Photosensitive resin composition, cured product thereof, pattern forming method, and method for producing 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 comprising a polysilsesquioxane binder and exhibiting excellent developability and pattern characteristics, 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 a photosensitive resin composition, and more specifically to a photosensitive resin composition, its cured product, a patterning method, and a method for preparing a photosensitive resin composition, wherein the photosensitive resin composition comprises a polysilsesquioxane binder and exhibits excellent developability and patterning properties. 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 tetramethylammonium 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] Negative photosensitive resin compositions may contain alkali-soluble resins or binders to remove unexposed portions. For example, acrylic resins, polyimide resins, phenolic resins, polyurethane resins, polyester resins, polyvinyl alcohol resins, epoxy resins, and similar resins have been proposed as binders.

[0007] Furthermore, polysilsesquioxane adhesives are polysiloxane copolymers that exhibit excellent heat resistance, flexibility, transparency, and durability when used in photosensitive resin compositions. However, because polysilsesquioxanes are synthesized via an acid / base-catalyzed sol-gel reaction, it is difficult to incorporate acid functional groups into the adhesive itself as with 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 exhibits excellent developability and patterning properties by incorporating a dispersant having an acid value and amine value within a certain range and contains a polysilsesquioxane binder.

[0009] Technical solutions

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

[0011] The pigment dispersion comprises pigment, dispersant, and dispersing solvent.

[0012] The adhesive comprises a polysilsesquioxane compound, and

[0013] The dispersant has an acid value and an amine value.

[0014] Preferably, the dispersant has an acid value in the range of 10 mgKOH / g to 200 mgKOH / g.

[0015] Preferably, the dispersant has an amine value in the range of 10 mgKOH / g to 200 mgKOH / g.

[0016] Preferably, the photosensitive resin composition further comprises:

[0017] Photopolymerization monomers, photoinitiators, and solvents.

[0018] Preferably, the pigment dispersion comprises:

[0019] 3 to 30 parts by weight of the pigment;

[0020] 1 to 10 parts by weight of the dispersant; and

[0021] 20 to 200 parts by weight of the dispersion solvent.

[0022] Preferably, the photosensitive resin composition comprises: 10 parts by weight to 30 parts by weight of the adhesive;

[0023] 40 to 60 parts by weight of the pigment dispersion;

[0024] From 1 part by weight to 10 parts by weight of the aforementioned photopolymerizable monomer;

[0025] 0.1 to 5 parts by weight of the photoinitiator; and

[0026] From 10 to 50 parts by weight of the solvent.

[0027] Preferably, the polysilsesquioxane compound is prepared by copolymerizing the following substances:

[0028] Able to form RSiO 3 / 2 At least two silane compounds of the unit; and

[0029] Able to form RSiO 4 / 2 At least one silane compound of the unit.

[0030] According to another aspect of the present invention, a cured product is provided, which is prepared by curing the photosensitive resin composition.

[0031] 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

[0032] The coated photosensitive resin composition is exposed in a position-selective manner, followed by development.

[0033] Beneficial effects

[0034] Embodiments of the present invention provide a photosensitive resin composition that improves the pigment dispersibility of a pigment dispersion by incorporating a dispersant having acid functional groups, while simultaneously improving developability to form high-resolution photoresist patterns.

[0035] Embodiments of the present invention provide a photosensitive resin composition that exhibits excellent properties in terms of coatability, developability, and compatibility between binders and dispersants. 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 terms “comprising,” “including,” and / or “containing” (and their grammatical variations) used in this specification indicate the presence of the stated components and / or steps, but do 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 include a binder and a pigment dispersion.

[0040] The adhesive may contain polysilsesquioxane compounds.

