Photosensitive resin composition, cured product thereof, pattern formation method, and method for preparing 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 preparing the photosensitive resin composition. Specifically, the present invention relates to a photosensitive resin composition which contains a polysilsesquioxane binder and exhibits excellent developability and pattern characteristics, a cured product, a method for forming a pattern, and a method for preparing the photosensitive resin composition.

Description

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

[0001] 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, and more particularly, to a photosensitive resin composition comprising a polysilsesquioxane binder and having excellent developability and pattern characteristics, a cured product thereof, a method for forming a pattern, and a method for producing a photosensitive resin composition.

[0002] Traditionally, OLED pixels have been patterned using methods such as screen printing, roll-to-roll, and laser direct patterning. Additionally, photolithography using a photoresist composition is now being used in the patterning process of OLED display manufacturing. Photolithography enables large-area patterning of OLED pixels, and can also pattern ultra-fine OLED pixels, enabling the implementation of high-resolution display screens.

[0003] To realize high-density, ultra-high-resolution OLED display screens, forming ultra-fine patterns remains crucial. Methods for forming ultra-fine patterns include positive and negative methods. Positive methods involve removing the exposed portion of a photoresist composition to form a pattern, while negative methods involve removing the unexposed portion of the photoresist composition to form a pattern.

[0004] The photoresist compositions used in both positive and negative methods are distinct. Among these, the negative photoresist composition must have developability so that the unexposed portion can be removed. Conventional negative photoresist photosensitive resin compositions contain acid functional groups in the binder, and thus development is performed using an alkaline developer such as KOH or TMAH (Tetramethyl Ammonium Hydroxide). Negative photosensitive resin compositions with improved developability have been disclosed, for example, in Korean Patent No. 10-2585445 (October 5, 2023), Korean Patent No. 10-1787651 (October 18, 2017), and Korean Patent No. 10-1306778 (September 17, 2013).

[0005] The negative photosensitive resin composition may contain an alkali-soluble resin or binder to enable removal of unexposed portions. Examples of binders proposed include acrylic resins, polyimide resins, phenol resins, polyurethane resins, polyester resins, polyvinyl alcohol resins, and epoxy resins.

[0006] In addition, polysilsesquioxane binders are copolymers of polysiloxanes and have excellent heat resistance, flexibility, transparency, and durability, making them suitable for use in photosensitive resin compositions. However, since polysilsesquioxane is synthesized through a sol-gel reaction using an acid / base catalyst, it has been difficult to introduce acid functional groups into the binder itself, as in conventional binders. As a result, most polysilsesquioxane binders do not dissolve well in alkaline developers, resulting in poor developability. Despite the above-mentioned physical properties of polysilsesquioxane binders, it is difficult to apply them to negative-type photosensitive resin compositions.

[0007] Accordingly, the present invention sought to provide a photosensitive resin composition containing a polysilsesquioxane binder and having excellent developability and pattern characteristics using a dispersant having a certain range of acid and amine values.

[0008] According to one aspect of the present invention, a composition comprising a binder and a pigment dispersion,

[0009] The above pigment dispersion liquid contains a pigment, a dispersant, and a dispersing solvent,

[0010] The above binder comprises a polysilsesquioxane compound,

[0011] The above dispersant can provide a photosensitive resin composition characterized by having an acid value and an amine value.

[0012] Preferably, a photosensitive resin composition can be provided in which the acid value of the dispersant is in the range of 10 to 200 mgKOH / g.

[0013] Preferably, a photosensitive resin composition can be provided in which the amine value of the dispersant is in the range of 10 to 200 mgKOH / g.

[0014] Preferably, the photosensitive resin composition comprises:

[0015] A photosensitive resin composition can be provided, further comprising a photopolymerizable monomer, a photoinitiator, and a solvent.

[0016] Preferably, the pigment dispersion liquid is

[0017] 3 to 30 parts by weight of the above pigment;

[0018] 1 to 10 parts by weight of the dispersant; and

[0019] A photosensitive resin composition can be provided, which comprises 20 to 200 parts by weight of a dispersing solvent.

[0020] Preferably, the binder is 10 to 30 parts by weight;

[0021] The pigment dispersion is 40 to 60 parts by weight;

[0022] The above photopolymerizable monomer is 1 to 10 parts by weight;

[0023] The photoinitiator is 0.1 to 5 parts by weight; and

[0024] The above solvent can provide a photosensitive resin composition having 10 to 50 parts by weight.

