Photosensitive resin composition, photosensitive resin film, pattern formation method and light-emitting element

Abstract

To provide a photosensitive resin composition which enables easy formation of a film having high lithography resolution and good light-emitting characteristics, a photosensitive resin film obtained using the photosensitive resin composition, a pattern formation method using them, and a light-emitting element having a cured film obtained by using the photosensitive resin film.SOLUTION: A photosensitive resin composition contains (A) a resin having a (meth)acryloyl group, (B) a photoradical generator, and (C) a polymer obtained by copolymerization of quantum dots obtained by subjecting a silane coupling agent to coordinate treatment, alkoxysilane, an alkoxysilane hydrolysate or its condensate.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a photosensitive resin composition, a photosensitive resin film using the photosensitive resin composition, a pattern forming method, and a light-emitting device. [Background technology]

[0002] Various methods have been proposed to create displays with red, green and blue subpixels. One method involves converting the light from an LED array from shorter wavelengths, blue, to longer wavelengths, red and green, through a color conversion structure, using quantum dots.

[0003] In recent years, LED arrays have become micro-sized, and micro LED displays using these have been attracting attention. One method for forming a color conversion structure on an LED array is a lithography process using a photosensitive material (Patent Document 1), but in recent years, further miniaturization is required for application to small displays. In addition, there are high demands for light emission characteristics in terms of display clarity. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent Publication No. 2021-089347 [Non-patent literature]

[0005] [Non-Patent Document 1] Journal of Photopolymer Science and Technology, Vol 23, 2010, p115-119 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention has been made in view of the above circumstances, and has an object to provide a photosensitive resin composition capable of easily forming a film having high lithography resolution and good light-emitting properties, a photosensitive resin film obtained using the photosensitive resin composition, and a pattern formation method using these, as well as a light-emitting element provided with a cured film obtained using the photosensitive resin film. [Means for solving the problem]

[0007] In order to solve the above problems, the present invention provides a photosensitive resin composition, comprising: (A) a resin having a (meth)acryloyl group, (B) a photoradical generator, and (C) A polymer obtained by copolymerizing quantum dots coordinated with a silane coupling agent and an alkoxysilane, an alkoxysilane hydrolyzate, or a condensate thereof; The present invention provides a photosensitive resin composition comprising:

[0008] Such a photosensitive resin composition can easily form a film having high lithography resolution and good light emitting properties.

[0009] In the present invention, the component (C) preferably contains a skeleton having a radical-reactive functional group in the surface coating layer of the quantum dots.

[0010] Such a photosensitive resin composition can prevent the quantum dots from escaping during development, and can provide a pattern with high light-emitting properties.

[0011] In the present invention, the silane coupling agent of the component (C) preferably has, as a coordinating substituent, at least one of an amino group, a thiol group, a carboxy group, a phosphino group, a phosphine oxide group, and an ammonium ion.

[0012] Such a photosensitive resin composition has higher lithography resolution.

[0013] In the present invention, the photosensitive resin composition preferably contains the component (C) in an amount of 5 to 80% by mass.

[0014] Such a photosensitive resin composition makes it possible to form a fine pattern while maintaining good light emitting properties.

[0015] In the present invention, the double bond equivalent of the component (A) is preferably 240 to 1,000 g / mol.

[0016] Such a photosensitive resin composition has a high crosslink density and can form a pattern with a good shape after development.

[0017] In the present invention, the component (A) is preferably an acrylic resin having a weight average molecular weight Mw of 5,000 to 100,000 g / mol.

[0018] With such a photosensitive resin composition, the film thickness of the exposed area is less likely to be reduced during development, and the solubility of the unexposed area is good.

[0019] In the present invention, it is preferable that the composition further contains a surfactant (D).

[0020] Such a photosensitive resin composition can improve the coatability.

[0021] In the present invention, it is preferable that the composition further contains a silane coupling agent (E).

[0022] Such a photosensitive resin composition can improve the adhesion to a substrate.

[0023] In the present invention, it is preferable that the composition further contains (F) a crosslinking agent having two or more functional (meth)acryloyl groups.

[0024] If such a photosensitive resin composition is used, the resulting cured film will have high reliability.

[0025] In the present invention, it is preferable that the composition further contains a solvent (G).

[0026] Such a photosensitive resin composition can improve the coatability.

[0027] The present invention also provides a photosensitive resin film which is a dried product of the above-described photosensitive resin composition.

[0028] Such a photosensitive resin film has high lithography resolution and good light emitting properties.

[0029] The present invention also provides a pattern forming method, comprising the steps of: (i) applying the above-described photosensitive resin composition onto a substrate to form a photosensitive resin film on the substrate; (ii) exposing the photosensitive resin film to light; and (iii) A step of developing the exposed photosensitive resin film with a developer to dissolve and remove the non-exposed areas to form a pattern. The present invention provides a pattern forming method comprising the steps of:

[0030] Such a pattern formation method makes it possible to form a pattern with high lithographic resolution, and to obtain a film pattern having good light-emitting properties.

[0031] The present invention also provides a light-emitting device comprising the above-described photosensitive resin film having a pattern formed thereon and a cured film.

[0032] Such a light emitting element has high lithography resolution and good light emitting characteristics. Effect of the Invention

[0033] The photosensitive resin composition of the present invention contains a polymer obtained by copolymerizing a resin having a (meth)acryloyl group, a photoradical generator, quantum dots coordinated with a silane coupling agent, and an alkoxysilane, an alkoxysilane hydrolysate, or a condensate thereof, and thus can easily form a film having high resolution and good luminescence properties, and is therefore suitable for light-emitting devices. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0034] As described above, there has been a need for the development of a photosensitive resin composition capable of easily forming a film having high lithography resolution and good light-emitting properties, a photosensitive resin film obtained using the photosensitive resin composition, a pattern formation method using the composition, and a light-emitting element including a cured film obtained using the photosensitive resin film.

