Naphthalimide-based schiff base derivative, and preparation method therefor and use thereof

Abstract

Disclosed in the present disclosure are a naphthalimide-based Schiff base derivative, and a preparation method therefor and a use thereof. The structural formula of the naphthalimide-based Schiff base derivative is: (1) or (2), wherein R1, R2, R3, and R4 are each independently H or an alkyl group having 1-4 carbon atoms.

Description

Naphthalimide Schiff base derivatives and preparation methods and applications thereof Technical Field

[0001] The present disclosure belongs to the technical field of organic light-emitting materials, and particularly relates to a naphthylimide Schiff base derivative and a preparation method and application thereof. Background Art

[0002] Static volumetric 3D display is a very important branch of 3D display technology. It generally uses a light beam to address the inside of the display medium to generate voxel light, and forms a volumetric 3D pattern through an array of multiple voxel points.

[0003] Among the currently reported methods, the most common ones are using rare earth material upconversion luminescence or laser ionization of air to achieve static volumetric 3D display. However, these technologies require expensive high-energy light beams and pose significant safety risks. Photochromism refers to the ability of material A to undergo a specific change in response to light, producing an isomer B with different properties. This is then restored by another light beam or heat, without the need for a high-energy light beam. When the reaction speed is fast enough, photochromic materials can also achieve photoaddressing to produce voxel luminescence. Among these, salicylaldehyde primary amine Schiff base molecules, when excited, undergo rapid intramolecular proton transfer, producing photochromic and thermochromic phenomena, which have applications in information storage, optical switching, and information display. However, the low luminescence intensity of the keto structure of salicylaldehyde primary amine Schiff bases after photochromism hinders their application in static volumetric 3D display systems. Summary of the Invention

[0004] The present disclosure aims to at least partially address one of the technical problems in the related art. To this end, one objective of the present disclosure is to provide a naphthaleneimide Schiff base derivative, its preparation method, and its application. This naphthaleneimide Schiff base derivative can enhance the luminescence intensity of the Schiff base keto isomer, thereby enhancing the luminescence intensity of voxels generated by beam addressing when used as a static volumetric three-dimensional display medium.

[0005] In the first aspect of the present disclosure, the present disclosure provides a naphthalene imide Schiff base derivative. According to an embodiment of the present disclosure, the structural formula of the naphthalene imide Schiff base derivative is:

[0006] wherein R1, R2, R3 and R4 are each independently H or an alkyl group having 1 to 4 carbon atoms.

[0007] According to the naphthylimide Schiff base derivatives of the above embodiments of the present disclosure, their structure is an enol form and has photochromic properties. Based on the principle of excited-state proton transfer, they can rapidly isomerize from the enol form to the keto form under ultraviolet light stimulation, and the absorption spectrum and excitation wavelength also change. In addition, their keto isomer is a metastable structure that can quickly revert to the enol structure. When ultraviolet light and the excitation light of the keto isomer intersect, voxel points can be generated in three-dimensional space to emit light. When the ultraviolet light or the excitation light of the keto isomer is turned off, the voxel points immediately disappear, and dual-beam addressing in the medium space can be achieved. At the same time, the 1,8-naphthalimide group in its aldehyde structure has strong fluorescence, and the phenyl group connected to the nitrogen atom in the 1,8-naphthalimide structure is a rigid group, which can reduce the non-radiative transition of electrons, thereby increasing the luminescence intensity of the Schiff base keto isomer, so that it can be used as a static volume three-dimensional display medium, which can improve the luminescence intensity of the voxel points generated by beam addressing, and the generated voxel points have high luminescence contrast, fast refresh speed, and good stability.

[0008] In a second aspect of the present disclosure, a method for preparing the aforementioned naphthylimide Schiff base derivative is provided. According to an embodiment of the present disclosure, the method comprises: conducting a first reaction in a first organic solvent with N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid)aniline to obtain the naphthylimide Schiff base derivative, wherein the first compound has the structural formula:

[0009] wherein R1, R2, R3 and R4 are each independently H or an alkyl group having 1 to 4 carbon atoms.

