CN107602392A - A kind of reactive liquid crystalline monomeric compound, preparation method and application - Google Patents
A kind of reactive liquid crystalline monomeric compound, preparation method and application Download PDFInfo
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- CN107602392A CN107602392A CN201710829288.7A CN201710829288A CN107602392A CN 107602392 A CN107602392 A CN 107602392A CN 201710829288 A CN201710829288 A CN 201710829288A CN 107602392 A CN107602392 A CN 107602392A
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Abstract
The invention discloses a kind of reactive liquid crystalline monomeric compound, preparation method and application, the general structure of the compound is：In formula, R is H or methyl, and n is 2~8 natural number.Starting compound E, Pentafluorophenol obtain reactive liquid crystalline monomeric compound by reaction, post processing and purge process, and the compound is used for the application for reducing the driving voltage of blue phase liquid crystal.
Description
Technical field
The invention belongs to field of liquid crystals, is related to blue phase liquid crystal, and in particular to a kind of reactive liquid crystalline monomeric compound, is applicable
Converging network is generated when mixed liquid crystal is prepared to widen the temperature range of blue phase, reduces driving voltage.
Background technology
After polymer stabilizing blue phase technology successfully widens the temperature range of blue phase, blue phase liquid crystal is described as liquid crystal display of future generation
Hope.Blue phase liquid crystal Display Technique based on Kerr effect has relatively wide temperature range, the gray-tone response of sub- Millisecond
Speed, it is easy to large-size screen monitors making, and show in plane the features such as without oriented layer and cause increasing concern with optics aspect.
Blue phase liquid crystal is respectively that temperature range is not wide enough and driving voltage is higher in the presence of two big problems.The blue phase liquid crystal system that will have polymerize
In liquid crystal elution after, then pour into achiral liquid crystal, the temperature range that the method for this polymer stabilizing solves blue phase substantially is asked
Topic.But the driving voltage of blue phase liquid crystal is too high to turn into researcher's urgent problem, practical to blue phase liquid crystal have
Important meaning and value.In the prior art, for blue phase liquid crystal driving voltage it is too high the problem of can by using height turn round
The compound of square reduces driving voltage, but this kind of compound structure is complicated, synthetic route length, high expensive, is unfavorable for producing
Industry.
The content of the invention
In view of the deficienciess of the prior art, it is an object of the present invention to provide the present invention to provide a kind of reactive liquid crystalline
Monomeric compound, preparation method and application, solves the high technical problem of the driving voltage of blue phase liquid crystal in the prior art.
In order to solve the above-mentioned technical problem, the present invention, which adopts the following technical scheme that, is achieved：
A kind of reactive liquid crystalline monomeric compound, the general structure of the compound are：
In formula, R is H or methyl, and n is 2~8 natural number.
The present invention also has following distinguishing feature：
Preferably, described n is 2~6 natural number.
It is furthermore preferred that described n is 2,3,6.
The present invention gives a kind of preparation method of reactive liquid crystalline monomeric compound described above, and this method is included such as
Lower reaction equation：
Specifically course of reaction is：
Starting compound E, Pentafluorophenol, dicyclohexylcarbodiimide and DMAP are added, by reacting, after
Processing and purifying obtain reactive liquid crystalline monomeric compound；
Wherein, the proportion relation between raw material is：1mol compound E are often added, corresponds to and adds 1~2mol Pentafluorophenols, 1
~2mol dicyclohexylcarbodiimides, 0.03~1mol DMAPs.
Further, the course of reaction of this method is as follows：
This method specifically includes following steps：
Step 1, compound A and compound B obtain compound C in the basic conditions；
Step 2, compound C obtain compound D by being acidified after alkaline hydrolysis；
Step 3, compound D react to obtain compound E with methacrylic acid, acrylic acid or acryloyl chloride；
Step 4, compound E are esterified to obtain compound F with Pentafluorophenol.
Reactive liquid crystalline monomeric compound as described above is used for the application for reducing the driving voltage of blue phase liquid crystal.
The present invention compared with prior art, has the following technical effect that：
The reactive liquid crystalline monomeric compound of present invention raw material in preparation process is easy to get, and synthetic route is simple, suitable rule
Modelling produces.Its polarity is bigger with respect to other fluorobenzene classes, there is larger application value.
