Copper phthalocyanine, green photosensitive resin composition and application thereof

Abstract

The invention relates to copper phthalocyanine, a green photosensitive resin composition and application thereof, the copper phthalocyanine is prepared by substituting benzene ring sites on the periphery of a parent nucleus of copper phthalocyanine through multifunctional groups, the structural formula of the copper phthalocyanine is shown in the specification, R1 to R16 are independently selected from any one of hydrogen atoms, chlorine atoms, alkyl groups, aryl groups or heteroaryl substituent groups, and R2 to R3 are selected from hydrogen atoms, chlorine atoms, alkyl groups, aryl groups or heteroaryl substituent groups. And R1 to R16 at least comprise one naphthalimide group. The green photosensitive resin composition is obtained by mixing a coloring agent, resin containing a double-bond structure or / and an epoxy structure, a monomer containing the double-bond structure or / and the epoxy structure, a photoinitiator, an additive and a solvent containing an ether group. Compared with the prior art, the prepared copper phthalocyanine has excellent solubility, high green color purity and photo-thermal stability, and the prepared green photosensitive resin composition containing the copper phthalocyanine can be prepared into a thin coloring layer, has high color purity and can be used as a color photoresist for preparing a color filter.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of dye preparation, and particularly relates to a copper phthalocyanine, green photosensitive resin composition and application thereof. BACKGROUND

[0002] With the popularization of the fifth generation mobile communication (5G) technology, the iteration of virtual reality (VR / AR) terminals and the implementation of ultra-high definition (8K / 16K) display standards, display and optoelectronic sensor devices are facing the stringent technical requirements of synchronous improvement of optical performance and manufacturing process. The color filter for liquid crystal display is usually a red (R), green (G), and blue (B) three-color pixel point with fixed shape and size coated on a transparent glass substrate, which only transmits light in the required wavelength region under white backlight illumination, thereby realizing the display of color images. The pigment dispersion method widely used in the industry to prepare color filters includes: micron-level precision coating (spin coating / slot coating) based on a transparent substrate black matrix, 365nm waveband photoresist patterning exposure, development to remove uncured areas, and 230℃ high-temperature post-curing and other process steps. Among them, the synergistic effect of each component of the photosensitive composition containing colorants, photosensitive resin, photopolymerization monomer, photoinitiator, additive and solvent directly determines the functional characteristics of the color filter. Although the color filter prepared by the pigment dispersion method has good photo-thermal stability and chemical stability, it has the following defects: (1) the pigment particles form sub-micron aggregates with a size of 400-800nm in the photosensitive resin composition, causing the combined light scattering effect of Mie scattering and Rayleigh scattering, resulting in a visible light transmittance decay of the filter film of 12-18%, which seriously weakens the display brightness and causes color shift; (2) during the post-curing stage, the change of the particle surface causes secondary agglomeration, resulting in reduced stability and color coordinate shift of the prepared filter; (3) in order to achieve the high color saturation required by the BT.2020 color gamut standard, compensation pigments have to be added, but the difference in Hansen solubility parameters between heterogeneous pigments causes microphase separation, resulting in visible defects at the edge of the developed film layer and accompanied by spectral broadening. These bottleneck problems jointly restrict the industrial upgrading demand of high-specification display equipment towards ultra-large size, ultra-thin and flexible direction.

[0003] In order to break through the above-mentioned bottlenecks, the development and design of new dyes is the key to improving the quality of filters and even liquid crystal panels. Compared with pigments, dyes dissolve in the medium and exist in molecular form, which reduces light scattering. In addition, the molecular structure of dyes is clear, and there is a clear structure-activity relationship between their molecular structure and photophysical properties, so they have greater potential in achieving excellent optical performance. Although dyes can generally produce color filters with high transmittance and high contrast, their heat resistance and light resistance are poor, and chromaticity changes are prone to occur during the high-temperature heating step in the color filter preparation process. In addition, to meet industrial production requirements, dyes need to meet the following conditions: first, they have high solubility in industrial solvents; second, they have good color purity; and third, they have good photothermal stability. However, traditional dyes often find it difficult to meet these requirements: (1) Traditional dyes lack solubilizing groups, and their measured solubility in industrial solvents such as propylene glycol methyl ether acetate (PGMEA) is generally less than 3.5wt%, which cannot meet the requirement of ≥5wt% for photosensitive resin composition systems; (2) Current dyes usually have a single main absorption peak in the visible light region, making it difficult to cover multiple light regions well at the same time, resulting in poor color purity; (3) Molecular dyes are unstable under high-temperature post-baking processes (230℃ / 30min) and long-term ultraviolet light exposure conditions, and dye degradation may occur, causing the filter to fade and age, ultimately affecting the overall optical performance and service life of the device.

[0004] Copper phthalocyanine, as a typical metal phthalocyanine dye with a strong π-conjugated structure, is widely used in organic optoelectronic devices, color filters, and functional coatings due to its high molar extinction coefficient, excellent visible light absorption performance, and molecular spectral tunability. At present, color photoresist green dyes have also been developed based on the copper phthalocyanine core (for example: CN111240155B, CN103890658B, CN103890658A, CN119471885A). However, in actual application, copper phthalocyanine molecules have obvious low solubility, low color purity, and poor thermal stability. These defects seriously restrict the stability of their optical properties and the long-term reliability of devices: (1) The dye used to prepare the color filter must be soluble in the solvent used, such as PGMEA. Traditionally, the industry requires the solubility of the dye in PGMEA to exceed 5wt%. Due to the strong interaction between molecules caused by the conjugated planar structure of copper phthalocyanine, it exhibits relatively poor solubility in organic solvents. (2) Copper phthalocyanine molecules have a large-area π-π conjugated system, which is prone to intermolecular accumulation in solutions and polymer matrices, causing problems such as broadening of the absorption band and reduction of the main absorption peak intensity, ultimately leading to a decrease in the color purity and color saturation of the green filter. (3) The interfacial compatibility between copper phthalocyanine dyes and commonly used photosensitive resin polymers (such as polymethacrylate PMMA and polyimide PI) is poor, lacking synergistic sites, further promoting intermolecular aggregation and forming micron-scale dye-enriched areas during coating, resulting in increased film roughness and enhanced scattering (optical transmittance decreased by about 10%). (4) The thermal stability of the filter prepared with copper phthalocyanine dyes decreased during high-temperature heat treatment. In accelerated heat aging tests and ultraviolet light aging tests, the filter can be observed to have a red shift of the maximum absorption wavelength by 8–15 nm, the CIE1931 color coordinate y value deviation is as high as 0.2–0.4, and the color difference value is much greater than 3, which does not meet industry standards. (5) Copper phthalocyanine itself has a narrow absorption band, with the main absorption peak located between 600–700 nm. The overall color is bluish-green, and the green color purity is low. Therefore, it is urgent to inhibit the aggregation behavior of copper phthalocyanine and improve its photothermal stability and color purity to meet the comprehensive requirements of new display and optoelectronic devices. Summary of the Invention

