Wavelength conversion film formation composition and its applications

Abstract

Provided is a composition capable of forming a wavelength conversion film that has a high residual film ratio and high conversion efficiency even when developed after exposure in an air atmosphere. [Solution to Problem] A composition for forming a wavelength conversion film, comprising (A) a phosphor and (B) a binder, wherein the (B) binder contains a compound represented by the following general formula (1). TIFF2026170499000028.tif1628 [In general formula (1), R 1 and R 2 each independently represent any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, and an aralkyl group; R 3 represents any one selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, and an aralkyl group; R 4 represents any one selected from the group consisting of a (meth)acryloyl group, a styryl group, and an alkenyl group having 2 to 6 carbon atoms; X represents NH or O; and n represents any integer of 1 to 5.]

Description

[Technical Field]

[0001] The present invention relates to a composition for forming a wavelength conversion film and its applications (for example, a composition for forming a wavelength conversion film for displays and a wavelength conversion film containing a composition for forming a wavelength conversion film). [Background technology]

[0002] MicroLED displays are expected to be the next generation of displays, following LCDs and OLEDs, due to their high contrast and brightness capabilities, as well as their wide range of applications, including large screens and transparent displays. In microLED displays, typically a tiny LED chip is placed for each pixel. One method for arranging these LED chips is the RGB-LED method, which implements three colors of LEDs. However, this method has drawbacks such as the complexity of controlling the LED's light emission and the low performance of the red LED. Therefore, wavelength conversion methods that can solve these problems are attracting attention. The wavelength conversion method uses only blue LED chips, and uses wavelength conversion materials to extract red and green light. This method has the advantage of being able to produce the three primary colors using only blue LED chips.

[0003] Conventionally, technologies using organic light-emitting materials have been proposed as wavelength conversion materials. For example, those using pyridine-phthalimide condensates (Patent Document 1, etc.), those using coumarin derivatives (Patent Document 2, etc.), those using perylene derivatives (Patent Document 3, etc.), those using rhodamine derivatives (Patent Document 4), and those using pyromethene derivatives (Patent Documents 5, 6, etc.) have been disclosed.

[0004] These wavelength conversion materials generally require properties such as good wavelength conversion efficiency, color purity, and lightfastness. In this regard, for example, Patent Document 7 discloses that a composition comprising a binder resin made of a specific methacrylic polymer, a specific fluorescent dye, and a photopolymerizable acrylic acid ester can be used as a high-performance, lightfast red conversion material. Furthermore, techniques for adding light stabilizers to prevent degradation of organic light-emitting materials and improve their durability have also been disclosed (e.g., Patent Document 8). Furthermore, it is known that by adding fine particles to the wavelength conversion material, the optical path length increases due to the scattering of light within the color conversion layer, improving the blue light absorption rate, and the luminous efficiency is improved by the rescattering of light reflected at the interface (Patent Documents 9, 10, etc.). [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2002-348568 [Patent Document 2] Japanese Patent Publication No. 2007-273440 [Patent Document 3] Japanese Patent Publication No. 2002-317175 [Patent Document 4] Japanese Patent Publication No. 2001-164245 [Patent Document 5] Japanese Patent Publication No. 2011-241160 [Patent Document 6] Japanese Patent Publication No. 2014-136771 [Patent Document 7] Japanese Patent Publication No. 2006-89724 [Patent Document 8] Japanese Patent Publication No. 2011-149028 [Patent Document 9] International Publication No. 2020 / 189678 [Patent Document 10] International Publication No. 2019 / 181698 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] However, when a wavelength conversion film formed using conventional wavelength conversion materials is exposed to air and developed, the film thickness decreases, and the desired properties of the wavelength conversion film cannot be effectively exhibited. On the other hand, in order to maintain a sufficient film thickness, it becomes necessary to design the material in a way that maintains the film thickness at the expense of the desired properties of the wavelength conversion film (especially conversion efficiency) (for example, while giving importance to the relationship with development conditions such as the type of developer). In other words, conventional wavelength conversion materials have the problem that when a wavelength conversion film formed using conventional wavelength conversion materials is exposed to air and developed, it is difficult to maintain a sufficient film thickness while also effectively exhibiting the desired properties of the wavelength conversion film (especially conversion efficiency). Therefore, there is a need for the development of a wavelength conversion material that can sufficiently maintain its original film thickness (i.e., the film thickness before development) even after exposure to air and development, and that can effectively exhibit the characteristics of a wavelength conversion film (especially conversion efficiency). Specifically, this refers to the ratio (%) of the film thickness after development to the film thickness immediately before development (original film thickness) even after exposure to air and development (this is also called the "residual film rate"). Furthermore, when a wavelength conversion film formed from a conventional wavelength conversion material using a photoradical polymerization initiator is exposed to air and then developed with a developer, there is a problem that the curing process during the formation of the wavelength conversion film is inhibited by oxygen (i.e., the polymerization reaction is stopped by oxygen in the air), resulting in insufficient curing and the formed wavelength conversion film dissolving in the developer. The present invention has been made in view of the above circumstances, and aims to provide a composition (i.e., a composition for forming a wavelength conversion film) that can form a wavelength conversion film having a high residual film rate (specifically, 50% or more, preferably 70% or more) and a high conversion efficiency (specifically, 30% or more, preferably 35% or more) even after development following exposure in the atmosphere. The present invention also aims to provide a composition (i.e., a composition for forming a wavelength conversion film) that can form a wavelength conversion film with excellent insolubility in the developer solution during development after exposure in air, even when a photoradical polymerization initiator is used as the photopolymerization initiator to form the wavelength conversion film. The present invention also aims to provide a composition (i.e., a composition for forming a wavelength conversion film) that, when formed by inkjet coating, has excellent photocurability even in air and, after film formation, has a high conversion efficiency (specifically, 30% or more, preferably 35% or more).

[0007] The inventors of the present invention conducted extensive research to solve the above problems and found that the above problems can be solved by a wavelength conversion film-forming composition containing a phosphor and a predetermined binder, thereby completing the present invention.

[0008] In other words, the present invention provides the following compositions for forming wavelength conversion films. [1] A composition for forming a wavelength conversion film, comprising (A) a phosphor and (B) a binder, wherein (B) the binder contains a compound represented by the following general formula (1). [ka] [In general formula (1), R 1 and R 2 Each of these independently represents one of the groups selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, and an aralkyl group, R 3 R represents one of the groups selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, aryl groups, and aralkyl groups. 4 [wherein X represents one of the groups selected from the group consisting of (meth)acryloyl groups, styryl groups, and alkenyl groups having 2 to 6 carbon atoms, and X represents NH or O, and n represents any integer from 1 to 5.] [2] R in the above general formula (1) 1 and R 2 is a hydrogen atom, and R 3is a methyl group, n is 1 to 4, and R 4 is a (meth)acryloyl group or a styryl group, and X is O, the composition for forming a wavelength conversion film according to [1]. [3] The composition for forming a wavelength conversion film according to [1] or [2], wherein the general formula (1) below is the following general formula (2).

Chemical Formula

[10] The composition for forming a wavelength conversion film according to any one of [1] to [9], further comprising (C) light-scattering particles.

[11] The composition for forming a wavelength conversion film according to

[10] , wherein the (C) light-scattering particles are titanium oxide particles.

[12] Furthermore, a wavelength conversion film-forming composition according to any one of [1] to

[11] , comprising (D) a thermal crosslinking agent.

[13] The wavelength conversion film forming composition according to

[12] , wherein the (D) thermal crosslinking agent is an epoxy crosslinking agent.

[14] A wavelength conversion film-forming composition according to any one of [1] to

[13] , wherein the content of the above (A) phosphor is 0.1% by mass or more in solid content.

[15] The wavelength conversion film forming composition according to any one of

[10] to

[14] , wherein the content of (C) light scattering particles is 1% by mass or more in the solid content.

[16] The wavelength conversion film-forming composition according to any one of [1] to

[15] , wherein the haze value of the film formed from the above composition is 18% or more.

[17] A wavelength conversion film forming composition for display, as described in any of [1] to

[16] .

[18] A wavelength conversion film made from a wavelength conversion film-forming composition described in any of [1] to

[17] . [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a composition (i.e., a composition for forming a wavelength conversion film) that can form a wavelength conversion film having a high residual film rate (specifically, 50% or more, preferably 70% or more) and a high conversion efficiency (specifically, 30% or more, preferably 35% or more), and the wavelength conversion film itself. According to the present invention, when a wavelength conversion film formed using a photoradical polymerization initiator as a photopolymerization initiator is developed after exposure to air, the problem of insufficient curing due to oxygen inhibition during the curing process of the wavelength conversion film, resulting in dissolution in the developer, can be avoided. In other words, according to the present invention, even when a photoradical polymerization initiator is used as a photopolymerization initiator, a composition (i.e., a composition for forming a wavelength conversion film) and the wavelength conversion film can be provided that can form a wavelength conversion film having suitable curability that avoids the above problem. The present invention also makes it possible to provide a composition (i.e., a composition for forming a wavelength conversion film) and a wavelength conversion film that, when formed by inkjet coating, has excellent photocurability even in air and, after film formation, has a high conversion efficiency (specifically, 30% or more, preferably 35% or more). The present invention also provides a wavelength conversion film-forming composition and a wavelength conversion film that can form a wavelength conversion film in which a phosphor can absorb a large amount of light. For example, it provides a wavelength conversion film-forming composition and a wavelength conversion film that can form a wavelength conversion film having a haze value of 18% or more. The present invention also provides wavelength conversion film formation compositions for various applications, for example, wavelength conversion film formation compositions for displays (particularly microLED displays). [Modes for carrying out the invention]

[0010] The present invention will be described in more detail below. The wavelength conversion film-forming composition of the present invention contains (A) a phosphor and (B) a binder, wherein (B) the binder contains a compound represented by the following general formula (1). [ka] [In general formula (1), R 1 and R 2 Each of these independently represents one of the groups selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, and an aralkyl group, R 3 R represents one of the groups selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, aryl groups, and aralkyl groups. 4 [wherein X represents one of the groups selected from the group consisting of (meth)acryloyl groups, styryl groups, and alkenyl groups having 2 to 6 carbon atoms, and X represents NH or O, and n represents any integer from 1 to 5.] In the following explanation, "solid content" refers to components other than the solvent that make up the wavelength conversion film-forming composition.

[0011] [(A) Phosphor] (A) The phosphor is not particularly limited as long as it can achieve the objectives of the present invention. It is acceptable as long as it is suitable as a phosphor while maintaining the desired residual film ratio even after forming a wavelength conversion film, exposing the wavelength conversion film to air, and developing it. It is preferable that the phosphor exhibits better properties. For example, when forming a wavelength conversion film for a micro-LED display, it is preferable that the phosphor exhibits better properties such as wavelength conversion efficiency, color purity, and lightfastness as a micro-LED display while maintaining the desired residual film ratio even after exposing the wavelength conversion film to air and developing it.

[0012] (A) The phosphor can be appropriately selected from conventionally known inorganic phosphors, organic dyes, quantum dots, etc., but organic dyes are preferred. Examples of organic pigments include compounds having condensed aryl rings such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluorantene, fluorene, and indene, as well as their derivatives; furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobicilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, and naphthene. Compounds containing heteroaryl rings such as tyridine, quinoxaline, and pyrrolopyridine, and their derivatives; stilbene compounds such as 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)ethenyl)biphenyl, and 4,4'-bis(N-(stilbene-4-yl)-N-phenylamino)stilbene; aromatic acetylene compounds; tetraphenylbutadiene compounds; aldazine compounds; pyromethene compounds; diketopyrrolo[3,4-c]pyrrole compounds; coumarins 6. Coumarin compounds such as those disclosed in Patent Document 7, Coumarin 7, Coumarin 153, and Patent Document 7; Azole compounds such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and their metal complexes; Cyanine compounds such as indocyanine green; Xanthene compounds such as fluorescein, eosin, and rhodamine, and thioxanthene compounds; Polyphenylene compounds, naphthalimide compounds, phthalocyanine compounds, and their metals Examples include, but are not limited to, complexes, porphyrin compounds and their metal complexes; oxazine compounds such as Nile Red and Nile Blue; helicene compounds; aromatic amine compounds such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine; and organometallic complex compounds such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re).

[0013] Furthermore, perylene compounds can also be suitably used as the organic dye (A) phosphor in the wavelength conversion film-forming composition of the present invention. Perylene compounds are compounds having perylene as a backbone, and preferred perylene compounds include, but are not limited to, the compound represented by the following formula (2) (Oracet® FL Red 305, manufactured by BASF), Lumogen® F Yellow 083 (manufactured by BASF), Solvent Green 5, and the compound represented by the following formula (Y1). The compound represented by the following formula (2) (Oracet® FL Red 305, manufactured by BASF) and the compound represented by the following formula (Y1) are more preferred.

[0014] [ka]

[0015] The compound represented by the following formula (Y1). [ka] [In the formula, R A and R B These are, independently, groups represented by the following formulas (2) or (3). [ka] (G 1 is O or NR E And, A 1 is an ethylene group or a propylene group, n is an integer between 1 and 10. R CThis is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkylcarbonyl group, an optionally substituted alkenylcarbonyl group, an optionally substituted arylcarbonyl group, or an optionally substituted heteroarylcarbonyl group. R E This is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. The dashed lines represent connections. [ka] (G 2 is O or NR E And, L 2 This is an alkylene group which may have a single bond or substituent. R D This includes a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkylcarbonyl group, an optionally substituted alkenylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted heteroarylcarbonyl group, or OR F And, R E This is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. R FThis is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkylcarbonyl group, an optionally substituted alkenylcarbonyl group, an optionally substituted arylcarbonyl group, or an optionally substituted heteroarylcarbonyl group. G 2 NR E And L 2 When it is a single bond, R D and R E These may bond with each other to form a ring with nitrogen atoms. L 2 When it is a single bond, R D is OR F This will not happen. L 2 When R is an alkylene group which may have substituents, D It will never become a hydrogen atom. R D When L is an alkyl group which may have substituents, 2 It is a single bond, The dashed lines represent connections.

[0016] G 1 O is preferred. A 1 An ethylene group is preferred. n is preferably 1 to 8, and more preferably 1 to 6.

[0017] R C The alkyl group represented by may be linear or branched, and specific examples include alkyl groups having 1 to 40 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-octyl group, decyl group, and eicosanyl group, with alkyl groups having 1 to 20 carbon atoms being preferred.

[0018] The above R CThe alkyl group represented by may have substituents. Examples of substituents include halogen atoms, cycloalkyl groups, aryl groups, heteroaryl groups, hydroxyl groups, cyano groups, and nitro groups, as described below. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0019] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0020] R C Examples of cycloalkyl groups represented by include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups, which have 3 to 10 carbon atoms, with cycloalkyl groups having 3 to 8 carbon atoms being preferred.

[0021] The above R C The cycloalkyl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkenyl group described below, the alkynyl group described below, the aryl group described below, the heteroaryl group described below, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0022] Examples of alkynyl groups include ethynyl group, 1-propynyl group, 2-propynyl group, butynyl group, isobutynyl group, s-butynyl group, and t-butynyl group.

[0023] R C Examples of alkenyl groups represented by include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, butenyl group, isobutenyl group, s-butenyl group, t-butenyl group, etc.

[0024] The above R CThe alkenyl group represented by may have substituents. Examples of substituents include the halogen atom, the aryl group described below, the heteroaryl group described below, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0025] R C The aryl group represented by can be a monocyclic aryl group, a fused aryl group, or a polycyclic aryl group. Specific examples include the phenyl group as a monocyclic aryl group, the naphthyl group, anthracenyl group, phenantrenyl group, fluorenyl group, pyrenyl group, triphenylenyl group, etc., as fused aryl groups, and aryl groups having 6 to 18 carbon atoms such as the biphenyl group and terphenyl group, with aryl groups having 6 to 14 carbon atoms being preferred.

[0026] The above R C The aryl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halides described later, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group described later, a hydroxyl group, a cyano group, a nitro group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0027] Examples of alkyl halogens include trifluoromethyl groups and pentafluoroethyl groups.

[0028] R C The heteroaryl group represented by may be either a monocyclic heteroaryl group or a fused heteroaryl group. Examples of monocyclic heteroaryl groups include pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, pyridyl, and pyrazyl groups, while examples of fused heteroaryl groups include indolyl, isoindolyl, benzimidazolyl, quinolyl, isoquinolyl, and quinoxalyl groups.