[0035] Means for Solving the Problems The present inventors have conducted intensive research in order to achieve the above-mentioned object, and as a result have found that a photosensitive resin composition comprising (A) a resin having a (meth)acryloyl group, (B) a photoradical generator, and (C) a polymer obtained by copolymerizing quantum dots coordinated with a silane coupling agent and an alkoxysilane, an alkoxysilane hydrolysate, or a condensate thereof has high lithography resolution and can easily form a film (photosensitive resin film) having good luminescence properties, thereby completing the present invention.

[0036] That is, the present invention is a photosensitive resin composition, (A) a resin having a (meth)acryloyl group, (B) a photoradical generator, and (C) A polymer obtained by copolymerizing quantum dots coordinated with a silane coupling agent and an alkoxysilane, an alkoxysilane hydrolyzate, or a condensate thereof; The present invention provides a photosensitive resin composition comprising:

[0037] The present invention will be described in detail below, but the present invention is not limited thereto.

[0038] [Photosensitive resin composition] The photosensitive resin composition of the present invention contains a polymer obtained by copolymerizing (A) a resin having a (meth)acryloyl group, (B) a photoradical generator, and (C) quantum dots coordinated with a silane coupling agent, and an alkoxysilane, an alkoxysilane hydrolyzate, or a condensate thereof. If necessary, the composition may further contain other components such as (D) a surfactant, (E) a silane coupling agent, (F) a crosslinking agent having two or more functional (meth)acryloyl groups, and (G) a solvent. Each component constituting the photosensitive resin composition will be described below.

[0039] [(A) Resin having a (meth)acryloyl group] The (A) resin having a (meth)acryloyl group used in the present invention is not particularly limited as long as it has a (meth)acryloyl group.

[0040] In the present invention, the resin (A) having a (meth)acryloyl group is preferably an acrylic resin having a weight average molecular weight Mw in the range of 5,000 to 100,000 g / mol, more preferably an acrylic resin having a weight average molecular weight Mw in the range of 10,000 to 50,000 g / mol. If the weight average molecular weight of the resin (A) having a (meth)acryloyl group is within the above range, the film is less likely to be reduced in the exposed area during development, and the solubility of the non-exposed area is good. In addition, the acrylic resin is transparent and colorless, making it suitable for display applications. The acrylic resin referred to here refers to a polymer of an acrylic acid ester or a methacrylic acid ester. The weight average molecular weight is a value obtained as a weight average molecular weight (weight average degree of polymerization) converted into polystyrene by GPC (gel permeation chromatography) analysis using toluene as a developing solvent.

[0041] In the present invention, the (A) resin having a (meth)acryloyl group preferably has a double bond equivalent in the range of 240 to 1,000 g / mol, more preferably in the range of 240 to 700 g / mol. The double bond equivalent is the weight of the resin per one (meth)acryloyl group. If the double bond equivalent of the (A) resin having a (meth)acryloyl group is within the above range, a pattern having a high crosslink density and a good shape after development can be formed.

[0042] In the present invention, the (A) resin having a (meth)acryloyl group preferably has an acid value in the range of 0 to 150 mgKOH / g. If the acid value is less than 30 mgKOH / g, the solubility in an alkaline developer is low, so development with an organic solvent is preferable. If the acid value is 150 mgKOH / g or less, the pattern does not peel off during alkaline development.

[0043] In the present invention, the (A) resin having a (meth)acryloyl group may be used alone or in combination of two or more kinds. The (A) resin having a (meth)acryloyl group is preferably in the range of 10 to 90 mass % relative to the total amount of the photosensitive resin composition. More preferably, it is in the range of 15 to 85 mass %.

[0044] [(B) Photoradical generator] The photoradical generator used in the present invention is not particularly limited, but examples thereof include acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, and oxime-based compounds.

[0045] 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.

[0046] Examples of benzophenone-based 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.

[0047] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.

[0048] Examples of the benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0049] 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. 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphth-1-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.

[0050] Examples of oxime compounds include 1,2-octanedione, O-acyloxime compounds, 2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(O-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, and O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one. Specific examples of O-acyloxime compounds include 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-one oxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate.

[0051] In addition to the above compounds, the (B) photoradical generator may also include carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, non-imidazole compounds, and fluorene compounds.

[0052] The content of the photoradical generator (B) is preferably in the range of 0.1 to 10% by mass, more preferably in the range of 0.5 to 6% by mass, based on the total amount of the photosensitive resin composition. When the content of the photoradical generator is within the above range, a pattern with excellent resolution and excellent balance between sensitivity and developability during exposure without residual film can be obtained. The photoradical generator may be used alone or in combination of two or more kinds.

[0053] [(C) A polymer obtained by copolymerizing quantum dots coordinated with a silane coupling agent and an alkoxysilane, an alkoxysilane hydrolyzate, or a condensate thereof] Quantum dots are nano-sized semiconductor materials. Atoms form molecules, and molecules form small molecular aggregates called clusters to form nanoparticles. When such nanoparticles show semiconductor properties, they are called quantum dots (quantum dot particles).

[0054] When a quantum dot receives energy from the outside and reaches an elevated state, it autonomously emits energy (emits light) according to the corresponding energy band gap.

[0055] The quantum dots used in the present invention are not particularly limited and can be in any form. Quantum dots are mainly nanoparticles of 10 nm or less, but they can also be nanowires, nanorods, nanotubes, nanocubes, etc., and any shape can be used.

[0056] The quantum dots used in the present invention can be made of any suitable material, for example, a semiconductor material selected from the group consisting of II-VI group, III-V group, IV group, IV-VI group, I-III-VI group, II-IV-V group, mixed crystals or alloys thereof, or compounds having a perovskite structure. Specific examples of compounds include, but are not limited to, ZnS, ZnSe, ZnTe, CdS, CdSe, CdTe, AlN, AlP, AlAs, AlSb, GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, Si, Ge, Sn, Pb, PbS, PbSe, PbTe, SnS, SnSe, SnTe, AgGaS2, AgInS2, AgGaSe2, AgInSe2, CuGaS2, CuGaSe2, CuInS2, CuInSe2, ZnSiP2, ZnGeP2, CdSiP2, CdGeP2, CsPbCl3, CsPbBr3, CsPbI3, CsSnCl3, CsSnBr3, and CsSnI3.

