CN108251128B - Liquid crystal compound with negative dielectric anisotropy and preparation method and application thereof - Google Patents
Liquid crystal compound with negative dielectric anisotropy and preparation method and application thereof Download PDFInfo
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- CN108251128B CN108251128B CN201810100783.9A CN201810100783A CN108251128B CN 108251128 B CN108251128 B CN 108251128B CN 201810100783 A CN201810100783 A CN 201810100783A CN 108251128 B CN108251128 B CN 108251128B
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- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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Abstract
The invention relates toAnd a liquid crystal compound with negative dielectric anisotropy, a preparation method and application thereof. The liquid crystal compound with negative dielectric anisotropy has a structure shown in a general formula I. The invention also discloses a preparation method and application thereof. The liquid crystal compound has a very large absolute value of dielectric anisotropy, a high clearing point, good stability and UV resistance.
Description
Technical Field
The invention relates to a liquid crystal compound with negative dielectric anisotropy and a preparation method and application thereof.
Background
Liquid crystals were found a century ago, but research on their application has been rapidly developed in recent decades. The anisotropy of the liquid crystal molecular structure determines the liquid crystal property anisotropy. Liquid crystal displays generally utilize the properties of optical anisotropy and dielectric anisotropy of liquid crystal materials to perform the display function. Liquid crystals can be classified into positive dielectric anisotropy liquid crystals and negative dielectric anisotropy liquid crystals according to the positive and negative of the dielectric anisotropy. The liquid crystal with negative dielectric anisotropy has wide application and becomes one of the current research hotspots. However, in addition to the need to consider the negative dielectric anisotropy of liquid crystal compounds, the clearing point, stability and UV resistance are also important properties of liquid crystal properties. Therefore, it is necessary to provide an effective solution to the above problems.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, the present invention provides a liquid crystal compound having negative dielectric anisotropy. The liquid crystal compound has a very large absolute value of dielectric anisotropy, a high clearing point, good stability and UV resistance.
The technical scheme for solving the technical problems is as follows:
a liquid crystal compound having negative dielectric anisotropy, said compound having the general structure i:
wherein R is1、R2May be the same or different; r1，R2Each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms;
m, n, o each independently represent 0 or 1;
Z1、Z2each independently represents a single bond, -CH2O-、-CH2CH2-or-CH ═ CH-.
Preferably, when n is 0, Z2Represents a single bond, Z1Is represented by-CH2O-; when n is 1, Z1、Z2Simultaneously represent-CH2O-or-CH2CH2-。
Preferably, R1、R2Each independently represents an alkyl group having 1 to 5 carbon atoms.
Preferably, the first and second liquid crystal materials are,to represent
Preferably, the compound of formula I is selected from one of the following formulae I-1 to I-12:
has the advantages that:
the liquid crystal compound obtained by the invention has the advantages of extremely large absolute value of dielectric anisotropy, higher clearing point, better stability and UV resistance.
The present invention also provides a method for preparing the liquid crystal compound having the structure of formula I-1 as described above, comprising the steps of:
(1) reacting the compound of the formula A with thionyl chloride at 75-85 ℃ for 3h under the catalysis of a small amount of DMF to obtain a compound of a formula B;
(2) reacting the formula B with ammonia water at 20-30 ℃ for 12h in the presence of an organic solvent to obtain a formula C;
(3) mixing the formula C with acetic anhydride, reacting for 4 hours at 135-140 ℃, and performing dehydration reaction to obtain a formula D;
(4) reacting the formula D with NaH at 0 ℃ for 2h in the presence of an organic solvent, cooling to-30 ℃, dropwise adding the reaction product into an organic solvent of dibromomethane, naturally stirring and heating, and reacting at 20-30 ℃ for 6h to obtain a formula E;
(5) mixing the formula E and the formula F in the presence of an organic solvent, adding sodium carbonate, and reacting at 80 ℃ for 12h to obtain the compound of the general formula I-1.
