Photosensitive resin composition and display device including the same

Abstract

Disclosed are a photosensitive resin composition and a display device including the same. The photosensitive resin composition includes: a) an acrylic copolymer obtained by copolymerizing i) an unsaturated compound containing a hydroxyl group, ii) an unsaturated carboxylic acid, an unsaturated carboxylic anhydride or a mixture thereof, iii) an unsaturated compound containing an epoxy group, and iv) an olefinic unsaturated compound; b) a 1,2-quinonediazide-5-sulfonate compound having a phenol compound including a compound represented by the above chemical formula A as a ballast; c) an alkane coupling agent; and d) a solvent.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0116423 filed in the Korean Intellectual Property Office on September 28, 2018, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments of the present disclosure relate to a photosensitive resin composition and a display device including the same. Background Art

[0004] Generally, widely used display devices include a liquid crystal display (LCD), an organic light emitting device (OLED), and the like.

[0005] A liquid crystal display (LCD) and an organic light emitting device (OLED) may include an insulating film or a planarizing film, the insulating film being included to insulate between wirings and the planarizing film being included to planarize between wirings.

[0006] The above information disclosed in this Background section is only for enhancement of understanding of the background of the present disclosure and therefore it may contain information that is already known in this country to a person of ordinary skill in the art and does not constitute the prior art. Summary of the invention

[0007] Embodiments of the present disclosure are to provide a photosensitive resin composition having characteristics of excellent resolution, curing process margin, transparency, thermal discoloration resistance, and heat resistance, and particularly excellent sensitivity and adhesion, and a display device including the same.

[0008] An exemplary embodiment of the present disclosure provides a photosensitive resin composition, the photosensitive resin composition including: a) an acrylic copolymer obtained by copolymerizing i) a hydroxyl group-containing unsaturated compound, ii) an unsaturated carboxylic acid, an unsaturated carboxylic anhydride or a mixture thereof, iii) an epoxy group-containing unsaturated compound, and iv) an olefin-based unsaturated compound; b) a 1,2-quinonediazide-5-sulfonate compound having a phenol compound including a compound represented by the following Chemical Formula A as a ballast; c) a silane coupling agent; and d) a solvent:

[0009]

[0010]

[0011] Where R 1 and R 2are cyclopropyl, cyclobutyl, cyclopentyl, or an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, respectively, R 3 and R 4 H or CH 3 , and R is independently H, CH 3 or The * indicates the connection site with the adjacent atom.

[0012] The hydroxyl group-containing unsaturated compound may include at least one selected from the group consisting of compounds represented by the following Chemical Formulae 1 to 8:

[0013]

[0014]

[0015] Wherein, in Chemical Formulas 1 to 8, R is independently H or CH 3 , and in Chemical Formula 3, n1 and n2 are integers selected from 0 to 4, respectively.

[0016] The photosensitive resin composition may further include a compound represented by the following Chemical Formula B:

[0017]

[0018] In the chemical formula B, R is H, CH 3 or The * indicates the connection site with the adjacent atom.

[0019] The compound represented by Chemical Formula A may include at least one selected from the group consisting of compounds represented by the following Chemical Formulas A-1, A-2, A-3, A-4, A-5, and A-6:

[0020]

[0021]

[0022]

[0023] In the chemical formulas A-1 to A-6, R 3 and R 4 H or CH 3 , and in chemical formulas A-2 to A-6, R is The * indicates the connection site with the adjacent atom.

[0024] The photosensitive resin composition may include at least one selected from the group consisting of compounds represented by the following chemical formulas B-1, B-2, B-3, B-4, and B-5:

[0025]

[0026]

[0027] Wherein, in chemical formulas B-1 to B-5, R is The * indicates the connection site with the adjacent atom.

[0028] The photosensitive resin composition may include: a) 100 parts by weight of an acrylic copolymer obtained by copolymerizing i) 5 to 70 parts by weight of an unsaturated compound containing a hydroxyl group, ii) 5 to 40 parts by weight of an unsaturated carboxylic acid, an unsaturated carboxylic anhydride or a mixture thereof, iii) 10 to 70 parts by weight of an unsaturated compound containing an epoxy group, and iv) 5 to 70 parts by weight of an olefinic unsaturated compound; b) 5 to 50 parts by weight of a 1,2-quinonediazide-5-sulfonate compound having a phenol compound including a compound represented by Chemical Formula A as a ballast, or a 1,2-quinonediazide-5-sulfonate compound having a phenol compound including a compound represented by Chemical Formula A and a compound represented by Chemical Formula B as a ballast; and c) 0.1 to 30 parts by weight of a silane coupling agent.

[0029] The solvent may be included so that the solid content including a), b), and c) is 10 wt % to 50 wt % based on the total weight of the photosensitive resin composition.

[0030] The unsaturated carboxylic acid, unsaturated carboxylic anhydride or mixture thereof of a) ii) may include one or more selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid and unsaturated carboxylic anhydrides thereof.

[0031] The epoxy group-containing unsaturated compound of a)iii) may include one or more selected from the group consisting of glycidyl acrylate, glycidyl methacrylate, α-ethyl glycidyl acrylate, α-n-propyl glycidyl acrylate, α-n-butyl glycidyl acrylate, β-methyl glycidyl acrylate, β-methyl glycidyl methacrylate, β-ethyl glycidyl acrylate, β-ethyl glycidyl methacrylate, 3,4-epoxybutyl acrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7-epoxyheptyl methacrylate, α-ethyl 6,7-epoxyheptyl acrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, 3,4-epoxycyclohexyl methacrylate, 3,4-epoxycyclohexyl methyl methacrylate, 3,4-epoxycyclohexyl acrylate, and 3,4-epoxycyclohexyl methyl acrylate.

[0032] The olefinic unsaturated compound of a) iv) may include one or more selected from the group consisting of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, methyl acrylate, isopropyl acrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, dicyclopentenyl acrylate, dicyclopentane acrylate, dicyclopentenyl methacrylate, dicyclopentane methacrylate, 1-adamantyl acrylate, 1-adamantyl methacrylate, dicyclopentyloxyethyl methacrylate, isobornyl methacrylate, cyclohexyl acrylate, 2-methylcyclohexyl acrylate, dicyclopentyloxyethyl acrylate, isobornyl methacrylate, phenyl methacrylate, phenyl acrylate, benzyl acrylate, 2-hydroxyethyl methacrylate, styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene.

