Photosensitive resin composition

Abstract

To provide a photosensitive resin composition that can be repurposed as a photoresist and facilitates the formation of a high-resolution wavelength conversion layer. [Solution] A photosensitive resin composition comprising a photopolymerizable compound, a dispersant consisting of a first unit represented by general formula (1) and a second unit represented by a specific formula, a solvent, and perovskite phosphor particles. JPEG2026074739000014.jpg6260

Description

[Technical Field]

[0001] This invention relates to a photosensitive resin composition. [Background technology]

[0002] In recent years, there has been research into applying quantum dots as wavelength conversion materials to display elements. One proposed display element using quantum dots is a color filter that has a wavelength conversion layer containing quantum dots between partitions on an organic light-emitting pixel array, which serves as the light source. In this color filter with a wavelength conversion layer, wavelength conversion layers containing quantum dots with different emission wavelengths due to wavelength conversion are arranged adjacent to each pixel region.

[0003] The wavelength conversion layer containing quantum dots is formed by curing an ink made of a photocurable composition. Patent Document 1 discloses a photocurable composition in which fluorescent particles containing a perovskite compound are dispersed in a photopolymerizable compound with a dispersant such as a phosphoric acid compound or a carboxylic acid compound.

[0004] Furthermore, Patent Document 2 discloses an inkjet ink that uses a photocurable composition as the ink and has a surfactant added to adjust the surface tension and ensure the wettability of the ink on the printing substrate. In addition, Patent Document 3 discloses an ink composition that ensures dispersibility in a dispersion medium by using a ligand that forms a zwitterionic bond with the perovskite. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2020-70444 [Patent Document 2] Japanese Patent Publication No. 2020-45440 [Patent Document 3] Japanese Patent Publication No. 2023-81339 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] However, as light-emitting pixels become more detailed, inkjet methods require even smaller ink droplets. This miniaturization significantly reduces the accuracy of the ink droplets, making the formation of the wavelength conversion layer in the desired layout not always easy. Photolithography offers a simple yet highly detailed formation method.

[0007] However, in order to convert these inks into photoresists that can be patterned using photolithography, it is necessary to achieve both the dispersibility of the perovskite compound in a photopolymerizable compound soluble in the developer, and a contrast in solubility in the developer between the photosensitive and non-photosensitive areas, requiring many improvements.

[0008] This invention has been made in view of the above background art, and aims to provide a photosensitive resin composition that can be repurposed as a photoresist and facilitates the formation of a high-resolution wavelength conversion layer. [Means for solving the problem]

[0009] To achieve the above objectives, the present invention provides: Photopolymerizable compounds, Dispersant and Solvent and, Perovskite phosphor particles dispersed in the photopolymerizable compound with the aforementioned dispersant and Includes, The dispersant comprises a first unit and a second unit, The first unit includes a unit represented by the following general formula (1): The aforementioned second unit includes a unit represented by the following general formula (2): A part of the unit represented by the general formula (1) has a side chain C having a zwitterionic portion consisting of a combination of A and B, The side chain R2 of the unit represented by the general formula (2) has a hydrogen atom, or a part of the molecular chain of the side chain R2 has any one functional group selected from the group consisting of a carboxy group, a sulfate group, a phosphate group, and a hydroxy group. The photosensitive resin composition is characterized by this.

Chemical formula

Chemical formula

Chemical formula

Advantages of the Invention

[0010] According to the present invention, it is possible to provide a photosensitive resin composition that can be applied to a photoresist and facilitates the formation of a high-definition wavelength conversion layer.

Modes for Carrying Out the Invention

[0011] <One Embodiment> Hereinafter, embodiments of the present invention will be described in detail. The photosensitive resin composition according to the embodiment of the present invention has the following characteristics. The photosensitive resin composition of the present invention contains a photopolymerizable compound, a dispersant, a solvent, perovskite phosphor particles dispersed in the photopolymerizable compound by the dispersant, and includes, the dispersant includes a first unit and a second unit, The first unit includes a unit represented by the following general formula (1): The aforementioned second unit includes a unit represented by the following general formula (2): A part of the unit represented by the general formula (1) has a side chain C having a zwitterionic portion consisting of a combination of A and B, The side chain R2 of the unit represented by the general formula (2) is characterized in that it has a hydrogen atom, or a part of the molecular chain of the side chain R2 has one functional group selected from the group consisting of a carboxyl group, a sulfate group, a phosphate group, and a hydroxyl group. [ka] [ka] (In the above general formulas (1) and (2), R1 represents a hydrogen atom or a methyl group, A represents a dialkylammonium diyl group, or a group represented by the following formula (3): B represents one selected from the group consisting of sulfonate groups, carboxhate groups, and quaternary ammonium groups. k, l, m, and n each represent an integer. [ka] Furthermore, the structure can be confirmed using a nuclear magnetic resonance (NMR) spectrometer. Embodiments of the present invention will be described below with reference to the drawings.

[0012] The photosensitive resin composition of this embodiment comprises a photopolymerizable compound, a dispersant, a solvent, and perovskite phosphor particles dispersed in the photopolymerizable compound with the dispersant. A specific example of the photopolymerizable compound of this embodiment is a composition comprising a base polymer having a photopolymerizable crosslinking portion and a photopolymerization initiator. In addition to these, the photopolymerizable compound may also contain a polymerizable crosslinking agent.

[0013] In this embodiment, the photosensitive resin composition preferably contains an alkali-soluble photopolymerizable compound. By imparting alkali solubility to the photopolymerizable compound, a photosensitive resin composition that can be developed with alkali becomes available. A suitable method for imparting alkali solubility to the photopolymerizable compound is to introduce hydroxyl groups and carboxyl groups into the molecule.

[0014] Here, alkali solubility in the present invention refers to dissolution in a general alkaline developer. Specifically, it refers to dissolution in a widely used 2.38% aqueous solution of tetraammonium hydroxide (TMAH). The mechanism of dissolution is the H of any of the carboxyl group, sulfate group, phosphate group, and hydroxyl group. + The proton forms a salt with an alkali cation and dissolves in an alkaline aqueous solution as a soluble group.

[0015] In this embodiment, it is preferable that the unexposed portion (unphotosensitive portion) of the photosensitive resin composition is an alkali-developable negative-type resist that is alkali-soluble. To use the photosensitive resin composition of this embodiment as a photoresist, it can be used in either a positive type, where the exposed portion is easily soluble in the developer compared to the unexposed portion, or a negative type, where the exposed portion is less soluble in the developer compared to the unexposed portion. However, in the positive type, in a system where different perovskite phosphor particle patterns are successively formed on a substrate by multiple photolithography processes, the pattern formed in the first process becomes the exposed portion in the second photolithography process.

