A circularly polarized luminescent property adjustable electric response material, device and preparation method

Abstract

The present invention provides an electro-responsive material, device and preparation method with tunable circularly polarized luminescence properties, which relates to the field of intelligent dimming technology. The electro-responsive material with tunable circularly polarized luminescence properties includes an electrochromic acid, an electrochromic base and an acid-base responsive circularly polarized optical switch molecule. The electrochromic acid is an aniline derivative, and the electrochromic base is a p-benzoquinone derivative. In the structural formula of the circularly polarized optical switch molecule, R1 and R2 are hydrogen or alkyl substituents, R3 and R4 are hydrogen, phenyl or alkyl substituents, and R3 and R4 are different types of substituents. By utilizing the characteristics that the "electrochromic acid" aniline derivative and the "electrochromic base" p-benzoquinone derivative can reversibly release or capture protons during the process of electrochemical oxidation or reduction, and combining with the circularly polarized optical switch molecule that responds to both acids and bases, an electro-responsive material with tunable circularly polarized luminescence properties under the action of an electric field can be obtained. The required raw materials are simple and easy to obtain, and the device construction cost is low.

Description

Technical Field

[0001] The present invention relates to the field of intelligent dimming technology, and in particular to an electrically responsive material, a device and a preparation method thereof with adjustable circularly polarized luminescence properties. Background Art

[0002] Circularly polarized luminescence refers to the phenomenon that chiral luminescent materials emit left-handed or right-handed circularly polarized light after being excited by light or electricity. Materials with intelligently switchable circularly polarized luminescence properties have great application potential in the fields of three-dimensional display, intelligent optical communication, etc., and have attracted widespread attention.

[0003] So far, circular polarization optical switch materials based on a variety of stimulation methods have been developed, mainly solvents, acid / base, mechanical force, electricity, etc. Among them, electrically responsive materials and devices have always been a hot topic of research due to their unique advantages in the preparation of optoelectronic devices. However, due to the limitations of material types and the difficulty of device construction, the number of electrically responsive circular polarization optical switch materials and devices currently developed is extremely limited, and the optical switching performance is not ideal, for example: there are few types of adjustable circular polarization optical states and the optical switching stability is poor. Summary of the invention

[0004] The problem solved by the present invention is that the number of electrically responsive circularly polarized optical switch materials and devices developed in the prior art is extremely limited, and at least one aspect of the optical switching performance is not ideal.

[0005] To solve the above problems, the present invention provides an electrically responsive material with adjustable circularly polarized luminescence properties, comprising

[0006] Electroacid, electrobase, and acid-base responsive circularly polarized optical switch molecules;

[0007] The electroacid is an aniline derivative,

[0008] The electrobase is a benzoquinone derivative,

[0009] The structural formula of the circular polarization optical switch molecule is:

[0010]

[0011] Wherein, R1 and R2 are hydrogen or alkyl substituents, R3 and R4 are hydrogen, phenyl or alkyl substituents, and R3 and R4 are heterogeneous substituents.

[0012] Preferably, the method for preparing the circularly polarized optical switch molecule comprises the following steps:

[0013] Step S1, adding aminoketo acid derivative A and resorcinol to acidic solvent B at 50-200° C., and purifying to obtain product C after sufficient reaction.

[0014] Step S2, adding the above-mentioned product C and hexamethylenetetramine into an acidic solvent D, reacting them at 50-200° C. and then purifying them to obtain product E.

[0015] Step S3, adding the product E and chiral benzylamine F to an organic solvent G, and purifying after sufficient reaction to obtain the circularly polarized optical switch molecule.

[0016] Preferably, in step S1, the molar ratio of the aminoketo acid derivative A to the resorcinol is 1.0-1.2; the aminoketo acid derivative A includes 4-diethylaminoketo acid or 4-diisopropylaminoketo acid; and the acidic solvent B includes trifluoroacetic acid or methanesulfonic acid.

[0017] In step S2, the molar ratio of the product C to the hexamethylenetetramine is 1.0-1.5; and the acidic solvent D includes trifluoroacetic acid or methanesulfonic acid.

