Colored photosensitive composition, cured product, color filter, solid-state imaging element, image display device, and asymmetric diketopyrrolopyrrole compound

Abstract

The present invention provides a colored photosensitive composition, a cured product of the colored photosensitive composition, a color filter, a solid-state imaging element, or an image display device having the cured product, or a novel asymmetric diketopyrrolopyrrole compound. The colored photosensitive composition comprises a pigment and a diketopyrrolopyrrole compound A represented by Formula 1, wherein the molar contents of the diketopyrrolopyrrole compounds A and B represented by Formula 1 are set to m A 、m B When, m A / (m A +m B ) is 10 mol% to 100 mol%, and the content of the pigment is 35% by mass or more relative to the total solid content in the colored photosensitive composition. 1 represents a monovalent organic group having an acidic or basic functional group, B 1 represents a monovalent organic group having no acidic or basic functional group. 1 and B 1 It represents a monovalent organic group with an acidic or basic functional group. #imgabs0#

Description

Technical Field

[0001] The present invention relates to a colored photosensitive composition, a cured product, a color filter, a solid-state imaging element, an image display device, and an asymmetric diketopyrrolopyrrole compound. Background Art

[0002] Color filters are essential components of solid-state imaging devices and image display devices. These devices sometimes generate noise through the reflection of visible light. Therefore, light-shielding films are used in these devices to suppress this noise.

[0003] As a method for producing such a color filter and a light-shielding film, a method is known in which a colored photosensitive composition containing a colorant, a polymerizable compound, a photopolymerization initiator, and an alkali-soluble resin is used to form a colored photosensitive composition layer, and the colored photosensitive composition layer is exposed and developed to form a pattern.

[0004] As conventional colored photosensitive compositions or photosensitive compositions, compositions described in Patent Documents 1 to 3 are known.

[0005] Patent Document 1: Japanese Patent Application Laid-Open No. 2013-182230

[0006] Patent Document 2: International Publication No. 2018 / 159541

[0007] Patent Document 3: Japanese Patent Application No. 2011-523433 Summary of the Invention

[0008] Technical issues to be solved by the invention

[0009] An object of the present invention is to provide a colored photosensitive composition having an excellent adhesiveness of a cured product.

[0010] Furthermore, another problem to be solved by an embodiment of the present invention is to provide a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state imaging element or image display device including the color filter.

[0011] Furthermore, another problem to be solved by the embodiments of the present invention is to provide a novel asymmetric diketopyrrolopyrrole compound.

[0012] Means for solving technical problems

[0013] Means for solving the above-mentioned problems include the following aspects.

[0014] <1> A colored photosensitive composition comprising a pigment and a diketopyrrolopyrrole compound A represented by the following formula 1, wherein the molar content of the diketopyrrolopyrrole compound A represented by the following formula 1 in the colored photosensitive composition is set to m A The molar content of the diketopyrrolopyrrole compound B represented by the following formula 1 is set to m B When, m A / (m A +m B ) is 10 mol% to 100 mol%, and the content of the pigment is 35 mass% or more relative to the total solid content in the colored photosensitive composition.

[0015] [Chemical Formula 1]

[0016]

[0017] In formula 1,

[0018] Diketopyrrolopyrrole compound A:A 1 represents a monovalent organic group having an acidic or basic functional group, B 1 represents a monovalent organic group having no acidic functional group and no basic functional group, R each independently represents a hydrogen atom or a monovalent substituent,

[0019] Diketopyrrolopyrrole compound B:A 1 and B 1 represents a monovalent organic group having an acidic or basic functional group, A 1 and B 1 They may be the same or different, and each R independently represents a hydrogen atom or a monovalent substituent.

[0020] <2> according to <1> The colored photosensitive composition, wherein

[0021] The diketopyrrolopyrrole compound A includes an asymmetric diketopyrrolopyrrole compound represented by the following formula 2.

[0022] [Chemical Formula 2]

[0023]

[0024] In formula 2, A 2 Each independently represents a monovalent organic group having an acidic functional group or a basic functional group, 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, C 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, n1 represents an integer of 1 to 5, n2 represents an integer of 0 to 5, and n3 represents an integer of 0 to 4.2 and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups.

[0025] <3> according to <1> or <2> The colored photosensitive composition, wherein

[0026] The above m A / (m A +m B ) is greater than 90 mol% and less than 100 mol%.

[0027] <4> according to <1> The colored photosensitive composition, wherein

[0028] A 1 It is a monovalent organic group having a basic functional group.

[0029] <5> according to <1> to <4> The colored photosensitive composition according to any one of the preceding claims, wherein

[0030] The above-mentioned pigments include diketopyrrolopyrrole pigments other than the compound represented by Formula 1.

[0031] <6> according to <1> The colored photosensitive composition according to any one of <5>, wherein

[0032] The above-mentioned pigment includes a diketopyrrolopyrrole red pigment other than the compound represented by Formula 1.

[0033] <7> according to <1> to <6> The colored photosensitive composition according to any one of the preceding claims, wherein

[0034] The above pigments include a diaryldiketopyrrolopyrrole red pigment having an electron-donating group on an aromatic ring other than the compound represented by Formula 1.

[0035] <8> according to <1> to <7> The colored photosensitive composition according to any one of the preceding claims, wherein

[0036] Content of the said pigment is 50 mass % or more with respect to the total solid content in the coloring photosensitive composition.

[0037] <9> according to <1> to <8> The colored photosensitive composition according to any one of the preceding claims, wherein

[0038] The content M of the pigment in the colored photosensitive composition P and the content M of the diketopyrrolopyrrole compound A A The mass ratio is M P / M A =95 / 5~50 / 50.

[0039] <10> according to <1> to <9> The colored photosensitive composition according to any one of the preceding claims further contains a resin.

[0040] <11> according to <10> The colored photosensitive composition, wherein

[0041] The above resins include resins having an acidic functional group.

[0042] <12> according to <1> to <11> The colored photosensitive composition according to any one of the preceding claims further contains a polymerizable compound and a photopolymerization initiator.

[0043] <13> A solidified material, which is <1> to <12> The colored curable composition described in any one of the above is cured.

[0044] <14> A color filter having <13> The solidified material.

[0045] <15> A solid-state imaging element having <14> The color filter.

[0046] <16> An image display device having <14> The color filter.

[0047] <17> An asymmetric diketopyrrolopyrrole compound represented by the following formula 3.

[0048] [Chemical Formula 3]

[0049]

[0050] In formula 3, A 3 Each independently represents an acidic functional group or a basic functional group, B 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, C 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, X 1 Each independently represents an ether bond, a thioether bond, a sulfonamide bond or a urea bond, L 1 Each independently represents a single bond or an ether bond, L 2 and L 3 Each independently represents an alkylene group, n2 represents an integer of 0 to 5, n3 represents an integer of 0 to 4, n4 independently represents 0 or 1, n5 represents an integer of 1 to 5, and the terminal has A 3 The group and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups, L 1 In the case of an ether bond, B 2It is an electron-donating group having no acidic functional group and no basic functional group, and n2 represents an integer of 1-5.

[0051] Effects of the Invention

[0052] According to an embodiment of the present invention, a colored photosensitive composition having an excellent adhesiveness of a cured product is provided.

[0053] Furthermore, according to another embodiment of the present invention, there is provided a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state imaging element or image display device including the color filter.

[0054] In addition, according to another embodiment of the present invention, a novel asymmetric diketopyrrolopyrrole compound is provided. DETAILED DESCRIPTION

[0055] Hereinafter, the content of the present invention will be described in detail. Although the description of the constituent elements described below may be made based on representative embodiments of the present invention, the present invention is not limited to such embodiments.

[0056] In addition, in the present invention, "to" indicating a numerical range is used to mean that the numerical values described before and after it are included as the lower limit and the upper limit.

[0057] In the numerical ranges described in stages throughout the present invention, the upper limit or lower limit of one numerical range may be replaced by the upper limit or lower limit of another numerical range described in stages. Furthermore, in the numerical ranges described in the present invention, the upper limit or lower limit of the numerical range may also be replaced by the values shown in the Examples.

[0058] In the present invention, when a plurality of substances corresponding to each component are present in the composition, unless otherwise specified, the amount of each component in the composition refers to the total amount of the corresponding plurality of substances present in the composition.

[0059] Furthermore, in the present invention, in the notation of groups (atomic groups), not indicating whether or not substituted includes groups without substitution as well as groups with substitution. For example, "alkyl" includes not only alkyl groups without substitution (unsubstituted alkyl groups) but also alkyl groups with substitution (substituted alkyl groups).

[0060] In the present invention, unless otherwise specified, "Me" represents a methyl group, "Et" represents an ethyl group, "Pr" represents a propyl group, "Bu" represents a butyl group, and "Ph" represents a phenyl group.

[0061] In the present invention, “(meth)acrylic acid” is a term used as a concept including both acrylic acid and methacrylic acid, and “(meth)acryloyl” is a term used as a concept including both acryloyl and methacryloyl.

[0062] Furthermore, in the present invention, the term "process" encompasses not only independent processes but also processes that achieve the intended purpose of the process even if they cannot be clearly distinguished from other processes.

[0063] In the present invention, "total solids" refers to the total mass of the components of the composition excluding the solvent. As described above, "solids" refers to components other than the solvent and may be solid or liquid at 25°C, for example.

[0064] In the present invention, "mass %" has the same meaning as "weight %", and "parts by mass" has the same meaning as "parts by weight".

[0065] Furthermore, in the present invention, a combination of two or more preferred aspects is a more preferred aspect.

[0066] In addition, unless otherwise specified, the weight average molecular weight (Mw) and number average molecular weight (Mn) in the present invention are molecular weights calculated using polystyrene as a standard substance using a gel permeation chromatography (GPC) analyzer using a TSKgel GMHxL, TSKgel G4000HxL, or TSKgel G2000HxL (all product names, manufactured by TOSOH CORPORATION) column, using a THF (tetrahydrofuran) solvent and a differential refractometer for detection.

[0067] In this specification, a pigment refers to a compound that is difficult to dissolve in a solvent.

[0068] In this specification, a dye refers to a compound that is easily soluble in a solvent.

[0069] The present invention is described in detail below.

[0070] (Coloring photosensitive composition)

[0071] The colored photosensitive composition of the present invention comprises a pigment and a diketopyrrolopyrrole compound A represented by the following formula 1. The molar content of the diketopyrrolopyrrole compound A represented by the following formula 1 in the colored photosensitive composition is set to m A The molar content of the diketopyrrolopyrrole compound B represented by the following formula 1 is set to m B When, m A / (m A +m B) is 10 mol% to 100 mol%, and the content of the pigment is 35 mass% or more relative to the total solid content in the colored photosensitive composition.

[0072] [Chemical Formula 4]

[0073]

[0074] In formula 1,

[0075] Diketopyrrolopyrrole compound A:A 1 represents a monovalent organic group having an acidic or basic functional group, B 1 represents a monovalent organic group having no acidic functional group and no basic functional group, R each independently represents a hydrogen atom or a monovalent substituent,

[0076] Diketopyrrolopyrrole compound B:A 1 and B 1 represents a monovalent organic group having an acidic or basic functional group, A 1 and B 1 They may be the same or different, and each R independently represents a hydrogen atom or a monovalent substituent.

[0077] In recent years, with the increasing pixel count in image sensors, patterns have become increasingly finer and thinner. This has led to a relative increase in pigment concentration and a relative decrease in the amount of curable components in color filters. The present inventors conducted detailed research and discovered that conventional colored photosensitive compositions containing a pigment content of 35% by mass or more relative to the total solids content of the colored photosensitive composition may exhibit insufficient adhesion to substrates and the like.

[0078] As a result of intensive research, the present inventors have found that the above-mentioned structure allows the obtained cured product to have excellent adhesion.

[0079] The content of the pigment is 35% by mass or more relative to the total solid content in the colored photosensitive composition, and the diketopyrrolopyrrole compound A represented by the above formula 1 is contained. The molar content of the diketopyrrolopyrrole compound A represented by the following formula 1 in the colored photosensitive composition is set to m A , the molar content of the diketopyrrolopyrrole compound B represented by the following formula 1 is set to m B When, m A / (m A +m B) is 10 to 100 mol%. Therefore, even in a colored photosensitive composition with a high pigment concentration as described above, when the diketopyrrolopyrrole compound A is adsorbed on the pigment surface to form a pigment particle-asymmetric diketopyrrolopyrrole compound A structure, the acidic or basic functional groups are more likely to be located on the side opposite to the pigment side compared to symmetrical diketopyrrolopyrrole compounds, and the compound is more likely to interact with other components such as the dispersant. Therefore, due to the excellent adsorption of the pigment based on the diketopyrrolopyrrole ring structure, and the easy arrangement of the diketopyrrolopyrrole compound A on the surface of the pigment particles, it is speculated that the interaction between the pigment particles and the diketopyrrolopyrrole compound A, as well as the interaction between other components and the diketopyrrolopyrrole compound A, is enhanced, and the resulting cured product has excellent adhesion (hereinafter also referred to as "adhesion").

[0080] <Diketopyrrolopyrrole compounds A and B>

[0081] The colored photosensitive composition of the present invention contains the diketopyrrolopyrrole compound A represented by the above formula 1. The molar content of the diketopyrrolopyrrole compound A represented by the above formula 1 in the colored photosensitive composition is set to m A The molar content of the diketopyrrolopyrrole compound B represented by the above formula 1 is set to m B When, m A / (m A +m B ) is 10 mol% to 100 mol%.

[0082] In the present invention, the pigments mentioned above are pigments other than the diketopyrrolopyrrole compounds A and B represented by the above formula 1.

[0083] From the viewpoint of adhesion and storage stability, the above m in the present invention A / (m A +m B ) is preferably 50 mol% to 100 mol%, more preferably 80 mol% to 100 mol%, particularly preferably greater than 90 mol% and 100 mol%.

[0084] In the colored photosensitive composition of the present invention, the content of the isomer with the largest content in the diketopyrrolopyrrole compound A represented by the above formula 1 is set to m AA From the viewpoint of adhesion and storage stability, the above m in the present invention AA / m A The value of is preferably 80 mol % to 100 mol %, more preferably 90 mol % to 100 mol %, particularly preferably 95 mol % to 100 mol %.

[0085] From the viewpoint of adhesion and storage stability, A in Formula 1 1 and B 1 The acidic functional group in is preferably a sulfo group, a salt of a sulfo group, a carboxyl group, a phosphoric acid functional group, a hydroxyl group or a boric acid functional group, and more preferably a sulfo group, a salt of a sulfo group or a carboxyl group.

[0086] From the viewpoint of adhesion and storage stability, the counter ion of the salt of the sulfonic group is preferably a metal ion, a monoalkylammonium ion having 1 to 12 carbon atoms, a dialkylammonium ion having 2 to 24 carbon atoms, a trialkylammonium ion having 3 to 36 carbon atoms, or a tetraalkylammonium ion having 4 to 48 carbon atoms; more preferably a metal ion, a monoalkylammonium ion having 1 to 12 carbon atoms, a dialkylammonium ion having 2 to 24 carbon atoms, or a trialkylammonium ion having 3 to 36 carbon atoms; further preferably a metal ion, and particularly preferably an alkali metal ion.

[0087] From the viewpoint of adhesion and storage stability, A in Formula 1 1 and B 1 The basic functional group in is preferably a group having a nitrogen atom, more preferably -NR 1A R 2A or a heterocyclic group containing a nitrogen atom, more preferably a piperidinyl group, a morpholinyl group or -NR 1A R 2A , particularly preferably -NR 1A R 2A .

[0088] -NR 1A R 2A R in 1A and R 2A Preferably, each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, more preferably an alkyl group, an aryl group, or a heteroaryl group, further preferably an alkyl group, and particularly preferably an alkyl group having 1 to 4 carbon atoms.

[0089] R 1A and R 2A The alkyl group in the group may have a substituent, and examples thereof include a halogen atom, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, and a dialkylamino group.

[0090] R 1A and R 2A The aryl group and heteroaryl group in the group may have a substituent, and examples thereof include a halogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, and a dialkylamino group.

[0091] And, -NR 1A R 2A R in 1A With R 2A They may be bonded to form a ring, preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring.

[0092] As R 1A With R 2A The ring formed by bonding, except for R 1A and R 2A In addition to the nitrogen atom to which the ring is bonded, the ring may have a heteroatom as a ring member and may have a substituent. Examples of the substituent that the ring may have include a halogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, and an alkylthio group.

[0093] The heterocyclic group containing a nitrogen atom is preferably an imidazolyl group, a pyrazolyl group, a triazolyl group, a piperazinyl group, a pyridinyl group, a pyrrolyl group, a thiazolyl group, an oxazolyl group, a benzoxazolyl group, an indolyl group, a benzothiazolyl group, a benzimidazolyl group, a benzotriazolyl group, a morpholinyl group, a piperidinyl group or a pyrrolidinyl group, and more preferably a piperidinyl group or a morpholinyl group.

[0094] Among them, from the viewpoint of adhesion and storage stability, the A of the diketopyrrolopyrrole compound A is 1 A monovalent organic group having a basic functional group is preferred.

[0095] Furthermore, from the viewpoint of adhesion and storage stability, the A of the diketopyrrolopyrrole compound B is 1 and B 1 A monovalent organic group having a basic functional group is preferred.

[0096] Furthermore, from the viewpoint of adhesion and storage stability, R in Formula 1 is preferably independently a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 10 carbon atoms, further preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and particularly preferably a hydrogen atom.

[0097] Furthermore, from the viewpoint of adhesion and storage stability, B of the diketopyrrolopyrrole compound A 1 An aryl group which may have a substituent is preferred, and a phenyl group which may have a substituent is more preferred.

[0098] B as the diketopyrrolopyrrole compound A 1 The substituents that the aryl group and the phenyl group in the phenyl group may have are preferably alkyl, alkoxy, phthalimide alkyl, acyl, halogen, phenyl, naphthyl, cyano, trifluoromethyl, alkoxycarbonyl, alkylthio, -CONH2, -CON(R 11 )R 12 、-COOR 13 、-SONR 14 R 15 、-NR 16 SO2R 17 、-NR 18 COR19 , more preferably an alkyl group, a phenyl group, a naphthyl group, an alkoxy group or a halogen atom, further preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or a halogen atom, particularly preferably a methyl group, a methoxy group or a chlorine atom.

[0099] R 11 ~R 19 Each independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group.

[0100] Furthermore, the above-mentioned substituents may further have a substituent.

[0101] From the viewpoint of adhesion and storage stability, the A of the diketopyrrolopyrrole compound A is 1 The number of carbon atoms in the moiety is preferably 8-80, more preferably 9-60, particularly preferably 9-40.

[0102] From the viewpoint of adhesion and storage stability, the B of the diketopyrrolopyrrole compound A is 1 The number of carbon atoms in the moiety is preferably 6-80, more preferably 6-60, and particularly preferably 6-40.

[0103] Furthermore, from the viewpoint of adhesion and storage stability, the A of the diketopyrrolopyrrole compound B is 1 and B 1 It is preferably 8-80, more preferably 9-60, and particularly preferably 9-40.

[0104] From the viewpoint of adhesion and storage stability, the diketopyrrolopyrrole compound A preferably contains an asymmetric diketopyrrolopyrrole compound represented by the following formula 2.