[0033] The acrylic copolymer of a) may have a weight average molecular weight (Mw) of 3,000 to 20,000 in terms of polystyrene.

[0034] The silane coupling agent c) may include one or more selected from the group consisting of: (3-glycidoxypropyl)trimethoxysilane, (3-glycidoxypropyl)triethoxysilane, (3-glycidoxypropyl)methyldimethoxysilane, (3-glycidoxypropyl)methyldiethoxysilane, (3-glycidoxypropyl)dimethylethoxysilane, 3,4-epoxybutyltrimethoxysilane, 3,4-epoxybutyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, alkyl, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, aminopropyltrimethoxysilane, aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylene)propylamine, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and (3-isocyanatopropyl)triethoxysilane.

[0035] The solvent of d) may include one or more selected from the group consisting of diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate, propylene glycol propyl ether propionate, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, butylene glycol monomethyl ether, butylene glycol monoethyl ether, dibutylene glycol dimethyl ether, dibutylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol butyl ethyl ether, triethylene glycol dimethyl ether, triethylene glycol butyl methyl ether, diethylene glycol tert-butyl ether, tetraethylene glycol dimethyl ether, diethylene glycol ethyl hexyl ether, diethylene glycol methyl hexyl ether, dipropylene glycol butyl methyl ether, dipropylene glycol ethyl hexyl ether and dipropylene glycol methyl hexyl ether.

[0036] The display device according to the exemplary embodiment includes a cured body (eg, a cured product) of the photosensitive resin composition as described above.

[0037] The display device may include an organic insulating film including a cured body of the photosensitive resin composition.

[0038] The display device may further include a substrate, a thin film transistor on the substrate, a pixel electrode coupled to the thin film transistor, and a color filter superimposed on the thin film transistor.

[0039] A color filter may be between the organic insulating film and the thin film transistor.

[0040] A display device according to an exemplary embodiment includes a substrate, a thin film transistor on the substrate, a pixel electrode coupled to the thin film transistor, and an organic insulating film stacked on the substrate, and

[0041] The organic insulating film includes a cured body (e.g., a cured product) of a photosensitive resin composition, the photosensitive resin composition including: a) an acrylic copolymer obtained by copolymerizing i) a hydroxyl-containing unsaturated compound, ii) an unsaturated carboxylic acid, an unsaturated carboxylic anhydride or a mixture thereof, iii) an epoxy-containing unsaturated compound, and iv) an olefin-based unsaturated compound; b) a 1,2-quinonediazide-5-sulfonate compound having a phenol compound including a compound represented by the following Chemical Formula A as a ballast; and c) a silane coupling agent.

[0042]

[0043] Where R 1 and R 2 are cyclopropyl, cyclobutyl or cyclopentyl, R 3 and R 4 H or CH 3 , and R is independently H, CH 3or The * indicates the connection site with the adjacent atom.

[0044] According to exemplary embodiments, the photosensitive resin composition has excellent resolution, curing process margin, transparency, heat discoloration resistance and heat resistance, and may have excellent sensitivity and adhesion in particular. In addition, a display device including an organic insulating film or a planarization film formed of the photosensitive resin composition may have improved reliability. BRIEF DESCRIPTION OF THE DRAWINGS

[0045] The drawings, together with the specification, illustrate embodiments of the presently disclosed subject matter, and, together with the description, serve to explain principles of embodiments of the presently disclosed subject matter. Figure 1 is a schematic cross-sectional view of a portion of one pixel according to an exemplary embodiment. DETAILED DESCRIPTION

[0046] Hereinafter, various exemplary embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings so that those skilled in the art to which the present disclosure pertains can easily implement the present disclosure. The subject matter of the present disclosure can be implemented in various different forms and is not limited to the exemplary embodiments described herein.

[0047] In order to clearly describe the subject matter of the present disclosure, parts irrelevant to the relevant description are omitted, and the same reference numerals denote the same or similar constituent elements throughout the specification.

[0048] In addition, since the size and thickness of each component shown in the drawings may be optionally represented for convenience of description, the present disclosure is not necessarily limited to the sizes and thicknesses shown in the drawings.

[0049] In addition, it should be understood that when an element, such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element or there may be intervening elements. Conversely, when an element is referred to as being "directly" "on" another element, there are no intervening elements. In addition, "above" or "on" a reference element is understood to be "on" or "below" the reference element, but is not necessarily understood to be "on" or "above" in the opposite direction of gravity.

[0050] In addition, unless explicitly described to the contrary, the word “comprise” and variations such as “comprises” or “comprising” will be understood to imply the inclusion of stated elements but not the exclusion of any other elements.

[0051] In addition, throughout this specification, the term "on a plane" refers to when an object is viewed from above, and the term "in cross section" refers to when a cross section of an object cut vertically is viewed from the side.

[0052] Hereinafter, a photosensitive resin composition according to an exemplary embodiment will be described.

[0053] The photosensitive resin composition according to the exemplary embodiment may include: a) an acrylic copolymer obtained by copolymerizing i) a hydroxyl-containing unsaturated compound including at least one selected from the compounds represented by the following chemical formulas 1 to 8, ii) an unsaturated carboxylic acid, an unsaturated carboxylic acid anhydride or a mixture thereof, iii) an epoxy-containing unsaturated compound, and iv) an olefin-based unsaturated compound; b) a 1,2-quinonediazide 5-sulfonic acid ester compound having a phenol compound including a compound represented by the following chemical formula A as a ballast; c) a silane coupling agent; and d) a solvent. In addition, the photosensitive resin composition according to the exemplary embodiment may further include a compound represented by the following chemical formula B.

[0054]

[0055] Wherein, in chemical formula 1-8, R is H or CH 3 , and in Chemical Formula 3, n1 and n2 are integers selected from 0 to 4 independently of each other.

[0056]

[0057] In the chemical formula B, R is H, CH 3 or Where * indicates the connection site with the adjacent atom, R 1 and R 2 are independently cyclopropyl, cyclobutyl, cyclopentyl, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and R 3 and R 4 are independently H or CH 3 .