[0018] In step S3, the molar ratio of the product D to the chiral benzylamine F is 1.0-1.5; the chiral benzylamine F includes R-(+)-α-methylbenzylamine or (R)-1-(pyridin-4-yl)ethylamine; and the organic solvent G includes anhydrous ethanol or dimethyl sulfoxide.

[0019] Compared with the prior art, the present invention utilizes the properties of "electroacidic" aniline derivatives and "electroalkaline" benzoquinone derivatives that can reversibly release protons or capture protons during electrochemical oxidation or reduction, and combines them with circularly polarized optical switch molecules that respond to both acid and base. It is possible to obtain an electro-responsive material with adjustable circularly polarized luminescence properties under the action of an electric field. The required raw materials are simple and easy to obtain, and the device construction cost is low.

[0020] In order to solve the above technical problems, the present invention also provides an electrical device with adjustable circularly polarized luminescence properties, comprising two transparent conductive electrodes and the electrical response material with adjustable circularly polarized luminescence properties.

[0021] Compared with the prior art, the electrical device with adjustable circularly polarized luminescence properties of the present invention can realize reversible regulation of three circularly polarized luminescence states in the visible light band under the control of appropriate electrical parameters, namely, non-circularly polarized luminescence properties, left-handed circularly polarized luminescence properties and right-handed circularly polarized luminescence properties, and has good stability, and has important application value in the field of intelligent optical modulation.

[0022] In order to solve the above technical problems, the present invention also provides a method for preparing an electric response device with adjustable circularly polarized luminescence properties, comprising the following steps:

[0023] Step T1, preparing a circular polarization optical switching layer solution, an ion conductive layer solution and an ion storage layer solution,

[0024] Step T2, scrape the circularly polarized optical switching layer solution onto a transparent conductive electrode, scrape the ion storage layer solution and the ion conductive layer solution onto another transparent conductive electrode, and after the solvent evaporates, squeeze the two transparent conductive electrodes loaded with functional materials together to obtain an electrically responsive device with adjustable circular polarization optical properties.

[0025] Preferably, in step T1, the method for preparing the circularly polarized optical switching layer solution comprises:

[0026] A film-forming agent with a mass fraction of 0%-99%, an electrolyte with a mass fraction of 0%-99%, a high boiling point organic solvent with a mass fraction of 0.01%-99.9%, a circularly polarized optical switch molecule with a mass fraction of 0.01%-99.9%, an electrobase with a mass fraction of 0.01%-99.9% and an electroacid with a mass fraction of 0.01%-99.9% are stirred in a low boiling point organic solvent until they are completely dissolved.

[0027] Preferably, the method for configuring the ion conductive layer solution includes:

[0028] 0.01%-99.9% by mass of the film former, 0.01%-99.9% by mass of the electrolyte and 0.01%-99.9% by mass of the high boiling point organic solvent are stirred in the low boiling point organic solvent until they are completely dissolved.

[0029] Preferably, the method for preparing the ion storage layer solution comprises:

[0030] 0.01%-99.9% by mass of a film-forming agent, 0.01%-99.9% by mass of an electrolyte, 0.01%-99.9% by mass of the high-boiling-point organic solvent, 0.01%-99.9% by mass of a functional molecule having a reducing property, and 0.01%-99.9% by mass of a functional molecule having an oxidized property are stirred in the low-boiling-point organic solvent until they are completely dissolved.

[0031] Preferably, the functional molecules having the property of being reduced include p-benzoquinone, nitrobenzene, benzophenone, anthraquinone or dichlorobenzoquinone.

[0032] Preferably, the functional molecules having oxidation properties include phenol, hydroquinone, aniline, p-phenylenediamine or thiophene.

