Photosensitive resin composition, photosensitive resin film, display device, and method for producing photosensitive resin film

Abstract

To provide a photosensitive resin composition which is sufficiently cured even at low temperature, is transparent, and has a high refractive index.SOLUTION: A photosensitive resin composition contains (A) a binder resin, (B) a photopolymerizable monomer which contains a thianthrene and is represented by a specific formula, (C) a photopolymerization initiator, and (D) a solvent.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present disclosure relates to a photosensitive resin composition, a photosensitive resin film, a display device, and a method for producing a photosensitive resin film. [Background technology]

[0002] Recently, there has been growing interest in self-emissive micro OLED display panels, which emit light themselves, as display panels applied to VR (Virtual Reality), AR (Augmented Reality), and MR (Mixed Reality) devices.

[0003] In the case of micro OLED display panels, which have pixel sizes about 10 times smaller than those of general OLED display panels, it is difficult to precisely form the red (R), green (G), and blue (B) light-emitting layers using conventional FMM (Fine Metal Mask) technology. In other words, when applying conventional LCD displays to devices such as VR and AR, the pattern size of the color filter is large, making it difficult to increase the resolution.

[0004] In recent years, OLEDoS (OLED on Silicon) technology has been introduced to achieve high resolutions of over 4000 ppi. This technology uses an OLED deposited on a silicon wafer as a backlight, on which a color filter is patterned. Conventional color filters used in LCDs are patterned with a thickness of approximately 100 μm on glass, exposed to light, and then hardened through a post-bake process at temperatures above 230°C. However, color filters formed on OLEDoS cannot undergo high-temperature processes due to the nature of OLEDs, and must be cured at low temperatures. Another issue is the low efficiency of emitted light due to the characteristics of OLEDs. Therefore, ongoing research is being conducted into transparent materials with high refractive indexes that can be cured at low temperatures. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Korean Patent Publication No. 2020-0131755 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of one embodiment is to provide a photosensitive resin composition that is sufficiently cured even at low temperatures, is transparent, and has a high refractive index.

[0007] Another embodiment of the present invention provides a photosensitive resin film produced using the photosensitive resin composition.

[0008] Another object of another embodiment is to provide a display device including the photosensitive resin film.

[0009] Furthermore, an object of another embodiment is to provide a method for producing the photosensitive resin film. [Means for solving the problem]

[0010] One embodiment provides a photosensitive resin composition comprising (A) a binder resin, (B) a photopolymerizable monomer, (C) a photopolymerization initiator, and (D) a solvent, wherein the photopolymerizable monomer is represented by the following chemical formula 1:

[0011] [Chemical formula 1] [ka]

[0012] In chemical formula 1, R 1 and R 2 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, R 3 and R 4are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, L 1 and L 2 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, or a substituted or unsubstituted C6 to C20 arylene group, L 3 ~L 6 are each independently a substituted or unsubstituted C1 to C20 alkylene group, m and n each independently represent an integer of 0 to 4.

[0013] L 1 and L 2 may each independently be an unsubstituted C6 to C20 arylene group.

[0014] L 1 and L 2 may each independently be a C6 to C20 arylene group substituted with a halogen group and / or a C1 to C20 alkyl group substituted with a halogen group.

[0015] L 1 and L 2 may each independently be an unsubstituted C1 to C20 alkylene group.

[0016] L 1 and L 2 may each independently be an unsubstituted C3 to C20 cycloalkylene group.

[0017] L 3 ~L 6 may all be the same.

[0018] The photopolymerizable monomer may be represented by any one of the following chemical formulas 1-1 to 1-7.

[0019] [Chemical formula 1-1] [ka]

[0020] [Chemical formula 1-2] [ka]

[0021] [Chemical formula 1-3] [ka]

[0022] [Chemical formula 1-4] [ka]

[0023] [Chemical formula 1-5] [ka]

[0024] [Chemical formula 1-6] [ka]

[0025] [Chemical formula 1-7] [ka]

[0026] The photosensitive resin composition can contain, relative to the total amount of the photosensitive resin composition, (A) 10% by weight to 30% by weight of a binder resin, (B) 3% by weight to 15% by weight of a photopolymerizable monomer, (C) 0.1% by weight to 5% by weight of a photopolymerization initiator, and (D) a remaining amount of solvent.

[0027] The photosensitive resin composition may further contain additives such as malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a surfactant, a polymerization inhibitor, or a combination thereof.

[0028] The photosensitive resin composition may have a refractive index of 1.62 or more at 550 nm.

[0029] The photosensitive resin composition may have a transmittance of 90% or more at 400 nm to 700 nm.

[0030] Another embodiment provides a photosensitive resin film produced using the photosensitive resin composition.

[0031] The photosensitive resin film may be transparent.

[0032] Another embodiment provides a display device including the photosensitive resin film.

[0033] The display device may be a micro OLED display device including an OLED substrate deposited on a silicon wafer, and a color filter layer located on the OLED substrate for converting white light generated by the OLED substrate into a plurality of color lights, wherein a photosensitive resin film is located on the OLED substrate and the color filter layer, and the color filter layer includes a red color filter, a green color filter, and a blue color filter.

[0034] Furthermore, another embodiment provides a method for producing a photosensitive resin film, including the steps of applying the photosensitive resin composition, pre-baking the applied composition at a temperature of 100°C or less, exposing the pre-baked composition to i-rays, and developing the applied composition.