Fluorine-containing polymer monomer has relatively low surface tension, and it is applied can in polymer stabilizing blue phase liquid crystal
The grappling effect to blue phase liquid crystal is reduced, so as to effectively reduce the driving voltage of blue phase liquid crystal, and improves hesitation.
Brief description of the drawings
Fig. 1 is M6BA 1HNMR collection of illustrative plates.
Fig. 2 is compound M6BAF GC-MS collection of illustrative plates.
Fig. 3 is compound M6BAF1HNMR collection of illustrative plates.
Fig. 4 is compound M6BAF13CNMR collection of illustrative plates.
Fig. 5 is compound M6BAF19FNMR collection of illustrative plates.
Fig. 6 is M2BA1HNMR collection of illustrative plates.
Fig. 7 is M4BA1HNMR collection of illustrative plates.
Fig. 8 is M4BA FTIR collection of illustrative plates.
Fig. 9 is A6BA GC-MS collection of illustrative plates.
Explanation is further explained in detail to the particular content of the present invention with reference to embodiments.
Embodiment
The present invention is to very slightly a kind of reactive liquid crystalline monomeric compound, the general structure of the compound are：
The concrete structure formula of described reactive liquid crystalline monomeric compound and corresponding abbreviation code are as follows：
It should be noted that：Above-mentioned pentafluorophenyl esters are that Pentafluorophenol is made with corresponding acid by being esterified, and are prepared on above-mentioned
State corresponding sour abbreviation code used by pentafluorophenyl esters be followed successively by A2BA, M2BA, A3BA, M3BA, A4BA, M4BA,
A5BA、M5BA、A6BA、M6BA、A7BA、M7BA、A8BA、M8BA。
It should be noted that：In the present invention in the sampling result of gas-chromatography or liquid chromatogram, certain so-called material
Content is less than 0.5% and referred in the obtained spectrogram of detection, and the percentage that the peak area of the material accounts for total peak area is less than
0.5%.
Specific embodiment of the invention given below is, it is necessary to which explanation is that the invention is not limited in implement in detail below
Example, all equivalents done on the basis of technical scheme each fall within protection scope of the present invention.
Embodiment 1：
The present embodiment provides a kind of reactive liquid crystalline monomeric compound, the structural formula such as abbreviation code M6BAF of the compound
It is shown, i.e. compound 4- (6- (methacryloxy) hexyloxy) benzoic acid pentafluorophenyl esters.
The preparation method of the compound of the present embodiment specifically includes following steps：
Step 1：The synthesis of 4- (6- acetyl oxygen hexyloxy)-methyl benzoate
DMF (abbreviation DMF) 110g is added into 250mL there-necked flasks, stirring is opened, is separately added into 6-
Mecoral acetic acid esters 12.6g, methyl p-hydroxybenzoate 9g, KI 0.5g, potassium carbonate 13.50g.Open and be heated to 130
DEG C, after the reaction 2 hours of 127~133 DEG C of temperature control, gas chromatographic detection is sampled every half an hour, treats raw material P-hydroxybenzoic acid first
Ester, which is less than 0.5%, to be stopped reacting.When being cooled to 40 DEG C, filter while hot, filter out inorganic salts, filtrate decompression concentration, steam about 100g
DMF, 40 DEG C are cooled to, add 300mL water, stirred 20min, be filtrated to get yellow crude 15.4g, GC：96%, yield：
88.45%.
Step 2：The synthesis of 4- (6- hydroxyls hexyloxy) benzoic acid
90g ethanol is added in 250mL there-necked flasks, stirring, it is thick to add 4- (6- acetyl oxygen hexyloxy)-methyl benzoate
Product 30g, 12g sodium hydroxide, heating response, there are a large amount of white solids to produce.Back flow reaction 3h, liquid chromatographic detection, raw material
Less than 0.5%, heating is closed, stops reaction.About 40 DEG C are cooled to, adds water 100g, 38g concentrated hydrochloric acid is slowly added to, pH is adjusted
To 1, stir 2 hours, fully acidifying.White solid is filtrated to get, respectively with 10g water and 10g ethanol rinse filter cakes.Obtain white
Powder 22.6g, liquid chromatogram content are more than 99.5%, yield：93.06%.50 DEG C of vacuum drying 12h.