[0005] The purpose of the present invention is to provide a copper phthalocyanine, a green photosensitive resin composition and their application. The copper phthalocyanine has excellent solubility and light and heat stability, and the green photosensitive resin composition can be made into a thinner colored layer and has high color purity.

[0006] The purpose of the present invention can be achieved by the following technical solutions:

[0007] One of the purposes of the present invention is to provide a copper phthalocyanine, which is prepared by substituting the benzene ring sites around the copper phthalocyanine mother core with a multifunctional group, and its structural formula is as follows:

[0008]

[0009] Among them, R1~R 16 are independently selected from any one of hydrogen atom, chlorine atom, alkyl, aryl or heteroaryl substituents, and R1 to R 16 The present invention comprises at least one naphthalimide group.

[0010] Preferably, the alkyl group is selected from any one of an alkyl group having 1-18 carbon atoms, a carboxyalkyl group having 1-18 carbon atoms, an ether bond having 1-18 carbon atoms, an ester group having 1-18 carbon atoms, an olefin having 2-18 carbon atoms, a hydroxyalkyl group having 1-18 carbon atoms, an amino group having 1-18 carbon atoms, or an aldehyde group having 1-18 carbon atoms.

[0011] Preferably, the heteroaryl group is selected from any one of a condensed heterocyclic group, a monocyclic aromatic heterocyclic group and a polycyclic aromatic heterocyclic group.

[0012] Preferably, the fused heterocyclic group is obtained by bonding any one of a monocyclic aromatic or non-aromatic heterocyclic group or a polycyclic aromatic heterocyclic group with at least one of an aryl group, a halogenated aryl group and an arylamine group.

[0013] Preferably, the aryl group includes an unsubstituted aryl group (such as phenyl), an alkyl-substituted aryl group (such as tolyl) and a polyaryl group (such as biphenyl).

[0014] Preferably, the halogenated aryl group is a group formed by replacing an aryl group with at least one halogen atom selected from the group consisting of F, Cl, Br, and I.

[0015] More preferably, the halogenated aryl group is a group formed by replacing an aryl group with a Br atom.

[0016] Preferably, the aromatic amine group includes any one of a diphenylamine group and a triphenylamine group.

[0017] Preferably, the heteroatoms contained in the fused heterocyclic group include N, S, and O heteroatoms, the number of the heteroatoms is 1-7, and the types of heteroatoms in the fused heterocyclic group include any one, any two, or any three of N, S, and O heteroatoms.

[0018] Preferably, R1 to R 16 In the present invention, at least 12 hydrogen atoms or chlorine atoms are contained, and the remaining substituent groups can be of the same type or different types.

[0019] More preferably, R1 to R 16 There are at least 12 hydrogen atoms or chlorine atoms, and the remaining substituent groups are of the same type.

[0020] Preferably, the structural formula of the naphthalimide group is as follows:

[0021]

[0022] Wherein, L is selected from one of the following formulas (A-1) to (A-15):

[0023]

[0024] Preferably, the curve in the general formula (II) represents R1 to R 16 The connecting bond with the copper phthalocyanine mother core in formula (I).

[0025] Preferably, the curved lines in formulae (A-1) to (A-15) represent the bonds between L and its adjacent O atoms and N atoms.

[0026] Preferably, N1 and N2 are each independently selected from a hydrogen atom, or a substituted or unsubstituted group:

[0027] Any one of a C1 to C60 chain alkyl group, a C1 to C60 branched alkyl group, a C1 to C60 chain alkenyl group, a C1 to C60 chain alkynyl group, a C3 to C60 cycloalkyl group, a C4 to C60 cycloalkenyl group, a C4 to C60 cycloalkynyl group, a C1 to C60 alkoxy group, a C1 to C60 branched alkoxy group, a C1 to C60 thioalkoxy group, a C6 to C60 aryl group, a C3 to C60 heteroaryl group, and a C4 to C60 aryloxy group, and at least one of N1 and N2 is an amino functional group.

[0028] Preferably, N1 and N2 are each independently selected from any one of formulas (B-1) to (B-49):

[0029]

[0030] Preferably, the curved lines in formulae (B-1) to (B-49) represent the connecting bonds between N1, N2 and the naphthaleneimide group in general formula (II).

[0031] Optionally, the structural formula of the copper phthalocyanine includes any one of the following:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040] A second object of the present invention is to provide a green photosensitive resin composition comprising the following components in parts by weight:

[0041]

[0042] Wherein, the colorant includes the copper phthalocyanine as described above; and the solid content of the green photosensitive resin composition is 12-37%.

[0043] Preferably, the green photosensitive resin composition comprises the following components in parts by weight:

[0044]

[0045] Further preferably, the colorant comprises copper phthalocyanine as described above.

[0046] Further preferably, the solid content of the green photosensitive resin composition is 29%.

[0047] Preferably, the resin containing a double bond structure and / or an epoxy structure includes one or more of acrylic polyurethane resin, acrylic polyester resin, acrylic epoxy resin, acrylic polyether resin, acrylic alkyd resin, acrylic melamine resin, and acrylic silicone resin.

[0048] Preferably, the monomer containing a double bond structure or / and an epoxy structure includes one or more of dipentaerythritol pentaacrylate, trimethylolpropane triacrylate, polyvinyl cinnamate monomer, N-benzylmaleimide, epoxy acrylate, and epoxy acrylamide.

