Photosensitive colored resin composition, pigment dispersion, cured product, partition wall, organic electroluminescent element, color filter, and image display device

Abstract

Provided is a photosensitive colored resin composition having a high residual film ratio. The photosensitive colored resin composition is characterized by containing a coloring agent (A), a dispersant (B), an alkali-soluble resin (C), and a photopolymerization initiator (D). The photosensitive colored resin composition is also characterized in that the coloring agent (A) contains an organic pigment (A-1) and the alkali-soluble resin (C) contains a resin (C1) having a structural unit represented by general formula (1).

Description

Photosensitive colored resin composition, pigment dispersion, cured product, partition wall, organic electroluminescent device, color filter, and image display device

[0001] The present invention relates to a photosensitive colored resin composition, a pigment dispersion, a cured product, a partition wall, an organic electroluminescent device, a color filter, and an image display device. 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.

[0002] Liquid crystal displays (LCDs) utilize the property that liquid crystal molecules change their alignment when a voltage is applied to the liquid crystal. Many of the components that make up LCD cells are formed using photosensitive compositions, such as photolithography. These photosensitive compositions are finding wider applications because they are easy to form into fine structures and can be easily processed on substrates for large screens.

[0003] Image display devices including organic electroluminescent elements (also referred to as organic EL) have attracted attention as next-generation flat panel displays (FPDs) due to their excellent visibility and response, such as contrast and viewing angle, as well as the potential for low power consumption, thinness and weight reduction, and flexibility of the display body. Organic electroluminescent elements have a structure in which an organic layer including a light-emitting layer or various functional layers is sandwiched between a pair of electrodes, at least one of which is light-transmitting. Image display devices display images by driving a panel in which organic electroluminescent elements are arranged for each pixel. Conventionally, such organic electroluminescent elements have been manufactured by forming partition walls (banks) on a substrate and then laminating a light-emitting layer or various functional layers within the area surrounded by the partition walls.

[0004] To form a film of an emitting layer or the like within the region surrounded by the partition wall, a deposition method is mainly used, in which a material is sublimated in a vacuum and deposited on a substrate to form a film. In recent years, wet process film formation methods such as casting, spin coating, and inkjet printing have attracted attention. In particular, inkjet printing can reduce film thickness unevenness when applied to a large area, and can achieve high-definition displays by applying different colors during application, reduce material usage, and improve yield, making it a suitable method for forming organic layers in large panels.

[0005] A known method for easily forming the partition wall is to form it by photolithography using a photosensitive composition. Also, a known method for imparting light-shielding properties to the partition wall and suppressing light leakage between pixels is to include a colorant in the photosensitive composition.

[0006] Patent Document 1 describes a photosensitive colored resin composition that uses a specific organic black pigment and a dispersant to have high light-shielding properties and a low dielectric constant.

[0007] Furthermore, Patent Document 2 describes a photosensitive colored resin composition used for partition walls of organic electroluminescent devices, which is effective in suppressing outgassing by using a specific organic black pigment and an alkali-soluble resin.

[0008] International Publication No. WO 2015 / 46178 International Publication No. WO 2018 / 101314

[0009] A known method for preparing a photosensitive colored resin composition for use in a light-shielding partition wall application involves adding a pigment as a colorant, dispersing the pigment using a dispersant, and mixing the resulting pigment dispersion with other components. However, in such pigment dispersions, sufficient dispersibility and storage stability may not be ensured depending on the type of pigment, dispersant, and dispersing resin. Furthermore, if the residual film rate of the photosensitive colored resin composition is low during the development and baking steps in the production of partition walls, the developer resistance and heat resistance during baking may be poor, and decomposition products, by-products, uncured materials, etc. in the composition may remain on or re-adhere to the anode.

[0010]

[0013] The present inventors have conducted studies and found that, when a partition wall is used in an organic electroluminescent device, sufficient luminance may not be obtained due to residues and redeposited matter on the anode when the device current density relative to the applied voltage is low, and that the photosensitive colored resin compositions described in Patent Documents 1 and 2 do not provide sufficient film remaining rates and device current densities.

[0011] Therefore, a first object of the present invention has been made in consideration of the above circumstances, and it is an object of the present invention to provide a photosensitive color resin composition having a high film retention rate. Another object of the present invention is to provide a photosensitive color resin composition having a high film retention rate and having a high device current density when used in a partition wall for an organic electroluminescent device. Another object of the present invention is to provide an organic electroluminescent device and an image display device having high brightness.

[0012] A second object of the present invention is to provide a pigment dispersion liquid having excellent dispersibility, a photosensitive colored resin composition, an organic electroluminescent device, and an image display device.

[0013] As a result of extensive research, the present inventors have found that the above problems can be solved by using a specific alkali-soluble resin and an organic pigment, and have thus completed the present invention.

[0014] That is, the gist of the present invention is as follows: [1] A photosensitive color resin composition containing (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin, and (D) a photopolymerization initiator, characterized in that the (A) colorant contains an organic pigment (A-1), and the (C) alkali-soluble resin contains a resin (C1) having a structural unit represented by the following general formula (1):

[0015]

[0016] (In formula (1), R 1 represents a hydrogen atom or a methyl group. 2each independently represents an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms, and has, as a substituent, at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid. * represents a bond.) [2] The photosensitive color resin composition of [1], wherein the resin (C1) has a structural unit represented by the following general formula (2):

[0017]

[0018] (In formula (2), A represents a hydrogen atom or a polybasic acid residue. R 1 represents a hydrogen atom or a methyl group. 2 each independently represents an alkyl group having 1 to 4 carbon atoms. * represents a bond.) [3] The photosensitive colored resin composition of [1] or [2], wherein the organic pigment (A-1) comprises an organic black pigment. [4] The photosensitive colored resin composition of [3], wherein the organic black pigment comprises a benzodifuranone-based organic black pigment. [5] The photosensitive colored resin composition of [4], wherein the organic black pigment comprises an organic black pigment that is a compound represented by the following general formula (A-1-1), a geometric isomer thereof, a salt thereof, or a salt of the geometric isomer:

[0019]

[0020] (In formula (A-1-1), R 611 and R 616 each independently represents a hydrogen atom, CH3, CF3, a fluorine atom, or a chlorine atom; R 612 , R 613 , R 614 , R 615 , R 617 , R 618 , R 619 and R 620 are each independently a hydrogen atom, a halogen atom, R 621 , COOH, COOR 621 , COO - , CONH2, CONHR 611 , C.O.R. 621 R 622 , CN, OH, OR 621 , COCR 621 , OOCNH2, OOCNHR 621 , OOCNR 621 R 622, NO2, NH2, NHR 621 , N.R. 621 R 622 , NHCOR 622 , N.R. 621 COR 622 , N=CH2, N=CHR 621 , N=CR 621 R 622 , S.H., S.R. 621 , SOR 621 , SO2R 621 , SO3R 621 , SO3H, SO3 - , SO2NH2, SO2NHR 621 or SO2NR 621 R 622 represents; R 612 and R 613 , R 613 and R 614 , R 614 and R 615 , R 617 and R 618 , R 618 and R 619 , and R 619 and R 620 may be directly bonded to each other or may be bonded to an oxygen atom, a sulfur atom, an NH or an NR 621 may be connected to each other by bridges; R 621 and R 622 each independently represents 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 colored resin composition of [1] or [2], wherein the (B) dispersant contains an acrylic dispersant having a tertiary amino group and / or a quaternary ammonium group. [7] The photosensitive colored resin composition of [1] or [2], wherein the (C) alkali-soluble resin contains an epoxy (meth)acrylate resin (C2). [8] The photosensitive colored resin composition of [1] or [2], wherein the (C) alkali-soluble resin contains an isocyanuric skeleton-containing resin (C3). [9] The photosensitive colored resin composition of [1] or [2], wherein the content of the resin (C1) in the alkali-soluble resin (C) is in the range of 4 to 80 mass%.

[0021]

[10] A pigment dispersion containing (A) a colorant, (B) a dispersant, and (C) an alkali-soluble resin, wherein the (A) colorant contains an organic pigment (A-1), and the (C) alkali-soluble resin contains a resin (C1) having a structural unit represented by the following general formula (1):

[0022]

[0023] (In formula (1), R 1 represents a hydrogen atom or a methyl group. 2 each independently represents an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms, and has, as a substituent, at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid. * represents a bond.)

[11] The pigment dispersion of

[10] , wherein the resin (C1) has a structural unit represented by the following general formula (2):

[0024]

[0025] (In formula (2), A represents a hydrogen atom or a polybasic acid residue. R 1 represents a hydrogen atom or a methyl group. 2 each independently represents an alkyl group having 1 to 4 carbon atoms. * represents a bond.)

[12] The pigment dispersion of

[10] or

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

[13] The pigment dispersion of

[12] , wherein the organic black pigment contains a benzodifuranone-based organic black pigment.

[14] The pigment dispersion of

[13] , wherein the organic black pigment contains an organic black pigment that is a compound represented by the following general formula (A-1-1), a geometric isomer thereof, a salt thereof, or a salt of the geometric isomer:

[0026]

[0027] (In formula (A-1-1), R 611 and R 616 each independently represents a hydrogen atom, CH3, CF3, a fluorine atom, or a chlorine atom; R 612 , R 613 , R 614 , R 615 , R 617 , R 618 , R619 and R 620 are each independently a hydrogen atom, a halogen atom, R 621 , COOH, COOR 621 , COO - , CONH2, CONHR 621 , C.O.R. 621 R 622 , CN, OH, OR 621 , COCR 621 , OOCNH2, OOCNHR 621 , OOCNR 621 R 622 , NO2, NH2, NHR 621 , N.R. 621 R 622 , NHCOR 622 , N.R. 621 COR 622 , N=CH2, N=CHR 621 , N=CR 621 R 622 , S.H., S.R. 621 , SOR 621 , SO2R 621 , SO3R 621 , SO3H, SO3 - , SO2NH2, SO2NHR 621 or SO2NR 621 R 622 represents; R 612 and R 613 , R 613 and R 614 , R 614 and R 615 , R 617 and R 618 , R 618 and R 619 , and R 619 and R 620 may be directly bonded to each other or may be bonded to an oxygen atom, a sulfur atom, an NH or an NR 621 may be connected to each other by bridges; R 621 and R 622each independently represents 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

[10] or

[11] , wherein the (B) dispersant contains an acrylic dispersant having a tertiary amino group and / or a quaternary ammonium group.

[0028]

[16] A photosensitive colored resin composition comprising the pigment dispersion of

[10] or

[11] and (D) a photopolymerization initiator.

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

[16] .

[18] A partition wall formed from the cured product of

[17] .

[19] An organic electroluminescent device comprising the partition wall of

[18] .

[20] A color filter containing luminescent nanocrystalline particles comprising the partition wall of

[19] .

[21] An image display device comprising the partition wall of

[19] .

[0029]

[22] A compound having a structural unit represented by the following general formula (1):

[0030]

[0031] (In formula (1), R 1 represents a hydrogen atom or a methyl group. 2 each independently represents an alkyl group having 1 to 4 carbon atoms; L represents an alkylene group having 2 to 6 carbon atoms, and has at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid as a substituent; * represents a bond.

[0032] According to the present invention, it is possible to provide a photosensitive color resin composition having a high film retention rate, a pigment dispersion liquid having excellent dispersibility, and an organic electroluminescent device and an image display device.

[0033] FIG. 1 is a schematic cross-sectional view of an example of a color filter having partition walls of the present invention.

[0034] The following describes specific embodiments of the present invention. However, the present invention is not limited to the following embodiments and can be modified in various ways within the scope of the present invention. In the present invention, "(meth)acrylic" means "acrylic and / or methacrylic," and the same applies to "(meth)acrylate" and "(meth)acryloyl." "Acrylic resin" refers to a (co)polymer containing (meth)acrylic acid or a (co)polymer containing a (meth)acrylic acid ester having a carboxy group. "Total solids" refers to all components other than the solvent contained in the photosensitive colored resin composition or pigment dispersion. Even if components other than the solvent are liquid at room temperature, these components are not included in the solvent but are included in the total solids. "(Co)polymer" refers to both homopolymers and copolymers, and "acid (anhydride)" and "(anhydride)...acid" refer to both acids and their anhydrides. "Monomer" is a term that is the opposite of a so-called high molecular substance (polymer) and includes not only monomers in the narrow sense but also dimers, trimers, and oligomers. "Weight average molecular weight" refers to the weight average molecular weight (Mw) calculated in terms of polystyrene by GPC (gel permeation chromatography). "Amine value" refers to the amine value calculated in terms of effective solids, unless otherwise specified, and is a value expressed as the mass of KOH equivalent to the amount of base per gram of solids in the dispersant. The measurement method will be described later. "Acid value" refers to the acid value calculated in terms of effective solids, unless otherwise specified, and is calculated by neutralization titration. With respect to pigments, "C.I." means Color Index. In this specification, percentages and parts expressed by "mass" are synonymous with percentages and parts expressed by "weight".

[0035] The photosensitive colored resin composition related to the first aspect of the present invention contains (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin, and (D) a photopolymerization initiator, (A) the colorant contains an organic pigment (A-1), and (C) the alkali-soluble resin contains a resin (C1) represented by formula (1).

[0036] The pigment dispersion related to the second aspect of the present invention contains (A) a colorant, (B) a dispersant, and (C) an alkali-soluble resin, wherein the (A) colorant contains an organic pigment (A-1), and the (C) alkali-soluble resin contains a resin (C1) represented by formula (1).

[0037] Hereinafter, unless otherwise specified, (A) colorant, (B) dispersant, (C) alkali-soluble resin, (D) photopolymerization initiator refer to the constituent elements of both the photosensitive color resin composition related to the first aspect and the pigment dispersion related to the second aspect.

[0038] [Photosensitive Colored Resin Composition] The photosensitive colored resin composition of the present invention contains: (A) a colorant; (B) a dispersant; (C) an alkali-soluble resin; and (D) a photopolymerization initiator.

[0039] <(A) Colorant> The photosensitive color resin composition of the present invention contains (A) colorant. By containing (A) colorant, it is possible to obtain appropriate light absorption properties, particularly appropriate light blocking properties when used for forming light blocking members such as partition walls. The (A) colorant of the present invention contains an organic pigment (A-1). By containing the organic pigment (A-1), insulation properties tend to be improved.

[0040] The pigment contained in the (A) colorant may be one type alone or two or more types. From the viewpoint of achieving both uniform light blocking in the visible region and OD per unit film thickness, two or more types are preferably used. The organic pigment that can be used as the (A) colorant is not particularly limited, and examples thereof include organic color pigments and organic black pigments. Here, the organic color pigment means an organic pigment that exhibits a color other than black, and examples thereof include red pigments, orange pigments, blue pigments, purple pigments, green pigments, and yellow pigments.

[0041] Among organic pigments, organic color pigments are preferred from the viewpoints of suppressing ultraviolet absorption, improving curability, and facilitating control of the shape of the cured product, while organic black pigments are preferred from the viewpoints of improving light-shielding properties and enabling a lower pigment concentration relative to the solid content.

[0042] Examples of organic black pigments include perylene-based black pigments, aniline-based black pigments, and benzodifuranone-based black pigments. Examples of perylene-based black pigments include Lumogen Black (registered trademark) FK4281, K0087, and Paliogen Black (registered trademark) EH0788 (all manufactured by BASF). Examples of aniline-based black pigments include Paliotol Black (registered trademark) L0080, D0080, and K0080 (all manufactured by BASF).

[0043] As the organic black pigment, from the viewpoints of light-shielding properties, dispersibility, developability, and luminescence properties, benzodifuranone-based black pigments are preferred. Among the benzodifuranone-based black pigments, from the viewpoints of light-shielding properties, dispersibility, developability, and luminescence properties, it is preferable to use an organic black pigment containing at least one selected from the group consisting of a compound represented by the following general formula (A-1-1) (hereinafter, sometimes referred to as "compound (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) (hereinafter, sometimes referred to as "organic black pigment represented by general formula (A-1-1)").

[0044]

[0045] In formula (A-1-1), R 611 and R 616 each independently represents a hydrogen atom, CH3, CF3, a fluorine atom, or a chlorine atom; R 612 , R 613 , R 614 , R 615 , R 617 , R 618 , R 619 and R 620 are each independently a hydrogen atom, a halogen atom, R 621 , COOH, COOR 621 , COO - , CONH2, CONHR 621 , C.O.R. 621 R 622 , CN, OH, OR 621 , COCR 621 , OOCNH2, OOCNHR 621 , OOCNR621 R 622 , NO2, NH2, NHR 621 , N.R. 621 R 622 , NHCOR 622 , N.R. 621 COR 622 , N=CH2, N=CHR 621 , N=CR 621 R 622 , S.H., S.R. 621 , SOR 621 , SO2R 621 , SO3R 621 , SO3H, SO3 - , SO2NH2, SO2NHR 621 or SO2NR 621 R 622 represents; R 612 and R 613 , R 613 and R 614 , R 614 and R 615 , R 617 and R 618 , R 618 and R 619 , and R 619 and R 620 may be directly bonded to each other or may be bonded to an oxygen atom, a sulfur atom, an NH or an NR 621 may be connected to each other by bridges; R 621 and R 622 each independently represents 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.

[0046] Compound (A-1-1) and the geometric isomers of compound (A-1-1) have the following core structure (substituents in the structural formula are omitted), and the trans-trans isomer is probably the most stable.

[0047]

[0048] When compound (A-1-1) is anionic, it is preferably a salt in which its charge is compensated with any known suitable cation, for example, a metal, organic, inorganic, or metal-organic 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 a geometric isomer of compound (A-1-1) is anionic, it is preferably a similar salt.

[0049] The following substituents in formula (A-1-1) and their definitions tend to have a high shielding rate, and are therefore preferred. This is because the following substituents have no absorption and are thought not to affect the hue of the pigment. R 612 , R 614 , R 615 , R 617 , R 619 and R 620 are each independently preferably a hydrogen atom, a fluorine atom, or a chlorine atom, and more preferably a hydrogen atom. 613 and R 618 are each independently preferably a hydrogen atom, NO2, OCH3, OC2H5, a bromine atom, a chlorine atom, CH3, C2H5, N(CH3)2, N(CH3)(C2H5), N(C2H5)2, α-naphthyl, β-naphthyl, SO3H, or SO3 - is more preferably a hydrogen atom or SO3H, and particularly preferably a hydrogen atom.

[0050] R 611 and R 616 are each independently preferably a hydrogen atom, CH or CF, more preferably a hydrogen atom. 611 and R 616 , R 612 and R 617 , R 613 and R 618 , R 614 and R 619 , and R 615 and R 620 At least one combination selected from the group consisting of R 611 is R616 is the same as R 612 is R 617 is the same as R 613 is R 618 is the same as R 614 is R 619 and R 615 is R 620 is the same as

[0051] Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a 2-methylbutyl group, an n-pentyl group, a 2-pentyl group, a 3-pentyl group, a 2,2-dimethylpropyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, a 1,1,3,3-tetramethylbutyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group.

[0052] Examples of the cycloalkyl group having 3 to 12 carbon atoms include a cyclopropyl group, a cyclopropylmethyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexylmethyl group, a trimethylcyclohexyl group, a thujyl group, a norbornyl group, a bornyl group, a norcaryl group, a caryl group, a menthyl group, a norpinyl group, a pinyl group, an adamantan-1-yl group, and an adamantan-2-yl group.

[0053] Examples of the alkenyl group having 2 to 12 carbon atoms include a vinyl group, an allyl group, a 2-propen-2-yl group, a 2-buten-1-yl group, a 3-buten-1-yl group, a 1,3-butadien-2-yl group, a 2-penten-1-yl group, a 3-penten-2-yl group, a 2-methyl-1-buten-3-yl group, a 2-methyl-3-buten-2-yl group, a 3-methyl-2-buten-1-yl group, a 1,4-pentadien-3-yl group, a hexenyl group, an octenyl group, a nonenyl group, a decenyl group, and a dodecenyl group.

[0054] Examples of the cycloalkenyl group having 3 to 12 carbon atoms include a 2-cyclobuten-1-yl group, a 2-cyclopenten-1-yl group, a 2-cyclohexen-1-yl group, a 3-cyclohexen-1-yl group, a 2,4-cyclohexadien-1-yl group, a 1-p-menthen-8-yl group, a 4(10)-thujen-10-yl group, a 2-norbornen-1-yl group, a 2,5-norbornadien-1-yl group, a 7,7-dimethyl-2,4-norcaradien-3-yl group, and a camphenyl group.

[0055] Examples of the alkynyl group having 2 to 12 carbon atoms include a 1-propyn-3-yl group, a 1-butyn-4-yl group, a 1-pentyn-5-yl group, a 2-methyl-3-butyn-2-yl group, a 1,4-pentadiyn-3-yl group, a 1,3-pentadiyn-5-yl group, a 1-hexyn-6-yl group, a cis-3-methyl-2-penten-4-yn-1-yl group, a trans-3-methyl-2-penten-4-yn-1-yl group, a 1,3-hexadiyn-5-yl group, a 1-octyn-8-yl group, a 1-nonyne-9-yl group, a 1-decyn-10-yl group, and a 1-dodecyn-12-yl group.

[0056] The halogen atom is, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0057] The organic black pigment represented by formula (A-1-1) is preferably an organic black pigment containing at least one member selected from the group consisting of a compound represented by the following general formula (A-1-2) (hereinafter also referred to as "compound (A-1-2)") and a geometric isomer of compound (A-1-2):

[0058]

[0059] An example of compound (A-1-2) is the trade name Irgaphor (registered trademark) Black S 0100 CF (manufactured by BASF). This organic black pigment is preferably dispersed using a dispersant, solvent, and method described below. Furthermore, the presence of a sulfonic acid derivative of compound (A-1-1), particularly a sulfonic acid derivative of compound (A-1-2), during dispersion can improve dispersibility and storage stability, so it is preferable that the organic black pigment contain these sulfonic acid derivatives.

[0060] The chemical structure of the organic color pigment is not particularly limited, but examples thereof include azo, phthalocyanine, quinacridone, benzimidazolone, isoindolinone, dioxazine, indanthrene, and perylene pigments. Specific examples of pigments that can be used are listed below by pigment number. The "C.I." in "C.I. Pigment Red 2" and other pigments listed below stands for Color Index.

[0061] Examples of red pigments include C.I. Pigment Red 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, 149, 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, 232, 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 properties and dispersibility, preferred are C.I. Pigment Red 48:1, 122, 149, 168, 177, 179, 194, 202, 206, 207, 209, 224, 242, 254, and more preferred are C.I. Pigment Red 177, 209, 224, 254. In terms of dispersibility and light-blocking properties, it is preferable to use C.I. Pigment Red 177, 254, and 272. When the photosensitive colored resin composition is cured with ultraviolet light, it is preferable to use a red pigment with low ultraviolet absorption, and from this viewpoint, it is more preferable to use C.I. Pigment Red 254 and 272.

[0062] Examples of orange pigments include C.I. Pigment 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 viewpoint of dispersibility and light-blocking properties, it is preferable to use C.I. Pigment Orange 13, 43, 64, and 72. When the photosensitive colored resin composition is cured with ultraviolet light, it is preferable to use an orange pigment with low ultraviolet absorption, and from this viewpoint, it is more preferable to use C.I. Pigment Orange 64 and 72.

[0063] Examples of blue pigments include C.I. 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, preferred examples include C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, and 60, and more preferred examples include C.I. Pigment Blue 15:6. In terms of dispersibility and light-blocking properties, it is preferable to use C.I. Pigment Blue 15:6, 16, and 60. When the photosensitive colored resin composition is cured with ultraviolet light, it is preferable to use a blue pigment having a low ultraviolet absorption rate, and from this viewpoint, it is more preferable to use C.I. Pigment Blue 60.

[0064] Examples of purple pigments include C.I. Pigment Violet 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, C.I. Pigment Violet 19, 23, and 29 are preferred, and C.I. Pigment Violet 23 is more preferred. In terms of dispersibility and light-blocking properties, it is preferable to use C.I. Pigment Violet 23 and 29. When the photosensitive colored resin composition is cured with ultraviolet light, it is preferable to use a purple pigment with low ultraviolet absorption, and from this viewpoint, it is more preferable to use C.I. Pigment Violet 29.

[0065] Examples of green pigments include C.I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, and 59. Preferred examples include C.I. Pigment Green 7 and 36.

[0066] Examples of yellow pigments include C.I. 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, 134, 136, 13 8, 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, 191:1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208 can be mentioned. Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180, and 185, and more preferably C.I. Pigment Yellow 83, 138, 139, 150, and 180.

[0067] From the viewpoint of the light-shielding properties of the cured product and shape control, it is preferable to use at least one pigment selected from the group consisting of red pigments, orange pigments, blue pigments and purple pigments.

[0068] From the viewpoint of the light-blocking properties of the cured product and shape control, it is preferable to contain at least one of the following pigments: Red pigment: C.I. Pigment Red 177, 254, 272 Orange pigment: C.I. Pigment Orange 43, 64, 72 Blue pigment: C.I. Pigment Blue 15:6, 60 Purple pigment: C.I. Pigment Violet 23, 29

[0069] When two or more organic color pigments are used in combination, the combination of organic color pigments is not particularly limited, but from the viewpoint of light-blocking properties, it is preferable to contain at least one selected from the group consisting of a red pigment and an orange pigment, and at least one selected from the group consisting of a blue pigment and a violet pigment. The color combination is not particularly limited, but from the viewpoint of light-blocking properties, examples of the combination include a combination of a red pigment and a blue pigment, a combination of a blue pigment and an orange pigment, and a combination of a blue pigment, an orange pigment and a violet pigment.

