CN102093377B - Chiral compound and liquid crystal composition containing the compound - Google Patents
Chiral compound and liquid crystal composition containing the compound Download PDFInfo
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- CN102093377B CN102093377B CN2009102534318A CN200910253431A CN102093377B CN 102093377 B CN102093377 B CN 102093377B CN 2009102534318 A CN2009102534318 A CN 2009102534318A CN 200910253431 A CN200910253431 A CN 200910253431A CN 102093377 B CN102093377 B CN 102093377B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 63
- 150000001875 compounds Chemical class 0.000 title claims abstract description 41
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 11
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 abstract description 12
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical group 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 10
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229960002479 isosorbide Drugs 0.000 description 9
- 239000007787 solid Substances 0.000 description 7
- KLDXJTOLSGUMSJ-BXKVDMCESA-N (3s,3as,6s,6as)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@H]2[C@@H](O)CO[C@H]21 KLDXJTOLSGUMSJ-BXKVDMCESA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000011049 filling Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 acryl functional group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- Liquid Crystal Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明提供一种手性化合物，具有如式(I)或式(II)的结构：
The present invention provides a chiral compound having a structure of formula (I) or formula (II):
Description
Technical field
The present invention relates to a kind of chipal compounds (chiral compound), and particularly relates to the liquid-crystal compsn that a kind of light with high screw twisted power is replied the type chipal compounds and contained this compound.
Background technology
Cholesteric liquid crystal display has does not need backlight and polaroid to get final product the characteristic in reflect ambient light source; Thereby general display mode has more and can save energy; Spontaneous reflection ray characteristic can be directed against the different wavelengths of light line reflection, does not therefore need colored filter can reach the demand of color monitor.
Cholesteric liquid crystal material (Cholesteric liquid crystal) can be described as Chinrally nematic (chiralnematic) liquid crystal material again; Form by simple nematic liquid crystal and special chiral additives (chiral dopant); The liquid crystal material that originally presents the nematic arrangement receives the influence of chiral additives; Generation than TN (twisted nematic, stable twisted nematic) or STN (super twisted nematic, STN Super TN type liquid crystal) more intensive reverse.
The pitch p of cholesteric liquid crystal material by the concentration of chiral additives (concentration, C) with its screw twisted power (helical twisting power, HTP) decision has following relational expression:
p＝1/(HTP·C)。
Because the wavelength of cholesteryl liquid crystal reflection determines by pitch, and the pitch of prescription filled a prescription in the screw twisted power of employed chiral additives control with concentration.Therefore, under specific pitch required, screw twisted power (HTP) was high more, and the chiral molecules concentration of required interpolation is just low more.If liquid crystal parent (multilayer nematic liquid crystal) is not good for the solubleness of this optically-active liquid crystal molecule, with making the regulation and control of liquid-crystal compsn be restricted.
Making the optical-write-in mode cholesteric liquid crystal display need use the light with high screw twisted power to reply the type chipal compounds; Make it in liquid crystal, can produce the configuration change of molecule because of irradiation; And then generation screw twisted power (HTP) changes; The pitch (p) of cholesteryl liquid crystal is changed, reach the different reflected light colors of change.Yet,, be not suitable for the cholesteryl liquid crystal prescription of optical-write-in mode if chipal compounds itself has the color that color (the for example azo molecules of orange) is added into meeting noisy reflection light in the nematic liquid crystal parent yet.
Therefore, light is replied the type chipal compounds and need be possessed high screw twisted power, have good solubleness, characteristic such as colourless can be added in the dispensing liquid crystal, but just can reach the effect that light writes color with dispensing liquid crystal.On the other hand, the liquid-crystal compsn of gained should have high color purity and stable temperature dependency characteristics such as (temperaturedependence).
Summary of the invention
The object of the present invention is to provide a kind of chipal compounds that is applicable to the cholesteryl liquid crystal prescription of optical-write-in mode.
The present invention provides a kind of chipal compounds, has the structure suc as formula (I) or formula (II):
R wherein
1, R
2Independent separately, be to select from hydrogen, hydroxyl, halogen, amido, nitro, itrile group, C
1-10Alkyl, C
1-10Alkoxyl group, aromatic base, assorted aromatic base, naphthenic base or heterocyclic radical.
