CN117756803A

CN117756803A - Naphthalimide derivative, dye and application thereof

Info

Publication number: CN117756803A
Application number: CN202311779129.2A
Authority: CN
Inventors: 薛杰; 孔伶鑫; 张建华; 辛涵申; 李佳霖
Original assignee: University of Shanghai for Science and Technology
Current assignee: University of Shanghai for Science and Technology
Priority date: 2023-12-22
Filing date: 2023-12-22
Publication date: 2024-03-26

Abstract

The invention relates to a naphthalimide derivative, a dye and application thereof, wherein the naphthalimide derivative has the following general formula (I):wherein R is ₁ 、R ₂ 、R ₃ 、R ₄ 、R ₅ 、R ₆ Each independently represents a hydrogen atom or a substituent. The photosensitive resin composition comprises the following components in parts by weight: 90-110 parts of naphthalimide derivative, 230-270 parts of solvent and 90-percent of polyfunctional monomer110 parts of alkali-soluble resin 90-110 parts, photoinitiator 4-6 parts and other additives 0.4-0.6 part. Compared with the prior art, the invention adopts the ring-closed condensed ring pi-conjugated naphthalimide with high chemical bond energy as a mother nucleus structure, thereby ensuring the photochemical stability of the dye. Meanwhile, aggregation among chromophores can be inhibited by modifying molecular chain segments at the periphery, so that the thermal stability and the solubility in solvents and the compatibility with other components of the color photoresist are improved.

Description

Naphthalimide derivative, dye and application thereof

Technical Field

The invention belongs to the technical field of dyes, and particularly relates to a naphthalimide derivative, a dye and application thereof.

Background

Displays are the most important media in the information age. Since the late century, flat panel displays have replaced the market share of CRTs (cathode ray tubes). Among flat panel displays, LCDs (electronic modulation optics, which are composed of a plurality of parts filled with liquid crystals, are arranged in front of a light source (backlight) to generate color images) occupy the largest market share due to advantages of low cost, low power consumption, and flexibility. Color filters that convert white backlight into colored light of red (R), green (G) and blue (B) are key components in the development of display technology because of their great potential to improve image quality. Typically, only 6.3% of the backlight can pass through the entire panel, including polarizing filters, TFT arrays, LC cells, and color filters, with minimal transmission through the color filters (30%). Therefore, development of a high transmittance color filter is essential for saving energy consumption and improving a high quality display.

Currently, a pigment dispersion method of forming RGB patterned pixels using a photolithography method has been widely used to produce color filters because color filters having superior stability can be manufactured. Although the color filters produced by this method have good thermal and photochemical stability, they have low color characteristics due to the light scattering problem of pigment particles used as colorants, which reduces the transmittance of the corresponding prepared aggregation-behaving color filters. Dyes can overcome this problem and become a substitute for pigments because they dissolve in the medium and exist in molecular form, thereby reducing light scattering. However, dyes generally produce color filters having high transmittance and high contrast, but have poor heat resistance and light resistance, and have a problem that chromaticity change is likely to occur when the color filters are heated at high temperatures in the color filter step. In addition, they should be highly soluble in industrial solvents and have strong absorption peaks to obtain excellent optical properties. Specifically, there are problems in that:

(1) Dyes in a molecular dispersion state are generally inferior in light resistance and heat resistance to pigments forming molecular aggregates. In particular, when an Indium Tin Oxide (ITO) film widely used for an electrode of a liquid crystal display or the like is formed, optical properties are changed by a high temperature process.

(2) Dyes in the molecularly dispersed state are generally in solvent resistance variance compared to pigments that form molecular aggregates.

(3) Dyes tend to inhibit free radical polymerization reactions and so have difficulty in the design of colored curable compositions for systems that use free radical polymerization as a cure mode.

(4) Conventional dyes exhibit low solubility in alkaline aqueous solutions or organic solvents, and thus it is difficult to obtain colored curable compositions with a desired spectrum.

(5) Dyes generally exhibit interactions with other components in the colored curable composition, so it is difficult to control the solubility (developability) of the exposed and unexposed portions.

(6) When the molar absorptivity epsilon of the dye is low, a large amount of dye needs to be added. Therefore, the amount of other components such as polymerizable compounds (monomers), binders or photopolymerization initiators in the colored curable composition has to be relatively reduced, thereby reducing the curability, heat resistance after curing, and developability of the composition.

Therefore, a new dye with light and heat stability and good compatibility is still to be developed.