[0016] Specifically, when a pattern of red-emitting perovskite phosphor particles is formed adjacent to a pattern of green-emitting perovskite phosphor particles, the green-emitting perovskite phosphor particle pattern becomes the exposed area. In the above system, a negative type is preferred because a positive type may dissolve in the developer. In this embodiment, the photoresist refers to one in which the solubility contrast between the exposed and unexposed areas in the developer is 5 or higher.

[0017] Examples of base polymers for the photopolymerizable compounds in this embodiment include the following compounds. For example, diisocyanates, methacrylates of bisphenol-type epoxy resins or their partially acid anhydride-modified products, carboxyl-containing urethane resins obtained by polyaddition reactions of carboxyl-containing dialcohol compounds and diol compounds, or those having an aromatic ring within the molecule.

[0018] Furthermore, examples include carboxyl group-containing resins obtained by reacting a polyfunctional epoxy resin with methacrylic acid and adding dibasic acid anhydrides such as phthalic anhydride, tetrahydrophthalic anhydride, or hexahydrophthalic anhydride to the hydroxyl groups present in the side chains, or resins having an aromatic ring within the molecule.

[0019] Other examples include acrylicates obtained by copolymerization of unsaturated carboxylic acids such as methacrylic acid with unsaturated group-containing compounds such as styrene, alkyl methacrylate, methylstyrene, and isobutylene, or those having an aromatic ring within the molecule.

[0020] Other examples include carboxyl group-containing urethane resins or those having aromatic rings within the molecule, which are produced by polyaddition reactions of diol compounds such as polyester polyols, polycarbonate polyols, polyether polyols, acrylic polyols, bisphenol alkylene oxide adduct diols, compounds having phenolic hydroxyl groups, and compounds having alcoholic hydroxyl groups.

[0021] The photopolymerization initiator is selected appropriately depending on the wavelength used for exposure. In this embodiment, known photopolymerization initiators can be used. The main active species that initiate the polymerization reaction include radical polymerization initiators that generate radicals and cationic polymerization initiators that generate acids, and these may be used in combination.

[0022] Examples of photoradical polymerization initiators that generate radicals using active energy rays include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl methyl ketal, ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-1-(O-acetyloxime), 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzoyloxime)], and 4-(2-hydroxyethoxy) Examples of acetophenones include phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butane, oligo[2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone], and 2-hydroxy-1-[4-[4-(2-hydroxy-2-methylpropionyl)benzyl]phenyl]-2-methylpropan-1-one; benzoins include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; and 2,4,6-trimethylbenzoyl-diphenylphosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, but are not limited to these.

[0023] Commercially available photopolymerization initiators may also be used, such as "ADEKA Optomer SP-170," "ADEKA Optomer SP-172," and "SP-150" (product names) from ADEKA Corporation, "BBI-103" and "BBI-102" (product names) from Midori Chemical Co., Ltd., "IBPF," "IBCF," "TS-01," and "TS-91" (product names) from Sanwa Chemical Co., Ltd., "CPI-210," "CPI-300," and "CPI-410" (product names) from Sunapro Co., Ltd., and "Irgacure® 290" (product name) from BASF Japan. Two or more of these photopolymerization initiators can also be used in combination.

[0024] Examples of cationic polymerization initiators include oxime sulfonate compounds, sulfonimide compounds, onium salts, diazomethane compounds, halogen-containing compounds, sulfone compounds, sulfonic acid ester compounds, carboxylic acid ester compounds, and quinone diazide compounds, which may be used individually or in combination of two or more.

[0025] Examples of cationic polymerization initiators include (camphorsulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile and 2-(octylsulfonyloxyimino)-2-(4-methoxyphenyl)acetonitrile. (5-p-toluenesulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile, (5-propylsulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile, benzothiazonium salt, tetrahydrothiophenium salt, diphenyliodonium salt, triphenylsulfonium salt, sulfonium salt, benzylsulfonium salt, benzylsulfonium salt, 4,7-di-n-butoxy-1-naphthyltetrahydrothiophenium trifluoromethanesulfonate, N-(trifluoromethylsulfonyloxy)succinimide, N-(camphorsulfonyloxy)succinimide, N-(4-methylphenylsulfonyloxy)succinimide, 4,7-di-n-butoxy-1-naphthyltetrahydrothiophenium trifluoromethanesulfonate, N-(camphorsulfonyloxy)phthalimide, N-(2-trifluoromethylphenylsulfonyloxy)phthalimide , benzyl-4-hydroxyphenylmethylsulfonium hexafluorophosphate, N-(2-trifluoromethylphenylsulfonyloxy)succinimide, N-(4-fluorophenylsulfonyloxy)succinimide, N-(trifluoromethylsulfonyloxy)phthalimide, N-(2-fluorophenylsulfonyloxy)phthalimide, N-(trifluoromethylsulfonyloxy)diphenylmaleimide, N-(camphasulfonyloxy)diphenylmaleimide, 4-methylphenylsulfonyloxy)diphenylmaleimide, N-hydroxynaphthalimide-trifluoromethanesulfonic acid ester, tetrahydroxybenzophenone, bis(p-hydroxyphenyl)methane, tris(p-hydroxyphenyl)methane, 1,1,1-tris(p-hydroxyphenyl)ethane, bis(2,3,4-trihydroxyphenyl)methane, 2,2-bis(2,3,4-trihydroxyphenyl)propane, 1,1,3-tris(2,Examples include, but are not limited to, 5-dimethyl-4-hydroxyphenyl)-3-phenylpropane, 4,4'-[1-[4-[1-[4-hydroxyphenyl]-1-methylethyl]phenyl]ethylidene]bisphenol, bis(2,5-dimethyl-4-hydroxyphenyl)-2-hydroxyphenylmethane, 3,3,3',3'-tetramethyl-1,1'-spirovindene-5,6,7,5',6',7'-hexanol, and 2,2,4-trimethyl-7,2',4'-trihydroxyflavan.

[0026] In this embodiment, the photosensitive resin composition preferably contains an acrylate monomer having a carboxyl group or a hydroxyl group as a polymerization crosslinking agent in the photopolymerizable compound. This facilitates the formation of a higher-resolution wavelength conversion layer from the photosensitive resin composition of the present invention.

[0027] As polymerization crosslinking agents, compounds capable of photocrosslinking reactions can be used. For example, monofunctional acrylate compounds, monofunctional methacrylate compounds, difunctional acrylate compounds, difunctional methacrylate compounds, trifunctional or more functional acrylate compounds, trifunctional or more functional methacrylate compounds, hydroxyl group-containing acrylate compounds, hydroxyl group-containing methacrylate compounds, carboxyl group-containing acrylate compounds, carboxyl group-containing methacrylate compounds, vinyl compounds, and the like can be used.