[0010] The naphthaleneimide Schiff base derivative prepared using this method can enhance the luminescence intensity of the Schiff base keto isomer, thereby enhancing the luminescence intensity of voxels generated by beam-addressed display media. Furthermore, the resulting voxels exhibit high contrast, fast refresh rates, and excellent stability. Furthermore, the method offers high yield and low cost, making it suitable for industrial production.

[0011] In addition, the method for preparing the naphthylimide Schiff base derivative according to the above embodiment of the present disclosure may also have the following additional technical features:

[0012] In some embodiments of the present disclosure, the molar ratio of N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid)aniline to the first compound is 1:(0.9-1.1).

[0013] In some embodiments of the present disclosure, the first organic solvent includes at least one of methanol, ethanol, and dimethyl sulfoxide.

[0014] In some embodiments of the present disclosure, N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline is prepared by the following steps: (1) subjecting 4-bromo-1,8-naphthalene dicarboxylic anhydride to a second reaction with aniline in a first acidic solvent to obtain a second compound; (2) subjecting the second compound to a third reaction with a methoxy reagent in a second organic solvent containing a catalyst to obtain a third compound; (3) subjecting the third compound to a fourth reaction with a hydrohalic acid to obtain a fourth compound; and (4) subjecting the fourth compound to a fifth reaction with hexamethylenetetramine in a second acidic solvent to obtain N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline.

[0015] In some embodiments of the present disclosure, the first acidic solvent and the second acidic solvent independently include glacial acetic acid and / or trifluoroacetic acid.

[0016] In some embodiments of the present disclosure, in step (1), the molar ratio of 4-bromo-1,8-naphthalene dicarboxylic anhydride to aniline is 1:(1.5-3.5).

[0017] In some embodiments of the present disclosure, in step (2), the molar ratio of the second compound, the methoxy reagent, and the catalyst is 1:(7-8):(0.1-0.3).

[0018] In some embodiments of the present disclosure, the second organic solvent includes at least one of methanol, N,N-dimethylformamide, and dimethyl sulfoxide.

[0019] In some embodiments of the present disclosure, the methoxy reagent includes sodium methoxide and / or potassium methoxide.

[0020] In some embodiments of the present disclosure, the catalyst includes at least one of copper sulfate, copper phosphate, copper acetate, and copper nitrate.

[0021] In some embodiments of the present disclosure, in step (3), the hydrohalic acid includes HI and / or HBr.

[0022] In some embodiments of the present disclosure, the concentration of the hydrohalic acid is not less than 57 wt %.

[0023] In some embodiments of the present disclosure, the content of the third compound in the hydrohalic acid is 60 mmol / L-100 mmol / L.

[0024] In some embodiments of the present disclosure, in step (4), the molar ratio of the fourth compound to hexamethylenetetramine is 1:(1-3).

[0025] In a third aspect of the present disclosure, the present disclosure proposes the use of the above-mentioned naphthylimide Schiff base derivative in a static volume 3D display system, thereby solving the problem of luminescence intensity of the keto isomer of Schiff base used in the static volume 3D display system.

[0026] Additional aspects and advantages of the present disclosure will be given in part in the description that follows and, in part, will be obvious from the description that follows, or will be learned through practice of the present disclosure. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] The above and / or additional aspects and advantages of the present disclosure will become apparent and readily understood from the description of the embodiments in conjunction with the following drawings, in which:

[0028] FIG1 is a schematic flow diagram of a method for preparing N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline according to one embodiment of the present disclosure;

[0029] FIG2 is a flow chart of a method for preparing a naphthylimide Schiff base derivative according to Example 1 of the present disclosure;