[0033] The advantages of the electrically responsive device with adjustable circularly polarized luminescence properties described in the present invention and the electrically responsive material with adjustable circularly polarized luminescence properties over the prior art are the same and will not be elaborated herein. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 is the NMR spectrum of the electroacid molecule Urea-N in the embodiment of the present invention;

[0035] Figure 2 It is a flow chart of the preparation method of the circularly polarized optical switch molecule R-Rhodol-A which responds to both acid and alkali in an embodiment of the present invention;

[0036] Figure 3 is the nuclear magnetic spectrum of the circularly polarized optical switch molecule R-Rhodol-A that responds to both acid and base in the embodiment of the present invention;

[0037] Figure 4 This is an acid response property analysis diagram of the circularly polarized optical switch molecule R-Rhodol-A that responds to both acid and alkali in an embodiment of the present invention;

[0038] Figure 5 This is a diagram analyzing the base response properties of the circularly polarized optical switch molecule R-Rhodol-A that responds to both acid and base in an embodiment of the present invention;

[0039] Figure 6 is a flow chart of a method for preparing an electrically responsive device with adjustable circular polarization optical properties in an embodiment of the present invention;

[0040] Figure 7 is a CPL spectrum diagram of the reversible conversion between triple circular polarization optical states of the electric response device with adjustable circular polarization optical properties in an embodiment of the present invention;

[0041] Figure 8 It is a fluorescence emission spectrum diagram of the reversible conversion between triple circular polarization optical states of the electric response device with adjustable circular polarization optical properties in the embodiment of the present invention. DETAILED DESCRIPTION

[0042] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, specific embodiments of the present invention are described in detail below with reference to the accompanying drawings.

[0043] It should be noted that, in the description of this specification, the description of the term "in some preferred embodiments" means that the specific features, structures, materials or characteristics described in conjunction with the embodiment or example are included in at least one preferred embodiment or preferred example of the present invention. In this specification, the schematic representation of the above terms does not necessarily refer to the same implementation or example. Moreover, the specific features, structures, materials or characteristics described can be combined in any one or more embodiments or examples in a suitable manner.

[0044] Combination Figure 1-5 As shown, an embodiment of the present invention provides an electrically responsive material with adjustable circularly polarized luminescence properties, comprising

[0045] Electroacid, electrobase, and acid-base responsive circularly polarized optical switch molecules;

[0046] The electroacid is an aniline derivative,

[0047] The electrobase is a benzoquinone derivative,

[0048] The structural formula of the circular polarization optical switch molecule is:

[0049]

[0050] Wherein, R1 and R2 are hydrogen or alkyl substituents, R3 and R4 are hydrogen, phenyl or alkyl substituents, and R3 and R4 are heterogeneous substituents.

[0051] It should be noted that, R1 and R2 are hydrogen or alkyl substituents, and R1 and R2 can be the same substituent or different substituents, and R3 and R4 are heterogeneous substituents, which means that R3 and R4 are not the same substituents and must be different substituents.

[0052] This embodiment utilizes the property of "electroacidic" aniline derivatives and "electroalkaline" quinone derivatives that can reversibly release protons or capture protons during electrochemical oxidation or reduction, and combines them with circularly polarized optical switch molecules that respond to both acids and bases. It is possible to obtain an electroresponsive material with adjustable circularly polarized luminescence properties under the action of an electric field. The required raw materials are simple and easy to obtain, and the device construction cost is low.

[0053] In some preferred embodiments, the electroacid is selected from Urea-N, hydroquinone or p-phenylenediamine.

[0054] In some specific embodiments, Urea-N is prepared by the following method:

[0055] After the p-toluene isocyanate is stirred and dissolved into a clear and transparent solution, it is added dropwise into a tetrahydrofuran solution of N,N-dimethyl-p-phenylenediamine under ice bath conditions. The reaction is carried out for 8-12 hours, and a large amount of gray precipitate is precipitated. After the reaction is completed, the electroacid is obtained after suction filtration and recrystallization, and the light gray solid is obtained.

[0056] In some preferred embodiments, the molar ratio of p-toluene isocyanate to N,N-dimethyl-p-phenylenediamine is 1:1-1:1.2.

[0057] In some preferred embodiments, the electrobasic molecule is selected from coenzyme Q0, p-benzoquinone or tetramethoxybenzoquinone.

[0058] Combination Figure 2 As shown, in some preferred embodiments, the method for preparing the circularly polarized optical switch molecule comprises the following steps:

[0059] Step S1, adding aminoketo acid derivative A and resorcinol to acidic solvent B at 50-200° C., and purifying to obtain product C after sufficient reaction.

