CN102453037A - Isosorbitol derivative and liquid crystal display containing same - Google Patents
Isosorbitol derivative and liquid crystal display containing same Download PDFInfo
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- CN102453037A CN102453037A CN2010105294342A CN201010529434A CN102453037A CN 102453037 A CN102453037 A CN 102453037A CN 2010105294342 A CN2010105294342 A CN 2010105294342A CN 201010529434 A CN201010529434 A CN 201010529434A CN 102453037 A CN102453037 A CN 102453037A
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- isosorbide
- liquid crystal
- verivate
- solution
- crystal display
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- 0 CC(C)(c1ccc(C(C)(*)*(CC2)CC*2N)cc1)[N+]([O-])OC(COC12)C1OCC2O[N+](C(C)(C)c1ccc(C(C)(*)*(CC2)CC*2N=N)cc1)[O-] Chemical compound CC(C)(c1ccc(C(C)(*)*(CC2)CC*2N)cc1)[N+]([O-])OC(COC12)C1OCC2O[N+](C(C)(C)c1ccc(C(C)(*)*(CC2)CC*2N=N)cc1)[O-] 0.000 description 2
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Abstract
The invention relates to an isosorbitol derivative, wherein it has the following chemical formulas (I): FORMULA, wherein Z is -CH2-CH2-, -CH=CH-, -C is equivalent to C-, -CH2-O-, -CH2-S-, -CH=N-O-, -CO-O-, -CO-S-, a single bond, -ph-, -CO-O-ph- or -CO-O-ph-CO-O-, wherein ph is a phenylene radical; R1 and R2 are independently to be alkyls, -CN, -NCS, -CH3 or -OCX3, which have 1-25 carbons, wherein X is halogen; m and n are independently to be 0, 1 or 2. The invention also provides a liquid crystal display containing the isosorbitol derivative.
Description
Technical field
The present invention relates to a kind of isosorbide (isosorbide) verivate, particularly relates to a kind of isosorbide verivate that is doped in liquid-crystal display.
Background technology
In recent years; Because the prosperity of liquid crystal industry, reason answer the liquid crystal material of various different demands to be developed successively, wherein; Cholesteryl liquid crystal (cholesteric liquid crystal) is owing to have bistability (bistability); And under no impressed voltage situation, still can keep the picture performance, therefore, have an opportunity to become the plane technique of display of a new generation.
Cholesteric liquid crystal material has had spirane structure and liquid crystal characteristic concurrently.Its spirane structure normally is doped in chiral dopant (chiral dopant) in the cholesteric liquid crystal molecules of not being with chirality and forms.Therefore, (helical twisting power HTP) promptly is the principal element of decision cholesteryl liquid crystal screw twisted degree to the screw twisted power of chiral molecules.In general, every kind of chiral structure has its different HTP.
Chiral dopant is a kind of optically active substance.Chiral dopant is added tool when being listed as the liquid crystal of (nematic) phase, can make the liquid crystal rotation become the cholesteryl liquid crystal phase.Screw twisted power (HTP) size of chiral molecules mainly is the characteristic that depends on chiral dopant itself, but also can receive like main nematic liquid crystal material (nematic liquid crystal host) and Influence of Temperature simultaneously.
Summary of the invention
The object of the present invention is to provide a kind of novel cpd that can be used for cholesteric liquid crystal display.
In the embodiment of the present invention, a kind of isosorbide verivate is provided, has chemical formula (I):
Wherein Z is-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-CH
2-O-,-CH
2-S-,-CH=N-O-,-CO-O-,-CO-S-, singly-bound ,-ph-,-CO-O-ph-or-CO-O-ph-CO-O-, wherein ph is the penylene base; R
1With R
2Be independently carbon number 1～25 alkyl ,-CN ,-NCS ,-CX
3Or-OCX
3, wherein X is a halogen; And m and n are 0,1 or 2 independently.