[0030] FIG3 is a hydrogen NMR spectrum of the target product obtained according to Example 1 of the present disclosure;

[0031] FIG4 is an absorption spectrum of the target product obtained according to Example 1 of the present disclosure;

[0032] FIG5 shows the phenomenon of luminescence of voxel points inside the solution prepared according to Example 3 of the present disclosure. DETAILED DESCRIPTION

[0033] The following embodiments of the present disclosure are described in detail. The embodiments described below are exemplary and are intended only to explain the present disclosure and are not to be construed as limiting the present disclosure. Where specific techniques or conditions are not specified in the embodiments, the techniques or conditions described in the literature in the art or in the product instructions were used. Reagents or instruments used without specifying the manufacturer are all commercially available conventional products.

[0034] In the first aspect of the present disclosure, the present disclosure provides a naphthalene imide Schiff base derivative. According to an embodiment of the present disclosure, the structural formula of the naphthalene imide Schiff base derivative is:

[0035] wherein R1, R2, R3 and R4 are each independently H or an alkyl group having 1 to 4 carbon atoms.

[0036] According to the naphthylimide Schiff base derivatives of the above embodiments of the present disclosure, their structure is an enol form and has photochromic properties. Based on the principle of excited-state proton transfer, they can rapidly isomerize from the enol form to the keto form under ultraviolet light stimulation, and the absorption spectrum and excitation wavelength also change. In addition, their keto isomer is a metastable structure that can quickly revert to the enol structure. When ultraviolet light and the excitation light of the keto isomer intersect, voxel points can be generated in three-dimensional space to emit light. When the ultraviolet light or the excitation light of the keto isomer is turned off, the voxel points immediately disappear, and dual-beam addressing in the medium space can be achieved. At the same time, the 1,8-naphthalimide group in its aldehyde structure has strong fluorescence, and the phenyl group connected to the nitrogen atom in the 1,8-naphthalimide structure is a rigid group, which can reduce the non-radiative transition of electrons, thereby increasing the luminescence intensity of the Schiff base keto isomer, so that it can be used as a static volume three-dimensional display medium, which can improve the luminescence intensity of the voxel points generated by beam addressing, and the generated voxel points have high luminescence contrast, fast refresh speed, and good stability.

[0037] In a second aspect of the present disclosure, a method for preparing the aforementioned naphthylimide Schiff base derivative is provided. According to an embodiment of the present disclosure, the method comprises: conducting a first reaction in a first organic solvent with a first compound and N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline to obtain a naphthylimide Schiff base derivative, wherein the structural formula of N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline is: The structural formula of the first compound is: wherein R1, R2, R3, and R4 are each independently H or an alkyl group having 1-4 carbon atoms. Thus, the naphthylimide Schiff base derivative prepared by the above method can enhance the luminescence intensity of the Schiff base keto isomer, thereby enabling its use as a static volumetric three-dimensional display medium. This can enhance the luminescence intensity of voxels generated by beam addressing, and the resulting voxels exhibit high contrast, fast refresh rate, and excellent stability. Furthermore, this method offers high yield, low cost, and suitability for industrial production.

[0038] Specifically, the first compound can be mixed with N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline in a first organic solvent and refluxed for 2-6 hours to obtain a naphthylimide Schiff base derivative. This is beneficial for promoting the first reaction and improving the utilization rate of the reaction raw materials.

[0039] According to a specific embodiment of the present disclosure, the molar ratio of N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline to the first compound can be 1:(0.9-1.1), for example, it can be 1:0.9, 1:0.92, 1:0.94, 1:0.96, 1:0.98, 1:1, 1:1.02, 1:1.04, 1:1.06, 1:1.08, 1:1.1, etc. The inventors have found that a molar ratio of N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline to the first compound that is too large or too small may reduce the yield of the first reaction. The present disclosure can improve the yield of the first reaction by controlling the molar ratio of N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline to the first compound within the above range.

