CN108774536A - A kind of preparation method of flexure type liquid crystal new material - Google Patents
A kind of preparation method of flexure type liquid crystal new material Download PDFInfo
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- CN108774536A CN108774536A CN201810492593.6A CN201810492593A CN108774536A CN 108774536 A CN108774536 A CN 108774536A CN 201810492593 A CN201810492593 A CN 201810492593A CN 108774536 A CN108774536 A CN 108774536A
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- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3477—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom
- C09K19/348—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom containing at least two nitrogen atoms
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Abstract
The present invention relates to field of new material preparation, particularly with regard to a kind of preparation method of flexure type liquid crystal new material；A kind of preparation method of flexure type liquid crystal phase transition temperature new material disclosed in the method for the present invention, with 2,5- bis-（P-hydroxybenzene）Molecule centered on -1,3,4- oxadiazoles, ester bond is bridged bond, and straight chained alkyl is end group, and design synthesizes a kind of flexure type liquid crystal new material, with lower nematic phase transition temperature and wider nematic temperature range, be conducive to the research of the mixed preparing and its photoelectric properties and application of liquid crystal.
Description
Technical field
The present invention relates to field of material preparation, particularly with regard to a kind of preparation method of flexure type liquid crystal new material.
Background technology
Curved liquid-crystal compounds is the another new branch in thermotropic liquid crystal field after rod shaped liquid crystal, discotic mesogenic.Its
Unique anti-iron characteristic and unique molecular configuration cause the extensive concern of people.
CN106978193A discloses two kinds of flexure type liquid-crystal compounds A and B and their synthetic method.The invention
Flexure type liquid-crystal compounds A and B, there is flexure mode structure, can induce and generate blue phase, while end introduces activity larger third
Olefin(e) acid ester structure can further stablize blue phase by ultraviolet polymerization.Chiral nematic phase liquid crystal system (67.2%SLC9023 and
Wide warm blue phase, especially flexure type LCD compound can be generated in 32.8%R811) after doping flexure type liquid-crystal compounds A or B
Object B its warm area after uv-exposure has reached room temperature, has larger application value.
CN201273978Y discloses a kind of optical-compensation bent liquid crystal display panel, the optical-compensation bent liquid crystal
Display panel includes upper substrate and lower substrate, parallel to each other to be oppositely arranged；And liquid crystal layer, be sandwiched in the upper substrate and it is described under
Between substrate, and the dielectric anisotropy of the liquid crystal molecule in the liquid crystal layer is just；Wherein, in the upper substrate and described
Correspondingly form the acclive raised image of tool on lower substrate, and the acclive raised image surface coating of the tool without
The negativity oriented layer of friction.The liquid crystal display panel of the utility model can obtain wide viewing angle, and be not required to apply voltage acquisition
Bend alignment state reduces production cost so as to greatly simplify production technology, improves display effect.
A kind of liquid crystal composite of CN101586031A offers and its manufacturing method, liquid crystal composite include a LCD compound
Object and a nano-particle, wherein liquid-crystal compounds are optical-compensation bent liquid-crystal compounds, and the main chain of nano-particle or side
At least there is an acryl functional group on chain.The content of nano-particle in liquid crystal composite compositing formula is 0.1-2wt%,
Weight percent system is on the basis of the weight of liquid crystal composite.When nano-particle is added to original liquid-crystal compounds, liquid can be made
Crystalline substance is rapidly diverted to bending status by divergence state, makes liquid crystal display device that can be rapidly achieved stable state in initial driving, without spy
The driving circuit of different high voltage, has faster answer speed.
The flexure type liquid crystal new material of the above invention and prior art preparation is there are nematic phase transition temperature is higher, nematic
The relatively narrow problem of phase temperature range limits the further application and development of this kind of material.
Invention content
To solve the above-mentioned problems, the present invention provides a kind of preparation methods of flexure type liquid crystal new material.
