CN112920814B - Double transition metal-based composite liquid crystal material and preparation method thereof - Google Patents
Double transition metal-based composite liquid crystal material and preparation method thereof Download PDFInfo
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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
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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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
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
- C09K19/3857—Poly(meth)acrylate derivatives containing at least one asymmetric carbon atom
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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
- C09K2019/0425—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect
- C09K2019/0433—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect the specific unit being a luminescent or electroluminescent unit
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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
- C09K2019/523—Organic solid particles
Abstract
The invention discloses a double transition metal-based composite liquid crystal material and a preparation method thereof. And (3) treating the mixture liquid to obtain the double-transition metal-based three-dimensional network nano particles, and adding a solvent into the double-transition metal-based three-dimensional network nano particles to obtain a mixture I. Fully mixing a liquid crystal polymer monomer, a chiral dopant, an initiator, a modifier monomer and a fluorescent dye to obtain a mixed solution II; and adding the mixture I into the mixture solution II, and continuously stirring for reaction to obtain the double transition metal-based composite liquid crystal material. The invention can improve the photoelectric property of the electrochromic liquid crystal and reduce the threshold voltage of the electrochromic liquid crystal device. The doping of three-dimensional network nano particles in the liquid crystal phase can reduce the maximum photopolymerization reaction rate of the system, improve the phase separation degree of the polymer dispersed liquid crystal system and improve the light wave utilization rate.
Description
Technical Field
The invention belongs to the technical field of composite liquid crystal materials, and particularly relates to a double transition metal matrix composite liquid crystal material and a preparation method thereof.
Background
The liquid crystal material is a mesophase between solid and liquid, can flow, has optical properties of crystallization, and is widely applied to electronic products at present. Based on the handwriting function of cholesteric bistable liquid crystal and the energy-saving characteristic of maintaining display without continuous power supply, the liquid crystal has been widely used in the field of handwriting boards. The cholesteric liquid crystal for display has two stable states, namely an FC state and a P state, becomes the P state when being pressed, can reflect a fixed wavelength relation at the moment, and is apparent as a display handwriting, the P state is changed into the FC state after an electric field is applied, the display handwriting is transparent, and the handwriting is cleared. Selective reflection and circular dichroism of cholesteric liquid crystals is believed to reflect only a very small fraction of the light of the incident light source, and thus for reflective cholesteric liquid crystal devices they do not have a backlight and do not themselves emit light, which would greatly affect their display in the case of weaker incident light sources. Therefore, the response performance, photoelectric conversion performance and the like of the cholesteric liquid crystal material directly influence the experience effect of the handwriting board. How to widen the available light wave band, improve the light availability, reduce the threshold voltage is always the research focus in the field of liquid crystal materials.
There are reports of doping conductive graphene and the like into cholesteric liquid crystal to adjust reflection bands and improve light utilization rate. However, the doping of graphene is prone to agglomeration, resulting in unstable broadband reflection effects; meanwhile, the graphene is high in price and complex in preparation process, and the production cost of the composite liquid crystal is greatly increased.
Disclosure of Invention
In order to solve the technical problems, the invention adopts the following technical scheme: a preparation method of a double transition metal-based composite liquid crystal material comprises the following steps: adding a transition metal source precursor A, a transition metal source precursor B and an organic ligand unit into a reactor at the same time, adding an organic solvent, stirring to fully dissolve the transition metal source precursor A and the transition metal source precursor B, and reacting at 25-180 ℃ for 0.5-168 hours to prepare a mixture liquid with a transition metal base three-dimensional network nano material;
centrifuging, filtering and drying the mixture liquid to finally obtain the double-transition metal-based three-dimensional network nano particles;
weighing a certain amount of the double transition metal-based three-dimensional network nano particles, adding a certain amount of solvent into the nano particles, and performing ultrasonic dispersion to obtain a mixture I;
then, fully mixing a liquid crystal polymer monomer, a chiral dopant, an initiator, a modifier monomer and a fluorescent dye according to a certain proportion to obtain a mixed solution II;
and adding the mixture I into the mixture solution II, continuously stirring, and carrying out illumination reaction for 0.5-24h under vacuum condition to obtain the double transition metal matrix composite liquid crystal material.