[0041] Polysilsesquioxane adhesives are polysilsesquioxane compounds prepared by polymerizing silane-based monomers. For example, polysilsesquioxane adhesives can be prepared by polymerizing silane-based monomers. 3 / 2 The unit's silane compound and the ability to form RSiO 4 / 2 It is prepared by copolymerization of silane compounds of unit cells, preferably by enabling the formation of RSiO. 3 / 2 At least two silane compounds of the unit and capable of forming RSiO 4 / 2 It is prepared by copolymerization of at least one silane compound of the unit, more preferably by enabling the formation of RSiO. 3 / 2 At least three silane compounds of the unit and capable of forming RSiO 4 / 2 It is prepared by copolymerization of at least one silane compound of the unit. Silane monomers may include alkoxy, oxime, acetoxy, 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 by hydrolysis dehydration condensation reaction. 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.

[0042] Able to form RSiO 3 / 2The 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.

[0043] Able to form RSiO 4 / 2 The silane compounds of the unit include, but are not limited to, tetraethoxysilane, tetramethoxysilane, tetrapropoxysilane, tetrabutoxysilane, and tetrapentoxysilane.

[0044] Polysilsesquioxane adhesives can be prepared, for example, by mixing two or more silane monomers and reacting the mixture with a hydrochloric acid solution, followed by stirring the reaction solution. The resulting product can then be washed and purified to obtain the polysilsesquioxane compound. 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 weight ratio of the silane compounds in the unit can be between 1:1 and 5:1, preferably 1.5:1 to 3:1, and more preferably 2:1 to 2.5:1.

[0045] The photosensitive resin composition according to embodiments of the present invention may contain a polysilsesquioxane compound as a binder, thereby improving heat resistance, flexibility, transparency and durability.

[0046] Pigment dispersions may contain pigments, dispersants, and dispersion solvents.

[0047] The dispersant may have both an acid value and an amine value within a certain range, preferably both within a certain range. When the dispersant has both an acid value and an amine value within a certain range, it can ensure good developability of the photosensitive resin composition containing the pigment dispersion while ensuring good dispersibility of the pigment dispersion and good compatibility with the binder.

[0048] Specifically, the dispersant may have an acid value in the range of 10 mgKOH / g to 200 mgKOH / g, preferably 10 mgKOH / g to 150 mgKOH / g, and more preferably 20 mgKOH / g to 100 mgKOH / g. Within this acid value range of the dispersant, photosensitive resin compositions containing polysilsesquioxane compounds may exhibit improved developability.

[0049] Specifically, the dispersant may have an amine value in the range of 10 mgKOH / g to 200 mgKOH / g, preferably 25 mgKOH / g to 150 mgKOH / g, and more preferably 35 mgKOH / g to 100 mgKOH / g. Within this amine value range, the dispersant can ensure good dispersibility of the pigment dispersion.

[0050] Dispersants may comprise fatty acid compounds, phosphoric acid compounds, carboxylic acid compounds, polyurethane compounds, polyamine compounds, polyacrylate compounds, polyacrylic acid compounds, or structured copolymer compounds. Suitable functional groups may be incorporated into fatty acid compounds, phosphoric acid compounds, carboxylic acid compounds, polyurethane compounds, polyamine compounds, polyacrylate compounds, polyacrylic acid compounds, or structured copolymer compounds to provide acid value, amine value, or both.

[0051] Pigments may include, but are not limited to, black, red, blue, green, yellow, and similar pigments. For example, black pigment may be used alone to ensure that the photosensitive resin composition exhibits excellent opacifying properties. Preferably, at least one pigment selected from the group consisting of red, blue, green, yellow, and similar pigments is used in conjunction with black pigment to prevent internal uncuring of the photosensitive resin composition, which may occur when black pigment is used alone.

[0052] Black pigments may include, but are not limited to, aniline black, titanium black, carbon black, lactam 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.

[0053] 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.

[0054] The dispersing solvent may be an organic solvent, such as at least one selected from the group consisting of: 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 diethyl ether... Esters, propylene glycol diacetate, 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 ethyl 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, diethoxypropane, lactone, butyrolactone, γ-valerolactone, amide derivatives, dimethylacetamide, dimethylformamide, anisole, and mixtures thereof.

[0055] The pigment dispersion may contain 3 to 30 parts by weight of pigment, 1 to 10 parts by weight of dispersant and 20 to 200 parts by weight of dispersing solvent, preferably containing 8 to 25 parts by weight of pigment, 2 to 8 parts by weight of dispersant and 40 to 160 parts by weight of dispersing solvent, more preferably containing 10 to 20 parts by weight of pigment, 3 to 6 parts by weight of dispersant and 60 to 120 parts by weight of dispersing solvent.

