CN103131427A - Liquid crystal compound and liquid crystal display and light-induced discoloration indicating materials including the same - Google Patents
Liquid crystal compound and liquid crystal display and light-induced discoloration indicating materials including the same Download PDFInfo
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- CN103131427A CN103131427A CN2011104008653A CN201110400865A CN103131427A CN 103131427 A CN103131427 A CN 103131427A CN 2011104008653 A CN2011104008653 A CN 2011104008653A CN 201110400865 A CN201110400865 A CN 201110400865A CN 103131427 A CN103131427 A CN 103131427A
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- 0 *c1ccc(C=O)cc1 Chemical compound *c1ccc(C=O)cc1 0.000 description 4
- CGOJOQBYEAVATL-QPJJXVBHSA-N COc1ccc(/C=C/C(Cl)=O)cc1 Chemical compound COc1ccc(/C=C/C(Cl)=O)cc1 CGOJOQBYEAVATL-QPJJXVBHSA-N 0.000 description 1
- CLRPMWZIZXAXFE-SREVYHEPSA-N Cc1ccc(/C=C\C(C=NC2)=CC=C2C(O)=O)cc1 Chemical compound Cc1ccc(/C=C\C(C=NC2)=CC=C2C(O)=O)cc1 CLRPMWZIZXAXFE-SREVYHEPSA-N 0.000 description 1
- AUHOOONALCXGNL-UHFFFAOYSA-N Oc1cc(CCC(CCc2cccc(O)c2)=O)ccc1 Chemical compound Oc1cc(CCC(CCc2cccc(O)c2)=O)ccc1 AUHOOONALCXGNL-UHFFFAOYSA-N 0.000 description 1
- WOHFCBMZGVNRBL-FIFLTTCUSA-N Oc1cccc(/C=C/C(/C=C/c2cc(O)ccc2)=O)c1 Chemical compound Oc1cccc(/C=C/C(/C=C/c2cc(O)ccc2)=O)c1 WOHFCBMZGVNRBL-FIFLTTCUSA-N 0.000 description 1
Abstract
The invention provides a liquid crystal compound. The liquid crystal compound is provided with a following chemical formula (I), wherein A is a phenylene group, a naphthalene group, a pyridine group, a furfuran group, a thiophene group or a single bond, D is a phenylene group, a naphthalene group, a pyridine group, a furfuran group, a thiophene group or a single bond, R1 and R2 are alkyl groups with 1-10 carbon numbers, alkoxy groups with 1-10 carbon numbers, fluorine or trifluoromethyl, E is a phenylene group, a naphthalene group, a pyridine group, a furfuran group, a thiophene group or a single bond, W is -CO-O-, -O-CO-, -O-, -CH2-CH2-, -CH=CH-, -CH2-O- or a single bond, Z is phenylene group, a naphthalene group, a pyridine group, a furfuran group, a thiophene group or a single bond, Y is hydrogen, methyl, ethyl or propyl, m is 0, 1 or 2, p is 0, 1 or 2, r is o, 1 or 2, q is 0, 1 or 2, and n is o, 1, 2 or 3. The invention further provides a liquid crystal display and light-induced discoloration indicating materials including the liquid crystal compound.
Description
Technical field
The present invention relates to a kind of liquid crystalline cpd, particularly relate to a kind of liquid crystalline cpd of high stability and comprise the liquid-crystal display of this compound.
Background technology
Reflective flexible display (reflective ﹠amp; Flexible display) be most important electronic console of future generation.Reflected displaying device with plastics as baseplate material, to replace the traditional glass substrate, have light, thin, the anti-characteristic such as fall, can be made into curling indicating meter, to be applied in numerous aspects such as electric label, e-book, smart card, flat-panel screens, large-scale advertisement billboard and hand-written computer.
Cholesterol with " selective reflection (selective reflection) " and principle show shades of colour, in addition, its bistable (bistability) characteristic in assembly, also can make picture in the situation that do not need impressed voltage " stop " get off, as showing as the same painting or book, drive it with voltage again when needing image switching.So operation, will significantly save indicating meter current consumption, make it be more convenient for carrying and read, and this direction is also one of important directions of research and development e-book.