[0035] Other specific aspects of the present invention are included in the detailed description below. [Effects of the Invention]

[0036] The photosensitive resin composition according to one embodiment is a transparent photosensitive resin composition that can be cured at a low temperature of 100°C or less, has a high refractive index at 550 nm, and has high transmittance in the visible light region (400 nm to 700 nm). Since the above-mentioned effects can be achieved with only a pre-bake temperature of 100°C or less and photo-curing (i-line exposure), the composition can be suitably used as a microlens layer (micro lens array) in a micro OLED display device, which can realize fine patterns. [Brief explanation of the drawings]

[0037] [Figure 1] 1 is a schematic diagram illustrating the structure of a micro OLED display device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0038] DETAILED DESCRIPTION OF THE INVENTION The following detailed description of the preferred embodiments of the present invention is provided by way of example only and is not intended to limit the scope of the present invention, which is defined solely by the scope of the claims set forth below.

[0039] Unless otherwise specified in this specification, an "alkyl group" means a C1 to C20 alkyl group, an "alkenyl group" means a C2 to C20 alkenyl group, a "cycloalkenyl group" means a C3 to C20 cycloalkenyl group, a "heterocycloalkenyl group" means a C3 to C20 heterocycloalkenyl group, an "aryl group" means a C6 to C20 aryl group, an "arylalkyl group" means a C6 to C20 arylalkyl group, an "alkylene group" means a C1 to C20 alkylene group, an "arylene group" means a C6 to C20 arylene group, an "alkylarylene group" means a C6 to C20 alkylarylene group, a "heteroarylene group" means a C3 to C20 heteroarylene group, and an "alkoxyylene group" means a C1 to C20 alkoxyylene group.

[0040] Unless otherwise specified in this specification, "substituted" means that at least one hydrogen atom has been replaced with a halogen atom (F, Cl, Br, I), a hydroxy group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, an azide group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof ... C1 to C20 alkoxy group, a C1 to C20 alkoxy group, a C1 to C20 alkoxy group, a C1 to C20 alkoxy group, a C1 to C20 alkoxy group, a C1 to C20 alkoxy group, a C1 to C20 alkoxy It means being substituted with a substituent selected from a C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C3-C20 cycloalkyl group, a C3-C20 cycloalkenyl group, a C3-C20 cycloalkynyl group, a C2-C20 heterocycloalkyl group, a C2-C20 heterocycloalkenyl group, a C2-C20 heterocycloalkynyl group, a C3-C20 heteroaryl group, or a combination thereof.

[0041] Unless otherwise specified herein, "hetero" means that at least one heteroatom of at least one of N, O, S, and P is included in the chemical formula.

[0042] Unless otherwise specified in this specification, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" means that both "acrylic acid" and "methacrylic acid" are possible.

[0043] Unless otherwise defined herein, "combination" means a mixture or copolymerization, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymerization or random copolymerization.

[0044] Unless otherwise defined in the chemical formulas herein, when no chemical bond is drawn at a position where a chemical bond should be drawn, this means that a hydrogen atom is bonded at that position.

[0045] Unless otherwise defined herein, "*" means a moiety connected to the same or different atom or chemical formula.

[0046] A photosensitive resin composition according to one embodiment includes (A) a binder resin, (B) a photopolymerizable monomer represented by the following chemical formula 1, (C) a photopolymerization initiator, and (D) a solvent.

[0047] [Chemical formula 1] [ka]

[0048] In chemical formula 1, R 1 and R 2 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, R 3 and R 4 are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, L 1 and L 2 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, or a substituted or unsubstituted C6 to C20 arylene group, L 3 ~L 6 are each independently a substituted or unsubstituted C1 to C20 alkylene group, m and n each independently represent an integer of 0 to 4.

[0049] Liquid crystal display (LCD) devices, a type of display device, are becoming increasingly popular in notebook computers, monitors, and TVs due to their advantages of light weight, thinness, low cost, low power consumption, and excellent compatibility with integrated circuits. These LCD devices comprise a lower substrate on which a black matrix, color filters, and ITO pixel electrodes are formed, and an upper substrate on which an active circuit consisting of a liquid crystal layer, thin film transistors, and a storage capacitor layer, as well as ITO pixel electrodes, are formed. A color filter is constructed by sequentially stacking a black matrix layer formed in a predetermined pattern on a transparent substrate to shield the boundaries between pixels, and pixel regions in which multiple colors (usually the three primary colors of red (R), green (G), and blue (B)) are arranged in a predetermined order to form each pixel. The pigment dispersion method, one method for producing color filters, involves coating a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix, exposing the resulting pattern to light, removing the unexposed areas with a solvent, and then thermally curing the resulting layer. This process forms a colored thin film. The colored photosensitive resin composition used in the production of color filters using the pigment dispersion method generally consists of an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method, which has the above-mentioned characteristics, is widely used in the production of LCDs for mobile phones, laptops, monitors, TVs, etc.

[0050] However, applying LCD color filter manufacturing technology to VR and AR devices, which have recently attracted market interest, has been limited by resolution limitations. OLEDoS (OLED on Silicon) technology has been introduced to achieve high resolutions of over 4000 ppi. This technology involves patterning a color filter on an OLED deposited on a silicon wafer as a backlight. While color filters used in conventional LCDs are cured through a post-bake process at temperatures above 230°C, color filters formed on OLEDoS must be cured at low temperatures to ensure the durability of the OLED material. Furthermore, fine patterning is essential to achieve the desired resolution within the small dimensions of VR and AR devices. However, since this technology requires curing at a low temperature (100°C), there is a potential problem of color discoloration due to its low chemical resistance. To address this issue, it is essential to increase the degree of curing of the resist.

[0051] Displays such as OLEDs generally have a problem in that the efficiency of the generated light being emitted to the outside is low.To solve this problem, a technology that uses a high refractive index layer or a high refractive index pattern to control the refractive index difference, which is one of the causes of loss when light is emitted to the outside, is known.

[0052] In an attempt to enhance the functionality of polymer compounds, polyimide polymer materials containing sulfur atoms have been developed as a way to ensure a high refractive index (>1.60). However, polyimide materials have the property of absorbing light in the wavelength range around 400 nm, making them unsuitable for microlenses that receive light in the visible light range (400 nm to 700 nm).