[0056] Pigment dispersions can be prepared by feeding pigments, dispersants, and dispersing solvents into a dispersion apparatus, followed by dispersion until the pigment dispersion has a particle size (D50) within a certain range. The dispersion apparatus is not particularly limited. For example, pigments, dispersants, and dispersing solvents can be fed into a horizontal bead mill, and the resulting mixture can be dispersed using 0.1 mm beads until the pigment dispersion has a particle size (D50) of 5 nm to 100 nm.

[0057] According to one embodiment of the present invention, the photosensitive resin composition may further include a photopolymerizable monomer, a photoinitiator, and a solvent.

[0058] As photopolymerizable monomers, tetrafunctional monomers or monomers with higher functionality can be used to improve reactivity to ultraviolet (UV) light. For example, photopolymerizable monomers may include at least one selected from the group consisting of: dipentaerythritol pentaacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ditrimethylolpropane tetraacrylate, and pentaerythritol ethoxylated tetraacrylate.

[0059] Photoinitiators may include, for example, 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, oligo[2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]-propanone], methyldiethanolamine, triethanolamine and similar compounds.

[0060] 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 diacetic acid. Esters, propylene glycol diacetate, 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 ethyl 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 and mixtures thereof.

[0061] According to one embodiment of the present invention, the photosensitive resin composition may comprise 10 to 30 parts by weight of a binder, 40 to 60 parts by weight of a pigment dispersion, 1 to 10 parts by weight of a photopolymerizable monomer, 0.1 to 5 parts by weight of a photoinitiator, and 10 to 50 parts by weight of a solvent. Preferably, the photosensitive resin composition may comprise 10 to 25 parts by weight of a binder, 45 to 60 parts by weight of a pigment dispersion, 1 to 7 parts by weight of a photopolymerizable monomer, 0.1 to 3 parts by weight of a photoinitiator, and 20 to 40 parts by weight of a solvent; more preferably, it comprises 10 to 20 parts by weight of a binder, 45 to 55 parts by weight of a pigment dispersion, 1 to 5 parts by weight of a photopolymerizable monomer, 0.5 to 3 parts by weight of a photoinitiator, and 25 to 35 parts by weight of a solvent.

[0062] 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.

[0063] 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.

[0064] Implementation Plan

[0065] The invention will be described in more detail below with reference to examples and comparative examples.

[0066] Preparation Example 1: Preparation of Polysilsesquioxane Compounds

[0067] In a 500 ml three-necked round-bottom flask, 39 parts by weight of methyltrimethoxysilane, 90 parts by weight of phenyltrimethoxysilane, 85 parts by weight of tetraethoxysilane, and 71 parts by weight of methacryloxypropyltrimethoxysilane were added, 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 compound. The obtained product was washed with deionized water and ethyl acetate to purify it, and distilled under reduced pressure to remove unreacted material and impurities. Finally, a polysilsesquioxane compound with a solids content of 50% was obtained by dissolving the resulting product in PGMEA.

[0068] Preparation Example 2: Preparation of Pigment Dispersion

[0069] 7.5 parts by weight of lactam black as pigment, 2.3 parts by weight of dispersant and 40.2 parts by weight of PGMEA as dispersion solvent were charged into a horizontal bead mill, and the resulting mixture was then dispersed using 0.1 mm beads until the pigment dispersion had a particle size of 50 nm (D50).

[0070] As dispersants, dispersant A (amine value: 2 mgKOH / g), dispersant B (amine value: 4 mgKOH / g), dispersant C (amine value: 48 mgKOH / g), dispersant D (acid value: 38 mgKOH / g; amine value: 44 mgKOH / g), dispersant E (acid value: 94 mgKOH / g; amine value: 94 mgKOH / g), dispersant F (acid value: 53 mgKOH / g), or dispersant G (acid value: 36 mgKOH / g) are used.