Making optical-write-in mode cholesterin liquid-crystal display need use has high screw twisted power (helical twisting power, HTP) the light type of replying revolves optically active compounds, it changes because irradiation produces molecular conformation in liquid crystal, and then change screw twisted power, the spacing (pitch) that causes cholesterol liquid crystal changes, and reaches the effect that changes different reflected light colors.Wish to synthesize a kind of opticity admixture (chiral dopant) with higher screw twisted power value, after making it add liquid crystal, more do not affect the liquid crystal performance, only need a small amount of doping, can reach identical torsion effect, in addition, also can not cause the problem of solubleness.In addition, this light is replied the type optically active compounds also can not have color, otherwise can the noisy reflection optical wavelength.
Therefore, light is replied the type optically active compounds and need be possessed high screw twisted power (HTP) value, with dispensing liquid crystal, good solubility and the characteristic such as colourless be arranged, and can be added in dispensing liquid crystal.
Summary of the invention
One embodiment of the invention provide a kind of liquid crystalline cpd, have following chemical formula (I):
Wherein A is penylene base, naphthylene base (naphthalene), pyridine support base (pyridine), furans support base (furan), thiophene support base (thiophene) or singly-bound; D is penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound; R1, R2 are the alkyl of carbon number 1～10, alkoxyl group, fluorine or the trifluoromethyl of carbon number 1～10; E is penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound; W is-CO-O-,-O-CO-,-O-,-CH
2-CH
2-,-CH=CH-,-CH
2-O-or singly-bound; Z is penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound; Y is hydrogen, methyl, ethyl or propyl group; M is 0,1 or 2; P is 0,1 or 2; R is 0,1 or 2; Q is 0,1 or 2; And n is 0,1,2 or 3.
One embodiment of the invention provide a kind of liquid-crystal display, comprising: upper substrate; The hypocoxa that is oppositely arranged with this upper substrate; And being arranged at liquid crystal layer between this upper substrate and this hypocoxa, this liquid crystal layer comprises above-mentioned liquid crystalline cpd with chemical formula (I).
One embodiment of the invention provide a kind of phototropic indication material, comprising: a substrate; And a micella liquid crystal layer of coating this substrate, this micella liquid crystal layer comprises above-mentioned liquid crystalline cpd with chemical formula (I).
The light that the invention discloses a kind of novelty is replied the type optically active compounds, it has high screw twisted power (HTP) but value, change slow control accurate cholesterol liquid crystal colorize wavelength with the good solubility of dispensing liquid crystal, stable temperature dependency, wavelength with respect to the irradiation time and make the cholesterol liquid crystal characteristics such as the environment stability inferior is good around.
Embodiment
For above-mentioned purpose of the present invention, feature and advantage can be become apparent, a preferred embodiment cited below particularly elaborates.
One embodiment of the invention provide a kind of liquid crystalline cpd, have following chemical formula (I):
In chemical formula (I), A can be penylene base, naphthylene base (naphthalene), pyridine support base (pyridine), furans support base (furan), thiophene support base (thiophene) or singly-bound.
D can be penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound.
R1, R2 can be the alkyl of carbon number 1～10, alkoxyl group, fluorine or the trifluoromethyl of carbon number 1～10.
E can be penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound.
W can be-CO-O-,-O-CO-,-O-,-CH
2-CH
2-,-CH=CH-,-CH
2-O-or singly-bound.
Z can be penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound.
Y can be hydrogen, methyl, ethyl or propyl group.In one embodiment, Y also can be fluorine (F), chlorine (Cl), bromine (Br) ,-CN or-OR (R can be methyl, ethyl or propyl group).
M can be 0,1 or 2.
P can be 0,1 or 2.
R can be 0,1 or 2.
Q can be 0,1 or 2.
N can be 0,1,2 or 3.
Below enumerate the specific liquid crystalline cpd of the present invention, for example
One embodiment of the invention provide a kind of liquid-crystal display, comprise a upper substrate, one hypocoxa that is oppositely arranged with upper substrate, and a liquid crystal layer that is arranged between upper substrate and hypocoxa, liquid crystal layer comprises above-mentioned liquid crystalline cpd with chemical formula (I).
Above-mentioned upper substrate and hypocoxa can be (the array on color filter substrate of array substrate on colored filter substrate, array substrate, colored filter, AOC), array filter sheet base plate (the color filter on array substrate that enamels, COA) or transparency carrier, for example glass substrate or plastic base.
Another embodiment of the present invention provides a kind of phototropic indication material, comprises a substrate, and a micella liquid crystal layer of coating substrate, and the micella liquid crystal layer comprises above-mentioned liquid crystalline cpd with chemical formula (I).
