CN114015459B - Liquid crystal containing dinaphthyl monomer, and preparation method and application thereof - Google Patents
Liquid crystal containing dinaphthyl monomer, and preparation method and application thereof Download PDFInfo
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- CN114015459B CN114015459B CN202111559298.6A CN202111559298A CN114015459B CN 114015459 B CN114015459 B CN 114015459B CN 202111559298 A CN202111559298 A CN 202111559298A CN 114015459 B CN114015459 B CN 114015459B
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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
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- 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
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- 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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Abstract
The invention relates to a liquid crystal containing a dinaphthyl monomer, which has the following structural formula:x in the formula I is any one of alkenyl, alkynyl or alkyl, and R 1 、R 2 、R 3 、R 4 、R 5 Is independently selected from one of H, C-C6 fatty compounds or aromatic compounds. The monomer liquid crystal contains a dinaphthyl rigid group, so that the polarity of molecules is enhanced, the product has a wider nematic phase temperature range, and simultaneously has larger anisotropy and possibly higher resistivity, can be used as a liquid crystal component, improves the property of a liquid crystal material, and can also be used for preparing a microwave liquid crystal antenna. Meanwhile, compared with the traditional thiophosgene and other methods, the preparation method of the monomer containing the dinaphthyl provided by the invention has the advantages that the toxicity of the used raw materials is low, the reaction process is free from danger, the post-treatment is simple and convenient, and the preparation method is suitable for large-scale production.
Description
Technical Field
The invention relates to a liquid crystal containing a dinaphthyl monomer, a preparation method and application thereof, belonging to the technical field of liquid crystal materials.
Background
As a display device for a counter and a clock at the time of counting, a Liquid Crystal Display (LCDS) has been developed for over 40 years in the first 70 th century, and has spread over the aspects of our daily lives. Meanwhile, in satisfying the increasing technical demands of thin film transistor liquid crystal displays (TFT-LCDs), there are increasing demands for them, such as high definition of their motion pictures, high brightness, high response speed, wide operating temperature range, low power consumption, low driving voltage, etc., in which the performance of the liquid crystal material is critical.
With the continuous development of liquid crystal materials, liquid crystal compounds have suitable optical anisotropy (delta n), dielectric anisotropy (delta epsilon), viscosity (gamma) and other characteristics, and in recent years, many documents indicate that the liquid crystal compounds can meet some characteristics required by microwave technology components. For example: N.Martin, N.Tentillier, P.Laurent, B.Splingart.Electrically Microwave Tunable Components Using Liquid Crystals, 32 et al European conference on microwaves, pages 393-396, milan, 2002, report the use of liquid crystal materials in electrically tunable microwave components.
As a liquid crystal material applied to LCDs, it is required to have low viscosity, high voltage holding ratio, low threshold voltage, and optical anisotropy matching with TFT-LCDs in addition to good physical and chemical stability and wide operating temperature range.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention provides a monomer liquid crystal containing dinaphthyl, a preparation method and application thereof, wherein the monomer liquid crystal has wider nematic phase temperature, can improve the clearing point of liquid crystal components, has larger anisotropism, can improve the performance of the liquid crystal components, is applied to liquid crystal compositions and microwave liquid crystal antennas, and simultaneously provides a novel isothiocyanamide preparation method.
The technical scheme for solving the technical problems is as follows: a liquid crystal containing a dinaphthyl monomer, which has the following structural formula:
x in the formula I is any one of alkenyl, alkynyl or alkyl, and R 1 、R 2 、R 3 、R 4 、R 5 Is independently selected from one of H, C-C6 fatty compounds or aromatic compounds.
Preferably, X isOne of them.
Preferably, said R 1 、R 2 、R 3 、R 4 、R 5 Independently selected from H, One of them.