[0029] The above R CThe heteroaryl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halide, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the cyano group, the nitro group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0030] R CThe alkylcarbonyl groups represented by are methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, i-propylcarbonyl group, c-propylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group, s-butylcarbonyl group, t-butylcarbonyl group, c-butylcarbonyl group, 1-methyl-c-propylcarbonyl group, 2-methyl-c-propylcarbonyl group, n-pentylcarbonyl group, 1-methyl-n-butylcarbonyl group, 2-methyl-n-butylcarbonyl group, 3-methyl-n-butylcarbonyl group, and 1,1-di Methyl-n-propylcarbonyl group, 1,2-dimethyl-n-propylcarbonyl group, 2,2-dimethyl-n-propylcarbonyl group, 1-ethyl-n-propylcarbonyl group, c-pentylcarbonyl group, 1-methyl-c-butylcarbonyl group, 2-methyl-c-butylcarbonyl group, 3-methyl-c-butylcarbonyl group, 1,2-dimethyl-c-propylcarbonyl group, 2,3-dimethyl-c-propylcarbonyl group, 1-ethyl-c-propylcarbonyl group, 2-ethyl-c-propylcarbonyl group, n-hexylcarbonyl group, 1-methyl-n -Pentylcarbonyl group, 2-methyl-n-pentylcarbonyl group, 3-methyl-n-pentylcarbonyl group, 4-methyl-n-pentylcarbonyl group, 1,1-dimethyl-n-butylcarbonyl group, 1,2-dimethyl-n-butylcarbonyl group, 1,3-dimethyl-n-butylcarbonyl group, 2,2-dimethyl-n-butylcarbonyl group, 2,3-dimethyl-n-butylcarbonyl group, 3,3-dimethyl-n-butylcarbonyl group, 1-ethyl-n-butylcarbonyl group, 2-ethyl-n-butylcarbonyl group, 1,1,2-trimethyl-n-propyl Carbonyl group, 1,2,2-trimethyl-n-propylcarbonyl group, 1-ethyl-1-methyl-n-propylcarbonyl group, 1-ethyl-2-methyl-n-propylcarbonyl group, c-hexylcarbonyl group, 1-methyl-c-pentylcarbonyl group, 2-methyl-c-pentylcarbonyl group, 3-methyl-c-pentylcarbonyl group, 1-ethyl-c-butylcarbonyl group, 2-ethyl-c-butylcarbonyl group, 3-ethyl-c-butylcarbonyl group, 1,2-dimethyl-c-butylcarbonyl group, 1,3-dimethyl-c-butylcarbonyl group, 2,2-dimethyl-c-butylcarbonyl group, 2,3-dimethyl-c-butylcarbonyl group, 2,4-dimethyl-c-butylcarbonyl group, 3,3-dimethyl-c-butylcarbonyl group, 1-n-propyl-c-propylcarbonyl group, 2-n-propyl-c-propylcarbonyl group, 1-i-propyl-c-propylcarbonyl group, 2-i-propyl-c-propylcarbonyl group, 1,2,2-trimethyl-c-propylcarbonyl group, 1 Examples include alkylcarbonyl groups having 2 to 11 carbon atoms, such as 2,3-trimethyl-c-propylcarbonyl group, 2,2,3-trimethyl-c-propylcarbonyl group, 1-ethyl-2-methyl-c-propylcarbonyl group, 2-ethyl-1-methyl-c-propylcarbonyl group, 2-ethyl-2-methyl-c-propylcarbonyl group, and 2-ethyl-3-methyl-c-propylcarbonyl group, with alkylcarbonyl groups having 2 to 6 carbon atoms being preferred.

[0031] The above R C The alkylcarbonyl group represented by may have substituents. Examples of substituents include the halogen atom, the cycloalkyl group, the aryl group, the heteroaryl group, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0032] R CThe alkenylcarbonyl groups represented by include ethenylcarbonyl group, 1-propenylcarbonyl group, 2-propenylcarbonyl group, 1-methyl-1-ethenylcarbonyl group, 1-butenylcarbonyl group, 2-butenylcarbonyl group, 3-butenylcarbonyl group, 2-methyl-1-propenylcarbonyl group, 2-methyl-2-propenylcarbonyl group, 1-ethylethenylcarbonyl group, 1-methyl-1-propenylcarbonyl group, 1-methyl-2-propenylcarbonyl group, 1-pentenylcarbonyl group, 2-pentenylcarbonyl group, 3-pentenylcarbonyl group, 4-pentenylcarbonyl group, and 1-n -Propylethenylcarbonyl group, 1-methyl-1-butenylcarbonyl group, 1-methyl-2-butenylcarbonyl group, 1-methyl-3-butenylcarbonyl group, 2-ethyl-2-propenylcarbonyl group, 2-methyl-1-butenylcarbonyl group, 2-methyl-2-butenylcarbonyl group, 2-methyl-3-butenylcarbonyl group, 3-methyl-1-butenylcarbonyl group, 3-methyl-2-butenylcarbonyl group, 3-methyl-3-butenylcarbonyl group, 1,1-dimethyl-2-propenylcarbonyl group, 1-i-propylethenylcarbonyl group, 1,2-dimethyl-1-propenylcarbonyl group, 1,2-dimethyl-2-propenylcarbonyl group, 1-c-pentenylcarbonyl group, 2-c-pentenylcarbonyl group, 3-c-pentenylcarbonyl group, 1-hexenylcarbonyl group, 2-hexenylcarbonyl group, 3-hexenylcarbonyl group, 4-hexenylcarbonyl group, 5-hexenylcarbonyl group, 1-methyl-1-pentenylcarbonyl group, 1-methyl-2-pentenylcarbonyl group, 1-methyl-3-pentenylcarbonyl group, 1-methyl-4-pentenylcarbonyl Group, 1-n-butylethenylcarbonyl group, 2-methyl-1-pentenylcarbonyl group, 2-methyl-2-pentenylcarbonyl group, 2-methyl-3-pentenylcarbonyl group, 2-methyl-4-pentenylcarbonyl group, 2-n-propyl-2-propenylcarbonyl group, 3-methyl-1-pentenylcarbonyl group, 3-methyl-2-pentenylcarbonyl group, 3-methyl-3-pentenylcarbonyl group, 3-methyl-4-pentenylcarbonyl group, 3-ethyl-3-butenylcarbonyl Nyl group, 4-methyl-1-pentenylcarbonyl group, 4-methyl-2-pentenylcarbonyl group, 4-methyl-3-pentenylcarbonyl group, 4-methyl-4-pentenylcarbonyl group, 1,1-dimethyl-2-butenylcarbonyl group, 1,1-dimethyl-3-butenylcarbonyl group, 1,2-dimethyl-1-butenylcarbonyl group, 1,2-dimethyl-2-butenylcarbonyl group, 1,2-dimethyl-3-butenylcarbonyl group, 1-methyl-2-ethyl-2-propenylcarbonyl 1-s-butylethenylcarbonyl group, 1,3-dimethyl-1-butenylcarbonyl group, 1,3-dimethyl-2-butenylcarbonyl group, 1,3-dimethyl-3-butenylcarbonyl group, 1-i-butylethenylcarbonyl group, 2,2-dimethyl-3-butenylcarbonyl group, 2,3-dimethyl-1-butenylcarbonyl group, 2,3-dimethyl-2-butenylcarbonyl group, 2,3-dimethyl-3-butenylcarbonyl group, 2-i-propyl-2-propenylcarbonyl group, 3,3-dimethyl-1-butenylcarbonyl group, 1-ethyl-1-butenylcarbonyl group, 1-ethyl-2-butenylcarbonyl group, 1-ethyl-3-butenylcarbonyl group, 1-n-propyl-1-propenylcarbonyl group, 1-n-propyl-2-propenylcarbonyl group, 2-ethyl-1-butenylcarbonyl group, 2-ethyl-2-butenylcarbonyl group, 2-ethyl-3-butenylcarbonyl group, 1,1,2- methyl-2-propenylcarbonyl group, 1-t-butylethenylcarbonyl group, 1-methyl-1-ethyl-2-propenylcarbonyl group, 1-ethyl-2-methyl-1-propenylcarbonyl group, 1-ethyl-2-methyl-2-propenylcarbonyl group, 1-i-propyl-1-propenylcarbonyl group, 1-i-propyl-2-propenylcarbonyl group, 1-methyl-2-c-pentenylcarbonyl group, 1-methyl -3-c-pentenylcarbonyl group, 2-methyl-1-c-pentenylcarbonyl group, 2-methyl-2-c-pentenylcarbonyl group, 2-methyl-3-c-pentenylcarbonyl group, 2-methyl-4-c-pentenylcarbonyl group, 2-methyl-5-c-pentenylcarbonyl group, 2-methylene-c-pentylcarbonyl group, 3-methyl-1-c-pentenylcarbonyl group, 3-methyl-2-c-pentenylcarbonyl group Examples include C3-C-11 alkenylcarbonyl groups such as the nyl group, 3-methyl-3-c-pentenylcarbonyl group, 3-methyl-4-c-pentenylcarbonyl group, 3-methyl-5-c-pentenylcarbonyl group, 3-methylene-c-pentylcarbonyl group, 1-c-hexenylcarbonyl group, 2-c-hexenylcarbonyl group, and 3-c-hexenylcarbonyl group, with C3-C-6 alkenylcarbonyl groups being preferred.

[0033] The above R C The alkenylcarbonyl group represented by may have substituents. Examples of substituents include the halogen atom, the aryl group, the heteroaryl group, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0034] R CExamples of arylcarbonyl groups represented by include arylcarbonyl groups having 7 to 16 carbon atoms, such as benzoyl groups, naphthoyl groups, and anthracenyl groups, with arylcarbonyl groups having 7 to 11 carbon atoms being preferred.

[0035] The above R C The arylcarbonyl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halide, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the cyano group, the nitro group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0036] R C Examples of heteroarylcarbonyl groups represented by include heteroarylcarbonyl groups having 4 to 12 carbon atoms, such as pyrrolylcarbonyl group, thienylcarbonyl group, furanylcarbonyl group, imidazolylcarbonyl group, pyrazolylcarbonyl group, thiazolylcarbonyl group, oxazolylcarbonyl group, pyridylcarbonyl group, pyrazylcarbonyl group, indolylcarbonyl group, isoindolylcarbonyl group, benzimidazolylcarbonyl group, quinolylcarbonyl group, isoquinolylcarbonyl group, and quinoxalylcarbonyl group, with heteroarylcarbonyl groups having 4 to 10 carbon atoms being preferred.

[0037] The heteroarylcarbonyl group may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halide, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the cyano group, the nitro group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0038] R EThe alkyl group represented by may be linear or branched, and specific examples include alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, and tert-butyl group, with alkyl groups having 1 to 6 carbon atoms being preferred.

[0039] The above R E The alkyl group represented by may have substituents. Examples of substituents include the halogen atom, the cycloalkyl group described below, the aryl group described below, the heteroaryl group described below, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0040] R E Examples of cycloalkyl groups represented by include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups, which have 3 to 10 carbon atoms, with cycloalkyl groups having 3 to 8 carbon atoms being preferred.

[0041] The above R E The cycloalkyl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkenyl group described below, the alkynyl group described below, the aryl group described below, the heteroaryl group described below, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0042] R E Examples of alkenyl groups represented by include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, butenyl group, isobutenyl group, s-butenyl group, t-butenyl group, etc.

[0043] The above R EThe alkenyl group represented by may have substituents. Examples of substituents include halogen atoms, aryl groups, heteroaryl groups, hydroxyl groups, cyano groups, and nitro groups, as described below. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0044] R E The aryl group represented by can be a monocyclic aryl group, a fused aryl group, or a polycyclic aryl group. Specific examples include the phenyl group as a monocyclic aryl group, the naphthyl group, anthracenyl group, phenantrenyl group, fluorenyl group, pyrenyl group, triphenylenyl group, etc., as fused aryl groups, and aryl groups having 6 to 18 carbon atoms such as the biphenyl group and terphenyl group, with aryl groups having 6 to 14 carbon atoms being preferred.

[0045] The above R E The aryl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halide, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group described later, the hydroxyl group, the cyano group, the nitro group, the pentafluorosulfanil group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0046] R E The heteroaryl group represented by may be either a monocyclic heteroaryl group or a fused heteroaryl group. Examples of monocyclic heteroaryl groups include pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, pyridyl, and pyrazyl groups, while examples of fused heteroaryl groups include indolyl, isoindolyl, benzimidazolyl, quinolyl, isoquinolyl, and quinoxalyl groups.

[0047] The above R EThe heteroaryl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halide, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the cyano group, the nitro group, the pentafluorosulfanil group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0048] G 2 is O or NR E It is preferably O or NH.

[0049] L 2 The alkylene group represented by may be linear, branched, or cyclic. Specific examples include alkylene groups having 1 to 20 carbon atoms, such as methylene, methylmethylene, dimethylmethylene, ethylene, 1,2-dimethylethylene, tetramethylethylene, trimethylene, propylene, tetramethylene, pentamethylene, hexamethylene, 1,2-cyclohexylene, 1,3-cyclohexylene, and 1,4-cyclohexylene, with alkylene groups having 1 to 14 carbon atoms being preferred.

[0050] The above L 2 The alkylene group represented by may have substituents. Examples of substituents include the halogen atom, the cycloalkyl group, the aryl group, the heteroaryl group, the alkylcarbonyloxy group, hydroxyl group, cyano group, nitro group, oxo group, etc. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0051] Examples of alkylcarbonyloxy groups include methylcarbonyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, c-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, s-butylcarbonyloxy group, t-butylcarbonyloxy group, c-butylcarbonyloxy group, 1-methyl-c-propylcarbonyloxy group, 2-methyl-c-propylcarbonyloxy group, and n-pentylcarbonyloxy group. Nyloxy group, 1-methyl-n-butylcarbonyloxy group, 2-methyl-n-butylcarbonyloxy group, 3-methyl-n-butylcarbonyloxy group, 1,1-dimethyl-n-propylcarbonyloxy group, 1,2-dimethyl-n-propylcarbonyloxy group, 2,2-dimethyl-n-propylcarbonyloxy group, 1-ethyl-n-propylcarbonyloxy group, c-pentylcarbonyloxy group, 1-methyl-c-butylcarbonyloxy group, 2-methyl-c-butylcarbonyloxy group Xyl group, 3-methyl-c-butylcarbonyloxy group, 1,2-dimethyl-c-propylcarbonyloxy group, 2,3-dimethyl-c-propylcarbonyloxy group, 1-ethyl-c-propylcarbonyloxy group, 2-ethyl-c-propylcarbonyloxy group, n-hexylcarbonyloxy group, 1-methyl-n-pentylcarbonyloxy group, 2-methyl-n-pentylcarbonyloxy group, 3-methyl-n-pentylcarbonyloxy group, 4-methyl-n-pentylcarbonyloxy group C group, 1,1-dimethyl-n-butylcarbonyloxy group, 1,2-dimethyl-n-butylcarbonyloxy group, 1,3-dimethyl-n-butylcarbonyloxy group, 2,2-dimethyl-n-butylcarbonyloxy group, 2,3-dimethyl-n-butylcarbonyloxy group, 3,3-dimethyl-n-butylcarbonyloxy group, 1-ethyl-n-butylcarbonyloxy group, 2-ethyl-n-butylcarbonyloxy group, 1,1,2-trimethyl-n-propylcarbonyloxy group, 1,2,2-trimethyl-n-propylcarbonyloxy group, 1-ethyl-1-methyl-n-propylcarbonyloxy group, 1-ethyl-2-methyl-n-propylcarbonyloxy group, c-hexylcarbonyloxy group, 1-methyl-c-pentylcarbonyloxy group, 2-methyl-c-pentylcarbonyloxy group, 3-methyl-c-pentylcarbonyloxy group, 1-ethyl-c-butylcarbonyloxy group, 2-ethyl-c-butylcarbonyloxy group, 3-ethyl-c-butylcarbonyloxy group, 1,2-dimethyl-c-butylcarbonyloxy group, 1,3-dimethyl-c-butylcarbonyloxy group, 2,2-dimethyl-c-butylcarbonyloxy group, 2,3-dimethyl-c-butylcarbonyloxy group, 2,4-dimethyl-c-butylcarbonyloxy group, 3,3-dimethyl-c-butyl Examples of alkylcarbonyloxy groups having 2 to 11 carbon atoms include carbonyloxy groups, 1-n-propyl-c-propylcarbonyloxy groups, 2-n-propyl-c-propylcarbonyloxy groups, 1-i-propyl-c-propylcarbonyloxy groups, 2-i-propyl-c-propylcarbonyloxy groups, 1,2,2-trimethyl-c-propylcarbonyloxy groups, 1,2,3-trimethyl-c-propylcarbonyloxy groups, 2,2,3-trimethyl-c-propylcarbonyloxy groups, 1-ethyl-2-methyl-c-propylcarbonyloxy groups, 2-ethyl-1-methyl-c-propylcarbonyloxy groups, 2-ethyl-2-methyl-c-propylcarbonyloxy groups, and 2-ethyl-3-methyl-c-propylcarbonyloxy groups, with alkylcarbonyloxy groups having 2 to 6 carbon atoms being preferred.

[0052] R D The alkyl group represented by may be linear or branched, and specific examples include alkyl groups having 1 to 40 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-octyl group, decyl group, and eicosanyl group, with alkyl groups having 1 to 20 carbon atoms being preferred.

[0053] The above RD The alkyl group represented by may have substituents. Examples of substituents include halogen atoms, cycloalkyl groups, aryl groups, heteroaryl groups, hydroxyl groups, cyano groups, nitro groups, oxo groups, epoxy groups, etc. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0054] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0055] R D Examples of cycloalkyl groups represented by include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups, which have 3 to 10 carbon atoms, with cycloalkyl groups having 3 to 8 carbon atoms being preferred.

[0056] The above R D The cycloalkyl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkenyl group described below, the alkynyl group described below, the aryl group described below, the heteroaryl group described below, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0057] Examples of alkynyl groups include ethynyl group, 1-propynyl group, 2-propynyl group, butynyl group, isobutynyl group, s-butynyl group, and t-butynyl group.