Disclosure of Invention

The invention aims to overcome the defect that the traditional dye is difficult to achieve light and heat stability and good compatibility, and provides a naphthalimide derivative, a dye and application thereof.

The aim of the invention can be achieved by the following technical scheme:

a naphthalimide derivative having the following general formula (I):

wherein R1, R2, R3, R4, R5 and R6 each independently represent a hydrogen atom or a substituent.

Further, the R ₁ To R ₆ Each independently selected from the group consisting of hydrogen atoms, cyano groups, substituted or unsubstituted: c1 to C100 alkenyl, C1 to C100 alkynyl, C3 to C100 cycloalkyl, C4 to C100 cycloalkenyl, C4 to C100 cycloalkynyl, C1 to C100 alkoxy, C1 to C100 thioalkoxy, carbonyl, carboxyl, nitro, C6 to C100 aryl, C3 to C100 heteroaryl, C4 to C100 aryloxy.

Further, the R ₁ To R ₆ Each independently selected from one or more of the groups represented by the following formulas (B-1) to (B-2):

wherein L1 to L5 each independently represent any one of a hydrogen atom, a C1 to C50 chain alkyl group, a C1 to C50 chain alkenyl group, a C1 to C50 alkoxy group, a C3 to C50 heteroaryl group, a C3 to C50 phenoxy group, and a C3 to C50 phenylthio group.

Further, the R ₁ To R ₆ Each independently selected from one or more of the groups represented by the following formulas (C-1) to (C-10):

wherein X is ₁ ～X ₃ Each independently represents any of a hydrogen atom, a C1 to C50 chain alkyl group, a C1 to C50 chain alkenyl group, a C1 to C50 alkoxy group, a C3 to C50 heteroaryl group, a C3 to C50 phenoxy group, a C3 to C50 phenylthio groupOne of the two.

Further, the R ₁ To R ₆ Each independently selected from one or more of the groups represented by the following formulas (A-1) to (A-49):

wherein the broken line represents the connection bond of R1 to R6 in the general formula (I).

Further, the naphthalimide derivative is selected from the following formulas (1) to (332):

the invention also provides a preparation method of the naphthalimide derivative, which comprises the following steps:

synthesis of S1 intermediate: adding dibromohydantoin into 1,4,5, 8-naphthalene tetracarboxylic anhydride (NDA) and concentrated sulfuric acid to perform substitution reaction to obtain 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic acid bisimide; adding arylamine into 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic acid bisimide for substitution reaction, and purifying to obtain the intermediate;

preparation of S2 naphthalimide derivative: adding aryl amine or cycloalkyl amine into the intermediate obtained in the step (1) for substitution reaction, and purifying to obtain the naphthalimide derivative;

further, the arylamine is selected from amine derivatives of formula (B-1), and the cycloalkylamine is selected from amine derivatives of formula (B-2).

The invention also provides a photosensitive resin composition, which comprises the naphthalimide derivative, wherein the photosensitive resin composition comprises the following components in parts by weight:

further, the multifunctional monomer comprises one or more of dipentaerythritol hexaacrylate and trimethylolpropane propoxylate trimethacrylate.

Further, the solvent includes one or more of propylene glycol methyl ether acetate or propylene glycol methyl ether.

The invention also provides application of the photosensitive resin composition in an optical filter, an image sensor and a display device.

Compared with the prior art, the invention has the following beneficial effects:

(1) The invention adopts a closed-loop condensed ring pi conjugated parent nucleus structure such as Naphthalimide (NDI), and the closed-loop and pi conjugated characteristics of the closed-loop condensed ring pi conjugated parent nucleus structure can enable a molecular framework to have high chemical bond energy, so that a foundation of good photo-thermal chemical stability is provided. At the same time, the optical properties of the naphthalimide derivative can be tuned by substitution at the parent nucleus or imide position while maintaining light and thermal stability.

(2) The invention solves the problem that the naphthalimide is easy to gather in an organic solvent by modifying the naphthalimide, and the ligand with resin monomer is connected at the mother nucleus to improve the migration resistance of the naphthalimide dye in the color photoresist.

(3) The naphthalimide dye has better solubility and compatibility in a color photoresist solvent, and higher color purity, and can be used as a dye with excellent performance in display and sensing device filters such as liquid crystal displays, image sensors and the like.

Drawings

Fig. 1 is a mass spectrum of intermediate 1.

FIG. 2 is a mass spectrum of example 1-1.

