CN108774536B - A kind of preparation method of flexure type liquid crystal material - Google Patents
A kind of preparation method of flexure type liquid crystal material Download PDFInfo
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- CN108774536B CN108774536B CN201810492593.6A CN201810492593A CN108774536B CN 108774536 B CN108774536 B CN 108774536B CN 201810492593 A CN201810492593 A CN 201810492593A CN 108774536 B CN108774536 B CN 108774536B
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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
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) -1,3,4- oxadiazoles are center molecule, and ester bond is bridged bond, straight chained alkyl is end group, design synthesizes a kind of flexure type liquid crystal new material, has lower nematic phase transition temperature and wider nematic temperature range, is 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 material.
Background technique
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, have flexure mode structure, can induce generate blue phase, while end introduce activity biggish third
Olefin(e) acid ester structure, can further stable 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 biggish 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 positive;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.
CN101586031A provides a kind of liquid crystal composite and its manufacturing method, and liquid crystal composite includes a liquid-crystal compounds
With a nanoparticle, wherein liquid-crystal compounds is optical-compensation bent liquid-crystal compounds, and the main chain of nanoparticle or side chain
On at least have an acryl functional group.The content of nanoparticle in liquid crystal composite compositing formula is 0.1-2wt%, heavy
Percentage system is measured on the basis of the weight of liquid crystal composite.When nanoparticle is added to original liquid-crystal compounds, liquid crystal can be made
Bending status is rapidly diverted to by divergence state, makes liquid crystal display device that can be rapidly achieved stable state in initial driving, without special
The driving circuit of high voltage has faster answer speed.
The flexure type liquid crystal material of the above invention and prior art preparation is there are nematic phase transition temperature is higher, nematic phase
The relatively narrow problem of temperature range limits the further application and development of this kind of material.
Summary of the invention
To solve the above-mentioned problems, the present invention provides a kind of preparation methods of flexure type liquid crystal material.
A kind of preparation method of flexure type liquid crystal 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
Intermediate, 42-48 parts of N, N- dicyclohexylcarbodiimide, 6.1-6.8 parts of N, N- lutidines, the 1 of 0.1-0.5 parts,
3- di-imidogen isoindoline, 0.1-1 parts of N, bis- (4- pyridyl group) the naphthalene 4 formyl-2-imides of 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
Alkane is added to by then vacuumizing in thoroughly dry reaction kettle, then uses the air in high pure nitrogen replacement reaction kettle, most
After be filled with high pure nitrogen protection;Then 18-28h is reacted at room temperature;Then it filters, the total solvent of filtrate is evaporated, is obtained
To solid in 150-200 part of solvent be added be heated to 50-60 DEG C of dissolution, cool after stirring 20-30min and tied again
Crystalline substance, filtering is dry after washing, and a kind of flexure type liquid crystal material can be obtained.
The solvent is dehydrated 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 dichloro of 150-200 parts of pyridine and 500-600 part
Methane is added in reaction kettle, is vacuumized after stirring and dissolving, with the air in high pure nitrogen replacement reaction kettle, when vacuumizing every time
Finally 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 parts of chloro-carbonic acid -9- fluorenyl methyl ester, adds in 50-70min, continues to stir 5-10min, system is made to heat up naturally
To room temperature, 15-20h is reacted;Reactant is added to precipitating in 1500-2000 parts of ice water after completing reaction, is filtered, washing,
Obtained 80-90 part solid and 140-180 parts of chromium trioxide are dissolved in 400-500 parts of glacial acetic acid solution after drying,
It is heated to solvent refluxing, reacts the purified water of 150-200 parts of addition after 4-8h, control reaction temperature is -1 ~ 4 DEG C, reacts 15-
It filters, washs after 20h, obtain intermediate after dry.
The glacial acetic acid solution concentration is 65%-95%.
A kind of preparation method of flexure type liquid crystal material, this programme disclosed in the method for the present invention synthesize a kind of flexure type liquid crystal
Material, have lower nematic phase transition temperature and wider nematic temperature range, be conducive to liquid crystal mixed preparing and its
The research of photoelectric properties and application.