[0071] Example 1: Preparation of photosensitive resin composition

[0072] A photosensitive resin composition was prepared by mixing 16 parts by weight of the polysilsesquioxane compound of Preparation Example 1, 50 parts by weight of the pigment dispersion of Preparation Example 2, 3 parts by weight of dipentaerythritol hexaacrylate as a photopolymerization monomer, 1 part by weight of the photoinitiator (OXE-01), and 30 parts by weight of PGMEA as a solvent.

[0073] For the pigment dispersion used in Example 1, dispersant A with an amine value of 2 mgKOH / g was used as the dispersant.

[0074] Examples 2 to 7 and Comparative Examples 1 to 2: Preparation of photosensitive resin compositions

[0075] The resin compositions of Examples 2 to 7 were prepared in the same manner as in Example 1, except that dispersant B to dispersant F were used instead of dispersant A.

[0076] The resin composition of Comparative Example 1 was prepared in the same manner as in Example 1 without using a pigment dispersion. The resin composition of Comparative Example 2 was prepared in the same manner as in Example 1, except that lactam black was used alone as the pigment instead of the pigment dispersion.

[0077] The compositions of photosensitive resins prepared in the examples and comparative examples are listed in Table 1.

[0078] Table 1

[0079]

[0080] Experimental Example 1: Evaluation of the compatibility between binder and pigment dispersion

[0081] The compatibility of the pigment dispersions (containing dispersants A to F, respectively) and the pigments alone (Comparative Example 2) used in Examples 1 to 7 with the polysilsesquioxane adhesive was examined.

[0082] The polysilsesquioxane binder prepared in Preparation Example 1, the pigment dispersion or individual pigment used in Examples 1 to 7, and the solvent (PGMEA) were mixed in a weight ratio of 1:1:1. The changes in phase separation, turbidity, and sedimentation of the mixed solution were then visually inspected.

[0083] If the mixed solution exhibits phase separation, low transparency, or sedimentation, it is rated as X; and if the mixed solution is well mixed, exhibits no phase separation and sedimentation, and is transparent to the naked eye, it is rated as ○. The evaluation results are shown in Table 2.

[0084] [Table 2]

[0085]

[0086] In the case of a single pigment (Comparative Example 2), the compatibility is poor because it does not contain a dispersant.

[0087] Although the pigment dispersions used in Examples 1 and 2 have amine values, the amine values ​​are too low, resulting in poor compatibility. Furthermore, the pigment dispersion in Example 5 exhibits poor compatibility due to its excessively high acid and amine values.

[0088] Conversely, the pigment dispersions in Examples 3, 4, 6 and 7 exhibited good compatibility because their acid and amine values ​​fell within a certain range.

[0089] Experimental Example 2: Evaluation of the dispersibility of pigment dispersions

[0090] The dispersibility of the pigment dispersions (containing dispersants A to F, respectively) used in Examples 1 to 7 and the individual pigments (Comparative Example 2) was examined.

[0091] The polysilsesquioxane binder of Preparation Example 1, the pigment dispersion or individual pigment used in Examples 1 to 7, and the solvent (PGMEA) were mixed in a weight ratio of 1:1:1. The changes in viscosity and particle size of the resulting mixture were then examined.

[0092] Increased viscosity or gelation indicates poor dispersibility. Uneven particle size or lack of increased particle size also indicates poor dispersibility. Poor dispersibility is indicated by X, and good dispersibility by ○. The evaluation results are shown in Table 3.

[0093] [Table 3]

[0094]

[0095] In the case of a single pigment (Comparative Example 2), the dispersibility is extremely poor because it does not contain a dispersant.

[0096] Although the pigment dispersions used in Examples 1 and 2 have amine values, the amine values ​​are too low, resulting in poor dispersion. Furthermore, the pigment dispersions in Examples 6 and 7 exhibit poor dispersibility due to the lack of amine values.

[0097] Conversely, Examples 3 to 5 exhibited good dispersibility because their amine values ​​fell within a specific range.

