CN110669529A - Color liquid crystal material and application thereof - Google Patents
Color liquid crystal material and application thereof Download PDFInfo
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- CN110669529A CN110669529A CN201910855198.4A CN201910855198A CN110669529A CN 110669529 A CN110669529 A CN 110669529A CN 201910855198 A CN201910855198 A CN 201910855198A CN 110669529 A CN110669529 A CN 110669529A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/323—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a binaphthyl
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
Abstract
The invention discloses a color liquid crystal material and application thereof; synthesizing an acrylate additive containing groups such as isosorbide and synthesizing an acrylate liquid crystal molecule containing p-hydroxy toluene; by mixing the acrylate additive with liquid crystal molecules, bright and colorful liquid crystal materials can be obtained. The method has the advantages of simple process route, low raw material consumption, short reaction time and convenient operation.
Description
Technical Field
The invention belongs to the field of liquid crystal, and particularly relates to a preparation method of a liquid crystal material containing an additive.
Background
Liquid crystals are a special form of matter, having both the fluidity of a liquid and the anisotropy of a portion of the crystal molecules. The liquid crystal luminescent material has great application potential in the fields of displays and sensors, but the most commonly encountered problem when the liquid crystal material is used is how to adjust the diversity and the brightness of the reflection color. The prior art discloses some methods for modifying liquid crystal, but the defects of poor compatibility, low HTP value and the like exist; therefore, there is a high need for a system that provides compatibility and has a high HTP value, and thus a high performance color liquid crystal material.
Disclosure of Invention
The invention synthesizes an acrylate additive containing groups such as isosorbide and synthesizes an acrylate liquid crystal molecule containing p-hydroxy toluene; by mixing the acrylate additive with liquid crystal molecules, bright and colorful liquid crystal materials can be obtained. The method has the advantages of simple process route, low raw material consumption, short reaction time and convenient operation.
The technical scheme of the invention is as follows:
a color liquid crystal material comprises an acrylate additive and liquid crystal molecules.
The invention also discloses a preparation method of the color liquid crystal material, which comprises the following steps of heating and mixing the acrylate additive and the liquid crystal molecules to obtain the color liquid crystal material.
The color liquid crystal material is prepared from an acrylate additive and liquid crystal molecules, wherein the mass of the acrylate additive is 5.0 ~ 7.5.5% of the mass of the liquid crystal molecules.
In the invention, the chemical structural formula of the acrylate additive is as follows:
the chemical structural formula of the liquid crystal molecules is as follows:
wherein A is1、A2Independently selected from hydrogen or methyl, n, m independently selected from 4 ~ 9;B1、B2independently represent an aromatic group of C6 ~ C18, i.e. an aromatic group containing 6 ~ 18 carbon atoms, such as:
m is the following group:
n is the following group:
in the invention, the heating and mixing consists of 1 ~ 10 times of heating and stirring, the liquid crystal and the additive in the system can be mixed more uniformly and the color is more uniform by increasing the times of heating and stirring, the temperature of each heating and stirring is 80 ~ 150 ℃, and the time is 4 ~ 15 minutes.
The synthesis method of the acrylate additive comprises the following steps of reacting acrylic ester benzoic acid, p-hydroxybenzoate, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a solvent under the protection of nitrogen to obtain the acrylate additive. Preferably, after the reaction is finished, the reaction solution is filtered, the collected filtrate is subjected to reduced pressure distillation and spin drying, and then is recrystallized by methanol to obtain a white solid which is the acrylate additive.
The method for synthesizing the liquid crystal molecules comprises the following steps of reacting acrylic ester benzoic acid, hydroxybenzene, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a solvent under the protection of nitrogen to obtain the liquid crystal molecules. Preferably, after the reaction is finished, the reaction solution is filtered, and the collected filtrate is subjected to reduced pressure distillation and spin-drying and then is recrystallized by methanol to obtain a white solid which is a liquid crystal molecule.
In the preparation method, the solvent is tetrahydrofuran, the reaction time is 1 ~ 3 days, the acrylate benzoic acid is acrylate six-carbon benzoic acid, the p-hydroxybenzoate ester is p-hydroxybenzoate isosorbide, p-hydroxybenzoate binaphthyl diphenol ester or 4,4 '-dihydroxyazophenyl p-hydroxybenzoate, and the hydroxybenzene is 2, 5-dihydroxytoluene or 4, 4' -dihydroxyazophenyl p-hydroxybenzoate.