[0058] The photosensitive resin composition according to the exemplary embodiment may include: a) 100 parts by weight of an acrylic copolymer, wherein the acrylic copolymer is prepared by i) 5 to 70 parts by weight of an unsaturated compound containing a hydroxyl group, wherein the unsaturated compound containing a hydroxyl group includes at least one selected from the compounds represented by the above Chemical Formulas 1 to 8, ii) 5 to 40 parts by weight of an unsaturated carboxylic acid, an unsaturated carboxylic anhydride, or a mixture thereof, iii) 10 to 70 parts by weight of an unsaturated compound containing an epoxy group, and iv) 5 to 70 parts by weight of an epoxy group. b) 5 to 50 parts by weight of a 1,2-quinonediazide 5-sulfonate compound having a phenol compound including a compound represented by Chemical Formula A as a ballast, or a 1,2-quinonediazide 5-sulfonate compound having a phenol compound including a compound represented by Chemical Formula A and a compound represented by Chemical Formula B as a ballast; c) 0.1 to 30 parts by weight of a silane coupling agent; and d) a solvent, so that the solid content in the photosensitive resin composition is 10 wt % to 50 wt %.

[0059] Hereinafter, components used in the photosensitive resin composition according to exemplary embodiments will be described in more detail.

[0060] The acrylic copolymer of a) according to the exemplary embodiment can be obtained by using i) a hydroxyl-containing unsaturated compound including at least one selected from the compounds represented by Chemical Formulas 1 to 8, ii) an unsaturated carboxylic acid, an unsaturated carboxylic anhydride or a mixture thereof, iii) an epoxy-containing unsaturated compound, and iv) an olefin-based unsaturated compound as monomers. The compounds of i) to iv) are subjected to a radical reaction in the presence of a solvent and a polymerization initiator to perform a synthesis reaction, and then unreacted monomers are removed through a purification process, thereby obtaining an acrylic copolymer.

[0061] The hydroxyl-containing unsaturated compound a)i) including at least one selected from the compounds represented by Chemical Formulas 1 to 8 may be included in an amount of 5 to 70 parts by weight based on the total weight of the monomers. When the content is less than 5 parts by weight, the sensitivity of the photosensitive resin composition may be reduced, and when the content is greater than 70 parts by weight, the solubility in an alkaline aqueous solution may be excessively increased.

[0062] As the unsaturated carboxylic acid, unsaturated carboxylic anhydride or mixture thereof of a) ii), unsaturated monocarboxylic acids such as acrylic acid and methacrylic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid and itaconic acid, or unsaturated carboxylic anhydrides thereof, etc. may be used alone or in combination of two or more. As examples, acrylic acid, methacrylic acid or anhydrous maleic acid may be included. When acrylic acid, methacrylic acid or anhydrous maleic acid is used, copolymerization reactivity is excellent, and solubility in an alkaline aqueous solution (which is a developing solution) is appropriate or suitable.

[0063] The unsaturated carboxylic acid, unsaturated carboxylic anhydride or a mixture thereof may be included in an amount of 5 to 40 parts by weight based on the total weight of the monomers. When the content is less than 5 parts by weight, the unsaturated carboxylic acid, unsaturated carboxylic anhydride or the mixture may be difficult to dissolve in an alkaline aqueous solution, and when the content is greater than 40 parts by weight, the solubility in the alkaline aqueous solution may be excessively or inappropriately increased.

[0064] The epoxy group-containing unsaturated compound of a) iii) may include glycidyl acrylate, glycidyl methacrylate, α-ethyl glycidyl acrylate, α-n-propyl glycidyl acrylate, α-n-butyl glycidyl acrylate, β-methyl glycidyl acrylate, β-methyl glycidyl methacrylate, β-ethyl glycidyl acrylate, β-ethyl glycidyl methacrylate, 3,4-epoxybutyl acrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7-epoxyheptyl methacrylate, α-ethyl 6,7-epoxyheptyl acrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, 3,4-epoxycyclohexyl methacrylate, and the like, and these compounds may be used alone or in combination of two or more. As an example, the epoxy-containing unsaturated compound may include at least one selected from the following: glycidyl methacrylate, β-methyl glycidyl methacrylate, 6,7-epoxyheptyl methacrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, 3,4-epoxycyclohexyl methacrylate, etc., thereby improving the copolymerization reactivity and the heat resistance of the pattern obtained by the photosensitive resin composition.

[0065] The epoxy-containing unsaturated compound may be included in an amount of 10 to 70 parts by weight based on the total weight of the monomers. Within this range, heat resistance of the organic insulating film and storage stability of the photosensitive resin composition may be simultaneously (eg, simultaneously or substantially simultaneously) suitable or satisfactory.

[0066] The olefinic unsaturated compound of a) iv) may include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, methyl acrylate, isopropyl acrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, dicyclopentenyl acrylate, dicyclopentane acrylate, dicyclopentenyl methacrylate, dicyclopentane methacrylate, 1-adamantyl acrylate, 1-adamantyl methacrylate, dicyclopentanyloxyethyl methacrylate, isobornyl methacrylate, cyclohexyl acrylate, 2-methylcyclohexyl acrylate, dicyclopentanyloxyethyl acrylate, isobornyl methacrylate, phenyl methacrylate, phenyl acrylate, benzyl acrylate, 2-hydroxyethyl methacrylate, styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, 1,3-butadiene, isoprene or 2,3-dimethyl-1,3-butadiene, and the like, and these compounds may be used alone or in combination of two or more.

[0067] The olefinic unsaturated compound may be included in an amount of 5 to 70 parts by weight based on the total weight of the monomers. Within this range, swelling after development of the photosensitive resin composition may be suppressed or reduced, and appropriate or suitable solubility in an alkaline aqueous solution (which is a developing solution) may be provided.

[0068] A solvent and a polymerization initiator may be further included to form an acrylic copolymer using the monomer. As an example, the solvent may include one or more selected from the following: methanol, tetrahydrofuran, toluene and dioxane. The polymerization initiator may include a free radical polymerization initiator, and as an example, may include 2,2-azobisisobutyronitrile, 2,2-azobis(2,4-dimethylvaleronitrile), 2,2-azobis(4-methoxy 2,4-dimethylvaleronitrile), 1,1-azobis(cyclohexane-1-nitrile), 2,2'-azobisisobutyric acid dimethyl ester, etc.

