Naphthalimide compounds, methods of making and using the same

Abstract

The application provides a naphthalimide compound, a preparation method and application thereof, has a structure of a general formula (I), the preparation method is that a 1,4,5,8-naphthalene tetracarboxylic anhydride derivative compound is hydrolyzed under alkaline conditions to obtain a hydrolysis product, and the hydrolysis product is subjected to a condensation reaction with a methoxy polyethylene glycol amine compound under weak acid conditions, and the application solves the problems of poor storage stability of zinc oxide nanoparticles and low efficiency and poor stability of a device based on a zinc oxide nanoparticle electron transport layer.According to the 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxo-2,3-dihydro-1H-benzoisoquinoline-6,7-dicarboxylic acid with the structure of the general formula (I) of the present application, when a metal oxide such as zinc oxide, tin dioxide is matched to form a composite electron transport layer, the efficiency and stability of a photoelectric device based on different active layers can be effectively and synergistically improved.

Description

Technical Field

[0001] This invention relates to the field of organic semiconductor materials. Specifically, it relates to a class of naphthalimide compounds, their preparation methods, and applications; more specifically, this invention relates to a method for preparing a compound used as an n-type semiconductor material, and an optoelectronic device comprising said compound. Background Technology

[0002] Currently, organic solar cells (OSCs) boast photoelectric conversion efficiency (PCE) exceeding 19%, demonstrating immense application potential in building-integrated semiconductor devices and wearable electronic devices due to their flexibility, low cost, and large-area printability. It is well known that a fundamental requirement for the commercialization of OSCs is that the devices possess both high efficiency and good stability. Numerous studies have shown that reverse-structure devices typically exhibit better stability and are more compatible with roll-to-roll printing. The electron transport layer (ETL) plays a crucial role in the fabrication of reverse-structure devices. Zinc oxide (ZnO), prepared via the sol-gel method, possesses high electron mobility and a simple preparation process, making it widely used as an ETL material in reverse OSCs. However, this material faces challenges in industrial production. On one hand, its UV-induced catalytic decomposition of the active layer components leads to reduced OSC stability; on the other hand, it requires high-temperature post-processing (typically 200°C), while the heat resistance of flexible substrates generally does not exceed 120°C. Therefore, its application in flexible devices and roll-to-roll OSC manufacturing is significantly limited. Zinc oxide nanoparticles (ZnO NPs) and tin dioxide nanoparticles (SnO2 NPs) can be prepared and processed at relatively low temperatures, making them ideal for the fabrication of low-cost, flexible, large-area devices. However, due to surface defects in zinc oxide nanoparticles, OSCs based on ZnO NPs typically exhibit lower efficiency than devices using sol-gel ZnO. Furthermore, ZnO NPs readily aggregate in the post-processed solution, leading to poor storage stability. Summary of the Invention

[0003] This disclosure provides naphthalimide (NDI) derivative compounds having the structure of general formula (I) to address the problems associated with poor storage stability of zinc oxide nanoparticles and low efficiency and stability of devices based on zinc oxide nanoparticle electron transport layers. The polyethylene glycol-substituted naphthalimide (NDI) derivative compounds of general formula (I) according to this disclosure, when combined with metal oxides such as zinc oxide and tin dioxide to form composite electron transport layers (also referred to as hybrid electron transport layers), can effectively and synergistically improve the efficiency and stability of optoelectronic devices based on different active layers.

[0004] The technical solution of the present invention is as follows:

[0005] A class of polyethylene glycol-substituted naphthalimide compounds have the structure of general formula (I):

[0006]

[0007] Among them, a class of polyethylene glycol-substituted naphthalimide compounds and their preparation methods and applications, R1, R2, R3, and R4 are each independently substituted by hydrogen, halogen, or C1-C12 alkyl groups;

[0008] A1 and A2 are each independently selected from hydrogen, carboxylic acid group, and phosphate group, and A1 and A2 are not both hydrogen; n is a natural number from 1 to 5, preferably a natural number from 3 to 4.

[0009] The naphthalimide compound, A1 and A2, are each independently selected from: -COOH and H.

[0010] The naphthalimide compound is preferably of general formula (I) including any one of formulas (I) to (4); or a monocarboxylic acid derivative of polyethylene glycol-substituted naphthalimide (NDI);

[0011] Formula (2) is a dicarboxylic acid derivative of polyethylene glycol-substituted naphthalimide (NDI);

[0012] Formula (3) Monophosphate derivatives of polyethylene glycol-substituted naphthalimide (NDI);

[0013] Formula (4) diphosphate derivatives of polyethylene glycol-substituted naphthalimide (NDI);

[0014]

[0015] in,

[0016] R1, R2, R3, and R4 can each be independently substituted with hydrogen, halogen, or C1-C12 alkyl groups;

[0017] A1 and A2 are each independently selected from hydrogen, carboxylic acid group, and phosphate group, and A1 and A2 are not both hydrogen;

[0018] n is a natural number from 1 to 5, preferably a natural number from 3 to 4.

[0019] The naphthalimide compound, more preferably, is 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid; its structural formula is:

[0020]

[0021] The method for preparing a class of naphthalimide compounds of the present invention includes the following steps:

[0022] (a) Hydrolyzing a 1,4,5,8-naphthalenetetracarboxylic anhydride derivative having the structure of general formula (II) under alkaline conditions to obtain the hydrolysis product;

[0023] (b) The hydrolysis product is subjected to a condensation reaction with a methoxy polyethylene glycol amine compound having the structure of general formula (III) under weakly acidic conditions;

[0024]

[0025] In the case of general formula (Ⅲ) methoxy polyethylene glycol amine compounds, the definition of n is the same as that in general formula (I) polyethylene glycol-substituted naphthalimide (NDI) derivatives.