[0057] The quantum dots used in the present invention can have a core-shell structure. The shell material capable of forming the core-shell structure is not particularly limited, but is preferably one having a large band gap and low lattice mismatch with respect to the core material, and can be arbitrarily combined according to the core material. Specific shell materials include ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdTe, AlN, AlP, AlAs, AlSb, GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, BeS, BeSe, BeTe, MgS, MgSe, MgTe, PbS, PbSe, PbTe, SnS, SnSe, SnTe, CuF, CuCl, CuBr, CuI, etc., and the above materials may be selected as a single or multiple mixed crystals, but are not limited thereto.

[0058] There are various methods for producing the quantum dots used in the present invention, such as a liquid phase method or a gas phase method, and the method is not particularly limited in the present invention. However, from the viewpoint of exhibiting high fluorescence emission efficiency, it is preferable to use semiconductor nanoparticles obtained by a hot soap method or a hot injection method, in which a precursor species is reacted at high temperature in a nonpolar solvent with a high boiling point, and it is desirable that an organic ligand is coordinated to the surface in order to impart dispersibility in the nonpolar solvent and reduce surface defects.

[0059] From the viewpoint of dispersibility, the organic ligand preferably contains an aliphatic hydrocarbon. Examples of such organic ligands include oleic acid, stearic acid, palmitic acid, myristic acid, lauric acid, decanoic acid, octanoic acid, oleylamine, stearyl (octadecyl)amine, dodecyl (lauryl)amine, decylamine, octylamine, octadecanethiol, hexadecanethiol, tetradecanethiol, dodecanethiol, decanethiol, octanethiol, trioctylphosphine, trioctylphosphine oxide, triphenylphosphine, triphenylphosphine oxide, tributylphosphine, and tributylphosphine oxide, and the like, and these may be used alone or in combination.

[0060] The component (C) preferably contains a skeleton having a radical-reactive functional group in the surface coating layer of the quantum dots.

[0061] The quantum dot surface is subjected to surface treatment with a silane coupling agent. The silane coupling agent preferably has at least one of an amino group, a thiol group, a carboxyl group, a phosphino group, a phosphine oxide group, and an ammonium ion as a coordinated substituent. Examples of the silane coupling agent include 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, aminophenyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyl(dimethoxy)methylsilane, triethoxysilylpropylmaleamic acid, [(3-triethoxysilyl)propyl]succinic anhydride, X-12-1135 (manufactured by Shin-Etsu Chemical Co., Ltd.), diethylphosphatoethyltriethoxysilane, 3-trihydroxypropylmethylphosphonate sodium salt, and trimethyl[3-(trimethoxysilyl)propyl]ammonium chloride.

[0062] In one embodiment, the quantum dots surface-treated with a silane coupling agent are copolymerized with an alkoxysilane or a condensate of an alkoxysilane hydrolysate. The copolymerization method is not particularly limited. For example, the surface-treated quantum dots and the condensate of an alkoxysilane or an alkoxysilane hydrolysate are mixed in a mixed solvent of toluene and ethanol, and a small amount of water and a catalyst are added to react, so that the quantum dots and the condensate of an alkoxysilane or an alkoxysilane hydrolysate can be copolymerized. The type of catalyst is not particularly limited, and an acid or an alkali can be used. Examples of the catalyst include formic acid, hydrochloric acid, nitric acid, acetic acid, aqueous ammonia, and tetramethylammonium hydroxide.

[0063] The condensate of the alkoxysilane or alkoxysilane hydrolysate is not particularly limited in structure, such as a cage structure, a ladder structure, or a random structure, and can be appropriately selected according to the purpose. A random structure is preferred from the viewpoints of dispersibility and uniformity in the photosensitive resin. The functional group contained in the condensate of the alkoxysilane or alkoxysilane hydrolysate is not limited, and may be appropriately substituted according to the purpose. Those having an acrylic group or a methacrylic group as a substituent that can undergo a crosslinking reaction with the photosensitive resin are particularly preferred from the viewpoint of improving the patterning property of the resin composition.

[0064] In one embodiment, quantum dots surface-treated with a silane coupling agent are copolymerized with alkoxysilane or alkoxysilane hydrolysate. The copolymerization method is not particularly limited. As a synthesis method, a method such as that described in Non-Patent Document 1 is known. For example, the surface-treated quantum dots and alkoxysilane are mixed in a mixed solvent of toluene and ethanol, and a small amount of water and a catalyst are added to react with each other to obtain the copolymer. There are no particular limitations on the type or amount of catalyst added, and acids or alkalis can be used. Examples of catalysts include formic acid, hydrochloric acid, nitric acid, acetic acid, aqueous ammonia, and tetramethylammonium hydroxide.

[0065] The silane coupling agent is not particularly limited and can be appropriately selected according to the desired resin properties. The silane coupling agent preferably has a vinyl group, an allyl group, a glycidyl group, a phenyl group, an acryl group, a methacryl group, or a thiol group as a functional group. In addition, an alkoxysilane having not only one type of functional group but also two or more types of functional groups may be used. Examples of silane coupling agents include trimethoxyvinylsilane, triethoxyvinylsilane, trimethoxy(4-vinylphenyl)silane, allyltriethoxysilane, allyltrimethoxysilane, triethoxy(3-glycidyloxypropyl)silane, 3-glycidyloxypropyltrimethoxysilane, [8-(glycidyloxy)-n-octyl]trimethoxysilane, KBM-573 (manufactured by Shin-Etsu Chemical Co., Ltd.), (3-methacryloyloxypropyl)triethoxysilane, (3-methacryloyloxypropyl)trimethoxysilane, 3-(trimethoxysilyl)propyl acrylate, 3-mercaptopropyltriethoxysilane, and 3-mercaptopropyltrimethoxysilane.

