Photosensitive coloring resin compositions, pigment dispersions, cured products, separators, organic electroluminescent elements, color filters, and image display devices.

Abstract

A photosensitive coloring resin composition with high residual film yield is provided. The photosensitive coloring resin composition of the present invention is characterized in that it contains (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin and (D) a photopolymerization initiator, wherein the aforementioned (A) colorant comprises an organic pigment (A-1) and the aforementioned (C) alkali-soluble resin comprises a resin (C1) having a structural unit having the following general formula (1).

Description

Technical Field

[0001] This invention relates to photosensitive coloring resin compositions, pigment dispersions, cured products, separators, organic electroluminescent elements, color filters, and image display devices.

[0002] This application claims priority based on Japanese Patent Application No. 2022-127367, filed in Japan on August 9, 2022, the contents of which are incorporated herein by reference. Background Technology

[0003] Liquid crystal displays (LCDs) utilize the property that the arrangement of liquid crystal molecules changes according to the voltage applied to and removed from the liquid crystal. On the other hand, most of the components that make up an LCD cell are formed using methods that utilize photosensitive compositions, such as photolithography.

[0004] This photosensitive composition is easy to form microstructures and is also easy to process for substrates used in large-screen applications. For these reasons, its application range is expanding.

[0005] Image display devices containing organic electroluminescent elements (also known as organic EL) are attracting much attention as the next generation of flat panel displays (FPDs) due to their excellent visual recognition such as contrast and viewing angle, responsiveness, low power consumption, thin and lightweight design, and flexible display body.

[0006] Organic electroluminescent elements have the following structure: an organic layer containing a light-emitting layer or various functional layers is sandwiched between a pair of electrodes, at least one of which is transparent. Image display devices display images by driving a panel in which organic electroluminescent elements are disposed at each pixel.

[0007] Traditionally, such organic electroluminescent devices have been manufactured by forming partitions (banks) on a substrate and then stacking light-emitting layers or various functional layers within the area surrounded by the partitions.

[0008] When forming a film such as a light-emitting layer in an area surrounded by a partition wall, the following vapor deposition method is mainly used: the material is sublimated and attached to the substrate under vacuum, thereby forming a film.

[0009] In recent years, wet film-forming methods such as casting, spin coating, and inkjet printing have attracted much attention. In particular, inkjet printing can reduce film thickness unevenness when producing large areas, and can achieve high precision in displays, reduce material consumption, and improve yield by coating separately. Therefore, it is suitable as a film-forming method for organic layers in large panels.

[0010] As a method for easily forming separators, a method using photolithography with a photosensitive composition is known. Additionally, as a method for imparting light-blocking properties to the separators and suppressing light leakage between pixels, a method of containing a colorant in the photosensitive composition is known.

[0011] Patent document 1 describes a photosensitive coloring resin composition that has high opacity and low dielectric constant by using a specific organic black pigment and dispersant.

[0012] In addition, Patent Document 2 describes a photosensitive coloring resin composition used in the partition wall of an organic electroluminescent element, which effectively suppresses the generation of exhaust gas by using a specific organic black pigment and an alkali-soluble resin.

[0013] Prior art literature

[0014] Patent Literature

[0015] Patent Document 1: International Publication No. 2015 / 46178

[0016] Patent Document 2: International Publication No. 2018 / 101314 Summary of the Invention

[0017] Problems to be solved by the invention

[0018] As a method for preparing photosensitive coloring resin compositions for use in light-shielding partitions, there is a known method of mixing a pigment dispersion, obtained by adding a pigment as a colorant and dispersing it with a dispersant, with other components. However, in the aforementioned pigment dispersion, depending on the type of pigment, dispersant, and dispersing resin, it is sometimes impossible to ensure sufficient dispersibility and storage stability.

[0019] In addition, during the development and calcination processes in the manufacturing of the separator, if the residual film rate of the photosensitive coloring resin composition is low, the developer resistance and heat resistance during calcination are poor. Therefore, sometimes decomposition products, by-products, uncured substances, etc. in the composition may remain or re-attach on the anode.

[0020] The inventors' research revealed that when using a separator wall in an organic electroluminescent element, sufficient brightness is sometimes not achieved due to the low element current density relative to the applied voltage caused by residues and reattachments on the anode. Furthermore, the photosensitive coloring resin compositions described in Patent Documents 1 and 2 do not have sufficient residual film rate and element current density.

[0021] Therefore, the first objective of the present invention is to provide a photosensitive coloring resin composition with high residual film yield. Furthermore, it aims to provide a photosensitive coloring resin composition with high residual film yield and high element current density when used as a separator wall for organic electroluminescent elements. Moreover, it aims to provide an organic electroluminescent element and an image display device with high brightness.

[0022] Furthermore, a second objective of the present invention is to provide a pigment dispersion with excellent dispersibility. Moreover, an objective is to provide a photosensitive coloring resin composition, an organic electroluminescent element, and an image display device.

[0023] Solutions for solving problems

[0024] The inventors conducted in-depth research and discovered that the above-mentioned problems could be solved by using specific alkali-soluble resins and organic pigments, thus completing the present invention.

[0025] That is, the gist of the present invention is as described below.

[0026] [1] A photosensitive coloring resin composition, characterized in that it contains (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin and (D) a photopolymerization initiator.

[0027] The aforementioned colorant (A) includes an organic pigment (A-1).

[0028] The aforementioned (C) alkali-soluble resin contains a resin (C1) having the structural unit shown in the following general formula (1).

[0029]

[0030] (In equation (1), R) 1 It represents a hydrogen atom or a methyl group.

[0031] R 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0032] L represents an alkylene group having 2 to 6 carbon atoms, and having at least a hydroxyl group, or a hydroxyl group and an ester group of a polybasic acid as substituents.

[0033] *Each represents a connection key.

[0034] [2] According to the photosensitive coloring resin composition of [1], wherein the aforementioned resin (C1) has the structural unit shown in the following general formula (2).

[0035]

[0036] (In formula (2), A represents a hydrogen atom or a polyacid residue.)

[0037] R 1 It represents a hydrogen atom or a methyl group.

[0038] R 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0039] *Each represents a connection key.

[0040] [3] The photosensitive coloring resin composition according to [1] or [2], wherein the aforementioned organic pigment (A-1) comprises an organic black pigment.

[0041] [4] According to the photosensitive coloring resin composition of [3], wherein the aforementioned organic black pigment comprises a benzodifuranone-based organic black pigment.

[0042] [5] The photosensitive coloring resin composition according to [4], wherein the aforementioned organic black pigment comprises an organic black pigment as a compound represented by the following general formula (A-1-1), its geometric isomer, its salt or a salt of its geometric isomer.

[0043]

[0044] (In formula (A-1-1), R) 611 and R 616 Each can independently represent a hydrogen atom, CH3, CF3, fluorine atom, or chlorine atom;

[0045] R 612 R 613 R 614 R 615 R 617 R 618 R 619 and R 620 Each independently represents a hydrogen atom, a halogen atom, and R. 621 COOH, COOR 621 COO - CONH2, CONHR 611 CONR 621 R 622 CN, OH, OR 621 COCR 621 、OOCNH2、OOCNHR 621 OOCNR 621 R 622 NO2, NH2, NHR 621 NR 621 R 622 , NHCOR 622 NR 621 COR 622N=CH2, N=CHR 621 N = CR 621 R 622 SH, SR 621 、SOR 621 、SO2R 621 SO3R 621 SO3H, SO3 - SO2NH2, SO2NHR 621 or SO2NR 621 R 622 ;

[0046] Choose freely R 612 With R 613 R 613 With R 614 R 614 With R 615 R 617 With R 618 R 618 With R 619 and R 619 With R 620 At least one combination in the group is optionally directly bonded to each other, or optionally bonded via an oxygen atom, sulfur atom, NH or NR atom. 621 Bridges connect them to each other;

[0047] R 621 and R 622 Each can independently represent an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an alkynyl group having 2 to 12 carbon atoms.

[0048] [6] The photosensitive coloring resin composition according to [1] or [2], wherein the aforementioned (B) dispersant comprises an acrylic dispersant having tertiary amino and / or quaternary ammonium groups.

[0049] [7] The photosensitive coloring resin composition according to [1] or [2], wherein the aforementioned (C) alkali-soluble resin contains (C2) epoxy (meth) acrylate resin.

[0050] [8] The photosensitive coloring resin composition according to [1] or [2], wherein the aforementioned (C) alkali-soluble resin contains (C3) a resin containing an isocyanuric acid backbone.

[0051] [9] The photosensitive coloring resin composition according to [1] or [2], wherein the content of the aforementioned resin (C1) in the aforementioned alkali-soluble resin is in the range of 4 to 80% by mass.

[0052]

[10] A pigment dispersion, characterized in that it contains (A) a colorant, (B) a dispersant and (C) an alkali-soluble resin,

[0053] The aforementioned colorant (A) includes an organic pigment (A-1).

[0054] The aforementioned (C) alkali-soluble resin contains a resin (C1) having the structural unit shown in the following general formula (1).

[0055]

[0056] (In equation (1), R) 1 It represents a hydrogen atom or a methyl group.

[0057] R 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0058] L represents an alkylene group having 2 to 6 carbon atoms, and having at least a hydroxyl group, or a hydroxyl group and an ester group of a polybasic acid as substituents.

[0059] *Each represents a connection key.

[0060]

[11] The pigment dispersion according to

[10] , wherein the aforementioned resin (C1) has the structural unit shown in the following general formula (2).

[0061]

[0062] (In formula (2), A represents a hydrogen atom or a polyacid residue.)

[0063] R 1 It represents a hydrogen atom or a methyl group.

[0064] R 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0065] *Each represents a connection key.

[0066]

[12] The pigment dispersion according to

[10] or

[11] , wherein the aforementioned organic pigment (A-1) comprises an organic black pigment.

[0067]

[13] The pigment dispersion according to

[12] , wherein the aforementioned organic black pigment comprises benzodifuranone-based organic black pigment.

[0068]

[14] The pigment dispersion according to

[13] , wherein the aforementioned organic black pigment comprises an organic black pigment as a compound, a geometric isomer thereof, a salt thereof, or a salt of a geometric isomer thereof, represented by the following general formula (A-1-1).

[0069]

[0070] (In formula (A-1-1), R) 611 and R 616 Each can independently represent a hydrogen atom, CH3, CF3, fluorine atom, or chlorine atom;

[0071] R 612 R 613 R 614 R 615 R 617 R 618 R 619 and R 620 Each independently represents a hydrogen atom, a halogen atom, and R. 621 COOH, COOR 621 COO - CONH2, CONHR 621 CONR 621 R 622 CN, OH, OR 621 COCR 621 、OOCNH2、OOCNHR 621 OOCNR 621 R 622 NO2, NH2, NHR 621 NR 621 R 622 , NHCOR 622 NR 621 COR 622 N=CH2, N=CHR 621 N = CR 621 R 622 SH, SR 621 、SOR 621 、SO2R 621 SO3R 621 SO3H, SO3 - SO2NH2, SO2NHR 621 or SO2NR 621 R 622 ;

[0072] Choose freely R 612 With R 613 R 613 With R 614 R 614 With R 615 R 617 With R 618 R 618 With R 619 and R 619 With R 620At least one combination in the group is optionally directly bonded to each other, or optionally bonded via an oxygen atom, sulfur atom, NH or NR atom. 621 Bridges connect them to each other;

[0073] R 621 and R 622 Each can independently represent an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an alkynyl group having 2 to 12 carbon atoms.

[0074]

[15] The pigment dispersion according to

[10] or

[11] , wherein the aforementioned (B) dispersant comprises an acrylic dispersant having tertiary amino and / or quaternary ammonium groups.

[0075]

[16] A photosensitive coloring resin composition comprising the pigment dispersion described in

[10] or

[11] and (D) photopolymerization initiator.

[0076]

[17] A cured product obtained by curing the photosensitive coloring resin composition described in any one of [1] to [9] and

[16] .

[0077]

[18] A partition wall formed from the solidified material described in

[17] .

[0078]

[19] An organic electroluminescent element having the partition wall described in

[18] .

[0079]

[20] A color filter having the partition wall described in

[18] and comprising luminescent nanocrystal particles.

[0080]

[21] An image display device comprising the organic electroluminescent element described in

[19] .

[0081]

[22] A compound having the structural unit shown in the following general formula (1).

[0082]

[0083] (In equation (1), R) 1 It represents a hydrogen atom or a methyl group.

[0084] R 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0085] L represents an alkylene group having 2 to 6 carbon atoms, and having at least a hydroxyl group, or a hydroxyl group and an ester group of a polybasic acid as substituents.

[0086] *Each represents a connection key.

[0087] The effects of the invention

[0088] According to the present invention, a photosensitive coloring resin composition with high residual film yield can be provided. Furthermore, a pigment dispersion with excellent dispersibility can be provided. Consequently, it can improve organic electroluminescent elements and image display devices. Attached Figure Description

[0089] Figure 1 This is a cross-sectional schematic diagram of an example of a color filter equipped with the partition wall of the present invention. Detailed Implementation

[0090] The embodiments of the present invention will be described in detail below, but the present invention is not limited to the following embodiments, and various modifications can be made within the scope of its spirit.

[0091] In this invention, "(meth)acrylic acid" refers to "acrylic acid and / or methacrylic acid", and the same applies to "(meth)acrylate" and "(meth)acryloyl".

[0092] "Acrylic resins" refer to (co)polymers containing (meth)acrylic acid or (co)polymers containing (meth)acrylates with carboxyl groups.

[0093] "All solid components" refers to all components in a photosensitive coloring resin composition or pigment dispersion, excluding the solvent. Even if the components other than the solvent are liquid at room temperature, they are not included in the solvent but are included in the total solid components.

[0094] "(Co)polymer" refers to both homopolymer and copolymer, while "acid (anhydride)" and "(anhydrous)...acid" refer to both acid and its anhydride.

[0095] "Monomer" is a term that is used in contrast to so-called high molecular weight substances (polymers). It includes not only monomers in the narrow sense, but also dimers, trimers, and oligomers.

[0096] "Weight-average molecular weight" refers to the weight-average molecular weight (Mw) of polystyrene based on GPC (gel permeation chromatography).

[0097] Unless otherwise specified, the "amine value" represents the amine value converted from the effective solid component, expressed as the mass of KOH equivalent to the amount of alkali per 1g of the dispersant solid component. The determination method will be described later.

[0098] Unless otherwise stated, "acid value" refers to the acid value converted from the effective solid components, calculated through neutralization titration.

[0099] Regarding pigments, "CI" refers to Color Index.

[0100] In this specification, the percentages and parts expressed as "mass" have the same meaning as the percentages and parts expressed as "weight".

[0101] The photosensitive coloring resin composition of the first aspect of the present invention contains (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin and (D) a photopolymerization initiator, wherein (A) the colorant comprises an organic pigment (A-1) and (C) the alkali-soluble resin comprises a resin (C1) as shown in formula (1).

[0102] The pigment dispersion of the second embodiment of the present invention contains (A) a colorant, (B) a dispersant and (C) an alkali-soluble resin, (A) a colorant comprising an organic pigment (A-1) and (C) an alkali-soluble resin comprising a resin (C1) as shown in formula (1).

[0103] Unless otherwise specified, (A) colorant, (B) dispersant, (C) alkali-soluble resin, and (D) photopolymerization initiator refer to the technical features of the photosensitive coloring resin composition of the first method and the pigment dispersion of the second method.

[0104] [Photosensitive coloring resin composition]

[0105] The photosensitive coloring resin composition of the present invention contains:

[0106] (A) Coloring agent

[0107] (B) Dispersant

[0108] (C) Alkali-soluble resin

[0109] (D) Photopolymerization initiator.

[0110] <(A) Coloring agent>

[0111] The photosensitive coloring resin composition of the present invention contains (A) a colorant. By containing (A) a colorant, moderate light absorption can be obtained, and moderate light-blocking properties can be obtained, especially when used for forming light-blocking components such as partition walls.

[0112] The colorant (A) of the present invention contains an organic pigment (A-1). By containing an organic pigment (A-1), it tends to have good insulation properties.

[0113] (A) The pigment contained in the colorant may be a single type or two or more types. From the viewpoint of balancing uniform light blocking in the visible area and OD per unit film thickness, two or more types are preferred.

[0114] There are no particular limitations on the organic pigments that can be used as colorants in (A). Examples include organic coloring pigments and organic black pigments. Here, organic coloring pigments refer to organic pigments that exhibit colors other than black, such as red pigments, orange pigments, blue pigments, purple pigments, green pigments, and yellow pigments.

[0115] Among organic pigments, organic coloring pigments are preferred from the viewpoint of suppressing ultraviolet absorption, resulting in high curability, and easy control over the shape of the cured product. On the other hand, organic black pigments are preferred from the viewpoint of high opacity and the ability to reduce the pigment concentration relative to the solid component.

[0116] Examples of organic black pigments include perylene black pigments, aniline black pigments, and benzodifuranone black pigments.

[0117] Examples of perylene black pigments include Lumogen Black (registered trademark) FK4281, K0087, and Paliogen Black (registered trademark) EH0788 (all manufactured by BASF).

[0118] Examples of aniline-based black pigments include Paliotol Black (registered trademark) L0080, D0080, and K0080 (all manufactured by BASF).

[0119] From the viewpoints of opacity, dispersibility, developability, and luminescence properties, benzodifuranone-based black pigments are preferred as organic black pigments.

[0120] Among benzodifuranone-based black pigments, from the viewpoints of opacity, dispersibility, developability, and luminescence properties, an organic black pigment comprising at least one of the following groups (hereinafter sometimes referred to as "organic black pigment of general formula (A-1-1)"), a geometric isomer of compound (A-1-1), a salt of compound (A-1-1), and a salt of a geometric isomer of compound (A-1-1) is preferred.

[0121]

[0122] In equation (A-1-1), R 611 and R 616 Each can independently represent a hydrogen atom, CH3, CF3, fluorine atom, or chlorine atom;

[0123] R 612 R 613 R 614 R 615 R617 R 618 R 619 and R 620 Each independently represents a hydrogen atom, a halogen atom, and R. 621 COOH, COOR 621 COO - CONH2, CONHR 621 CONR 621 R 622 CN, OH, OR 621 COCR 621 、OOCNH2、OOCNHR 621 OOCNR 621 R 622 NO2, NH2, NHR 621 NR 621 R 622 , NHCOR 622 NR 621 COR 622 N=CH2, N=CHR 621 N = CR 621 R 622 SH, SR 621 、SOR 621 、SO2R 621 SO3R 621 SO3H, SO3 - SO2NH2, SO2NHR 621 or SO2NR 621 R 622 ;

[0124] Choose freely R 612 With R 613 R 613 With R 614 R 614 With R 615 R 617 With R 618 R 618 With R 619 and R 619 With R 620 At least one combination in the group is optionally directly bonded to each other, or optionally bonded via an oxygen atom, sulfur atom, NH or NR atom. 621 Bridges connect them to each other;

[0125] R 621 and R 622 Each can be independently represented as an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an alkynyl group having 2 to 12 carbon atoms.

[0126] The geometric isomers of compound (A-1-1) have the following core structures (where substituents in the structural formulas have been omitted), and the trans-trans isomer is probably the most stable.

[0127]

[0128] When compound (A-1-1) is anionic, it is preferably a salt formed by compensating for its charge using any known suitable cation, such as a metal, organic, inorganic, or organometallic cation, specifically an alkali metal, alkaline earth metal, transition metal, primary ammonium, secondary ammonium, tertiary ammonium such as trialkylammonium, quaternary ammonium such as tetraalkylammonium, or an organometallic complex. Furthermore, when the geometric isomers of compound (A-1-1) are anionic, the same salt is preferably used.

[0129] In formula (A-1-1) and their definitions, the following substituents are preferred based on the tendency to improve the hiding power. This is because the following substituents are considered to have no absorption and will not affect the hue of the pigment.

[0130] R 612 R 614 R 615 R 617 R 619 and R 620 Each atom is preferably a hydrogen atom, a fluorine atom, or a chlorine atom, and is more preferably a hydrogen atom.

[0131] R 613 and R 618 Each of the following is preferably an independent hydrogen atom, NO2, OCH3, OC2H5, bromine atom, chlorine atom, CH3, C2H5, N(CH3)2, N(CH3)(C2H5), N(C2H5)2, α-naphthyl, β-naphthyl, SO3H or SO3 - Further preferred are hydrogen atoms or SO3H, with hydrogen atoms being particularly preferred.

[0132] R 611 and R 616 Each atom is preferably a hydrogen atom, CH3 or CF3, and more preferably a hydrogen atom.

[0133] Preferred selection of free R 611 With R 616 R 612 With R 617 R 613 With R 618 R 614 With R 619 and R 615 With R 620At least one combination in the group is the same, more preferably R 611 With R 616 Same, R 612 With R 617 Same, R 613 With R 618 Same, R 614 With R 619 Same, and R 615 With R 620 same.

[0134] Alkyl groups having 1 to 12 carbon atoms are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, n-hexyl, n-heptyl, n-octyl, 1,1,3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, decyl, undecyl, or dodecyl.

[0135] Cycloalkyl groups having 3 to 12 carbon atoms are, for example, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, trimethylcyclohexyl, thujyl, norbornyl, bornyl, norcareyl, careyl, menthyl, norpinyl, pinyl, adamantane-1-yl or adamantane-2-yl.

[0136] Alkenes having 2 to 12 carbon atoms are, for example, vinyl, allyl, 2-propen-2-yl, 2-buten-1-yl, 3-buten-1-yl, 1,3-butadien-2-yl, 2-penten-1-yl, 3-penten-2-yl, 2-methyl-1-buten-3-yl, 2-methyl-3-buten-2-yl, 3-methyl-2-buten-1-yl, 1,4-pentadien-3-yl, hexenyl, octenyl, nonenyl, decenyl, or dodecenyl.

[0137] Cycloalkenyl groups with 3 to 12 carbon atoms are, for example, 2-cyclobuten-1-yl, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, 2,4-cyclohexadien-1-yl, 1-p-menthene-8-yl, 4(10)-thujene-10-yl, 2-norbornen-1-yl, 2,5-norbornadien-1-yl, 7,7-dimethyl-2,4-norcarbapen-3-yl or camphenyl.

[0138] Examples of alkynyl groups with 2 to 12 carbon atoms include 1-propyn-3-yl, 1-butyn-4-yl, 1-pentyn-5-yl, 2-methyl-3-butyn-2-yl, 1,4-pentadiyn-3-yl, 1,3-pentadiyn-5-yl, 1-hexyn-6-yl, cis-3-methyl-2-penten-4-yn-1-yl, trans-3-methyl-2-penten-4-yn-1-yl, 1,3-hexadiyn-5-yl, 1-octyne-8-yl, 1-nonyn-9-yl, 1-decyn-10-yl, or 1-dodecyn-12-yl.

[0139] Halogen atoms can be, for example, fluorine, chlorine, bromine, or iodine atoms.

[0140] The organic black pigment shown in formula (A-1-1) is preferably an organic black pigment comprising at least one of the following groups: a compound (hereinafter also referred to as "compound (A-1-2)") and a geometrical isomer of compound (A-1-2).

[0141]

[0142] As a compound (A-1-2), for example, the trade name Irgaphor (registered trademark) Black S 0100CF (manufactured by BASF) can be cited.

[0143] The organic black pigment is preferably dispersed using the dispersant, solvent, and method described later. Furthermore, the presence of sulfonic acid derivatives of compound (A-1-1), particularly sulfonic acid derivatives of compound (A-1-2), during dispersion can sometimes improve dispersibility and shelf life; therefore, the organic black pigment preferably contains these sulfonic acid derivatives.

[0144] The chemical structure of organic pigments is not particularly limited; examples include azo, phthalocyanine, quinacridone, benzimidazolone, isoindolinone, dioxazine, indanisole, and perylene series. Below, pigment codes are used to represent specific examples of usable pigments. In the following examples such as "CI Pigment Red 2," "CI" refers to the Color Index.

[0145] As red pigments, examples of CI pigments include 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53: 3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147,1 49, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 23 2, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276. From the viewpoint of light-blocking and dispersibility, CI Pigment Red 48 can be preferentially listed as: 1, 122, 149, 168, 177, 179, 194, 202, 206, 207, 209, 224, 242, 254, and CI Pigment Red 177, 209, 224, 254 can be further preferentially listed. It should be noted that, from the perspective of dispersibility and light-blocking properties, CI Pigment Red 177, 254, and 272 are preferred. When using ultraviolet light to cure the photosensitive coloring resin composition, it is preferable to use a pigment with low ultraviolet absorption rate as the red pigment. From this point of view, CI Pigment Red 254 and 272 are more preferred.

[0146] Examples of orange pigments include CI pigments Orange 1, 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, and 79. From the viewpoints of dispersibility and opacity, CI pigments Orange 13, 43, 64, and 72 are preferred. When curing a photosensitive coloring resin composition using ultraviolet light, pigments with low ultraviolet absorption are preferred as orange pigments; from this viewpoint, CI pigments Orange 64 and 72 are more preferred.

[0147] Examples of blue pigments include CI Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79. From the viewpoint of light-blocking properties, CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, and 60 are preferred, and CI Pigment Blue 15:6 is even more preferred. It should be noted that from the perspective of dispersibility and light-blocking properties, CI Pigment Blue 15:6, 16, and 60 are preferred. When using ultraviolet light to cure a photosensitive resin coloring composition, it is preferable to use a pigment with low ultraviolet absorption rate as the blue pigment. From this point of view, CI Pigment Blue 60 is more preferably used.

[0148] Examples of purple pigments include CI pigments 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50. From the viewpoint of light-blocking properties, CI pigments 19, 23, and 29 are preferred, and CI pigment 23 is even more preferred. It should be noted that CI pigments 23 and 29 are preferred from the perspective of dispersibility and light-blocking properties. When the photosensitive coloring resin composition is cured using ultraviolet light, a pigment with low ultraviolet absorption rate is preferred as the purple pigment, and from this viewpoint, CI pigment 29 is more preferred.

[0149] Examples of green pigments include CI pigments 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, and 59. CI pigments 7 and 36 are preferred examples.

[0150] Examples of yellow pigments include CI pigment yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62:1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127:1, 128, 129, 133, 1 34, 136, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208. CI pigment yellows 83, 117, 129, 138, 139, 150, 154, 155, 180, and 185 can be preferentially listed, and CI pigment yellows 83, 138, 139, 150, and 180 can be further preferentially listed.

[0151] From the viewpoint of the light-blocking properties and shape control of the cured product, it is preferable to use at least one pigment selected from the group consisting of red, orange, blue and purple pigments.

[0152] From the viewpoint of the light-blocking properties and shape control of the cured product, it is preferable to contain at least one of the following pigments.

[0153] Red pigments: CI Pigment Red 177, 254, 272

[0154] Orange pigments: CI pigments orange 43, 64, 72

[0155] Blue pigment: CI Pigment Blue 15:6,60

[0156] Purple pigments: CI pigments purple 23 and 29

[0157] Regarding the combination of organic coloring pigments when using two or more organic coloring pigments in combination, there are no particular limitations. From the viewpoint of light-blocking properties, it is preferable to include at least one pigment selected from the group consisting of red and orange pigments and at least one pigment selected from the group consisting of blue and purple pigments.

[0158] There are no particular limitations on color combinations. From the perspective of light-blocking properties, examples include combinations of red and blue pigments, blue and orange pigments, and blue, orange, and purple pigments.