The preparation method disclosed by the invention can be exemplified as follows:
(1) synthesis of acrylate additives:
weighing acrylic ester benzoic acid (7.95 ~ 12.71.71 g), p-hydroxybenzoic acid isosorbide (5 ~ 8 g), Dicyclohexylcarbodiimide (DCC) (3.47 ~ 5.55.55 g) and 4-Dimethylaminopyridine (DMAP) (0.316 ~ 0.506.506 g) into a 100mL three-neck flask for later use, weighing 50 ~ 150mL of fresh Tetrahydrofuran (THF), adding into the flask, reacting for 1 ~ 3 days under the protection of nitrogen, filtering the reaction liquid after the reaction is finished, collecting the filtrate, performing reduced pressure distillation and spin drying on the filtrate, and recrystallizing with methanol to obtain a white solid which is the acrylic ester additive.
(2) Synthesis of liquid crystal molecules:
acrylate benzoic acid (4 ~ 9 g), 2, 5-dihydroxytoluene (0.85 ~ 1.91.91 g), DCC (3.10 ~ 6.98.98 g) and DMAP (0.167 ~ 0.376.376 g) are weighed and put into a 100mL three-neck flask for standby application, 50 ~ 150mL of fresh THF is weighed and added into the flask, the reaction is carried out for 1 ~ 3 days under the protection of nitrogen, the reaction solution is filtered after the reaction is finished, the filtrate is collected, is subjected to reduced pressure distillation and spin drying and then is recrystallized by methanol, and white solid which is liquid crystal molecules is obtained.
(3) Preparation of liquid crystal material:
weighing acrylate additives (40 ~ 120mg, 0.053 mmol) and liquid crystal molecules (1 g, 1.1 mmol), adding into a sample bottle, heating at 80 ~ 150 ℃ until the mixture is clear, keeping for 4 ~ 15 minutes, stirring by using a vortex oscillator for one-time heating, repeating the heating and stirring step for 4 ~ 10 times, and uniformly mixing the sample to obtain the target liquid crystal material.
Dipping a small amount of liquid crystal material samples, smearing the samples on a cover glass, covering a layer of cover glass to form a sandwich structure, and observing bright colors after the sandwich structure is naturally cooled.
The invention has the advantages that:
1. the invention prepares the additive containing groups such as isosorbide, and the isosorbide can provide high HTP value and can achieve larger distortion effect with less addition amount.
2. The additive and the liquid crystal molecules have similar long carbon chains and better compatibility, and the problem of crystallization of the liquid crystal mixture in the prior art is solved.
3. The additive and the liquid crystal molecules are both terminated by acrylate, can easily generate cross-linking reaction to generate a colorful high-molecular polymer film, and has wide application prospect in optical active optical films.
Drawings
FIG. 1 is a color photograph of a liquid crystal material 1 of each formulation of example one a ~ f;
FIG. 2 is a DSC curve of liquid crystal material 1 of each formulation of example one a ~ b;
FIG. 3 is a DSC curve of liquid crystal material 1 of each formulation of example one c ~ d;
FIG. 4 is a DSC curve of liquid crystal material 1 of formulation E ~ f;
FIG. 5 is a photomicrograph of a polarizing microscope showing the liquid crystal material 1 of each formulation of example one a ~ f;
FIG. 6 is a nuclear magnetic diagram of a liquid crystal molecule according to an embodiment;
FIG. 7 is a photograph of the color of the liquid crystal material 2 of each formulation of example two.
Detailed Description
The invention is further illustrated by the following examples.
The preparation method of the color liquid crystal material comprises the following step of heating and mixing the acrylate additive and the liquid crystal molecules to obtain the color liquid crystal material.
Example one
Preparing a liquid crystal material 1 comprising the following structure:
acrylate additive A
Liquid crystal molecule A
(1) Synthesis of acrylate additive a:
acrylate six-carbon benzoic acid (7,945 g, 27.2 mmol), p-hydroxybenzoic acid isosorbide (5 g, 12.9 mmol), DCC (3.468 g, 16.8 mmol), DMAP (0.316 g, 2.59 mmol) were weighed into a 100mL three-necked flask for use. 70mL of freshly distilled THF was measured and added to the flask and reacted under nitrogen for two days. After the reaction is finished, the reaction solution is filtered, the filtrate is collected, is subjected to reduced pressure distillation and spin drying, and is recrystallized by methanol, so that a white solid which is the acrylate additive A is obtained, and the yield is 91%.
