Photosensitive resin composition, cured product thereof, method for forming a pattern, and method for producing a photosensitive resin composition

Abstract

The present invention relates to a photosensitive resin composition, a cured product thereof, a method for forming a pattern, and a method for producing a photosensitive resin composition. Specifically, the present invention relates to a photosensitive resin composition containing a polysilsesquioxane binder and exhibiting excellent storage stability, surface coating properties, and resolution, a cured product thereof, a method for forming a pattern, and a method for producing a photosensitive resin composition.

Description

Technical Field

[0001] This invention relates to a photosensitive resin composition, its cured product, a patterning method, and a method for preparing the photosensitive resin composition, and more specifically to a photosensitive resin composition comprising a polysilsesquioxane binder and exhibiting excellent properties in terms of storage stability, surface coatability, and resolution, its cured product, a patterning method, and a method for preparing the photosensitive resin composition. Background Technology

[0002] Traditionally, OLED pixels are patterned using methods such as screen printing, roll-to-roll, laser direct patterning, and similar techniques. Furthermore, photolithography using photoresist compositions is employed in the patterning process of OLED display manufacturing, enabling large-area and ultra-fine patterning of OLED pixels, thereby achieving high-resolution display screens.

[0003] To achieve densely integrated, ultra-high-resolution OLED displays, forming ultra-fine patterns remains crucial. Methods for forming ultra-fine patterns include positive and negative methods. Positive methods refer to processes where patterns are formed by removing exposed portions of the photoresist composition, while negative methods refer to processes where patterns are formed by removing unexposed portions of the photoresist composition.

[0004] The photoresist compositions used in positive and negative methods are different. Specifically, photoresist compositions used in negative methods are required to be developable so that unexposed areas can be removed. Since typical negative photoresist photosensitive resin compositions contain acidic functional groups in the binder, development is performed using alkaline developers such as KOH and tetramethyl ammonium hydroxide (TMAH). Positively developed negative photosensitive resin compositions are disclosed in, for example, Korean Patent Registration No. 10-2585445 (October 5, 2023), Korean Patent Registration No. 10-1787651 (October 18, 2017), Korean Patent Registration No. 10-1306778 (September 17, 2013), and similar patents. Summary of the Invention

[0005] Technical issues

[0006] In recent years, the display industry has shifted its focus from liquid crystal displays (LCDs) to OLED displays, which generate images through an organic light-emitting layer that produces light without a backlight unit. These OLED displays utilize pixel define layers (PDLs) to define and insulate the boundaries of individual pixels. Acrylic compounds, known for their excellent photosensitivity, are often used to form PDLs. However, due to the instability of acrylic compounds at high temperatures and their relatively high dielectric constant, alternative compounds are needed.

[0007] Polysilsesquioxane compounds are polysiloxane copolymers exhibiting high heat resistance, high transparency, and low dielectric properties suitable for use in photosensitive resin compositions. However, because polysilsesquioxanes are synthesized via an acid / base-catalyzed sol-gel reaction, it is difficult to incorporate acidic functional groups into the adhesive itself as in typical adhesives. Therefore, despite the advantageous properties of most polysilsesquioxane adhesives, they exhibit poor developability due to their low solubility in alkaline developers, making them difficult to apply in negative photosensitive resin compositions.

[0008] Therefore, embodiments of the present invention provide a photosensitive resin composition that ensures excellent storage stability, surface coatability, and resolution by incorporating a polysilsesquioxane binder that exhibits suitable developability in an alkaline aqueous solution.

[0009] Technical solutions

[0010] According to one aspect of the present invention, a photosensitive resin composition comprises: a binder; a pigment; a multifunctional monomer; a photoinitiator; and a solvent, wherein...

[0011] The adhesive includes a polysilsesquioxane-based adhesive, and

[0012] The polysilsesquioxane-based adhesive has an acid value by introducing acid functional groups into the adhesive.

[0013] Preferably, the adhesive contains carboxyl groups introduced by a succinic acid compound.

[0014] Preferably, the succinic acid compound is a succinic anhydride compound.

[0015] Preferably, the photosensitive resin composition comprises:

[0016] The adhesive comprises 18% to 50% by weight of the total weight of the photosensitive resin composition;

[0017] 1% to 20% by weight of the pigment;

[0018] 0.1% to 10% by weight of the multifunctional monomer;

[0019] 0.1% to 5% by weight of the photoinitiator; and

[0020] The solvent is used in amounts ranging from 30% to 80% by weight.