The present invention also provides a kind of liquid-crystal compsn, comprising: the liquid crystal main body of 100 weight parts; And, 3-20 weight part such as aforesaid chipal compounds.
The invention has the advantages that: chipal compounds of the present invention has single light and replys the functional group, thereby less by the crest halfwidth (Δ λ) of the cholesteryl liquid crystal prescription that it made, and therefore presents preferable purity of color; Possesses high screw twisted power (HTP＞30 μ m
-1), add in nematic liquid crystal, can produce the cholesteryl liquid crystal phase on a small quantity; Good and own colourless with dispensing liquid crystal solubleness; The temperature dependency low (absolute value of d λ/dT is less than 1) of the reflection wavelength of the cholesteryl liquid crystal prescription of gained has more stable display quality.
For let above and other objects of the present invention, feature and advantage can be more obviously understandable, the hereinafter spy enumerates preferred embodiment, and cooperates appended accompanying drawing, elaborates as follows:
Description of drawings
Fig. 1 shows embodiment 1 and the crest halfwidth of comparative example 1 prepared dispensing liquid crystal at different wave length;
Fig. 2 shows the reflection wavelength of comparative example 2 prepared dispensing liquid crystals and the graph of a relation of temperature;
Fig. 3 shows the reflection wavelength of embodiment 1 prepared dispensing liquid crystal and the graph of a relation of temperature.
Embodiment
Make the optical-write-in mode cholesteric liquid crystal display and need use the light with high screw twisted power to reply the type chipal compounds, this light is replied the type chipal compounds can not have color, otherwise can the noisy reflection light wavelength.In order to reach the demand; The present invention is with asymmetric 1; 4:3; 6-two dehydration N.F,USP MANNITOL (isomannide) and Isosorbide (isosorbide) chiral molecules are done derive (as follows), and this structure has good HTP (HelicalTwisting Power) interpolation can produce the cholesteryl liquid crystal phase on a small quantity in nematic liquid crystal, and the acryl functional group of arranging in pairs or groups again in the structure is to reach the effect that light is replied.
Chipal compounds of the present invention has the structure suc as formula (I) or formula (II):
R wherein
1, R
2Independent separately, be to select from hydrogen, hydroxyl, halogen, amido, nitro, itrile group, C
1-10Alkyl, C
1-10Alkoxyl group, aromatic base, assorted aromatic base, naphthenic base or heterocyclic radical.C wherein
1-10Alkyl, C
1-10Alkoxyl group can be straight chain or has the side chain person.In one embodiment, R
1, R
2Independent separately, be to select from hydrogen, C
1-10Alkyl or C
1-10Alkoxyl group.In another embodiment, R
1, R
2Be all alkoxyl group.
In above-mentioned, " aromatic base (aryl) " represents the hydrocarbon aromatic nucleus of a monocycle or multi-loop system, for example: phenyl; Tolyl, naphthyl, tetrahydro naphthyl (tetrahydronaphthyl); Xenyl (biphenyl), phenanthryl (phenanthryl), anthryl (anthracyl) etc.
Contain the substituted aromatic base of one or more heteroatoms (like nitrogen, oxygen, sulphur) in " assorted aromatic base (heteroaryl) " representative structure, pyridyl (pyridyl) for example, furyl (furyl), thienyl (thienyl), imidazolyl (imidazolyl) etc.
" naphthenic base (cycloalkyl) " represents hydrocarbon monocycle or many rings of a non-aromatic, can contain 3～12 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, ring octyl group, two ring [2.2.1] octyl groups etc.
Contain the substituted naphthenic base of one or more heteroatoms (like nitrogen, oxygen, sulphur) in " heterocyclic radical (heterocyclic) " representative structure; For example 1; The 3-dioxolane (1,3-dioxolane), pyrrolidyl (pyrrolidinyl), pyrazolinyl (pyrazolinyl), piperidyl (piperidinyl), piperazinyl (piperazinyl), tetrahydrofuran base (tetrahydrofuryl) etc.