The present invention also provides a method for preparing the liquid crystal compound having the structure of formula I-10 as described above, comprising the steps of:
(1) mixing 2, 3-difluorobromobenzene and diethyl malonate, and coupling in an organic solvent under the action of a catalyst to obtain a formula G;
(2) mixing the formula G with anhydrous lithium chloride, reacting for 18H at 140 ℃ in DMF, and decarboxylating to obtain a formula H;
(3) mixing the formula H with sodium borohydride, stirring in an organic solvent at 0 ℃ for 0.5H, naturally heating to room temperature, stirring for 2H, and reducing to obtain a formula I;
(4) dissolving the formula I and triethylamine in an organic solvent, cooling to 0 ℃, dropwise adding SEM-Cl, naturally heating to room temperature, and stirring for 8 hours to obtain a formula J;
(5) dissolving the formula J in an organic solvent, cooling to-78 ℃, dropwise adding butyl lithium, stirring at the same temperature for 1h, dropwise adding tributyl borate, stirring at the same temperature for 1h, and hydrolyzing and acidifying to obtain a formula K;
(6) mixing the formula K with 1, 2-dibromoethane, and stirring for 8 hours at 100 ℃ in an organic solvent in the presence of a catalyst to obtain a formula L;
(7) reacting the formula D with NaH at 0 ℃ for 2h in the presence of an organic solvent, cooling to-30 ℃, dripping the obtained solution into the organic solvent containing the formula L, naturally heating to room temperature, and stirring for 6h to obtain a formula M;
(8) dissolving the formula M in an organic solvent, adding TBAF 20-30 ℃, and stirring for 12 h. Obtaining a formula N;
(9) mixing the formula N with NBS, and stirring for 12h at room temperature in an organic solvent to obtain a formula O;
(10) reacting the compound P with NaH at 0 ℃ for 2h in the presence of an organic solvent, cooling to-30 ℃, dropping the obtained solution into the organic solvent containing the compound O, naturally heating to room temperature, and stirring for 6h to obtain the compound I-10.
The invention also provides a liquid crystal composition comprising any one of the liquid crystal compounds with negative dielectric anisotropy.
The invention also provides application of the liquid crystal composition in the field of liquid crystal displays.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
Example 1:
compound V1
The synthetic route is as follows:
55.52g of n-butylcyclohexanecarboxylic acid, 200ml of thionyl chloride and 0.05g of DMF are heated under reflux for 3 hours and then spin-dried; the solid obtained is dissolved in 200ml THF, added dropwise at 0 ℃ to 100ml THF containing 10g ammonia, stirred for 12h, and spin-dried; adding 100ml of acetic anhydride, heating and refluxing for 4 hours, and spin-drying; 200ml of EA was added, and the mixture was washed 2 times with 100ml of a saturated sodium carbonate solution and 2 times with a saturated saline solution, dried and spin-dried to obtain 48g of Compound 1.
Dissolving 48g of compound 1 in 200ml of THF, adding 12g of sodium hydride at 0 ℃ for 5 times, and stirring for 2 hours; the obtained solution is dropped into THF containing 80g of dibromomethane at the temperature of minus 30 ℃, naturally heated to room temperature, stirred for 6h, and then spin-dried, EA is added, and the mixture is washed, dried and spin-dried to obtain 70g of compound 2.
Dissolving 47g of 1, 2-difluoropropylbenzene in 200ml of THF, cooling to-78 ℃, dropping 157ml of LDA, and stirring for 2 hours; at-78 ℃, dropwise adding 77g of tributyl borate, naturally heating to room temperature, and stirring for 3 hours; adding 60ml of 10% diluted hydrochloric acid, stirring for 0.5h, layering, adding 100ml of 30% hydrogen peroxide into the organic phase, and stirring for 2h at room temperature; the THF was distilled off at atmospheric pressure, extracted twice with DCM, the organic phases were combined, spin dried and recrystallized with ethanol to give 35g of 2, 3-difluoro-3-propylphenol.
70g of compound 2, 51g of 2, 3-difluoro-3-propylphenol, 32g of sodium carbonate and 300ml of acetonitrile are stirred at 80 ℃ for 12h, spin-dried, water and DCM are added, the layers are separated, the organic phase is washed 2 times with saturated saline, dried, spin-dried and recrystallized with petroleum ether to obtain 63g of compound V1.