[0021] Preferably, the succinic acid compound is triethoxysilylpropyl succinic anhydride, trimethoxysilylpropyl succinic anhydride, triethoxysilylbutyl succinic anhydride, or trimethoxysilylbutyl succinic anhydride.

[0022] Preferably, the adhesive has an acid value of 5 mgKOH / g to 38 mgKOH / g.

[0023] Preferably, the adhesive has an alkali dissolution rate of 300 to 1000 Å / sec.

[0024] Preferably, the patterned cured layer formed from the photosensitive resin composition has no residue.

[0025] Preferably, the patterned cured layer formed from the photosensitive resin composition has a minimum size of less than 10 μm as measured on the patterned cured layer.

[0026] Preferably, the patterned cured layer formed from the photosensitive resin composition prepared using the adhesive stored at room temperature (23°C) for 30 days has no residue, and

[0027] It has a minimum size of less than 10 μm as measured on the patterned and cured layer.

[0028] Preferably, the photosensitive resin composition is used to form a pixel defined layer (PDL) in an organic light-emitting diode (OLED) display.

[0029] According to another aspect of the present invention, a cured product is provided, which is prepared by curing the photosensitive resin composition.

[0030] According to another aspect of the present invention, a pattern forming method is provided, the pattern forming method comprising: coating the photosensitive resin composition; and

[0031] The coated photosensitive resin composition is exposed in a position-selective manner, followed by development.

[0032] Beneficial effects

[0033] Embodiments of the present invention provide a photosensitive resin composition comprising a polysilsesquioxane-based adhesive, wherein the polysilsesquioxane-based adhesive exhibits developability in an alkaline aqueous solution by controlling the acid functional groups and double bonds within the polysilsesquioxane structure.

[0034] Furthermore, embodiments of the present invention provide a photosensitive resin composition exhibiting excellent properties in terms of storage stability and surface coating properties.

[0035] Furthermore, embodiments of the present invention provide a photosensitive resin composition for forming a pixel-defined layer (PDL) in an OLED display. Detailed Implementation

[0036] Exemplary embodiments of the present invention will be described below.

[0037] Unless otherwise stated, all terms used herein (including technical and scientific terms) have the meanings commonly understood by one of ordinary skill in the art. It should also be understood that terms (e.g., those defined in common dictionaries) should be interpreted as having the meaning consistent with their meaning in the context of the specification and related technology, and should not be interpreted as having an idealized or overly formal meaning unless explicitly defined herein.

[0038] The term “comprising” as used in this specification indicates the presence of a stated component and / or step, but does not exclude the presence or addition of one or more other components and / or steps unless otherwise stated.

[0039] According to one embodiment of the present invention, a photosensitive resin composition may comprise a binder, a pigment, a multifunctional monomer, and a photoinitiator.

[0040] Adhesives may include polysilsesquioxane-based adhesives. A polysilsesquioxane-based adhesive is a polysilsesquioxane compound prepared by polymerizing a silane monomer with a compound containing an acid functional group; or by polymerizing a silane monomer, a compound containing an acid functional group, and a compound containing a double bond. For example, it can be prepared by polymerizing a compound capable of forming RSiO2. 3 / 2 The unit's silane compound can form RSiO 4 / 2 Polysilsesquioxane adhesives are prepared by copolymerizing silane compounds, compounds containing acid functional groups, and compounds containing double bonds. Preferably, this is achieved by enabling the formation of RSiO 3 / 2 At least two silane compounds of the unit, capable of forming RSiO 4 / 2Polysilsesquioxane adhesives are prepared by polymerizing at least one silane compound, a compound containing an acid functional group, and a compound containing a double bond. Silane monomers may include alkoxy, oxime, acetoxy, epoxy, vinyl, cyclic aliphatic, and similar groups. However, it should be understood that silane monomers are not limited to these and may be selected from any silane monomer capable of forming polysilsesquioxanes through hydrolysis dehydration condensation reactions. Here, R represents a monovalent hydrocarbon group and may independently be, for example: alkyl, such as methyl, ethyl, and propyl; alkenyl, such as vinyl, allyl, isopropenyl, butenyl, hexenyl, and cycloalkenyl; aryl, such as phenyl and xylyl; aralkyl, such as benzyl; or haloalkyl.