[0159] As the colorant (A) in the photosensitive coloring resin composition of the present invention, other colorants besides organic pigments (A-1) may also be used in combination. There are no particular limitations on the colorants that can be used in combination; pigments or dyes may be used. Other colorants used in combination with organic pigments may be used individually or in combination of two or more.

[0160] From a durability point of view, pigments are preferred. Inorganic pigments are an example.

[0161] From the perspective of higher opacity, inorganic black pigments are preferred as inorganic pigments.

[0162] Examples of inorganic black pigments include carbon black, acetylene black, lampblack, bone black, graphite, iron black, cyanine black, and titanium black.

[0163] From the perspective of light-blocking properties and image characteristics, carbon black is the preferred choice.

[0164] Examples of carbon black include the following.

[0165] Manufactured by Mitsubishi Chemical Corporation: MA7, MA8, MA11, MA77, MA100, MA100R, MA100S, MA220, MA230, MA600, MCF88, #5, #10, #20, #25, #30, #32, #33, #40, #44, #45, #47, #50, #52, #55, #650, #750, #850, #900, #950, #9 60, #970, #980, #990, #1000, #2200, #2300, #2350, #2400, #2600, #2650, #3030, #3050, #315 0, #3250, #3400, #3600, #3750, #3950, #4000, #4010, OIL7B, OIL9B, OIL11B, OIL30B, OIL31B.

[0166] Made by DEGUSSA: Printex (registered trademark, the same below) 3, Printex3OP, Printex30, Printex30OP, Printex40, Printex45, Printex55, Printex60, Printex75, Printex80, Printex85, Printex90, Printex A, Printex L, Printex G, Printex P, Printex U, PrintexV, PrintexG, SpecialBlack550, SpecialBlack350, SpecialBlack250, SpecialBlack100, SpecialBlack6, SpecialBlack5, SpecialBlack4, Color Black FW1, Color Black FW2, Color Black FW2V, Color Black FW18, Color Black FW200, Color Black S160, ColorBlack S170.

[0167] Manufactured by Cabot Corporation: Monarch (registered trademark, same below) 120, Monarch 280, Monarch 460, Monarch 800, Monarch 880, Monarch 900, Monarch 1000, Monarch 1100, Monarch 1300, Monarch 1400, Monarch 4630, REGAL (registered trademark, same below) 99, REGAL 99R, REGAL 415, REGAL 415R, REGAL 250, REGAL 250R, REGAL 330, REGAL 400R, REGAL 550R, REGAL 660R, BLACK PEARLS 480, PEARLS 130, VULCAN (registered trademark, same below) XC72R, ELFTEX (registered trademark) -8.

[0168] Birla Manufactured by Corporation: RAVEN (registered trademark, the same below) 11, RAVEN14, RAVEN15, RAVEN16, RAVEN22, RAVEN30, RAVEN35, RAVEN40, RAVEN410, RAVEN420, RAVEN450, RAVEN500, RAVEN780, RAVEN850, RAVEN890H, RAVEN 1000, RAVEN1020, RAVEN1040, RAVEN1060U, RAVEN1080U, RAVEN1170, RAVEN1190U, RAVEN1250, RAVEN1500, RAVEN2000, RAVEN2500U, RAVEN3500, RAVEN5000, RAVEN5250, RAVEN5750, RAVEN7000.

[0169] Carbon black that has undergone acid treatment on its surface can be used. For example, the carbon black described in Japanese Patent No. 3674086 can be used suitably. Alternatively, resin-coated carbon black can also be used. Using resin-coated carbon black improves the adhesion to the glass substrate and reduces the volume resistivity. As a resin-coated carbon black, the carbon black described in Japanese Patent Application Publication No. 09-71733 can be used suitably. Resin-coated carbon black is preferred in terms of volume resistivity and dielectric constant.

[0170] These pigments are preferably used in a manner where the average particle size is preferably 1 μm or less, more preferably 0.5 μm or less, and even more preferably 0.25 μm or less. Here, the average particle size is based on the number of pigment particles.

[0171] In the photosensitive coloring resin composition of the present invention, the average particle size of the pigment is a value determined by measuring the pigment particle size using dynamic light scattering (DLS). The particle size determination is performed on a sufficiently diluted photosensitive coloring resin composition (typically, dilution is performed to adjust the pigment concentration to approximately 0.005–0.2% by mass. However, if a recommended concentration is available in the measuring equipment, that concentration is used), and at 25°C.

[0172] In addition to the organic and inorganic pigments mentioned above, dyes can also be used. Examples of dyes that can be used as coloring agents include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinone imine dyes, quinoline dyes, nitro dyes, carbonyl dyes, and methylene dyes.

[0173] Examples of azo dyes include CI Acid Yellow 11, CI Acid Orange 7, CI Acid Red 37, CI Acid Red 180, CI Acid Blue 29, CI Direct Red 28, CI Direct Red 83, CI Direct Yellow 12, CI Direct Orange 26, CI Direct Green 28, CI Direct Green 59, CI Reactive Yellow 2, CI Reactive Red 17, CI Reactive Red 120, CI Reactive Black 5, CI Disperse Orange 5, CI Disperse Red 58, CI Disperse Blue 165, CI Basic Blue 41, CI Basic Red 18, CI Mordant Red 7, CI Mordant Yellow 5, and CI Mordant Black 7.

[0174] Examples of anthraquinone dyes include CI Vat Blue 4, CI Acid Blue 40, CI Acid Green 25, CI Reactive Blue 19, CI Reactive Blue 49, CI Disperse Red 60, CI Disperse Blue 56, and CI Disperse Blue 60.

[0175] Examples of phthalocyanine dyes include CI Variant Blue 5.

[0176] Examples of quinone imine dyes include Basic Blue 3 and Basic Blue 9.

[0177] Examples of quinoline dyes include CI Solvent Yellow 33, CI Acid Yellow 3, and CI Disperse Yellow 64.

[0178] Examples of nitro dyes include CI Acid Yellow 1, CI Acid Orange 3, and CI Disperse Yellow 42.

[0179] <(B) Dispersant>

[0180] To ensure quality stability, and in order to finely disperse (A) the colorant and stabilize its dispersion, the photosensitive coloring resin composition of the present invention includes (B) a dispersant.

[0181] As the dispersant (B), a polymeric dispersant with functional groups is preferred. Furthermore, from the perspective of dispersion stability, polymeric dispersants with functional groups such as carboxyl groups, phosphate groups, sulfonic acid groups, or their salts, primary, secondary, or tertiary amine groups, quaternary ammonium groups, or groups derived from nitrogen-containing heterocycles such as pyridine, pyrimidine, and pyrazine are preferred. In particular, polymeric dispersants with basic functional groups such as primary, secondary, or tertiary amine groups, quaternary ammonium groups, or groups derived from nitrogen-containing heterocycles such as pyridine, pyrimidine, and pyrazine are especially preferred from the viewpoint that pigments can be dispersed with a small amount of dispersant.

[0182] Examples of polymeric dispersants include urethane dispersants, acrylic dispersants, polyethyleneimine dispersants, polyallylamine dispersants, dispersants containing monomers with amino groups and macromonomers, polyoxyethylene alkyl ether dispersants, polyoxyethylene diester dispersants, polyether phosphoric acid dispersants, polyester phosphoric acid dispersants, sorbitan aliphatic ester dispersants, and aliphatic modified polyester dispersants.

[0183] Examples of such dispersants, listed by trade name, include EFKA (registered trademark, manufactured by BASF), DISPERBYK (registered trademark, manufactured by BYK-Chemie), DISPARLON (registered trademark, manufactured by Kusunoki Chemical Co., Ltd.), SOLSPERSE (registered trademark, manufactured by Lubrizol Corporation), KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), and AJISPER (registered trademark, manufactured by Ajinomoto Co., Ltd.).

[0184] Polymer dispersants can be used alone or in combination of two or more.

[0185] From the viewpoint of pigment dispersibility, (B) the dispersant preferably includes either or both of a urethane polymeric dispersant and an acrylic polymeric dispersant having functional groups, and particularly preferably includes an acrylic polymeric dispersant.

[0186] From the perspective of dispersibility and preservation, polymeric dispersants with basic functional groups, polyester bonds, and polyether bonds, or both, are preferred.

[0187] As a urethane and acrylic polymeric dispersant, examples include the DISPERBYK-160~167, 182 series (all urethane), DISPERBYK-2000, 2001, and BYK-LPN21116 (all acrylic) (all manufactured by BYK-Chemie).

[0188] The amine value of the polymeric dispersant with basic functional groups is not particularly limited, but is preferably 1 mg KOH / g or more, more preferably 10 mg KOH / g or more, further preferably 20 mg KOH / g or more, even more preferably 40 mg KOH / g or more, and particularly preferably 50 mg KOH / g or more. Furthermore, it is preferably 140 mg KOH / g or less, more preferably 120 mg KOH / g or less, further preferably 100 mg KOH / g or less, even more preferably 90 mg KOH / g or less, and particularly preferably 80 mg KOH / g or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1–140 mg KOH / g, more preferably 10–120 mg KOH / g, further preferably 20–100 mg KOH / g, even more preferably 40–90 mg KOH / g, and particularly preferably 50–80 mg KOH / g. By setting it to the aforementioned lower limit value or above, there is a tendency for improved dispersibility. By setting it below the aforementioned upper limit, there is a tendency for improved compatibility with (C) alkali-soluble resin.

[0189] From a dispersibility perspective, acrylic dispersants are preferably AB or BAB block copolymers composed of A blocks having the aforementioned functional groups and B blocks not having the aforementioned functional groups. In this case, the A blocks may contain, in addition to partial structures derived from monomers containing unsaturated groups that include the aforementioned functional groups, partial structures derived from monomers containing unsaturated groups that do not include the aforementioned functional groups. These partial structures may also be included in the A blocks in any manner, either through random copolymerization or block copolymerization. The proportion of the partial structures in the A blocks that do not contain functional groups is preferably 80% by mass or less, more preferably 50% by mass or less, further preferably 30% by mass or less, even more preferably 10% by mass or less, and particularly preferably 0% by mass.

[0190] From the perspective of dispersion, the B block is preferably composed only of partial structures derived from monomers containing unsaturated groups that do not contain the above-mentioned functional groups. A B block may also contain partial structures derived from two or more monomers, which can be included in the B block in any manner of random copolymerization or block copolymerization.

[0191] AB or BAB block copolymers are prepared, for example, by the living polymerization method shown below.

[0192] Living polymerization methods include anionic living polymerization, cationic living polymerization, and free radical living polymerization. Among them, the active species in anionic living polymerization is anion, as shown in the following roadmap.

[0193] (Anionic Living Polymerization)

[0194]

[0195] In the above route map, Ar 1 Ar is a monovalent organic group. 2 To be with Ar 1 Different monovalent organic groups, M is a metal atom, and s and t are integers greater than or equal to 1.

[0196] The active species in free radical living polymerization are free radicals, as shown in the following roadmap.

[0197] (Free radical living polymerization)

[0198] (Nitroacyl method)

[0199]

[0200] (ATRP method)

[0201]

[0202] In the above route map, Ar 1 Ar is a monovalent organic group. 2 To be with Ar 1 Different monovalent organic groups, j and k are integers greater than 1, R a R is a hydrogen atom or a monovalent organic group. b To be with R a Different hydrogen atoms or monovalent organic groups.

[0203] In synthesizing this acrylic dispersant, the following methods can be used: Japanese Patent Application Publication No. 9-62002, P. Lutz, P. Masson et al, Polym. Bull. 12, 79 (1984), BC Anderson, GD Andrews et al, Macromolecules, 14, 1601 (1981), K. Hatada, K. Ute, et al, Polym. J. 17, 977 (1985), K. Hatada, K. Ute, et al. The known methods described in al, Polym.J.18,1037 (1986), Koichi Uezu, Koichi Hatada, Polymer Processing, 36,366 (1987), Toshinobu Higashimura, Mitsuo Sawamoto, Collected Papers on Polymers, 46,189 (1989), M. Kuroki, T. Aida, J. Am. Chem. Sic, 109,4737 (1987), Takuzo Aida, Shohei Inoue, Organic Synthetic Chemistry, 43,300 (1985), DY Sogoh, WR Hertler et al, Macromolecules, 20,1473 (1987), etc.

[0204] The acrylic dispersant used in this invention can be an AB block copolymer or a BAB block copolymer. The A-block / B-block ratio of the copolymer is not particularly limited, but preferably 1 / 99 to 80 / 20 (mass ratio), more preferably 5 / 95 to 60 / 40 (mass ratio). By setting it within this range, there is a tendency to easily ensure a balance between dispersibility and storage stability.

[0205] In this invention, the amount of quaternary ammonium groups in 1g of the AB block copolymer or BAB block copolymer is preferably 0.1 to 10 mmol. By setting it within this range, it is easier to ensure good dispersibility.

[0206] Such acrylic dispersants may also contain amino groups. The amine value of the acrylic dispersant is preferably 1 mg KOH / g or more, more preferably 10 mg KOH / g or more, further preferably 20 mg KOH / g or more, even more preferably 40 mg KOH / g or more, and particularly preferably 50 mg KOH / g or more. Furthermore, it is preferably 140 mg KOH / g or less, more preferably 120 mg KOH / g or less, further preferably 100 mg KOH / g or less, even more preferably 90 mg KOH / g or less, and particularly preferably 80 mg KOH / g or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1–140 mg KOH / g, more preferably 10–120 mg KOH / g, further preferably 20–100 mg KOH / g, even more preferably 40–90 mg KOH / g, and particularly preferably 50–80 mg KOH / g. By setting it to the aforementioned lower limit or above, there is a tendency for improved dispersibility. By setting it below the aforementioned upper limit, there is a tendency for improved compatibility with (C) alkali-soluble resin.

[0207] Here, the amine value of acrylic dispersants is expressed as the mass of KOH equivalent to the amount of alkali per 1g of solid component in the dispersant sample after solvent removal, and is determined using the following method.

[0208] Accurately weigh 0.5–1.5 g of the dispersant sample into a 100 mL beaker and dissolve it in 50 mL of acetic acid. Using an automatic titration apparatus equipped with a pH electrode, neutralize and titrate the solution with 0.1 mol / L HClO4 acetic acid solution. Take the inflection point of the pH titration curve as the titration endpoint and calculate the amine value using the following formula.

[0209] Amine value [mgKOH / g] = (561 × V) / (W × S)

[0210] [Where, W: represents the amount of dispersant sample weighed [g], V: represents the titration volume at the titration endpoint [mL], and S: represents the concentration of the solid component of the dispersant sample [mass %].]

[0211] The weight-average molecular weight (Mw) of the acrylic dispersant is not particularly limited, but is preferably 1000 or more, more preferably 3000 or more, further preferably 4000 or more, and particularly preferably 5000 or more. Additionally, it is preferably 50000 or less, more preferably 20000 or less, and further preferably 15000 or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1000 to 50000, more preferably 3000 to 50000, further preferably 4000 to 20000, and particularly preferably 5000 to 15000. By setting it to the aforementioned lower limit or above, there is a tendency for better dispersibility; conversely, by setting it to the aforementioned upper limit or below, there is a tendency for viscosity changes to be less likely.

[0212] As an acrylic dispersant, it is preferred to have tertiary amino and / or quaternary ammonium groups.

[0213] When an acrylic dispersant has a quaternary ammonium group as a functional group, the chemical structure of the repeating unit containing the quaternary ammonium group is not particularly limited. From the viewpoint of dispersibility, an acrylic dispersant preferably has a repeating unit shown in the following general formula (V) (hereinafter sometimes referred to as "repeating unit (V)").

[0214]

[0215] In equation (V), R 31 ~R 33 Each is independently a hydrogen atom, optionally an alkyl group with substituents, optionally an aryl group with substituents, or optionally an aralkyl group with substituents, R 31 ~R 33 Two or more of them can bond together to form a ring structure. R 34 It can be a hydrogen atom or a methyl group. X 31 It is a divalent linker, Y - To counteract anions.

[0216] R of equation (V) 31 ~R 33 The alkyl group with substituents can be either straight-chain or branched. Additionally, it may contain cyclic structures such as cyclohexyl or cyclohexylmethyl. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 or more, more preferably 10 or less, more preferably 6 or less, further preferably 4 or less, and particularly preferably 2 or less. For example, it is preferably 1 to 10, more preferably 1 to 6, further preferably 1 to 4, and particularly preferably 1 to 2.

[0217] Examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl, with methyl, ethyl, propyl, butyl, pentyl, and hexyl being preferred, methyl, ethyl, propyl, and butyl being more preferred, and methyl and ethyl being even more preferred.

[0218] R of equation (V) 31 ~R 33 The number of carbon atoms in the aryl group with substituents is not particularly limited, but is preferably 6 or more, and more preferably 16 or less, and more preferably 12 or less. For example, 6 to 16 is preferred, and more preferably 6 to 12. Examples of aryl groups include phenyl, methylphenyl, ethylphenyl, dimethylphenyl, diethylphenyl, naphthyl, and anthracene, with phenyl, methylphenyl, ethylphenyl, dimethylphenyl, and diethylphenyl being preferred, and phenyl, methylphenyl, and ethylphenyl being more preferred.

[0219] R of equation (V) 31 ~R 33 The number of carbon atoms in the optional aralkyl group with substituents is not particularly limited, but is preferably 7 or more, and more preferably 16 or less, more preferably 12 or less, further preferably 10 or less, and particularly preferably 8 or less. For example, 7 to 16 is preferred, more preferably 7 to 12, further preferably 7 to 10, and particularly preferably 7 to 8. Examples of aralkyl groups include phenylmethyl, phenylethyl, phenylpropyl, phenylbutyl, and phenylisopropyl, with phenylmethyl, phenylethyl, phenylpropyl, and phenylbutyl being preferred, and phenylmethyl and phenylethyl being more preferred.

[0220] From a decentralized perspective, R 31 ~R 33 Each is preferably an alkyl or aralkyl group, R 31 ~R 33 Each of them is preferably methyl or phenylmethyl.

[0221] Y in equation (V) - For example, Cl can be listed - ,Br - , I - ClO4 - BF4 - CH3COO - PF - .

[0222] In addition, the aromatic dicarboxylic acid imide anion, aromatic sulfonic acid anion, aromatic phosphonic acid anion, and aromatic carboxylic acid anion described in International Publication No. 2018 / 079659; and the alkyl sulfate anion and alkyl sulfonic acid anion described in International Publication No. 2019 / 107020 may also be used appropriately.

[0223] As Y- From the viewpoint of development morphology, Cl is preferred. - From the viewpoint of luminescent properties, alkyl sulfonic acid anions are preferred.

[0224] When a polymeric dispersant has a tertiary amine as a functional group, from the viewpoint of dispersibility and luminescence properties, it is preferable to have a repeating unit as shown in the following general formula (VI) (hereinafter sometimes referred to as "repeating unit (VI)").

[0225]

[0226] In equation (VI), R 35 and R 36 Each is independently a hydrogen atom, optionally an alkyl group with substituents, optionally an aryl group with substituents, or optionally an aralkyl group with substituents, R 35 and R 36 They can be arbitrarily bonded together to form a ring structure. R 37 It can be a hydrogen atom or a methyl group. Z 31 It is a divalent linker.

[0227] R as in equation (VI) 35 and R 36 The optional alkyl group having a substituent may preferably be used as R in formula (V). 31 ~R 33 The exemplified groups.

[0228] R as in equation (VI) 35 and R 36 The optional aryl group with substituents in formula (V) can preferably be used as R. 31 ~R 33 The exemplified groups.

[0229] R as in equation (VI) 35 and R 36 The optional aryl group in the formula (V) may preferably be used as R. 31 ~R 33 The exemplified groups.

[0230] From the perspective of dispersibility and luminescence properties, R 35 and R 36 Preferably, each is an alkyl group that has optional substituents, more preferably methyl or ethyl.

[0231] R as in equation (V) 31 ~R 33 and R of formula (VI) 35 and R 36The alkyl, aralkyl, or aryl groups may optionally have substituents, such as halogen atoms, alkoxy groups, benzoyl groups, and hydroxyl groups.

[0232] As X in equation (V) 31 and Z in equation (VI) 31 Examples include alkylene groups with 1 to 10 carbon atoms, aryl groups with 6 to 12 carbon atoms, and -CONH-R groups. 43 -base, -COOR 44 -Base (where R) 43 and R 44 It is a single bond, an alkylene group having 1 to 10 carbon atoms, or an ether group (alkoxyalkyl) having 2 to 10 carbon atoms, preferably -COO-R. 44 --based, more preferably -COO-C2H4-based.

[0233] From the viewpoint of dispersion, it is preferable to have repeating units (V), and further, from the viewpoint of luminescence properties, it is preferable to have repeating units (V) and repeating units (VI).

[0234] The proportion of the repeating unit (V) in all the repeating units of the dispersant is not particularly limited, but from the viewpoint of dispersibility, it is preferably 1 mol% or more, more preferably 3 mol% or more, further preferably 5 mol% or more, and particularly preferably 8 mol% or more. In addition, it is preferably 50 mol% or less, more preferably 30 mol% or less, further preferably 20 mol% or less, and particularly preferably 15 mol% or less.

[0235] The proportion of the repeating unit (VI) in all repeating units of the dispersant is not particularly limited, but from the viewpoint of dispersibility, it is preferably 5 mol% or more, more preferably 10 mol% or more, further preferably 15 mol% or more, and particularly preferably 20 mol% or more. Additionally, it is preferably 60 mol% or less, more preferably 40 mol% or less, further preferably 30 mol% or less, and particularly preferably 25 mol% or less.

[0236] From the viewpoint of improving compatibility with alkali-soluble resin components such as solvents and improving dispersion stability, acrylic dispersants preferably have repeating units shown in the following general formula (VII) (hereinafter sometimes referred to as "repeating unit (VII)").

[0237]

[0238] In equation (VII), R 40 It is ethylene or propylene, R 41 R is an alkyl group that is optionally substituted. 42 It can be a hydrogen atom or a methyl group. n is an integer from 1 to 20.

[0239] R in equation (VII) 41 The alkyl group with substituents can be either straight-chain or branched. Additionally, it may include cyclic structures such as cyclohexyl or cyclohexylmethyl. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less. Examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl, with methyl, ethyl, propyl, butyl, pentyl, and hexyl being preferred, and methyl, ethyl, propyl, and butyl being more preferred.

[0240] From the viewpoint of compatibility and dispersibility with alkali-soluble resin components such as solvents, n in formula (VII) is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 10 or less, more preferably 5 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 2 to 5.

[0241] The proportion of the repeating unit (VII) in all repeating units of the dispersant is not particularly limited, but is preferably 1 mol% or more, more preferably 2 mol% or more, and even more preferably 4 mol% or more. Furthermore, it is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1 to 30 mol%, more preferably 2 to 20 mol%, and even more preferably 4 to 10 mol%. Within the aforementioned ranges, there is a tendency to easily balance compatibility with alkali-soluble resin components such as solvents and dispersion stability.

[0242] From the viewpoint of improving the compatibility of dispersants with alkali-soluble resin components such as solvents and improving dispersion stability, acrylic dispersants preferably have repeating units shown in the following general formula (VIII) (hereinafter sometimes referred to as "repeating unit (VIII)").

[0243]

[0244] In equation (VIII), R 38 R can be an alkyl group with a substituent, an aryl group with a substituent, or an aralkyl group with a substituent. 39 It can be a hydrogen atom or a methyl group.

[0245] R in equation (VIII) 38The alkyl group with substituents can be either straight-chain or branched. Additionally, it may include cyclic structures such as cyclohexyl or cyclohexylmethyl. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 or more, more preferably 2 or more, and even more preferably 4 or more. Furthermore, it is preferably 10 or less, more preferably 8 or less. Examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and 2-ethylhexyl, with methyl, ethyl, propyl, butyl, pentyl, hexyl, and 2-ethylhexyl being more preferred, and methyl, ethyl, propyl, butyl, and 2-ethylhexyl being even more preferred.

[0246] R in equation (VIII) 38 The number of carbon atoms in the aryl group with substituents is not particularly limited, but is preferably 6 or more. Furthermore, it is preferably 16 or less, more preferably 12 or less, and even more preferably 8 or less. For example, 6 to 16 is preferred, more preferably 6 to 12, and even more preferably 6 to 8. Examples of aryl groups include phenyl, methylphenyl, ethylphenyl, dimethylphenyl, diethylphenyl, naphthyl, and anthracene, with phenyl, methylphenyl, ethylphenyl, dimethylphenyl, and diethylphenyl being preferred, and phenyl, methylphenyl, and ethylphenyl being even more preferred.

[0247] R in equation (VIII) 38 The number of carbon atoms in the optional aralkyl group with substituents is not particularly limited, but is preferably 7 or more, and more preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less. For example, 7 to 16 is preferred, more preferably 7 to 12, and even more preferably 7 to 10. Examples of aralkyl groups include phenylmethyl, phenylethyl, phenylpropyl, phenylbutyl, and phenylisopropyl, with phenylmethyl, phenylethyl, phenylpropyl, or phenylbutyl being preferred, and phenylmethyl or phenylethyl being more preferred.

[0248] From the perspective of solvent compatibility and dispersion stability, R is preferred. 38 It is an alkyl or aralkyl group, more preferably methyl, ethyl, butyl, 2-ethylhexyl or phenylmethyl.

[0249] As R 38 The alkyl group may optionally have substituents, such as halogen atoms and alkoxy groups. The aryl or aralkyl group may optionally have substituents, such as chain-like alkyl groups, halogen atoms, and alkoxy groups. R 38 The chain-like alkyl groups shown include either straight-chain or branched-chain forms.

[0250] From a dispersibility perspective, the proportion of the repeating unit (VIII) in all repeating units of the dispersant is preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 50 mol% or more. Furthermore, it is preferably 80 mol% or less, more preferably 70 mol% or less. The above upper and lower limits can be combined arbitrarily. For example, 30-80 mol% is preferred, more preferably 40-80 mol%, and even more preferably 50-70 mol%.

[0251] Acrylic dispersants may also have repeating units other than repeating units (V), (VI), (VII), and (VIII). Examples of such repeating units include: styrene-based monomers such as styrene and α-methylstyrene; (meth)acrylate monomers such as (meth)acryloyl chloride; (meth)acrylamide monomers such as (meth)acrylamide and N-hydroxymethylacrylamide; and repeating units of monomers such as vinyl acetate, acrylonitrile, allyl glycidyl ether, crotonic glycidyl ether, and N-methacryloylmorpholine.

[0252] From the viewpoint of further improving dispersibility, acrylic dispersants are preferably block copolymers comprising A blocks having repeating units (V) and (VI) and B blocks not having repeating units (V) and (VI). The block copolymers are preferably AB block copolymers or BAB block copolymers. Surprisingly, by introducing not only quaternary ammonium groups but also tertiary amine groups into the A blocks, the dispersing ability of the dispersant tends to be significantly improved. Furthermore, the B blocks preferably have repeating units (VII), and more preferably also have repeating units (VIII).

[0253] In an A block, repeating units (V) and repeating units (VI) can be contained in any manner, such as random copolymerization or block copolymerization. Furthermore, repeating units (V) and repeating units (VI) can each contain more than two types in one A block; in this case, each repeating unit can be contained in the A block in any manner, such as random copolymerization or block copolymerization.

[0254] Block A may also contain repeating units other than repeating units (V) and (VI). Examples of such repeating units include repeating units derived from the aforementioned (meth)acrylate monomers. The content of repeating units other than repeating units (V) and (VI) in block A is preferably 0 to 50 mol%, more preferably 0 to 20 mol%, and particularly preferably, block A does not contain such repeating units.