[0058] R D Examples of alkenyl groups represented by include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, butenyl group, isobutenyl group, s-butenyl group, t-butenyl group, etc.

[0059] The above R DThe alkenyl group represented by may have substituents. Examples of substituents include the halogen atom, the aryl group described below, the heteroaryl group described below, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0060] R D The aryl group represented by can be a monocyclic aryl group, a fused aryl group, or a polycyclic aryl group. Specific examples include the phenyl group as a monocyclic aryl group, the naphthyl group, anthracenyl group, phenantrenyl group, fluorenyl group, pyrenyl group, triphenylenyl group, etc., as fused aryl groups, and aryl groups having 6 to 18 carbon atoms such as the biphenyl group and terphenyl group, with aryl groups having 6 to 14 carbon atoms being preferred.

[0061] The above R D The aryl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halides described later, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group described later, a hydroxyl group, a cyano group, a nitro group, a pentafluorosulfanil group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0062] Examples of alkyl halogens include trifluoromethyl groups and pentafluoroethyl groups.

[0063] R D The heteroaryl group represented by may be either a monocyclic heteroaryl group or a fused heteroaryl group. Examples of monocyclic heteroaryl groups include pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, pyridyl, and pyrazyl groups, while examples of fused heteroaryl groups include indolyl, isoindolyl, benzimidazolyl, quinolyl, isoquinolyl, and quinoxalyl groups.

[0064] The above RD The heteroaryl group represented by may have substituents. Examples of substituents include the halogen atom, the alkyl group, the alkyl halide, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the cyano group, the nitro group, and the like. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0065] R DThe alkylcarbonyl groups represented by are methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, i-propylcarbonyl group, c-propylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group, s-butylcarbonyl group, t-butylcarbonyl group, c-butylcarbonyl group, 1-methyl-c-propylcarbonyl group, 2-methyl-c-propylcarbonyl group, n-pentylcarbonyl group, 1-methyl-n-butylcarbonyl group, 2-methyl-n-butylcarbonyl group, 3-methyl-n-butylcarbonyl group, and 1,1-di Methyl-n-propylcarbonyl group, 1,2-dimethyl-n-propylcarbonyl group, 2,2-dimethyl-n-propylcarbonyl group, 1-ethyl-n-propylcarbonyl group, c-pentylcarbonyl group, 1-methyl-c-butylcarbonyl group, 2-methyl-c-butylcarbonyl group, 3-methyl-c-butylcarbonyl group, 1,2-dimethyl-c-propylcarbonyl group, 2,3-dimethyl-c-propylcarbonyl group, 1-ethyl-c-propylcarbonyl group, 2-ethyl-c-propylcarbonyl group, n-hexylcarbonyl group, 1-methyl-n -Pentylcarbonyl group, 2-methyl-n-pentylcarbonyl group, 3-methyl-n-pentylcarbonyl group, 4-methyl-n-pentylcarbonyl group, 1,1-dimethyl-n-butylcarbonyl group, 1,2-dimethyl-n-butylcarbonyl group, 1,3-dimethyl-n-butylcarbonyl group, 2,2-dimethyl-n-butylcarbonyl group, 2,3-dimethyl-n-butylcarbonyl group, 3,3-dimethyl-n-butylcarbonyl group, 1-ethyl-n-butylcarbonyl group, 2-ethyl-n-butylcarbonyl group, 1,1,2-trimethyl-n-propyl Carbonyl group, 1,2,2-trimethyl-n-propylcarbonyl group, 1-ethyl-1-methyl-n-propylcarbonyl group, 1-ethyl-2-methyl-n-propylcarbonyl group, c-hexylcarbonyl group, 1-methyl-c-pentylcarbonyl group, 2-methyl-c-pentylcarbonyl group, 3-methyl-c-pentylcarbonyl group, 1-ethyl-c-butylcarbonyl group, 2-ethyl-c-butylcarbonyl group, 3-ethyl-c-butylcarbonyl group, 1,2-dimethyl-c-butylcarbonyl group, 1,3-dimethyl-c-butylcarbonyl group, 2,2-dimethyl-c-butylcarbonyl group, 2,3-dimethyl-c-butylcarbonyl group, 2,4-dimethyl-c-butylcarbonyl group, 3,3-dimethyl-c-butylcarbonyl group, 1-n-propyl-c-propylcarbonyl group, 2-n-propyl-c-propylcarbonyl group, 1-i-propyl-c-propylcarbonyl group, 2-i-propyl-c-propylcarbonyl group, 1,2,2-trimethyl-c-propylcarbonyl group, 1 Examples include alkylcarbonyl groups having 2 to 11 carbon atoms, such as 2,3-trimethyl-c-propylcarbonyl group, 2,2,3-trimethyl-c-propylcarbonyl group, 1-ethyl-2-methyl-c-propylcarbonyl group, 2-ethyl-1-methyl-c-propylcarbonyl group, 2-ethyl-2-methyl-c-propylcarbonyl group, and 2-ethyl-3-methyl-c-propylcarbonyl group, with alkylcarbonyl groups having 2 to 6 carbon atoms being preferred.

[0066] The above R D The alkylcarbonyl group represented by may have substituents. Examples of substituents include the halogen atom, the cycloalkyl group, the aryl group, the heteroaryl group, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0067] R DThe alkenylcarbonyl groups represented by include ethenylcarbonyl group, 1-propenylcarbonyl group, 2-propenylcarbonyl group, 1-methyl-1-ethenylcarbonyl group, 1-butenylcarbonyl group, 2-butenylcarbonyl group, 3-butenylcarbonyl group, 2-methyl-1-propenylcarbonyl group, 2-methyl-2-propenylcarbonyl group, 1-ethylethenylcarbonyl group, 1-methyl-1-propenylcarbonyl group, 1-methyl-2-propenylcarbonyl group, 1-pentenylcarbonyl group, 2-pentenylcarbonyl group, 3-pentenylcarbonyl group, 4-pentenylcarbonyl group, and 1-n -Propylethenylcarbonyl group, 1-methyl-1-butenylcarbonyl group, 1-methyl-2-butenylcarbonyl group, 1-methyl-3-butenylcarbonyl group, 2-ethyl-2-propenylcarbonyl group, 2-methyl-1-butenylcarbonyl group, 2-methyl-2-butenylcarbonyl group, 2-methyl-3-butenylcarbonyl group, 3-methyl-1-butenylcarbonyl group, 3-methyl-2-butenylcarbonyl group, 3-methyl-3-butenylcarbonyl group, 1,1-dimethyl-2-propenylcarbonyl group, 1-i-propylethenylcarbonyl group, 1,2-dimethyl-1-propenylcarbonyl group, 1,2-dimethyl-2-propenylcarbonyl group, 1-c-pentenylcarbonyl group, 2-c-pentenylcarbonyl group, 3-c-pentenylcarbonyl group, 1-hexenylcarbonyl group, 2-hexenylcarbonyl group, 3-hexenylcarbonyl group, 4-hexenylcarbonyl group, 5-hexenylcarbonyl group, 1-methyl-1-pentenylcarbonyl group, 1-methyl-2-pentenylcarbonyl group, 1-methyl-3-pentenylcarbonyl group, 1-methyl-4-pentenylcarbonyl Group, 1-n-butylethenylcarbonyl group, 2-methyl-1-pentenylcarbonyl group, 2-methyl-2-pentenylcarbonyl group, 2-methyl-3-pentenylcarbonyl group, 2-methyl-4-pentenylcarbonyl group, 2-n-propyl-2-propenylcarbonyl group, 3-methyl-1-pentenylcarbonyl group, 3-methyl-2-pentenylcarbonyl group, 3-methyl-3-pentenylcarbonyl group, 3-methyl-4-pentenylcarbonyl group, 3-ethyl-3-butenylcarbonyl Nyl group, 4-methyl-1-pentenylcarbonyl group, 4-methyl-2-pentenylcarbonyl group, 4-methyl-3-pentenylcarbonyl group, 4-methyl-4-pentenylcarbonyl group, 1,1-dimethyl-2-butenylcarbonyl group, 1,1-dimethyl-3-butenylcarbonyl group, 1,2-dimethyl-1-butenylcarbonyl group, 1,2-dimethyl-2-butenylcarbonyl group, 1,2-dimethyl-3-butenylcarbonyl group, 1-methyl-2-ethyl-2-propenylcarbonyl 1-s-butylethenylcarbonyl group, 1,3-dimethyl-1-butenylcarbonyl group, 1,3-dimethyl-2-butenylcarbonyl group, 1,3-dimethyl-3-butenylcarbonyl group, 1-i-butylethenylcarbonyl group, 2,2-dimethyl-3-butenylcarbonyl group, 2,3-dimethyl-1-butenylcarbonyl group, 2,3-dimethyl-2-butenylcarbonyl group, 2,3-dimethyl-3-butenylcarbonyl group, 2-i-propyl-2-propenylcarbonyl group, 3,3-dimethyl-1-butenylcarbonyl group, 1-ethyl-1-butenylcarbonyl group, 1-ethyl-2-butenylcarbonyl group, 1-ethyl-3-butenylcarbonyl group, 1-n-propyl-1-propenylcarbonyl group, 1-n-propyl-2-propenylcarbonyl group, 2-ethyl-1-butenylcarbonyl group, 2-ethyl-2-butenylcarbonyl group, 2-ethyl-3-butenylcarbonyl group, 1,1,2- methyl-2-propenylcarbonyl group, 1-t-butylethenylcarbonyl group, 1-methyl-1-ethyl-2-propenylcarbonyl group, 1-ethyl-2-methyl-1-propenylcarbonyl group, 1-ethyl-2-methyl-2-propenylcarbonyl group, 1-i-propyl-1-propenylcarbonyl group, 1-i-propyl-2-propenylcarbonyl group, 1-methyl-2-c-pentenylcarbonyl group, 1-methyl -3-c-pentenylcarbonyl group, 2-methyl-1-c-pentenylcarbonyl group, 2-methyl-2-c-pentenylcarbonyl group, 2-methyl-3-c-pentenylcarbonyl group, 2-methyl-4-c-pentenylcarbonyl group, 2-methyl-5-c-pentenylcarbonyl group, 2-methylene-c-pentylcarbonyl group, 3-methyl-1-c-pentenylcarbonyl group, 3-methyl-2-c-pentenylcarbonyl group Examples include C3-C-11 alkenylcarbonyl groups such as the nyl group, 3-methyl-3-c-pentenylcarbonyl group, 3-methyl-4-c-pentenylcarbonyl group, 3-methyl-5-c-pentenylcarbonyl group, 3-methylene-c-pentylcarbonyl group, 1-c-hexenylcarbonyl group, 2-c-hexenylcarbonyl group, and 3-c-hexenylcarbonyl group, with C3-C-6 alkenylcarbonyl groups being preferred.

[0068] The above R D The alkenylcarbonyl group represented by may have substituents. Examples of substituents include the halogen atom, the aryl group, the heteroaryl group, the hydroxyl group, the cyano group, the nitro group, and so on. If substituents are present, the number is preferably 1 to 6, and more preferably 1 to 3.

[0069] R DExamples of the arylcarbonyl group represented by include arylcarbonyl groups having 7 to 16 carbon atoms such as benzoyl group, naphthoyl group, and anthracenylcarbonyl group, and arylcarbonyl groups having 7 to 11 carbon atoms are preferred.

[0070] The above R D The arylcarbonyl group represented by may have a substituent. Examples of the substituent include the aforementioned halogen atom, the aforementioned alkyl group, the aforementioned halogenated alkyl group, the aforementioned alkenyl group, the aforementioned alkynyl group, the aforementioned aryl group, the aforementioned heteroaryl group, cyano group, nitro group and the like. When the group has a substituent, the number thereof is preferably 1 to 6, and more preferably 1 to 3.

[0071] R D Examples of the heteroarylcarbonyl group represented by include heteroarylcarbonyl groups having 4 to 12 carbon atoms such as pyrrolylcarbonyl group, thienylcarbonyl group, furanylcarbonyl group, imidazolylcarbonyl group, pyrazolylcarbonyl group, thiazolylcarbonyl group, oxazolylcarbonyl group, pyridylcarbonyl group, pyrazylcarbonyl group, indolylcarbonyl group, isoindolylcarbonyl group, benzimidazolylcarbonyl group, quinolylcarbonyl group, isoquinolylcarbonyl group, and quinoxalylcarbonyl group, and heteroarylcarbonyl groups having 4 to 10 carbon atoms are preferred.

[0072] The aforementioned heteroarylcarbonyl group may have a substituent. Examples of the substituent include the aforementioned halogen atom, the aforementioned alkyl group, the aforementioned halogenated alkyl group, the aforementioned alkenyl group, the aforementioned alkynyl group, the aforementioned aryl group, the aforementioned heteroaryl group, cyano group, nitro group and the like. When the group has a substituent, the number thereof is preferably 1 to 6, and more preferably 1 to 3.

[0073] R Eis a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group, and examples of the substituents that these alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, and heteroaryl groups, as well as these groups possess, include those for R in the above formula (2) E the same groups as the exemplified groups can be mentioned.

[0074] R F is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkylcarbonyl group, an optionally substituted alkenylcarbonyl group, an optionally substituted arylcarbonyl group, or an optionally substituted heteroarylcarbonyl group, and examples of the substituents that these alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkylcarbonyl groups, alkenylcarbonyl groups, arylcarbonyl groups, and heteroarylcarbonyl groups, as well as these groups possess, include those for the above R D the same groups as the exemplified groups in can be mentioned.

[0075] Note that, in formula (2), G 2 is NR E and L 2 is a single bond, R D and R E may be bonded to each other to form a ring together with the nitrogen atom, and when L 2 is a single bond, R 2 will not be OR F , and when L 2 is an optionally substituted alkylene group, R D will not be a hydrogen atom, and when R D is an optionally substituted alkyl group, L 2 is a single bond.

[0076] The above R Aand R B These elements may be identical or different from each other, but it is more preferable that they be the same base.

[0077] The above R A and R B The bonding positions to the perylene structure are not particularly limited, but the bonding positions represented by the following formulas (Y1a) to (Y1c) are preferred.

[0078] [ka] (In the formula, R A and R B (This is the same as above.)

[0079] The group represented by formula (2) above is preferably one of the following formulas (2-1) to (2-4). [ka] (In the formula, R C (and n are the same as above.)

[0080] The group represented by formula (3) above is preferably a group represented by any of the following formulas (3-1) to (3-2). [ka] (In the formula, m is an integer between 1 and 20. R D (This is the same as above.)

[0081] Specific examples of the phosphor represented by (Y1) above include the phosphors represented by the following formulas (Y1-1) to (Y1-13).

[0082] [ka]

[0083] [ka]

[0084] The compound represented by the above formula (Y1) can be synthesized by referring to known methods, but the synthesis method is not particularly limited as long as the desired compound is obtained.

[0085] In the present invention, the content of (A) phosphor (i.e., the content of the phosphor which is component (A) of the wavelength conversion film forming composition of the present invention) is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, and even more preferably 0.5% by mass or more, considering the wavelength conversion efficiency of the obtained wavelength conversion film. On the other hand, there is no particular upper limit to the content of (A) phosphor, but considering that the fluorescence quantum yield decreases when the phosphor is concentrated to a high level, it is preferably 30% by mass or less, more preferably 10% by mass or less, even more preferably 7% by mass or less, and even more preferably 5% by mass or less, considering the fluorescence quantum yield decreases when the phosphor is concentrated to a high level, and the content is preferably 30% by mass or less, more preferably 10% by mass or less, and even more preferably 7% by mass or less, and even more preferably 5% by mass or less, considering the wavelength conversion efficiency of the obtained wavelength conversion film. The above-mentioned phosphors may be used individually or in combination of two or more types.

[0086] [(B) Binder (and (B-2) Compound represented by general formula (1))] (B) The binder (i.e., the binder which is component (B) of the wavelength conversion film-forming composition of the present invention) contains a compound represented by the following general formula (1). [ka] [In general formula (1), R 1 and R 2 Each of these independently represents one of the groups selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, and an aralkyl group, R 3 R represents one of the groups selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, aryl groups, and aralkyl groups. 4[wherein X represents one of the groups selected from the group consisting of (meth)acryloyl groups, styryl groups, and alkenyl groups having 2 to 6 carbon atoms, and X represents NH or O, and n represents any integer from 1 to 5.]

[0087] R 1 , R 2 and R 3 Examples of C1-C6 alkyl groups represented by include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.

[0088] R 1 , R 2 and R 3 Examples of alkenyl groups with 2 to 6 carbon atoms represented by include vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, hexenyl (cis-3-hexenyl, etc.), and cyclohexenyl groups.

[0089] R 1 , R 2 and R 3 Examples of aryl groups represented by this include phenyl, tolyl, xylyl, and naphthyl groups.

[0090] R 1 , R 2 and R 3 Examples of aralkyl groups represented by this include the benzyl group, 2-phenylethyl group, 2-naphthylethyl group, and diphenylmethyl group.

[0091] R 1 and R 2Each is preferably selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, even more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and particularly preferably a hydrogen atom or a methyl group. Among these, R 1 and R 2 It is preferable that both are hydrogen atoms.

[0092] Also R 3 It is preferably selected from the group consisting of alkyl groups having 1 to 6 carbon atoms and alkenyl groups having 2 to 6 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, even more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group.