[0041] Able to form RSiO 3 / 2 The silane compounds of the unit include, but are not limited to, methyltrimethoxysilane, methacryloxypropyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltriisopropoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, vinyltrimethoxysilane, and vinyltriethoxysilane.

[0042] Able to form RSiO 4 / 2 The silane compounds of the unit include, but are not limited to, tetraethoxysilane, tetramethoxysilane, tetrapropoxysilane, tetrabutoxysilane, and tetrapentoxysilane.

[0043] Polysilsesquioxane adhesives may contain double bonds in their molecules, which is generated by polymerization using compounds containing double bonds. Here, the double bonds may be derived from ester compounds, methacryloyloxy compounds, acryloyloxy compounds, methacrylate compounds, acrylic acid compounds, carboxylic acid compounds, sulfinyl compounds, or sulfonyl compounds. Preferably, the double bonds are derived from ester compounds, methacryloyloxy compounds, acryloyloxy compounds, methacrylate compounds, or acrylic acid compounds.

[0044] Compounds containing double bonds may include, for example, ester compounds, compounds containing methacryloxy groups, compounds containing acryloxy groups, compounds containing methacrylic acid groups, compounds containing acrylic acid groups, carboxylic acid compounds, sulfinyl compounds, sulfonyl compounds, and compounds containing double bonds in -C(=O)O-, -C(=O)-, -C(=O)OH, -S(=O)-, or -S(=O)(=O)-. Such double bonds can be retained in the polysilsesquioxane binder after polymerization.

[0045] When silane monomers, compounds containing acid functional groups, and compounds containing double bonds are referred to as monomers used for polymerizing polysilsesquioxane adhesives, the molar fraction of each molecule of a compound containing a single double bond is about 0.1 to 0.5, preferably about 0.2 to 0.5, and more preferably about 0.2 to 0.45, based on the total number of monomers used for polymerizing polysilsesquioxane adhesives. Here, the molar fraction may vary depending on the number of double bonds per molecule in the compound containing double bonds.

[0046] Polysilsesquioxane adhesives may also contain acid functional groups, which arise from the polymerization of compounds containing acid functional groups. Here, the acid functional groups may be derived from carboxylic acid compounds, sulfinyl compounds, or sulfonyl compounds, and specifically may include carboxylic acid groups, sulfinyl groups, sulfonic acid groups, and similar groups.

[0047] When polysilsesquioxane adhesives are polymerized from carboxylic acid compounds, sulfinyl compounds, or sulfonyl compounds, polysilsesquioxane adhesives may contain both acid functional groups and double bonds.

[0048] Polysilsesquioxane adhesives allow for reproducible control of the development rate of resin compositions by incorporating acid functional groups and double bonds into the adhesive's structure, and exhibit developability in alkaline aqueous solutions. Specifically, the acid functional groups may include carboxylic acid groups, sulfinic acid groups, sulfonic acid groups, and similar groups, preferably including carboxylic acid groups. Since the acid functional groups contain double bonds, these double bonds can also be incorporated into the polysilsesquioxane adhesives. To incorporate acid functional groups into the structure of the polysilsesquioxane adhesives, succinic acid compounds, specifically succinic anhydride compounds, can be used. Succinic anhydride compounds include, but are not limited to, compounds such as, triethoxysilylpropyl succinic anhydride, trimethoxysilylpropyl succinic anhydride, triethoxysilylbutyl succinic anhydride, and trimethoxysilylbutyl succinic anhydride. Due to the introduction of acid functional groups, polysilsesquioxane-based adhesives can have an acid value of about 5 mg KOH / g to 38 mg KOH / g, preferably about 10 mg KOH / g to 35 mg KOH / g, and more preferably about 10 mg KOH / g to 33 mg KOH / g.

[0049] Polysilsesquioxane adhesives can be prepared, for example, by mixing two or more silane monomers with a compound containing an acid group, reacting the mixture with a hydrochloric acid solution, and then stirring the reaction solution. Alternatively, polysilsesquioxane adhesives can be prepared by mixing two or more silane monomers, a compound containing an acid functional group, and a compound containing a double bond, reacting the mixture with a hydrochloric acid solution, and then stirring the reaction solution. The resulting product can then be washed and purified to obtain the polysilsesquioxane adhesive. The silane monomers may include those capable of forming RSiO2. 3 / 2 Silane compounds of the unit and those capable of forming RSiO 4 / 2 The unit is a silane compound. Here, RSiO can be formed. 3 / 2 The silane compounds of the unit are capable of forming RSiO 4 / 2 The molar ratio of the silane compounds in the unit can be between 1:1 and 5:1, preferably between 1.5:1 and 3:1, and more preferably between 2:1 and 3:1.