[0028] Examples of monofunctional (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, benzyl (meth)acrylate, and 3,3,5-trimethicyl Lucyclohexyl acrylate, methoxyethyl (meth)acrylate, ethyl carbitol (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, phenoxyethyl (meth)acrylate, isobornyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, and (3-ethyloxetan-3-yl)methyl (meth)acrylate can be used.

[0029] Examples of difunctional (meth)acrylates that can be used include 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol 200 di(meth)acrylate, polyethylene glycol 300 di(meth)acrylate, polyethylene glycol 400 di(meth)acrylate, polyethylene glycol 600 di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polypropylene glycol 400 di(meth)acrylate, polypropylene glycol 700 di(meth)acrylate, and neopentyl glycol di(meth)acrylate.

[0030] Examples of trifunctional (meth)acrylates that can be used include trimethylolpropane tri(meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, glycerin propoxy tri(meth)acrylate, tris(acryloxyethyl) isocyanurate, pentaerythritol tri(meth)acrylate, and EO-modified pentaerythritol tetraacrylate.

[0031] Examples of vinyl compounds that can be used include vinyl acetate, vinyl benzoate, vinyl pivalate, vinyl methacrylate, and N-vinylpyrrolidone. Cationic polymerizable compounds can be either photopolymerizable or thermally polymerizable. These may be used individually or in combination of two or more types. Typical cationic polymerizable compounds include, for example, epoxy compounds, oxacene compounds, and vinyl ether compounds.

[0032] The photosensitive resin composition of this embodiment preferably contains one or more solvents selected from the group consisting of toluene, xylene, and mesitylene. Suitable solvents for use in the photosensitive resin composition include propylene glycol monomethyl ether acetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, and propylene glycol. Monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether propionate benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-butanone, o-xylene, m-xylene, p-xylene, mesitylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylformamide N,N-dimethylacetamide, n-butylbenzene, n-propyl acetate, toluene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, propylene carbonate, isobutyl alcohol, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monohexyl ether, ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene Examples include ethylene glycol monobutyl ether, methyl isobutyl ketone, methylcyclohexanol diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropylene ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, and benzyl alcohol propylene glycol diacetate.

[0033] In this embodiment, commercially available photoresists may be used. For example, "GLR series" from Osaka Organic Chemical Industry Co., Ltd., "Photoclear" from Toray Industries, Ltd., "VPA" from Nippon Steel Chemical & Materials Co., Ltd., and "Acrycure" from Nippon Shokubai Co., Ltd. can be used. Commercially available photoresists contain photopolymerizable compounds, solvents, etc., and the photosensitive resin composition of this embodiment can be prepared by adding perovskite phosphor particles and dispersants.

[0034] In this embodiment, when the amount of polymerizable compound in the photosensitive resin composition is 100 parts by mass, the amount of perovskite phosphor particles is preferably 0.5 parts by mass or more and 10 parts by mass or less. This makes it easier to form a higher-resolution wavelength conversion layer from the photosensitive resin composition of the present invention. The amount of perovskite phosphor particles can be confirmed by mass spectrometry.

[0035] The perovskite phosphor particles used in this embodiment are particulate, having at least one length of 500 nm or less. Their shape may be any geometric shape, such as spherical, cube-shaped, rod-shaped, or disc-shaped.

[0036] The perovskite phosphor particles have a perovskite-type crystalline structure with components A, B, and X. The perovskite compound with components A, B, and X is not particularly limited and may have any of the following structures: three-dimensional, two-dimensional, or pseudo-two-dimensional. In the case of a three-dimensional structure, the perovskite compound is represented as ABX3, and in the case of a two-dimensional structure, it is represented as A2BX4.

[0037] Specific examples of perovskite compounds with a three-dimensional structure represented by ABX3 include CsPbBr3, CsPbCl3, CsPbI3, and CsPbBr (3-y) I y (0 <y<3)、CsPbBr (3-y) Cl y (0 <y<3)、FAPbBr3、FAPbCl3、FAPbI3、FAPbBr (3-y) I y(0 < y < 3), FAPbBr (3-y) Cl y (0 < y < 3), FAPbBr (3-y) Cl y (0 < y < 3) (FA is formamidinium), MAPbBr3, MAPbCl3, MAPbI3, MAPbBr (3-y) I y (0 < y < 3), MAPbBr (3-y) Cl y (0 < y < 3) (MA is methylammonium) can be mentioned.

[0038] Preferred specific examples of the two-dimensional perovskite compound represented by A2BX4 include Cs2PbBr4, Cs2PbCl4, Cs2PbI4, Cs2PbBr (4-y) I y (0 < y < 4), Cs2PbBr (4-y) Cl y (0 < y < 4), FA2PbBr4, FA2PbCl4, FA2PbI4, FA2PbBr (4-y) I y (0 < y < 4), FA2PbBr (4-y) Cl y (0 < y < 4), FA2PbBr (4-y) Cl y (0 < y < 4) (FA is formamidinium), MA2PbBr4, MA2PbCl4, MA2PbI4, MA2PbBr (4-y) I y (0 < y < 4), MA2PbBr (4-y) Cl y (0 < y < 4) (MA is methylammonium) can be mentioned. In addition, perovskite compounds doped with Eu, Gd, Yb, Mn, Ce, Bi, Sm, Ho, Tb may also be used.

[0039] The photosensitive resin composition of this embodiment includes a dispersant comprising a first unit and a second unit, wherein the first unit comprises a unit represented by the general formula (1), and the second unit comprises a unit represented by the general formula (2). The presence and structure of the first and second units can be confirmed using a nuclear magnetic resonance (NMR) spectrometer. The main chain is formed by direct or indirect linkage between the unit represented by the general formula (1) itself, or the unit represented by the general formula (2). Indirect linkage in this embodiment means linkage via compounds other than the units represented by the general formulas (1) and (2).

[0040] The photosensitive resin composition of the present invention preferably contains a third unit as a dispersant, the third unit preferably containing (meth)acrylate. This facilitates the formation of a higher-resolution wavelength conversion layer from the photosensitive resin composition of the present invention. The third unit can be confirmed using a nuclear magnetic resonance (NMR) spectrometer.

[0041] In this embodiment, the unit represented by general formula (1) is designated as the first unit, the unit represented by general formula (2) as the second unit, and any other compound linked to these units as the third unit. The third unit is provided with functions that are lacking in the first and second units, such as solubility, surface tension, viscosity, and dispersibility in the solvent. Linking the third unit to the first and second units can be easily carried out by copolymerization.