[0093] R 4 This represents one of the groups selected from the group consisting of (meth)acryloyl groups, styryl groups, and alkenyl groups having 2 to 6 carbon atoms. In this specification, "(meth)acryloyl group" means that either an acryloyl group or a methacryloyl group may be used. The same applies to (meth)acrylic acid, (meth)acrylate, and (meth)acryloyloxy groups.

[0094] R 4 Examples of C2-C6 alkenyl groups represented by include vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, hexenyl (cis-3-hexenyl, etc.), and cyclohexenyl groups, with C2-C5 alkenyl groups being preferred.

[0095] Among these, R 4 It is preferable that the group be a (meth)acryloyl group or a styryl group, and more preferably a (meth)acryloyl group, for reasons such as being able to function effectively as a polymerizable group and allowing the effects of the present invention to be more effectively achieved.

[0096] In general formula (I), n represents any integer from 1 to 5. Preferably, n is any integer from 1 to 4, more preferably 1 or 2, and even more preferably 1. Compounds of general formula (I) have multiple polymerizable functional groups, so they can be cured by polymerization, and because the influence of intermolecular interactions is kept low, they have the characteristic of not easily becoming highly viscous.

[0097] X can be either NH or O, but is preferably O.

[0098] Specific examples of compounds represented by the above general formula (1) include, for example, the following compounds.

[0099] [ka]

[0100] The compound represented by the above general formula (1) is preferably a compound represented by the following general formula (II), taking into account the availability of raw materials and other factors, from the viewpoint of achieving the effects of the present invention more efficiently and / or effectively.

[0101] [ka]

[0102] In general formula (II), R 5 R represents a hydrogen atom or a methyl group. 5 If it is a methyl group, it is IPEMA (isoprenyl methacrylate).

[0103] In the wavelength conversion film-forming composition of the present invention, the compound represented by the general formula (1) may be present as one type or as two or more types.

[0104] In the wavelength conversion film-forming composition of the present invention, there are no particular restrictions on the content of the compound represented by the above general formula (1). However, from the viewpoint of more effectively achieving the effects of the present invention, it is preferable that the content be 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, in the solid content. Furthermore, it is preferable that the content be 99.9% by mass or less, more preferably 95% by mass or less, and even more preferably 90% by mass or less, in the solid content.

[0105] (B) The binder may include, in addition to the compound represented by the above general formula (1), a compound having two or more polymerizable functional groups in its molecule and different from the compound represented by the above general formula (1), a compound having one polymerizable functional group in its molecule, a photopolymerization initiator, and a resin. In this case, for convenience, the present application may refer to the photopolymerization initiator as "(B-1) photopolymerization initiator" or simply "(B-1)", the compound represented by the above general formula (1) as "(B-2) compound represented by the above general formula (1)" or simply "(B-2)", a compound having two or more polymerizable functional groups in its molecule and different from the compound represented by the above general formula (1) as "(B-3) compound having two or more polymerizable functional groups in its molecule and different from the compound represented by the above general formula (1)" or simply "(B-3)", a compound having one polymerizable functional group in its molecule as "(B-4) compound having one polymerizable functional group in its molecule" or simply "(B-4)", and the resin as "(B-5) resin (base polymer)" or simply "(B-5)".

[0106] In the wavelength conversion film-forming composition of the present invention, there are no particular restrictions on the content of the compound represented by the above general formula (1). However, from the viewpoint of more effectively achieving the effects of the present invention, it is preferable that the content be 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, based on 100% by mass of the total of components (B-2), (B-3), and (B-4). Furthermore, it is preferable that the content be 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less, based on 100% by mass of the total of components (B-2), (B-3), and (B-4).

[0107] [(B-3) Compounds having two or more polymerizable functional groups in the molecule and different from compounds represented by general formula (1)] Here, (B-3) refers to a compound having two or more polymerizable functional groups in its molecule and being different from the compound represented by the general formula (1) above, meaning a compound having two or more polymerizable functional groups in its molecule (excluding the compound represented by the general formula (1) above). The polymerizable functional group is preferably a radical polymerizable functional group. The radical polymerizable functional group is particularly preferably a radical polymerizable functional group that undergoes polymerization by a radical induced by a photopolymerization initiator. Specifically, examples include radical polymerizable functional groups such as (meth)acryloyl groups and vinyl groups. Among these, (meth)acryloyl groups are preferred. Examples of (B-3) include polyvalent (meth)acrylic acid esters having two or more (meth)acryloyloxy groups in their molecule. The polyvalent (meth)acrylic acid ester may also be a hydroxyl group-containing polyvalent (meth)acrylic acid ester. In the composition of the present invention, (B-3) may consist of only one type or two or more types.

[0108] As polyhydric (meth)acrylic acid esters, (meth)acrylic acid esters of polyhydric alcohols such as diols and triols can be used, more specifically, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexamethylene di(meth)acrylate, neopentyl glycol di(meth)acrylate, Examples include 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, tricyclodecanedimethanol di(meth)acrylate, glycerin di(meth)acrylate, hydrogenated bisphenol A or hydrogenated bisphenol F di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and trimethylolpropane tri(meth)acrylate.

[0109] Examples of hydroxyl group-containing polyhydric (meth)acrylic acid esters include glycerol di(meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol di(meth)acrylate, and dipentaerythritol monohydroxypenta(meth)acrylate.

[0110] Among these, as for (B-3) above, from the viewpoint of more effectively achieving the effects of the present invention, polyvalent (meth)acrylic acid esters are preferred, and 1,6-hexamethylenedi(meth)acrylate, 1,9-nonanediol di(meth)acrylate, pentaerythritol tri(meth)acrylate, and dipentaerythritol hexa(meth)acrylate are more preferred.

[0111] There are no particular restrictions on the content of (B-3) in the composition of the present invention, but from the viewpoint of more effectively achieving the effects of the present invention, it is preferable that the content be 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, based on 100% by mass of the total of components (B-2), (B-3), and (B-4). The upper limit of the content can be appropriately set depending on the use of the composition, but for example, it is preferable that the content be 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less, based on 100% by mass of the total of components (B-2), (B-3), and (B-4).

[0112] [(B-4) Compounds having one polymerizable functional group in the molecule] (B) When (B-1), (B-2), and (B-3) above are combined as a binder, a compound having one polymerizable functional group in its molecule (in this application, also referred to as "(B-4) a compound having one polymerizable functional group in its molecule") may be optionally added.

[0113] (B-4) The polymerizable functional group in a compound having one polymerizable functional group in its molecule is preferably a radical polymerizable functional group. The radical polymerizable functional group is particularly preferably a radical polymerizable functional group that undergoes polymerization reaction by a radical induced by a photopolymerization initiator. Specifically, examples include radical polymerizable functional groups such as (meth)acryloyl groups and vinyl groups. Among these, (meth)acryloyl groups are preferred. An example of the above (B-4) is a (meth)acrylic acid ester having a (meth)acryloyloxy group in its molecule. In the composition of the present invention, the above (B-4) may consist of only one type or two or more types.

[0114] Specific examples of compounds having one polymerizable functional group in the molecule include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, dodecyl (meth)acrylate, hexadecyl (meth)acrylate, octadecyl (meth)acrylate, cyclohexyl (meth)acrylate, methoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, phenoxyethyl (meth)acrylate, nonylphenoxyethyl (meth)acrylate, glycidyl (meth)acrylate, and dimethylaminoethyl (meth)acrylate. Examples include diethylaminoethyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, benzyl (meth)acrylate, phenylbenzyl (meth)acrylate, mono(2-acryloyloxyethyl) succinate, N-[2-(acryloyloxy)ethyl]phthalimide, N-[2-(acryloyloxy)ethyl]tetrahydrophthalimide, etc.

[0115] Among these, ethoxyethoxyethyl (meth)acrylate is more preferred as (B-4) above from the viewpoint of more effectively achieving the effects of the present invention.

[0116] When the composition contains component (B-4), there are no particular restrictions on the amount of (B-4). However, from the viewpoint of more effectively achieving the effects of the present invention, the amount of (B-4) in the composition of the present invention is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, based on 100% by mass of the total of components (B-2), (B-3), and (B-4). The upper limit of this amount can be appropriately set depending on the use of the composition, but for example, it is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less, based on 100% by mass of the total of components (B-2), (B-3), and (B-4).

[0117] There are no particular restrictions on the total content of components (B-2), (B-3), and (B-4) in the composition of the present invention. However, from the viewpoint of more effectively achieving the effects of the present invention, it is preferable that the total content be 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, based on the solid content. The upper limit of the content can be appropriately set depending on the intended use of the composition, but for example, it is preferable that the total content be 99% by mass or less, more preferably 95% by mass or less, and even more preferably 90% by mass or less, based on the solid content.

[0118] [(B-1) Photopolymerization initiator] (B-1) There are no particular restrictions on the photopolymerization initiator as long as it can achieve the objectives of the present invention. In the present invention, it is preferable to use a photoradical polymerization initiator as (B-1) above. It is also suitable as a general method for manufacturing wavelength conversion members. Furthermore, according to the present invention, even if a photoradical polymerization initiator is used as (B-1) above, a cured film with excellent insolubility in the developer can be formed as a wavelength conversion film without oxygen inhibition in the curing process.

[0119] As photoradical polymerization initiators, molecular cleavage type or hydrogen abstraction type photoradical polymerization initiators are preferably used.

[0120] Examples of molecular cleavage-type photoradical polymerization initiators include benzoin isobutyl ether, 2,4-diethylthioxanthone, 2-isopropylthioxanthone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl phenyl(2,4,6-trimethylbenzoyl)phosphinate, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and (2,4,6-trimethylbenzoyl)ethoxyphenylphosphine oxide. Other molecular cleavage-type photoradical polymerization initiators that may be used in combination include, for example, 1-hydroxycyclohexylphenyl ketone, benzoin ethyl ether, benzyldimethyl ketal, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2,2-dimethoxy-2-phenylacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, and 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one.

[0121] Examples of hydrogen abstraction-type photoradical polymerization initiators include benzophenone, 4-phenylbenzophenone, isophthalphenone, and 4-benzoyl-4'-methyl-diphenyl sulfide. A molecular cleavage-type photoradical polymerization initiator and a hydrogen abstraction-type photoradical polymerization initiator may be used in combination.

[0122] Photoradical polymerization initiators are also available commercially. Such commercially available products include acylphosphine oxide compounds such as Omnirad (registered trademark; hereinafter the same) TPO-H, Omnirad TPO-L, and Omnirad 819 from IGM Resin; alkylphenone compounds such as Omnirad 651, Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127, Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG; intramolecular hydrogen abstraction compounds such as Omnirad MBF and Omnirad 754 from BASF Japan; and Irgacure (registered trademark; hereinafter the same) OXE01, Irgacure OXE02, Irgacure OXE03, and Irgacure Examples of oxime ester compounds include OXE04, TR-PBG-304 and TR-PBG-305 from Changzhou Strong Electronic New Materials Co., Ltd., and NCI-730, NCI-831, and NCI-930 from ADEKA Corporation.

[0123] Other examples of oxime ester compounds include those described in Japanese Patent Publication No. 2004-534797, Japanese Patent Application Publication No. 2000-80068, International Publication No. 2012 / 45736, International Publication No. 2015 / 36910, Japanese Patent Application Publication No. 2006-36750, Japanese Patent Application Publication No. 2008-179611, International Publication No. 2009 / 131189, Japanese Patent Publication No. 2012-526185, Japanese Patent Publication No. 2012-519191, International Publication No. 2006 / 18973, International Publication No. 2008 / 78678, and Japanese Patent Application Publication No. 2011-132215.

[0124] When using a photoradical polymerization initiator as described above (B-1), a chain transfer agent may be used in combination. Using a chain transfer agent can increase the reaction rate of the photoradical reaction.

[0125] Chain transfer agents are defined on pages 683-684 of the Polymer Dictionary, Third Edition (edited by the Society of Polymer Science, Japan, 2005). Examples of chain transfer agents include compounds having SH, PH, SiH, and GeH groups in their molecules. These can generate radicals by donating hydrogen to low-activity radical species, or by being oxidized and then deprotonated. Thiol compounds (e.g., 2-mercaptobenzimidazoles, 2-mercaptobenzuthiazoles, 2-mercaptobenzuxazoles, 3-mercaptotriazoles, 5-mercaptotetrazoles, etc.) are particularly preferred, and polyfunctional thiol compounds are especially preferred. As polyfunctional thiols, any compound having two or more thiol (SH) groups is acceptable. Examples of polyfunctional thiol compounds include ethylene glycol bisthiopropionate (EGTP), butanediol bisthiopropionate (BDTP), trimethylolpropane tristhiopropionate (TMTP), pentaerythritol tetrakisthiopropionate (PETP), tetraethylene glycol bis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), pentaerythritol tetrakis(thioglycolate), Karenz (registered trademark, hereinafter the same) MT BD1, Karenz MT PE1, Karenz MT NR1 (all manufactured by Resonac Co., Ltd.), etc.

[0126] There are no particular restrictions on the content of (B-1) above, but from the viewpoint of more effectively achieving the effects of the present invention, it is preferable that it be 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more, in the solid content. Furthermore, from the viewpoint of more effectively achieving the effects of the present invention, the upper limit of its content is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less, in the solid content.

[0127] [(B-5) Resin (Base Polymer)] (B) When (B-1), (B-2), and (B-3) above are blended as a binder, a base polymer (also referred to in this application as "(B-5) resin") may be further blended. In the wavelength conversion film-forming composition of the present invention, it is preferable to blend an alkali-soluble resin as the (B-5) resin. By further blending an alkali-soluble resin, it can also be used as a composition for forming a resist film.

[0128] The alkali-soluble resins mentioned above are resins that have alkali-soluble groups. Specific examples of alkali-soluble groups include phenolic hydroxyl groups, carboxyl groups, acid anhydride groups, imide groups, sulfonyl groups, phosphoric acid, boronic acid groups, and activated methylene groups.

[0129] An active methylene group is a methylene group (-CH2-) that has a carbonyl group adjacent to it and exhibits reactivity with nucleophiles.

[0130] As the active methylene group, the group represented by the following formula (b1) is more preferred.

[0131] [ka] (In the formula, R b (The symbols represent alkyl groups, alkoxy groups, or phenyl groups, and the dashed lines represent bonding bonds.)

[0132] In the above equation (b1), R b Examples of alkyl groups represented by include alkyl groups having 1 to 20 carbon atoms, with alkyl groups having 1 to 5 carbon atoms being preferred. Specific examples of such alkyl groups include methyl, ethyl, n-propyl, and i-propyl groups. Among these, methyl, ethyl, and n-propyl groups are preferred.

[0133] In the above equation (b1), R bExamples of alkoxy groups represented by include alkoxy groups having 1 to 20 carbon atoms, with alkoxy groups having 1 to 5 carbon atoms being preferred. Specific examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, and t-butoxy groups. Among these, methoxy, ethoxy, and n-propoxy groups are preferred.

[0134] Specific examples of the group represented by formula (b1) above include, but are not limited to, the groups represented by formulas (b1-1) to (b1-5) below. In the structural formulas, dashed lines represent bonds.

[0135] [ka]

[0136] Among the alkali-soluble groups mentioned above, it is preferable that the alkali-soluble resin has at least one organic group selected from the group consisting of phenolic hydroxyl groups and carboxyl groups, and has a number-average molecular weight of 2,000 to 50,000.

[0137] As described above, the alkali-soluble resin is preferably one with a number-average molecular weight in the range of 2,000 to 50,000. However, if the number-average molecular weight is 50,000 or less, development residue is less likely to occur, and the required sensitivity can be obtained. On the other hand, if the number-average molecular weight is 2,000 or more, film thinning in the exposed area is less likely to occur during development, and sufficient curability can be obtained.

[0138] The alkali-soluble resin described above only needs to have the above structure, and is not particularly limited in terms of the backbone of the main chain and the type of side chains of the polymer constituting the resin.

[0139] Examples of the alkali-soluble resins mentioned above include acrylic resins, polyhydroxystyrene resins, polyimide precursors, polyimides, or polyesters.

[0140] Furthermore, in the present invention, an alkali-soluble resin consisting of a copolymer obtained by polymerizing multiple types of monomers can also be used. Moreover, the alkali-soluble resin may be a blend of multiple types of alkali-soluble resins.

[0141] As the alkali-soluble resin mentioned above, an acrylic polymer, which is an acrylic resin, can be used. In the present invention, an acrylic polymer refers to a resin obtained by the polymerization reaction of monomers having unsaturated double bond groups, in which the unsaturated double bond group portion reacts. Examples of alkali-soluble acrylic polymers include copolymers formed using monomers that exhibit alkali solubility, i.e., monomers having at least one selected from the aforementioned alkali-soluble groups, and at least one monomer selected from the group of monomers copolymerizable with these monomers, as essential structural units. The number-average molecular weight of the above alkali-soluble resin is preferably 2,000 to 50,000. If the number-average molecular weight is 50,000 or less, residue is less likely to be generated.

[0142] The above-mentioned "monomers having at least one selected from alkali-soluble groups" include monomers having a carboxyl group, a phenolic hydroxyl group, and an imide group. These monomers are not limited to having one carboxyl group or phenolic hydroxyl group, but may also have multiple groups.