[0066] The alkoxysilane may contain not only trialkoxysilane but also dialkoxysilane or monoalkoxysilane. Trialkoxysilane, dialkoxysilane, and monoalkoxysilane may have the same functional group or different functional groups. The functional group is not limited and may be appropriately substituted according to the purpose. Those having an acrylic group or a methacrylic group capable of crosslinking with a photosensitive resin as a substituent are particularly preferred from the viewpoint of improving the patterning property of the resin composition. By containing dialkoxysilane or monoalkoxysilane, the degree of crosslinking of the alkoxysilane or the condensate of the alkoxysilane hydrolyzate obtained by copolymerization can be controlled, and the viscosity of the obtained resin composition can be controlled, and the viscosity can be adjusted according to the manufacturing process. The type and ratio of these alkoxysilanes are not particularly limited and can be appropriately selected according to the purpose.

[0067] The content of the copolymer of the quantum dots (C) coordinated with a silane coupling agent and an alkoxysilane, an alkoxysilane hydrolysate, or a condensate thereof in the photosensitive resin composition is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, based on the total amount of the photosensitive resin composition. If the content of the quantum dot particles is within the above range, fine patterns can be formed while maintaining good light-emitting properties.

[0068] [(D) Surfactant] The photosensitive resin composition of the present invention may further contain a surfactant (D) in order to improve the coatability.

[0069] Examples of the surfactant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene sterial ether, polyoxyethylene cetyl ether, and polyoxyethylene olein ether; polyoxyethylene alkyl allyl ethers such as polyoxyethylene octylphenol ether and polyoxyethylene nonylphenol ether; polyoxyethylene polyoxypropylene block copolymers; sorbitan fatty acid esters such as sorbitan monolaurate, sorbitan monopalmitate, and sorbitan monostearate; polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyether silicone, polyoxyethylene sorbitan trioleate, and polyoxyethylene sorbitan tristearate. nonionic surfactants of polyoxyethylene sorbitan fatty acid esters such as sorbitol, EFTOP EF301, EF303, EF352 (manufactured by Tochem Products Co., Ltd.), Megafac F171, F172, F173 (manufactured by DIC Corporation), Fluorad FC-4430, FC-430, FC-431 (manufactured by Sumitomo 3M Limited), Surfynol E1004 (manufactured by Nissin Chemical Industry Co., Ltd.), Asahiguard AG710, Surflon S-381, Examples of such surfactants include fluorosurfactants such as S-382, SC101, SC102, SC103, SC104, SC105, SC106, KH-10, KH-20, KH-30, and KH-40 (manufactured by AGC Seimi Chemical Co., Ltd.), organosiloxane polymers KP-341, X-70-092, and X-70-093 (manufactured by Shin-Etsu Chemical Co., Ltd.), and acrylic acid- or methacrylic acid-based Polyflow No. 75 and No. 95 (manufactured by Kyoeisha Chemical Co., Ltd.).

[0070] The amount of the surfactant (D) is preferably 0.01 to 3 mass %, more preferably 0.02 to 1 mass %, based on the total amount of the photosensitive resin composition. These can be used alone or in combination of two or more kinds.

[0071] [(E) Silane coupling agent] The photosensitive resin composition of the present invention may further contain (E) a silane coupling agent in order to improve adhesion to a substrate.

[0072] Examples of the silane coupling agent include amino group-containing silane coupling agents, epoxy group-containing silane coupling agents, (meth)acryloyl group-containing silane coupling agents, mercapto group-containing silane coupling agents, vinyl group-containing silane coupling agents, ureido group-containing silane coupling agents, styryl group-containing silane coupling agents, and silane coupling agents having a cyclic anhydride structure. Among these, (meth)acryloyl group-containing silane coupling agents are preferred.

[0073] Examples of amino group-containing silane coupling agents include KBM-602, KBM-603, KBM-903, and KBM-573 (manufactured by Shin-Etsu Chemical Co., Ltd.). Examples of epoxy group-containing silane coupling agents include KBM-303, KBM-402, KBM-403, and KBE-402 (manufactured by Shin-Etsu Chemical Co., Ltd.). Examples of (meth)acryloyl group-containing silane coupling agents include KBM-502, KBM-503, KBE-502, KBE-503, and KBM-5103 (manufactured by Shin-Etsu Chemical Co., Ltd.). Examples of mercapto group-containing silane coupling agents include KBM-802 and KBM-803 (manufactured by Shin-Etsu Chemical Co., Ltd.). Examples of vinyl group-containing silane coupling agents include KBM-1003 and KBE-1003 (manufactured by Shin-Etsu Chemical Co., Ltd.). Examples of ureido group-containing silane coupling agents include KBE-585A (manufactured by Shin-Etsu Chemical Co., Ltd.). Examples of styryl group-containing silane coupling agents include KBM-1403 (manufactured by Shin-Etsu Chemical Co., Ltd.). Examples of silane coupling agents having a cyclic anhydride structure include X-12-967C (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0074] The amount of the silane coupling agent (E) is preferably 0.01 to 5 mass %, more preferably 0.05 to 4 mass %, based on the total amount of the photosensitive resin composition. These may be used alone or in combination of two or more.

[0075] [(F) Crosslinking agent] The photosensitive resin composition of the present invention may further contain a crosslinking agent (F). The crosslinking agent is a component that undergoes a crosslinking reaction with the resin (A) having a (meth)acryloyl group and the surface coating layer of the quantum dots contained in the component (C) to facilitate the formation of a pattern with a good shape, and therefore a crosslinking agent having two or more functional (meth)acryloyl groups is preferred.

[0076] Examples of crosslinking agents having two or more functional (meth)acryloyl groups include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, trimethylol propionate, and the like. Pentaerythritol tri(meth)acrylate, glycerin di(meth)acrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate acrylate, 2,2-bis(4-(meth)acryloxydiethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxypolyethoxyphenyl)propane, 2-hydroxy-3-(meth)acryloyloxypropyl(meth)acrylate, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di(meth)acrylate, phthalic acid diglycidyl ester di(meth)acrylate, glycerin triacrylate, glyceryl Examples of the polyfunctional monomer include polyglycidyl ether poly(meth)acrylate, urethane (meth)acrylate (i.e., a reaction product of tolylene diisocyanate, trimethylhexamethylene diisocyanate, hexamethylene diisocyanate, or the like, with 2-hydroxyethyl (meth)acrylate), methylene bis(meth)acrylamide, (meth)acrylamide methylene ether, a condensation product of a polyhydric alcohol and N-methylol (meth)acrylamide, and triacryl formal.