[0053] The present invention is not an invention about a color photoresist used in the manufacture of conventional color filters as described above, but an invention about a microlens applied to a Micro OLED display device, which has a high refractive index of 1.62 or more, for example, 1.63 or more, for example, 1.64 or more, for example, 1.65 or more, for example, 1.66 or more at 550 nm, and a very high transmittance of 90% or more, for example, 95% or more in the visible light region, making it very suitable for use as a microlens that receives light.

[0054] Each component will be specifically described below.

[0055] (A) Binder resin The binder resin may include an acrylic binder resin.

[0056] The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing one or more acrylic repeating units.

[0057] The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxy groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

[0058] The first ethylenically unsaturated monomer may be contained in an amount of 5% by weight to 50% by weight, for example 10% by weight to 40% by weight, based on the total amount of the acrylic binder resin.

[0059] Examples of the second ethylenically unsaturated monomer include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzyl methyl ether; unsaturated carboxylic acid ester compounds such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, and phenyl (meth)acrylate; unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; cyanide vinyl compounds such as (meth)acrylonitrile; and unsaturated amide compounds such as (meth)acrylamide. These can be used alone or in combination.

[0060] Specific examples of acrylic binder resins include (meth)acrylic acid / benzyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene copolymer, (meth)acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc., but are not limited thereto, and these can be used alone or in combination of two or more.

[0061] The acrylic binder resin may have a weight-average molecular weight of 3,000 g / mol to 20,000 g / mol and a double bond equivalent of 340 g / mol or more. When the weight-average molecular weight and double bond equivalent of the acrylic binder resin are within the above ranges, the resulting thin film has excellent pattern formability and excellent mechanical and thermal properties.

[0062] The binder resin may further include an epoxy-based binder resin.

[0063] The binder resin can improve heat resistance by further containing an epoxy-based binder resin, such as, but not limited to, phenol novolac epoxy resin, tetramethylbiphenyl epoxy resin, bisphenol A epoxy resin, bisphenol F epoxy resin, alicyclic epoxy resin, or a combination thereof.

[0064] The binder resin including the epoxy-based binder resin ensures the dispersion stability of colorants such as pigments, which will be described later, and also helps form pixels with a desired resolution during the development process.

[0065] The epoxy binder resin may be contained in an amount of 1 to 10% by weight, for example, 5 to 10% by weight, based on the total amount of binder resins. When the epoxy binder resin is contained in the above range, the film retention rate and chemical resistance can be significantly improved.

[0066] The epoxy equivalent weight of the epoxy binder resin may be 150 g / eq to 200 g / eq. When an epoxy binder resin having an epoxy equivalent weight within the above range is contained in the binder resin, there is an advantageous effect in improving the degree of hardening of the formed pattern and in fixing the colorant within the structure in which the pattern is formed.

[0067] The binder resin may be contained in an amount of 10 to 30% by weight, specifically 10 to 25% by weight, based on the total amount of the photosensitive resin composition. When the binder resin is contained within the above range, excellent sensitivity, developability, resolution, and linearity of the pattern can be obtained.

[0068] (B) Photopolymerizable monomer The photopolymerizable monomer in the photosensitive resin composition according to one embodiment may be a single compound or a mixture of two different compounds.

[0069] For example, the photopolymerizable monomer may be a trifunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond, and specifically, the photopolymerizable monomer is represented by the above chemical formula 1.

[0070] As the photopolymerizable monomer is represented by Chemical Formula 1, sufficient polymerization occurs upon exposure in the pattern formation process, enabling the formation of patterns with excellent heat resistance, light resistance, and chemical resistance, as well as a high refractive index at 550 nm and high transmittance in the visible light region.

[0071] For example, L 1 and L 2 may each independently be an unsubstituted C6 to C20 arylene group, for example, L 1 and L 2 may all be unsubstituted C6 arylene groups (for example, phenylene groups) or unsubstituted C10 arylene groups (for example, naphthylene groups).

[0072] For example, L 1 and L 2 may each independently be a C6 to C20 arylene group substituted with a "halogen group and / or a C1 to C20 alkyl group substituted with a halogen group." The halogen group may be a fluoro group, a chloro group, a bromo group, or an iodo group, and the C1 to C20 alkyl group substituted with a halogen group may be, for example, a trifluoromethyl group.

[0073] For example, L 1 and L 2 may each independently be an unsubstituted C1 to C20 alkylene group or an unsubstituted C1 to C10 alkylene group.

[0074] For example, L 1 and L 2 may each independently be an unsubstituted C3 to C20 cycloalkylene group, an unsubstituted C6 cycloalkylene group, or a cyclohexylene group.

[0075] For example, L 3 ~L 6 may all be the same, and L 3 ~L 6 may all be methylene groups or ethylene groups.

[0076] For example, the photopolymerizable monomer is represented by any one of the following chemical formulas 1-1 to 1-7, but is not necessarily limited thereto.

[0077] [Chemical formula 1-1] [ka]

[0078] [Chemical formula 1-2] [ka]

[0079] [Chemical formula 1-3] [ka]

[0080] [Chemical formula 1-4] [ka]

[0081] [Chemical formula 1-5] [ka]

[0082] [Chemical formula 1-6] [ka]

[0083] [Chemical formula 1-7] [ka]

[0084] The photosensitive resin composition according to an embodiment may further contain, in addition to the photopolymerizable monomer represented by Chemical Formula 1, a photopolymerizable monomer having a different structure.

[0085] Specific examples of photopolymerizable monomers having a structure different from that of Chemical Formula 1 include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, ) acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy (meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(meth)acryloyloxyethyl phosphate, novolac epoxy (meth)acrylate, ethoxylated bisphenylfluorene diacrylate, ethoxylated naphthalene type diacrylate, ethoxylated sulfur type diacrylate, and the like.