[0143] The following are specific examples of the above monomers, but are not limited to these. Examples of monomers having a carboxyl group include acrylic acid, methacrylic acid, crotonic acid, mono-(2-(acryloyloxy)ethyl) phthalate, mono-(2-(methacryloyloxy)ethyl) phthalate, N-(carboxyphenyl)maleimide, N-(carboxyphenyl)methacrylamide, and N-(carboxyphenyl)acrylamide.

[0144] Examples of monomers having a phenolic hydroxyl group include hydroxystyrene, N-(hydroxyphenyl)acrylamide, N-(hydroxyphenyl)methacrylamide, N-(hydroxyphenyl)maleimide, and 4-hydroxyphenyl methacrylate.

[0145] Examples of monomers having an imide group include maleimide.

[0146] In the production of the alkali-soluble acrylic polymer described above, the ratio of alkali-soluble groups to monomers having unsaturated double bond groups is preferably 5 to 90 mol%, more preferably 10 to 60 mol%, and most preferably 10 to 40 mol% of all monomers used in the production of the alkali-soluble acrylic polymer. Sufficient alkali solubility can be obtained when the ratio of alkali-soluble groups to monomers having unsaturated double bond groups is 10 mol% or more.

[0147] The above alkali-soluble acrylic polymer may be further copolymerized with a monomer having a hydroxyalkyl group and an unsaturated double bond group in order to further stabilize the pattern shape after curing.

[0148] Specific examples of monomers having a hydroxyalkyl group and an unsaturated double bond group include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 2,3-dihydroxypropyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, 2,3-dihydroxypropyl methacrylate, glycerin monomethacrylate, and 5-acryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone.

[0149] In the production of the above alkali-soluble acrylic polymer, the ratio of monomers having a hydroxyalkyl group and an unsaturated double bond group is preferably 10 to 60% by mass, more preferably 15 to 50% by mass, and even more preferably 20 to 40% by mass. When the ratio of monomers having a hydroxyalkyl group and an unsaturated double bond group is 10% by mass or more, a stabilizing effect on the pattern shape of the copolymer is obtained. When the ratio is 60% by mass or less, the content of alkali-soluble groups is within an appropriate range, and sufficient developability and other properties are obtained.

[0150] The above alkali-soluble acrylic polymer may be further copolymerized with an N-substituted maleimide compound to increase the Tg of the copolymer.

[0151] Specific examples of N-substituted maleimide compounds include N-methylmaleimide, N-ethylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide. From the viewpoint of transparency, compounds without aromatic rings are preferred, and from the viewpoint of developability, transparency, and heat resistance, compounds having an alicyclic skeleton are more preferred, with cyclohexylmaleimide being even more preferred.

[0152] In the production of the above alkali-soluble acrylic polymer, the ratio of N-substituted maleimide is preferably 10 to 60% by mass, more preferably 15 to 50% by mass, and even more preferably 20 to 40% by mass. When the ratio of N-substituted maleimide is 10% by mass or more, the Tg of the copolymer increases, and therefore the Tg of the wavelength conversion film obtained in the end also increases, resulting in sufficient heat resistance and light resistance. When the ratio is 60% by mass or less, sufficient transparency is obtained.

[0153] Furthermore, in the present invention, the alkali-soluble acrylic polymer may be a copolymer containing monomers other than those described above (hereinafter referred to as "other monomers") as constituent units. Specifically, the other monomers are not particularly limited as long as they are copolymerizable with at least one selected from the group consisting of monomers having a carboxyl group and monomers having a phenolic hydroxyl group, as long as the properties of the alkali-soluble acrylic polymer are not impaired. Specific examples of such monomers include acrylic acid ester compounds, methacrylic acid ester compounds, acrylamide compounds, acrylonitrile, styrene compounds, and vinyl compounds. The following are some specific examples of such other monomers, but are not limited to these.

[0154] Specific examples of the above acrylic acid ester compounds include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthyl acrylate, anthyl methyl acrylate, phenyl acrylate, glycidyl acrylate, phenoxyethyl acrylate, 2,2,2-trifluoroethyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, and methoxytriethylene glycol acrylate. Examples include rilate, 2-ethoxyethyl acrylate, 2-aminoethyl acrylate, tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, 2-methyl-2-adamantyl acrylate, 2-propyl-2-adamantyl acrylate, 8-methyl-8-tricyclodecyl acrylate, 8-ethyl-8-tricyclodecyl acrylate, diethylene glycol monoacrylate, caprolactone 2-(acryloyloxy)ethyl ester, and poly(ethylene glycol) ethyl ether acrylate.

[0155] Specific examples of the above methacrylate ester compounds include methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthlyl methacrylate, anthlyl methyl methacrylate, phenyl methacrylate, glycidyl methacrylate, phenoxyethyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, 2-methoxyethyl methacrylate, methoxytriethylene glycol methacrylate, Examples include 2-ethoxyethyl methacrylate, 2-aminomethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate, 2-methyl-2-adamantyl methacrylate, γ-butyrolactone methacrylate, 2-propyl-2-adamantyl methacrylate, 8-methyl-8-tricyclodecyl methacrylate, 8-ethyl-8-tricyclodecyl methacrylate, diethylene glycol monomethacrylate, caprolactone 2-(methacryloyloxy)ethyl ester, and poly(ethylene glycol) ethyl ether methacrylate.

[0156] Specific examples of the above acrylamide compounds include N-methylacrylamide, N-methylmethacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-methoxymethylacrylamide, N-methoxymethylmethacrylamide, N-butoxymethylacrylamide, and N-butoxymethylmethacrylamide.

[0157] Specific examples of the vinyl compounds mentioned above include, for example, methyl vinyl ether, benzyl vinyl ether, cyclohexyl vinyl ether, vinyl naphthalene, vinyl anthracene, vinyl carbazole, allyl glycidyl ether, 3-ethenyl-7-oxabicyclo[4.1.0]heptane, 1,2-epoxy-5-hexene, and 1,7-octadiene monoepoxide.

[0158] Examples of the styrene compounds mentioned above include styrene without a hydroxyl group. Specific examples include styrene, α-methylstyrene, chlorostyrene, and bromostyrene.

[0159] In the production of the alkali-soluble acrylic polymer described above, the ratio of the other monomers is preferably 80% by mass or less, more preferably 50% by mass or less, and even more preferably 20% by mass or less. When the ratio of the other monomers is 80% by mass or less, the effects of the present invention can be fully obtained.

[0160] The method for obtaining the above-mentioned alkali-soluble acrylic polymer is not particularly limited, but for example, it can be obtained by polymerizing it at a temperature of 50 to 110°C in a solvent containing: a monomer having at least one selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a group that generates a carboxylic acid by the action of heat or acid, and a group that generates a phenolic hydroxyl group by the action of heat or acid; a monomer having a hydroxyalkyl group; optionally, a monomer having at least one group selected from crosslinkable groups such as N-alkoxymethyl group, N-hydroxymethyl group, alkoxysilyl group, epoxy group, oxetane group, vinyl group, and blocked isocyanate group, and self-crosslinkable groups such as N-alkoxymethyl group, N-hydroxymethyl group, alkoxysilyl group, epoxy group, vinyl group, and blocked isocyanate group; optionally, other copolymerizable monomers; and optionally, a polymerization initiator. The solvent used is not particularly limited as long as it dissolves the monomers constituting the alkali-soluble acrylic polymer and the alkali-soluble acrylic polymer. Specific examples include the following solvents.

[0161] Examples of solvents used in the above reaction include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-butanone, and 3-methyl-2-pentanone. Examples include 2-pentanone, 2-heptanone, γ-butyrolactone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone. Among these, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 2-heptanone, propylene glycol propyl ether, propylene glycol propyl ether acetate, ethyl lactate, and butyl lactate are preferred from the viewpoint of good film-forming properties and high safety. These may be used individually or in combination of two or more.

[0162] The alkali-soluble acrylic polymer obtained in this way is usually in the form of a solution dissolved in a solvent.

[0163] Furthermore, the solution of the specific copolymer obtained as described above can be added to a stirring solution such as diethyl ether or water to reprecipitate it. After filtering and washing the resulting precipitate, the specific copolymer can be dried at room temperature or under atmospheric pressure or reduced pressure to obtain a powder. This operation removes polymerization initiators and unreacted monomers coexisting with the specific copolymer, resulting in a purified powder of the specific copolymer. If sufficient purification is not achieved in a single operation, the obtained powder can be redissolved in a solvent and the above operation can be repeated. In the present invention, the powder of the specified copolymer may be used as is, or the powder may be redissolved in a suitable solvent, for example, the solvent used in the polymerization reaction described above, and used in solution form.

[0164] Furthermore, as the alkali-soluble resin mentioned above, polyimides such as polyamic acid, polyamic acid esters, polyimide precursors such as partially imidized polyamic acid, and carboxylic acid group-containing polyimides can also be used, and as long as they are alkali-soluble, their type is not particularly limited.

[0165] The polyamic acid described above, which is a polyimide precursor, can generally be obtained by polycondensation of (a) a tetracarboxylic dianhydride and (b) a diamine compound.

[0166] The above (a) tetracarboxylic dianhydride is not particularly limited, and specific examples include aromatic tetracarboxylic acids such as pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 3,3',4,4'-diphenylethertetracarboxylic dianhydride, and 3,3',4,4'-diphenylsulfonetetracarboxylic dianhydride, as well as 1,2,3,4-cyclobutanetetracarboxylic dianhydride and 1,2-dimethyl-1,2,3,4-cyclo Examples include alicyclic tetracarboxylic dianhydrides such as butanetetracarboxylic dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,3,4-cyclohexanetetracarboxylic dianhydride, and 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalenesuccinic acid dianhydride, as well as aliphatic tetracarboxylic dianhydrides such as 1,2,3,4-butanetetracarboxylic dianhydride. These may be used individually or in combination of two or more.

[0167] Furthermore, the above (b) diamine compounds are not particularly limited, and specific examples include 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, 3,5-diaminobenzoic acid, 4,6-diamino-1,3-benzenedicarboxylic acid, 2,5-diamino-1,4-benzenedicarboxylic acid, bis(4-amino-3-carboxyphenyl) ether, bis(4-amino-3,5-dicarboxyphenyl) ether, bis(4-amino-3-carboxyphenyl) sulfone, bis(4-amino-3,5-dicarboxyphenyl) sulfone, and 4,4'-diamino-3,3'-dicarboxybif phenyl, 4,4'-diamino-3,3'-dicarboxy-5,5'-dimethylbiphenyl, 4,4'-diamino-3,3'-dicarboxy-5,5'-dimethoxybiphenyl, 1,4-bis(4-amino-3-carboxyphenoxy)benzene, 1,3-bis(4-amino-3-carboxyphenoxy)benzene, bis[4-(4-amino-3-carboxyphenoxy)phenyl]sulfone, bis[4-(4-amino-3-carboxyphenoxy)phenyl]propane, 2,2-bis[4-(4-amino-3-carboxyphenoxy)phenyl]hexafluoropropane; 2,4-diaminophenol, 3,5-diaminophenol, 2,5-diaminophenol, 4,6-diaminoresorcinol, 2,5-diaminohydroquinone, bis(3-amino-4-hydroxyphenyl) ether, bis(4-amino-3-hydroxyphenyl) ether, bis(4-amino-3,5-dihydroxyphenyl) ether, bis(3-amino-4-hydroxyphenyl)methane, bis(4-amino-3-hydroxyphenyl)methane, bis(4-amino-3,5-dihydroxyphenyl)methane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(4-amino-3-hydroxyphenyl)sulfone, bis(4-amino-3,5-dihydroxyphenyl)sulfone, 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, 2,2-bis(4-amino-3-hydroxyphenyl)hexafluoropropane, 2,2-bis(4- Diamine compounds having phenolic hydroxyl groups, such as amino-3,5-dihydroxyphenyl)hexafluoropropane, 4,4'-diamino-3,3'-dihydroxybiphenyl, 4,4'-diamino-3,3'-dihydroxy-5,5'-dimethylbiphenyl, 4,4'-diamino-3,3'-dihydroxy-5,5'-dimethoxybiphenyl, 1,4-bis(3-amino-4-hydroxyphenoxy)benzene, 1,3-bis(3-amino-4-hydroxyphenoxy)benzene, 1,4-bis(4-amino-3-hydroxyphenoxy)benzene, 1,3-bis(4-amino-3-hydroxyphenoxy)benzene, bis[4-(3-amino-4-hydroxyphenoxy)phenyl]sulfone, bis[4-(3-amino-4-hydroxyphenoxy)phenyl]propane, and 2,2-bis[4-(3-amino-4-hydroxyphenoxy)phenyl]hexafluoropropane; Examples include diamine compounds having a thiophenol group, such as 1,3-diamino-4-mercaptobenzene, 1,3-diamino-5-mercaptobenzene, 1,4-diamino-2-mercaptobenzene, bis(4-amino-3-mercaptophenyl) ether, and 2,2-bis(3-amino-4-mercaptophenyl)hexafluoropropane; and diamine compounds having a sulfonic acid group, such as 1,3-diaminobenzene-4-sulfonic acid, 1,3-diaminobenzene-5-sulfonic acid, 1,4-diaminobenzene-2-sulfonic acid, bis(4-aminobenzene-3-sulfonic acid) ether, 4,4'-diaminobiphenyl-3,3'-disulfonic acid, and 4,4'-diamino-3,3'-dimethylbiphenyl-6,6'-disulfonic acid. Also, p-phenylenediamine, m-phenylenediamine, 4,4'-methylene-bis(2,6-ethylaniline), 4,4'-methylene-bis(2-isopropyl-6-methylaniline), 4,4'-methylene-bis(2,6-diisopropylaniline), 2,4,6-trimethyl-1,3-phenylenediamine, 2,3,5,6-tetramethyl-1,4-phenylenediamine, o-tolidine, m-tolidine, 3,3',5,5'-tetramethylbenzidine, bis[4-(3-aminophenoxy)phenyl]sulfone, 2,2-bis[4-(3-aminophenoxy)phenyl]propane, 2,2-bis[4-(3-aminophenoxy)phenyl]hexafluoropropane, 4,4'-diamino-3,3'-dimethyldicyclohexyl Examples of diamine compounds include rumethane, 4,4'-diaminodiphenyl ether, 3,4-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 2,2-bis(4-anilino)hexafluoropropane, 2,2-bis(3-anilino)hexafluoropropane, 2,2-bis(3-amino-4-toluyl)hexafluoropropane, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, bis[4-(4-aminophenoxy)phenyl]sulfone, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, and 2,2'-bis(trifluoromethyl)benzidine.These may be used individually or in combination of two or more types.

[0168] When the above polyamic acid is produced from (a) a tetracarboxylic dianhydride and (b) a diamine compound, the ratio of the two compounds, i.e., the total number of moles of the diamine compound (b) / the total number of moles of the tetracarboxylic dianhydride (a), is preferably 0.7 to 1.2. As with typical polycondensation reactions, the closer this molar ratio is to 1, the higher the degree of polymerization of the resulting polyamic acid and the greater the molecular weight.

[0169] Furthermore, when polymerizing using an excess of a diamine compound, the terminal amino groups of the remaining polyamic acid can be protected by reacting them with a carboxylic acid anhydride. Examples of such carboxylic acid anhydrides include phthalic anhydride, trimellitic anhydride, maleic anhydride, naphthalic anhydride, hydrogenated phthalic anhydride, methyl-5-norbornene-2,3-dicarboxylic acid anhydride, itaconic anhydride, and tetrahydrophthalic anhydride.

[0170] In the production of polyamic acid, the reaction temperature for the reaction between the diamine compound and the tetracarboxylic dianhydride can be selected from any temperature, usually between -20 and 150°C, preferably between -5 and 100°C. To obtain high molecular weight polyamic acid, the reaction temperature can be appropriately selected from 5 to 40°C and the reaction time from 1 to 48 hours. To obtain a low molecular weight polyamic acid with high storage stability and partial imidization, it is more preferable to select a reaction temperature of 40 to 90°C and a reaction time of 10 hours or more. Furthermore, when protecting the terminal amino group with an acid anhydride, the reaction temperature can be selected from any temperature between -20 and 150°C, preferably between -5 and 100°C.

[0171] The reaction between diamine compounds and tetracarboxylic dianhydrides can be carried out in a solvent. Suitable solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-vinylpyrrolidone, N-methylcaprolactam, dimethyl sulfoxide, tetramethylurea, pyridine, dimethyl sulfone, hexamethyl sulfoxide, m-cresol, γ-butyrolactone, ethyl acetate, butyl acetate, ethyl lactate, methyl 3-methoxypropionate, methyl 2-methoxypropionate, ethyl 3-methoxypropionate, ethyl 2-methoxypropionate, ethyl 3-ethoxypropionate, ethyl 2-ethoxypropionate, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether. Examples include diethylene glycol methyl ethyl ether, propylene glycol dimethyl ether, dipropylene glycol dimethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, carbitol acetate, ethyl cellosolve acetate, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, 2-heptanone, etc. These may be used individually or in combination of two or more. Furthermore, even solvents that do not dissolve polyamic acid may be mixed with the above solvents as long as the polyamic acid produced by the polymerization reaction does not precipitate.

[0172] The solution containing the polyamic acid obtained in this manner can be used directly in the preparation of a negative-type photosensitive resin composition. Alternatively, the polyamic acid can be precipitated and isolated in a poor solvent such as water, methanol, or ethanol, and then recovered for use.