[0025] Preferably, the polysilsesquioxane compound is

[0026] RSiO 3 / 2 Two or more silane compounds capable of forming a unit; and

[0027] RSiO 4 / 2 A photosensitive resin composition can be provided, which is a copolymer of one or more silane compounds capable of forming a unit.

[0028] According to another aspect of the present invention, a cured product manufactured by curing the photosensitive resin composition can be provided.

[0029] According to another aspect of the present invention, the photosensitive resin composition is applied,

[0030] A method for forming a pattern can be provided, which includes selectively exposing an applied photosensitive resin composition to light and then developing it.

[0031] According to the present invention, a photosensitive resin composition can be provided that can form a high-resolution photoresist pattern by improving the pigment dispersibility of a pigment dispersant and at the same time improving the developability by using a dispersant having an acid functional group introduced therein.

[0032] In addition, a photosensitive resin composition having excellent compatibility between a binder and a dispersant and improved coatability and developability can be provided.

[0033] Hereinafter, the present invention will be described.

[0034] All terms (including technical and scientific terms) used in this specification, unless otherwise defined, may be used in their common sense by those of ordinary skill in the art to which the present invention pertains. Furthermore, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0035] Additionally, throughout this specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0036]

[0037] As one embodiment of the present invention, the photosensitive resin composition may include a binder and a pigment dispersion.

[0038] The above binder may include a polysilsesquioxane compound.

[0039] Polysilsesquioxane compounds can be manufactured by polymerizing silane monomers, for example, RSiO 3 / 2 Silane compounds capable of forming units and RSiO 4 / 2 It can be manufactured by copolymerizing a silane compound capable of forming a unit, preferably RSiO 3 / 2 Two or more silane compounds capable of forming a unit and RSiO 4 / 2 It can be manufactured by copolymerizing one or more silane compounds capable of forming a unit, and more preferably RSiO 3 / 2 Three or more silane compounds capable of forming units and RSiO 4 / 2It can be produced by copolymerizing one or more silane compounds capable of forming a unit. The silane monomer may include an alkoxy group, an oxime group, an acetoxy group, etc., but is not limited thereto as long as it can form polysilsesquioxane by a hydrolysis, dehydration, and condensation reaction. The R is a monovalent hydrocarbon group, and may be, for example, an alkyl group such as methyl, ethyl, or propyl independently; an alkenyl group such as vinyl, allyl, isopropenyl, butenyl, hexenyl, and cycloalkenyl; an aryl group such as phenyl or xylyl; an aralkyl group such as benzyl; or a halogenated alkyl group.

[0040] RSiO 3 / 2 Examples of silane compounds capable of forming the unit include, but are not limited to, methyltrimethoxysilane, methacryloxypropyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltriisopropoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, vinyltrimethoxysilane, and vinyltriethoxysilane.

[0041] RSiO 4 / 2 Examples of silane compounds capable of forming units include, but are not limited to, tetraethoxysilane, tetramethoxysilane, tetrapropoxysilane, tetrabutoxysilane, and tetrapentoxysilane.

[0042] A polysilsesquioxane compound can be prepared, for example, by mixing two or more silane monomers, reacting them with an aqueous hydrochloric acid solution, and stirring the reaction solution. Afterwards, the reaction solution can be washed and purified to obtain a polysilsesquioxane compound. The silane monomer is RSiO. 3 / 2 Silane compounds capable of forming units and RSiO 4 / 2 Silane compounds that can form units can be used, RSiO 3 / 2 Silane compounds capable of forming units and RSiO 4 / 2The weight ratio of the silane compounds capable of forming the unit may be 1:1 to 5:1, preferably 1.5:1 to 3:1, and more preferably 2:1 to 2.5:1.

[0043]

[0044] The photosensitive resin composition of the present invention can improve heat resistance, flexibility, transparency, and durability by including a polysilsesquioxane compound as a binder.

[0045]

[0046] The above pigment dispersion may include a pigment, a dispersant, and a dispersing solvent.

[0047] The dispersant may have both a certain range of acid values ​​and amine values, and preferably, it should have a certain range of acid values ​​and amine values. When the dispersant has a certain range of acid values ​​and amine values, the photosensitive resin composition can be provided with good dispersibility of the pigment dispersion and excellent compatibility between the binder and the dispersant, and at the same time, the developability of the photosensitive resin composition including the pigment dispersion can be improved.