Specific embodiment
The invention is described further below by specific embodiment:
Embodiment 1
A kind of preparation method of flexure type liquid crystal 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 of N, N- dicyclohexylcarbodiimide, 6.5 parts of N, N- lutidines, 0.3 part of 1,3- di-imidogen isoindoline,
Bis- (4- pyridyl group) the naphthalene 4 formyl-2-imides of 0.7 part of N, N'-, 0.02 part of soybean oil base ethyl morpholine nitrogen ethyl sulfuric acid
Salt, 0.02 part of chloroplatinic acid tetrabutylammonium and 350 parts of methylene chloride are added in the reaction kettle by thoroughly drying, so
After vacuumize, then with the air in high pure nitrogen replacement reaction kettle, be finally filled with high pure nitrogen protection;Then in room temperature condition
Lower reaction is for 24 hours;Then filter, the total solvent of filtrate be evaporated, be added in obtained solid 180 parts of solvent be heated to 55 DEG C it is molten
It solves, cools and recrystallized after stirring 25min, filtered, it is dry after washing, a kind of flexure type liquid crystal material can be obtained.
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, and 180 parts
Pyridine and 550 parts of methylene chloride 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 ester, adds in 60min, continues to stir 8min, keeps system natural
It is warming up to room temperature, reacts 17h;Reactant is added to precipitating in 1700 parts of ice water after completing reaction, is filtered, is washed, it is dry
Obtain 85 parts of solids and 160 parts of chromium trioxide are dissolved in 450 parts of glacial acetic acid solution afterwards, are heated to solvent refluxing,
180 parts of purified water is added after reaction 6h, controlling reaction temperature is 2 DEG C, filters, washing after reacting 18h, is in obtaining after dry
Mesosome.
The glacial acetic acid solution concentration is 75%.
Embodiment 2
A kind of preparation method of flexure type liquid crystal 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 of N, N- dicyclohexylcarbodiimide, 6.8 parts of N, N- lutidines, 0.1 part of 1,3- di-imidogen isoindoline,
Bis- (4- pyridyl group) the naphthalene 4 formyl-2-imides of 0.1 part of N, N'-, 0.01 part of soybean oil base ethyl morpholine nitrogen ethyl sulfuric acid
Salt, 0.01 part of chloroplatinic acid tetrabutylammonium and 300 parts of methylene chloride are added in the reaction kettle by thoroughly drying, so
After vacuumize, then with the air in high pure nitrogen replacement reaction kettle, be finally filled with high pure nitrogen protection;Then in room temperature condition
Lower reaction 28h;Then filter, the total solvent of filtrate be evaporated, be added in obtained solid 200 parts of solvent be heated to 60 DEG C it is molten
It solves, cools and recrystallized after stirring 30min, filtered, it is dry after washing, a kind of flexure type liquid crystal material can be obtained.
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, and 150 parts
Pyridine and 500 parts of methylene chloride 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 ester, adds in 50min, continues to stir 5min, rises system naturally
Temperature arrives room temperature, reacts 15h;Reactant is added to precipitating in 1500 parts of ice water after completing reaction, is filtered, washing, after dry
Obtain 80 parts of solids and 140 parts of chromium trioxide are dissolved in 400 parts of glacial acetic acid solution, are heated to solvent refluxing, instead
It answers 150 parts of purified water is added after 4h, control reaction temperature is -1 DEG C, filters, washs after reacting 15h, is obtained after dry
Mesosome.
The glacial acetic acid solution concentration is 65%.
Embodiment 3
A kind of preparation method of flexure type liquid crystal 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 of N, N- dicyclohexylcarbodiimide, 6.8 parts of N, N- lutidines, 0.5 part of 1,3- di-imidogen iso-indoles
Quinoline, 1 part of N, bis- (4- pyridyl group) the naphthalene 4 formyl-2-imides of N'-, 0.06 part of soybean oil base ethyl morpholine nitrogen ethyl sulfuric acid
Salt, 0.05 part of chloroplatinic acid tetrabutylammonium and 400 parts of methylene chloride are added in the reaction kettle by thoroughly drying, so
After vacuumize, then with the air in high pure nitrogen replacement reaction kettle, be finally filled with high pure nitrogen protection;Then in room temperature condition
Lower reaction 28h;Then filter, the total solvent of filtrate be evaporated, be added in obtained solid 200 parts of solvent be heated to 60 DEG C it is molten
It solves, cools and recrystallized after stirring 30min, filtered, it is dry after washing, a kind of flexure type liquid crystal material can be obtained.