[0086] Examples of commercially available photopolymerizable monomers having a structure different from that of Chemical Formula 1 are as follows: Examples of monofunctional esters of (meth)acrylic acid include Aronix (registered trademark) M-101, M-111, and M-114 manufactured by Toagosei Chemical Industry Co., Ltd., KAYARAD (registered trademark) TC-110S and TC-120S manufactured by Nippon Kayaku Co., Ltd., and V-158 and V-2311 manufactured by Osaka Organic Chemical Industry Ltd. Examples of bifunctional esters of (meth)acrylic acid include Aronix M-210, M-240, and M-6200 manufactured by Toagosei Chemical Industry Co., Ltd.; KAYARAD HDDA, HX-220, and R-604 manufactured by Nippon Kayaku Co., Ltd.; V-260, V-312, and V-335HP manufactured by Osaka Organic Chemical Industry Ltd.; and BPF-022, BPF-022B, BPF-022L, BPF-022G, BPF-102, BPF-152, BPF-202, BPF-302, BN-042, BN-102, TBP-042, and TBP-102 manufactured by Hanno Chemical Co., Ltd. Examples of trifunctional esters of (meth)acrylic acid include Aronix M-309, M-400, M-405, M-450, M-710, M-8030, and M-8060 manufactured by Toagosei Chemical Industry Co., Ltd., KAYARAD TMPTA, DPCA-20, DPCA-30, DPCA-60, and DPCA-120 manufactured by Nippon Kayaku Co., Ltd., and V-295, V-300, V-360, V-GPT, V-3PA, and V-400 manufactured by Osaka Organic Chemical Industry Co., Ltd. These products can be used alone or in combination of two or more.

[0087] The photopolymerizable monomer can also be used after being treated with an acid anhydride in order to impart better developability.

[0088] For example, the photopolymerizable monomer may be contained in an amount of 3 to 15% by weight, or 5 to 10% by weight, based on the total amount of the photosensitive resin composition. For example, the photopolymerizable monomer may be contained in an amount of 20 to 60% by weight, or 30 to 50% by weight, based on the total amount of solids constituting the photosensitive resin composition. When the photopolymerizable monomer is contained within the above ranges, sufficient curing occurs upon exposure in the pattern formation step, resulting in excellent reliability and excellent developability in an alkaline developer.

[0089] (C) Photopolymerization initiator The photosensitive resin composition according to an embodiment includes a photopolymerization initiator, such as an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, or an oxine-based compound.

[0090] Examples of acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one.

[0091] Examples of benzophenone compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

[0092] Examples of thioxanthone compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, and 2,4-diisopropylthioxanthone.

[0093] Examples of the benzoin-based compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0094] Examples of triazine compounds include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine. azine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphth1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, and the like.

[0095] Examples of oxine compounds that can be used include O-acyloxine compounds, 2-(O-benzoyloxine)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(O-acetyloxine)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, and O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one. Specific examples of O-acyloxine compounds that can be used include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxine-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione-2-oxine-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-oneoxine-O-acetate, 1-(4-phenylsulfanylphenyl)-butan-1-one, and oxine-O-acetate.

[0096] In addition to the above compounds, the photopolymerization initiator may also be a carbazole-based compound, a diketone compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, a non-imidazole-based compound, or the like.

[0097] For example, the photopolymerization initiator may be contained in an amount of 0.1 to 5% by weight, or 0.5 to 3% by weight, based on the total amount of the photosensitive resin composition. For example, the photopolymerization initiator may be contained in an amount of 1 to 5% by weight, or 1.5 to 3% by weight, based on the total amount of solids constituting the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, sufficient photopolymerization occurs upon exposure in the pattern formation process for manufacturing microlenses, resulting in excellent sensitivity and improved transmittance.

[0098] (D) Solvent The solvent may be a substance that is compatible with, and does not react with, the polymer resin, the photopolymerizable monomer, and the photopolymerization initiator.

[0099] Examples of the solvent include alcohols such as methanol and ethanol, ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methyl phenyl ether, and tetrahydrofuran, glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and ethylene glycol dimethyl ether, cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate, carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, and diethylene glycol diethyl ether, propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate, aromatic hydrocarbons such as toluene and xylene, methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methylpropional, methyl ... ketones such as methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactic acid esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; alcohols such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; alkyl esters of alkoxypropionates such as methyl 3-oxypropionate and ethyl 3-oxypropionate; alkyl esters of 3-alkoxypropionates such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, and methyl 3-ethoxypropionate; alkyl esters of 2-oxypropionates such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; methyl 2-methoxypropionate;2-alkoxypropionic acid alkyl esters such as ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; or monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate, and 2-hydroxypropionic acid alkyl esters. esters such as methyl 3-methylbutanoate, and ketone acid esters such as ethyl pyruvate, as well as high-boiling solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

[0100] Of these, in consideration of compatibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and diethylene glycol ethyl methyl ether, ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate, esters such as ethyl 2-hydroxypropionate, carbitols such as diethylene glycol monomethyl ether, and propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be preferably used.

[0101] For example, the solvent may be contained in an amount of 50 to 90% by weight, 60 to 80% by weight, or 70 to 80% by weight relative to the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has an appropriate viscosity, which results in excellent processability when producing a photosensitive resin film, specifically a microlens.

[0102] (E) Other additives Meanwhile, the photosensitive resin composition may further contain additives such as malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a surfactant, a polymerization inhibitor, or a combination thereof.