[0048] Specifically, the acid value of the dispersant may be in the range of 10 to 200 mgKOH / g, preferably in the range of 10 to 150 mgKOH / g, and more preferably in the range of 20 to 100 mgKOH / g. By having the acid value of the dispersant in a certain range, the developability of the photosensitive resin composition including the polysilsesquioxane compound may be improved.

[0049] Specifically, the amine value of the dispersant may be in the range of 10 to 200 mgKOH / g, preferably in the range of 25 to 150 mgKOH / g, and more preferably in the range of 35 to 100 mgKOH / g. By having an amine value of the dispersant within a certain range, the dispersibility of the pigment dispersion can be improved.

[0050] Dispersants may be fatty acid-based, phosphoric acid-based, carboxylic acid-based, polyurethane-based, polyamine-based, polyacrylate-based, polyacrylic-based compounds, or structured copolymer compounds. To have an acid value, an amine value, or both an acid value and an amine value, an appropriate functional group may be introduced into fatty acid-based, phosphoric acid-based, carboxylic acid-based, polyurethane-based, polyamine-based, polyacrylate-based, polyacrylic-based compounds, or structured copolymer compounds.

[0051] The pigment may be a black pigment, a red pigment, a blue pigment, a green pigment, a yellow pigment, etc., and is not particularly limited thereto. For example, a black pigment may be used alone, in which case the light-blocking properties of the photosensitive resin composition are excellent. Preferably, one or more pigments selected from the group consisting of a red pigment, a blue pigment, a green pigment, a yellow pigment, etc. may be mixed with a black pigment and used, and in this case, the problem of internal non-curing of the photosensitive resin composition that may occur when a black pigment is used alone can be resolved.

[0052] Examples of black pigments that can be used include, but are not limited to, aniline black, titanium black, carbon black, and lactam black. When using a black pigment alone, lactam black can be used, and its high light transmittance in the 350 to 400 nm ultraviolet range allows the photoinitiator to efficiently initiate the reaction.

[0053] The red pigment may be CI Pigment Red 177, CI Pigment Red 254, or derivatives thereof, the blue pigment may be CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 60, and 64, the green pigment may be CI Pigment Green 6, 7, 10, 36, 37, 58, 59, 62, and 63, the yellow pigment may be CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, You can use 37, 37:1, 40, etc., but are not limited to these.

[0054]

[0055] The dispersion solvent may be an organic solvent, for example, propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, 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, glycol ether ester derivatives, ethyl cellosolve acetate, methyl cellosolve acetate, propylene glycol monomethyl ether acetate (PGMEA), carboxylate, ethyl acetate, n-butyl acetate, amyl acetate, carboxylate of dibasic acid, diethyl oxylate, diethyl malonate, dicarboxylate of glycol, ethylene glycol diacetate, propylene glycol Diacetate, hydroxycarboxylate, methyl lactate, ethyl lactate, ethyl glycolate, ethyl-3-hydroxypropionate, ketone ester, methyl pyruvate, ethyl pyruvate, alkoxycarboxylic acid ester, 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, acetol, diacetone alcohol, ketal, acetal, 1,3-dioxalane, diethoxypropane, lactone, butyrolactone, gamma valerolactone, amide derivatives, It may be at least one selected from the group consisting of dimethylacetamide, dimethylformamide, anisole, and mixtures thereof.

[0056] The pigment dispersion may contain 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, preferably 8 to 25 parts by weight of the pigment, 2 to 8 parts by weight of the dispersant, and 40 to 160 parts by weight of the dispersion solvent, and more preferably 10 to 20 parts by weight of the pigment, 3 to 6 parts by weight of the dispersant, and 60 to 120 parts by weight of the dispersion solvent.

[0057] Pigment dispersions can be manufactured by placing pigment, dispersant, and solvent into a dispersion device and dispersing the mixture until a certain particle size (D50) is achieved. The dispersion device is not particularly limited. For example, pigment, dispersant, and solvent can be placed into a horizontal bead mill, 0.1 mm beads can be added, and dispersion can be performed until the particle size (D50) of the pigment dispersion reaches 5 to 100 nm.