As the optimization of the technical proposal, the transition metal source precursor A is a copper-based metal source precursor, the copper-based metal source precursor is any one of copper nitrate, copper chloride, copper sulfate and copper acetate, the transition metal source precursor B is any one of chromium chloride, cobalt nitrate, cobalt chloride, cobalt sulfate, cobalt acetate, ferric nitrate, ferric chloride, ferric sulfate, ferric acetate, aluminum nitrate, zinc acetate, zinc chloride, zinc sulfate, aluminum chloride, aluminum sulfate, aluminum acetate, nickel nitrate, nickel chloride, nickel sulfate, nickel acetate, manganese nitrate, manganese chloride, manganese sulfate, manganese acetate, titanium nitrate, titanium chloride, titanium sulfate, silver nitrate and chloroauric acid, the organic ligand unit is one or more of terephthalic acid, trimesic acid, 2-amino terephthalic acid, 2-hydroxy terephthalic acid, 2-bromo terephthalic acid, 2, 5-dihydroxy terephthalic acid, 2 '-bipyridine-5, 5' -dicarboxylic acid, 2,4, 6-tri (4-carboxyphenyl) -1,3, 5-triazine, azobenzene-4, 4-dicarboxylic acid, 2, 5-diamino terephthalic acid and 4- (4-pyridyl) benzoic acid, the organic solvent is any one of absolute methanol, absolute ethanol, N-butanol, acetone, N-hexane, ethyl acetate, N-dimethylformamide, N-diethylformamide, dichloromethane, trichloromethane, tetrachloromethane, petroleum ether, tetrahydrofuran, dimethyl sulfoxide, pyridine, pyrrole, acetonitrile, toluene and 1, 4-dioxane, and the solvent is any one of acetone, N-hexane, ethyl acetate, dichloromethane, trichloromethane, tetrachloromethane, any one of tetrahydrofuran, pyridine and pyrrole, wherein the liquid crystal polymer monomer is one or more of the following molecules, and n=1-6:
the chiral dopant is one or more of R6N, S, 6N, R5011, S5011, R2011, S2011, R1011, S1011, R811 and S811:
the initiator is any one of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylbenzophenone (IRG 2959), 2-benzyl-2-dimethylamino-1- (4-morpholinophenone) (IRG 369), 2-methyl-1- (4-methylthiophenyl) -2-morpholino-1-propanone (IRG 907), methyl Benzoyl Formate (MBF), 4-Methylbenzophenone (MBZ) and 4, 4-bis (diethylamino) benzophenone (EHA); the modifier monomer is ethoxyethoxyethyl acrylate (EOEOEA), hexadecyl acrylate (HDA), isobornyl acrylate (IBOA), isobornyl methacrylate (IBOMA), isodecyl acrylate (IDA), lauryl Methacrylate (LMA), 4' -diaminodiphenyl ether (ODA), (3) ethoxyphenolic acrylate (PH-3 EA), 2-phenoxyethyl acrylate (PHEA), (4) ethoxynonylphenol acrylate (NP-4 EA), lauryl Acrylate (LA), dipropylene glycol diacrylate (DPGDA), (10) ethoxylated bisphenol A diacrylate (EO 10-BPADA), neopentyl glycol diacrylate (NPA), diethylene glycol phthalate diacrylate (PDDA), tripropylene glycol diacrylate (TPGDA), ethoxylated bisphenol A diacrylate (EO 4-BPADA), hexanediol diacrylate (HDDA), (2) propoxylated neopentyl glycol diacrylate (PO 2-NPGDA), pentaerythritol triacrylate (PEEO), trimethylolpropane Trimethacrylate (TMA), (9) ethoxylated trimethylolpropane triacrylate (9-trimethylolpropane), trimethylolpropane triacrylate (DPPTA), or Ditetrahydrofluropropanacrylate (DPPTA), (5) Ethoxylated pentaerythritol tetraacrylate (DO 5-PETA); the fluorescent dye is any one of perylene, diisobutyl perylene diacid, rhodamine 123, coumarin and Cy 5.
As a preferable mode of the above technical scheme, the part ratio of the transition metal source precursor a, the transition metal source precursor B and the functional organic ligand unit is 1-1000:1-1000:1-500.
As the optimization of the technical scheme, the part ratio of the double transition metal-based three-dimensional network nano particles to the solvent in the mixture I is 1-10:1-500.