[0042] Linking becomes possible by copolymerizing the following (meth)acrylate as a third unit. By using a monofunctional methacrylate, the solubility in the solvent and the dispersibility of the perovskite phosphor particles in the solvent can be adjusted. Examples of monofunctional methacrylates include, but are not limited to, those having ester and ether structures such as hexyl methacrylate, cyclohexyl acrylate, isoamyl acrylate, isobonyl acrylate, benzyl methacrylate, and 2-methoxyethyl methacrylate.

[0043] For example, surface tension and refractive index can be adjusted by using fluorine-containing acrylates. Examples of fluorine-containing acrylates include, but are not limited to, 2,2,2-trifluoroethyl acrylate, 2,2,3,3-tetrafluoropropyl acrylate, 1H,1H,5H-octafluoropentyl acrylate, and 1H,1H,5H-octafluoropentyl methacrylate. Furthermore, tackiness can be adjusted by using dimer acid esters.

[0044] Examples of dimer acid esters include, but are not limited to, tetrahydrofurfuryl alcohol acrylic acid polymer ester, ethoxyethoxyethanol acrylic acid polymer ester, and 1,6-hexanediol acrylic acid polymer ester.

[0045] On the other hand, in this embodiment, a side chain refers to a molecular chain portion that branches off from the main chain. In this embodiment, a part of the unit represented by the general formula (1) has a side chain C having a zwitterionic portion consisting of a combination of A and B, and the side chain R2 of the unit represented by the general formula (2) has a hydrogen atom, or a part of the molecular chain of the side chain R2 has one functional group selected from the group consisting of a carboxyl group, a sulfate group, a phosphate group, and a hydroxyl group.

[0046] The unit represented by general formula (1) serves to protect the perovskite phosphor particles, while the unit represented by general formula (2) primarily functions in dispersibility and developability in photopolymerizable compounds. Specifically, the zwitterionic portion of the unit represented by general formula (1) firmly coordinates to the ionic surface of the perovskite, protecting the perovskite phosphor particles.

[0047] The side chain R2 of the unit represented by general formula (2) functions to provide affinity for the hydroxyl and carboxyl groups of the base polymer of the photopolymerizable compound, which is introduced for alkali solubility. In this way, the perovskite phosphor particles can be dispersed into the base polymer of the photopolymerizable compound by a dispersant. Therefore, when the photosensitive resin composition is used as a photoresist, it becomes possible to pattern the photosensitive resin composition in which the perovskite phosphor particles are dispersed by photolithography.

[0048] Furthermore, since the side chain R2 acts as a soluble group in alkaline developer, the generation of development residue derived from the dispersant is suppressed, resulting in the perovskite phosphor particles being patterned. Therefore, since perovskite phosphor particles that exhibit different emission colors upon wavelength conversion can be patterned on the same surface, it can be used in the manufacture of high-resolution, narrow-pitch wavelength-converting color filters, among other applications.

[0049] The unit represented by general formula (1) in this embodiment has a side chain C having a zwitterionic portion consisting of a combination of A and B. When A in side chain C is the group represented by formula (3), B represents a quaternary ammonium group, and when A is a dialkylammonium diyl group, B represents a sulfonate group or a carboxylate group.

[0050] The zwitterionic moiety can strongly coordinate to the surface of perovskite phosphor particles. Furthermore, since the dispersant of this embodiment has multiple zwitterionic moieties within the same molecule, even if some coordination is detached from the surface of the nanoparticles due to some stimulus, it can easily re-coordinate.

[0051] The amount of ligand is preferably 0.1 parts by mass or more and 10 parts by mass or less when the amount of perovskite phosphor particles is 1 part by mass, more preferably 0.2 parts by mass or more and 4 parts by mass or less, and even more preferably 0.3 parts by mass or more and 3 parts by mass or less. If the amount of ligand is less than 0.1 parts by mass or greater than 3 parts by mass, the dispersion stability of the perovskite phosphor particles may be insufficient.

[0052] The copolymerization ratio n / m of the dispersant in this embodiment is appropriately selected based on the dispersibility of the photopolymerizable compound and its solubility in the solvent and developer. If the copolymerization ratio n / m is too high, dispersibility improves, but solubility in the solvent tends to decrease. If the copolymerization ratio n / m is too low, solubility in the solvent improves, but dispersibility tends to decrease.

[0053] The photosensitive resin composition of this embodiment preferably has a copolymerization ratio n / m, which is the value obtained by dividing n by m, of 0.25 or more and 20 or less, more preferably greater than 0.25 and less than 20, even more preferably 4 or more and 10 or less, even more preferably 1 or more and 10 or less, and particularly preferably 1 or more and 5 or less. When the copolymerization ratio is within the above range, the dispersant is strongly coordinated to the perovskite phosphor particles, and solubility in the solvent is easily ensured. The value of n / m can be confirmed by nuclear magnetic resonance (NMR) spectrometer.

[0054] In this embodiment, the number-average molecular weight of the dispersant in the photosensitive resin composition is preferably 5,000 to 50,000, more preferably 1,000 to 50,000, and even more preferably 1,000 to 30,000. When the number-average molecular weight of the dispersant is within the above range, stability and solubility in polar solvents are easily ensured. The number-average molecular weight of the dispersant can be confirmed by gel permeation chromatography (GPC).

[0055] We will now explain the case where A in the side chain C of general formula (1) is negatively charged, representing the group represented by formula (3), and B represents a quaternary ammonium group with a positive charge.

[0056] In this embodiment, the main chain and the side chain C, when A is the group represented by formula (3), are linked by an ester bond. The linkage in this embodiment is not limited to an ester bond, but may also be an amide bond, an ether bond, an alkylene bond, or an arylene bond.

[0057] The alkylene group constituting the alkylene bond may be linear or branched, and an alkylene group having 1 to 2 carbon atoms is preferred. Examples of alkylene groups having 1 to 2 carbon atoms include the methylene group and the ethylene group. Examples of arylene groups constituting the arylene bond include the 1,2-phenylene group, the 1,3-phenylene group, the 1,4-phenylene group, the naphthalene-1,4-diyl group, the naphthalene-1,5-diyl group, and the naphthalene-2,6-diyl group.

[0058] However, from the viewpoint of raw material availability and ease of manufacture, an ester bond is preferred for the linkage between the main chain and the side chain C when A is the group represented by formula (3) above. For R1, examples include hydrogen, methyl, ethyl, n-propyl, isopropyl, and n-butyl groups, but from the viewpoint of producing polymer compounds (polymerizability), a hydrogen atom and a methyl group are preferred.