Aforesaid substrate can be (the array on color filter substrate of array substrate on colored filter substrate, array substrate, colored filter, AOC), array filter sheet base plate (the color filter on array substrate that enamels, COA) or transparency carrier, for example glass substrate or plastic base.
The light that the invention discloses a kind of novelty is replied the type optically active compounds, it has high screw twisted power (HTP) but value, change slow control accurate cholesterol liquid crystal colorize wavelength with the good solubility of dispensing liquid crystal, stable temperature dependency, wavelength with respect to the irradiation time and make the cholesterol liquid crystal characteristics such as the environment stability inferior is good around.
[embodiment 1]
Liquid crystalline cpd I's of the present invention is synthetic
Step I-1
At room temperature, 42.08 gram potassium hydroxide (700mmol) are dissolved in the 180mL ethanolic soln.This solution is cooled to 5 ℃ under condition of ice bath.Add lentamente 73.2 gram 3-hydroxy benzaldehydes (600mmol), temperature can raise slightly.After again this yellow mud shape thing is cooling, dropwise add 22.05mL acetone (300mmol) with addition funnel, stir about 30 minutes (temperature can rise and descend) under ice bath.Remove ice bath, under room temperature, stir about is 4.5 hours.The red solution that produces is poured in the 300mL frozen water.Add 45mL acetic acid neutralization reaction, solution colour can change glassy yellow mud shape thing, stir about 15 minutes into by redness again.This mud shape thing was poured in Erlenmeyer flask standing 10 minutes, collected lower floor's glassy yellow mud shape thing.Afterwards, filter after cooling the temperature to 5 ℃, first with a large amount of flushing with clean water, then rinse with a small amount of ethanol/water (1: 2 (v/v)) solution.The a small amount of water of product solid recycling rinses, and is positioned over air drying, obtains 48.06 gram glassy yellow solids (180mmol), productive rate 80%.
Step I-2
Getting the 5.00 resulting products of gram step I-1 (18.79lmmol) is dissolved in 18.8mL ethyl propenoate (EA).Get 0.15 gram catalyzer RaNi.First use the tetrahydrofuran (THF) washing catalyst three times (removing the solvent that originally was coated on the RaNi surface), then add in reaction flask.First utilize vacuum system with after in reaction flask, air removes, at room temperature utilize hydrogen balloon to react.Reaction is carried out having heat release slightly when initial, until room temperature is down in reaction, reaction approximately 10 hours determines that with TLC sheet (silicon-dioxide) reaction finishes.Utilize carefully diatomite (celite) to filter.Rinse bottle with a small amount of ethyl propenoate (EA).Utilize the concentrating under reduced pressure machine to drain liquid, obtain the 4.81 thick liquid of gram (17.79mmol), productive rate approximately 95%.
Step I-3
Under condition of ice bath, get the 29.35 resulting products of gram step I-2 (108.6mmol) and be dissolved in the 108mL acetonitrile.Add again 1.2mL bromine water (24mmol).(217.4mmol) dividing four times the inferior acid amides of 38.74 gram bromo ambers (NBS) adds, often add once, Nei Wenyue rises 12 ℃, equitemperature descends 5 ℃ and just can add next time, the time that adds for four times is wanted more than 30 minutes, after adding for the last time, stirs 1 hour under ice bath, stirred again ㄧ hour after being back to room temperature, with HPLC (ethyl propenoate: hexane=1: 1) determine that reaction finishes.After reaction is completed, utilize the concentrating under reduced pressure machine to drain, can obtain the inferior amides of product and by product amber.With mixture stir about 1 hour in 55 ℃, 300mL water, remove by product.After air exhaust filtering, then rinse solid with a small amount of water.Afterwards, standing and drying in air obtains 43.25 gram colour of skin products (101mmol), productive rate 93%.