Upon detection, compound V1 purity: 99.9 percent.
Example 2:
compound V2
The synthetic route is as follows:
51.0g of n-propyl cyclohexanecarboxylic acid, 200ml of thionyl chloride and 0.05g of DMF are heated under reflux for 3 hours and are spin-dried; the solid obtained is dissolved in 200ml THF, added dropwise at 0 ℃ to 100ml THF containing 10g ammonia, stirred for 12h, spin-dried; adding 100ml of acetic anhydride, heating and refluxing for 4 hours, and spin-drying; 200ml of EA were added, washed 2 times with 100ml of saturated sodium carbonate solution, 2 times with saturated brine, dried and spun-dried 43g of Compound 3.
43g of compound 3 are dissolved in 200ml of THF, 12.2g of sodium hydride are added in 5 portions at 0 ℃ and stirred for 2 h; the obtained solution is dropped into THF containing 80g of dibromomethane at the temperature of minus 30 ℃, naturally warmed to room temperature, stirred for 6h, and spin-dried, EA is added, and then the mixture is washed, dried and spin-dried to obtain 64g of compound 4.
64g of the compound 4, 47.2g of 2, 3-difluoro-3-propylphenol (preparation method same as 2, 3-difluoro-3-propylphenol preparation method in example 1), 30.5g of sodium carbonate, 300ml of acetonitrile at 80 ℃ stirring for 12h, spin-drying, adding water and DCM, and layering; the organic phase was washed 2 times with saturated brine, dried and spin-dried. Recrystallization from petroleum ether gave 61g of compound V2.
Purity of compound V2: 99.9 percent.
Example 3:
compound V3
The synthetic route is as follows:
71.0g of compound 5, 200ml of thionyl chloride and 0.05g of DMF are heated under reflux for 3h and then spin-dried; the solid obtained is dissolved in 200ml THF, added dropwise at 0 ℃ to 100ml THF containing 10g ammonia, stirred for 12h, spin-dried; 100ml of acetic anhydride was added, heated under reflux for 4 hours, spin-dried, 200ml of EA was added, washed 2 times with 100ml of saturated sodium carbonate solution, 2 times with saturated saline, dried, and spin-dried 64g of Compound 6.
Dissolving 64g of compound 6 in 200ml of THF, adding 12.4g of sodium hydride at 0 ℃ for 5 times, and stirring for 2 hours; the resulting solution was added dropwise to THF containing 80g of dibromomethane at-30 ℃ and allowed to warm to room temperature, stirred for 6h, spin-dried, EA added, washed, dried, and spin-dried to give 82g of Compound 7.
82g of Compound 7, 47.5g of 2, 3-difluoro-3-propylphenol (preparation method same as 2, 3-difluoro-3-propylphenol preparation method in example 1), 30.8g of sodium carbonate, 300ml of acetonitrile were stirred at 80 ℃ for 12 hours. Spin-drying, adding water and DCM, and layering; the organic phase was washed 2 times with saturated brine, dried and spin-dried. Recrystallization from petroleum ether gave 70g of compound V3.
Purity of compound V3: 99.9 percent.
Example 4:
compound V4
The synthetic route is as follows:
75.6g of compound 8, 200ml of thionyl chloride and 0.05g of DMF are heated under reflux for 3h and then spin-dried; the solid obtained is dissolved in 200ml THF, added dropwise at 0 ℃ to 100ml THF containing 10g ammonia, stirred for 12h, spin-dried; 100ml of acetic anhydride was added, heated under reflux for 4 hours, spin-dried, 200ml of EA was added, washed 2 times with 100ml of saturated sodium carbonate solution, 2 times with saturated brine, dried, and spin-dried 67g of Compound 9.
67g of compound 9 are dissolved in 200ml of THF, 12.2g of sodium hydride are added in 5 portions at 0 ℃ and stirred for 2 h; the obtained solution was dropped into THF containing 80g of dibromomethane at-30 ℃ and naturally warmed to room temperature, stirred for 6 hours, spin-dried, added with EA, washed, dried, and spin-dried to obtain 85g of compound 10.