[0255] The B block may also contain repeating units other than repeating units (VII) and (VIII). Examples of such repeating units include: styrene-based monomers such as styrene and α-methylstyrene; (meth)acrylate-based monomers such as (meth)acryloyl chloride; (meth)acrylamide-based monomers such as (meth)acrylamide and N-hydroxymethylacrylamide; and repeating units of monomers such as vinyl acetate, acrylonitrile, allyl glycidyl ether, crotonic glycidyl ether, and N-methacryloylmorpholine. The proportion of repeating units other than repeating units (VII) and (VIII) in the B block is preferably 0 to 50 mol%, more preferably 0 to 20 mol%, and particularly preferably, the B block does not contain such repeating units.

[0256] These acrylic dispersants can be used alone or in combination of two or more.

[0257] <(C) Alkali-soluble resin>

[0258] The photosensitive coloring resin composition of the present invention contains (C) an alkali-soluble resin. (C) The alkali-soluble resin contains a resin (C1) having a structural unit represented by the following general formula (1).

[0259]

[0260] In equation (1), R 1 It represents a hydrogen atom or a methyl group.

[0261] R 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0262] L represents an alkylene group having 2 to 6 carbon atoms, and having at least a hydroxyl group, or a hydroxyl group and an ester group of a polybasic acid as substituents.

[0263] *Each represents a connection key.

[0264] Resin (C1) has a high affinity for pigments and contains methylene groups in its main chain, giving it flexibility to follow pigments and thus tending to exhibit high pigment dispersibility. Furthermore, resin (C1) contains a large number of aromatic rings in its main chain, resulting in high developer resistance during development and high heat resistance during calcination in photosensitive coloring resin compositions, thus tending to have a higher residual film rate. A high residual film rate tends to prevent decomposition products, byproducts, uncured substances, etc., from remaining or re-adhering to the electrode (anode) in the composition.

[0265] Furthermore, when using a separator obtained by curing a photosensitive coloring resin composition to form an organic electroluminescent element, by reducing the residue and reattachment on the anode, less accumulation occurs in the pixel portion, and the current density when voltage is applied tends to increase and the brightness of the light-emitting element tends to increase.

[0266] (R 2 )

[0267] R in equation (1) 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0268] From the perspective of solvent solubility, R 2 The alkyl group in the alkyl group preferably has 1 or more carbon atoms, and more preferably 3 or less, and more preferably 2 or less.

[0269] The alkyl group can be straight-chain or branched. Examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, and tert-butyl. From a dispersibility point of view, methyl is preferred.

[0270] (L)

[0271] L represents an alkylene group having 2 to 6 carbon atoms, and having at least a hydroxyl group, or a hydroxyl group and an ester group of a polybasic acid as substituents.

[0272] L is preferably 3 or more carbon atoms, more preferably 4 carbon atoms. Additionally, it is preferably 5 or less. For example, it can be 3 to 6, 3 to 5, 4 to 6, or 4 to 5.

[0273] L has at least a hydroxyl group, or a hydroxyl group and an ester group of a polyacid as a substituent, and can also be replaced by a methoxy or ethoxy group.

[0274] Here, "polyacid" refers to the polyacids listed in the polyacid residues described below. Additionally, "ester group of a hydroxyl group with a polyacid" refers to the group where the hydroxyl group bonded to L forms an ester with the polyacid.

[0275] In the structural unit of formula (1), it is preferred to have the structural unit described in the following general formula (2).

[0276]

[0277] (In formula (2), A represents a hydrogen atom or a polyacid residue.)

[0278] R 1 It represents a hydrogen atom or a methyl group.

[0279] R 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0280] *Each represents a connection key.

[0281] (A)

[0282] In formula (1), A represents a hydrogen atom or a polyacid residue.

[0283] A polybasic acid residue refers to a monovalent or divalent group obtained by removing one or two OH groups from a polybasic acid. Examples of such polybasic acids include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenone tetracarboxylic acid, methylhexahydrophthalic acid, methylenetetrahydrophthalic acid, chloramphenicol, methyltetrahydrophthalic acid, and biphenyltetracarboxylic acid.

[0284] From the viewpoint of dispersion stability, maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, and biphenyl tetracarboxylic acid are preferred, and phthalic acid, succinic acid, trimellitic acid, and pyromellitic acid are more preferred.

[0285] Especially when the acid value is set to the same, trimellitic acid is preferred because the number of hydroxyl groups with high solvent affinity is relatively increased compared to the aforementioned polybasic acid residues.

[0286] (R 1 )

[0287] R in equation (1) 1 This represents a hydrogen atom or a methyl group. From the viewpoint of curability, a hydrogen atom is preferred.

[0288] (R 2 )

[0289] R in equation (1) 2 Each can be used independently to represent an alkyl group having 1 to 4 carbon atoms.

[0290] From the perspective of solvent solubility, R 2 The alkyl group in the alkyl group preferably has 1 or more carbon atoms, and more preferably 3 or less, and more preferably 2 or less.

[0291] The alkyl group can be straight-chain or branched. Examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, and tert-butyl. From a dispersibility point of view, methyl is preferred.

[0292] The partial structure represented by formula (1) contained in the resin (C1) can be one type or two or more types. For example, it can be a mixture of a structure where A is a hydrogen atom and a structure where A is a polybasic acid residue.

[0293] As a resin (C1), for example, the structures shown in the following general formulas (C1-1) to (C1-8) can be listed.

[0294]

[0295]

[0296]

[0297] From the viewpoint of dispersion stability, the structure shown in formula (C1-1), formula (C1-3), formula (C1-7), and formula (C1-8) is preferred as the resin (C1).

[0298] The acid value of the resin (C1) is not particularly limited, but is preferably 10 mg KOH / g or more, more preferably 30 mg KOH / g or more, further preferably 40 mg KOH / g or more, and even more preferably 50 mg KOH / g or more. It is also preferably 200 mg KOH / g or less, more preferably 150 mg KOH / g or less, even more preferably 100 mg KOH / g or less, and particularly preferably 80 mg KOH / g or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 10–200 mg KOH / g, more preferably 30–150 mg KOH / g, further preferably 40–100 mg KOH / g, and even more preferably 50–80 mg KOH / g. By setting it to the aforementioned lower limit or above, there is a tendency for improved developing solubility and better resolution. By setting it to the aforementioned upper limit or below, there is a tendency for better residual film yield.

[0299] The method of manufacturing the resin (C1) is not particularly limited. For example, it can be obtained by adding (meth)acrylic acid to the epoxy resin shown in the following general formula (1-2) and then reacting it with a polybasic acid and / or its anhydride.

[0300]

[0301] R in equation (1-2) 2 The meaning of 'and' is the same as that of equation (1).

[0302] Examples of epoxy resins that can be used as the epoxy resins shown in formula (1-2) include the following epoxy resins.

[0303]

[0304] In the above formula, m represents an integer from 2 to 8.

[0305] As a method for adding (meth)acrylic acid to the epoxy resin shown in formula (1-2), known techniques can be used. For example, the epoxy resin can be reacted with (meth)acrylic acid at a temperature of 50–150°C in the presence of an esterification catalyst. Examples of esterification catalysts used herein include tertiary amines such as triethylamine, trimethylamine, benzyldimethylamine, and benzyldiethylamine; and quaternary ammonium salts such as tetramethylammonium chloride, tetraethylammonium chloride, and dodecyltrimethylammonium chloride.

[0306] Examples of polybasic acids and / or their anhydrides include the aforementioned polybasic acids and their anhydrides. Addition reactions of polybasic acids and / or their anhydrides can be carried out using well-known methods.

[0307] The photosensitive coloring resin composition used in this invention may contain an alkali-soluble resin (C) other than resin (C1). There are no particular limitations on any resin exhibiting alkali solubility; examples include resins containing carboxyl or hydroxyl groups. More specifically, examples include epoxy (meth)acrylate resins, acrylic resins, carboxyl-containing epoxy resins, carboxyl-containing urethane resins, phenolic varnish resins, polyvinylphenol resins, and resins containing an isocyanuric acid backbone. As an alkali-soluble resin (C) other than resin (C1), the following resins are particularly suitable from the viewpoint of excellent plate-making properties.

[0308] (C2) Epoxy (meth)acrylate resin

[0309] (C3) Resins containing isocyanuric acid backbone

[0310] (C4) Acrylic copolymer resin

[0311] They can be used individually or in combination of two or more.

[0312] <(C2)Epoxy (meth)acrylate resin>

[0313] The (C2) epoxy (meth)acrylate resin in this invention is a (C) alkali-soluble resin other than (C1). It is obtained by further reacting a hydroxyl group generated through the reaction of an epoxy compound (epoxy resin) with an α,β-unsaturated monocarboxylic acid and / or an α,β-unsaturated monocarboxylic acid ester having a carboxyl group in the ester moiety with a compound having two or more substituents capable of reacting with a polybasic acid and / or its anhydride. However, the (C3) resin containing an isocyanuric acid backbone, described later, is not included.

[0314] Resins obtained by reacting a compound having two or more substituents capable of reacting with a hydroxyl group before reacting the aforementioned polybasic acid and / or its anhydride with a hydroxyl group are also included in (C2) epoxy (meth) acrylate resins.

[0315] From the viewpoints of residual film rate, venting, and plate-making properties, as an alkali-soluble resin, it is preferable to have an epoxy (meth) acrylate resin in addition to resin (C1).

[0316] Resins obtained by reacting the carboxyl group of the resin obtained through the above reaction with a compound having a functional group capable of further reaction are also included in (C2) epoxy (meth) acrylate resins.

[0317] Epoxy (meth)acrylate resins do not actually have epoxy groups in their chemical structure and are not limited to "(meth)acrylate". However, since epoxy compounds (epoxy resins) are used as raw materials and "(meth)acrylate" is a representative example, it is conventionally named in this way.

[0318] As the (C2) epoxy (meth) acrylate resin used in this invention, from the viewpoint of developability and reliability, the following epoxy (meth) acrylate resin (C2-1) and / or epoxy (meth) acrylate resin (C2-2) (hereinafter sometimes referred to as "carboxyl-containing epoxy (meth) acrylate resin") are suitable.

[0319] From the perspective of degassing, resins with aromatic rings in the main chain are more suitable as (C2) epoxy (meth)acrylate resins.

[0320] <Epoxy (meth)acrylate resin (C2-1)>

[0321] An alkali-soluble resin is obtained by adding an epoxy resin to an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester with a carboxyl group, and then reacting it with a polybasic acid and / or its anhydride.

[0322] <Epoxy (meth)acrylate resin (C2-2)>

[0323] An alkali-soluble resin is obtained by adding an epoxy resin to an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester with a carboxyl group, and then reacting it with a polyol, a polyacid, and / or its anhydride.

[0324] Here, epoxy resin refers to the raw material compound that is formed by thermosetting. This epoxy resin can be appropriately selected from known epoxy resins. Alternatively, the epoxy resin can be a compound obtained by reacting a phenolic compound with a surface haloalcohol. The phenolic compound is preferably a compound having two or more phenolic hydroxyl groups, and can be a monomer or a polymer.

[0325] As for the types of epoxy resins used as raw materials, suitable options include cresol varnish-type epoxy resins, phenol varnish-type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, triphenol methane type epoxy resins, biphenol varnish-type epoxy resins, naphthol varnish-type epoxy resins, epoxy resins that are the reaction products of the addition polymerization reaction of dicyclopentadiene with phenol or cresol and epihaloalcohols, adamantyl-containing epoxy resins, fluorene type epoxy resins, and epoxy resins with aromatic rings in the main chain are more suitable.

[0326] As epoxy resins, suitable materials include, for example, bisphenol A type epoxy resins (e.g., "jER828", "jER1001", "jER1002", "jER1004", etc. manufactured by Mitsubishi Chemical Co., Ltd.), epoxy resins obtained by reacting the alcoholic hydroxyl groups of bisphenol A type epoxy resin with epichlorohydrin (e.g., "NER-1302" (epoxy equivalent 323, softening point 76°C) manufactured by Nippon Kayaku Co., Ltd.), and bisphenol F type resins (e.g., "jER828" manufactured by Mitsubishi Chemical Co., Ltd.). Epoxy resins obtained by reacting the alcoholic hydroxyl groups of bisphenol F type epoxy resin with epichlorohydrin (e.g., Nippon Kayaku Co., Ltd.'s "NER-7406" (epoxy equivalent 350, softening point 66℃)), bisphenol S type epoxy resin, biphenyl glycidyl ether (e.g., Mitsubishi Chemical Co., Ltd.'s "YX-4000"), phenolic varnish type epoxy resins (e.g., Nippon Kayaku Co., Ltd.'s "EPPN-201", Mitsubishi Chemical Co., Ltd.'s "EP-152", "EP-154", Dow Chemical Co., Ltd.'s...). The following are examples of epoxy resins: (DEN-438), (ortho, meta, para-)cresol phenolic varnish type epoxy resins (e.g., EOCN-102S, EOCN-1020, EOCN-104S manufactured by Nippon Kayaku Co., Ltd.), triphenol methane type epoxy resins (e.g., EPPN-501, EPPN-502, EPPN-503 manufactured by Nippon Kayaku Co., Ltd.), alicyclic epoxy resins (CELLOXIDE 2021P, CELLOXIDE EHPE manufactured by Celebr. Ltd.), epoxy resins obtained by glycidylating phenolic resins obtained by reacting dicyclopentadiene with phenol (e.g., EXA-7200 manufactured by DIC Co., Ltd., NC-7300 manufactured by Nippon Kayaku Co., Ltd.), and epoxy resins with the following general formulas (C2α) to (C2δ). Specifically, for example, epoxy resins represented by the following general formula (C2α) include "XD-1000" manufactured by Nippon Kayaku Co., Ltd.; epoxy resins represented by the following general formula (C2β) include "NC-3000" and "NC-3500" manufactured by Nippon Kayaku Co., Ltd.; epoxy resins represented by the following general formula (C2γ) include "E-201" manufactured by Osaka Organic Chemical Industry Co., Ltd.; and epoxy resins represented by the following general formula (C2δ) include "ESF-300" manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd.

[0327]

[0328] In formula (C2α), a is the average value, representing a number from 0 to 10, and R... 111Each of these can independently represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 8 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a phenyl group, a naphthyl group, or a biphenyl group. It should be noted that multiple R groups present in one molecule... 111 Each can choose to be the same as or different from the other.

[0329]

[0330] In equation (C2β), b1 and b2 are average values, each independently representing a number from 0 to 10, and R 121 Each of these can independently represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 8 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a phenyl group, a naphthyl group, or a biphenyl group. It should be noted that multiple R groups present in one molecule... 121 Each can choose to be the same as or different from the other.

[0331]

[0332] In formula (C2γ), X represents the linking group shown in the following general formula (C2γ-1) or (C2γ-2).

[0333] The molecular structure contains more than one adamantane structure. 'c' indicates 2 or 3.

[0334]

[0335] In equations (C2γ-1) and (C2γ-2), R 131 ~R 134 and R 135 ~R 137 Each of the following can be independently represented as an optional adamantyl group with substituents, a hydrogen atom, an optional alkyl group with 1 to 12 carbon atoms with substituents, or an optional phenyl group with substituents; * indicates a connecting bond.

[0336]

[0337] In equation (C2δ), p and q each independently represent integers from 0 to 4, and R 141 and R 142 Each independently represents an alkyl or halogen atom having 1 to 4 carbon atoms, R 143 and R 144 Each of the two groups independently represents an alkylene group having 1 to 4 carbon atoms, and x and y independently represent integers greater than 0.

[0338] As the epoxy resin, it is preferred to use an epoxy resin represented by any of the formulas (C2α) to (C2δ).

[0339] Examples of α,β-unsaturated monocarboxylic acids or α,β-unsaturated monocarboxylic acid esters with a carboxyl group include: (meth)acrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid or p-vinylbenzoic acid, α-haloalkyl, alkoxy, halogen, nitro, cyano-substituted monocarboxylic acids; 2-(meth)acryloyloxyethyl succinic acid, 2-(meth)acryloyloxyethyl adipic acid, 2-(meth)acryloyloxyethyl phthalic acid, 2-(meth)acryloyloxyethyl hexahydrophthalic acid, 2-(meth)acryloyloxyethyl maleic acid, 2-(meth)acryloyloxypropyl succinic acid, 2-(meth)acryloyloxypropyl adipic acid, 2-(meth)acryloyloxypropyl tetrahydrophthalic acid. Acids, 2-(meth)acryloyloxypropylphthalic acid, 2-(meth)acryloyloxypropylmaleic acid, 2-(meth)acryloyloxybutylsuccinic acid, 2-(meth)acryloyloxybutyladipic acid, 2-(meth)acryloyloxybutylhydrophthalic acid, 2-(meth)acryloyloxybutylphthalic acid, 2-(meth)acryloyloxybutylmaleic acid; monomers as products obtained by adding lactones such as ε-caprolactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone to (meth)acrylic acid; or monomers obtained by adding acids such as succinic acid (anhydride), phthalic acid (anhydride), and maleic acid (anhydride) to hydroxyalkyl esters of (meth)acrylic acid and pentaerythritol tri(meth)acrylate; (meth)acrylic acid dimers. From the perspective of sensitivity, (meth)acrylic acid is preferred.

[0340] As a method for adding α,β-unsaturated monocarboxylic acids or α,β-unsaturated monocarboxylic acid esters having a carboxyl group to epoxy resin, known techniques can be used. For example, α,β-unsaturated monocarboxylic acids or α,β-unsaturated monocarboxylic acid esters having a carboxyl group can be reacted with epoxy resin in the presence of an esterification catalyst at a temperature of 50–150°C. As esterification catalysts used herein, tertiary amines such as triethylamine, trimethylamine, benzyldimethylamine, and benzyldiethylamine; and quaternary ammonium salts such as tetramethylammonium chloride, tetraethylammonium chloride, and dodecyltrimethylammonium chloride can be used, for example.

[0341] The epoxy resin, α,β-unsaturated monocarboxylic acid or α,β-unsaturated monocarboxylic acid esters with carboxyl groups, and the esterification catalyst can be used individually or in combination of two or more components.

[0342] The amount of α,β-unsaturated monocarboxylic acid or α,β-unsaturated monocarboxylic acid esters having a carboxyl group is preferably 0.5 to 1.2 equivalents, more preferably 0.7 to 1.1 equivalents, relative to the epoxy group of the epoxy resin. By setting the amount of α,β-unsaturated monocarboxylic acid or α,β-unsaturated monocarboxylic acid esters having a carboxyl group to the aforementioned lower limit or above, insufficient introduction of unsaturated groups can be suppressed, and there is a tendency to ensure sufficient subsequent reaction with polybasic acids and / or their anhydrides. By setting it to the aforementioned upper limit or below, unreacted residues of α,β-unsaturated monocarboxylic acid or α,β-unsaturated monocarboxylic acid esters having a carboxyl group can be suppressed, and a tendency to easily achieve good curing properties can be confirmed.

[0343] Examples of polybasic acids and / or their anhydrides include, for example, maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenone tetracarboxylic acid, methylhexahydrophthalic acid, methylenetetrahydrophthalic acid, chloramphenic acid, methyltetrahydrophthalic acid, biphenyl tetracarboxylic acid, and their anhydrides.

[0344] Maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, biphenyl tetracarboxylic acid, and their anhydrides are preferred. Tetrahydrophthalic acid, biphenyl tetracarboxylic acid, and their anhydrides are particularly preferred.

[0345] The addition reaction of polybasic acids and / or their anhydrides can be carried out using known methods. The reaction can be continued under the same conditions as the addition reaction of α,β-unsaturated monocarboxylic acids or α,β-unsaturated monocarboxylic acid esters with carboxyl groups to epoxy resins to obtain the target product. The addition amount of the polybasic acid and / or its anhydride is preferably such that the acid value of the resulting carboxyl-containing epoxy (meth)acrylate resin reaches 10–150 mg KOH / g, more preferably 20–140 mg KOH / g. Setting the value above the aforementioned lower limit tends to improve alkali developability. Setting the value below the aforementioned upper limit tends to improve curing performance.

[0346] In addition reactions of polybasic acids and / or their anhydrides, polyfunctional alcohols (polyols) such as trimethylolpropane, bis(trimethylolpropane), pentaerythritol, dipentaerythritol, trimethylolethane, and 1,2,3-propanetriol can be added to introduce a multi-branched structure. In this case, the mixing order of the polybasic acid and / or its anhydride with the polyfunctional alcohol is not particularly restricted. Upon heating, the polybasic acid and / or its anhydride undergo an addition reaction with any hydroxyl group present in the mixture of epoxy resin and α,β-unsaturated monocarboxylic acid or α,β-unsaturated monocarboxylic acid esters with carboxyl groups and the polyfunctional alcohol.

[0347] By using polyols, there is a tendency to increase the molecular weight of (C2) epoxy (meth)acrylate resins, introduce branched chains into the molecule, and achieve a balance between molecular weight and viscosity. Additionally, there is a tendency to increase the introduction rate of acid groups into the molecule, making it easier to achieve a balance in sensitivity, adhesion, etc.

[0348] In addition to the aforementioned substances, the substances described in Korean Patent Publication No. 10-2013-0022955 can be cited as examples of carboxyl-containing epoxy (meth)acrylate resins.

[0349] The weight-average molecular weight (Mw) of the carboxyl-containing epoxy (meth)acrylate resin, determined by gel permeation chromatography (GPC) based on polystyrene, is preferably 1000 or more, more preferably 1500 or more, further preferably 2000 or more, even more preferably 3000 or more, even more preferably 4000 or more, and particularly preferably 5000 or more. Additionally, it is preferably 30000 or less, more preferably 20000 or less, and even more preferably 15000 or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1000 to 30000, more preferably 1500 to 20000, even more preferably 1500 to 15000, and even more preferably 2000 to 15000. By setting it to the aforementioned lower limit or above, the tendency for the solubility in the developer to become excessively high is suppressed. By setting it to the aforementioned upper limit or below, the tendency for good solubility in the developer is easily achieved.

[0350] The acid value of the carboxyl-containing epoxy (meth)acrylate resin is not particularly limited, but is preferably 20 mg KOH / g or more, more preferably 40 mg KOH / g or more, further preferably 60 mg KOH / g or more, even more preferably 80 mg KOH / g or more, and particularly preferably 100 mg KOH / g or more. Additionally, it is preferably 200 mg KOH / g or less, more preferably 150 mg KOH / g or less, further preferably 130 mg KOH / g or less, and particularly preferably 120 mg KOH / g or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 20–200 mg KOH / g, more preferably 60–150 mg KOH / g, further preferably 80–130 mg KOH / g, and even more preferably 100–130 mg KOH / g. By setting it to the aforementioned lower limit or above, there is a tendency for improved developing solubility and better resolution. By setting it to the aforementioned upper limit or below, there is a tendency for a better residual film rate in the photosensitive coloring resin composition.

[0351] (C2) The chemical structure of the epoxy (meth)acrylate resin is not particularly limited. From the viewpoint of developability and reliability, it is preferred to contain an epoxy (meth)acrylate resin having a partial structure shown in the following general formula (C2-I) (hereinafter, sometimes simply referred to as "(C2-I) epoxy (meth)acrylate resin") and / or an epoxy (meth)acrylate resin having a partial structure shown in the following general formula (C2-II) (hereinafter, sometimes simply referred to as "(C2-II) epoxy (meth)acrylate resin").

[0352]

[0353] In formula (C2-I), R 11 R represents a hydrogen atom or a methyl group. 12 This indicates a divalent hydrocarbon group with optional substituents, k indicates 1 or 2, and * indicates a linking bond.

[0354] The benzene ring in formula (C2-I) may be further substituted with any substituents.

[0355]

[0356] In formula (C2-II), R 13 Each can independently represent a hydrogen atom or a methyl group, R 14 R represents a divalent hydrocarbon group with a cyclic hydrocarbon group as a side chain. 15 and R 16 Each of the substituents independently represents a divalent aliphatic group, m and n independently represent integers from 0 to 2, and * represents a linking bond.

[0357] <(C2-I)Epoxy (Meth)acrylate Resins>

[0358]

[0359] In formula (C2-I), R 11 R represents a hydrogen atom or a methyl group. 12 This indicates a divalent hydrocarbon group with optional substituents, k indicates 1 or 2, and * indicates a linking bond.

[0360] The benzene ring in formula (C2-I) may be further substituted with any substituents.

[0361] (R 12 )

[0362] In formula (C2-I), R 12 This indicates an optional divalent hydrocarbon group with substituents.

[0363] As divalent hydrocarbon groups, examples include divalent aliphatic groups, divalent aromatic cyclic groups, and groups obtained by connecting one or more divalent aliphatic groups to one or more divalent aromatic cyclic groups.

[0364] Divalent aliphatic groups can be categorized as linear, branched, or cyclic aliphatic groups. From the viewpoint of development solubility, linear aliphatic groups are preferred. On the other hand, from the viewpoint of reducing developer penetration into the exposed area, cyclic aliphatic groups are preferred. The number of carbon atoms is preferably 1 or more, more preferably 3 or more, and even more preferably 6 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 20 is preferred, more preferably 1 to 15, and even more preferably 1 to 10. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to reduce surface roughness during development and improve adhesion to the substrate. By setting the value to the aforementioned upper limit or below, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0365] Examples of divalent linear aliphatic groups include methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, and n-heptylene. From the viewpoint of skeletal rigidity, methylene is preferred.

[0366] As divalent branched aliphatic groups, structures with, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl as side chains can be listed.

[0367] The number of rings in the divalent cyclic aliphatic group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 12 or less, more preferably 10 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 12 is preferred, 1 to 10 is more preferred, and 2 to 10 is even more preferred. By setting it to the aforementioned lower limit or above, a robust film is formed, and substrate adhesion tends to improve. By setting it to the aforementioned upper limit or below, sensitivity degradation can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0368] Examples of divalent cyclic aliphatic groups include those obtained by removing two hydrogen atoms from the rings of cyclohexane, cycloheptane, cyclodecane, cyclododecane, norbornene, isocamphene, adamantane, dicyclopentadiene, and dicyclopentane. From the viewpoint of skeletal rigidity, groups obtained by removing two hydrogen atoms from the dicyclopentadiene, dicyclopentane, or adamantane rings are preferred.

[0369] Substituents that can be optionally present as divalent aliphatic groups include, for example, alkoxy groups with 1 to 5 carbon atoms such as methoxy and ethoxy; hydroxyl groups; nitro groups; cyano groups; and carboxyl groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0370] Examples of divalent aromatic cyclic groups include divalent aromatic hydrocarbon cyclic groups and divalent aromatic heterocyclic groups. The number of carbon atoms is not particularly limited, but is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 20 is preferred, more preferably 5 to 15, and even more preferably 6 to 10. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency for surface roughness during development to be less likely to occur, resulting in better adhesion to the substrate. By setting the value to the aforementioned upper limit or below, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate after development and improved resolution.

[0371] The aromatic hydrocarbon ring in a divalent aromatic hydrocarbon ring group can be a monocyclic or fused ring. Examples of divalent aromatic hydrocarbon ring groups include those with two free valence atoms, such as benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, perylene rings, tetraphenylene rings, pyrene rings, and benzo[a]pyrene rings. Rings, benzo[a]phenanthrene ring, acenaphthene ring, fluoranthene ring, fluorene ring.