[0049] Preferably, the photoinitiator with high absorption characteristics at 365nm includes one or more of oximes, benzoins, acetophenones, imidazoles (for example, 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl oxime), α,α-diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-methyl-2-morpholino-1-(4-methylphenylthio)propane-1-one, thioxanthone, 1,2'-bis(2-chlorophenyl)-tetraphenylbiimidazole, etc.).

[0050] Preferably, the additives for improving film-forming property and / or stability include one or more of a surface flattening agent, a defoaming agent, a stabilizer, and a plasticizer.

[0051] Preferably, the solvent containing an ether group includes one or more of propylene glycol monomethyl ether, propylene glycol methyl ether acetate, propylene glycol monoethyl ether, 3-methoxybutyl acetate, and N,N-dimethylformamide.

[0052] The third object of the present invention is to provide a use of the green photosensitive resin composition as a color photoresist in the preparation of a color filter.

[0053] Preferably, the green photosensitive resin composition can be applied to filters of display and sensing devices such as liquid crystal displays and image sensors.

[0054] The present invention designs and develops a series of copper phthalocyanines: First, to address the problem of poor solubility of copper phthalocyanine, the present invention introduces substituents with steric hindrance effects at the peripheral benzene ring sites of the copper phthalocyanine molecule, effectively destroying its π-π stacking configuration at the molecular level, thereby improving the solubility of the dye in commonly used industrial solvents such as PGMEA, and achieving the goal of stable dispersion of the dye in solution. Second, to address the problem of easy aggregation of copper phthalocyanine dyes, the present invention blocks the stacking of dye molecules by increasing the steric hindrance effect between molecules, thereby significantly reducing their aggregation tendency. Third, to address the problem of poor compatibility between copper phthalocyanine and the components in the photosensitive resin composition, the present invention introduces solvent-affinity side chains with polar or flexible characteristics to improve the molecular compatibility between the dye molecules and the polymer chains in the system, and inhibit phase separation and deposition aggregation caused by solvent evaporation during the film formation process. Fourth, to address the problem of poor thermal stability of copper phthalocyanine, the introduction of large steric groups at the benzene ring sites outside the copper phthalocyanine mother core can form a protective shell around the molecule, effectively inhibiting the intermolecular π-π stacking under thermal induction, thereby improving the thermal dispersion stability of the copper phthalocyanine dye; in addition, the introduction of conjugated extended structural units effectively extends its molecular π system, which not only increases the molecular weight, but also enhances the intermolecular π-π conjugated forces and van der Waals forces. This type of copper phthalocyanine molecule has a high molecular weight and good skeleton rigidity and conformational stability under high temperature conditions. Fifth, to address the problem of low color purity of green copper phthalocyanine dye, the present invention improves the absorption of the dye in the blue light region (400-500nm) by introducing a functional group with blue light absorption characteristics (naphthalimide group), and synthesizes a high color purity green dye.

[0055] The present invention further synthesizes a highly stable green dye-green photosensitive resin composition based on copper phthalocyanine. This overcomes the problems of poor solubility of the copper phthalocyanine dye and poor compatibility with the components of the photosensitive resin composition, as well as reduced photothermal stability and low green color purity. Furthermore, the colored layer prepared from the copper phthalocyanine-based green photosensitive resin composition exhibits excellent solubility, photothermal stability, high coloration, and high color purity, even at a relatively thin thickness. This green photosensitive resin composition can be used as a color photoresist and in the preparation of color filters.

[0056] In summary, the present invention utilizes a copper phthalocyanine core structure and modifies the phthalocyanine plane with a photochemically stable blue region absorption module (naphthalimide group) to obtain a dye with excellent color purity and stable photochemical and photophysical properties. Furthermore, the modification of the alkoxy and phenoxy molecular chain groups not only enhances the thermal stability of the dye but also effectively improves the solubility of the phthalocyanine dye in organic solvents and its compatibility with other components of the color photoresist, thereby providing a green photosensitive resin composition based on copper phthalocyanine. Furthermore, based on its excellent stability and high color purity, this green photosensitive resin composition can be used as a color photoresist in filters for display and sensing devices such as liquid crystal displays and image sensors.

[0057] Compared with the prior art, the present invention has the following beneficial effects:

[0058] (1) The present invention replaces the benzene ring sites around the copper phthalocyanine mother core with various substituents including naphthalimide groups, thereby providing a copper phthalocyanine and a green photosensitive resin composition prepared based on the copper phthalocyanine. The copper phthalocyanine has excellent solubility and light and heat stability. The green photosensitive resin composition can be made into a thinner colored layer. At the same time, the naphthalimide groups provide the dye with good blue light absorption ability, thereby having high green color purity.

[0059] (2) The present invention suppresses the strong π-π interaction of the phthalocyanine plane by introducing a copper phthalocyanine green dye synthesized by a bulky functional group, overcomes the problem of poor solubility, and can be well adapted to commonly used industrial solvents such as the color photoresist solvent PGMEA.

[0060] (3) The present invention adopts a copper phthalocyanine core structure with high chemical bond energy and introduces a π-conjugated naphthaleneimide group with good stability, so the prepared copper phthalocyanine dye has good light and thermochemical stability.

[0061] (4) The present invention prepares a copper phthalocyanine green photosensitive resin composition, which is designed by modifying the copper phthalocyanine molecular structure to introduce large steric substituents and polar functional groups, and is coordinated with an appropriate photosensitive resin matrix (such as an acrylic resin) and functional additives (such as a high-efficiency dispersant, a solubilizer, etc.), thereby achieving molecular-level uniform dispersion of the copper phthalocyanine dye in the photosensitive resin system and avoiding the problems of dye migration, aggregation and phase separation.

[0062] (5) The green photosensitive resin composition prepared by the present invention can be used as a color photoresist to prepare a color layer with a thin thickness (1.5-2.0 μm) and high coloring degree. The prepared color layer also has good system compatibility, heat resistance, and solvent resistance, and can be used in color filters of display and sensing devices such as liquid crystal displays and image sensors.

[0063] (6) The color filter prepared by the green photosensitive resin composition prepared by the present invention has excellent anti-migration property, ΔE ab Both are less than 3.