(2) Synthesis of liquid crystal molecules A:
acrylate six-carbon benzoic acid (4 g, 13.68 mmol), 2, 5-dihydroxytoluene (0.85 g, 6.84 mmol), DCC (3.103 g, 15.05 mmol), DMAP (0.167 g, 1.368 mmol) were weighed into a 100mL three-necked flask for use. 70mL of freshly distilled THF was measured and added to the flask and reacted under nitrogen for two days. After the reaction is finished, the reaction solution is filtered, the filtrate is collected, is subjected to reduced pressure distillation and spin drying, and is recrystallized by methanol, so that a white solid which is liquid crystal molecule A is obtained, and the yield is 72%.
(3) Preparation of liquid crystal material 1:
weighing acrylate additive A (50 mg, 0.053 mmol) and liquid crystal molecule A (1 g, 1.1 mmol), adding into a sample bottle, heating in 130 deg.C oil bath until the mixture is clear, stirring the sample with a vortex oscillator for 5 min, repeating the heating and stirring steps for 5 times; then dipping a small amount of sample and smearing on a cover glass, covering a layer of cover glass to form a sandwich structure, and observing bright orange after the sandwich structure is naturally cooled, as shown in figure 1-a.
The formula is shown in table 1, the color of the liquid crystal material is shown as a ~ f in fig. 1, the color of the color liquid crystal material is uniform, the compatibility of the liquid crystal and the additive is good, and no phase separation phenomenon exists, the physical property table of the liquid crystal material 1 with various colors can be obtained by combining the DSC curve data, the ellipsometer data and the reflection circle dichroism data of the liquid crystal material 1 with various formulas in fig. 2, 3 and 4, fig. 5 is a polarization microscope photograph of the liquid crystal material 1 with various formulas in example a ~ f, and fig. 6 is a nuclear magnetic diagram of a liquid crystal molecule in example a.
Table 1 and DSC tests can illustrate liquid crystallinity; when the acrylate additive A is 35mg and the liquid crystal molecule A is 1g, the material prepared by the same method has no color; when the acrylate additive A is 100mg and the liquid crystal molecule A is 1g, the material prepared by the same method has no color; the liquid crystal molecules were obtained by replacing the 2, 5-dihydroxytoluene with an equimolar amount of 5-fluororesorcinol (CAS No. 75996-29-1), and heating and mixing 1g of the above mixture with 60mg of the acrylate additive A in the same manner as described above, whereby the resulting liquid crystal material also exhibited a greenish hue, but had a low HTP value of 45.6.
Example two a liquid crystal material 2 was prepared comprising the following components:
acrylate additive B
Liquid crystal molecule A
(1) Synthesis of acrylate additive B:
acrylate six-carbon benzoic acid (6 g, 20.5 mmol), p-hydroxybenzoic acid binaphthyl diphenol ester (2.25 g, 9.78 mmol), DCC (8.06 g, 39.12 mmol), DMAP (0.477 g, 3.9 mmol) were weighed into a 100mL three-necked flask for use. 60mL of freshly distilled THF was measured and added to the flask and reacted under nitrogen for two days. After the reaction is finished, the reaction solution is filtered, and the filtrate is subjected to reduced pressure distillation and spin drying and then is recrystallized by methanol to obtain a product.
(2) Synthesis of liquid crystal molecules A:
synthesized in the same procedure as in example one.
(3) Preparation of liquid crystal material 2:
weighing a certain proportion of acrylate additive B, adding liquid crystal molecule A into a sample bottle, heating in 150 ℃ oil bath until the mixture is clarified, stirring the sample by using a vortex oscillator, keeping for 5 minutes, heating and stirring once, and repeating the heating and stirring step for 5 times. Dipping a small amount of sample, smearing on a cover glass, covering a layer of cover glass to form a sandwich structure, and naturally cooling to obtain the liquid crystal material 2. FIG. 7 is a photograph showing the colors of the liquid crystal material 2 of each of the formulations of the second example, wherein the liquid crystal molecules A are 1g, and the acrylic additive B has the masses of 50mg, 55mg, 60mg, 65mg, 70mg and 75mg, which correspond to the six colors from the left to the right in FIG. 7, respectively.
Example three a liquid crystal material 3 was prepared comprising the following components:
acrylate additive A
Liquid crystal molecule B
(1) Synthesis of acrylate additive a:
synthesized in the same procedure as in example one.