[0105] [Chemical Formula 5]

[0106]

[0107] In formula 2, A 2 Each independently represents a monovalent organic group having an acidic functional group or a basic functional group, 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, C 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, n1 represents an integer of 1 to 5, n2 represents an integer of 0 to 5, and n3 represents an integer of 0 to 4. 2 and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups.

[0108] A in Formula 2 2 The preferred embodiment of the acidic functional group and the basic functional group in the above formula 1 is the same as that of A1 The preferred aspects of the acidic functional group and the basic functional group are the same.

[0109] From the viewpoint of adhesion and storage stability, A in Formula 2 2 It is preferably bonded to the benzene ring of Formula 2 via an alkylene group, and more preferably bonded to the benzene ring of Formula 2 via a methylene group.

[0110] A in Formula 2 2 The number of carbon atoms in the moiety is preferably 2-60, more preferably 3-40, particularly preferably 9-20.

[0111] Furthermore, from the viewpoint of adhesion and storage stability, A in Formula 2 2 Preferred is -XYZ.

[0112] X represents a single bond, -CH2-, or -(CH2) q O-, -O-, -(CH2) q S-, -S-, -(CH2) q COO-, -(CH2) q SO2NR 101 -、-(CH2) q NR 101 SO2-, -(CH2) q NR 101 CO-, -(CH2) q CONR 101 -、-(CH2) q NHCOCH2NH-、-(CH2) q NHCONH-、-(CH2) q SO2-, -(CH2) q CO-, -(CH2) q NHCOCH2-、-(CH2) q CONHC6H4CO-、-(CH2) q CONHC6H4- or -(CH2) q NH-,

[0113] q represents an integer from 0 to 10,

[0114] R 101 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a phenyl group which may have a substituent,

[0115] Y represents a single bond, a hydrocarbon group which may have a substituent, an arylene group which may have a substituent, or a heteroaromatic ring which may have a substituent. These groups may be selected from -NR 101 -, -O-, -SO2- or CO- in a divalent linking group and bonded to each other,

[0116] Z represents a group represented by any one of the following formulas (Z1) to (Z6),

[0117] [Chemical Formula 6]

[0118]

[0119] R 301 and R 302 Each independently represents an optionally substituted saturated or unsaturated alkyl group or a heterocyclic ring containing a nitrogen, oxygen or sulfur atom and which may be substituted,

[0120] R 303 、R 304 、R 305 and R 306 Each independently represents a hydrogen atom, a saturated or unsaturated alkyl group or an aryl group which may be substituted,

[0121] R 307 represents a saturated or unsaturated alkyl or aryl group which may be substituted,

[0122] R 308 and R 309 Each independently represents a group represented by any one of the following formulas (Z7) and (Z8), or -O-(CH2). 350 、-OR 351 、-NR 352 R 353 , -Cl or -F, R 308 and R 309 Any one of them is a group represented by any one of the following formulas (Z7) or (Z8), -O-(CH2). -R 350 、-OR 351 or -NR 352 R 353 , o represents an integer from 1 to 8,

[0123] R 350 represents a heterocyclic residue which may have a substituent,

[0124] R 351 ~R 353 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a phenyl group which may have a substituent,

[0125] M each independently represents a metal ion,

[0126] R 310 ~R 313 Each independently represents a hydrogen atom, a saturated or unsaturated alkyl group or an aryl group which may be substituted,

[0127] R 314 ~R318 Each independently represents a hydrogen atom, an alkoxy group, an amino group, a sulfo group, a carboxyl group or a phosphoric acid functional group,

[0128] [Chemical Formula 7]

[0129]

[0130] Z 1 Indicates -NR 370 -, -CONH- or -O-,

[0131] Z 2 represents an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or an arylene group which may have a substituent,

[0132] These groups can be selected from -NR 370 -, -O-, -SO2- and CO- are bonded to each other through divalent linking groups.

[0133] R 370 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a phenyl group which may have a substituent,

[0134] R 360 and R 361 Each independently represents an alkyl group which may have a substituent, an alkenyl group which may have a substituent, a phenyl group which may have a substituent, or a group containing R 360 and R 361 another nitrogen, oxygen or sulfur atom which is integrated into a heterocyclic ring which may have a substituent,

[0135] [Chemical Formula 8]

[0136]

[0137] Z 3 represents a single bond connecting the triazine ring and the nitrogen atom, -NR 380 -、-NR 380 -Z 4 -CO-、-NR 380 -Z 4 -CONR 381 -、-NR 380 -Z 4 -SO2-、-NR 380 -Z 4 -SO2NR 381 -、-OZ 4 -CO-、-OZ 4 -CONR 380 -、-OZ 4 -SO2- or -OZ 4 -SO2NR380 -,

[0138] R 362 ~R 366 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, a phenyl group which may have a substituent, or a polyoxyalkylene group,

[0139] R 380 and R 381 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a phenyl group which may have a substituent,

[0140] Z 4 represents an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or an arylene group which may have a substituent,

[0141] The wavy lines indicate the bonding positions with other structures.

[0142] Among them, from the viewpoint of adhesion and storage stability, X is preferably -CH2-O-, -CH2-, -O-, -S-, -CH2-S-, -CH2-NHSO2-, or -NHSO2-.

[0143] Furthermore, from the viewpoint of adhesion and storage stability, Y is preferably a single bond or a substituted or unsubstituted linear or branched hydrocarbon group having 1 to 8 carbon atoms.

[0144] Furthermore, from the viewpoint of adhesion and storage stability, Z is preferably a group represented by any one of the above formulas (Z1) to (Z4), more preferably a group represented by any one of the above formulas (Z1) to (Z3), and particularly preferably a group represented by the above formula (Z1).

[0145] Furthermore, from the viewpoint of adhesion and storage stability, A in Formula 2 2 Preferred are -alkylene-acidic or basic functional groups, -heteroatom-containing linking group-alkylene-acidic or basic functional groups, or -alkylene-heteroatom-containing linking group-alkylene-acidic or basic functional groups, and more preferably -alkylene-acidic or basic functional groups, or -heteroatom-containing linking group-alkylene-acidic or basic functional groups.

[0146] From the viewpoint of adhesion and storage stability, the alkylene group is preferably a linear or branched alkylene group having 1 to 8 carbon atoms, and more preferably a linear alkylene group having 1 to 3 carbon atoms.

[0147] From the viewpoint of adhesion and storage stability, the heteroatom-containing linking group is preferably an ether bond, a thioether bond, a sulfonamide bond, or a urea bond, more preferably an ether bond, a sulfonamide bond, or a urea bond, further preferably an ether bond or a sulfonamide bond, and particularly preferably an ether bond.

[0148] From the viewpoint of adhesion and storage stability, B in formula 2 2 and C 2 Preferably, each independently represents an alkyl group, an alkoxy group, a phthalimide alkyl group, an acyl group, a halogen atom, a phenyl group, a naphthyl group, a cyano group, a trifluoromethyl group, an alkoxycarbonyl group, an alkylthio group, -CONH2, -CON(R 11 )R 12 、-COOR 13 、-SONR 14 R 15 、-NR 16 SO2R 17 、-NR 18 COR 19 , more preferably an alkyl group, a phenyl group, a naphthyl group, an alkoxy group or a halogen atom, further preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a phenyl group or a halogen atom, particularly preferably a methyl group, a methoxy group, a phenyl group, a chlorine atom or a bromine atom.

[0149] R 11 ~R 19 Each independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group.

[0150] Furthermore, the above B 2 and C 2 The alkyl group, alkoxy group, phthalimide alkyl group, acyl group, halide group, phenyl group, naphthyl group, cyano group, trifluoromethyl group, alkoxycarbonyl group, and alkylthio group in the group may have a substituent.

[0151] Examples of the substituent include an alkyl group, an alkoxy group, a phthalimide alkyl group, an acyl group, a halogen atom, a phenyl group, a naphthyl group, a cyano group, a trifluoromethyl group, an alkoxycarbonyl group, an alkylthio group, -CONH2, -CON(R 11 )R 12 、-COOR 13 、-SONR 14 R 15 、-NR 16 SO2R 17 、-NR 18 COR 19 .

[0152] Furthermore, B in Equation 2 2 and C 2 The number of carbon atoms in each independently is preferably 0 to 60, more preferably 0 to 20, particularly preferably 0 to 8.

[0153] From the viewpoint of adhesion and storage stability, n1 in Formula 2 is preferably 1 or 2, and more preferably 1.

[0154] From the viewpoint of adhesion and storage stability, n2 in Formula 2 is preferably an integer of 0 to 2, and more preferably 0 or 1.

[0155] From the viewpoint of adhesion and storage stability, n3 in Formula 2 is preferably 0 or 1, and more preferably 0.

[0156] Furthermore, A in Formula 2 2 、B 2 and C 2 The bonding position of is not particularly limited, but from the viewpoint of adhesion and storage stability, it is preferred to have at least A in the para position relative to the bonding position of the diketopyrrolopyrrole ring in the benzene ring of formula 2. 2 .

[0157] In addition, when n2 is 1 or more, it is preferred that at least B be present in the para position relative to the bonding position of the diketopyrrolopyrrole ring in the benzene ring of Formula 2 from the viewpoint of adhesion and storage stability. 2 .

[0158] Furthermore, from the viewpoint of adhesion and storage stability, the diketopyrrolopyrrole compound A more preferably contains an asymmetric diketopyrrolopyrrole compound represented by the following formula 3.

[0159] [Chemical Formula 9]

[0160]

[0161] In formula 3, A 3 Each independently represents an acidic functional group or a basic functional group, B 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, C 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, X 1 Each independently represents an ether bond, a thioether bond, a sulfonamide bond or a urea bond, L 1 Each independently represents a single bond or an ether bond, L 2 and L 3 Each independently represents an alkylene group, n2 represents an integer of 0 to 5, n3 represents an integer of 0 to 4, n4 independently represents 0 or 1, n5 represents an integer of 1 to 5, and the terminal has A 3 The group and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups, L 1 In the case of an ether bond, B 2It is an electron-donating group having no acidic functional group and no basic functional group, and n2 represents an integer of 1-5.

[0162] A in Formula 3 3 The preferred embodiment of the acidic functional group and the basic functional group in the above formula 1 is the same as that of A 1 The preferred aspects of the acidic functional group and the basic functional group are the same.

[0163] B in Formula 3 2 、C 2 , n2 and n3 are respectively the same as B in the above formula 2 except for the following descriptions. 2 、C 2 , n2 and n3 have the same meaning and the preferred method is also the same.

[0164] From the perspective of storage stability, L in Formula 3 1 A single bond is preferred, and from the viewpoint of adhesion, L in Formula 3 is 1 An ether bond is preferred.

[0165] And, when L 1 When it is an ether bond, from the viewpoint of adhesion, B 2 The electron-donating group in is preferably an alkyl group or an alkoxy group, more preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, and particularly preferably a methyl group or a methoxy group.

[0166] In addition, when L 1 In the case of an ether bond, n2 is preferably an integer of 1 to 3, more preferably 1 or 2, and particularly preferably 1, from the viewpoint of adhesion.

[0167] From the viewpoint of adhesion and storage stability, L in Formula 3 2 Each independently is preferably a linear or branched alkylene group having 1 to 8 carbon atoms, more preferably a linear alkylene group having 1 to 3 carbon atoms, and particularly preferably a methylene group.

[0168] From the viewpoint of adhesion and storage stability, X in Formula 3 1 An ether bond, a sulfonamide bond, or a urea bond is preferred, an ether bond or a sulfonamide bond is more preferred, and an ether bond is particularly preferred.

[0169] From the viewpoint of adhesion and storage stability, L in Formula 3 3 Each of the groups independently is preferably a linear or branched alkylene group having 1 to 8 carbon atoms, more preferably a linear or branched alkylene group having 2 or 3 carbon atoms, and particularly preferably a linear alkylene group having 2 or 3 carbon atoms.

[0170] From the viewpoint of adhesion and storage stability, n4 in Formula 3 is preferably 0.

[0171] From the viewpoint of adhesion and storage stability, n5 in Formula 3 is preferably 1 or 2, and more preferably 1.

[0172] From the viewpoint of adhesion and storage stability, the molecular weight of the diketopyrrolopyrrole compound A is preferably 1,200 or less, more preferably 800 or less, further preferably 600 or less, and particularly preferably 340 or more and 600 or less.

[0173] The colored photosensitive composition of the present invention may contain the above-mentioned diketopyrrolopyrrole compound A alone or in combination of two or more.

[0174] The colored photosensitive composition of the present invention may not contain the diketopyrrolopyrrole compound B, may contain one type alone, or may contain two or more types.

[0175] From the viewpoint of adhesion and storage stability, the content of the diketopyrrolopyrrole compound A in the colored photosensitive composition of the present invention is preferably 0.01% by mass to 40% by mass, more preferably 0.05% by mass to 30% by mass, and particularly preferably 0.1% by mass to 20% by mass, relative to the total solid content of the colored photosensitive composition.

[0176] Furthermore, from the viewpoint of adhesion and storage stability, the total content of the diketopyrrolopyrrole compounds A and B in the colored photosensitive composition of the present invention is preferably 0.01% by mass to 40% by mass, more preferably 0.05% by mass to 30% by mass, and particularly preferably 0.1% by mass to 20% by mass, relative to the total solid content of the colored photosensitive composition.

[0177] From the viewpoint of adhesion and storage stability, the content M of the pigment in the colored photosensitive composition is P and the content M of the diketopyrrolopyrrole compound A A The mass ratio is preferably M P / M A =95 / 5 to 50 / 50, more preferably 94.9 / 5.1 to 55 / 45, further preferably 94.5 / 5.5 to 64 / 36, particularly preferably 94 / 6 to 82 / 18.

[0178] Specific examples of the diketopyrrolopyrrole compound A are shown below, including DPP-1 to DPP-26, but the present invention is not limited thereto.

[0179] [Chemical Formula 10]

[0180]

[0181] [Chemical Formula 11]

[0182]

[0183] [Chemical Formula 12]

[0184]

[0185] [Chemical Formula 13]

[0186]

[0187] [Chemical Formula 14]

[0188]

[0189] -Production method of diketopyrrolopyrrole compound A-

[0190] The method for producing the diketopyrrolopyrrole compound A is not particularly limited and can be produced by referring to known methods. Examples include methods derived from pigments, methods of condensing two or more cyano compounds, and methods of condensing a cyano compound and a ketopyrrole compound.

[0191] Among these, an asymmetric diketopyrrolopyrrole compound can be produced by condensing a cyano compound with a 3-alkoxycarbonyl-5-ketopyrrole compound in the presence of a base.

[0192] -Method for adding diketopyrrolopyrrole compounds A and B-

[0193] The method for adding the diketopyrrolopyrrole compounds A and B to the colored photosensitive composition is not particularly limited, and known addition methods and known mixing methods can be used. For example, preferably, the diketopyrrolopyrrole compound A is used as a composite pigment that is pre-mixed with a pigment (dry or wet) and dried, or is added during pigment grinding, or is added together with the dispersion medium during pigment dispersion, or is added to the pigment dispersion.

[0194] <Pigment>

[0195] The colored photosensitive composition of the present invention contains a pigment.

[0196] In addition, the above-mentioned pigment in the present invention is a pigment other than the diketopyrrolopyrrole compounds A and B represented by the above-mentioned Formula 1 (also referred to as "compound represented by Formula 1").

[0197] The pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment. Furthermore, pigments obtained by substituting a portion of an inorganic pigment or an organic-inorganic pigment with an organic chromophore may also be used. Substituting an organic chromophore for an inorganic pigment or an organic-inorganic pigment facilitates color design.

[0198] The colored photosensitive composition of the present invention can be preferably used as a colored photosensitive composition for forming colored pixels in a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Among them, red pixels are preferably used.

[0199] The average primary particle size of the pigment is preferably 1 nm to 200 nm. The lower limit is preferably 5 nm or more, more preferably 10 nm or more. The upper limit is preferably 180 nm or less, more preferably 150 nm or less, and further preferably 100 nm or less. If the average primary particle size of the pigment is within the above range, the dispersion stability of the pigment in the colored photosensitive composition is good. In addition, in the present invention, the primary particle size of the pigment can be obtained by observing the primary particles of the pigment through a transmission electron microscope and calculating it from the image photograph obtained. Specifically, the projected area of the primary particles of the pigment is calculated, and the corresponding circle equivalent diameter is calculated as the primary particle size of the pigment. In addition, the average primary particle size in the present invention is set to the arithmetic mean of the primary particle sizes of 400 primary particles of the pigment. In addition, the primary particles of the pigment refer to independent particles that are not agglomerated.

[0200] The amount of the pigment dissolved in 100 g of propylene glycol methyl ether acetate at 25° C. is preferably less than 0.01 g, more preferably less than 0.005 g, and even more preferably less than 0.001 g.

[0201] Examples of the organic pigment include phthalocyanine pigments, dioxazine pigments, quinacridone pigments, anthraquinone pigments, perylene pigments, azo pigments, diketopyrrolopyrrole pigments, pyrrolopyrrole pigments, isoindoline pigments, quinophthalone pigments, triarylmethane pigments, xanthene pigments, methine pigments, and quinoline pigments.

[0202] Among them, as a pigment, from the viewpoint of adhesion and storage stability, it is preferred to contain a diketopyrrolopyrrole pigment other than the compound represented by Formula 1, more preferably contain a diketopyrrolopyrrole red pigment other than the compound represented by Formula 1, further preferably contain a diaryldiketopyrrolopyrrole red pigment other than the compound represented by Formula 1, and particularly preferably contain a diaryldiketopyrrolopyrrole red pigment having an electron-donating group on the aromatic ring other than the compound represented by Formula 1.

[0203] Specific examples of the organic pigment include the following.

[0204] Color Index (CI) Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 1 37, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, 215, 228, 231, 232 (methine series), 233 (quinoline series), 234 (aminoketone series), 235 (aminoketone series), 236 (aminoketone series), etc. (the above are yellow pigments),

[0205] CI Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. (the above are orange pigments),

[0206] CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 270, 272, 279, 294 (xanthene, Organo Ultramarine, Bluish Red), 295 (monoazo), 296 (diazo), 297 (aminoketone), etc. (all red pigments)

[0207] CI Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64 (phthalocyanine series), 65 (phthalocyanine series), 66 (phthalocyanine series), etc. (the above are green pigments),

[0208] CI Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60 (triarylmethane series), 61 (xanthene series), etc. (the above are purple pigments),

[0209] CI Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87 (monoazo series), 88 (methine series), etc. (the above are blue pigments).

[0210] As red pigments, diketopyrrolopyrrole compounds in which at least one bromine atom is substituted in the structure described in Japanese Patent Application Laid-Open No. 2017-201384, diketopyrrolopyrrole compounds described in paragraphs 0016 to 0022 of Japanese Patent No. 6248838, diketopyrrolopyrrole compounds described in International Publication No. 2012 / 102399, diketopyrrolopyrrole compounds described in International Publication No. 2012 / 117965, naphthol azo compounds described in Japanese Patent Application Laid-Open No. 2012-229344, red pigments described in Japanese Patent No. 6516119, and red pigments described in Japanese Patent No. 6525101 can also be used. Furthermore, as the red pigment, a compound having a structure in which an aromatic ring group and a diketopyrrolopyrrole skeleton are bonded, wherein a group having an oxygen atom, a sulfur atom, or a nitrogen atom bonded to the aromatic ring is introduced into the aromatic ring group.