[0058]

[0059] As one embodiment of the present invention, the photosensitive resin composition may further include a photopolymerization monomer, a photoinitiator, and a solvent.

[0060] The photopolymerizable monomer may be a polyfunctional monomer having four or more functional groups to increase reactivity to UV. For example, at least one selected from the group consisting of dipentaerythritol pentaacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ditrimethylolpropane tetraacrylate, and pentaerythritol ethoxylated tetraacrylate may be used.

[0061] Photoinitiators that can be used include, for example, benzoin, 1-hydroxy-cyclohexyl-phenyl ketone, α,α-dimethoxy-α-hydroxy acetophenone, 1-(4-isopropylenyl)-2-hydroxy-2-methyl-propan-1-one, 1-[4-(2hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-propan-1-one, oligo[2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]-propanone, methyldiethanolamine, and triethanolamine.

[0062] The solvent may be an organic solvent, for example, propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, 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, glycol ether ester derivatives, ethyl cellosolve acetate, methyl cellosolve acetate, propylene glycol monomethyl ether acetate (PGMEA), carboxylate, ethyl acetate, n-butyl acetate, amyl acetate, carboxylate of dibasic acid, diethyl oxylate, diethyl malonate, dicarboxylate of glycol, ethylene glycol diacetate, propylene glycol Diacetate, hydroxycarboxylate, methyl lactate, ethyl lactate, ethyl glycolate, ethyl-3-hydroxypropionate, ketone ester, methyl pyruvate, ethyl pyruvate, alkoxycarboxylic acid ester, 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, acetol, diacetone alcohol, ketal, acetal, 1,3-dioxalane and diethoxypropane, lactone, butyrolactone, gamma valerolactone, amide derivatives, It may be at least one selected from the group consisting of dimethylacetamide, dimethylformamide, anisole, and mixtures thereof.

[0063]

[0064] As one embodiment of the present invention, the photosensitive resin composition may include 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 include 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, and more preferably, the photosensitive resin composition may include 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.

[0065]

[0066] As one embodiment of the present invention, a cured product can be manufactured by curing the photosensitive resin composition. For example, when lactam black is used as a black pigment, curing of the photosensitive resin composition can be achieved by irradiating it with ultraviolet rays in the range of 350 to 400 nm, which is a region in which lactam black has high light transmittance. At this time, a photoinitiator that initiates the reaction in the range of 350 to 400 nm ultraviolet rays can be selected and used.

[0067] As one embodiment of the present invention, a method for forming a pattern may include applying the photosensitive resin composition, selectively exposing the applied photosensitive resin composition to light, and then developing the photosensitive resin composition. Specifically, selectively exposing the photosensitive resin composition to light may be performed by using a photomask having a desired pattern formed thereon to distinguish between exposed and unexposed areas.

[0068] Hereinafter, the present invention is specifically described with reference to examples and comparative examples of the present invention.

[0069]

[0070] Manufacturing Example 1. Synthesis of polysilsesquioxane compounds

[0071] In a 500 ml three-necked round-bottomed 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 stirred at room temperature for 10 minutes. Then, 200 g of a 5% hydrochloric acid aqueous solution dissolved in deionized water was slowly added dropwise at a reaction temperature of 50°C or lower and reacted. After stirring the reaction solution for 10 minutes, the temperature was increased to 80°C to polymerize the polysilsesquioxane compound. After washing and purifying with deionized water and ethyl acetate, unreacted materials and impurities were removed by distillation under reduced pressure. Thereafter, PGMEA was added to obtain a polysilsesquioxane compound having a solid content of 50%.

[0072]

[0073] Manufacturing Example 2. Manufacturing of pigment dispersion

[0074] After placing 7.5 parts by weight of lactam black as a pigment, 2.3 parts by weight of dispersant, and 40.2 parts by weight of PGMEA as a dispersing solvent into a horizontal bead mill, 0.1 mm beads were added and dispersed until the particle size (D50) of the pigment dispersion became 50 nm.

[0075] The dispersant used was 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).

[0076]

[0077] Example 1. Preparation of photosensitive resin composition

[0078] A photosensitive resin composition was prepared by mixing 16 parts by weight of the polysilsesquioxane compound of Manufacturing Example 1, 50 parts by weight of the pigment dispersion of Manufacturing Example 2, 3 parts by weight of dipentaerythritol hexaacrylate as a photopolymerization monomer, 1 part by weight of a photoinitiator (trade name OXE-01), and 30 parts by weight of PGMEA as a solvent.

