CN1928004A - Liquid crystal compound 4'-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof - Google Patents
Liquid crystal compound 4'-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof Download PDFInfo
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- CN1928004A CN1928004A CN200610139011.3A CN200610139011A CN1928004A CN 1928004 A CN1928004 A CN 1928004A CN 200610139011 A CN200610139011 A CN 200610139011A CN 1928004 A CN1928004 A CN 1928004A
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- allyloxy
- fluoro
- liquid crystal
- phenylazobenzoic acid
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- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 24
- 150000001875 compounds Chemical class 0.000 title abstract description 15
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 230000005494 condensation Effects 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- BEYOBVMPDRKTNR-UHFFFAOYSA-N chembl79759 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=CC=C1 BEYOBVMPDRKTNR-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 abstract description 4
- 239000002131 composite material Substances 0.000 abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- -1 phenyl ester Chemical class 0.000 abstract 2
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UVOKEWIIBKIDIY-UHFFFAOYSA-N 2-phenyldiazenylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1N=NC1=CC=CC=C1 UVOKEWIIBKIDIY-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical group ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to one kind of substituted azophenyl carboxylate containing fluorine atom and cyan group as liquid crystal compound and its preparation process. The compound has the chemical structure of 4'-allyloxy-4- azophenyl carboxylic acid-3-fluoro-4-cyan phenyl ester. The preparation process includes the first Williamson etherification to introduce allyloxy radical to the 4'-place of p-hydroxy azophenyl carboxylic acid so as to produce 4'-allyloxy-4-azophenyl carboxylic acid; and the subsequent DCC dehydrating condensation of 4'-allyloxy-4-azophenyl carboxylic acid and 2-fluoro-4-hydroxyl phenyl nitrile to obtain the required compound. The present invention also relates to the use of the compound, and the monomer liquid crystal compound may be used in compounding composite liquid crystal for LCD.
Description
Technical field
The present invention relates to technical field of organic synthesis, especially relate to a kind of replacement phenylazobenzoic acid esters liquid crystal compound and preparation method and purposes that contains fluorine atom and cyano group.
Background technology
In recent years, liquid crystalline cpd and liquid crystal material become one of focus of applied chemistry and materials chemistry research, obtained widely using in each side such as electronics, optics, acoustics, biotechnology, chemical industry, and wherein the most extensive and the most important thing is its application aspect the electronics demonstration.Along with the development of information industry, to the requirement of liquid crystal material also in continuous raising.Though the report of relevant liquid crystal material aspect is existing a lot, but they all are not suitable in the display device, must satisfy requirements such as broad operating temperature range, lower operating voltage, low-viscosity, response fast, high stability because show the liquid crystal material of usefulness.
With 2-fluoro-4-4-hydroxy-benzonitrile is the advantage that the liquid crystalline cpd of intermediate has fluorinated liquid crystal and cyano group liquid crystal concurrently, be the important liquid crystalline cpd of a class that satisfies above-mentioned condition, represents the liquid crystal development trend, and therefore 2-fluoro-4-4-hydroxy-benzonitrile also become intermediate important in the liquid crystal chemical industry.This intermediate is at first the most synthetic by Japanese Sumitomo Chemical Co.Ltd. as far back as nineteen eighty-two, after this people use this intermediate to synthesize hundreds of liquid crystalline cpds, these compounds all have the advantage of high clearing point, wide liquid crystal working range, low-viscosity, are suitable as the moiety of the demonstration liquid crystal material of excellent property.
Summary of the invention
The purpose of this invention is to provide a kind of replacement phenylazobenzoic acid esters liquid crystal compound that contains fluorine atom and cyano group, its structural formula is
This compound has the advantage that chemical property is stable, clearing point is high, liquid crystal range is wide, is the moiety and the photoelectric conversion material moiety of potential liquid crystal display material.
This compound is made by organic synthesis technology.The main points of the method for synthetic this compound are:
1) with the ethanol-water solution be mixed solvent, wherein the alcoholic acid volume percent is 70%～95%; Adding soluble alkali metal oxyhydroxide makes the potential of hydrogen of solution reach pH＞10, in solvent, add 3-propylene halide (so-called " halo " means that fluorine replaces, chlorine replaces, bromine replaces or iodine replaces) and p hydroxyazobenzene carboxylic acid, the ratio of both amount of substances is 2～5: 1, and the massfraction of p hydroxyazobenzene carboxylic acid in solution is 5%～30%.Under this condition, make both that condensation reaction take place.Temperature of reaction is 50～80 ℃.
