CN108130102A - A kind of preparation method containing lateral fluorochemical monomer liquid crystal - Google Patents
A kind of preparation method containing lateral fluorochemical monomer liquid crystal Download PDFInfo
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- CN108130102A CN108130102A CN201711458063.1A CN201711458063A CN108130102A CN 108130102 A CN108130102 A CN 108130102A CN 201711458063 A CN201711458063 A CN 201711458063A CN 108130102 A CN108130102 A CN 108130102A
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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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- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
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- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C09K19/06—Non-steroidal liquid crystal compounds
- 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
- 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
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
- C09K2019/3036—Cy-C2H4-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- 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
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
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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
- C09K19/3001—Cyclohexane rings
- C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
- C09K2019/3053—Cy-CH=CH-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- 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
- C09K19/3001—Cyclohexane rings
- C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
- C09K2019/3054—Cy-Cy-CH=CH-Ph
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Abstract
The present invention relates to field of liquid crystals, more particularly to a kind of preparation method containing lateral fluorochemical monomer liquid crystal, the structural formula containing lateral fluorochemical monomer liquid crystal is as follows：In formula, R C1~C9Straight chained alkyl；R1 is C1~C9Unbranched alkoxy, n 1,2.Preparation method provided by the invention is easy to operate, and the cost of raw material is cheap, and raw material is readily available, and technology and equipment barrier are low, conducive to industrialized production.
Description
Technical field
It is more particularly to a kind of applied to containing laterally in liquid-crystal composition and liquid crystal display the present invention relates to field of liquid crystals
The preparation method of fluorinated monomer liquid crystal.
Background technology
As LCD technology develops rapidly, liquid crystal material is also fast-developing required by TFT-LCD, such material requirements liquid crystal
Compound has the requirements such as low viscosity, voltage retention height.And containing lateral fluorochemical monomer class liquid crystal material, have good
The excellent performances such as dissolubility and good photochemical stability can reduce the viscosity of mixed liquid crystal, they have become STN- now
The main component of LCD, TFT-LCD liquid crystal material.
Invention content
The technical problems to be solved by the invention are to provide a kind of preparation method containing lateral fluorochemical monomer liquid crystal, the preparation
Method is easy to operate, and the cost of raw material is low, and raw material is readily available, and technology and equipment barrier are low, conducive to industrialized production.
The technical solution that the present invention solves above-mentioned technical problem is as follows：
One kind contains lateral fluorochemical monomer liquid crystal, which is characterized in that the structural formula containing lateral fluorochemical monomer liquid crystal is as follows：
In formula, R C1~C9Straight chained alkyl；R1 is C1~C9Unbranched alkoxy, n 1,2.
A kind of preparation method containing lateral fluorochemical monomer liquid crystal, follows the steps below：
1) Grignard reagents are prepared：Chemical compounds I is reacted 4~8 hours with magnesium metal under 20~70 DEG C of temperature conditions,
The molar ratio of chemical compounds I and magnesium metal is 1:0.95~1.1, obtain Grignard reagents；
2) prepare compound III：According to molar ratio it is 1 by Grignard reagents and compound II:0.95~1.1 mixing,
It carries out Grignard and compound III is obtained by the reaction；
3) prepare compound IV：Compound III carries out dehydration 1~5 hour, obtains compound IV；
4) it prepares containing lateral fluorinated monomer liquid crystal：Compound IV is urged under an atmosphere of hydrogen using noble metal catalyst
Change hydrogenation, the reaction time is 4~8 hours, is obtained described containing lateral fluorinated monomer liquid crystal；Wherein,
The structural formula of the chemical compounds I is：
The structural formula of the compound ii is：
The structural formula of the compound III is：
The structural formula of the compound IV is:
The structural formula containing lateral fluorochemical monomer is:
In formula, R C1~C9Straight chained alkyl；R1 is C1~C9Unbranched alkoxy, n 1,2.
Specifically, the molar ratio of the prepare compound III, compound I and compound II are 1:0.95；
The prepare compound III, reaction temperature are 60~65 DEG C；
The compound III progress dehydration times are 2 hours；
The compound IV carries out hydrogenation, and reaction temperature is 20~40 DEG C, reaction dissolvent is toluene, ethyl alcohol it is mixed
Bonding solvent, the noble metal catalyst are one kind in palladium carbon or platinum carbon, and the reaction time is 6 hours.