[0211] Furthermore, from the viewpoint of color tone and light resistance, preferred examples of the red pigment include CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 264, and CI Pigment Red 272, and more preferred examples include CI Pigment Red 254 and CI Pigment Red 272.

[0212] Furthermore, as the pigment, from the viewpoint of color tone, it is preferred to use CI Pigment Red 254 and CI Pigment Red 272 in combination.

[0213] Furthermore, from the viewpoint of color tone, the mass ratio of CI Pigment Red 254 to CI Pigment Red 272 is preferably CI Pigment Red 254 content:CI Pigment Red 272 content = 2:1 to 1:2, more preferably 1.5:1 to 1:1.5, further preferably 1.2:1 to 1:1.2, and particularly preferably 1.2:1 to 1:1.

[0214] Furthermore, from the viewpoint of color tone, the pigment preferably contains a red pigment and a yellow pigment.

[0215] Furthermore, the mass ratio of the red pigment to the yellow pigment is preferably red pigment content:yellow pigment content = 1:1 to 5:1, more preferably 1.5:1 to 3:1, from the viewpoint of color tone.

[0216] Furthermore, as yellow pigments, compounds described in Japanese Patent Application Laid-Open No. 2017-201003, compounds described in Japanese Patent Application Laid-Open No. 2017-197719, compounds described in paragraphs 0011 to 0062 and 0137 to 0276 of Japanese Patent Application Laid-Open No. 2017-171912, compounds described in paragraphs 0010 to 0062 and 0138 to 0295 of Japanese Patent Application Laid-Open No. 2017-171913, compounds described in paragraphs 0011 to 0062 and 0139 to 0190 of Japanese Patent Application Laid-Open No. 2017-171914, compounds described in paragraphs 0010 to 0065 and 0142 to 022 of Japanese Patent Application Laid-Open No. 2017-171915, The compounds described in paragraph 2, the quinophthalone compounds described in paragraphs 0011 to 0034 of Japanese Patent Application Laid-Open No. 2013-054339, the quinophthalone compounds described in paragraphs 0013 to 0058 of Japanese Patent Application Laid-Open No. 2014-026228, the isoindoline compounds described in Japanese Patent Application Laid-Open No. 2018-062644, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2018-203798, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2018-062578, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 6432076, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2018-155881, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2018- Quinophthalone compounds described in Japanese Patent Application Laid-Open No. 111757, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2018-040835, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2017-197640, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2016-145282, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2014-085565, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2014-021139, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2013-209614, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2013-209435, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2013-181015 Quinophthalone compounds described in JP-A-2013-061622, quinophthalone compounds described in JP-A-2013-032486, quinophthalone compounds described in JP-A-2012-226110, quinophthalone compounds described in JP-A-2008-074987, quinophthalone compounds described in JP-A-2008-081565, quinophthalone compounds described in JP-A-2008-074986, quinophthalone compounds described in JP-A-2008-074985, quinophthalone compounds described in JP-A-2008-050420,Quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2008-031281, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 48-032765, quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2019-008014, quinophthalone compounds described in Japanese Patent No. 6607427, methine dyes described in Japanese Patent Application Laid-Open No. 2019-073695, methine dyes described in Japanese Patent Application Laid-Open No. 2019-073696, Japanese Methine dyes described in Japanese Patent Application Laid-Open No. 2019-073697, methine dyes described in Japanese Patent Application Laid-Open No. 2019-073698, compounds described in Korean Patent Application Laid-Open No. 10-2014-0034963, compounds described in Japanese Patent Application Laid-Open No. 2017-095706, compounds described in Taiwan Patent Application Laid-Open No. 201920495, compounds described in Japanese Patent No. 6607427, etc. Furthermore, from the viewpoint of improving color value, it is also preferable to use a compound obtained by polymerizing these compounds.

[0217] Furthermore, as yellow pigments, from the viewpoint of color tone and light resistance, CI Pigment Yellow 139 and CI Pigment Yellow 185 are preferably mentioned.

[0218] Furthermore, as green pigments, zinc phthalocyanine halides having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule can also be used. Specific examples include compounds described in International Publication No. 2015 / 118720. Furthermore, as green pigments, compounds described in the specification of Chinese Patent Application Publication No. 106909027, phthalocyanine compounds having a phosphate ester as a ligand described in International Publication No. 2012 / 102395, phthalocyanine compounds described in Japanese Patent Application Publication No. 2019-008014, phthalocyanine compounds described in Japanese Patent Application Publication No. 2018-180023, and compounds described in Japanese Patent Application Publication No. 2019-038958 can also be used.

[0219] Furthermore, as a blue pigment, an aluminum phthalocyanine compound having a phosphorus atom can also be used. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A-2012-247591 and paragraph 0047 of JP-A-2011-157478.

[0220] Furthermore, pigments used in the present invention preferably include those having an X-ray diffraction pattern produced by specific CuKα radiation. Specific examples include phthalocyanine pigments described in Japanese Patent No. 6561862, diketopyrrolopyrrole pigments described in Japanese Patent No. 6413872, and azo pigments (CT Pigment Red 269) described in Japanese Patent No. 6281345.

[0221] The content of the pigment is 35% by mass or more relative to the total solids in the colored photosensitive composition. From the perspective of adhesion and storage stability, it is preferably 40% by mass or more, more preferably 45% by mass or more, and particularly preferably 50% by mass or more. The upper limit is preferably 70% by mass or less.

[0222] <Resin>

[0223] The colored photosensitive composition of the present invention preferably contains a resin. The resin is incorporated, for example, to disperse particles such as pigments in the colored photosensitive composition or to serve as a binder. Resins primarily used to disperse particles such as pigments are also referred to as dispersants. However, these uses of the resin are merely examples, and the resin may also be used for purposes other than these.

[0224] The weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000. The upper limit is more preferably 1,000,000 or less, particularly preferably 500,000 or less. The lower limit is more preferably 4,000 or more, particularly preferably 5,000 or more.

[0225] Examples of the resin include (meth)acrylic resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamide-imide resins, polyolefin resins, cyclic olefin resins, polyester resins, and styrene resins. These resins may be used alone or in combination of two or more. Furthermore, the resins described in paragraphs 0041 to 0060 of Japanese Patent Application Publication No. 2017-206689, the resins described in paragraphs 0022 to 007 of Japanese Patent Application Publication No. 2018-010856, the resins described in Japanese Patent Application Publication No. 2017-057265, the resins described in Japanese Patent Application Publication No. 2017-032685, the resins described in Japanese Patent Application Publication No. 2017-075248, and the resins described in Japanese Patent Application Publication No. 2017-066240 can also be used.

[0226] The colored photosensitive composition of the present invention preferably includes a resin having an acidic functional group as a resin. This improves the developability of the colored photosensitive composition and facilitates the formation of pixels with excellent rectangularity. Examples of the acidic functional group include a carboxyl group, a phosphoric acid functional group, a sulfonic group, and a phenolic hydroxyl group, with a carboxyl group being preferred. The resin having an acidic functional group can be used, for example, as an alkali-soluble resin.

[0227] Furthermore, from the viewpoint of adhesion and storage stability, the colored photosensitive composition of the present invention preferably contains the above-mentioned A 1 A diketopyrrolopyrrole compound represented by formula (1) which is a monovalent organic group having a basic functional group, and a resin having an acidic functional group.

[0228] The resin having an acidic functional group preferably contains repeating units having an acidic functional group on the side chain, and more preferably contains 5 to 70 mol% of repeating units having an acidic functional group on the side chain among all repeating units in the resin. The upper limit of the content of repeating units having an acidic functional group on the side chain is preferably 50 mol% or less, more preferably 30 mol% or less. The lower limit of the content of repeating units having an acidic functional group on the side chain is preferably 10 mol% or more, more preferably 20 mol% or more.

[0229] The resin having an acidic functional group also preferably contains repeating units derived from a monomer component containing at least one monomer selected from a compound represented by the following formula (ED1) and a compound represented by the following formula (ED2) (hereinafter, these compounds may also be referred to as "ether dimers").

[0230] [Chemical Formula 15]

[0231]

[0232] In formula (ED1), R 1 and R 2 Each independently represents a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a substituent.

[0233] [Chemical Formula 16]

[0234]

[0235] In formula (ED2), R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. For details of formula (ED2), reference can be made to the description of Japanese Patent Application Laid-Open No. 2010-168539, the contents of which are incorporated herein.

[0236] As specific examples of ether dimers, reference can be made to the description in paragraph 0317 of JP-A-2013-029760, for example, the contents of which are incorporated herein.

[0237] The resin used in the present invention also preferably contains a repeating unit derived from a compound represented by the following formula (X).

[0238] [Chemical Formula 17]

[0239]

[0240] In formula (X), R1 represents a hydrogen atom or a methyl group, R2 represents an alkylene group having 2 to 10 carbon atoms, and R3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may contain a benzene ring. n represents an integer of 1 to 15.

[0241] Regarding resins having acidic functional groups, reference can be made to paragraphs 0558 to 0571 of Japanese Patent Application Publication No. 2012-208494 (paragraphs 0685 to 0700 of the corresponding U.S. Patent Application Publication No. 2012 / 0235099) and paragraphs 0076 to 0099 of Japanese Patent Application Publication No. 2012-198408, the contents of which are incorporated herein. Commercially available resins having acidic functional groups can be used.

[0242] The acid value of the resin having an acidic functional group is preferably 30 mgKOH / g to 500 mgKOH / g. The lower limit is more preferably 40 mgKOH / g or higher, and particularly preferably 50 mgKOH / g or higher. The upper limit is more preferably 400 mgKOH / g or lower, further preferably 300 mgKOH / g or lower, and particularly preferably 200 mgKOH / g or lower. The weight average molecular weight (Mw) of the resin having an acidic functional group is preferably 5,000 to 100,000. Furthermore, the number average molecular weight (Mn) of the resin having an acidic functional group is preferably 1,000 to 30,000.

[0243] The method for introducing an acidic functional group into a resin is not particularly limited, and examples thereof include the method described in Japanese Patent No. 6349629.

[0244] Another method for introducing an acidic functional group into a resin is to react an acid anhydride with a hydroxyl group generated by a ring-opening reaction of an epoxy group in a dispersant (especially a dispersant having an ethylenically unsaturated group) or an alkali-soluble resin to introduce an acid group.

[0245] In the present invention, a resin having a basic functional group is preferably used as the resin. This improves the developability of the colored photosensitive composition and facilitates the formation of pixels with excellent rectangularity. Examples of the basic functional group include amino groups and heteroaryl groups containing nitrogen atoms. An amino group is preferred, and a tertiary amino group is more preferred. Resins having a basic functional group can be used, for example, as alkali-soluble resins.

[0246] The amine value of the resin having an amino group as a basic functional group is preferably 20 mgKOH / g to 200 mgKOH / g. The lower limit is more preferably 30 mgKOH / g or more, and particularly preferably 40 mgKOH / g or more. The upper limit is more preferably 180 mgKOH / g or less, further preferably 160 mgKOH / g or less, and particularly preferably 140 mgKOH / g or less. The weight average molecular weight (Mw) of the resin having an amino group is preferably 5,000 to 100,000. Furthermore, the number average molecular weight (Mn) of the resin having an amino group is preferably 1,000 to 20,000.

[0247] The colored photosensitive composition of the present invention can contain a resin as a dispersant. Examples of the dispersant include acidic dispersants (acidic resins) and alkaline dispersants (alkaline resins). Here, the acidic dispersant (acidic resin) refers to a resin in which the amount of acidic functional groups is greater than the amount of alkaline functional groups. When the total amount of the acidic functional groups and the amount of the alkaline functional groups is set to 100 mol%, the acidic dispersant (acidic resin) is preferably a resin in which the amount of acidic functional groups accounts for 70 mol% or more, and more preferably a resin that substantially only contains acidic functional groups. The acidic functional group possessed by the acidic dispersant (acidic resin) is preferably a carboxyl group. The acid value of the acidic dispersant (acidic resin) is preferably 30 mgKOH / g to 105 mgKOH / g, more preferably 40 mgKOH / g to 105 mgKOH / g, and even more preferably 50 mgKOH / g to 105 mgKOH / g. Furthermore, a basic dispersant (basic resin) refers to a resin having a greater amount of basic functional groups than acidic functional groups. When the total amount of acidic and basic functional groups is taken as 100 mol%, the basic dispersant (basic resin) preferably contains more than 50 mol% of basic functional groups. The basic functional groups in the basic dispersant are preferably amino groups.

[0248] The resin used as the dispersant preferably contains a repeating unit having an acidic functional group. When the resin used as the dispersant contains a repeating unit having an acidic functional group, the generation of development residues can be further suppressed during pattern formation by photolithography.

[0249] The resin used as the dispersant is preferably a grafted resin. The details of the grafted resin can be found in paragraphs 0025 to 0094 of JP-A-2012-255128, which are incorporated herein by reference.

[0250] The resin used as the dispersant is also preferably a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and side chains. Preferred polyimine-based dispersants include a main chain and side chains, with at least one of the main chain and side chains containing a basic nitrogen atom, the main chain containing a partial structure having a functional group with a pKA of 14 or less, and the side chains containing 40 to 10,000 atoms. There are no particular limitations on the basic nitrogen atom, as long as it is basic. For information on polyimine-based dispersants, reference can be made to paragraphs 0102 to 0166 of Japanese Patent Application Publication No. 2012-255128, which is incorporated herein by reference.

[0251] The resin used as the dispersant is also preferably a resin having a structure in which multiple polymer chains are bonded to a core portion. Examples of such resins include dendritic polymers (including star polymers). Specific examples of dendritic polymers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.

[0252] Furthermore, the above-mentioned resin having an acidic functional group (alkali-soluble resin) can also be used as a dispersant.

[0253] Furthermore, the resin used as the dispersant is preferably a resin containing repeating units having a group containing an ethylenically unsaturated bond in its side chain. The content of repeating units having a group containing an ethylenically unsaturated bond in its side chain is preferably 10 mol% or more, more preferably 10 mol% to 80 mol%, and even more preferably 20 mol% to 70 mol%, based on all repeating units in the resin.

[0254] Furthermore, as the dispersant, preferably, a resin having an aromatic carboxyl group (hereinafter referred to as "resin B") is used.

[0255] In Resin B, the aromatic carboxyl groups may be contained in the main chain of the repeating unit or in the side chain of the repeating unit. Due to excellent developability and fading properties, the aromatic carboxyl groups are preferably contained in the main chain of the repeating unit. Although the details are unclear, it is speculated that the presence of aromatic carboxyl groups near the main chain further enhances these properties. In this specification, an aromatic carboxyl group refers to a group having a structure in which one or more carboxyl groups are bonded to an aromatic ring. Among the aromatic carboxyl groups, the number of carboxyl groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.

[0256] The resin B used in the present invention is preferably a resin containing at least one repeating unit selected from the repeating unit represented by formula (b-1) and the repeating unit represented by formula (b-10).

[0257] [Chemical Formula 18]

[0258]

[0259] In formula (b-1), Ar 1 represents a group containing an aromatic carboxyl group, L 1 Indicates -COO- or -CONH-, L 2 represents a divalent linking group.

[0260] In formula (b-10), Ar 10 represents a group containing an aromatic carboxyl group, L 11 Indicates -COO- or -CONH-, L 12 represents a trivalent linking group, P 10 represents a polymer chain.

[0261] First, the formula (b-1) is described. In the formula (b-1), Ar 1 Examples of the group containing an aromatic carboxyl group include a structure derived from an aromatic tricarboxylic anhydride, a structure derived from an aromatic tetracarboxylic anhydride, etc. Examples of the aromatic tricarboxylic anhydride and the aromatic tetracarboxylic anhydride include compounds having the following structures.

[0262] [Chemical Formula 19]

[0263]

[0264] In the above formula, Q 1 It represents a single bond, -O-, -CO-, -COOCH2CH2OCO-, -SO2-, -C(CF3)2-, a group represented by the following formula (Q-1), or a group represented by the following formula (Q-2).

[0265] [Chemical Formula 20]

[0266]

[0267] Specific examples of the aromatic tricarboxylic anhydride include benzenetricarboxylic anhydride (such as 1,2,3-benzenetricarboxylic anhydride and trimellitic anhydride [1,2,4-benzenetricarboxylic anhydride]), naphthalenetricarboxylic anhydride (such as 1,2,4-naphthalenetricarboxylic anhydride, 1,4,5-naphthalenetricarboxylic anhydride, 2,3,6-naphthalenetricarboxylic anhydride and 1,2,8-naphthalenetricarboxylic anhydride), 3,4,4'-benzophenonetricarboxylic anhydride, 3,4,4'-biphenylethertricarboxylic anhydride, 3,4,4'-biphenyltricarboxylic anhydride, 2,3,2'-biphenyltricarboxylic anhydride, 3,4,4'-biphenylmethanetricarboxylic anhydride, and 3,4,4'-biphenylsulfonetricarboxylic anhydride. Specific examples of aromatic tetracarboxylic anhydrides include pyromellitic dianhydride, ethylene glycol trimellitic anhydride, propylene glycol trimellitic anhydride, butanediol trimellitic anhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 3,3',4,4'-biphenylsulfone tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, 2,3,6,7-naphthalene tetracarboxylic dianhydride, 3,3',4,4'-diphenyl sulfone tetracarboxylic dianhydride, 4,4'-biphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-dimethyldiphenylsilane tetracarboxylic dianhydride, 3,3',4,4'-tetraphenylsilane tetracarboxylic dianhydride, 1,2,3,4-furan tetracarboxylic dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride, 4,4'-bis(3,4 -dicarboxyphenoxy)diphenylpropane dianhydride, 3,3',4,4'-perfluoroisopropylidene diphthalic acid dianhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, bis(phthalic acid)phenylphosphine oxide dianhydride, p-phenylene-bis(triphenylphthalic acid) dianhydride, m-phenylene-bis(triphenylphthalic acid) dianhydride, bis(triphenylphthalic acid)-4,4'-diphenyl ether dianhydride anhydride, bis(triphenylphthalate)-4,4'-diphenylmethane dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride, 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic acid dianhydride or 3,4-dicarboxy-1,2,3,4-tetrahydro-6-methyl-1-naphthalene succinic acid dianhydride, etc.

[0268] As Ar 1 Specific examples of the group containing an aromatic carboxyl group include a group represented by formula (Ar-1), a group represented by formula (Ar-2), a group represented by formula (Ar-3), and the like.

[0269] [Chemical Formula 21]

[0270]

[0271] In formula (Ar-1), n1 represents an integer of 1 to 4, preferably an integer of 1 to 2, and more preferably 2.

[0272] In formula (Ar-2), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 to 2, and even more preferably 2.

[0273] In formula (Ar-3), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 to 2, and further preferably 1. However, at least one of n3 and n4 is an integer of 1 or greater.