[0077] The amount of the crosslinking agent (F) is preferably 0.5 to 100 parts by mass, and more preferably 1 to 50 parts by mass, per 100 parts by mass of the component (A). These may be used alone or in combination of two or more.

[0078] [(G) Solvent] The photosensitive resin composition of the present invention may contain a solvent as component (G). The solvent (G) is not particularly limited as long as it can dissolve and disperse the above-mentioned components (A) to (F) and other various additives.

[0079] As the (G) solvent, organic solvents are preferred, for example, ketones such as cyclohexanone, cyclopentanone, methyl-2-n-pentyl ketone, etc.; alcohols such as 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, etc.; ethers such as propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, diethylene glycol dimethyl ether, etc.; esters such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, tert-butyl acetate, tert-butyl propionate, propylene glycol-mono-tert-butyl ether acetate, γ-butyrolactone, etc. These may be used alone or in combination of two or more.

[0080] As the (G) solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, cyclopentanone, and mixed solvents thereof are preferable, which have excellent solubility for the (A) resin having a (meth)acryloyl group and the (B) photoradical generator.

[0081] From the viewpoints of compatibility and viscosity of the photosensitive resin composition, the content of the component (G) is preferably from 25 to 85 mass %, and more preferably from 35 to 75 mass %, based on the total amount of the photosensitive resin composition.

[0082] [Photosensitive resin film] The photosensitive resin film of the present invention is a dried product of the above-described photosensitive resin composition.

[0083] [Pattern formation method using photosensitive resin composition] The pattern forming method using the photosensitive resin composition of the present invention comprises the steps of: (i) applying the above-described photosensitive resin composition onto a substrate to form a photosensitive resin film on the substrate; (ii) exposing the photosensitive resin film to light; and (iii) A step of developing the exposed photosensitive resin film with a developer to dissolve and remove the non-exposed areas to form a pattern. Includes.

[0084] Step (i) is a step of applying the above-described photosensitive resin composition onto a substrate to form a photosensitive resin film on the substrate. The photosensitive resin film is a dried product of the above-described photosensitive resin composition. Examples of the substrate include silicon wafers, glass wafers, quartz wafers, plastic circuit boards, and ceramic circuit boards.

[0085] The coating method may be a known method, such as a dipping method, a spin coating method, a roll coating method, etc. The coating amount can be appropriately selected depending on the purpose, but it is preferable to coat so that the thickness of the obtained photosensitive resin film (dried product of the photosensitive resin composition) is preferably 0.1 to 200 μm, more preferably 1 to 150 μm.

[0086] Here, in order to efficiently carry out the photocuring reaction, the solvent and the like may be evaporated in advance by preheating (prebaking) as necessary. Prebaking can be carried out, for example, at 40 to 140° C. for about 1 minute to 1 hour.

[0087] Next, (ii) the photosensitive resin film is exposed to light. In this case, the exposure is preferably performed with light having a wavelength of 10 to 600 nm, and more preferably with light having a wavelength of 190 to 500 nm. Examples of light having such wavelengths include light of various wavelengths generated by a radiation generator, such as ultraviolet light such as g-line, h-line, and i-line, and far ultraviolet light (248 nm, 193 nm). Of these, light having a wavelength of 248 to 436 nm is particularly preferred. The exposure dose is 10 to 10,000 mJ / cm. 2 is preferred.

[0088] The exposure may be performed through a photomask. The photomask may be, for example, a photomask having a desired pattern cut out. The material of the photomask is not particularly limited, but is preferably a material that blocks light of the wavelength. For example, a photomask having chromium as a light-shielding film is preferably used, but is not limited thereto.

[0089] (iii) After exposure, the film is developed with a developer to form a pattern. As the developer, for example, organic solvents such as alcohols such as IPA, ketones such as cyclohexanone, glycols such as propylene glycol monomethyl ether, and known alkaline developers such as an aqueous solution of tetramethylammonium hydroxide are preferred. As the development method, there are conventional methods such as a dip method in which a substrate on which a pattern has been formed is immersed in a developer, a paddle method in which a developer is dispensed with a paddle, and a spray method in which a developer is sprayed with a spray. By developing in this way, the non-exposed portion is dissolved and removed, and a pattern is formed. Thereafter, washing, rinsing, drying, etc. are performed as necessary to obtain a cured film having a desired pattern.

[0090] The pattern forming method using the photosensitive resin composition of the present invention allows easy formation of fine patterns. For example, the photosensitive resin composition of the present invention is formed into a film so as to cover a large number of blue micro LEDs arranged on a substrate, and then fine patterns are formed to form a cured film containing red and green quantum dots on each part of the blue micro LED, which can also emit red and green light, making it possible to fabricate a full-color light-emitting device.

[0091] [Light emitting element] The light-emitting device of the present invention comprises a cured coating obtained by the above-described pattern forming method. That is, the light-emitting device of the present invention comprises a cured coating in which a pattern is formed on the above-described photosensitive resin film. EXAMPLES

[0092] The present invention will be described in more detail below with reference to synthesis examples, examples, and comparative examples, but the present invention is not limited to the following examples. Note that InP / ZnSe / ZnS core-shell quantum dots are used as quantum dot materials, and the core synthesis method is as shown in [1-1] (red quantum dots) and [1-2] (green quantum dots) described later, and the subsequent shell synthesis method is as shown in [2].

[0093] [1-1] Red quantum dot core synthesis process Two flasks were prepared, and 0.23g (0.9mmol) of palmitic acid, 0.088g (0.3mmol) of indium acetate, and 10mL of 1-octadecene were added to each flask. The mixture was heated and stirred at 100°C under reduced pressure, and degassed for 1 hour while dissolving the raw materials. Nitrogen was then purged into the two flasks, and 0.75mL (0.15mmol) of tristrimethylsilylphosphine / trioctylphosphine solution (0.2M) was added to both flasks. One flask was then heated to 300°C, and the solution was colored from yellow to red, confirming that core particles had been generated. The solution was removed from the flask that had not been heated, and added to the flask heated to 300°C, and the desired particle diameter was adjusted.