Step I-4
At room temperature, 100ml methylsulfuric acid (1.54mol) is slowly added the product 1 that 16 gram step I-3 synthesize is housed, two (the 5-bromo-3-hydroxy phenyls)-1 of 5-, in the reaction flask of 4-penta-3-ketone (37.37mmol) and make its uniform stirring, after about 30 minutes, solid can dissolve fully, interior Wen Zehui rises a little, has at last throw out to separate out.Through after one hour, after adding a large amount of 200 gram ice cubes to stir in reaction flask, add 100ml toluene and 5 gram diatomite to reaction flask again, stir by diatomite filtration.Solid cleans with minimum toluene.Get organic layer after filtration with the extraction of 50ml distilled water.Get organic layer and remove water filtration through sodium sulfate.Concentrating under reduced pressure vacuumizes the removal solvent.Head product is dissolved in 30mL diisopropyl ether (IPE).Add 120ml normal heptane vigorous stirring to form muddy, stir and filter out impurity after 30 minutes.Again organic layer is drained concentratedly, obtained 11.71 gram products (28.55mmol), productive rate approximately 76%.
Step I-5
Get the dibromospirobiindane (28.55mmol) that 11.71 gram step I-4 synthesize and be placed in reaction flask, add 80mL ethyl acetate and 23mL distilled water, 80mL triethylamine (Et3N) (0.58mol), 1.16 gram catalyst P d/C (10%Pd/C), add hydrogen balloon, reaction meeting heat release a little utilizes the HPLC following response, after confirming to react completely, mixture is through diatomite filtration.Organic layer after filtration with 5%, the 10mL aqueous hydrochloric acid cleans, get organic layer through sodium sulfate except water filtration.Concentrating under reduced pressure vacuumizes the removal solvent, and utilizes ethyl propenoate: hexane=1: 10 tubing string chromatography, obtaining product is white solid, productive rate approximately 65%.
Step I-6
Get the 0.5 resulting product of gram step I-5 (racemization two alcohol (racemic diol)) and (1.98mmol) be dissolved in the 5mL ethyl acetate.Under ice bath, (interior temperature is lower than 5 ℃) add 0.7mL triethylamine (4.9mmol), 0.024 gram DMAP (DMAP) (0.19mmol).Slowly splash into 0.9mL methyl-chloroformate ((-)-methyl chloroformate) in 15 minutes (4.16mmol), meeting heat release a little in the process that adds, interior temperature rise is arrived approximately 15 ℃, and has white precipitate formation, and reaction remained on low-temperature condition 30 minutes.Add 5% under ice bath, the 3mL aqueous hydrochloric acid.This mixture can get a small amount of solid (product) through filtering.These solids are got the organic layer of filtrate and merge with tetrahydrofuran (THF) (THF) with 1.50mL tetrahydrofuran (THF) (THF) dissolving, and except water filtration, concentrating under reduced pressure vacuumizes the removal solvent through sal epsom.Add the 2.50mL normal heptane to stir 30 minutes under acetone/ice bath.Filter and use minimum ice normal heptane to clean solid, making it at air drying, obtaining colorless solid product (two carbonate (bis-carbonate)) ((S)-9), productive rate approximately 40%.
Step I-7
Get the 41.1 resulting products of gram step I-6 (two carbonate (bis-carbonate)) ((S)-9) and (66.6mmol) be dissolved in 50mL tetrahydrofuran (THF) (THF), add (333mmol) reflux 80 minutes of 16mL hydrazine hydrate (hydrazine hydrate).Pour in reaction flask ice 5%, the 250mL aqueous sodium hydroxide solution.This mixture extracts with the 200mL diisopropyl ether, removes and keeps water layer.With organic layer again with 5%, the 100mL aqueous sodium hydroxide solution extracts once, mixes the water layer of twice extraction, adds carefully 65mL concentrated hydrochloric acid (pH≤2), have precipitation and form this moment.This solution is cooled to below 5 ℃ with ice bath, cross the leaching solid, and with a small amount of water flushing, make it at air drying, obtain colorless solid product (two alcohol (diol)) ((S)-3), productive rate approximately 87%.
Step I-8
Get the 1 resulting product of gram step I-7 (chiral diol (chiral diol)) ((S)-3) and (3.96mmol) be dissolved in 10mL tetrahydrofuran (THF) (THF).Under ice bath (interior temperature is lower than 5 ℃), add 1.4mL triethylamine (10.04mmol), 0.05 gram DMAP (DMAP) (0.4mmol).Slowly add 0.77 gram acyl chlorides (3.96mmol), can heat release a little in the process that adds, and have white precipitate and form, reaction was got back to after room temperature stir about 1 hour.Under ice bath, add 5%, the 20mL aqueous hydrochloric acid.Add the 20mL ethyl acetate extraction, get organic layer and remove water filtration through sodium sulfate, concentrating under reduced pressure vacuumizes the removal solvent.With normal hexane and ethyl acetate for rush extract via the tubing string chromatography after, can get white solid, productive rate approximately 65%.