[0040] It should be noted that the specific composition of the first organic solvent is not particularly limited and can be selected by those skilled in the art according to actual needs. For example, the first organic solvent may include at least one of methanol, ethanol and dimethyl sulfoxide.

[0041] According to a specific embodiment of the present disclosure, with reference to FIG1 , N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid)aniline can be prepared by the following steps:

[0042] S100: Performing a second reaction of 4-bromo-1,8-naphthalene dicarboxylic anhydride with aniline in a first acidic solvent

[0043] In this step, 4-bromo-1,8-naphthalene dicarboxylic anhydride and aniline are subjected to a second reaction in a first acidic solvent to obtain a second compound. The structural formula of the second compound is:

[0044] Specifically, 4-bromo-1,8-naphthalene dicarboxylic anhydride and aniline can be mixed in a first acidic solvent and refluxed for 4-8 hours under an inert gas (such as nitrogen) to obtain the second compound. This is beneficial for promoting the progress of the second reaction and improving the utilization rate of the reaction raw materials.

[0045] According to specific embodiments of the present disclosure, the molar ratio of 4-bromo-1,8-naphthalene dicarboxylic anhydride to aniline can be 1:(1.5-3.5), for example, 1:1.5, 1:1.7, 1:2, 1:2.3, 1:2.5, 1:2.7, 1:3, 1:3.3, 1:3.5, etc. The present disclosure can improve the yield of the second reaction by controlling the molar ratio of 4-bromo-1,8-naphthalene dicarboxylic anhydride to aniline within the above range.

[0046] It should be noted that the specific composition of the first acidic solvent is not particularly limited and can be selected by those skilled in the art according to actual needs. For example, it may include glacial acetic acid and / or trifluoroacetic acid (TFA).

[0047] S200: performing a third reaction on the second compound and the methoxy reagent in a second organic solvent containing a catalyst

[0048] In this step, the second compound and the methoxy reagent are subjected to a third reaction in a second organic solvent containing a catalyst to obtain a third compound. The structural formula of the third compound is:

[0049] Specifically, the second compound and the methoxy reagent can be mixed in a second organic solvent and refluxed for 6-10 hours under an inert gas (such as nitrogen) to obtain the third compound. This is conducive to promoting the progress of the third reaction and improving the utilization rate of the reaction raw materials.

[0050] According to specific embodiments of the present disclosure, the molar ratio of the second compound, the methoxy reagent, and the catalyst can be 1:(7-8):(0.1-0.3), for example, 1:7:0.1, 1:7:0.2, 1:7:0.3, 1:8:0.1, 1:8:0.2, 1:8:0.3, etc. The present disclosure can improve the yield of the third reaction by controlling the molar ratio of the second compound, the methoxy reagent, and the catalyst within the above range.

[0051] Specifically, the methoxy reagent may include sodium methoxide and / or potassium methoxide; the second organic solvent may include at least one of methanol, N,N-dimethylformamide and dimethyl sulfoxide; and the catalyst may include at least one of copper sulfate, copper phosphate, copper acetate and copper nitrate.

[0052] S300: performing a fourth reaction on the third compound and the hydrohalic acid

[0053] In this step, the third compound is subjected to a fourth reaction with a hydrohalic acid to obtain a fourth compound. The hydrohalic acid may include HI and / or HBr; the fourth compound has the structural formula:

[0054] Specifically, the third compound can be mixed with a hydrohalic acid and refluxed under an inert gas (such as nitrogen) for 8-12 hours to obtain the fourth compound. This is beneficial to promoting the fourth reaction and improving the utilization rate of the reaction raw materials.

[0055] According to a specific embodiment of the present disclosure, the concentration of the hydrohalic acid is not less than 57 wt %, which is beneficial to promoting the fourth reaction and thus improving the utilization rate of the reaction raw materials.