[0059] In this embodiment, the k value in the side chain C of the photosensitive resin composition is preferably in the range of 2 to 3, from the viewpoint of raw material availability and ease of manufacturing. This makes it easier to form a higher-resolution wavelength conversion layer from the photosensitive resin composition of the present invention. The value of k can be confirmed using a nuclear magnetic resonance (NMR) spectrometer.

[0060] The zwitterionic structural unit exhibits zwitterionic properties because it has positive and negative charges at non-adjacent positions within the same molecule, resulting in the molecule as a whole having no charge. Therefore, the value of l in C is preferably in the range of 2 to 4, taking into account the availability of raw materials and ease of manufacturing. This facilitates the formation of a higher-resolution wavelength conversion layer from the photosensitive resin composition of the present invention. The value of l can be confirmed using a nuclear magnetic resonance (NMR) spectrometer.

[0061] The quaternary ammonium group contained in B, which has a positive charge, will now be described. Except for the bond with the group represented by formula (3), alkyl groups are bonded to the nitrogen atom of the quaternary ammonium group, forming a quaternary ammonium group. Preferably, the alkyl group has 1 to 18 carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, n-octyl, 2-ethylhexyl, dodecyl, and octadecyl groups. These alkyl groups may be further substituted and bonded to each other, forming a ring.

[0062] This section explains the case in general formula (1) where A represents a positively charged dialkylammonium diyl group and B represents a negatively charged sulfonate group or carboxylate group.

[0063] In this embodiment, the link between the main chain and the side chain C, when A is a dialkylammonium diyl group, is an ester bond. The link in this embodiment is not limited to an ester bond, but may also be an amide bond, ether bond, alkylene bond, or arylene bond.

[0064] The alkylene group constituting the alkylene bond may be linear or branched, and an alkylene group having 1 to 2 carbon atoms is preferred. Examples of alkylene groups having 1 to 2 carbon atoms include the methylene group and the ethylene group. Examples of arylene groups constituting the arylene bond include the 1,2-phenylene group, the 1,3-phenylene group, the 1,4-phenylene group, the naphthalene-1,4-diyl group, the naphthalene-1,5-diyl group, and the naphthalene-2,6-diyl group.

[0065] However, from the viewpoint of raw material availability and ease of manufacture, an ester bond is preferred for the link between the main chain and the side chain C when A is a dialkylammonium diyl group. For R1, examples include hydrogen, methyl, ethyl, n-propyl, isopropyl, and n-butyl groups, but from the viewpoint of producing high-molecular-weight compounds (polymerizability), a hydrogen atom and a methyl group are preferred. The k in the side chain C is preferably in the range of 1 to 3 from the viewpoint of raw material availability and ease of manufacture.

[0066] The nitrogen atom of the dialkylammonium diyl group is bonded to the aforementioned linkage and is bonded to the sulfobetaine and the hydrocarbon chain of 2 ≤ 1 ≤ 4. The remaining two nitrogen atoms of the dialkylammonium diyl group are bonded to alkyl groups, forming a dialkylammonium diyl group. C1 to C18 alkyl groups are preferred. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, n-octyl, 2-ethylhexyl, dodecyl, and octadecyl groups. These alkyl groups may be further substituted and bonded to each other to form a ring.

[0067] This section describes the case where B, which is the counteranion of the dialkylammonium diyl group, represents a sulfonate group or a carboxylate group. Since zwitterionic structural units have positive and negative charges at non-adjacent positions within the same molecule, and the molecule as a whole exhibits zwitterionic properties with no charge, the value of l in C is preferably in the range of 2 to 4, taking into account the availability of raw materials and ease of manufacturing. This facilitates the formation of a higher-resolution wavelength conversion layer from the photosensitive resin composition of the present invention. The value of l can be confirmed using a nuclear magnetic resonance (NMR) spectrometer.

[0068] In this embodiment, the side chain R2 of the unit represented by general formula (2) has a hydrogen atom, or a portion of the molecular chain of the side chain R2 has one functional group selected from the group consisting of a carboxyl group, a sulfate group, a phosphate group, and a hydroxyl group. The main chain and the side chain R2 are linked by an ester bond.

[0069] The linkage in this embodiment is not limited to ester bonds, but may also be amide bonds, ether bonds, alkylene bonds, or arylene bonds. The alkylene group constituting the alkylene bond may be linear or branched, and an alkylene group having 1 to 2 carbon atoms is preferred. Examples of alkylene groups having 1 to 2 carbon atoms include methylene groups and ethylene groups. Examples of arylene groups constituting the arylene bond include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, naphthalene-1,4-diyl group, naphthalene-1,5-diyl group, and naphthalene-2,6-diyl group.

[0070] However, in this embodiment, ester bonds are preferred for linking from the viewpoint of raw material availability and ease of manufacture. Examples of R1 include hydrogen, methyl, ethyl, n-propyl, isopropyl, and n-butyl groups, but from the viewpoint of producing polymer compounds (polymerizability), hydrogen atoms and methyl groups are preferred.

[0071] The dispersibility of a photopolymerizable compound to which alkali solubility has been conferred is improved if the side chain R2 of the unit represented by general formula (2) has a hydrogen atom, or if a part of the molecular chain of the side chain R2 has one functional group selected from the group consisting of a carboxyl group, a sulfate group, a phosphate group, and a hydroxyl group.

[0072] This is because the hydroxyl and carboxyl groups of the photopolymerizable compound, which are introduced for alkali solubility, have a high affinity for the carboxyl, sulfate, phosphate, and hydroxyl groups introduced into part of the molecular chain of the side chain R2. As a result, the perovskite phosphor particles are dispersed in the photopolymerizable compound, forming a photosensitive resin composition.

[0073] This allows perovskite phosphor particles to be patterned when the photosensitive resin composition is used as a photoresist. Furthermore, introducing a carboxyl group, sulfate group, phosphate group, or hydroxyl group to R2 improves alkaline developability and also suppresses the generation of development residue derived from the dispersant.

[0074] In this embodiment, the alkyl group of the side chain R2 is preferably an alkyl group having 1 to 30 carbon atoms. Examples include methyl group, ethyl group, n-propyl group, n-butyl group, n-hexyl group, n-decyl group, n-hexadecyl group, octadecyl group, docosyl group, and triacontyl group.

[0075] Examples of aryl groups in the molecular chain of side chain R2 in this embodiment include aryl groups such as phenyl group, 1-naphthyl group, and 2-naphthyl group. Examples of carboxylic acid ester groups include methyl ester group, ethyl ester group, n-propyl ester group, isopropyl ester group, n-butyl ester group, tert-butyl ester group, octyl ester group, 2-ethylhexyl ester group, dodecyl ester group, octadecyl ester group, docosyl ester group, triacontyl ester group, phenyl ester group, and 2-hydroxyethyl ester group.