[0026] The molar ratio of the 1,4,5,8-naphthalenetetracarboxylic anhydride derivative of general formula (II) to the methoxy polyethylene glycol amine compound of general formula (III) is 1:1 to 10; more preferably about 1:1.

[0027] The preferred compound of the present invention is prepared by a method comprising the following steps: 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid.

[0028] (a) Prepare an aqueous solution of 1,4,5,8-naphthalenetetracarboxylic anhydride with a concentration of 3 mg / ml-25 mg / ml, add potassium hydroxide aqueous solution and stir at room temperature until the reaction system becomes clear; add phosphoric acid aqueous solution to the reaction system to adjust the pH of the reaction system to 5-7;

[0029] (b) Add 3,6,9-trioxa-1-aminodecane to the reaction system, and add aqueous phosphoric acid solution to adjust the pH of the reaction system to 5-7; heat the reaction system and reflux for 20-24 h; after the reaction system cools to room temperature, filter the reaction solution, add hydrochloric acid to the filtrate to adjust the pH to 1-3; extract the crude product with ethyl acetate, wash the organic phase with brine, and dry it with anhydrous sodium sulfate; the compound obtained is 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid.

[0030] The hydrogen spectrum of the prepared 2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid is as follows: 11¹H NMR (400MHz, DMSO-d⁶) δ 13.59 (s, 2H), 8.57 (d, J = 7.5Hz, 2H), 8.20 (d, J = 7.5Hz, 2H), 4.24 (t, J = 6.3Hz, 2H), 3.67 (t, J = 6.3Hz, 2H), 3.56–3.52 (m, 2H), 3.49–3.43 (m, 2H), 3.43–3.39 (m, 2H), 3.29–3.24 (m, 2H), 3.13 (s, 3H); ... spectrum is as follows: 13 C10 NMR (100MHz, DMSO-d6): δ (ppm) 168.4, 162.8, 136.6, 130.1, 129.2, 128.5, 125.4, 124.4, 71.1, 69.7, 69.6, 69.5, 66.7, 57.9. High-resolution mass spectrometry (HRMS, m / z, ESI): calculated C10 NMR values. 21 H 21 NO9[M+Na] + :454.1216, measured value:454.1108.

[0031] The application of the naphthalimide compound of the present invention as an electron transport layer in optoelectronic devices.

[0032] The application of the naphthalimide compound of the present invention as an electron transport layer in optoelectronic devices includes the following steps:

[0033] (a) A polyethylene glycol-substituted naphthalimide (NDI) derivative compound of general formula (I) is mixed with a zinc oxide nanoparticle dispersion. The solvent is selected from methanol, ethanol, isopropanol, and butanol. The mixing ratio is 1:1 to 1:5. The concentration is 5 mg / ml to 15 mg / ml. After mixing, the mixture is sonicated for 10 min to 60 min or stirred for 4 h to 8 h. The carboxyl groups form chemical bonds with the hydroxyl groups on the surface of the metal oxide to obtain dispersion (I). (b) After cleaning and ozone treatment, dispersion (I) is... Spin-coat dispersion (I) onto TO glass at 1000-4000 rpm and heat-anneal for 5-15 minutes at 0-120°C. After cooling, spin-coat an alcoholic solution of polyethylene glycol-substituted naphthalimide (NDI) derivatives of general formula (I) at 3000-5000 rpm and heat-anneal for 5-15 minutes at 0-120°C. The electron transport layer is then prepared. After cooling, spin-coat the active layer and vapor-deposit MoO. x , vapor-deposited silver electrode.

[0034] Electron transport layers (ETLs) play a crucial role in the fabrication of inverting OSCs. Zinc oxide (ZnO), prepared by the sol-gel method, possesses high electron mobility and a simple preparation process, making it widely used as an ETL material in inverting OSCs. However, industrial production of this material faces challenges. On one hand, its UV-induced catalytic decomposition of the active layer components leads to a decrease in OSC stability. On the other hand, it requires high-temperature post-processing (typically 200°C), while the heat resistance of flexible substrates generally does not exceed 120°C, thus significantly limiting its application in flexible devices and roll-to-roll OSC fabrication. Zinc oxide nanoparticles (ZnO NPs) and tin dioxide nanoparticles (SnO2 NPs) can be prepared and processed at relatively low temperatures, making them ideal for low-cost, flexible, and large-area device fabrication. However, due to surface defects in zinc oxide nanoparticles, ZnO NP-based OSCs typically exhibit lower efficiency than devices using sol-gel ZnO. Furthermore, ZnO nanoparticles (NPs) readily aggregate in the processed solution, leading to poor storage stability. Numerous efforts have been made to address these ZnO-related challenges, but satisfactory OSC performance in terms of efficiency and stability has not been achieved. This disclosure develops a class of polyethylene glycol-substituted naphthalimide compounds, with the preferred structure being 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid (NMO). NMO serves a dual purpose: effectively dispersing ZnO nanoparticles (ZnO NPs) and acting as a modifying layer at the ZnO NP interface. The hybrid electron transport layer ZnO:NMO / NMO, prepared by mixing NMO with ZnO NPs and interface modification, significantly improves the efficiency and stability of OSC. An inverting OSC based on the PM6:Y6 system and utilizing a ZnO:NMO / NMO ETL achieved an impressive power conversion efficiency of 18.31%, and the device exhibited excellent stability during maximum power point tracking under illumination. Furthermore, the ZnO:NMO / NMO interface layer demonstrated good versatility, as OSCs using NMO based on different active layer systems or metal oxide electron transport layers all showed significantly improved efficiency and stability. An inverting device based on the PM6:BTP-eC9:HDO-4Cl active layer system achieved a power conversion efficiency of 19.09%, which is the highest efficiency reported to date for an inverting single-junction OSC.