FIG. 3 is a schematic representation of ultraviolet absorption-transmission at PGMEA (propylene glycol methyl ether acetate) for the naphthalimide dyes and C.I. solvent blue 106 of examples 1-1 and examples 1-11.

Detailed Description

The invention will now be described in detail with reference to the drawings and specific examples. The present embodiment is implemented on the premise of the technical scheme of the present invention, and a detailed implementation manner and a specific operation process are given, but the protection scope of the present invention is not limited to the following examples.

Unless specifically indicated otherwise, the reagents, methods, apparatus and devices employed in the present invention are those conventional in the art. Reagents and materials used in the following examples are commercially available unless otherwise specified.

The preparation method of the intermediate involved in the embodiment of the invention is as follows:

synthesis of intermediate 1:

(1) 1,4,5, 8-naphthalene tetracarboxylic anhydride (20 mmol) and concentrated sulfuric acid (60 ml) are sequentially added into a 150ml thick-wall pressure-resistant bottle, stirring and dissolving are carried out at room temperature, dibromohydantoin (DBH) is added in batches to prevent caking, sealing and stirring are carried out at 80 ℃ for 24 hours, cooling to room temperature after the reaction is finished, the product is introduced into ice water, sodium sulfite prepared in advance is added, water is washed for three times for acid removal, ethanol is washed for three times for water removal, drying is carried out at 80 ℃, and the yield is 85%, thus obtaining 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic acid bisimide.

After high resolution mass spectrum, ESI source and positive ion mode detection, the molecular formula of the intermediate 1 is C ₁₄ H ₂ Br ₂ N ₂ O ₆ The detection value is 425.22, and the theoretical value is 425.97, as shown in fig. 1; detecting element content (%): c,39.53; h,0.54; br,37.58; o,22.96. Theoretical element content (%): c,39,48; h,0.47; br,37.52; o,22.54. The above analysis shows that the obtained product is the expected product.

Synthesis of intermediate 2:

the reaction mass, bromo-hydroxy acid diester (2 mmol), a mixture of starting material 1 (4 mmol) and acetic acid (30 ml) was stirred under nitrogen at 120 ℃ for 2h, after the reaction was completed cooled to room temperature, the mixture was poured into cold water, the solid was filtered, the filtrate was washed with water and methanol, dried in vacuo and purified by column chromatography with dichloromethane: petroleum ether=2:3, 76% yield.

After high resolution mass spectrum, ESI source and positive ion mode detection, the molecular formula of the intermediate 2 is C ₃₈ H ₃₆ Br ₂ N ₂ O ₄ Mass spectrum detection value is 744.21, theoretical value is 744.52; detecting element content (%): c,61,55; h,4.96; br,21.54; n,3.92; o,8.77. Theoretical element content (%): c,61,30; h,4.87; br,21.46; n,3.76; o,8.60. The above analysis shows that the obtained product is the expected product.

The synthesis of intermediates 3-5 is similar to equation 2, except that starting material 1 is selected from other corresponding structures, experimental steps and operations are not specifically shown here, and the structures of the other starting materials are as follows:

the structure of the synthesized intermediate is as follows:

experimental data for intermediates 3-5 are set forth in the following table:

TABLE 1

Synthesis of intermediate 6:

intermediate 1 (2 mmol), a mixture of starting material 1 (6 mmol) and acetic acid (30 ml) was stirred under nitrogen at 135 ℃ for 6h, after the reaction was cooled to room temperature, the mixture was poured into cold water, the solid was filtered, the filtrate was washed with water and methanol, dried in vacuo and purified by chromatography on ethyl acetate: petroleum ether=1:40 column in 70% yield.

After high resolution mass spectrum, ESI source and positive ion mode detection, the molecular formula of the intermediate 6 is C ₅₀ H ₅₄ BrN ₂ O ₄ Mass spectrum detection value is 839.11, theoretical value is 839.32; detecting element content (%): c,71.53; h,6.55; br,9.58; n,5.11; o,7.67. Theoretical element content (%): c,71.42; h,6.47; br,9.50; n,5.00; o,7.61. The above analysis shows that the obtained product is the expected product.

The synthesis of intermediates 7 to 9 is similar to that of equation 3, and only requires the replacement of initiator 1 with the corresponding other initiator, the experimental steps and operations are not specifically illustrated herein, and the structures of the other initiators are as follows:

the structural formula of the synthesized intermediate is shown as follows:

experimental data for intermediates 7-9 are set forth in the following table:

TABLE 2

Intermediate products	Starting material	Intermediate mass spectrometry data	Intermediate elemental analysis data	Yield rate
					7	2	755.29	C,69.92；H,5.62；Br,10.63；N,5.77；O,8.52	79％
8	3	923.52	C,72.80；H,7.26；Br,8.71；N,4.62；O,7.03	74％
					9	4	1091.72	C,74.82；H,8.36；Br,7.38；N,3.91；O,5.91	68％

Further description will be provided below in connection with specific examples.