[0060] Step S2, adding the above-mentioned product C and hexamethylenetetramine into an acidic solvent D, reacting them at 50-200° C. and then purifying them to obtain product E.

[0061] Step S3, adding the product E and chiral benzylamine F to an organic solvent G, and purifying after sufficient reaction to obtain the circularly polarized optical switch molecule.

[0062] In some embodiments, in step S1, the molar ratio of the aminoketo acid derivative A to the resorcinol is 1.0-1.2; the aminoketo acid derivative A includes 4-diethylaminoketo acid or 4-diisopropylaminoketo acid; and the acidic solvent B includes trifluoroacetic acid or methanesulfonic acid. In step S2, the molar ratio of the product C to the hexamethylenetetramine is 1.0-1.5; and the acidic solvent D includes trifluoroacetic acid or methanesulfonic acid. In step S3, the molar ratio of the product D to the chiral benzylamine F is 1.0-1.5; and the chiral benzylamine F includes R-(+)-α-methylbenzylamine or (R)-1-(pyridin-4-yl)ethylamine; and the organic solvent G includes anhydrous ethanol or dimethyl sulfoxide.

[0063] In some specific embodiments, the method for preparing the circularly polarized optical switch molecule comprises the following steps:

[0064] Step S1, dissolving 4-diethylamino keto acid and resorcinol in trifluoroacetic acid, reacting at a temperature of 85-95° C. for 12-16 hours, cooling to room temperature and drying the trifluoroacetic acid by vacuum rotary evaporation, dissolving the obtained solid in dichloromethane, and extracting with a saturated sodium bicarbonate aqueous solution, and separating and purifying the obtained crude product to obtain an orange-red solid product;

[0065] Step S2, dissolving the orange-red solid product and hexamethylenetetramine in trifluoroacetic acid, reacting at a temperature of 85-95° C. for 12-16 hours, adding deionized water and continuing the reaction for 1-3 hours, cooling to room temperature and drying the trifluoroacetic acid by vacuum rotary evaporation, dissolving the obtained solid in dichloromethane, extracting with a saturated sodium bicarbonate aqueous solution, and separating and purifying the obtained crude product to obtain an orange solid product;

[0066] Step S3, after dissolving the orange solid product in anhydrous ethanol, adding R-(+)-α-methylbenzylamine thereto, heating and refluxing for 4-6 hours, drying the anhydrous ethanol by vacuum rotary evaporation, and separating and purifying the obtained crude product to obtain the circularly polarized optical switch molecule.

[0067] In some preferred embodiments, in steps S1-S3, the separation and purification adopts column chromatography, and the eluents are methanol and dichloromethane, and in step S1, the eluent ratio is methanol: dichloromethane = 1:10-1:20, in step S2, the eluent ratio is methanol: dichloromethane = 1:70-1:100, and in step S3, the eluent ratio is methanol: dichloromethane = 1:60-1:100.

[0068] In some preferred embodiments, in step S1, the molar ratio of the 4-diethylamino keto acid to the resorcinol is 1.0-1.2;

[0069] In step S2, the molar ratio of the orange-red solid product to the hexamethylenetetramine is 1.0-1.5;

[0070] In step S3, the molar ratio of the orange solid product to the R-(+)-α-methylbenzylamine is 1.0-1.5.

[0071] Another embodiment of the present invention also provides an electrical device with adjustable circular polarization luminescence properties, comprising two transparent conductive electrodes and the electrical response material with adjustable circular polarization luminescence properties.

[0072] The electrical device with adjustable circularly polarized luminescence properties in this embodiment can realize reversible regulation of three circularly polarized luminescence states in the visible light band under the control of appropriate electrical parameters, namely, non-circularly polarized luminescence properties, left-handed circularly polarized luminescence properties and right-handed circularly polarized luminescence properties, and has good stability, and has important application value in the field of intelligent optical modulation.