[0035] Furthermore, the preparation method of this type of compound obtained by hydrolysis and reamidation according to this disclosure has outstanding advantages such as simplicity, high efficiency, low environmental pollution, large-scale preparation capability, and low cost, which is of great significance for the application and promotion of this type of interface modification layer material. Attached Figure Description

[0036] Figure 1 The 1H NMR spectrum of the compound 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, prepared in Example 2.

[0037] Figure 2 The carbon NMR spectrum of the compound 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, prepared in Example 2.

[0038] Figure 3 The high-resolution mass spectrometry of the compound 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, prepared in Example 2.

[0039] Figure 4 The 1H NMR spectrum of the compound 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, prepared in Example 3.

[0040] Figure 5 The 1H NMR spectrum of the compound 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, prepared in Example 4.

[0041] Figure 6 The ultraviolet-visible light transmission spectra of the zinc oxide film, ZnO:NMO film, and ZnO:NMO / NMO film prepared in Example 5 are shown.

[0042] Figure 7 The photoelectron spectroscopy curves are shown for the zinc oxide thin film prepared in Example 5, the hybrid electron transport layer ZnO:NMO formed by the two, and the ZnO:NMO / NMO thin film.

[0043] Figure 8 The current density-voltage curves of the solar cells in Example 6, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0044] Figure 9 The external quantum efficiency response spectra of the solar cells in Example 6, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, respectively.

[0045] Figure 10 The photostability curves of the solar cells in Example 6, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0046] Figure 11 The current density-voltage curves of the solar cells in Example 7, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as active layers, are shown.

[0047] Figure 12 The external quantum efficiency response spectra of the solar cells in Example 7, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as active layers, respectively.

[0048] Figure 13 The photostability curves of the solar cells in Example 7, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as active layers, are shown.

[0049] Figure 14 The current density-voltage curves of the solar cells in Example 8, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4Cl as active layers, are shown.

[0050] Figure 15 The external quantum efficiency response spectra of the solar cells in Example 8, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4Cl as active layers, are shown.

[0051] Figure 16 The photostability curves of the solar cells in Example 8, which used ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4Cl as active layers, are shown.

[0052] Figure 17 The current density-voltage curves of the solar cells in Example 9, which use Sol-gel ZnO and Sol-gel Zn / NMO as electron transport layers and PM6:Y6 as active layers, respectively.

[0053] Figure 18 The external quantum efficiency response spectra of the solar cells in Example 9, which use Sol-gel ZnO and Sol-gel Zn / NMO as electron transport layers and PM6:Y6 as active layers, respectively.

[0054] Figure 19The current density-voltage curves of the solar cells in Example 10, which use SnO2 and SnO2 / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0055] Figure 20 The external quantum efficiency response spectra of the solar cells in Example 10, which use SnO2 and SnO2 / NMO as electron transport layers and PM6:Y6 as active layers, respectively.

[0056] Figure 21 The image shows the dynamic light scattering spectrum of the freshly prepared ZnO NPs and ZnO:NMO mixed dispersion in Example 11 after 70 days of storage. Detailed Implementation

[0057] The present disclosure is described in detail below through specific embodiments, but this does not imply any adverse limitation thereof. The present disclosure has been described in detail herein through specific embodiments, and various changes to the specific embodiments of the present disclosure will be apparent to those skilled in the art without departing from the spirit and scope thereof. All reagents used in this disclosure are commercially available and can be used without further purification.

[0058] Example

[0059] The invention is further illustrated by the following examples. The examples below are non-limiting and represent various aspects of this disclosure only. In the following examples, unless otherwise specified, reagents and instruments are commercially available products, and unless explicitly stated otherwise, experimental conditions and procedures are generally the same.

[0060] Example 1: Preparation of compound 2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, as shown in formula (I-1).

[0061]

[0062] At room temperature, add 0.3g-2g (3.75mg / ml-20mg / ml) of formula (II) 1,4,5,8-naphthalenetetracarboxylic anhydride (1.12-7.46mmol) to 80-100ml of water to form a suspension, then add 10-15ml of 1M potassium hydroxide aqueous solution and stir at room temperature until the reaction system becomes clear. Next, add 1M phosphoric acid aqueous solution to adjust the pH of the reaction system to 5-7. Add 0.22-1.46g (1.34-8.95mmol) of 3,6,9-trioxa-1-aminodecane to the reaction system, and again add 1M phosphoric acid aqueous solution to adjust the pH to 5-7. Heat the reaction system and reflux for 20-24h. After the reaction system cools to room temperature, filter the reaction solution, and add hydrochloric acid to the filtrate to adjust the pH to 1-3. Extract the crude product with ethyl acetate, wash the organic phase with brine, and dry it with anhydrous sodium sulfate. The target molecule NMO (0.19-1.54 g, 40%-48% yield) was obtained by column chromatography with ethyl acetate and methanol (v:v = 1:1) as a pale yellow solid compound.

[0063] Example 2: Preparation of compound 2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, as shown in formula (I-1).

[0064]

[0065] At room temperature, 0.3 g of formula (II) 1,4,5,8-naphthalenetetracarboxylic anhydride (1.12 mmol, 3.75 mg / ml) was added to 80 ml of water to form a suspension. Then, 6 ml of 1 M potassium hydroxide aqueous solution was added, and the mixture was stirred at room temperature until the reaction system became clear. Subsequently, 1 M phosphoric acid aqueous solution was added to the reaction system to adjust the pH to 5. 3,6,9-trioxa-1-aminodecane (0.22 g, 1.34 mmol) was added to the reaction system, and 1 M phosphoric acid aqueous solution was added again to adjust the pH to 5. The reaction system was heated and refluxed for 20 h. After the reaction system cooled to room temperature, the reaction solution was filtered, and hydrochloric acid was added to the filtrate to adjust the pH to 3. The crude product was extracted with ethyl acetate, the organic phase was washed with brine, and dried over anhydrous sodium sulfate. Column chromatography with ethyl acetate and methanol (v:v = 1:1) yielded the target molecule NMO (0.19 g, 40% yield) as a pale yellow solid compound.