[0050] When silane monomers, compounds containing acid functional groups, and compounds containing double bonds are referred to as monomers for polymerizing polysilsesquioxane adhesives, the molar fraction of compounds containing one acid functional group per molecule in the total monomers used for polymerizing polysilsesquioxane adhesives can be from about 0.01 to 0.5, preferably from about 0.02 to 0.4, and more preferably from about 0.06 to 0.4. Here, the molar fraction can vary depending on the number of acid functional groups per molecule in the compound containing the acid functional group. For example, when using succinic anhydride compounds, the molar fraction of succinic anhydride compounds (compounds containing acid functional groups) in the total monomers used for polymerizing polysilsesquioxane adhesives can be in the range of from about 0.01 to 0.20, preferably from about 0.03 to 0.20.

[0051] The polysilsesquioxane adhesive may be present in an amount of about 18% to 50% by weight, preferably about 18% to 40% by weight, and more preferably about 18% to 35% by weight, based on the total weight of the photosensitive resin composition.

[0052] Pigments may include at least one of inorganic or organic pigments. For example, pigments may include, but are not limited to, black pigments, red pigments, blue pigments, green pigments, yellow pigments, and similar pigments. Specifically, pigments may include, but are not limited to, at least one selected from the group consisting of: black pigments, red pigments, blue pigments, green pigments, yellow pigments, and mixtures thereof.

[0053] The pigment may be present in an amount of about 1% to 20% by weight, preferably about 5% to 15% by weight, based on the total weight of the photosensitive resin composition. Within this pigment content range, the photosensitive resin composition can be sufficiently cured due to its high permeability to ultraviolet (UV) light upon exposure. Insufficient pigment may degrade the light-blocking effect, while excessive pigment may lead to incomplete curing of the resin composition due to a significant reduction in UV transmittance.

[0054] Black pigments may include, but are not limited to, aniline black, titanium black, carbon black, lactam black, perylene black, and similar pigments. If a black pigment is used alone, lactam black may be used. Lactam black has high transmittance in the ultraviolet band of 350 nm to 400 nm, thus allowing photoinitiators to initiate reactions efficiently.

[0055] Red pigments may include CI Pigment Red 177, CI Pigment Red 254, or derivatives thereof; blue pigments may include CI Pigment Blue 15, CI Pigment Blue 15:1, CI Pigment Blue 15:2, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 16, CI Pigment Blue 22, CI Pigment Blue 60, CI Pigment Blue 64, and similar pigments; green pigments may include CI Pigment Green 6, CI Pigment Green 7, CI Pigment Green 10, CI Pigment Green 36, CI Pigment Green 37, CI Pigment Green 58, CI Pigment Green 59, CI Pigment Green 62, CI Pigment Green 63, and similar pigments; and yellow pigments may... Including, but not limited to, CI Pigment Yellow 1, CI Pigment Yellow 2, CI Pigment Yellow 3, CI Pigment Yellow 4, CI Pigment Yellow 5, CI Pigment Yellow 6, CI Pigment Yellow 10, CI Pigment Yellow 12, CI Pigment Yellow 13, CI Pigment Yellow 14, CI Pigment Yellow 15, CI Pigment Yellow 16, CI Pigment Yellow 17, CI Pigment Yellow 18, CI Pigment Yellow 20, CI Pigment Yellow 24, CI Pigment Yellow 31, CI Pigment Yellow 32, CI Pigment Yellow 34, CI Pigment Yellow 35, CI Pigment Yellow 35:1, CI Pigment Yellow 36, CI Pigment Yellow 36:1, CI Pigment Yellow 37, CI Pigment Yellow 37:1, CI Pigment Yellow 40, and similar pigments.

[0056] As a multifunctional monomer, a tetrafunctional monomer or a monomer with higher functionality can be used to improve reactivity to UV light. For example, the multifunctional monomer may include at least one selected from the group consisting of: dipentaerythritol pentaacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ditrimethylolpropane tetraacrylate, pentaerythritol ethoxylated tetraacrylate, and hexanediol diacrylate. The multifunctional monomer may be present in an amount from about 0.1% to about 10% by weight, preferably from about 1% to about 5% by weight, based on the total weight of the photosensitive resin composition. Within this range, the photosensitive resin composition can achieve patterning (high resolution), high heat resistance, and good reliability by sufficient curing upon exposure to UV light. Insufficient amounts of multifunctional monomers may result in poor resolution or low film retention due to incomplete curing upon exposure to UV light. Conversely, excessive amounts of multifunctional monomers may cause poor resolution in the photosensitive resin composition and may result in residues due to over-curing.