Example 1-1: synthesis of dye (5)

Intermediate 2 (0.54 mmol), starting material 5 (5 mmol), dimethylformamide (DMF) (20 ml) was added to a two-port flask inN ₂ Under protection, the mixture is heated and refluxed for 10 hours at 135 ℃. After stopping the reaction, the mixture was cooled to room temperature and then quenched with saturated aqueous sodium bicarbonate. The aqueous layer was extracted with dichloromethane (3×100 mL) and the combined organic extracts were dried over MgSO ₄ Drying, using petroleum ether: dichloromethane = 1: the eluent of 1 is separated and purified on a silica gel column. 1.77g of a blue solid was obtained in 84% yield.

After high resolution mass spectrum, ESI source and positive ion mode detection, the molecular formula of the structural formula (5) is C ₆₂ H ₇₂ N ₄ O ₄ The detection value is 937.06, and the theoretical value is 937.28, as shown in fig. 2; detecting element content (%): c,79.55; h,7.64; n,5.88; o,6.93. Theoretical element content (%): c,79.45; h,7.74; n,5.98; o,6.83. The above analysis shows that the obtained product is the expected product.

The reactions of other examples are similar to those of the above formula, and only the starting materials 5 and the intermediate 2 need to be replaced by corresponding other starting materials and intermediates, the experimental steps and operations are not specifically shown here, the intermediates are synthesized intermediates 3 to 9, and the structures of the other starting materials are as follows:

the synthesis of examples 1-2 to 1-72 was similar to that of example 1-1, with the only difference being the intermediates and starting materials used, and the molecular structure identification data for the desired intermediates and compounds and products are shown in Table 3:

TABLE 3 Table 3

The following examples each use the naphthalimide dye prepared in the above examples to prepare a color photosensitive resin composition, and were subjected to photolithography development to compare the relevant properties of the photosensitive resin composition.

Example 2-1:

the present embodiment provides a blue photosensitive resin composition and a method for preparing the same.

200 parts by weight of a colorant (composed of 100 parts by weight of the dye (5) of example 1-1 and 100 parts by weight of the solvent Q1), 50 parts by weight of the polyfunctional monomer M1, 50 parts by weight of the polyfunctional monomer M2, 100 parts by weight of the alkali-soluble resin N, 0.2 part by weight of the additive 01, 0.3 part by weight of the additive 02, and 5 parts by weight of the photoinitiator P were added to about 100 parts by weight of the solvent Q1 and about 50 parts by weight of the solvent Q2, and the mixture was sufficiently dissolved and mixed to control the solid content to about 20%, thereby obtaining a blue photosensitive resin composition.

Wherein, the polyfunctional monomer M1: dipentaerythritol hexaacrylate (analytically pure), available from sand dama corporation; polyfunctional monomer M2: trimethylolpropane trimethacrylate (analytically pure), purchased from taiwan double bond chemical industry; alkali-soluble resin N: trade name Sarbox SB400 (analytically pure), available from sartomer company; additive 01: f-556 (trade name, available from DIC Co.); additive 02: KH570 (γ -methacryloxypropyl trimethoxysilane), purchased from carbofuran; photoinitiator P: IRGACURE OXE 01 (trade name, available from Basf Co.); solvent Q1: PGMEA (propylene glycol methyl ether acetate), purchased from dow chemical; solvent Q2: PM (propylene glycol methyl ether), available from Dow chemical.

The formulations of examples 2-2 to 2-72 refer to example 2-1, except that the dye in the colorant is a naphthalimide derivative of the corresponding example, and as shown in table 4, other components are not described again.

Comparative example 2-1:

this comparative example provides a blue photosensitive resin composition using c.i. solvent blue 106 as a dye.

200 parts by weight of a colorant (composed of 100 parts by weight of c.i. solvent blue 106 and 100 parts by weight of solvent Q1), 50 parts by weight of a polyfunctional monomer M1, 50 parts by weight of a polyfunctional monomer M2, 100 parts by weight of an alkali-soluble resin N, 0.2 part by weight of an additive 01, 0.3 part by weight of an additive 02, and 5 parts by weight of a photoinitiator P were added to about 100 parts by weight of the solvent Q1 and about 50 parts by weight of the solvent Q2, and the mixture was sufficiently dissolved and mixed to control the solid content to about 20%, thereby obtaining a blue photosensitive resin composition.