In addition, above-mentioned aromatic base, one or more Wasserstoffatoms on assorted aromatic base, naphthenic base or the heterocyclic radical can be further by halogen, hydroxyl, amido or other functional group replacements.
Can know that by formula (I), (II) chipal compounds of the present invention is asymmetric 1,4:3,6-two dehydration N.F,USP MANNITOL and Isosorbide (isomannide/isosorbide) chipal compounds, and have a light and reply (photosensitive) functional group.Have a compound (disclosed like US6589445) that two light are replied the functional group compared to known, the chipal compounds that this single light is replied base can promote the purity of color of cholesteryl liquid crystal.
The chipal compounds of formula (I) can be from 1,4:3, and 6-two dehydration N.F,USP MANNITOL (isomannide) forms via two step esterifications, and its reaction formula is (R as follows
1, R
2Definition the same, X representative-OH or-Cl):
Likewise, the chipal compounds of formula (II) can form via two step esterifications from Isosorbide (isosorbide), and its reaction formula is (R as follows
1, R
2Definition the same, X representative-OH or-Cl):
First esterification can be carried out about 4 hours to room temperature at 0 ℃ usually, and second esterification can be carried out under about 80 ℃ about 20 hours usually.Detailed step about esterification can be referring to the description of following examples.
Prepared chipal compounds is a white solid, and good solubleness is arranged in the nematic liquid crystal prescription, and dissolving back be colourless, so color that can noisy reflection light.In addition, chipal compounds of the present invention has greater than 30 μ m usually
-1High screw twisted power (HTP), in preferred embodiment, screw twisted power (HTP) can reach 60 μ m
-1Therefore, being applied in only needs in the liquid-crystal compsn to add a spot of chipal compounds, can avoid too high mesomorphic phase behavior and the photoelectric characteristic to liquid-crystal compsn of addition to exert an adverse impact.
Liquid-crystal compsn of the present invention comprises:
(a) the liquid crystal main body of 100 weight parts; And
(b) formula of 3-20 weight part (I) or formula (II) chipal compounds; Preferable about 5-15 weight part.
Chipal compounds of the present invention can be used as the chiral additives that light is replied type, is added into nematic (Nematic) liquid crystal, smectic type (Smectic) liquid crystal or plate-like (discotic) liquid crystal.The preferably can be added on and form the cholesteryl liquid crystal prescription in the nematic liquid crystal, as the application of optical-write-in mode cholesteric liquid crystal display.
Employed liquid crystal main body can contain or not contain polymerizable functionalities base (polymerizable group).In addition, liquid-crystal compsn of the present invention also can optionally add polymerisable monomer, polymerization starter, binding resin (binder resin), solvent, tensio-active agent, tackifier, ultraviolet absorbers or other chiral additives.Specific examples relevant for liquid crystal main body and other composition can be with reference to US 6589445.
Light of the present invention is replied the type chipal compounds can produce the configuration change of molecule because of irradiation, and then produces screw twisted power (HTP) change, and the pitch (p) of cholesteryl liquid crystal is changed, and reaches to change different reflected light colors.According to irradiation time length, can make liquid-crystal compsn of the present invention produce the wavelength shift that 50～250nm does not wait, appear with scope and comprise redness (R), green (G), blue specific reflection wavelength such as (B) at visible light (380nm-800nm).The employed light source of irradiation is preferable with UV-light, because of it has higher energy, can shorten molecular configuration and change the required time.
Have a compound that two light are replied the functional group compared to known, it is less to utilize the single light of the present invention to reply functional group's the crest halfwidth (Δ λ) of the cholesteryl liquid crystal that chipal compounds made prescription, therefore presents preferable purity of color.In addition, the temperature dependency low (absolute value of d λ/dT is less than 1) of the reflection wavelength of the cholesteryl liquid crystal of gained prescription has more stable display quality.
Liquid-crystal compsn of the present invention also can form mixing solutions with high polymer monomer; Utilize the mode of heat or irradiation to make the high polymer monomer polymerization; Reduce to produce with solubleness between monomer in the polymerization process and liquid crystal and be separated; Liquid crystal is dispersed in the polymer with the droplet uniform form, become high-molecular dispersed cholesteryl liquid crystal (polymer dispersed cholesteric liquid crystal, PDChLC).