[0066] The proton NMR spectrum of the product is as follows: Figure 1 As shown, the carbon spectrum is as follows Figure 2 As shown, the high-resolution mass spectrum is as follows: Figure 3 As shown, the characterization data is as follows:

[0067] 11 H NMR (400MHz, DMSO-d6) δ13.59(s,2H),8.57(d,J=7.5Hz,2H),8.20(d,J=7.5Hz,2H),4.24(t,J=6.3Hz,2H),3. 67(t,J=6.3Hz,2H),3.56-3.52(m,2H),3.49-3.43(m,2H),3.43-3.39(m,2H),3.29-3.24(m,2H),3.13(s,3H).

[0068] 13 C NMR (100MHz, DMSO-d6): δ (ppm) 168.4, 162.8, 136.6, 130.1, 129.2, 128.5, 125.4, 124.4, 71.1, 69.7, 69.6, 69.5, 66.7, 57.9.

[0069] HRMS(m / z,ESI): Calculated value C 21 H 21 NO9[M+Na] + :454.1216, Measured value:454.1108.

[0070] Example 3: Preparation of compound 2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, as shown in formula (I-1).

[0071]

[0072] At room temperature, 1.2 g of formula (II) 1,4,5,8-naphthalenetetracarboxylic anhydride (4.48 mmol, 13.3 mg / ml) was added to 90 ml of water to form a suspension. Then, 20 ml of 1 M potassium hydroxide aqueous solution was added, and the mixture was stirred at room temperature until the reaction system became clear. Subsequently, 1 M phosphoric acid aqueous solution was added to the reaction system to adjust the pH to 6. 3,6,9-trioxa-1-aminodecane (0.87 g, 5.37 mmol) was added to the reaction system, and 1 M phosphoric acid aqueous solution was added again to adjust the pH to 6. The reaction system was heated and refluxed for 22 h. After the reaction system cooled to room temperature, the reaction solution was filtered, and hydrochloric acid was added to the filtrate to adjust the pH to 2. The crude product was extracted with ethyl acetate, the organic phase was washed with brine, and dried over anhydrous sodium sulfate. The target molecule NMO (0.93 g, 48% yield) was obtained by column chromatography with ethyl acetate and methanol (v:v = 1:1) as a pale yellow solid compound.

[0073] The proton NMR spectrum of the product is as follows: Figure 4 As shown, the characterization data is as follows:

[0074] 11 H NMR (400MHz, DMSO-d6) δ13.59(s,2H),8.57(d,J=7.5Hz,2H),8.20(d,J=7.5Hz,2H),4.24(t,J=6.3Hz,2H),3. 67(t,J=6.3Hz,2H),3.56-3.52(m,2H),3.49-3.43(m,2H),3.43-3.39(m,2H),3.29-3.24(m,2H),3.13(s,3H).

[0075] Example 4: Preparation of compound 2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid, abbreviated as NMO, as shown in formula (I-1).

[0076]

[0077] At room temperature, 2 g of formula (II) 1,4,5,8-naphthalenetetracarboxylic anhydride (7.46 mmol, 20 mg / ml) was added to 100 ml of water to form a suspension, followed by 40 ml of 1 M potassium hydroxide aqueous solution. The mixture was stirred at room temperature until the reaction system became clear. Then, 1 M phosphoric acid aqueous solution was added to adjust the pH of the reaction system to 7. 3,6,9-trioxa-1-aminodecane (1.46 g, 8.95 mmol) was added to the reaction system, and 1 M phosphoric acid aqueous solution was added again to adjust the pH to 7. The reaction system was heated and refluxed for 24 h. After the reaction system cooled to room temperature, the reaction solution was filtered, and hydrochloric acid was added to the filtrate to adjust the pH to 1. The crude product was extracted with ethyl acetate, the organic phase was washed with brine, and dried over anhydrous sodium sulfate. Column chromatography with ethyl acetate and methanol (v:v = 1:1) yielded the target molecule NMO (1.44 g, 45% yield) as a pale yellow solid.

[0078] The proton NMR spectrum of the product is as follows: Figure 5 As shown, the characterization data is as follows:

[0079] 11H NMR (400MHz, DMSO-d6) δ13.59(s,2H),8.57(d,J=7.5Hz,2H),8.20(d,J=7.5Hz,2H),4.24(t,J=6.3Hz,2H),3. 67(t,J=6.3Hz,2H),3.56-3.52(m,2H),3.49-3.43(m,2H),3.43-3.39(m,2H),3.29-3.24(m,2H),3.13(s,3H).

[0080] Example 5: Preparation of hybrid electron transport layer ZnO:NMO

[0081] (1) Zinc oxide nanoparticles are dispersed in an alcohol solution, preferably methanol or butanol; the compound (NMO) of formula (1-1) is dissolved in methanol; the zinc oxide nanoparticle dispersion is mixed with the solution at a mass ratio of 1:0.15, and the concentration is 5mg / ml to 15mg / ml. After mixing, the mixture is sonicated for 10min to 30min or stirred for 4h to 8h, and the carboxyl group forms a chemical bond with the hydroxyl group on the surface of the metal oxide to obtain dispersion (I).

[0082] (2) Spin-coating dispersion (I) onto cleaned and ozone-treated ITO glass at a speed of 3000 r and then heat-annealing for 10 min at a temperature of 120 °C to obtain ZnO:NMO thin film.

[0083] (3) Dissolve the compound (NMO) of formula (1-1) in methanol to prepare a solution of 0.4 mg / ml.

[0084] (4) The solution obtained in step (3) is spin-coated onto the film obtained in step (2) at a rotation speed of 5000 rpm. The resulting hybrid electron transport layer is then heat-annealed at 120°C for 10 min to obtain the electron transport layer film ZnO:NMO / NMO.