[0070] As the colorant (A) that can be used in the photosensitive color resin composition of the present invention, a colorant other than the organic pigment (A-1) may be used in combination. The colorant that can be used in combination is not particularly limited, and a pigment or a dye may be used. The other colorant used in combination with the organic pigment may be used alone or in combination of two or more. From the viewpoint of durability, it is preferable to use a pigment. For example, an inorganic pigment may be used.

[0071] As the inorganic pigment, it is preferable to use an inorganic black pigment from the viewpoint of higher light-shielding properties. Examples of inorganic black pigments include carbon black, acetylene black, lamp black, bone black, graphite, iron black, cyanine black, and titanium black. From the viewpoint of light-shielding properties and image characteristics, carbon black can be preferably used.

[0072] Examples of carbon black include the following carbon blacks 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, and #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. Degussa: Printex (registered trademark, hereinafter the same) 3, Printex3OP, Printex30, Printex30OP, Printex40, Printex45, Printex55, Printex60, Printex75, Printex80, Printex85, Printex90, Printex A, Printex L, Printex G, Printex P, Printex U, Printex V, PrintexG, SpecialBlack550, SpecialBlack350, SpecialBlack250, Sp specialBlack100, SpecialBlack6, SpecialBlack5, SpecialBlack4, Color Black FW1, Color Black FW2, Color Black FW2V, Color Black FW18, Color Black FW200, Color Black S160, Color Black S170. Cabot Corporation: Monarch (registered trademark, the same applies hereinafter) 120, Monarch 280, Monarch 460, Monarch 800, Monarch 880, Monarch 900, Monarch 1000, Monarch 1100, Monarch 1300, Monarch 1400, Monarch 4630, REGAL (registered trademark, the same applies hereinafter).) 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, the same applies below) XC72R, ELFTEX (registered trademark)-8. Biller: RAVEN (registered trademark, the same applies hereinafter) 11, RAVEN 14, RAVEN 15, RAVEN 16, RAVEN 22, RAVEN 30, RAVEN 35, RAVEN 40, RAVEN 410, RAVEN 420, RAVEN 450, RAVEN 500, RAVEN 780, RAVEN 850, RAVEN 890H, RAVEN 100 0, RAVEN1020, RAVEN1040, RAVEN1060U, RAVEN1080U, RAVEN1170, RAVEN1190U, RAVEN1250, RAV EN1500, RAVEN2000, RAVEN2500U, RAVEN3500, RAVEN5000, RAVEN5250, RAVEN5750, RAVEN7000.

[0073] Carbon black whose surface has been treated with an acid may be used. For example, the carbon black described in Japanese Patent No. 3674086 can be preferably used. Carbon black coated with a resin may also be used. The use of resin-coated carbon black has the effect of improving adhesion to the glass substrate and volume resistivity. For example, the carbon black described in Japanese Patent Application Laid-Open No. 09-71733 can be preferably used as resin-coated carbon black. Resin-coated carbon black is preferably used in terms of volume resistivity and dielectric constant.

[0074] These pigments are preferably dispersed and used so that 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. In the photosensitive colored resin composition of the present invention, the average particle size of the pigment is a value determined from the pigment particle size measured by dynamic light scattering (DLS). Particle size measurement is performed on a sufficiently diluted photosensitive colored resin composition (usually diluted to prepare a pigment concentration of about 0.005 to 0.2 mass %; however, if a concentration recommended by the measuring instrument is available, that concentration should be followed), and the measurement is performed at 25°C.

[0075] In addition to the above-mentioned organic pigments and inorganic pigments, dyes may also be used. Examples of dyes that can be used as colorants include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinoneimine dyes, quinoline dyes, nitro dyes, carbonyl dyes, and methine dyes.

[0076] Examples of azo dyes include C.I. Acid Yellow 11, C.I. Acid Orange 7, C.I. Acid Red 37, C.I. Acid Red 180, C.I. Acid Blue 29, C.I. Direct Red 28, C.I. Direct Red 83, C.I. Direct Yellow 12, C.I. Direct Orange 26, C.I. Direct Green 28, C.I. Direct Green 59, C.I. Reactive Yellow 2, C.I. Reactive Red 17, C.I. Reactive Red 120, C.I. Reactive Black 5, C.I. Disperse Orange 5, C.I. Disperse Red 58, C.I. Disperse Blue 165, C.I. Basic Blue 41, C.I. Basic Red 18, C.I. Examples of suitable pigments include C.I. Mordant Red 7, C.I. Mordant Yellow 5, and C.I. Mordant Black 7.

[0077] Examples of anthraquinone dyes include C.I. Vat Blue 4, C.I. Acid Blue 40, C.I. Acid Green 25, C.I. Reactive Blue 19, C.I. Reactive Blue 49, C.I. Disperse Red 60, C.I. Disperse Blue 56, and C.I. Disperse Blue 60.

[0078] Examples of phthalocyanine dyes include C.I. Vat Blue 5. Examples of quinoneimine dyes include C.I. Basic Blue 3 and C.I. Basic Blue 9. Examples of quinoline dyes include C.I. Solvent Yellow 33, C.I. Acid Yellow 3, and C.I. Disperse Yellow 64. Examples of nitro dyes include C.I. Acid Yellow 1, C.I. Acid Orange 3, and C.I. Disperse Yellow 42.

[0079] <(B) Dispersant> In order to ensure the stability of quality, (A) colorant is finely dispersed and its dispersion state is stabilized, so the photosensitive color resin composition of the present invention contains (B) dispersant.As (B) dispersant, polymer dispersant having functional group is preferred, and further, from the viewpoint of dispersion stability, polymer dispersant having functional group such as carboxyl group; phosphate group; sulfonic acid group; or their base; primary, secondary or tertiary amino group; quaternary ammonium group; group derived from nitrogen-containing heterocycle such as pyridine, pyrimidine, pyrazine, etc. is preferred.In particular, polymer dispersant having basic functional group such as primary, secondary or tertiary amino group; quaternary ammonium group; group derived from nitrogen-containing heterocycle such as pyridine, pyrimidine, pyrazine, etc. is particularly preferred from the viewpoint that pigment can be dispersed with a small amount of dispersant.

[0080] Examples of polymeric dispersants include urethane-based dispersants, acrylic-based dispersants, polyethyleneimine-based dispersants, polyallylamine-based dispersants, dispersants consisting of a monomer and a macromonomer having an amino group, polyoxyethylene alkyl ether-based dispersants, polyoxyethylene diester-based dispersants, polyether phosphate-based dispersants, polyester phosphate-based dispersants, sorbitan aliphatic ester-based dispersants, and aliphatic-modified polyester-based dispersants.

[0081] Examples of such dispersants include trade names such as EFKA (registered trademark, manufactured by BASF), DISPERBYK (registered trademark, manufactured by BYK-Chemie), DISPARLON (registered trademark, manufactured by Kusumoto Chemicals 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., Inc.) One type of polymer dispersant may be used alone, or two or more types may be used in combination.

[0082] From the viewpoint of pigment dispersibility, the dispersant (B) preferably contains either or both of a urethane-based polymer dispersant and an acrylic-based polymer dispersant having a functional group, and particularly preferably contains an acrylic-based polymer dispersant. From the viewpoints of dispersibility and storage stability, a polymer dispersant having a basic functional group and either or both of a polyester bond and a polyether bond is preferred.

[0083] Examples of urethane-based and acrylic-based polymer dispersants include DISPERBYK-160 to 167, 182 series (all urethane-based), DISPERBYK-2000, 2001, BYK-LPN21116 (all acrylic-based) (all manufactured by BYK-Chemie).

[0084] The amine value of the polymer dispersant having a basic functional group is not particularly limited, but is preferably 1 mgKOH / g or more, more preferably 10 mgKOH / g or more, even more preferably 20 mgKOH / g or more, even more preferably 40 mgKOH / g or more, and particularly preferably 50 mgKOH / g or more. It is also preferably 140 mgKOH / g or less, more preferably 120 mgKOH / g or less, even more preferably 100 mgKOH / g or less, even more preferably 90 mgKOH / g or less, and particularly preferably 80 mgKOH / g or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 1 to 140 mgKOH / g, more preferably 10 to 120 mgKOH / g, even more preferably 20 to 100 mgKOH / g, even more preferably 40 to 90 mgKOH / g, and particularly preferably 50 to 80 mgKOH / g. Setting it to be equal to or greater than the lower limit tends to improve dispersibility. By adjusting the content to the upper limit or less, compatibility with the alkali-soluble resin (C) tends to be good.

[0085] From the viewpoint of dispersibility, the acrylic dispersant is preferably an A-B or B-A-B block copolymer composed of an A block having the above-mentioned functional group and a B block not having the above-mentioned functional group. In this case, in addition to the partial structure derived from the unsaturated group-containing monomer having the above-mentioned functional group, the A block may also contain a partial structure derived from the unsaturated group-containing monomer not having the above-mentioned functional group, and these may be contained in the A block in either a random copolymerization or block copolymerization manner. The content of the partial structure not having a functional group in the A block is preferably 80% by mass or less, more preferably 50% by mass or less, even more preferably 30% by mass or less, still more preferably 10% by mass or less, and particularly preferably 0% by mass.

[0086] From the viewpoint of dispersibility, it is preferable that the B block is composed only of a partial structure derived from an unsaturated group-containing monomer that does not contain the above functional group, and partial structures derived from two or more types of monomers may be contained in one B block, and these may be contained in the B block in the form of either random copolymerization or block copolymerization. The A-B or B-A-B block copolymer is prepared, for example, by the living polymerization method shown below. Living polymerization methods include anionic living polymerization, cationic living polymerization, and radical living polymerization. Of these, anionic living polymerization uses an anion as the active polymerization species, and is represented, for example, by the following scheme:

[0087]

[0088] In the above scheme, Ar 1 is a monovalent organic group, and Ar 2 is Ar 1 M is a metal atom, and s and t are each an integer of 1 or more.

[0089] In the radical living polymerization method, the active species for polymerization are radicals, and for example, the method is shown in the following scheme.

[0090]

[0091] In the above scheme, Ar 1 is a monovalent organic group, and Ar 2 is Ar 1 j and k are each an integer of 1 or more, and R a is a hydrogen atom or a monovalent organic group, and R b is R a is a hydrogen atom or a monovalent organic group different from

[0092] In synthesizing this acrylic dispersant, the following methods have been used: Japanese Patent Application Laid-Open No. 9-62002; P. Lutz, P. Masson et al., Polym. Bull. 12, 79 (1984); B. C. Anderson, G. D. Andrews et al., Macromolecules, 14, 1601 (1981); K. Hatada, K. Ute, et al., Polym. J. 17, 977 (1985); K. Hatada, K. Ute, et al., Polym. J. 18, 1037 (1986), Koichi Migite, Koichi Hatada, Polymer Processing, 36, 366 (1987), Toshinobu Higashimura, Mitsuo Sawamoto, Polymer Research Papers, 46, 189 (1989), M. Kuroki, T. Aida, J. Am. Chem. Sic, 109, 4737 (1987), Takuzo Aida, Shohei Inoue, Organic Synthetic Chemistry, 43, 300 (1985), D. Y. Sogoh, W. R. Hertler et al., Macromolecules, 20, 1473 (1987), and other known methods can be employed.

[0093] The acrylic dispersant that can be used in the present invention may be an A-B block copolymer or a B-A-B block copolymer, and the A block / B block ratio constituting the copolymer is not particularly limited, but is preferably 1 / 99 to 80 / 20 (mass ratio), and more preferably 5 / 95 to 60 / 40 (mass ratio). By keeping the ratio within this range, it tends to be easier to ensure a balance between dispersibility and storage stability. The amount of quaternary ammonium groups per 1 g of the A-B block copolymer or B-A-B block copolymer that can be used in the present invention is preferably 0.1 to 10 mmol. By keeping the ratio within this range, it tends to be easier to ensure good dispersibility.

[0094] Such an acrylic dispersant may contain an amino group. The amine value of the acrylic dispersant is preferably 1 mgKOH / g or more, more preferably 10 mgKOH / g or more, even more preferably 20 mgKOH / g or more, even more preferably 40 mgKOH / g or more, and particularly preferably 50 mgKOH / g or more. It is also preferably 140 mgKOH / g or less, more preferably 120 mgKOH / g or less, even more preferably 100 mgKOH / g or less, even more preferably 90 mgKOH / g or less, and particularly preferably 80 mgKOH / g or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 1 to 140 mgKOH / g, more preferably 10 to 120 mgKOH / g, even more preferably 20 to 100 mgKOH / g, even more preferably 40 to 90 mgKOH / g, and particularly preferably 50 to 80 mgKOH / g. By adjusting the amine value to be equal to or greater than the lower limit, dispersibility tends to be improved. By keeping the content below the upper limit, compatibility with (C) the alkali-soluble resin tends to be improved. The amine value of an acrylic dispersant is expressed as the mass of KOH equivalent to the amount of base per gram of solids, excluding the solvent, in the dispersant sample, and is measured using the following method. 0.5 to 1.5 g of the dispersant sample is accurately weighed into a 100 mL beaker and dissolved in 50 mL of acetic acid. Using an automatic titrator equipped with a pH electrode, this solution is neutralized with a 0.1 mol / L HClO4 acetic acid solution. The inflection point on the titration pH curve is used as the titration endpoint, and the amine value is calculated using the following formula:

[0095] Amine value [mg KOH / g] = (561 × V) / (W × S) (where W represents the weighed amount of the dispersant sample [g], V represents the titration amount at the titration endpoint [mL], and S represents the solids concentration of the dispersant sample [% by mass].)

[0096] The weight-average molecular weight (Mw) of the acrylic dispersant is not particularly limited, but is preferably 1,000 or more, more preferably 3,000 or more, even more preferably 4,000 or more, and particularly preferably 5,000 or more. It is also preferably 50,000 or less, more preferably 20,000 or less, and even more preferably 15,000 or less. The above upper and lower limits can be combined arbitrarily. For example, it is preferably 1,000 to 50,000, more preferably 3,000 to 50,000, even more preferably 4,000 to 20,000, and particularly preferably 5,000 to 15,000. Setting it to equal to or greater than the lower limit tends to improve dispersibility, while setting it to equal to or less than the upper limit tends to reduce viscosity changes.

[0097] The acrylic dispersant preferably has a tertiary amino group and / or a quaternary ammonium group.

[0098] When the 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, it is preferable that the acrylic dispersant has a repeating unit represented by the following general formula (V) (hereinafter, sometimes referred to as "repeating unit (V)"):

[0099]

[0100] In formula (V), R 31 ~R 33 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group, and R 31 ~R 33 Two or more of R may be bonded to each other to form a cyclic structure. 34 is a hydrogen atom or a methyl group; X is a divalent linking group; Y - is the counteranion.

[0101] R in formula (V) 31 ~R 33The alkyl group, which may have a substituent, in the formula (I) may be either linear or branched. It may also have a cyclic structure, such as a cyclohexyl group or a cyclohexylmethyl group. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 or more, and is preferably 10 or less, more preferably 6 or less, even more preferably 4 or less, and particularly preferably 2 or less. For example, 1 to 10 carbon atoms are preferred, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 to 2. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. Methyl, ethyl, propyl, butyl, pentyl, and hexyl groups are preferred, methyl, ethyl, propyl, and butyl groups are more preferred, and methyl and ethyl groups are even more preferred.

[0102] R in formula (V) 31 ~R 33 The number of carbon atoms of the aryl group, which may have a substituent, is not particularly limited, but is preferably 6 or more, and is preferably 16 or less, and more preferably 12 or less. For example, 6 to 16 is preferred, and 6 to 12 is more preferred. Examples of the aryl group include a phenyl group, a methylphenyl group, an ethylphenyl group, a dimethylphenyl group, a diethylphenyl group, a naphthyl group, and an anthracenyl group. A phenyl group, a methylphenyl group, an ethylphenyl group, a dimethylphenyl group, and a diethylphenyl group are preferred, and a phenyl group, a methylphenyl group, and an ethylphenyl group are more preferred.

[0103] R in formula (V) 31 ~R 33The number of carbon atoms in the aralkyl group which may have a substituent is not particularly limited, but is preferably 7 or more, and is also preferably 16 or less, more preferably 12 or less, even more preferably 10 or less, and particularly preferably 8 or less. For example, 7 to 16 is preferred, more preferably 7 to 12, even more preferably 7 to 10, and particularly preferably 7 to 8. Examples of the aralkyl group include a phenylmethyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, and a phenylisopropyl group, of which a phenylmethyl group, a phenylethyl group, a phenylpropyl group, and a phenylbutyl group are preferred, and a phenylmethyl group and a phenylethyl group are more preferred.

[0104] From the viewpoint of dispersibility, R 31 ~R 33 are each independently an alkyl group or an aralkyl group, and R 31 ~R 33 are preferably each independently a methyl group or a phenylmethyl group. - Examples of the chlorine atom include Cl. - ,Br - , I - , ClO - , BF4 - , CH3COO - , P.F. - In addition, aromatic dicarboxylic acid imide anions, aromatic sulfonic acid anions, aromatic phosphonic acid anions, and aromatic carboxylic acid anions described in WO 2018 / 079659; and alkyl sulfate anions and alkyl sulfonic acid anions described in WO 2019 / 107020; can also be suitably used. - From the viewpoint of development form, - In terms of light-emitting properties, alkylsulfonate anions are preferred.

[0105] When the polymer dispersant has a tertiary amine as a functional group, from the viewpoint of dispersibility and light-emitting properties, it preferably has a repeating unit represented by the following general formula (VI) (hereinafter, sometimes referred to as "repeating unit (VI)").

[0106]

[0107] In formula (VI), R 35 and R 36 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group, and R 35 and R 36 may be bonded to each other to form a cyclic structure. 37 is a hydrogen atom or a methyl group. Z is a divalent linking group.

[0108] R in formula (VI) 35 and R 36 In the formula (V), the alkyl group which may have a substituent is R 31 ~R 33 The R in formula (VI) can be preferably used. 35 and R 36 The optionally substituted aryl group in formula (V) is R 31 ~R 33 The R in formula (VI) can be preferably used. 35 and R 36 The optionally substituted aralkyl group in the formula (V) is R 31 ~R 33 The examples given below can be preferably used.

[0109] From the viewpoint of dispersibility and luminescence characteristics, R 35 and R 36 are each independently preferably an alkyl group which may have a substituent, and more preferably a methyl group or an ethyl group.

[0110] R in formula (V) 31 ~R 33 and R of formula (VI) 35 and R 36 Examples of the substituent that the alkyl group, aralkyl group or aryl group in the formula (I) may have include a halogen atom, an alkoxy group, a benzoyl group and a hydroxyl group.

[0111] X in formula (V) and Z in formula (VI) are each, for example, an alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 12 carbon atoms, -CONH-R 43 - group, -COOR 44 - group (wherein R 43 and R 44 is a single bond, an alkylene group having 1 to 10 carbon atoms, or an ether group (alkyloxyalkyl group) having 2 to 10 carbon atoms, and preferably —COO—R 44 - group, more preferably -COO-C ２ H ４ From the viewpoint of dispersibility, it is preferable to have the repeating unit (V), and further from the viewpoint of light-emitting properties, it is preferable to have the repeating unit (V) and the repeating unit (VI).

[0112] The content of the repeating unit (V) in the total 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, even more preferably 5 mol% or more, and particularly preferably 8 mol% or more, and is preferably 50 mol% or less, more preferably 30 mol% or less, even more preferably 20 mol% or less, and particularly preferably 15 mol% or less.

[0113] The content 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, even more preferably 15 mol% or more, and particularly preferably 20 mol% or more, and is preferably 60 mol% or less, more preferably 40 mol% or less, even more preferably 30 mol% or less, and particularly preferably 25 mol% or less.

[0114] From the viewpoint of increasing compatibility with alkali-soluble resin components such as solvents and improving dispersion stability, the acrylic dispersant preferably has a repeating unit represented by the following general formula (VII) (hereinafter, sometimes referred to as “repeating unit (VII)”):

[0115]

[0116] In formula (VII), R 40 is an ethylene group or a propylene group, and R41 is an alkyl group which may have a substituent, and R 42 is a hydrogen atom or a methyl group, and n is an integer of 1 to 20.

[0117] R in formula (VII) 41 The alkyl group in the formula (I) may have a substituent and may be either linear or branched. It may also contain a cyclic structure such as a cyclohexyl group or a cyclohexylmethyl group. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. It is also preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. Methyl, ethyl, propyl, butyl, pentyl, and hexyl groups are preferred, and methyl, ethyl, propyl, and butyl groups are more preferred.

[0118] In formula (VII), n is preferably 1 or more, more preferably 2 or more, from the viewpoint of compatibility and dispersibility in an alkali-soluble resin component such as a solvent. Furthermore, n is preferably 10 or less, more preferably 5 or less. The upper and lower limits can be arbitrarily combined. For example, n is preferably 1 to 10, more preferably 2 to 5.

[0119] The content of the repeating unit (VII) in the total 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. It is also 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 arbitrarily combined. 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 above ranges, compatibility with alkali-soluble resin components such as solvents and dispersion stability tend to be compatible.

[0120] From the viewpoint of increasing the compatibility of the dispersant with alkali-soluble resin components such as solvents and improving dispersion stability, the acrylic dispersant preferably has a repeating unit represented by the following general formula (VIII) (hereinafter, sometimes referred to as "repeating unit (VIII)"):

[0121]

[0122] In formula (VIII), R 38 R is an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent. 39 is a hydrogen atom or a methyl group.

[0123] R in formula (VIII) 38 The alkyl group in the formula (I) may have a substituent, and may be either linear or branched. It may also contain a cyclic structure such as a cyclohexyl group or a cyclohexylmethyl group. 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. It is also preferably 10 or less, and more preferably 8 or less. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a 2-ethylhexyl group. A methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a 2-ethylhexyl group are preferred, and a methyl group, an ethyl group, a propyl group, a butyl group, and a 2-ethylhexyl group are more preferred.

[0124] R in formula (VIII) 38In the formula (I), the number of carbon atoms of the aryl group, which may have a substituent, is not particularly limited, but is preferably 6 or more. It is also preferably 16 or less, more preferably 12 or less, and even more preferably 8 or less. For example, 6 to 16 is preferred, 6 to 12 is more preferred, and 6 to 8 is still more preferred. Examples of the aryl group include a phenyl group, a methylphenyl group, an ethylphenyl group, a dimethylphenyl group, a diethylphenyl group, a naphthyl group, and an anthracenyl group. A phenyl group, a methylphenyl group, an ethylphenyl group, a dimethylphenyl group, or a diethylphenyl group is preferred, and a phenyl group, a methylphenyl group, or an ethylphenyl group is more preferred.

[0125] R in formula (VIII) 38 The number of carbon atoms in the aralkyl group which may have a substituent is not particularly limited, but is preferably 7 or more, and is preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less. For example, 7 to 16 is preferred, 7 to 12 is more preferred, and 7 to 10 is still more preferred. Examples of the aralkyl group include a phenylmethyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, and a phenylisopropyl group. A phenylmethyl group, a phenylethyl group, a phenylpropyl group, or a phenylbutyl group is preferred, and a phenylmethyl group or a phenylethyl group is more preferred.

[0126] From the viewpoint of solvent compatibility and dispersion stability, R 38 is preferably an alkyl group or an aralkyl group, and more preferably a methyl group, an ethyl group, a butyl group, a 2-ethylhexyl group or a phenylmethyl group. 38 In the formula (R), examples of the substituent that the alkyl group may have include a halogen atom and an alkoxy group. Examples of the substituent that the aryl group or aralkyl group may have include a chain alkyl group, a halogen atom, and an alkoxy group. 38 The chain alkyl group represented by the formula (I) includes both straight chain and branched chain alkyl groups.

[0127] From the viewpoint of dispersibility, the content 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. Also, it is preferably 80 mol% or less, more preferably 70 mol% or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 30 to 80 mol%, more preferably 40 to 80 mol%, and even more preferably 50 to 70 mol%.

[0128] The acrylic dispersant may have a repeating unit other than the repeating unit (V), the repeating unit (VI), the repeating unit (VII), and the repeating unit (VIII). Examples of such a repeating unit include a styrene-based monomer such as styrene or α-methylstyrene; a (meth)acrylate-based monomer such as (meth)acrylic acid chloride; a (meth)acrylamide-based monomer such as (meth)acrylamide or N-methylolacrylamide; and a repeating unit derived from a monomer such as vinyl acetate, acrylonitrile, allyl glycidyl ether, crotonate glycidyl ether, or N-methacryloylmorpholine.

[0129] From the viewpoint of further enhancing dispersibility, the acrylic dispersant is preferably a block copolymer having an A block having repeating units (V) and (VI) and a B block having no repeating units (V) and (VI). The block copolymer is preferably an A-B block copolymer or a B-A-B block copolymer. Unexpectedly, by introducing not only a quaternary ammonium group but also a tertiary amino group into the A block, the dispersing ability of the dispersant tends to be significantly improved. Furthermore, it is preferable that the B block has repeating units (VII), and more preferably has repeating units (VIII).

[0130] In the A block, the repeating unit (V) and the repeating unit (VI) may be contained in either a random copolymerization or a block copolymerization form. Furthermore, two or more types of each of the repeating unit (V) and the repeating unit (VI) may be contained in one A block, and in this case, each repeating unit may be contained in the A block in either a random copolymerization or a block copolymerization form.

[0131] The A block may contain repeating units other than the repeating unit (V) and the repeating unit (VI), and examples of such repeating units include the repeating units derived from the above-mentioned (meth)acrylic acid ester monomers. The content of repeating units other than the repeating unit (V) and the repeating unit (VI) in the A block is preferably 0 to 50 mol %, more preferably 0 to 20 mol %, and it is particularly preferred that such repeating units are not contained in the A block.