The photosensitive resin compositions of examples 2-1 to 2-72 of the present invention were tested for their performance by a lithographic imaging method comprising the steps of:

cleaning and drying the glass sheet, and coating the glass sheet with a rotary coating machine to obtain a uniform film layer with the thickness of 1.5-2.0 mu m. Pre-baking at 90deg.C for 120s, exposing with 365nm ultraviolet light with exposure of 40mJ/cm ² The mask plate and the coating film are 180 μm apart, developed at 23 ℃ for 50s, post-baked at 230 ℃ for 20min, and the subsequent relevant properties are tested, and the results are shown in Table 4.

Performance testing and evaluation method:

(1) Chromaticity: and detecting by adopting a Konica Minolta CM-5 spectrocolorimeter.

(2) System compatibility: the photosensitive resin composition is placed in an environment of 0-10 ℃ and kept in a dark place, the viscosity change (at least six months) of the photosensitive resin composition is tested, and photoetching is carried out according to the process conditions, and whether particles appear on the surface of a color film is inspected under an optical microscope (Optical Microscope, which is called OM hereinafter) of which the x500 times is used.

The evaluation criteria were as follows:

o: viscosity change value < + -5% mpa.s and no particles on x500 surface;

delta: viscosity change value < + -10% mpa.s and no particles on x500 surface;

x: viscosity change value > + -10% mPa.s or x500 surface has particles;

(3) Heat resistance test: verifying heat resistance of the photosensitive resin composition by chromatic aberration, post-baking at 230 ℃ for 20min, repeating the post-baking twice, and measuring the film thickness by an XP-2 step instrument; the color difference is the color difference value between the second post-baked sample and the first post-baked sample, and is measured by Meinada CM-5, if delta E _ab Less than 3, the heat resistance is better;

(4) Solvent resistance evaluation:

soaking post-baked sample in isopropanol at room temperature for 5min, baking in oven at 150deg.C for 30min, and measuring color difference before and after, if delta E _ab < 3, good solvent resistance is indicated.

(5) Evaluation of anti-transfer dyeing properties:

according to the manufacturing process of the color filter, red or blue pixels A are firstly prepared on TFT glass. Then coating the sample, drying the surface of the color filter after development is finished, measuring the color difference before and after the pixel A, and if delta E _ab And < 3, it shows good transfer resistance.

(6) Line width, edge trim, and development process margin:

line width and edge uniformity were tested by 500 times OM, and mask line width was 140 μm.

During process margin evaluation, other process conditions are fixed, and edge uniformity and edge residue or edge peeling conditions of images obtained in the development time of 40-100s are inspected, wherein peeling performance judgment is judged by referring to a measuring method of adhesive force in the field.

The edge line uniformity evaluation criteria are as follows:

o: the development 50s has neat edge line and no residue at the edge;

delta: the edge of the developed 50s image has burrs, and is irregular or has residues at the edge;

x: image deletion

Specific criteria for development process margin evaluation are as follows:

o: the development is carried out for 40-100s, the edge lines are neat, no residue and no stripping are generated at the edge;

delta: the development is carried out for 50-80s, the edge lines are neat, no residue and no stripping are generated at the edge;

x: the development 50-80s has irregular edge, or has residues at the edge, or has stripping at the edge;

the above-mentioned alkaline developer, such as aqueous solution of alkaline compound of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium carbonate, ammonia water, diethylamine or tetramethylammonium hydroxide, etc., has an [ OH- ] concentration of 0.2 to 1.0%, preferably 0.4 to 0.6%. All of the examples used sodium hydroxide solution.

The evaluation results of the blue photosensitive resin compositions of examples 2-1 to 2-72 are shown in Table 4.

TABLE 4 Table 4

As a comparison of the experimental results of FIG. 3 and Table 4 shows, the C.I. solvent blue 106 of comparative example 2-1 is generally soluble in PGMEA, whereas the dyes of examples 2-1 to 2-72 are very good in solubility in the color photoresist solvent PGMEA and have higher blue color purity. Meanwhile, the photosensitive resin compositions using examples 2-1 to 2-72 have more excellent heat resistance and similarly good process properties such as system compatibility, edge trim, development process margin, and the like, as compared with the photosensitive resin composition using c.i. solvent blue 106 of comparative example 2-1.