In the embodiment of the present invention, a kind of liquid-crystal display is provided, comprises: a upper substrate; One hypocoxa is oppositely arranged with this upper substrate; And a liquid crystal layer, be arranged between this upper substrate and this hypocoxa, comprise an isosorbide verivate, have chemical formula (I):
Wherein Z is-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-CH
2-O-,-CH
2-S-,-CH=N-O-,-CO-O-,-CO-S-, singly-bound ,-ph-,-CO-O-ph-or-CO-O-ph-CO-O-, wherein ph is the penylene base, R
1With R
2Be independently carbon number 1～25 alkyl ,-CN ,-NCS ,-CX
3Or-OCX
3, wherein X is a halogen, and m and n are 0,1 or 2 independently.
The present invention develops a kind of isosorbide verivate chiral dopant of novelty, and its core texture is to be made up of an isosorbide, and connects structure with piperazine as its side chain.Isosorbide verivate of the present invention confirmation after testing for example can effectively promote the temperature stability of cholesteryl liquid crystal (its temperature dependency (temperature dependence) is less than or equal 0.2nm/ ℃); In addition, this isosorbide verivate also has bigger screw twisted power (HTP) (for example can be greater than 45 μ m
-1), for the screw twisted degree that promotes cholesteryl liquid crystal suitable help is arranged.
For letting above-mentioned purpose of the present invention, characteristic and the advantage can be more obviously understandable, hereinafter is special lifts a preferred embodiment, elaborates as follows:
Embodiment
One embodiment of the invention provide a kind of isosorbide verivate, have chemical formula (I):
In chemical formula (I), Z can be-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-CH
2-O-,-CH
2-S-,-CH=N-O-,-CO-O-,-CO-S-, singly-bound ,-ph-,-CO-O-ph-or-CO-O-ph-CO-O-, above-mentioned ph represents the penylene base.
R
1With R
2Can be independently carbon number 1～25 alkyl ,-CN ,-NCS ,-CX
3Or-OCX
3, above-mentioned X represents halogen.
M and n can be 0,1 or 2 independently.
Below enumerate the particular instance of isosorbide verivate of the present invention:
(compd A-2C1),
(compd A-2C5),
(compd A-2IC5),
(compd A-2BC5),
(compd A-C1C5),
(compd A-2aBC1),
(compd A-2CN),
(compd A-2CF3).
One embodiment of the invention provide a kind of liquid-crystal display, comprise a upper substrate, and a hypocoxa is oppositely arranged with upper substrate, and a liquid crystal layer, is arranged between upper substrate and the hypocoxa, comprise an isosorbide verivate, have chemical formula (I):
In chemical formula (I), Z can be-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-CH
2-O-,-CH
2-S-,-CH=N-O-,-CO-O-,-CO-S-, singly-bound ,-ph-,-CO-O-ph-or-CO-O-ph-CO-O-, above-mentioned ph represents the penylene base.
R
1With R
2Can be independently carbon number 1～25 alkyl ,-CN ,-NCS ,-CX
3Or-OCX
3, above-mentioned X represents halogen.
M and n can be 0,1 or 2 independently.
Isosorbide verivate of the present invention can be doped in the for example liquid-crystal display of cholesteryl liquid crystal.
The present invention develops a kind of isosorbide verivate chiral dopant of novelty, and its core texture is to be made up of an isosorbide, and connects structure with piperazine as its side chain.Isosorbide verivate of the present invention confirmation after testing for example can effectively promote the temperature stability of cholesteryl liquid crystal (its temperature dependency is less than or equal 0.2nm/ ℃); In addition, this isosorbide verivate also has bigger screw twisted power (HTP) (for example can be greater than 45 μ m
-1), for the screw twisted degree that promotes cholesteryl liquid crystal suitable help is arranged.