2) after condensation reaction finishes, react with the ethanol-water mixed solvent solution of soluble alkali metal oxyhydroxide and the mixed solution of previous step reaction gained, remove the by product that generates in the step 1) by hydrolysis reaction, make 4 ' pure-allyloxy-4-phenylazobenzoic acid.The ratio of the amount of substance of employed p hydroxyazobenzene carboxylic acid is 2～5: 1 in used solubility oxyhydroxide and the step 1), the pH of reaction system＞12, and temperature of reaction is 50～80 ℃, the alcoholic acid volume percent is 60%～80% in the mixed solvent.
3) with DCC (N, the N-dicyclohexylcarbodiimide) is dewatering agent, DMAP (N, the N-Dimethylamino pyridine) is catalyzer, anhydrous tetrahydro furan is a solvent, impel 4 '-allyloxy-4-phenylazobenzoic acid and 2-fluoro-4-4-hydroxy-benzonitrile by dehydration condensation, generate target compound 4 '-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester.The ratio of the amount of substance of DCC, 4 '-allyloxy-4-phenylazobenzoic acid, 2-fluoro-4-4-hydroxy-benzonitrile, DMAP is 1～1.5: 1～2: 1: 0.01～0.02, and the initial mass mark of 2-fluoro-4-4-hydroxy-benzonitrile in solution is 5%～20%.Temperature of reaction is 0～30 ℃.
To help to understand the present invention by following experiment, but following experiment does not limit content of the present invention.
Implement 1
1) 0.01mol p hydroxyazobenzene carboxylic acid and 0.02mol potassium hydroxide are dissolved in 40ml 95% (volume fraction) ethanol, speed with about 1ml/min dropwise adds 0.03mol 3-bromopropylene, back flow reaction 24h, 70% (volume fraction) ethanolic soln meter 14ml that adds 0.02mol potassium hydroxide again continues backflow 2h.Add entry 100ml, concentrated hydrochloric acid 20ml, behind the heating 15min, cold filtration with distilled water wash, drying, with 95% (volume fraction) ethyl alcohol recrystallization, obtains 4 '-allyloxy-4-phenylazobenzoic acid again, is orange red tabular crystal, productive rate 44%.
2) in there-necked flask, add 0.01mol 4 '-allyloxy-4-phenylazobenzoic acid and 20ml anhydrous tetrahydro furan, after stirring is dissolved it fully, DCC (the N that adds 0.01mol, the N-dicyclohexylcarbodiimide), after waiting to become turbid, with 0.01mol 2-fluoro-4-4-hydroxy-benzonitrile and a small amount of DMAP[4-(N, the N-dimethylamino) pyridine] be dissolved in wiring solution-forming in the 20ml anhydrous tetrahydro furan, slowly splash in the flask, about 10 ℃, stir 24h, after reaction finishes, remove by filter by product N, the N-dicyclohexylurea (DCU), adding distil water is precipitated out product in filtrate, dry back gets pure product 0.68g by column chromatography for separation, productive rate about 17%.
Implement 2
1) 0.02mol p hydroxyazobenzene carboxylic acid and 0.06mol potassium hydroxide are dissolved in 100ml95% (volume fraction) ethanol, add 0.05mol 3-iodopropylene again, back flow reaction 60h.70% (volume fraction) ethanolic soln meter 35ml that adds 0.03mol potassium hydroxide afterwards continues backflow 2h.Add entry 100ml, concentrated hydrochloric acid 40ml mixes, and behind the heating 20min, cold filtration with distilled water wash, drying, with 95% (volume fraction) ethyl alcohol recrystallization, obtains 4 '-allyloxy-4-phenylazobenzoic acid again, is orange red tabular crystal, productive rate 40%.
2) in there-necked flask, add 0.015mol 4 '-allyloxy-4-phenylazobenzoic acid and 50ml anhydrous tetrahydro furan, after stirring is dissolved it fully, DCC (the N that adds 0.01mol, the N-dicyclohexylcarbodiimide), after waiting to become turbid, with 0.015mol 2-fluoro-4-4-hydroxy-benzonitrile and a small amount of DMAP[4-(N, the N-dimethylamino) pyridine] be dissolved in wiring solution-forming in the 35ml anhydrous tetrahydro furan fully, slowly splash in the flask, about 20 ℃, stir 24h, after reaction finishes, remove by filter by product N, the N-dicyclohexylurea (DCU), adding distil water is precipitated out product in filtrate, dry back gets pure product 0.91g by column chromatography for separation, productive rate about 15%.
By IR,
1H NMR method characterizes institute's synthetic compound, to confirm its structure.