[0132] The B block may contain repeating units other than the repeating unit (VII) and the repeating unit (VIII). Examples of such repeating units include styrene-based monomers such as styrene and α-methylstyrene; (meth)acrylate-based monomers such as (meth)acrylic acid chloride; (meth)acrylamide-based monomers such as (meth)acrylamide and N-methylolacrylamide; and repeating units derived from monomers such as vinyl acetate, acrylonitrile, allyl glycidyl ether, crotonate glycidyl ether, and N-methacryloylmorpholine. The content of repeating units other than the repeating unit (VII) and the repeating unit (VIII) in the B block is preferably 0 to 50 mol %, more preferably 0 to 20 mol %, and it is particularly preferred that such repeating units are not contained in the B block. These acrylic dispersants may be used alone or in combination of two or more.

[0133] <(C) Alkali-Soluble Resin> The photosensitive color resin composition of the present invention contains (C) an alkali-soluble resin. The (C) alkali-soluble resin contains a resin (C1) having a structural unit represented by the following general formula (1):

[0134]

[0135] In formula (1), R 1 represents a hydrogen atom or a methyl group. 2 each independently represents an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms and has at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid as a substituent. * represents a bond.

[0136] Resin (C1) has high affinity with pigments, and contains methylene groups in its main chain, giving it flexibility that allows it to conform to the pigments, and therefore tends to exhibit high pigment dispersibility. Furthermore, since resin (C1) contains many aromatic rings in its main chain, in the photosensitive colored resin composition, it has high developer resistance during development and high heat resistance during baking, and therefore tends to have a high residual film rate. A high residual film rate tends to prevent decomposition products, by-products, uncured materials, etc. in the composition from remaining on or re-adhering to the electrode (anode). Furthermore, when an organic electroluminescent device is formed using a partition wall obtained by curing the photosensitive colored resin composition, the amount of residue and re-adhesion on the anode is reduced, which reduces deposition in the pixel area, increases the current density when a voltage is applied to the organic electroluminescent device, and tends to improve the brightness of the light-emitting device.

[0137] (R 2 ) R in formula (1) 2 R each independently represents an alkyl group having 1 to 4 carbon atoms. 2 In terms of solvent solubility, the number of carbon atoms in the alkyl group is preferably 1 or more, and preferably 3 or less, and more preferably 2 or less. The alkyl group may be linear or branched. Examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. In terms of dispersibility, a methyl group is preferred.

[0138] (L) L represents an alkylene group having 2 to 6 carbon atoms and has at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid as a substituent. L preferably has 3 or more carbon atoms, more preferably 4 carbon atoms. Also, 5 or less carbon atoms is preferred. For example, it may be 3 to 6, 3 to 5, 4 to 6, or 4 to 5. L has at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid as a substituent, and may be further substituted with a methoxy group or an ethoxy group. Here, "polybasic acid" refers to a polybasic acid listed in the polybasic acid residue described below. Furthermore, "ester group of a hydroxyl group and a polybasic acid" refers to a group in which the hydroxyl group bonded to L forms an ester with a polybasic acid. Of the structural units of formula (1), it is preferable to have a structural unit described in the following general formula (2).

[0139]

[0140] (In formula (2), A represents a hydrogen atom or a polybasic acid residue. R 1 represents a hydrogen atom or a methyl group. 2 Each independently represents an alkyl group having 1 to 4 carbon atoms. * represents a bond.

[0141] (A) In formula (1), A represents a hydrogen atom or a polybasic acid residue. The polybasic acid residue refers to a monovalent or divalent group obtained by removing one or two OH groups from a polybasic acid. Examples of the polybasic acid include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenonetetracarboxylic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid, and biphenyltetracarboxylic acid. Among these, from the viewpoint of dispersion stability, preferred are maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, and biphenyltetracarboxylic acid, and more preferred are phthalic acid, succinic acid, trimellitic acid, and pyromellitic acid. In particular, trimellitic acid is preferred because, when the acid value is the same, the number of hydroxyl groups having high solvent affinity is relatively increased compared to the other basic acid residues.

[0142] (R 1 ) R in formula (1) 1 represents a hydrogen atom or a methyl group. From the viewpoint of curability, a hydrogen atom is preferred.

[0143] (R 2 ) R in formula (1) 2 R each independently represents an alkyl group having 1 to 4 carbon atoms. 2 In terms of solvent solubility, the number of carbon atoms in the alkyl group is preferably 1 or more, and preferably 3 or less, and more preferably 2 or less. The alkyl group may be linear or branched. Examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. In terms of dispersibility, a methyl group is preferred. The partial structure represented by formula (1) contained in resin (C1) may be one type or two or more types, and for example, there may be a mixture of a structure in which A is a hydrogen atom and a structure in which A is a polybasic acid residue.

[0144] Examples of the resin (C1) include structures represented by the following general formulas (C1-1) to (C1-8).

[0145]

[0146]

[0147]

[0148] From the viewpoint of dispersion stability, the resin (C1) is preferably a structure represented by formula (C1-1), formula (C1-3), formula (C1-7) or formula (C1-8).

[0149] The acid value of the resin (C1) is not particularly limited, but is preferably 10 mgKOH / g or more, more preferably 30 mgKOH / g or more, even more preferably 40 mgKOH / g or more, and even more preferably 50 mgKOH / g or more. It is also preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less, even more preferably 100 mgKOH / g or less, and particularly preferably 80 mgKOH / g or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 10 to 200 mgKOH / g, more preferably 30 to 150 mgKOH / g, even more preferably 40 to 100 mgKOH / g, and even more preferably 50 to 80 mgKOH / g. By setting the acid value at or above the lower limit, the developer solubility tends to be improved and the resolution tends to be good. By setting the acid value at or below the upper limit, the residual film ratio tends to be good.

[0150] The method for producing resin (C1) is not particularly limited. For example, resin (C1) can be obtained by adding (meth)acrylic acid to an epoxy resin represented by the following general formula (1-2), and then reacting the resulting mixture with a polybasic acid and / or an anhydride thereof.

[0151]

[0152] R in formula (1-2) 2 and * have the same meaning as in formula (1).

[0153] Examples of the epoxy resin represented by formula (1-2) include the following epoxy resins.

[0154]

[0155] In the above formula, m represents an integer of 2 to 8.

[0156] Known methods can be used to add (meth)acrylic acid to the epoxy resin represented by formula (1-2). For example, the epoxy resin can be reacted with (meth)acrylic acid in the presence of an esterification catalyst at a temperature of 50 to 150°C. Examples of the esterification catalyst that can be used here include tertiary amines such as triethylamine, trimethylamine, benzyldimethylamine, and benzyldiethylamine, and quaternary ammonium salts such as tetramethylammonium chloride, tetraethylammonium chloride, and dodecyltrimethylammonium chloride.

[0157] The polybasic acid and / or anhydride thereof may be the above-mentioned polybasic acid or anhydride thereof. The addition reaction of the polybasic acid and / or anhydride thereof may be carried out by a known method.

[0158] The photosensitive colored resin composition used in the present invention may contain an alkali-soluble resin (C) other than resin (C1). There are no particular limitations on the alkali-soluble resin, as long as it is alkali-soluble. Examples include resins containing carboxyl groups or hydroxyl groups. More specifically, examples include epoxy (meth)acrylate resins, acrylic resins, carboxyl-containing epoxy resins, carboxyl-containing urethane resins, novolac resins, polyvinylphenol resins, and isocyanuric skeleton-containing resins. As alkali-soluble resins (C) other than resin (C1), the following are particularly suitable from the viewpoint of excellent plate-making properties: (C2) epoxy (meth)acrylate resins, (C3) isocyanuric skeleton-containing resins, and (C4) acrylic copolymer resins. These resins can be used alone or in combination of two or more.

[0159] <(C2) Epoxy (meth)acrylate Resin> The (C2) epoxy (meth)acrylate resin in the present invention is an alkali-soluble resin (C) other than resin (C1), and is a resin obtained by reacting an epoxy compound (epoxy resin) with an α,β-unsaturated monocarboxylic acid and / or an α,β-unsaturated monocarboxylic acid ester having a carboxy group in the ester moiety to generate hydroxyl groups, followed by reaction with a compound having two or more substituents reactive with hydroxyl groups, such as a polybasic acid and / or an anhydride thereof. However, this does not include the (C3) isocyanuric skeleton-containing resin described below. The (C2) epoxy (meth)acrylate resin also includes a resin obtained by reacting a compound having two or more substituents reactive with hydroxyl groups with the polybasic acid and / or anhydride thereof prior to reacting the polybasic acid and / or anhydride thereof with the hydroxyl groups, followed by reaction with the polybasic acid and / or anhydride thereof.

[0160] From the viewpoints of film retention, outgassing, and plate-making properties, it is preferable to contain an epoxy (meth)acrylate resin (C2) in addition to the resin (C1) as the alkali-soluble resin.

[0161] Resins obtained by reacting the carboxyl groups of the resin obtained by the above reaction with a compound having a functional group capable of further reacting are also included in (C2) epoxy (meth)acrylate resins. Epoxy (meth)acrylate resins have substantially no epoxy groups in their chemical structure, and are not limited to "(meth)acrylate," but are named as such according to convention because epoxy compounds (epoxy resins) are used as raw materials and "(meth)acrylate" is a typical example.

[0162] As the epoxy (meth)acrylate resin (C2) used in the present invention, the following epoxy (meth)acrylate resin (C2-1) and / or epoxy (meth)acrylate resin (C2-2) (hereinafter sometimes referred to as "carboxy group-containing epoxy (meth)acrylate resin") are preferably used from the viewpoint of developability and reliability. As the epoxy (meth)acrylate resin (C2), those having an aromatic ring in the main chain are more preferably used from the viewpoint of outgassing.

[0163] <Epoxy (meth)acrylate resin (C2-1)> An alkali-soluble resin obtained by adding an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester having a carboxy group to an epoxy resin, and then reacting with a polybasic acid and / or an anhydride thereof. <Epoxy (meth)acrylate resin (C2-2)> An alkali-soluble resin obtained by adding an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester having a carboxy group to an epoxy resin, and then reacting with a polyhydric alcohol and a polybasic acid and / or an anhydride thereof.

[0164] Here, the term "epoxy resin" refers to raw material compounds before they are thermoset to form a resin, and the epoxy resin can be appropriately selected from known epoxy resins. Furthermore, the epoxy resin can be a compound obtained by reacting a phenolic compound with an epihalohydrin. The phenolic compound is preferably a compound having a divalent or higher phenolic hydroxyl group, and may be a monomer or a polymer. Suitable types of epoxy resins used as raw materials include cresol novolac epoxy resins, phenol novolac epoxy resins, bisphenol A epoxy resins, bisphenol F epoxy resins, trisphenolmethane epoxy resins, biphenyl novolac epoxy resins, naphthalene novolac epoxy resins, epoxy resins that are the reaction products of a polyaddition reaction product of dicyclopentadiene with phenol or cresol and epihalohydrin, adamantyl group-containing epoxy resins, and fluorene epoxy resins. Those having an aromatic ring in the main chain are more preferred.

[0165] Examples of epoxy resins include bisphenol A type epoxy resins (e.g., "jER (registered trademark, the same applies hereinafter) 828," "jER1001," "jER1002," and "jER1004" manufactured by Mitsubishi Chemical Corporation), epoxy resins obtained by reacting an alcoholic hydroxyl group of a bisphenol A type epoxy resin with epichlorohydrin (e.g., "NER-1302" manufactured by Nippon Kayaku Co., Ltd. (epoxy equivalent: 323, softening point: 76°C)), and bisphenol F type resins (e.g., "JER-1302" manufactured by Nippon Kayaku Co., Ltd. (epoxy equivalent: 323, softening point: 76°C)). "jER807", "EP-4001", "EP-4002", "EP-4004" manufactured by Mitsubishi Chemical Co., Ltd., etc.), epoxy resins obtained by reacting the alcoholic hydroxyl group of bisphenol F type epoxy resin with epichlorohydrin (for example, "NER-7406" manufactured by Nippon Kayaku Co., Ltd. (epoxy equivalent: 350, softening point: 66°C)), bisphenol S type epoxy resin, biphenyl glycidyl ether (for example, "YX-4000" manufactured by Mitsubishi Chemical Co., Ltd.), phenol novolac type epoxy resin epoxy resins (for example, "EPPN-201" manufactured by Nippon Kayaku Co., Ltd., "EP-152" and "EP-154" manufactured by Mitsubishi Chemical Corporation, and "DEN-438" manufactured by Dow Chemical Company), (o-, m-, p-)cresol novolac epoxy resins (for example, "EOCN (registered trademark, the same applies hereinafter)-102S," "EOCN-1020," and "EOCN-104S" manufactured by Nippon Kayaku Co., Ltd.), trisphenolmethane epoxy resins (for example, "EPPN (registered trademark, the same applies hereinafter)-50" manufactured by Nippon Kayaku Co., Ltd.), 1," "EPPN-502," and "EPPN-503"), alicyclic epoxy resins (Daicel Corporation's "CELLOXIDE (registered trademark, the same applies hereinafter) 2021P" and "CELLOXIDE EHPE"), epoxy resins obtained by glycidylating phenolic resins obtained by reacting dicyclopentadiene with phenol (for example, DIC Corporation's "EXA-7200," Nippon Kayaku Co., Ltd.'s "NC-7300"), and epoxy resins represented by the following general formulas (C2α) to (C2δ) can be suitably used.Specific examples include "XD-1000" manufactured by Nippon Kayaku Co., Ltd. as an epoxy resin represented by the following general formula (C2α), "NC-3000" and "NC-3500" manufactured by Nippon Kayaku Co., Ltd. as epoxy resins represented by the following general formula (C2β), "E-201" manufactured by Osaka Organic Chemical Industry Ltd. as an epoxy resin represented by the following general formula (C2γ), and "ESF-300" manufactured by Nippon Steel & Sumikin Chemical Co., Ltd. as an epoxy resin represented by the following general formula (C2δ).

[0166]

[0167] In formula (C2α), a is an average value and represents a number from 0 to 10; 111 Each of R independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group, a naphthyl group, or a biphenyl group. 111 may be the same or different.

[0168]

[0169] In formula (C2β), b1 and b2 are average values, each independently representing a number from 0 to 10; 121 Each of R independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group, a naphthyl group, or a biphenyl group. 121 may be the same or different.

[0170]

[0171] In formula (C2γ), X represents a linking group represented by the following general formula (C2γ-1) or (C2γ-2), provided that the molecular structure contains one or more adamantane structures. c represents 2 or 3.

[0172]

[0173] In formulas (C2γ-1) and (C2γ-2), R 131 ~R 134 and R 135 ~R 137each independently represents an adamantyl group which may have a substituent, a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or a phenyl group which may have a substituent, and * represents a bond.

[0174]

[0175] In formula (C2δ), p and q each independently represent an integer of 0 to 4; 141 and R 142 each independently represents an alkyl group having 1 to 4 carbon atoms or a halogen atom; R 143 and R 144 each independently represents an alkylene group having 1 to 4 carbon atoms, and x and y each independently represent an integer of 0 or greater.

[0176] As the epoxy resin, it is preferable to use an epoxy resin represented by any one of formulas (C2α) to (C2δ).

[0177] Examples of α,β-unsaturated monocarboxylic acids or α,β-unsaturated monocarboxylic acid esters having a carboxy group include monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-, m- or p-vinylbenzoic acid, and (meth)acrylic acid substituted with haloalkyl, alkoxyl, halogen, nitro, or cyano at the α-position; 2-(meth)acryloyloxyethyl succinic acid, 2-(meth)acryloyloxyethyl adipate, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxyethyl maleate, 2-(meth)acryloyloxypropyl succinic acid, 2-(meth)acryloyloxypropyl adipate, 2-(meth)acryloyloxypropyl tetrahydrophthalate, 2-(meth)acryloyloxyethyl methyl esters. Examples of suitable monomers include 2-(meth)acryloyloxypropyl phthalate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxybutyl succinate, 2-(meth)acryloyloxybutyl adipic acid, 2-(meth)acryloyloxybutyl hydrophthalate, 2-(meth)acryloyloxybutyl phthalate, and 2-(meth)acryloyloxybutyl maleate; monomers obtained by adding lactones such as ε-caprolactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone to (meth)acrylic acid; monomers obtained by adding acids (anhydrides) such as succinic acid anhydride, phthalic acid anhydride, and maleic acid anhydride to hydroxyalkyl (meth)acrylate or pentaerythritol tri(meth)acrylate; and (meth)acrylic acid dimers. From the viewpoint of sensitivity, (meth)acrylic acid is preferred.

[0178] Known methods can be used to add an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester having a carboxy group to an epoxy resin. For example, an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester having a carboxy group can be reacted with an epoxy resin in the presence of an esterification catalyst at a temperature of 50 to 150° C. Examples of esterification catalysts that can be used here include tertiary amines such as triethylamine, trimethylamine, benzyldimethylamine, and benzyldiethylamine, and quaternary ammonium salts such as tetramethylammonium chloride, tetraethylammonium chloride, and dodecyltrimethylammonium chloride.

[0179] The epoxy resin, the α,β-unsaturated monocarboxylic acid or the α,β-unsaturated monocarboxylic acid ester having a carboxy group, and the esterification catalyst may each be used singly or in combination of two or more. The amount of the α,β-unsaturated monocarboxylic acid or the α,β-unsaturated monocarboxylic acid ester having a carboxy group used is preferably 0.5 to 1.2 equivalents, more preferably 0.7 to 1.1 equivalents, per equivalent of the epoxy group in the epoxy resin. By using an amount of the α,β-unsaturated monocarboxylic acid or the α,β-unsaturated monocarboxylic acid ester having a carboxy group that is equal to or greater than the lower limit, the introduction of an insufficient amount of unsaturated groups can be prevented, and the subsequent reaction with the polybasic acid and / or its anhydride tends to be sufficient. By using an amount equal to or less than the upper limit, the amount of unreacted α,β-unsaturated monocarboxylic acid or the α,β-unsaturated monocarboxylic acid ester having a carboxy group can be prevented, and good curing properties tend to be obtained.

[0180] Examples of polybasic acids and / or anhydrides thereof include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenonetetracarboxylic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid, biphenyltetracarboxylic acid, and anhydrides thereof.

[0181] Preferred are maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, biphenyltetracarboxylic acid, and anhydrides thereof, and particularly preferred are tetrahydrophthalic acid, biphenyltetracarboxylic acid, and anhydrides thereof.

[0182] The addition reaction of a polybasic acid and / or anhydride thereof can be carried out using known techniques, and the target product can be obtained by continuing the reaction under conditions similar to those of the addition reaction of an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester having a carboxy group to an epoxy resin. The amount of polybasic acid and / or anhydride thereof added is preferably such that the acid value of the resulting carboxy-containing epoxy (meth)acrylate resin is 10 to 150 mgKOH / g, more preferably 20 to 140 mgKOH / g. By adjusting the amount to be equal to or greater than the lower limit, alkaline developability tends to be improved. By adjusting the amount to be equal to or less than the upper limit, curing performance tends to be improved.

[0183] During the addition reaction of the polybasic acid and / or its anhydride, a polyfunctional alcohol (polyhydric alcohol) such as trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, trimethylolethane, or 1,2,3-propanetriol may be added to introduce a multi-branched structure. In this case, there are no particular restrictions on the order of mixing the polybasic acid and / or its anhydride with the polyfunctional alcohol. By heating, the polybasic acid and / or its anhydride undergoes an addition reaction with any hydroxyl group present in the mixture of the reaction product of the epoxy resin with an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester having a carboxy group and the polyfunctional alcohol.

[0184] The use of a polyhydric alcohol increases the molecular weight of the epoxy (meth)acrylate resin (C2), allows branching to be introduced into the molecule, and tends to balance the molecular weight and viscosity. In addition, the introduction rate of acid groups into the molecule can be increased, which tends to make it easier to balance sensitivity, adhesion, and the like.

[0185] In addition to the above-mentioned carboxyl group-containing epoxy (meth)acrylate resins, for example, those described in Korean Patent Publication No. 10-2013-0022955 can be mentioned.

[0186] The weight average molecular weight (Mw) of the carboxyl group-containing epoxy (meth)acrylate resin, measured by gel permeation chromatography (GPC) in terms of polystyrene, is preferably 1,000 or more, more preferably 1,500 or more, even more preferably 2,000 or more, even more preferably 3,000 or more, particularly preferably 4,000 or more, and particularly preferably 5,000 or more. It is also preferably 30,000 or less, more preferably 20,000 or less, and even more preferably 15,000 or less. The above upper and lower limits can be arbitrarily combined. For example, 1,000 to 30,000 is preferred, 1,500 to 20,000 is more preferred, 1,500 to 15,000 is even more preferred, and 2,000 to 15,000 is even more preferred. Setting the Mw at or above the lower limit tends to prevent excessive solubility in the developer. Setting the Mw at or below the upper limit tends to facilitate good solubility in the developer.

[0187] The acid value of the carboxyl group-containing epoxy (meth)acrylate resin is not particularly limited, but is preferably 20 mgKOH / g or more, more preferably 40 mgKOH / g or more, even more preferably 60 mgKOH / g or more, even more preferably 80 mgKOH / g or more, and particularly preferably 100 mgKOH / g or more. Also, it is preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less, even more preferably 130 mgKOH / g or less, and particularly preferably 120 mgKOH / g or less. The above upper and lower limits can be arbitrarily combined. For example, 20 to 200 mgKOH / g is preferred, 60 to 150 mgKOH / g is more preferred, 80 to 130 mgKOH / g is even more preferred, and 100 to 130 mgKOH / g is even more preferred. Setting the acid value at or above the lower limit tends to improve development solubility and improve resolution. Setting the acid value at or below the upper limit tends to improve the residual film rate of the photosensitive colored resin composition.

[0188] The chemical structure of the (C2) epoxy(meth)acrylate resin is not particularly limited, but from the viewpoint of developability and reliability, it is preferable for the resin to contain an epoxy(meth)acrylate resin having a partial structure represented by the following general formula (C2-I) (hereinafter may be abbreviated as "(C2-I) epoxy(meth)acrylate resin") and / or an epoxy(meth)acrylate resin having a partial structure represented by the following general formula (C2-II) (hereinafter may be abbreviated as "(C2-II) epoxy(meth)acrylate resin"):

[0189]

[0190] In formula (C2-I), R 11 represents a hydrogen atom or a methyl group, R 12 represents a divalent hydrocarbon group which may have a substituent, k represents 1 or 2, and * represents a bond. The benzene ring in formula (C2-I) may be further substituted with any substituent.

[0191]

[0192] In formula (C2-II), R 13 each independently represents a hydrogen atom or a methyl group; R 14 represents a divalent hydrocarbon group having a cyclic hydrocarbon group as a side chain, and R 15 and R 16 each independently represents a divalent aliphatic group which may have a substituent, m and n each independently represents an integer of 0 to 2, and * represents a bond.

[0193] <(C2-I) Epoxy (meth)acrylate resin>

[0194]

[0195] In formula (C2-I), R 11 represents a hydrogen atom or a methyl group, R 12 represents a divalent hydrocarbon group which may have a substituent, k represents 1 or 2, and * represents a bond. The benzene ring in formula (C2-I) may be further substituted with any substituent.

[0196] (R 12In formula (C2-I), R 12 represents a divalent hydrocarbon group which may have a substituent. Examples of the divalent hydrocarbon group include a divalent aliphatic group, a divalent aromatic ring group, and a group in which one or more divalent aliphatic groups are linked to one or more divalent aromatic ring groups.

[0197] Examples of the divalent aliphatic group include linear, branched, and cyclic aliphatic groups. From the viewpoint of development solubility, linear aliphatic groups are preferred. On the other hand, from the viewpoint of reducing penetration of the developer 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. It is also preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The above upper and lower limits can be arbitrarily combined. For example, 1 to 20 is preferred, 1 to 15 is more preferred, and 1 to 10 is even more preferred. By setting the carbon number at or above the lower limit, a strong film is more likely to be obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the carbon number at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high and resolution tends to be improved.

[0198] 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, a methylene group is preferred. Examples of divalent branched aliphatic groups include structures in which the aforementioned linear divalent aliphatic groups have, as side chains, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl groups. 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. Also, 12 or less is preferred, and 10 or less is more preferred. The above upper and lower limits can be arbitrarily combined. For example, 1 to 12 is preferred, 1 to 10 is more preferred, and 2 to 10 is even more preferred. By setting the number at or above the lower limit, a strong film tends to be formed, and substrate adhesion tends to be improved. By setting it to the upper limit or less, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high and resolution tends to be improved. Examples of the divalent cyclic aliphatic group include groups obtained by removing two hydrogen atoms from a ring such as a cyclohexane ring, a cycloheptane ring, a cyclodecane ring, a cyclododecane ring, a norbornane ring, an isobornane ring, an adamantane ring, a dicyclopentadiene ring, or a dicyclopentane ring. From the viewpoint of the rigidity of the skeleton, groups obtained by removing two hydrogen atoms from a dicyclopentadiene ring, a dicyclopentane ring, or an adamantane ring are preferred.

[0199] Examples of the substituent that the divalent aliphatic group may have include an alkoxy group having 1 to 5 carbon atoms, such as a methoxy group or an ethoxy group; a hydroxyl group; a nitro group; a cyano group; and a carboxy group. From the viewpoint of ease of synthesis, it is preferable that the divalent aliphatic group is unsubstituted.