As the preferable choice of the technical scheme, the part ratio of the liquid crystal polymer monomer, the chiral dopant, the initiator, the modifier monomer and the fluorescent dye in the mixed solution II is 1-50:1-50:1-50:1-50:1-10.
As the preferable choice of the technical scheme, the part ratio of the mixture I to the mixture solution II is 1-10:1-100.
The double transition metal-based composite liquid crystal material is prepared by the preparation method of the double transition metal-based composite liquid crystal material.
The beneficial effects of the invention are as follows: the double transition metal-based composite liquid crystal material can improve the photoelectric property of electrochromic liquid crystal and reduce the threshold voltage of an electrochromic liquid crystal device. The doping of the three-dimensional network nano particles in the liquid crystal phase can reduce the maximum photopolymerization reaction rate of the system, increase the gelation time, finally improve the phase separation degree of the polymer dispersed liquid crystal system and improve the light wave utilization rate.
Drawings
FIG. 1 is a scanning electron microscope image of a dual transition metal matrix composite liquid crystal material;
FIG. 2 is a graph of contrast and driving voltage for a dual transition metal matrix composite liquid crystal material system.
Detailed Description
The following description of the embodiments of the present invention will be made apparent and fully in view of the accompanying drawings, in which some, but not all embodiments of the invention are shown. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
180 parts of copper nitrate, 60 parts of titanium tetrachloride and 35 parts of 2-amino terephthalic acid are respectively weighed into a three-neck flask, then 120 parts of dimethyl sulfoxide and 30 parts of n-butanol are added into the three-neck flask, stirring is continued for 15min until the copper nitrate and the titanium tetrachloride are completely dissolved, and the reaction is carried out for 24h at 45 ℃; centrifuging and filtering the mixed solution, washing the collected product with acetone for 3 times, and freeze-drying for 48 hours to obtain Cu-Ti double transition metal-based three-dimensional network nano particles;
dispersing the prepared Cu-Ti double transition metal-based three-dimensional network nano particles in acetone to prepare a mixed solution with the mass fraction of 0.5wt%, transferring 5.2 parts into a three-neck flask, and performing ultrasonic dispersion for 30min to obtain a mixture I for later use.
Subsequently, the liquid crystal polymer monomers a (n=2) and F (n=6), R5011, IRG369, EOEOEA, perylene, and the like were sufficiently mixed in a ratio of 30 parts by mass to 10 parts by mass to 5 parts by mass to 1 part by mass to obtain a liquid crystal mixed solution II.
Adding the mixture I into the mixture solution II, continuously stirring at 45 ℃, and carrying out light reaction for 24 hours under vacuum condition to finally obtain the Cu-Ti double transition metal matrix composite liquid crystal material.
Example 2
220 parts of copper sulfate, 110 parts of silver nitrate and 165 parts of 2, 5-diamino terephthalic acid are respectively weighed into a three-neck flask, 100 parts of N, N-dimethylformamide and 10 parts of N-butanol are added into the three-neck flask, stirring is continued for 30min until the three-neck flask is completely dissolved, and the three-neck flask is reacted for 12h at 80 ℃; centrifuging and filtering the mixed solution, washing the collected product with acetone for 3 times, and freeze-drying for 72 hours to obtain Cu-Ag double-transition metal-based three-dimensional network nano particles;
dispersing the prepared Cu-Ag double transition metal-based three-dimensional network nano particles in acetone to prepare a mixed solution with the mass fraction of 0.5wt%, taking 5.1 parts of the mixed solution into a three-neck flask, and performing ultrasonic dispersion for 50min to obtain a mixture I for later use.
Subsequently, the liquid crystal polymer monomer a (n=6), R2011, IRG2959, IDA, perylene, etc. were sufficiently mixed in a ratio of 45 parts to 8 parts to 5 parts to 2 parts to 0.05 part, to obtain a liquid crystal mixed solution II.
And adding the mixture I into the mixture solution II, continuously stirring at 60 ℃, and carrying out light reaction for 8 hours under vacuum condition to finally obtain the Cu-Ag double transition metal matrix composite liquid crystal material.