Step 3：The synthesis of 4- (6- (methacryloxy) hexyloxy) benzoic acid (M6BA)
85g toluene, 30g methacrylic acids are added in 250mL there-necked flasks, is stirred, adds 8.0g 4- (the own oxygen of 6- hydroxyls
Base)-benzoic acid, 2.0g p-methyl benzenesulfonic acid (abbreviation TsOH) and 0.6g DBPC 2,6 ditertiary butyl p cresols (abbreviation BHT).Nitrogen is protected
Shield, heating, when system rises to certain temperature (70 DEG C or so), is become to clarify, quick backflow divides water to separate to anhydrous by suspension
When, liquid chromatographic detection is sampled, when raw material is less than 0.2%, cooling, stops reaction.
40g ethyl acetate and 30g water stirring 30min are added into system, is heated to 60 DEG C, 300mL is washed 2 times,
System temperature is down to 25 DEG C, filtering, then 50 DEG C of washing organic phases of 300g every time, washs 2 times, to aqueous phase pH=6 or so, point
Go out organic phase, be concentrated under reduced pressure into solid precipitation, add 25g ethanol, heat of solution, be cooled to 50 DEG C, blowing, freezed after cooling
4h, filtering, white solid 7.18g is obtained, main content is more than 98%, yield：69.81%.50 DEG C of vacuum drying 12h.
M6BA's1HNMR collection of illustrative plates is as shown in figure 1, specific nuclear magnetic data is as follows：
1H-NMR(CDCl3/TMS):δ=1.505~1.569 (m, 4H), 1.747~1.881 (m, 4H), 1.981 (s,
1H), 4.053~4.079 (t, 2H, J=6.5), 4.191~4.218 (t, 2H, J=6.5), 5.586 (s, 1H), 6.137 (s,
1H), 6.954~6.971 (d, 2H, J=8.5), 8.085~8.102 (d, 2H, J=8.5).
It is M6BA that the compound is can be inferred that from Fig. 1.
Step 4：The synthesis of 4- (6- (methacryloxy) hexyloxy) benzoic acid pentafluorophenyl esters (M6BAF)
10g (32.64mmol) M6BA, 7.2g (39.12mmol) Pentafluorophenol, 60mL dichloros are added in 100mL single port bottles
Methane, 8.8g (42.65mmol) dicyclohexylcarbodiimide (abbreviation DCC) and 0.4g (3.27mmol) DMAP
(abbreviation DMAP), stirring at normal temperature reaction 16h, liquid chromatogram sampling raw material M6BA are less than 0.5%, stop reaction, filter, concentration.
Silica gel column chromatography obtains white solid product 12.4g, liquid chromatogram content 99.5%, yield 80.41%.
The GC-MS collection of illustrative plates of product as shown in Fig. 21HNMR collection of illustrative plates as shown in figure 3,13CNMR collection of illustrative plates as shown in figure 4,19FNMR
As shown in figure 5, specific nuclear magnetic data is as follows：
1H-NMR(CDCl3/TMS,500MHz):δ=1.462~1.577 (m, 4H), 1.708~1.764 (m, 2H),
1.827~1.882 (m, 2H), 1.948 (s, 3H), 4.054~4.079 (t, 2H, J=6.5), 4.160~4.187 (t, 2H, J
=6.5), 5.556~5.562 (t, 1H, J=1.5), 6.105 (s, 1H), 6.983~7.001 (d, 2H, J=9), 8.130~
8.148 (d, 2H, J=9).
13C-NMR(CDCl3/TMS,125MHz):δ=18.343,25.678,25.772,28.546,28.936,
64.592,68.260,114.633,118.816,125.296,133.004,136.489,136.918,138.961,
140.403,142.506,162.292,164.352,167.559。
19F-NMR(CDCl3/TMS,470MHz):δ=- 162.550 (t, 2F, J=20.92), -158.364 (t, 1F, J=
22.80), -152.578 (d, 2F, J=19.27).
Characterization result from Fig. 2 to Fig. 5 is it can be concluded that product manufactured in the present embodiment is M6BAF.
Reactive liquid crystalline monomeric compound made from the present embodiment is used for the application for reducing the driving voltage of blue phase liquid crystal.
Embodiment 2：
The present embodiment provides a kind of reactive liquid crystalline monomeric compound, the structural formula such as abbreviation code M2BAF of the compound
It is shown, i.e. compound 4- (2- (methacryloxy) ethyoxyl) benzoic acid pentafluorophenyl esters.