[0076] Examples of carboxylic acid amide groups in part of the molecular chain of side chain R2 in this embodiment include amide groups such as N-methylamide group, N,N-dimethylamide group, N,N-diethylamide group, N-isopropylamide group, N-tert-butylamide group, Nn-decylamide group, Nn-hexadecylamide group, N-octadecylamide group, N-docosylamide group, N-triacontilamide group, and N-phenylamide group.

[0077] If a substituent of any of the following groups—carboxyl, sulfate, phosphate, or hydroxyl—is introduced to a portion of the side chain R2, other substituents may also be introduced. In this case, examples of substituents that may be substituted include alkoxy groups such as methoxy and ethoxy groups, amino groups such as N-methylamino and N,N-dimethylamino groups, acyl groups such as acetyl groups, and halogen atoms such as fluorine and chlorine atoms. However, an appropriate substituent may be selected depending on the application.

[0078] The nitrogen atom of the quaternary ammonium group is bonded to an alkyl group, except for the bond with the group represented by formula (3), to form a quaternary ammonium group. Preferably, the alkyl group has 1 to 18 carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, n-octyl, 2-ethylhexyl, dodecyl, and octadecyl groups. These alkyl groups may be further substituted and bonded to each other to form a ring.

[0079] In this embodiment, the photosensitive resin composition may be mixed with, if necessary, oxygen scavengers, antioxidants, scattering agents such as titanium dioxide, surfactants, antifungal agents, light stabilizers, and other additives that impart various properties.

[0080] When the photosensitive resin composition of this embodiment is used as a photoresist, the exposure machine used for exposure is not particularly limited, and any known exposure machine can be used. As exposure light, known types such as carbon arc lamps, mercury vapor arc lamps, high-pressure mercury lamps (g-line (436nm), h-line (405nm), i-line (365nm)), xenon lamps, YAG lasers, Ar ion lasers, semiconductor lasers, F2 excimer lasers (157nm), ArF excimer lasers (193nm), and KrF excimer lasers (248nm) can be used.

[0081] The exposure light should be appropriately selected to match the photosensitive wavelength of the photosensitive resin composition being used. Suitable exposure devices include projection exposure devices with a single wavelength light source, such as i-line exposure steppers and KrF steppers, and projection exposure devices with a broad wavelength light source, such as the Mask Aligner MPA-600Super (product name, manufactured by Canon).

[0082] There are no particular restrictions on the developer used, but alkaline aqueous solutions such as sodium hydroxide, potassium hydroxide, sodium silicate, ammonia, ethylamine, diethylamine, triethylamine, triethanolamine, and tetramethylammonium hydroxide (TMAH) can be used. Furthermore, known coating methods such as spin coating, gravure coating, bar coating, spray coating, dip coating, and die coating can be used as coating methods. [Examples]

[0083] The present invention will be described in more detail below with reference to specific examples. The dispersants of Examples 1 to 10 and Comparative Example 1 are shown in Table 1. (Example 1) In this embodiment, a copolymer of 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, methacrylic acid, and hexyl methacrylate is used as a dispersant. The first unit is derived from 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, the second unit from methacrylic acid, and the third unit from hexyl methacrylate.

[0084] In this example, the dispersant has a carboxyl group where R2 in the ester portion of the linkage is hydrogen. CsPbBr3 is used as the perovskite phosphor particles. CsPbBr3 is dispersed with the dispersant to prepare a 5% by mass toluene dispersion. In this example, a commercially available alkali-developable resist, GLR-A200 manufactured by Osaka Organic Chemical Industry Co., Ltd., is used. GLR-A200 is a photocurable resist containing an acrylic monomer. Since the acrylic monomer contains a carboxyl group or a hydroxyl group in its molecule, it is an alkali-soluble resist.

[0085] The resist used in this embodiment contains a base polymer having a photopolymerizable crosslinking portion, a photopolymerization initiator, and propylene glycol monomethyl ether acetate as a polymerizable crosslinking agent and solvent. A toluene dispersion containing 5% by mass of CsPbBr3 is added to the resist while stirring.

[0086] A photosensitive resin composition is prepared by adding CsPbBr3 to 100 parts by mass of the base polymer until the total volume is 5 parts by mass. The solvents for the photosensitive resin composition are propylene glycol monomethyl ether acetate and toluene. The perovskite phosphor particles disperse well in the base polymer, and no precipitate forms in the photosensitive resin composition. A photosensitive resin composition is applied to a 4-inch diameter glass substrate by spin coating at 1000 rpm for 20 minutes. The mixture is then baked in a nitrogen oven at 90°C for 80 seconds.

[0087] Photolithography is performed as follows: A photomask is used, which consists of an 8 × 28 μm non-light-shielding pattern arranged in an array at a 30 μm pitch. The photomask is placed on a photosensitive resin composition on a glass substrate, and an exposure dose of 90 mJ / cm² is applied. 2 When exposed to light, a latent image pattern arranged in an 8 × 28 μm area with a 30 μm pitch is observed on the photosensitive resin composition.

[0088] A 0.05% by mass potassium hydroxide aqueous solution is used as the developer, and development is performed for 60 seconds, followed by rinsing with pure water for 30 seconds. An array-like pattern, 4 μm thick, 8 × 28 μm in size, and arranged at a 30 μm pitch, is formed on the glass substrate. The unexposed areas between the patterns are dissolved by the developer, exposing the surface of the glass substrate, and no development residue is observed.

[0089] When blue light from a light-emitting diode with a maximum peak wavelength of 445 nm is transmitted, green fluorescence with a peak emission wavelength of 521 nm, 68% PLQY, and 20 nm FWHM is observed in the array-like pattern. Thus, it is possible to convert the photosensitive resin composition into a photoresist, and it is easy to form a high-resolution wavelength conversion layer.

[0090] (Example 2) In this example, a photosensitive resin composition is prepared in the same manner as in Example 1, except that a copolymer of 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, 2-hydroxyethyl methacrylate, and dodecyl acrylate is used as the dispersant, and CsPb(Br / I)3 is used for the perovskite phosphor particles.

[0091] The dispersant in this example has a carboxyl group at the end of the linear chain of R2. The perovskite phosphor particles disperse well in the base polymer and do not precipitate in the photosensitive resin composition. The array pattern of Example 1, which is 4 μm thick, 8 × 28 μm in size, and arranged at a 30 μm pitch, is formed on a glass substrate, which is then spin-coated and photolithography is performed as follows.