[0103] The silane coupling agent may have a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, or an epoxy group in order to improve adhesion to the substrate, etc. However, even if a silane coupling agent is used, since the photosensitive resin composition according to one embodiment is a colorant-free composition, i.e., a transparent photosensitive resin composition, if the refractive index at 550 nm of the polymer resin is not controlled as described above, the effect of improving adhesion to the color filter may not be obtained.

[0104] Examples of silane coupling agents include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and the like, which can be used alone or in combination of two or more.

[0105] The silane coupling agent may be contained in an amount of 0.01 to 10 parts by weight relative to 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is contained within the above range, the composition has excellent adhesion, storage stability, and the like.

[0106] Furthermore, the photosensitive resin composition may further contain a surfactant, such as a fluorine-based surfactant and / or a silicone-based surfactant, if necessary, to improve coating properties and prevent the formation of defects.

[0107] Examples of fluorine-based surfactants that can be used include those commercially available under the names BM-1000 and BM-1100 manufactured by BM Chemie; Megafac (registered trademark) F142D, F172, F173, F183, F554, and F556 manufactured by Dainippon Ink and Chemicals, Inc.; Fluorad FC-135, FC-170C, FC-430, and FC-431 manufactured by Sumitomo 3M Limited; Surflon (registered trademark) S-112, S-113, S-131, S-141, and S-145 manufactured by Asahi Glass Co., Ltd.; and SH-28PA, SH-190, SH-193, SZ-6032, and SF-8428 manufactured by Toray Silicone Co., Ltd.

[0108] As the silicone surfactant, those commercially available from BYK Chem under the names BYK-307, BYK-333, BYK-361N, BYK-051, BYK-052, BYK-053, BYK-067A, BYK-077, BYK-301, BYK-322, BYK-325, etc. can be used.

[0109] The surfactant can be used in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is used in an amount within this range, coating uniformity is ensured, staining does not occur, and wetting to IZO substrates or glass substrates is excellent.

[0110] The polymerization inhibitor may include, but is not limited to, a catechol-based compound. When the photosensitive resin composition according to an embodiment further includes a catechol-based compound, room temperature crosslinking during exposure after coating of the photosensitive resin composition can be prevented.

[0111] For example, catechol-based compounds can include, but are not necessarily limited to, catechol, t-butylcatechol, 4-methoxyphenol, pyrogallol, 2,6-di-t-butyl-4-methylphenol, 2-naphthol, and tris(N-hydroxy-N-nitrosophenylaminato-O,O')aluminum.

[0112] The catechol compound can be used in the form of a dispersion, and the polymerization inhibitor in the dispersion form can be contained in an amount of 0.001 to 3% by weight, or 0.01 to 1% by weight, based on the total amount of the photosensitive resin composition. When the polymerization inhibitor is contained within the above range, the problem of aging at room temperature can be solved, and at the same time, a decrease in sensitivity and surface peeling can be prevented.

[0113] Furthermore, the photosensitive resin composition may contain a certain amount of other additives such as stabilizers within a range that does not impair the physical properties.

[0114] The photosensitive resin composition according to an embodiment may be a positive type or a negative type, but is preferably a negative type in order to more completely remove residues in areas where a pattern is exposed after exposure and development of a composition having light-blocking properties.

[0115] Meanwhile, the photosensitive resin composition according to an embodiment may have a refractive index (at 550 nm) of 1.62 or more, for example, a refractive index (at 550 nm) of 1.62 or more and 1.8 or less, by including the photopolymerizable monomer represented by Chemical Formula 1. Furthermore, the photosensitive resin composition according to an embodiment may have a transmittance in the visible light region (400 nm to 700 nm) of 90% or more, 95% or more, 96% or more, or 97% or more by including the photopolymerizable monomer represented by Chemical Formula 1. When the refractive index at 550 nm and the transmittance in the visible light region of the photosensitive resin composition including the photopolymerizable monomer represented by Chemical Formula 1 are controlled as described above, the loss of white light generated from the OLED substrate when it exits to the outside can be significantly reduced, which is advantageous for improving developability and fine patterning. Due to these characteristics, the photosensitive resin composition according to an embodiment is highly suitable as a microlens material for OLEDoS.

[0116] Another embodiment provides a photosensitive resin film manufactured by low-temperature curing, exposing, and developing the above-described photosensitive resin composition. This method differs from conventional LCD and semiconductor processes in that it does not require a post-curing (post-bake) process.

[0117] The photosensitive resin film is produced as follows.

[0118] (1) Application and coating film formation step (low temperature curing) The photosensitive resin composition is applied to a substrate such as a silicon wafer that has been pretreated to a desired thickness using methods such as spin or slit coating, roll coating, screen printing, or applicator, and then heated at 100°C for 1 to 10 minutes to remove the solvent, forming a photosensitive resin film. This step can improve image quality and staining.

[0119] (2) Exposure step To form the required pattern in the resulting photosensitive resin film, the film is irradiated with i-rays through a mask. The light source used for irradiation can be a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, an argon gas laser, or, in some cases, X-rays or electron beams.

[0120] The exposure dose varies depending on the type and amount of each component of the composition and the thickness of the dried film, but when using a high-pressure mercury lamp, it is 500 mJ / cm 2 (with a 365nm sensor) or less. This step allows for fine tuning of pixel size, enabling higher resolution.

[0121] (3) Development step The development method involves using an alkaline aqueous solution as a developer following the exposure step to dissolve and remove unwanted areas, leaving only the exposed areas to form a pattern. This step allows for the formation of a profile, achieving high resolution, ensuring color uniformity and improving clarity.

[0122] Another embodiment provides a display device including a photosensitive resin film.

[0123] The display device may be a micro organic light emitting diode (OLED) display device.