The preparation method of the compound of the present embodiment specifically includes following steps：
Step 1：The synthesis of 4- (2- acetyl oxygen ethyoxyl)-methyl benzoate
DMF 110g are added into 250mL there-necked flasks, stirring is opened, ethylene chlorhydrin acetic acid esters 15g is separately added into, to hydroxyl
Methyl benzoate 16.76g, KI 0.5g, potassium carbonate 16.50g.Open and be heated to 130 DEG C, 127-133 DEG C of reaction 2 of temperature control
After hour, gas chromatographic detection is sampled every half an hour, treats that raw material methyl p-hydroxybenzoate is less than 0.5% and stops reacting.Drop
When temperature is to 40 DEG C, filter while hot, filter out inorganic salts, filtrate decompression concentration, steam about 100g DMF, be cooled to 40 DEG C, add
300mL water, 20min is stirred, is filtrated to get yellow crude 26g, GC：98%, yield：89.16%.
Step 2：The synthesis of 4- (2- hydroxyl-oxethyls)-benzoic acid
90g ethanol is added in 250mL there-necked flasks, stirring, it is thick to add 4- (2- acetyl oxygen ethyoxyl)-methyl benzoate
Product 20g, 10g sodium hydroxide, heating response, there are a large amount of white solids to produce.Back flow reaction 3h, liquid chromatographic detection, raw material
Less than 0.5%, heating is closed, stops reaction.About 40 DEG C are cooled to, adds water 100g, 35g concentrated hydrochloric acid is slowly added to, pH is adjusted
To 1, stir 2 hours, fully acidifying.White solid is filtrated to get, respectively with 10g water and 10g ethanol rinse filter cakes.Obtain white
Powder 14.8g, liquid chromatogram content are more than 99.5%, yield：96.77%.50 DEG C of vacuum drying 12h.
Step 3：The synthesis of 4- (2- (methacryloxy) ethyoxyl) benzoic acid (M2BA)
85g toluene, 30g methacrylic acids are added in 250mL there-necked flasks, is stirred, adds 6.4g 4- (2- '-hydroxyethoxies
Base) benzoic acid, 2.0g TsOH and 0.6g BHT.Nitrogen is protected, heating, when system rises to certain temperature (70 DEG C or so), by hanging
Turbid becomes to clarify, and when quick backflow divides water to anhydrous separate, samples liquid chromatographic detection, when raw material is less than 0.2%, cooling,
Stop reaction.
40g ethyl acetate and 30g water stirring 30min are added into system, is heated to 60 DEG C, 300mL is washed 2 times,
System temperature is down to 25 DEG C, filtering, then 50 DEG C of washing organic phases of 300g every time, washs 2 times, to aqueous phase pH=6 or so, point
Go out organic phase, be concentrated under reduced pressure into solid precipitation, add 25g ethanol, heat of solution, be cooled to 50 DEG C, blowing, freezed after cooling
4h, filtering, white solid 6.7g is obtained, main content is more than 98%, yield：76.21%.50 DEG C of vacuum drying 12h.
M2BA's1HNMR is shown in accompanying drawing 6, can be inferred that the compound is M2BA from Fig. 6.
Step 4：The synthesis of 4- (2- (methacryloxy) ethyoxyl) benzoic acid pentafluorophenyl esters (M2BAF)
10g (39.96mmol) M2BA, 8.8g (47.81mmol) Pentafluorophenol, 60mL dichloros are added in 100mL single port bottles
Methane, 8.8g (42.65mmol) DCC and 0.4g (3.27mmol) DMAP, stirring at normal temperature reaction 16h, liquid chromatogram sampling raw material
M2BA is less than 0.5%, stops reaction, filters, concentration.Silica gel column chromatography obtains white solid product 12g, liquid chromatogram content
99.5%, yield 72.14%.
Reactive liquid crystalline monomeric compound made from the present embodiment is used for the application for reducing the driving voltage of blue phase liquid crystal.
Embodiment 3：
The present embodiment provides a kind of reactive liquid crystalline monomeric compound, the structural formula such as abbreviation code A3BAF of the compound
It is shown, i.e. compound 4- (6- (acryloxy) propoxyl group) benzoic acid pentafluorophenyl esters.