Step I-9
Get the 1 resulting product of gram step I-8 (2.4mmol) and be dissolved in 20mL tetrahydrofuran (THF) (THF).Under ice bath (interior temperature is lower than 5 ℃), add 0.84mL triethylamine (6.02mmol), 0.03 gram DMAP (DMAP) (0.24mmol).Slowly add 1.29 gram acyl chlorides (3.6mmol), can heat release a little in the process that adds, and have white precipitate and form, reaction was got back to after room temperature stir about 1 hour.Under ice bath, add 5%, the 20mL aqueous hydrochloric acid.Add the 20mL ethyl acetate extraction, get organic layer and remove water filtration through sodium sulfate, concentrating under reduced pressure vacuumizes the removal solvent.With normal hexane and ethyl acetate for rush extract via the tubing string chromatography after, can get white solid, productive rate approximately 79%.
[embodiment 2]
Liquid crystalline cpd II's of the present invention is synthetic
Step II-1
Get the 1 resulting product of gram step I-8 (2.42mmol) and be dissolved in 20mL tetrahydrofuran (THF) (THF).Under ice bath (interior temperature is lower than 5 ℃), add 0.84mL triethylamine (6.02mmol), 0.03 gram DMAP (DMAP) (0.24mmol).Slowly add 0.53 gram acyl chlorides (3.6mmol), can heat release a little in the process that adds, and have white precipitate and form, reaction was got back to after room temperature stir about 1 hour.Under ice bath, add 5%, the 20mL aqueous hydrochloric acid.Add the 20mL ethyl acetate extraction, get organic layer and remove water filtration through sodium sulfate, concentrating under reduced pressure vacuumizes the removal solvent.With normal hexane and ethyl acetate for rush extract via the tubing string chromatography after, can get white solid, productive rate approximately 56%.
[embodiment 3]
Liquid crystalline cpd III's of the present invention is synthetic
Step II I-1
With 1 gram 4-(brooethyl) phenylformic acid (4-(bromomethyl) benzoic acid) (4.65mmol) and 1.46 gram triphenyl phosphorus (triphenylphosphine) (5.57mmol) insert in single neck round-bottomed bottle.Afterwards, add 10ml toluene.Set up condensing works, heat 110 ℃, refluxed 16 hours.After reaction stops, rinsing, filter with hexane, get white solid.
The 3 resulting products of gram previous step (6.28mmol) are inserted in two neck round-bottomed bottles.Vacuumize, fill with nitrogen and inject tetrahydrofuran (THF) (THF).Under-78 ℃ of environment, slowly splash into 5ml n-Butyl Lithium (n-BuLi) (2.5M), stir about 1 hour.Slowly add 1.2 gram 4-(hexyloxy) phenyl aldehydes (4-(hexyloxy) benzaldehyde) (5.8mmol) under ice bath, under 0 ℃ of condition, stir half an hour, at room temperature stirred 16 hours.Follow the trail of with NMR, after reacting completely, extract, concentrate with ethyl acetate, get the light green solid.Under ethyl acetate and hexane condition, carry out purifying through the tubing string chromatography again, get white solid (productive rate 50%).
The 1.26 resulting white solids of gram previous step (3.67mmol) are inserted round-bottomed bottle.Add 52ml toluene, then add 52 milligrams of iodine, reflux is spent the night, and causes white solid and separates out.Filter and rinse out with toluene the color of iodine.Vacuum is drained rear weighing (productive rate 87%).
Get the 1 resulting product of gram step I-7 (chiral diol) ((S)-3) and (3.96mmol) be dissolved in 10mL tetrahydrofuran (THF) (THF).Under ice bath (interior temperature is lower than 5 ℃), add 1.4mL triethylamine (10.04mmol), 0.05 gram DMAP (DMAP) (0.4mmol).Slowly add 1.37 gram acyl chlorides (3.96mmol), can heat release a little in the process that adds, and have white precipitate and form, reaction was got back to after room temperature stir about 1 hour.Under ice bath, add 5%, the 20mL aqueous hydrochloric acid.Add the 20mL ethyl acetate extraction, get organic layer and remove water filtration through sodium sulfate, concentrating under reduced pressure vacuumizes the removal solvent.With normal hexane and ethyl acetate for rush extract via the tubing string chromatography after, can get white solid, productive rate approximately 60%.