[0085] Figure 6 The ultraviolet-visible light transmission and absorption spectra of the zinc oxide film, ZnO:NMO film, and ZnO:NMO / NMO film prepared in Example 2 are shown.

[0086] Figure 7 The photoelectron spectroscopy curves are shown for the zinc oxide thin film prepared in Example 2, the hybrid electron transport layer ZnO:NMO formed by the two, and the ZnO:NMO / NMO thin film.

[0087] Example 6: Fabrication and performance of organic optoelectronic devices based on ZnO or ZnO:NMO / NMO hybrid electron transport layer and PM6:Y6 active layer.

[0088] The optoelectronic device structure is ITO / ETL / donor material:acceptor material / MoO3 / Ag. The fabrication process is as follows: Pretreatment of ITO (indium tin oxide) glass: The ITO-sputtered glass substrate was sequentially ultrasonically treated in deionized water, acetone, and isopropanol for 15 minutes each, dried by nitrogen purging, and then treated under UV-ozone for 20 minutes. ZnO thin films or hybrid ZnO:NMO / NMO thin films were sequentially deposited on the ozone-treated ITO substrate. Then, an active layer of approximately 100 nm thick, PM6:Y6, was deposited. The preparation of the PM6:Y6 solution and the post-treatment of the film were performed according to the literature (Joule, 3, 4, 1140-1151, (2019)). Then, under a vacuum degree less than 2 × 10⁻⁶… -4 A 6 nm layer of MoO3 was deposited as a hole transport layer under Pa conditions, and then, under the cover of a mask, the hole transport layer was deposited at a vacuum level of less than 2 × 10⁻⁶. -4 Under Pa conditions, 150 nm Ag is deposited as the anode, and the effective cell area is approximately 4 mm². 2 The device performance was tested under standard sunlight (AM 1.5G) irradiation conditions using a computer-controlled Keithley 2400 digital source meter.

[0089] Figure 8 The current density-voltage curves of the solar cells in Example 6, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0090] Figure 9 The external quantum efficiency response spectra of the solar cells in Example 6, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0091] Figure 10 The photostability curves of the solar cells in Example 6, which used ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0092] Table 1: Performance comparison of solar cells prepared with ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, respectively.

[0093]

[0094] As shown in Table 1, the reverse organic solar cell devices based on the ZnO:NMO / NMO interface layer in Example 6 exhibit superior performance compared to those based on the ZnO interface layer. In this example, it can be observed that the ZnO:NMO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell in the PM6:Y6 active layer system compared to the ZnO interface layer. Figure 8The figures show the current density-voltage curves of the solar cells in Example 6, using ZnO and ZnO:NMO / NMO as the electron transport layer and PM6:Y6 as the active layer, respectively. As can be seen from the figures, the ZnO:NMO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell in the PM6:Y6 active layer system compared to the ZnO interface layer. Figure 9 The figures show the external quantum efficiency response spectra of solar cells in Example 6, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:Y6 as active layers, respectively. As can be seen from the figures, the ZnO:NMO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell system compared to the ZnO interface layer. This is manifested in the significantly improved external quantum efficiency response spectra of the devices fabricated based on the ZnO:NMO / NMO interface layer. Figure 10 The figures show the photostability curves of solar cells in Example 6, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as the active layer, respectively. The figures demonstrate that the ZnO:NMO / NMO interface layer significantly improves the photostability of the reverse organic solar cell in the PM6:Y6 active layer system compared to the ZnO interface layer.

[0095] Example 7: Fabrication and performance of organic optoelectronic devices based on ZnO or ZnO:NMO / NMO hybrid electron transport layer and PM6:BTP-eC9 active layer

[0096] The optoelectronic device structure is ITO / ETL / donor material:acceptor material / MoO3 / Ag. The fabrication process is as follows: Pretreatment of ITO (indium tin oxide) glass: The ITO-sputtered glass substrate was sequentially ultrasonicated in deionized water, acetone, and isopropanol for 15 minutes each, dried by nitrogen purging, and then treated under UV-ozone for 20 minutes. On the ozone-treated ITO substrate, ZnO thin films or hybrid ZnO:NMO / NMO thin films were sequentially deposited. Then, an active layer of approximately 100 nm thick, PM6:BTP-eC9, was deposited. The preparation of the PM6:BTP-eC9 solution and the post-treatment of the film were based on the literature (Nature Communications.|14,1760(2023)). Then, under a vacuum degree less than 2×10⁻⁶… -4 A 6 nm layer of MoO3 was deposited as a hole transport layer under Pa conditions, and then, under the cover of a mask, the hole transport layer was deposited at a vacuum level of less than 2 × 10⁻⁶. -4 Under Pa conditions, 150 nm Ag is deposited as the anode, and the effective cell area is approximately 4 mm². 2 The device performance was tested under standard sunlight (AM 1.5G) irradiation conditions using a computer-controlled Keithley 2400 digital source meter.

[0097] Figure 11The current density-voltage curves of the solar cells in Example 7, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as active layers, are shown.

[0098] Figure 12 The external quantum efficiency response spectra of the solar cells in Example 7, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as active layers, are shown.

[0099] Figure 13 The light stability curves of the solar cells in Example 7, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as active layers, are shown.

[0100] Table 2: Performance comparison of solar cells prepared with ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as active layers, respectively.