Preferably, the liquid crystal containing the dinaphthyl monomer is any one of the following structural formulas:
the invention also discloses a preparation method of the liquid crystal containing the dinaphthyl monomer, which comprises the following reaction steps:
(n＝1,2,3,4,5，……,20)
(1) Preparation of intermediate Cn-B: adding magnesium chips and an organic solvent into a reaction system, and slowly dripping R under the protection of nitrogen 1 Preparing Grignard reagent by mixing Br and THF, reacting at 40-50 ℃ for 2 hours, preparing a reaction bottle, adding Cn-A, organic solvent and catalyst, heating to 30-50 ℃, dripping the Grignard reagent, adding hydrochloric acid for quenching, washing and passing through after the reactionObtaining an intermediate Cn-B by a column; intermediate Cn-B is represented by the following formula:
(5) Preparation of intermediate Cn-C: adding Cn-B and an organic solvent into a reaction system, cooling to-10-0 ℃, dripping boron tribromide, reacting for 3 hours at a temperature, adding water to quench the reaction after the reaction is finished, washing with water, removing the solvent, and recrystallizing with toluene and petroleum ether to obtain an intermediate Cn-C, wherein the intermediate Cn-C is shown in the following formula:
(6) Preparation of intermediate Cn-D: adding Cn-C, triethylamine and an organic solvent into a reaction system, cooling to-10-0 ℃, slowly dropwise adding trifluoromethanesulfonic anhydride, keeping the temperature after the dropwise addition, reacting for 1 hour, adding water for quenching reaction after the reaction is finished, washing with water, removing the solvent, and passing through a silica gel column after petroleum ether is dissolved to obtain an intermediate Cn-D, wherein the intermediate Cn-D is shown in the following formula:
(7) Preparation of intermediate Cn-E: adding Cn-D, 2-methyl-2-hydroxy-3-butyne, DMAP, a catalyst, cuI and triethylamine into a reaction system, heating to reflux, carrying out heat preservation reaction for 6 hours, washing an organic phase to be neutral again after the reaction is finished, removing a dry solvent, dissolving petroleum ether, passing through a silica gel column, removing the dry solvent, and recrystallizing by toluene and absolute ethyl alcohol to obtain an intermediate Cn-E; intermediate Cn-E is represented by the following formula:
(5) Intermediate Cn-F preparation: adding Cn-E, KOH and organic solvent into a reaction system, heating to reflux, preserving heat for 30 minutes, cooling the system to room temperature after the reaction is finished, adding water for quenching reaction, washing an organic phase to be neutral, drying the solvent, passing through a silica gel column after petroleum ether solvent is removed, and drying the solvent to obtain an intermediate Cn-F; intermediate Cn-F is represented by the following formula:
(6) Preparation of intermediate Cn-H: cn-F, cn-G, DMAP, catalyst and PPh 3 Adding CuI and triethylamine into a reaction system, heating to reflux, preserving heat for 3 hours, evaporating most of triethylamine after the reaction is finished, cooling the system to room temperature, adding toluene and dilute hydrochloric acid, washing an organic phase to be neutral, removing a dry solvent, and carrying out column chromatography on toluene and petroleum ether to obtain an intermediate Cn-H; intermediate Cn-H is represented by the following formula:
(7) Preparation of intermediate Cn-I: adding Cn-H and an organic solvent into a reaction system, cooling to-10-0 ℃, dripping boron tribromide, adding water to quench the reaction after the reaction is finished, washing an organic phase to be neutral, and removing the solvent to obtain an intermediate Cn-I; intermediate Cn-I is represented by the following formula:
(10) Preparation of intermediate Cn-J: adding Cn-I, triethylamine and dichloroethane into a reaction system, cooling to-10-0 ℃, slowly dropwise adding trifluoromethanesulfonic anhydride, keeping the temperature after the dropwise addition for reaction for 1 hour, adding water for quenching reaction after the reaction is finished, washing an organic phase to be neutral, removing a dry solvent, and recrystallizing by toluene and absolute ethyl alcohol to obtain an intermediate Cn-J; intermediate Cn-J is represented by the following formula:
(11) Preparation of target Cn: adding Cn-J, isothiocyanate, a catalyst and an organic solvent into a reaction system, heating to 110-120 ℃, preserving heat, reacting for 2 hours, adding water to quench the reaction after the reaction is finished, precipitating a large amount of solids in the system, carrying out suction filtration, taking a filter cake, and carrying out toluene and petroleum ether column chromatography to obtain a target object Cn; the target Cn is represented by the following formula:
further, in step (1), R 1 -Br is selected from one of bromohexane, bromoethane, bromopropane, bromobutane, isopropyl bromide and tert-butyl bromide, and the organic solvent is selected from one or more of dichloromethane, chloroform, dichloroethane and tetrahydrofuran; the raw material Cn-A is selected from one of 2-bromo-6-methoxynaphthalene, 6-bromo-1-ethyl-2-methoxynaphthalene, 6-bromo-2-methoxy-1-methylnaphthalene, 6-bromo-2-methoxy-1-phenylnaphthalene, 6-bromo-1-isopropyl-2-methoxynaphthalene and 6-bromo-1-tert-butyl-2-methoxynaphthalene;
further, in the step (3), the organic solvent is selected from one or more of dichloromethane, dichloroethane, tetrahydrofuran, petroleum ether, n-hexane and ethyl acetate;
further, in the step (4), the catalyst is selected from tetra (triphenylphosphine) palladium, palladium acetate, pd 2 (dba) 3 、Pd(dppf)Cl 2 One or more of the following;
further, in the step (5), the organic solvent is selected from one or more of absolute ethyl alcohol, toluene, tetrahydrofuran, ethyl acetate and dichloroethane;
further, in the step (6), the raw material Cn-G is selected from one of 2-bromo-6-methoxynaphthalene, 6-bromo-1-ethyl-2-methoxynaphthalene, 6-bromo-2-methoxy-1-methylnaphthalene, 6-bromo-2-methoxy-1-phenylnaphthalene, 6-bromo-1-isopropyl-2-methoxynaphthalene, 6-bromo-1-tert-butyl-2-methoxynaphthalene; the catalyst is selected from one or more of tetra (triphenylphosphine) palladium, palladium acetate, tris (dibenzylideneacetone) dipalladium, and 1,1' -bis (diphenylphosphino) ferrocene palladium dichloride;
further, in the step (7), the organic solvent is selected from one or more of dichloroethane, dichloromethane and tetrahydrofuran;
further, in the step (9), the isothiocyanate is selected from one or more of sodium isocyanate, potassium isothiocyanate and amine isothiocyanate; the catalyst is one or more of tetra (triphenylphosphine) palladium, palladium acetate, tris (dibenzylideneacetone) dipalladium and 1,1 '-bis (diphenylphosphino) ferrocene palladium dichloride, and the ligand is one or more of tri-tert-butylphosphine tetrafluoroborate, 4, 5-bis-diphenylphosphine-9, 9-dimethylxanthene, tricyclohexylphosphine tetrafluoroborate, 2-dicyclohexylphosphine-2', 6 '-dimethoxybiphenyl, 2-dicyclohexylphosphine-2', 4',6' -triisopropylbiphenyl, 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl and triphenylphosphine; the organic solvent is selected from one or more of tetrahydrofuran, toluene, acetonitrile, dichloroethane, dioxane and N, N-dimethylformamide.
The invention also discloses application of the liquid crystal containing the dinaphthyl monomer, and the liquid crystal containing the dinaphthyl monomer is applied to a liquid crystal composition; or the liquid crystal containing the dinaphthyl monomer is applied to a liquid crystal display; or the monomer liquid crystal containing the binaphthyl is applied to high-frequency technical components.
The high-frequency technical component is a liquid crystal base antenna original, a phase shifter, a tunable filter or a tunable metamaterial structure.
The beneficial effects of the invention are as follows:
the liquid crystal containing the dinaphthyl monomer contains dinaphthyl rigid groups, enhances the polarity of molecules, has wider nematic phase temperature, can improve the clear point of a liquid crystal component, has larger anisotropism, can be used as the liquid crystal component, can improve the performance of the liquid crystal component, and can also be used for preparing a microwave liquid crystal antenna;
compared with traditional thiophosgene and other methods, the preparation method of the liquid crystal containing the dinaphthyl monomer has the advantages of low toxicity of the used raw materials, no danger in the reaction process, simple and convenient post-treatment and suitability for large-scale production.
Drawings
FIG. 1 is a mass spectrum of a liquid crystal compound C1 in example 1;
FIG. 2 is a hydrogen nuclear magnetic resonance chart of the liquid crystal compound C1 in example 1;
FIG. 3 is a carbon nuclear magnetic resonance chart of the liquid crystal compound C1 in example 1;
FIG. 4 is a mass spectrum of a liquid crystal compound C5 in example 2;
FIG. 5 is a hydrogen nuclear magnetic resonance chart of the liquid crystal compound C5 in example 2;
FIG. 6 is a carbon nuclear magnetic resonance chart of the liquid crystal compound C5 in example 2.