[0056] According to a specific embodiment of the present disclosure, the content of the third compound in the hydrohalic acid can be 60 mmol / L-100 mmol / L, for example, 60 mmol / L, 65 mmol / L, 70 mmol / L, 75 mmol / L, 80 mmol / L, 85 mmol / L, 90 mmol / L, 95 mmol / L, 100 mmol / L, etc. The present disclosure can improve the yield of the fourth reaction by controlling the content of the third compound in the hydrohalic acid within the above range.

[0057] S400: performing a fifth reaction on the fourth compound and urotropine in a second acidic solvent

[0058] In this step, the fourth compound is reacted with hexamethylenetetramine (HMTA) in a second acidic solvent to obtain N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid) aniline. The second acidic solvent may include glacial acetic acid and / or trifluoroacetic acid.

[0059] Specifically, the mixture of the fourth compound and hexamethylenetetramine can be refluxed in glacial acetic acid and / or trifluoroacetic acid for 8-12 hours, thereby promoting the fifth reaction and improving the utilization rate of the reaction raw materials.

[0060] According to specific embodiments of the present disclosure, the molar ratio of the fourth compound to hexamine can be 1:(1-3), for example, 1:1, 1:1.2, 1:1.4, 1:1.6, 1:1.8, 1:2, 1:2.2, 1:2.4, 1:2.6, 1:2.8, 1:3, etc. The present disclosure can increase the yield of the fifth reaction by controlling the molar ratio of the fourth compound to hexamine within the above range.

[0061] In a third aspect of the present disclosure, the present disclosure proposes the use of the above-mentioned naphthylimide Schiff base derivative in a static volume 3D display system, thereby solving the problem of luminescence intensity of the keto isomer of Schiff base used in the static volume 3D display system.

[0062] Specifically, the naphthaleneimide Schiff base derivative can be dispersed in an organic solvent or cured in a polymer material such as epoxy resin, polymethyl methacrylate, or polydimethylsiloxane to serve as a volumetric 3D display medium. The voxel excitation light source uses two light beams of different wavelengths, which intersect within the display medium for addressing. When the light source scanning speed exceeds the refresh rate of the human eye, a multi-voxel array is formed, thereby displaying a 3D image.

[0063] The present disclosure is described below with reference to specific embodiments. It should be noted that these embodiments are merely illustrative and do not limit the present disclosure in any way.

[0064] Example 1

[0065] As shown in FIG2 , the preparation method of the naphthylimide Schiff base derivative is as follows:

[0066] Mix 27.7 g (0.1 mol) of 4-bromo-1,8-naphthalenedicarboxylic anhydride and 18.6 g (0.2 mol) of aniline in 300 mL of glacial acetic acid. Reflux at 120°C under nitrogen for 6.5 h. After cooling, pour the mixture into water to produce a yellow precipitate. Filter and recrystallize to obtain pale yellow crystals, the second compound.

[0067] 17.6 g (0.05 mol) of the second compound, 20.2 g (0.375 mol) of sodium methoxide, and 1.6 g (0.01 mol) of copper sulfate were dispersed in 200 mL of dry methanol. The mixture was refluxed at 65°C under nitrogen for 8 h. The resulting solution was cooled to room temperature and filtered to obtain a pale yellow solid. The solid was then washed with 10 wt% hydrochloric acid (30 mL x 3) and water (20 mL x 3) to obtain the third compound.

[0068] 6.0 g (0.02 mol) of the third compound was mixed with 200 mL of 57 wt% hydroiodic acid and refluxed under nitrogen for 12 h. The resulting solution was cooled to room temperature, filtered, and the crude product was washed with water (50 mL x 3) to obtain a yellow-green solid. The crude product was purified by column chromatography to obtain the fourth compound.