In sum, chipal compounds of the present invention provides following advantage at least:
1. possesses high screw twisted power (HTP＞30 μ m
-1).
2. good and own colourless with dispensing liquid crystal solubleness.
3. the cholesteryl liquid crystal prescription of being prepared has high color purity.
4. has stable temperature dependency (absolute value of d λ/dT is less than 1).
Through chipal compounds of the present invention; Can make the stable optical-write-in mode cholesteric liquid crystal display of a high color purity, display quality to do various widespread uses; For example electric label, e-book, smart card, flat-panel screens, large-scale advertisement billboard, and hand-written computingmachine etc.
Liquid-crystal compsn of the present invention also can be used for making the display unit of other type, for example stable twisted nematic (TN) indicating meter, STN Super TN type (STN) indicating meter, colored STN Super TN type (CSTN) indicating meter and film transistor type (TFT) indicating meter.In addition, liquid-crystal compsn of the present invention still can be used for making reflecting type polarizing plate, cholesteric type reflecting type polarizing plate, reflector, optical compensation films, phase shift films, colorized optical filtering, photochromic coating or liquid crystalline dyes etc.
[comparative example 1: two light are replied the chipal compounds 1 of base]
(10.7g 60mmol) puts into two-neck bottle, and the good return line of frame, utilizes filling tube with SOCl to take by weighing 4-methoxy cinnamic acid (4-Methoxycinnamic acid)
2Splash into, 50 ℃ of down reactions after about 3 hours, with vacuum pump with unnecessary SOCl
2Take out remaining weak yellow liquid.On the other hand, with isomannide (7.3g 50mmol) is dissolved in pyridine (pyridine) (20ml) and in the methylene dichloride (50ml), slowly splashes into liquid with filling tube, about 20 hours of room temperature reaction, reaction finishes with HCl
(aq)And CH
2Cl
2Extraction, after getting organic layer and draining faint yellow oily thing, with the MeOH recrystallize, can obtain white solid, productive rate be 28.7% (6.7g, 14.4mmol).The HTP=45 μ m of product
-1
[comparative example 2: two light are replied the chipal compounds 2 of base]
Synthesis step is with comparative example 1, but changes isomannide into isosorbide, and products therefrom is a white solid, HTP=45 μ m
-1
[embodiment 1]
(10.7g 60mmol) puts into two-neck bottle, and the good return line of frame, utilizes filling tube with SOCl to take by weighing 4-methoxy cinnamic acid (4-Methoxycinnamic acid)
2Splash into, 50 ℃ of down reactions after about 3 hours, with vacuum pump with unnecessary SOCl
2Take out remaining weak yellow liquid.On the other hand, (7.3g 50mmol) is dissolved in pyridine (20ml) and the methylene dichloride (50ml), slowly splashes into liquid with filling tube, and ice bath reacted about 4 hours down, and reaction finishes with HCl with isosorbide
(aq)And CH
2Cl
2Extraction, after getting organic layer and draining faint yellow oily thing, use the MeOH recrystallize earlier, obtain by product not after, can get product with the tubing string chromatographic separation again, productive rate be 33.3% (5.1g, 16.7mmol).