[0064] (7) The color filter prepared by using the green photosensitive resin composition prepared by the present invention has good edge line regularity and development process margin. BRIEF DESCRIPTION OF THE DRAWINGS

[0065] Figure 1 The mass spectrum of compound (10) prepared in Example 4;

[0066] Figure 2 This is a physical picture of the green photosensitive resin composition D1 prepared in Example 1-1;

[0067] Figure 3 is the UV-visible absorption spectrum of the green photosensitive resin composition D1 prepared in Example 1-1;

[0068] Figure 4 2-1 and 2-2 are CIE chromaticity diagrams of Example 1-1 and Comparative Example 2-1. DETAILED DESCRIPTION

[0069] The present invention is described in detail below with reference to the accompanying drawings and specific embodiments. This embodiment is implemented based on the technical solution of the present invention, and provides a detailed implementation method and specific operation process, but the protection scope of the present invention is not limited to the following embodiments.

[0070] Unless otherwise specified, the reagents, methods, instruments and equipment used in the present invention are conventional reagents, methods, instruments and equipment in the art. Unless otherwise specified, the reagents and materials used in the following examples are commercially available.

[0071] Example 1:

[0072] Synthesis of compound (1):

[0073]

[0074] Dissolve 4-bromonaphthalic anhydride (1 mmol) and p-bromophenol (2 mmol) in ethanol (30 mL) and stir at 90°C under nitrogen for 24 hours. After the reaction, cool to room temperature and pour the mixture into ice water to precipitate a solid. Filter the mixture to obtain a solid, which is then dried to obtain Intermediate 1.

[0075] Intermediate 1 (1 mmol), 4-(2-methoxyethoxy)aniline (1 mmol), tetrakistriphenylphosphine palladium (0.05 mmol), and potassium tert-butoxide (1.5 mmol) were heated under reflux at 110°C for 24 h in a toluene (20 mL) solution. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane and saturated brine. The organic layer was collected and dried over anhydrous magnesium sulfate, and then the organic solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluent: dichloromethane: petroleum ether = 4:1) to obtain Intermediate 2.

[0076] Intermediate 2 (4 mmol), 4-nitrophthalonitrile (4 mmol), and potassium carbonate (8 mmol) were dissolved in N'N-dimethylformamide (50 mL) and stirred at 160°C for 24 h under nitrogen. After the reaction, the mixture was cooled to room temperature and poured into ice water to precipitate a solid. The mixture was filtered to obtain a solid, which was then dried and purified by column chromatography on silica gel (eluent: petroleum ether: dichloromethane = 6:1) to obtain Intermediate 3.

[0077] Intermediate 3 (4 mmol) and copper chloride (1 mmol) were dissolved in n-pentanol (20 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and the organic solvent was removed by evaporation under reduced pressure to obtain a crude product. The crude product was dried and purified by column chromatography on silica gel (eluent: dichloromethane:methanol = 45:1) to obtain compound (1) as a green solid in a yield of 77%.

[0078] After high-resolution mass spectrometry, ESI source, and positive ion mode detection, the molecular formula of compound (1) is C 144 H 112 CuN 16 O 20 , detected value 2449.7630, theoretical value 2449.7631; detected element content (%): C, 70.59; H, 4.62; Cu, 2.59; N, 9.14; O, 13.06. Theoretical element content (%): C, 70.59; H, 4.61; Cu, 2.59; N, 9.15; O, 13.06. These analytical results indicate that the product obtained is the expected product.

[0079] The starting reactants were replaced with corresponding reactants, and the synthesis of the compounds involved in Examples 2-4 was completed by referring to the preparation method of Example 1. The specific results are shown in Table 1.

[0080] Table 1

[0081]

[0082] Figure 1This is the mass spectrum of compound (10) prepared in Example 4, which shows that compound (10) was successfully prepared.

[0083] Example 5:

[0084] Synthesis of compound (24):

[0085]

[0086] Dissolve 4-bromonaphthalic anhydride (1 mmol) and p-bromophenol (2 mmol) in ethanol (30 mL) and stir at 90°C under nitrogen for 24 hours. After the reaction, cool to room temperature and pour the mixture into ice water to precipitate a solid. Filter the mixture to obtain a solid, which is then dried to obtain Intermediate 1.

[0087] Intermediate 1 (1 mmol), 3,5-diisopropylaniline (1 mmol), tetrakistriphenylphosphine palladium (0.05 mmol), and potassium tert-butoxide (1.5 mmol) were heated under reflux at 110°C for 24 h in a toluene (20 mL) solution. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane and saturated brine. The organic layer was collected and dried over anhydrous magnesium sulfate, and then the organic solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluent: dichloromethane:petroleum ether = 5:1) to obtain Intermediate 4.

[0088] Intermediate 4 (4 mmol), 3-nitrophthalonitrile (4 mmol), and potassium carbonate (8 mmol) were dissolved in N'N-dimethylformamide (50 mL) and stirred at 160°C for 24 h under nitrogen. After the reaction, the mixture was cooled to room temperature and poured into ice water to precipitate a solid. The mixture was filtered to obtain a solid, which was then dried and purified by column chromatography on silica gel (eluent: petroleum ether: dichloromethane = 7:1) to obtain Intermediate 5.

[0089] Intermediate 5 (4 mmol) and copper chloride (1 mmol) were dissolved in n-pentanol (20 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and the organic solvent was removed by evaporation under reduced pressure to obtain a crude product. The crude product was dried and purified by column chromatography on silica gel (eluent: dichloromethane:methanol = 47:1) to obtain compound (24) as a green solid in a yield of 78%.

[0090] After high-resolution mass spectrometry, ESI source, and positive ion mode detection, the molecular formula of compound (24) is C 156 H 136 CuN 16 O 12, detected value 2489.9927, theoretical value 2489.9926; detected element content (%): C, 75.23; H, 5.50; Cu, 2.56, N, 9.00; O, 7.71. Theoretical element content (%): C, 75.24; H, 5.50; Cu, 2.55, N, 9.00; O, 7.71. These analytical results indicate that the product obtained is the expected product.