[0092] Similar to Example 1, a photomask is used in which 8 × 28 μm non-shielding patterns are arranged at a 30 μm pitch. After alignment so that the non-shielding patterns are adjacent to the pattern formed in Example 1 at a 1 μm interval, exposure is performed. After development and rinsing, a pattern is formed at a position 1 μm away from the pattern formed in Example 1.

[0093] When light from a blue light-emitting diode with a maximum peak wavelength of 445 nm is transmitted, a pattern exhibiting red fluorescence with an emission peak wavelength of 623 nm and an FWHM of 34 nm is observed next to the green fluorescence of the pattern formed in Example 1. Thus, it is clear that the photosensitive resin composition can be converted into a photoresist, and that it is easy to form a high-definition wavelength conversion layer.

[0094] (Example 3) In this example, the photosensitive resin composition is the same as in Example 1, except that a copolymer of 3-[[2-(acryloyloxy)ethyl]dimethylammonio]propane-1-sulfonic acid and 1-[2-(methacryloyloxy)ethyl] succinate is used as a dispersant, and CsPbBr3 is added to 100 parts by mass of the base polymer until the amount is 0.5 parts by mass to prepare the photosensitive resin composition.

[0095] The dispersant in this example has a carboxyl group at the end of the linear chain of R2. Similar to Example 1, the photosensitive resin composition of this example was patterned using photolithography, and the resulting pattern exhibited green fluorescence upon wavelength conversion. Thus, it is possible to convert the photosensitive resin composition into a photoresist, and to easily form a high-resolution wavelength conversion layer.

[0096] (Example 4) In this example, the photosensitive resin composition is the same as in Example 1, except that 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate and a copolymer of 2-(methacryloyloxy)ethyl phosphate and benzyl methacrylate are used as dispersants, and a 5% by mass o-xylene dispersion obtained by dispersing CsPbBr3 with a dispersant is used.

[0097] The dispersant in this example has a phosphate group at the end of the linear chain of R2. The solvents for the photosensitive resin composition are propylene glycol monomethyl ether acetate and o-xylene. Similar to Example 1, the photosensitive resin composition of this example was patterned using photolithography, and the pattern exhibited green fluorescence upon wavelength conversion. Thus, it is evident that the photosensitive resin composition can be converted into a photoresist, and that the formation of a high-resolution wavelength conversion layer is easily achieved.

[0098] (Example 5) In this example, the photosensitive resin composition is the same as in Example 1, except that 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate and a copolymer of 2-hydroxyethyl methacrylate and dodecyl acrylate are used as dispersants, and a 5% by mass mesitylene dispersion obtained by dispersing CsPbBr3 with a dispersant is used.

[0099] The dispersant in this example has a carboxyl group at the end of the linear chain of R2. The solvents for the photosensitive resin composition are propylene glycol monomethyl ether acetate and mesitylene. The photosensitive resin composition of this example was patterned by photolithography in the same manner as in Example 1, and the pattern showed green fluorescence upon wavelength conversion. Thus, it can be seen that the photosensitive resin composition can be converted into a photoresist, and that it is easy to form a high-resolution wavelength conversion layer.

[0100] (Example 6) In this example, the photosensitive resin composition is the same as in Example 1, except that a copolymer of 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate and 2-hydroxy-3-phenoxypropyl acrylate is used as the dispersant. The dispersant in this example has a carboxyl group in part of the linear chain of R2.

[0101] The photosensitive resin composition of this embodiment was patterned by photolithography, similar to Example 1, and the pattern exhibited green fluorescence upon wavelength conversion. Thus, it is possible to convert the photosensitive resin composition into a photoresist, and it is clear that the formation of a high-resolution wavelength conversion layer is easy.

[0102] (Example 7) In this example, the photosensitive resin composition is the same as in Example 1, except that 4-[[2-(methacryloyloxy)ethyl]dimethylammonio]butane-1-sulfonic acid and a copolymer of 2,3-dihydroxypropyl methacrylate and hexyl methacrylate are used as the dispersant, FAPbBr3 is dispersed with the dispersant, and the photosensitive resin composition is prepared by adding FAPbBr3 to 10 parts by mass per 100 parts by mass of the base polymer until the amount is 10 parts by mass. The dispersant in this example has carboxyl groups at two locations: part of the linear chain of R2 and at the terminal.

[0103] The photosensitive resin composition of this embodiment, like that of Example 1, was patterned by photolithography, and the pattern exhibited green fluorescence upon wavelength conversion. Thus, it is evident that the photosensitive resin composition can be converted into a photoresist, and that the formation of a high-resolution wavelength conversion layer is easily achieved.

[0104] (Example 8) In this example, a copolymer of 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, methacrylic acid, and hexyl methacrylate is used as the dispersant. The first unit is derived from 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, the second unit from 2-sulfoethyl methacrylate, and the third unit from 2-methoxyethyl methacrylate. In this example, the R2 group of the ester portion of the dispersant is a sulfonic acid group. The solvent for the photosensitive resin composition is propylene glycol monomethyl ether acetate and mesitylene.

[0105] The photosensitive resin composition of this embodiment was patterned by photolithography, similar to Example 1, and the pattern exhibited green fluorescence upon wavelength conversion. Thus, it is possible to convert the photosensitive resin composition into a photoresist, and it is clear that the formation of a high-resolution wavelength conversion layer is easy.

[0106] (Example 9) In this example, a copolymer of 3-[(3-acrylamidopropyl)dimethylammonio]propanoate, methacrylic acid, and hexyl methacrylate is used as the dispersant. The first unit is derived from 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, the second unit from 2-sulfoethyl methacrylate, and the third unit from 2-methoxyethyl methacrylate. In this example, the R2 group of the ester portion of the dispersant is a sulfonic acid group. The solvent for the photosensitive resin composition is propylene glycol monomethyl ether acetate and mesitylene.

[0107] The photosensitive resin composition of this embodiment was patterned by photolithography, similar to Example 1, and the pattern exhibited green fluorescence upon wavelength conversion. Thus, it is possible to convert the photosensitive resin composition into a photoresist, and it is clear that the formation of a high-resolution wavelength conversion layer is easy.

[0108] (Example 10) In this example, a copolymer of 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, methacrylic acid, and 2-methoxyethyl methacrylate is used as the dispersant. The first unit is derived from 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate, the second unit from methacrylic acid, and the third unit from 2-methoxyethyl methacrylate. In this example, the R2 in the ester portion of the dispersant is hydrogen, forming a carboxyl group. The solvent for the photosensitive resin composition is propylene glycol monomethyl ether acetate and xylene.

[0109] The photosensitive resin composition of this embodiment was patterned by photolithography, similar to Example 1, and the pattern exhibited green fluorescence upon wavelength conversion. Thus, it is possible to convert the photosensitive resin composition into a photoresist, and it is clear that the formation of a high-resolution wavelength conversion layer is easy.