[0173] Furthermore, any polyimide can be used as the alkali-soluble resin. The polyimide used in this invention is obtained by chemically or thermally imidizing a polyimide precursor such as the polyamic acid mentioned above by 50% or more.

[0174] The above polyimide preferably has a group selected from a carboxyl group and a phenolic hydroxyl group in order to provide alkali solubility. Methods for introducing carboxyl groups or phenolic hydroxyl groups into polyimides include using monomers having carboxyl groups or phenolic hydroxyl groups, sealing the amine ends with acid anhydrides having carboxyl groups or phenolic hydroxyl groups, and reducing the imidation rate to 99% or less when imidizing polyimide precursors such as polyamic acids.

[0175] Such polyimides can be obtained by synthesizing polyimide precursors such as the polyamic acid mentioned above, followed by chemical or thermal imidation. Generally, chemical imidation involves adding excess acetic anhydride and pyridine to a polyimide precursor solution and reacting it at room temperature to 100°C. Alternatively, thermal imidation generally involves heating the polyimide precursor solution at 180-250°C while simultaneously dehydrating it.

[0176] Furthermore, phenol novolac resin can be used as the alkali-soluble resin.

[0177] Furthermore, polyester polycarboxylic acid can also be used as the alkali-soluble resin. Polyester polycarboxylic acid can be obtained from an acidic dianhydride and a diol by the method described in International Publication No. 2009 / 051186. Examples of acidic dianhydrides include the tetracarboxylic dianhydride (a) mentioned above. Examples of diols include aromatic diols such as bisphenol A, bisphenol F, 4,4'-dihydroxybiphenyl, benzene-1,3-dimethanol, and benzene-1,4-dimethanol; alicyclic diols such as hydrogenated bisphenol A, hydrogenated bisphenol F, 1,4-cyclohexanediol, 1,3-cyclohexanedimethanol, and 1,4-cyclohexanedimethanol; and aliphatic diols such as ethylene glycol, propylene glycol, 1,4-butanediol, and 1,6-hexanediol.

[0178] In the present invention, the alkali-soluble resin may be a copolymer that further has a self-crosslinking group, or a group that reacts with at least one group selected from the group consisting of a hydroxyl group, a carboxyl group, an amide group, and an amino group (hereinafter also referred to as a crosslinking group).

[0179] Specific examples of the self-crosslinking groups mentioned above include N-alkoxymethyl groups, N-hydroxymethyl groups, alkoxysilyl groups, epoxy groups, oxetanyl groups, vinyl groups, and blocked isocyanate groups.

[0180] Specific examples of the above-mentioned crosslinkable groups include N-alkoxymethyl groups, N-hydroxymethyl groups, alkoxysilyl groups, epoxy groups, oxetanyl groups, vinyl groups, and blocked isocyanate groups.

[0181] When such self-crosslinking groups or crosslinking groups are included in an alkali-soluble resin, the content is preferably 0.1 to 0.9 groups per repeating unit in the alkali-soluble resin, and more preferably 0.1 to 0.8 groups from the viewpoint of developability and solvent resistance.

[0182] If the alkali-soluble resin further has repeating units having at least one selected from the above-mentioned crosslinkable group and self-crosslinkable group, for example, in the case of an alkali-soluble acrylic polymer, it is possible to copolymerize it with an unsaturated compound that has radical polymerizability and further has at least one selected from the above-mentioned crosslinkable group and self-crosslinkable group.

[0183] Specific examples of the unsaturated compound having radical polymerizability and further having an N-alkoxymethyl group include N-butoxymethylacrylamide, N-isobutoxymethylacrylamide, N-methoxymethylacrylamide, N-methoxymethylmethacrylamide, N-methylolacrylamide and the like.

[0184] Specific examples of the monomer having radical polymerizability and further having a hydroxymethylamide group include N-hydroxymethylacrylamide, N-hydroxymethylmethacrylamide and the like.

[0185] Specific examples of the monomer having radical polymerizability and further having an alkoxysilyl group include 3-acryloyloxytrimethoxysilane, 3-acryloyloxytriethoxysilane, 3-methacryloyloxytrimethoxysilane, 3-methacryloyloxytriethoxysilane and the like.

[0186] Specific examples of the unsaturated compound having radical polymerizability and further having an epoxy group include glycidyl acrylate, glycidyl methacrylate, glycidyl α-ethylacrylate, glycidyl α-n-propylacrylate, glycidyl α-n-butylacrylate, 3,4-epoxybutyl acrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7-epoxyheptyl methacrylate, 6,7-epoxyheptyl α-ethylacrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether and the like. Among these, glycidyl methacrylate, 6,7-epoxyheptyl methacrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, and 3,4-epoxycyclohexyl methacrylate are preferred. These may be used singly or in combination of two or more kinds.

[0187] Examples of unsaturated compounds that have radical polymerizability and also contain an oxetanyl group include (meth)acrylic acid esters containing an oxetanyl group. Specific examples of such monomers include 3-(methacryloyloxymethyl)oxetane, 3-(acryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyl-oxetane, 3-(acryloyloxymethyl)-3-ethyl-oxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(acryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl)-2-phenyl-oxetane, 3-(acryloyloxymethyl)-2-phenyl-oxetane, 2-(methacryloyloxymethyl)oxetane, 2-(acryloyloxymethyl)oxetane, 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane, and 2-(acryloyloxymethyl)-4-trifluoromethyloxetane. Among these, 3-(methacryloyloxymethyl)-3-ethyl-oxetane and 3-(acryloyloxymethyl)-3-ethyl-oxetane are preferred.

[0188] Specific examples of monomers that have radical polymerization properties and also contain a vinyl group include 2-(2-vinyloxyethoxy)ethyl acrylate and 2-(2-vinyloxyethoxy)ethyl methacrylate.

[0189] Specific examples of monomers that have radical polymerizability and also have a blocked isocyanate group include 2-(0-(1'-methylpropyleneneamino)carboxyamino)ethyl methacrylate and 2-(3,5-dimethylpyrazolyl)carbonylamino)ethyl methacrylate.

[0190] In the alkali-soluble resin of the present invention, the content of a constituent unit derived from an unsaturated compound having radical polymerizability and at least one group selected from the above-mentioned crosslinkable group and self-crosslinkable group is preferably 10 to 70% by mass, more preferably 20 to 60% by mass, of all repeating units of the alkali-soluble resin. When the content of this constituent unit is 10% by mass or more, the heat resistance and surface hardness of the cured film are improved. On the other hand, when the content of this constituent unit is 70% by mass or less, the storage stability of the radiation-sensitive resin composition is improved.

[0191] When the alkali-soluble resin of the present invention is used in combination with a binder (B) containing the above-mentioned (B-1), (B-2), and (B-3), it is preferable that the alkali-soluble resin has substituents that can react with (B-2) and (B-3). Examples of substituents that can react with (B-2) and (B-3) include radical polymerizable groups such as ethylenically unsaturated groups. Here, a radical polymerizable group refers to a group in which the polymerization reaction is initiated in the presence of a radical and the reaction proceeds in a chain reaction.

[0192] The method for obtaining an alkali-soluble resin having substituents that can react with (B-2) and (B-3) above is not particularly limited as long as it yields a resin with stable properties. Examples include copolymerizing monomers having substituents that can react with (B-2) and (B-3) above, and synthesizing an alkali-soluble resin without substituents that can react with (B-2) and (B-3) above, and then adding a compound having substituents that can react with (B-2) and (B-3) above by thermal reaction. When the alkali-soluble resin is an alkali-soluble acrylic polymer and an ethylenically unsaturated group is incorporated, the former method may cause the substituents that can react with (B-2) and (B-3) above to react during the polymerization process, potentially leading to gelation. Therefore, synthesis by the latter method is preferred.

[0193] As a method for incorporating ethylenically unsaturated groups into alkali-soluble resins, for example, one method involves adding glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, etc., to an alkali-soluble acrylic polymer synthesized using a monomer that has radical polymerizability and further has a carboxyl group or a phenolic hydroxyl group. In this case, by reducing the molar ratio of the monomer added to the carboxyl group or phenolic hydroxyl group in the resin, substituents that can react with (B-2) and (B-3) above can be introduced while maintaining the alkali solubility of the resin derived from the carboxyl group or phenolic hydroxyl group. Another example is a method of adding monomers having substituents that can react with (B-2) and (B-3) above, which can react with thermally reactive groups in the resin, to an alkali-soluble acrylic polymer obtained by copolymerizing monomers that have radical polymerizability and also have thermally reactive groups. Specifically, this involves adding (meth)acrylic acid, (meth)acrylic acid 2-carboxyethyl, etc., to an alkali-soluble acrylic polymer obtained by copolymerizing glycidyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, etc.

[0194] In the alkali-soluble resin of the present invention, the proportion of repeating units having substituents that can react with (B-2) and (B-3) is preferably 5 to 60% by mass, more preferably 10 to 50% by mass, and even more preferably 10 to 40% by mass, of all repeating units in the alkali-soluble resin. When the content of these constituent units is 5% by mass or more, the heat resistance and chemical resistance of the cured film are improved. On the other hand, when the content of these constituent units is 60% by mass or less, the pattern-forming properties of the radiation-sensitive resin composition are improved.

[0195] Furthermore, in the present invention, the alkali-soluble resin may be a mixture of multiple types of alkali-soluble resins.

[0196] When using the alkali-soluble resin described above, there are no particular restrictions on its content, but from the viewpoint of film-forming properties, it is preferable that the content be 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, based on 100% by mass of the total of (B-2) and (B-3) and the alkali-soluble resin. Furthermore, from the viewpoint of pattern-forming properties, the upper limit of its content is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less.

[0197] (B) There are no particular restrictions on the binder content, but it is preferably 70 to 99.9% by mass, more preferably 85 to 99.7% by mass, and even more preferably 90 to 99% by mass, based on the solid content.

[0198] [(C) Light scattering particles] The wavelength conversion film forming composition of the present invention may further contain (C) light scattering particles. The light scattering particles have the function of scattering light that enters the wavelength conversion film within the film, thereby substantially extending the optical path length in the wavelength conversion film and improving the light absorption rate, and further scattering the light that is reflected at the interface of the wavelength conversion film and returns into the wavelength conversion film, thereby improving the luminescence efficiency.

[0199] The above-mentioned light scattering particles can be appropriately selected depending on the purpose, and may be organic or inorganic fine particles. Of these, inorganic fine particles with a high refractive index are preferred in order to enhance the scattering performance of the particles.

[0200] The above-mentioned light scattering particles can be appropriately selected depending on the purpose, and may be organic or inorganic fine particles. Of these, inorganic fine particles with a high refractive index are preferred in order to enhance the scattering performance of the particles.

[0201] Examples of the above-mentioned organic fine particles include polymethyl methacrylate beads, acrylic-styrene copolymer beads, melamine beads, polycarbonate beads, styrene beads, cross-linked polystyrene beads, polyvinyl chloride beads, and benzoguanamine-melamineformaldehyde beads.

[0202] Examples of the above inorganic fine particles include inorganic oxide particles consisting of at least one oxide selected from silicon, zirconium, titanium, indium, zinc, antimony, cerium, niobium, tungsten, and the like. Specifically, examples of the above inorganic oxide particles include SiO2, ZrO2, TiO2 (sometimes referred to as titanium oxide particles in this application), BaTiO3, In2O3, ZnO, Sb2O3, ITO, CeO2, Nb2O5, and WO3. Of these, TiO2, BaTiO3, ZrO2, CeO2, and Nb2O5 are preferred, and TiO2 is more preferred. Furthermore, among TiO2, the rutile type is preferred over the anatase type because it has lower catalytic activity, resulting in higher film durability, and also has a higher refractive index.

[0203] These particles may also be surface-treated. When surface treatment is performed, specific materials for surface treatment include heterogeneous inorganic oxides such as silicon dioxide and zirconium oxide, metal hydroxides such as aluminum hydroxide, organosiloxanes, and organic acids such as stearic acid. These surface treatment materials may be used individually or in combination of multiple types.

[0204] The average particle diameter of the light-scattering particles is greater than 50 nm and less than 300 nm. From the viewpoint of wavelength conversion efficiency, the lower limit of the average particle diameter is preferably 60 nm or more, and more preferably 70 nm or more. In addition to the viewpoint of wavelength conversion efficiency, considering the patterning characteristics, an average particle diameter greater than 100 nm is more preferable from the viewpoint of low total light reflectance in the i-line (365 nm). The upper limit of the average particle diameter is preferably 290 nm or less, and more preferably 200 nm or less, from the viewpoint of storage stability of the composition, as particles that are too large tend to settle. The average particle diameter of the light-scattering particles is the average particle diameter obtained from transmission electron microscope observation.

[0205] As the light-scattering particles, commercially available products may be used. For example, specific examples of titanium oxide particles include PT-401M (rutile type, average particle diameter 70 nm), PT-401L (rutile type, average particle diameter 130 nm), and PT-501R (rutile type, average particle diameter 180 nm) manufactured by Ishihara Sangyo Co., Ltd., but are not limited thereto. The average particle diameter of the exemplified light-scattering particles may have a variation of ±10 nm.

[0206] The content of the (C) light-scattering particles is preferably 0.1 to 20% by mass, more preferably 0.2 to 15% by mass, and even more preferably 0.3 to 10% by mass in the solid content, in consideration of wavelength conversion efficiency.

[0207] [(D) Thermal Crosslinking Agent] The composition for forming a wavelength conversion film of the present invention may further contain (D) a thermal crosslinking agent. The (D) thermal crosslinking agent refers to a material that causes a curing reaction under heat. Examples thereof include compounds having a structure capable of forming a crosslinked structure through a thermal reaction with a thermally reactive site (for example, a carboxyl group and / or a phenolic hydroxy group) that may be present in the alkali-soluble resin. The thermal crosslinking agent is not particularly limited as long as the object of the present invention can be achieved. Examples of the (D) thermal crosslinking agent include crosslinkable compounds (D1) having two or more substituents selected from an alkoxymethyl group and a hydroxymethyl group, and crosslinkable compounds (D2) represented by formula (4) described later. These crosslinking agents may be used alone or in combination of two or more types.

[0208] (D1) Crosslinkable Compound Having Two or More Substituents Selected from Alkoxymethyl Group and Hydroxymethyl Group The crosslinkable compound of component (D1) having two or more substituents selected from an alkoxymethyl group and a hydroxymethyl group is a compound that undergoes a crosslinking reaction via a dehydration condensation reaction when exposed to high temperatures during thermal curing. Examples of such a compound include compounds such as alkoxymethylated glycoluril, alkoxymethylated benzoguanamine, and alkoxymethylated melamine, as well as phenoplast-based compounds.

[0209] Specific examples of alkoxymethylated glycoluryls include, for example, 1,3,4,6-tetrakis(methoxymethyl) glycoluryl, 1,3,4,6-tetrakis(butoxymethyl) glycoluryl, 1,3,4,6-tetrakis(hydroxymethyl) glycoluryl, 1,3-bis(hydroxymethyl)urea, 1,1,3,3-tetrakis(butoxymethyl)urea, 1,1,3,3-tetrakis(methoxymethyl)urea, 1,3-bis(hydroxymethyl)-4,5-dihydroxy-2-imidazolinone, and 1,3-bis(methoxymethyl)-4,5-dimethoxy-2-imidazolinone. Examples of commercially available products include glycoluryl compounds (product names: Cymel® 1170, Powderlink® 1174) manufactured by Mitsui Cytec Co., Ltd. (now Ornex Co.), methylated urea resin (product name: UFR® 65), butylated urea resin (product names: UFR® 300, U-VAN10S60, U-VAN10R, U-VAN11HV); and urea / formaldehyde resins (high condensation type, product names: Beccamine® J-300S, P-955, N) manufactured by DIC Corporation.

[0210] Specific examples of alkoxymethylated benzoguanamine include tetramethoxymethylbenzoguanamine. Commercially available products include those manufactured by Mitsui Cytec Co., Ltd. (now Ornex Co., Ltd.) (product name: Cymel® 1123) and Sanwa Chemical Co., Ltd. (product names: Nikalac® BX-4000, BX-37, BL-60, BX-55H).

[0211] Specific examples of alkoxymethylated melamines include, for example, hexamethoxymethyl melamine. Commercially available products include methoxymethyl type melamine compounds (product names: Cymel® 300, 301, 303, 350) and butoxymethyl type melamine compounds (product names: Mycoat® 506, 508) manufactured by Mitsui Cytec Co., Ltd. (now Ornex Co., Ltd.), methoxymethyl type melamine compounds (product names: Nikalac® MW-30, MW-22, MW-11, MW-100LM, MS-001, MX-002, MX-730, MX-750, MX-035) and butoxymethyl type melamine compounds (product names: Nikalac® MX-45, MX-410, MX-302) manufactured by Sanwa Chemical Co., Ltd.

[0212] Furthermore, the compounds may be obtained by condensing melamine compounds, urea compounds, glycoluryl compounds, and benzoguanamine compounds in which the hydrogen atoms of such amino groups are substituted with methylol groups or alkoxymethyl groups. For example, high molecular weight compounds produced from melamine compounds and benzoguanamine compounds described in U.S. Patent No. 6,323,310 are examples. Examples of commercially available melamine compounds include trade name: Cymel® 303 (manufactured by Mitsui Cytec Co., Ltd. (now Ornex Corporation)), and examples of commercially available benzoguanamine compounds include trade name: Cymel® 1123 (manufactured by Mitsui Cytec Co., Ltd. (now Ornex Corporation)).