[0091] The starting reactants were replaced with corresponding reactants, and the synthesis of the compounds involved in Examples 6-8 was completed by referring to the preparation method of Example 5. The specific results are shown in Table 2.

[0092] Table 2

[0093]

[0094]

[0095] Example 9:

[0096] Synthesis of compound (37):

[0097]

[0098] Dissolve 4-bromonaphthalic anhydride (1 mmol) and p-bromophenol (2 mmol) in ethanol (30 mL) and stir at 90°C under nitrogen for 24 hours. After the reaction, cool to room temperature and pour the mixture into ice water to precipitate a solid. Filter the mixture to obtain a solid, which is then dried to obtain Intermediate 1.

[0099] Intermediate 1 (1 mmol), 3,4,5-trimethylaniline (1 mmol), tetrakistriphenylphosphine palladium (0.05 mmol), and potassium tert-butoxide (1.5 mmol) were heated under reflux at 110°C for 24 h in a toluene (20 mL) solution. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane and saturated brine. The organic layer was collected and dried over anhydrous magnesium sulfate, and then the organic solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluent: dichloromethane: petroleum ether = 4:1) to obtain Intermediate 6.

[0100] Intermediate 6 (4 mmol), 3,4,5,6-tetrachlorophthalonitrile (4 mmol), and potassium carbonate (8 mmol) were dissolved in N'N-dimethylformamide (50 mL) and stirred at 160°C for 24 h under nitrogen. After the reaction, the mixture was cooled to room temperature and poured into ice water to precipitate a solid. The mixture was filtered to obtain a solid, which was then dried and purified by column chromatography on silica gel (eluent: petroleum ether: dichloromethane = 3:1) to obtain Intermediate 7.

[0101] Intermediate 7 (4 mmol) and copper chloride (1 mmol) were dissolved in n-pentanol (20 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and the organic solvent was removed by evaporation under reduced pressure to obtain a crude product. The crude product was dried and purified by column chromatography on silica gel (eluent: dichloromethane:methanol = 50:1) to obtain compound (37) as a green solid in a yield of 77%.

[0102] After high-resolution mass spectrometry, ESI source, and positive ion mode detection, the molecular formula of compound (37) is C 140 H 100 Cl 12 CuN 16 O 12 , detected value 2687.3284, theoretical value 2687.3283; detected element content (%): C, 62.57; H, 3.75; Cl, ​​15.82; Cu, 2.36; N, 8.34; O, 7.15. Theoretical element content (%): C, 62.57; H, 3.75; Cl, ​​15.83; Cu, 2.36; N, 8.34; O, 7.14. The above analysis results indicate that the obtained product is the expected product.

[0103] The starting reactants were replaced with corresponding reactants, and the synthesis of the compounds involved in Examples 10-12 was completed by referring to the preparation method of Example 9. The specific results are shown in Table 3.

[0104] Table 3

[0105]

[0106] Example 13:

[0107] Synthesis of compound (53):

[0108]

[0109] Dissolve 4-bromonaphthalene anhydride (1 mmol) and ethanolamine (2 mmol) in ethanol (30 mL) and stir at 90°C under nitrogen for 24 hours. After the reaction, cool to room temperature and pour the mixture into ice water to precipitate a solid. Filter the mixture to obtain a solid, which is then dried to obtain Intermediate 8.

[0110] Intermediate 8 (1 mmol), methylbutylamine (1 mmol), tetrakistriphenylphosphine palladium (0.05 mmol), and potassium tert-butoxide (1.5 mmol) were heated under reflux at 110°C for 24 h in a toluene (20 mL) solution. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and saturated brine. The organic layer was collected and dried over anhydrous magnesium sulfate, and then the organic solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluent: dichloromethane: petroleum ether = 7:1) to obtain Intermediate 9.

[0111] Intermediate 9 (4 mmol), 4-nitrophthalonitrile (4 mmol), and potassium carbonate (8 mmol) were dissolved in N'N-dimethylformamide (50 mL) and stirred at 160°C for 24 h under nitrogen. After the reaction, the mixture was cooled to room temperature and poured into ice water to precipitate a solid. The mixture was filtered to obtain a solid, which was then dried and purified by column chromatography on silica gel (eluent: petroleum ether: dichloromethane = 4:1) to obtain Intermediate 10.

[0112] Intermediate 10 (4 mmol) and copper chloride (1 mmol) were dissolved in n-pentanol (20 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and the organic solvent was removed by evaporation under reduced pressure to obtain a crude product. The crude product was dried and purified by column chromatography on silica gel (eluent: dichloromethane:methanol = 43:1) to obtain compound (53) as a green solid in a yield of 71%.

[0113] After high-resolution mass spectrometry, ESI source, and positive ion mode detection, the molecular formula of compound (53) is C 112 H 112 CuN 16 O 12 , detected value 1937.8047, theoretical value 1937.8048; detected element content (%): C, 69.43; H, 5.83; Cu, 3.28; N, 11.56; O, 9.91. Theoretical element content (%): C, 69.42; H, 5.83; Cu, 3.28; N, 11.57; O, 9.91. These analytical results indicate that the product obtained is the expected product.

[0114] The starting reactants were replaced with corresponding reactants, and the synthesis of the compounds involved in Examples 14-16 was completed by referring to the preparation method of Example 13. The specific results are shown in Table 4.

[0115] Table 4

[0116]

[0117] Example 17:

[0118] Synthesis of compound (71):

[0119]

[0120] Dissolve 4-bromonaphthalene anhydride (1 mmol) and 3-amino-1-propanol (2 mmol) in ethanol (30 mL) and stir at 90°C under nitrogen for 24 hours. After the reaction, cool to room temperature and pour the mixture into ice water to precipitate a solid. Filter the mixture to obtain a solid, which is then dried to obtain Intermediate 11.

[0121] Intermediate 11 (1 mmol), cyclopropylmethylamine (1 mmol), tetrakistriphenylphosphine palladium (0.05 mmol), and potassium tert-butoxide (1.5 mmol) were heated under reflux at 110°C for 24 h in a toluene (20 mL) solution. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane and saturated brine. The organic layer was collected and dried over anhydrous magnesium sulfate, and then the organic solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluent: dichloromethane: petroleum ether = 5:1) to obtain Intermediate 12.