Example 3
260 parts of copper sulfate, 190 parts of chromium chloride and 51 parts of 4- (4-pyridyl) benzoic acid are respectively weighed into a three-neck flask, 190 parts of N, N-dimethylformamide and 20 parts of N-butanol are added into the three-neck flask, stirring is continued for 60 minutes until complete dissolution is achieved, and the reaction is carried out for 48 hours at 180 ℃; centrifuging and filtering the mixed solution, washing the collected product with acetone for 3 times, and freeze-drying for 72 hours to obtain Cu-Cr double-transition metal-based three-dimensional network nano particles;
dispersing the prepared Cu-Cr double transition metal-based three-dimensional network nano particles in acetone to prepare a mixed solution with the mass fraction of 5.5wt%, and taking 1.3 parts of the mixed solution into a three-neck flask for ultrasonic dispersion for 20min to obtain a mixture I for later use.
Subsequently, liquid crystal polymer monomers B (n=6) and E (n=2), R1011, IRG907, PETA, rhodamine 123, and the like were sufficiently mixed in a ratio of 10 parts by 31 parts by 10 parts by 7.5 parts by 1.8 parts by 0.12 parts to obtain a liquid crystal mixed solution II.
And adding the mixture I into the mixture solution II, continuously stirring at 85 ℃, and carrying out light reaction for 10 hours under vacuum conditions to finally obtain the Cu-Cr double transition metal matrix composite liquid crystal material.
The copper-based double-transition metal three-dimensional network nanoparticle doped composite liquid crystal materials prepared in the above examples 1-3 are respectively prepared into glass liquid crystal boxes: the ITO conductive glass was cut into 2.5X2.5 cm pieces 2 The conductive surfaces are opposite after the specification, wherein the distance between the tail ends is 0.2cm, the edges are sealed by glue, and the mixed copper-based double-transition metal three-dimensional network nanoparticle doped type composite liquid crystal material is poured in by utilizing capillary action to obtain the corresponding liquid crystal box.
Comparative example
The liquid crystal polymer monomer, the chiral dopant, the initiator, the modifier monomer, the fluorescent dye and the like are directly and fully mixed according to the mass ratio in the embodiment, so as to obtain liquid crystal mixed solutions respectively. Then, the reaction is carried out under the same condition, and the traditional blank contrast liquid crystal material is obtained.
The blank glass liquid crystal boxes without the double transition metal matrix composite liquid crystal material are prepared by adopting the glass liquid crystal box method and are used as blank examples 1, 2 and 3.
The light availability and photoelectric conversion performance of the corresponding materials were tested for the reflective bands (including the center wavelength), contrast, and driving voltage, respectively, for examples 1-3 and the corresponding blank examples. Wherein the reflection band test adopts an ultraviolet-visible-near infrared spectrophotometer test, and the test results are shown in the following table:
examples 1-3 and corresponding blank contrast and drive voltage test procedure the drive voltage and contrast for the transition of the different liquid crystal systems from the planar state to the focal conic state in the above examples were tested, where contrast cr=t Plane state /T Focal conic state I.e., the transmittance in the planar state at the center reflection wavelength of the same sample is divided by the transmittance in the focal conic state. The test results are shown in figure 2.
Compared with the traditional liquid crystal material, the wavelength band of the available light and the central wavelength of the available light are obviously improved, and the reason is that the doping of the transition metal-based three-dimensional network nano particles in the liquid crystal phase can reduce the maximum photopolymerization reaction rate of the system, increase the gelation time, finally improve the phase separation degree of the polymer dispersed liquid crystal system and improve the light wave utilization rate. . In addition, the threshold voltage is significantly lower than that of conventional liquid crystal materials, since the doped copper component can improve the conductivity of the liquid crystal material and lower the threshold voltage. The liquid crystal handwriting board is suitable for preparing the liquid crystal handwriting board.
It should be noted that the technical features of the reactor and the like related to the present application should be considered as the prior art, and the specific structure, the working principle, and the control manner and the spatial arrangement that may be related to the technical features should be selected conventionally in the art, and should not be considered as the point of the invention of the present application, and the present application is not further specifically developed in detail.
While the preferred embodiments of the present invention have been described in detail, it should be appreciated that numerous modifications and variations may be made in accordance with the principles of the present invention by those skilled in the art without undue burden, and thus, all technical solutions which may be obtained by logic analysis, reasoning or limited experimentation based on the principles of the present invention as defined by the claims are within the scope of protection as defined by the present invention.