[0200] Examples of divalent aromatic ring groups include divalent aromatic hydrocarbon ring 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. It is also preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The above upper and lower limits can be arbitrarily combined. For example, 4 to 20 is preferred, 5 to 15 is more preferred, and 6 to 10 is even more preferred. By setting the number at or above the lower limit, a strong film is more likely to be obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the number at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high, and resolution tends to be improved.

[0201] The aromatic hydrocarbon ring in the divalent aromatic hydrocarbon ring group may be a single ring or a condensed ring. Examples of the divalent aromatic hydrocarbon ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring, each of which has two free valences. The aromatic heterocyclic ring in the divalent aromatic heterocyclic group may be a single ring or a condensed ring. Examples of divalent aromatic heterocyclic groups include furan rings, benzofuran rings, thiophene rings, benzothiophene rings, pyrrole rings, pyrazole rings, imidazole rings, oxadiazole rings, indole rings, carbazole rings, pyrroloimidazole rings, pyrrolopyrazole rings, pyrrolopyrrole rings, thienopyrrole rings, thienothiophene rings, furopyrrole rings, furofuran rings, thienofuran rings, benzisoxazole rings, benzisothiazole rings, benzimidazole rings, pyridine rings, pyrazine rings, pyridazine rings, pyrimidine rings, triazine rings, quinoline rings, isoquinoline rings, cinnoline rings, quinoxaline rings, phenanthridine rings, perimidine rings, quinazoline rings, quinazolinone rings, and azulene rings, each having two free valences. From the viewpoint of patterning properties, a benzene ring or naphthalene ring having two free valences is preferred, and a benzene ring having two free valences is more preferred.

[0202] Examples of the substituent that the divalent aromatic ring group may have include a hydroxy group, a methyl group, a methoxy group, an ethyl group, an ethoxy group, a propyl group, and a propoxy group. From the viewpoint of solubility in development, it is preferably unsubstituted.

[0203] Examples of the group linking one or more divalent aliphatic groups and one or more divalent aromatic ring groups include a group linking one or more of the aforementioned divalent aliphatic groups with one or more of the aforementioned divalent aromatic ring groups. The number of divalent aliphatic groups is not particularly limited, but is preferably one or more, more preferably two or more, and is preferably 10 or less, more preferably five or less, and even more preferably three or less. The above upper and lower limits can be arbitrarily combined. For example, 1 to 10 is preferred, 1 to 5 is more preferred, 1 to 3 is even more preferred, and 2 to 3 is particularly preferred. By setting the number at or above the lower limit, a strong film tends to be easily obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the number at or below the upper limit, deterioration of sensitivity can be suppressed, and the remaining film rate after development tends to be high, and resolution tends to be improved. The number of divalent aromatic ring groups is not particularly limited, but is preferably one or more, more preferably two or more, and is preferably 10 or less, more preferably five or less, and even more preferably three or less. The above upper and lower limits can be arbitrarily combined. For example, 1 to 10 is preferred, 1 to 5 is more preferred, 1 to 3 is even more preferred, and 2 to 3 is particularly preferred. By setting the content at or above the lower limit, a strong film is easily obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the content at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high, and resolution tends to be improved.

[0204] Examples of the group formed by linking one or more divalent aliphatic groups with one or more divalent aromatic ring groups include groups represented by the following formulae (C2-IA) to (C2-IF). In the following formulae (C2-IA) to (C2-IF), * represents a bond. From the viewpoints of skeleton rigidity and film hydrophobicity, the group represented by the following formula (C2-IA) is preferred.

[0205]

[0206] In formula (C2-I), k represents 1 or 2. From the viewpoints of adhesion and plate-making properties, k is preferably 1. From the viewpoint of sensitivity, k is preferably 2. Furthermore, the epoxy (meth)acrylate (C2-I) may contain both a partial structure where k is 1 and a partial structure where k is 2.

[0207] The benzene ring in formula (C2-I) may be further substituted with any substituent. Examples of the substituent include a hydroxy group, a methyl group, a methoxy group, an ethyl group, an ethoxy group, a propyl group, and a propoxy group. The number of substituents is not particularly limited, and may be one or two or more. From the viewpoint of plate-making properties, it is preferably unsubstituted.

[0208] From the viewpoint of ease of synthesis, the partial structure represented by formula (C2-I) is preferably a partial structure represented by the following general formula (C2-I-1).

[0209]

[0210] In formula (C2-I-1), R 11 , R 12 and k have the same meaning as in formula (C2-I), and R X represents a hydrogen atom or a polybasic acid residue, and * represents a bond. The benzene ring in formula (C2-I-1) may be further substituted with any substituent.

[0211] The 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, benzophenonetetracarboxylic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid, and biphenyltetracarboxylic acid. From the viewpoint of patterning properties, preferred are maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, and biphenyltetracarboxylic acid, and more preferred are tetrahydrophthalic acid, biphenyltetracarboxylic acid, and biphenyltetracarboxylic acid.

[0212] The benzene ring in formula (C2-I-1) may be further substituted with any substituent. As the substituent, those exemplified for the benzene ring in formula (C2-I) can be preferably used.

[0213] (C2-I) The partial structure represented by formula (C2-I-1) contained in one molecule of the epoxy (meth)acrylate resin may be one type or two or more types, and for example, R X is a hydrogen atom, and R X However, polybasic acid residues may be present in the mixture.

[0214] The number of partial structures represented by formula (C2-I) contained in one molecule of the epoxy (meth)acrylate resin (C2-I) is not particularly limited, but is preferably 1 or more, more preferably 3 or more. It is also preferably 20 or less, and even more preferably 15 or less. The above upper and lower limits can be arbitrarily combined. 1 to 20 is preferred, 1 to 15 is more preferred, and 3 to 15 is even more preferred. By making the number equal to or greater than the lower limit, a strong film tends to be easily obtained, and surface roughness that occurs during development tends to be less likely to occur. By making the number equal to or less than the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high, and resolution tends to be improved.

[0215] The weight average molecular weight (Mw) of the epoxy (meth)acrylate resin (C2-I) measured by gel permeation chromatography (GPC) in terms of polystyrene is not particularly limited, but is preferably 1,000 or more, more preferably 1,500 or more, even more preferably 2,000 or more, even more preferably 3,000 or more, particularly preferably 4,000 or more, and most preferably 5,000 or more. It is also preferably 30,000 or less, more preferably 20,000 or less, and even more preferably 15,000 or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 1,000 to 30,000, more preferably 1,500 to 2,000, even more preferably 1,500 to 15,000, and even more preferably 2,000 to 1,500. By setting it to the lower limit or higher, the film remaining rate of the photosensitive color resin composition tends to be good. By setting it to the upper limit or lower, the solubility in the developer tends to be good.

[0216] The acid value of the epoxy (meth)acrylate resin (C2-I) is not particularly limited, but is preferably 20 mgKOH / g or more, more preferably 40 mgKOH / g or more, even more preferably 60 mgKOH / g or more, even more preferably 80 mgKOH / g or more, and particularly preferably 100 mgKOH / g or more. Also, it is preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less, even more preferably 130 mgKOH / g or less, and particularly preferably 120 mgKOH / g or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 20 to 200 mgKOH / g, more preferably 60 to 150 mgKOH / g, even more preferably 80 to 130 mgKOH / g, and even more preferably 100 to 130 mgKOH / g. By ensuring that the acid value is equal to or greater than the lower limit, the developer solubility is improved, and the resolution tends to be favorable. By making the content equal to or less than the upper limit, the remaining film rate of the photosensitive color resin composition tends to be good.

[0217] Specific examples of (C2-I) epoxy (meth)acrylate resins are listed below. In the examples, * indicates a bond.

[0218]

[0219]

[0220]

[0221]

[0222] <(C2-II) Epoxy (meth)acrylate resin>

[0223]

[0224] In formula (C2-II), R 13 each independently represents a hydrogen atom or a methyl group; R 14 represents a divalent hydrocarbon group having a cyclic hydrocarbon group as a side chain, and R 15 and R 16 each independently represents a divalent aliphatic group which may have a substituent, m and n each independently represents an integer of 0 to 2, and * represents a bond.

[0225] The structure of formula (C2-II) is preferable in terms of light-emitting properties.

[0226] (R 14 In formula (C2-II), R 14 represents a divalent hydrocarbon group having a cyclic hydrocarbon group as a side chain. Examples of the cyclic hydrocarbon group include an aliphatic cyclic group and an aromatic cyclic group.

[0227] The number of rings in the aliphatic cyclic group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. It is also preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. The upper and lower limits above can be combined arbitrarily. For example, 1 to 10 is preferred, 1 to 5 is more preferred, 1 to 3 is even more preferred, and 2 to 3 is particularly preferred. By setting the number at or above the lower limit, a strong film tends to be easily obtained, and surface roughness during development tends to be less likely to occur. By setting the number at or below the upper limit, deterioration in sensitivity can be suppressed, and the residual film rate after development tends to be high, and resolution tends to be improved.

[0228] The number of carbon atoms in the aliphatic cyclic group is not particularly limited, but is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. It is also 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 arbitrarily combined. For example, 4 to 40 is preferred, 4 to 30 is more preferred, 6 to 20 is even more preferred, and 8 to 15 is particularly preferred. By setting the number of carbon atoms at or above the lower limit, a strong film tends to be easily obtained, and surface roughness during development tends to be less likely to occur. By setting the number of carbon atoms at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high, and resolution tends to be improved. Examples of the aliphatic ring in the aliphatic cyclic group include a cyclohexane ring, a cycloheptane ring, a cyclodecane ring, a cyclododecane ring, a norbornane ring, an isobornane ring, and an adamantane ring. From the viewpoint of the residual film rate and resolution of the photosensitive color resin composition, an adamantane ring is preferred.

[0229] 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. It is also 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 in any combination. For example, 1 to 10 is preferred, 1 to 5 is more preferred, 1 to 4 is even more preferred, 2 to 4 is even more preferred, and 3 to 4 is particularly preferred. By setting the number at or above the lower limit, a strong film tends to be obtained, and surface roughness that occurs during development tends to be less likely to occur. By setting the number at or below the upper limit, deterioration of sensitivity can be suppressed, the residual film rate after development tends to be high, and resolution tends to be improved. Examples of aromatic ring groups include aromatic hydrocarbon ring groups and aromatic heterocyclic groups. The number of carbon atoms in the aromatic ring group is not particularly limited, but is preferably 4 or more, more preferably 6 or more, even more preferably 8 or more, even more preferably 10 or more, and particularly preferably 12 or more. It is also 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 in any combination. For example, 4 to 40 is preferred, 6 to 40 is more preferred, 8 to 30 is even more preferred, 10 to 20 is even more preferred, and 12 to 15 is particularly preferred. By setting the value at or above the lower limit, a strong film is more likely to be obtained, and surface roughness during development tends to be less likely to occur. By setting the value at or below the upper limit, patterning properties tend to be improved. Examples of aromatic rings in the aromatic ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring. From the viewpoint of patterning properties, a fluorene ring is preferred.

[0230] The divalent hydrocarbon group in the divalent hydrocarbon group having a cyclic hydrocarbon group as a side chain is not particularly limited, and examples thereof include a divalent aliphatic group, a divalent aromatic ring group, and a group in which one or more divalent aliphatic groups are linked to one or more divalent aromatic ring groups.

[0231] Examples of the divalent aliphatic group include linear, branched, and cyclic aliphatic groups. From the viewpoint of development solubility, linear aliphatic groups are preferred, while cyclic aliphatic groups are preferred from the viewpoint of reducing penetration of the developer into the exposed area. 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. Also, 25 or less is preferred, more preferably 20 or less, and even more preferably 15 or less. The above upper and lower limits can be arbitrarily combined. For example, 1 to 25 is preferred, 3 to 20 is more preferred, and 6 to 15 is even more preferred. By setting the carbon atom number at or above the lower limit, a strong film is more likely to be obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the carbon atom number at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high and resolution tends to be improved.

[0232] 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, a methylene group is preferred. Examples of divalent branched aliphatic groups include structures in which the aforementioned linear divalent aliphatic groups have a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, or tert-butyl group as a side chain. 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. Also, 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 arbitrarily combined. For example, 1 to 10 is preferred, 1 to 5 is more preferred, 1 to 3 is even more preferred, and 2 to 3 is particularly preferred. By setting the content to be equal to or greater than the lower limit, a strong film is formed, and the substrate adhesion tends to be good. Furthermore, by setting the content to be equal to or less than the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high, and the resolution tends to be improved. Examples of divalent cyclic aliphatic groups include groups in which two hydrogen atoms have been removed from a cyclohexane ring, a cycloheptane ring, a cyclodecane ring, a cyclododecane ring, a norbornane ring, an isobornane ring, and an adamantane ring. From the viewpoint of the rigidity of the skeleton, a group in which two hydrogen atoms have been removed from an adamantane ring is preferred.

[0233] Examples of the substituent that the divalent aliphatic group may have include an alkoxy group having 1 to 5 carbon atoms, such as a methoxy group or an ethoxy group; a hydroxyl group; a nitro group; a cyano group; and a carboxy group. From the viewpoint of ease of synthesis, it is preferable that the divalent aliphatic group is unsubstituted.

[0234] Examples of divalent aromatic ring groups include divalent aromatic hydrocarbon ring 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. It is also preferably 30 or less, more preferably 20 or less, and even more preferably 15 or less. The above upper and lower limits can be arbitrarily combined. For example, 4 to 30 is preferred, 5 to 20 is more preferred, and 6 to 15 is even more preferred. By setting the number at or above the lower limit, a strong film is more likely to be obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the number at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high, and resolution tends to be improved.

[0235] The aromatic hydrocarbon ring in the divalent aromatic hydrocarbon ring group may be a single ring or a condensed ring. Examples of the divalent aromatic hydrocarbon ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring, each of which has two free valences. The aromatic heterocyclic ring in the divalent aromatic heterocyclic group may be a single ring or a condensed ring. Examples of divalent aromatic heterocyclic groups include furan rings, benzofuran rings, thiophene rings, benzothiophene rings, pyrrole rings, pyrazole rings, imidazole rings, oxadiazole rings, indole rings, carbazole rings, pyrroloimidazole rings, pyrrolopyrazole rings, pyrrolopyrrole rings, thienopyrrole rings, thienothiophene rings, furopyrrole rings, furofuran rings, thienofuran rings, benzisoxazole rings, benzisothiazole rings, benzimidazole rings, pyridine rings, pyrazine rings, pyridazine rings, pyrimidine rings, triazine rings, quinoline rings, isoquinoline rings, cinnoline rings, quinoxaline rings, phenanthridine rings, perimidine rings, quinazoline rings, quinazolinone rings, and azulene rings, each having two free valences. From the viewpoint of patterning properties, a benzene ring or naphthalene ring having two free valences is preferred, and a benzene ring having two free valences is more preferred.

[0236] Examples of the substituent that the divalent aromatic ring group may have include a hydroxy group, a methyl group, a methoxy group, an ethyl group, an ethoxy group, a propyl group, and a propoxy group. From the viewpoint of solubility in development, it is preferably unsubstituted.

[0237] Examples of the group linking one or more divalent aliphatic groups and one or more divalent aromatic ring groups include a group linking one or more of the aforementioned divalent aliphatic groups with one or more of the aforementioned divalent aromatic ring groups. The number of divalent aliphatic groups is not particularly limited, but is preferably one or more, more preferably two 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, 1 to 5 is more preferred, 1 to 3 is even more preferred, and 2 to 3 is particularly preferred. By setting the number at or above the lower limit, a strong film tends to be easily obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the number at or below the upper limit, deterioration of sensitivity can be suppressed, and the remaining film rate after development tends to be high, and resolution tends to be improved. The number of divalent aromatic ring groups is not particularly limited, but is preferably one or more, more preferably two 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, 1 to 5 is more preferred, 1 to 3 is even more preferred, and 2 to 3 is particularly preferred. By setting the content at or above the lower limit, a strong film is easily obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the content at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high, and resolution tends to be improved.

[0238] Examples of the group formed by linking one or more divalent aliphatic groups with one or more divalent aromatic ring groups include the groups represented by the above-mentioned formulas (C2-IA) to (C2-IF). From the viewpoints of the rigidity of the skeleton and the hydrophobicity of the film, the group represented by formula (C2-IC) is preferred.

[0239] The bonding mode of the cyclic hydrocarbon group as a side chain to these divalent hydrocarbon groups is not particularly limited, but examples include a mode in which one hydrogen atom of an aliphatic group or aromatic ring group is substituted with the cyclic hydrocarbon group as a side chain, and a mode in which one carbon atom of an aliphatic group is included to form the cyclic hydrocarbon group as a side chain.

[0240] (R 15 , R 16 In formula (C2-II), R 15 and R16 each independently represents a divalent aliphatic group which may have a substituent.

[0241] Examples of the divalent aliphatic group include linear, branched, and cyclic aliphatic groups. From the viewpoint of development solubility, linear aliphatic groups are preferred, while cyclic aliphatic groups are preferred from the viewpoint of reducing penetration of the developer into the exposed area. 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. Also, 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 arbitrarily combined. For example, 1 to 20 is preferred, more preferably 3 to 15, and even more preferably 6 to 10. By setting the carbon atom number at or above the lower limit, a strong film is easily obtained, surface roughness during development is less likely to occur, and adhesion to the substrate tends to be good. By setting the carbon atom number at or below the upper limit, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high and resolution tends to be improved.

[0242] 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, a methylene group is preferred. Examples of divalent branched aliphatic groups include structures in which the aforementioned divalent linear aliphatic groups have, as side chains, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl groups. 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 arbitrarily combined. For example, 1 to 12 is preferred, and 2 to 10 is more preferred. By setting the number at or above the lower limit, a strong film tends to be formed, and substrate adhesion tends to be improved. By setting it to the upper limit or less, deterioration of sensitivity can be suppressed, and the residual film rate after development tends to be high and resolution tends to be improved. Examples of the divalent cyclic aliphatic group include groups obtained by removing two hydrogen atoms from a cyclohexane ring, a cycloheptane ring, a cyclodecane ring, a cyclododecane ring, a norbornane ring, an isobornane ring, an adamantane ring, and a dicyclopentadiene ring. From the viewpoint of skeleton rigidity, groups obtained by removing two hydrogen atoms from a dicyclopentadiene ring and an adamantane ring are preferred.

[0243] Examples of the substituent that the divalent aliphatic group may have include an alkoxy group having 1 to 5 carbon atoms, such as a methoxy group or an ethoxy group; a hydroxyl group; a nitro group; a cyano group; and a carboxy group. From the viewpoint of ease of synthesis, it is preferable that the divalent aliphatic group is unsubstituted.

[0244] (m, n) In formula (C2-II), m and n each independently represent an integer of 0 to 2. By making m or n equal to or greater than the lower limit, patterning suitability becomes good and surface roughness that occurs during development tends to be less likely to occur, while by making m or n equal to or less than the upper limit, developability tends to be good. From the viewpoint of developability, m and n are preferably 0. From the viewpoint of patterning suitability and suppressing surface roughness that occurs during development, m and n are preferably 1 or greater.

[0245] The partial structure represented by formula (C2-II) is preferably a partial structure represented by the following general formula (C2-II-1) from the viewpoint of adhesion to a substrate.

[0246]

[0247] In formula (C2-II-1), R 13 , R 15 , R 16 , m and n are defined as in formula (C2-II), and R α represents a monovalent cyclic hydrocarbon group which may have a substituent, p represents an integer of 1 or greater, and * represents a bond. The benzene ring in formula (C2-II-1) may be further substituted with any substituent.

[0248] (R α In formula (C2-II-1), R α represents a monovalent cyclic hydrocarbon group which may have a substituent. Examples of the cyclic hydrocarbon group include an aliphatic cyclic group and an aromatic cyclic group.

[0249] The number of rings in the aliphatic cyclic group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. It is also 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 in any combination. For example, 1 to 6 is preferred, 1 to 4 is more preferred, 1 to 3 is even more preferred, and 2 to 3 is particularly preferred. By setting the number at or above the lower limit, a strong film tends to be easily obtained, and surface roughness that occurs during development tends to be less likely to occur. By setting the number at or below the upper limit, patterning characteristics tend to be improved. The number of carbon atoms in the aliphatic cyclic group is not particularly limited, but is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. It is also preferably 40 or less, more preferably 30 or less, even more preferably 20 or less, and especially preferably 15 or less. The above upper and lower limits can be combined in any combination. For example, 4 to 40 is preferred, 4 to 30 is more preferred, 6 to 20 is even more preferred, and 8 to 15 is particularly preferred. By setting the number at or above the lower limit, a strong film tends to be easily obtained, and surface roughness that occurs during development tends to be less likely to occur. By setting the content to the upper limit or less, patterning properties tend to be good. Examples of the aliphatic ring in the aliphatic ring group include a cyclohexane ring, a cycloheptane ring, a cyclodecane ring, a cyclododecane ring, a norbornane ring, an isobornane ring, and an adamantane ring. From the viewpoint of strong film properties, an adamantane ring is preferred.

[0250] 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 more preferably 3 or more. It is also preferably 10 or less, and more preferably 5 or less. The above upper and lower limits can be combined in any combination. For example, 1 to 10 is preferred, 1 to 5 is more preferred, 2 to 5 is even more preferred, and 3 to 5 is particularly preferred. By setting the number at or above the lower limit, a strong film tends to be obtained, and surface roughness during development tends to be less likely to occur. By setting the number at or below the upper limit, patterning characteristics tend to be improved. Examples of aromatic ring groups include aromatic hydrocarbon ring groups and aromatic heterocyclic groups. The number of carbon atoms in the aromatic ring group is also not particularly limited, but is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more. It is also 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 in any combination. For example, 4 to 30 is preferred, 5 to 20 is more preferred, and 6 to 15 is even more preferred. By setting the content to the lower limit or more, a strong film is easily obtained, and surface roughness during development tends to be less likely to occur. By setting the content to the upper limit or less, patterning properties tend to be good. Examples of the aromatic ring in the aromatic ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a fluorene ring. From the viewpoint of development solubility, a fluorene ring is preferred.

[0251] Examples of the substituent that the cyclic hydrocarbon group may have include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, and isoamyl; alkoxy groups having 1 to 5 carbon atoms, such as methoxy and ethoxy; hydroxyl; nitro; cyano; and carboxy. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0252] p represents an integer of 1 or more, preferably 2 or more, and preferably 3 or less. For example, 1 to 3 is preferred, and 2 to 3 is more preferred. By making p equal to or greater than the lower limit, the film hardness and film remaining rate tend to be good. By making p equal to or less than the upper limit, the developability tends to be good.

[0253] From the viewpoint of strong film hardness, Rα is preferably a monovalent aliphatic cyclic group, more preferably an adamantyl group.

[0254] The benzene ring in formula (C2-II-1) may be further substituted with an arbitrary substituent. Examples of the substituent include a hydroxy group, a methyl group, a methoxy group, an ethyl group, an ethoxy group, a propyl group, and a propoxy group. The number of substituents is not particularly limited, and may be one or two or more. From the viewpoint of patterning properties, it is preferably unsubstituted.

[0255] Specific examples of the partial structure represented by formula (C2-II-1) are shown below. In the examples, * represents a bond.

[0256]

[0257]

[0258]

[0259]

[0260]

[0261] The partial structure represented by formula (C2-II) is preferably a partial structure represented by the following general formula (C2-II-2) from the viewpoints of skeleton rigidity and membrane hydrophobicity.

[0262]

[0263] In formula (C2-II-2), R 13 , R 15 , R 16 , m and n are defined as in formula (C2-II), and R β represents a divalent cyclic hydrocarbon group which may have a substituent, and * represents a bond. The benzene ring in formula (C2-II-2) may be further substituted with any substituent.

[0264] (R β In formula (C2-II-2), R β represents a divalent cyclic hydrocarbon group which may have a substituent. Examples of the cyclic hydrocarbon group include an aliphatic cyclic group and an aromatic cyclic group.

[0265] The number of rings in the aliphatic cyclic group is not particularly limited, but is preferably 1 or more, more preferably 2 or more. It is also preferably 10 or less, more preferably 5 or less. The above upper and lower limits can be combined in any combination. For example, 1 to 10 is preferred, and 2 to 5 is more preferred. By setting the number at or above the lower limit, a strong film is more likely to be obtained, and surface roughness during development tends to be less likely to occur. By setting the number at or below the upper limit, deterioration in sensitivity can be suppressed, the residual film rate after development tends to be high, and resolution tends to be improved. The number of carbon atoms in the aliphatic cyclic group is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. It is also 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 in any combination. For example, 4 to 40 is preferred, more preferably 6 to 35, and even more preferably 8 to 30. By setting the number at or above the lower limit, roughness of the film surface during development tends to be suppressed. By setting the number at or below the upper limit, deterioration in sensitivity can be suppressed, the residual film rate after development tends to be high, and resolution tends to be improved. Examples of the aliphatic ring in the aliphatic ring group include a cyclohexane ring, a cycloheptane ring, a cyclodecane ring, a cyclododecane ring, a norbornane ring, an isobornane ring, and an adamantane ring. From the viewpoints of the residual film rate after development and resolution, an adamantane ring is preferred.