[embodiment]
Synthetic 1 of [embodiment 1] isosorbide verivate of the present invention
Compd A-2C1
At first; With 4-[4-methyl-piperazine-1-the yl]-phenylformic acid (4-[4-Methyl-piperazin-1-yl]-benzoic acid) of 2.2 grams (10mmol) and 2.43 restrain 1; 1 "-carbonyl dimidazoles (1; 1 "-Carbonyldiimidazole, CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, in nitrogen (N
2) under the environment, squeeze into 30 milliliters anhydrous tetrahydro furan (THF)., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (3mmol) of 0.45 gram is placed another round-bottomed bottle, and under ice bath, add the THF dissolving.Afterwards, add sodium hydride (NaH), promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol (MeOH) to carry out recrystallization, can obtain the compd A-2C1 of 1.15 grams, productive rate 70%, outward appearance is a white solid.
The Synthetic 2 of [embodiment 2] isosorbide verivate of the present invention
Compd A-2C5
At first, with 4-[4-amyl group-piperazine-1-the yl]-phenylformic acid (4-[4-Pentyl-piperazin-1-yl]-benzoic acid) of 2.76 grams (10mmol) and 2.43 restrain 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, in nitrogen (N
2) under the environment, squeeze into 30 milliliters anhydrous tetrahydro furan (THF)., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (3mmol) of 0.45 gram is placed another round-bottomed bottle, and under ice bath, add THF (THF) and dissolve it.Afterwards, add sodium hydride (NaH), promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol (MeOH) to carry out recrystallization, can obtain the compd A-2C5 of 1.25 grams, productive rate 63%, outward appearance is a white solid.
Synthetic 3 of [embodiment 3] isosorbide verivate of the present invention
Compd A-2IC5
At first; With 4-[4-(1-methyl-butyl)-piperazine-1-yl]-phenylformic acid (4-[4-(1-Methyl-butyl)-piperazin-1-y1]-benzoic acid) of 2.76 grams (10mmol) and 2.43 restrain 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, under nitrogen environment, squeeze into 30 milliliters anhydrous tetrahydro furan., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (3mmol) of 0.45 gram is placed another round-bottomed bottle, and under ice bath, add the THF dissolving.Afterwards, add sodium hydride, promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol to carry out recrystallization, can obtain the compd A-2IC5 of 1.29 grams, productive rate 65%, outward appearance is a white solid.
Synthetic 4 of [embodiment 4] isosorbide verivate of the present invention
Compd A-2BC5
At first; With 4-[4-(4-amyl group-phenyl)-piperazine-1-yl]-phenylformic acid (4-[4-(4-Pentyl-phenyl)-piperazin-1-y1]-benzoic acid) of 3.52 grams (10mmol) and 2.43 restrain 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, under nitrogen environment, squeeze into 30 milliliters anhydrous tetrahydro furan., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (3mmol) of 0.45 gram is placed another round-bottomed bottle, and under ice bath, add the THF dissolving.Afterwards, add sodium hydride, promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol to carry out recrystallization, can obtain the compd A-2BC5 of 1.61 grams, productive rate 66%, outward appearance is a white solid.
Synthetic 5 of [embodiment 5] isosorbide verivate of the present invention
Compd A-C1C5
At first, with 4-[4-methyl-piperazine-1-the yl]-phenylformic acid (4-[4-Methyl-piperazin-1-yl]-benzoic acid) of 2.2 grams (10mmol) and 2.43 restrain 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, under nitrogen environment, squeeze into 30 milliliters anhydrous tetrahydro furan., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (13mmol) of 1.9 grams is placed another round-bottomed bottle, and under ice bath, add the THF dissolving.Afterwards, add sodium hydride, promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, carry out tubing string chromatography (with ETHYLE ACETATE EA: normal hexane HEX=1: 1 as extract), obtain the midbody (6mmol) of 2.1 grams, productive rate 66%.