[0124] A micro organic light emitting device (OLED) display device includes an OLED substrate deposited on a silicon wafer and a color filter layer positioned on the OLED substrate to convert white light generated by the OLED substrate into multiple color lights. The color filter layer may include red, green, and blue color filters. A photosensitive resin film, i.e., a microlens layer, is positioned on the OLED substrate and the color filter layer. That is, the microlens layer may surround the color filter layer on the OLED substrate.

[0125] For example, a micro organic light emitting device (OLED) display device may include an OLED substrate deposited on a silicon wafer, an inorganic layer stacked on the OLED substrate, and a color filter layer stacked on the inorganic layer to convert white light generated by the OLED substrate into multiple color lights. The color filter layer may include a red color filter, a green color filter, and a blue color filter. A photosensitive resin film, i.e., a microlens layer, is positioned on the inorganic layer and the color filter layer. That is, the microlens layer may surround the color filter layer on the inorganic layer.

[0126] For example, a micro organic light emitting device (OLED) display device may include an OLED substrate deposited on a silicon wafer, an inorganic layer stacked on the OLED substrate, an adhesive protective layer stacked on the inorganic layer, and a color filter layer stacked on the adhesive protective layer to convert white light generated by the OLED substrate into multiple color lights. The color filter layer may include a red color filter, a green color filter, and a blue color filter. A photosensitive resin film, i.e., a microlens layer, is positioned on the adhesive protective layer and the color filter layer. That is, the microlens layer may surround the color filter layer on the adhesive protective layer.

[0127] While conventional OLED substrates have been used, in which OLEDs are deposited on glass or polyimide substrates, a micro OLED display device according to an embodiment has OLEDs deposited on a silicon wafer, which is advantageous for realizing a micro display. Such micro displays are attracting attention as next-generation displays and are expected to be applied to devices such as mixed reality. In fact, Apple, Meta, and LG Display have all either already entered the next-generation mixed reality device market or have announced their intention to enter it.

[0128] In the micro OLED display device with the above structure, WOLED is deposited on a highly integrated silicon wafer and driven in pixel units, and the transmitted wavelength can be easily controlled through the color filter layer patterned with a resolution of 3μm or less, which is advantageous for ensuring high color reproduction and high resolution.

[0129] For example, the thickness of the adhesive protective layer may be 1 μm or less, which maximizes the effects described above, namely, the improvement of adhesive strength to the color filter and the effect of reducing residue.

[0130] For example, the thickness of the color filter layer may be 1.1 μm to 1.6 μm.

[0131] When the thickness of the color filter layer is controlled as above, it is more advantageous to realize a micro OLED display device.

[0132] For example, the thickness of the inorganic layer may be 2 μm or less. Even in WOLEDs, light does not always diffuse only in the direction perpendicular to the OLED substrate, so red, green, and blue color mixing inevitably occurs. Conventionally, to prevent this color mixing, an inorganic layer has been deposited on the OLED substrate. However, since color mixing cannot be completely prevented even by depositing an inorganic layer, in one embodiment, the inorganic layer is thinned, for example, the thickness of the inorganic layer is controlled to 2 μm or less, thereby preventing minute light leakage.

[0133] As described above, the photosensitive resin composition according to one embodiment can produce a cured film by only pre-baking at a low temperature (100°C) and curing with i-line light, as described above, and therefore has a significant difference in achievable resolution compared to conventional display devices.

[0134] Preferred examples of the present invention will be described below, but the following examples are merely preferred examples of the present invention and the present invention is not limited to these examples. [Example]

[0135] <Production Example 1: Synthesis of Compound Represented by Chemical Formula 1> (Reaction Scheme 1) [ka]

[0136] Compound 1a (10.0 mmol) was added to 30.0 mL of N,N-dimethylformamide (DMF) together with compound 1b (4.00 mmol) and potassium carbonate (K2CO3, 4.00 mmol), and the mixture was refluxed overnight. After confirming the consumption of compound 1a by thin-layer chromatography, the reaction mixture was added to distilled water to produce a precipitate. The precipitate was separated by vacuum filtration, washed with distilled water, and recrystallized with toluene to obtain compound 1c.

[0137] (Reaction Scheme 2) [ka]

[0138] Compound 1c (5.00 mmol) was added to 20.0 mL of 1,4-dioxane / HO (v / v = 1 / 1) together with compound 1d (50.0 mmol) and potassium carbonate (K2CO3, 25.0 mmol) and stirred overnight at room temperature. After confirming the reduction of compound 1c by thin-layer chromatography, the reaction mixture was added to distilled water to produce a precipitate. The precipitate was separated by vacuum filtration, washed with distilled water, and dried overnight in a vacuum oven. Compound 1e was obtained by recrystallization using toluene.

[0139] (Reaction Scheme 3) [ka]

[0140] Compound 1e (10.0 mmol) was added to 30.0 mL of toluene together with compound 1f (30.0 mmol), tetrabutylphosphonium bromide (TBPB, 1.00 mmol), and butylated hydroxytoluene (BHT, 0.50 mmol), and the mixture was refluxed overnight. After removing the solvent under reduced pressure, the residue was purified by column chromatography (eluent: n-hexane / EtOAc) to obtain compound 1g.

[0141] (Reaction Scheme 4) [ka]

[0142] Compound 1g (10.0 mmol) was added to 10.0 mL of tetrahydrofuran (THF) together with compound 1h (20.5 mmol) and 4-dimethylaminopyridine (4-DMAP, 1.00 mmol), and the mixture was refluxed overnight. After removing the solvent under reduced pressure, the residue was purified by column chromatography (eluent: DCM / MeOH) to obtain the compound represented by formula 1.

[0143] The analytical results of the compound represented by Chemical Formula 1 are as follows: MALDI-TOF MS: 1017.13 m / z

[0144] <Production Example 2: Synthesis of Compound Represented by Chemical Formula 2> (Reaction Scheme 5) [ka]

[0145] The compound represented by the chemical formula 2 was synthesized in the same manner as in the synthesis of the compound represented by the chemical formula 1, except that the compound 2a was used instead of the compound 1h.