[0266] 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. It is also preferably 10 or less, and more preferably 5 or less. The above upper and lower limits can be combined in any combination. For example, 1 to 10 is preferred, 1 to 5 is more preferred, 2 to 5 is even more preferred, and 3 to 5 is particularly preferred. By setting the number of rings at or above the above lower limit, a strong film tends to be obtained, and surface roughness that occurs during development tends to be less likely to occur. By setting the number of rings at or below the above upper limit, deterioration of sensitivity and film loss tend to be easily suppressed, and resolution tends to be improved. Examples of aromatic ring groups include aromatic hydrocarbon ring groups and aromatic heterocyclic groups. The number of carbon atoms in the aromatic ring group is preferably 4 or more, more preferably 6 or more, even more preferably 8 or more, and even more preferably 10 or more. It is also 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 in any combination. For example, 4 to 40 is preferred, 6 to 30 is more preferred, 8 to 20 is even more preferred, and 10 to 15 is particularly preferred. By setting the value at or above the lower limit, a strong film tends to be obtained, and surface roughness during development tends to be less likely to occur. By setting the value at or below the upper limit, deterioration of sensitivity and film loss tend to be easily suppressed, and resolution tends to be improved. Examples of aromatic rings in the aromatic ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a fluorene ring. From the viewpoint of film retention rate, a fluorene ring is preferred. Because the plane forming the fluorene ring is perpendicular to the bond connecting the two benzene rings, the bulkiness results in a more rigid skeleton, which is less likely to cause penetration of a developer and shrinkage during baking, and it is presumed that this results in a higher film retention rate.

[0267] Examples of the substituent that the cyclic hydrocarbon group may have include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, and isoamyl; alkoxy groups having 1 to 5 carbon atoms, such as methoxy and ethoxy; hydroxyl; nitro; cyano; and carboxy. From the viewpoint of ease of synthesis, unsubstituted groups are preferred.

[0268] From the viewpoint of suppressing film loss and resolution, R β is preferably a divalent aliphatic cyclic group, and more preferably a divalent adamantane cyclic group. β is preferably a divalent aromatic ring group, and more preferably a divalent fluorene ring group.

[0269] The benzene ring in formula (C2-II-2) may be further substituted with any substituent. Examples of the substituent include a hydroxy group, a methyl group, a methoxy group, an ethyl group, an ethoxy group, a propyl group, and a propoxy group. The number of substituents is not particularly limited and may be one or two or more. Furthermore, two benzene rings may be linked via a substituent. In this case, examples of the substituent include divalent groups such as -O-, -S-, -NH-, and -CH2-. From the viewpoint of patterning properties, it is preferably unsubstituted. Furthermore, from the viewpoint of making it less likely to cause film loss, etc., it is preferably substituted with a methyl group.

[0270] Specific examples of the partial structure represented by formula (C2-II-2) are shown below. In the examples, * indicates a bond.

[0271]

[0272]

[0273]

[0274]

[0275] The partial structure represented by formula (C2-II) is preferably a partial structure represented by the following general formula (C2-II-3) from the viewpoint of the coating film remaining rate and patterning characteristics.

[0276]

[0277] In formula (C2-II-3), R 13 , R 14 , R 15 , R 16 , m and n are defined as in formula (C2-II), and R Z represents a hydrogen atom or a polybasic acid residue.

[0278] The polybasic acid residue refers to a monovalent or divalent group obtained by removing one or two OH groups from a polybasic acid. Z That is, R Z A plurality of Formula (C2-II-3) may be linked via an intermediate. Examples of polybasic acids include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenonetetracarboxylic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid, and biphenyltetracarboxylic acid. From the viewpoint of patterning properties, preferred are maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, and biphenyltetracarboxylic acid, and more preferred are tetrahydrophthalic acid, biphenyltetracarboxylic acid, and biphenyltetracarboxylic acid.

[0279] (C2-II) The partial structure represented by formula (C2-II-3) contained in one molecule of the epoxy (meth)acrylate resin may be one type or two or more types, and for example, R Z is a hydrogen atom, and R Z However, polybasic acid residues may be present in the mixture.

[0280] The number of partial structures represented by formula (C2-II) contained in one molecule of the epoxy (meth)acrylate resin (C2-II) is not particularly limited, but is preferably 1 or more, more preferably 3 or more. It is also preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The upper and lower limits above can be combined arbitrarily. For example, 1 to 20 is preferred, 1 to 15 is more preferred, and 3 to 10 is even more preferred. By setting the number at or above the lower limit, a strong film tends to be easily obtained, and surface roughness that occurs during development tends to be less likely to occur. By setting the number at or below the upper limit, it is easy to suppress deterioration in sensitivity and film loss, and resolution tends to be improved.

[0281] The weight average molecular weight (Mw) of the epoxy (meth)acrylate resin (C2-II) measured by gel permeation chromatography (GPC) in terms of polystyrene is not particularly limited, but is preferably 1,000 or more, more preferably 1,500 or more, even more preferably 2,000 or more, even more preferably 3,000 or more, particularly preferably 4,000 or more, and particularly preferably 5,000 or more. It is also preferably 10,000 or less, more preferably 8,000 or less, and even more preferably 7,000 or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 1,000 to 10,000, more preferably 1,500 to 10,000, even more preferably 1,500 to 8,000, even more preferably 2,000 to 8,000, and particularly preferably 2,000 to 7,000. By setting it to the lower limit or above, the film remaining rate of the photosensitive color resin composition tends to be good. By setting it to the upper limit or below, the solubility in the developer tends to be good.

[0282] The acid value of the epoxy (meth)acrylate resin (C2-II) is not particularly limited, but is preferably 20 mgKOH / g or more, more preferably 40 mgKOH / g or more, even more preferably 60 mgKOH / g or more, even more preferably 80 mgKOH / g or more, and particularly preferably 100 mgKOH / g or more. Also, it is preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less, even more preferably 130 mgKOH / g or less, and particularly preferably 120 mgKOH / g or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 20 to 200 mgKOH / g, more preferably 60 to 150 mgKOH / g, even more preferably 80 to 130 mgKOH / g, and even more preferably 100 to 130 mgKOH / g. By ensuring that the acid value is equal to or greater than the lower limit, the developer solubility is improved, and the resolution tends to be favorable. By making the content equal to or less than the upper limit, the remaining film rate of the photosensitive color resin composition tends to be good.

[0283] The epoxy (meth)acrylate resin (C2) may be used alone or in combination of two or more types.

[0284] <(C3) Isocyanuric Skeleton-Containing Resin> The photosensitive color resin composition of the present invention may use an isocyanuric skeleton-containing resin having an ethylenic double bond and a carboxy group as the alkali-soluble resin (C) other than the resin (C1). (Hereinafter, this may be simply referred to as the isocyanuric skeleton-containing resin (C3).) By having an isocyanuric skeleton, an ethylenic double bond, and a carboxy group, chemical resistance and heat resistance are improved, and the amount of decomposition products during development and baking is reduced, which tends to increase the current density when a voltage is applied to an organic electric field element. The isocyanuric skeleton-containing resin (C3) is an alkali-soluble resin (C) other than the resin (C1), and is not particularly limited as long as it has an ethylenic double bond, a carboxy group, and an isocyanuric skeleton. Examples include the following resins (C3-1) and (C3-2).

[0285] (C3-1) A resin obtained by further reacting a reaction product of an epoxy group-containing compound having an isocyanuric skeleton with an α,β-unsaturated monocarboxylic acid and / or an ester compound with a polybasic acid and / or an anhydride thereof.

[0286] Examples of epoxy group-containing compounds having an isocyanuric skeleton include compounds represented by the following general formula (C3-1-1):

[0287]

[0288] In formula (C3-1-1), R ４ ~R ６ each independently represents an alkylene group, and the alkylene group may be interrupted by an etheric oxygen atom.

[0289] The alkylene group preferably has 1 or more carbon atoms. It also preferably has 6 or fewer carbon atoms, more preferably 4 or fewer carbon atoms, and even more preferably 2 or fewer carbon atoms. The above upper and lower limits can be combined arbitrarily. For example, 1 to 6 carbon atoms are preferred, 1 to 4 carbon atoms are more preferred, and 1 to 2 carbon atoms are even more preferred. The alkylene group may be linear or branched. By setting the carbon number at or below the upper limit, developability tends to be improved and gas barrier properties tend to be improved. Examples of the alkylene group include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, an isobutylene group, an n-pentylene group, and an n-hexylene group. Examples of the alkylene group interrupted by an etheric oxygen atom include groups in which 1 to 10 carbon atoms of an alkylene chain having 4 to 30 carbon atoms, which may be linear or branched, are replaced with oxygen atoms, such as a group having 2 to 9 ethoxy groups linked thereto and a group having 2 to 7 propoxy groups linked thereto. Of these, from the viewpoint of gas barrier properties, a methylene group, an ethylene group, and an n-propylene group are preferred, and a methylene group is more preferred.

[0290] Examples of the α,β-unsaturated monocarboxylic acid and / or ester compound include monocarboxylic acids such as (meth)acrylic acid, α-position haloalkyl, alkoxyl, halogen, nitro, and cyano-substituted (meth)acrylic acid; 2-(meth)acryloyloxyethyl succinic acid, 2-(meth)acryloyloxyethyl adipate, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxyethyl maleate, 2-(meth)acryloyloxypropyl succinic acid, 2-(meth)acryloyloxypropyl adip ... hexahydrophthalate, 2-(meth)acryloyloxyethyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acryloyloxypropyl maleate, 2-(meth)acry Examples of the monomer include propyltetrahydrophthalic acid, 2-(meth)acryloyloxypropyl phthalic acid, 2-(meth)acryloyloxypropyl maleic acid, 2-(meth)acryloyloxybutyl succinic acid, 2-(meth)acryloyloxybutyl adipic acid, 2-(meth)acryloyloxybutyl hydrophthalic acid, 2-(meth)acryloyloxybutyl phthalic acid, and 2-(meth)acryloyloxybutyl maleic acid; and monomers obtained by adding an acid (anhydride) such as succinic acid anhydride, phthalic acid anhydride, or maleic acid anhydride to a hydroxyalkyl (meth)acrylate or pentaerythritol tri(meth)acrylate. From the viewpoint of sensitivity, (meth)acrylic acid is preferred.

[0291] As a method for adding an α,β-unsaturated monocarboxylic acid or an α,β-unsaturated monocarboxylic acid ester having a carboxy group to an epoxy resin, the same techniques as those used for the epoxy (meth)acrylate resin (C2) can be used.

[0292] Examples of polybasic acids and / or anhydrides thereof include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenonetetracarboxylic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid, biphenyltetracarboxylic acid, and anhydrides thereof.

[0293] Preferred are succinic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, biphenyltetracarboxylic acid, and anhydrides thereof, and particularly preferred are pyromellitic acid and anhydrides thereof.

[0294] The addition reaction of the polybasic acid and / or its anhydride can be carried out by the same method as in the case of (C2) epoxy (meth)acrylate resin. Examples of the α,β-unsaturated monocarboxylic acid and / or ester compound include the same compounds as those described in the section on (C2) epoxy (meth)acrylate resin. Examples of the polybasic acid and / or its anhydride include the same compounds as those described in the section on resin (C1).

[0295] (C3-2) A resin obtained by reacting a compound obtained by reacting a polyisocyanate compound having an isocyanuric skeleton with an acid or an acid anhydride, and then reacting the compound with an epoxy group-containing (meth)acrylate compound. Examples of the resin (C3-2) include the resins described in JP 2020-75994 A and intermediates thereof.

[0296] The weight-average molecular weight (Mw) of the isocyanuric skeleton-containing resin (C3) is not particularly limited, but is preferably 1,000 or more, more preferably 1,500 or more, even more preferably 2,000 or more, even more preferably 3,000 or more, particularly preferably 4,000 or more, and particularly preferably 5,000 or more. It is also preferably 10,000 or less, more preferably 8,000 or less, and even more preferably 7,000 or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 1,000 to 10,000, more preferably 1,500 to 10,000, even more preferably 1,500 to 8,000, even more preferably 2,000 to 8,000, and particularly preferably 2,000 to 7,000. By setting it to be equal to or greater than the lower limit, it tends to be possible to prevent the solubility in the developer from becoming too high. By setting it to be equal to or less than the upper limit, it tends to be possible to easily achieve good solubility in the developer.

[0297] The acid value of the isocyanuric skeleton-containing resin (C3) is not particularly limited, but is preferably 20 mgKOH / g or more, more preferably 40 mgKOH / g or more, even more preferably 60 mgKOH / g or more, even more preferably 80 mgKOH / g or more, and particularly preferably 100 mgKOH / g or more. Also, it is preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less. The above upper and lower limits can be arbitrarily combined. For example, 20 to 200 mgKOH / g is preferred, and 60 to 150 mgKOH / g is more preferred. By setting it to the lower limit or more, the development solubility tends to be improved and the resolution tends to be good. By setting it to the upper limit or less, the residual film rate of the photosensitive color resin composition tends to be good.

[0298] <(C4) Acrylic Copolymer Resin> As the alkali-soluble resin (C), an acrylic copolymer resin (C4) may be used in addition to the resin (C1) from the viewpoint of compatibility with pigments, dispersants, etc. As the acrylic copolymer resin (C4), for example, those described in JP 2014-137466 A can be preferably used.

[0299] Examples of the (C4) acrylic copolymer resin include copolymers of an ethylenically unsaturated monomer having one or more carboxy groups (hereinafter referred to as "unsaturated monomer (C4-1)") and another copolymerizable ethylenically unsaturated monomer (hereinafter referred to as "unsaturated monomer (C4-2)"). Examples of the unsaturated monomer (C4-1) include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid; unsaturated dicarboxylic acids or anhydrides thereof such as maleic acid, maleic anhydride, fumaric acid, citraconic acid, citraconic anhydride, and mesaconic acid; mono[(meth)acryloyloxyalkyl] esters of divalent or higher polycarboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; mono(meth)acrylates of polymers having a carboxy group and a hydroxyl group at both ends, such as ω-carboxypolycaprolactone mono(meth)acrylate; and p-vinylbenzoic acid. These unsaturated monomers (C4-1) can be used alone or in combination of two or more.

[0300] Examples of the unsaturated monomer (C4-2) include N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide; aromatic vinyl compounds such as styrene, α-methylstyrene, p-hydroxystyrene, p-hydroxy-α-methylstyrene, p-vinylbenzyl glycidyl ether, and acenaphthylene;

[0301] Methyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, allyl (meth)acrylate, benzyl (meth)acrylate, 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 (meth)acrylate, isobornyl (meth)acrylate, tricyclo[5.2.1.0] 2,6 (meth)acrylic acid esters such as ]decan-8-yl (meth)acrylate, dicyclopentenyl (meth)acrylate, glycerol mono(meth)acrylate, 4-hydroxyphenyl (meth)acrylate, ethylene oxide-modified (meth)acrylate of para-cumylphenol, glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-[(meth)acryloyloxymethyl]oxetane, and 3-[(meth)acryloyloxymethyl]-3-ethyloxetane;

[0302] Cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo[5.2.1.0 2,6vinyl ethers such as decan-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, and 3-(vinyloxymethyl)-3-ethyloxetane; and macromonomers having a mono(meth)acryloyl group at the end of the polymer molecular chain, such as polystyrene, polymethyl(meth)acrylate, poly-n-butyl(meth)acrylate, and polysiloxane. These unsaturated monomers (C4-2) can be used alone or in combination of two or more.

[0303] In the copolymer of the unsaturated monomer (C4-1) and the unsaturated monomer (C4-2), the copolymerization ratio of the unsaturated monomer (C4-1) is preferably 5 to 50 mass%, more preferably 10 to 40 mass%. By copolymerizing the unsaturated monomer (C4-1) in such a range, it tends to be possible to obtain a photosensitive colored resin composition that is excellent in alkali developability and storage stability.

[0304] Examples of the copolymer of the unsaturated monomer (C4-1) and the unsaturated monomer (C4-2) include the copolymers disclosed in Japanese Patent Application Laid-Open Nos. 7-140654, 8-259876, 10-31308, 10-300922, 11-174224, 11-258415, 2000-56118, and 2004-101728. The copolymer of the unsaturated monomer (C4-1) and the unsaturated monomer (C4-2) can be produced by known methods. For example, the structure, Mw, and Mw / Mn (Mn is the number average molecular weight) can be controlled by the methods disclosed in JP-A-2003-222717, JP-A-2006-259680, and WO 2007 / 029871.

[0305] In addition to the above, the resins described in WO 2016 / 194619 and WO 2017 / 154439 may also be used as the acrylic copolymer resin (C4).

[0306] <(D) Photopolymerization initiator> The photosensitive color resin composition of the present invention contains (D) a photopolymerization initiator. (D) The photopolymerization initiator is a component that directly absorbs light, causes a decomposition reaction or a hydrogen abstraction reaction, and has the function of generating polymerization active radicals. If necessary, an additive such as a polymerization accelerator (chain transfer agent) or a sensitizing dye may be added and used. Examples of the photopolymerization initiator include metallocene compounds including titanocene compounds described in JP-A-59-152396 and JP-A-61-151197; hexaarylbiimidazole derivatives described in JP-A-2000-56118; halomethylated oxadiazole derivatives and halomethyl-s-triazine derivatives described in JP-A-10-39503; α-aminoalkylphenone derivatives; and oxime ester compounds described in JP-A-2000-80068 and JP-A-2006-36750.

[0307] Examples of the metallocene compound include dicyclopentadienyltitanium dichloride, dicyclopentadienyltitanium bisphenyl, dicyclopentadienyltitanium bis(2,3,4,5,6-pentafluorophenyl-1-yl), dicyclopentadienyltitanium bis(2,3,5,6-tetrafluorophenyl-1-yl), dicyclopentadienyltitanium bis(2,4,6-trifluorophenyl-1-yl), dicyclopentadienyltitanium Examples of the titanium bis(2,6-difluorophenyl-1-yl) include titanium dioxide (2,6-difluorophenyl-1-yl), titanium dioxide (2,6-difluorophenyl-1-yl), titanium dioxide (2,6-difluorophenyl-1-yl), titanium dioxide (2,6-difluorophenyl-1-yl), titanium dioxide (2,6-difluoro-3-(pyrro-1-yl)-phenyl-1-yl), and titanium dioxide (2,6-difluoro-3-(pyrro-1-yl)-phenyl-1-yl).

[0308] Examples of hexaarylbiimidazole derivatives include 2-(2'-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(2'-chlorophenyl)-4,5-bis(3'-methoxyphenyl)imidazole dimer, 2-(2'-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(2'-methoxyphenyl)-4,5-diphenylimidazole dimer, and (4'-methoxyphenyl)-4,5-diphenylimidazole dimer.

[0309] Examples of halomethylated oxadiazole derivatives include 2-trichloromethyl-5-(2'-benzofuryl)-1,3,4-oxadiazole, 2-trichloromethyl-5-[β-(2'-benzofuryl)vinyl]-1,3,4-oxadiazole, 2-trichloromethyl-5-[β-(2'-(6''-benzofuryl)vinyl)]-1,3,4-oxadiazole, and 2-trichloromethyl-5-furyl-1,3,4-oxadiazole.

[0310] 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.

[0311] Examples of α-aminoalkylphenone derivatives include 2-methyl-1[4-(methylthio)phenyl]-2-morpholinopropan-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.

[0312] As the (D) photopolymerization initiator, an oxime ester compound is particularly effective in terms of sensitivity and plate-making properties, and for example, when an alkali-soluble resin containing a phenolic hydroxyl group is used, such an oxime ester compound having excellent sensitivity is particularly useful. Since the oxime ester compound has a structure that absorbs ultraviolet light, a structure that transmits light energy, and a structure that generates radicals, it has high sensitivity even in a small amount and is stable against thermal reactions, and it is possible to obtain a highly sensitive photosensitive colored resin composition with a small amount.

[0313] Examples of the oxime ester compound include compounds represented by the following general formula (IV).

[0314]

[0315] In formula (IV), R 21a represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent. 21b represents an optional substituent containing an aromatic ring. 22a represents an alkanoyl group which may have a substituent or an aroyl group which may have a substituent, and n represents an integer of 0 or 1.

[0316] R 21a The number of carbon atoms in the alkyl group in the formula (I) is not particularly limited, but from the viewpoint of solubility in a solvent and sensitivity, it is preferably 1 or more, more preferably 2 or more, and is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and a cyclopentylethyl group. Examples of the substituent that the alkyl group may have include an aromatic ring group, a hydroxyl group, a carboxy group, a halogen atom, an amino group, an amide group, a 4-(2-methoxy-1-methyl)ethoxy-2-methylphenyl group, and an N-acetyl-N-acetoxyamino group. From the viewpoint of ease of synthesis, it is preferably unsubstituted.

[0317] R 21aExamples of the aromatic ring group in include an aromatic hydrocarbon ring group and an aromatic heterocyclic group. The number of carbon atoms in the aromatic ring group is not particularly limited, but is preferably 5 or more from the viewpoint of solubility in the photosensitive color resin composition. Also, 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.

[0318] Examples of the aromatic ring group include a phenyl group, a naphthyl group, a pyridyl group, and a furyl group. From the viewpoint of developability, a phenyl group or a naphthyl group is preferred, and a phenyl group is more preferred. Examples of the substituent that the aromatic ring group may have include a hydroxyl group, a carboxyl group, a halogen atom, an amino group, an amide group, an alkyl group, an alkoxy group, and a group in which these substituents are linked. From the viewpoint of developability, an alkyl group, an alkoxy group, and a group in which these are linked are preferred, and linked alkoxy groups are more preferred. From the viewpoint of developability, R 21a is preferably an aromatic ring group which may have a substituent, and more preferably an aromatic ring group which has a linked alkoxy group as a substituent.

[0319] R 21b Examples of the alkyl group include an optionally substituted carbazolyl group, an optionally substituted thioxanthonyl group, an optionally substituted diphenyl sulfide group, an optionally substituted fluorenyl group, and an optionally substituted indolyl group. From the viewpoint of sensitivity, an optionally substituted carbazolyl group is preferred. From the viewpoint of electrical reliability, an optionally substituted diphenyl sulfide group is preferred.

[0320] R 22aThe number of carbon atoms in the alkanoyl group in the formula (I) is not particularly limited, but from the viewpoint of solubility in a solvent and sensitivity, it is preferably 2 or more, and is preferably 20 or less, more preferably 15 or less, even more preferably 10 or less, and particularly preferably 5 or less. Examples of the alkanoyl group include an acetyl group, a propanoyl group, and a butanoyl group. Examples of the substituent that the alkanoyl group may have include an aromatic ring group, a hydroxyl group, a carboxy group, a halogen atom, an amino group, and an amide group. From the viewpoint of ease of synthesis, it is preferably unsubstituted.

[0321] R 22a The number of carbon atoms in the aroyl group in is not particularly limited, but from the viewpoint of solubility in a solvent and sensitivity, it is preferably 7 or more, more preferably 8 or more, and also preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. Examples of the aroyl group include a benzoyl group and a naphthoyl group. Examples of the substituent that the aroyl group may have include a hydroxyl group, a carboxy group, a halogen atom, an amino group, an amide group, and an alkyl group. From the viewpoint of ease of synthesis, it is preferably unsubstituted. From the viewpoint of sensitivity, R 22a is preferably an alkanoyl group which may have a substituent, more preferably an unsubstituted alkanoyl group, and even more preferably an acetyl group.

[0322] For example, Japanese Patent No. 4454067, WO 2002 / 100903, WO 2012 / 45736, WO 2015 / 36910, WO 2006 / 18973, WO 2008 / 78678, Japanese Patent No. 4818458, WO 2005 / 80338, WO 2008 / 75564, WO 2009 / 131189, WO 2009 / 131189, WO 2010 / 133077, WO 2010 / 102502, photopolymerization initiators described in WO 2012 / 68879 can be used.

[0323] The initiators described in JP 2016-133574 A can also be suitably used because they reduce contamination by colorants.

[0324] The photopolymerization initiator may be used alone or in combination of two or more. If necessary, a sensitizing dye and a polymerization accelerator according to the wavelength of the image exposure light source may be blended with the photopolymerization initiator for the purpose of increasing sensitivity. Examples of sensitizing dyes include xanthene dyes described in JP-A-4-221958 and JP-A-4-219756, coumarin dyes having a heterocycle described in JP-A-3-239703 and JP-A-5-289335, 3-ketocoumarin compounds described in JP-A-3-239703 and JP-A-5-289335, pyrromethene dyes described in JP-A-6-19240, and the like. Examples of dyes having a dialkylaminobenzene skeleton include those described in JP-B No. 45-37377, JP-A No. 48-84183, JP-A No. 52-112681, JP-A No. 58-15503, JP-A No. 60-88005, JP-A No. 59-56403, JP-A No. 2-69, JP-A No. 57-168088, JP-A No. 5-107761, JP-A No. 5-210240, and JP-A No. 4-288818.

[0325] The sensitizing dye is preferably an amino group-containing sensitizing dye, and more preferably a compound having an amino group and a phenyl group in the same molecule. Examples thereof include benzophenone compounds such as 4,4'-dimethylaminobenzophenone, 4,4'-diethylaminobenzophenone, 2-aminobenzophenone, 4-aminobenzophenone, 4,4'-diaminobenzophenone, 3,3'-diaminobenzophenone, and 3,4-diaminobenzophenone; 2-(p-dimethylaminophenyl)benzoxazole, 2-(p-diethylaminophenyl)benzoxazole, 2-(p-dimethylaminophenyl)benzo[4,5]benzoxazole, 2-(p-dimethylaminophenyl)benzo[6,7]benzoxazole, 2,5-bis(p-diethylaminophenyl)-1,3,4-oxazole, and 2-(p-dimethylaminophenyl)benzo[4,5]benzoxazole.

[0039] Preferred are p-dialkylaminophenyl group-containing compounds such as (p-phenyl)benzothiazole, 2-(p-diethylaminophenyl)benzothiazole, 2-(p-dimethylaminophenyl)benzimidazole, 2-(p-diethylaminophenyl)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, and (p-diethylaminophenyl)pyrimidine, with 4,4'-dialkylaminobenzophenone being particularly preferred. One type of sensitizing dye may be used alone, or two or more types may be used in combination.