Afterwards, with 4-[4-amyl group-piperazine-1-the yl]-phenylformic acid (4-[4-Pentyl-piperazin-1-yl]-benzoic acid) of 2.21 grams (8mmol) and 2.43 restrain 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, under nitrogen environment, squeeze into 30 milliliters anhydrous tetrahydro furan., put after four hours in reflux, promptly accomplish the preparation of C solution to room temperature.
Then, above-mentioned midbody is placed another round-bottomed bottle, and under ice bath, the dissolving of adding THF.Afterwards, add sodium hydride, promptly accomplish the preparation of D solution.After two hours, above-mentioned C solution is poured in the D solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol to carry out recrystallization, can obtain the compd A-C1C5 of 1.83 grams, productive rate 50%, outward appearance is a white solid.
Synthetic 6 of [embodiment 6] isosorbide verivate of the present invention
Compd A-2aBC1
At first; With 4-(4-carboxyl-phenyl)-piperazine-1-carboxylic acid-p-tolyl ester (4-(4-Carboxy-phenyl)-piperazin-1-carboxylic acid-p-tolyl ester) of 3.40 grams (10mmol) and 2.43 grams 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, under nitrogen environment, squeeze into 30 milliliters anhydrous tetrahydro furan., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (3mmol) of 0.45 gram is placed another round-bottomed bottle, and under ice bath, add the THF dissolving.Afterwards, add sodium hydride, promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol to carry out recrystallization, can obtain the compd A-2aBC1 of 1.54 grams, productive rate 65%, outward appearance is a white solid.
Synthetic 7 of [embodiment 7] isosorbide verivate of the present invention
Compd A-2CN
At first, with 4-(4-cyanic acid-piperazine-1-the yl)-phenylformic acid (4-(4-cyano-piperazin-1-yl)-benzoic acid) of 2.31 grams (10mmol) and 2.43 restrain 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, under nitrogen environment, squeeze into 30 milliliters anhydrous tetrahydro furan., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (3mmol) of 0.45 gram is placed another round-bottomed bottle, and under ice bath, add the THF dissolving.Afterwards, add sodium hydride, promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol to carry out recrystallization, can obtain the compd A-2CN of 0.9 gram, productive rate 68%, outward appearance is a white solid.
Synthetic 8 of [embodiment 8] isosorbide verivate of the present invention
Compd A-2CF3
At first; With 4-(4-trifluoromethyl-piperazine-1-the yl)-phenylformic acid (4-(4-Trifluoromethyl-piperazin-1-yl)-benzoic acid) of 2.74 grams (10mmol) and 2.43 restrain 1,1 "-carbonyl dimidazoles (CDI) (15mmol) places two neck round-bottomed bottles of 100 milliliters.Afterwards, under nitrogen environment, squeeze into 30 milliliters anhydrous tetrahydro furan., put after four hours in reflux, promptly accomplish the preparation of A solution to room temperature.
Then, the isosorbide (3mmol) of 0.45 gram is placed another round-bottomed bottle, and under ice bath, add the THF dissolving.Afterwards, add sodium hydride, promptly accomplish the preparation of B solution.After two hours, above-mentioned A solution is poured in the B solution, and be stirred to room temperature about two hours.After draining, can obtain yellow solid.Then, use methyl alcohol to carry out recrystallization, can obtain the compd A-2CF3 of 1.18 grams, productive rate 60%, outward appearance is a white solid.
The screw twisted power (HTP) and the temperature dependency of [embodiment 9] isosorbide verivate of the present invention
The relevant physicochemical characteristic of isosorbide verivate of the present invention (compd A-2C1, A-2C5, A-2IC5, A-2BC5, A-C1C5, A-2aBC1, A-2CN, A-2CF3); Screw twisted power (helicaltwisting power for example; HTP) and temperature dependency (temperature dependence, d λ/dT) are shown in following table 1.Measuring temperature is 20～50 ℃.