[0146] The analytical results of the compound represented by Chemical Formula 2 are as follows: MALDI-TOFMS: 1153.10 m / z

[0147] <Production Example 3: Synthesis of Compound Represented by Chemical Formula 3> (Reaction Scheme 6) [ka]

[0148] The compound represented by the chemical formula 3 was synthesized in the same manner as in the synthesis of the compound represented by the chemical formula 1, except that the compound 3a was used instead of the compound 1h.

[0149] The analytical results of the compound represented by Chemical Formula 3 are as follows: MALDI-TOFMS: 1117.16 m / z

[0150] <Production Example 4: Synthesis of Compound Represented by Chemical Formula 4> (Reaction Scheme 7) [ka]

[0151] Compound 4b was synthesized in the same manner as in the synthesis of compound 1g, except that compound 4a was used instead of compound 1f.

[0152] (Reaction Scheme 8) [ka]

[0153] The compound represented by the formula 4 was synthesized in the same manner as in the synthesis of the compound represented by the formula 1, except that the compound 4c was used instead of the compound 1h.

[0154] The analytical results of the compound represented by Chemical Formula 4 are as follows: MALDI-TOFMS: 1117.12 m / z

[0155] <Production Example 5: Synthesis of Compound Represented by Chemical Formula 5> (Reaction Scheme 9) [ka]

[0156] Compound 5b was synthesized in the same manner as in the synthesis of compound 1c, except that compound 5a was used instead of compound 1b.

[0157] (Reaction Scheme 10) [ka]

[0158] Compound 5c was synthesized in the same manner as in the synthesis of compound 1e, except that compound 5b was used instead of compound 1c.

[0159] (Reaction Scheme 11) [ka]

[0160] Compound 5d was synthesized in the same manner as in the synthesis of compound 1g, except that compound 5c was used instead of compound 1e.

[0161] (Reaction Scheme 12) [ka]

[0162] The compound represented by the chemical formula 5 was synthesized in the same manner as in the synthesis of the compound represented by the chemical formula 1, except that the compound 5d was used instead of the compound 1g.

[0163] The analytical results of the compound represented by Chemical Formula 5 are as follows: MALDI-TOFMS: 1073.19 m / z

[0164] <Production Example 6: Synthesis of Compound Represented by Chemical Formula 6> (Reaction Scheme 13) [ka]

[0165] The compound represented by the chemical formula 6 was synthesized in the same manner as in the synthesis of the compound represented by the chemical formula 1, except that the compound 6a was used instead of the compound 1h.

[0166] The analytical results of the compound represented by Chemical Formula 6 are as follows: MALDI-TOFMS: 921.13 m / z

[0167] <Production Example 7: Synthesis of Compound Represented by Chemical Formula 7> (Reaction Scheme 14) [ka]

[0168] The compound represented by the chemical formula 7 was synthesized in the same manner as in the synthesis of the compound represented by the chemical formula 1, except that the compound 7a was used instead of the compound 1h.

[0169] The analytical results of the compound represented by Chemical Formula 7 are as follows: MALDI-TOFMS: 1029.22 m / z

[0170] <Comparative Production Example 1: Synthesis of Compound Represented by Chemical Formula C-1> (Reaction Scheme 15) [ka]

[0171] A solution of compound 8a (25.0 mmol) and potassium tert-butoxide (KOt-Bu, 25.0 mmol) in 25.0 mL of DMF was stirred at room temperature for 1 hour. Compound 1a (10.0 mmol) was then added, and the temperature was raised to 120°C and stirred for 12 hours. After confirming the consumption of compound 1a through thin-layer chromatography, the reaction mixture was added to distilled water to produce a precipitate. The precipitate was separated by filtration under reduced pressure, washed with distilled water, and recrystallized using toluene to obtain compound 8b.

[0172] (Reaction Scheme 16) [ka]

[0173] N,N-dimethylaniline (15.0 mmol) was added to a solution of compound 8b (5.00 mmol) in 30.0 mL of THF. After cooling the solution to 0°C, a solution of compound 8c (20.0 mmol) in 10.0 mL of THF was slowly added. The reaction mixture was stirred overnight at room temperature, and then saturated aqueous sodium bicarbonate solution was added. The solution was diluted with distilled water and extracted with chloroform. The organic layer was passed through MgSO4, concentrated under reduced pressure, and purified by column chromatography (eluent: DCM / n-hexane) to obtain the compound represented by chemical formula C-1.

[0174] The analytical results of the compound represented by the chemical formula C-1 are as follows: MALDI-TOFMS: 477.02 m / z

[0175] <Comparative Production Example 2: Synthesis of Compound Represented by Chemical Formula C-2> (Reaction Scheme 17) [ka]

[0176] The compound represented by the chemical formula C-2 was synthesized in the same manner as in the synthesis of the compound represented by the chemical formula C-1, except that the compound 1c was used instead of the compound 8b.

[0177] The analytical results of the compound represented by chemical formula C-2 are as follows: MALDI-TOFMS: 573.02 m / z

[0178] <Production of Photosensitive Resin Composition> (Examples 1 to 7, Comparative Examples 1 and 2) A photopolymerization initiator was dissolved in a solvent according to the composition shown in Table 1 below, and then stirred at room temperature for 2 hours. A binder resin and a photopolymerizable monomer were added to the solution, and the solution was stirred at room temperature (25°C) for 1 hour, and then the entire solution was stirred again for 2 hours. The solution was filtered three times with a 0.45 μm filter to remove impurities, and a photosensitive resin composition was prepared.