[0326] Examples of the polymerization accelerator include aromatic amines such as ethyl p-dimethylaminobenzoate and 2-dimethylaminoethyl benzoate, aliphatic amines such as n-butylamine and N-methyldiethanolamine, and mercapto compounds described below. One type of polymerization accelerator may be used alone, or two or more types may be used in combination.

[0327] <(E) Ethylenically Unsaturated Compound> The photosensitive coloring resin composition of the present invention may contain (E) an ethylenically unsaturated compound. By containing (E) an ethylenically unsaturated compound, sensitivity tends to be improved. The (E) ethylenically unsaturated compound used in the present invention is a compound having at least one ethylenically unsaturated group in the molecule. Specific examples include (meth)acrylic acid, (meth)acrylic acid alkyl ester, acrylonitrile, styrene, a carboxylic acid having one ethylenically unsaturated bond, and a monoester of a polyhydric or monohydric alcohol.

[0328] In the present invention, it is particularly preferable to use a polyfunctional ethylenic monomer having two or more ethylenically unsaturated groups per molecule. The number of ethylenically unsaturated groups in the polyfunctional ethylenic 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 fewer, and more preferably seven or fewer. The above upper and lower limits can be arbitrarily combined. 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. Setting the number at or above the lower limit tends to result in high sensitivity. Setting the number at or below the upper limit tends to result in improved solubility in solvents. Examples of polyfunctional ethylenic 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 of polyvalent hydroxy compounds, such as aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds, with unsaturated carboxylic acids and polybasic carboxylic acids.

[0329] Examples of esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids include acrylic acid esters of aliphatic polyhydroxy compounds such as ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolethane triacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, and glycerol acrylate; methacrylic acid esters in which these acrylates are replaced with methacrylate; itaconic acid esters in which these acrylates are replaced with itaconate; crotonate esters in which these acrylates are replaced with crotonate; and maleic acid esters in which these acrylates are replaced with maleate.

[0330] Examples of esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids include acrylic acid esters and methacrylic acid esters of aromatic polyhydroxy compounds such as hydroquinone diacrylate, hydroquinone dimethacrylate, resorcinol diacrylate, resorcinol dimethacrylate, and pyrogallol triacrylate.

[0331] The ester obtained by the esterification reaction of a polybasic carboxylic acid and an unsaturated carboxylic acid with a polyvalent hydroxy compound is not necessarily a single compound, but examples thereof include a condensate of acrylic acid, phthalic acid, and ethylene glycol, a condensate of acrylic acid, maleic acid, and diethylene glycol, a condensate of methacrylic acid, terephthalic acid, and pentaerythritol, and a condensate of acrylic acid, adipic acid, butanediol, and glycerin.

[0332] Other examples of the polyfunctional ethylenic monomer used in the present invention include urethane (meth)acrylates obtained by reacting a polyisocyanate compound with a hydroxyl group-containing (meth)acrylic acid ester or a polyisocyanate compound with a polyol and a hydroxyl group-containing (meth)acrylic acid ester; epoxy acrylates such as addition reaction products of a polyfunctional epoxy compound with a hydroxy(meth)acrylate or (meth)acrylic acid; acrylamides such as ethylenebisacrylamide; allyl esters such as diallyl phthalate; and vinyl group-containing compounds such as divinyl phthalate.

[0333] Examples of urethane (meth)acrylates include DPHA-40H, UX-5000, UX-5002D-P20, UX-5003D, and UX-5005 (manufactured by Nippon Kayaku Co., Ltd.), U-2PPA, U-6LPA, U-10PA, U-33H, UA-53H, UA-32P, and UA-1100H (manufactured by Shin-Nakamura Chemical Co., Ltd.), UA-306H, UA-510H, and UF-8001G (manufactured by Kyoeisha Chemical Co., Ltd.), and UV-1700B, UV-7600B, UV-7605B, UV-7630B, and UV7640B (manufactured by Mitsubishi Chemical Corporation).

[0334] From the viewpoint of curability, it is preferable to use, as the (E) ethylenically unsaturated compound, a (meth)acrylic acid alkyl ester, a urethane (meth)acrylate obtained by reacting a polyisocyanate compound with a hydroxyl group-containing (meth)acrylic acid ester, or a polyisocyanate compound with a polyol and a hydroxyl group-containing (meth)acrylic acid ester, and it is more preferable to use a polyisocyanate compound with a hydroxyl group-containing (meth)acrylic acid ester. These may be used alone or in combination of two or more.

[0335] <Other components of the photosensitive colored resin composition> In addition to the above-mentioned components, the photosensitive colored resin composition of the present invention can be appropriately blended with additives such as adhesion improvers such as silane coupling agents, surfactants, pigment derivatives, photoacid generators, crosslinking agents, mercapto compounds, polymerization inhibitors, etc.

[0336] (1) Adhesion improver The photosensitive color resin composition of the present invention may contain an adhesion improver to improve adhesion to the substrate.As the adhesion improver, a silane coupling agent or a phosphate group-containing compound is preferred.As the silane coupling agent, for example, various types such as epoxy-based, (meth)acrylic-based, and amino-based may be used alone or in combination of two or more.

[0337] Examples of silane coupling agents include (meth)acryloxysilanes such as 3-methacryloxypropylmethyldimethoxysilane and 3-methacryloxypropyltrimethoxysilane; epoxysilanes such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane and 3-glycidoxypropyltriethoxysilane; ureidosilanes such as 3-ureidopropyltriethoxysilane; and isocyanatesilanes such as 3-isocyanatopropyltriethoxysilane. Epoxysilane silane coupling agents are particularly preferred. Phosphoric acid group-containing compounds are preferably (meth)acryloyl group-containing phosphates, and those represented by the following general formula (g1), (g2), or (g3) are preferred.

[0338]

[0339] In formulas (g1), (g2) and (g3), R 51 represents a hydrogen atom or a methyl group, l and l' are integers of 1 to 10, and m is 1, 2, or 3. These phosphate group-containing compounds may be used alone or in combination of two or more.

[0340] (2) Surfactant The photosensitive color resin composition of the present invention may contain a surfactant to improve coating properties.

[0341] As the surfactant, various types of surfactants can be used, such as anionic, cationic, nonionic, and amphoteric surfactants. Nonionic surfactants are preferred because they are less likely to adversely affect various properties, and fluorine-based or silicone-based surfactants are more preferred in terms of application properties. Examples of such surfactants include TSF4460 (manufactured by Momentive Performance Materials), DFX-18 (manufactured by Neos Corporation), BYK-300, BYK-325, and BYK-330 (manufactured by BYK-Chemie), KP340 (manufactured by Shin-Etsu Silicones), F-470, F-475, F-478, F-554, and F-559 (manufactured by DIC Corporation), SH7PA (manufactured by Dow Corning Toray Co., Ltd.), DS-401 (manufactured by Daikin Corporation), L-77 (manufactured by Nippon Unicar Co., Ltd.), and FC4430 (manufactured by 3M). One type of surfactant may be used, or two or more types may be used in combination.

[0342] (3) Pigment Derivative The photosensitive colored resin composition of the present invention may contain a pigment derivative as a dispersing aid to improve dispersibility and storage stability. Examples of pigment derivatives include azo-based, phthalocyanine-based, quinacridone-based, benzimidazolone-based, quinophthalone-based, isoindolinone-based, dioxazine-based, anthraquinone-based, indanthrene-based, perylene-based, perinone-based, diketopyrrolopyrrole-based, and dioxazine-based derivatives, with phthalocyanine-based and quinophthalone-based derivatives being preferred. Examples of substituents on the pigment derivative include sulfonic acid groups, sulfonamide groups and their quaternary salts, phthalimidomethyl groups, dialkylaminoalkyl groups, hydroxyl groups, carboxy groups, and amide groups bonded to the pigment skeleton directly or via, for example, an alkyl group, an aryl group, or a heterocyclic group, with sulfonic acid groups being preferred. Multiple substituents may be substituted on one pigment skeleton, or multiple types of substituents may be substituted.

[0343] 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. These may be used alone or in combination of two or more.

[0344] (4) Mercapto Compound The photosensitive color resin composition of the present invention may contain a mercapto compound as a polymerization accelerator and for improving adhesion to a substrate.

[0345] Examples of the mercapto compound include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, hexanedithiol, decanedithiol, 1,4-dimethylmercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, ethylene glycol bis( 3-mercaptobutyrate), butanediol bis(3-mercaptobutyrate), 1,4-bis(3-mercaptobutyryloxy)butane, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptobutyrate), pentaerythritol tris(3-mercaptobutyrate), ethylene glycol bis(3-mercaptoisobutyrate), butanediol bis(3-mercaptoisobutyrate), trimethylolpropane tris(3-mercaptoisobutyrate), 1,3,5-tris(3-mercaptobutyloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, and other mercapto compounds having a heterocycle, such as 1,3,5-tris(3-mercaptobutyloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione. These compounds may be used singly or in combination of two or more.

[0346] (5) Polymerization Inhibitor The photosensitive colored resin composition of the present invention may contain a polymerization inhibitor from the viewpoint of controlling the shape of the cured product. The inclusion of a polymerization inhibitor inhibits radical polymerization of the lower layer of the coating film, which is thought to enable control of the taper angle (the angle between the support and the cured product in the cross section of the cured product). Examples of polymerization inhibitors include hydroquinone, hydroquinone monomethyl ether, methylhydroquinone, methoxyphenol, and 2,6-di-tert-butyl-4-cresol (BHT). 2,6-di-tert-butyl-4-cresol is preferred from the viewpoint of shape control. Hydroquinone monomethyl ether and methylhydroquinone are preferred from the viewpoint of particularly excellent safety to the human body. One polymerization inhibitor may be used alone, or two or more polymerization inhibitors may be used in combination. (C) When producing the alkali-soluble resin, a polymerization inhibitor may be contained in the resin. This may be used as the polymerization inhibitor of the present invention. Alternatively, in addition to the polymerization inhibitor, a polymerization inhibitor identical to or different from the polymerization inhibitor may be added to the resin during production of the photosensitive colored resin composition.

[0347] When the photosensitive colored resin composition contains a polymerization inhibitor, its content is not particularly limited, but 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, relative to the total solid content of the photosensitive colored resin composition. It is also 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 arbitrarily combined. For example, 0.0005% by mass to 0.3% by mass is preferred, 0.001% by mass to 0.2% by mass is more preferred, and 0.01% by mass to 0.1% by mass is even more preferred. By setting the content at or above the lower limit, the shape of the cured product tends to be controllable. By setting the content at or below the upper limit, the required sensitivity tends to be maintained.

[0348] (6) Solvent The photosensitive colored resin composition of the present invention preferably contains a solvent. By containing a solvent, the colorant can be dispersed or dissolved in the solvent, and application becomes easy. The photosensitive colored resin composition of the present invention is used in a state in which, for example, (A) colorant, (B) dispersant, (C) alkali-soluble resin, (D) photopolymerization initiator and other various materials used as needed are dissolved or dispersed in the solvent. From the viewpoint of dispersibility and application property, an organic solvent is preferred.

[0349] From the viewpoint of coatability, it is preferable to select an organic solvent having a boiling point of 100 to 300° C., more preferably 120 to 280° C. The boiling point here means the boiling point at a pressure of 1013.25 hPa, and the same applies to all boiling points hereinafter.

[0350] Examples of such organic solvents include glycol monoalkyl ethers such as 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 t-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, methoxymethyl pentanol, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methoxybutanol, 3-methyl-3-methoxybutanol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, and tripropylene glycol methyl ether; glycol dialkyl ethers 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;

[0351] Glycol alkyl ether acetates such as 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, and 3-methyl-3-methoxybutyl acetate; glycol diacetates such as ethylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexylene glycol diacetate; Alkyl acetates such as cyclohexanol acetate; ethers such as amyl ether, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, diamyl ether, ethyl isobutyl ether, and dihexyl ether;

[0352] Ketones such as acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl nonyl ketone, and methoxymethyl pentanone; monohydric or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, butanediol, diethylene glycol, dipropylene glycol, triethylene glycol, methoxymethyl pentanol, glycerin, and benzyl alcohol; aliphatic hydrocarbons such as n-pentane, n-octane, diisobutylene, n-hexane, hexene, isoprene, dipentene, and dodecane; alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, and bicyclohexyl;

[0353] aromatic hydrocarbons such as benzene, toluene, xylene, and cumene; chain or cyclic esters such as 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 caprylate, butyl stearate, ethyl benzoate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, butyl 3-methoxypropionate, and γ-butyrolactone; alkoxycarboxylic acids such as 3-methoxypropionic acid and 3-ethoxypropionic acid; halogenated hydrocarbons such as butyl chloride and amyl chloride; ether ketones such as methoxymethylpentanone; and nitriles such as acetonitrile and benzonitrile.

[0354] Examples of commercially available organic solvents that can be used include mineral spirits, Balsol #2, Apco #18 Solvent, Apco Thinner, Socal 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 diglyme (all trade names). These organic solvents may be used alone or in combination of two or more.

[0355] When the partition walls are formed by photolithography, the organic solvent to be selected preferably has a boiling point of 100 to 240°C, more preferably 120 to 200°C, and even more preferably 120 to 170°C.

[0356] Glycol alkyl ether acetates are preferred because they have a good balance of application properties, surface tension, etc., and the solubility of the components in the composition is relatively high. Glycol alkyl ether acetates may be used alone or in combination with two or more. Glycol alkyl ether acetates may be used alone, or may be used in combination with other organic solvents. Glycol monoalkyl ethers are preferred as the organic solvent to be used in combination. Propylene glycol monomethyl ether is preferred in terms of the solubility of the components in the composition. Glycol monoalkyl ethers have high polarity, and if added in excessive amounts, the pigment tends to aggregate, and the storage stability of the resulting photosensitive colored resin composition tends to decrease, such as increasing the viscosity. Therefore, the proportion of glycol monoalkyl ethers in the solvent is preferably 5 to 30% by mass, more preferably 5 to 20% by mass.

[0357] By using an organic solvent with a boiling point of 150°C or higher (hereinafter sometimes referred to as a "high-boiling point solvent") in combination, the photosensitive color resin composition becomes less likely to dry, but the high-boiling point solvent may be used in combination because it has the effect of preventing the uniform dispersion of the pigment in the composition from being destroyed by rapid drying. For example, it has the effect of preventing the occurrence of foreign matter defects due to precipitation and solidification of the colorant, etc. at the tip of the slit nozzle. Because of this high effect, when a high-boiling point solvent is used in combination, it is preferable to use diethylene glycol mono-n-butyl ether, diethylene glycol mono-n-butyl ether acetate, or diethylene glycol monoethyl ether acetate in combination.

[0358] When a high-boiling-point solvent is used in combination, the content of the high-boiling-point solvent 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 at or above the lower limit, it tends to be possible to prevent, for example, the colorant or the like from precipitating and solidifying at the tip of the slit nozzle, which could cause foreign matter defects. By setting the content at or below the upper limit, it tends to be possible to prevent the drying time of the composition from becoming long, and to prevent problems such as poor tact time in the reduced-pressure drying process and pin marks during pre-baking.

[0359] The high-boiling point solvent may be a glycol alkyl ether acetate or a glycol alkyl ether. In this case, it is not necessary to separately contain a high-boiling point solvent. Preferred high-boiling point solvents include, for example, diethylene glycol mono-n-butyl ether acetate, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,6-hexanol diacetate, and triacetin.

[0360] <Content ratio of each component in the photosensitive colored resin composition> The content ratio of the colorant (A) in the photosensitive colored 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 colored resin composition. Also, 40% by mass or less is preferred, 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 arbitrarily combined. For example, 5 to 40% by mass is preferred, 10 to 30% by mass is more preferred, 15 to 30% by mass is even more preferred, 15 to 25% by mass is even more preferred, and 15 to 20% by mass is particularly preferred. By setting the content at or above the lower limit, light-blocking properties tend to be ensured. By setting the content at or below the upper limit, the amount of dispersant can be reduced, which tends to suppress surface roughness.

[0361] The content of the organic pigment (A-1) in the photosensitive color 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, based on the total solid content of the photosensitive color resin composition. Also, 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 arbitrarily combined. 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 at or above the lower limit, light-blocking properties tend to be ensured. By setting it at or below the upper limit, the residual film ratio tends to be higher.

[0362] When the photosensitive color resin composition of the present invention contains an organic black pigment, the content of the organic black pigment in the photosensitive color 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, based on the total solid content of the photosensitive color resin composition. Also, 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 arbitrarily combined. 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 at or above the lower limit, light-blocking properties tend to be ensured. By setting it at or below the upper limit, the residual film ratio tends to be higher.

[0363] When the photosensitive colored resin composition of the present invention contains a colorant other than the organic pigment (A-1), the content ratio thereof is not particularly limited, but is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more, based on the total solid content of the photosensitive colored resin composition. Also, it is preferably 30% by mass or less, more preferably 20% by mass or less. The above upper and lower limits can be arbitrarily combined. 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 at or above the lower limit, the light-blocking properties tend to be improved while suppressing the loss of ultraviolet light required for curing. By setting it at or below the upper limit, the residual film ratio tends to be higher.

[0364] The content of (B) dispersant is not particularly limited, but is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more, relative to the total solid content of the photosensitive colored resin composition. It is also 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 upper and lower limits can be arbitrarily combined. For example, 1 to 20% by mass is preferred, 2 to 15% by mass is more preferred, 3 to 10% by mass is even more preferred, and 3 to 7% by mass is particularly preferred. By setting the content at or above the lower limit, sufficient dispersibility tends to be easily obtained. By setting the content at or below the upper limit, outgassing tends to be reduced.

[0365] The content ratio of (B) dispersant relative to 100 parts by mass of (A) colorant is not particularly limited, but is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, and is preferably 50 parts by mass or less, more preferably 30 parts by mass or less. The above upper and lower limits can be arbitrarily combined. For example, 5 to 50 parts by mass is preferred, 10 to 50 parts by mass is more preferred, and 15 to 30 parts by mass is even more preferred. By setting the content at or above the lower limit, sufficient dispersibility tends to be easily obtained. By setting the content at or below the upper limit, the residual film rate tends to be high.

[0366] The content of the alkali-soluble resin (C) is not particularly limited, but is preferably 5% by mass or more, more preferably 10% 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, relative to the total solids content of the photosensitive colored resin composition. It is also preferably 85% by mass or less, more preferably 80% by mass or less, even 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 arbitrarily combined. For example, 5 to 80% by mass is preferred, 10 to 70% by mass is more preferred, 20 to 60% by mass is even more preferred, 30 to 60% by mass is even more preferred, 30 to 55% by mass is particularly preferred, and 40 to 55% by mass is particularly preferred. By setting the content at or above the lower limit, it is possible to suppress a decrease in the solubility of the unexposed portion in the developer and to suppress development defects. By setting the content at or below the upper limit, it is possible to maintain appropriate sensitivity, suppress dissolution of the exposed portion in the developer, and tend to reduce the taper angle.

[0367] The content of resin (C1) is not particularly limited, but is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, relative to the total solid content of the photosensitive color resin composition. It is also 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 upper and lower limits can be arbitrarily combined. For example, 1 to 20% by mass is preferred, 3 to 17% by mass is more preferred, 3 to 15% by mass is even more preferred, and 5 to 10% by mass is particularly preferred. By setting the content at or above the lower limit, dispersion stability tends to be improved. By setting the content at or below the upper limit, solubility in the developer tends to be good.

[0368] The content of resin (C1) is not particularly limited, but is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more, of the alkali-soluble resin (C). It is also 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 arbitrarily combined. For example, 1 to 100% by mass is preferred, 5 to 80% by mass is more preferred, 10 to 60% by mass is even more preferred, 10 to 40% by mass is even more preferred, and 10 to 20% by mass is particularly preferred. By setting the content at or above the lower limit, a decrease in the solubility of the unexposed portions in the developer tends to be suppressed, and development defects tend to be suppressed. By setting the content at or below the upper limit, appropriate sensitivity can be maintained, dissolution of the exposed portions in the developer can be suppressed, and a decrease in the sharpness and adhesion of the pattern tends to be suppressed.

[0369] When the photosensitive colored resin composition of the present invention contains an epoxy (meth)acrylate resin (C2), the content of the epoxy (meth)acrylate resin (C2) is not particularly limited, but is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, particularly preferably 30% by mass or more, particularly preferably 40% by mass or more, based on the total solids content of the photosensitive colored resin composition of the present invention. It is also preferably 80% by mass or less, more 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 arbitrarily combined. For example, 5 to 80% by mass is preferred, 10 to 70% by mass is more preferred, 15 to 60% by mass is even more preferred, 20 to 60% by mass is even more preferred, 30 to 55% by mass is even more preferred, and 40 to 55% by mass is particularly preferred. By setting the content at or above the lower limit, the solubility of the unexposed portion in the developer tends to be ensured. By setting the content to the upper limit or less, appropriate sensitivity can be maintained, dissolution of exposed areas by a developer can be suppressed, and deterioration in the sharpness and adhesion of the pattern can be suppressed.

[0370] When the alkali-soluble resin (C) contains an epoxy (meth)acrylate resin (C2), the content of the epoxy (meth)acrylate resin (C2) 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, even more preferably 40% by mass or more, and is 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 arbitrarily combined. For example, 20 to 100% by mass is preferred, 30 to 90% by mass is more preferred, and 40 to 80% by mass is even more preferred. Setting the content at or above the lower limit tends to ensure the solubility of the unexposed portion in the developer. Setting the content at or below the upper limit tends to maintain appropriate sensitivity, suppress dissolution of the exposed portion in the developer, and suppress deterioration of the sharpness and adhesion of the pattern.

[0371] When the alkali-soluble resin (C) contains an isocyanuric skeleton-containing resin (C3), the content of the isocyanuric skeleton-containing resin (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, even more preferably 40% by mass or more, and is 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 arbitrarily combined. For example, 20 to 90% by mass is preferred, 30 to 80% by mass is more preferred, and 40 to 70% by mass is even more preferred. By setting the content at or above the lower limit, light-emitting properties tend to improve. By setting the content at or below the upper limit, developability tends to improve.

[0372] The content of the (D) photopolymerization initiator is not particularly limited, but is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, even more preferably 2% by mass or more, particularly preferably 3% by mass or more, relative to the total solids content of the photosensitive colored resin composition of the present invention. It is also preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 8% by mass or less, and particularly preferably 6% by mass or less. The above upper and lower limits can be arbitrarily combined. For example, 0.1 to 15% by mass is preferred, 0.5 to 15% by mass is more preferred, 1 to 10% by mass is even more preferred, 2 to 8% by mass is even more preferred, and 3 to 6% by mass is particularly preferred. By setting the content at or above the lower limit, sensitivity degradation tends to be suppressed. By setting the content at or below the upper limit, it is possible to suppress a decrease in the solubility of the unexposed portion in the developer, and development defects tend to be suppressed.

[0373] When a polymerization accelerator is used together with the (D) photopolymerization initiator, the content of the polymerization accelerator is not particularly limited, but is preferably 0.05% by mass or more, and preferably 10% by mass or less, more preferably 5% by mass or less, relative to the total solids content of the photosensitive colored resin composition of the present invention. For example, 0.05 to 10% by mass is preferred, and 0.05 to 5% by mass is more preferred. Furthermore, the polymerization accelerator is preferably used in an amount of 0.1 to 50 parts by mass, more preferably 0.1 to 20 parts by mass, relative to 100 parts by mass of the (D) photopolymerization initiator. By setting the content of the polymerization accelerator at or above the lower limit, a decrease in sensitivity to exposure light tends to be suppressed. By setting the content at or below the upper limit, a decrease in the solubility of the unexposed portion in the developer tends to be suppressed, and development defects tend to be suppressed.

[0374] (D) When a sensitizing dye is used together with the photopolymerization initiator, the content ratio of the sensitizing dye is not particularly limited, but from the viewpoint of sensitivity, it is preferably 20 mass% or less, more preferably 15 mass% or less, and even more preferably 10 mass% or less, based on the total solid content in the photosensitive colored resin composition.

[0375] When the photosensitive colored resin composition of the present invention contains an ethylenically unsaturated compound (E), the content of the ethylenically unsaturated compound (E) is not particularly limited, but is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 10% by mass or more, particularly preferably 15% by mass or more, and is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less, relative to the total solids content of the photosensitive colored resin composition of the present invention. The upper and lower limits can be arbitrarily combined. For example, 1 to 30% by mass is preferred, 5 to 25% by mass is more preferred, 10 to 25% by mass is even more preferred, and 15 to 20% by mass is particularly preferred. By setting the content at or above the lower limit, appropriate sensitivity can be maintained, dissolution of the exposed area by the developer can be suppressed, and a decrease in the sharpness and adhesion of the pattern can be suppressed. By setting the content at or below the upper limit, increased penetration of the developer into the exposed area can be suppressed, making it easier to obtain a good image.

[0376] When the photosensitive colored resin composition of the present invention contains an ethylenically unsaturated compound (E), the content ratio of the alkali-soluble resin (C) relative to 100 parts by mass of the ethylenically unsaturated compound (E) is not particularly limited, but is preferably 100 parts by mass or more, more preferably 200 parts by mass or more, even more 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. Also, it is preferably 700 parts by mass or less, more preferably 500 parts by mass or less, even more preferably 450 parts by mass or less, and particularly preferably 400 parts by mass or less. The above upper and lower limits can be arbitrarily combined. For example, it is preferably 100 to 700 parts by mass, more preferably 200 to 700 parts by mass, even more 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 at or above the lower limit, an appropriate dissolution and development state without peeling or the like tends to be achieved. By adjusting the content to the upper limit or less, it is likely that an appropriate dissolution time in the developer can be obtained.