85g of compound 10, 47.3g of 2, 3-difluoro-3-propylphenol (preparation method same as 2, 3-difluoro-3-propylphenol preparation method in example 1), 30.5g of sodium carbonate, 300ml of acetonitrile at 80 ℃ stirring for 12h, spin-drying, adding water and DCM, and layering; washing the organic phase with saturated saline solution for 2 times, drying, and spin-drying; recrystallization from petroleum ether gave 71g of compound V4.
Purity of compound V4: 99.9 percent.
Example 5:
compound V5
The synthetic route is as follows:
24.3g of Compound 4, 14.6g of Compound 11, 11.1g of sodium carbonate and 200ml of acetonitrile are stirred at 80 ℃ for 12h and then spin-dried to obtain Compound 12.
Stirring the obtained compound 12, 26g of the compound 2, 11.1g of sodium carbonate and 200ml of acetonitrile at 80 ℃ for 12 hours, and spin-drying; adding water and DCM, layering, washing the organic phase with saturated saline water for 2 times, drying, and spin-drying; recrystallization from ethanol gave 30g of compound V5.
Purity of compound V5: 99.9 percent.
Example 6:
compound V6
The synthetic route is as follows:
57.9g of 2, 3-difluorobromobenzene, 100g of potassium phosphate, 50g of diethyl malonate, 0.5g of Pd (dba), 0.4g of tri-tert-butylphosphine and 400ml of toluene were stirred under nitrogen atmosphere at 90 ℃ for 8 h. After cooling and concentration, EA was added, and the mixture was washed with saturated brine for 3 times, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain 80g of Compound 13.
80g of compound 13, 13g of lithium chloride and 300ml of DMF are stirred at 140 ℃ for 18h under nitrogen. Cool, pour into water, extract 3 times with EA, wash the EA phase 4 times with saturated brine, dry, filter, spin dry to give 52g of compound 14.
52g of compound 14, 10.4g of sodium borohydride and 200ml of absolute ethanol are stirred at 0 ℃ for 0.5h, naturally warmed to room temperature and stirred for 2 h. Quenched with water, spin dried, EA added and washed 3 times with saturated brine. Spin-dry to give 45g of Compound 15.
45g of compound 15 and 27.8g of triethylamine are dissolved in 200ml of DCM, cooled to 0 ℃ and 44.2g of SEM-Cl are added dropwise, allowed to warm to room temperature naturally and stirred for 8 h. The DCM phase was washed 3 times with saturated brine and spin dried to give 75g of compound 16.
75g of compound 16 are dissolved in 300ml of THF, cooled to-78 ℃ and 108ml of butyllithium are added dropwise at-70 ℃ and slowly heated to-50 ℃ and stirred for 1 h. Cooled to-78 ℃, 62.4g of tributyl borate is slowly dropped into the solution, the solution is naturally raised to the room temperature, and the solution is stirred for 1 hour. 200ml of water containing 83ml of concentrated hydrochloric acid were added, stirred for 0.5h, the layers were separated and the organic layer was spin-dried. Washed with petroleum ether and dried to give 80g of Compound 17.
80g of the compound 17, 90g of 1, 2-dibromoethane, 90g of potassium phosphate, 0.5g of Pd (dba), 0.4g of PCy3300ml of dioxane, and stirring for 8 hours at 100 ℃ under the protection of nitrogen. Cooling, concentrating, adding EA, washing with saturated brine for 3 times, drying over anhydrous sodium sulfate, filtering, and spin-drying to obtain 90g of compound 18.
38.5g of compound 1 are dissolved in 200ml of THF, 10.3g of sodium is added in 5 portions at 0 ℃ and stirred for 2 h; the resulting solution was added dropwise to THF containing 90g of Compound 18 at-30 ℃ and allowed to warm to room temperature, followed by stirring for 6 hours. Spin-dry, add EA, wash, dry, spin-dry to give 91g of compound 19.
91g of compound 19, 400ml of ethanol, 0.1g of TBAF were stirred for 12 h. And (5) spin-drying to obtain the compound 20.