[0094] [1-2] Green quantum dot core synthesis process 0.23g (0.9mmol) of palmitic acid, 0.088g (0.3mmol) of indium acetate, and 10mL of 1-octadecene were added to the flask, and the mixture was heated and stirred at 100℃ under reduced pressure to dissolve the raw materials and degassed for 1 hour. After that, nitrogen was purged into the flask, and 0.75mL (0.15mmol) of a solution prepared by mixing tristrimethylsilylphosphine with trioctylphosphine to adjust the concentration to 0.2M was added, and the temperature was raised to 300℃. It was confirmed that the solution turned from yellow to red and that core particles were formed.

[0095] [2] Quantum dot shell layer synthesis process Next, 2.85g (4.5mmol) of zinc stearate and 15mL of 1-octadecene were added to another flask, and the mixture was heated and stirred at 100°C under reduced pressure to dissolve and degassed for 1 hour to prepare a 0.3M zinc stearate octadecene solution. 3.0mL (0.9mmol) was added to the reaction solution after the core synthesis and cooled to 200°C. Next, 0.474g (6mmol) of selenium and 4mL of trioctylphosphine were added to another flask and heated to 150°C to dissolve, preparing a 1.5M selenium trioctylphosphine solution. The reaction solution after the core synthesis step, which had been cooled to 200°C, was heated to 320°C over 30 minutes, while the selenium trioctylphosphine solution was added in 0.1mL increments to a total of 0.6mL (0.9mmol), and the mixture was held at 320°C for 10 minutes and then cooled to room temperature. 0.44g (2.2mmol) of zinc acetate was added and dissolved by heating and stirring at 100℃ under reduced pressure. The flask was purged again with nitrogen and heated to 230℃, and 0.98mL (4mmol) of 1-dodecanethiol was added and held for 1 hour. The resulting solution was cooled to room temperature to produce a core-shell quantum dot-containing solution. The red core-shell quantum dot-containing solution synthesized through steps [1-1] to [2] was designated R-1, and the green core-shell quantum dot-containing solution synthesized through steps [1-2] to [2] was designated G-1.

[0096] [3] Surface treatment process After the reaction was completed, the solution was cooled to room temperature, ethanol was added to precipitate the reaction solution, and the solution was centrifuged to remove the supernatant. The same purification was carried out once more, and the solution was dispersed in toluene. The toluene solution of the quantum dots was placed in a flask with nitrogen replaced. 0.24 mL (1.0 mmol) of (3-mercaptopropyl)triethoxysilane was added to the solution, and the solution was stirred at room temperature for 24 hours to perform surface treatment. The quantum dots surface-treated using R-1 were designated R-2, and the quantum dots surface-treated using G-1 were designated G-2.

[0097] [4] Condensation step of alkoxysilane or alkoxysilane hydrolysate 10 mL of 3-(methacryloyloxy)propyltrimethoxysilane, 20 mL of toluene, and 10 mL of methanol were mixed in a nitrogen-substituted flask, and 4.0 mL of 1.0 N hydrochloric acid was added dropwise in small amounts while stirring at room temperature. After the addition, the mixture was stirred at room temperature for 60 minutes, and the solution temperature was increased to 60°C and refluxed for 60 minutes. The system was then evacuated for 2 hours at 60°C to distill off the solvent. In the flask, a condensation product of alkoxysilane or alkoxysilane hydrolyzate having a methacryl group was obtained.

[0098] [5] Copolymerization of quantum dots with alkoxysilane or condensation product of alkoxysilane hydrolysate The condensate of the alkoxysilane or alkoxysilane hydrolysate obtained and the quantum dot solution obtained in [3] that had been subjected to surface treatment were added to a nitrogen-substituted flask so that the solid concentration was 20 mass%, and 20 mL of toluene and 10 mL of methanol were further added and mixed. 4.0 mL of 1.0 N hydrochloric acid was added dropwise to the mixture while stirring at room temperature. After the dropwise addition, the mixture was stirred at room temperature for 60 minutes, and the solution temperature was increased to 60 ° C. and refluxed for 60 minutes. After that, PGMEA was added, and the toluene solvent was removed by distillation under reduced pressure to obtain a copolymer of the quantum dot and the condensate of the alkoxysilane or alkoxysilane hydrolysate. The copolymer of R-2 and the condensate of the alkoxysilane or alkoxysilane hydrolysate was designated R-3, and the condensate of G-2 and the alkoxysilane or alkoxysilane hydrolysate was designated G-3.

[0099] [6] Copolymerization of quantum dots with alkoxysilane or alkoxysilane hydrolysate 7 mL of 3-(methacryloyloxy)propyltrimethoxysilane, 3 mL of ethoxytrimethylsilane, and the quantum dot solution obtained in [3] that had been subjected to surface treatment were added to a nitrogen-substituted flask so that the solid content concentration was 20 mass%, and then 20 mL of toluene and 10 mL of methanol were added and mixed. 4.0 mL of 1.0 N hydrochloric acid was added dropwise to the solution while stirring at room temperature. After the addition, the solution was stirred at room temperature for 60 minutes, and the solution was refluxed at 60 °C for 60 minutes. PGMEA was then added, and the toluene solvent was removed by distillation under reduced pressure to obtain a copolymer of quantum dots and alkoxysilane or alkoxysilane hydrolysate. The copolymer of R-2 and alkoxysilane or alkoxysilane hydrolysate was designated R-4, and the copolymer of G-2 and alkoxysilane or alkoxysilane hydrolysate was designated G-4.

[0100] [7] Preparation and evaluation of photosensitive resin composition [Examples 1 to 16 and Comparative Examples 1 to 24] The components were mixed according to the amounts shown in Tables 1 to 4, then stirred and mixed at room temperature and microfiltered through a 1.0 μm glass filter to obtain photosensitive resin compositions of Examples 1 to 16 and Comparative Examples 1 to 24.