[0073] Combination Figure 6 As shown, another embodiment of the present invention also provides a method for preparing an electric response device with adjustable circularly polarized luminescence properties, comprising the following steps:

[0074] Step T1, preparing a circular polarization optical switching layer solution, an ion conductive layer solution and an ion storage layer solution,

[0075] Step T2, scrape the circularly polarized optical switching layer solution onto a transparent conductive electrode, scrape the ion storage layer solution and the ion conductive layer solution onto another transparent conductive electrode, and after the solvent evaporates, squeeze the two transparent conductive electrodes loaded with functional materials together to obtain an electrically responsive device with adjustable circular polarization optical properties.

[0076] It should be noted that the transparent conductive electrode in this embodiment includes ITO glass or FTO glass, and the material is easily available.

[0077] In some preferred embodiments, in step T1, the method for configuring the circularly polarized optical switching layer solution includes:

[0078] A film-forming agent with a mass fraction of 0%-99%, an electrolyte with a mass fraction of 0%-99%, a high boiling point organic solvent with a mass fraction of 0.01%-99.9%, a circularly polarized optical switch molecule with a mass fraction of 0.01%-99.9%, an electrobase with a mass fraction of 0.01%-99.9% and an electroacid with a mass fraction of 0.01%-99.9% are stirred in a low boiling point organic solvent until they are completely dissolved.

[0079] In some preferred embodiments, the method for preparing the ion conductive layer solution comprises:

[0080] 0.01%-99.9% by mass of the film former, 0.01%-99.9% by mass of the electrolyte and 0.01%-99.9% by mass of the high boiling point organic solvent are stirred in the low boiling point organic solvent until they are completely dissolved.

[0081] In some preferred embodiments, the method for preparing the ion storage layer solution comprises:

[0082] 0.01%-99.9% by mass of a film-forming agent, 0.01%-99.9% by mass of an electrolyte, 0.01%-99.9% by mass of the high-boiling-point organic solvent, 0.01%-99.9% by mass of a functional molecule having a reducing property, and 0.01%-99.9% by mass of a functional molecule having an oxidized property are stirred in the low-boiling-point organic solvent until they are completely dissolved.

[0083] The film-forming agent described in the above embodiments includes polymethyl methacrylate, polyethylene, polystyrene, polyethylene glycol, polyethylene oxide or polyoxyethylene. The material is easily available and has good film-forming effect.

[0084] The electrolyte includes an inorganic salt such as lithium perchlorate, lithium chloride, sodium chloride or potassium iodide, or an organic salt such as tetrabutylammonium tetrafluoroborate or tetramethylammonium hexafluorophosphate.

[0085] The high boiling point organic solvent includes propylene carbonate, ethylene carbonate, dimethyl sulfoxide, butyrolactone, anisole, nitrobenzene or trimethyl phosphate, and has a good dissolving effect.

[0086] The low boiling point organic solvent includes dichloromethane, chloroform, ethyl acetate, methanol or ethanol, and has a good dissolving effect.

[0087] The functional molecules with the property of being reduced include p-benzoquinone, nitrobenzene, benzophenone, anthraquinone or dichlorobenzoquinone. The materials are easily available and can be easily reduced.

[0088] The functional molecules with oxidation characteristics include phenol, hydroquinone, aniline, p-phenylenediamine or thiophene. The materials are easy to obtain and can be easily oxidized.

[0089] The advantages of the electrically responsive device with adjustable circularly polarized luminescence properties described in the present invention and the electrically responsive material with adjustable circularly polarized luminescence properties over the prior art are the same and will not be elaborated herein.

[0090] Example 1

[0091] This embodiment provides an electrically responsive material with adjustable circularly polarized luminescence properties, including:

[0092] Electroacid, electrobase, and acid-base responsive circularly polarized optical switch molecules.

[0093] In this embodiment, the electroacid is prepared by the following method: 0.68g N, N-dimethyl-p-phenylenediamine is added to a 100mL single-mouth round-bottom flask, and then 15mL tetrahydrofuran is added as a solvent. After stirring and dissolving into a clear and transparent solution, 0.67g p-toluene isocyanate is dissolved in 15mL tetrahydrofuran, and added dropwise to the above-mentioned tetrahydrofuran solution of N, N-dimethyl-p-phenylenediamine under ice bath conditions. The reaction is carried out for 10 hours, and a large amount of gray precipitate is precipitated. After the reaction is completed, the solid is filtered out and recrystallized with methanol. The final product is a light gray solid Urea-N with a yield of about 87%. The specific synthesis route is as follows:

[0094]

[0095] The nuclear magnetic spectrum of the electroacid prepared in this example is as follows: Figure 1 shown.