Detailed Description
The following detailed description of the present invention will provide further details in order to make the above-mentioned objects, features and advantages of the present invention more comprehensible. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. The present invention may be embodied in many other forms than described herein and similarly modified by those skilled in the art without departing from the spirit of the invention, whereby the invention is not limited to the specific embodiments disclosed below.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
Example 1
The structural formula of the liquid crystal compound C1 is as follows:
the specific synthetic route is as follows:
the method comprises the following specific steps:
(1) Preparation of C1-B:
a500 mL three-necked flask was prepared, magnesium turnings (9.8 g,0.405 mol) were added, and a mixture of 1-bromopentane (58.9 g,0.390 mol) and 177.0g of tetrahydrofuran was slowly dropped under nitrogen protection, and the temperature was raised to 40-50℃to initiate the reaction. After the solution is dropped, the reaction is carried out for 2 hours.
A1L three-necked flask was prepared, 2-bromo-6-methoxynaphthalene (71.1 g,0.300 mol) and 178.0g of tetrahydrofuran were added thereto, and after stirring and dissolution, 1' -bis (diphenylphosphino) ferrocene palladium dichloride (0.220 g, 3.0X10) -4 mol), heating to 35-45 ℃, dripping the solution prepared in 1), and reacting for 2 hours with heat preservation. After the reaction is finished, dilute hydrochloric acid is added to quench the reaction, toluene is added, and the organic phase is washed to be neutral by water and the solvent is removed. After petroleum ether is dissolved, the mixture is passed through a silica gel column and the solvent is removed to obtain 68.1g of pale yellow solid with GC purity: 98.62%, yield: 99.4%, GC-MS (m/s): 228.
(2) Preparation of C1-C:
a250 mL three-necked flask was prepared, and C1-B (22.0 g,0.096 mol) and 70.0g of dichloroethane were added under nitrogen protection, followed by stirring and cooling to-10 to 0 ℃. Boron tribromide (14.53 g,0.058 mol) was added dropwise, and the reaction was continued for 3 hours at the end of the addition. After the reaction was completed, the reaction was quenched with water, the organic phase was washed with water to neutrality, and the solvent was removed to give 20.1g of a colorless oil. Toluene and petroleum ether were recrystallized to give 18.2g of white solid, GC purity: 99.95%, yield: 88.2%, GC-MS (m/s): 214.
(3) Preparation of C1-D:
a250 ml three-necked flask was prepared, and C1-C (18.0 g,0.084 mol), triethylamine (10.6 g,0.105 mol) and 80.0g of dichloroethane were added under nitrogen protection, followed by stirring and cooling to-10 to 0 ℃. Trifluoromethanesulfonic anhydride (27.3 g,0.097 mol) was slowly added dropwise, and the reaction was continued for 1 hour at a constant temperature after the completion of the addition. After the reaction was completed, the reaction was quenched with water, the organic phase was washed with water to neutrality, and the solvent was dried to obtain 27.3g of a tan liquid. After petroleum ether is dissolved, the mixture is passed through a silica gel column and the solvent is removed to obtain 25.4g of white solid with GC purity: 99.74%, yield: 87.3%, GC-MS (m/s): 346.
(4) Preparation of C1-E:
a500 mL three-necked flask was prepared, and C1-D (38.0 g,0.110 mol) and 2-methyl-2-hydroxy-3-butyne (13.8 g, 0) were introduced under nitrogen atmosphere165 mol), 4-dimethylaminopyridine (1.34 g,0.01 mol), 1' -bis (diphenylphosphino) ferrocene palladium dichloride (0.40 g, 5.5X10) -4 mol)、CuI(0.21g，1.10×10 -3 mol) and 150.0g of triethylamine, heating to reflux, and reacting for 6 hours with heat preservation. After the reaction was completed, most of triethylamine was distilled off, and after the system was cooled to room temperature, toluene and diluted hydrochloric acid were added, and the organic phase was washed with water again to neutrality, and the solvent was removed to obtain 41.0g of brown liquid. Petroleum ether was dissolved, passed through a silica gel column, dried, recrystallized from toluene and absolute ethanol to give 24.5g of a white solid, GC purity: 98.86%, yield: 79.5%, GC-MS (m/s): 280.