[0069] The acrylic copolymer obtained by subjecting the above monomers to a free radical reaction in the presence of a solvent and a polymerization initiator to synthesis and removing unreacted monomers through a purification process may have a weight average molecular weight (Mw) of 3,000 to 20,000 in terms of polystyrene. When the weight average molecular weight is less than 3,000 in terms of polystyrene, developability or residual film ratio may be deteriorated or reduced, or pattern development or heat resistance may be deteriorated or reduced, and when the weight average molecular weight is greater than 20,000, pattern development may be deteriorated or reduced.

[0070] The 1,2-quinonediazide 5-sulfonic acid ester compound b) having a phenol compound including a compound represented by Chemical Formula A or B as a ballast can be obtained by reacting a 1,2-quinonediazide 5-sulfonic acid halide and a phenol compound under a weak base (eg, in the presence of a weak base).

[0071] The photosensitive resin composition according to the exemplary embodiment includes a 1,2-quinonediazide 5-sulfonate compound having a compound represented by Chemical Formula A as a ballast, and may further include a 1,2-quinonediazide 5-sulfonate compound having a compound represented by Chemical Formula B as a ballast.

[0072] The photosensitive resin composition according to the exemplary embodiment may include at least one selected from the group consisting of compounds represented by Chemical Formulas A-1, A-2, A-3, A-4, A-5, and A-6 as an example of a ballast of a 1,2-quinonediazide 5-sulfonate compound:

[0073]

[0074]

[0075] In the chemical formulas A-1 to A-6, R 3 and R 4 H or CH 3 , and in chemical formulas A-2 to A-6, R is The * indicates the connection site with the adjacent atom.

[0076] The photosensitive resin composition according to the exemplary embodiment may further include at least one selected from compounds represented by the following Chemical Formulas B-1, B-2, B-3, B-4, and B-5 as an example of a ballast of the 1,2-quinonediazide 5-sulfonate compound:

[0077]

[0078]

[0079] Where R is The * indicates the connection site with the adjacent atom.

[0080] At least one compound selected from the group consisting of Chemical Formulas A-1 to A-6 and Chemical Formulas B-1 to B-5 may react with a compound including an -OH group in a light exposure process to form a cured body (eg, a cured product), which may be represented as follows:

[0081]

[0082] The 1,2-quinonediazide 5-sulfonic acid ester compound may be included in an amount of 5 to 50 parts by weight based on 100 parts by weight of a) the acrylic copolymer. When the content is less than 5 parts by weight, the difference in solubility between the exposed portion and the unexposed portion is reduced, so that pattern formation may be difficult, and when the content is greater than 50 parts by weight, when irradiated with light for a short time, unreacted 1,2-quinonediazide 5-sulfonic acid ester compound is still in a large amount, and the solubility in the alkaline aqueous solution (which is a developing solution) is excessively or inappropriately reduced, thereby making development difficult.

[0083] c) The silane coupling agent can improve the adhesion to the lower substrate. The silane coupling agent may include (3-glycidoxypropyl)trimethoxysilane, (3-glycidoxypropyl)triethoxysilane, (3-glycidoxypropyl)methyldimethoxysilane, (3-glycidoxypropyl)methyldiethoxysilane, (3-glycidoxypropyl)dimethylethoxysilane, 3,4-epoxybutyltrimethoxysilane, 3,4-epoxybutyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, aminopropyltrimethoxysilane, Silane, aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylene)propylamine, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, (3-isocyanatepropyl)triethoxysilane, (3-isocyanatepropyl)trimethoxysilane, etc. are given as examples and can be used alone or in combination of two or more.

[0084] The silane coupling agent may be included in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of a) the acrylic copolymer. When the amount is less than 0.1 parts by weight, adhesion to the lower substrate is reduced, and when the amount is greater than 30 parts by weight, storage stability and developability are deteriorated or reduced and resolution may be deteriorated or reduced.

[0085] The solvent of d) may include one or more selected from the group consisting of diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate, propylene glycol propyl ether propionate, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, butylene glycol monomethyl ether, butylene glycol monoethyl ether, dibutylene glycol dimethyl ether, dibutylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol butyl ethyl ether, triethylene glycol dimethyl ether, triethylene glycol butyl methyl ether, diethylene glycol tert-butyl ether, tetraethylene glycol dimethyl ether, diethylene glycol ethyl hexyl ether, diethylene glycol methyl hexyl ether, dipropylene glycol butyl methyl ether, dipropylene glycol ethyl hexyl ether and dipropylene glycol methyl hexyl ether.

[0086] The solvent of d) may be included so that the solid content of the photosensitive resin composition is 10 wt % to 50 wt %. When the solid content is less than 10 wt %, the applied thickness is small so that the coating uniformity may be reduced, and when the solid content is greater than 50 wt %, the applied thickness is large and the coating equipment may be overloaded during coating.

[0087] As an example, when the solid content of the entire photosensitive resin composition is 10 wt % to 25 wt %, a slit coater is used, and when the solid content is 25 wt % to 50 wt %, a spin coater or a slit and spin coater may be used.

[0088] The photosensitive resin composition according to the exemplary embodiment may have a solid content of 10 wt % to 50 wt %, and may be used after being filtered through a 0.1 μm to 0.2 μm microporous filter or the like.

[0089] In a process of manufacturing a display device using the above-mentioned photosensitive resin composition, an embodiment of a method of forming an insulating film is as follows.

[0090] The photosensitive resin composition according to the exemplary embodiment is coated on the substrate surface by spin coating, slit and spin coating, slit coating or roller coating. Thereafter, the solvent is removed by free baking to form a coating film. At this time, the free baking can be performed at a temperature of 100° C. to 120° C. for 1 minute to 3 minutes.

[0091] Next, visible light, ultraviolet light, extreme ultraviolet light, electron beam, X-ray, etc. are irradiated onto the formed coating film according to the previously prepared pattern, and developed with a developing solution to remove unnecessary or undesired portions, thereby forming a set of predetermined patterns.