[0179] [Table 1]

[0180] (A) Binder resin Acrylic binder resin (SP-RY38; Resonac)

[0181] (B) Photopolymerizable monomer (B-1) Photopolymerizable monomer of Production Example 1 (B-2) Photopolymerizable monomer of Production Example 2 (B-3) Photopolymerizable monomer of Production Example 3 (B-4) Photopolymerizable monomer of Production Example 4 (B-5) Photopolymerizable monomer of Production Example 5 (B-6) Photopolymerizable monomer of Production Example 6 (B-7) Photopolymerizable monomer of Production Example 7 (B-8) Photopolymerizable monomer of Comparative Production Example 1 (B-9) Photopolymerizable monomer of Comparative Production Example 2

[0182] (C) Photopolymerization initiator Oxine initiator (SPI-03, Samyang)

[0183] (D) Solvent Oxidant Propylene glycol monomethyl ether acetate (PGMEA, Daicel)

[0184] <Evaluation> After confirming that the photosensitive resin compositions of Examples 1 to 7 and Comparative Examples 1 and 2 were all transparent, their refractive indices at 550 nm were measured. Each of these compositions was then coated onto an 8-inch silicon wafer using a SEMES K-SPIN at a rotation speed that yielded a similar thickness. The wafer was then soft-baked on a 100°C hot plate and subjected to pattern exposure using a Nikon i-line stepper under exposure conditions of (Dose: 200 ms / Focus: -0.3). The thickness was measured using a TENCOR during the exposure process, followed by development to form a pattern. EHD-100S solution (TMAH) was used as the developer, and the time (seconds) for the resulting pattern to appear (BP) was measured.

[0185] After development was completed, the pattern formed on the patterned substrate was examined using a Hitachi CD-SEM to check the sensitivity of the pattern and the presence of residues around the pattern. The pattern was confirmed to be an intaglio pattern of 96 μm, and large-area residues were examined using an Olympus optical microscope. The results are shown in Table 2 below. The evaluation criteria for developability and pattern linearity are shown in Table 3 below.

[0186] [Table 2]

[0187] [Table 3]

[0188] From the above evaluation, it can be seen that the photosensitive resin composition according to one embodiment is a transparent photosensitive resin composition that not only has a very high refractive index at 550 nm, but also has excellent pattern linearity and residue characteristics even when cured at low temperature, making it suitable for use as a microlens surrounding a color filter in a micro OLED.

[0189] The present invention is not limited to the above-described embodiments, and can be manufactured in various different forms, and it should be understood that a person skilled in the art to which the present invention pertains can embody other specific forms without changing the technical idea or essential features of the present invention. Therefore, it should be understood that the above-described embodiments are illustrative in all respects and not limiting.

Claims

1. (A) a binder resin, (B) a photopolymerizable monomer, (C) a photopolymerization initiator, and (D) a solvent, The photopolymerizable monomer is a photosensitive resin composition represented by the following chemical formula 1. [Chemical formula 1] 【Chemistry 1】 (In the above Chemical Formula 1, R １ and R ２ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, R ３ and R ４ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, L １ and L ２ are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, or a substituted or unsubstituted C6 to C20 arylene group; L ３ ~L ６ are each independently a substituted or unsubstituted C1 to C20 alkylene group, m and n are each independently an integer of 0 to 4.

2. Said L １ and L ２ are each independently an unsubstituted C6 to C20 arylene group.

3. Said L １ and L ２ are each independently a C6 to C20 arylene group substituted with a halogen group and / or a C1 to C20 alkyl group substituted with a halogen group.

4. Said L １ and L ２ are each independently an unsubstituted C1 to C20 alkylene group.

5. Said L １ and L ２ are each independently an unsubstituted C3 to C20 cycloalkylene group.

6. Said L ３ ~L ６ The photosensitive resin composition according to claim 1 , wherein all of

7. The photosensitive resin composition according to claim 1, wherein the photopolymerizable monomer is represented by any one of the following chemical formulas 1-1 to 1-7. [Chemical formula 1-1] 【Chemistry 2】 [Chemical formula 1-2] 【Transformation 3】 [Chemical formula 1-3] 【Chemistry 4】 [Chemical formula 1-4] 【Transformation 5】 [Chemical formula 1-5] 【Transformation 6】 [Chemical formula 1-6] 【Transformation 7】 [Chemical formula 1-7] 【Transformation 8】

8. The photosensitive resin composition contains, relative to the total amount of the photosensitive resin composition, 10% by weight to 30% by weight of the binder resin (A), 3% by weight to 15% by weight of the (B) photopolymerizable monomer, 0.1% by weight to 5% by weight of the (C) photopolymerization initiator, and The photosensitive resin composition according to claim 1 , further comprising (D) a residual solvent.

9. 2. The photosensitive resin composition according to claim 1, further comprising an additive selected from the group consisting of malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a surfactant, a polymerization inhibitor, and combinations thereof.

10. The photosensitive resin composition according to claim 1 , wherein the photosensitive resin composition has a refractive index of 1.62 or more at 550 nm.

11. 2. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition has a transmittance of 90% or more at 400 nm to 700 nm.

12. A photosensitive resin film produced by using the photosensitive resin composition according to any one of claims 1 to 11.

13. A display device comprising the photosensitive resin film according to claim 12.

14. The display device is an OLED substrate deposited on a silicon wafer; and a color filter layer located on the OLED substrate and converting white light generated by the OLED substrate into a plurality of color lights; the photosensitive resin film is located on the OLED substrate and the color filter layer; 14. The display device of claim 13, wherein the color filter layer includes a red color filter, a green color filter, and a blue color filter.

15. A step of applying the photosensitive resin composition according to any one of claims 1 to 11; After the coating, pre-baking at a temperature of 100°C or less; After the pre-baking, exposing to i-line light; and A method for producing a photosensitive resin film, comprising the step of developing.

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