[0079] Among the pigment dispersions used in Example 1, dispersant A having an amine value of 2 mgKOH / g was used.

[0080]

[0081] Examples 2 to 7 and Comparative Examples 1 to 2. Preparation of photosensitive resin compositions

[0082] The resin compositions of Examples 2 to 7 were prepared in the same manner as the resin composition of Example 1, but instead of dispersant A, dispersants B to F were used, respectively.

[0083] The resin composition of Comparative Example 1 was prepared in the same manner as the resin composition of Example 1, but did not include a pigment dispersion. The resin composition of Comparative Example 2 was prepared in the same manner as the resin composition of Example 1, but contained only lactam black as a pigment instead of a pigment dispersion.

[0084] The presence or absence and weight ratio of the components used to prepare the photosensitive resin compositions of the examples and comparative examples are described in Table 1.

[0085] Comparative composition example Example 121234567 Pigment dispersion solution Pigment-○○○○○○○○ Dispersant acid value-----38945336 Amine value--24484494--Weight ratio Binder 16161616161616161616 Pigment dispersion solution Pigment-7.57.57.57.57.57.57.57.5 Dispersant--2.32.32.32.32.32.32.3 Dispersing solvent--40.240.240.240.240.240.240.240.2 Photopolymerization monomer 33333333 Photoinitiator 111111111 Solvent 8072.530303030303030

[0086]

[0087] Experimental Example 1. Evaluation of Compatibility between Binder and Pigment Dispersion

[0088] The compatibility of the pigment dispersions used in Examples 1 to 7 (each including dispersants A to F) and the pigment alone (Comparative Example 2) with the polysilsesquioxane binder was examined.

[0089] The polysilsesquioxane binder of Manufacturing Example 1, one of the pigment dispersions and single pigments used in Examples 1 to 7, and the solvent (PGMEA) were mixed in a weight ratio of 1:1:1, and changes in phase separation, turbidity, and precipitation were visually observed.

[0090] If the mixed solution is phase separated, has poor transparency, or contains sediment, it is evaluated as X. If the mixed solution is evenly mixed, does not separate phases or contain sediment, and is transparent to the naked eye, it is evaluated as ○, and this is shown in Table 2.

[0091]

[0092] Comparative example of physical properties Example 121234567 Compatibility-×××○○×○○

[0093]

[0094] In the case of a single pigment (Comparative Example 2), compatibility was poor because no dispersant was included.

[0095] In the case of the pigment dispersion used in Examples 1 and 2, the amine value is present but is too low, resulting in poor compatibility. In the case of the pigment dispersion used in Example 5, both the acid value and the amine value appear to be excessively high, resulting in poor compatibility.

[0096] On the other hand, the pigment dispersions used in Examples 3, 4, 6 and 7 had acid and amine values ​​within a certain range and exhibited good compatibility.

[0097]

[0098] Experimental Example 2. Evaluation of the dispersibility of pigment dispersions

[0099] The dispersibility was examined for the pigment dispersions used in Examples 1 to 7 (each including dispersants A to F) and the pigment alone (Comparative Example 2).

[0100] The polysilsesquioxane binder of Manufacturing Example 1, one of the pigment dispersions and single pigments used in Examples 1 to 7, and the solvent (PGMEA) were mixed in a weight ratio of 1:1:1, and changes in the viscosity and particle size of the pigment dispersion were confirmed.

[0101] If the viscosity increased or gelation progressed, the dispersibility was evaluated as poor. If the particle size was not maintained uniformly or the particle size did not increase, the dispersibility was evaluated as poor. Poor dispersibility was evaluated as X, and good dispersibility was evaluated as ○, and this is shown in Table 3.

[0102]

[0103] Comparative example of physical properties Example 121234567 Dispersibility-×××○○○××

[0104]

[0105] In the case of a single pigment (Comparative Example 2), the dispersibility was very poor because no dispersant was included at all.

[0106] In the case of the pigment dispersion used in Examples 1 and 2, the dispersant had an amine value, but it was too low, resulting in poor dispersibility. In the case of Examples 6 and 7, the dispersant had no amine value, resulting in poor dispersibility.

[0107] On the other hand, examples 3 to 5 showed good dispersibility by having an amine value within a certain range.