[0096] In this embodiment, the electro-alkaline molecule is selected from coenzyme Q0, namely 2,3-dimethoxy-5-methyl-1,4-benzoquinone, which is directly purchased.

[0097] In this embodiment, the synthesis route of the circular polarization optical switch molecule R-Rhodol-A is as follows:

[0098]

[0099] The specific preparation method comprises the following steps:

[0100] Step S1, add 1.25g 4-diethylamino keto acid and 0.44g resorcinol into a 30mL pressure tube, add about 15mL trifluoroacetic acid as a solvent, and stir and dissolve the above raw materials. The system is heated to 90°C and stirred at this temperature for 12 hours. After the reaction is completed, it is naturally cooled to room temperature, and the trifluoroacetic acid is rotary evaporated to dryness under vacuum, and the obtained solid is dissolved in 35mL dichloromethane. Then, it is extracted with 35mL of saturated sodium bicarbonate aqueous solution, repeated three times, and the organic phase is collected. The crude product is separated and purified by column chromatography, and the eluent ratio is methanol: dichloromethane = 1:10, and the final product is orange-red solid Rhodol. The yield is about 60%.

[0101] Step S2, add 2.52g orange-red solid Rhodol and 1.00g hexamethylenetetramine to a 100mL single-mouth round-bottom flask, then add about 30mL of trifluoroacetic acid as a solvent, and stir and dissolve the above raw materials. The system is heated to 90°C, stirred and reacted at this temperature for 14h, and then 5mL of deionized water is added to the reaction system, and the reaction is continued at this temperature for 2h. After the reaction is completed, it is naturally cooled to room temperature, and the trifluoroacetic acid is rotary evaporated to dryness under vacuum, and the obtained solid is dissolved in 80mL of dichloromethane. Then, it is extracted with 80mL of saturated sodium bicarbonate aqueous solution, repeated three times, and the organic phase is collected. The crude product is separated and purified by column chromatography, and the eluent ratio is methanol: dichloromethane = 1:70. The final product is an orange solid Rhodol-CHO with a yield of about 40%.

[0102] Step S3, add 0.30g of orange solid Rhodol-CHO to a 100mL single-mouth round-bottom flask, add about 40mL of anhydrous ethanol as a solvent, and stir to dissolve. Then, add 102μL of R-(+)-ɑ-methylbenzylamine to the above solution, and heat the reaction solution to reflux for 5h. After the reaction is completed, the anhydrous ethanol is rotary evaporated to dryness under vacuum. The crude product is separated and purified by column chromatography, and the eluent ratio is methanol: dichloromethane = 1:60 to obtain the circularly polarized optical switch molecule R-Rhodol-A, which is an orange-red solid with a yield of about 40%. The nuclear magnetic spectrum of the obtained circularly polarized optical switch molecule is shown as follows Figure 3 The acid-base response properties of R-Rhodol-A are shown in Figure 4 and Figure 5 ,in, Figure 4Figure A shows the changes in the circular dichroism properties of R-Rhodol-A acetonitrile solution under different acid addition conditions; Figure B shows the changes in the photoluminescence properties of R-Rhodol-A under different acid addition conditions; Figure C shows the changes in the absorbance properties of R-Rhodol-A acetonitrile solution under different acid addition conditions; Figure D shows the actual picture of the color and fluorescence changes of R-Rhodol-A acetonitrile solution under different acid addition conditions. Figure 5 Figure A shows the changes in the circular dichroism of R-Rhodol-A acetonitrile solution under different alkali conditions; Figure B shows the changes in the photoluminescence of R-Rhodol-A under different alkali conditions; Figure C shows the changes in the absorbance of R-Rhodol-A acetonitrile solution under different alkali conditions; Figure D shows the actual picture of the color and fluorescence changes of R-Rhodol-A acetonitrile solution under different alkali conditions. It can be seen that after adding different equivalents of chemical acid and chemical base to the acetonitrile solution of R-Rhodol-A, the chiral properties (circular dichroism), color and fluorescence of R-Rhodol-A all change significantly, and the properties of acid and base responses are different.