[0069] A mixture of 2.9 g (0.01 mol) of the fourth compound and 2.8 g (0.02 mol) of methenamine was refluxed in trifluoroacetic acid for 8 h, and the resulting reaction mixture was then cooled to room temperature. The reaction mixture was diluted with distilled water, and the resulting precipitate was filtered. The precipitate was washed several times with distilled water and dried. It was then dissolved in dichloromethane and purified using a short silica plug to obtain N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid)aniline;

[0070] 0.63 g (2 mmol) of N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid)aniline and 0.24 g (2 mmol) of (S)-α-methylbenzylamine were mixed in 20 mL of ethanol, refluxed for 4 h, filtered and washed to obtain the target compound.

[0071] Example 2

[0072] The preparation method of the naphthalene imide Schiff base derivative is as follows:

[0073] 0.63 g (2 mmol) of N-(3-formyl-4-hydroxy-1,8-naphthalene dicarboxylic acid)aniline and 0.24 g (2 mmol) of (R)-α-methylbenzylamine were mixed in 20 mL of ethanol, refluxed for 4 h, filtered and washed to obtain the target compound.

[0074] The target product obtained in Example 1-2 was tested by hydrogen nuclear magnetic resonance spectrum and ultraviolet-visible absorption spectrum.

[0075] The H NMR spectrum of the target product obtained in Example 1 is shown in FIG3 . 1 H NMR (400 MHz, DMSO-d6) chemical shift (δ): 8.96 (d, J = 12.7 Hz, 1H), 8.60 (d, J = 6.8 Hz, 1H), 8.43 (d, J = 6.8 Hz, 2H), 7.69 (d, J = 9.7 Hz, 1H), 7.51 (d, J = 7.2 Hz, 3H), 7.48–7.43 (m, 5H), 7.38 (s, 1H), 7.31 (t, J = 5.8 Hz, 2H), 5.13 (d, J = 9.6 Hz, 1H), 1.24 (s, 4H). The number and position of H atoms in the H NMR spectrum correspond to those in the naphthalene imide Schiff base derivative, indicating that a naphthalene imide Schiff base derivative having the required structure was prepared in Example 1. The H NMR spectrum of the target product obtained in Example 2 is similar to that of Example 1, indicating that Example 2 prepared a naphthylimide Schiff base derivative with a structure that meets the requirements. The UV-visible absorption spectrum test results of the target product obtained in Example 1 are shown in Figure 4. The UV-visible absorption spectrum test results of the target product obtained in Example 2 are similar to those of Example 1.

[0076] Example 3

[0077] The three-dimensional application method of the naphthylimide Schiff base derivative is as follows:

[0078] The naphthaleneimide Schiff base derivative obtained in Example 1 was fully dissolved in cyclohexane to prepare a 0.01 mmol / L cyclohexane solution of the naphthaleneimide Schiff base derivative. This solution was then placed in a quartz container. As shown in Figure 5, by selecting a suitable light source, such as a 405 nm laser and a 488 nm laser, high-intensity luminescence was observed at the voxel point. The reaction equation is as follows:

[0079] By controlling dual-beam scanning to address the solution, volumetric 3D display can be achieved. Thus, the naphthylimide Schiff base derivative obtained in Example 1 can be applied to a beam-addressable static volumetric 3D display system. This demonstrates that the disclosed naphthylimide Schiff base derivative can enhance the luminescence intensity of the Schiff base keto isomer, thereby enabling its use as a static volumetric 3D display medium to enhance the luminescence intensity of voxels generated by beam addressing.

[0080] In this disclosure, the terms "first" and "second" are used for descriptive purposes only and should not be understood to indicate or imply relative importance or implicitly specify the number of technical features indicated. Therefore, a feature defined as "first" or "second" may explicitly or implicitly include at least one of such features. In the description of this disclosure, "plurality" means at least two, for example, two, three, etc., unless otherwise specifically defined.