A kind of preparation method of flexure type liquid crystal new material, technology of preparing scheme are as follows：
According to mass fraction, by 23.5-26.5 parts of 2,5- bis-（P-hydroxybenzene）- 1,3,4- oxadiazoles, 85-91 parts of centre
Body, 42-48 parts of N, N- dicyclohexylcarbodiimides, 6.1-6.8 parts of N, N- lutidines, 0.1-0.5 parts of 1,3- bis-
Bis- (4- pyridyl groups) the naphthalene 4 formyl-2-imides of imido grpup isoindoline, 0.1-1 parts of N, N'-, 0.01-0.06 parts of soybean oil base
Ethyl morpholine nitrogen sulfovinate, 0.01-0.05 parts of chloroplatinic acid tetrabutylammonium and 300-400 parts of dichloromethane add
Enter in by thoroughly dry reaction kettle, then vacuumize, then uses the air in high pure nitrogen replacement reaction kettle, finally fill
Enter high pure nitrogen protection；Then 18-28h is reacted at ambient temperature；Then it filters, the total solvent of filtrate is evaporated, is obtained
150-200 parts of solvent is added in solid and is heated to 50-60 DEG C of dissolving, stirring 20-30min postcoolings cooling is recrystallized,
Filtering, it is dry after washing, you can to obtain a kind of flexure type liquid crystal new material.
The solvent is absolute ethyl alcohol or ethyl acetate or acetone.
The recrystallization temperature is 4-8 DEG C.
The intermediate is prepared according to following scheme：
According to mass fraction, by 37-45 parts of parahydroxyben-zaldehyde, the dichloromethane of 150-200 parts of pyridine and 500-600 part
It is added in reaction kettle, is vacuumized after stirring and dissolving, it is last when vacuumizing every time with the air in high pure nitrogen replacement reaction kettle
Be filled with high pure nitrogen, then under the conditions of ice-water bath, be slowly added to 95-115 parts to dodecyloxy chlorobenzoyl chloride, 0.1-
0.7 part of chloro-carbonic acid -9- fluorenyl methyl esters, add in 50-70min, continue to stir 5-10min, system is made to be warming up to naturally often
Temperature reacts 15-20h；It completes that reactant is added to precipitating in 1500-2000 parts of ice water after reacting, filters, wash, it is dry
Obtained 80-90 part solids and 140-180 parts of chromium trioxide are dissolved in 400-500 parts of glacial acetic acid solution afterwards, heated
To solvent refluxing, the purified water of 150-200 parts of addition after 4-8h is reacted, controlling reaction temperature is -1 ~ 4 DEG C, after reacting 15-20h
Filtering, washing obtain intermediate after dry.
A concentration of 65%-95% of the glacial acetic acid solution.
A kind of preparation method of flexure type liquid crystal new material disclosed in the method for the present invention, this programme synthesize a kind of flexure type liquid
Brilliant new material has lower nematic phase transition temperature and wider nematic temperature range, is conducive to the mixed preparing of liquid crystal
And its research of photoelectric properties and application.
Specific implementation mode
The invention is described further below by specific embodiment：
Embodiment 1
A kind of preparation method of flexure type liquid crystal new material, technology of preparing scheme are as follows：
According to mass fraction, by 24.5 parts of 2,5- bis-（P-hydroxybenzene）- 1,3,4- oxadiazoles, 88 parts of intermediate, 45 parts
N, N- dicyclohexylcarbodiimides, 6.5 parts of N, N- lutidines, 0.3 part of 1,3- di-imidogens isoindoline, 0.7
The N of part, bis- (4- pyridyl groups) the naphthalene 4 formyl-2-imides of N'-, 0.02 part of soybean oil base ethyl morpholine nitrogen sulfovinate,
0.02 part of chloroplatinic acid tetrabutylammonium and 350 parts of dichloromethane are added to by thoroughly dry reaction kettle, then taking out
Then vacuum uses the air in high pure nitrogen replacement reaction kettle, be finally filled with high pure nitrogen protection；Then anti-at ambient temperature
It should for 24 hours；Then it filters, the total solvent of filtrate is evaporated, 180 parts of solvent is added in obtained solid and is heated to 55 DEG C of dissolvings,
Stirring 25min postcoolings cooling is recrystallized, and is filtered, dry after washing, you can to obtain a kind of flexure type liquid crystal new material.