Specific embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit
Determine the scope of the present invention.
Embodiment 1 is propyl as R, and R1 is ethyoxyl, during n=2；
1) synthesis of compound 4a
In the 500ml three neck round bottom flask for thering is nitrogen to protect, 4.8g (0.2mol) magnesium metal is added in, then adds in 5ml
51.3g (0.2mol) compound 2a, 150gTHF solution, 0.2g bromoethanes are heated to 60~65 DEG C, and initiation reaction is then refluxed for
Remaining compound 2a, THF solution is added dropwise, insulation reaction 3 hours, in insulating process, magnesium metal fades away, and heat preservation finishes
Afterwards, room temperature is cooled to, 35.3g (0.19) compound 3a, 100gTHF solution, insulation reaction 1 hour, drop are added dropwise in 20~25 DEG C
Hydrochloric acid, aqueous solution is added to terminate reaction, toluene is added in and is layered, separate organic phase, carry out next step reaction, Y：100%, through GC
Chromatography test purity is 90%
2) compound 5a is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, the toluene of the 4a Han 77.5g (0.19mol) compounds is added in
Then solution adds in 3.6g p-methyl benzenesulfonic acid, then heating distillation carries out reflux heat preservation to 108 DEG C, keeps the temperature 2 hours, carry out water
Solution, layering after toluene extraction, carry out desolventizing, after taking off, add in ethyl alcohol recrystallization, cooling filtering obtains 66.7g whites
Crystal, Y：90%.It is 99.5% through GC chromatographies test purity.
3) compound 1a is synthesized
In the 2L autoclave pressures for having nitrogen to protect, 66.7g (0.17mol) compounds 5a, 500g toluene, 200 ethyl alcohol are added in,
Then 0.6g metallic catalysts are added in, 0.5~1.5MPa of Hydrogen Vapor Pressure room temperature is kept to keep the temperature 6 hours, then filters out metal catalytic
Agent carries out desolventizing, after taking off, adds in ethyl alcohol recrystallization, cooling filtering obtains 60.3g white crystals, Y：90%.Through GC
Chromatography test purity is 99.8%.
Embodiment 2 is propyl as R, and R1 is ethyoxyl, during n=1；
1) compound 4b is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, 4.8g (0.2mol) magnesium metal is added in, then adds in 5ml
34.9g (0.2mol) compound 2b, 150gTHF solution, 0.2g bromoethanes are heated to 60~65 DEG C, and initiation reaction is then refluxed for
Remaining compound 2b, THF solution is added dropwise, insulation reaction 3 hours, in insulating process, magnesium metal fades away, and heat preservation finishes
Afterwards, room temperature is cooled to, 35.3g (0.19) compound 3b, 100gTHF solution, insulation reaction 1 hour, drop are added dropwise in 20~25 DEG C
Hydrochloric acid, aqueous solution is added to terminate reaction, toluene is added in and is layered, separate organic phase, carry out next step reaction, Y：100%, through GC
Chromatography test purity is 92%
2) compound 5b is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, the toluene of the 4a Han 61.9g (0.19mol) compounds is added in
Then solution adds in 3.6g p-methyl benzenesulfonic acid, then heating distillation carries out reflux heat preservation to 108 DEG C, keeps the temperature 2 hours, carry out water
Solution, layering after toluene extraction, carry out desolventizing, after taking off, obtain the nearly colourless liquids of 52.7g, Y：90%.It is surveyed through GC chromatographies
It is 95% to try purity.
3) compound 1b is synthesized
In the 2L autoclave pressures for thering is nitrogen to protect, 52.7g (0.17mol) compounds 5a, 400g toluene, 200 isopropyls are added in
Then alcohol adds in 0.6g metallic catalysts, 0.5~1.0MPa of Hydrogen Vapor Pressure room temperature is kept to keep the temperature 6 hours, metal is then filtered out and urges
Agent carries out desolventizing, after taking off, adds in ethyl alcohol recrystallization, cooling filtering obtains 47.7g white crystals, Y：90%.Through
GC chromatographies test purity is 99.5%.
