyclohexyl)-2,3-two fluorobenzene;
4) down slough the ortho-hydrogens atom and lithiumation at-70 ℃ with the n-Butyl Lithium reaction ,-70 ℃ and tributyl borate, or trimethyl borate, or triisopropyl borate ester reacts and obtains intermediate 4-(trans-the 4-alkyl-cyclohexyl)-2,3-two fluorobenzoic boric acids.
2. the preparation of intermediate 4-bromo-2-fluorophenyl alkyl oxide
1) synthetic is raw material with adjacent fluorophenol, under the salt of wormwood effect with methyl iodide, or monobromethane, or bromopropane reaction obtains 2-fluorophenyl alkyl oxide;
2) at solvent C HCl
3, or CCl
4In carry out bromo-reaction and obtain intermediate 4-bromo-2-fluorophenyl alkyl oxide.
Target product 4 '-(trans-the 4-alkyl-cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-alkoxyl group biphenyl synthetic
Intermediate 4-(trans-the 4-alkyl-cyclohexyl)-2,3-two fluorobenzoic boric acids and 4-bromo-2-fluorophenyl alkyl oxide close palladium at four (triphenylphosphines), or palladium, or carry out under zeroth order palladium (Pd/C) catalysis of loading type the Suzuki linked reaction obtain target product 4 of the present invention '-(trans-the 4-alkyl-cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-alkoxyl group biphenyl.
Embodiment
The invention will be further described below in conjunction with embodiment.
Embodiment 1
1. 1-(4-n-pentyl-1-hydroxyl-cyclohexyl)-2, the preparation of 3-two fluorobenzene
With 57g (0.5mol) 1,2-Difluorobenzene, 500ml exsiccant tetrahydrofuran (THF) joins in the 2000ml four-hole boiling flask under the nitrogen protection, and liquid nitrogen cooling drips the hexane solution 200ml of the n-Butyl Lithium of 2.5M to-70 ℃.Dropwised the back insulated and stirred 3～4 hours.Keep temperature-70 ℃ dropping to be dissolved with the 300ml dry tetrahydrofuran of 4g (0.5mol) 4-n-pentyl pimelinketone, drip off the back and be warming up to room temperature naturally.Pour reaction product in cryosel acid hydrolysis.Divide oil-yielding stratum, anhydrous magnesium sulfate drying.Remove solvent under reduced pressure, get yellow oily liquid.
Adopt same quadrat method, use 4-ethyl cyclohexanone, 4-n-propyl pimelinketone respectively, 4-normal-butyl pimelinketone, 4-n-hexyl pimelinketone, 4-n-heptyl pimelinketone substitutes positive 4-n-pentyl pimelinketone, prepares:
1-(4-ethyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-propyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-normal-butyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-hexyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-heptyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene.
2. 1-(4-n-pentyl-1-cyclohexenyl)-2, the preparation of 3-two fluorobenzene
To go up step reaction products therefrom 1-(4-n-pentyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene, the 1g tosic acid, 500ml toluene adds in the 1000ml there-necked flask.Reflux water-dividing reaction 4 hours.Cooling after washing 2 times, anhydrous magnesium sulfate drying.The filtering siccative removes solvent under reduced pressure and gets yellow oily liquid.
Adopt same quadrat method, use respectively:
1-(4-ethyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-propyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-normal-butyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-hexyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-heptyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene.Substitute 1-(4-n-pentyl-1-hydroxyl-cyclohexyl)-2,3-two fluorobenzene are prepared:
1-(4-ethyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-n-propyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-normal-butyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-n-hexyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-n-heptyl-1-cyclohexenyl)-2,3-two fluorobenzene.
3. 1-(4-n-pentyl cyclohexyl)-2, the preparation of 3-two fluorobenzene
To go up step reaction products therefrom and add in the 1000ml there-necked flask, add 500ml ethanol, 20g 5% palladium/carbon, catalytic hydrogenation 24 hours.Filtering palladium/carbon removes solvent under reduced pressure, gets yellow oily liquid.
Adopt same quadrat method, use respectively:
1-(4-ethyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-n-propyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-normal-butyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-n-hexyl-1-cyclohexenyl)-2,3-two fluorobenzene;
1-(4-n-heptyl-1-cyclohexenyl)-2,3-two fluorobenzene.Substitute 1-(4-n-pentyl-1-cyclohexenyl)-2,3-two fluorobenzene are prepared:
1-(4-ethyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-propyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-normal-butyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-hexyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-heptyl cyclohexyl)-2,3-two fluorobenzene.