[0108]

[0109] Experimental Example 3. Evaluation of Coating Properties of Photosensitive Resin Compositions

[0110] Each of the photosensitive resin compositions of Examples 1 to 7 and Comparative Examples 1 to 2 was spun at 1300 rpm using a spin coater to create a 1 μm thick film sample. The coatability of each sample was evaluated based on the following criteria, and is shown in Table 4.

[0111] - ○ (Good): No pinholes or stains

[0112] - △ (Normal): If there are less than 2 pinholes and stains

[0113] - X (Defective): If there are 2 or more pinholes and stains

[0114]

[0115] Comparative example of physical properties Example 121234567 Coating properties ○×××△○×××

[0116]

[0117] Although the resin composition of Comparative Example 1 did not contain a pigment dispersion, its own coating properties were found to be good. In the case of Comparative Example 2, Examples 1 to 2, and Examples 5 to 7, two or more pinholes and stains were found, indicating poor coating properties.

[0118] In the case of Example 3, one pinhole occurred, indicating average coating properties, and in the case of Example 4, no pinholes or stains occurred at all, indicating good coating properties.

[0119]

[0120] Experimental Example 4. Evaluation of the Developability of Photosensitive Resin Compositions

[0121] The coated films of Examples 1 to 7 and Comparative Examples 1 to 2, manufactured in Experimental Example 3, were exposed to ultraviolet light using a photomask so that the exposed / unexposed portions could be distinguished. The developability was confirmed after full-body immersion in a 2.38% aqueous solution of TMAH (tetramethylammonium hydroxide) at 23°C. The developability of each composition was evaluated based on the following criteria, and is shown in Table 5.

[0122] - ○ (Good): Developed within 70 to 100 seconds in a 2.38% TMAH aqueous solution.

[0123] - X (bad): developed after 100 seconds or more in a 2.38% TMAH aqueous solution.

[0124]

[0125] Comparative example of physical properties Example 121234567 Phenomenon ×××××○○○○

[0126]

[0127] The resin composition of Comparative Example 1 was a polysilsesquioxane composition, and thus had poor developability. The resin composition of Comparative Example 2 contained a pigment, but its compatibility and dispersibility were poor, resulting in poor developability. Examples 1 to 3 showed poor developability due to the lack of an acid value in the dispersant. On the other hand, Examples 4 to 7, which contained a dispersant with an acid value within a certain range, showed good developability.

[0128]

[0129] It is obvious to a person skilled in the art that the present invention is not limited to the above embodiments, and that various modifications or changes can be made without departing from the technical spirit of the present invention.

Claims

1. Contains a binder and pigment dispersion liquid, The above pigment dispersion liquid contains a pigment, a dispersant and a dispersing solvent. The above binder comprises a polysilsesquioxane compound, A photosensitive resin composition, characterized in that the dispersant has an acid value and an amine value.

2. In claim 1, A photosensitive resin composition, wherein the acid value of the dispersant is in the range of 10 to 200 mgKOH / g.

3. In claim 1, A photosensitive resin composition, wherein the amine value of the dispersant is in the range of 10 to 200 mgKOH / g.

4. In claim 1, The above photosensitive resin composition, A photosensitive resin composition further comprising a photopolymerizable monomer, a photoinitiator and a solvent.

5. In claim 1, The above pigment dispersion liquid is, 3 to 30 parts by weight of the pigment; 1 to 10 parts by weight of the dispersant; and A photosensitive resin composition comprising 20 to 200 parts by weight of a dispersing solvent.

6. In claim 4, The above binder is 10 to 30 parts by weight; The pigment dispersion is 40 to 60 parts by weight; The above photopolymerizable monomer is 1 to 10 parts by weight; The photoinitiator is 0.1 to 5 parts by weight; and A photosensitive resin composition wherein the solvent is 10 to 50 parts by weight.

7. In claim 1, The above polysilsesquioxane compound is, RSiO 3 / 2 Two or more silane compounds capable of forming a unit; and RSiO 4 / 2 A photosensitive resin composition comprising one or more silane compounds capable of forming a unit, which are copolymerized.

8. A cured product manufactured by curing the photosensitive resin composition of any one of claims 1 to 7.

9. Applying the photosensitive resin composition of any one of claims 1 to 7, A method for forming a pattern, comprising selectively exposing a coated photosensitive resin composition to light and then developing it.