Embodiment 3 is heptyl as R, and R1 is ethyoxyl, during n=1；
1) synthesis of compound 4c
In the 500ml three neck round bottom flask for thering is nitrogen to protect, 4.8g (0.2mol) magnesium metal is added in, then adds in 5ml
46.1g (0.2mol) compound 2c, 150gTHF solution, 0.2g bromoethanes are heated to 60~65 DEG C, and initiation reaction is then refluxed for
Remaining compound 2c, THF solution is added dropwise, insulation reaction 3 hours, in insulating process, magnesium metal fades away, and heat preservation finishes
Afterwards, room temperature is cooled to, 35.3g (0.19) compound 3c, 100gTHF solution, insulation reaction 1 hour, drop are added dropwise in 20~25 DEG C
Hydrochloric acid, aqueous solution is added to terminate reaction, toluene is added in and is layered, separate organic phase, carry out next step reaction, Y：100%, through GC
Chromatography test purity is 90%
2) compound 5c is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, the toluene of the 4c Han 72.6g (0.19mol) compounds is added in
Then solution adds in 3.6g p-methyl benzenesulfonic acid, then heating distillation carries out reflux heat preservation to 108 DEG C, keeps the temperature 2 hours, carry out water
Solution, layering after toluene extraction, carry out desolventizing, after taking off, obtain 62.2g shadows, Y：90%.It is tested through GC chromatographies pure
Spend is 95%.
3) compound 1c is synthesized
In the 2L autoclave pressures for thering is nitrogen to protect, 62.2g (0.171mol) compounds 5c, 500g toluene, 200 second are added in
Then alcohol adds in 0.6g metallic catalysts, 0.5~1.5MPa of Hydrogen Vapor Pressure room temperature is kept to keep the temperature 6 hours, metal is then filtered out and urges
Agent carries out desolventizing, after taking off, adds in ethyl alcohol recrystallization, cooling filtering obtains 56.3g white crystals, Y：90%.Through
GC chromatographies test purity is 99.8%.
Embodiment 4 is amyl as R, and R1 is ethyoxyl, during n=1；
1) compound 4d is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, 4.8g (0.2mol) magnesium metal is added in, then adds in 5ml
40.5g (0.2mol) compound 2d, 150gTHF solution, 0.2g bromoethanes are heated to 60~65 DEG C, and initiation reaction is then refluxed for
Remaining compound 2d, THF solution is added dropwise, insulation reaction 3 hours, in insulating process, magnesium metal fades away, and heat preservation finishes
Afterwards, room temperature is cooled to, 35.3g (0.19) compound 3d, 100gTHF solution, insulation reaction 1 hour, drop are added dropwise in 20~25 DEG C
Hydrochloric acid, aqueous solution is added to terminate reaction, toluene is added in and is layered, separate organic phase, carry out next step reaction, Y：100%, through GC
Chromatography test purity is 90%
2) compound 5d is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, the toluene of the 4d Han 67.3g (0.19mol) compounds is added in
Then solution adds in 3.6g p-methyl benzenesulfonic acid, then heating distillation carries out reflux heat preservation to 108 DEG C, keeps the temperature 2 hours, carry out water
Solution, layering after toluene extraction, carry out desolventizing, after taking off, obtain the nearly colourless liquids of 57.4g, Y：90%.It is surveyed through GC chromatographies
It is 95% to try purity.
3) compound 1d is synthesized
In the 2L autoclave pressures for thering is nitrogen to protect, 57.4g (0.17mol) compounds 5d, 400g toluene, 200 isopropyls are added in
Then alcohol adds in 0.6g metallic catalysts, 0.5~1.0MPa of Hydrogen Vapor Pressure room temperature is kept to keep the temperature 6 hours, metal is then filtered out and urges
Agent carries out desolventizing, after taking off, adds in ethyl alcohol recrystallization, cooling filtering obtains 51.7g white crystals, Y：90%.Through
GC chromatographies test purity is 99.5%.