[0372] Aromatic heterocycles, as divalent aromatic heterocyclic groups, can be monocyclic or fused rings. Examples of divalent aromatic heterocyclic groups include those with two free valences, such as furan rings, benzofuran rings, thiophene rings, benzothiophene rings, pyrrole rings, pyrazole rings, imidazole rings, oxadiazole rings, indole rings, carbazole rings, pyrroloimidazolium rings, pyrrolopyrazole rings, pyrrolopyrrole rings, thienopyrrole rings, thienothiophene rings, furanolopyrrole rings, furanolofuran rings, thienofuran rings, benzoisoxazole rings, benzoisothiazolium rings, benzimidazole rings, pyridine rings, pyrazine rings, pyridazine rings, pyrimidine rings, triazine rings, quinoline rings, isoquinoline rings, borazine rings, quinoxaline rings, phenanthridine rings, primidine rings, quinazoline rings, quinazolineone rings, and azurite rings.

[0373] From the viewpoint of patterning properties, a benzene ring or naphthalene ring with two free atomic valences is preferred, and a benzene ring with two free atomic valences is more preferred.

[0374] Substituents that can be optionally present in the divalent aromatic cyclic group include, for example, hydroxyl, methyl, methoxy, ethyl, ethoxy, propyl, and propoxy. From the viewpoint of developing solubility, unsubstituted substituents are preferred.

[0375] Examples of groups obtained by linking one or more divalent aliphatic groups to one or more divalent aromatic cyclic groups include groups obtained by linking one or more of the aforementioned divalent aliphatic groups to one or more of the aforementioned divalent aromatic cyclic groups.

[0376] The number of divalent aliphatic groups is not particularly limited, but is preferably 1 or more, more preferably 2 or more, and preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2 to 3. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to reduce surface roughness during development and improve adhesion to the substrate. By setting the value to the aforementioned upper limit or below, sensitivity degradation can be suppressed, and there is a tendency to achieve a high residual film rate and improved resolution after development.

[0377] The number of divalent aromatic ring groups is not particularly limited, but is preferably 1 or more, more preferably 2 or more, and preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2 to 3. By setting the value above the aforementioned lower limit, a robust film is easily obtained, and there is a tendency to reduce surface roughness during development and improve adhesion to the substrate. By setting the value below the aforementioned upper limit, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0378] As a group obtained by linking one or more divalent aliphatic groups to one or more divalent aromatic cyclic groups, examples include groups shown in formulas (C2-IA) to (C2-IF). In formulas (C2-IA) to (C2-IF), * indicates a linking bond. From the viewpoint of rigidity of the framework and hydrophobicity of the membrane, groups shown in formula (C2-IA) are preferred.

[0379]

[0380] In formula (C2-I), k represents 1 or 2. From the viewpoint of adhesion and printability, k is preferably 1. From the viewpoint of sensitivity, k is preferably 2. Alternatively, the (C2-I) epoxy (meth)acrylate may contain both a partial structure with k=1 and a partial structure with k=2.

[0381] The benzene ring in formula (C2-I) may be further substituted with any substituents.

[0382] Examples of substituents include hydroxyl, methyl, methoxy, ethyl, ethoxy, propyl, and propoxy. The number of substituents is not particularly limited; there can be one or more.

[0383] From a design perspective, the preferred option is the unreplaced one.

[0384] From the viewpoint of ease of synthesis, the partial structure represented by formula (C2-I) is preferably the partial structure shown in the following general formula (C2-I-1).

[0385]

[0386] In formula (C2-I-1), R 11 R 12 And k has the same meaning as equation (C2-I), R X * indicates a hydrogen atom or a polybasic acid residue, and * indicates a linking bond.

[0387] The benzene ring in formula (C2-I-1) may be further substituted with any substituents.

[0388] A polybasic acid residue refers to a monovalent or divalent group obtained by removing one or two OH groups from a polybasic acid. Examples of polybasic acids include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenone tetracarboxylic acid, methylhexahydrophthalic acid, methylenetetrahydrophthalic acid, chloramphenicol, methyltetrahydrophthalic acid, and biphenyltetracarboxylic acid.

[0389] From the viewpoint of patterning properties, maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, and biphenyl tetracarboxylic acid are preferred, and tetrahydrophthalic acid, biphenyl tetracarboxylic acid, and biphenyl tetracarboxylic acid are more preferred.

[0390] The benzene ring in formula (C2-I-1) may be further substituted with any substituents. As substituents, groups listed above the benzene ring in formula (C2-I) are preferred.

[0391] The partial structure represented by formula (C2-I-1) contained in one molecule of an epoxy (meth)acrylate resin can be one or more types. For example, it can be R X The structure of the hydrogen atom and R X It exists as a mixture of polyacid residues.

[0392] The number of the partial structures represented by formula (C2-I) contained in one molecule of (C2-I) epoxy (meth)acrylate resin is not particularly limited, but is preferably 1 or more, more preferably 3 or more. Furthermore, it is preferably 20 or less, and even more preferably 15 or less. The above upper and lower limits can be combined arbitrarily. Preferably 1 to 20, more preferably 1 to 15, and even more preferably 3 to 15. By setting it to the aforementioned lower limit or above, a strong film is easily obtained, and there is a tendency to avoid surface roughness during development. By setting it to the aforementioned upper limit or below, the deterioration of sensitivity can be suppressed, and there is a tendency to have a high residual film rate and improved resolution after development.

[0393] The weight-average molecular weight (Mw) of the (C2-I) epoxy (meth)acrylate resin, determined by gel permeation chromatography (GPC) based on polystyrene, is not particularly limited, but is preferably 1000 or more, more preferably 1500 or more, further preferably 2000 or more, even more preferably 3000 or more, particularly preferably 4000 or more, most preferably 5000 or more, preferably 30000 or less, more preferably 20000 or less, and even more preferably 15000 or less. The above upper and lower limits can be combined arbitrarily. For example, 1000 to 30000 is preferred, more preferably 1500 to 20000, further preferably 1500 to 15000, and even more preferably 2000 to 15000. By setting the value to the aforementioned lower limit or above, the residual film rate of the photosensitive coloring resin composition tends to become better. By setting the value to the aforementioned upper limit or below, the solubility in the developing solution tends to become better.

[0394] The acid value of the (C2-I) epoxy (meth)acrylate resin is not particularly limited, but is preferably 20 mg KOH / g or more, more preferably 40 mg KOH / g or more, further preferably 60 mg KOH / g or more, even more preferably 80 mg KOH / g or more, and particularly preferably 100 mg KOH / g or more. Additionally, it is preferably 200 mg KOH / g or less, more preferably 150 mg KOH / g or less, even more preferably 130 mg KOH / g or less, and particularly preferably 120 mg KOH / g or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 20–200 mg KOH / g, more preferably 60–150 mg KOH / g, further preferably 80–130 mg KOH / g, and even more preferably 100–130 mg KOH / g. By setting it to the aforementioned lower limit or above, there is a tendency for improved developing solubility and better resolution. By setting it to the aforementioned upper limit or below, there is a tendency for a better residual film rate in the photosensitive coloring resin composition.

[0395] The following are specific examples of (C2-I) epoxy (meth)acrylate resins. It should be noted that * in the examples indicates a linking bond.

[0396]

[0397]

[0398] <(C2-II) Epoxy (Meth)acrylate Resins>

[0399]

[0400] In formula (C2-II), R 13 Each can independently represent a hydrogen atom or a methyl group, R 14 R represents a divalent hydrocarbon group with a cyclic hydrocarbon group as a side chain. 15 and R 16 Each of the substituents independently represents a divalent aliphatic group, m and n independently represent integers from 0 to 2, and * represents a linking bond.

[0401] From the viewpoint of luminescence properties, a structure having formula (C2-II) is preferred.

[0402] (R 14 )

[0403] In formula (C2-II), R 14 This indicates a divalent hydrocarbon group with a cyclic hydrocarbon group as a side chain.

[0404] As cyclic hydrocarbon groups, aliphatic cyclic groups or aromatic cyclic groups can be listed.

[0405] The number of rings in the aliphatic ring group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2 to 3. By setting it to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to avoid surface roughness during development. By setting it to the aforementioned upper limit or below, the deterioration of sensitivity can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0406] The number of carbon atoms in the aliphatic ring group is not particularly limited, but is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. Furthermore, it is preferably 40 or less, more preferably 30 or less, even more preferably 20 or less, and particularly preferably 15 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 40 is preferred, more preferably 4 to 30, even more preferably 6 to 20, and particularly preferably 8 to 15. By setting it to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to avoid surface roughness during development. By setting it to the aforementioned upper limit or below, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0407] Examples of aliphatic rings among aliphatic ring groups include cyclohexane, cycloheptane, cyclodecane, cyclododecane, norbornene, isobornene, and adamantane. From the viewpoint of residual film yield and resolution of the photosensitive coloring resin composition, adamantane is preferred.

[0408] The number of rings in the aromatic ring group is not particularly limited, but is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more. Furthermore, it is preferably 10 or less, more preferably 5 or less, and even more preferably 4 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 1 to 4, and still more preferably 2 to 4, particularly preferably 3 to 4. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to avoid surface roughness during development. By setting the value to the aforementioned upper limit or below, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0409] Aromatic cyclic groups include aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups. The number of carbon atoms in the aromatic cyclic group is not particularly limited, but is preferably 4 or more, more preferably 6 or more, further preferably 8 or more, even more preferably 10 or more, and particularly preferably 12 or more. Additionally, it is preferably 40 or less, more preferably 30 or less, further preferably 20 or less, and particularly preferably 15 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 40 is preferred, more preferably 6 to 40, further preferably 8 to 30, even more preferably 10 to 20, and particularly preferably 12 to 15. By setting the value above the aforementioned lower limit, a robust film is easily obtained, and there is a tendency for surface roughness to occur during development. By setting the value below the aforementioned upper limit, there is a tendency for patterning characteristics to become better.

[0410] Aromatic rings, as components of aromatic cyclic groups, can be exemplified by, for example, benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, perylene rings, tetraphenylene rings, pyrene rings, and benzo[a]pyrene rings. The rings include benzo[a]phenanthrene ring, acenaphthene ring, fluoranthene ring, and fluorene ring. From the viewpoint of patterning properties, the fluorene ring is preferred.

[0411] The divalent hydrocarbon group in the divalent hydrocarbon group having a cyclic hydrocarbon group as a side chain is not particularly limited. For example, divalent aliphatic groups, divalent aromatic cyclic groups, and groups obtained by connecting one or more divalent aliphatic groups with one or more divalent aromatic cyclic groups can be listed.

[0412] Divalent aliphatic groups can be categorized as linear, branched, or cyclic aliphatic groups. From the viewpoint of development solubility, linear aliphatic groups are preferred; conversely, from the viewpoint of reducing the penetration of the developer into the exposed section, cyclic aliphatic groups are preferred. The number of carbon atoms is not particularly limited, but is preferably 1 or more, more preferably 3 or more, and even more preferably 6 or more. Furthermore, it is preferably 25 or less, more preferably 20 or less, and even more preferably 15 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 25 is preferred, more preferably 3 to 20, and even more preferably 6 to 15. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to reduce surface roughness during development and improve adhesion to the substrate. By setting the value to the aforementioned upper limit or below, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0413] Examples of divalent linear aliphatic groups include methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, and n-heptylene. From the viewpoint of skeletal rigidity, methylene is preferred.

[0414] Examples of divalent branched aliphatic groups include structures with methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl as side chains on the aforementioned divalent straight-chain aliphatic groups.

[0415] The number of rings in the divalent cyclic aliphatic group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2 to 3. By setting it to the aforementioned lower limit or above, a robust film is formed, tending to have good substrate adhesion. Furthermore, by setting it to the aforementioned upper limit or below, sensitivity degradation can be suppressed, tending to result in high residual film rate and improved resolution after development.

[0416] Examples of divalent cyclic aliphatic groups include those obtained by removing two hydrogen atoms from the rings of cyclohexane, cycloheptane, cyclodecane, cyclododecane, norbornene, isocamphene, and adamantane. From the viewpoint of skeletal rigidity, groups obtained by removing two hydrogen atoms from the adamantane ring are preferred.

[0417] Substituents that can be optionally present as divalent aliphatic groups include, for example, alkoxy groups with 1 to 5 carbon atoms such as methoxy and ethoxy; hydroxyl groups; nitro groups; cyano groups; and carboxyl groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0418] Examples of divalent aromatic cyclic groups include divalent aromatic hydrocarbon cyclic groups and divalent aromatic heterocyclic groups. The number of carbon atoms is not particularly limited, but is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more. Furthermore, it is preferably 30 or less, more preferably 20 or less, and even more preferably 15 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 30 is preferred, more preferably 5 to 20, and even more preferably 6 to 15. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency for surface roughness during development to be less likely to occur, and good adhesion to the substrate to become more desirable. By setting the value to the aforementioned upper limit or below, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate after development and improved resolution.

[0419] The aromatic hydrocarbon ring in a divalent aromatic hydrocarbon ring group can be a monocyclic or fused ring. Examples of divalent aromatic hydrocarbon ring groups include those with two free valence atoms, such as benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, perylene rings, tetraphenylene rings, pyrene rings, and benzo[a]pyrene rings. Rings, benzo[a]phenanthrene ring, acenaphthene ring, fluoranthene ring, fluorene ring.

[0420] Aromatic heterocycles, as divalent aromatic heterocyclic groups, can be monocyclic or fused rings. Examples of divalent aromatic heterocyclic groups include those with two free valences, such as furan rings, benzofuran rings, thiophene rings, benzothiophene rings, pyrrole rings, pyrazole rings, imidazole rings, oxadiazole rings, indole rings, carbazole rings, pyrroloimidazolium rings, pyrrolopyrazole rings, pyrrolopyrrole rings, thienopyrrole rings, thienothiophene rings, furanolopyrrole rings, furanolofuran rings, thienofuran rings, benzoisoxazole rings, benzoisothiazolium rings, benzimidazole rings, pyridine rings, pyrazine rings, pyridazine rings, pyrimidine rings, triazine rings, quinoline rings, isoquinoline rings, borazine rings, quinoxaline rings, phenanthridine rings, primidine rings, quinazoline rings, quinazolineone rings, and azurite rings. From the viewpoint of patterning properties, benzene rings and naphthalene rings with two free atomic valences are preferred, and benzene rings with two free atomic valences are more preferred.

[0421] Substituents that can be optionally present in the divalent aromatic cyclic group include, for example, hydroxyl, methyl, methoxy, ethyl, ethoxy, propyl, and propoxy. From the viewpoint of developing solubility, unsubstituted substituents are preferred.

[0422] Examples of groups obtained by linking one or more divalent aliphatic groups to one or more divalent aromatic cyclic groups include groups obtained by linking one or more of the aforementioned divalent aliphatic groups to one or more of the aforementioned divalent aromatic cyclic groups.

[0423] The number of divalent aliphatic groups is not particularly limited, but is preferably 1 or more, more preferably 2 or more, preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2 to 3. By setting the value above the aforementioned lower limit, a robust film is easily obtained, and there is a tendency for surface roughness to occur during development and for good adhesion to the substrate. By setting the value below the aforementioned upper limit, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0424] The number of divalent aromatic ring groups is not particularly limited, but is preferably 1 or more, more preferably 2 or more, preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2 to 3. By setting the value above the aforementioned lower limit, a robust film is easily obtained, and there is a tendency for surface roughness to occur during development and for good adhesion to the substrate. By setting the value below the aforementioned upper limit, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0425] As a group obtained by linking one or more divalent aliphatic groups to one or more divalent aromatic cyclic groups, examples include the groups shown in formulas (C2-IA) to (C2-IF). From the viewpoint of rigidity of the skeleton and hydrophobicity of the membrane, the group shown in formula (C2-IC) is preferred.

[0426] There are no particular restrictions on the bonding mode of these divalent hydrocarbon groups for the cyclic hydrocarbon groups that serve as side chains. Examples include the way that one hydrogen atom of an aliphatic group or an aromatic cyclic group is replaced by a cyclic hydrocarbon group that serves as a side chain, and the way that one carbon atom of an aliphatic group is included to form a cyclic hydrocarbon group that serves as a side chain.

[0427] (R 15 R 16 )

[0428] In formula (C2-II), R 15 and R 16 Each can be independently represented as a divalent aliphatic group with substituents.

[0429] Divalent aliphatic groups can be categorized as linear, branched, or cyclic aliphatic groups. From the viewpoint of development solubility, linear aliphatic groups are preferred; conversely, from the viewpoint of reducing the penetration of the developer into the exposed section, cyclic aliphatic groups are preferred. The number of carbon atoms is not particularly limited, but is preferably 1 or more, more preferably 3 or more, and even more preferably 6 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 20 is preferred, more preferably 3 to 15, and even more preferably 6 to 10. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to reduce surface roughness during development and improve adhesion to the substrate. By setting the value to the aforementioned upper limit or below, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0430] Examples of divalent linear aliphatic groups include methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, and n-heptylene. From the viewpoint of skeletal rigidity, methylene is preferred.

[0431] As divalent branched aliphatic groups, structures with, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl as side chains can be listed.

[0432] The number of rings in the divalent cyclic aliphatic group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 12 or less, more preferably 10 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 12 is preferred, more preferably 2 to 10. By setting it to the aforementioned lower limit or above, a robust film is formed, tending to have good substrate adhesion. By setting it to the aforementioned upper limit or below, sensitivity degradation can be suppressed, tending to result in high residual film rate and improved resolution after development.

[0433] Examples of divalent cyclic aliphatic groups include those obtained by removing two hydrogen atoms from cyclohexane, cycloheptane, cyclodecane, cyclododecane, norbornene, isocamphene, adamantane, and dicyclopentadiene rings. From the viewpoint of skeletal rigidity, groups obtained by removing two hydrogen atoms from dicyclopentadiene or adamantane rings are preferred.

[0434] Substituents that can be optionally present as divalent aliphatic groups include, for example, alkoxy groups with 1 to 5 carbon atoms such as methoxy and ethoxy; hydroxyl groups; nitro groups; cyano groups; and carboxyl groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0435] (m, n)

[0436] In formula (C2-II), m and n each independently represent integers from 0 to 2. By setting them to the aforementioned lower limit or higher, there is a tendency for good patterning adaptability and less surface roughness during development. Conversely, by setting them to the aforementioned upper limit or lower, there is a tendency for good developability. From the viewpoint of developability, m and n are preferably 0. From the viewpoint of patterning adaptability and suppressing surface roughness during development, m and n are preferably 1 or higher.

[0437] From the viewpoint of ensuring a tight seal on the substrate, the partial structure shown in formula (C2-II) is preferably the partial structure shown in the following general formula (C2-II-1).

[0438]

[0439] In formula (C2-II-1), R 13 R 15 R 16 m and n have the same meaning as in equation (C2-II), R α The symbol represents a monovalent cyclic hydrocarbon group with optional substituents, p represents an integer greater than 1, and * represents a linking bond. The benzene ring in formula (C2-II-1) may be further substituted with any substituents.

[0440] (R α )

[0441] In formula (C2-II-1), R α This indicates a monovalent cyclic hydrocarbon group that may be optionally substituted.

[0442] As cyclic hydrocarbon groups, aliphatic cyclic groups or aromatic cyclic groups can be listed.

[0443] The number of rings in the aliphatic ring group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 6 or less, more preferably 4 or less, and even more preferably 3 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 6 is preferred, more preferably 1 to 4, even more preferably 1 to 3, and particularly preferably 2 to 3. By setting it to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to avoid surface roughness that occurs during development. By setting it to the aforementioned upper limit or below, there is a tendency for patterning characteristics to become better.

[0444] The number of carbon atoms in the aliphatic ring group is not particularly limited, but is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. Furthermore, it is preferably 40 or less, more preferably 30 or less, even more preferably 20 or less, and particularly preferably 15 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 40 is preferred, more preferably 4 to 30, even more preferably 6 to 20, and particularly preferably 8 to 15. By setting it to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to avoid surface roughness that occurs during development. By setting it to the aforementioned upper limit or below, there is a tendency for patterning characteristics to become better.

[0445] Examples of aliphatic rings among aliphatic cyclic groups include cyclohexane, cycloheptane, cyclodecane, cyclododecane, norbornene, isocamphene, and adamantane. From the viewpoint of robust membrane properties, the adamantane ring is preferred.

[0446] The number of rings in the aromatic ring group is not particularly limited, but is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more. Furthermore, it is preferably 10 or less, and even more preferably 5 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, further preferably 2 to 5, and particularly preferably 3 to 5. By setting the value above the aforementioned lower limit, it is easier to obtain a robust film, and there is a tendency to avoid surface roughness that occurs during development. By setting the value below the aforementioned upper limit, there is a tendency for patterning characteristics to become better.

[0447] Examples of aromatic cyclic groups include aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups. Furthermore, the number of carbon atoms in the aromatic cyclic group is not particularly limited, but is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more. Additionally, it is preferably 30 or less, more preferably 20 or less, and even more preferably 15 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 30 is preferred, more preferably 5 to 20, and even more preferably 6 to 15. By setting the value above the aforementioned lower limit, it is easier to obtain a robust film, and there is a tendency to avoid surface roughness that occurs during development. By setting the value below the aforementioned upper limit, there is a tendency for patterning characteristics to become better.

[0448] Examples of aromatic rings in aromatic ring groups include benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and fluorene rings. From the viewpoint of developing solubility, fluorene rings are preferred.

[0449] Substituents that can be optionally present in the cyclic hydrocarbon group include, for example, alkyl groups with 1 to 5 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, and isopentyl; alkoxy groups with 1 to 5 carbon atoms such as methoxy and ethoxy; hydroxyl groups; nitro groups; cyano groups; and carboxyl groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0450] p represents an integer greater than or equal to 1, preferably greater than or equal to 2. Furthermore, it is preferably less than or equal to 3. For example, 1 to 3 is preferred, and 2 to 3 is more preferred. By setting it to the aforementioned lower limit or higher, there is a tendency for the film curing degree and residual film rate to become better. By setting it to the aforementioned upper limit or lower, there is a tendency for the developability to become better.

[0451] From the perspective of robust film curing, R α Preferably, it is a monovalent aliphatic cyclic group, and more preferably, it is an adamantyl group.

[0452] The benzene ring in formula (C2-II-1) may be further substituted with any substituents. Examples of substituents include hydroxyl, methyl, methoxy, ethyl, ethoxy, propyl, and propoxy. The number of substituents is not particularly limited and may be one or more.

[0453] From the perspective of patterning characteristics, unsubstituted is preferred.

[0454] The following are specific examples of some of the structures shown in equation (C2-II-1).

[0455] In the following examples, * represents a connector key.

[0456]

[0457]

[0458] From the viewpoint of rigidity of the skeleton and hydrophobicity of the membrane, the partial structure shown in formula (C2-II) is preferably the partial structure shown in the following general formula (C2-II-2).

[0459]

[0460] In formula (C2-II-2), R 13 R 15 R 16 m and n have the same meaning as in equation (C2-II), R β * indicates a divalent cyclic hydrocarbon group with optional substituents, and * indicates a linking bond.

[0461] The benzene ring in formula (C2-II-2) may be further substituted with any substituents.

[0462] (R β )

[0463] In formula (C2-II-2), R β This indicates a divalent cyclic hydrocarbon group that may be optionally substituted.

[0464] As cyclic hydrocarbon groups, aliphatic cyclic groups or aromatic cyclic groups can be listed.

[0465] The number of rings in the aliphatic ring group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. Furthermore, it is preferably 10 or less, more preferably 5 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 2 to 5. By setting the value above the aforementioned lower limit, a robust film is easily obtained, and there is a tendency to avoid surface roughness that occurs during development. By setting the value below the aforementioned upper limit, sensitivity deterioration can be suppressed, and there is a tendency for high residual film rate and improved resolution after development.

[0466] The aliphatic cyclic group preferably has 4 or more carbon atoms, more preferably 6 or more, and even more preferably 8 or more. Furthermore, it is preferably 40 or less, more preferably 35 or less, and even more preferably 30 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 40 is preferred, more preferably 6 to 35, and even more preferably 8 to 30. By setting it to the aforementioned lower limit or above, there is a tendency to suppress roughness of the film surface during development. By setting it to the aforementioned upper limit or below, it is possible to suppress the deterioration of sensitivity, and there is a tendency for high residual film rate and improved resolution after development.

[0467] Examples of aliphatic rings among aliphatic ring groups include cyclohexane, cycloheptane, cyclodecane, cyclododecane, norbornene, isocamphene, and adamantane. From the viewpoint of residual film yield and resolution after development, adamantane is preferred.

[0468] The number of rings in the aromatic ring group is not particularly limited, but is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more. Furthermore, it is preferably 10 or less, more preferably 5 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 10 is preferred, more preferably 1 to 5, even more preferably 2 to 5, and particularly preferably 3 to 5. By setting it to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to avoid surface roughness during development. By setting it to the aforementioned upper limit or below, it is easier to suppress sensitivity deterioration and film reduction, and there is a tendency to improve resolution.

[0469] As aromatic cyclic groups, examples include aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups.

[0470] The aromatic ring group preferably has 4 or more carbon atoms, more preferably 6 or more, further preferably 8 or more, and even more preferably 10 or more. Additionally, it is preferably 40 or less, more preferably 30 or less, further preferably 20 or less, and particularly preferably 15 or less. The above upper and lower limits can be combined arbitrarily. For example, 4 to 40 is preferred, more preferably 6 to 30, further preferably 8 to 20, and particularly preferably 10 to 15. By setting it to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to avoid surface roughness during development. By setting it to the aforementioned upper limit or below, it is easier to suppress sensitivity deterioration and film reduction, and there is a tendency to improve resolution.

[0471] Aromatic rings, such as benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and fluorene rings, can be listed as aromatic rings. From the viewpoint of residual film yield, fluorene rings are preferred. It is speculated that the plane forming the fluorene ring is orthogonal to the bonds connecting it to the two benzene rings, thus increasing its volume and creating a more rigid framework. This makes it less prone to developer penetration and shrinkage during calcination, resulting in a higher residual film yield.

[0472] Substituents that can be optionally present in the cyclic hydrocarbon group include, for example, alkyl groups with 1 to 5 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, and isopentyl; alkoxy groups with 1 to 5 carbon atoms such as methoxy and ethoxy; hydroxyl groups; nitro groups; cyano groups; and carboxyl groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0473] From the perspective of inhibition and resolution due to reduced membrane thickness, R β Preferably, it is a divalent aliphatic cyclic group, more preferably a divalent adamantane cyclic group. From the viewpoint of patterning properties, R β Preferably, it is a divalent aromatic cyclic group, more preferably a divalent fluorene cyclic group.

[0474] The benzene ring in formula (C2-II-2) may be further substituted with any substituents. Examples of substituents include hydroxyl, methyl, methoxy, ethyl, ethoxy, propyl, and propoxy. The number of substituents is not particularly limited and may be one or more.

[0475] Alternatively, the two benzene rings can be linked by substituents. Examples of substituents in this case include divalent groups such as -O-, -S-, -NH-, and -CH2-. From the viewpoint of patterning properties, unsubstituted groups are preferred. Furthermore, from the viewpoint of minimizing film loss, methyl-substituted groups are preferred.

[0476] The following are specific examples of some of the structures shown in equation (C2-II-2). It should be noted that * in the examples represents a connecting key.

[0477]

[0478]

[0479] From the viewpoint of coating residual film rate and patterning characteristics, the partial structure shown in formula (C2-II) is preferably the partial structure shown in the following general formula (C2-II-3).