[0092] As the developing solution, an alkaline aqueous solution can be used. For example, an aqueous solution of one or more of the following can be used: an inorganic base such as sodium hydroxide, potassium hydroxide and sodium carbonate; a primary amine such as ethylamine and n-propylamine; a secondary amine such as diethylamine and dipropylamine; a tertiary amine such as trimethylamine, methyldiethylamine, dimethylethylamine and triethylamine; an alcohol amine such as dimethylethanolamine, methyldiethanolamine and triethanolamine; or a quaternary ammonium salt such as tetramethylammonium hydroxide and tetraethylammonium hydroxide.

[0093] 100 parts by weight of the developing solution may include 0.1 parts by weight to 10 parts by weight of a basic compound, and an appropriate or suitable amount of an aqueous organic solvent such as methanol and ethanol, and a surfactant.

[0094] The coated film is developed with a developing solution, washed with ultrapure water for 30 seconds to 90 seconds to remove unnecessary or undesirable portions and dried, thereby forming a pattern.

[0095] Light, such as, for example, ultraviolet light, is irradiated onto the formed pattern, and heat treatment is performed at a temperature of 150° C. to 400° C. for 30 minutes to 90 minutes by a heating device, such as an oven, to obtain a final pattern.

[0096] The final pattern may include a cured body (eg, a cured product) formed of the above-mentioned photosensitive resin composition. The description of the photosensitive resin composition will not be repeated unnecessarily below.

[0097] Below, we will refer to Figure 1 A display device including a cured body (eg, a cured product) of the above-described photosensitive resin composition is described. Figure 1 A cross-sectional view schematically showing a portion of a pixel included in a display device.

[0098] refer to Figure 1 , the lower panel 100 includes a first substrate 110, and includes a gate line including a gate electrode 124. A gate insulating film 140 is on the gate electrode 124, and a semiconductor layer 154 is on the gate insulating film 140 superimposed on the gate electrode 124.

[0099] Then, a data line including a source electrode 173 and a drain electrode 175 is on the semiconductor layer 154. The source electrode 173 and the drain electrode 175 may face each other around a channel region included in the semiconductor layer 154.

[0100] The gate electrode 124 , the semiconductor layer 154 , the source electrode 173 , and the drain electrode 175 form one thin film transistor, and a channel may be formed on the semiconductor layer 154 between the source electrode 173 and the drain electrode 175 .

[0101] The protection film 180 is on the source electrode 173 and the drain electrode 175 .

[0102] The color filter 230 is on the protective film 180 and may inherently represent one of the primary colors. As examples of the primary colors, three primary colors such as red, green, and blue, or yellow, cyan, magenta, etc. may be included.

[0103] The organic insulating film 190 is on the color filter 230. The organic insulating film 190 may planarize one surface of the color filter 230.

[0104] The organic insulating film 190 may be formed using the above-mentioned photosensitive resin composition, and includes a cured body of the above-mentioned photosensitive resin composition. Therefore, further description of the photosensitive resin composition will not be repeated here.

[0105] The protection film 180 and the organic insulating film 190 have a contact hole 185 superimposed on the drain electrode 175 , and the drain electrode 175 and the pixel electrode 191 may be electrically and physically coupled to each other through the contact hole 185 .

[0106] The upper panel 200 includes a second substrate 210 facing the first substrate 110. A light blocking member 220 is on a portion between the second substrate 210 and the liquid crystal layer 3. The light blocking member 220 is also called a black matrix and may block light leakage.

[0107] In the present specification, a configuration in which the light blocking member 220 is in the upper panel 200 has been described, but the present disclosure is not limited thereto, and the light blocking member 220 may be in the lower panel 100 .

[0108] The overcoat layer 250 is between the light blocking member 220 and the liquid crystal layer 3. The overcoat layer 250 may be formed of an organic insulating material. The overcoat layer 250 prevents or reduces exposure of the light blocking member 220 and provides a planarized surface. According to an exemplary embodiment, the overcoat layer 250 may be omitted.

[0109] The common electrode 270 may be between the overcoat layer 250 and the liquid crystal layer 3. The common electrode 270 may include the same or substantially the same material as the pixel electrode 191. The common electrode 270 may be formed in the form of a planar surface and a common voltage is applied thereto.

[0110] In some embodiments, an alignment layer (not shown) may be between the pixel electrode 191 and the liquid crystal layer 3 , and between the common electrode 270 and the liquid crystal layer 3 .

[0111] The liquid crystal layer 3 is between the lower panel 100 and the upper panel 200. The liquid crystal layer 3 has negative dielectric anisotropy, and liquid crystal molecules 31 of the liquid crystal layer 3 have major axes perpendicular (eg, substantially perpendicular) to the surfaces of the lower panel 100 and the upper panel 200 in the absence of an electric field.

[0112] The organic insulating film 190 including the photosensitive resin composition according to the exemplary embodiment has excellent planarization and transmittance, and particularly excellent sensitivity, and has excellent adhesion, contrast and chemical resistance under high temperature and high humidity. A display device including the organic insulating film may also have improved reliability.

[0113] In the present specification, a display device using the photosensitive resin composition has been described, but the present disclosure is not limited thereto and the photosensitive resin composition may be applied to various components used in an organic light-emitting device, such as an interlayer insulating film, a column spacer, a partition, and the like.

[0114] Hereinafter, exemplary embodiments are presented to help understand the subject matter of the present disclosure, however, the following embodiments merely illustrate implementation modes of the present disclosure, and the scope of the present disclosure is not limited to the following contents.