[0103] This embodiment utilizes the property of "electroacidic" aniline derivatives and "electroalkaline" quinone derivatives that can reversibly release protons or capture protons during electrochemical oxidation or reduction, and combines them with circularly polarized optical switch molecules that respond to both acids and bases. It is possible to obtain an electroresponsive material with adjustable circularly polarized luminescence properties under the action of an electric field. The required raw materials are simple and easy to obtain, and the device construction cost is low.

[0104] Example 2

[0105] This embodiment provides a method for preparing an electric response device with adjustable circularly polarized luminescence properties, comprising the following steps:

[0106] Step T1, preparing a circular polarization optical switching layer solution, an ion conductive layer solution and an ion storage layer solution,

[0107] Step T2, scrape the circularly polarized optical switching layer solution onto a transparent conductive electrode, scrape the ion storage layer solution and the ion conductive layer solution onto another transparent conductive electrode, and after the solvent evaporates, squeeze the two transparent conductive electrodes loaded with functional materials together to obtain an electrically responsive device with adjustable circular polarization optical properties.

[0108] In this embodiment, in step T1, the method for configuring the circularly polarized optical switching layer solution includes:

[0109] 0.1 g of polymethyl methacrylate, 0.042 g of tetrabutylammonium hexafluorophosphate, 0.021 mL of propylene carbonate, 2 mg of R-Rhodol-A, 0.15 mg of coenzyme Q0 and 0.225 mg of Urea-N were stirred in 1 mL of acetonitrile until completely dissolved.

[0110] In this embodiment, in step T1, the method for preparing the ion conductive layer solution includes:

[0111] 3.6 g of polymethyl methacrylate, 1.5 g of tetrabutylammonium hexafluorophosphate and 0.75 mL of propylene carbonate were stirred in 20 ml of acetonitrile until completely dissolved.

[0112] In this embodiment, the method for configuring the ion storage layer solution includes:

[0113] 0.72 g of polymethyl methacrylate, 0.30 g of tetrabutylammonium hexafluorophosphate, 0.15 mL of propylene carbonate, 54 mg of p-benzoquinone, and 110 mg of hydroquinone were stirred in 10 mL of acetonitrile until they were completely dissolved.

[0114] Combination Figure 7-8 As shown, the electric response device with adjustable circularly polarized luminescence properties prepared in this embodiment exhibits different circularly polarized luminescence properties under different voltage parameters. When no voltage is applied, there is no circularly polarized luminescence property. At -1.5V, the device exhibits a left-handed CPL signal with an emission peak at 558nm, and at +1.5V, it exhibits a left-handed CPL signal with an emission peak at 572nm. When a smaller reverse voltage (+0.5V / -0.5V) is applied, it can reversibly return to the initial state.

[0115] Although the disclosure is disclosed as above, the protection scope of the disclosure is not limited thereto. Those skilled in the art may make various changes and modifications without departing from the spirit and scope of the disclosure, and these changes and modifications will fall within the protection scope of the present invention.

Claims

1. An electrically responsive material with adjustable circularly polarized luminescence properties, characterized in that: include: Electroacid, electrobase, and acid-base responsive circularly polarized optical switch molecules; The electroacid is an aniline derivative, The electrobase is a benzoquinone derivative, The structural formula of the circular polarization optical switch molecule is: ， wherein R1 and R2 are hydrogen or alkyl substituents, R3 and R4 are hydrogen, phenyl or alkyl substituents, and R3 and R4 are heterogeneous substituents, The preparation method of the circular polarization optical switch molecule comprises the following steps: Step S1, adding aminoketo acid derivative A and resorcinol to acidic solvent B at 50-200° C., reacting sufficiently and then purifying to obtain product C; Step S2, adding the above-mentioned product C and hexamethylenetetramine into an acidic solvent D, reacting them at 50-200° C. and then purifying them to obtain a product E; Step S3, adding the product E and chiral benzylamine F to an organic solvent G, and purifying after sufficient reaction to obtain the circularly polarized optical switch molecule.