The solvent is acetone.
The recrystallization temperature is 6 DEG C.
The intermediate is prepared according to following scheme：According to mass fraction, by 42 parts of parahydroxyben-zaldehyde, 180 parts
Pyridine and 550 parts of dichloromethane be added in reaction kettle, vacuumized after stirring and dissolving, in high pure nitrogen replacement reaction kettle
Air, high pure nitrogen is finally filled with when vacuumizing every time, then under the conditions of ice-water bath, be slowly added to 105 parts to 12
Alkoxy benzene formyl chloride, 0.3 part of chloro-carbonic acid -9- fluorenyl methyl esters, adds in 60min, continues to stir 8min, makes system certainly
It is so warming up to room temperature, reacts 17h；It completes that reactant is added to precipitating in 1700 parts of ice water after reacting, filters, wash, do
Obtain 85 parts of solids and 160 parts of chromium trioxide are dissolved in 450 parts of glacial acetic acid solution after dry, solvent is heated to and returns
It flows, 180 parts of purified water is added after reaction 6h, controlling reaction temperature is 2 DEG C, is filtered after reacting 18h, washing, after drying to obtain the final product
To intermediate.
The glacial acetic acid solution a concentration of 75%.
Embodiment 2
A kind of preparation method of flexure type liquid crystal new material, technology of preparing scheme are as follows：
According to mass fraction, by 23.5 parts of 2,5- bis-（P-hydroxybenzene）- 1,3,4- oxadiazoles, 85 parts of intermediate, 42 parts
N, N- dicyclohexylcarbodiimides, 6.8 parts of N, N- lutidines, 0.1 part of 1,3- di-imidogens isoindoline, 0.1
The N of part, bis- (4- pyridyl groups) the naphthalene 4 formyl-2-imides of N'-, 0.01 part of soybean oil base ethyl morpholine nitrogen sulfovinate,
0.01 part of chloroplatinic acid tetrabutylammonium and 300 parts of dichloromethane are added to by thoroughly dry reaction kettle, then taking out
Then vacuum uses the air in high pure nitrogen replacement reaction kettle, be finally filled with high pure nitrogen protection；Then anti-at ambient temperature
Answer 28h；Then it filters, the total solvent of filtrate is evaporated, 200 parts of solvent is added in obtained solid and is heated to 60 DEG C of dissolvings,
Stirring 30min postcoolings cooling is recrystallized, and is filtered, dry after washing, you can to obtain a kind of flexure type liquid crystal new material.
The solvent is ethyl acetate.
The recrystallization temperature is 6 DEG C.
The intermediate is prepared according to following scheme：According to mass fraction, by 37 parts of parahydroxyben-zaldehyde, 150 parts
Pyridine and 500 parts of dichloromethane be added in reaction kettle, vacuumized after stirring and dissolving, in high pure nitrogen replacement reaction kettle
Air, high pure nitrogen is finally filled with when vacuumizing every time, then under the conditions of ice-water bath, be slowly added to 95 parts to dodecane
Oxygroup chlorobenzoyl chloride, 0.1 part of chloro-carbonic acid -9- fluorenyl methyl esters, adds in 50min, continues to stir 5min, keeps system natural
It is warming up to room temperature, reacts 15h；It completes that reactant is added to precipitating in 1500 parts of ice water after reacting, filters, wash, it is dry
Obtain 80 parts of solids and 140 parts of chromium trioxide are dissolved in 400 parts of glacial acetic acid solution afterwards, are heated to solvent refluxing,
150 parts of purified water is added after reaction 4h, controlling reaction temperature is -1 DEG C, filters, washs after reacting 15h, is obtained after drying
Intermediate.
The glacial acetic acid solution a concentration of 65%.