Take by weighing 3-(4-methoxyl group-phenyl)-vinylformic acid 6-hydroxyl-six hydrogen-fluorine [3; 2-b] furans-3-base ester (3-(4-Methoxy-phenyl)-acrylic acid 6-hydroxy-hexahydro-furo [3; 2-b] furan-3-ylester) (3.8g; 15mmol) put into two-neck bottle, and the good return line of frame, utilize filling tube with SOCl
2Splash into, 50 ℃ of down reactions after about 3 hours, with vacuum pump with unnecessary SOCl
2Take out remaining white solid.On the other hand, (1.5g 5mmol) is dissolved in the pyridine (50ml) with back gained white solid; Slowly splash into liquid with filling tube; Add a small amount of 4-dimethylamino pyridine (4-Dimethylaminopyridine) again, be heated to about 20 hours of 80 ℃ of reactions, reaction finishes with HCl
(aq)And ethyl acetate extraction, after getting organic layer and draining faint yellow oily thing, utilize the tubing string chromatographic separation can get product and be white solid, productive rate be 21% (0.6g, 1mmol).The HTP=60 μ m of product
-1
[embodiment 2]
Synthesis step is with embodiment 1, but changes isosorbide into isomannide, and products therefrom is a white solid, HTP=33 μ m
-1
[irradiation assessment result]
The chipal compounds of 0.15 gram embodiment 1 is disposed in 2.94 grams nematic liquid crystal main body BL-087 (Merck) in (degree of birefringence is 0.24), with UV lamp (365nm;～2mW/cm
2) cholesteryl liquid crystal wavelength before the irradiation is 568nm, irradiation was 782nm after 270 seconds, wavelength shift is up to 214nm.
[purity of color analysis]
Respectively the chiral molecules of 0.50 gram comparative example 1 and embodiment 1 is disposed among the 6.81 gram nematic liquid crystal main body BL-087 (Merck) in (degree of birefringence is 0.24), with UV lamp (365nm;～2mW/cm
2) irradiation 0～60 second, measure its crest halfwidth (Δ λ), result such as table 1 and shown in Figure 1.
Table 1
Can know by table 1 and Fig. 1 and to find out that the Δ λ of the photosensitive pattern cholesteryl liquid crystal that chiral molecules made of embodiment 1 is less, demonstrates preferable purity of color.This is because the molecule of embodiment 1 has only a light to reply base, and the photoisomerization reaction of trans to cis is simple; The molecule of comparative example one because of have two light reply base then need pass through (trans, trans) to (cis, trans) or (trans, cis) transition state is at last just to (cis cis), causes Δ λ bigger.
[temperature dependency analysis]
Respectively the chiral molecules of 0.40 gram comparative example 2 with embodiment 1 is disposed among the 4.63 gram nematic liquid crystal main body BL-087 (Merck).The cholesteryl liquid crystal of gained is filled a prescription in 0 ℃～50 ℃ following its reflection wavelengths of measuring, obtain like Fig. 2 and graph of a relation shown in Figure 3, parallel linear regression obtains slope (d λ/dT) be respectively-1.05 (comparative example 2) ,-0.51 (embodiment 1).Hence one can see that, and the cholesteryl liquid crystal prescription of gained of the present invention is more insensitive for temperature, can have more stable display quality.
Though the present invention discloses as above with several preferred embodiments; Right its is not in order to limit the present invention; Has common knowledge the knowledgeable in the technical field under any; Do not breaking away from the spirit and scope of the present invention, when can changing arbitrarily and retouching, so protection scope of the present invention is as the criterion when looking the scope that the accompanying Claim book defined.
Claims (6)
1. chipal compounds has the structure suc as formula (I) or formula (II):
R wherein
1, R
2Be-OCH
3
2. liquid-crystal compsn comprises:
The liquid crystal main body of 100 weight parts; And
The chipal compounds according to claim 1 of 3-20 weight part.
3. liquid-crystal compsn according to claim 2, (absolute value of d λ/dT) is less than 1 for the temperature dependency of its reflection wavelength.
4. liquid-crystal compsn according to claim 2, its reflection wavelength is between 380-800nm.
5. liquid-crystal compsn according to claim 2, wherein this liquid crystal main body is a nematic liquid crystal.
6. liquid-crystal compsn according to claim 2, it is the dispensing liquid crystal as the optical-write-in mode cholesteric liquid crystal display.
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Non-Patent Citations (2)
| Title |
|---|
| Lub, J. et al..Photoisomerizable chiral compounds derived from isosorbide and cinnamic acid.《Liquid Crystals》.2007,第32卷(第8期),1031-1044. * |
| Lub, Johan, et al..Synthesis and properties of photoisomerizable derivatives of isosorbide and their use in cholesteric filters.《Advanced Functional Materials》.2005,第15卷(第12期),1961-1972. * |
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