The present invention provides a compound having excellent performance for use as a dye in a display and sensor device filter such as a liquid crystal display, an image sensor, or the like. The invention adopts a ring-closed condensed ring pi-conjugated parent nucleus structure such as Naphthalimide (NDI), and the ring-closed and pi-conjugated characteristics can lead the molecular skeleton to have high chemical bond energy, so that the naphthalimide derivative has good photo-thermal chemical stability. The optical properties of NDI can be easily tuned by substitution at the NDI core or imide position while maintaining light and thermal stability. Based on the excellent stability of the naphthalimide mother nucleus, the naphthalimide derivative can be used as a dye to be applied to display and sensing device filters of liquid crystal displays, image sensors and the like.

The invention solves the problems of insufficient photophysical property and thermal stability of the traditional dye and poor solubility and compatibility in a color photoresist system, and simultaneously provides a method for improving the migration resistance of the dye in the color photoresist by modifying naphthalimide to solve the phenomenon that the naphthalimide is easy to aggregate in an organic solvent and connecting a ligand with a resin monomer at a mother nucleus.

The previous description of the embodiments is provided to facilitate a person of ordinary skill in the art in order to make and use the present invention. It will be apparent to those skilled in the art that various modifications can be readily made to these embodiments and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-described embodiments, and those skilled in the art, based on the present disclosure, should make improvements and modifications without departing from the scope of the present invention.

Claims

1. A naphthalimide derivative characterized by having the following general formula (I):

wherein R is ₁ 、R ₂ 、R ₃ 、R ₄ 、R ₅ 、R ₆ Each independently represents a hydrogen atom or a substituent.

2. A naphthalimide derivative according to claim 1, wherein R is ₁ To R ₆ Each independently selected from the group consisting of hydrogen atoms, cyano groups, substituted or unsubstituted: c1 to C100 alkenyl, C1 to C100 alkynyl, C3 to C100 cycloalkyl, C4 to C100 cycloalkenyl, C4 to C100 cycloalkynyl, C1 to C100 alkoxy, C1 to C100 thioalkoxy, carbonyl, carboxyl, nitro, C6 to C100 aryl, C3 to C100 heteroaryl, C4 to C100 aryloxy.

3. A naphthalimide derivative according to claim 2, wherein R is ₁ To R ₆ Each independently selected from one or more of the groups represented by the following formulas (B-1) to (B-2):

4. A naphthalimide derivative according to claim 3, wherein R is ₁ To R ₆ Each independently selectOne or more of the groups represented by the following formulas (C-1) to (C-10):

wherein X is ₁ ～X ₃ Each independently represents any one of a hydrogen atom, a C1 to C50 chain alkyl group, a C1 to C50 chain alkenyl group, a C1 to C50 alkoxy group, a C3 to C50 heteroaryl group, a C3 to C50 phenoxy group, a C3 to C50 phenylthio group;

5. A naphthalimide derivative according to claim 4, wherein R is ₁ To R ₆ Each independently selected from one or more of the groups represented by the following formulas (A-1) to (A-49):

wherein the dotted line represents R in formula (I) ₁ ～R ₆ Is a connecting key of (a).

6. A naphthalimide derivative according to any of claims 1 to 5, wherein the naphthalimide derivative is selected from the following formulae (1) to (332):

7. a process for producing a naphthalimide derivative according to any of claims 1 to 6, characterized by comprising the steps of:

synthesis of S1 intermediate: adding dibromohydantoin into 1,4,5, 8-naphthalene tetracarboxylic anhydride and concentrated sulfuric acid to perform substitution reaction to obtain 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic bisimide; adding arylamine into 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic acid bisimide for substitution reaction, and purifying to obtain the intermediate;

the aryl amine is selected from amine derivatives of formula (B-1), and the cycloalkyl amine is selected from amine derivatives of formula (B-2).

8. A photosensitive resin composition comprising the naphthalimide derivative according to any one of claims 1 to 6, the photosensitive resin composition comprising the following components in parts by weight:

9. the photosensitive resin composition of claim 8, wherein said polyfunctional monomer comprises one or more of dipentaerythritol hexaacrylate, trimethylolpropane propoxylate trimethacrylate;

the solvent comprises one or more of propylene glycol methyl ether acetate or propylene glycol methyl ether.

10. Use of the photosensitive resin composition according to any one of claims 8 to 9 in optical filters, image sensors and display devices.