Embodiment 3
A kind of preparation method of flexure type liquid crystal new material, technology of preparing scheme are as follows：
According to mass fraction, by 26.5 parts of 2,5- bis-（P-hydroxybenzene）- 1,3,4- oxadiazoles, 91 parts of intermediate, 48 parts
N, N- dicyclohexylcarbodiimides, 6.8 parts of N, N- lutidines, 0.5 part of 1,3- di-imidogens isoindoline, 1 part
N, bis- (4- pyridyl groups) the naphthalene 4 formyl-2-imides of N'-, 0.06 part of soybean oil base ethyl morpholine nitrogen sulfovinate, 0.05
The chloroplatinic acid tetrabutylammonium and 400 parts of dichloromethane of part are added to by thoroughly dry reaction kettle, then taking out true
Then sky uses the air in high pure nitrogen replacement reaction kettle, be finally filled with high pure nitrogen protection；Then it reacts at ambient temperature
28h；Then it filters, the total solvent of filtrate is evaporated, 200 parts of solvent is added in obtained solid and is heated to 60 DEG C of dissolvings, stirs
It mixes the cooling of 30min postcoolings to be recrystallized, filter, it is dry after washing, you can to obtain a kind of flexure type liquid crystal new material.
The solvent is absolute ethyl alcohol.
The recrystallization temperature is 8 DEG C.
The intermediate is prepared according to following scheme：According to mass fraction, by 45 parts of parahydroxyben-zaldehyde, 200 parts
Pyridine and 600 parts of dichloromethane be added in reaction kettle, vacuumized after stirring and dissolving, in high pure nitrogen replacement reaction kettle
Air, high pure nitrogen is finally filled with when vacuumizing every time, then under the conditions of ice-water bath, be slowly added to 115 parts to 12
Alkoxy benzene formyl chloride, 0.7 part of chloro-carbonic acid -9- fluorenyl methyl esters, adds in 70min, continues to stir 10min, makes system certainly
It is so warming up to room temperature, reacts 20h；It completes that reactant is added to precipitating in 2000 parts of ice water after reacting, filters, wash, do
Obtain 90 parts of solids and 180 parts of chromium trioxide are dissolved in 500 parts of glacial acetic acid solution after dry, solvent is heated to and returns
It flows, 200 parts of purified water is added after reaction 8h, controlling reaction temperature is 4 DEG C, is filtered after reacting 20h, washing, after drying to obtain the final product
To intermediate.
The glacial acetic acid solution a concentration of 95%.
Comparative example 1
It is not added with pyridine, the other the same as in Example 1.
Comparative example 2
It is not added with 1,3- di-imidogen isoindolines, the other the same as in Example 1.
Comparative example 3
It is not added with N, N- dicyclohexylcarbodiimides, the other the same as in Example 1.
Comparative example 4
It is not added with N, bis- (4- pyridyl groups) the naphthalene 4 formyl-2-imides of N'-, the other the same as in Example 1.
Comparative example 5
It is not added with soybean oil base ethyl morpholine nitrogen sulfovinate, the other the same as in Example 1.
Comparative example 6
It is not added with chloroplatinic acid tetrabutylammonium, the other the same as in Example 1.
Comparative example 7
It is not added with chloro-carbonic acid -9- fluorenyl methyl esters, the other the same as in Example 1.
Table：The performance for the test specimen that different process is made compares.
Claims (5)
1. a kind of preparation method of flexure type liquid crystal new material, technology of preparing scheme are as follows：
According to mass fraction, by 23.5-26.5 parts of 2,5- bis-（P-hydroxybenzene）- 1,3,4- oxadiazoles, 85-91 parts of centre
Body, 42-48 parts of N, N- dicyclohexylcarbodiimides, 6.1-6.8 parts of N, N- lutidines, 0.1-0.5 parts of 1,3- bis-
Bis- (4- pyridyl groups) the naphthalene 4 formyl-2-imides of imido grpup isoindoline, 0.1-1 parts of N, N'-, 0.01-0.06 parts of soybean oil base
Ethyl morpholine nitrogen sulfovinate, 0.01-0.05 parts of chloroplatinic acid tetrabutylammonium and 300-400 parts of dichloromethane add
Enter in by thoroughly dry reaction kettle, then vacuumize, then uses the air in high pure nitrogen replacement reaction kettle, finally fill
Enter high pure nitrogen protection；Then 18-28h is reacted at ambient temperature；Then it filters, the total solvent of filtrate is evaporated, is obtained
150-200 parts of solvent is added in solid and is heated to 50-60 DEG C of dissolving, stirring 20-30min postcoolings cooling is recrystallized,
Filtering, it is dry after washing, you can to obtain a kind of flexure type liquid crystal new material.