[0101]

[0102] As shown in Table 2, the reverse organic solar cell devices based on the ZnO:NMO / NMO interface layer in Example 7 all exhibit superior performance compared to those based on the ZnO interface layer. In this example, it can be observed that the ZnO:NMO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell in the PM6:BTP-eC9 active layer system compared to the ZnO interface layer, further demonstrating the universal applicability of the ZnO:NMO / NMO interface layer to different active layer systems. Figure 11 The figures show the current density-voltage curves of solar cells in Example 4, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as the active layer, respectively. The figures show that the ZnO:NMO / NMO interface layer significantly improves the reverse organic solar cell efficiency of the PM6:BTP-eC9 active layer system compared to the ZnO interface layer. Figure 12 The figures show the external quantum efficiency response spectra of solar cells in Example 4, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as the active layer, respectively. As can be seen from the figures, the ZnO:NMO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell system of PM6:BTP-eC9 active layer compared to the ZnO interface layer. This is manifested in the significantly improved external quantum efficiency response spectra of the devices fabricated based on the ZnO:NMO / NMO interface layer. Figure 13The figures show the photostability curves of solar cells in Example 4, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9 as the active layer, respectively. The figures demonstrate that the ZnO:NMO / NMO interface layer significantly improves the photostability of the reverse organic solar cell system with the PM6:BTP-eC9 active layer compared to the ZnO interface layer.

[0103] Example 8: Fabrication and Performance of Organic Optoelectronic Devices Based on ZnO or ZnO:NMO / NMO Hybrid Electron Transport Layer and PM6:BTP-eC9:HDO-4Cl Active Layer. The optoelectronic device structure is ITO / ETL / donor material:acceptor material / MoO3 / Ag. The fabrication process is as follows: Pretreatment of ITO (Indium Tin Oxide) Glass: The glass substrate sputtered with ITO was ultrasonically treated in deionized water, acetone, and isopropanol for 15 minutes each, dried by nitrogen purging, and then treated under ultraviolet-ozone for 20 minutes. ZnO thin films or hybrid ZnO:NMO / NMO thin films were sequentially deposited on the ozone-treated ITO substrate. Then, an active layer of about 100 nm thick PM6:BTP-eC9:HDO-4Cl was deposited. The preparation of the PM6:BTP-eC9:HDO-4Cl solution and the post-treatment of the film were all in accordance with the literature (Joule. 5, 2408-2419 (2021)). Then, in a vacuum degree less than 2×10 -4 A 6 nm layer of MoO3 was deposited as a hole transport layer under Pa conditions, and then, under the cover of a mask, the hole transport layer was deposited at a vacuum level of less than 2 × 10⁻⁶. -4 Under Pa conditions, 150 nm Ag is deposited as the anode, and the effective cell area is approximately 4 mm². 2 The device performance was tested under standard sunlight (AM 1.5G) irradiation conditions using a computer-controlled Keithley 2400 digital source meter.

[0104] Figure 14 The current density-voltage curves of the solar cells in Example 8, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4CL as active layers, are shown.

[0105] Figure 15 The external quantum efficiency response spectra of the solar cells in Example 8, which use ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4CL as active layers, are shown.

[0106] Figure 16 The figures show the photostability curves of the solar cells in Example 8, which used ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4CL as active layers, respectively.

[0107] Table 3: Performance comparison of solar cells prepared with ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4CL as active layers, respectively.

[0108]

[0109] As shown in Table 3, the reverse organic solar cell devices based on the ZnO:NMO / NMO interface layer in Example 8 all exhibit superior performance compared to those based on the ZnO interface layer. In this example, it can be observed that the ZnO:NMO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell in the PM6:BTP-eC9:HDO-4Cl active layer system compared to the ZnO interface layer, further demonstrating the universal applicability of the ZnO:NMO / NMO interface layer to different active layer systems. Figure 14 The figures show the current density-voltage curves of the solar cells in Example 8, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4Cl as active layers, respectively. The figures show that the ZnO:NMO / NMO interface layer significantly improves the reverse organic solar cell efficiency of the PM6:BTP-eC9:HDO-4Cl active layer system compared to the ZnO interface layer. Figure 15 The figures show the external quantum efficiency response spectra of solar cells in Example 8, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4Cl as active layers, respectively. The figures show that the ZnO:NMO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell system compared to the ZnO interface layer. This is manifested in the significantly improved external quantum efficiency response spectra of the devices fabricated based on the ZnO:NMO / NMO interface layer. Figure 16 The figures show the photostability curves of the solar cells in Example 8, using ZnO and ZnO:NMO / NMO as electron transport layers and PM6:BTP-eC9:HDO-4Cl as active layers, respectively. The figures demonstrate that the ZnO:NMO / NMO interface layer significantly improves the photostability of the reverse organic solar cell system with the PM6:BTP-eC9:HDO-4Cl active layer compared to the ZnO interface layer.

[0110] Example 9: Fabrication and Performance of Organic Optoelectronic Devices Based on Sol-gel ZnO and Sol-gel Zn / NMO Hybrid Electron Transport Layers and PM6:Y6 Active Layers. The optoelectronic device structure is ITO / ETL / donor material:acceptor material / MoO3 / Ag. The fabrication process is as follows: Pretreatment of ITO (Indium Tin Oxide) Glass: The glass substrate sputtered with ITO was ultrasonically treated in deionized water, acetone, and isopropanol for 15 minutes each, purged and dried with nitrogen, and then treated under ultraviolet-ozone for 20 minutes. Sol-gel ZnO films or hybrid Sol-gel Zn / NMO films were sequentially deposited on the ozone-treated ITO substrate. Then, an active layer of about 100 nm thick PM6:Y6 was deposited. The preparation of the PM6:Y6 solution and the post-treatment of the film were all in accordance with the literature (Joule, 3, 1140-1151, (2019)). Then, under a vacuum degree of less than 2×10 -4 A 6 nm layer of MoO3 was deposited as a hole transport layer under Pa conditions, and then, under the cover of a mask, the hole transport layer was deposited at a vacuum level of less than 2 × 10⁻⁶. -4 Under Pa conditions, 150 nm Ag is deposited as the anode, and the effective cell area is approximately 4 mm². 2 The device performance was tested under standard sunlight (AM 1.5G) irradiation conditions using a computer-controlled Keithley 2400 digital source meter.