[0480]

[0481] In formula (C2-II-3), R 13 R 14 R 15 R 16 m and n have the same meaning as in equation (C2-II), R Z It represents a hydrogen atom or a polyacid residue.

[0482] A polybasic acid residue refers to a monovalent or divalent group obtained by removing one or two OH groups from a polybasic acid. It should be noted that another OH group can also be further removed, resulting in a residue similar to the R group in other molecules shown in formula (C2-II-3). Z Shared. That is, multiple equations (C2-II-3) can be used with the help of R. Z And the connection.

[0483] Examples of polybasic acids include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenone tetracarboxylic acid, methylhexahydrophthalic acid, methylmethylenetetrahydrophthalic acid, chloramphenic acid, methyltetrahydrophthalic acid, and biphenyltetracarboxylic acid.

[0484] From the viewpoint of patterning properties, maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, and biphenyl tetracarboxylic acid are preferred, and tetrahydrophthalic acid, biphenyl tetracarboxylic acid, and biphenyl tetracarboxylic acid are more preferred.

[0485] The partial structure represented by formula (C2-II-3) contained in one molecule of (C2-II) epoxy (meth)acrylate resin can be one or more types. For example, it can be R Z The structure of the hydrogen atom and R Z It exists as a mixture of polyacid residues.

[0486] The number of the partial structures represented by formula (C2-II) contained in one molecule of (C2-II) epoxy (meth)acrylate resin is not particularly limited, but is preferably 1 or more, more preferably 3 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The above upper and lower limits can be combined arbitrarily. For example, 1 to 20 is preferred, more preferably 1 to 15, and even more preferably 3 to 10. By setting the value to the aforementioned lower limit or above, a robust film is easily obtained, and there is a tendency to reduce surface roughness during development. By setting the value to the aforementioned upper limit or below, it is easier to suppress sensitivity deterioration and film reduction, and there is a tendency to improve resolution.

[0487] The weight-average molecular weight (Mw) of the (C2-II) epoxy (meth)acrylate resin, determined by gel permeation chromatography (GPC) based on polystyrene, is not particularly limited, but is preferably 1000 or more, more preferably 1500 or more, further preferably 2000 or more, even more preferably 3000 or more, even more preferably 4000 or more, and particularly preferably 5000 or more. Furthermore, it is preferably 10000 or less, more preferably 8000 or less, and even more preferably 7000 or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1000 to 10000, more preferably 1500 to 10000, further preferably 1500 to 8000, even more preferably 2000 to 8000, and particularly preferably 2000 to 7000. By setting it to the aforementioned lower limit or above, there is a tendency for the residual film rate of the photosensitive coloring resin composition to become better. By setting it to the aforementioned upper limit or below, there is a tendency for the developability to become better.

[0488] The acid value of the (C2-II) epoxy (meth)acrylate resin is not particularly limited, but is preferably 20 mg KOH / g or more, more preferably 40 mg KOH / g or more, further preferably 60 mg KOH / g or more, even more preferably 80 mg KOH / g or more, and particularly preferably 100 mg KOH / g or more. Additionally, it is preferably 200 mg KOH / g or less, more preferably 150 mg KOH / g or less, even more preferably 130 mg KOH / g or less, and particularly preferably 120 mg KOH / g or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 20–200 mg KOH / g, more preferably 60–150 mg KOH / g, further preferably 80–130 mg KOH / g, and even more preferably 100–130 mg KOH / g. By setting it to the aforementioned lower limit or above, there is a tendency for improved developing solubility and better resolution. By setting it to the aforementioned upper limit or below, there is a tendency for a better residual film rate in the photosensitive coloring resin composition.

[0489] (C2) Epoxy (meth)acrylate resins can be used alone or in combination with two or more resins.

[0490] <(C3) Resins containing isocyanuric acid backbone>

[0491] In the photosensitive coloring resin composition of the present invention, as the (C) alkali-soluble resin other than resin (C1), a resin containing an isocyanuric acid backbone having olefinic double bonds and carboxyl groups can be used. (Hereinafter sometimes abbreviated as (C3) resin containing an isocyanuric acid backbone.)

[0492] By possessing an isocyanuric acid skeleton, olefinic double bonds, and carboxyl groups, the chemical resistance and heat resistance are improved, and the amount of decomposition products during development and calcination is reduced. As a result, in organic electroluminescent elements, there is a tendency for the current density to increase when a voltage is applied.

[0493] (C3) Resins containing isocyanuric acid skeletons are (C) alkali-soluble resins other than resins (C1). There are no particular limitations as long as they have olefinic double bonds, carboxyl groups and isocyanuric acid skeletons. For example, the following resins (C3-1) and (C3-2) can be listed.

[0494] (C3-1) A resin obtained by further reacting a compound containing an epoxy group with an isocyanuric acid skeleton and an α,β-unsaturated monocarboxylic acid and / or ester compound with a polybasic acid and / or its anhydride.

[0495] Examples of epoxy-containing compounds having an isocyanuric acid skeleton include compounds represented by the following general formula (C3-1-1).

[0496]

[0497] In equation (C3-1-1), R 4 ~R 6 Each can be independently represented as an alkylene group, which can be truncated midway by an ether-type oxygen atom.

[0498] As an alkylene group, it is preferably composed of 1 or more carbon atoms. Furthermore, it is preferably composed of 6 or fewer carbon atoms, more preferably 4 or fewer, and even more preferably 2 or fewer. The above upper and lower limits can be combined arbitrarily. For example, 1 to 6 carbon atoms are preferred, more preferably 1 to 4, and even more preferably 1 to 2. The alkylene group can be linear or branched. By setting it to the aforementioned upper limit value or below, there is a tendency for improved developability and gas barrier properties.

[0499] Examples of alkylene groups include methylene, ethylene, n-propylene, isopropylene, n-butylene, isobutylene, n-pentylene, and n-hexylene. Furthermore, as alkylene groups truncated by an ether-type oxygen atom, examples include groups with 4 to 30 carbon atoms, optionally having a straight or branched alkylene chain, in which 1 to 10 carbon atoms are replaced by oxygen atoms; examples include groups containing 2 to 9 ethoxy groups or 2 to 7 propoxy groups.

[0500] From the viewpoint of gas barrier properties, methylene, ethylene, and n-propylene are preferred, with methylene being more preferred.

[0501] Examples of α,β-unsaturated monocarboxylic acids and / or ester compounds include: (meth)acrylic acid, monocarboxylic acids with α-haloalkyl, alkoxy, halogen, nitro, or cyano substituents at the α-position of (meth)acrylic acid; 2-(meth)acryloyloxyethyl succinic acid, 2-(meth)acryloyloxyethyl adipic acid, 2-(meth)acryloyloxyethyl phthalic acid, 2-(meth)acryloyloxyethyl hexahydrophthalic acid, 2-(meth)acryloyloxyethyl maleic acid, 2-(meth)acryloyloxypropyl succinic acid, 2-(meth)acryloyloxypropyl adipic acid, 2-(meth)acryloyloxypropyl adipic acid, 2-(meth)acryloyloxypropyl adipic acid, etc. Monomers obtained by adding methacryloyloxypropyltetrahydrophthalic acid, 2-(meth)acryloyloxypropylphthalic acid, 2-(meth)acryloyloxypropylmaleic acid, 2-(meth)acryloyloxybutylsuccinic acid, 2-(meth)acryloyloxybutyladipic acid, 2-(meth)acryloyloxybutylhydrophthalic acid, 2-(meth)acryloyloxybutylphthalic acid, 2-(meth)acryloyloxybutylmaleic acid; or by adding succinic acid (anhydride), phthalic acid (anhydride), maleic acid (anhydride), etc., to hydroxyalkyl esters of (meth)acrylate or pentaerythritol tri(meth)acrylate. From a sensitivity perspective, (meth)acrylic acid is preferred.

[0502] As a method for adding α,β-unsaturated monocarboxylic acids or α,β-unsaturated monocarboxylic acid esters with carboxyl groups to epoxy resins, the same method as for (C2) epoxy (meth)acrylate resins can be used.

[0503] Examples of polybasic acids and / or their anhydrides include, for example, maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenone tetracarboxylic acid, methylhexahydrophthalic acid, methylenetetrahydrophthalic acid, chloramphenic acid, methyltetrahydrophthalic acid, biphenyl tetracarboxylic acid, and their anhydrides.

[0504] Succinic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, biphenyl tetracarboxylic acid, and their anhydrides are preferred. Pyromellitic acid and its anhydrides are particularly preferred.

[0505] The addition reaction of polybasic acids and / or their anhydrides can be performed using the same method as with (C2) epoxy (meth)acrylate resins.

[0506] As α,β-unsaturated monocarboxylic acids and / or ester compounds, the same compounds as those described in the section on (C2) epoxy (meth)acrylate resins can be listed.

[0507] Furthermore, as polybasic acids and / or their anhydrides, compounds identical to those described in the section on resins (C1) can be listed.

[0508] (C3-2) A resin obtained by reacting a polyisocyanate compound having an isocyanuric acid skeleton with an acid or anhydride, and then reacting the resulting compound with an epoxy-containing (meth)acrylate compound.

[0509] As a resin of (C3-2), examples include the resin and its intermediates described in Japanese Patent Application Publication No. 2020-75994.

[0510] (C3) The weight-average molecular weight (Mw) of the resin containing the isocyanuric acid backbone is not particularly limited, but is preferably 1000 or more, more preferably 1500 or more, further preferably 2000 or more, even more preferably 3000 or more, even more preferably 4000 or more, and particularly preferably 5000 or more. Additionally, it is preferably 10000 or less, more preferably 8000 or less, and even more preferably 7000 or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1000 to 10000, more preferably 1500 to 10000, further preferably 1500 to 8000, even more preferably 2000 to 8000, and particularly preferably 2000 to 7000. By setting it to the aforementioned lower limit or above, the tendency for solubility in the developer to become excessively high can be suppressed. By setting it to the aforementioned upper limit or below, there is a tendency for good solubility in the developer.

[0511] (C3) The acid value of the resin containing the isocyanuric acid backbone is not particularly limited, but is preferably 20 mg KOH / g or more, more preferably 40 mg KOH / g or more, even more preferably 60 mg KOH / g or more, even more preferably 80 mg KOH / g or more, and particularly preferably 100 mg KOH / g or more. Furthermore, it is preferably 200 mg KOH / g or less, more preferably 150 mg KOH / g or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 20 to 200 mg KOH / g, more preferably 60 to 150 mg KOH / g. By setting it to the aforementioned lower limit or above, there is a tendency for improved developing solubility and better resolution. By setting it to the aforementioned upper limit or below, there is a tendency for a better residual film rate in the photosensitive coloring resin composition.

[0512] <(C4) Acrylic Copolymer Resin>

[0513] From the viewpoint of compatibility with pigments, dispersants, etc., (C4) acrylic copolymer resins can be used as (C1) alkali-soluble resins. As (C4) acrylic copolymer resins, the resin described in Japanese Patent Application Publication No. 2014-137466 is preferred, for example.

[0514] As a (C4) acrylic copolymer resin, examples include copolymers of an olefinic unsaturated monomer having one or more carboxyl groups (hereinafter referred to as "unsaturated monomer (C4-1)") with other copolymerizable olefinic unsaturated monomers (hereinafter referred to as "unsaturated monomer (C4-2)").

[0515] Examples of unsaturated monomers (C4-1) include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid; unsaturated dicarboxylic acids or their anhydrides such as maleic acid, maleic anhydride, fumaric acid, citraconic acid, citraconic anhydride, and mesocarboxylic acid; mono[(meth)acryloyloxyalkyl] esters of polycarboxylic acids with two or more members, such as succinate mono[2-(meth)acryloyloxyethyl] ester and phthalate mono[2-(meth)acryloyloxyethyl] ester; mono(meth)acrylates of polymers having carboxyl and hydroxyl groups at both ends, such as ω-carboxylated polycaprolactone mono(meth)acrylate; and p-vinylbenzoic acid.

[0516] These unsaturated monomers (C4-1) can be used alone or in combination of two or more.

[0517] Examples of unsaturated monomers (C4-2) include N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide.

[0518] Aromatic vinyl compounds such as styrene, α-methylstyrene, p-hydroxystyrene, p-hydroxy-α-methylstyrene, p-vinylbenzyl glycidyl ether, and acenaphthene;

[0519] Methyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate, 2-hydroxyethyl methacrylate, allyl methacrylate, benzyl methacrylate, polyethylene glycol (degree of polymerization 2-10) methyl ether (meth)acrylate, polypropylene glycol (degree of polymerization 2-10) methyl ether (meth)acrylate, polyethylene glycol (degree of polymerization 2-10) mono(meth)acrylate, polypropylene glycol (degree of polymerization 2-10) mono(meth)acrylate, cyclohexyl methacrylate, isobornyl methacrylate, tricyclohexyl methacrylate [5.2.1.0] 2,6 Decane-8-ester, dicyclopentenyl (meth)acrylate, glyceryl mono(meth)acrylate, 4-hydroxyphenyl (meth)acrylate, ethylene oxide-modified (meth)acrylate of p-cumylphenol, glycidyl (meth)acrylate, 3,4-epoxycyclohexyl methyl (meth)acrylate, 3-[(meth)acryloyloxymethyl]oxetane, 3-[(meth)acryloyloxymethyl]-3-ethyloxetane, etc. (meth)acrylates;

[0520] Cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo[5.2.1.0] 2,6 Vinyl ethers such as decane-8-yl vinyl ether, pentacyclic pentadecyl vinyl ether, and 3-(vinyloxymethyl)-3-ethyloxetane;

[0521] Macromonomers with mono(meth)acryloyl groups at the ends of polymer molecular chains such as polystyrene, poly(meth)acrylate, poly(n-butyl)methacrylate, and polysiloxane.

[0522] These unsaturated monomers (C4-2) can be used alone or in combination of two or more.

[0523] In the copolymer of unsaturated monomer (C4-1) and unsaturated monomer (C4-2), the copolymerization ratio of unsaturated monomer (C4-1) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass. By copolymerizing the unsaturated monomer (C4-1) within such a range, there is a tendency to obtain a photosensitive coloring resin composition with excellent alkali developability and storage stability.

[0524] Examples of copolymers of unsaturated monomers (C4-1) and unsaturated monomers (C4-2) include those disclosed in Japanese Patent Application Publication Nos. 7-140654, 8-259876, 10-31308, 10-300922, 11-174224, 11-258415, 2000-56118, and 2004-101728.

[0525] Copolymers of unsaturated monomers (C4-1) and (C4-2) can be manufactured by known methods, for example, by methods disclosed in Japanese Patent Application Publication No. 2003-222717, Japanese Patent Application Publication No. 2006-259680, and International Patent Application Publication No. 2007 / 029871, which control their structure, Mw, and Mw / Mn (Mn being the number average molecular weight).

[0526] In addition to the above, the resins described in International Publication No. 2016 / 194619 and International Publication No. 2017 / 154439 may also be used as (C4) acrylic copolymer resins.

[0527] <(D) Photopolymerization initiators>

[0528] The photosensitive coloring resin composition of the present invention contains a (D) photopolymerization initiator. The (D) photopolymerization initiator is a component that directly absorbs light, undergoes a decomposition reaction or a hydrogen abstraction reaction, and thus has the function of generating polymerization-active free radicals. Additives such as polymerization accelerators (chain transfer agents) and sensitized pigments may also be added or used as needed.

[0529] Examples of photopolymerization initiators include: metallocene compounds, including dititanium compounds, as described in Japanese Patent Application Publication Nos. 59-152396 and 61-151197; hexaaryl biimidazole derivatives as described in Japanese Patent Application Publication No. 2000-56118; halomethylated oxadiazole derivatives and halomethyltriazine derivatives as described in Japanese Patent Application Publication No. 10-39503; α-aminoalkyl phenyl ketone derivatives; and oxime ester compounds as described in Japanese Patent Application Publication Nos. 2000-80068 and 2006-36750.

[0530] Examples of metallocene compounds include dicyclopentadienyl titanium dichloride, dicyclopentadienyl titanium bisphenyl, dicyclopentadienyl titanium bis(2,3,4,5,6-pentafluorobenzene-1-yl), dicyclopentadienyl titanium bis(2,3,5,6-tetrafluorobenzene-1-yl), dicyclopentadienyl titanium bis(2,4,6-trifluorobenzene-1-yl), dicyclopentadienyl titanium di(2,6-difluorobenzene-1-yl), dicyclopentadienyl titanium di(2,4-difluorobenzene-1-yl), di(methylcyclopentadienyl)titanium bis(2,3,4,5,6-pentafluorobenzene-1-yl), di(methylcyclopentadienyl)titanium bis(2,6-difluorobenzene-1-yl), and dicyclopentadienyl titanium [2,6-di-fluoro-3-(pyrrole-1-yl)-phenyl-1-yl].

[0531] Examples of hexaaryl biimidazole derivatives include 2-(2'-chlorophenyl)-4,5-diphenylimidazolium dimer, 2-(2'-chlorophenyl)-4,5-bis(3'-methoxyphenyl)imidazolium dimer, 2-(2'-fluorophenyl)-4,5-diphenylimidazolium dimer, 2-(2'-methoxyphenyl)-4,5-diphenylimidazolium dimer, and (4'-methoxyphenyl)-4,5-diphenylimidazolium dimer.

[0532] Examples of halomethylated oxadiazole derivatives include 2-trichloromethyl-5-(2'-benzofuranyl)-1,3,4-oxadiazole, 2-trichloromethyl-5-[β-(2'-benzofuranyl)vinyl]-1,3,4-oxadiazole, 2-trichloromethyl-5-[β-(2'-(6”-benzofuranyl)vinyl)]-1,3,4-oxadiazole, and 2-trichloromethyl-5-furanyl-1,3,4-oxadiazole.

[0533] Examples of halomethyl-s-triazine derivatives include 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(4-ethoxycarbonylnaphthyl)-4,6-bis(trichloromethyl)-s-triazine.

[0534] Examples of α-aminoalkylphenyl ketone derivatives include: 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholinophenyl)butan-1-one, and 3,6-bis(2-methyl-2-morpholinopropionyl)-9-octylcarbazole.

[0535] Oxime ester compounds are effective as (D) photopolymerization initiators, particularly in terms of sensitivity and printability. For example, such highly sensitive oxime ester compounds are especially useful when using alkali-soluble resins containing phenolic hydroxyl groups. Because oxime ester compounds simultaneously possess structures for absorbing ultraviolet light, transmitting light energy, and generating free radicals, they exhibit high sensitivity even in small quantities and are thermally stable, enabling the production of highly sensitive photosensitive coloring resin compositions in small amounts.

[0536] Examples of oxime ester compounds include those represented by the general formula (IV) below.

[0537]

[0538] In equation (IV), R 21a Represents a hydrogen atom, an alkyl group optionally having a substituent, or an aromatic cyclogroup optionally having a substituent.

[0539] R 21b It represents any substituent containing an aromatic ring.

[0540] R 22a This indicates an alkyl acyl group or an aromatic acyl group that may optionally have a substituent.

[0541] n represents an integer that is either 0 or 1.

[0542] R 21a The number of carbon atoms in the alkyl group is not particularly limited, but from the viewpoint of solubility and sensitivity in the solvent, it is preferably 1 or more, more preferably 2 or more, and preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. Examples of alkyl groups include methyl, ethyl, propyl, and cyclopentylethyl.

[0543] Examples of substituents that may be optionally present in the alkyl group include aromatic cyclic groups, hydroxyl groups, carboxyl groups, halogen atoms, amino groups, amide groups, 4-(2-methoxy-1-methyl)ethoxy-2-methylphenyl groups, and N-acetyl-N-acetoxyamino groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0544] As R 21a The aromatic ring group in the composition can include aromatic hydrocarbon ring groups and aromatic heterocyclic ring groups. The number of carbon atoms in the aromatic ring group is not particularly limited, but from the viewpoint of solubility in the photosensitive coloring resin composition, it is preferably 5 or more. Furthermore, from the viewpoint of developability, it is preferably 30 or less, more preferably 20 or less, and even more preferably 12 or less. For example, it is preferably 5 to 30, more preferably 5 to 20, and even more preferably 5 to 12.

[0545] Examples of aromatic cyclic groups include phenyl, naphthyl, pyridyl, and furanyl. From the viewpoint of reproducibility, phenyl or naphthyl is preferred, and phenyl is more preferred.

[0546] As optional substituents in an aromatic cyclic group, examples include hydroxyl, carboxyl, halogen, amino, amide, alkyl, alkoxy, and groups formed by linking these substituents. From the viewpoint of reproducibility, alkyl, alkoxy, or groups formed by linking these substituents are preferred, and linked alkoxy groups are more preferred.

[0547] From the perspective of radioactivity, R 21a Preferably, the aromatic cyclic group has a substituent, and more preferably, the substituent is an aromatic cyclic group with a linked alkoxy group.

[0548] As R 21b Examples of substituted carbazole groups, optionally substituted thioxanone groups, optionally substituted diphenyl sulfide groups, optionally substituted fluorenyl groups, or optionally substituted indole groups may be included. From the viewpoint of sensitivity, optionally substituted carbazole groups are preferred. From the viewpoint of electrical reliability, optionally substituted diphenyl sulfide groups are preferred.

[0549] R 22a The number of carbon atoms in the alkyl acyl group is not particularly limited, but from the viewpoint of solubility and sensitivity in the solvent, it is preferably 2 or more, more preferably 20 or less, more preferably 15 or less, even more preferably 10 or less, and particularly preferably 5 or less. For example, acetyl, propionyl, and butyryl can be listed as alkyl acyl groups.

[0550] Examples of substituents that can be optionally present on the alkyl acyl group include aromatic cyclic groups, hydroxyl groups, carboxyl groups, halogen atoms, amino groups, and amide groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0551] R 22a The number of carbon atoms in the aryl group is not particularly limited, but from the viewpoint of solubility and sensitivity in the solvent, it is preferably 7 or more, more preferably 8 or more, and preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. Examples of aryl groups include benzoyl and naphthyl.

[0552] Examples of substituents that can be optionally present on the aryl group include hydroxyl, carboxyl, halogen, amino, amide, and alkyl groups. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0553] From the perspective of sensitivity, R 22a Preferably, it is an alkyl acyl group with a substituent, more preferably an unsubstituted alkyl acyl group, and even more preferably an acetyl group.

[0554] For example, photopolymerization initiators described in Japanese Patent No. 4454067, International Publication No. 2002 / 100903, International Publication No. 2012 / 45736, International Publication No. 2015 / 36910, International Publication No. 2006 / 18973, International Publication No. 2008 / 78678, Japanese Patent No. 4818458, International Publication No. 2005 / 80338, International Publication No. 2008 / 75564, International Publication No. 2009 / 131189, International Publication No. 2009 / 131189, International Publication No. 2010 / 133077, International Publication No. 2010 / 102502, and International Publication No. 2012 / 68879 can be used.

[0555] From the perspective of reducing pollution caused by colorants, the initiator described in Japanese Patent Application Publication No. 2016-133574 may also be used.

[0556] Photopolymerization initiators can be used alone or in combination of two or more.

[0557] As needed, to improve sensitivity, sensitizing pigments and polymerization accelerators matching the wavelength of the image exposure light source can be mixed into the photopolymerization initiator. Examples of sensitizing pigments include, for instance, the xanthan pigments described in Japanese Patent Application Publications Nos. 4-221958 and 4-219756; heterocyclic coumarin pigments described in Japanese Patent Application Publications Nos. 3-239703 and 5-289335; 3-ketocoumarin compounds described in Japanese Patent Application Publications Nos. 3-239703 and 5-289335; pyrrolemethylammonium pigments described in Japanese Patent Application Publications No. 6-19240; and Japanese Patent Application Publications Nos. 47-2528 and 54-155292. Pigments having a dialkylaminobenzene skeleton as described in the following publications: Japanese Patent Publication No. 45-37377, Japanese Patent Application Publication No. 48-84183, Japanese Patent Application Publication No. 52-112681, Japanese Patent Application Publication No. 58-15503, Japanese Patent Application Publication No. 60-88005, Japanese Patent Application Publication No. 59-56403, Japanese Patent Application Publication No. 2-69, Japanese Patent Application Publication No. 57-168088, Japanese Patent Application Publication No. 5-107761, Japanese Patent Application Publication No. 5-210240, and Japanese Patent Application Publication No. 4-288818.

[0558] As a sensitizing pigment, an amino-containing sensitizing pigment is preferred, and a compound having both an amino group and a phenyl group within the same molecule is more preferred. For example, benzophenone compounds such as 4,4'-dimethylaminobenzophenone, 4,4'-diethylaminobenzophenone, 2-aminobenzophenone, 4-aminobenzophenone, 4,4'-diaminobenzophenone, 3,3'-diaminobenzophenone, and 3,4-diaminobenzophenone are preferred; benzophenone-based compounds such as 2-(p-dimethylaminophenyl)benzoxazole, 2-(p-diethylaminophenyl)benzoxazole, 2-(p-dimethylaminophenyl)benzo[4,5]benzoxazole, 2-(p-dimethylaminophenyl)benzo[6,7]benzoxazole, and 2,5-bis(p-diethylaminophenyl)-1,3,4-oxazole are preferred. Compounds containing p-dialkylaminophenyl, such as 2-(p-dimethylaminophenyl)benzothiazole, 2-(p-diethylaminophenyl)benzothiazole, 2-(p-dimethylaminophenyl)benzimidazole, 2,5-bis(p-diethylaminophenyl)-1,3,4-thiadiazole, (p-dimethylaminophenyl)pyridine, (p-diethylaminophenyl)pyridine, (p-dimethylaminophenyl)quinoline, (p-diethylaminophenyl)quinoline, (p-dimethylaminophenyl)pyrimidine, (p-diethylaminophenyl)pyrimidine, etc., are particularly preferred to be 4,4'-dialkylaminobenzophenone.

[0559] Sensitizing pigments can be used alone or in combination of two or more.

[0560] As polymerization accelerators, aromatic amines such as ethyl p-dimethylaminobenzoate and 2-dimethylaminoethyl benzoate; aliphatic amines such as n-butylamine and N-methyldiethanolamine; and thiol compounds described later can be used. A single polymerization accelerator can be used alone, or two or more can be used in combination.

[0561] <(E) olefinic unsaturated compounds>

[0562] The photosensitive coloring resin composition of the present invention may contain (E) olefin unsaturated compounds. By containing (E) olefin unsaturated compounds, there is a tendency to improve sensitivity.

[0563] The (E) olefin unsaturated compounds used in this invention are compounds having at least one olefin unsaturated group within their molecule. Specifically, examples include (meth)acrylic acid, alkyl (meth)acrylates, acrylonitrile, styrene, carboxylic acids having one olefin unsaturated bond, and monoesters of polyols or monohydric alcohols.

[0564] In this invention, polyfunctional olefin monomers having two or more olefin unsaturated groups per molecule are particularly preferred. The number of olefin unsaturated groups in the polyfunctional olefin monomer is not particularly limited, but is preferably two or more, more preferably four or more, even more preferably five or more, and preferably eight or less, even more preferably seven or less. The above upper and lower limits can be combined arbitrarily. For example, 2 to 8 groups are preferred, more preferably 2 to 7, even more preferably 4 to 7, and particularly preferably 5 to 7. By setting the value to the aforementioned lower limit or above, there is a tendency to achieve high sensitivity. Furthermore, by setting the value to the aforementioned upper limit or below, there is a tendency to improve solubility in solvents.