Compound 20, 61g of triphenylphosphine, 35.7g (0.296mol) of NBS, was stirred at room temperature for 12h in 400ml of THF under nitrogen. Spin dry, add EA, wash 3 times with saturated brine. Gradient-passing through the column by using petroleum ether and EA to obtain 70g of a compound 21.
28.2g of compound 3 are dissolved in 200ml of THF, 7.5g of sodium is added in 5 portions at 0 ℃ and stirred for 2 h; the resulting solution was added dropwise to THF containing 70g of Compound 21 at-30 ℃ and allowed to warm to room temperature, followed by stirring for 6 hours. Spin-drying, adding EA, washing, drying and spin-drying; chromatography with EA, petroleum ether column gave 70g of compound V6.
Purity of compound V6: 99.9 percent.
The invention leads the epsilon of liquid crystal molecules to exist due to the lateral electron-withdrawing groups CN and F//Less than epsilon⊥So that Δ ε < 0.
The liquid crystal compound with negative dielectric anisotropy and lateral CN and F groups is used for adjusting the parameters of the liquid crystal composition so as to improve the performance of a display device.
The present invention may be embodied in other specific forms without departing from its spirit or essential characteristics. The above-described embodiments of the invention are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims, and not by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims (4)
1. A liquid crystal compound having negative dielectric anisotropy, wherein the compound is selected from one of the following general formulae i-7 to i-12:
Ⅰ-10
wherein R is1、R2May be the same or different; r1，R2Each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms.
2. A process for preparing a liquid crystal compound having a structure of formula i-10 as claimed in claim 1, comprising the steps of:
(1) mixing 2, 3-difluorobromobenzene and diethyl malonate, and coupling in an organic solvent under the action of a catalyst to obtain a formula G;
(2) mixing the formula G with anhydrous lithium chloride, reacting for 18H at 140 ℃ in DMF, and decarboxylating to obtain a formula H;
(3) mixing the formula H with sodium borohydride, stirring in an organic solvent at 0 ℃ for 0.5H, naturally heating to room temperature, stirring for 2H, and reducing to obtain a formula I;
(4) dissolving the formula I and triethylamine in an organic solvent, cooling to 0 ℃, dropwise adding SEM-Cl, naturally heating to room temperature, and stirring for 8 hours to obtain a formula J;
(5) dissolving the formula J in an organic solvent, cooling to-78 ℃, dropwise adding butyl lithium, stirring at the same temperature for 1h, dropwise adding tributyl borate, stirring at the same temperature for 1h, and hydrolyzing and acidifying to obtain a formula K;
(6) mixing the formula K with 1, 2-dibromoethane, and stirring for 8 hours at 100 ℃ in an organic solvent in the presence of a catalyst to obtain a formula L;
(7) reacting the formula D with NaH at 0 ℃ for 2h in the presence of an organic solvent, cooling to-30 ℃, dripping the obtained solution into the organic solvent containing the formula L, naturally heating to room temperature, and stirring for 6h to obtain a formula M;
(8) dissolving the formula M in an organic solvent, adding TBAF, and stirring at 20-30 ℃ for 12h to obtain a formula N;
(9) mixing the formula N with NBS, and stirring for 12h at room temperature in an organic solvent to obtain a formula O;
(10) reacting P with NaH at 0 deg.C for 2h in the presence of organic solvent, cooling to-30 deg.C, dropping the obtained solution into organic solvent containing O, naturally heating to room temperature, stirring for 6h to obtain general formula I-10
。
3. A liquid crystal composition comprising the liquid crystal compound having negative dielectric anisotropy according to claim 1.
4. Use of a liquid crystal composition according to claim 3 in the field of liquid crystal displays.
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| CN110396413B (en) * | 2019-07-25 | 2023-07-11 | 河北迈尔斯通电子材料有限公司 | Liquid crystal composition for VA-LCD with low threshold value, low power consumption and wide temperature range |
| CN110577833B (en) * | 2019-08-15 | 2021-03-23 | 河北迈尔斯通电子材料有限公司 | Negative liquid crystal compound and preparation method thereof |
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