[0122] Intermediate 12 (4 mmol), 3-nitrophthalonitrile (4 mmol), and potassium carbonate (8 mmol) were dissolved in N'N-dimethylformamide (50 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and poured into ice water to precipitate a solid. The mixture was filtered to obtain a solid, which was then dried and purified by column chromatography on silica gel (eluent: petroleum ether: dichloromethane = 6:1) to obtain Intermediate 13.

[0123] Intermediate 13 (4 mmol) and copper chloride (1 mmol) were dissolved in n-pentanol (20 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and the organic solvent was removed by evaporation under reduced pressure to obtain a crude product. The crude product was dried and purified by column chromatography on silica gel (eluent: dichloromethane:methanol = 41:1) to obtain compound (71) as a green solid in a yield of 79%.

[0124] After high-resolution mass spectrometry, ESI source, and positive ion mode detection, the molecular formula of compound (71) is C 112 H 104 CuN 16 O 12, detected value 1929.7423, theoretical value 1929.7422; detected element content (%): C, 69.72; H, 5.43; Cu, 3.28; N, 11.61; O, 9.95. Theoretical element content (%): C, 69.71; H, 5.43; Cu, 3.29; N, 11.61; O, 9.95. The above analytical results indicate that the obtained product is the expected product.

[0125] The starting reactants were replaced with corresponding reactants respectively, and the synthesis of the compounds involved in Examples 18-20 was completed by referring to the preparation method of Example 17. The specific results are shown in Table 5.

[0126] Table 5

[0127]

[0128] Example 21:

[0129] Synthesis of compound (91):

[0130]

[0131] Dissolve 4-bromonaphthalene anhydride (1 mmol) and 6-amino-1-hexanol (2 mmol) in ethanol (30 mL) and stir at 90°C under nitrogen for 24 hours. After the reaction, cool to room temperature and pour the mixture into ice water to precipitate a solid. Filter the mixture to obtain a solid, which is then dried to obtain Intermediate 14.

[0132] Intermediate 14 (1 mmol), N,N-dimethylethylenediamine (1 mmol), tetrakistriphenylphosphine palladium (0.05 mmol), and potassium tert-butoxide (1.5 mmol) were heated under reflux at 110°C for 24 h in a toluene (20 mL) solution. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane and saturated brine. The organic layer was collected and dried over anhydrous magnesium sulfate, and then the organic solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluent: dichloromethane: petroleum ether = 8:1) to obtain Intermediate 15.

[0133] Intermediate 15 (4 mmol), 3,4,5,6-tetrachlorophthalonitrile (4 mmol), and potassium carbonate (8 mmol) were dissolved in N'N-dimethylformamide (50 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and poured into ice water to precipitate a solid. The mixture was filtered to obtain a solid, which was then dried and purified by column chromatography on silica gel (eluent: petroleum ether: dichloromethane = 4:1) to obtain Intermediate 16.

[0134] Intermediate 16 (4 mmol) and copper chloride (1 mmol) were dissolved in n-pentanol (20 mL) and stirred at 160°C under nitrogen for 24 h. After the reaction, the mixture was cooled to room temperature and the organic solvent was removed by evaporation under reduced pressure to obtain a crude product. The crude product was dried and purified by column chromatography on silica gel (eluent: dichloromethane:methanol = 50:1) to obtain compound (91) as a green solid in a yield of 75%.

[0135] After high-resolution mass spectrometry, ESI source, and positive ion mode detection, the molecular formula of compound (91) is C 120 H 128 Cl 12 CuN 20 O 12 , detected value 2531.5596, theoretical value 2531.5597; detected element content (%): C, 56.93; H, 5.10; Cl, ​​16.80; Cu, 2.51; N, 11.07; O, 7.59. Theoretical element content (%): C, 56.94; H, 5.10; Cl, ​​16.80; Cu, 2.51; N, 11.07; O, 7.58. These analytical results indicate that the product obtained is the expected product.

[0136] The starting reactants were replaced with corresponding reactants respectively, and the synthesis of the compounds involved in Examples 22-24 was completed by referring to the preparation method of Example 21. The specific results are shown in Table 6.

[0137] Table 6

[0138]

[0139]

[0140] Example 1-1

[0141] Preparation of green photosensitive resin composition D1

[0142] A green photosensitive resin composition D1 was prepared using the copper phthalocyanine dye of formula (1) prepared in Example 1, and subjected to photolithographic development to compare the properties of the photosensitive resin composition. The photolithographic development method is a conventional method used by those skilled in the art.

[0143] formula:

[0144] 3.5 parts by weight of a colorant, 20 parts by weight of a resin containing a double bond structure, 4 parts by weight of a monomer containing a double bond structure, 0.5 parts by weight of a photoinitiator having high absorption characteristics at 365 nm, 0.25 parts by weight of an additive for improving film-forming properties and / or stability, and 71 parts by weight of an ether-containing solvent are thoroughly mixed and dissolved, and the solid content is controlled at about 28% to obtain a green photosensitive resin composition. Figure 2 shown.

[0145] in,

[0146] Colorant: Copper phthalocyanine (Formula (1))

[0147] Resins containing double bond structures or / and epoxy structures: acrylic polyester resin (analytical grade), purchased from Titan Corporation;

[0148] Monomers containing double bond structures or / and epoxy structures: dipentaerythritol pentaacrylate monomer (analytical grade), purchased from Titan Corporation;

[0149] Photoinitiator with high absorption characteristics at 365 nm: α,α-diethoxyacetophenone (analytical grade), purchased from Titan Company;

[0150] Additives for improving film-forming property and / or stability: defoaming agent (analytical grade), purchased from Titan Company;

[0151] Ether-containing solvents: Propylene glycol methyl ether acetate (analytical grade), purchased from Titan Corporation.

[0152] Comparative Example 2-1

[0153] Preparation of green photosensitive resin composition E1

[0154] 3.5 parts by weight of a colorant, 20 parts by weight of a resin containing a double bond structure, 4 parts by weight of a monomer containing a double bond structure, 0.5 parts by weight of a photoinitiator having high absorption characteristics at 365 nm, 0.25 parts by weight of an additive for improving film-forming properties and / or stability, and 71 parts by weight of an ether-containing solvent are thoroughly mixed and dissolved, and the solid content is controlled at about 28% to obtain a green photosensitive resin composition. Figure 1 shown.