[0565] Examples of polyfunctional olefin monomers include: esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids; esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids; and esters obtained by esterification reactions of polyhydroxy compounds such as aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds with unsaturated carboxylic acids and polycarboxylic acids.

[0566] Examples of esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids include ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolethane triacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, and glyceryl acrylate; methacrylates obtained by replacing these acrylates with methacrylates; itaconic acid esters obtained by replacing these acrylates with itaconic acid esters; crotonic acid esters obtained by replacing these acrylates with crotonic acid esters; and maleic acid esters obtained by replacing these acrylates with maleic acid esters.

[0567] Examples of esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids include hydroquinone diacrylate, hydroquinone dimethacrylate, resorcinol diacrylate, resorcinol dimethacrylate, pyrogallol triacrylate, and other acrylates and methacrylates of aromatic polyhydroxy compounds.

[0568] Esters, obtained through the esterification reaction of polycarboxylic acids and unsaturated carboxylic acids with polyhydroxy compounds, are not necessarily single compounds. Examples include condensates of acrylic acid, phthalic acid, and ethylene glycol; condensates of acrylic acid, maleic acid, and diethylene glycol; condensates of methacrylic acid, terephthalic acid, and pentaerythritol; and condensates of acrylic acid, adipic acid, butanediol, and glycerol.

[0569] Furthermore, examples of polyfunctional olefin monomers used in this invention include: urethane (meth)acrylates obtained by reacting a polyisocyanate compound with a hydroxyl (meth)acrylate or a polyisocyanate compound with a polyol and a hydroxyl (meth)acrylate; epoxy acrylates such as addition reactions of polyepoxides with hydroxyl (meth)acrylates or (meth)acrylic acid; acrylamides such as ethylene bisacrylamide; allyl esters such as diallyl phthalate; and vinyl compounds such as divinyl phthalate.

[0570] Examples of urethane (meth)acrylates include: DPHA-40H, UX-5000, UX-5002D-P20, UX-5003D, UX-5005 (manufactured by Nippon Kayaku Co., Ltd.), U-2PPA, U-6LPA, U-10PA, U-33H, UA-53H, UA-32P, UA-1100H (manufactured by Shin-Nakamura Chemical Co., Ltd.), UA-306H, UA-510H, UF-8001G (manufactured by Kyoesha Chemical Co., Ltd.), UV-1700B, UV-7600B, UV-7605B, UV-7630B, and UV7640B (manufactured by Mitsubishi Chemical Co., Ltd.).

[0571] From the viewpoint of curability, as (E) olefinic unsaturated compounds, alkyl (meth)acrylates, polyisocyanate compounds reacting with hydroxyl-containing (meth)acrylates, or polyisocyanate compounds reacting with polyols and hydroxyl-containing (meth)acrylates to obtain urethane (meth)acrylates are preferred, and polyisocyanate compounds and hydroxyl-containing (meth)acrylates are more preferred.

[0572] They can be used individually or in combination of two or more.

[0573] <Other Components in the Formulation of the Photosensitive Coloring Resin Composition>

[0574] In addition to the above-mentioned components, the photosensitive coloring resin composition of the present invention may also be appropriately mixed with binders such as silane coupling agents, surfactants, pigment derivatives, photoacid generators, crosslinking agents, mercapto compounds, polymerization inhibitors, and other additives.

[0575] (1) Adhesion enhancer

[0576] In order to improve adhesion to the substrate, the photosensitive coloring resin composition of the present invention may contain an adhesion improver. Preferably, the adhesion improver is a silane coupling agent or a phosphate-containing compound.

[0577] As a silane coupling agent, one type of epoxy, (meth)acrylic, amino, or other silane coupling agent can be used alone, or two or more can be used in combination.

[0578] Examples of silane coupling agents include: (meth)acryloyloxysilanes such as 3-methacryloyloxypropylmethyldimethoxysilane and 3-methacryloyloxypropyltrimethoxysilane; epoxy silanes such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-epoxypropoxypropyltrimethoxysilane, 3-epoxypropoxypropylmethyldiethoxysilane and 3-epoxypropoxypropyltriethoxysilane; ureosilanes such as 3-ureopropyltriethoxysilane; and isocyanate silanes such as 3-isocyanate-propyltriethoxysilane. Epoxy silane coupling agents are particularly preferred.

[0579] As a phosphate-containing compound, it is preferably a phosphate ester containing (meth)acryloyl group, and preferably a substance shown in the following general formula (g1), (g2) or (g3).

[0580]

[0581] In equations (g1), (g2), and (g3), R 51 Represents a hydrogen atom or a methyl group, where l and l' are integers from 1 to 10, and m is 1, 2, or 3.

[0582] These phosphate-containing compounds can be used alone or in combination of two or more.

[0583] (2) Surfactants

[0584] To improve coatability, the photosensitive coloring resin composition of the present invention may contain a surfactant.

[0585] As surfactants, various surfactants can be used, such as anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants. From the perspective of minimizing the possibility of adverse effects on various properties, nonionic surfactants are preferred, and from the perspective of coatability, fluorinated and silicone surfactants are more preferred.

[0586] Examples of such surfactants include: TSF4460 (manufactured by Momentive Performance Materials), DFX-18 (manufactured by NEOS), BYK-300, BYK-325, BYK-330 (manufactured by BYK-Chemie), KP340 (manufactured by Shin-Etsu Silicones), F-470, F-475, F-478, F-554, F-559 (manufactured by DIC), SH7PA (manufactured by Dow Corning Toray), DS-401 (manufactured by Daikin), L-77 (manufactured by Unicar Corporation of Japan), and FC4430 (manufactured by 3M).

[0587] One surfactant can be used, or two or more surfactants can be used in combination.

[0588] (3) Pigment derivatives

[0589] To improve dispersibility and shelf life, the photosensitive coloring resin composition of the present invention may also contain pigment derivatives as dispersing aids.

[0590] Examples of pigment derivatives include azo, phthalocyanine, quinacridone, benzimidazolone, quinophthalone, isoindolineone, dioxazine, anthraquinone, indanthrene, perylene, perinone, diketopyrrolopyrrole, and dioxazine derivatives, with phthalocyanine and quinophthalone derivatives being preferred.

[0591] Substituents used in pigment derivatives include, for example, sulfonic acid groups, sulfonamide groups and their quaternary salts, phthalimide methyl groups, dialkylaminoalkyl groups, hydroxyl groups, carboxyl groups, and amide groups, which are directly or indirectly bonded to the pigment skeleton via, for example, alkyl, aryl, or heterocyclic groups. Sulfonic acid groups are preferred. Multiple substituents can be substituted on a pigment skeleton.

[0592] Examples of pigment derivatives include sulfonic acid derivatives of phthalocyanine, sulfonic acid derivatives of quinophthalone, sulfonic acid derivatives of anthraquinone, sulfonic acid derivatives of quinacridone, sulfonic acid derivatives of diketopyrrolopyrrole, and sulfonic acid derivatives of dioxazine. They can be used individually or in combination of two or more.

[0593] (4) Thiol compounds

[0594] In the photosensitive coloring resin composition of the present invention, a mercapto compound may be included as a polymerization accelerator in order to improve adhesion to the substrate.

[0595] Examples of thiol compounds include: 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, hexanedithiol, decanedithiol, 1,4-dimethylmercaptobenzene, butylene dimercaptopropionate, butylene dimercaptoacetate, ethylene glycol dimercaptoacetate, trimethylolpropane trimercaptoacetate, butylene dimercaptopropionate, trimethylolpropane trimercaptopropionate, pentaerythritol tetramercaptopropionate, pentaerythritol tetramercaptoacetate, trihydroxyethyl trimercaptopropionate, ethylene glycol bis(3-mercaptobutyrate), and butylene glycol bis(3-mercaptopropionate). Heterocyclic thiol compounds and aliphatic polyfunctional thiol compounds, such as 3-mercaptobutyrate, 1,4-bis(3-mercaptobutyryloxy)butane, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetra(3-mercaptobutyrate), pentaerythritol tris(3-mercaptobutyrate), ethylene glycol bis(3-mercaptoisobutyrate), butanediol bis(3-mercaptoisobutyrate), trimethylolpropane tris(3-mercaptoisobutyrate), and 1,3,5-tris(3-mercaptobutoxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, can be used. These substances can be used alone or in combination of two or more.

[0596] (5) Polymerization inhibitors

[0597] From the viewpoint of controlling the shape of the cured product, the photosensitive coloring resin composition of the present invention may contain a polymerization inhibitor. It is believed that by containing a polymerization inhibitor, the free radical polymerization of the underlayer of the coating film is hindered, thereby controlling the cone angle (the angle between the support and the cured product in the cross-section of the cured product).

[0598] Examples of polymerization inhibitors include hydroquinone, hydroquinone monomethyl ether, methyl hydroquinone, methoxyphenol, and 2,6-di-tert-butyl-4-cresol (BHT). From the viewpoint of shape control, 2,6-di-tert-butyl-4-cresol is preferred. From the viewpoint of particularly excellent safety for human health, hydroquinone monomethyl ether and methyl hydroquinone are preferred.

[0599] A single polymerization inhibitor can be used alone, or two or more can be used in combination.

[0600] In the manufacture of (C) alkali-soluble resin, the resin may sometimes contain a polymerization inhibitor, which can be used as the polymerization inhibitor of the present invention. In addition to the polymerization inhibitor in the resin, the same or different polymerization inhibitors may also be added during the manufacture of the photosensitive coloring resin composition.

[0601] When the photosensitive coloring resin composition contains a polymerization inhibitor, its content ratio is not particularly limited. Relative to the total solid content of the photosensitive coloring resin composition, it is preferably 0.0005% by mass or more, more preferably 0.001% by mass or more, and even more preferably 0.01% by mass or more. Furthermore, it is preferably 0.3% by mass or less, more preferably 0.2% by mass or less, and even more preferably 0.1% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 0.0005% to 0.3% by mass, more preferably 0.001% to 0.2% by mass, and even more preferably 0.01% to 0.1% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to control the shape of the cured product. By setting it to the aforementioned upper limit or below, there is a tendency to maintain the desired sensitivity.

[0602] (6) Solvent

[0603] The photosensitive coloring resin composition of the present invention preferably contains a solvent. By including a solvent, the colorant can be dispersed or dissolved in the solvent, and coating becomes easier.

[0604] The photosensitive coloring resin composition of the present invention is used, for example, in a state in which (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin, (D) a photopolymerization initiator, and various other materials used as needed are dissolved or dispersed in a solvent. From the viewpoint of dispersibility and coatability, organic solvents are preferred.

[0605] From a coating properties perspective, organic solvents with a boiling point of 100–300°C are preferred, and those with a boiling point of 120–280°C are more preferred. It should be noted that the boiling point referred to here is the boiling point at a pressure of 1013.25 hPa, and the same applies to boiling points in the following text.

[0606] Examples of such organic solvents include: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-butyl ether, propylene glycol tert-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, methoxymethylpentanol, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methoxybutanol, 3-methyl-3-methoxybutanol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, tripropylene glycol methyl ether, and other diethylene glycol monoalkyl ethers;

[0607] Dialkyl ethers of glycols, such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, and dipropylene glycol dimethyl ether;

[0608] Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, methoxybutyl acetate, 3-methoxybutyl acetate, methoxypentyl acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-butyl ether acetate, dipropylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether acetate, triethylene glycol monoethyl ether acetate, 3-methyl-3-methoxybutyl acetate, and other diol alkyl ether acetates;

[0609] Diol diacetates such as ethylene glycol diacetate, 1,3-butanediol diacetate, and 1,6-hexanediol diacetate;

[0610] Alkyl acetates such as cyclohexanol acetate;

[0611] Ethers such as pentyl ether, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, dipentyl ether, ethyl isobutyl ether, and dihexyl ether;

[0612] Ketones such as acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isopentyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl nonyl ketone, and methoxymethyl amyl ketone;

[0613] Monohydric or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, butanediol, diethylene glycol, dipropylene glycol, triethylene glycol, methoxymethylpentanol, glycerol, and benzyl alcohol;

[0614] Aliphatic hydrocarbons such as n-pentane, n-octane, diisobutylene, n-hexane, hexene, isoprene, dipentene, and dodecane;

[0615] Alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, and dicyclohexane;

[0616] Aromatic hydrocarbons such as benzene, toluene, xylene, and cumene;

[0617] Amyl formate, ethyl formate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, methyl isobutyrate, ethylene glycol acetate, ethyl propionate, propyl propionate, butyl butyrate, isobutyl butyrate, methyl isobutyrate, ethyl octanoate, butyl stearate, ethyl benzoate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, butyl 3-methoxypropionate, γ-butyrolactone, and other chain or cyclic esters;

[0618] Alkoxycarboxylic acids such as 3-methoxypropionic acid and 3-ethoxypropionic acid;

[0619] Halogenated hydrocarbons such as chlorobutane and chloropentane;

[0620] Ether ketones such as methoxymethylpentanone;

[0621] Nitriles such as acetonitrile and benzonitrile.

[0622] Commercially available organic solvents include, for example, mineral spirit, Varsol#2, Apco#18 Solvent, Apco thinner, Sorcal solvent No.1 and No.2, Solvesso#150, Shell TS28 Solvent, carbitol, ethyl carbitol, butyl carbitol, methyl cellosolve (“cellosolve” is a registered trademark, the same applies hereinafter), ethyl cellosolve, ethyl cellosolve acetate, methyl cellosolve acetate, and diethylene glycol dimethyl ether (diglyme) (all trade names).

[0623] These organic solvents can be used alone or in combination of two or more.

[0624] When forming the partition wall using photolithography, the organic solvent preferably has a boiling point of 100 to 240°C, more preferably has a boiling point of 120 to 200°C, and even more preferably has a boiling point of 120 to 170°C.

[0625] From the perspective of good balance of coatability and surface tension, and high solubility of the constituent components in the composition, glycol alkyl ether acetates are preferred.

[0626] Diol alkyl ether acetates can be used alone or in combination of two or more.

[0627] Diol alkyl ether acetates can be used alone, or in combination with other organic solvents. As organic solvents used in combination, monoalkyl glycol ethers are preferred. From the perspective of the solubility of the constituent components in the composition, propylene glycol monomethyl ether is preferred.

[0628] Diol monoalkyl ethers are highly polar. If too much is added, the pigments tend to aggregate easily, and the viscosity of the resulting photosensitive coloring resin composition increases, leading to a decrease in storage stability. Therefore, the proportion of diol monoalkyl ethers in the solvent is preferably 5 to 30% by mass, more preferably 5 to 20% by mass.

[0629] By combining organic solvents with boiling points above 150°C (hereinafter sometimes referred to as "high-boiling-point solvents"), although the photosensitive coloring resin composition becomes more difficult to dry, it has the effect of preventing the uniform dispersion of pigments in the composition from being destroyed by rapid drying. Therefore, high-boiling-point solvents can be used in combination. For example, it has the effect of preventing the generation of foreign matter defects caused by the precipitation / curing of colorants at the tip of the slit nozzle. From the perspective of high effectiveness, when using high-boiling-point solvents in combination, it is preferable to use diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, and diethylene glycol monoethyl ether acetate in combination.

[0630] When using high-boiling-point solvents in combination, the content of high-boiling-point solvents in the organic solvent is preferably 3 to 50% by mass, more preferably 5 to 40% by mass, and particularly preferably 5 to 30% by mass. By setting the content to the aforementioned lower limit or above, it is possible to suppress, for example, the tendency for colorants or the like to precipitate / cure at the tip of the slit nozzle, causing foreign matter defects. By setting the content to the aforementioned upper limit or below, it is possible to suppress the increase in drying time of the composition, thereby suppressing problems such as poor cycle time in the vacuum drying process and pin marks from pre-baking.

[0631] The high-boiling-point solvent can be a glycol alkyl ether acetate or a glycol alkyl ether. In this case, it is also possible not to contain an additional high-boiling-point solvent.

[0632] Preferred high-boiling-point solvents include, for example, diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butanediol diacetate, 1,6-hexanol diacetate, and glyceryl triacetate.

[0633] <Proportion of each component in the photosensitive coloring resin composition>

[0634] The proportion of colorant (A) in the photosensitive coloring resin composition of the present invention is not particularly limited, but is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, relative to the total solid content of the photosensitive coloring resin composition. Furthermore, it is preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 5 to 40% by mass, more preferably 10 to 30% by mass, even more preferably 15 to 30% by mass, even more preferably 15 to 25% by mass, and particularly preferably 15 to 20% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to ensure light-blocking properties. By setting it to the aforementioned upper limit or below, there is a tendency to reduce the dispersion dosage and suppress surface roughness.

[0635] The proportion of organic pigment (A-1) in the photosensitive coloring resin composition of the present invention is not particularly limited, but is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, relative to the total solid content of the photosensitive coloring resin composition. Furthermore, it is preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 5 to 40% by mass, more preferably 10 to 30% by mass, even more preferably 15 to 30% by mass, even more preferably 15 to 25% by mass, and particularly preferably 15 to 20% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to ensure light-blocking properties. By setting it to the aforementioned upper limit or below, there is a tendency for the residual film rate to increase.

[0636] When the photosensitive coloring resin composition of the present invention contains an organic black pigment, the proportion of the organic black pigment in the photosensitive coloring resin composition is not particularly limited, but is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, relative to the total solid content of the photosensitive coloring resin composition. Furthermore, it is preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 5 to 40% by mass, more preferably 10 to 30% by mass, even more preferably 15 to 30% by mass, even more preferably 15 to 25% by mass, and particularly preferably 15 to 20% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to ensure light-blocking properties. By setting it to the aforementioned upper limit or below, there is a tendency for the residual film rate to increase.

[0637] When the photosensitive coloring resin composition of the present invention contains a colorant other than the organic pigment (A-1), the proportion of the colorant is not particularly limited, but it is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more in the total solid components of the photosensitive coloring resin composition. Furthermore, it is preferably 30% by mass or less, more preferably 20% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1 to 30% by mass, more preferably 5 to 20% by mass, and even more preferably 10 to 20% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to suppress the loss of ultraviolet light required for curing and to increase the light-blocking property. By setting it to the aforementioned upper limit or below, there is a tendency to increase the residual film rate.

[0638] (B) The proportion of the dispersant is not particularly limited, but relative to the total solid content of the photosensitive coloring resin composition, it is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more. Furthermore, it is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, and even more preferably 7% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1 to 20% by mass, more preferably 2 to 15% by mass, even more preferably 3 to 10% by mass, and particularly preferably 3 to 7% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to easily obtain sufficient dispersibility. By setting it to the aforementioned upper limit or below, there is a tendency to reduce venting.

[0639] The proportion of dispersant (B) relative to 100 parts by weight of colorant (A) is not particularly limited, but is preferably 5 parts by weight or more, more preferably 10 parts by weight or more, and even more preferably 15 parts by weight or more. It is also preferably 50 parts by weight or less, and even more preferably 30 parts by weight or less. The above upper and lower limits can be combined arbitrarily. For example, 5 to 50 parts by weight is preferred, more preferably 10 to 50 parts by weight, and even more preferably 15 to 30 parts by weight. By setting it to the aforementioned lower limit or above, there is a tendency to easily obtain sufficient dispersibility. By setting it to the aforementioned upper limit or below, there is a tendency for the residual film rate to increase.

[0640] (C) The proportion of alkali-soluble resin is not particularly limited, but relative to the total solid content of the photosensitive coloring resin composition, it is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 20% by mass or more, even more preferably 30% by mass or more, particularly preferably 40% by mass or more, and preferably 85% by mass or less, more preferably 80% by mass or less, further preferably 70% by mass or less, even more preferably 60% by mass or less, particularly preferably 55% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, further preferably 20 to 60% by mass, even more preferably 30 to 60% by mass, even more preferably 30 to 55% by mass, and particularly preferably 40 to 55% by mass. By setting it to the aforementioned lower limit or above, it is possible to suppress the decrease in solubility of the unexposed portion in the developer and suppress the tendency for poor development. By setting it to the aforementioned upper limit or below, it is possible to maintain suitable sensitivity and suppress the tendency for the exposed portion to dissolve due to the developer and for the cone angle to decrease.

[0641] The content of resin (C1) is not particularly limited, but relative to the total solid content of the photosensitive coloring resin composition, it is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. Furthermore, it is preferably 20% by mass or less, more preferably 17% by mass or less, even more preferably 15% by mass or less, and even more preferably 10% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1 to 20% by mass, more preferably 3 to 17% by mass, even more preferably 3 to 15% by mass, and particularly preferably 5 to 10% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to improve dispersion stability. By setting it to the aforementioned upper limit or below, there is a tendency to improve solubility in the developer.

[0642] The content of resin (C1) is not particularly limited, but in the alkali-soluble resin (C), it is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more. Furthermore, it is preferably 100% by mass or less, more preferably 80% by mass or less, even more preferably 60% by mass or less, even more preferably 40% by mass or less, and particularly preferably 20% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1 to 100% by mass, more preferably 5 to 80% by mass, even more preferably 10 to 60% by mass, even more preferably 10 to 40% by mass, and particularly preferably 10 to 20% by mass. By setting it to the aforementioned lower limit or above, it is possible to suppress the decrease in solubility of unexposed portions in the developer and suppress poor development. By setting it to the aforementioned upper limit or below, it is possible to maintain suitable sensitivity, suppress the dissolution of exposed portions due to the developer, and suppress the decrease in pattern clarity and adhesion.

[0643] When the photosensitive coloring resin composition of the present invention contains a (C2) epoxy (meth)acrylate resin, the content ratio of the (C2) epoxy (meth)acrylate resin is not particularly limited. However, relative to the total solid content of the photosensitive coloring resin composition of the present invention, it is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and particularly preferably 40% by mass or more. Furthermore, it is preferably 80% by mass or less, more preferably 70% by mass or less, even more preferably 60% by mass or less, and particularly preferably 55% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, further preferably 15 to 60% by mass, even more preferably 20 to 60% by mass, even more preferably 30 to 55% by mass, and particularly preferably 40 to 55% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to ensure the solubility of the unexposed portion in the developing solution. By setting the value below the aforementioned upper limit, it is possible to maintain appropriate sensitivity, suppress the dissolution of the exposed area due to the developer, and suppress the reduction in pattern clarity and adhesion.

[0644] When the alkali-soluble resin (C) includes a (C2) epoxy (meth)acrylate resin, the proportion of the (C2) epoxy (meth)acrylate resin in the alkali-soluble resin (C) is not particularly limited, but is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 40% by mass or more. It is also preferably 100% by mass or less, more preferably 90% by mass or less, and even more preferably 80% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, 20 to 100% by mass is preferred, more preferably 30 to 90% by mass, and even more preferably 40 to 80% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to ensure the solubility of the unexposed portion in the developer. By setting it to the aforementioned upper limit or below, there is a tendency to maintain suitable sensitivity, suppress the dissolution of the exposed portion due to the developer, and suppress the reduction of pattern clarity and adhesion.

[0645] When the alkali-soluble resin (C) includes a resin containing an isocyanuric acid backbone (C3), the proportion of the resin containing the isocyanuric acid backbone (C3) in the alkali-soluble resin (C) is not particularly limited, but is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 40% by mass or more. It is also preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, 20-90% by mass is preferred, more preferably 30-80% by mass, and even more preferably 40-70% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to improve luminescent properties. By setting it to the aforementioned upper limit or below, there is a tendency to improve developability.

[0646] (D) The proportion of the photopolymerization initiator is not particularly limited, but relative to the total solid content of the photosensitive coloring resin composition of the present invention, it is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, further preferably 1% by mass or more, even more preferably 2% by mass or more, particularly preferably 3% by mass or more, and preferably 15% by mass or less, more preferably 10% by mass or less, further preferably 8% by mass or less, particularly preferably 6% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 0.1 to 15% by mass, more preferably 0.5 to 15% by mass, further preferably 1 to 10% by mass, even more preferably 2 to 8% by mass, and particularly preferably 3 to 6% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to suppress the decrease in sensitivity. By setting it to the aforementioned upper limit or below, there is a tendency to suppress the decrease in the solubility of the unexposed portion in the developer and suppress poor development.

[0647] When using a polymerization accelerator in conjunction with the (D) photopolymerization initiator, the content ratio of the polymerization accelerator is not particularly limited. It is preferably 0.05% by mass or more relative to the total solid content of the photosensitive coloring resin composition of the present invention, and more preferably 10% by mass or less, and more preferably 5% by mass or less. For example, it is preferably 0.05 to 10% by mass, and more preferably 0.05 to 5% by mass. Furthermore, the polymerization accelerator is preferably used in a ratio of 0.1 to 50 parts by mass relative to 100 parts by mass of the (D) photopolymerization initiator, and more preferably 0.1 to 20 parts by mass. By setting the content ratio of the polymerization accelerator to the aforementioned lower limit or above, there is a tendency to suppress the decrease in sensitivity to exposure light. By setting it to the aforementioned upper limit or below, there is a tendency to suppress the decrease in solubility of the unexposed portion in the developer and suppress poor development.

[0648] When using sensitized pigments with (D) photopolymerization initiator, the proportion of sensitized pigments is not particularly limited. From the viewpoint of sensitivity, it is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less, relative to the total solid content in the photosensitive coloring resin composition.

[0649] When the photosensitive coloring resin composition of the present invention contains an (E) olefin unsaturated compound, the content ratio of the (E) olefin unsaturated compound is not particularly limited. However, relative to the total solid content of the photosensitive coloring resin composition of the present invention, it is preferably 1% by mass or more, more preferably 5% by mass or more, further preferably 10% by mass or more, particularly preferably 15% by mass or more, and preferably 30% by mass or less, more preferably 25% by mass or less, further preferably 20% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1 to 30% by mass, more preferably 5 to 25% by mass, further preferably 10 to 25% by mass, and particularly preferably 15 to 20% by mass. By setting it to the aforementioned lower limit or above, there is a tendency to maintain suitable sensitivity, suppress the dissolution of the exposed portion due to the developer, and suppress the reduction of pattern clarity and adhesion. By setting it to the aforementioned upper limit or below, there is a tendency to suppress the increased penetration of the developer into the exposed portion and easily obtain a good image.

[0650] When the photosensitive coloring resin composition of the present invention contains an (E) olefinically unsaturated compound, the content ratio of (C) alkali-soluble resin relative to 100 parts by mass of the (E) olefinically unsaturated compound is not particularly limited, but is preferably 100 parts by mass or more, more preferably 200 parts by mass or more, further preferably 250 parts by mass or more, even more preferably 300 parts by mass or more, and particularly preferably 350 parts by mass or more. Furthermore, it is preferably 700 parts by mass or less, more preferably 500 parts by mass or less, further preferably 450 parts by mass or less, and particularly preferably 400 parts by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 100 to 700 parts by mass, more preferably 200 to 700 parts by mass, further preferably 250 to 500 parts by mass, even more preferably 300 to 450 parts by mass, and particularly preferably 350 to 400 parts by mass. By setting it to the aforementioned lower limit or above, there is a tendency to achieve a suitable dissolution and development state without peeling, etc. By setting it to the aforementioned upper limit or below, there is a tendency to obtain a suitable dissolution time relative to the developing solution.

[0651] When using an adhesion enhancer, its content is not particularly limited, but is preferably 0.1 to 5% by mass, more preferably 0.2 to 3% by mass, and even more preferably 0.4 to 2% by mass relative to the total solid content of the photosensitive coloring resin composition. By setting it to the aforementioned lower limit or above, there is a tendency to obtain a sufficient adhesion enhancement effect. By setting it to the aforementioned upper limit or below, there is a tendency to suppress defects such as decreased sensitivity or residual residue after development.