[0115] Example

[0116] Synthesis Example 1 (Preparation of acrylic copolymer (A))

[0117] A mixed solution of 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following chemical formula 1A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene and 30 parts by weight of glycidyl methacrylate is added to a flask equipped with a cooler and an agitator. The liquid composition is appropriately mixed at 600 rpm in a flask, and then 15 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) is added thereto. The polymerized mixed solution is slowly heated to 55°C, maintained at this temperature for 24 hours, and cooled to room temperature (e.g., about 25°C), and 500 ppm of hydrobezophenone as a polymerization initiator is added thereto to obtain a polymer solution having a solid content of 25wt%. In order to remove unreacted monomers from the polymer solution, 1000 parts by weight of n-hexane are used to precipitate 100 parts by weight of the polymer solution. After precipitation, a sieve is used to perform a filtration process to remove the poor solvent in which the unreacted material is dissolved. In order to remove the solvent containing unreacted monomers remaining even after the filtration process, vacuum drying was performed at a temperature of 30° C. or less to substantially completely remove the solvent to prepare an acrylic copolymer. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

[0118]

[0119]

[0120] Synthesis Example 2 (Preparation of acrylic copolymer (B))

[0121] An acrylic copolymer (B) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following Chemical Formula 2A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene, and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 5,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0122]

[0123] Synthesis Example 3 (Preparation of acrylic copolymer (C))

[0124] An acrylic copolymer (C) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following Chemical Formula 3A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene, and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 5,500. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0125]

[0126]

[0127] Synthesis Example 4 (Preparation of acrylic copolymer (D))

[0128] An acrylic copolymer (D) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following Chemical Formula 4A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene, and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0129]

[0130] Synthesis Example 5 (Preparation of acrylic copolymer (E))

[0131] An acrylic copolymer (E) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following Chemical Formula 5A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene, and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0132]

[0133]

[0134] Synthesis Example 6 (Preparation of acrylic copolymer (F))

[0135] An acrylic copolymer (F) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following Chemical Formula 6A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene, and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0136]

[0137] Synthesis Example 7 (Preparation of acrylic copolymer (G))

[0138] An acrylic copolymer (G) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following Chemical Formula 7A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene, and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0139]

[0140] Synthesis Example 8 (Preparation of acrylic copolymer (H))

[0141] An acrylic copolymer (H) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of an unsaturated compound represented by the following Chemical Formula 8A, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene, and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0142]

[0143] Synthesis Example 9 (Preparation of 1,2-quinonediazide 5-sulfonic acid ester compound)

[0144] 1 mol of a phenol compound represented by the following Chemical Formula Aa and 2.0 mol of 1,2-naphthoquinonediazide-5-sulfonic acid [chloride] were subjected to a condensation reaction to prepare a 1,2-naphthoquinonediazide-5-sulfonic acid ester compound as a 1,2-quinonediazide 5-sulfonic acid ester compound.

[0145]

[0146] Synthesis Example 10 (Preparation of 1,2-quinonediazide 5-sulfonic acid ester compound)

[0147] 1 mol of a phenol compound represented by the following chemical formula Ba and 2.0 mol of 1,2-naphthoquinonediazide-5-sulfonic acid [chloride] were subjected to a condensation reaction to prepare a 1,2-naphthoquinonediazide-5-sulfonic acid ester compound as a 1,2-quinonediazide 5-sulfonic acid ester compound.

[0148]

[0149]

[0150] Comparative Synthesis Example 1 (Preparation of Acrylic Copolymer (I))

[0151] An acrylic copolymer (I) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of hydroxyethyl methacrylate, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0152] Comparative Synthesis Example 2 (Preparation of Acrylic Copolymer (J))

[0153] An acrylic copolymer (J) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of hydroxybutyl methacrylate, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0154] Comparative Synthesis Example 3 (Preparation of Acrylic Copolymer (K))

[0155] An acrylic copolymer (K) was prepared in substantially the same manner as in Synthesis Example 1, except that 400 parts by weight of tetrahydrofuran, 30 parts by weight of methyl methacrylate, 20 parts by weight of methacrylic acid, 20 parts by weight of styrene and 30 parts by weight of glycidyl methacrylate were added to the flask equipped with a cooler and a stirrer of Synthesis Example 1. The acrylic copolymer had a weight average molecular weight of 6,000. Here, the weight average molecular weight is a weight average molecular weight with respect to polystyrene measured by GPC.

[0156] Example 1 (Preparation of photosensitive resin composition)

[0157] 30 parts by weight of the 1,2-naphthoquinonediazide-5-sulfonic acid ester compound prepared in Synthesis Example 9, 3 parts by weight of (3-glycidoxypropyl)trimethoxysilane as a silane coupling agent, and 100 parts by weight of the acrylic copolymer prepared in Synthesis Example 1 were dissolved in propylene glycol monomethyl ether acetate so that the solid content of the mixture was 20 wt % based on 100 wt % of the resulting composition, and then the solution was filtered with a 0.1 μm microporous filter to prepare a photosensitive resin composition.

[0158] Example 2 (Preparation of photosensitive resin composition)

[0159] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (B) of Synthesis Example 2 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0160] Example 3 (Preparation of photosensitive resin composition)

[0161] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (C) of Synthesis Example 3 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0162] Example 4 (Preparation of photosensitive resin composition)

[0163] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (D) of Synthesis Example 4 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0164] Example 5 (Preparation of photosensitive resin composition)

[0165] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (E) of Synthesis Example 5 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0166] Example 6 (Preparation of photosensitive resin composition)

[0167] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (F) of Synthesis Example 6 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0168] Example 7 (Preparation of photosensitive resin composition)

[0169] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (G) of Synthesis Example 7 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0170] Example 8 (Preparation of photosensitive resin composition)

[0171] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (H) of Synthesis Example 8 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0172] Example 9 (Preparation of photosensitive resin composition)

[0173] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that 15 parts by weight of the 1,2-naphthoquinonediazide-5-sulfonate compound of Synthesis Example 9 and 15 parts by weight of the 1,2-naphthoquinonediazide-5-sulfonate compound of Synthesis Example 10 were used instead of 30 parts by weight of the 1,2-naphthoquinonediazide-5-sulfonate compound of Synthesis Example 9 in Example 1.

[0174] Example 10 (Preparation of photosensitive resin composition)

[0175] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that (3-isocyanatepropyl)trimethoxysilane was used instead of (3-glycidoxypropyl)trimethoxysilane in Example 1 as the silane coupling agent.

[0176] Comparative Example 1 (Preparation of a photosensitive resin composition)

[0177] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (I) of Comparative Synthesis Example 1 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0178] Comparative Example 2 (Preparation of Photosensitive Resin Composition)

[0179] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (J) of Comparative Synthesis Example 2 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0180] Comparative Example 3 (Preparation of Photosensitive Resin Composition)

[0181] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that the acrylic copolymer (K) of Comparative Synthesis Example 3 was used instead of the acrylic copolymer (A) of Synthesis Example 1 in Example 1.