[0101] [Table 1]

[0102] [Table 2]

[0103] [Table 3]

[0104] [Table 4]

[0105] In Tables 1 to 4, the resins are acrylic resins manufactured by Negami Chemical Industry Co., Ltd. under the trade names "RA-4101" (Mw: 30,000 g / mol, acid value: 90 mg KOH / g, double bond equivalent: 350 g / mol), "RA-3631P" (Mw: 18,000 g / mol, acid value: 5 mg KOH / g, double bond equivalent: 250 g / mol), and acrylic resins manufactured by Taisei Fine Chemical Co., Ltd. under the trade names "8KQ-2001" (Mw: 20,000 g / mol, acid value: 130 mg KOH / g, double bond equivalent: 540 g / mol), and "8KQ-7052" (Mw: 19,000 g / mol, acid value: 7 mg KOH / g, double bond equivalent: 500 g / mol).

[0106] In Tables 1 to 4, the photoradical generators are "Irgacure184" (1-hydroxycyclohexyl-phenyl ketone) and "IrgacureOXE01", both manufactured by BASF. [ka]

[0107] In Tables 1 to 4, the surfactant is a polyether-type siloxane under the trade name "KP-341" manufactured by Shin-Etsu Chemical Co., Ltd.

[0108] In Tables 1 to 4, the silane coupling agent is the product name "KBM-503" (3-methacryloxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd.

[0109] In Tables 1 to 4, the crosslinking agents are trade name "Aronix (registered trademark) M-940" (dipentaerythritol hexaacrylate) manufactured by Toagosei Co., Ltd., and trade name "DPCA-20" manufactured by Nippon Kayaku Co., Ltd. [ka]

[0110] In Tables 1 to 4, the quantum dots R-5 are S-BE030 manufactured by Shoei Chemical Co., Ltd. (particle size 5 to 10 nm, material InP:ZnS:SeZn = 25:50:25), R-6 are 900514-1ML manufactured by Aldrich (particle size 5 to 10 nm, material CdSe (core) / CdS (shell) core-shell type), G-5 are S-BE029 manufactured by Shoei Chemical Co., Ltd. (particle size 3 to 5 nm, material InP:ZnS:SeZn = 25:50:25), and G-6 are 900511-1ML manufactured by Aldrich (particle size 3 to 5 nm, material CdSe (core) / CdS (shell) core-shell type).

[0111] [8] Evaluation of photosensitive resin composition (1) Confirmation of aggregates in the film Each photosensitive resin composition was coated on a silicon wafer with a film thickness of 20 μm using a spin coater. In order to remove the solvent from the composition, the substrate was placed on a hot plate and heated and dried at 110° C. for 4 minutes. The agglomerates in the obtained photosensitive resin film were confirmed with an optical microscope, and the results are shown in Tables 5 to 8, with agglomerates of 1 μm or more in size in a 10 mm×10 mm area being marked with ×, and those without agglomerates or with a size of less than 1 μm being marked with ○.

[0112] (2) Pattern formation and its evaluation The obtained photosensitive resin film was exposed to light using an i-line stepper NSR-2205i11D (Nikon Corporation) through a mask to form a square island pattern with a pitch width of 1:1 with the adjacent pattern. After irradiation, paddle development was performed for 90 seconds with an aqueous solution of 2.38% tetramethylammonium hydroxide for the odd-numbered examples and comparative examples, and with PGMEA for the even-numbered examples and comparative examples, to form a pattern. Thereafter, the formed island patterns with sides of 50 μm, 40 μm, 30 μm, 20 μm, and 10 μm were observed with a scanning electron microscope (SEM), and the minimum pattern size that was not connected to the adjacent island pattern (pitch width of 1:1) was determined as the limiting resolution. In addition, those in which the resolution did not reach 50 μm or the pattern peeled off during development were marked with ×. The results are shown in Tables 5 to 8.

[0113] (3) Evaluation of the luminescence characteristics of the formed patterns Using LabRAM HR Evolution manufactured by Horiba Techno Service Co., Ltd., the patterned sample prepared in (2) above was irradiated with 457 nm laser light (0.03 mW), the photoconverted island pattern area was measured, and the emission intensity, emission wavelength, and half-width of the photoconverted light were measured. In addition, the sample prepared in (1) above after the heat drying process was similarly measured to measure the emission intensity of the photoconverted light. The results are shown in Tables 5 to 8 (M: million).

[0114] (4) Reliability test evaluation In addition, a laser light resistance test was performed on the patterned measurement sample of (2) above by continuously irradiating it with a 454 nm, 1 W laser in an oven at 85° C. The emission intensity of the photoconverted light before and after the test was measured in the same manner as in (3), and the rate of change (rate of decrease) from the initial state was confirmed (rate of change = ((emission intensity after test / emission intensity before test)-1) x 100). The results are shown in Tables 5 to 8.

[0115] (5) Adhesion test evaluation A silicon wafer was coated with the photosensitive resin composition shown in Tables 1 to 4 in a film thickness of 50 μm using a spin coater. To remove the solvent from the composition, the substrate was placed on a hot plate and dried by heating at 110° C. for 10 minutes. The entire surface of the obtained photosensitive resin film was exposed to light at 365 nm using a contact aligner type exposure device and cured. A cross-cut peel test (JIS K 5400) was performed to evaluate the adhesion to the substrate. The number of cross-cuts that peeled off out of 100 cross-cuts is shown in Tables 5 to 8.

[0116] [Table 5]

[0117] [Table 6]

[0118] [Table 7]

[0119] [Table 8]

[0120] The above results demonstrate that the photosensitive resin composition of the present invention can form a good photosensitive resin film free of aggregates (or if any, the aggregates are extremely small), and can provide a cured film (cured coating) that has high lithography resolution, high luminescence characteristics that do not change before and after the lithography process, good reliability (low rate of change in luminescence intensity in a laser light resistance test), and high adhesion to a substrate, and is suitable for a light-emitting device.