[0057] Photoinitiators may include, for example, 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyl oxime) (Yanjiagu OXE-01), benzoin, 1-hydroxy-cyclohexyl-phenyl ketone, α,α-dimethoxy-α-hydroxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methyl-propane-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-propane-1-one, oligomeric [2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]-propanone], methyldiethanolamine, triethanolamine, Yanjiagu OXE-02, Yanjiagu OXE-03, TPO, TPO-L and similar compounds. The photoinitiator may be present in an amount from about 0.1% to about 5% by weight, preferably from about 0.5% to about 3% by weight, based on the total weight of the photosensitive resin composition. Within this range, photosensitive resin compositions can achieve patterning (high resolution), high heat resistance, and good reliability through sufficient curing upon exposure to UV light. Insufficient photoinitiator may result in poor resolution or low film retention due to incomplete curing upon exposure to UV light. Conversely, excessive photoinitiator may degrade the properties of the photosensitive resin composition due to unreacted photoinitiators.

[0058] The solvent may be, for example, an organic solvent selected from at least one of the following groups: propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, ethylene glycol ether derivatives, ethyl cellosolve, methyl cellosolve, propylene glycol monomethyl ether (PGME), diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol dimethyl ether, propylene glycol n-propyl ether, diethylene glycol dimethyl ether, ethylene glycol ether ester derivatives, ethyl cellosolve acetate, methyl cellosolve acetate, propylene glycol monomethyl ether acetate (PGMEA), carboxylic acid esters, ethyl acetate, n-butyl acetate, amyl acetate, carboxylic acid esters of dicarboxylic acids, diethyl oxalate, diethyl malonate, ethylene glycol dicarboxylic acid esters, ethylene glycol diacetate, propylene glycol diethyl ether... Esters, hydroxycarboxylic acid esters, methyl lactate, ethyl lactate, ethyl glycolate, ethyl 3-hydroxypropionate, ketone esters, methyl pyruvate, ethyl pyruvate, alkoxycarboxylic acid esters, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, ethyl 2-hydroxy-2-methylpropionate, methyl ethoxypropionate, ketone derivatives, methyl ketone, acetylacetone, cyclopentanone, cyclohexanone, 2-heptanone, ketone ether derivatives, diacetone alcohol methyl ether, ketone alcohol derivatives, acetone alcohol, diacetone alcohol, ketal, acetal, 1,3-dioxolane and diethoxypropane, lactone, butyrolactone, γ-valerolactone, amide derivatives, dimethylacetamide, dimethylformamide, anisole, tetrahydrofuran, toluene, methanol, ethanol, and mixtures thereof. When the solvent is present in an amount of about 30% to about 80% by weight of the total weight of the photosensitive resin composition, the photosensitive resin composition exhibits a viscosity suitable for processing.

[0059] According to another embodiment, a cured product can be generated by curing the photosensitive resin composition. For example, when using lactam black as a black pigment, the photosensitive resin composition can be cured by irradiating it with UV light at a wavelength of 350 nm to 400 nm, at which wavelength lactam black has high light transmittance. Here, a photoinitiator that allows the reaction to be initiated in the ultraviolet wavelength range of 350 nm to 400 nm can be used.

[0060] According to another embodiment, the pattern forming method may include coating a photosensitive resin composition and exposing the coated photosensitive resin composition in a position-selective manner, followed by development. Specifically, selective exposure may be performed using a photomask having the desired pattern, thereby distinguishing the exposed portions from the unexposed portions.

[0061] Implementation Plan

[0062] The invention will be described in more detail below with reference to examples and comparative examples.