[0098] Experimental Example 3: Evaluation of the coatability of photosensitive resin compositions

[0099] Each of the photosensitive resin compositions of Examples 1 to 7 and Comparative Examples 1 to 2 was spin-coated at 1,300 rpm using a spin coater to prepare a 1 μm thick coated sample. The coatability of each sample was evaluated according to the following criteria, and the evaluation results are shown in Table 4.

[0100] - ○ (Good): No pinholes, no stains

[0101] - △ (General): Fewer than two pinholes and stains

[0102] - X (Defective): 2 or more pinholes and stains

[0103] [Table 4]

[0104]

[0105] Despite the lack of pigment dispersion, the resin composition of Comparative Example 1 still exhibited good coatability. The resin compositions of Comparative Example 2, as well as Examples 1, 2, 5, 6, and 7, had two or more pinholes and blemishes, indicating poor coatability.

[0106] The resin composition of Example 3 has a single pinhole, indicating general coatability, while the resin composition of Example 4 has no pinholes or blemishes, indicating good coatability.

[0107] Experimental Example 4: Evaluation of the developability of photosensitive resin compositions

[0108] Each of the coating films prepared in Experimental Example 3 (Examples 1 to 7) and Comparative Examples 1 to 2 was exposed to ultraviolet light using a photomask, so that the exposed and unexposed portions could be distinguished. The developability was then checked after complete immersion in a 2.38% aqueous solution of TMAH (tetramethylammonium hydroxide) at 23°C. The developability of each composition was evaluated according to the following criteria, and the evaluation results are shown in Table 5.

[0109] - ○ (Good): Develops in 2.38% TMAH aqueous solution within 70 to 100 seconds.

[0110] - X (Defective): Developed in 2.38% TMAH aqueous solution after more than 100 seconds.

[0111] [Table 5]

[0112]

[0113] The composition of Comparative Example 1 was a polysilsesquioxane composition exhibiting poor developability. Despite the presence of pigment, the resin composition of Comparative Example 2 also exhibited poor developability due to poor compatibility and dispersibility. The compositions of Examples 1 to 3 exhibited poor developability due to a lack of acid value in the dispersant. Conversely, the compositions of Examples 4 to 7, each containing a dispersant with an acid value within a certain range, exhibited good developability.

[0114] Although 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, changes, alterations and equivalent substitutions without departing from the spirit and scope of the present invention.

Claims

1. A photosensitive resin composition comprising: a binder; and a pigment dispersion, wherein... The pigment dispersion comprises pigment, dispersant, and dispersing solvent. The adhesive comprises a polysilsesquioxane compound, and The dispersant has an acid value and an amine value.

2. The photosensitive resin composition according to claim 1, wherein the dispersant has an acid value in the range of 10 mgKOH / g to 200 mgKOH / g.

3. The photosensitive resin composition according to claim 1, wherein the dispersant has an amine value in the range of 10 mgKOH / g to 200 mgKOH / g.

4. The photosensitive resin composition according to claim 1 further comprises: a photopolymerizable monomer, a photoinitiator, and a solvent.

5. The photosensitive resin composition according to claim 1, wherein the pigment dispersion comprises: 3 to 30 parts by weight of the pigment; 1 to 10 parts by weight of the dispersant; and 20 to 200 parts by weight of the dispersion solvent.

6. The photosensitive resin composition according to claim 4, comprising: 10 to 30 parts by weight of the adhesive; 40 to 60 parts by weight of the pigment dispersion; From 1 part by weight to 10 parts by weight of the aforementioned photopolymerizable monomer; 0.1 to 5 parts by weight of the photoinitiator; and From 10 to 50 parts by weight of the solvent.

7. The photosensitive resin composition according to claim 1, wherein the polysilsesquioxane compound is prepared by copolymerizing the following substances: Able to form RSiO 3 / 2 At least two silane compounds of the unit; and Able to form RSiO 4 / 2 At least one silane compound of the unit.

8. A cured product prepared by curing a photosensitive resin composition as described in any one of claims 1 to 7.

9. A method for forming a pattern, comprising: Coating with the photosensitive resin composition as described in any one of claims 1 to 7, and The coated photosensitive resin composition is exposed in a position-selective manner, followed by development.

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