[0274] In formula (Ac-3), Q 1 It represents a single bond, -O-, -CO-, -COOCH2CH2OCO-, -SO2-, -C(CF3)2-, a group represented by the above formula (Q-1), or a group represented by the above formula (Q-2).

[0275] In formula (b-1), L 1 represents -COO- or -CONH-, preferably represents -COO-.

[0276] In formula (b-1), as L 2 The divalent linking group represented by can be exemplified by alkylene, arylene, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and groups formed by combining two or more of these. The number of carbon atoms of the alkylene is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The alkylene group can be any of linear, branched, and cyclic. The number of carbon atoms of the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The alkylene and arylene groups may have substituents. Examples of the substituents include hydroxyl groups and the like. L 2 The divalent linking group represented by is preferably -OL 2a -O- represented by the group. 2a Examples include: an alkylene group; an arylene group; a group formed by combining an alkylene group and an arylene group; and a group formed by combining at least one selected from an alkylene group and an arylene group with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 15. The alkylene group may be linear, branched, or cyclic. The alkylene group and the arylene group may have substituents. Examples of substituents include hydroxyl groups.

[0277] Next, the formula (b-10) will be described. In the formula (b-10), Ar 10 The group containing an aromatic carboxyl group represented by 1 The meanings are the same, and the preferred ranges are also the same.

[0278] In formula (b-10), L11 represents -COO- or -CONH-, preferably represents -COO-.

[0279] In formula (b-10), as L 12 The trivalent linking group represented by is exemplified by hydrocarbon groups, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and groups formed by combining two or more of these. Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbons. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be any of linear, branched, and cyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include hydroxyl groups and the like. L 12 The trivalent linking group represented is preferably a group represented by the following formula (L12-1), more preferably a group represented by formula (L12-2).

[0280] [Chemical Formula 22]

[0281]

[0282] L 12a and L 12b Each independently represents a trivalent linking group, X 1 represents S, *1 represents L in formula (b-10) 11 The bonding position of *2 indicates the bonding position with P of formula (b-10) 10 bonding position.

[0283] As L 12a and L 12b Examples of the trivalent linking group represented by include a hydrocarbon group; and a group formed by combining a hydrocarbon group with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-.

[0284] In formula (b-10), P 10 Represents a polymer chain. 10 The polymer chain represented preferably has at least one repeating unit selected from the group consisting of poly(meth)acrylic acid repeating units, polyether repeating units, polyester repeating units, and polyol repeating units. 10 The weight average molecular weight of is preferably 500 to 20,000. The lower limit is more preferably 500 or more, particularly preferably 1,000 or more. The upper limit is more preferably 10,000 or less, further preferably 5,000 or less, particularly preferably 3,000 or less. 10When the weight average molecular weight of the pigment is within the above range, the dispersibility of the pigment in the composition is good. When the resin B is a resin having a repeating unit represented by formula (b-10), the resin B is preferably used as a dispersant.

[0285] In formula (b-10), P 10 The polymer chain represented is preferably a polymer chain containing repeating units represented by the following formulae (P-1) to (P-5), and more preferably a polymer chain containing a repeating unit represented by (P-5).

[0286] [Chemical Formula 23]

[0287]

[0288] In the above formula, R P1 and R P2 Each represents an alkylene group. P1 and R P2 The alkylene group represented by is preferably a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably a linear or branched alkylene group having 2 to 16 carbon atoms, and still more preferably a linear or branched alkylene group having 3 to 12 carbon atoms.

[0289] In the above formula, R P3 represents a hydrogen atom or a methyl group.

[0290] In the above formula, L P1 represents a single bond or an arylene group, L P2 Represents a single bond or a divalent linking group. P1 Preferably it is a single bond. P2 Examples of the divalent linking group represented include alkylene groups (preferably alkylene groups having 1 to 12 carbon atoms), arylene groups (preferably arylene groups having 6 to 20 carbon atoms), -NH-, -SO-, -SO2-, -CO-, -O-, -COO-, -OCO-, -S-, -NHCO-, -CONH-, and groups formed by combining two or more of these.

[0291] R P4Represents a hydrogen atom or a substituent. As a substituent, a hydroxyl group, a carboxyl group, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkyl sulfide group, an aryl sulfide group, a heteroaryl sulfide group, a (meth) acryloyl group, an oxetane group, a blocked isocyanate group, etc. can be listed. In addition, the blocked isocyanate group in the present invention is a group that can generate an isocyanate group by heat. For example, it is possible to preferably list a group that allows a blocking agent to react with an isocyanate group and protect the isocyanate group. As a blocking agent, an oxime compound, a lactam compound, a phenol compound, an alcohol compound, an amine compound, an active methylene compound, a pyrazole compound, a thiol compound, an imidazole compound, an imide compound, etc. can be listed. As a blocking agent, the compounds described in paragraphs 0115 to 0117 of Japanese Patent Application Laid-Open No. 2017-067930 can be listed, and the content is incorporated into this specification. Furthermore, the blocked isocyanate group is preferably a group capable of generating an isocyanate group by heat at 90°C to 260°C.

[0292] P 10 The represented polymer chain preferably has at least one group selected from (meth) acryloyl, oxetanyl, blocked isocyanate and tert-butyl (hereinafter also referred to as "functional group A"). Functional group A is more preferably at least one selected from (meth) acryloyl, oxetanyl and blocked isocyanate. When the polymer chain contains functional group A, it is easy to form a film with excellent solvent resistance. In particular, when it contains at least one group selected from (meth) acryloyl, oxetanyl and blocked isocyanate, the above effect is significant. In addition, when functional group A has a tert-butyl group, it is preferred that the composition contains a compound having an epoxy group or an oxetanyl group. When functional group A has a blocked isocyanate group, it is preferred that the composition contains a compound having a hydroxyl group.

[0293] Moreover, P 10 The polymer chain represented is more preferably a polymer chain having a repeating unit containing the functional group A in the side chain. 10 The proportion of repeating units containing the functional group A on the side chain in all repeating units is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 20% by mass or more. The upper limit can be set to 100% by mass, preferably 90% by mass or less, and more preferably 60% by mass or less.

[0294] Moreover, P 10The polymer chain preferably also contains repeating units containing an acidic functional group. Examples of the acidic functional group include a carboxyl group, a phosphoric acid functional group, a sulfonic group, and a phenolic hydroxyl group. This embodiment can further improve the dispersibility of the pigment in the composition. Furthermore, the developability can also be improved. The proportion of repeating units containing an acidic functional group is preferably 1% to 30% by mass, more preferably 2% to 20% by mass, and even more preferably 3% to 10% by mass.

[0295] Resin B can be produced by reacting at least one acid anhydride selected from aromatic tetracarboxylic anhydrides and aromatic tricarboxylic anhydrides with a hydroxyl-containing compound. Examples of the aromatic tetracarboxylic anhydrides and aromatic tricarboxylic anhydrides include the above-mentioned acid anhydrides. The hydroxyl-containing compound is not particularly limited as long as it has a hydroxyl group in the molecule, but is preferably a polyol having two or more hydroxyl groups in the molecule. Furthermore, compounds having two hydroxyl groups and one thiol group in the molecule are also preferably used as the hydroxyl-containing compound. Examples of compounds having two hydroxyl groups and one thiol group in the molecule include 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethylene glycol, 3-mercapto-1,2-propylene glycol (thioglycerol), 2-mercapto-1,2-propylene glycol, 2-mercapto-2-methyl-1,3-propylene glycol, 2-mercapto-2-ethyl-1,3-propylene glycol, 1-mercapto-2,2-propylene glycol, 2-mercaptoethyl-2-methyl-1,3-propylene glycol, or 2-mercaptoethyl-2-ethyl-1,3-propylene glycol. Examples of other hydroxyl group-containing compounds include those described in paragraphs 0084 to 0095 of JP-A-2018-101039, the contents of which are incorporated herein.

[0296] The molar ratio of the acid anhydride group in the acid anhydride to the hydroxyl group in the hydroxyl group-containing compound (acid anhydride group / hydroxyl group) is preferably 0.5 to 1.5.

[0297] Furthermore, the resin containing the repeating unit represented by the above formula (b-10) can be synthesized by the methods shown in the following synthesis methods (1) and (2).

[0298] [Synthesis method (1)]

[0299] A method for producing a vinyl polymer having two hydroxyl groups at one terminal region by free radical polymerization of a polymerizable monomer having an ethylenically unsaturated group in the presence of a hydroxyl-containing thiol compound (preferably a compound having two hydroxyl groups and one thiol group in the molecule), and then reacting the synthesized vinyl polymer with one or more aromatic anhydrides selected from aromatic tetracarboxylic anhydrides and aromatic tricarboxylic anhydrides.

[0300] [Synthesis method (2)]

[0301] A method for producing a polymerizable monomer having an ethylenically unsaturated group by reacting a hydroxyl group-containing compound (preferably a compound having two hydroxyl groups and one thiol group in the molecule) with one or more aromatic anhydrides selected from aromatic tetracarboxylic anhydrides and aromatic tricarboxylic anhydrides, and then radically polymerizing a polymerizable monomer having an ethylenically unsaturated group in the presence of the obtained reactants. In the synthesis method (2), the polymerizable monomer having a hydroxyl group can be radically polymerized and then further reacted with a compound having an isocyanate group (for example, a compound having an isocyanate group and the functional group A). In this way, the functional group A can be introduced into the polymer chain P. 10 .

[0302] Furthermore, resin B can also be synthesized according to the method described in paragraphs 0120 to 0138 of JP-A-2018-101039.

[0303] The weight-average molecular weight of resin B is preferably 2,000 to 35,000. The upper limit is more preferably 25,000 or less, further preferably 20,000 or less, and particularly preferably 15,000 or less. The lower limit is more preferably 4,000 or greater, further preferably 6,000 or greater, and particularly preferably 7,000 or greater. When the weight-average molecular weight of resin B is within this range, the effects of the present invention can be more significantly achieved. Furthermore, the storage stability of the colored photosensitive composition can be improved.

[0304] Dispersants are also commercially available. Specific examples include the DISPERBYK series (e.g., DISPERBYK-111, 161, etc.) manufactured by BYK Chemie GmbH and the SOLSPERSE series (e.g., SOLSPERSE 76500, etc.) manufactured by Lubrizol Japan Limited. Furthermore, the pigment dispersants described in paragraphs 0041 to 0130 of JP-A-2014-130338 can also be used, and the contents are incorporated herein. Furthermore, the resins described as dispersants above can also be used for purposes other than dispersants. For example, they can also be used as binders.

[0305] When the colored photosensitive composition of the present invention contains a resin, the content of the resin in the total solids of the colored photosensitive composition is preferably 5% to 50% by mass. The lower limit is more preferably 10% by mass or more, and particularly preferably 15% by mass or more. The upper limit is more preferably 40% by mass or less, further preferably 35% by mass or less, and particularly preferably 30% by mass or less. Furthermore, the content of the resin having an acidic functional group (alkali-soluble resin) in the total solids of the colored photosensitive composition is preferably 5% to 50% by mass. The lower limit is more preferably 10% by mass or more, and particularly preferably 15% by mass or more. The upper limit is more preferably 40% by mass or less, further preferably 35% by mass or less, and particularly preferably 30% by mass or less. Furthermore, from the perspective of easily obtaining excellent developability, the content of the resin having an acidic functional group (alkali-soluble resin) in the total amount of the resin is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 70% by mass or more, and particularly preferably 80% by mass or more. The upper limit can be 100% by mass, 95% by mass, or 90% by mass or less. In the colored photosensitive composition of the present invention, only one resin may be used, or two or more resins may be used in combination. When two or more resins are used in combination, the total amount of these resins is preferably within the above range.

[0306] <Pigment derivatives>

[0307] The colored photosensitive composition of the present invention may contain a pigment derivative. In addition, the "pigment derivative" in the present invention refers to a pigment derivative other than the diketopyrrolopyrrole compounds A and B represented by the above formula 1.

[0308] As pigment derivatives, compounds with a structure formed by replacing a part of a chromophore with an acidic functional group or a basic functional group can be enumerated. As the chromophore constituting the pigment derivative, quinoline skeleton, benzimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, phthalocyanine skeleton, anthraquinone skeleton, quinacridone skeleton, dioxazine skeleton, purple ring ketone skeleton, perylene skeleton, thioindigo skeleton, isoindoline skeleton, isoindolinone skeleton, quinophthalone skeleton, styrene skeleton, metal complex skeleton etc. can be enumerated, preferably quinoline skeleton, benzimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, quinophthalone skeleton, isoindoline skeleton and phthalocyanine skeleton, more preferably azo skeleton and benzimidazolone skeleton. As acidic functional group, sulfo group, carboxyl group, phosphoric acid functional group and the salt thereof can be enumerated. As the atom or atomic group constituting the salt, alkali metal ion (Li ion) can be enumerated. + 、Na + , K + etc.), alkaline earth metal ions (Ca 2+ Mg 2+Examples of the basic functional group include amino, pyridyl, and salts thereof, ammonium salts, and phthalimidomethyl groups. Examples of the atom or atomic group constituting the salt include hydroxide, halide, carboxylate, sulfonate, and phenoxide.

[0309] As the pigment derivative, a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative) can also be used. The maximum value (εmax) of the molar absorption coefficient of the transparent pigment derivative in the wavelength range of 400 nm to 700 nm is preferably 3,000 L·mol -1 cm -1 Below, more preferably 1,000 L·mol -1 cm -1 Below, more preferably 100 L·mol -1 cm -1 Below. The lower limit of εmax is, for example, 1 L·mol -1 cm -1 Above, can also be 10L·mol -1 cm -1 above.

[0310] Specific examples of the pigment derivatives include Japanese Patent Application Laid-Open No. 56-118462, Japanese Patent Application Laid-Open No. 63-264674, Japanese Patent Application Laid-Open No. 01-217077, Japanese Patent Application Laid-Open No. 03-009961, Japanese Patent Application Laid-Open No. 03-026767, Japanese Patent Application Laid-Open No. 03-153780, Japanese Patent Application Laid-Open No. 03-0456 62, Japanese Patent Application Laid-Open No. 04-285669, Japanese Patent Application Laid-Open No. 06-145546, Japanese Patent Application Laid-Open No. 06-212088, Japanese Patent Application Laid-Open No. 06-240158, Japanese Patent Application Laid-Open No. 10-030063, Japanese Patent Application Laid-Open No. 10-195326, International Publication No. 2011 / 024896, 0086 to 0098, paragraphs 0063 to 0094 of International Publication No. 2012 / 102399, paragraph 0082 of International Publication No. 2017 / 038252, paragraph 0171 of Japanese Patent Application Publication No. 2015-151530, paragraphs 0162 to 0183 of Japanese Patent Application Publication No. 2011-252065, Japanese Patent Application Publication No. 2003-081972, Japanese Patent Application Publication No. Compounds described in Japanese Patent No. 5299151, Japanese Patent Application Laid-Open No. 2015-172732, Japanese Patent Application Laid-Open No. 2014-199308, Japanese Patent Application Laid-Open No. 2014-085562, Japanese Patent Application Laid-Open No. 2014-035351, Japanese Patent Application Laid-Open No. 2008-081565, and Japanese Patent Application Laid-Open No. 2019-109512.

[0311] The content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass, relative to 100 parts by mass of the pigment.

[0312] <Polymerizable Compound>

[0313] The colored photosensitive composition of the present invention preferably contains a polymerizable compound. As the polymerizable compound, known compounds that can be crosslinked by free radicals, acids, or heat can be used. In the present invention, the polymerizable compound is preferably a compound having an ethylenically unsaturated group, for example. Examples of the ethylenically unsaturated group include vinyl, (meth)allyl, and (meth)acryloyl groups. The polymerizable compound used in the present invention is preferably a free radical polymerizable compound.

[0314] The polymerizable compound can be in any chemical form, such as a monomer, prepolymer, or oligomer, but is preferably a monomer. The molecular weight of the polymerizable compound is preferably 100 to 3,000. The upper limit is more preferably 2,000 or less, and even more preferably 1,500 or less. The lower limit is more preferably 150 or more, and even more preferably 250 or more.

[0315] The polymerizable compound is preferably a compound containing three or more ethylenically unsaturated groups, more preferably a compound containing three to 15 ethylenically unsaturated groups, and even more preferably a compound containing three to six ethylenically unsaturated groups. Furthermore, the polymerizable compound is preferably a trifunctional to pentafunctional (meth)acrylate compound, and more preferably a trifunctional to hexafunctional (meth)acrylate compound. Specific examples of polymerizable compounds include compounds described in paragraphs 0095 to 0108 of JP-A-2009-288705, paragraph 0227 of JP-A-2013-029760, paragraphs 0254 to 0257 of JP-A-2008-292970, paragraphs 0034 to 0038 of JP-A-2013-253224, paragraph 0477 of JP-A-2012-208494, JP-A-2017-048367, Japanese Patent No. 6057891, and Japanese Patent No. 6031807, the contents of which are incorporated into this specification.

[0316] Preferred polymerizable compounds include dipentaerythritol triacrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (commercially available as KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available as KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available as KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., NK Ester A-DPH-12E; manufactured by Shin Nakamura Chemical Co., Ltd.), and compounds having a structure in which these (meth)acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues (for example, SR454 and SR499 commercially available from Sartomer Company, Inc.). In addition, as the polymerizable compound, diglycerol EO (ethylene oxide)-modified (meth)acrylate (commercially available product M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (manufactured by Shin Nakamura Chemical Co., Ltd., NK Ester A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), ARONIX TO-2349 (manufactured by Toagosei Co., Ltd.), NK OLIGO UA-7200 (manufactured by Shin Nakamura Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), LIGHTACRYLATE POB-A0 (manufactured by KYOEISHA CHEMICAL Co., Ltd.), etc.

[0317] As the polymerizable compound, trifunctional (meth)acrylate compounds such as trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide-modified tri(meth)acrylate, trimethylolpropane ethylene oxide-modified tri(meth)acrylate, isocyanurate ethylene oxide-modified tri(meth)acrylate, and pentaerythritol tri(meth)acrylate are also preferably used. Examples of commercially available trifunctional (meth)acrylate compounds include ARONIX M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305, M-303, M-452, and M-450 (manufactured by TOAGOSEICO, LTD.), NK ESTERA 9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A-TMPT, and TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.). o ., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.), etc.

[0318] As the polymerizable compound, a polymerizable compound having an acidic functional group can also be used. By using a polymerizable compound having an acidic functional group, the unexposed portion of the colored photosensitive composition can be easily removed during development, and the generation of development residues can be suppressed. Examples of the acidic functional group include carboxyl groups, sulfonic groups, and phosphoric acid functional groups, with carboxyl groups being preferred. Commercially available polymerizable compounds having an acidic functional group include ARONIX M-510, M-520, and ARONIX TO-2349 (manufactured by TOAGOSEICO, LTD.). The preferred acid value of the polymerizable compound having an acidic functional group is 0.1 mgKOH / g to 40 mgKOH / g, and more preferably 5 mgKOH / g to 30 mgKOH / g. If the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in the developer is good, and if it is 40 mgKOH / g or less, it is advantageous in production or handling.

[0319] As the polymerizable compound, a polymerizable compound having a caprolactone structure can also be used. Polymeric compounds having a caprolactone structure are commercially available, for example, from NIPPON KAYAKU CO., LTD. as the KAYARAD DPCA series, including DPCA-20, DPCA-30, DPCA-60, and DPCA-120.