[0377] When an adhesion improver is used, its content is not particularly limited, but is preferably 0.1 to 5 mass%, more preferably 0.2 to 3 mass%, and even more preferably 0.4 to 2 mass% relative to the total solid content of the photosensitive color resin composition. By making it equal to or greater than the lower limit, there is a tendency that the effect of improving adhesion can be sufficiently obtained. By making it equal to or less than the upper limit, there is a tendency that it is possible to suppress a decrease in sensitivity and the remaining residue after development that causes defects.

[0378] When a surfactant is used, its content is not particularly limited, but is preferably 0.001 to 10 mass%, more preferably 0.005 to 1 mass%, even more preferably 0.01 to 0.5 mass%, and particularly preferably 0.03 to 0.3 mass%, relative to the total solid content of the photosensitive color resin composition. By making the content equal to or greater than the lower limit, the smoothness and uniformity of the coating film tend to be easily exhibited. By making the content equal to or less than the upper limit, the smoothness and uniformity of the coating film tend to be easily exhibited, and deterioration of other properties also tends to be suppressed.

[0379] The photosensitive color resin composition of the present invention is prepared by using a solvent so that the total solid content is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and 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 arbitrarily combined. For example, the composition is prepared so that the total solid content is preferably 5 to 50% by mass, more preferably 10 to 30% by mass, and even more preferably 15 to 25% by mass.

[0380] <Physical Properties of Photosensitive Colored Resin Composition> The optical density (OD) per μm of the coating film of the photosensitive colored resin composition of the present invention is not particularly limited, but is preferably 0.2 or more, more preferably 0.5 or more, even more preferably 0.7 or more, even more preferably 0.9 or more, and 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 arbitrarily combined. For example, 0.2 to 4.0 is preferred, 0.5 to 4.0 is more preferred, 0.5 to 3.0 is even more preferred, 0.5 to 2.0 is even more preferred, 0.7 to 2.0 is particularly preferred, and 0.9 to 1.5 is particularly preferred. By setting the OD at or above the lower limit, sufficient light-shielding properties tend to be obtained. By setting the OD at or below the upper limit, surface roughness of the electrode is suppressed, and the residual film rate tends to be high. The optical density (OD) per μm of coating film thickness can be measured using a coating film cured from the photosensitive colored resin composition of the present invention, and can be measured using a coating film of about 0.5 to 1.5 μm thick that has been heat-cured at 230°C for 20 minutes. Optical density refers to the transmission optical density, where the spectral sensitivity characteristics of the light-receiving section are indicated by the ISO Visual Density in the ISO 5-3 standard. Typically, the light source used is the A light source specified by the CIE (International Commission on Illumination). An example of a measuring instrument that can be used to measure transmission optical density is the X-Rite 361T(V) from Sakata Inx Engineering Co., Ltd.

[0381] [Pigment Dispersion] The components constituting the pigment dispersion of the present invention and its composition will be described. The pigment dispersion of the present invention contains (A) a colorant, (B) a dispersant, and (C) an alkali-soluble resin, and in particular, the (A) colorant contains an organic pigment (A-1), and the (C) alkali-soluble resin contains a resin (C1). It is also preferable that the pigment dispersion contains a solvent. As the components of the pigment dispersion of the present invention, those listed in the same item for the photosensitive color resin composition of the present invention can be preferably used.

[0382] Since the resin (C1) has high affinity with pigments and also contains methylene groups in the main chain, giving it flexibility that allows it to conform to the pigments, the pigment dispersion of the present invention tends to exhibit high pigment dispersibility. Furthermore, the photosensitive color resin composition using the pigment dispersion of the present invention tends to have a high film residual rate. As described above, this is because the resin (C1) contains many aromatic rings in the main chain, so it tends to have high developer resistance during development and high heat resistance during baking. Furthermore, when an organic electroluminescent device is formed using partition walls obtained from the photosensitive color resin composition, the current density tends to be high when a voltage is applied, as described above.

[0383] <Content of Each Component in the Pigment Dispersion> In the pigment dispersion of the present invention, the content of the colorant (A) relative to the total solid content in the pigment dispersion is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, particularly preferably 50% by mass or more, and particularly preferably 55% by mass or more. It is also 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 content at or above the lower limit, the photosensitive colored resin composition can be produced with an appropriate solid content concentration, and by setting the content at or below the upper limit, dispersibility tends to be improved. The combination of the upper and lower limits is preferably 10 to 80% by mass, more preferably 20 to 80% by mass, even more 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.

[0384] In the pigment dispersion of the present invention, the content of the organic pigment (A-1) is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, particularly preferably 50% by mass or more, and particularly preferably 55% by mass or more, based on the total solids content of the pigment dispersion. Furthermore, 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 content at or above the lower limit, the photosensitive colored resin composition can be produced with an appropriate solids concentration, while setting the content at or below the upper limit tends to improve dispersibility. The combination of the upper and lower limits is preferably 10 to 80% by mass, more preferably 20 to 80% by mass, even more 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.

[0385] In the pigment dispersion of the present invention, the content of the organic black pigment is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, particularly preferably 50% by mass or more, and particularly preferably 55% by mass or more, based on the total solids content of the pigment dispersion. Furthermore, 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 content at or above the lower limit, the photosensitive colored resin composition can be produced with an appropriate solids concentration, while setting the content at or below the upper limit tends to improve dispersibility. The combination of the upper and lower limits is preferably 10 to 80% by mass, more preferably 20 to 80% by mass, even more 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.

[0386] In the pigment dispersion of the present invention, the content of the dispersant (B) is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more, based on the total solids content of the pigment dispersion. It is also 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 the content at or above the lower limit, dispersibility tends to be improved. By setting the content at or below the upper limit, excess dispersant can be prevented from being lost, and the developability of the resulting photosensitive colored resin composition tends to be improved. The combination of the upper and lower limits 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 8 to 15% by mass.

[0387] When the pigment dispersion of the present invention contains an acrylic dispersant as dispersant (B), the content of the acrylic dispersant is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more, based on the total solids content of the pigment dispersion. It is also 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 the content at or above the lower limit, dispersibility tends to be improved and pattern adhesion tends to be improved during development of the cured product. Setting the content at or below the upper limit tends to improve the developability of the resulting photosensitive colored resin composition. The combination of the upper and lower limits 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.

[0388] In the pigment dispersion of the present invention, the content of the alkali-soluble resin (C) is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 25% by mass or more, based on the total solids content of the pigment dispersion. It is also preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less. By setting the content at or above the lower limit, dispersibility tends to be improved. By setting the content at or below the upper limit, the amount of colorant in the resulting photosensitive color resin composition can be optimized, and sufficient light-blocking properties tend to be ensured. The combination of the upper and lower limits is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, even more preferably 15 to 35% by mass, even more preferably 20 to 35% by mass, and particularly preferably 25 to 35% by mass. In the pigment dispersion of the present invention, the content of resin (C1) is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 25% by mass or more, based on the total solid content of the pigment dispersion. It is also preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less. By setting the content at or above the lower limit, dispersibility tends to be improved, while by setting the content at or below the upper limit, the amount of colorant in the resulting photosensitive color resin composition can be optimized, and sufficient light-blocking properties tend to be ensured. The combination of the upper and lower limits is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, even more preferably 15 to 35% by mass, even more preferably 20 to 35% by mass, and particularly preferably 25 to 35% by mass.

[0389] The pigment dispersion of the present invention is prepared using the organic solvent described above so that the solid content concentration is preferably 5 to 50% by mass, more preferably 10 to 30% by mass.

[0390] <Physical Properties of Pigment Dispersion> 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. It is also 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.

[0391] [Method for producing pigment dispersion] The pigment dispersion of the present invention is produced by a conventional method. (A) The colorant is preferably dispersed in advance using a paint conditioner, sand grinder, ball mill, roll mill, stone mill, jet mill, homogenizer, etc. The dispersion treatment results in the colorant (A) being microparticulated, which tends to improve the coating properties of the photosensitive color resin composition and reduce the surface roughness.

[0392] The dispersion treatment is preferably carried out in a system in which (A) a colorant, (B) a dispersant, and a solvent, and part or all of (C) an alkali-soluble resin are used in combination, or in a system in which (A) a colorant, (B) a dispersant, and a solvent, and part or all of (C) an alkali-soluble resin are used in combination. In particular, using a polymer dispersant as the (B) dispersant is preferred because it suppresses the thickening of the resulting pigment dispersion and photosensitive colored resin composition over time, i.e., it has excellent dispersion stability. As the (A) colorant, (B) dispersant, and solvent that can be used in the pigment dispersion, those described as being usable in the photosensitive colored resin composition can be preferably used.

[0393] When a dispersion treatment is performed on a liquid containing all the components to be incorporated into the photosensitive colored resin composition, the heat generated during the dispersion treatment may cause denaturation of highly reactive components. Therefore, it is preferable to perform the dispersion treatment in a system containing a polymer dispersant. When dispersing the colorant (A) using a sand grinder, glass beads or zirconia beads with a particle size of approximately 0.1 to 8 mm are preferably used. Regarding dispersion treatment conditions, a temperature of 0°C to 100°C is preferred, and room temperature to 80°C is more preferred. The appropriate dispersion time varies depending on the composition of the liquid and the size of the dispersion treatment device, so it should be adjusted appropriately. A guideline for dispersion is to control the gloss of the pigment dispersion so that the 20° specular gloss (JIS Z8741) of the photosensitive colored resin composition is in the range of 50 to 300. When the gloss of a photosensitive colored resin composition is low, the dispersion treatment is often insufficient, leaving coarse pigment (colorant) particles, which may result in insufficient developability, adhesion, resolution, surface roughness, etc. If the dispersion treatment is carried out until the gloss value exceeds the above range, the pigment will be crushed to produce a large number of ultrafine particles, which tends to impair dispersion stability. The dispersed particle size of the pigment dispersed in the pigment dispersion is preferably 0.03 to 0.3 μm, and can be measured by dynamic light scattering.

[0394] [Production method of photosensitive colored resin composition] Next, the pigment dispersion obtained by the above-mentioned dispersion treatment and other components contained in the photosensitive colored resin composition are mixed to make a uniform solution or dispersion.In the production process of photosensitive colored resin composition, fine dust may be mixed in the liquid, so it is desirable to filter the obtained photosensitive colored resin composition with a filter or the like.

[0395] [Cured Product] The cured product of the present invention can be obtained by curing the photosensitive colored resin composition of the present invention. The cured product obtained by curing the photosensitive colored resin composition of the present invention can be suitably used as a black matrix, an insulating film, or a partition wall, and is more suitably used as a partition wall. The film thickness of the cured product is preferably 0.5 μm or more, more preferably 0.7 μm or more, and even more preferably 0.9 μm or more. It is also 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. From the viewpoint of light-blocking properties, the optical density (OD) per μm of the cured product of the present invention is preferably 0.2 or more, more preferably 0.5 or more, even more preferably 0.7 or more, and particularly 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 especially preferably 1.5 or less. For example, the optical density (OD) is preferably 0.2 to 4.0, more preferably 0.5 to 4.0, even more preferably 0.5 to 3.0, still more preferably 0.5 to 2.0, particularly 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 below.

[0396] Next, the cured product using the photosensitive colored resin composition of the present invention will be described according to the method for producing the same.

[0397] (1) Support The material of the support for forming the cured product is not particularly limited as long as it has adequate strength. Substrates are mainly used, and examples of 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, thermosetting resin sheets such as epoxy resins, unsaturated polyester resins, and poly(meth)acrylic resins, and various types of glass. Glass and heat-resistant resins are preferred from the perspective of heat resistance. In addition, transparent electrodes such as ITO and IZO, or metal electrodes such as silver, gold, platinum, aluminum, and magnesium may be formed on the surface of the substrate. In addition to the above-mentioned substrates, it is also possible to form the substrate on a TFT array.

[0398] To improve surface properties such as adhesiveness, the support may be subjected to, for example, corona discharge treatment, ozone treatment, or thin film formation treatment using various resins such as silane coupling agents or urethane resins, as needed. The thickness of the support is preferably in the range of 0.05 to 10 mm, more preferably 0.1 to 7 mm. When thin film formation treatment using various resins is performed, the film thickness is preferably in the range of 0.01 to 10 μm, more preferably 0.05 to 5 μm.

[0399] The photosensitive colored resin composition is applied in the form of a film or pattern by coating or other methods onto a support on which a cured product is to be formed, and the solvent is dried. Subsequently, a pattern is formed by a method such as photolithography, which involves exposure and development. Thereafter, a cured product is formed on the substrate by performing additional exposure or heat curing treatment as necessary.

[0400] (2) Method of supplying to a support The photosensitive colored resin composition of the present invention is preferably supplied onto a support in a state dissolved or dispersed in a solvent. The supplying method can be a conventionally known method, such as a spinner method, a wire bar method, a flow coating method, a die coating method, a roll coating method, or a spray coating method. It may also be supplied in a pattern by, for example, an inkjet method or a printing method. The die coating method is preferable from an overall viewpoint, since it significantly reduces the amount of coating liquid used, is completely free from the influence of mist or the like that adheres when using a spin coating method, and suppresses the generation of foreign matter.

[0401] The amount of coating varies depending on the application, but is preferably applied so that the dry film thickness is 0.5 to 10 μm, more preferably 1 to 9 μm, and particularly preferably 1 to 7 μm. It is important that the dry film thickness or the height of the finally formed cured product is uniform across the entire support. Minimizing variation results in uniform light-blocking properties within the support, and when used as a partition wall, it is possible to produce a uniform light-emitting layer and suppress display defects during light emission.

[0402] When the photosensitive colored resin composition of the present invention is used to form cured products of different heights in a batch by photolithography, the heights of the finally formed cured products will be different.

[0403] (3) Drying method After supplying the photosensitive color resin composition onto the support, it is preferable to dry it by a drying method using a hot plate, an IR oven, or a convection oven. It may also be combined with a reduced pressure drying method in which drying is performed in a reduced pressure chamber without increasing the temperature.

[0404] Drying conditions can be appropriately selected depending on the type of solvent component, the performance of the dryer used, etc. The drying time is selected depending on the type of solvent component, the performance of the dryer used, etc., preferably 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.

[0405] (4) Exposure method Exposure is carried out by superposing a negative mask pattern on the coating film of the photosensitive colored resin composition, and irradiating a light source of ultraviolet or visible light through this mask pattern. When exposure is carried out using an exposure mask, a method of bringing the exposure mask close to the coating film of the photosensitive colored resin composition, or a method of placing the exposure mask at a position away from the coating film of the photosensitive colored resin composition and projecting the exposure light through the exposure mask may be used. A scanning exposure method using laser light without using a mask pattern may also be used. If necessary, in order to prevent a decrease in the sensitivity of the photopolymerizable layer due to oxygen, exposure may be carried out in a deoxygenated atmosphere, or after forming an oxygen-blocking layer such as a polyvinyl alcohol layer on the photopolymerizable layer.

[0406] When simultaneously forming cured products of different heights using photolithography, for example, an exposure mask is used that has a light-shielding portion (light transmittance 0%) and multiple openings, each of which has a lower average light transmittance (intermediate-transmitting openings) than the opening with the highest average light transmittance (fully-transmitting openings). This method generates a difference in film remaining rate due to the difference in average light transmittance between the intermediate-transmitting openings and the fully-transmitting openings, i.e., the difference in exposure dose. A known method for producing intermediate-transmitting openings is, for example, a matrix-shaped light-shielding pattern having minute polygonal light-shielding units. A known method for producing the intermediate-transmitting openings is to control the light transmittance using a film of a chromium-based, molybdenum-based, tungsten-based, or silicone-based material as an absorber.

[0407] The light source used for exposure is not particularly limited. Examples of the light source include lamp light sources such as 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 arcs, and fluorescent lamps, and laser light 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, an optical filter can also be used.

[0408] The optical filter may be, for example, a thin film type capable of controlling the light transmittance at the exposure wavelength, and in this case, examples of the material include Cr compounds (Cr oxides, nitrides, oxynitrides, fluorides, etc.), MoSi, Si, W, and Al.

[0409] The exposure dose is not particularly limited, but is preferably 1 mJ / cm 2 More preferably, 5 mJ / cm 2 More preferably, 10 mJ / cm 2 or more, and preferably 300 mJ / cm 2 or less, more preferably 200 mJ / cm 2 More preferably, 150 mJ / cm or less 2 The following is the result.

[0410] (5) Development Method After the above-mentioned exposure, an image pattern can be formed on the support by development using an aqueous solution of an alkaline compound or an organic solvent. The aqueous solution of the alkaline compound may further contain, for example, a surfactant, an organic solvent, a buffer, a complexing agent, a dye, or a pigment.

[0411] Examples of alkaline compounds include inorganic alkaline 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 alkaline compounds such as mono-, di-, or triethanolamine, mono-, di-, or trimethylamine, mono-, di-, or triethylamine, mono- or diisopropylamine, n-butylamine, mono-, di-, or triisopropanolamine, ethyleneimine, ethylenediimine, tetramethylammonium hydroxide (TMAH), and choline. These alkaline compounds may be used alone or in combination of two or more.

[0412] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, and monoglyceride alkyl esters; anionic surfactants such as alkylbenzenesulfonates, alkylnaphthalenesulfonates, alkyl sulfates, alkylsulfonates, and sulfosuccinate salts; and amphoteric surfactants such as alkylbetaines and amino acids.

[0413] Examples of organic solvents include isopropyl alcohol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol, and diacetone alcohol. These organic solvents may be used in combination of two or more. Furthermore, the organic solvent may be used alone or in combination with water or an aqueous solution of an alkaline compound.

[0414] The conditions for the development treatment are not particularly limited, and the development temperature is preferably 10 to 50° C., more preferably 15 to 45° C., and even more preferably 20 to 40° C. The development method can be, for example, an immersion development method, a spray development method, a brush development method, or an ultrasonic development method.

[0415] (6) Post-exposure and heat-curing treatment The developed substrate may be subjected to post-exposure treatment using a method similar to the above-mentioned exposure method, if necessary. After development or post-exposure, a heat-curing treatment (also called baking) may be performed. The heat-curing treatment conditions are preferably a temperature of 100 to 280°C, more preferably 150 to 250°C, and a time of 5 to 60 minutes.

[0416] [Partition Wall] The photosensitive color resin composition of the present invention can be suitably used to form a partition wall, particularly a partition wall for separating an organic layer of an organic electroluminescent element. Examples of the organic layer used in an organic electroluminescent element include an organic layer used as a hole injection layer, a hole transport layer, or a hole transport layer on a hole injection layer, as described in JP 2016-165396 A.

[0417] When the present invention is used as a partition wall, the size, shape, etc. are appropriately adjusted depending on the specifications of the organic electroluminescent device to which it is applied, but the film thickness and optical density (OD) per μm of the partition wall formed from the photosensitive color resin composition of the present invention are the same as the values ​​of the cured film.

[0418] [Organic Electroluminescent Device] The organic electroluminescent device of the present invention comprises a cured product, such as a partition wall, formed from the photosensitive colored resin composition of the present invention. For example, various organic electroluminescent devices are manufactured using a substrate having a partition wall pattern manufactured by the above-described method. The method for forming the organic electroluminescent device is not particularly limited, but preferably, after forming a partition wall pattern on the substrate by the above-described method, organic layers such as pixels are formed by a vapor deposition method in which a functional material is sublimated in a vacuum and deposited in the area surrounded by the partition walls on the substrate to form a film, or a wet process such as a casting method, a spin coating method, or an inkjet printing method, to manufacture the organic electroluminescent device.

[0419] Examples of organic electroluminescent devices include bottom-emission and top-emission devices. Bottom-emission devices are fabricated, for example, by forming a partition wall on a glass substrate on which a transparent electrode is laminated, and then laminating a hole transport layer, a light-emitting layer, an electron transport layer, and a metal electrode layer in the opening surrounded by the partition wall. On the other hand, top-emission devices are fabricated, for example, by forming a partition wall on a glass substrate on which a metal electrode layer is laminated as a reflective layer, and then laminating an electron transport layer, a light-emitting layer, a hole transport layer, and a transparent electrode layer in the opening surrounded by the partition wall. In many cases, an anode is disposed on a support, but this is not a limitation. Examples of light-emitting layers include organic electroluminescent layers such as those described in Japanese Patent Publication No. 2009-146691 and Japanese Patent Publication No. 5734681. Quantum dots such as those described in Japanese Patent Publication No. 5653387 and Japanese Patent Publication No. 5653101 may also be used.

[0420] The layer structure is not limited to this, and for example, each of the hole transport layer and the electron transport layer may have a laminate structure consisting of two or more layers from the viewpoint of luminous efficiency. The thickness of each layer is not particularly limited, but is preferably 1 to 500 nm from the viewpoint of luminous efficiency and brightness.

[0421] The organic electroluminescent element may be formed with each RGB color separated for each opening, or two or more colors may be stacked in one opening. The organic electroluminescent element may have a sealing layer from the viewpoint of improving reliability. The sealing layer has the function of preventing moisture in the air from being adsorbed to the organic electroluminescent element and reducing the luminous efficiency. The organic electroluminescent element may have a low-reflection film at the interface with air from the viewpoint of improving light extraction efficiency. By disposing the low-reflection film at the interface between air and the element, the refractive index gap can be reduced, and it is expected that reflection at the interface can be suppressed. For example, moth-eye structure and super multilayer film technology can be applied to such a low-reflection film.

[0422] When organic electroluminescent elements are used as pixels of an image display device, it is necessary to prevent light from the light-emitting layer of one pixel from leaking to other pixels. Furthermore, when the electrodes or the like are made of metal, it is necessary to prevent degradation of image quality due to reflection of external light. Therefore, it is preferable to impart light-shielding properties to the partition walls constituting the organic electroluminescent element. Since it is necessary to provide electrodes on the upper and lower surfaces of the partition walls in organic electroluminescent elements, it is preferable that the partition walls have high resistance and low dielectric constant from the viewpoint of insulation. Therefore, when a colorant is used to impart light-shielding properties to the partition walls, it is preferable to use the above-mentioned organic pigment having high resistance and low dielectric constant.

[0423] [Color filter containing luminescent nanocrystalline particles] The color filter containing the luminescent nanocrystalline particles of the present invention is not particularly limited as long as it has the partition walls of the present invention, and examples include those in which pixels are formed in areas partitioned by the partition walls.

[0424] Fig. 1 is a schematic cross-sectional view of an example of a color filter including a partition wall of the present invention. As shown in Fig. 1, the color filter 100 includes a substrate 10, a partition wall 20 provided on the substrate, a red pixel 30, a green pixel 40, and a blue pixel 50. The red pixel 30, the green pixel 40, and the blue pixel 50 are arranged in a lattice pattern, repeating in this order. The partition wall 20 is provided between these adjacent pixels. In other words, these adjacent pixels are separated by the partition wall 20.

[0425] The red pixel 30 contains red-emitting nanocrystalline particles 2, and the green pixel 40 contains green-emitting nanocrystalline particles 1. The blue pixel 50 is a pixel that transmits blue light from the light source.

[0426] These nanocrystalline particles are nano-sized crystals that absorb excitation light and emit fluorescence or phosphorescence, and are, for example, crystals whose maximum particle size as measured by a transmission electron microscope or a scanning electron microscope is 100 nm or less.

[0427] The luminescent nanocrystalline particles are capable of absorbing light of a predetermined wavelength and emitting light (fluorescence or phosphorescence) of a wavelength different from the absorbed wavelength. For example, red-luminescent nanocrystalline particles 2 emit light having a peak emission wavelength in the range of 605 to 665 nm (red light), and green-luminescent nanocrystalline particles 1 emit light having a peak emission wavelength in the range of 500 to 560 nm (green light).

[0428] According to the solution of the Schrodinger wave equation of the well-well potential model, the wavelength (emission color) of light emitted by luminescent nanocrystalline particles depends on the size (e.g., particle diameter) of the luminescent nanocrystalline particles, but also on the energy gap of the luminescent nanocrystalline particles. Therefore, the emission color can be selected by changing the constituent material and size of the luminescent nanocrystalline particles used. Examples of luminescent nanocrystalline particles include quantum dots.

[0429] The method for producing a color filter containing luminescent nanocrystalline particles is not particularly limited, but examples thereof include a method of preparing a substrate having partition walls formed from the cured product of the present invention and forming a layer containing luminescent nanocrystalline particles in the areas partitioned by the partition walls. The method for forming the layer containing luminescent nanocrystalline particles is not particularly limited, but the color filter can be produced, for example, by a method of selectively depositing an ink composition containing luminescent nanocrystalline particles by an inkjet method and curing the ink composition by irradiation with active energy rays or heating.

[0430] [Image Display Device] Examples of the image display device of the present invention include an organic EL display device having a partition wall or organic electroluminescent element containing the cured product of the present invention. The organic EL display device is not particularly limited in type or structure as long as it contains the above-mentioned organic electroluminescent element, and can be assembled, for example, by a conventional method using active-drive organic electroluminescent elements. For example, it can be formed by a method such as that described in "Organic EL Display" (Ohmsha, published August 20, 2004, by Tokito Shizuo, Adachi Chinaya, and Murata Hideyuki). For example, an image can be displayed by combining an organic electroluminescent element that emits white light with a color filter, or by combining organic electroluminescent elements that emit different colors of light, such as RGB.

[0431] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples as long as it does not deviate from the gist of the invention. The components of the photosensitive colored resin composition used in the following examples and comparative examples, and the evaluation methods thereof, are as follows.