[0063] Synthesis Example 1: Synthesis of Polysilsesquioxane-based Adhesives

[0064] In a 500 ml three-necked round-bottom flask, methyltrimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane, methacryloxypropyltrimethoxysilane, and triethoxysilylpropylsuccinic anhydride were added in a molar ratio of 17:30:30:20:3, and the mixture was stirred at room temperature for 10 minutes. Then, at a reaction temperature of 50°C or below, 200 g of a 5% deionized hydrochloric acid solution was slowly added to the resulting mixture. The reaction solution was stirred for 10 minutes and then heated to 80°C to polymerize the polysilsesquioxane-based binder. The obtained product was washed with deionized water and ethyl acetate and purified, and distilled under reduced pressure to remove unreacted residues and impurities. Subsequently, PGMEA was added to obtain a polysilsesquioxane-based binder with a solids content of 50% and a weight average molecular weight of about 5,000 g / mol to 7,000 g / mol.

[0065] Synthesis Examples 2 to 5: Synthesis of Polysilsesquioxane-based Adhesives

[0066] Polysilsesquioxane adhesives for Synthetic Examples 2 to 5 were prepared in the same manner as in Synthetic Example 1, except that the molar ratios of methyltrimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane, methacryloxypropyltrimethoxysilane, and triethoxysilylpropylsuccinic anhydride were changed. Table 1 shows the molar ratios of methyltrimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane, methacryloxypropyltrimethoxysilane, and triethoxysilylpropylsuccinic anhydride used in each adhesive.

[0067] Synthesis Example 6: Synthesis of Polysilsesquioxane-based Adhesives

[0068] Polysilsesquioxane adhesives were prepared in the same manner as in Synthesis Example 2, except that 200 g of 5% potassium carbonate deionized water solution was used as the alkaline catalyst instead of hydrochloric acid solution.

[0069] [Table 1]

[0070]

[0071] The acid value and ADR (alkali dissolution rate of the polysilsesquioxane adhesives prepared in Synthesis Examples 1 to 6) were determined.

[0072] For Synthesis Example 6, although triethoxysilylpropyl succinic anhydride was added, the acid value could not be measured because the carboxyl groups failed to incorporate into the copolymer due to the reaction with the base catalyst.

[0073] ADR refers to the alkali dissolution rate, and a higher ADR indicates a faster pattern development rate. Since over- or under-development of the photosensitive resin composition may lead to poor resolution or poor film retention, an ADR in the range of 300 Å / sec to 1,000 Å / sec is preferred.

[0074] Example 1: Preparation of photosensitive resin composition

[0075] The resin composition of Example 1 was prepared by mixing 17% by weight of the polysilsesquioxane adhesive of Synthetic Example 1, 9% by weight of lactam black as a pigment, 3% by weight of dipentaerythritol hexaacrylate as a polyfunctional monomer, 1% by weight of photoinitiator (Yanjiagu OXE-02) and 70% by weight of PGMEA as a solvent, and then stirring at room temperature.

[0076] Examples 2 to 3 and Comparative Examples 1 to 3: Preparation of photosensitive resin compositions

[0077] The resin compositions of Examples 2 to 3 and Comparative Examples 1 to 3 were prepared in the same manner as in Example 1, except that the polysilsesquioxane adhesives of Synthetic Examples 2 to 6 were used instead of the polysilsesquioxane adhesives of Synthetic Example 1.

[0078] Experimental Example 1: Evaluation of Residues in Photosensitive Resin Compositions

[0079] Each of the resin compositions of Examples 1 to 3 and Comparative Examples 1 to 3 was spin-coated onto an indium tin oxide (ITO) substrate, and then soft-baked on a hot plate at approximately 110°C for approximately 70 seconds. The mixture was then subjected to a predetermined pattern mask using a wavelength of 365 nm and an intensity of 50 mW / cm². 2 After irradiation with ultraviolet light, the resin composition was developed for approximately 70 seconds in a 2.38 wt% tetramethylammonium hydroxide (TMAH) aqueous solution at 23 ± 1 °C, and then washed with ultrapure water. It was then hard-baked in an oven at 230 °C for approximately 30 minutes to form a 1 μm thick patterned cured film. The presence of residues on the patterned film was determined using an optical microscope. Residues were defined as undeveloped portions of the resin composition remaining on the un-UV-irradiated film surface, as confirmed by an optical microscope. Residues were evaluated according to the following criteria, and the evaluation results are shown in Table 2.

[0080] - No residue ◎: No residue is observed when viewed under an optical microscope.

[0081] - General residues △: A small amount of residue (5 or fewer) is observed when viewed under an optical microscope.

[0082] - Residue X present: A large number of residues (more than 5) are observed when viewed under an optical microscope.

[0083] Experimental Example 2: Evaluation of the resolution of the photosensitive resin composition

[0084] A patterned cured film was formed in the same manner as in Experimental Example 1.