[0320] As the polymerizable compound, a polymerizable compound having an alkyleneoxy group can also be used. The polymerizable compound having an alkyleneoxy group is preferably a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group, more preferably a polymerizable compound having an ethyleneoxy group, and still more preferably a trifunctional to hexafunctional (meth)acrylate compound having 4 to 20 ethyleneoxy groups. Commercially available polymerizable compounds having an alkyleneoxy group include, for example, SR-494 manufactured by Sartomer Company, Inc., a tetrafunctional (meth)acrylate having 4 ethyleneoxy groups, and KAYARAD TPA-330, a trifunctional (meth)acrylate having 3 oxyisobutylene groups.

[0321] As the polymerizable compound, a polymerizable compound having a fluorene skeleton can also be used. Commercially available polymerizable compounds having a fluorene skeleton include OGSOL EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton).

[0322] As the polymerizable compound, it is also preferable to use a compound that does not substantially contain environmentally regulated substances such as toluene. Examples of commercially available products of these compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).

[0323] As the polymerizable compound, it is also preferable to use the polyurethane acrylates described in Japanese Patent Publication No. 48-041708, Japanese Patent Application Laid-Open No. 51-037193, Japanese Patent Application Laid-Open No. 02-032293, and Japanese Patent Application Laid-Open No. 02-016765, the urethane ester compounds having an ethylene oxide skeleton described in Japanese Patent Publication No. 58-049860, Japanese Patent Publication No. 56-017654, Japanese Patent Application Laid-Open No. 62-039417, and Japanese Patent Application Laid-Open No. 62-039418, and the polymerizable compounds having an amino structure or a sulfide structure in the molecule described in Japanese Patent Application Laid-Open No. 63-277653, Japanese Patent Application Laid-Open No. 63-260909, and Japanese Patent Application Laid-Open No. 01-105238. In addition, as polymerizable compounds, commercially available products such as UA-7200 (manufactured by Shin Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, and LINC-202UA (manufactured by KYOEISHA CHEMICAL Co., Ltd.) can also be used.

[0324] When the colored photosensitive composition of the present invention contains a polymerizable compound, the content of the polymerizable compound in the total solids content of the colored photosensitive composition is preferably 0.1% to 50% by mass. The lower limit is more preferably 0.5% by mass or greater, and even more preferably 1% by mass or greater. The upper limit is more preferably 45% by mass or less, and even more preferably 40% by mass or less.

[0325] Furthermore, from the perspectives of curability, developability, and film-forming properties, the total content of the polymerizable compound and the resin in the total solids content of the colored photosensitive composition is preferably 10 to 65% by mass. The lower limit is more preferably 15% by mass or more, further preferably 20% by mass or more, and particularly preferably 30% by mass or more. The upper limit is more preferably 60% by mass or less, further preferably 50% by mass or less, and particularly preferably 40% by mass or less. Furthermore, it is preferred that 30 to 300 parts by mass of the resin be contained per 100 parts by mass of the polymerizable compound. The lower limit is more preferably 50 parts by mass or more, and particularly preferably 80 parts by mass or more. The upper limit is more preferably 250 parts by mass or less, and particularly preferably 200 parts by mass or less.

[0326] In the colored photosensitive composition of the present invention, the polymerizable compound may be used alone or in combination of two or more. When two or more polymerizable compounds are used, the total amount thereof is preferably within the above range.

[0327] <Photopolymerization Initiator>

[0328] The colored photosensitive composition of the present invention preferably contains a photopolymerization initiator. In particular, when the colored photosensitive composition of the present invention contains a polymerizable compound, the colored photosensitive composition of the present invention also preferably contains a photopolymerization initiator. The photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound that is photosensitized to light in the ultraviolet to visible range is preferred. The photopolymerization initiator is preferably a photoradical polymerization initiator.

[0329] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, sulfur compounds, ketone compounds, aromatic onium salts, α-hydroxyketone compounds, α-aminoketone compounds, etc. From the viewpoint of exposure sensitivity, the photoradical polymerization initiator is preferably a compound selected from trihalomethyltriazine compounds, benzyldimethylketal compounds, α-hydroxyketone compounds, α-aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, triarylimidazole dimers, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds, and 3-aryl-substituted coumarin compounds. More preferably, it is a compound selected from oxime compounds, α-hydroxyketone compounds, α-aminoketone compounds, and acylphosphine compounds, and even more preferably, it is an oxime compound. In addition, examples of photopolymerization initiators include compounds described in paragraphs 0065 to 0111 of Japanese Patent Publication No. 2014-130173, Japanese Patent Publication No. 6301489, peroxide-based photopolymerization initiators described in MATERIAL STAGE 37 to 60p, vol. 19, No. 3, 2019, photopolymerization initiators described in International Publication No. 2018 / 221177, photopolymerization initiators described in International Publication No. 2018 / 110179, photopolymerization initiators described in Japanese Patent Publication No. 2019-043864, photopolymerization initiators described in Japanese Patent Publication No. 2019-044030, and organic peroxides described in Japanese Patent Publication No. 2019-167313, and the contents are incorporated into this specification.

[0330] Examples of commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins B.V.), and Irgacure 184, Irgacure 1173, Irgacure 2959, and Irgacure 127 (all manufactured by BASF). Examples of commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG (all manufactured by IGM Resins B.V.), and Irgacure 907, Irgacure 369, Irgacure 369E, and Irgacure 379EG (all manufactured by BASF). Examples of commercially available acylphosphine compounds include Omnirad 819 and Omnirad TPO (both manufactured by IGM Resins B.V.), Irgacure 819 and Irgacure TPO (both manufactured by BASF), and the like.

[0331] Examples of the oxime compound include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, compounds described in JCS Perkin II (1979, pp. 1653-1660), compounds described in JCS Perkin II (1979, pp. 156-162), and compounds described in Journal of Photopolymer Science and Technology. Technology (1995, pp. 202-232), compounds described in Japanese Patent Application Laid-Open No. 2000-066385, compounds described in Japanese Patent Application Laid-Open No. 2000-080068, compounds described in Japanese Patent Application Laid-Open No. 2004-534797, compounds described in Japanese Patent Application Laid-Open No. 2006-342166, compounds described in Japanese Patent Application Laid-Open No. 2017-019766, Compounds described in Japanese Patent No. 6065596, compounds described in International Publication No. 2015 / 152153, compounds described in International Publication No. 2017 / 051680, compounds described in Japanese Patent Unexamined Publication No. 2017-198865, compounds described in paragraphs 0025 to 0038 of International Publication No. 2017 / 164127, and compounds described in International Publication No. 2013 / 167515. Specific examples of oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3-(4-toluenesulfonyloxy)iminobutane-2-one and 2-ethoxycarbonyloxyimino-1-phenylpropane-1-one. Commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, and Irgacure OXE04 (all manufactured by BASF), TR-PBG-304 (manufactured by Changzhou Tronly New Electronic Materials Co., Ltd.), and Adeka Optomer N-1919 (manufactured by ADEKA Corporation, a photopolymerization initiator 2 described in Japanese Patent Application Laid-Open No. 2012-014052). Furthermore, it is also preferred to use a non-coloring compound or a highly transparent compound that is less susceptible to discoloration as the oxime compound.Examples of commercially available products include ADEKA ARKLS NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA CORPORATION).

[0332] As the photopolymerization initiator, an oxime compound having a fluorene ring can also be used. Specific examples of the oxime compound having a fluorene ring include compounds described in JP-A-2014-137466.

[0333] As the photopolymerization initiator, an oxime compound having a skeleton in which at least one benzene ring in a carbazole ring is replaced by a naphthalene ring can also be used. Specific examples of such oxime compounds include the compounds described in International Publication No. 2013 / 083505.

[0334] As the photopolymerization initiator, an oxime compound having a fluorine atom can also be used. Specific examples of the oxime compound having a fluorine atom include the compounds described in JP-A-2010-262028, compounds 24, 36 to 40 described in JP-A-2014-500852, and compound (C-3) described in JP-A-2013-164471.

[0335] As the photopolymerization initiator, an oxime compound having a nitro group can be used. It is also preferred to form an oxime compound having a nitro group in the form of a dimer. Specific examples of oxime compounds having a nitro group include the compounds described in paragraphs 0031 to 0047 of Japanese Patent Application Laid-Open No. 2013-114249, paragraphs 0008 to 0012 and paragraphs 0070 to 0079 of Japanese Patent Application Laid-Open No. 2014-137466, the compounds described in paragraphs 0007 to 0025 of Japanese Patent Application No. 4223071, and ADEKA ARKLS NC[-831 (manufactured by ADEKA Corporation).

[0336] As the photopolymerization initiator, an oxime compound having a benzofuran skeleton can also be used. Specific examples include OE-01 to OE-75 described in International Publication No. 2015 / 036910.

[0337] As a photopolymerization initiator, an oxime compound having a substituent having a hydroxyl group bonded to a carbazole skeleton can also be used. As these photopolymerization initiators, compounds described in International Publication No. 2019 / 088055 can be cited.

[0338] Specific examples of the oxime compound preferably used in the present invention are shown below, but the present invention is not limited thereto.

[0339] [Chemical Formula 24]

[0340]

[0341] [Chemical Formula 25]

[0342]

[0343] The oxime compound is preferably a compound having a maximum absorption wavelength in the range of 350 nm to 500 nm, more preferably a compound having a maximum absorption wavelength in the range of 360 nm to 480 nm. Furthermore, from the viewpoint of sensitivity, the molar absorptivity of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1,000 to 300,000, further preferably 2,000 to 300,000, and particularly preferably 5,000 to 200,000. The molar absorptivity of the compound can be measured using a known method. For example, it is preferably measured using ethyl acetate at a concentration of 0.01 g / L using a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).

[0344] As photopolymerization initiators, bifunctional, trifunctional, or higher-functional photoradical polymerization initiators can be used. By using these photoradical polymerization initiators, two or more free radicals are generated from one molecule of the photoradical polymerization initiator, thereby achieving excellent sensitivity. Furthermore, when using asymmetric compounds, crystallinity is reduced, solubility in solvents is improved, and precipitation over time is less likely to occur, thereby improving the temporal stability of the colored photosensitive composition. Specific examples of bifunctional or trifunctional or higher-functional photoradical polymerization initiators include dimers of oxime compounds described in JP-A-2010-527339, JP-A-2011-524436, International Publication No. 2015 / 004565, paragraphs 0407 to 0412 of JP-A-2016-532675, and paragraphs 0039 to 0055 of International Publication No. 2017 / 033680, and compound (E) described in JP-A-2013-522445. and compound (G), Cmpd1 to 7 described in International Publication No. 2016 / 034963, the oxime ester photoinitiator described in paragraph 0007 of Japanese Unexamined Patent Application Publication No. 2017-523465, the photoinitiator described in paragraphs 0020 to 0033 of Japanese Unexamined Patent Application Publication No. 2017-167399, the photopolymerization initiator (A) described in paragraphs 0017 to 0026 of Japanese Unexamined Patent Application Publication No. 2017-151342, the oxime ester photoinitiator described in Japanese Patent No. 6469669, etc.

[0345] When the colored photosensitive composition of the present invention contains a photopolymerization initiator, the content of the photopolymerization initiator in the total solids content of the colored photosensitive composition is preferably 0.1% to 30% by mass. The lower limit is more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more. The upper limit is more preferably 20% by mass or less, and particularly preferably 15% by mass or less. In the colored photosensitive composition of the present invention, only one type of photopolymerization initiator may be used, or two or more types may be used in combination. When two or more types are used, the total amount of these initiators is preferably within the above range.

[0346] <Compound Having a Cyclic Ether Group>

[0347] The colored photosensitive composition of the present invention may contain a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. The compound having a cyclic ether group is preferably a compound having an epoxy group. Examples of the compound having an epoxy group include compounds having one or more epoxy groups in one molecule, and preferably compounds having two or more epoxy groups. Preferably, one molecule contains 1 to 100 epoxy groups. The upper limit of the epoxy group can be, for example, 10 or less, or 5 or less. The lower limit of the epoxy group is preferably 2 or more. As compounds having an epoxy group, compounds described in paragraphs 0034 to 0036 of JP-A-2013-011869, paragraphs 0147 to 0156 of JP-A-2014-043556, paragraphs 0085 to 0092 of JP-A-2014-089408, and compounds described in JP-A-2017-179172 can also be used. These contents are incorporated into this specification.

[0348] The compound having an epoxy group may be a low molecular weight compound (e.g., a molecular weight of less than 2,000, or even less than 1,000) or a high molecular weight compound (e.g., a polymer having a molecular weight of 1,000 or more, having a weight average molecular weight of 1,000 or more). The weight average molecular weight of the compound having an epoxy group is preferably 200 to 100,000, more preferably 500 to 50,000. The upper limit of the weight average molecular weight is more preferably 10,000 or less, particularly preferably 5,000 or less, and most preferably 3,000 or less.

[0349] Epoxy resins are preferably used as compounds having epoxy groups. Examples of epoxy resins include epoxy resins that are glycidyl ethers of phenolic compounds, epoxy resins that are glycidyl ethers of various novolac resins, alicyclic epoxy resins, aliphatic epoxy resins, heterocyclic epoxy resins, glycidyl ester epoxy resins, glycidyl amine epoxy resins, epoxy resins obtained by glycidylating halogenated phenols, condensates of silicon compounds having epoxy groups with other silicon compounds, and copolymers of polymerizable unsaturated compounds having epoxy groups with other polymerizable unsaturated compounds. The epoxy equivalent weight of the epoxy resin is preferably 310 g / eq to 3,300 g / eq, more preferably 310 g / eq to 1,700 g / eq, and even more preferably 310 g / eq to 1,000 g / eq.

[0350] Commercially available products of compounds having a cyclic ether group include, for example, EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DICCORPORATION), Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by DICCORPORATION and are polymers containing epoxy groups).

[0351] When the colored photosensitive composition of the present invention contains a compound having a cyclic ether group, the content of the compound having a cyclic ether group in the total solids of the colored photosensitive composition is preferably 0.1% to 20% by mass. The lower limit is more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more. The upper limit is more preferably 15% by mass or less, and particularly preferably 10% by mass or less. In the colored composition of the present invention, the compound having a cyclic ether group may be used alone or in combination of two or more. When two or more compounds are used, the total amount of these compounds is preferably within the above range.

[0352] <Silane coupling agent>

[0353] The colored photosensitive composition of the present invention may contain a silane coupling agent. This method can further improve the adhesion to the support of the obtained film. In the present invention, a silane coupling agent refers to a silane compound having a hydrolyzable group and other functional groups. Furthermore, a hydrolyzable group refers to a substituent that directly bonds to a silicon atom and can produce a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of hydrolyzable groups include halogen atoms, alkoxy groups, and acyloxy groups, with alkoxy groups being preferred. In other words, the silane coupling agent is preferably a compound having an alkoxysilyl group. Furthermore, examples of functional groups other than hydrolyzable groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, mercapto groups, epoxy groups, oxetanyl groups, amino groups, urea groups, thioether groups, isocyanate groups, and phenyl groups, with amino groups, (meth)acryloyl groups, and epoxy groups being preferred. Specific examples of the silane coupling agent include N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N-β-aminoethyl-γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N-β-aminoethyl-γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE ... Silane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloyloxymethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-502), 3-methacryloyloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-503), etc. Specific examples of silane coupling agents include the compounds described in paragraphs 0018 to 0036 of JP-A-2009-288703 and the compounds described in paragraphs 0056 to 0066 of JP-A-2009-242604, the contents of which are incorporated into this specification.

[0354] When the colored photosensitive composition of the present invention contains a silane coupling agent, the content of the silane coupling agent in the total solids content of the colored photosensitive composition is preferably 0.1% to 5% by mass. The upper limit is more preferably 3% by mass or less, and particularly preferably 2% by mass or less. The lower limit is more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more. In the colored photosensitive composition of the present invention, only one silane coupling agent may be used, or two or more silane coupling agents may be used. When two or more silane coupling agents are used, the total amount of these silane coupling agents is preferably within the above range.

[0355] <Organic Solvents>

[0356] The colored photosensitive composition of the present invention preferably contains an organic solvent. Examples of organic solvents include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. For details on these, please refer to paragraph 0223 of International Publication No. 2015 / 166779, which is incorporated herein. Cyclic alkyl-substituted ester solvents and cyclic alkyl-substituted ketone solvents are also preferably used. Specific examples of the organic solvent include polyethylene glycol monomethyl ether, methylene chloride, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropionamide, 3-butoxy-N,N-dimethylpropionamide, etc. However, for environmental reasons, it may be preferable to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as the organic solvent (for example, it can be reduced to 50 mass ppm (parts per million) or less, 10 mass ppm or less, or 1 mass ppm or less relative to the total amount of the organic solvent).

[0357] In the present invention, it is preferred to use an organic solvent with a low metal content. For example, the metal content of the organic solvent is preferably 10 parts per billion (ppb) or less. If necessary, organic solvents with a ppt (parts per trillion) mass content can be used. Such organic solvents are provided, for example, by Toyo Gosei Co., Ltd. (Chemical Industry Daily, November 13, 2015).

[0358] Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation or thin film distillation) or filtration using a filter. The pore size of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The filter is preferably made of polytetrafluoroethylene, polyethylene, or nylon.

[0359] The organic solvent may contain isomers (compounds having the same number of atoms but different structures). The isomers may be present in one or more species.

[0360] In the present invention, the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially no peroxide is contained.

[0361] The content of the solvent in the colored photosensitive composition is preferably 20% by mass to 95% by mass, more preferably 30% by mass to 90% by mass, and still more preferably 40% by mass to 90% by mass.

[0362] Furthermore, from the perspective of environmental regulations, the colored photosensitive composition of the present invention preferably contains substantially no environmentally regulated substances. In the present invention, "substantially no environmentally regulated substances" means that the content of environmentally regulated substances in the colored photosensitive composition is 50 ppm by mass or less, preferably 30 ppm by mass or less, more preferably 10 ppm by mass or less, and particularly preferably 1 ppm by mass or less. Examples of environmentally regulated substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene. These are registered as environmentally regulated substances under regulations such as REACH (Registration Evaluation Authorization and Restriction of Chemicals), the PRTR (Pollutant Release and Transfer Register), and VOC (Volatile Organic Compounds) regulations, and their usage and disposal methods are strictly regulated. These compounds may be used as solvents during the production of the various components used in the colored photosensitive composition of the present invention and may be incorporated into the colored photosensitive composition as residual solvents. From the perspective of human safety and environmental considerations, it is preferable to minimize the amount of these substances. As a method for reducing environmental control substances, the system interior can be enumerated to be heated and decompressed to above the boiling point of the environmental control substances, and the method for distilling and removing the environmental control substances from the system interior and reducing them. In addition, in the case of distilling and removing a small amount of environmental control substances, it is also useful to azeotrope with a solvent having the same boiling point as the solvent in order to improve efficiency. In addition, when containing a compound with free radical polymerizability, it can be removed by decompression distillation after adding a polymerization inhibitor to suppress the free radical polymerization reaction in the decompression distillation removal, resulting in cross-linking between molecules. These distillation removal methods can be carried out in any stage of the raw material stage, the stage of the product of the raw material reaction (such as the resin solution and the multifunctional monomer solution after polymerization) or the stage of the colored photosensitive composition made by mixing these compounds.