[0432] <Alkali-soluble resin-I>

[0433]

[0434] 70 parts by mass of an epoxy compound (epoxy equivalent 273) having a repeating unit represented by the formula above, 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 charged into a reaction vessel and stirred. Next, 7.6 parts by mass of phthalic anhydride and 37.1 parts by mass of propylene glycol monomethyl ether acetate were added and reacted. The alkali-soluble resin-I thus obtained had a weight average molecular weight Mw of 2456 and an acid value of 64 mg KOH / g as measured by GPC, and corresponds to resin (C1) and a structure represented by formula (C1-1).

[0435] <Alkali-Soluble Resin-II> 155 parts by mass of EPICLON HP7200HH (dicyclopentadiene-phenol polymerized polyglycidyl ether, weight-average molecular weight 1000, epoxy equivalent 270) manufactured by DIC Corporation, 41 parts by mass of acrylic acid, 0.1 parts by mass of p-methoxyphenol, 2.5 parts by mass of triphenylphosphine, and 270 parts by mass of propylene glycol monomethyl ether acetate were charged into a reaction vessel and heated with stirring at 100°C until the acid value reached 3.0 mgKOH / g or less. It took 9 hours for the acid value to reach the target value (acid value 2.9 mgKOH / g). Next, 74 g of tetrahydrophthalic anhydride was added, and the mixture was reacted at 120°C for 4 hours. The alkali-soluble resin-II thus obtained had a weight-average molecular weight Mw of 3500 and an acid value of 60 mgKOH / g, and does not correspond to resin (C1).

[0436] <Alkali-soluble resin-III> "ZCR-1664H" manufactured by Nippon Kayaku Co., Ltd. (weight average molecular weight Mw = 5200, acid value = 60 mgKOH / g). It has a partial structure represented by the following formula, in which * represents a bond. Alkali-soluble resin-III does not fall under the category of resin (C1).

[0437]

[0438] <Alkali-soluble resin-IV> "CCR-1342H" manufactured by Nippon Kayaku Co., Ltd. (weight average molecular weight Mw = 6500, acid value = 60 mgKOH / g). It has a partial structure represented by the following formula, in which * represents a bond. Alkali-soluble resin-IV does not fall under the category of resin (C1).

[0439]

[0440] <Alkali-soluble resin-V>

[0441]

[0442] 240 parts by weight of the epoxy compound (epoxy equivalent 264) of the above structure, 68.3 parts by weight of acrylic acid, 263.1 parts by weight of methoxybutyl acetate, 6.4 parts by weight of triphenylphosphine, and 0.16 parts by weight of paramethoxyphenol, a thermometer, a stirrer, a flask equipped with a condenser, was added with stirring at 90 ° C. until the acid value was 5 mg KOH / g or less for 12 hours. Next, 9.2 parts by weight of trimethylolpropane (TMP), 115.6 parts by weight of biphenyltetracarboxylic dianhydride (BPDA), 25.1 parts by weight of tetrahydrophthalic anhydride (THPA), a thermometer, a stirrer, a flask equipped with a condenser, was added to the reaction solution obtained by the above reaction, and the temperature was slowly raised to 105 ° C. while stirring. The solid acid value was 104 mg KOH / g, and the weight average molecular weight (Mw) measured by GPC in terms of polystyrene was 2660. An alkali-soluble resin-V was obtained. Alkali-soluble resin-V corresponds to (C2) epoxy (meth)acrylate resin.

[0443] <Alkali-soluble resin-VI> "KBR-201" manufactured by KISCO Corporation. A resin having a fluorene bisphenol skeleton. Weight-average molecular weight: 5107, acid value: 113 mg KOH / g. Alkali-soluble resin-VI corresponds to (C2) epoxy (meth)acrylate resin.

[0444] <Alkali-soluble resin-VII>

[0445]

[0446] 50.0 parts by mass of an epoxy compound having the chemical structure represented by the above formula, 170.3 parts by mass of propylene glycol monomethyl ether acetate, 0.89 parts by mass of 2,4,6-trisdimethylaminomethylphenol, and 0.050 parts by mass of p-methoxyphenol were stirred while purging with nitrogen, and the temperature was raised to 100°C. To this was added 44.3 parts by mass of methacrylic acid dropwise over 30 minutes. The mixture was further reacted at 100°C for 8 hours until the acid value reached 10 mgKOH / g or less, yielding epoxy (meth)acrylate solution A.

[0447]

[0448] 50.0 parts by weight of epoxy (meth)acrylate solution A (solids concentration 35.9% by weight) containing the epoxy (meth)acrylate compound of the above chemical structure and 3.1 parts by weight of propylene glycol monomethyl ether acetate were stirred while purging with nitrogen. 3.48 parts by weight of pyromellitic dianhydride (PDMA) and 2.36 parts by weight of phthalic anhydride were added, the temperature was raised to 80°C, and the reaction was allowed to proceed for 5 hours to obtain Alkali-Soluble Resin-VII, which had a solids content of 40% by weight, an acid value of 145 mg KOH / g, and a weight average molecular weight (Mw) of 2800 in terms of polystyrene as measured by GPC. Alkali-Soluble Resin-VII corresponds to (C3) isocyanuric skeleton-containing resin.

[0449] <Alkali-soluble resin-VIII>

[0450]

[0451] 100 parts by mass of an epoxy compound (epoxy equivalent 273) having a repeating unit represented by the 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 charged into a reaction vessel and stirred. Next, 22.8 parts by mass of trimellitic anhydride and 48.9 parts by mass of propylene glycol monomethyl ether acetate were added and reacted. The alkali-soluble resin-I thus obtained had a weight average molecular weight Mw of 1668 and an acid value of 96.3 mg KOH / g as measured by GPC, and corresponded to resin (C1) and the structure represented by formula (C1-1).

[0452] <Colorant-I> Irgaphor (registered trademark) Black S 0100 CF (having a chemical structure represented by the following formula (A-1-2)), manufactured by BASF.

[0453]

[0454] <Dispersant-I> A block copolymer consisting of an A block containing a repeating unit having a solvent-philic group and a B block containing a repeating unit having a tertiary amino group. <Dispersant-II> A block copolymer consisting of an A block containing a repeating unit having a solvent-philic group and a B block containing a repeating unit having a tertiary amino group and a quaternary ammonium group.

[0455] <Solvent-I> PGMEA: Propylene glycol monomethyl ether acetate <Solvent-II> MB: 3-methoxy-1-butanol <Solvent-III> MBA: 3-methoxy-butyl acetate.

[0456] <Photopolymerization initiator-I> An oxime ester photopolymerization initiator having the following chemical structure.

[0457]

[0458] <Ethylenically Unsaturated Compound-I> DPHA: manufactured by Nippon Kayaku Co., Ltd. A mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate.

[0459] <Surfactant-I> Megafac F-559 manufactured by DIC Corporation.

[0460] <Viscosity Evaluation> Using a RE-85L viscometer manufactured by Toki Sangyo Co., Ltd. (measurement conditions: 23°C, 20 rpm), the viscosity of the pigment dispersion was measured immediately after preparation, after leaving the pigment dispersion to stand at room temperature (24°C) for 1 day, and after leaving it to stand for 3 days after preparation, and was judged as follows. From the viewpoint of the coatability and stability over time of the photosensitive colored resin composition, a lower viscosity of the pigment dispersion is preferable. A: Viscosity is 10 mPa·s or less B: Viscosity is greater than 10 mPa·s C: Unable to disperse and solidifies

[0461] <Preparation of Substrate for Evaluating Film Remaining Rate> Using a spinner, the photosensitive colored resin composition of each Example and Comparative Example was applied onto a substrate having an indium tin oxide (ITO) film formed on the surface of a glass substrate with a film thickness of 0.7 mm, so that the thickness after heat curing (baking) would be 1.5 μm. Thereafter, a drying treatment was carried out in a vacuum dryer for 60 seconds. Subsequently, the coating was dried by heating for 100 seconds on a hot plate heated to 100°C, to obtain a coated film substrate. The film thickness of the heated and dried coating film was measured by the method described below, and the film thickness T1 (μm) was determined. The obtained coated film substrate was exposed to light using a photomask. A mirror projection type exposure machine (MPA-600FA) manufactured by Canon Inc. was used, and the exposure dose was 80 mJ / cm. ２ The exposure time was 20 seconds so that the illuminance was 500 mW / cm ２ The slit width was 1.6 mm. A mask with lattice-shaped openings (having a 50 μm square-shaped covered area and a plurality of the coated areas separated by 50 μm exposed areas) was used as the photomask. Subsequently, using a developer consisting of an aqueous solution containing 0.05% by mass of potassium hydroxide and 0.08% by mass of a nonionic surfactant ("A-60" manufactured by Kao Corporation), shower development was performed at 24°C under a water pressure of 0.05 MPa. Development was then stopped by flushing the developer with pure water, and the substrate was washed for 10 seconds with a water spray. The shower development time was 1.6 times the time required for the unexposed areas of the coating to be dissolved and removed. The photosensitive colored resin composition was washed away from the areas corresponding to the square light-shielding areas after development, exposing the ITO substrate and forming holes. This substrate was then heat-cured (baked) in an oven at 230°C for 30 minutes to obtain a patterned substrate for measuring patterning properties. The film thickness T2 (μm) at this time was measured.

[0462] <Calculation of Remaining Film Ratio> The thickness of the coating film on the patterned substrate during each process (after drying and baking) was measured using a non-contact surface / layer cross-sectional shape measurement system, VertScan® 2.0, manufactured by Ryoka Systems Co., Ltd. The ratio of the baked film thickness (T2) to the dried film thickness (T1) among the measured film thicknesses was calculated as the remaining film ratio. Remaining film ratio (%) = (T2 / T1) × 100 (%) The calculated remaining film ratio was evaluated as follows: A indicates the highest and best remaining film ratio, and a remaining film ratio of 75% or more tends to be satisfactory for practical use. A: Remaining film ratio 80% or more B: Remaining film ratio less than 80% and 75% or more C: Remaining film ratio less than 75% Note that the remaining film ratio is related to the exposure sensitivity of the resist, its solubility in the developer, and its thermal decomposition during baking, and the higher the remaining film ratio, the better.

[0463] <Measurement of optical density per unit film thickness (unit OD value)> The optical density per unit film thickness was measured by the following procedure. Using a spinner, the photosensitive colored resin composition of each Example and Comparative Example was applied to a glass substrate so that the thickness would be 1.5 μm after heat curing (baking). Thereafter, a drying treatment was carried out in a vacuum dryer for 60 seconds. Subsequently, the coating was heated and dried for 100 seconds on a hot plate heated to 100°C. The resulting coating film was exposed to light without using an exposure mask. A mirror projection type exposure machine (MPA-600FA) manufactured by Canon Inc. was used as the irradiation light source, and the exposure amount was 80 mJ / cm. ２ The exposure time was 20 seconds so that the illuminance was 500 mW / cm ２ The resist-coated substrate 1 was then heated and cured in an oven at 230°C for 30 minutes to obtain a resist-coated substrate 1. The optical density (OD value) of the obtained resist-coated substrate 1 was measured using an X-Rite 361T(V) transmission densitometer (color temperature of illumination light source: approximately 2850K (equivalent to CIE standard illuminant A), spectral sensitivity characteristics of the light-receiving section: ISO visual density according to ISO 5-3 standard), and the film thickness was measured using a VertScan® 2.0 non-contact surface / layer cross-sectional shape measurement system manufactured by Ryoka Systems Co., Ltd., and the optical density (unit OD value) per unit film thickness (1 μm) was calculated from the optical density (OD value) and film thickness. The OD value is a value that indicates the light-shielding ability, with a larger value indicating a higher light-shielding ability.

[0464] <Preparation of Patterned Substrate for Organic Electroluminescent Device> A substrate in which a transparent conductive film of indium tin oxide (ITO) was deposited to a thickness of 70 nm on glass was used to form an anode using ordinary photolithography techniques and hydrochloric acid etching, and the photosensitive colored resin composition of each Example and Comparative Example was applied using a spinner. The substrate was then subjected to a drying treatment for 60 seconds in a vacuum dryer. Subsequently, the substrate was heated and dried for 100 seconds on a hot plate heated to 100°C. The resulting coated substrate was exposed to light using a photomask. A mirror projection exposure machine (MPA-600FA) manufactured by Canon Inc. was used, and the exposure dose was 80 mJ / cm. ２ The exposure time was 20 seconds so that the illuminance was 500 mW / cm ２ The slit width was 1.6 mm. The photomask used was a mask with lattice-shaped openings (having rectangular covering portions measuring 40 μm in length and 80 μm in width, with a plurality of the covering portions separated by 20 μm exposed portions in the long and short axis directions). Subsequently, using a developer consisting of an aqueous solution containing 0.05% by mass of potassium hydroxide and 0.08% by mass of a nonionic surfactant ("A-60" manufactured by Kao Corporation), shower development was performed at 24°C and a water pressure of 0.05 MPa. Development was then stopped by flushing the developer with pure water, and the substrate was washed with a water spray for 10 seconds. The shower development time was 1.6 times the time it took for the unexposed portions of the coating film to be dissolved and removed. These operations developed and removed the openings, yielding an electrode substrate with a partition wall pattern. The electrode substrate with the pattern formed thereon was heat-cured (baked) in an oven at 230°C for 30 minutes to obtain a patterned substrate for an organic electroluminescent element.

[0465] <Preparation of Device for Evaluating Organic Electroluminescent Devices> An organic electroluminescent device was prepared by vacuum deposition of layers stacked in this order on the entire surface of the prepared patterned substrate for organic electroluminescent devices: molybdenum oxide to a thickness of 10 nm as a hole injection layer, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine to a thickness of 60 nm as a hole transport layer, tris(8-hydroxyquinolinato)aluminum to a thickness of 60 nm as a light-emitting layer, 8-hydroxyquinolinolato-lithium to a thickness of 1 nm as an electron injection layer, and aluminum to a thickness of 80 nm as a cathode. Next, a sealing glass having a central recess was provided with a desiccant attached to the recess, and a UV-curable resin was applied to the frame portion surrounding the recess. The sealing glass was arranged so that the recessed portion of the sealing glass covered all of the organic electroluminescent elements on the electrode substrate, the sealing glass was attached to the electrode substrate, the UV curable resin was irradiated with UV light to harden it, and the hollow structure was sealed, thereby producing a device for evaluating organic electroluminescent elements.

[0466] <Evaluation of Light-Emitting Properties of Organic Electroluminescent Device> A direct current was passed through the prepared device for evaluating organic electroluminescent devices, and the current density was measured at a driving voltage of 4 V. The measured current density was judged as follows: A higher current density is preferable, and a current density of 0.6 mA / cm ２ A: Current density of 0.8 mA / cm or more tends to pose no practical problems. ２ B: Current density 0.6mA / cm ２ 0.8 mA / cm or more ２ C: Current density 0.6 / cm ２ less than

[0467] <Preparation of Pigment Dispersions 1 to 9> The pigments, dispersants, alkali-soluble resins, and solvents shown in Tables 1 and 2 were mixed in the mass ratios shown in Table 1. This mixture was subjected to a dispersion treatment using a paint shaker at a temperature range of 25 to 45°C for 3 hours. Zirconia beads with a diameter of 0.5 mm were used as beads, and 2.5 times the mass of the dispersion was added. After dispersion was completed, the beads and the dispersion were separated using a filter. Pigment Dispersions 1 to 9 were prepared. The amount of solvent in Tables 1 and 2 includes the amount of solvent derived from the dispersant and alkali-soluble resin.

[0468]

[0469]

[0470] As shown in Table 1, Examples 1 to 4, which used alkali-soluble resin-I, were observed to have low viscosity and excellent dispersibility. On the other hand, Comparative Examples 1, 3, and 4 were unable to disperse and solidified, while Comparative Example 2 was dispersible but had high viscosity and poor dispersibility. Furthermore, as shown in Table 2, Examples 3 to 5 maintained stable viscosity even three days after preparation of the pigment dispersion, while Comparative Example 5 was observed to gradually increase in viscosity immediately after preparation of the pigment dispersion. Regarding the above phenomenon, Resin (C1) contains many aromatic rings in its main chain, giving it high affinity with pigments. Furthermore, the main chain also contains methylene groups, providing flexibility that allows it to conform to the surface shape of the pigment, which is thought to be highly effective in improving pigment dispersibility. Alkali-soluble resin-I and alkali-soluble resin-VIII are considered to correspond to resin (C1) and exhibit high pigment dispersibility. Furthermore, Alkali-soluble resin-VIII has an increased number of hydroxyl groups, which have higher solvent affinity than alkali-soluble resin-I, which is thought to have improved pigment dispersibility and viscosity stability. While alkali-soluble resin-II has a low content of aromatic rings in its main chain, it has a bulky dicyclopentane skeleton, which is thought to result in a low pigment dispersibility.Also, alkali-soluble resins-III and IV contain many aromatic rings in their main chains, but their main chains are rigid and lack flexibility, which is disadvantageous in terms of conforming to the surface shape of the pigment, and therefore are thought to result in a low pigment dispersibility.

[0471] [Examples 5 to 9, Comparative Examples 6 and 7] In Examples 5 to 9 and Comparative Examples 6 and 7, each component was added to pigment dispersions 7 to 9 so that the content ratio of the solid content of each component in the total solid content was the value shown in Table 2, and further a solvent was added so that the content ratio of the total solid content was 17 mass% with PGMEA / MB / MBA = 72 / 20 / 8, and the mixture was stirred and dissolved to prepare photosensitive colored resin compositions of Examples 5 to 10 and Comparative Examples 6 and 7. The evaluation results of the unit OD value and residual film rate are shown in Tables 3 and 4.

[0472]

[0473]

[0474] As shown in Tables 3 and 4, it was observed that the film retention rates of Examples 6 to 12 were better than those of Comparative Examples 6 and 7. This is thought to be because resin (C1) contains many aromatic rings in its main chain, which improves developer resistance during development and increases the film retention rate. It is thought that alkali-soluble resin-I corresponds to resin (C1) and showed a high film retention rate. A comparison of Examples 8 to 10 and 12 revealed that the film retention rate was further improved when alkali-soluble resin-VI was used. This is thought to be because the structure of alkali-soluble resin-VI contains more aromatic rings than alkali-soluble resins-V and -VII.

[0475] The organic electroluminescent devices fabricated using the prepared photosensitive colored resin compositions of Examples 6, 8, and 10 and Comparative Examples 6 and 7 were evaluated. Table 5 shows the evaluation results.

[0476]

[0477] Examples 6, 8, and 10 in Table 5 tend to have high current densities during light emission. This is presumably because Alkali-Soluble Resin-I and Alkali-Soluble Resin-VIII contain many aromatic rings in their main chains, improving developer resistance during development and reducing the accumulation of decomposition products in the pixel areas of the organic electroluminescent device during development. Furthermore, Alkali-Soluble Resin-VII has a highly heat-resistant isocyanuric skeleton, which is thought to reduce the accumulation of thermal decomposition products in the pixels during baking, thereby demonstrating even higher current density values. On the other hand, Comparative Examples 6 and 7 tend to have low current densities. This is presumably because the fewer aromatic rings contained in the main chains reduce developer resistance, resulting in increased accumulation of decomposition products in the pixel areas of the organic electroluminescent device during development.

[0478] 1 Green-emitting nanocrystalline particle 2 Red-emitting nanocrystalline particle 10 Substrate 20 Partition wall 30 Red pixel 40 Green pixel 50 Blue pixel 100 Color filter

Claims

1. A photosensitive color resin composition comprising (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin, and (D) a photopolymerization initiator, The colorant (A) contains an organic pigment (A-1), A photosensitive colored resin composition, characterized in that the (C) alkali-soluble resin contains a resin (C1) having a structural unit represented by the following general formula (1): 【Chemistry 1】 (In formula (1), R 1 represents a hydrogen atom or a methyl group. R 2 each independently represents an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms and has at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid as a substituent. * represents a bond.)

2. The photosensitive colored resin composition according to claim 1, wherein the resin (C1) has a structural unit represented by the following general formula (2): 【Chemistry 2】 In formula (2), A represents a hydrogen atom or a polybasic acid residue. R 1 represents a hydrogen atom or a methyl group. R 2 each independently represents an alkyl group having 1 to 4 carbon atoms. * represents a bond.)

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

4. 4. The photosensitive colored resin composition according to claim 3, wherein the organic black pigment comprises a benzodifuranone-based organic black pigment.

5. The organic black pigment is a compound represented by the following general formula (A-1-1), a geometric isomer thereof, a salt thereof, or a salt of the geometric isomer thereof. The photosensitive colored resin composition according to claim 4, comprising an organic black pigment. 【Chemistry 3】 (In formula (A-1-1), R 611 and R 616 Each independently represents a hydrogen atom, CH 3 , C.F. 3 , a fluorine atom or a 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, R 621 , COOH, COOR 621 , COO - , C.O.N.H. 2 , C.O.N.R. 611 , C.O.R. 621 R 622 , C.N., O.H., O.R. 621 , COCR 621 , O.O.C.N.H. 2 , OOCNHR 621 , OOCNR 621 R 622 , NO 2 , N.H. 2 , N.H.R. 621 , N.R. 621 R 622 , NHCOR 622 , N.R. 621 C.O.R. 622 , N=CH 2 , N=CHR 621 , N=CR 621 R 622 , S.H., S.R. 621 , S.O.R. 621 , S.O. 2 R 621 , S.O. 3 R 621 , S.O. 3 H, SO 3 - , S.O. 2 N.H. 2 , S.O. 2 NHR 621 Or S.O. 2 N.R. 621 R 622 represents; R 612 and R 613 , R 613 and R 614 , R 614 and R 615 , R 617 and R 618 , R 618 and R 619 , and R 619 and R 620 At least one combination selected from the group consisting of may be directly bonded to each other or may be bonded to an oxygen atom, a sulfur atom, NH, or NR 621 may be joined together by bridges; R 621 and R 622 each independently represents 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. 3. The photosensitive colored resin composition according to claim 1, wherein the dispersant (B) comprises an acrylic dispersant having a tertiary amino group and / or a quaternary ammonium group.

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

8. The photosensitive colored resin composition according to claim 1 or 2, wherein the (C) alkali-soluble resin contains (C3) an isocyanuric skeleton-containing resin.

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

10. A pigment dispersion comprising (A) a colorant, (B) a dispersant, and (C) an alkali-soluble resin, The colorant (A) contains an organic pigment (A-1), The pigment dispersion liquid, wherein the alkali-soluble resin (C) contains a resin (C1) having a structural unit represented by the following general formula (1): 【Chemistry 4】 (In formula (1), R 1 represents a hydrogen atom or a methyl group. R 2 each independently represents an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms and has at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid as a substituent. * represents a bond.)

11. The pigment dispersion according to claim 10 , wherein the resin (C1) has a structural unit represented by the following general formula (2): 【Chemistry 5】 In formula (2), A represents a hydrogen atom or a polybasic acid residue. R 1 represents a hydrogen atom or a methyl group. R 2 each independently represents an alkyl group having 1 to 4 carbon atoms. * represents a bond.)

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

13. 13. The pigment dispersion of claim 12, wherein the organic black pigment comprises a benzodifuranone-based organic black pigment.

14. The pigment dispersion according to claim 13, wherein the organic black pigment comprises a compound represented by the following general formula (A-1-1), a geometric isomer thereof, a salt thereof, or a salt of the geometric isomer thereof: 【Chemistry 6】 (In formula (A-1-1), R 611 and R 616 Each independently represents a hydrogen atom, CH 3 , C.F. 3 , a fluorine atom or a 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, R 621 , COOH, COOR 621 , COO - , C.O.N.H. 2 , C.O.N.R. 621 , C.O.R. 621 R 622 , C.N., O.H., O.R. 621 , COCR 621 , O.O.C.N.H. 2 , OOCNHR 621 , OOCNR 621 R 622 , NO 2 , N.H. 2 , N.H.R. 621 , N.R. 621 R 622 , NHCOR 622 , N.R. 621 C.O.R. 622 , N=CH 2 , N=CHR 621 , N=CR 621 R 622 , S.H., S.R. 621 , S.O.R. 621 , S.O. 2 R 621 , S.O. 3 R 621 , S.O. 3 H, SO 3 - , S.O. 2 N.H. 2 , S.O. 2 NHR 621 Or SO 2 N.R. 621 R 622 represents; R 612 and R 613 , R 613 and R 614 , R 614 and R 615 , R 617 and R 618 , R 618 and R 619 , and R 619 and R 620 At least one combination selected from the group consisting of may be directly bonded to each other or may be bonded to an oxygen atom, a sulfur atom, NH, or NR 621 may be joined together by bridges; R 621 and R 622 each independently represents 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 liquid according to claim 10 or 11, wherein the dispersant (B) comprises an acrylic dispersant having a tertiary amino group and / or a quaternary ammonium group.

16. A cured product obtained by curing the photosensitive colored resin composition according to claim 1 or 2.

17. A partition wall formed from the cured product according to claim 16.

18. An organic electroluminescence device comprising the partition wall according to claim 17 .

19. A color filter comprising luminescent nanocrystalline particles, the color filter comprising the partition wall according to claim 17.

20. An image display device comprising the partition wall according to claim 17.

21. A compound having a structural unit represented by the following general formula (1): 【Chemistry 7】 (In formula (1), R 1 represents a hydrogen atom or a methyl group. R 2 each independently represents an alkyl group having 1 to 4 carbon atoms. L represents an alkylene group having 2 to 6 carbon atoms and has at least a hydroxyl group or an ester group of a hydroxyl group and a polybasic acid as a substituent. * represents a bond.)

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