Step II I-2
Get the 1 resulting product of gram Step II I-1 (2.4mmol) and be dissolved in 20mL tetrahydrofuran (THF) (THF).Under ice bath (interior temperature is lower than 5 ℃), add 0.84mL triethylamine (6.02mmol), 0.03 gram DMAP (DMAP) (0.24mmol).Slowly add 1.29 gram acyl chlorides (3.6mmol), can heat release a little in the process that adds, and have white precipitate and form, reaction was got back to after room temperature stir about 1 hour.Under ice bath, add 5%, the 20mL aqueous hydrochloric acid.Add the 20mL ethyl acetate extraction, get organic layer and remove water filtration through sodium sulfate, concentrating under reduced pressure vacuumizes the removal solvent.With normal hexane and ethyl acetate for rush extract via the tubing string chromatography after, can get white solid, productive rate approximately 76%.
[embodiment 4]
Liquid crystalline cpd IV's of the present invention is synthetic
Step IV-1
Get the 1 resulting product of gram step I-7 (chiral diol) ((S)-3) and (3.96mmol) be dissolved in 10mL tetrahydrofuran (THF) (THF).Under ice bath (interior temperature is lower than 5 ℃), add 1.4mL triethylamine (10.04mmol), 0.05 gram DMAP (DMAP) (0.4mmol).Slowly add 0.62 gram acyl chlorides (3.96mmol), can heat release a little in the process that adds, and have white precipitate and form, reaction was got back to after room temperature stir about 1 hour.Under ice bath, add 5%, the 20mL aqueous hydrochloric acid.Add the 20mL ethyl acetate extraction, get organic layer and remove water filtration through sodium sulfate, concentrating under reduced pressure vacuumizes the removal solvent.With normal hexane and ethyl acetate for rush extract via the tubing string chromatography after, can get white solid, productive rate approximately 66%.
Step IV-2
Get the 1 resulting product of gram step IV-1 (2.4mmol) and be dissolved in 20mL tetrahydrofuran (THF) (THF).Under ice bath (interior temperature is lower than 5 ℃), add 0.84mL triethylamine (6.02mmol), 0.03 gram DMAP (DMAP) (0.24mmol).Slowly add 1.29 gram acyl chlorides (3.6mmol), can heat release a little in the process that adds, and have white precipitate and form, reaction was got back to after room temperature stir about 1 hour.Under ice bath, add 5%, the 20mL aqueous hydrochloric acid.Add the 20mL ethyl acetate extraction, get organic layer and remove water filtration through sodium sulfate, concentrating under reduced pressure vacuumizes the removal solvent.With normal hexane and ethyl acetate for rush extract via the tubing string chromatography after, can get white solid, productive rate approximately 79%.
The HTP of [embodiment 5] liquid crystalline cpd of the present invention (helical twisting power) value
Table 1 is the comparison of liquid crystalline cpd of the present invention and available liquid crystal compound H TP value.
Table 1
Available liquid crystal Compound I a:
Available liquid crystal Compound I Ia:
As shown in Table 1, the HTP value of liquid crystalline cpd of the present invention is large than the HTP value of available liquid crystal compound.
The temperature dependency of [embodiment 6] liquid crystalline cpd of the present invention
Table 2 is the comparison of liquid crystalline cpd of the present invention and available liquid crystal compound temperature interdependence.
Experiment condition: wavelength: 580nm measures temperature: 0～50 ℃
Table 2
| Available liquid crystal Compound I a | Available liquid crystal Compound I Ia | Liquid crystalline cpd I of the present invention | Liquid crystalline cpd II of the present invention | |
| dλ/dT | -0.74 | -0.63 | -0.26 | -0.33 |
As shown in Table 2, (d λ/dT) obviously stable than the temperature dependency of available liquid crystal compound is fit to be applied to cholesterin liquid-crystal display to the temperature dependency of liquid crystalline cpd of the present invention.
The relation of [embodiment 7] liquid crystalline cpd irradiation time of the present invention and wavelength change
Table 3 is the relation of liquid crystalline cpd of the present invention and available liquid crystal compound irradiation time and wavelength change.