IR (infrared spectra):
Cyano group (1, the stretching vibration of C ≡ N key, 2243cm
-1)
Phenyl ring (2, the stretching vibration of phenyl ring carbon skeleton, 1603,1501cm
-1)
Carbonyl (3, C=O stretching vibration, 1739cm
-1)
Carbon oxygen singly-bound (4, C-O-C stretching vibration, 1251,1146cm
-1)
1HNMR (proton nmr spectra):
Proton 1: δ=7.20 * 10
-6, 2H
Proton 2: δ=7.97 * 10
-6, 2H
Proton 3: δ=8.03 * 10
-6, 2H
Proton 4: δ=8.34 * 10
-6, 2H
Proton 5: δ=7.51 * 10
-6, 1H
Proton 6: δ=7.78 * 10
-6, 1H
Proton 7: δ=8.12 * 10
-6, 1H
Proton 8: δ=5.32～5.46 * 10
-6, 2H
Proton 9: δ=6.11 * 10
-6, 1H
Proton 10: δ=4.73 * 10
-6, 2H
The structure of confirming institute's synthetic compound thus is consistent with expection.
By orthogonal polarizing microscope institute's synthetic sample is observed, sample presents tabular crystal under the normal temperature under polarizing microscope, with the speed heating of sample with 5 ℃/min, the sample fusion enters liquid crystal state during to about 125 ℃, occurs a large amount of drops in the visual field, occurs numerous blackstreaks in the drop, the cross frosting phenomenon appears in infall, present typical striped texture, and flow rapidly, show that sample exists with the nematic liquid crystal attitude at present.This explanation 4 '-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester is a kind of monotropic thermotropic liquid crystal.
More than be suitable as the ideal moiety of liquid crystal composite used in the liquid-crystal display, be suitable in the used liquid crystal composite material of liquid-crystal displays such as TN, STN, TFT about the test result of liquid crystal property explanation 4 '-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester.
Claims (2)
1. a liquid crystalline cpd---4 '-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester, its structural formula is
2. a liquid crystalline cpd---the preparation method of 4 '-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester is characterized in that
1) under the potential of hydrogen of pH＞10,50～80 ℃ temperature, in solution, add 3-propylene halide and p hydroxyazobenzene carboxylic acid, make both that condensation reaction take place, generate 4 '-allyloxy-4-phenylazobenzoic acid,
2) after condensation finishes, under 50～80 ℃ of conditions, remove reactions steps 1 by hydrolysis reaction with the solution of highly basic in ethanol-water mixed solvent) in the by product that generates,
3) with N, the N-dicyclohexylcarbodiimide is a dewatering agent, and N, N-Dimethylamino pyridine are catalyzer, 0～30 ℃ of reaction down, impel 4 '-allyloxy-4-phenylazobenzoic acid to become 4 '-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester with 2-fluoro-4-4-hydroxy-benzonitrile dehydrating condensation.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101390113A CN100410347C (en) | 2006-09-21 | 2006-09-21 | Liquid crystal compound 4'-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101390113A CN100410347C (en) | 2006-09-21 | 2006-09-21 | Liquid crystal compound 4'-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof |
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| Publication Number | Publication Date |
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| CN1928004A true CN1928004A (en) | 2007-03-14 |
| CN100410347C CN100410347C (en) | 2008-08-13 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013532A (en) * | 2012-11-30 | 2013-04-03 | 浙江工业大学 | Azobenzene photochromic liquid crystal compound and method for synthesizing same |
| CN103013535A (en) * | 2012-12-28 | 2013-04-03 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514045A (en) * | 1981-06-22 | 1985-04-30 | Minnesota Mining And Manufacturing Company | Helichromic-smectic liquid crystal compositions and display cells |
| JP3579727B2 (en) * | 1994-05-06 | 2004-10-20 | チッソ株式会社 | Liquid crystal composition |
| CN1261407C (en) * | 2002-01-25 | 2006-06-28 | 中国科学院化学研究所 | Azo structure contained fluorine-aromatic diamine and preparation process and use thereof |
| CN1325456C (en) * | 2002-12-24 | 2007-07-11 | 株式会社艾迪科 | Perfluoroallyloxy compound and liquid-crystal composition containing the compound |
| JP4581706B2 (en) * | 2004-01-29 | 2010-11-17 | 住友ベークライト株式会社 | Positive photosensitive resin composition, semiconductor device and display element using the positive photosensitive resin composition, and method for manufacturing semiconductor device and display element |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013532A (en) * | 2012-11-30 | 2013-04-03 | 浙江工业大学 | Azobenzene photochromic liquid crystal compound and method for synthesizing same |
| CN103013535A (en) * | 2012-12-28 | 2013-04-03 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
| CN103013535B (en) * | 2012-12-28 | 2014-02-26 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
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