(2) Synthesis of liquid crystal molecules B:
acrylate six-carbon benzoic acid (7 g, 23.96 mmol), 4' -dihydroxyazophenyl p-hydroxybenzoate (2.63 g, 11.41 mmol), DCC (9.41 g, 45.64 mmol), DMAP (0.557 g, 4.56 mmol) were weighed into a 100mL three-necked flask for use. 80mL of freshly distilled THF was measured and added to the flask and reacted under nitrogen for two days. After the reaction is finished, the reaction solution is filtered, and the filtrate is subjected to reduced pressure distillation and spin drying and then is recrystallized by methanol to obtain a product.
(3) Preparation of liquid crystal material 3:
weighing a certain proportion of acrylate additive A, adding liquid crystal B into a sample bottle, heating in oil bath at 140 ℃ until the mixture is clarified, keeping for 7 minutes, stirring the sample by using a vortex oscillator, and repeating the heating and stirring step for 5 times to uniformly mix the sample. Dipping a small amount of sample, smearing on a cover glass, covering a layer of cover glass to form a sandwich structure, and naturally cooling to obtain the liquid crystal material 3. Wherein the liquid crystal molecule B is 1g, the mass of the acrylate additive A is 50mg, 55mg, 60mg, 65mg, 70mg and 75mg, which respectively correspond to six colors.
The invention adds a certain proportion of additive into the liquid crystal material to obtain cholesteric liquid crystal, and selectively reflects incident light, thereby emitting bright reflected light; the additive is a liquid crystal additive with high helical twisting power, and the optical activity and the high helical twisting power of the additive can enable liquid crystal molecules to reflect specific wavelengths, and the pitch of the liquid crystal molecules can be changed by adjusting the concentration of the additive; the performance of the chiral liquid crystal material is improved in two aspects of increasing the spiral twisting force constant (HTP value) of the additive and increasing the compatibility of the chiral molecules and the liquid crystal molecules; the invention solves the problems that the compatibility of the liquid crystal and the additive in the prior art is poor and the high HTP value can not be provided.
Claims (10)
1. A color liquid crystal material comprises an acrylate additive and liquid crystal molecules.
2. The colored liquid crystal material of claim 1, wherein the acrylate-based additive has the following chemical formula:
the chemical structural formula of the liquid crystal molecules is as follows:
3. the color liquid crystal material according to claim 2, wherein A is1、A2Independently selected from hydrogen or methyl, n, m independently selected from 4 ~ 9, B1、B2Independently represents a C6 ~ C18 aromatic group, M is the following group:
n is the following group:
4. the color liquid crystal material of claim 1, wherein the preparation method of the color liquid crystal material comprises the step of heating and mixing the acrylate additives and the liquid crystal molecules to obtain the color liquid crystal material.
5. The colored liquid crystal material of claim 4, wherein the mass of the acrylate-based additive is 5.0 ~ 7.5.5% of the mass of the liquid crystal molecules.
6. The colored liquid crystal material of claim 4, wherein the heat mixing is performed at 1 ~ 10 times of heat stirring, and the temperature of each heat stirring is 80 ~ 150 ℃ for 4 ~ 15 minutes.
7. The color liquid crystal material of claim 1, wherein the method for synthesizing the acrylate additive comprises the steps of reacting acrylic ester benzoic acid, p-hydroxybenzoate, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a solvent under the protection of nitrogen to obtain the acrylate additive; the synthesis method of the liquid crystal molecules comprises the following steps of reacting acrylic ester benzoic acid, hydroxybenzene, dicyclohexylcarbodiimide and 4-dimethylaminopyridine in a solvent under the protection of nitrogen to obtain the liquid crystal molecules.
8. The color liquid crystal material of claim 1, wherein the solvent is tetrahydrofuran, the reaction time is 1 ~ 3 days, the acrylate benzoic acid is hexa-carbon acrylate benzoic acid, the p-hydroxybenzoate ester is p-hydroxybenzoate isosorbide, p-hydroxybenzoate binaphthyl diphenol ester or p-hydroxybenzoate 4,4 '-dihydroxyazophenyl ester, and the hydroxybenzene is 2, 5-dihydroxytoluene or p-hydroxybenzoate 4, 4' -dihydroxyazophenyl ester.
9. The method for preparing a color liquid crystal material according to claim 1, comprising the step of heating and mixing the acrylate-based additive and the liquid crystal molecules to obtain the color liquid crystal material.
10. Use of the colored liquid crystal material according to claim 1 for the preparation of liquid crystal materials.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656667A (en) * | 2022-02-25 | 2022-06-24 | 苏州大学 | Epoxy liquid crystal film material and preparation method thereof |
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| CN114656667B (en) * | 2022-02-25 | 2022-11-15 | 苏州大学 | Epoxy liquid crystal film material and preparation method thereof |
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