[0652] When using a surfactant, its content is not particularly limited, but relative to the total solid content of the photosensitive coloring resin composition, it is preferably 0.001 to 10% by mass, more preferably 0.005 to 1% by mass, further preferably 0.01 to 0.5% by mass, and particularly preferably 0.03 to 0.3% by mass. By setting it to the aforementioned lower limit or above, the coated film tends to exhibit smoothness and uniformity. By setting it to the aforementioned upper limit or below, the coated film tends to exhibit smoothness and uniformity, and also tends to suppress the deterioration of other properties.

[0653] The photosensitive coloring resin composition of the present invention is adjusted by using a solvent to ensure that the content of all solid components is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more. Furthermore, it is preferably 50% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, it can be adjusted to preferably 5-50% by mass, more preferably 10-30% by mass, and even more preferably 15-25% by mass.

[0654] <Physical Properties of Photosensitive Coloring Resin Compositions>

[0655] The optical density (OD) of the photosensitive coloring resin composition of the present invention per 1 μm film thickness is not particularly limited, but is preferably 0.2 or more, more preferably 0.5 or more, further preferably 0.7 or more, and even more preferably 0.9 or more. It is also preferably 4.0 or less, more preferably 3.0 or less, even more preferably 2.0 or less, and particularly preferably 1.5 or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 0.2 to 4.0, more preferably 0.5 to 4.0, further preferably 0.5 to 3.0, even more preferably 0.5 to 2.0, still more preferably 0.7 to 2.0, and particularly preferably 0.9 to 1.5. By setting it to the aforementioned lower limit or above, there is a tendency to obtain sufficient light-blocking properties. By setting it to the aforementioned upper limit or below, there is a tendency to suppress surface roughness of the electrode and increase the residual film rate.

[0656] The optical density (OD) of the coating film per 1 μm thickness can be measured using a coating film formed by curing the photosensitive coloring resin composition of the present invention. A coating film with a thickness of 0.5 to 1.5 μm formed by heating and curing at 230°C for 20 minutes can be used for measurement.

[0657] Optical density refers to the transmittance of light as indicated by ISO Visualdensity in the ISO 5-3 standard, which describes the spectral sensitivity characteristics of a light receiver. Typically, an A-level light source, as specified by the CIE (International Commission on Illumination), is used as the light source. An example of an instrument that can be used to measure transmittance is the X-Rite 361T(V) from SAKATA INX ENG.CO.,LTD.

[0658] [Pigment Dispersion]

[0659] The components and composition of the pigment dispersion that constitutes the present invention will be described.

[0660] The pigment dispersion of the present invention contains (A) a colorant, (B) a dispersant and (C) an alkali-soluble resin, particularly the aforementioned (A) colorant containing an organic pigment (A-1) and (C) alkali-soluble resin containing a resin (C1). Additionally, a solvent is preferably included.

[0661] The components in the pigment dispersion of the present invention may preferably be those listed as the same items in the photosensitive coloring resin composition of the present invention.

[0662] The resin (C1) has a high affinity for pigments and also contains methylene groups in the main chain, giving it flexibility to follow the pigment. Therefore, the pigment dispersion of the present invention tends to exhibit high pigment dispersibility.

[0663] Furthermore, the photosensitive coloring resin composition using the pigment dispersion of the present invention tends to have a higher residual film rate. As mentioned above, since the resin (C1) contains a large number of aromatic rings in the main chain, it tends to have high developer resistance during development and high heat resistance during calcination.

[0664] Furthermore, when organic electroluminescent elements are formed using a separator obtained from a photosensitive coloring resin composition, as mentioned above, there is a tendency for the current density to increase when a voltage is applied.

[0665] <Proportion of each component in the pigment dispersion>

[0666] In the pigment dispersion of the present invention, the content of colorant (A) relative to the total solid components in the pigment dispersion is preferably 10% by mass or more, more preferably 20% by mass or more, further preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, and particularly preferably 55% by mass or more. Alternatively, it is typically 100% by mass or less, preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 65% ​​by mass or less. By setting the value to the aforementioned lower limit or above, a photosensitive coloring resin composition can be manufactured with an appropriate solid component concentration. Furthermore, by setting the value to the aforementioned upper limit or below, there is a tendency for improved dispersibility. As a combination of the upper and lower limits, it is preferably 10 to 80% by mass, more preferably 20 to 80% by mass, further preferably 30 to 70% by mass, even more preferably 40 to 70% by mass, particularly preferably 50 to 65% by mass, and most preferably 55 to 65% by mass.

[0667] In the pigment dispersion of the present invention, the content of organic pigment (A-1) relative to the total solid content in the pigment dispersion is preferably 10% by mass or more, more preferably 20% by mass or more, further preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, and particularly preferably 55% by mass or more. Alternatively, it is typically 100% by mass or less, preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 65% ​​by mass or less. By setting the value to the aforementioned lower limit or above, a photosensitive coloring resin composition can be manufactured with an appropriate solid content concentration. Furthermore, by setting the value to the aforementioned upper limit or below, there is a tendency for improved dispersibility. As a combination of the upper and lower limits, it is preferably 10 to 80% by mass, more preferably 20 to 80% by mass, further preferably 30 to 70% by mass, even more preferably 40 to 70% by mass, particularly preferably 50 to 65% by mass, and most preferably 55 to 65% by mass.

[0668] In the pigment dispersion of the present invention, the proportion of organic black pigment relative to the total solid content of the pigment dispersion is preferably 10% by mass or more, more preferably 20% by mass or more, further preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, and particularly preferably 55% by mass or more. Alternatively, it is typically 100% by mass or less, preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 65% ​​by mass or less. By setting the value to the aforementioned lower limit or above, a photosensitive coloring resin composition can be manufactured with an appropriate solid content concentration. Furthermore, by setting the value to the aforementioned upper limit or below, there is a tendency for improved dispersibility. As a combination of the upper and lower limits, it is preferably 10 to 80% by mass, more preferably 20 to 80% by mass, further preferably 30 to 70% by mass, even more preferably 40 to 70% by mass, particularly preferably 50 to 65% by mass, and most preferably 55 to 65% by mass.

[0669] In the pigment dispersion of the present invention, the content of (B) dispersant relative to the total solid components in the pigment dispersion is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more. Furthermore, it is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 20% by mass or less, and particularly preferably 15% by mass or less. By setting it to the aforementioned lower limit or above, there is a tendency for improved dispersibility; conversely, by setting it to the aforementioned upper limit or below, excess dispersant can be reduced, and there is a tendency for improved developability of the resulting photosensitive coloring resin composition. Examples of combinations of the upper and lower limits include preferably 2 to 50% by mass, more preferably 5 to 40% by mass, even more preferably 5 to 30% by mass, even more preferably 5 to 20% by mass, and particularly preferably 8 to 15% by mass.

[0670] When the pigment dispersion of the present invention contains an acrylic dispersant as (B) dispersant, the proportion of the acrylic dispersant relative to the total solid content in the pigment dispersion is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more. Furthermore, it is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 20% by mass or less, and particularly preferably 15% by mass or less. By setting it to the aforementioned lower limit or above, there is a tendency for improved dispersibility and improved pattern adhesion during development of the cured product. Furthermore, by setting it to the aforementioned upper limit or below, there is a tendency for improved developability of the resulting photosensitive coloring resin composition. As a combination of the upper and lower limits, it is preferably 2 to 50% by mass, more preferably 5 to 40% by mass, even more preferably 5 to 30% by mass, even more preferably 5 to 20% by mass, and particularly preferably 10 to 15% by mass.

[0671] In the pigment dispersion of the present invention, the content of (C) alkali-soluble resin relative to the total solid components in the pigment dispersion is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 25% by mass or more. Furthermore, it is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less. By setting it to the aforementioned lower limit or above, there is a tendency for improved dispersibility; conversely, by setting it to the aforementioned upper limit or below, there is a tendency for appropriate coloring dosage in the obtained photosensitive coloring resin composition to be achieved, ensuring sufficient opacity. As a combination of the upper and lower limits, it is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, further preferably 15 to 35% by mass, even more preferably 20 to 35% by mass, and particularly preferably 25 to 35% by mass.

[0672] The resin (Cl) content in the pigment dispersion of the present invention is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 25% by mass or more, relative to the total solid components in the pigment dispersion. Additionally, it is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less. By setting it to the aforementioned lower limit or above, there is a tendency for improved dispersibility; conversely, by setting it to the aforementioned upper limit or below, there is a tendency for appropriate coloring dosage in the obtained photosensitive coloring resin composition to be achieved, ensuring sufficient opacity. As a combination of the upper and lower limits, it is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, further preferably 15 to 35% by mass, even more preferably 20 to 35% by mass, and particularly preferably 25 to 35% by mass.

[0673] It should be noted that the pigment dispersion of the present invention is adjusted to a solid component concentration of preferably 5-50% by mass, more preferably 10-30% by mass, using the aforementioned organic solvent.

[0674] <Physical Properties of Pigment Dispersions>

[0675] The viscosity of the pigment dispersion is preferably 1 MPa·s or more, more preferably 3 MPa·s or more, and even more preferably 5 MPa·s or more. Furthermore, it is preferably 15 MPa·s or less, and even more preferably 10 MPa·s or less. The viscosity can be measured, for example, using a rotational viscometer.

[0676] [Method for manufacturing pigment dispersion]

[0677] The pigment dispersion of the present invention is manufactured according to conventional methods.

[0678] (A) The colorant is preferably pre-dispersed using a paint shaker, sand mill, ball mill, roller mill, stone mill, jet mill, homogenizer, etc. Through dispersion treatment, (A) the colorant is micronized, thus tending to improve the coating properties of the photosensitive coloring resin composition and reduce the surface roughness.

[0679] The dispersion treatment is preferably carried out in a system using a combination of (A) a colorant, (B) a dispersant and a solvent, and (C) a portion or all of an alkali-soluble resin. In particular, when a polymeric dispersant is used as (B) the dispersant, the thickening of the resulting pigment dispersion and photosensitive coloring resin composition over time can be suppressed, i.e., excellent dispersion stability is achieved, and therefore it is preferred.

[0680] Examples of substances described that can be used in photosensitive coloring resin compositions are preferred as (A) colorant, (B) dispersant, and solvent that can be used in pigment dispersions.

[0681] When dispersing a liquid containing all the components of a photosensitive coloring resin composition, the highly reactive components may be modified due to the exothermic reaction that occurs during the dispersion process. Therefore, it is preferable to perform the dispersion process using a system containing a polymeric dispersant.

[0682] When dispersing colorant (A) using a sand mill, glass beads or zirconia beads with a particle size of approximately 0.1 to 8 mm are preferably used. Regarding dispersion conditions, the temperature is preferably 0°C to 100°C, more preferably room temperature to 80°C. Regarding dispersion time, since the appropriate time varies depending on the composition of the liquid and the size of the dispersion apparatus, it should be adjusted accordingly. The standard for dispersion is to control the gloss of the pigment dispersion so that the 20-degree specular gloss (JIS Z8741) of the photosensitive coloring resin composition is in the range of 50 to 300. If the gloss of the photosensitive coloring resin composition is low, the dispersion treatment is usually insufficient, leaving behind coarse pigment (colorant) particles, which may lead to insufficient developability, adhesion, resolution, and surface roughness. If dispersion treatment is continued until the gloss value exceeds the above range, the pigment breaks down, producing a large number of ultrafine particles, thus tending to impair dispersion stability.

[0683] The preferred particle size of the pigment dispersed in the pigment dispersion is 0.03–0.3 μm, which can be determined by dynamic light scattering.

[0684] [Method for manufacturing photosensitive coloring resin composition]

[0685] Next, the pigment dispersion obtained through the above dispersion treatment is mixed with other components contained in the photosensitive coloring resin composition to prepare a homogeneous solution or dispersion. During the manufacturing process of the photosensitive coloring resin composition, since fine dust sometimes mixes into the liquid, it is ideal to filter the obtained photosensitive coloring resin composition using a filter or the like.

[0686] [cured material]

[0687] By curing the photosensitive coloring resin composition of the present invention, the cured product of the present invention can be obtained. The cured product obtained by curing the photosensitive coloring resin composition of the present invention can be suitably used as a black matrix, an insulating film, or a separator, and can be more suitably used as a separator.

[0688] The thickness of the cured film is preferably 0.5 μm or more, more preferably 0.7 μm or more, and even more preferably 0.9 μm or more. Furthermore, it is preferably 15 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. For example, it is preferably 0.5 to 15 μm, more preferably 0.7 to 10 μm, and even more preferably 0.9 to 5 μm.

[0689] From the viewpoint of light-shielding properties, the optical density (OD) per 1 μm of the cured product of the present invention is preferably 0.2 or more, more preferably 0.5 or more, further preferably 0.7 or more, and particularly preferably 0.9 or more. Furthermore, it is preferably 4.0 or less, more preferably 3.0 or less, further preferably 2.0 or less, and particularly preferably 1.5 or less. For example, it is preferably 0.2 to 4.0, more preferably 0.5 to 4.0, further preferably 0.5 to 3.0, even more preferably 0.5 to 2.0, still more preferably 0.7 to 2.0, and particularly preferably 0.9 to 1.5. Here, the optical density (OD) is a value measured by the method described later.

[0690] Next, the cured product using the photosensitive coloring resin composition of the present invention will be described according to its manufacturing method.

[0691] (1) Support

[0692] As a support for forming cured products, the material is not particularly limited as long as it has adequate strength. The main material used is a substrate, and examples of suitable materials include: polyester resins such as polyethylene terephthalate, polyolefin resins such as polypropylene and polyethylene, thermoplastic resin sheets such as polycarbonate, polymethyl methacrylate, and polysulfone, epoxy resins, unsaturated polyester resins, thermosetting resin sheets such as poly(meth)acrylic acid resins, and various types of glass. From a heat resistance perspective, glass and heat-resistant resins are preferred. Additionally, sometimes transparent electrodes such as ITO and IZO, or metal electrodes such as silver, gold, platinum, aluminum, and magnesium, are formed on the substrate surface. Besides the substrates mentioned above, these can also be formed on TFT arrays.

[0693] To improve surface properties such as adhesion, the support can be subjected to film formation treatments using various resins, such as corona discharge treatment, ozone treatment, silane coupling agents, and urethane resins, as needed.

[0694] The thickness of the support is preferably set to a range of 0.05 to 10 mm, more preferably 0.1 to 7 mm. Furthermore, when performing film formation treatments with various resins, the film thickness is preferably in the range of 0.01 to 10 μm, more preferably 0.05 to 5 μm.

[0695] On a support onto which the cured material is to be formed, a photosensitive coloring resin composition is supplied in a film or patterned form by means of coating or other methods, and the solvent is dried. Next, a pattern is formed by means of photolithography or other methods involving exposure and development. Afterward, additional exposure and thermal curing are performed as needed, thereby forming a cured material on the substrate.

[0696] (2) Supply method to the support

[0697] The photosensitive coloring resin composition of the present invention is preferably supplied to the support in a dissolved or dispersed state in a solvent. As a method of supply, it can be performed by conventionally known methods, such as spin coating, wire bar coating, flow coating, die coating, roller coating, and spray coating. Alternatively, it can be supplied in a patterned manner by, for example, inkjet printing or printing. When using die coating, it is preferred from the comprehensive viewpoints of significantly reducing the amount of coating liquid used, completely eliminating the effects of fogging and other contaminant formation as in spin coating, and suppressing the generation of foreign matter.

[0698] The coating amount varies depending on the application, and is preferably 0.5 μm to 10 μm, more preferably 1 μm to 9 μm, and particularly preferably 1 μm to 7 μm, based on the dried film thickness. Importantly, the dried film thickness or the height of the final cured product is uniform throughout the entire area of ​​the support. By reducing deviations, the light-blocking properties within the support become uniform. Furthermore, when used as a partition wall, a uniformly formed light-emitting layer can be produced, suppressing display defects during light emission.

[0699] When using the photosensitive coloring resin composition of the present invention to form cured products of different heights in a single step by photolithography, the final height of the cured products will be different.

[0700] (3) Drying method

[0701] Drying after supplying the photosensitive coloring resin composition to the support is preferably based on drying methods using a heated plate, an IR oven, or a convection oven. It can also be combined with a vacuum drying method, in which drying is carried out in a vacuum chamber without increasing the temperature.

[0702] The drying conditions can be appropriately selected based on the type of solvent and the performance of the dryer used. The drying time is preferably selected within the range of 15 seconds to 5 minutes at a temperature of 40 to 130°C, and more preferably within the range of 30 seconds to 3 minutes at a temperature of 50 to 110°C, depending on the type of solvent and the performance of the dryer used.

[0703] (4) Exposure method

[0704] Exposure is performed by overlaying a negative mask pattern onto a coated film of a photosensitive coloring resin composition, and then irradiating it with an ultraviolet or visible light source through the mask pattern. When using an exposure mask, methods include placing the exposure mask close to the coated film of the photosensitive coloring resin composition; or placing the exposure mask away from the coated film of the photosensitive coloring resin composition and projecting exposure light through the exposure mask. Alternatively, a scanning exposure method using a laser can be employed without a mask pattern. Depending on the need, to prevent a decrease in the sensitivity of the photopolymerizable layer due to oxygen, exposure can be performed in a deoxygenated atmosphere, or exposure can be performed after forming an oxygen barrier layer such as a polyvinyl alcohol layer on the photopolymerizable layer.

[0705] In the case of simultaneously forming cured materials with different heights using photolithography, for example, an exposure mask is used that has a light-blocking portion (0% transmittance) and multiple openings (medium transmittance openings) whose average transmittance is less than that of the opening with the highest average transmittance (fully transparent opening). With this method, the difference in residual film yield is generated due to the difference in average transmittance between the medium transmittance opening and the fully transparent opening, i.e., the difference in exposure amount.

[0706] Medium transmittance openings are known to be fabricated using a matrix-like light-blocking pattern with tiny polygonal light-blocking units. As absorbers, methods are known to be fabricated using films made of chromium-based, molybdenum-based, tungsten-based, or organosilicon-based materials, with controlled light transmittance.

[0707] There are no particular limitations on the light source used for exposure. Examples of light sources include xenon lamps, halogen lamps, tungsten lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, medium-pressure mercury lamps, low-pressure mercury lamps, carbon arc lamps, and fluorescent lamps; and laser sources such as argon ion lasers, YAG lasers, excimer lasers, nitrogen lasers, helium-cadmium lasers, blue-violet semiconductor lasers, and near-infrared semiconductor lasers. When using light of a specific wavelength, filters can also be used.

[0708] As a filter, it can be a type that allows the transmittance at the exposure wavelength to be controlled by a thin film. In this case, materials such as Cr compounds (Cr oxides, nitrides, oxynitrides, fluorides, etc.), MoSi, Si, W, and Al can be listed.

[0709] There is no specific limit to the exposure level, but 1 mJ / cm is preferred. 2 The above, and more preferably, is 5 mJ / cm 2 The above, and more preferably, is 10 mJ / cm 2 In addition, the preferred value is 300 mJ / cm³. 2 The following, and more preferably, is 200 mJ / cm 2 The following, and more preferably, is 150 mJ / cm 2 the following.

[0710] (5) Development method

[0711] After the above exposure, an image pattern can be formed on the support by developing it with an aqueous solution of an alkaline compound or an organic solvent. The aqueous solution of the alkaline compound may further contain, for example, surfactants, organic solvents, buffers, complexing agents, dyes, or pigments.

[0712] Examples of basic compounds include inorganic basic compounds such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium silicate, potassium silicate, sodium metasilicate, sodium phosphate, potassium phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, and ammonium hydroxide; and organic basic compounds such as monoethanolamine, diethanolamine or triethanolamine, monomethylamine, dimethylamine or trimethylamine, monoethylamine, diethylamine or triethylamine, monoisopropylamine or diisopropylamine, n-butylamine, monoisopropanolamine, diisopropanolamine or triisopropanolamine, ethyleneimine, ethylenediamine, tetramethylammonium hydroxide (TMAH), and choline. These basic compounds can be used alone or in combination of two or more.

[0713] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, and monoglyceride alkyl esters; anionic surfactants such as alkylbenzene sulfonates, alkylnaphthalene sulfonates, alkyl sulfates, alkyl sulfonates, and sulfosuccinates; and amphoteric surfactants such as alkyl betaines and amino acids.

[0714] Examples of organic solvents include isopropanol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol, and diacetone alcohol. Two or more of these organic solvents can also be used in combination. Furthermore, an organic solvent can be used alone or in combination with water or an aqueous solution of an alkaline compound.

[0715] There are no particular restrictions on the conditions for the developing process, but the developing temperature is preferably 10–50°C, more preferably 15–45°C, and even more preferably 20–40°C. Developing methods may include, for example, immersion developing, spray developing, brush developing, and ultrasonic developing.

[0716] (6) Additional exposure and thermosetting treatment

[0717] After development, the substrate can be further exposed using the same method as described above, as needed. After development or further exposure, a heat curing process (also known as calcination) can also be performed. Regarding the heat curing conditions, the preferred temperature is 100–280°C, more preferably 150–250°C, and the time is 5–60 minutes.

[0718] [Separator]

[0719] The photosensitive coloring resin composition of the present invention can be suitably used to form partitions, particularly partitions for dividing organic layers of organic electroluminescent elements. Examples of organic layers for organic electroluminescent elements include the organic layer described in Japanese Patent Application Publication No. 2016-165396, which is used for hole injection layers, hole transport layers, or hole transport layers on hole injection layers.

[0720] When the separator made according to the present invention is used, its size, shape, etc. can be appropriately adjusted according to the specifications of the organic electroluminescent element used therein. The film thickness and optical density (OD) per 1 μm of the separator formed by the photosensitive coloring resin composition of the present invention are the same as those of the cured film.

[0721] [Organic electroluminescent element]

[0722] The organic electroluminescent element of the present invention comprises a cured material, such as a separator, formed from the photosensitive coloring resin composition of the present invention.

[0723] For example, various organic light-emitting elements can be manufactured using a substrate with a partition wall pattern produced by the above method. The method for forming the organic light-emitting element is not particularly limited, but it is preferable to form an organic layer such as pixels by a wet process such as vapor deposition, casting, spin coating, or inkjet printing after forming the partition wall pattern on the substrate using the above method. The vapor deposition process involves sublimating the functional material under vacuum and depositing it onto the area enclosed by the partition walls on the substrate to form a film.

[0724] As types of organic electroluminescent elements, bottom-emitting type and top-emitting type can be listed.

[0725] In bottom-emitting types, partition walls are formed on a glass substrate, for example, where transparent electrodes are stacked, and a hole transport layer, a light-emitting layer, an electron transport layer, and a metal electrode layer are stacked in the opening surrounded by the partition walls. On the other hand, top-emitting types can be fabricated, for example, by forming partition walls on a glass substrate where a metal electrode layer serves as a reflective layer, and stacking an electron transport layer, a light-emitting layer, a hole transport layer, and a transparent electrode layer in the opening surrounded by the partition walls. In most cases, an anode is provided on a support, but this is not a limitation.

[0726] Examples of luminescent layers include organic electroluminescent layers as described in Japanese Patent Application Publication No. 2009-146691 and Japanese Patent Publication No. 5734681. Alternatively, quantum dots as described in Japanese Patent Publication No. 5653387 and Japanese Patent Publication No. 5653101 may also be used.

[0727] The layer structure is not limited to this. For example, from the viewpoint of luminous efficiency, each layer of the hole transport layer and the electron transport layer can be a stacked structure containing two or more layers. The thickness of each layer is not particularly limited, but from the viewpoint of luminous efficiency and brightness, it is preferably 1 to 500 nm.

[0728] Organic light-emitting diodes (OLEDs) can be configured with RGB colors in each opening, or multiple colors can be layered in a single opening. From a reliability perspective, OLEDs can incorporate a sealing layer. This sealing layer prevents moisture from the air from adsorbing onto the OLED and reducing its luminous efficiency. From a light extraction efficiency perspective, OLEDs can have a low-reflection film at the air interface. By placing the low-reflection film at the air-electrode interface, the difference in refractive index can be reduced, suppressing reflection at the interface. Such low-reflection films can utilize techniques such as moth-eye structures or multilayer films.

[0729] When organic electroluminescent elements are used as pixels in an image display device, it is necessary to prevent light from the light-emitting layer of some pixels from leaking into other pixels. Furthermore, when the electrodes are made of metal, it is necessary to prevent the degradation of image quality associated with the reflection of external light. Therefore, it is preferable to give the partition walls constituting the organic electroluminescent elements light-shielding properties.

[0730] In organic electroluminescent devices, since electrodes need to be provided on the upper and lower surfaces of the separator, from the viewpoint of insulation, it is preferable that the separator has high resistance and low dielectric constant. Therefore, when a colorant is used to impart light-shielding properties to the separator, the aforementioned organic pigment with high resistance and low dielectric constant is preferred.

[0731] [Color filter containing luminescent nanocrystal particles]

[0732] The color filter of the present invention, which includes luminescent nanocrystal particles, is not particularly limited as long as it has the partition wall of the present invention. Examples include color filters in which pixels are formed in the area divided by the partition wall.

[0733] Figure 1 This is a cross-sectional schematic diagram of an example of a color filter equipped with the partition wall of the present invention. Figure 1 As shown, the color filter 100 includes a substrate 10, partition walls 20 disposed on the substrate, red pixels 30, green pixels 40, and blue pixels 50. The red pixels 30, green pixels 40, and blue pixels 50 are arranged in a grid pattern in a repeating sequence. The partition walls 20 are disposed between these adjacent pixels. In other words, these adjacent pixels are separated from each other by the partition walls 20.

[0734] Red pixel 30 contains red luminescent nanocrystal particles 2, and green pixel 40 contains green luminescent nanocrystal particles 1. Blue pixel 50 is a pixel that can transmit blue light from a light source.

[0735] These nanocrystal particles are nanoscale crystals that emit fluorescence or phosphorescence upon absorbing excitation light. They are crystals with a maximum particle size of less than 100 nm, as measured by, for example, transmission electron microscopy or scanning electron microscopy.

[0736] Luminescent nanocrystal particles can emit light of a different wavelength (fluorescence or phosphorescence) by absorbing light of a specified wavelength. For example, red luminescent nanocrystal particles 2 emit light with a peak wavelength in the range of 605 to 665 nm (red light), and green luminescent nanocrystal particles 1 emit light with a peak wavelength in the range of 500 to 560 nm (green light).

[0737] According to the solution of the Schrödinger wave equation in the trap potential model, the wavelength (emission color) of the light emitted by luminescent nanocrystal particles depends on the size (e.g., particle size) of the nanocrystal particles and also on the band gap they possess. Therefore, by changing the constituent materials and size of the luminescent nanocrystal particles used, the emission color can be selected. Examples of luminescent nanocrystal particles include quantum dots.

[0738] The method for manufacturing a color filter containing luminescent nanocrystal particles is not particularly limited, but examples include: preparing a substrate having a partition wall formed by the cured product of the present invention, and forming a layer containing luminescent nanocrystal particles in the area defined by the partition wall. The method for forming the layer containing luminescent nanocrystal particles is not particularly limited, and can be manufactured, for example, by selectively attaching an ink composition containing luminescent nanocrystal particles using an inkjet method, and then curing the ink composition by irradiation or heating with active energy rays.