2. The electrically responsive material with adjustable circularly polarized luminescence properties according to claim 1, characterized in that: In step S1, the molar ratio of the aminoketo acid derivative A to the resorcinol is 1.0-1.2; the aminoketo acid derivative A includes 4-diethylaminoketo acid or 4-diisopropylaminoketo acid; the acidic solvent B includes trifluoroacetic acid or methanesulfonic acid; In step S2, the molar ratio of the product C to the hexamethylenetetramine is 1.0-1.5; the acidic solvent D comprises trifluoroacetic acid or methanesulfonic acid; In step S3, the molar ratio of the product E to the chiral benzylamine F is 1.0-1.5; the chiral benzylamine F includes R-(+)-α-methylbenzylamine or (R)-1-(pyridin-4-yl)ethylamine; and the organic solvent G includes anhydrous ethanol or dimethyl sulfoxide.

3. An electrical device with adjustable circularly polarized luminescence properties, characterized in that: The invention comprises two transparent conductive electrodes and an electrically responsive material with adjustable circularly polarized luminescence properties as described in any one of claims 1 to 2.

4. A method for preparing an electrically responsive device with adjustable circularly polarized luminescence properties, for preparing the electrically responsive device with adjustable circularly polarized luminescence properties as claimed in claim 3, characterized in that: The method comprises the following steps: Step T1, preparing a circular polarization optical switching layer solution, an ion conductive layer solution and an ion storage layer solution, Step T2, scrape the circularly polarized optical switching layer solution onto a transparent conductive electrode, scrape the ion storage layer solution and the ion conductive layer solution onto another transparent conductive electrode, and after the solvent evaporates, squeeze the two transparent conductive electrodes loaded with functional materials together to obtain the circularly polarized luminescence property adjustable electrical response device.

5. The method for preparing the electric response device with adjustable circularly polarized luminescence properties according to claim 4, characterized in that: In step T1, the method for preparing the circularly polarized optical switching layer solution includes: A film-forming agent with a mass fraction of 0%-99%, an electrolyte with a mass fraction of 0%-99%, a high boiling point organic solvent with a mass fraction of 0.01%-99.9%, a circularly polarized optical switch molecule with a mass fraction of 0.01%-99.9%, an electrobase with a mass fraction of 0.01%-99.9% and an electroacid with a mass fraction of 0.01%-99.9% are stirred in a low boiling point organic solvent until they are completely dissolved.

6. The method for preparing the electric response device with adjustable circularly polarized luminescence properties according to claim 4, characterized in that: The method for configuring the ion conductive layer solution comprises: 0.01%-99.9% by mass of a film-forming agent, 0.01%-99.9% by mass of an electrolyte and 0.01%-99.9% by mass of a high-boiling-point organic solvent are stirred in a low-boiling-point organic solvent until they are completely dissolved.

7. The method for preparing the electric response device with adjustable circularly polarized luminescence properties according to claim 4, characterized in that: The method for configuring the ion storage layer solution comprises: 0.01%-99.9% by mass of a film-forming agent, 0.01%-99.9% by mass of an electrolyte, 0.01%-99.9% by mass of a high-boiling point organic solvent, 0.01%-99.9% by mass of a functional molecule with a reducing property, and 0.01%-99.9% by mass of a functional molecule with an oxidized property are stirred in a low-boiling point organic solvent until they are completely dissolved.

8. The method for preparing the electric response device with adjustable circularly polarized luminescence properties according to claim 7, characterized in that: The functional molecules with the property of being reduced include p-benzoquinone, nitrobenzene, benzophenone, anthraquinone or dichlorobenzoquinone.

9. The method for preparing the electric response device with adjustable circularly polarized luminescence properties according to claim 7, characterized in that: The functional molecules having oxidation characteristics include phenol, hydroquinone, aniline, p-phenylenediamine or thiophene.

Images