The solvent is dehydrated 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, and 200 parts
Pyridine and 600 parts of methylene chloride 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 ester, adds in 70min, continues to stir 10min, makes system certainly
It is so warming up to room temperature, reacts 20h;Reactant is added to precipitating in 2000 parts of ice water after completing reaction, is filtered, is washed, is done
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
Stream reacts the purified water of 200 parts of addition after 8h, and control reaction temperature is 4 DEG C, filters, washs after reacting 20h, after drying to obtain the final product
To intermediate.
The glacial acetic acid solution concentration is 95%.
Comparative example 1
Pyridine, the other the same as in Example 1 is not added.
Comparative example 2
1,3- di-imidogen isoindoline, the other the same as in Example 1 is not added.
Comparative example 3
N, N- dicyclohexylcarbodiimide, the other the same as in Example 1 is not added.
Comparative example 4
N, bis- (4- pyridyl group) the naphthalene 4 formyl-2-imides of N'-, the other the same as in Example 1 is not added.
Comparative example 5
Soybean oil base ethyl morpholine nitrogen sulfovinate, the other the same as in Example 1 is not added.
Comparative example 6
Chloroplatinic acid tetrabutylammonium, the other the same as in Example 1 is not added.
Comparative example 7
Chloro-carbonic acid -9- fluorenyl methyl ester, the other the same as in Example 1 is not added.
Table: the performance for the test specimen that different process is made compares.
Claims (4)
1. a kind of preparation method of flexure type liquid crystal material, the preparation method is as follows: according to mass fraction, by 23.5-26.5 parts
(the p-hydroxybenzene) -1,3,4- of 2,5- bis- oxadiazoles, 85-91 parts of flexure type liquid crystal material intermediate, 42-48 parts of N, N- bis-
Carbodicyclo hexylimide, 6.1-6.8 parts of N, N- lutidines, 0.1-0.5 parts of 1,3- di-imidogen isoindoline, 0.1-
Bis- (4- pyridyl group) the naphthalene 4 formyl-2-imides of 1 part of N, N'-, 0.01-0.06 parts of soybean oil base ethyl morpholine nitrogen ethyl sulphur
Hydrochlorate, 0.01-0.05 parts of chloroplatinic acid tetrabutylammonium and 300-400 parts of methylene chloride are added to by thoroughly drying
It in reaction kettle, then vacuumizes, then with the air in high pure nitrogen replacement reaction kettle, is finally filled with high pure nitrogen protection;So
React 18-28h at room temperature afterwards;Then it filters, the total solvent of filtrate is evaporated, 150-200 is added in obtained solid
The solvent of part is heated to 50-60 DEG C of dissolution, cools and is recrystallized after stirring 20-30min, is filtered, dry after washing, i.e.,
A kind of flexure type liquid crystal material can be obtained,
The flexure type liquid crystal material intermediate is prepared according to following scheme: according to mass fraction, by 37-45 parts to hydroxyl
The methylene chloride of benzaldehyde, 150-200 parts of pyridine and 500-600 part is added in reaction kettle, is vacuumized, is used after stirring and dissolving
Air in high pure nitrogen replacement reaction kettle is finally filled with high pure nitrogen when vacuumizing every time, then under the conditions of ice-water bath, delay
It is slow be added 95-115 parts to dodecyloxy chlorobenzoyl chloride, 0.1-0.7 parts of chloro-carbonic acid -9- fluorenyl methyl ester, in 50-70min
It inside adds, continues to stir 5-10min, system is made to be warming up to room temperature naturally, react 15-20h;Reactant is added after completing reaction
The precipitating into 1500-2000 parts of ice water filters, washing, by obtained 80-90 part solid and the three of 140-180 parts after drying
Chromium oxide is dissolved in 400-500 parts of glacial acetic acid solution, is heated to solvent refluxing, is added 150-200 parts after reacting 4-8h
Purified water, control reaction temperature are -1-4 DEG C, filter, wash after reacting 15-20h, obtain flexure type liquid crystal material after dry
Intermediate.
2. a kind of preparation method of flexure type liquid crystal material according to claim 1, it is characterised in that: the solvent is
Dehydrated alcohol or ethyl acetate or acetone.
3. a kind of preparation method of flexure type liquid crystal material according to claim 1, it is characterised in that: the recrystallization
Temperature is 4-8 DEG C.
4. a kind of preparation method of flexure type liquid crystal material according to claim 1, it is characterised in that: the glacial acetic acid
Solution concentration is 65%-95%.
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