Embodiment 5 is amyl as R, and R1 is amoxy, during n=1；
1) compound 4e is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, 4.8g (0.2mol) magnesium metal is added in, then adds in 5ml
40.5g (0.2mol) compound 2e, 150gTHF solution, 0.2g bromoethanes are heated to 60~65 DEG C, and initiation reaction is then refluxed for
Remaining compound 2e, THF solution is added dropwise, insulation reaction 3 hours, in insulating process, magnesium metal fades away, and heat preservation finishes
Afterwards, room temperature is cooled to, 43.3g (0.19) compound 3e, 100gTHF solution, insulation reaction 1 hour, drop are added dropwise in 20~25 DEG C
Hydrochloric acid, aqueous solution is added to terminate reaction, toluene is added in and is layered, separate organic phase, carry out next step reaction, Y：100%, through GC
Chromatography test purity is 90%
2) compound 5e is synthesized
In the 500ml three neck round bottom flask for thering is nitrogen to protect, the toluene of the 4e Han 75.2g (0.19mol) compounds is added in
Then solution adds in 3.6g p-methyl benzenesulfonic acid, then heating distillation carries out reflux heat preservation to 108 DEG C, keeps the temperature 2 hours, carry out water
Solution, layering after toluene extraction, carry out desolventizing, after taking off, obtain the nearly colourless liquids of 64.6g, Y：90%.It is surveyed through GC chromatographies
It is 92% to try purity.
3) compound 1e is synthesized
In the 2L autoclave pressures for thering is nitrogen to protect, 64.3g (0.17mol) compounds 5e, 400g toluene, 200 isopropyls are added in
Then alcohol adds in 0.6g metallic catalysts, 0.5~1.0MPa of Hydrogen Vapor Pressure room temperature is kept to keep the temperature 6 hours, metal is then filtered out and urges
Agent carries out desolventizing, after taking off, adds in ethyl alcohol recrystallization, cooling filtering obtains 58.1g white crystals, Y：90%.Through
GC chromatographies test purity is 99.3%.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention.
Claims (6)
1. one kind contains lateral fluorochemical monomer liquid crystal, which is characterized in that the structural formula containing lateral fluorochemical monomer liquid crystal is as follows：
In formula, R C1~C9Straight chained alkyl；R1 is C1~C9Unbranched alkoxy, n 1,2.
2. a kind of preparation method containing lateral fluorochemical monomer liquid crystal, which is characterized in that follow the steps below：
1) Grignard reagents are prepared：Chemical compounds I is reacted 4~8 hours with magnesium metal under 20~70 DEG C of temperature conditions, chemical combination
The molar ratio of object I and magnesium metal is 1:0.95~1.1, obtain Grignard reagents；
2) prepare compound III：According to molar ratio it is 1 by Grignard reagents and compound II:0.95~1.1 mixing, carries out
Compound III is obtained by the reaction in Grignard；
3) prepare compound IV：Compound III carries out dehydration 1~5 hour, obtains compound IV；
4) it prepares containing lateral fluorinated monomer liquid crystal：Compound IV carries out catalysis hydrogen using noble metal catalyst under an atmosphere of hydrogen
Change reaction, the reaction time is 4~8 hours, is obtained described containing lateral fluorinated monomer liquid crystal；Wherein,
The structural formula of the chemical compounds I is：
The structural formula of the compound ii is：
The structural formula of the compound III is：
The structural formula of the compound IV is:
The structural formula containing lateral fluorochemical monomer is:
In formula, R C1~C9Straight chained alkyl；R1 is C1~C9Unbranched alkoxy, n 1,2.
3. the preparation method containing lateral fluorochemical monomer liquid crystal according to claim, which is characterized in that described in step 1)
The molar ratio of prepare compound III, compound I and compound II are 1:0.95.
4. the preparation method according to claim 1 containing lateral fluorochemical monomer liquid crystal, which is characterized in that described in step 2)
Prepare compound III, reaction temperature are 60~65 DEG C.
5. the preparation method according to claim 1 containing lateral fluorochemical monomer liquid crystal, which is characterized in that described in step 3)
The compound III progress dehydration times are 2 hours.
6. the preparation method according to claim 1 containing lateral fluorochemical monomer liquid crystal, which is characterized in that described in step 4)
Compound IV carry out hydrogenation, reaction temperature is 20~40 DEG C, and the noble metal catalyst is one in palladium carbon or platinum carbon
Kind, the reaction time is 6 hours.
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2017
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|---|---|---|---|---|
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