4. 4-(trans-4-n-pentyl cyclohexyl)-2, the preparation of 3-two fluorobenzoic boric acids
With 1-(4-n-pentyl cyclohexyl)-2,3-two fluorobenzene 27g (0.1mol), 150ml exsiccant tetrahydrofuran (THF) joins in the 500ml four-hole boiling flask, and liquid nitrogen cooling drips the hexane solution 40ml of the n-Butyl Lithium of 2.5M to-70 ℃.Dropwised the back insulated and stirred 3～4 hours.Keep dripping the 100ml dry tetrahydrofuran that is dissolved with 46g (0.2mol) tributyl borate below the temperature-70 ℃, drip off the back and be warming up to room temperature naturally.Pouring reaction product into cryosel acid stirred one hour.Divide oil-yielding stratum, anhydrous magnesium sulfate drying.Remove oil reservoir under reduced pressure, the sherwood oil recrystallization gets white crystal 22.7g, yield 84%.
Adopt same quadrat method, use respectively:
1-(4-ethyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-propyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-normal-butyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-hexyl cyclohexyl)-2,3-two fluorobenzene;
1-(4-n-heptyl cyclohexyl)-2,3-two fluorobenzene.
Substitute 1-(4-n-pentyl cyclohexyl)-2,3-two fluorobenzene are prepared:
4-(trans-4-ethyl cyclohexyl)-2,3-two fluorobenzoic boric acids;
4-(trans-4-n-propyl cyclohexyl)-2,3-two fluorobenzoic boric acids;
4-(trans-4-normal-butyl cyclohexyl)-2,3-two fluorobenzoic boric acids;
4-(trans-4-n-hexyl cyclohexyl)-2,3-two fluorobenzoic boric acids;
4-(trans-4-n-heptyl cyclohexyl)-2,3-two fluorobenzoic boric acids.
5. the preparation of 2-fluorobenzene ether
With the adjacent fluorophenol (1.0mol) of 112g, the 276g Anhydrous potassium carbonate, the 130g monobromethane, 1000ml acetone joins in the there-necked flask, and back flow reaction is 12 hours under the nitrogen protection.Cooling, the elimination insolubles removes acetone under reduced pressure, gets yellow oily liquid 129g, yield 92%.
Adopt same quadrat method, use methyl iodide, the 1-N-PROPYLE BROMIDE substitutes monobromethane respectively and prepares:
The 2-fluoroanisole;
2-fluorophenyl positive propyl ether.
6. the preparation of 4-bromo-2-fluorobenzene ether
With 56g 2-fluorobenzene ether (0.4mol), the 200ml tetracol phenixin joins in the there-necked flask, and cryosel is bathed and cooled to below 0 ℃, drips the chloroformic solution that is dissolved with the 64g bromine, drips off back stirring at room 1 hour.Remove chloroform under reduced pressure, get product 75g altogether, yield 86%.
Adopt same quadrat method, use the 2-fluoroanisole, 2-fluorophenyl positive propyl ether substitutes 2-fluorobenzene ether respectively and prepares:
4-bromo-2-fluoroanisole;
4-bromo-2-fluorophenyl positive propyl ether.
7. 4 '-(trans-4-n-pentyl cyclohexyl)-2 ', the preparation of 3 '-two fluoro-3-fluoro-4-ethoxybiphenyls
With 4-(trans-4-n-pentyl cyclohexyl)-2; 3-two fluorobenzoic boric acid 15g (0.05mol); 4-bromo-2-fluorobenzene ether 11g (0.05mol); four (triphenylphosphines) close palladium 0.8g, Tetrabutyl amonium bromide 3.5g, salt of wormwood 15g; ethanol 120ml; toluene 75ml, water 150ml, back flow reaction is 15 hours under the nitrogen protection.Cooling adds 500ml water, divides oil-yielding stratum, and filtration catalizer removes solvent under reduced pressure.Ethyl alcohol recrystallization obtains white crystal 15.7g, yield 78%.
The structure appraising datum:
Ultimate analysis: C
25H
31F
3O theoretical value: C 74.26 H 7.67 O 3.96 F 14.11;
Measured value: C 74.24 H 7.68 O 3.95 F 14.10.
IR(cm
-1，KBr)：2980，1562，1280，1130
1HNMR(δ，CCl
3D)：0.96(3H，t)；1.29～1.52(16H，m)；1.86(4H，m)；2.72(q，1H)；3.98(2H，q)；6.81(1H，m)；6.94(1H，m)；7.08(1H，m)；7.14(2H，m)。The material that confirmation obtains through above-mentioned reaction is 4 really '-(trans-4-n-pentyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-ethoxybiphenyls.