[0182] Comparative Example 4 (Preparation of photosensitive resin composition)

[0183] A photosensitive resin composition was prepared in substantially the same manner as in Example 1, except that (3-glycidoxypropyl)trimethoxysilane as the silane coupling agent in Example 1 was not used.

[0184] For Examples 1 to 10 and Comparative Examples 1 to 4, physical properties such as sensitivity, resolution, curing process margin, transmittance, thermal discoloration resistance, adhesion, and heat resistance were measured and are shown in the following Table 1. The photosensitive resin compositions according to Examples 1 to 10 and Comparative Examples 1 to 4 were coated on a glass substrate using a spin coater and free-baked on a hot plate at 100° C. for 2 minutes to form a film having a thickness of 4.0 μm.

[0185] A) Sensitivity - Using a set of predetermined pattern masks, 20 mW / cm2 was irradiated on the thus formed film at a sensitivity of 10 μm contact critical dimension (CD) reference volume. 2 The ultraviolet light with a broadband intensity of 400 mJ / cm was then developed with a 2.38 wt% tetramethylammonium hydroxide aqueous solution at 23°C for 1 minute and washed with ultrapure water for 1 minute. 2 20mW / cm at 365nm 2 The developed pattern was irradiated with ultraviolet rays of an intensity of 1000 μm and cured in an oven at 230° C. for 30 minutes to obtain a pattern film with a thickness of 3.0 μm.

[0186] B) Resolution - measures the minimum size of the 10 μm contact hole pattern formed when measuring sensitivity in A).

[0187] C) Curing process margin - A pattern film was formed in substantially the same manner as the sensitivity measurement in A), except that the CD change rate before and after curing was measured based on a 10 μm contact hole CD. Here, a change rate of 0%-10% is represented as ○, a change rate of 10%-20% is represented as △, and a change rate greater than 20% is represented as Х.

[0188] D) Transmittance - The transmittance was evaluated by measuring the transmittance of the pattern film formed when the sensitivity was measured in A) at 400 nm using a spectrophotometer. Here, a transmittance of 90% or more is represented by ○, a transmittance of 85%-90% is represented by △, and a transmittance of less than 80% is represented by Х.

[0189] E) Heat discoloration resistance - On the substrate measured when evaluating transmittance in D), curing was further performed in an oven at 230°C for 30 minutes twice, thereby evaluating heat discoloration resistance by the change in 400nm transmittance of the pattern film before and after curing. Here, a transmittance change rate of less than 3% is represented by ○, a transmittance change rate of 3%-5% is represented by △, and a transmittance change rate of more than 5% is represented by Х.

[0190] F) Adhesion - Adhesion was evaluated by observing the pattern film formed when measuring the sensitivity in A) to see whether the pattern was lost or not. The case where adhesion was ensured at a free baking temperature of 95°C or higher was indicated as ○, the case where adhesion was ensured at a free baking temperature of 100-105°C was indicated as △, and the case where adhesion was ensured or the pattern was lost at a free baking temperature of more than 105°C was indicated as Х.

[0191] G) Heat resistance - Heat resistance was measured using thermogravimetric analysis (TGA). The pattern formed when measuring sensitivity in A) was sampled, and the temperature was increased from room temperature (e.g., about 25°C) to 900°C at 10°C / min using TGA. The case of a 5 wt% loss temperature greater than 300°C was indicated as ○, the case of a 5 wt% loss temperature of 280-300°C was indicated as △, and the case of a 5 wt% loss temperature less than 280°C was indicated as Х.

[0192] Table 1

[0193]

[0194] As shown in Table 1 above, the photosensitive resin compositions prepared in Examples 1 to 10 have excellent properties, such as resolution, curing process margin, transmittance, heat discoloration resistance and heat resistance. For example, it is confirmed that the photosensitive resin compositions prepared in Examples 1 to 10 have excellent sensitivity compared with Comparative Examples 1 to 3, thereby reducing the time required for the process, and have excellent adhesion compared with Comparative Example 4 to ensure excellent panel reliability. In addition, as shown in Table 1, it is confirmed that the contour length according to the embodiment is a minimum of 12 μm to a maximum of 16 μm, and the contour length according to the comparative example is a minimum of 14 μm to a maximum of 20 μm. In Table 1, the contour length is obtained in SEM. In the case of an exemplary embodiment according to the present application, it is confirmed that the light exposure sensitivity is excellent so as to have a relatively short profile. In addition, in the case of having excellent light exposure sensitivity, the amount of light exposure required or used for the process is reduced, thereby improving productivity.

[0195] Although exemplary embodiments of the present disclosure have been described above, the scope of the present disclosure is not limited thereto, and many variations and modifications of the basic concepts of the present disclosure defined by the following claims and their equivalents by those skilled in the art also fall within the scope of the present disclosure.

[0196] Although the subject matter of the present disclosure has been described in conjunction with what are currently considered to be practicable exemplary embodiments, it should be understood that the present disclosure is not limited to the disclosed embodiments. Instead, it is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims and their equivalents.

Claims

1. A photosensitive resin composition, comprising: a) an acrylic copolymer obtained by copolymerizing: i) unsaturated compounds containing hydroxyl groups; ii) unsaturated carboxylic acid, unsaturated carboxylic anhydride or a mixture thereof; iii) an epoxy group-containing unsaturated compound; and iv) olefinic unsaturated compounds, b) a 1,2-quinonediazide 5-sulfonate compound having a phenol compound as a ballast, the phenol compound including a compound represented by the following Chemical Formula A, c) a silane coupling agent, and d) Solvent: Chemical formula A wherein R1 and R2 are independently cyclopropyl, cyclobutyl, cyclopentyl, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, R3 and R4 are independently H or CH3, and R is independently H, CH3 or Where * indicates the connection site with the adjacent atom, in: The hydroxyl-containing unsaturated compound includes at least one compound selected from the group consisting of the compounds represented by the following chemical formulas 1, 2, 4 to 8: Wherein, in Chemical Formulae 1, 2, 4 to 8, and R is independently H or CH3.

2. The photosensitive resin composition according to claim 1, further comprising: A compound represented by the following chemical formula B: Chemical formula B Wherein, in chemical formula B, R is H, CH3 or The * indicates the connection site with the adjacent atom.