[0363] <Polymerization Inhibitor>

[0364] The colored photosensitive composition of the present invention may contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), and N-nitrosophenylhydroxylamine salts (ammonium salts, cerium salts, etc.). Among them, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solids content of the colored photosensitive composition is preferably 0.0001% by mass to 5% by mass.

[0365] <Surfactant>

[0366] The colored photosensitive composition of the present invention may contain a surfactant. Examples of surfactants include fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants. Examples of surfactants include those described in WO 2015 / 166779, 0238-0245, which are incorporated herein by reference.

[0367] In the present invention, the surfactant is preferably a fluorinated surfactant. Including a fluorinated surfactant in the colored photosensitive composition can further enhance liquid properties (particularly fluidity) and improve liquid conservation. Furthermore, it can form a film with minimal thickness variations.

[0368] The fluorine content in the fluorine-based surfactant is preferably 3% to 40% by mass, more preferably 5% to 30% by mass, and particularly preferably 7% to 25% by mass. Fluorine-based surfactants with fluorine contents within this range are effective in terms of uniformity of coating film thickness and liquid conservation, and also have good solubility in the colored photosensitive composition.

[0369] Examples of the fluorine-based surfactant include surfactants described in paragraphs 0060 to 0064 of JP-A-2014-041318 (paragraphs 0060 to 0064 of the corresponding WO 2014 / 017669), and surfactants described in paragraphs 0117 to 0132 of JP-A-2011-132503, the contents of which are incorporated herein. Examples of commercially available fluorochemical surfactants include MEGAFACE F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, and MFS-330 (all manufactured by DIC Corporation), Fluorad FC430, FC431, and FC171 (all manufactured by Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, and KH-40 (all manufactured by AGC Inc.), and PolyFox PF636, PF656, PF6320, PF6520, PF7002 (all manufactured by OMNOVASOLUTIONS INC.), etc.

[0370] Furthermore, acrylic compounds can also be preferably used as fluorochemical surfactants. These acrylic compounds have a molecular structure having a functional group containing a fluorine atom, and when heat is applied, the functional group containing a fluorine atom is partially cut off and the fluorine atom is volatilized. Examples of these fluorochemical surfactants include the MEGAFACE DS series manufactured by DIC Corporation (Chemical Industry Daily (February 22, 2016), Nikkei Industry News (February 23, 2016)), for example, MEGAFACE DS-21.

[0371] Furthermore, the fluorine-based surfactant is preferably a polymer of a fluorine-containing vinyl ether compound having a fluorinated alkyl or fluorinated alkylene ether group and a hydrophilic vinyl ether compound. Such a fluorine-based surfactant can be described in Japanese Patent Application Laid-Open No. 2016-216602, the contents of which are incorporated into this specification.

[0372] Fluorine-based surfactants can also use block polymers. For example, the compounds described in Japanese Patent Application Laid-Open No. 2011-089090 can be cited. Fluorine-based surfactants can also preferably use fluorine-containing polymer compounds, which contain: repeating units derived from (meth)acrylate compounds having fluorine atoms; and repeating units derived from (meth)acrylate compounds having 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy and propyleneoxy). In addition, as the fluorine-containing surfactants described in paragraphs 0016 to 0037 of Japanese Patent Application Laid-Open No. 2010-032698 and the fluorine-based surfactants used in the present invention, the following compounds are also exemplified.

[0373] [Chemical Formula 26]

[0374]

[0375] The weight average molecular weight of the compound is preferably 3,000 to 50,000, for example, 14,000. In the compound, % indicating the ratio of repeating units is mol %.

[0376] Furthermore, fluoropolymers having ethylenically unsaturated groups in their side chains can also be used as fluorochemical surfactants. Specific examples include the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP-A-2010-164965, such as MEGAFACE RS-101, RS-102, RS-718K, and RS-72-K manufactured by DICCORPORATION. Furthermore, the compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used as fluorochemical surfactants.

[0377] Examples of the nonionic surfactant include glycerin, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid esters, PLURONIC L10, L31, L61, L62, 10R5, 17R2, and 25R2 (manufactured by BASF), TETRONIC 304, 701, 704, 901, 904, and 150R1 (manufactured by BASF), SOLSPERSE 20000 (manufactured by Lubrizol Japan Ltd.), NCW-101, NCW-1001, and NCW-1002 (manufactured by Fujifilm Wako). Pure Chemical Corporation), PIONIN D-6112, D-6112-W, D-6315 (manufactured by Takemoto Oil & Fat Co., Ltd.), OLFIN E1010, Surfynol 104, 400, 440 (manufactured by Nissin Chemical Co., Ltd.), etc.

[0378] Examples of the silicone surfactant include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, and Toray Silicone SH8400 (all manufactured by Dow Corning Toray Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, and TSF-4452 (all manufactured by Momentive Performance Materials Inc.), KP-341, KF-6001, and KF-6002 (all manufactured by Shin-Etsu Chemical Co., Ltd.), and BYK307, BYK323, and BYK330 (all manufactured by BYK Chemie GMBH).

[0379] The content of the surfactant in the total solid content of the colored photosensitive composition is preferably 0.001% to 5.0% by mass, more preferably 0.005% to 3.0% by mass. In the colored photosensitive composition of the present invention, only one surfactant may be used, or two or more surfactants may be used. When two or more surfactants are used, the total amount of these surfactants is preferably within the above range.

[0380] <Ultraviolet absorber>

[0381] The colored photosensitive composition of the present invention may contain a UV absorber. Examples of UV absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, and triazine compounds. Details of these compounds can be found in paragraphs 0052 to 0072 of JP-A-2012-208374, paragraphs 0317 to 0334 of JP-A-2013-068814, and paragraphs 0061 to 0080 of JP-A-2016-162946, all of which are incorporated herein. Commercially available UV absorbers include UV-503 (manufactured by Daito Chemical Co., Ltd.). Examples of benzotriazole compounds include the MYUA series manufactured by MIYOSHI OIL & FAT CO., LTD. (Chemical Industry Daily, February 1, 2016). Furthermore, as the ultraviolet absorber, compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.

[0382] The content of the ultraviolet absorber in the total solid content of the colored photosensitive composition is preferably 0.01% to 10% by mass, more preferably 0.01% to 5% by mass. In the colored photosensitive composition of the present invention, only one ultraviolet absorber may be used, or two or more ultraviolet absorbers may be used. When two or more ultraviolet absorbers are used, the total amount of these is preferably within the above range.

[0383] <Antioxidants>

[0384] The colored photosensitive composition of the present invention may contain an antioxidant. Examples of the antioxidant include phenolic compounds, phosphite compounds, and thioether compounds. As the phenolic compound, any phenolic compound known as a phenolic antioxidant may be used. Preferred phenolic compounds include hindered phenolic compounds. Compounds having a substituent at a position adjacent to the phenolic hydroxyl group (ortho position) are preferred. The substituent is preferably a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms. Furthermore, it is also preferred that the antioxidant be a compound having a phenolic group and a phosphite group in the same molecule. Furthermore, it is also preferred that a phosphorus-based antioxidant be used as the antioxidant. Examples of the phosphorus-based antioxidant include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphapin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphapin-2-yl)oxy]ethyl]amine, and ethylbis(2,4-di-tert-butyl-6-methylphenyl)phosphite. Commercially available antioxidants include, for example, ADKSTAB AO-20, ADKSTAB AO-30, ADKSTAB AO-40, ADKSTAB AO-50, ADKSTAB AO-50F, ADKSTAB AO-60, ADKSTAB AO-60G, ADKSTAB AO-80, and ADKSTAB AO-330 (all manufactured by ADEKA Corporation). Furthermore, antioxidants may include compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967 and compounds described in Korean Patent Publication No. 10-2019-0059371.

[0385] The content of the antioxidant in the total solids content of the colored photosensitive composition is preferably 0.01% to 20% by mass, and more preferably 0.3% to 15% by mass. In the colored photosensitive composition of the present invention, only one antioxidant may be used, or two or more antioxidants may be used. When two or more antioxidants are used, the total amount of these antioxidants is preferably within the above range.

[0386] <Other ingredients>

[0387] The colored photosensitive composition of the present invention may also contain a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer, and other auxiliary agents (e.g., conductive particles, fillers, defoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.) as needed. By appropriately incorporating these ingredients, the physical properties of the film and other properties can be adjusted. For example, these ingredients can be found in paragraphs 0183 and thereafter of JP-A-2012-003225 (paragraph 0237 of the corresponding U.S. Patent Application Publication No. 2013 / 0034812), and paragraphs 0101 to 0104 and 0107 to 0109 of JP-A-2008-250074, the contents of which are incorporated herein. In addition, the colored composition of the present invention may also contain a latent antioxidant as needed. As a latent antioxidant, a compound in which a protective group is protected as a site where an antioxidant functions can be cited, and the protective group is separated from and functions as an antioxidant by heating at 100°C to 250°C or heating at 80°C to 200°C in the presence of an acid / base catalyst. As a potential antioxidant, the compounds described in International Publication No. 2014 / 021023, International Publication No. 2017 / 030005, and Japanese Patent Application Publication No. 2017-008219 can be cited. As a commercially available product of a potential antioxidant, ADEKA ARKLS GPA-5001 (manufactured by ADEKA CORPORATION) can be cited. Furthermore, as described in Japanese Patent Application Publication No. 2018-155881, CI Pigment Yellow 129 can be added for the purpose of improving weather resistance.

[0388] The colored photosensitive composition of the present invention may contain a metal oxide to adjust the refractive index of the resulting film. Examples of the metal oxide include TiO2, ZrO2, Al2O3, and SiO2. The primary particle size of the metal oxide is preferably 1 nm to 100 nm, more preferably 3 nm to 70 nm, and particularly preferably 5 nm to 50 nm. The metal oxide may have a core-shell structure. In this case, the core may be hollow.

[0389] Furthermore, the colored photosensitive composition of the present invention may contain a light resistance improver. Examples of the light resistance improver include the compounds described in paragraphs 0036 to 0037 of Japanese Patent Application Laid-Open No. 2017-198787, the compounds described in paragraphs 0029 to 0034 of Japanese Patent Application Laid-Open No. 2017-146350, the compounds described in paragraphs 0036 to 0037 and 0049 to 0052 of Japanese Patent Application Laid-Open No. 2017-129774, and the compounds described in paragraphs 0049 to 0052 of Japanese Patent Application Laid-Open No. 201 The compounds described in paragraphs 0031 to 0034 and 0058 to 0059 of JP-A-2017-129674, the compounds described in paragraphs 0036 to 0037 and 0051 to 0054 of JP-A-2017-122803, the compounds described in paragraphs 0025 to 0039 of WO-2017 / 164127, and the compounds described in JP-A-2017-186546. The compounds described in paragraphs 0034 to 0047 of the publication, the compounds described in paragraphs 0019 to 0041 of JP-A-2015-025116, the compounds described in paragraphs 0101 to 0125 of JP-A-2012-145604, the compounds described in paragraphs 0018 to 0021 of JP-A-2012-103475, the compounds described in paragraphs 0019 to 0041 of JP-A-2011 The compounds described in paragraphs 0015 to 0018 of JP-A-257591, the compounds described in paragraphs 0017 to 0021 of JP-A-2011-191483, the compounds described in paragraphs 0108 to 0116 of JP-A-2011-145668, the compounds described in paragraphs 0103 to 0153 of JP-A-2011-253174, and the like.

[0390] In the colored photosensitive composition of the present invention, the content of free metals not bonded or coordinated to pigments, etc. is preferably 100 ppm or less, more preferably 50 ppm or less, even more preferably 10 ppm or less, and particularly preferably substantially free. This can be expected to achieve effects such as stabilization of pigment dispersibility (suppression of aggregation), improvement of spectral characteristics associated with improved dispersibility, stabilization of curable components, suppression of conductivity fluctuations associated with the dissolution of metal atoms / metal ions, and improvement of display characteristics. In addition, the effects described in Japanese Patent Publication No. 2012-153796, Japanese Patent Publication No. 2000-345085, Japanese Patent Publication No. 2005-200560, Japanese Patent Publication No. 08-043620, Japanese Patent Publication No. 2004-145078, Japanese Patent Publication No. 2014-119487, Japanese Patent Publication No. 2010-083997, Japanese Patent Publication No. 2017-090930, Japanese Patent Publication No. 2018-025612, Japanese Patent Publication No. 2018-025797, Japanese Patent Publication No. 2017-155228, Japanese Patent Publication No. 2018-036521, etc. can be obtained. Examples of the free metals include Na, K, Ca, Sc, Ti, Mn, Cu, Zn, Fe, Cr, Co, Mg, Al, Sn, Zr, Ga, Ge, Ag, Au, Pt, Cs, Ni, Cd, Pb, and Bi. Furthermore, the content of free halogens not bound or coordinated to pigments, etc., in the colored photosensitive composition of the present invention is preferably 100 ppm or less, more preferably 50 ppm or less, even more preferably 10 ppm or less, and particularly preferably substantially free. Examples of halogens include F, Cl, Br, I, and their anions. Methods for reducing the free metals or halogens in the colored photosensitive composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with ion-exchange resins.

[0391] Furthermore, the colored photosensitive composition of the present invention may contain a dye. As the dye, a known dye can be used.

[0392] The dye is not particularly limited, and examples thereof include pyrazole azo compounds, phenylamino azo compounds, triarylmethane compounds, anthraquinone compounds, anthrapyridone compounds, benzylene compounds, oxocyanine compounds, pyrazolotriazole azo compounds, pyridone azo compounds, cyanine compounds, phenothiazine compounds, pyrrolopyrazole methine azo compounds, xanthene compounds, phthalocyanine compounds, benzopyran compounds, indigo compounds, and pyrromethene compounds.

[0393] Furthermore, as dyes, methine dyes described in JP-A-2019-073695, methine dyes described in JP-A-2019-073696, methine dyes described in JP-A-2019-073697, and methine dyes described in JP-A-2019-073698 can also be used.

[0394] The colored photosensitive composition of the present invention can also use a pigment multimer. The pigment multimer is preferably a dye used by dissolving in a solvent. In addition, the pigment multimer can also form particles. When the pigment multimer is in the form of particles, it is usually used in a state dispersed in a solvent. Pigment multimers in a particle state can be obtained, for example, by emulsion polymerization, and the compounds and production methods described in Japanese Patent Application Laid-Open No. 2015-214682 can be cited as specific examples. The pigment multimer has two or more pigment structures in one molecule, preferably three or more pigment structures. The upper limit is not particularly limited, but can be set to 100 or less. The multiple pigment structures in one molecule can be the same pigment structure or different pigment structures. The weight average molecular weight (Mw) of the pigment multimer is preferably 2,000 to 50,000. The lower limit is more preferably 3,000 or more, and more preferably 6,000 or more. The upper limit is more preferably 30,000 or less, and more preferably 20,000 or less. As the pigment multimer, compounds described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, and International Publication No. 2016 / 031442 can also be used.

[0395] The content of dye is preferably less than that of pigment.

[0396] It is also preferred that the colored photosensitive composition of the present invention does not substantially contain terephthalic acid ester.

[0397] The water content of the colored photosensitive composition of the present invention is preferably 3% by mass or less, more preferably 0.01% by mass to 1.5% by mass, and particularly preferably 0.1% by mass to 1.0% by mass. The water content can be measured by the Karl Fischer method.

[0398] The colored photosensitive composition of the present invention can be used to adjust the viscosity for purposes such as adjusting the film surface shape (flatness, etc.) and film thickness. The viscosity value can be appropriately selected as needed; for example, it is preferably 0.3 MPa·s to 50 MPa·s at 23°C, and more preferably 0.5 MPa·s to 20 MPa·s. Viscosity can be measured, for example, using a viscometer RE85L manufactured by Toki Sangyo Co., Ltd. (rotor: 1°34' x R24, measuring range 0.6 to 1,200 MPa·s) at 23°C.

[0399] When the colored photosensitive composition of the present invention is used as a color filter for liquid crystal display devices, the voltage holding ratio of the liquid crystal display element equipped with the color filter is preferably 70% or more, more preferably 90% or more. Known means for obtaining a high voltage holding ratio can be appropriately incorporated. Typical means include the use of high-purity materials (e.g., reducing ionic impurities) and controlling the amount of acidic functional groups in the composition. The voltage holding ratio can be measured, for example, by the method described in paragraph 0243 of Japanese Patent Application Publication No. 2011-008004 and paragraphs 0123 to 0129 of Japanese Patent Application Publication No. 2012-224847.

[0400] <Storage Container>

[0401] The container for storing the colored photosensitive composition of the present invention is not particularly limited, and known containers can be used. Furthermore, as a container, for the purpose of suppressing the incorporation of impurities into the raw materials or the colored photosensitive composition, a multilayer bottle having an inner wall composed of six types of resins in six layers or a bottle having a seven-layer structure in which six types of resins are used is also preferred. Examples of such containers include those described in Japanese Patent Application Laid-Open No. 2015-123351. Furthermore, for the purpose of preventing metal from eluting from the inner wall of the container, improving the storage stability of the composition, or suppressing the deterioration of the components, it is also preferred that the inner wall of the colored photosensitive composition be made of glass or stainless steel. The storage conditions for the colored photosensitive composition of the present invention are not particularly limited, and conventionally known methods can be used. Furthermore, the method described in Japanese Patent Application Laid-Open No. 2016-180058 can also be used.

[0402] <Method for Preparing Colored Photosensitive Composition>

[0403] The colored photosensitive composition of the present invention can be prepared by mixing the above components. When preparing the colored photosensitive composition, all components can be dissolved and / or dispersed simultaneously in a solvent to prepare the colored photosensitive composition. Alternatively, each component can be prepared as two or more solutions or dispersions as needed and then mixed at the time of use (during coating).

[0404] Furthermore, when preparing a colored photosensitive composition, it is also preferred to include a step of dispersing the pigment. As mechanical forces used for dispersing the pigment in the step of dispersing the pigment, compression, squeezing, impact, shearing, cavitation, etc. can be cited. As specific examples of these steps, bead milling, sand milling, roller milling, ball milling, paint stirring, micro jets, high-speed impellers, sand mixing, jet mixing, high-pressure wet micronization, ultrasonic dispersion, etc. can be cited. Furthermore, in the pulverization of the pigment under a sand mill (bead mill), it is preferably treated under the following conditions, which are to improve the pulverization efficiency by using microbeads with a small diameter and increasing the filling rate of the microbeads. Furthermore, it is preferred to remove coarse particles by filtration, centrifugation, etc. after the pulverization process. Furthermore, the pigment dispersion step and the dispersing machine can preferably use the steps and dispersing machines described in paragraph 0022 of "Dispersion Technology Encyclopedia, JOHOKIKO CO., LTD. Issued on July 15, 2005" or "A Practical Comprehensive Data Set of Dispersion Technology and Industrial Applications Centered on Suspension (Solid / Liquid Dispersion System), Business Development Center Publishing Department Issued on October 10, 1978", and Japanese Patent Application Publication No. 2015-157893. Furthermore, in the pigment dispersion process, the particles can be miniaturized by a salt milling process. The raw materials, equipment, and processing conditions used in the salt milling process can be referred to, for example, the records of Japanese Patent Application Publication No. 2015-194521 and Japanese Patent Application Publication No. 2012-046629.