[0110] (Comparative Example 1) In this comparative example, N-methacryloyloxyethyl-N,N-dimethylammonium-α-N-methylcarboxybetaine and a copolymer of alkyl methacrylate 4-[[2-(methacryloyloxy)ethyl]dimethylammonio]butane-1-sulfonic acid and 2,3-dihydroxypropyl methacrylate are used as dispersants. Unlike the present invention, the dispersant in this comparative example does not have a hydrogen atom or any functional group such as a carboxyl group, sulfate group, phosphate group, or hydroxyl group in part of the molecular chain of the side chain R2, but is an alkyl group.

[0111] Similar to Example 1, CsPbBr3 is used as the perovskite phosphor particles. CsPbBr3 is dispersed with a dispersant to prepare a 5% by mass toluene dispersion. Similar to Example 1, the 5% by mass toluene dispersion of CsPbBr3 is added to the resist while stirring. When CsPbBr3 is added until the amount is 5 parts by mass per 100 parts by mass of base polymer, separation from the base polymer is observed, and precipitation of perovskite phosphor particles is confirmed.

[0112] Similar to Example 1, photolithography was performed and the material was developed. After rinsing with pure water, the patternability was checked, and development residue was observed between the array-like patterns. When blue light-emitting diode light was transmitted, no green fluorescence was observed from the array-like patterns.

[0113] [Table 1]

[0114] This embodiment includes the following configuration. (Composition 1) Photopolymerizable compounds, Dispersant and Solvent and, Perovskite phosphor particles dispersed in the photopolymerizable compound with the aforementioned dispersant and Includes, The dispersant comprises a first unit and a second unit, The first unit includes a unit represented by the following general formula (1): The aforementioned second unit includes a unit represented by the following general formula (2): A part of the unit represented by the general formula (1) has a side chain C having a zwitterionic portion consisting of a combination of A and B, A photosensitive resin composition characterized in that the side chain R2 of the unit represented by the general formula (2) has a hydrogen atom, or a part of the molecular chain of the side chain R2 has one functional group selected from the group consisting of a carboxyl group, a sulfate group, a phosphate group, and a hydroxyl group. [ka] [ka] (In the above general formulas (1) and (2), R1 represents a hydrogen atom or a methyl group, A represents a dialkylammonium diyl group, or a group represented by the following formula (3): B represents one selected from the group consisting of sulfonate groups, carboxhate groups, and quaternary ammonium groups. k, l, m, and n each represent an integer. [ka] (Configuration 2) The photosensitive resin composition according to configuration 1, wherein the photopolymerizable compound is alkali-soluble. (Composition 3) The photopolymerizable compound comprises an acrylate monomer having a carboxyl group or a hydroxyl group, as described in the photosensitive resin composition according to configuration 1 or 2. (Composition 4) The photosensitive resin composition according to any one of the three items, wherein the number average molecular weight of the dispersant is 1,000 or more and 50,000 or less. (Composition 5) The photosensitive resin composition according to any one of the four claims, wherein the unsensitive portion of the photosensitive resin composition is an alkali-developable negative-type resist that becomes alkali-soluble. (Composition 6) The photosensitive resin composition according to any one of claims 1 to 5, wherein the solvent comprises one or more selected from the group consisting of toluene, xylene, and mesitylene. (Composition 7) The photosensitive resin composition according to any one of the constructs 1 to 6, wherein n / m, which is the value obtained by dividing n by m, is greater than 0.25 and less than 20. (Composition 8) The photosensitive resin composition according to any one of the items 1 to 7, wherein k is 2 or more and 3 or less. (Composition 9) The photosensitive resin composition according to any one of the constituents 1 to 8, wherein l is 2 or more and 4 or less. (Composition 10) The photosensitive resin composition according to any one of the claims 1 to 9, wherein when the amount of the photopolymerizable compound is 100 parts by mass, the amount of the perovskite phosphor particles is 0.5 parts by mass or more and 10 parts by mass or less. (Composition 11) The dispersant comprises a third unit, The third unit is a photosensitive resin composition according to any one of the claims 1 to 10, comprising (meth)acrylate.

Claims

1. Photopolymerizable compounds, Dispersant and Solvent and, Perovskite phosphor particles dispersed in the photopolymerizable compound with the aforementioned dispersant and Includes, The dispersant comprises a first unit and a second unit, The first unit includes a unit represented by the following general formula (1): The second unit includes a unit represented by the following general formula (2): A part of the unit represented by the general formula (1) has a side chain C having a zwitterionic portion consisting of a combination of A and B, The side chain R of the unit represented by the general formula (2) ２ is a hydrogen atom, or a side chain R ２ A photosensitive resin composition characterized in that a portion of its molecular chain has one functional group selected from the group consisting of a carboxyl group, a sulfate group, a phosphate group, and a hydroxyl group. 【Chemistry 1】 【Chemistry 2】 (In the above general formulas (1) and (2), R １ represents a hydrogen atom or a methyl group. A represents a dialkylammonium diyl group, or a group represented by the following formula (3): B represents one selected from the group consisting of sulfonate groups, carboxhlate groups, and quaternary ammonium groups. k, l, m, and n each represent an integer. 【Transformation 3】

2. The photosensitive resin composition according to claim 1, wherein the photopolymerizable compound is alkali-soluble.

3. The photosensitive resin composition according to claim 1, wherein the photopolymerizable compound comprises an acrylate monomer having a carboxyl group or a hydroxyl group.

4. The photosensitive resin composition according to claim 1, wherein the number-average molecular weight of the dispersant is 1,000 or more and 50,000 or less.

5. The photosensitive resin composition according to claim 1, wherein the unsensitive portion of the photosensitive resin composition is an alkali-developable negative-type resist that becomes alkali-soluble.

6. The photosensitive resin composition according to claim 1, wherein the solvent comprises one or more selected from the group consisting of toluene, xylene, and mesitylene.

7. The photosensitive resin composition according to claim 1, wherein n / m, which is the value obtained by dividing n by m, is greater than 0.25 and less than 20.

8. The photosensitive resin composition according to claim 1, wherein k is 2 or more and 3 or less.

9. The photosensitive resin composition according to claim 1, wherein l is 2 or more and 4 or less.

10. The photosensitive resin composition according to claim 1, wherein when the amount of the photopolymerizable compound is 100 parts by mass, the amount of the perovskite phosphor particles is 0.5 parts by mass or more and 10 parts by mass or less.

11. The dispersant comprises a third unit, The photosensitive resin composition according to claim 1, wherein the third unit comprises (meth)acrylate.

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