Claims (2)
1. The preparation method of the double transition metal-based composite liquid crystal material is characterized by comprising the following steps of: adding a transition metal source precursor A, a transition metal source precursor B and an organic ligand unit into a reactor at the same time, adding an organic solvent, stirring, and reacting for 0.5-168 hours at 25-180 ℃ to prepare a mixture liquid with a transition metal base three-dimensional network nano material, wherein the part ratio of the transition metal source precursor A to the transition metal source precursor B to the functional organic ligand unit is 1-1000:1-1000:1-500;
centrifuging, filtering and drying the mixture liquid to finally obtain the double-transition metal-based three-dimensional network nano particles;
weighing a certain amount of the double-transition metal-based three-dimensional network nano particles, adding a certain amount of solvent into the mixture, and performing ultrasonic dispersion to obtain a mixture I, wherein the part ratio of the double-transition metal-based three-dimensional network nano particles to the solvent in the mixture I is 1-10:1-500;
then, fully mixing the liquid crystal polymer monomer, the chiral dopant, the initiator, the modifier monomer and the fluorescent dye according to a certain proportion to obtain a mixed solution II, wherein the part ratio of the liquid crystal polymer monomer to the chiral dopant to the initiator to the modifier monomer to the fluorescent dye in the mixed solution II is 1-50:1-50:1-50:1-50:1-10;
adding the mixture I into the mixture solution II, continuously stirring, and carrying out illumination reaction for 0.5-24h under vacuum condition to obtain the double transition metal-based composite liquid crystal material, wherein the part ratio of the mixture I to the mixture solution II is 1-10:1-100;
the transition metal source precursor A is a copper-based metal source precursor, the copper-based metal source precursor is any one of copper nitrate, copper chloride, copper sulfate and copper acetate, the transition metal source precursor B is any one of chromium chloride, cobalt nitrate, cobalt chloride, cobalt sulfate, cobalt acetate, ferric nitrate, ferric chloride, ferric sulfate, ferric acetate, aluminum nitrate, zinc acetate, zinc chloride, zinc sulfate, aluminum chloride, aluminum sulfate, aluminum acetate, nickel nitrate, nickel chloride, nickel sulfate, nickel acetate, manganese nitrate, manganese chloride, manganese sulfate, manganese acetate, titanium nitrate, titanium chloride, titanium sulfate, silver nitrate and chloroauric acid, the organic ligand unit is one or more of terephthalic acid, trimesic acid, 2-amino terephthalic acid, 2-hydroxy terephthalic acid, 2-bromo terephthalic acid, 2, 5-dihydroxy terephthalic acid, 2 '-bipyridine-5, 5' -dicarboxylic acid, 2,4, 6-tri (4-carboxyphenyl) -1,3, 5-triazine, azobenzene-4, 4-dicarboxylic acid, 2, 5-diamino terephthalic acid and 4- (4-pyridyl) benzoic acid, the organic solvent is any one of absolute methanol, absolute ethanol, N-butanol, acetone, N-hexane, ethyl acetate, N-dimethylformamide, N-diethylformamide, dichloromethane, trichloromethane, tetrachloromethane, petroleum ether, tetrahydrofuran, dimethyl sulfoxide, pyridine, pyrrole, acetonitrile, toluene and 1, 4-dioxane, and the solvent is any one of acetone, N-hexane, ethyl acetate, trichloromethane, tetrachloromethane, tetrahydrofuran, pyridine and pyrrole, the liquid crystal polymer monomer is one or more of the following molecules, wherein n=1-6:
the chiral dopant is one or more of R6N, S, 6N, R5011, S5011, R2011, S2011, R1011, S1011, R811 and S811, and the initiator is any one of IRG2959, IRG369, IRG907 and MBF, MBZ, EHA; the modifier monomer is any one of EOEOEA, HDA, IBOA, IBOMA, IDA, LMA, ODA, PH-3EA, PHEA, NP-4EA, LA, DPGDA, EO-BPADA, NPGDA, PDDA, TPGDA, EO4-BPADA, HDDA, PO2-NPGDA, PETA, TMPTMA, EO-TMPTA and Di-TMPTA, DPHA, DO 5-PETA; the fluorescent dye is any one of perylene, diisobutyl perylene diacid, rhodamine 123, coumarin and Cy 5.
2. A double transition metal-based composite liquid crystal material, characterized in that the double transition metal-based composite liquid crystal material is produced by the production method of the double transition metal-based composite liquid crystal material in claim 1.
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