Table 1
Can find out that by table 1 isosorbide verivate of the present invention (compd A-2C1, A-2C5, A-2IC5, A-2BC5, A-C1C5, A-2aBC1, A-2CN, A-2CF3) has bigger screw twisted power (HTP), for example all greater than 45 μ m
-1, and its temperature dependency is low, for example all is less than or equal to 0.2nm/ ℃, therefore, quite is fit to be applied to the for example liquid-crystal display of cholesteryl liquid crystal.
Though the present invention discloses as above with preferred embodiment; Right its is not in order to limiting the present invention, anyly has the knack of this art, do not breaking away from the spirit and scope of the present invention; When can doing to change and retouching, so protection scope of the present invention is as the criterion when looking the scope that accompanying Claim defines.
Claims (4)
1. isosorbide verivate has chemical formula (I):
Wherein
Z is-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-CH
2-O-,-CH
2-S-,-CH=N-O-,-CO-O-,-CO-S-, singly-bound ,-ph-,-CO-O-ph-or-CO-O-ph-CO-O-, wherein ph is the penylene base;
R
1With R
2Be independently carbon number 1～25 alkyl ,-CN ,-NCS ,-CX
3Or-OCX
3, wherein X is a halogen; And
M and n are 0,1 or 2 independently.
2. isosorbide verivate as claimed in claim 1, wherein this isosorbide verivate bag
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, comprises an isosorbide verivate, has chemical formula (I):
Wherein Z is-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-CH
2-O-,-CH
2-S-,-CH=N-O-,-CO-O-,-CO-S-, singly-bound ,-ph-,-CO-O-ph-or-CO-O-ph-CO-O-, wherein ph is the penylene base, R
1With R
2Be independently carbon number 1～25 alkyl ,-CN ,-NCS ,-CX
3Or-OCX
3, wherein X is a halogen, and m and n are 0,1 or 2 independently.
4. liquid-crystal display as claimed in claim 3, wherein this liquid-crystal display is a cholesteric liquid crystal display.
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|---|---|---|---|---|
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| CN1715309A (en) * | 2005-07-22 | 2006-01-04 | 东北大学 | Thermotropic front cholesteric liquid crystal polymer and its preparing method |
| TW200825158A (en) * | 2006-12-12 | 2008-06-16 | Ind Tech Res Inst | Additive for liquid crystal having high helical twisting power, synthesis method thereof and a liquid crystal composition containing the additive |
| EP2028253A1 (en) * | 2007-08-24 | 2009-02-25 | Chisso Corporation | Optically isotropic liquid crystal medium and optical device |
| CN101479362A (en) * | 2006-06-27 | 2009-07-08 | 西柏控股有限公司 | Cholesteric multi-layers |
-
2010
- 2010-10-25 CN CN201010529434.2A patent/CN102453037B/en active Active
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|---|---|---|---|---|
| US6022969A (en) * | 1994-09-23 | 2000-02-08 | Axys Pharmaceuticals, Inc. | Compositions and methods for treating mast-cell mediated conditions |
| CN1394862A (en) * | 2001-07-02 | 2003-02-05 | 默克专利股份有限公司 | Chiral compound |
| CN1715309A (en) * | 2005-07-22 | 2006-01-04 | 东北大学 | Thermotropic front cholesteric liquid crystal polymer and its preparing method |
| CN101479362A (en) * | 2006-06-27 | 2009-07-08 | 西柏控股有限公司 | Cholesteric multi-layers |
| TW200825158A (en) * | 2006-12-12 | 2008-06-16 | Ind Tech Res Inst | Additive for liquid crystal having high helical twisting power, synthesis method thereof and a liquid crystal composition containing the additive |
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| Title |
|---|
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| KENNETH D.RICE,等: "Dibasic inhibitors of human mast cell tryptase. Part 2: Structure–activity relationships and requirements for potent activity", 《BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS》, vol. 10, no. 20, 16 October 2000 (2000-10-16), pages 2361 - 2366 * |
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