[0155] in,

[0156] Colorant: Copper Phthalocyanine Dye L

[0157] Resins containing double bond structures or / and epoxy structures: acrylic polyester resin (analytical grade), purchased from Titan Corporation;

[0158] Monomers containing double bond structures or / and epoxy structures: dipentaerythritol pentaacrylate monomer (analytical grade), purchased from Titan Corporation;

[0159] Photoinitiator with high absorption at 365 nm: α,α-diethoxyacetophenone (analytical pure), purchased from Titan Company;

[0160] Additive to improve film-forming property or / and stability: defoaming agent (analytical pure), purchased from Titan Company;

[0161] Solvent containing ether group: propylene glycol methyl ether acetate (analytical pure), purchased from Titan Company.

[0162] The chemical structure of copper phthalocyanine dye L is as follows:

[0163]

[0164] The performance test of photosensitive resin compositions D1 and E1 was carried out by the following steps:

[0165] The glass sheet was cleaned and dried, and a uniform film layer of 1.5-2.0 μm was prepared by using a spin coater. Pre-baking was carried out at 90°C for 120 s, exposure was carried out using 365 nm ultraviolet light, the exposure amount was 40 mJ / cm 2 , the distance between the mask plate and the film was 180 μm, then development was carried out at 25°C for 5 s, post-baking was carried out at 230°C for 30 min, and then the subsequent related properties were tested, and the results are shown in Table 7.

[0166] Performance test and evaluation method:

[0167] (1) Colorimetric: detected by Konica Minolta CM-5 spectrophotometer.

[0168] (2) System compatibility: the photosensitive resin composition was stored in the dark at 0-10°C, the change in viscosity was tested (at least six months), and according to the process conditions of photolithography, the appearance of particles on the surface of the color film was observed under an optical microscope (OM) at x500.

[0169] The evaluation criteria are as follows:

[0170] ○: viscosity change value < ± 5% mPa·s and no particles on the surface at x500;

[0171] △: viscosity change value < ± 10% mPa·s and no particles on the surface at x500;

[0172] x: viscosity change value > ± 10% mPa·s or particles on the surface at x500;

[0173] (3) Heat resistance test: The heat resistance of the photosensitive resin composition was verified by color difference. The film was post-baked at 230°C for 20 minutes and repeated twice. The film thickness was measured by XP-2 step analyzer. The color difference was the color difference between the second post-baked sample and the first post-baked sample. The color difference was measured by Minolta CM-5. If ΔE ab <3, it indicates better heat resistance;

[0174] (4) Evaluation of solvent resistance:

[0175] Place the post-baked sample in isopropanol, soak it at room temperature for 5 minutes, bake it in an oven at 150℃ for 30 minutes, and measure the color difference before and after. If ΔE ab <3, indicating good solvent resistance.

[0176] (5) Evaluation of anti-migration performance:

[0177] According to the color filter manufacturing process, green or blue pixels are first prepared on thin film transistor (TFT) glass. Then the sample is coated and after the development is completed, the color filter surface is blown dry and the color difference before and after the pixel is measured. If ΔE ab <3, indicating good anti-migration properties.

[0178] (6) Line width, edge regularity, and development process margin:

[0179] The line width and edge uniformity were tested by x500 OM, and the mask line width was 140μm.

[0180] When evaluating process margin, other process conditions are fixed and the edge neatness, edge residue, or edge peeling of the image obtained with a development time between 40 and 100 seconds is examined. The peeling property is determined by referring to the adhesion measurement method in the art.

[0181] The evaluation criteria for edge neatness are as follows:

[0182] ○: The edges are neat and there is no residue at the edges after 50s of development;

[0183] △: After 50 seconds of development, the image edge has burrs, is not neat, or has residues at the edge;

[0184] ×: Image missing

[0185] The specific standards for evaluating the development process margin are as follows:

[0186] ○: The edges are neat and there is no residue or peeling at the edges after 40-100s of development;

[0187] △: The edges are neat and there is no residue or peeling at the edges after 50-80s of development;

[0188] X: 50-80s of developing edge line is not neat, or there is residual at the edge, or there is peeling at the edge;

[0189] The above-mentioned alkali developing solution is, for example, an aqueous solution of an alkali compound such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium carbonate, aqueous ammonia, diethylamine, or tetramethylammonium hydroxide, and the concentration of the alkali compound is preferably 0.2-1.0%, more preferably 0.4-0.6%. - ] concentration of 0.2-1.0%, preferably 0.4-0.6%.

[0190] The green photosensitive resin compositions D2-D24 of Examples 1-2 to 1-24 were prepared according to the same method and using the same materials as in Reference Example 1-1, except for the colorant. The results of the specific evaluation are shown in Table 7.

[0191] Table 7

[0192]

[0193] Figure 3 The UV-Vis absorption spectrum of the green photosensitive resin composition D1 prepared in Example 1-1 is shown in the figure. It can be seen from the figure that the green photosensitive resin composition prepared in the application has good absorption in the blue light region (400-500 nm) and the red light region (600-700 nm).

[0194] Figure 4 The CIE chromaticity diagram of Example 1-1 and Comparative Example 2-1 is shown in the figure. It can be seen from the figure that the green photosensitive resin composition prepared in the application has more excellent coloration and green color purity.

[0195] The comparison of the experimental results shows that, compared with the copper phthalocyanine dye L used in the comparative example, the copper phthalocyanine dyes in Examples 1-1 to 1-24 are coupled with large steric hindrance groups at the benzene ring position around the copper phthalocyanine mother nucleus, which effectively improves the solubility of the dye in the color photoresist solvent PGMEA; in addition, the dye in Examples 1-1 to 1-24 introduces a naphthalimide group with good stability π conjugated structure, and the prepared copper phthalocyanine dye has good green color purity and excellent heat resistance, light resistance and solvent resistance. At the same time, by modifying the molecular structure of copper phthalocyanine and introducing polar functional groups, the copper phthalocyanine dye is uniformly dispersed in the photosensitive resin composition, avoiding the problems of dye migration, aggregation and phase separation. Compared with the photosensitive resin composition E1 using the copper phthalocyanine dye L in the comparative example, the photosensitive resin compositions D1 to D24 using these copper phthalocyanine dyes have similar good process performance, such as system compatibility, edge line neatness and developing process margin.