(5) C1-F preparation:
a250 mL three-necked flask was prepared, and C1-E (20.0 g,0.071 mol), potassium hydroxide (0.4 g, 0.0070 mol), 16.0g of absolute ethanol and 100.0g of toluene were added under nitrogen protection, heated to reflux, and reacted at a constant temperature for 30 minutes. After the reaction was completed, the system was cooled to room temperature, quenched with water, the organic phase was washed with water to neutrality, and the solvent was dried to give 16.4g of brown liquid. Petroleum ether solvent was passed through a silica gel column and the solvent was then stripped to give 13.3g of yellow liquid, GC purity: 99.19%, yield: 83.6%, GC-MS (m/s): 222.
(6) Preparation of C1-H:
a250 mL three-necked flask was prepared, and C1-F (10.0 g,0.045 mol), 6-bromo-1-ethyl-2-methoxynaphthalene (11.9 g,0.045 mol), 4-dimethylaminopyridine (0.55 g, 4.5X10 mol) were added under nitrogen atmosphere -3 mol), 1' -bis (diphenylphosphino) ferrocene palladium dichloride (0.316 g, 4.5X10) -4 mol), triphenylphosphine (0.35 g, 1.35X10) -3 mol), cuprous iodide (0.171 g, 9.0X10) -4 mol) and 100.0g of triethylamine, heating to reflux, and keeping the temperature for reaction for 3 hours. After the reaction was completed, most of triethylamine was distilled off, and after the system was cooled to room temperature, toluene and diluted hydrochloric acid were added, and the organic phase was washed with water again to neutrality, and the solvent was removed to obtain 17.2g of a tan solid. Column chromatography on toluene and petroleum ether gave 15.6g of white solid, HPLC purity: 92.84%, yield: 85.2% HPLC-MS (m/s): 406.13.
(7) Preparation of C1-I:
a250 mL three-necked flask was prepared, and C1-H (39.0 g,0.096 mol) and 100.0g of dichloroethane were added under nitrogen protection, followed by stirring and cooling to-10 to 0 ℃. Boron tribromide (14.53 g,0.058 mol) was added dropwise, and the reaction was continued for 3 hours at the end of the addition. After the reaction was completed, the reaction was quenched with water, the organic phase was washed with water to neutrality, and the solvent was dried to obtain 39.4g of a yellow solid. Recrystallisation from toluene and absolute ethanol gives 30.0g of a pale yellow solid, HPLC purity: 98.16%, yield: 79.6% by HPLC-MS (m/s): 392.23.
(8) Preparation of C1-J
A250 mL three-necked flask was prepared, and C1-I (20.0 g,0.051 mol), triethylamine (6.4 g,0.064 mol) and 80.0g of dichloroethane were added under nitrogen protection, followed by stirring and cooling to-10 to 0 ℃. Trifluoromethanesulfonic anhydride (16.5 g,0.059 mol) was slowly added dropwise, and the reaction was continued for 1 hour after the completion of the addition. After the reaction was completed, the reaction was quenched with water, the organic phase was washed with water to neutrality, and the solvent was dried to obtain 25.5g of brown solid. After recrystallisation from toluene and absolute ethanol, 18.3g of a yellow solid are obtained, HPLC purity: 97.85%, yield: 68.5% HPLC-MS (m/s): 524.26.
(9) Preparation of C1
A500 mL three-necked flask was prepared, and under nitrogen atmosphere, C1-J (26.2 g,0.050 mol), sodium isothiocyanate (16.2 g,0.200 mol), tetrakis (triphenylphosphine) palladium (0.055 g, 5.00X10 g) -5 mol) and 200.0g of N, N-dimethylformamide, heating to 110-120 ℃, and preserving the heat for 2 hours. After the reaction is finished, adding water to quench the reaction, precipitating a large amount of solids in the system, and carrying out suction filtration. The filter cake was taken and subjected to column chromatography with toluene and petroleum ether to give 10.8g of white solid with HPLC purity: 99.94%, yield: 49.8%, HPLC-MS (m/s): 433.52.
Example 2
The structural formula of the liquid crystal compound C5 is as follows:
the specific synthetic route is as follows:
the method comprises the following specific steps:
(1) Preparation of C5-B:
the same preparation method and raw material ratio as those of the material C1-B prepared in example 1 were adopted, except that 2-bromo-6-methoxynaphthalene was changed to 6-bromo-1-ethyl-2-methoxynaphthalene, and the purity of the finally obtained material C5-B was 99.32% by GC detection, and GC-MS (m/s): 256.