[0081] In the description of this specification, the description with reference to the terms "one embodiment", "some embodiments", "example", "specific example", or "some examples" means that the specific features, structures, materials or characteristics described in conjunction with the embodiment or example are included in at least one embodiment or example of the present disclosure. In this specification, the schematic representations of the above terms do not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials or characteristics described may be combined in any one or more embodiments or examples in a suitable manner. In addition, those skilled in the art may combine and combine different embodiments or examples described in this specification and features of different embodiments or examples, unless they are mutually inconsistent.

[0082] Although the embodiments of the present disclosure have been shown and described above, it is understood that the above embodiments are illustrative and are not to be construed as limitations on the present disclosure. A person skilled in the art may change, modify, replace and vary the above embodiments within the scope of the present disclosure.

Claims

1. A naphthalimide-based Schiff base derivative, wherein, The structural formula of the naphthalimide-based Schiff base derivative is as follows: Wherein, R1, R2, R3 and R4 are each independently H or an alkyl group having 1 to 4 carbon atoms.

2. A method for preparing the naphthalimide-based Schiff base derivative according to claim 1, wherein, Comprising: The first compound is subjected to a first reaction with N-(3-formyl-4-hydroxy-1,8-naphthalenedicarboximide)aniline in a first organic solvent to obtain the naphthalimide-based Schiff base derivative, and the structural formula of the first compound is: Wherein, R1, R2, R3 and R4 are each independently H or an alkyl group having 1 to 4 carbon atoms.

3. The method according to claim 2, wherein, The molar ratio of N-(3-formyl-4-hydroxy-1,8-naphthalenedicarboximide)aniline to the first compound is 1:(0.9 - 1.1).

4. The method according to claim 2 or 3, wherein The first organic solvent includes at least one of methanol, ethanol and dimethyl sulfoxide.

5. The method according to any one of claims 2 to 4, wherein N-(3-formyl-4-hydroxy-1,8-naphthalenedicarboximide)aniline is prepared by the following steps: (1) React 4-bromo-1,8-naphthalic anhydride with aniline in a first acidic solvent to obtain a second compound; (2) React the second compound with a methoxy reagent in a second organic solvent containing a catalyst to obtain a third compound; (3) React the third compound with a hydrohalic acid to obtain a fourth compound; (4) React the fourth compound with hexamethylenetetramine in a second acidic solvent to obtain N-(3-formyl-4-hydroxy-1,8-naphthalenedicarboximide)aniline.

6. The method according to claim 5, wherein The first acidic solvent and the second acidic solvent each independently include glacial acetic acid and / or trifluoroacetic acid.

7. The method according to claim 5 or 6, wherein In step (1), the molar ratio of 4-bromo-1,8-naphthalic anhydride to aniline is 1:(1.5 - 3.5).

8. The method according to any one of claims 5 to 7, wherein In step (2), the molar ratio of the second compound, the methoxy reagent and the catalyst is 1:(7 - 8):(0.1 - 0.3).

9. According to the method according to any one of claims 5 to 8, wherein The second organic solvent includes at least one of methanol, N,N-dimethylformamide and dimethyl sulfoxide.

10. The method according to any one of claims 5 to 9, wherein, The methoxy reagent includes sodium methoxide and / or potassium methoxide.

11. According to the method according to any one of claims 5 to 10, wherein The catalyst includes at least one of copper sulfate, copper phosphate, copper acetate and copper nitrate.

12. The method according to any one of claims 5 to 11, wherein, In step (3), the hydrohalic acid includes HI and / or HBr.

13. The method according to any one of claims 5 to 12, wherein The concentration of the hydrohalic acid is not less than 57wt%.

14. The method according to any one of claims 5 to 13, wherein, The content of the third compound in the hydrohalic acid is 60 mmol / L - 100 mmol / L.

15. The method according to any one of claims 5 to 14, wherein, In step (4), the molar ratio of the fourth compound to hexamethylenetetramine is 1:(1 - 3).

16. Use of the naphthalimide-based Schiff base derivative according to claim 1 in a static volume three-dimensional display system.

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