[0213] Specific examples of phenoplast compounds include, for example, 2,6-bis(hydroxymethyl)phenol, 2,6-bis(hydroxymethyl)cresol, 2,6-bis(hydroxymethyl)-4-methoxyphenol, 3,3',5,5'-tetrakis(hydroxymethyl)biphenyl-4,4'-diol, 3,3'-methylenebis(2-hydroxy-5-methylbenzenemethanol), 4,4'-(1-methylethylidene)bis[2-methyl-6-hydroxymethylphenol], 4,4'-methylenebis[2-methyl-6-hydroxymethylphenol], 4,4'-(1-methylethylidene)bis[2,6-bis(hydroxymethyl)phenol], and 4,4'-methylenebis[2,6-bis(hydroxymethyl)phenol]. Examples include 2,6-bis(methoxymethyl)phenol, 2,6-bis(methoxymethyl)cresol, 2,6-bis(methoxymethyl)-4-methoxyphenol, 3,3',5,5'-tetrakis(methoxymethyl)biphenyl-4,4'-diol, 3,3'-methylenebis(2-methoxy-5-methylbenzenemethanol), 4,4'-(1-methylethylidene)bis[2-methyl-6-methoxymethylphenol], 4,4'-methylenebis[2-methyl-6-methoxymethylphenol], 4,4'-(1-methylethylidene)bis[2,6-bis(methoxymethyl)phenol], 4,4'-methylenebis[2,6-bis(methoxymethyl)phenol], etc. These are also available as commercially produced products, and specific examples include 26DMPC, 46DMOC, DM-BIPC-F, DM-BIOC-F, TM-BIP-A, BISA-F, BI25X-DF, and BI25X-TPA (all manufactured by Asahi Organic Chemicals Co., Ltd.).

[0214] Furthermore, as component (D1), polymers produced using acrylamide compounds or methacrylamide compounds substituted with hydroxymethyl or alkoxymethyl groups, such as N-hydroxymethylacrylamide, N-methoxymethylmethacrylamide, N-ethoxymethylacrylamide, and N-butoxymethylmethacrylamide, can also be used.

[0215] Examples of such polymers include poly(N-butoxymethylacrylamide), copolymers of N-butoxymethylacrylamide and styrene, copolymers of N-hydroxymethylmethacrylamide and methyl methacrylate, copolymers of N-ethoxymethylmethacrylamide and benzyl methacrylate, and copolymers of N-butoxymethylacrylamide, benzyl methacrylate and 2-hydroxypropyl methacrylate. The weight-average molecular weight of such polymers is 1,000 to 50,000, preferably 1,500 to 20,000, and more preferably 2,000 to 10,000.

[0216] (D2) Crosslinkable compound represented by formula (4) Furthermore, the photosensitive resin composition of the present invention may contain a crosslinkable compound represented by formula (4) as component (D2). [ka] (In the formula, k is an integer from 2 to 10, m is an integer from 0 to 4, R 11 (This represents a k-valent organic group.)

[0217] The (D2) component is not particularly limited as long as it is a compound having a cycloalkene oxide structure represented by formula (4). Specific examples include the compounds represented by formulas D2-1 and D2-2 below, as well as the commercially available products listed below. [ka] [ka]

[0218] Commercially available products include Epolide® GT-401, GT-403, GT-301, GT-302, Celoxide® 2021, Celoxide 2021P, Celoxide 3000 (product names manufactured by Daicel Corporation), Denacol® EX-252 (product name manufactured by Nagase ChemteX Corporation), CY175, CY177, CY179 (product names manufactured by Huntsman Corporation), Araldite® CY-182, CY-192, CY-184 (product names manufactured by Huntsman Corporation), Epiclon® 200, 400 (product names manufactured by DIC Corporation), and Epicort® 871, 872 (product names manufactured by Mitsubishi Chemical Corporation). "Epicort" is a product name from Resolution Research. Examples include ED-5661, ED-5662 (a registered trademark of Nederland Bethloten Vennootschap), which are trade names of Celanese Coatings Co., Ltd. These crosslinking compounds may be used individually or in combination of two or more types.

[0219] Of these, compounds represented by formulas D2-1 and D2-2, which have a cyclohexene oxide structure, are preferred from the viewpoint of heat resistance, solvent resistance, process resistance such as resistance to long-term firing, and transparency, as are Epolid® GT-401, GT-403, GT-301, GT-302, Celoxide® 2021, Celoxide 2021P, and Celoxide 3000.

[0220] Furthermore, as component D, compounds other than those indicated as components (D1) and (D2) can be used that can form a cross-linking structure through thermal reaction with the heat-reactive sites of the alkali-soluble resin (for example, carboxyl groups and / or phenolic hydroxyl groups and amide groups). Specifically, for example, epoxy compounds such as ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, 2,2-dibromo neopentyl glycol diglycidyl ether, 1,3,5,6-tetraglycidyl-2,4-hexanediol, N,N,N',N'-tetraglycidyl-m-xylenediamine, 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, and N,N,N',N'-tetraglycidyl-4,4'-diaminodiphenylmethane, VESTANAT® B1358 / 100, VESTAGON® BF Examples include isocyanate compounds such as 1540 (isocyanurate-type modified polyisocyanate, manufactured by Degussa Japan Co., Ltd.), Takenate® B-882N, and Takenate® B-7075 (both isocyanurate-type modified polyisocyanate, manufactured by Mitsui Chemicals, Inc.).

[0221] Furthermore, (D) as a thermal crosslinking agent, for example, a polymer having two or more structures that can form a crosslinking structure by thermal reaction with the thermally reactive sites of an alkali-soluble resin (e.g., carboxyl groups and / or phenolic hydroxyl groups and amide groups) can be used. Specifically, examples include polymers produced using compounds having epoxy groups such as glycidyl methacrylate and 3,4-epoxycyclohexylmethyl methacrylate; polymers produced using compounds having alkoxysilyl groups such as 3-methacryloxypropyltrimethoxysilane; compounds having isocyanate groups such as 2-isocyanatoethyl methacrylate (Kalenz MOI [registered trademark], manufactured by Resonac Co., Ltd.) and 2-isocyanatoethyl acrylate (Kalenz AOI [registered trademark], manufactured by Resonac Co., Ltd.); or polymers produced using compounds having blocked isocyanate groups such as 2-(0-[1'-methylpropyleneneamino]carboxyamino)ethyl methacrylate (Kalenz MOI-BM [registered trademark], manufactured by Resonac Co., Ltd.) and 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate (Kalenz MOI-BP [registered trademark], manufactured by Resonac Co., Ltd.). These compounds may be used individually or in combination to produce polymers, or they may be used in combination with other compounds to produce polymers.

[0222] If the alkali-soluble resin has a group that reacts with at least one group selected from the group consisting of hydroxyl groups, carboxyl groups, amide groups, and amino groups, then a compound having two or more groups selected from the group consisting of hydroxyl groups, carboxyl groups, amide groups, and amino groups, i.e., groups that are thermally reactive with the alkali-soluble resin, can be used as component D.

[0223] These crosslinkable compounds can be used individually or in combination of two or more.

[0224] In the photosensitive resin composition of the present invention, when the inclusion of component (D) crosslinking agent is selected, the content is 1 to 30 parts by mass, preferably 2 to 20 parts by mass, and more preferably 3 to 15 parts by mass, of the solid content. If the content of the crosslinking agent (crosslinkable compound) is low, the density of crosslinks formed by the crosslinkable compound may not be sufficient, and the effect of improving heat resistance, solvent resistance, and resistance to long-term firing after pattern formation may not be obtained. On the other hand, if it exceeds 50 parts by mass, uncrosslinked crosslinkable compounds may be present, which may reduce heat resistance, solvent resistance, and resistance to long-term firing after pattern formation, and may also worsen the storage stability of the photosensitive resin composition.

[0225] Furthermore, in addition to (A) phosphor and (B) binder, the wavelength conversion film-forming composition of the present invention may optionally contain various known additives such as (C) light scattering particles, (D) thermal crosslinking agents, light stabilizers, antioxidants, surfactants, polymer dispersants, flame retardants, clearing agents, ultraviolet absorbers, and fillers.

[0226] Examples of antioxidants include hindered phenol antioxidants, phenolic antioxidants, phosphorus antioxidants, and sulfur-based antioxidants. These may be used individually or in combination of two or more. Commercial antioxidants can be used, including Irganox 245 and Irganox 1010 from BASF Japan Ltd., and ADEKA Corporation's ADEKA Stab AO-20, ADEKA Stab AO-30, ADEKA Stab AO-40, ADEKA Stab AO-50, ADEKA Stab AO-60, ADEKA Stab AO-80, and ADEKA Stab AO330, but are not limited to these. When using antioxidants, there are no particular restrictions on the amount to be added, but it is preferable that the amount be 0.1 to 5.0% by mass of the solid content of the wavelength conversion film-forming composition, and more preferably 0.3 to 1.5% by mass.

[0227] As the surfactant, fluorine-based surfactants are preferred, and nonionic fluorine-based surfactants are more preferred. Specific examples include, but are not limited to, the F-Tergent series manufactured by Neos Corporation, such as the 212M, 215M, 250, 222F, FTX-218, and DFX-18. When a surfactant is used, there are no particular restrictions on the amount it is added, but it is preferably 0.01 to 1% by mass, and more preferably 0.01 to 0.5% by mass, of the solid content of the wavelength conversion film-forming composition.

[0228] The polymeric dispersant is a polymer compound having a weight-average molecular weight of 750 or more and having a functional group that has affinity for light-scattering particles. The polymeric dispersant has the function of dispersing light-scattering particles. The polymeric dispersant is adsorbed onto the light-scattering particles via the functional group that has affinity for the light-scattering particles, and the light-scattering particles are dispersed in the composition by electrostatic repulsion and / or steric repulsion between the polymeric dispersants. It is preferable that the polymeric dispersant is adsorbed onto the light-scattering particles by binding to their surface, but it may also be free in the wavelength conversion film-forming composition.

[0229] Examples of functional groups having affinity for the light scattering particles (C) above include acidic functional groups, basic functional groups, and nonionic functional groups. Acidic functional groups have dissociable protons and may be neutralized by bases such as amines and hydroxide ions, while basic functional groups may be neutralized by acids such as organic acids and inorganic acids.

[0230] Examples of acidic functional groups include carboxyl groups (-COOH), sulfo groups (-SO3H), sulfate groups (-OSO3H), phosphonic acid groups (-PO(OH)2), phosphate groups (-OPO(OH)2), phosphinic acid groups (-PO(OH)-), and mercapto groups (-SH).

[0231] Basic functional groups include primary amino groups, secondary amino groups, tertiary amino groups, ammonium groups, and imino groups, as well as nitrogen-containing heterocyclic groups such as pyridine, pyrimidine, pyrazine, imidazole, and triazole.

[0232] Examples of nonionic functional groups include hydroxyl groups, ether groups, thioether groups, sulfinyl groups (-SO-), sulfonyl groups (-SO2-), carbonyl groups, formyl groups, ester groups, carbonate ester groups, amide groups, carbamoyl groups, ureido groups, thioamide groups, thioureido groups, sulfamoyl groups, cyano groups, alkenyl groups, alkynyl groups, phosphine oxide groups, and phosphine sulfide groups.

[0233] The polymeric dispersant may be a polymer (homopolymer) of a single monomer, or a copolymer of multiple monomers. Furthermore, the polymeric dispersant may be a random copolymer, a block copolymer, or a graft copolymer. If the polymeric dispersant is a graft copolymer, it may be a comb-shaped graft copolymer or a star-shaped graft copolymer. Specific examples of polymeric dispersants include acrylic resins, polyester resins, polyurethane resins, polyamide resins, polyethers, phenolic resins, silicone resins, polyurea resins, amino resins, epoxy resins, polyethyleneimines, polyallylamines, and polyimides.

[0234] Commercial polymer dispersants can also be used, such as the DISPERBYK series and BYK series from BYK, the Efka series from BASF, the Solspers series from Lubrizol, the Azisper PB series from Ajinomoto Fine Techno Co., Ltd., the TEGO series from Evonik, and the Disparon series from Kusumoto Chemical Co., Ltd.

[0235] Specific examples of the above commercially available products include BYK's DISPERBYK-130, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-166, DISPERBYK-167, DISPERBYK-168, DISPERBYK-170, DISPERBYK-171, DISPERBYK-174, DISPERBYK-180, DISPERBYK-182, DISPERBYK-183, and DISPERBYK-1 84, DISPERBYK-185, DISPERBYK-2000, DISPERBYK-2001, DISPERBYK-2008, DISPERBYK-2009, DISPERBYK-2020, DISPERBYK-2022, DISPER BYK-2025, DISPERBYK-2050, DISPERBYK-2070, DISPERBYK-2096, DISPERBYK-2150, DISPERBYK-2155, DISPERBYK-2163, DISPERBYK-2164; BASF models EFKA4010, EFKA4015, EFKA4046, EFKA4047, EFKA4061, EFKA4080, EFKA4300, EFKA4310, EFKA4320, EFKA4330, EFKA4340, EFKA4560, EFKA4585, EFKA5207, EFKA1501, EFKA1502, EFKA1503, and EFKA PX-4701; Lubrizol's Solspers 3000, Solspers 9000, Solspers 13240, Solspers 13650, Solspers 13940, Solspers 11200, Solspers 13940, Solspers 16000, Solspers 17000, Solspers 18000, Solspers 20000, Solspers 21000, Solspers 24000, Solspers 26000, Solspers 27000, Solspers 280 00, Solspers 32000, Solspers 32500, Solspers 32550, Solspers 32600, Solspers 33000, Solspers 34750, Solspers 35100, Solspers 35200, Solspers 36000, Solspers 37500, Solspers 38500, Solspers 39000, Solspers 41000, Solspers 54000, Solspers 71000 and Solspers 76500; Ajisper PB821, Ajisper PB822, Ajisper PB881, PN411 and PA111, manufactured by Ajinomoto Fine Techno Co., Ltd. Examples include TEGO Dispers650, TEGO Dispers660C, TEGO Dispers662C, TEGO Dispers670, TEGO Dispers685, TEGO Dispers700, TEGO Dispers710, and TEGO Dispers760W manufactured by Evonik Corporation, as well as Disparon AQ-320, Disparon AQ-330, Disparon AQ-340, Disparon AQ-360, and Disparon AQ-380 manufactured by Kusumoto Kasei Co., Ltd.

[0236] When using a polymeric dispersant, there are no particular restrictions on the amount it can be added, but it is preferably 1 to 100% by mass relative to the light scattering particles, and more preferably 5 to 50% by mass.

[0237] Furthermore, the wavelength conversion film-forming composition of the present invention may optionally contain a solvent.Specific examples include aromatic or halogenated aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and chlorobenzene; aliphatic hydrocarbons such as n-heptane, n-hexane, and cyclohexane; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and cyclopentanone; and ethyl acetate, n-hexyl acetate, ethyl lactate, γ-butyrolactone, and propylene carbonate. Ester solvents such as diisopropyl malonate and ethyl 3-ethoxypropionate; halogenated hydrocarbon solvents such as methylene chloride, dichloromethane, 1,2-dichloroethane, and chloroform; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinone; alcohol solvents such as methanol, ethanol, isopropanol, n-propanol, cyclohexanol, diacetone alcohol, and 2-benzooxyethanol; ethylene glycol Examples of organic solvents include glycol ether solvents such as noethyl ether, ethylene glycol monobutyl ether, ethylene glycol diglycidyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, triethylene glycol monobutyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate; glycol solvents such as ethylene glycol, propylene glycol, hexylene glycol, 3-octylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, 1,3-butanediol, 2,3-butanediol, and 1,4-butanediol; nitrile solvents such as acetonitrile; and sulfur-containing solvents such as dimethyl sulfoxide.These may be used individually or in combination of two or more types.

[0238] Furthermore, the compound represented by formula (1) may exist as a solvate. The solvate is not particularly limited as long as it is a solvate of the compound represented by formula (1) and a solvent. Examples of solvents used to form the solvate include dichloromethane, chloroform, acetonitrile, diethyl ether, ethyl acetate, methanol, ethanol, cyclohexane, toluene, acetone, N,N-dimethylformamide, dimethyl sulfoxide, and tetrahydrofuran.

[0239] When a wavelength conversion film-forming composition contains a solvent, the solid content concentration of the wavelength conversion film-forming composition cannot be specified in general terms, as it varies depending on the desired thickness of the wavelength conversion film and the coating method, but it is usually 10 to 70% by mass, and preferably 15 to 60% by mass.

[0240] The upper limit of the viscosity of the above wavelength conversion film-forming composition at 25°C is 10,000 mPa·s or less, preferably 1,000 mPa·s or less. The lower limit is preferably 5 mPa·s or more, and more preferably 10 mPa·s or more, considering storage stability. In this invention, viscosity refers to the measurement value obtained using an EMS viscometer.

[0241] The wavelength conversion film-forming composition of the present invention can be prepared by mixing the above-mentioned (A) phosphor and (B) binder, optionally the above-mentioned (C) light scattering particles, other additives such as surfactants, and a solvent in any order.