[0405] When preparing a colored photosensitive composition, it is preferred to filter the colored photosensitive composition with a filter for the purpose of removing foreign matter and reducing defects. As a filter, any filter that has been used for filtering purposes can be used without particular limitation. For example, filters using raw materials such as fluororesins such as polytetrafluoroethylene (PTFE), polyamide resins such as nylon (e.g., nylon-6, nylon-6,6), and polyolefin resins such as polyethylene and polypropylene (PP) (including high-density, ultra-high molecular weight polyolefin resins) can be cited. Among these raw materials, polypropylene (including high-density polypropylene) and nylon are preferred.

[0406] The pore size of the filter is preferably 0.01 μm to 7.0 μm, more preferably 0.01 μm to 3.0 μm, and even more preferably 0.05 μm to 0.5 μm. As long as the pore size of the filter is within the above range, fine impurities can be removed more reliably. Regarding the pore size value of the filter, the nominal value of the filter manufacturer can be referred to. Various filters provided by NIHON PALL LTD. (DFA4201NIEY, etc.), Advantec Toyo Kaisha, Ltd., Nihon Entegris KK (formerly Nippon Mykrolis Corporation), and KITZ MICROFILTERCorporation can be used as the filter.

[0407] Furthermore, it is also preferable to use a fibrous filter material as the filter. Examples of fibrous filter materials include polypropylene fibers, nylon fibers, and glass fibers. Commercially available products include the SBP series (SBP008, etc.), TPR series (TPR002, TPR005, etc.), and SHPX series (SHPX003, etc.) manufactured by ROKI TECHNOCO., LTD.

[0408] When using filters, different filters (e.g., a first filter and a second filter) may be combined. In this case, filtration with each filter may be performed only once or twice or more. Furthermore, filters with different pore sizes may be combined within the above-mentioned range. Furthermore, filtration with the first filter may be performed only on the dispersion, and then, after mixing with other components, filtration may be performed with the second filter.

[0409] (cured material)

[0410] The cured product of the present invention is a cured product obtained by curing the colored photosensitive composition of the present invention. The cured product of the present invention can be used in color filters, etc. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more specifically, it can be preferably used as a red colored layer (red pixel) of a color filter.

[0411] The cured product of the present invention is preferably a film-like cured product, and its film thickness can be appropriately adjusted depending on the intended purpose. For example, the film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0412] (Color Filter)

[0413] Next, the color filter of the present invention will be described. The color filter of the present invention comprises the cured product of the present invention described above. More preferably, the pixels of the color filter comprise the cured film of the present invention. The color filter of the present invention can be used in solid-state imaging devices such as CCDs (charge-coupled devices) and CMOSs (complementary metal oxide semiconductors), image display devices, and the like.

[0414] In the color filter of the present invention, the film thickness of the present invention can be appropriately adjusted depending on the intended purpose. The film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0415] In the color filter of the present invention, the pixel width is preferably 0.5 μm to 20.0 μm. The lower limit is more preferably 1.0 μm or greater, and particularly preferably 2.0 μm or greater. The upper limit is more preferably 15.0 μm or less, and particularly preferably 10.0 μm or less. Furthermore, the pixel Young's modulus is preferably 0.5 GPa to 20 GPa, and more preferably 2.5 GPa to 15 GPa.

[0416] Each pixel contained in the color filter of the present invention preferably has high flatness. Specifically, the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less. There is no regulation on the lower limit, but for example, it is preferably 0.1 nm or more. The surface roughness of the pixel can be measured, for example, using AFM (atomic force microscope) Dimension3100 manufactured by Veeco. In addition, the contact angle of water on the pixel can be appropriately set to a preferred value, typically in the range of 50° to 110°. The contact angle can be measured, for example, using a contact angle meter CV-DT·A type (manufactured by Kyowa InterfaceScience Co., LTD.). In addition, the volume resistance value of the pixel is preferably high. Specifically, the volume resistance value of the pixel is preferably 10 9 Ω·cm or more, more preferably 10 11 Ω·cm or more. There is no upper limit, for example, it is preferably 10 14 The volume resistance value of a pixel can be measured using, for example, an ultra-high resistance meter 5410 (manufactured by Advantest Corporation).

[0417] Furthermore, the color filter of the present invention may be provided with a protective layer on the surface of the film of the present invention. By providing a protective layer, various functions such as oxidation resistance, low reflectivity, hydrophilicity and hydrophobicity, and shielding of light of a predetermined wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted. The thickness of the protective layer is preferably 0.01 μm to 10 μm, more preferably 0.1 μm to 5 μm. As methods for forming the protective layer, there are exemplified a method of coating a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of attaching a formed resin with an adhesive material. As the components constituting the protective layer, (meth) acrylic resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamide-imide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, polyurethane resin, aromatic polyamide resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluororesin, polycarbonate resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al2O3, Mo, SiO2, Si2N4, etc. can be mentioned, and two or more of these components can be contained. For example, in the case of a protective layer for preventing oxidation, the protective layer preferably includes polyol resin, SiO2 and Si2N4. In addition, in the case of a protective layer for low reflection, the protective layer preferably includes (meth) acrylic resin and fluororesin.

[0418] When applying resin composition and forming protective layer, as the coating method of resin composition, it is possible to use known methods such as spin coating, cast film, screen printing, inkjet method. Organic solvent contained in resin composition can use known organic solvent (for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate etc.). When forming protective layer by chemical vapor deposition, as chemical vapor deposition, it is possible to use known chemical vapor deposition (thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition).

[0419] The protective layer may also contain additives such as organic particles, inorganic particles, absorbents of light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), refractive index adjusters, antioxidants, adhesives, surfactants, etc. as needed. Examples of organic and inorganic particles include polymer particles (for example, silicone resin particles, polystyrene particles, melamine resin particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, silicon dioxide, calcium carbonate, barium sulfate, etc. Known absorbents can be used as absorbents of light of a given wavelength. The content of these additives can be appropriately adjusted, preferably 0.1% to 70% by mass, more preferably 1% to 60% by mass, relative to the total mass of the protective layer.

[0420] Furthermore, as the protective layer, the protective layer described in paragraphs 0073 to 0092 of Japanese Patent Application Laid-Open No. 2017-151176 can also be used.

[0421] The color filter may have a base layer. The base layer can also be formed using, for example, a composition obtained by removing the colorant from the coloring composition of the present invention described above. When measured with diiodomethane, the surface contact angle of the base layer is preferably 20° to 70°. Furthermore, when measured with water, it is preferably 30° to 80°. If the surface contact angle of the base layer is within the above range, the wettability of the resin composition is good. The surface contact angle of the base layer can be adjusted, for example, by adding a surfactant.

[0422] <Method for Manufacturing Color Filter>

[0423] Next, a method for producing a color filter using the colored photosensitive composition of the present invention will be described. The color filter production method can be performed by forming a colored photosensitive composition layer on a support using the colored photosensitive composition of the present invention, and then patterning the colored photosensitive composition layer using photolithography or dry etching. Since the colored photosensitive composition of the present invention can also suppress the generation of development residue, it is particularly effective when producing a color filter by patterning the colored photosensitive composition layer using photolithography.

[0424] -Photolithography-

[0425] First, the case of producing a color filter by patterning using photolithography will be described. This production method preferably includes a step of forming a colored photosensitive composition layer on a support using the colored photosensitive composition of the present invention, a step of exposing the colored photosensitive composition layer to a pattern, and a step of developing and removing the unexposed portions of the colored photosensitive composition layer to form a pattern (pixels). If necessary, a step of baking the colored photosensitive composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.

[0426] In the process of forming a colored photosensitive composition layer, the colored photosensitive composition of the present invention is used to form a colored photosensitive composition layer on a support. As a support, there is no particular limitation and it can be appropriately selected according to the purpose. For example, a glass substrate, a silicon substrate, etc. can be mentioned, preferably a silicon substrate. In addition, a charge coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. can be formed on the silicon substrate. In addition, a black matrix is sometimes formed on the silicon substrate to isolate each pixel. In addition, in order to improve the adhesion with the upper layer, prevent the diffusion of substances or the flattening of the substrate surface, a base layer can be provided on the silicon substrate. The base layer can be formed using a composition obtained by removing a colorant from the colored photosensitive composition described in this specification and a composition comprising a resin, a polymerizable compound, a surfactant, etc. described in this specification.

[0427] Known methods can be used to apply the colored photosensitive composition. Examples include droplet coating, slit coating, spraying, roll coating, spin coating, cast coating, slit and spin coating, pre-wetting methods (e.g., those described in Japanese Patent Application Laid-Open No. 2009-145395), various printing methods including ejection-based printing such as inkjet (e.g., drop-on-demand, piezoelectric, and thermal), nozzle spraying, flexographic printing, screen printing, gravure printing, reverse offset printing, and metal mask printing, transfer printing using a mold, and nanoimprinting. The inkjet application method is not particularly limited. Examples include the method described in "Inkjet for General Application - Infinite Possibilities Emerging from Patents," published in February 2005 by Sumitbe Techon Research Co., Ltd. (particularly pages 115 to 133), and methods described in Japanese Unexamined Patent Applications Nos. 2003-262716, 2003-185831, 2003-261827, 2012-126830, and 2006-169325. Regarding the coating method of the colored photosensitive composition, reference can be made to the descriptions of International Publication Nos. 2017 / 030174 and 2017 / 018419, the contents of which are incorporated herein.

[0428] The colored photosensitive composition layer formed on the support can be dried (prebaked). In the case of manufacturing the film by a low-temperature process, prebaking is not required. When prebaking is performed, the prebaking temperature is preferably 150°C or less, more preferably 120°C or less, and further preferably 110°C or less. The lower limit can be set to, for example, 50°C or more, or 80°C or more. The prebaking time is preferably 10 seconds to 300 seconds, more preferably 40 seconds to 250 seconds, and further preferably 80 seconds to 220 seconds. Prebaking can be performed using a hot plate, an oven, or the like.

[0429] <<Exposure Process>>

[0430] Next, the colored photosensitive composition layer is exposed in a pattern (exposure step). For example, the colored photosensitive composition layer can be exposed in a pattern by using a stepper or scanner exposure machine through a mask having a predetermined mask pattern. This allows the exposed portion to be cured.

[0431] Examples of radiation (light) that can be used for exposure include g-rays and i-rays. Furthermore, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 nm to 300 nm) can also be used. Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), with KrF rays (wavelength 248 nm) being preferred. Furthermore, light sources with a long wavelength of 300 nm or more can also be used.

[0432] Furthermore, during exposure, light can be irradiated continuously or in pulses (pulse exposure). Pulse exposure refers to an exposure method in which light is irradiated and paused repeatedly in a short cycle (e.g., milliseconds or less) to perform exposure.

[0433] The irradiation dose (exposure dose) is preferably 0.03 J / cm 2 ~2.5J / cm 2 , more preferably 0.05 J / cm 2 ~1.0J / cm 2 The oxygen concentration during exposure can be appropriately selected. In addition to being performed in the atmosphere, exposure can also be performed in a low-oxygen environment with an oxygen concentration of 19% by volume or less (e.g., 15% by volume, 5% by volume, or substantially no oxygen), or in a high-oxygen environment with an oxygen concentration greater than 21% by volume (e.g., 22% by volume, 30% by volume, or 50% by volume). Furthermore, the exposure illuminance can be appropriately set, preferably from 1,000 W / m 2 ~100,000W / m 2 (For example, 5,000W / m 2 , 15,000W / m 2 , or 35,000W / m 2 The oxygen concentration and exposure illuminance can be combined with appropriate conditions, for example, the illuminance can be set to 10,000 W / m at an oxygen concentration of 10% by volume. 2 , set the illumination to 20,000 W / m at an oxygen concentration of 35% by volume 2 wait.

[0434] Next, the unexposed portion of the colored photosensitive composition layer is developed and removed to form a pattern (pixel). The development and removal of the unexposed portion of the colored composition layer can be performed using a developer. As a result, the unexposed portion of the colored photosensitive composition layer in the exposure process is dissolved in the developer, and only the photocured portion remains. As the developer, an organic alkaline developer that does not damage the components or circuits of the substrate is preferably used. The temperature of the developer is preferably, for example, 20°C to 30°C. The development time is preferably 20 seconds to 180 seconds. In addition, in order to improve the residue removability, the following process can be repeated several times: the developer is shaken off every 60 seconds, and the developer is re-supplied.

[0435] Developer can enumerate organic solvents, alkaline developer etc., and alkaline developer can be preferably used. As alkaline developer, it is preferably an alkaline aqueous solution (alkaline developer) obtained by diluting an alkali agent with pure water. As alkali agent, for example, ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis(2-hydroxyethyl)ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo[5.4.0]-7-undecene and other organic alkaline compounds or sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium silicate, sodium metasilicate and other inorganic alkaline compounds can be listed. About alkali agent, compound with large molecular weight is preferred aspect environmental aspect and safety aspect. The concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001% by mass to 10% by mass, more preferably 0.01% by mass to 1% by mass. In addition, the developer may further contain a surfactant. As the surfactant, the above-mentioned surfactants can be listed, preferably a nonionic surfactant. From the perspective of convenient transportation or storage, the developer can be temporarily prepared as a concentrated solution and diluted to the desired concentration when used. The dilution ratio is not particularly limited, for example, it can be set in the range of 1.5 to 100 times. In addition, it is also preferred to wash (rinse) with pure water after development. In addition, rinsing is preferably carried out by rotating the support on which the developed colored photosensitive composition layer is formed while supplying a rinsing liquid to the developed colored photosensitive composition layer. In addition, it is also preferred to move the nozzle that discharges the rinsing liquid from the center of the support to the peripheral portion of the support. At this time, when the nozzle moves from the center of the support to the peripheral portion, it can be moved while gradually reducing the movement speed of the nozzle. By rinsing in this way, the in-plane deviation of the rinsing can be suppressed. Furthermore, the same effect can be achieved by gradually reducing the rotation speed of the support body while moving the nozzle from the center portion to the peripheral portion of the support body.

[0436] Preferably, after development, additional exposure treatment and heating treatment (post-baking) are performed after drying. Additional exposure treatment and post-baking are curing treatments after development for making a completely cured substance. The heating temperature in post-baking is preferably 100°C to 240°C, for example, and more preferably 200°C to 240°C. Regarding post-baking, the developed film can be subjected to the above-mentioned conditions by using a heating mechanism such as a hot plate or a convection oven (hot air circulation dryer), a high-frequency heater, etc., in a continuous or intermittent manner. In the case of performing additional exposure treatment, the light used for exposure is preferably light with a wavelength of less than 400nm. In addition, the additional exposure treatment can be performed by the method described in Korean Patent Gazette No. 10-2017-0122130.

[0437] -Dry etching method-

[0438] Next, the case of manufacturing a color filter by forming a pattern by dry etching is described. The pattern formation by dry etching preferably includes the following steps: forming a colored photosensitive composition layer on a support using the colored photosensitive composition of the present invention, and curing the colored photosensitive composition layer as a whole to form a cured layer; forming a photoresist layer on the cured layer; exposing the photoresist layer in a patterned manner, and then developing it to form a resist pattern; and dry etching the cured layer using an etching gas using the resist pattern as a mask. When forming the photoresist layer, it is preferred to further perform a pre-baking treatment. In particular, as a step of forming the photoresist layer, it is preferred to perform a heat treatment after exposure and a heat treatment after development (post-baking treatment). Regarding the pattern formation by dry etching, reference can be made to the description of paragraphs 0010 to 0067 of Japanese Patent Application Publication No. 2013-064993, which is incorporated into this specification.

[0439] (Solid-state imaging element)

[0440] The solid-state imaging device of the present invention preferably comprises the cured product of the present invention and the color filter of the present invention. The structure of the solid-state imaging device of the present invention is not particularly limited as long as it comprises the film of the present invention and functions as a solid-state imaging device. For example, the following structures can be mentioned.

[0441] On the substrate, there are a plurality of diodes and transfer electrodes made of polysilicon, etc., which constitute the light-receiving area of a solid-state imaging element (CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.), a shielding film having only the light-receiving portion of the diode opened on the diode and the transfer electrode, a device protection film having silicon nitride formed in a manner covering the entire surface of the shielding film and the light-receiving portion of the diode, and a structure having a color filter on the device protection film. Furthermore, it is possible to have a structure having a focusing mechanism (for example, a microlens, etc., the same applies hereinafter) on the device protection film and on the lower side of the color filter (the side close to the substrate), or a structure having a focusing mechanism on the color filter. Furthermore, the color filter may also have a structure in which each colored pixel is embedded in a space separated by a partition wall, for example, in a grid-like manner. In this case, the partition wall preferably has a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include those described in Japanese Patent Application Publication No. 2012-227478, Japanese Patent Application Publication No. 2014-179577, International Publication No. 2018 / 043654, and U.S. Patent Application Publication No. 2018 / 0040656. Imaging devices incorporating the solid-state imaging element of the present invention can be used as vehicle-mounted cameras or surveillance cameras, in addition to digital cameras and electronic devices with camera functionality (such as mobile phones).

[0442] Furthermore, as described in Japanese Patent Application Laid-Open No. 2019-211559, the solid-state imaging element of the present invention can improve the light resistance of the color filter by providing an ultraviolet absorption layer (UV cut filter) within the structure of the solid-state imaging element.

[0443] (Image Display Device)

[0444] The image display device of the present invention preferably has the cured product of the present invention and the color filter of the present invention. Examples of the image display device include a liquid crystal display device and an electroluminescent display device. The definition of an image display device or the details of each image display device are described in, for example, "Electronic Display Devices (written by Akio Sasaki, Kogyo Chosakai Publishing Co., Ltd., published in 1990)" and "Display Devices (written by Junsho Ibuki, Sangyo Tosho Publishing Co., Ltd., published in 1989)". In addition, regarding liquid crystal display devices, for example, they are described in "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Publishing Co., Ltd., published in 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied. For example, the various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology" can be applied.

[0445] (Asymmetric diketopyrrolopyrrole compound)

[0446] The asymmetric diketopyrrolopyrrole compound of the present invention is an asymmetric diketopyrrolopyrrole compound represented by the following formula 2, and preferably an asymmetric diketopyrrolopyrrole compound represented by the following formula 3.

[0447] [Chemical Formula 27]

[0448]

[0449] In formula 2, A 2 Each independently represents a monovalent organic group having an acidic functional group or a basic functional group, 2 Each independently represents a monovalent organic group, C 2 Each independently represents a monovalent organic group having no acidic functional group or basic functional group, n1 represents an integer of 1 to 5, n2 represents an integer of 0 to 5, and n3 represents an integer of 0 to 4. 2 and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups.