With corresponding 4-(trans-the 4-alkyl-cyclohexyl)-2,3-two fluorobenzoic boric acids, 4-bromo-2-fluorophenyl alkyl oxide, adopt and prepare following compounds with quadrat method:
4 '-(trans-4-n-pentyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-methoxyl biphenyls;
4 '-(trans-4-n-pentyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-propoxy-biphenyl;
4 '-(trans-4-ethyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-methoxyl biphenyls;
4 '-(trans-4-ethyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-ethoxybiphenyls;
4 '-(trans-4-ethyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-propoxy-biphenyl;
4 '-(trans-4-n-propyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-methoxyl biphenyls;
4 '-(trans-4-n-propyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-ethoxybiphenyls;
4 '-(trans-4-n-propyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-propoxy-biphenyl;
4 '-(trans-4-normal-butyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-methoxyl biphenyls;
4 '-(trans-4-normal-butyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-ethoxybiphenyls;
4 '-(trans-4-normal-butyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-propoxy-biphenyl;
4 '-(trans-4-n-hexyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-methoxyl biphenyls;
4 '-(trans-4-n-hexyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-ethoxybiphenyls;
4 '-(trans-4-n-hexyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-propoxy-biphenyl;
4 '-(trans-4-n-heptyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-methoxyl biphenyls;
4 '-(trans-4-n-heptyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-ethoxybiphenyls;
4 '-(trans-4-n-heptyl cyclohexyl)-2 ', 3 '-two fluoro-3-fluoro-4-propoxy-biphenyl.
Claims (3)
1, a kind of cyclohexyl biphenyls liquid crystal compounds, (I) is as follows for its general structure:
Wherein R is the straight chained alkyl of carbon number 1～9, and R ' is the alkyl of carbon number 1～5.
2, cyclohexyl biphenyls liquid crystal compounds according to claim 1 is characterized in that R is the straight chained alkyl of carbon number 2～7, and R ' is the straight chained alkyl of carbon number 1～5.
3, cyclohexyl biphenyls liquid crystal compounds according to claim 2 is characterized in that the straight chained alkyl of R carbon number 2～5, and R ' is the straight chained alkyl of carbon number 1～3.
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|---|---|---|---|
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102559201A (en) * | 2011-12-23 | 2012-07-11 | 陕西师范大学 | Allyloxy lateral multi-fluoric liquid crystal compound and preparation method thereof |
| CN101407719B (en) * | 2008-03-28 | 2012-12-12 | 河北迈尔斯通电子材料有限公司 | Negative dielectric anisotropy liquid crystal material composition and liquid crystal display device using the same |
| CN102826966A (en) * | 2012-08-15 | 2012-12-19 | 烟台万润精细化工股份有限公司 | Preparation method for liquid crystal monomer of o-difluoroalkoxybenzene derivative |
| CN106967443A (en) * | 2017-04-28 | 2017-07-21 | 烟台德润液晶材料有限公司 | The preparation method of alkyl cyclohexyl biphenyl nitrile liquid-crystal compounds |
| CN108239538A (en) * | 2016-12-23 | 2018-07-03 | 江苏和成显示科技有限公司 | A kind of dielectric anisotropy is the liquid-crystal composition and its application born |
-
2006
- 2006-04-10 CN CN 200610072804 patent/CN1827572A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101407719B (en) * | 2008-03-28 | 2012-12-12 | 河北迈尔斯通电子材料有限公司 | Negative dielectric anisotropy liquid crystal material composition and liquid crystal display device using the same |
| CN102559201A (en) * | 2011-12-23 | 2012-07-11 | 陕西师范大学 | Allyloxy lateral multi-fluoric liquid crystal compound and preparation method thereof |
| CN102559201B (en) * | 2011-12-23 | 2013-12-11 | 陕西师范大学 | Allyloxy lateral multi-fluoric liquid crystal compound and preparation method thereof |
| CN102826966A (en) * | 2012-08-15 | 2012-12-19 | 烟台万润精细化工股份有限公司 | Preparation method for liquid crystal monomer of o-difluoroalkoxybenzene derivative |
| CN102826966B (en) * | 2012-08-15 | 2014-11-26 | 烟台万润精细化工股份有限公司 | Preparation method for liquid crystal monomer of o-difluoroalkoxybenzene derivative |
| CN108239538A (en) * | 2016-12-23 | 2018-07-03 | 江苏和成显示科技有限公司 | A kind of dielectric anisotropy is the liquid-crystal composition and its application born |
| CN106967443A (en) * | 2017-04-28 | 2017-07-21 | 烟台德润液晶材料有限公司 | The preparation method of alkyl cyclohexyl biphenyl nitrile liquid-crystal compounds |
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