Experiment condition: wavelength: 365nm, power: 4mW/cm
2
Table 3
As shown in Table 3, under same irradiation condition, the wavelength change rate (nm/sec) of liquid crystalline cpd of the present invention is obviously slow than the wavelength change rate of available liquid crystal compound, but control accurate cholesterol liquid crystal colorize wavelength is fit to be applied to cholesterin liquid-crystal display.In addition, according to this characteristic, liquid crystalline cpd of the present invention also can be used the indicator as detecting UV-light (UV).
The optical stability of [embodiment 8] liquid crystalline cpd of the present invention
Table 4 is the comparison of liquid crystalline cpd of the present invention and available liquid crystal compound optical stability.
Experiment condition: wavelength: 365nm, power: 1 μ W/cm
2(indoor daylight lamp)
Table 4
As shown in Table 4, under same surrounding environment (general indoor daylight lamp), the blueness of liquid crystalline cpd of the present invention, green and red color obviously have better stability than blueness, green and the red color of available liquid crystal compound.
Although the present invention with preferred embodiment openly as above; so it is not to limit the present invention, any those skilled in the art, without departing from the spirit and scope of the present invention; can make an amendment and change, so protection scope of the present invention is defined with claims and is as the criterion.
Claims (4)
1. liquid crystalline cpd has following chemical formula (I):
Wherein
A is penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound;
D is penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound;
R1, R2 are the alkyl of carbon number 1～10, alkoxyl group, fluorine or the trifluoromethyl of carbon number 1～10;
E is penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound;
W is-CO-O-,-O-CO-,-O-,-CH
2-CH
2-,-CH=CH-,-CH
2-O-or singly-bound;
Z is penylene base, naphthylene base, pyridine support base, furans support base, thiophene support base or singly-bound;
Y is hydrogen, methyl, ethyl or propyl group;
M is 0,1 or 2;
P is 0,1 or 2;
R is 0,1 or 2;
Q is 0,1 or 2; And
N is 0,1,2 or 3.
2. liquid crystalline cpd as claimed in claim 1, wherein this liquid crystalline cpd comprises
3. liquid-crystal display comprises:
One upper substrate;
One hypocoxa is oppositely arranged with this upper substrate; And
One liquid crystal layer is arranged between this upper substrate and this hypocoxa, and this liquid crystal layer comprises liquid crystalline cpd as claimed in claim 1.
4. a phototropic is indicated material, comprising:
One substrate; And
One micella liquid crystal layer is coated this substrate, and this micella liquid crystal layer comprises liquid crystalline cpd as claimed in claim 1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018086197A1 (en) * | 2016-11-11 | 2018-05-17 | 南方科技大学 | Catalytic asymmetric synthesis method for chiral spinol derivate |
| CN109761774A (en) * | 2019-03-06 | 2019-05-17 | 苏州星火生物科技有限公司 | A kind of synthetic method of ligand loop coil diphenol |
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| JPS61282840A (en) * | 1985-06-10 | 1986-12-13 | Fuji Photo Film Co Ltd | Color photographic material |
| JP2005281215A (en) * | 2004-03-30 | 2005-10-13 | Sumitomo Chemical Co Ltd | Optical resolution reagent consisting of optically active spiro compound |
| US20060091357A1 (en) * | 2004-10-29 | 2006-05-04 | Welter Thomas R | Photochemically active chiral compounds and compositions containing the same |
| CN1842511A (en) * | 2003-08-29 | 2006-10-04 | 伊斯曼柯达公司 | Chiral compounds and compositions containing the same |
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| JPS61282840A (en) * | 1985-06-10 | 1986-12-13 | Fuji Photo Film Co Ltd | Color photographic material |
| CN1842511A (en) * | 2003-08-29 | 2006-10-04 | 伊斯曼柯达公司 | Chiral compounds and compositions containing the same |
| JP2005281215A (en) * | 2004-03-30 | 2005-10-13 | Sumitomo Chemical Co Ltd | Optical resolution reagent consisting of optically active spiro compound |
| US20060091357A1 (en) * | 2004-10-29 | 2006-05-04 | Welter Thomas R | Photochemically active chiral compounds and compositions containing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018086197A1 (en) * | 2016-11-11 | 2018-05-17 | 南方科技大学 | Catalytic asymmetric synthesis method for chiral spinol derivate |
| CN109761774A (en) * | 2019-03-06 | 2019-05-17 | 苏州星火生物科技有限公司 | A kind of synthetic method of ligand loop coil diphenol |
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