The preparation method of the compound of the present embodiment specifically includes following steps：
Step 1：The synthesis of 4- (3- acetyl oxygen propoxyl group)-methyl benzoate
DMF 110g are added into 250mL there-necked flasks, stirring is opened, 3- chloropropyl alcohol acetic acid esters 15g is separately added into, to hydroxyl
Methyl benzoate 15.88g, KI 0.5g, potassium carbonate 15.20g.Open and be heated to 130 DEG C, 127-133 DEG C of reaction 2 of temperature control
After hour, gas chromatographic detection is sampled every half an hour, treats that raw material methyl p-hydroxybenzoate is less than 0.5% and stops reacting.Drop
When temperature is to 40 DEG C, filter while hot, filter out inorganic salts, filtrate decompression concentration, steam about 100g DMF, be cooled to 40 DEG C, add
300mL water, 20min is stirred, is filtrated to get yellow crude 25.3g, GC：97%, yield：91.36%.
Step 2：The synthesis of 4- (3- hydroxy propyloxy groups) benzoic acid
90g ethanol is added in 250mL there-necked flasks, stirring, it is thick to add 4- (3- acetyl oxygen propoxyl group) methyl benzoate
Product 23g, 11.2g sodium hydroxide, heating response, there are a large amount of white solids to produce.Back flow reaction 3h, liquid chromatographic detection are former
Material is less than 0.5%, closes heating, stops reaction.About 40 DEG C are cooled to, adds water 100g, is slowly added to 39.5g concentrated hydrochloric acid, will
PH is adjusted to 1, stirs 2 hours, fully acidifying.White solid is filtrated to get, respectively with 10g water and 10g ethanol rinse filter cakes.Obtain
White powder 17.1g, liquid chromatogram content are more than 99.5%, yield：95.59%.50 DEG C of vacuum drying 12h.
Step 3：The synthesis of 4- (3- (acryloxy) propoxyl group) benzoic acid (A3BA)
80g toluene, 20g acrylic acid are added in 250mL there-necked flasks, is stirred, adds 9.0g 4- (3- hydroxy propyloxy groups)
Benzoic acid, 2.3g TsOH and 0.5g BHT.Nitrogen is protected, heating, when system rises to certain temperature (70 DEG C or so), by suspended
Liquid becomes to clarify, and when quick backflow divides water to anhydrous separate, samples liquid chromatographic detection, when raw material is less than 0.2%, cooling, stops
Only react.
40g ethyl acetate and 30g water stirring 30min are added into system, is heated to 60 DEG C, 300mL is washed 2 times,
System temperature is down to 25 DEG C, filtering, then 50 DEG C of washing organic phases of 300g every time, washs 2 times, to aqueous phase pH=6 or so, point
Go out organic phase, be concentrated under reduced pressure into solid precipitation, add 25g ethanol, heat of solution, be cooled to 50 DEG C, blowing, freezed after cooling
4h, filtering, white solid 8.05g is obtained, main content is more than 98%, yield：70.13%.50 DEG C of vacuum drying 12h.
Step 4：The synthesis of 4- (3- (acryloxy) propoxyl group) benzoic acid pentafluorophenyl esters (A3BAF)
8g (31.97mmol) A3BA, 6.5g (35.31mmol) Pentafluorophenol, 60mL dichloromethanes are added in 100mL single port bottles
Alkane, 7.8g (37.80mmol) DCC and 0.4g (3.27mmol) DMAP, stirring at normal temperature reaction 16h, liquid chromatogram sampling raw material
A3BA is less than 0.5%, stops reaction, filters, concentration.Silica gel column chromatography obtains white solid A3BAF 11.2g, and liquid chromatogram contains
Amount 99.5%, yield 84.16%.
In the step 3 of the present embodiment, acrylic acid can also be substituted with acryloyl chloride, obtain A3BA, concrete operations are as follows：
80g toluene and 9.0g 4- (3- hydroxy propyloxy groups) benzoic acid are added in 250mL there-necked flasks, under nitrogen protection, control temperature is 0
± 5 DEG C, 5.12g acryloyl chlorides are added dropwise, after being added dropwise completely, insulation reaction 1h samples liquid chromatographic detection, and raw material is less than 0.2%
When, cooling, stop reaction.
Post-processing operation is identical with step 3 post-processing operation.
Reactive liquid crystalline monomeric compound made from the present embodiment is used for the application for reducing the driving voltage of blue phase liquid crystal.
Embodiment 4：
The present embodiment provides a kind of reactive liquid crystalline monomeric compound, the structural formula such as abbreviation code M3BAF of the compound,
Shown in M4BAF, M5BAF, M7BAF and M8BAF.