[0739] [Image display device]

[0740] As an image display device of the present invention, an organic EL display device having a partition wall containing the cured material of the present invention and an organic electroluminescent element can be cited.

[0741] As long as an organic EL display device includes the aforementioned organic electroluminescent elements, there are no particular restrictions on the model or structure of the image display device. For example, active-drive organic electroluminescent elements can be used and assembled according to conventional methods. For example, it can be formed using the methods described in "Organic EL Display" (OHM Corporation, published August 20, 2016, authored by Shizushi Tokito, Chinatsu Adachi, and Hideyuki Murata). For example, an image display can be achieved by combining an organic electroluminescent element that emits white light with a color filter, or by combining organic electroluminescent elements that emit different colors such as RGB.

[0742] Example

[0743] The present invention will be described in more detail below with examples and comparative examples, but the present invention is not limited to the following examples as long as it does not deviate from its spirit.

[0744] The composition of the photosensitive coloring resin compositions used in the following examples and comparative examples, as well as their evaluation methods, are described below.

[0745] <Alkali-soluble resin-I>

[0746]

[0747] 70 parts by mass of an epoxy compound (epoxy equivalent 273) having repeating units as shown in the above formula, 18.5 parts by mass of acrylic acid, 1.77 parts by mass of triphenylphosphine, 0.0442 parts by mass of 4-methoxyphenol, and 59 parts by mass of propylene glycol monomethyl ether acetate were added to a reaction vessel and stirred. Then, 7.6 parts by mass of phthalic anhydride and 37.1 parts by mass of propylene glycol monomethyl ether acetate were further added, and the reaction was allowed to proceed. The resulting alkali-soluble resin-I had a weight-average molecular weight (Mw) of 2456 as determined by GPC, an acid value of 64 mg KOH / g, and was equivalent to resin (C1), corresponding to the structure shown in formula (C1-1).

[0748] <Alkali-soluble resin-II>

[0749] 155 parts by weight of EPICLON HP7200 HH (a polyglycidyl ether of dicyclopentadiene-phenol polymer, weight-average molecular weight 1000, epoxy equivalent 270) manufactured by DIC, 41 parts by weight of acrylic acid, 0.1 parts by weight of p-methoxyphenol, 2.5 parts by weight of triphenylphosphine, and 270 parts by weight of propylene glycol monomethyl ether acetate were added to a reaction vessel and heated and stirred at 100°C until the acid value reached below 3.0 mg KOH / g. The target acid value was reached in 9 hours (acid value 2.9 mg KOH / g). Next, 74 g of tetrahydrophthalic anhydride was added, and the reaction was carried out at 120°C for 4 hours. The resulting alkali-soluble resin-II had a weight-average molecular weight (Mw) of 3500 and an acid value of 60 mg KOH / g, and was not classified as a resin (C1).

[0750] <Alkali-soluble resin-III>

[0751] "ZCR-1664H" (weight-average molecular weight Mw = 5200, acid value = 60 mg KOH / g) manufactured by Nippon Kayaku Co., Ltd. has a partial structure as shown in the following formula, where * represents a connecting bond.

[0752] Alkali-soluble resin-III is not a resin (C1).

[0753]

[0754] <Alkali-soluble resin-IV>

[0755] Nippon Kayaku Co., Ltd.'s "CCR-1342H" (weight-average molecular weight Mw = 6500, acid value = 60 mg KOH / g) has a partial structure as shown in the following formula, where * represents a connecting bond.

[0756] Alkali-soluble resin-IV is not a resin (C1).

[0757]

[0758] <Alkali-soluble resin-V>

[0759]

[0760] 240 parts by mass of the epoxy compound with the above structure (epoxy equivalent 264), 68.3 parts by mass of acrylic acid, 263.1 parts by mass of methoxybutyl acetate, 6.4 parts by mass of triphenylphosphine, and 0.16 parts by mass of p-methoxyphenol were placed in a flask equipped with a thermometer, a stirrer, and a condenser. The mixture was stirred and reacted at 90°C for 12 hours until the acid value was below 5 mg KOH / g.

[0761] Next, in a flask equipped with a thermometer, stirrer, and condenser, 9.2 parts by mass of trimethylolpropane (TMP), 115.6 parts by mass of biphenyltetracarboxylic acid dianhydride (BPDA), and 25.1 parts by mass of tetrahydrophthalic anhydride (THPA) were added to the reaction solution obtained from the above reaction. The mixture was stirred and slowly heated to 105°C to carry out the reaction, yielding an alkali-soluble resin-V with a solid acid value of 104 mg KOH / g and a weight-average molecular weight (Mw) of 2660 converted from polystyrene as determined by GPC. Alkali-soluble resin-V belongs to the (C2) epoxy (meth)acrylate resin category.

[0762] <Alkali-soluble resin-VI>

[0763] KISCO manufactures "KBR-201". It is a resin with a fluorene-bisphenol backbone. The weight-average molecular weight is 5107, and the acid value is 113 mgKOH / g. It is an alkali-soluble resin-VI belonging to the (C2) epoxy (meth)acrylate resin category.

[0764] <Alkali-soluble resin-VII>

[0765]

[0766] While purging with nitrogen, 50.0 parts by mass of the epoxy compound with the chemical structure shown in the above formula, 170.3 parts by mass of propylene glycol monomethyl ether acetate, 0.89 parts by mass of 2,4,6-tris(dimethylaminomethyl)phenol, and 0.050 parts by mass of p-methoxyphenol were stirred and heated to 100°C. 44.3 parts by mass of methacrylic acid were added dropwise over 30 minutes. The reaction was then carried out at 100°C for 8 hours until the acid value became below 10 mg KOH / g, yielding epoxy (meth)acrylate solution A.

[0767]

[0768] While purging with nitrogen, 50.0 parts by weight of an epoxy (meth)acrylate solution A (35.9% by weight solids) containing the aforementioned chemical structure and 3.1 parts by weight of propylene glycol monomethyl ether acetate were stirred. 3.48 parts by weight of pyromellitic dianhydride (PDMA) and 2.36 parts by weight of phthalic anhydride were added, the mixture was heated to 80°C, and reacted for 5 hours to obtain alkali-soluble resin-VII with a solid content of 40% by weight, an acid value of 145 mg KOH / g, and a weight-average molecular weight (Mw) of 2800 converted from polystyrene as determined by GPC. Alkali-soluble resin-VII belongs to the (C3) resin family containing an isocyanuric acid backbone.

[0769] <Alkali-soluble resin-VIII>

[0770]

[0771] 100 parts by mass of an epoxy compound (epoxy equivalent 273) having repeating units as shown in the above formula, 26.42 parts by mass of acrylic acid, 2.53 parts by mass of triphenylphosphine, 0.0632 parts by mass of 4-methoxyphenol, and 84.28 parts by mass of propylene glycol monomethyl ether acetate were added to a reaction vessel and stirred. Then, 22.8 parts by mass of trimellitic anhydride and 48.9 parts by mass of propylene glycol monomethyl ether acetate were further added, and the reaction was allowed to proceed. The resulting alkali-soluble resin-VIII had a weight-average molecular weight (Mw) of 1668 as determined by GPC, an acid value of 96.3 mg KOH / g, and was equivalent to resin (C1), corresponding to the structure shown in formula (C1-1).

[0772] <Coloring Agent-I>

[0773] BASF Corporation, Irgaphor (registered trademark) Black S 0100CF (has the chemical structure shown in the following formula (A-1-2)).

[0774]

[0775] <Dispersant-I>

[0776] A block copolymer formed from an A block containing repeating units with solubilizing groups and a B block containing repeating units with tertiary amine groups.

[0777] <Dispersant-II>

[0778] A block copolymer formed by an A block containing repeating units with solubilizing groups and a B block containing repeating units with tertiary amino and quaternary ammonium groups.

[0779] <Solvent-I>

[0780] PGMEA: Propylene glycol monomethyl ether acetate.

[0781] Solvent-II

[0782] MB: 3-Methoxy-1-Butanol.

[0783] <Solvent-III>

[0784] MBA: 3-Methoxy-Butyl Acetate.

[0785] <Photopolymerization Initiator-I>

[0786] Oxime ester photopolymerization initiators having the following chemical structure.

[0787]

[0788] <Alkene Unsaturated Compounds-1>

[0789] DPHA: A mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate manufactured by Nippon Kayaku Co., Ltd.

[0790] <Surfactant-I>

[0791] DIC Corporation, MEGAFAC F-559

[0792] <Viscosity Evaluation>

[0793] The viscosity of the pigment dispersion was measured using a RE-85L viscometer manufactured by Toki Sangyo Co., Ltd. (measurement conditions: 23℃, 20rpm) immediately after preparation, after standing at room temperature (24℃) for 1 day, and after standing for 3 days. The results were as follows.

[0794] From the perspective of the coatability and stability over time of the photosensitive coloring resin composition, the pigment dispersion preferably has a low viscosity.

[0795] A: Viscosity below 10 mPa·s

[0796] B: Viscosity greater than 10 mPa·s

[0797] C: Unable to disperse and solidifies

[0798] Fabrication of substrates for evaluating residual film rate

[0799] On a glass substrate with an indium tin oxide (ITO) film formed on its surface (0.7 mm thick), the photosensitive coloring resin compositions of each example / comparative example were coated using a spin coater to a thickness of 1.5 μm after heat curing (calcination). Then, a vacuum dryer was used for 60 seconds. Next, the coated substrate was heated to 100°C and dried for 100 seconds to obtain the coated substrate.

[0800] The film thickness T1 (μm) was determined by measuring the film thickness after heating and drying using the method described later.

[0801] The coated substrate was exposed using a photomask. A Canon MPA-600FA mirror projection exposure machine was used, with an exposure dose of 80 mJ / cm². 2 A 20-second exposure was performed using this method. The illuminance was 500 mW / cm². 2 The slit width is 1.6 mm. The photomask uses a mask with a grid-like opening (with a 50 μm square covering portion, and multiple such covering portions separated by an exposure portion of 50 μm).

[0802] Next, using a developer solution containing an aqueous solution of 0.05% by mass potassium hydroxide and 0.08% by mass nonionic surfactant (Kao Corporation's "A-60"), spray development was performed at 24°C and a water pressure of 0.05 MPa. Development was then stopped by rinsing off the developer solution with pure water, followed by a 10-second water rinse using a spray gun. The spray development time was set to 1.6 times the time required for the unexposed portions of the coating to dissolve and be removed. After development, the portion corresponding to the square light-blocking area was exposed on the ITO substrate, forming a hole, as the photosensitive coloring resin composition was washed away.

[0803] The substrate was heated and cured (calcined) in an oven at 230°C for 30 minutes to obtain a patterned substrate for patternability measurement. The film thickness T2 (μm) was measured at this time.

[0804] <Calculation of Residual Film Rate>

[0805] The film thickness of the aforementioned patterned substrate at each stage (after drying and after firing) was measured using a VertScan® 2.0 non-contact surface / layer profile shape measurement system manufactured by Ryoka Systems Inc. The ratio of the fired film thickness (T2) to the dried film thickness (T1) in the film thickness measurement was calculated as the residual film rate.

[0806] Residual film rate (%) = (T2 / T1) × 100 (%)

[0807] The calculated residual film rate is judged as follows. A indicates the highest residual film rate, which is good. If the residual film rate is above 75%, it tends to be practically feasible.

[0808] A: Residual film rate of over 80%

[0809] B: Residual film rate is less than 80% and above 75%.

[0810] C: Residual film rate is less than 75%.

[0811] It should be noted that the residual film rate is related to the exposure sensitivity of the resist, its solubility in the developer, and its thermal decomposition during calcination. A higher residual film rate is preferred.

[0812] <Determination of optical concentration (OD value per unit film thickness)>

[0813] Determine the optical concentration per unit film thickness using the following steps.

[0814] Using a spin coater, the photosensitive coloring resin compositions of each example / comparative example were coated onto a glass substrate to a thickness of 1.5 μm after heat curing (calcination). Then, a vacuum dryer was used to perform a 60-second drying process. Next, the mixture was heated to 100°C and dried for 100 seconds.

[0815] The resulting coating was exposed without an exposure mask. A Canon MPA-600FA mirror projection exposure machine was used as the illumination source, with an exposure dose of 80 mJ / cm². 2 A 20-second exposure was performed using this method. The illuminance was 500 mW / cm². 2 Next, the substrate is heated and cured in an oven at 230°C for 30 minutes to obtain the resist-coated substrate 1.

[0816] The optical density (OD value) of the resist-coated substrate 1 was measured using a 361T(V) transmission densitometer manufactured by X-Rite (light source color temperature: approximately 2850K (equivalent to CIE standard light source A), spectral sensitivity characteristics of the light-receiving part: ISO Visual density under ISO 5-3 standard). The film thickness was measured using a VertScan(R) 2.0 non-contact surface / layer profile shape measurement system manufactured by Ryoka Systems Inc. The optical density (OD value) per unit film thickness (1μm) was calculated from the optical density (OD value) and the film thickness. It should be noted that the OD value represents the light-blocking ability; a higher value indicates higher light-blocking ability.

[0817] Fabrication of Patterned Substrates for Organic Electroluminescent Devices

[0818] For a substrate on which an indium tin oxide (ITO) transparent conductive film was deposited on glass at a thickness of 70 nm, and an anode was formed using conventional photolithography and hydrochloric acid etching, the photosensitive coloring resin compositions of each embodiment / comparative example were coated onto the substrate using a spin coater. Then, a 60-second drying process was performed using a vacuum dryer. Next, the substrate was heated and dried on a hot plate at 100°C for 100 seconds.

[0819] The coated substrate was exposed using a photomask. A Canon MPA-600FA mirror projection exposure machine was used, with an exposure dose of 80 mJ / cm². 2 A 20-second exposure was performed using this method. The illuminance was 500 mW / cm². 2 The slit width is 1.6 mm. The photomask uses a mask with a grid-like opening (a rectangular covering with a length of 40 μm and a width of 80 μm, which has multiple such coverings spaced 20 μm apart in the long axis and short axis directions of the exposure area).

[0820] Next, using a developer solution containing an aqueous solution of 0.05% by mass potassium hydroxide and 0.08% by mass nonionic surfactant (Kao Corporation's "A-60"), spray development was performed at 24°C and a water pressure of 0.05 MPa. Development was then stopped by rinsing off the developer solution with pure water, followed by a 10-second water wash with a spray gun. The spray development time was set to 1.6 times the time required for the unexposed portions of the coating to be dissolved and removed.

[0821] These operations are used to develop and remove the openings, resulting in an electrode substrate with patterned partition walls. The electrode substrate with the pattern is then heated and cured (calcined) in an oven at 230°C for 30 minutes to obtain a patterned substrate for organic electroluminescent devices.

[0822] Fabrication of Devices for Evaluating Organic Electroluminescent Elements

[0823] An organic electroluminescent element is fabricated by sequentially layering molybdenum oxide (10 nm thick) as a hole injection layer, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9H-fluorene-2-amine (60 nm thick) as a hole transport layer, tris(8-hydroxyquinoline)aluminum (60 nm thick) as a light-emitting layer, 8-hydroxyquinoline-lithium (1 nm thick) as an electron injection layer, and aluminum (80 nm thick) as a cathode on the entire surface of a patterned substrate for fabricating an organic electroluminescent element.

[0824] Next, a desiccant is adhered to the recessed portion of the sealing glass, and a UV-curable resin is applied to the frame portion surrounding the recess. The sealing glass is configured such that its recess covers the entire organic light-emitting element on the aforementioned electrode substrate. The sealing glass is then adhered to the electrode substrate, and the UV-curable resin is cured by UV irradiation, thus sealing the hollow structure and fabricating a device for evaluating organic light-emitting elements.

[0825] Evaluation of the luminescent properties of organic electroluminescent elements

[0826] The device used to evaluate the fabricated organic electroluminescent element was connected to a DC current, and the current density was measured when the driving voltage was 4V.

[0827] The determination of the measured current density is as follows: A higher current density is preferred; for example, a current density of 0.6 mA / cm² is preferred. 2 The above tends to be practically sound.

[0828] A: Current density 0.8 mA / cm² 2 above

[0829] B: Current density 0.6 mA / cm² 2 Above and below 0.8 mA / cm 2

[0830] C: Current density is less than 0.6 mA / cm² 2

[0831] <Preparation of Pigment Dispersions 1-9>

[0832] The pigments, dispersants, alkali-soluble resins, and solvents listed in Tables 1 and 2 were mixed in the mass ratios shown in Table 1. The mixture was dispersed using a paint mixer at a temperature of 25–45°C for 3 hours. As beads, [the following is used]. Zirconia beads were added to a dispersion at a ratio of 2.5 times their mass. After dispersion, the beads were separated from the dispersion using a filter. Pigment dispersions 1–9 were prepared.

[0833] It should be noted that the amounts of solvent in Tables 1 and 2 also include the amounts of solvent derived from dispersants and alkali-soluble resins.

[0834] [Table 1]

[0835]

[0836] [Table 2]

[0837]

[0838] As shown in Table 1, Examples 1 to 4 using alkali-soluble resin-I exhibited low viscosity and excellent dispersibility. On the other hand, Comparative Examples 1, 3, and 4 could not be dispersed and instead solidified, while Comparative Example 2, although able to be dispersed, had high viscosity, resulting in a lack of dispersibility.

[0839] In addition, as shown in Table 2, the viscosity of Examples 3 to 5 remained stable 3 days after the preparation of the pigment dispersion, but Comparative Example 5 showed a slow thickening from the moment the pigment dispersion was prepared.

[0840] Regarding the above phenomena, it is believed that resin (C1) contains a large number of aromatic rings in its main chain, thus exhibiting high affinity for pigments. Furthermore, the presence of methylene groups in the main chain provides flexibility to conform to the surface shape of the pigment, resulting in high pigment dispersibility. Alkali-soluble resin-I and alkali-soluble resin-VIII, belonging to resin (C1), are considered to exhibit high pigment dispersibility. Moreover, compared to alkali-soluble resin-I, alkali-soluble resin-VIII has an increased number of hydroxyl groups with high solvent affinity, thus resulting in better pigment dispersibility and viscosity stability.

[0841] It is believed that the aromatic ring content in the main chain of alkali-soluble resin-II is low, and on the other hand, it has a large dicyclopentane skeleton, thus resulting in low pigment dispersibility.

[0842] In addition, it is believed that although alkali-soluble resins III and IV contain a large number of aromatic rings in their main chain, the main chain is rigid and lacks flexibility, which is not conducive to following the surface shape of the pigment, and therefore the pigment dispersibility is low.

[0843] [Examples 5-9, Comparative Examples 6 and 7]

[0844] In Examples 5-9 and Comparative Examples 6 and 7, each component was added to pigment dispersions 7-9 in such a way that the content ratio of each component's solid component in the total solid component was the value recorded in Table 2. Then, a solvent was added in such a way that PGMEA / MB / MBA = 72 / 20 / 8 and the content ratio of the total solid component was 17% by mass. The mixture was stirred to dissolve the components, thus preparing the photosensitive coloring resin compositions of Examples 5-10 and Comparative Examples 6 and 7.

[0845] The evaluation results of unit OD value and residual film rate are shown in Tables 3 and 4.

[0846] [Table 3]

[0847]

[0848] [Table 4]

[0849]

[0850] As shown in Tables 3 and 4, the residual film rates of Examples 6-12 were observed to be better than those of Comparative Examples 6 and 7. This is believed to be because the resin (C1) contains a large number of aromatic rings in its main chain, thus improving the developer resistance during development and resulting in a higher residual film rate. It is believed that alkali-soluble resin-I belongs to resin (C1) and exhibits a high residual film rate.

[0851] As can be seen from the comparison of Examples 8-10 and 12, the residual film rate is further improved when using alkali-soluble resin-VI. This is believed to be because the structure of alkali-soluble resin-VI contains more aromatic rings than that of alkali-soluble resins-V and-VII.

[0852] The evaluation results of organic electroluminescent elements prepared using the photosensitive coloring resin compositions of Examples 6, 8, 10 and Comparative Examples 6 and 7 are shown in Table 5.

[0853] [Table 5]

[0854]

[0855] Examples 6, 8, and 10 in Table 5 show a tendency for high current density during luminescence. This is presumably because alkali-soluble resin-I and alkali-soluble resin-VIII contain a large number of aromatic rings in their main chains, which improves the resistance of the developer during development. As a result, less decomposition products accumulate in the pixel area of ​​the organic electroluminescent element during development.

[0856] In addition, it is believed that the alkali-soluble resin-VII has a heat-resistant isocyanuric acid skeleton, which reduces the accumulation of thermal decomposition products in the pixel during calcination, thus resulting in a higher current density.

[0857] On the other hand, in Comparative Examples 6 and 7, there was a tendency for low current density. This is presumably because the main chain contains fewer aromatic rings and the developer's resistance is reduced, resulting in more buildup of decomposition products in the pixel area of ​​the organic electroluminescent element during development.

[0858] Explanation of reference numerals in the attached figures

[0859] 1 Green luminescent nanocrystal particles

[0860] 2. Red luminescent nanocrystal particles

[0861] 10 substrate

[0862] 20 partition walls

[0863] 30 red pixels

[0864] 40 green pixels

[0865] 50 blue pixels

[0866] 100 color filter

Claims

1. A photosensitive coloring resin composition, characterized in that, It contains (A) colorant, (B) dispersant, (C) alkali-soluble resin and (D) photopolymerization initiator. The colorant (A) comprises an organic pigment (A-1). The (C) alkali-soluble resin contains a resin (C1) having the structural unit shown in the following general formula (1). In equation (1), R 1 Indicates a hydrogen atom or a methyl group. R 2 Each can independently represent an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms, and having at least a hydroxyl group, or a hydroxyl group and an ester group of a polybasic acid as substituents. *Each represents a connection key.

2. The photosensitive coloring resin composition according to claim 1, wherein, The resin (C1) has the structural unit shown in the following general formula (2), In formula (2), A represents a hydrogen atom or a polybasic acid residue. R 1 Indicates a hydrogen atom or a methyl group. R 2 Each can be independently represented as an alkyl group having 1 to 4 carbon atoms. *Each represents a connection key.

3. The photosensitive coloring resin composition according to claim 1 or 2, wherein, The organic pigment (A-1) comprises an organic black pigment.

4. The photosensitive coloring resin composition according to claim 3, wherein, The organic black pigment includes benzodifuranone-based organic black pigments.

5. The photosensitive coloring resin composition according to claim 4, wherein, The organic black pigment comprises an organic black pigment that is a compound, a geometric isomer thereof, a salt thereof, or a salt of a geometric isomer thereof, as shown in the following general formula (A-1-1). In equation (A-1-1), R 611 and R 616 Each can independently represent a hydrogen atom, CH3, CF3, fluorine atom, or chlorine atom; R 612 R 613 R 614 R 615 R 617 R 618 R 619 and R 620 Each independently represents a hydrogen atom, a halogen atom, and R. 621 COOH, COOR 621 COO - CONH2, CONHR 611 CONR 621 R 622 CN, OH, OR 621 COCR 621 、OOCNH2、OOCNHR 621 OOCNR 621 R 622 NO2, NH2, NHR 621 NR 621 R 622 , NHCOR 622 NR 621 COR 622 N=CH2, N=CHR 621 N = CR 621 R 622 SH, SR 621 SOR 621 SO2R 621 SO3R 621 SO3H, SO3 - SO2NH2, SO2NHR 621 or SO2NR 621 R 622 ; Choose freely R 612 With R 613 R 613 With R 614 R 614 With R 615 R 617 With R 618 R 618 With R 619 and R 619 With R 620 At least one of the groups may be directly bonded to each other, or may be bonded by oxygen, sulfur, NH or NR atoms. 621 Bridges connect them to each other; R 621 and R 622 Each can be independently represented as an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an alkynyl group having 2 to 12 carbon atoms.

6. The photosensitive coloring resin composition according to claim 1 or 2, wherein, The (B) dispersant comprises an acrylic dispersant having tertiary amino and / or quaternary ammonium groups.

7. The photosensitive coloring resin composition according to claim 1 or 2, wherein, The (C) alkali-soluble resin contains (C2) epoxy (meth)acrylate resin.

8. The photosensitive coloring resin composition according to claim 1 or 2, wherein, The (C) alkali-soluble resin contains (C3) a resin with an isocyanuric acid backbone.

9. The photosensitive coloring resin composition according to claim 1 or 2, wherein, The content of the resin (C1) in the alkali-soluble resin is in the range of 4 to 80% by mass.

10. A pigment dispersion, characterized in that, It contains (A) colorant, (B) dispersant and (C) alkali-soluble resin. The colorant (A) comprises an organic pigment (A-1). The (C) alkali-soluble resin contains a resin (C1) having the structural unit shown in the following general formula (1). In equation (1), R 1 Indicates a hydrogen atom or a methyl group. R 2 Each can independently represent an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms, and having at least a hydroxyl group, or a hydroxyl group and an ester group of a polybasic acid as substituents. *Each represents a connection key.

11. The pigment dispersion according to claim 10, wherein, The resin (C1) has the structural unit shown in the following general formula (2), In formula (2), A represents a hydrogen atom or a polybasic acid residue. R 1 Indicates a hydrogen atom or a methyl group. R 2 Each can independently represent an alkyl group having 1 to 4 carbon atoms. *Each represents a connection key.

12. The pigment dispersion according to claim 10 or 11, wherein, The organic pigment (A-1) comprises an organic black pigment.

13. The pigment dispersion according to claim 12, wherein, The organic black pigment includes benzodifuranone-based organic black pigments.

14. The pigment dispersion according to claim 13, wherein, The organic black pigment comprises an organic black pigment containing a compound, its geometric isomer, its salt, or a salt of a geometric isomer thereof, as shown in the following general formula (A-1-1). In equation (A-1-1), R 611 and R 616 Each can independently represent a hydrogen atom, CH3, CF3, fluorine atom, or chlorine atom; R 612 R 613 R 614 R 615 R 617 R 618 R 619 and R 620 Each independently represents a hydrogen atom, a halogen atom, and R. 621 COOH, COOR 621 COO - CONH2, CONHR 621 CONR 621 R 622 CN, OH, OR 621 COCR 621 、OOCNH2、OOCNHR 621 OOCNR 621 R 622 NO2, NH2, NHR 621 NR 621 R 622 , NHCOR 622 NR 621 COR 622 N=CH2, N=CHR 621 N = CR 621 R 622 SH, SR 621 SOR 621 SO2R 621 SO3R 621 SO3H, SO3 - SO2NH2, SO2NHR 621 or SO2NR 621 R 622 ; Choose freely R 612 With R 613 R 613 With R 614 R 614 With R 615 R 617 With R 618 R 618 With R 619 and R 619 With R 620 At least one combination in the group may be directly bonded to each other, or may be bonded by oxygen atom, sulfur atom, NH or NR atom. 621 Bridges connect them to each other; R 621 and R 622 Each can be independently represented as an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an alkynyl group having 2 to 12 carbon atoms.

15. The pigment dispersion according to claim 10 or 11, wherein, The (B) dispersant comprises an acrylic dispersant having tertiary amino and / or quaternary ammonium groups.

16. A cured product obtained by curing the photosensitive coloring resin composition according to any one of claims 1 to 9.

17. A partition wall formed from the solidified material of claim 16.

18. An organic electroluminescent element comprising the partition wall as described in claim 17.

19. A color filter having the partition wall of claim 17 and comprising luminescent nanocrystal particles.

20. An image display device comprising the organic electroluminescent element of claim 18.

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