3. The photosensitive resin composition according to claim 1, further comprising: At least one selected from the compounds represented by the following chemical formulas B-1, B-2, B-3, B-4 and B-5: Chemical formula B-1 Chemical formula B-2 Chemical formula B-3 Chemical formula B-4 Chemical formula B-5 Wherein, in chemical formulas B-1 to B-5, R is The * indicates the connection site with the adjacent atom.

4. The photosensitive resin composition according to claim 1, wherein: The compound represented by Chemical Formula A includes at least one selected from the group consisting of compounds represented by the following Chemical Formulas A-1, A-2, A-3, A-4, A-5 and A-6: Chemical formula A-1 Chemical formula A-2 Chemical formula A-3 Chemical formula A-4 Chemical formula A-5 Chemical formula A-6 Wherein, in chemical formulas A-1 to A-6, R3 and R4 are H or CH3, respectively, and in chemical formulas A-2 to A-6, R is The * indicates the connection site with the adjacent atom.

5. The photosensitive resin composition according to claim 2, comprising: a) 100 parts by weight of the acrylic copolymer, wherein the acrylic copolymer is obtained by copolymerizing: i) 5 to 70 parts by weight of the hydroxyl-containing unsaturated compound; ii) 5 to 40 parts by weight of the unsaturated carboxylic acid, the unsaturated carboxylic anhydride or the mixture thereof; iii) 10 to 70 parts by weight of the epoxy-containing unsaturated compound; and iv) 5 to 70 parts by weight of the olefinic unsaturated compound, b) 5 to 50 parts by weight of the 1,2-quinonediazide 5-sulfonate compound having the phenol compound including the compound represented by Chemical Formula A as a ballast; or a 1,2-quinonediazide 5-sulfonate compound having the phenol compound including the compound represented by Chemical Formula A and the compound represented by Chemical Formula B as a ballast, and c) 0.1 to 30 parts by weight of the silane coupling agent.

6. The photosensitive resin composition according to claim 5, wherein: The solvent is present in an amount such that the solid content of the components comprising a), b) and c) is from 10 wt % to 50 wt %.

7. The photosensitive resin composition according to claim 1, wherein: The unsaturated carboxylic acid, the unsaturated carboxylic anhydride or the mixture thereof of a) ii) includes one or more selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid and unsaturated carboxylic anhydrides thereof.

8. The photosensitive resin composition according to claim 1, wherein: a) The epoxy-containing unsaturated compound of iii) includes one or more selected from the group consisting of glycidyl acrylate, glycidyl methacrylate, α-ethyl glycidyl acrylate, α-n-propyl glycidyl acrylate, α-n-butyl glycidyl acrylate, β-methyl glycidyl acrylate, β-methyl glycidyl methacrylate, β-ethyl glycidyl acrylate, β-ethyl glycidyl methacrylate, 3,4-epoxybutyl acrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7-epoxyheptyl methacrylate, α-ethyl 6,7-epoxyheptyl acrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, 3,4-epoxycyclohexyl methacrylate, 3,4-epoxycyclohexyl methyl methacrylate, 3,4-epoxycyclohexyl acrylate and 3,4-epoxycyclohexyl methyl acrylate.

9. The photosensitive resin composition according to claim 1, wherein: a) The olefinic unsaturated compound of iv) includes one or more selected from the group consisting of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, methyl acrylate, isopropyl acrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, dicyclopentenyl acrylate, dicyclopentane acrylate, dicyclopentenyl methacrylate, dicyclopentane methacrylate, 1-adamantyl acrylate, 1-adamantyl methacrylate, dicyclopentyloxyethyl methacrylate, isobornyl methacrylate, cyclohexyl acrylate, 2-methylcyclohexyl acrylate, dicyclopentyloxyethyl acrylate, isobornyl methacrylate, phenyl methacrylate, phenyl acrylate, benzyl acrylate, 2-hydroxyethyl methacrylate, styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene.

10. The photosensitive resin composition according to claim 1, wherein: The acrylic copolymer of a) has a weight average molecular weight (Mw) of 3,000 to 20,000 in terms of polystyrene.

11. The photosensitive resin composition according to claim 1, wherein: c) The silane coupling agent comprises one or more selected from the group consisting of: (3-glycidoxypropyl)trimethoxysilane, (3-glycidoxypropyl)triethoxysilane, (3-glycidoxypropyl)methyldimethoxysilane, (3-glycidoxypropyl)methyldiethoxysilane, (3-glycidoxypropyl)dimethylethoxysilane, 3,4-epoxybutyltrimethoxysilane, 3,4-epoxybutyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, Silane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, aminopropyltrimethoxysilane, aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylene)propylamine, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and (3-isocyanatopropyl)triethoxysilane.

12. The photosensitive resin composition according to claim 1, wherein: The solvent of d) comprises one or more selected from the group consisting of diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate, propylene glycol propyl ether propionate, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, butylene glycol monomethyl ether, butylene glycol monoethyl ether, dibutylene glycol dimethyl ether, dibutylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol butyl ethyl ether, triethylene glycol dimethyl ether, triethylene glycol butyl methyl ether, diethylene glycol tert-butyl ether, tetraethylene glycol dimethyl ether, diethylene glycol ethyl hexyl ether, diethylene glycol methyl hexyl ether, dipropylene glycol butyl methyl ether, dipropylene glycol ethyl hexyl ether and dipropylene glycol methyl hexyl ether. 13 . A display device comprising a cured body of the photosensitive resin composition according to claim 1 .

14. The display device according to claim 13, comprising: An organic insulating film includes the cured product of the photosensitive resin composition.

15. The display device according to claim 14, further comprising: substrate, The thin film transistor on the substrate, a pixel electrode coupled to the thin film transistor, and A color filter is superimposed on the thin film transistor.

16. The display device according to claim 15, wherein: The color filter is between the organic insulating film and the thin film transistor.

17. A display device, comprising: substrate, The thin film transistor on the substrate, a pixel electrode coupled to the thin film transistor, and an organic insulating film superimposed on the substrate, The organic insulating film comprises a cured product of the photosensitive resin composition according to any one of claims 1 to 12.

Images