The preparation method of the compound of the present embodiment is：With reference to embodiment 1,6- Mecorals acetic acid esters in step 1 is distinguished
Replace with 3- chloropropyl alcohols acetic acid esters, 4- neoprenes alcohol acetic ester, 5- chlorine amylalcohols acetic acid esters, 7- chlorine enanthol acetic acid esters and 8- chlorine octanol second
Acid esters, other raw materials are identical with operation, obtain M3BAF, M4BAF, M5BAF, M7BAF and M8BAF compounds.
Wherein, M4BA1HNMR and FTIR collection of illustrative plates is shown in accompanying drawing 7 and accompanying drawing 8.
Reactive liquid crystalline monomeric compound made from the present embodiment is used for the application for reducing the driving voltage of blue phase liquid crystal.
Embodiment 5：
The present embodiment provides a kind of reactive liquid crystalline monomeric compound, the structural formula such as abbreviation code A2BAF of the compound,
Shown in A4BAF, A5BAF, A6BAF, A7BAF and A8BAF.
The preparation method of the compound of the present embodiment is：With reference to embodiment 3,3- chloropropyl alcohols acetic acid esters in step 1 is distinguished
Replace with ethylene chlorhydrin acetic acid esters, 4- neoprenes alcohol acetic ester, 5- chlorine amylalcohols acetic acid esters, 6- Mecorals acetic acid esters, 7- chlorine enanthol second
Acid esters and 8- chlorine octanol acetic acid esters, other raw materials are identical with operation, obtain A2BAF, A4BAF, A5BAF, A6BAF, A7BAF and
A8BAF compounds.
Wherein, A6BA GC-MS is shown in accompanying drawing 9.
Reactive liquid crystalline monomeric compound made from the present embodiment is used for the application for reducing the driving voltage of blue phase liquid crystal.
Claims (8)
1. a kind of reactive liquid crystalline monomeric compound, it is characterised in that the general structure of the compound is：
In formula, R is H or methyl, and n is 2~8 natural number.
2. reactive liquid crystalline monomeric compound as claimed in claim 1, it is characterised in that described n is 2~6 natural number.
3. reactive liquid crystalline monomeric compound as claimed in claim 2, it is characterised in that described n is 2,3 or 6.
4. a kind of preparation method of reactive liquid crystalline monomeric compound as described in claims 1 to 3 any claim, it is special
Sign is that this method includes following reaction equation：
Specifically course of reaction is：
Starting compound E, Pentafluorophenol, dicyclohexylcarbodiimide and DMAP are added, by reaction, post processing
Reactive liquid crystalline monomeric compound is obtained with purifying.
5. preparation method as claimed in claim 4, it is characterised in that the proportion relation between described raw material is：Often plus
Enter 1mol compound E, it is corresponding to add 1~2mol Pentafluorophenols, 1~2mol dicyclohexylcarbodiimides, 0.03~1mol 4- bis-
Methylamino pyridine.
6. preparation method as claimed in claim 4, it is characterised in that the course of reaction of this method is as follows：
This method specifically includes following steps：
Step 1, compound A and compound B obtain compound C in the basic conditions；
Step 2, compound C obtain compound D by being acidified after alkaline hydrolysis；
Step 3, compound D react to obtain compound E with methacrylic acid, acrylic acid or acryloyl chloride；
Step 4, compound E are esterified to obtain compound F with Pentafluorophenol.
7. the reactive liquid crystalline monomeric compound as described in claims 1 to 3 any claim is used for reducing blue phase liquid crystal
The application of driving voltage.
8. reactive liquid crystalline monomeric compound is used for made from the preparation method as described in claim 4 to 6 any claim
Reduce the application of the driving voltage of blue phase liquid crystal.
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| CN109534968A (en) * | 2018-11-15 | 2019-03-29 | 广东广山新材料股份有限公司 | A kind of unsaturation fluorocarbons and its preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109534968A (en) * | 2018-11-15 | 2019-03-29 | 广东广山新材料股份有限公司 | A kind of unsaturation fluorocarbons and its preparation method and application |
| CN109534968B (en) * | 2018-11-15 | 2022-07-08 | 广东广山新材料股份有限公司 | A kind of unsaturated fluorocarbon compound and its preparation method and application |
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