[0085] The resolution of each specimen was evaluated using a field emission scanning electron microscope (FE-SEM) according to the following criteria, and the evaluation results are shown in Table 2.

[0086] - ◎ (Good): Minimum pattern size less than 5 μm

[0087] -△ (General): Minimum pattern size is greater than or equal to 5 μm and less than 10 μm

[0088] - X (Defect): Minimum pattern size is greater than or equal to 10 μm.

[0089] Experimental Example 3: Evaluation of the storage stability of the photosensitive resin composition

[0090] After storing the polysilsesquioxane copolymers of Synthetic Examples 1 to 3 at room temperature (23°C) for 30 days, resin compositions containing the corresponding copolymers were prepared in the same manner as in Example 1, and these were referred to as Examples 4 to 6.

[0091] For Examples 4 to 6, the residue and resolution were examined in the same manner as in Experimental Examples 1 and 2.

[0092] For instances 4 to 6, storage stability was evaluated according to the following criteria, and the evaluation results are shown in Table 2.

[0093] For Comparative Examples 1 to 3, due to the poor results of residue and resolution evaluation in Experimental Examples 1 and 2, it may not be possible to perform storage stability evaluation.

[0094] - ◎ (Good): No residue and resolution (minimum pattern size) less than 5 μm

[0095] - X (Defect): Residue is produced and the resolution (minimum pattern size) is greater than or equal to 5 μm.

[0096] [Table 2]

[0097]

[0098] In summary, the results of Examples 1 to 3 confirm that the resin compositions of Examples 1 to 3 exhibit excellent properties in terms of residue formation and resolution. Specifically, even after storage at room temperature (23°C) for 30 days, no residue was formed, and the resolution remained excellent, thus confirming that the compositions also have outstanding storage stability.

[0099] While some embodiments have been described above, it should be understood that the above embodiments should not be construed as limiting the present invention, and those skilled in the art can make various modifications, alterations, changes and equivalent substitutions without departing from the spirit and scope of the present invention.

Claims

1. A photosensitive resin composition comprising: a binder; a pigment; a multifunctional monomer; a photoinitiator; and a solvent, wherein... The adhesive includes a polysilsesquioxane-based adhesive, and The polysilsesquioxane-based adhesive has an acid value by introducing acid functional groups into the adhesive.

2. The photosensitive resin composition of claim 1, wherein the adhesive comprises a carboxyl group introduced by a succinic acid compound.

3. The photosensitive resin composition according to claim 2, wherein the succinic acid compound is a succinic anhydride compound.

4. The photosensitive resin composition according to claim 1, comprising: Based on the total weight of the photosensitive resin composition, 18% to 50% by weight of the adhesive; 1% to 20% by weight of the pigment; 0.1% to 10% by weight of the multifunctional monomer; 0.1% to 5% by weight of the photoinitiator; and The solvent is used in amounts ranging from 30% to 80% by weight.

5. The photosensitive resin composition according to claim 2, wherein the succinic acid compound is triethoxysilylpropyl succinic anhydride, trimethoxysilylpropyl succinic anhydride, triethoxysilylbutyl succinic anhydride, or trimethoxysilylbutyl succinic anhydride.

6. The photosensitive resin composition according to claim 1, wherein the adhesive has an acid value of 5 mgKOH / g to 38 mgKOH / g.

7. The photosensitive resin composition according to claim 1, wherein the adhesive has an alkali dissolution rate of 300 to 1000 Å / sec.

8. The photosensitive resin composition according to claim 1, wherein the patterned cured layer formed from the photosensitive resin composition has no residue.

9. The photosensitive resin composition according to claim 1, wherein the patterned cured layer formed from the photosensitive resin composition has a minimum size of less than 10 μm as measured on the patterned cured layer.

10. The photosensitive resin composition according to claim 1, wherein the patterned cured layer formed from the photosensitive resin composition prepared using the adhesive stored at 23°C for 30 days is free of residue and has a minimum size of less than 10 μm as measured on the patterned cured layer.

11. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition is used to form a pixel defined layer (PDL) in an organic light-emitting diode (OLED) display.

12. A cured product prepared by curing the photosensitive resin composition as described in any one of claims 1 to 11.

13. A method for forming a pattern, comprising: Coating with the photosensitive resin composition as described in any one of claims 1 to 11, and The coated photosensitive resin composition is exposed in a position-selective manner, followed by development.

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