(2) Preparation of C5-C:
the same preparation and raw material ratios as those used for preparing materials C1-C in example 1 were employed, wherein only C1-B was changed to C5-B, and the purity of the finally obtained material C5-C was 99.29% by GC detection, GC-MS (m/s): 242.
(3) Preparation of C5-D:
the same preparation and raw material ratios as those used for preparing materials C1-D in example 1 were employed, wherein only C1-C was changed to C5-C, and the purity of the finally obtained material C5-D was 99.19% by GC detection, GC-MS (m/s): 374.
(4) Preparation of C5-E:
the same preparation and raw material ratios as in the preparation of materials C1-E of example 1 were employed, except that C1-D was changed to C5-D, and the final material C5-E was subjected to GC detection to have a purity of 96.74% and GC-MS (m/s): 308.
(5) C5-F preparation:
the same preparation and raw material ratios as those used for preparing materials C1-F in example 1 were employed, wherein only C1-E was changed to C5-E, and the purity of the finally obtained material C5-F was 98.50% by GC detection, GC-MS (m/s): 250.
(6) Preparation of C5-H:
the same preparation and raw material ratios as in the preparation of materials C1-H of example 1 were used, except that C1-G was changed to C5-G, and the final material C5-H was subjected to HPLC detection to a purity of 98.67% and HPLC-MS (m/s): 434.66.
(7) Preparation of C5-I
The same preparation and raw material ratios as in the preparation of material C1-I of example 1 were used, except that C1-H was changed to C5-H, and the purity of the finally obtained material C5-I was 98.67% by HPLC, HPLC-MS (m/s): 420.19.
(8) Preparation of C5-J
The same preparation and raw material ratios as for the preparation of materials C1-J in example 1 were used, except that C1-I was changed to C5-I, and the final material C5-J was subjected to HPLC detection to have a purity of 98.67% and HPLC-MS (m/s): 552.60.
(9) Preparation of C5
The same preparation and raw material ratios as in the preparation of material C1 of example 1 were employed, except that C1-J was replaced by C5-I, the catalyst was replaced by palladium acetate and the ligand tri-tert-butylphosphine tetrafluoroborate, and the resulting material C5 was detected to have a purity of 99.63% by HPLC, HPLC-MS (m/s): 461.38.
Application instance
The parameters of the single crystals C1 and C5 are as follows:
m is a parent mixed crystal, and the formula is as follows:
| name of the name | Proportion of |
| 3HHV | 20％ |
| 5HHV | 20％ |
| PCH301 | 30％ |
| PCH501 | 30％ |
The mother liquid crystals with M-1 to M-2 of 90% were mixed with 10% single crystal, and the parameters were as follows:
from the table above, it can be seen that the isothiocyanlike single crystal containing the dinaphthyl can improve the clearing point, and is beneficial to widening the working temperature range of the mixed crystal. The isothiocyano monocrystal containing the dinaphthyl has higher birefringence, is favorable for reducing the thickness of the device and shortens the response time.
Conclusion: from the above data, it can be seen that the mixed liquid crystal to which the novel liquid crystal monomer is added has excellent physical properties.
The structure of this embodiment is as follows:
the technical features of the above-described embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be considered as the scope of the description.
The above examples illustrate only a few embodiments of the invention, which are described in detail and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (5)
1. The liquid crystal containing the dinaphthyl monomer is characterized by being any one of the following structural formulas:
2. the use of a liquid crystal containing a dinaphthyl monomer according to claim 1, wherein the liquid crystal containing a dinaphthyl monomer is used in a liquid crystal composition.
3. The use of a liquid crystal containing a dinaphthyl monomer according to claim 1, wherein the liquid crystal containing a dinaphthyl monomer is used in a liquid crystal display.
4. The use of a liquid crystal containing a dinaphthyl monomer according to claim 1, characterized in that it is used in high-frequency technical components.
5. The use of a liquid crystal with a naphthalene monomer according to claim 4, wherein the high frequency technology component is a liquid crystal based antenna element, a phase shifter, a tunable filter or a tunable metamaterial structure.
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| CN202111559298.6A CN114015459B (en) | 2021-12-20 | 2021-12-20 | Liquid crystal containing dinaphthyl monomer, and preparation method and application thereof |
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