[0242] A wavelength conversion film can be obtained by applying the above-described wavelength conversion film-forming composition of the present invention to a substrate, for example, evaporating the solvent by heating (similar to "pre-baking") as needed, and further irradiating it with active energy rays (e.g., ultraviolet light) as needed. Coating methods include, for example, reverse roll coaters, blade coaters, slit die coaters, direct gravure coaters, offset gravure coaters, kiss coaters, natural roll coaters, air knife coaters, roll blade coaters, variable bar roll blade coaters, two-stream coaters, rod coaters, wire bar coaters, applicators, dip coaters, curtain coaters, spin coaters, knife coaters, and inkjet coatings.

[0243] Heating can be done using common heating devices such as ovens or hot plates. The heating conditions are not particularly limited as long as a film can be formed, but 60-200°C for 2 minutes to 2 hours is preferred, and 80-200°C for 15 minutes to 1 hour is more preferred. The film may also be cured in stages.

[0244] While there are no particular restrictions on the irradiation of ultraviolet light as long as a film can be formed, light sources such as mercury lamps, metal halide lamps, xenon lamps, and LEDs can be used, and if necessary, a bandpass filter can be used to remove light other than the desired exposure wavelength. The wavelength of the irradiated light is preferably 200 to 440 nm, and particularly preferably includes light with a wavelength of 300 to 400 nm. The exposure dose is 10 to 4,000 mJ / cm². 2 It is preferable.

[0245] The aforementioned heating step and ultraviolet light exposure step may be combined in any order. For example, heating may be performed first and then ultraviolet light irradiation may be performed, or ultraviolet light irradiation may be performed first and then heating may be performed, or heating may be performed first, then ultraviolet light irradiation may be performed, and then further heating may be performed.

[0246] The thickness of the wavelength conversion film (i.e., the wavelength conversion film immediately before exposure to ultraviolet light) is not particularly limited, but is usually 1 to 1,000 μm, preferably 3 to 500 μm, and more preferably 5 to 100 μm. The haze of the wavelength conversion film is not particularly limited, but from the viewpoint of increasing the amount of light that the phosphor can absorb by scattering incident light within the film, it is preferably 18% or more, more preferably 30% or more, and more preferably 40% or more. The upper limit of the haze value is not particularly limited, but is usually around 95%. In this invention, the haze value is measured according to ASTM D1003-61. In this invention, the measurement conditions for the above haze value include, for example, the conditions for measuring a 10 μm thick film formed from a composition containing 3% by mass of titanium dioxide particles.

[0247] The above-mentioned substrate can be appropriately selected from those used as base materials for forming this type of film, but glass substrates or polymer plates with a light transmittance of 50% or more in the visible region of 400 to 800 nm are preferred. Specific examples of glass include soda-lime glass, barium-strontium glass, lead glass, aluminosilicate glass, borosilicate glass, barium-borosilicate glass, and quartz. Specific examples of polymers include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.

[0248] In the present invention, along with (B-1), (B-2), and (B-3), the above-mentioned (B-5) resin is a composition containing an alkali-soluble resin (a so-called negative-type photosensitive resin composition). When a coating film is formed using this composition, a mask having a predetermined pattern is placed on the obtained coating film and irradiated with light such as ultraviolet light. By developing with an alkaline developer, the unexposed areas are washed out, and the remaining patterned film is heated at 80 to 140°C for 0.5 to 10 minutes as needed to obtain a sharp relief pattern on the edge.

[0249] Examples of the above-mentioned alkaline developers include aqueous solutions of alkali metal hydroxides such as potassium carbonate, sodium carbonate, potassium hydroxide, and sodium hydroxide; aqueous solutions of quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, and choline; and alkaline aqueous solutions of amines such as ethanolamine, propylamine, and ethylenediamine. Furthermore, surfactants known for use in developers may be added to these developers.

[0250] Among the above, a 0.1-2.58% by mass aqueous solution of tetraethylammonium hydroxide is commonly used as a developer for photoresists, and in the composition of the present invention, this alkaline developer can be used to develop the material well without causing problems such as swelling.

[0251] Furthermore, any of the following development methods can be used: the liquid-filling method, the dipping method, or the agitation immersion method. The development time in these cases is usually 15 to 180 seconds.

[0252] After development, the photosensitive resin film is washed with running water, and then air-dried using compressed air or compressed nitrogen, or by spinning, to remove moisture from the substrate and obtain a patterned film. In the above procedure, the washing time is usually about 20 to 120 seconds.

[0253] Next, the obtained pattern-forming film is heated for thermal curing (this heating is also called "post-bake") to obtain a film with excellent heat resistance, transparency, planarity, low water absorption, chemical resistance, etc., and a good relief pattern. A hot plate, oven, etc., can be used to heat the above pattern-forming film.

[0254] Post-baking methods generally involve heating at a temperature selected from the range of 140 to 270°C for 5 to 30 minutes on a hot plate, or for 30 to 90 minutes in an oven. By post-baking under these conditions, a cured film with a good pattern shape can be obtained.

[0255] The wavelength conversion film formed using the wavelength conversion film-forming composition of the present invention exhibits excellent wavelength conversion efficiency and residual film rate, making it suitable for use as a wavelength conversion film (color conversion film) for displays such as micro-LED displays, organic EL displays, and liquid crystal displays, as well as for lighting. [Examples]

[0256] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples.

[0257] [Molecular weight measurement] In this embodiment, the molecular weight of the polymer was measured using a GPC system manufactured by JASCO Corporation, with Shodex® KF-804L and 803L columns, under the following conditions. Column oven: 40℃ Flow rate: 1mL / min Eluent: Tetrahydrofuran

[0258] The meanings of the abbreviations used in this embodiment are as follows: MMA: Methyl methacrylate MAA: Methacrylic acid MAIB: 2,2'-Dimethyl azobis(isobutyrate) [Organic fluorescent dye (component (A))] FL-305: Oracet (registered trademark) FL Red 305 (product name) [Scattered particles ((C) component)] PT-401L: High-purity titanium dioxide (rutile type, average particle size 130nm) manufactured by Ishihara Sangyo Co., Ltd. [Particle dispersant] AQ-320: Disparon AQ-320 (product name) manufactured by Kusumoto Kasei Co., Ltd. [(B-2) component] IPEMA: Isoprenyl methacrylate manufactured by Kuraray Co., Ltd. [Photopolymerization initiator 1 (component B-1)] NCI-930: ADEKA Corporation NCI-930 (product name) [Photopolymerization initiator 2 (component (B-1))] Omnirad 184: Omnirad 184 (product name) manufactured by IGM Resin. [polymer] P1: Acrylic polymer (alkali-soluble resin) as described in Reference Synthesis Example 1 below. [Acrylic crosslinking agent 1 (component B-3)] V260: Viscoat V260 (product name) manufactured by Osaka Organic Chemical Co., Ltd. [Epoxy crosslinking agent 1 (component (D))] GT-401: Daicel Corporation's EPOLEED (registered trademark) GT-401 [Other additives] PE-1: Karens MT PE1 (product name) [Surfactants] DFX-18: Neos Co., Ltd. F-Tergent DFX-18 (product name) [solvent] CPN: Cyclopentanone PGMEA: Propylene glycol monomethyl ether acetate

[0259] Reference synthesis example 1 Synthesis of alkali-soluble resin P1 80.0 g of MMA, 20.0 g of MAA, and 7.0 g of MAIB were dissolved in 160.5 g of CPN and reacted at 100°C for 20 hours to obtain an acrylic polymer P1 solution (solid content concentration 40% by mass). The obtained acrylic polymer P1 had a manganese content of 5,022 and a manganese content of 8,070.

[0260] [Preparation Example 1] Preparation of a light scattering particle dispersion [CPN dispersion of component C] In a 1000 mL polypropylene container, light-scattering particles PT-401L and particle dispersant AQ-320 in an amount equivalent to 20% by mass relative to the PT-401L in terms of solid content were added. CPN was then added to adjust the solid content to 36% by mass, and the mixture was stirred at 1,500 rpm for 30 minutes to obtain a slurry. Next, the entire slurry was transferred to a slurry tank, and a light-scattering particle dispersion was obtained by performing 10 passes using an Ashizawa Finetech LabMinister DMS65 bead mill with 0.2 mm diameter zirconia beads packed at 60 volume percent, under conditions of a liquid delivery speed of 60 mL / min and a disk peripheral speed of 8 m / s. The particle size distribution of the obtained dispersion was measured using a Nanotrac UPA (Microtrac). CPN was used as the diluent, and the 50% cumulative diameter (D50) of particles in the dispersion was calculated on a volume basis using MicrotracDMS analysis software from Nikkiso Co., Ltd. from the scattering generated when the diluted sample was irradiated with laser light, and it was found to be 185 nm.

[0261] [Examples 1 to 3 and Comparative Examples 1 to 5] Preparation of compositions for wavelength conversion film formation A composition for wavelength conversion film formation was prepared by mixing each component in the compositions shown in Tables 1 to 3 and filtering the resulting mixture through a polytetrafluoroethylene (PTFE) filter with a pore size of 5.0 μm. The composition ratios in Tables 1 to 3 represent the mass ratio of solid content.

[0262] [Table 1]

[0263] [Table 2]

[0264] [Table 3]

[0265] [Film thickness measurement] The film thickness of each wavelength conversion film formed using the wavelength conversion film-forming compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 5 was measured as follows. The film thickness of the coating obtained by the methods described below in the Optical Properties Evaluation and Lithography Properties Evaluation sections was measured from the spectrum in the wavelength range from 1000 nm to 1600 nm using an interferometric film thickness meter, Filmetrics F20-EXR.

[0266] [Optical properties evaluation] The optical properties of each wavelength conversion film formed using the wavelength conversion film-forming compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 5 were evaluated as follows. The wavelength conversion film-forming compositions of Examples 1 to 3 and Comparative Examples 1 to 5 were applied to a quartz substrate using a spin coater, and then pre-baked on a hot plate at 110°C for 90 seconds to obtain a coated film sample with a thickness of 11 μm. Subsequently, the samples were cured using an ultraviolet curing apparatus manufactured by I-Graphics Co., Ltd. at a rate of 200 mJ / cm². 2 A coating sample with a thickness of 10 μm was obtained by irradiating it with ultraviolet light and then performing a post-bake at 230°C for 10 minutes. Next, the coating sample was placed on top of a blue LED light (emission peak wavelength 450 nm) manufactured by CCS Corporation, the LED light was turned on, and the light emitted through the coating sample was measured using a USR-45 spectroradiometer manufactured by Ushio Inc., and the result is (1). Similarly, the light emitted from only the LED light, excluding the coated film sample, was measured in the same manner and the result was (2). From the obtained spectral irradiance spectrum, the number of photons of light with wavelengths of 480 nm or less in result (2) was defined as the "excited photon number". Similarly, the number of photons of light with wavelengths of 480 nm or less in result (1) was defined as the "transmitted photon number". Similarly, the number of photons of light with wavelengths exceeding 480 nm in result (1) was defined as the "emitted photon number". The "blue light absorption rate" and "conversion efficiency" were calculated using the following formulas. Blue light absorption rate = (Number of excited photons - Number of transmitted photons) ÷ Number of excited photons Conversion efficiency = Number of emitted photons ÷ Number of excited photons

[0267] [Lithography Characteristic Evaluation] The lithographic characteristics of each wavelength conversion film formed using the wavelength conversion film-forming compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 5 were evaluated as follows. For Examples 1 to 3 and Comparative Examples 1 to 5, each composition was applied to a silicon substrate treated with hexamethyldisilazane using a spin coater, and then pre-baked on a hot plate at 110°C for 90 seconds to form a coating film with a thickness of 13 μm. After measuring the thickness of the coating film (thickness after pre-baking), the light intensity at 365 nm was measured on the coating film using a Canon PLA-600FA ultraviolet irradiation device, and the light intensity at 365 nm was measured at 3.4 mW / cm². 2 UV radiation at 200 mJ / cm² 2 The sample was irradiated with the specified exposure amount through a photomask having 5mm x 6mm light-transmitting sections spaced at 5mm x 6mm intervals. This coating was then immersed in a 0.045% by mass potassium hydroxide aqueous solution for 4 minutes and 30 seconds, followed by rinsing with ultrapure water for 30 seconds. After that, a patterned coating sample was obtained by drying with an air blower. In all of Examples 1 to 3 and Comparative Examples 1 to 5, no coating was observed on the substrate in the light-shielded areas during ultraviolet light irradiation, indicating that the film was removed by the development process, while the coating was maintained in the exposed areas. Next, the film thickness of the coating sample after development was measured, and the "residual film rate" was calculated using the film thickness after development and the film thickness after pre-baking according to the following formula. Residual film percentage = Film thickness after development ÷ Film thickness after pre-baking

[0268] Tables 4 and 5 show the optical properties and lithography characteristics of the wavelength conversion films formed using the wavelength conversion film-forming compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 5.

[0269] [Table 4]

[0270] [Table 5]

[0271] According to the results of Examples 1 to 3, which are embodiments of the present invention, in Examples 1 to 3, where 12 to 24% by mass of IPEMA was used as the wavelength conversion film-forming composition, the conversion efficiency exceeded 30% and the residual film rate exceeded 50% in all cases. In Examples 1 and 2, the conversion efficiency exceeded 35% and the residual film rate exceeded 70% in all cases. Furthermore, in Comparative Examples 1 to 4, where 0 to 6% by mass of IPEMA was used, and Comparative Example 5, where 30% by mass of IPEMA was used, it was found that in all cases the coating film was completely dissolved after development, and none of them exceeded a conversion efficiency of 30% or a residual film rate of 50%. Furthermore, since a photoradical polymerization initiator was used as the photopolymerization initiator in Examples 1 to 3, it was confirmed that a composition (i.e., a composition for forming a wavelength conversion film) and the wavelength conversion film itself can be provided, which are capable of forming a wavelength conversion film with excellent insolubility in the developer solution during development after exposure in air. [Industrial applicability]

[0272] According to the present invention, it is possible to provide a composition (i.e., a composition for forming a wavelength conversion film) that can form a wavelength conversion film having a high residual film rate and high conversion efficiency, and the wavelength conversion film itself. Therefore, it can be used as a composition for forming a wavelength conversion film for various applications, and is expected to have potential applications in a wide variety of industrial fields that require wavelength conversion films (particularly in the manufacturing of displays such as micro-LED displays).

Claims

1. A composition for forming a wavelength conversion film, comprising (A) a phosphor and (B) a binder, wherein (B) the binder contains a compound represented by the following general formula (1). 【Chemistry 1】 [In general formula (1), R １ and R ２ Each of these independently represents one of the groups selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, and an aralkyl group, R ３ R represents one of the groups selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, aryl groups, and aralkyl groups. ４ [wherein X represents one of the groups selected from the group consisting of (meth)acryloyl groups, styryl groups, and alkenyl groups having 2 to 6 carbon atoms, and X represents NH or O, and n represents any integer from 1 to 5.]

2. In the above general formula (1), R １ and R ２ is a hydrogen atom, R ３ is a methyl group, n is 1 to 4, R ４ The wavelength conversion film forming composition according to claim 1, wherein is a (meth)acryloyl group or a styryl group, and X is O.

3. The wavelength conversion film forming composition according to claim 1, wherein the above general formula (1) is the following general formula (2). 【Chemistry 2】 [In the formula, R ５ represents a hydrogen atom or a methyl group.]

4. The above binder (B) (B-1) Photopolymerization initiator, (B-2) The compound represented by the above general formula (1), (B-3) A compound having two or more polymerizable functional groups in its molecule and being different from the compound represented by the general formula (1) above, A wavelength conversion film-forming composition according to claim 1, comprising the above.

5. The wavelength conversion film-forming composition according to claim 4, wherein the polymerizable functional group in (B-3) above is a (meth)acryloyl group.

6. The above binder (B) (B-4) Compounds having one polymerizable functional group in the molecule A wavelength conversion film-forming composition according to claim 4, comprising the above.

7. The wavelength conversion film-forming composition according to claim 6, wherein the polymerizable functional group in (B-4) above is a (meth)acryloyl group.

8. The wavelength conversion film forming composition according to claim 4, wherein the above-mentioned (B) binder contains (B-5) resin.

9. The wavelength conversion film forming composition according to claim 8, wherein the above (B-5) resin contains an alkali-soluble resin.

10. Furthermore, the wavelength conversion film forming composition according to claim 1, further comprising (C) light scattering particles.

11. The wavelength conversion film forming composition according to claim 10, wherein the above (C) light scattering particles are titanium oxide particles.

12. Furthermore, the wavelength conversion film forming composition according to claim 1, further comprising (D) a thermal crosslinking agent.

13. The wavelength conversion film forming composition according to claim 12, wherein the (D) thermal crosslinking agent is an epoxy crosslinking agent.

14. The wavelength conversion film forming composition according to claim 1, wherein the content of the above-mentioned (A) phosphor is 0.1% by mass or more in the solid content.

15. The wavelength conversion film forming composition according to claim 10, wherein the content of (C) light scattering particles is 1% by mass or more in the solid content.

16. The wavelength conversion film forming composition according to claim 1, wherein the haze value of the film formed from the above composition is 18% or more.

17. The wavelength conversion film forming composition according to claim 1, which is a composition for forming a wavelength conversion film for displays.

18. A wavelength conversion film made from a wavelength conversion film forming composition according to any one of claims 1 to 17.

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