[0121] On the other hand, in Comparative Examples 1, 2, 5, 6, 9, 10, 13, 14, 17, 18, 21, and 22, which used R-1, R-2, G-1, and G-2, which are quantum dots not copolymerized with alkoxysilane, alkoxysilane hydrolysate, or condensate thereof as component (C), aggregates were confirmed, so a good photosensitive resin film could not be formed, and the lithography resolution, luminescence characteristics before and after the lithography process, rate of change in luminescence intensity in a laser light resistance test, and adhesion to the substrate were poorer than those of the photosensitive resin composition of the present invention, and a cured film (cured film) suitable for a light-emitting element was not obtained.

[0122] Similarly, in Comparative Examples 3, 4, 7, 8, 11, 12, 15, 16, 19, 20, 23, and 24, in which commercially available quantum dots R-5, R-6, G-5, and G-6 were used as component (C), aggregates were also confirmed, and a good photosensitive resin film could not be formed. The lithography resolution, the luminescence characteristics before and after the lithography process, the rate of change in luminescence intensity in a laser light resistance test, and the adhesion to the substrate were poorer than those of the photosensitive resin composition of the present invention, and a cured film (cured film) suitable for a light-emitting element was not obtained.

[0123] The present specification includes the following aspects. [1]: A photosensitive resin composition comprising: (A) a resin having a (meth)acryloyl group, (B) a photoradical generator, and (C) A polymer obtained by copolymerizing quantum dots coordinated with a silane coupling agent and an alkoxysilane, an alkoxysilane hydrolyzate, or a condensate thereof; A photosensitive resin composition comprising: [2]: The photosensitive resin composition according to [1] above, wherein the component (C) contains a skeleton having a radical-reactive functional group in the surface coating layer of the quantum dots. [3]: The photosensitive resin composition according to the above [1] or [2], characterized in that the silane coupling agent of the component (C) has one or more of an amino group, a thiol group, a carboxy group, a phosphino group, a phosphine oxide group, and an ammonium ion as a coordinating substituent. [4]: The photosensitive resin composition according to any one of [1] to [3] above, wherein the component (C) is contained in an amount of 5 to 80 mass % in the photosensitive resin composition. [5]: The photosensitive resin composition according to any one of [1] to [4] above, wherein the double bond equivalent of the component (A) is 240 to 1,000 g / mol. [6]: The photosensitive resin composition according to any one of [1] to [5] above, wherein the component (A) is an acrylic resin having a weight average molecular weight Mw of 5,000 to 100,000 g / mol. [7]: The photosensitive resin composition according to any one of [1] to [6] above, further comprising (D) a surfactant. [8]: The photosensitive resin composition according to any one of [1] to [7] above, further comprising (E) a silane coupling agent. [9]: The photosensitive resin composition according to any one of [1] to [8] above, further comprising (F) a crosslinking agent having two or more (meth)acryloyl groups.

[10] : The photosensitive resin composition according to any one of [1] to [9] above, further comprising (G) a solvent.

[11] : A photosensitive resin film, which is a dried product of the photosensitive resin composition according to any one of [1] to

[10] above.

[12] : A pattern forming method comprising the steps of: (i) applying any one of the photosensitive resin compositions [1] to

[10] above onto a substrate to form a photosensitive resin film on the substrate; (ii) exposing the photosensitive resin film to light; and (iii) A step of developing the exposed photosensitive resin film with a developer to dissolve and remove the non-exposed areas to form a pattern. A pattern forming method comprising the steps of:

[13] : A light-emitting device comprising the photosensitive resin film according to

[11] above, which has a cured film having a pattern formed thereon.

[0124] The present invention is not limited to the above-described embodiment. The above-described embodiment is merely an example, and anything that has substantially the same configuration as the technical idea described in the claims of the present invention and exhibits similar effects is included in the technical scope of the present invention.

Claims

1. A photosensitive resin composition comprising: (A) a resin having a (meth)acryloyl group, (B) a photoradical generator, and (C) a polymer obtained by copolymerizing quantum dots coordinated with a silane coupling agent and an alkoxysilane, an alkoxysilane hydrolysate, or a condensate thereof; A photosensitive resin composition comprising:

2. 2. The photosensitive resin composition according to claim 1, wherein the component (C) contains a skeleton having a radical-reactive functional group in a surface coating layer of the quantum dots.

3. 2. The photosensitive resin composition according to claim 1, wherein the silane coupling agent of the component (C) has at least one of an amino group, a thiol group, a carboxy group, a phosphino group, a phosphine oxide group, and an ammonium ion as a coordinating substituent.

4. 2. The photosensitive resin composition according to claim 1, wherein the component (C) is contained in an amount of 5 to 80% by mass in the photosensitive resin composition.

5. 2. The photosensitive resin composition according to claim 1, wherein the component (A) has a double bond equivalent of 240 to 1,000 g / mol.

6. 2. The photosensitive resin composition according to claim 1, wherein the component (A) is an acrylic resin having a weight average molecular weight Mw of 5,000 to 100,000 g / mol.

7. 2. The photosensitive resin composition according to claim 1, further comprising (D) a surfactant.

8. 2. The photosensitive resin composition according to claim 1, further comprising (E) a silane coupling agent.

9. 2. The photosensitive resin composition according to claim 1, further comprising (F) a crosslinking agent having two or more functional (meth)acryloyl groups.

10. 2. The photosensitive resin composition according to claim 1, further comprising (G) a solvent.

11. A photosensitive resin film, which is a dried product of the photosensitive resin composition according to any one of claims 1 to 10.

12. A pattern formation method comprising the steps of: (i) applying the photosensitive resin composition according to any one of claims 1 to 10 onto a substrate to form a photosensitive resin film on the substrate; (ii) exposing the photosensitive resin film to light; and (iii) A step of developing the exposed photosensitive resin film with a developer to dissolve and remove the non-exposed areas to form a pattern. A pattern forming method comprising the steps of:

13. A light-emitting device comprising a cured film having a pattern formed on the photosensitive resin film according to claim 11.