[0111] Figure 17 The current density-voltage curves of the solar cells in Example 9, which use Sol-gel ZnO and Sol-gel Zn / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0112] Figure 18 The external quantum efficiency response spectra of the solar cells in Example 9, which use Sol-gel ZnO and Sol-gel Zn / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0113] Table 4: Performance comparison of solar cells prepared with Sol-gel ZnO or Sol-gel ZnO / NMO as electron transport layer and PM6:Y6 as active layer, respectively.

[0114]

[0115] As shown in Table 4, the reverse organic solar cell device based on the Sol-gel ZnO / NMO interface layer in Example 9 exhibits superior performance compared to the Sol-gel ZnO interface layer. In this example, it can be observed that the Sol-gel ZnO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell in the PM6:Y6 active layer system compared to the ZnO interface layer, indicating that the NMO interface modification layer is applicable not only to ZnO NPs interfaces but also to Sol-gel ZnO interfaces. Figure 17 The figures show the current density-voltage curves of solar cells in Example 4, using Sol-gel ZnO / NMO and Sol-gel ZnO as the electron transport layer and PM6:Y6 as the active layer, respectively. The figures show that the Sol-gel ZnO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell in the PM6:Y6 active layer system compared to the ZnO interface layer. Figure 18 The figures show the external quantum efficiency response spectra of solar cells in Example 4, using Sol-gel ZnO / NMO and Sol-gel ZnO as the electron transport layer and PM6:Y6 as the active layer, respectively. As can be seen from the figures, the Sol-gel ZnO / NMO interface layer significantly improves the efficiency of the reverse organic solar cell system compared to the ZnO interface layer. This is manifested in the significantly improved external quantum efficiency response spectrum of the devices fabricated based on the Sol-gel ZnO / NMO interface layer.

[0116] Example 10: Fabrication and Performance of Organic Optoelectronic Devices Based on SnO2 and SnO2 / NMO Hybrid Electron Transport Layers and PM6:Y6 Active Layers. The optoelectronic device structure is ITO / ETL / donor material:acceptor material / MoO3 / Ag. The fabrication process is as follows: Pretreatment of ITO (Indium Tin Oxide) glass: The glass substrate sputtered with ITO was ultrasonically treated in deionized water, acetone, and isopropanol for 15 minutes each, purged and dried with nitrogen, and then treated under ultraviolet-ozone for 20 minutes. SnO2 thin films or hybrid SnO2 / NMO thin films were sequentially deposited on the ozone-treated ITO substrate. Then, an active layer of about 100 nm thick PM6:Y6 was deposited. The preparation of the PM6:Y6 solution and the post-treatment of the film were carried out in accordance with the literature (Joule, 3, 1140-1151, (2019)). Then, under a vacuum degree of less than 2×10 -4 A 6 nm layer of MoO3 was deposited as a hole transport layer under Pa conditions, and then, under the cover of a mask, the hole transport layer was deposited at a vacuum level of less than 2 × 10⁻⁶. -4 Under Pa conditions, 150 nm Ag is deposited as the anode, and the effective cell area is approximately 4 mm². 2 The device performance was tested under standard sunlight (AM 1.5G) irradiation conditions using a computer-controlled Keithley 2400 digital source meter.

[0117] Figure 19 The current density-voltage curves of the solar cells in Example 10, which use SnO2 and SnO2 / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0118] Figure 20 The external quantum efficiency response spectra of the solar cells in Example 10, which use SnO2 and SnO2 / NMO as electron transport layers and PM6:Y6 as active layers, are shown.

[0119] Table 5: Performance comparison of solar cells prepared with SnO2 and SnO2 / NMO as electron transport layers and PM6:Y6 as active layers, respectively.

[0120]

[0121] As shown in Table 5, the SnO2 / NMO interface layer in Example 10 exhibits superior performance compared to the SnO2 interface layer-based reverse organic solar cell device. In this example, it can be observed that the SnO2 / NMO interface layer significantly improves the efficiency of the PM6:Y6 active layer system compared to the SnO2 interface layer, demonstrating that the NMO interface modification layer is applicable not only to ZnONPs or Sol-gel ZnO interfaces but also to SnO2 interfaces. This further illustrates the universal applicability of the NMO interface modification layer to electron transport layers of different metal oxides. Figure 19 The figures show the current density-voltage curves of the solar cells in Example 10, using SnO2 and SnO2 / NMO as electron transport layers and PM6:Y6 as the active layer, respectively. As can be seen from the figures, the SnO2 / NMO interface layer significantly improves the efficiency of the reverse organic solar cell in the PM6:Y6 active layer system compared to the SnO2 interface layer. Figure 20 The figures show the external quantum efficiency response spectra of solar cells in Example 10, using SnO2 and SnO2 / NMO as electron transport layers and PM6:Y6 as active layers, respectively. As can be seen from the figures, the SnO2 / NMO interface layer significantly improves the efficiency of the reverse organic solar cell system compared to the SnO2 interface layer. This is manifested in the significantly improved external quantum efficiency response spectra of devices fabricated based on the SnO2 / NMO interface layer.

[0122] Example 11: Preparation and storage performance of ZnO NPs and ZnO NPs:NMO dispersions

[0123] Zinc oxide nanoparticles were dispersed in an alcohol solution, preferably methanol or butanol; the compound (NMO) of formula (1-1) was dissolved in methanol to prepare a methanol solution; the zinc oxide nanoparticle dispersion was mixed with this solution at a mass ratio of 1:0.15, and the concentration was 10 mg / ml. After mixing, the mixture was sonicated for 30 min, and the carboxyl groups formed chemical bonds with the hydroxyl groups on the surface of the metal oxide to obtain dispersion (I). The particle size distribution of the freshly prepared dispersion (I), the ZnO NPs dispersion, and the dispersion after 70 days of storage at room temperature (25 °C) was characterized using dynamic light scattering.