[0196] In summary, the present invention effectively improves the solubility of copper phthalocyanine dyes by replacing the benzene ring sites around the copper phthalocyanine mother nucleus with functional groups; inhibits the aggregation of the dye in the solid state and further improves the stability of the phthalocyanine dye; improves the optical properties of traditional copper phthalocyanine dyes, and prepares green dyes with high color purity and stable photochemical and photophysical properties; solves the problems of thermal stability and solvent resistance not meeting industrial production requirements, and poor solubility and compatibility in color photoresist systems; the screened copper phthalocyanine compounds with better performance can be used to prepare green photosensitive resin compositions, which can be used as color photoresists in filters of display and sensing devices such as liquid crystal displays and image sensors.

[0197] The above description of the embodiments is intended to facilitate understanding and use of the invention by those skilled in the art. It will be apparent that those skilled in the art can readily make various modifications to these embodiments and apply the general principles described herein to other embodiments without requiring inventive effort. Therefore, the present invention is not limited to the above-described embodiments. Improvements and modifications made by those skilled in the art based on the disclosure of the present invention, without departing from the scope of the present invention, should be within the scope of protection of the present invention.

Claims

1. A copper phthalocyanine, characterized in that It is prepared by substituting the benzene ring sites around the copper phthalocyanine core with multifunctional groups. Its structural formula is as follows: Among them, R1~R 16 are independently selected from any one of hydrogen atom, chlorine atom, alkyl, aryl or heteroaryl substituents, and R1 to R 16 The present invention comprises at least one naphthalimide group.

2. A copper phthalocyanine according to claim 1, characterized in that, The alkyl group is selected from any one of an alkyl group having 1-18 carbon atoms, a carboxyalkyl group having 1-18 carbon atoms, an ether bond having 1-18 carbon atoms, an ester group having 1-18 carbon atoms, an olefin having 2-18 carbon atoms, a hydroxyalkyl group having 1-18 carbon atoms, an amino group having 1-18 carbon atoms, or an aldehyde group having 1-18 carbon atoms.

3. The copper phthalocyanine according to claim 1, wherein The heteroaryl group is selected from any one of a fused heterocyclic group, a monocyclic aromatic heterocyclic group and a polycyclic aromatic heterocyclic group; The fused heterocyclic group is obtained by bonding any one of a monocyclic aromatic or non-aromatic heterocyclic group or a polycyclic aromatic heterocyclic group to at least one of an aryl group, a halogenated aryl group and an arylamine group; Wherein, the aryl group includes unsubstituted aryl, alkyl-substituted aryl and polyaryl; The halogenated aryl group is a group formed by replacing an aryl group with at least one halogen atom selected from the group consisting of F, Cl, Br, and I; The aromatic amine group includes any one of a diphenylamine group and a triphenylamine group; The heteroatoms contained in the fused heterocyclic group include N, S, and O heteroatoms, and the number of the heteroatoms is 1-7. The types of heteroatoms in the fused heterocyclic group include any one, any two, or any three of N, S, and O heteroatoms.

4. The copper phthalocyanine according to claim 1, wherein The structural formula of the naphthalene imide group is as follows: Wherein, L is selected from one of the following formulas (A-1) to (A-15), and the curved lines in the formulas (A-1) to (A-15) represent the bonds between L and its adjacent O atoms and N atoms:

5. The copper phthalocyanine according to claim 4, characterized in that N1 and N2 are each independently selected from a hydrogen atom, or a substituted or unsubstituted group: Any one of a C1 to C60 chain alkyl group, a C1 to C60 branched alkyl group, a C1 to C60 chain alkenyl group, a C1 to C60 chain alkynyl group, a C3 to C60 cycloalkyl group, a C4 to C60 cycloalkenyl group, a C4 to C60 cycloalkynyl group, a C1 to C60 alkoxy group, a C1 to C60 branched alkoxy group, a C1 to C60 thioalkoxy group, a C6 to C60 aryl group, a C3 to C60 heteroaryl group, and a C4 to C60 aryloxy group, and at least one of N1 and N2 is an amino functional group.

6. The copper phthalocyanine according to claim 4, characterized in that: N1 and N2 are each independently selected from any one of formulas (B-1) to (B-49), wherein the curve represents the connection between N1, N2 and the naphthalene imide group in general formula (II):

7. The copper phthalocyanine according to claim 1, characterized in that Its structural formula includes any of the following:

8. A green photosensitive resin composition, characterized in that: The composition comprises the following components in parts by weight: Wherein, the colorant comprises the copper phthalocyanine according to any one of claims 1 to 7; and the solid content of the green photosensitive resin composition is 12-37%.

9. The green photosensitive resin composition according to claim 8, characterized in that: Resins containing double bond structures or / and epoxy structures include one or more of acrylic polyurethane resins, acrylic polyester resins, acrylic epoxy resins, acrylic polyether resins, acrylic alkyd resins, acrylic melamine resins, and acrylic silicone resins; monomers containing double bond structures or / and epoxy structures include one or more of dipentaerythritol pentaacrylate, trimethylolpropane triacrylate, polyvinyl cinnamate monomer, N-benzylmaleimide, epoxy acrylate, and epoxy acrylamide; photoinitiators with high absorption characteristics at 365nm include one or more of oximes, benzoins, acetophenones, and imidazoles; additives for improving film-forming properties and / or stability include one or more of surface flattening agents, defoaming agents, stabilizers, and plasticizers; solvents containing ether groups include one or more of propylene glycol monomethyl ether, propylene glycol methyl ether acetate, propylene glycol monoethyl ether, 3-methoxybutyl acetate, and N,N-dimethylformamide.

10. Use of the green photosensitive resin composition according to any one of claims 8 to 9 as a color photoresist in the preparation of a color filter.

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