2. a kind of preparation method of flexure type liquid crystal new material according to claim 1, it is characterised in that：The solvent
For absolute ethyl alcohol or ethyl acetate or acetone.
3. a kind of preparation method of flexure type liquid crystal new material according to claim 1, it is characterised in that：The knot again
Brilliant temperature is 4-8 DEG C.
4. a kind of preparation method of flexure type liquid crystal new material according to claim 1, it is characterised in that：The centre
Body is prepared according to following scheme：
According to mass fraction, by 37-45 parts of parahydroxyben-zaldehyde, the dichloromethane of 150-200 parts of pyridine and 500-600 part
It is added in reaction kettle, is vacuumized after stirring and dissolving, it is last when vacuumizing every time with the air in high pure nitrogen replacement reaction kettle
Be filled with high pure nitrogen, then under the conditions of ice-water bath, be slowly added to 95-115 parts to dodecyloxy chlorobenzoyl chloride, 0.1-
0.7 part of chloro-carbonic acid -9- fluorenyl methyl esters, add in 50-70min, continue to stir 5-10min, system is made to be warming up to naturally
Room temperature reacts 15-20h；It completes that reactant is added to precipitating in 1500-2000 parts of ice water after reacting, filters, wash, do
Obtained 80-90 part solids and 140-180 parts of chromium trioxide are dissolved in 400-500 parts of glacial acetic acid solution after dry, added
Heat reacts the purified water of 150-200 parts of addition after 4-8h to solvent refluxing, and controlling reaction temperature is -1 ~ 4 DEG C, reacts 15-20h
After filter, wash, intermediate obtained after dry.
5. a kind of preparation method of flexure type liquid crystal new material according to claim 4, it is characterised in that：The ice vinegar
Acid solutions are 65%-95%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112175627A (en) * | 2020-09-24 | 2021-01-05 | 北京科技大学 | Preparation method of blue phase liquid crystal composite material containing fluorene core bending type compound |
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| EP2028253A1 (en) * | 2007-08-24 | 2009-02-25 | Chisso Corporation | Optically isotropic liquid crystal medium and optical device |
| CN101812003A (en) * | 2010-03-30 | 2010-08-25 | 北京航空航天大学 | Small-angle inverted V-shaped fluorine-containing lateral chain ferroelectric liquid crystal compound and synthesis method thereof |
| CN102660295A (en) * | 2012-04-11 | 2012-09-12 | 华南师范大学 | Fluorine-containing azacyclic liquid crystal compound, synthetic method thereof and application thereof |
| CN104204138A (en) * | 2012-03-22 | 2014-12-10 | 华东理工大学 | Liquid crystal blue phase |
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- 2018-05-22 CN CN201810492593.6A patent/CN108774536B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008142177A1 (en) * | 2007-05-23 | 2008-11-27 | Universitat Jaume I | New fluorescent chemical sensors for detection of citrate and citric acid |
| EP2028253A1 (en) * | 2007-08-24 | 2009-02-25 | Chisso Corporation | Optically isotropic liquid crystal medium and optical device |
| CN101812003A (en) * | 2010-03-30 | 2010-08-25 | 北京航空航天大学 | Small-angle inverted V-shaped fluorine-containing lateral chain ferroelectric liquid crystal compound and synthesis method thereof |
| CN104204138A (en) * | 2012-03-22 | 2014-12-10 | 华东理工大学 | Liquid crystal blue phase |
| CN102660295A (en) * | 2012-04-11 | 2012-09-12 | 华南师范大学 | Fluorine-containing azacyclic liquid crystal compound, synthetic method thereof and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112175627A (en) * | 2020-09-24 | 2021-01-05 | 北京科技大学 | Preparation method of blue phase liquid crystal composite material containing fluorene core bending type compound |
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