[0124] Figure 21 The image shows the dynamic light scattering spectrum of the freshly prepared ZnO and ZnO:NMO mixed dispersion in Example 11 after 70 days of storage.

[0125] Table 6: Statistical analysis of particle size of original ZnO and ZnO:NMO dispersions before and after 70 days of storage

[0126]

[0127] As shown in Table 6, the ZnO:NMO dispersion (I) prepared in Example 11 has better storage stability than the ZnO dispersion. Specifically, the particle size of the ZnO:NMO dispersion (I) hardly changed before and after 70 days of storage, while the particle size of the ZnO dispersion increased by nearly seven times after 70 days of storage. Figure 21 The image shows the dynamic light scattering spectrum of the newly prepared ZnO and ZnO:NMO mixed dispersions in Example 4 and Example 11 after 70 days of storage. As can be seen from the image, the ZnO:NMO dispersion (I) has better storage stability than the ZnO dispersion.

[0128] The above results demonstrate that the aromatic imide derivatives containing acidic functional groups described in this disclosure form a hybrid electron transport layer after modifying zinc oxide or tin dioxide thin films, thereby producing organic optoelectronic devices with superior photoelectric performance and improved long-term operational stability. This hybrid electron transport layer is universally applicable to different active layer systems. Various flexible and large-area devices can be fabricated based on this hybrid interface layer.

[0129] The above content is merely an exemplary embodiment of this disclosure and is not intended to limit the scope of this disclosure. Any modifications, equivalent substitutions, improvements, etc., made within the concept and principles of this disclosure should be included within the protection scope of this disclosure.

Claims

1. A class of naphthalimide compounds, characterized in that, It has a structure with general formula (I): General Formula (I) in, R1, R2, R3, and R4 are each independently selected from hydrogen, halogens, or C1-C12 alkyl groups; A1 and A2 are each independently selected from hydrogen and carboxylic acid groups, and A1 and A2 are not both hydrogen; n is a natural number from 1 to 5.

2. The naphthalimide compound according to claim 1, characterized in that, General formula (I) is selected from any compound of formula (I) to formula (2); Formula (1) Monocarboxylic acid derivatives of polyethylene glycol-substituted naphthalimide; Formula (2) dicarboxylic acid derivatives of polyethylene glycol-substituted naphthalimide; Equation (1) Equation (2) in, R1, R2, R3, and R4 are each independently selected from hydrogen, halogens, or C1-C12 alkyl groups; A1 and A2 are each independently selected from hydrogen and carboxylic acid groups, and A1 and A2 are not both hydrogen; n is a natural number from 1 to 5.

3. The naphthalimide compound according to claim 1, characterized in that, The compound is 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid; its structural formula is: 。 4. A method for preparing a class of naphthalimide compounds according to claim 1, characterized in that, Includes the following steps: (a) Hydrolyzing a 1,4,5,8-naphthalenetetracarboxylic anhydride derivative having the structure of general formula (II) under alkaline conditions to obtain the hydrolysis product; (b) The hydrolysis product is subjected to a condensation reaction with a methoxy polyethylene glycol amine compound having the structure of general formula (III) under weakly acidic conditions; In general formula (III) methoxy polyethylene glycol amine compounds, the definition of n is the same as in general formula (I) polyethylene glycol-substituted naphthalimide derivatives.

5. The preparation method according to claim 3, characterized in that, The molar ratio of the 1,4,5,8-naphthalenetetracarboxylic anhydride derivative of formula (II) to the methoxy polyethylene glycol amine of formula (III) is 1:1 to 10.

6. The method for preparing the naphthalimide compound as described in claim 3, characterized in that, Includes the following steps: (a) Prepare an aqueous solution of 1,4,5,8-naphthalenetetracarboxylic anhydride with a concentration of 3 mg / ml-25 mg / ml, add potassium hydroxide aqueous solution and stir at room temperature until the reaction system becomes clear; add phosphoric acid aqueous solution to the reaction system to adjust the pH of the reaction system to 5-7; (b) Add 3,6,9-trioxa-1-aminodecane to the reaction system, and add aqueous phosphoric acid solution to adjust the pH of the reaction system to 5-7; heat the reaction system and reflux for 20-24 h; after the reaction system cools to room temperature, filter the reaction solution, add hydrochloric acid to the filtrate to adjust the pH to 1-3; extract the crude product with ethyl acetate, wash the organic phase with brine, and dry it with anhydrous sodium sulfate; the compound obtained is 2-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-1,3-dioxa-2,3-dihydro-1H-benzisoquinoline-6,7-dicarboxylic acid.

7. The application of the polyethylene glycol-substituted naphthalimide compound of claim 1 as an electron transport layer in optoelectronic devices.

8. The application as described in claim 7, characterized in that, Includes the following steps: (a) A polyethylene glycol-substituted naphthalimide derivative compound of general formula (I) is mixed with a zinc oxide nanoparticle dispersion. The solvent is selected from methanol, ethanol, isopropanol, and butanol. The mixing ratio is 1:1 to 1:

5. The concentration is 5 mg / ml to 15 mg / ml. After mixing, the mixture is sonicated for 10 min to 60 min or stirred for 4 h to 8 h. The carboxyl group forms a chemical bond with the hydroxyl group on the surface of the metal oxide to obtain dispersion (I). (b) Spin-coating dispersion (I) onto cleaned and ozone-treated ITO glass at a speed of 1000 r to 4000 r and hot-annealing for 5 min to 15 min at a temperature of 0 °C to 120 °C; after cooling, spin-coating an alcohol solution of polyethylene glycol-substituted naphthalimide derivatives of general formula (I) at a speed of 3000 r to 5000 r and hot-annealing for 5 min to 15 min at a temperature of 0 °C to 120 °C; after the electron transport layer is prepared, spin-coating of the active layer after cooling, followed by the vapor deposition of MoOx and silver electrodes.

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