[0450] [Chemical Formula 28]

[0451]

[0452] In formula 3, A 3 Each independently represents an acidic functional group or a basic functional group, B 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, C 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, X 1 Each independently represents an ether bond, a thioether bond, a sulfonamide bond or a urea bond, L 1 Each independently represents a single bond or an ether bond, L 2 and L 3 Each independently represents an alkylene group, n2 represents an integer of 0 to 5, n3 represents an integer of 0 to 4, n4 independently represents 0 or 1, n5 represents an integer of 1 to 5, and the terminal has A 3 The group and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups, L 1 In the case of an ether bond, B 2 It is an electron-donating group having no acidic functional group and no basic functional group, and n2 represents an integer of 1-5.

[0453] Preferred embodiments of Formula 2 and Formula 3 in the asymmetric diketopyrrolopyrrole compound of the present invention are the same as preferred embodiments of Formula 2 and Formula 3 in the colored photosensitive composition of the present invention described above.

[0454] Example

[0455] Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.

[0456] In the present examples, "%" and "parts" mean "mass %" and "parts by mass," respectively, unless otherwise specified. In polymer compounds, unless otherwise specified, molecular weight refers to weight-average molecular weight (Mw), and the ratio of constituent units refers to mole percentage.

[0457] The weight average molecular weight (Mw) is a value measured as a polystyrene-equivalent value based on a gel permeation chromatography (GPC) method.

[0458] In addition, DPP-1 to 26 used in the examples are the same compounds as the above-mentioned DPP-1 to 26, respectively.

[0459] <Synthesis Example 1: DPP-1 synthesis>

[0460] To a nitrogen-purged three-necked flask, 160 parts of tert-amyl alcohol, 34 parts of compound A-1, and 54 parts of sodium tert-amyloxide were added, the mixture was heated to 110°C, and stirred. Next, 40 parts of compound B-1, synthesized according to the method described in Tetrahedron, 58 (2002), 5547-5565, were added. After reacting at 120°C for 4 hours, the mixture was cooled to 70°C, 320 parts of methanol and 400 parts of water were added, the mixture was filtered, and washed with methanol to obtain 39 parts of the asymmetric diketopyrrolopyrrole compound DPP-1.

[0461] <Synthesis Examples 2 to 20, 22, 23, 25, and 26: Synthesis of DPP-2 to 20, 22, 23, 25, and 26>

[0462] As shown in Table 1, DPP-2 to DPP-20, DPP-22, and DPP-23 were prepared in the same manner as in Synthesis Example 1 except that Compound A-1 and Compound B-1 were used as raw materials.

[0463] <Synthesis Example 21: Synthesis of DPP-21>

[0464] After synthesis using the same method as in Synthesis Example 1, 10 parts of a DPP precursor were added to 100 parts of acetic acid. After adding 15 parts of a 25% by mass oxybromide-acetic acid solution, the mixture was heated to 50°C and stirred for 3 hours. The mixture was cooled to 25°C, fractionated, and washed with acetonitrile to obtain 16 parts of an asymmetric diketopyrrolopyrrole compound, DPP-2.

[0465] <Synthesis Example 24: Synthesis of DPP-24>

[0466] Following synthesis using the same method as in Synthesis Example 1, 10 parts of a DPP precursor, 15 parts of potassium carbonate, and 15 parts of 1-bromohexane were added to 100 parts of NMP and 50 parts of DMF. After reaction at 120°C for 12 hours, the mixture was cooled to 50°C, 100 parts of methanol and 300 parts of water were added, and the mixture was filtered. The resulting filtrate was then added to 100 parts of acetic acid, followed by 15 parts of a 25% by mass solution of oxybromide in acetic acid. The mixture was then heated to 50°C and stirred for 3 hours. The mixture was cooled to 25°C, filtered, and washed with acetonitrile to obtain 3 parts of the asymmetric diketopyrrolopyrrole compound DPP-24.

[0467] Furthermore, for some of the obtained diketopyrrolopyrrole compounds, the following are shown: 1 H-NMR measurement data.

[0468] DPP-1: 1 H-NMR (DMSO-d6) δ (ppm) = 0.99, 2.40, 2.48, 3.60, 7.39, 7.50, 11.24.

[0469] DPP-2: 1 H-NMR (DMSO-d6) δ (ppm) = 0.99, 2.48, 3.61, 7.51, 7.67, 8.42, 8.48, 11.34

[0470] DPP-3: 1 H-NMR (DMSO-d6) δ (ppm) = 1.00, 2.48, 3.61, 7.51, 7.57, 8.43, 8.48, 11.29

[0471] DPP-4: 1 H-NMR (DMSO-d6) δ (ppm) = 2.17, 2.40, 3.47, 7.39, 7.47, 8.38, 8.42, 11.24

[0472] DPP-6: 1 H-NMR (DMSO-d6) δ (ppm) = 2.17, 2.40, 2.47, 3.55, 4.56, 7.39, 7.50, 8.39, 8.44, 11.26

[0473] DPP-10: 1H-NMR (DMSO-d6) δ (ppm) = 0.90, 1.52, 2.40, 2.94, 4.43, 7.18, 7.40, 7.55, 8.39, 8.45, 11.28

[0474] DPP-11: 1 H-NMR (DMSO-d6) δ (ppm) = 1.88, 2.16, 2.37, 2.39, 4.12, 7.12, 7.37, 8.35, 8.47, 11.17

[0475] DPP-23: 1 H-NMR (DMSO-d6) δ (ppm) = 1.87, 2.15, 2.36, 3.86, 4.11, 7.11, 7.13, 8.44, 8.46, 11.14

[0476] [Table 1]

[0477] Asymmetric DPP Raw material group A Raw material group B DPP-1 A-1 B-1 DPP-2 A-1 B-2 DPP-3 A-1 B-2 DPP-4 A-2 B-1 DPP-5 A-2 B-3 DPP-6 A-3 B-1 DPP-7 A-4 B-1 DPP-8 A-5 B-1 DPP-9 A-6 B-1 DPP-10 A-7 B-1 DPP-11 A-8 B-1 DPP-12 A-8 B-3 DPP-13 A-9 B-1 DPP-14 A-10 B-1 DPP-15 A-11 B-1 DPP-16 A-12 B-1 DPP-17 A-13 B-1 DPP-18 A-14 B-1 DPP-19 A-15 B-1 DPP-20 A-16 B-1 DPP-21 A-17 B-1 DPP-22 A-1 B-4 DPP-23 A-8 B-4 DPP-24 A-17 B-1 DPP-25 A-11 B-5 DPP-26 A-18 B-1

[0478] Compounds A-1 to A-18 and compounds B-1 to B-5 described in Table 1 are shown below.

[0479] [Chemical Formula 29]

[0480]

[0481] [Chemical formula 30]

[0482]

[0483] [Chemical Formula 31]

[0484]

[0485] [Chemical Formula 32]

[0486]

[0487] <Preparation of Pigment Composition>

[0488] The resins, pigments, DPP (diketopyrrolopyrrole compound), solvents and other components listed in Table 2 or Table 3 were mixed in the proportions listed in Table 2 or Table 3, and the resulting mixture was dispersed using a bead mill (zirconium dioxide beads 0.3 mm in diameter) for 3 hours. The mixture was then further dispersed using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) equipped with a pressure reducing mechanism at 2,000 kg / cm 3 The dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of . This dispersion treatment was repeated 10 times to obtain respective pigment compositions.

[0489]

[0490]

[0491] The "ratio of red pigment to derivative" in Tables 2 and 3 represents the value (mass ratio) of the content of the diketopyrrolopyrrole compound / the total content of Pigment 1 and Pigment 2, and the "ratio of yellow pigment to derivative" represents the value (mass ratio) of the content of SY-1 / the content of Pigment 3.

[0492] The details of the compounds listed in Tables 2 and 3 are shown below.

[0493] PR272: CI Pigment Red 272

[0494] PR254: CI Pigment Red 254

[0495] PY139: CI Pigment Yellow 139

[0496] PY185: CI Pigment Yellow 185

[0497] PY150: CI Pigment Yellow 150

[0498] PY138: CI Pigment Yellow 138

[0499] P071: CI Pigment Orange 71

[0500] PGMEA: Propylene glycol monomethyl ether acetate

[0501] SY-1: The following compound

[0502] [Chemical Formula 33]

[0503]

[0504] PB-1: the following compound, solid content 30% by mass, PGMEA solution, Mw 16,000, solid content acid value 55 mgKOH / g

[0505] PB-2: the following compound, solid content 30% by mass, PGMEA solution, Mw 8,000, solid content acid value 53 mgKOH / g

[0506] PB-3: the following compound, solid content 30% by mass, PGMEA solution, Mw 15,000, solid content acid value 70 mgKOH / g

[0507] PB-4: A product with a different acid value from PB-1, solid content acid value 40mgKOH / g

[0508] PB-5: A product with a different acid value from PB-1, solid content acid value 70mgKOH / g

[0509] PA-1: the following compound, solid content 30% by mass, PGMEA solution, Mw: 23,000, solid content acid value 30 mgKOH / g

[0510] [Chemical Formula 34]

[0511]

[0512] DPP-C1: The following diketopyrrolopyrrole compound (excluding the above-mentioned diketopyrrolopyrrole compound A).

[0513] DPP-C2: the following diketopyrrolopyrrole compound

[0514] [Chemical Formula 35]

[0515]

[0516] (Examples 1 to 82 and Comparative Examples 1 and 2)

[0517] <Preparation of Colored Photosensitive Composition>

[0518] The following components were mixed to prepare a colored photosensitive composition. The components listed in Table 4 or Table 5 were used for the pigment dispersion, resin, polymerizable compound, photopolymerization initiator, and solvent.

[0519] Pigment composition listed in Table 4 or Table 5: Amount listed in Table 4 or Table 5

[0520] Resins listed in Table 4 or Table 5: Quantities listed in Table 4 or Table 5

[0521] · Polymerizable compounds listed in Table 4 or Table 5: Amount listed in Table 4 or Table 5

[0522] Photopolymerization initiator listed in Table 4 or Table 5: the amount listed in Table 4 or Table 5

[0523] Surfactant (1 mass % PGMEA (propylene glycol monomethyl ether acetate) solution of the following compound (the ratio of the repeating unit is mole %, Mw: 14,000)): 1 mass part

[0524] p-Methoxyphenol: 0.01 parts by mass

[0525] Solvents listed in Table 4 or Table 5: Quantities listed in Table 4 or Table 5

[0526] [Chemical Formula 36]

[0527]

[0528] [Table 4]

[0529]

[0530] [Table 5]

[0531]

[0532] RP-1 to RP-54, RP-56 to RP-82, RP-C1, and RP-C2 are red photosensitive compositions, and RP-55 is a yellow photosensitive composition. Furthermore, RP-34 can be used not only for red pixels but also for orange pixels.

[0533] The compounds described in Table 4 and Table 5 other than the above are shown below.

[0534] -Resin-

[0535] PB-6: solid content 30% by mass, PGMEA solution, Mw: 30,000, solid content acid value 30 mgKOH / g

[0536] PB-7: solid content 30% by mass, PGMEA solution, Mw: 11,000, solid content acid value 70 mgKOH / g

[0537] [Chemical Formula 37]

[0538]

[0539] -Polymerizable compound-

[0540] M-1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)

[0541] M-2: NK ESTER A-TMMT (manufactured by Shin Nakamura Chemical Co., Ltd.)

[0542] M-3: Dipentaerythritol hexaacrylate

[0543] -Photopolymerization initiator-

[0544] I-1 to I-10: The following compounds

[0545] [Chemical Formula 38]

[0546]

[0547] -Solvents-

[0548] S-1: Propylene glycol monomethyl ether acetate (PGMEA)

[0549] S-2: Cyclohexanone

[0550] <Evaluation Method>

[0551] -Adhesion evaluation-

[0552] Each colored photosensitive composition was applied to an 8-inch (20.32 cm) silicon wafer using a spin coating method so that the film thickness after post-baking was 0.5 μm. Subsequently, it was pre-baked at 100°C for 2 minutes using a hot plate. Next, an i-ray stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.) was used through a mask having a Bayer pattern with a predetermined pixel (pattern) size at a rate of 200 mJ / cm 2 The exposure was performed with an exposure dose of 1.5 μm. In addition, a mask having a Bayer pattern in which a pixel pattern is formed with 0.7 μm square, 0.8 μm square, 0.9 μm square, 1.0 μm square, 1.1 μm square, 1.2 μm square, 1.3 μm square, 1.4 μm square, 1.5 μm square, 1.7 μm square, 2.0 μm square, 3.0 μm square, 5.0 μm square, and 10.0 μm square was used.

[0553] Next, spin immersion development was performed at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). The film was then rinsed with pure water using a spin shower. Subsequently, the film was heated (post-baked) at 200°C for 5 minutes using a hot plate to form a pattern (pixels).

[0554] Using a high-resolution FEB length measurement device (HITACHI CD-SEM) S9380II (manufactured by Hitachi High-Technologies Corporation), patterns of 0.7 μm square, 0.8 μm square, 0.9 μm square, 1.0 μm square, 1.1 μm square, 1.2 μm square, 1.3 μm square, 1.4 μm square, 1.5 μm square, 1.7 μm square, 2.0 μm square, 3.0 μm square, 5.0 μm square, and 10.0 μm square were observed. The minimum pattern size at which the pattern was formed without peeling was defined as the minimum close-line width. The smaller the minimum close-line width, the better the adhesion.

[0555] [Evaluation Criteria]

[0556] A: The minimum close-line width is 1.2 μm square or less.

[0557] B: The minimum close-line width is larger than 1.2 μm square and not more than 1.3 μm square.

[0558] C: The minimum close-line width is greater than 1.3 μm square and not more than 1.4 μm square.

[0559] D: The minimum close-line width is greater than 1.4 μm square and not more than 1.6 μm square.

[0560] E: The minimum close-fitting line width is greater than 1.6 μm square.

[0561] -Storage stability evaluation-

[0562] The viscosity of the colored photosensitive composition obtained above was measured using "RE-85L" manufactured by Toki Sangyo Co., Ltd., and then the colored photosensitive composition was allowed to stand for 3 days at 45°C, and then the viscosity was measured again. The storage stability was evaluated based on the difference in viscosity (ΔVis) before and after standing according to the following evaluation criteria. It is believed that the smaller the value of the viscosity difference (ΔVis), the better the storage stability. The viscosity of the colored photosensitive composition was measured at a temperature of 25°C. The evaluation criteria are as follows.

[0563] [Evaluation Criteria]

[0564] A: ΔVis is 0.5 mPa·s or less.

[0565] B: ΔVis is greater than 0.5 mPa·s and is 2.0 mPa·s or less.

[0566] C: ΔVis is greater than 2.0 mPa·s.

[0567] -Developability Evaluation-

[0568] CT-4000 (manufactured by FUJIFILM Flectronic Materials Co., Ltd.) was applied to a silicon wafer by spin coating to a film thickness of 0.1 μm, and a hot plate was used to heat the film at 220°C for 1 hour to form a base layer. Each curable composition was applied to the silicon wafer with the base layer by spin coating, and then heated at 100°C for 2 minutes using a hot plate to obtain a composition layer with a film thickness of 1 μm. For the composition layer, an i-ray stepper FPA-3000i5+ (manufactured by Canon Inc.) was used to irradiate a mask pattern in which square pixels with a side of 1.1 μm were arranged in an area of 4 mm × 3 mm on the substrate, and light with a wavelength of 365 nm was irradiated at an exposure amount of 200 mJ / cm 2Exposure was performed. The exposed composition layer was subjected to spin-immersion development for 60 seconds at 23°C using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. Subsequently, the composition layer was rinsed with water using a spin spray and then rinsed with pure water. Water droplets were then blown off with high-pressure air, and the silicon wafer was allowed to dry naturally before post-baking at 200°C for 300 seconds using a hot plate to form a pattern. The developability was evaluated by observing the presence of residual errors between patterns.

[0569] The area outside the pattern formation region (unexposed area) was observed using a scanning electron microscope (SEM) (magnification 10,000 times), and residues with a diameter of 0.1 μm or more were counted per 5 μm×5 μm area (one area) of the unexposed area. The residues were evaluated according to the following evaluation criteria.

[0570] A: There is absolutely no residue in any area.

[0571] B: The number of residues per area is less than 10.

[0572] C: The number of residues per region is 10 or more and less than 20.

[0573] D: The number of residues per region is 20 or more and less than 30.

[0574] [Table 6]

[0575]

[0576] As shown in Table 6, the colored photosensitive compositions in Examples 1 to 82 gave cured products having excellent adhesion compared to the colored photosensitive compositions in Comparative Examples 1 and 2.

[0577] Furthermore, as shown in Table 6, the colored photosensitive compositions in Examples 1 to 82 were also excellent in storage stability and developability.

[0578] (Examples 101 to 154 and Examples 156 to 182)

[0579] The Green composition was applied to a silicon wafer using a spin coating method to a film thickness of 1.0 μm. The film was then heated at 100°C for 2 minutes using a hot plate. The film was then exposed to light at 1,000 mJ / cm using an i-ray stepper exposure system FPA-3000i5+ (manufactured by Canon Inc.). 2Exposure was performed through a mask with a 2 μm square dot pattern. Next, spin immersion development was performed for 60 seconds at 23°C using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Rinsing was then performed using a rotary spray and further rinsed with pure water. Next, the green composition was patterned on the silicon wafer by heating at 200°C for 5 minutes using a hot plate. Similarly, the red composition and the blue composition were patterned in sequence to form red, green, and blue coloring patterns (Bayer patterns).

[0580] In Examples 101 to 154 and 156 to 182, the colored photosensitive compositions prepared in Examples 1 to 54 and 56 to 82 were used as Red compositions, respectively.

[0581] The Green composition and the Blue composition other than the above-mentioned colored photosensitive composition will be described later.

[0582] The Bayer pattern is a pattern in which a 2×2 array of color filter elements having one red element, two green elements, and one blue element is repeated, as disclosed in US Pat. No. 3,971,065.

[0583] The obtained color filter was embedded in a solid-state imaging element according to a known method. Even when any of the colored photosensitive compositions obtained in Examples 1 to 76 were used, it was confirmed that the solid-state imaging element had excellent adhesion within the cured film and exhibited suitable image recognition capabilities.

[0584] Green compositions and Blue compositions other than the colored photosensitive compositions used in Examples 101 to 154 and 156 to 182 are as follows.

[0585] -Green composition-

[0586] The following components were mixed and stirred, and then filtered through a nylon filter (manufactured by Nihon Pall Ltd.) having a pore size of 0.45 μm to prepare a Green composition.

[0587] Green pigment dispersion: 73.7 parts by mass

[0588] Resin 4 (40% by mass PGMEA solution): 0.3 parts by mass

[0589] Polymerizable compound 1: 1.2 parts by mass

[0590] Photopolymerization initiator 1: 0.6 parts by mass

[0591] Surfactant 1: 4.2 parts by mass

[0592] Ultraviolet absorber (UV-503, manufactured by Daito Chemical Co., Ltd.): 0.5 parts by mass

[0593] PGMEA: 19.5 parts by mass

[0594] -Blue composition-

[0595] The following components were mixed and stirred, and then filtered through a nylon filter (manufactured by Nihon Pall Ltd.) having a pore size of 0.45 μm to prepare a Blue composition.

[0596] Blue pigment dispersion: 44.9 parts by mass

[0597] Resin 4 (40% by mass PGMEA solution): 2.1 parts by mass

[0598] Polymerizable compound 1: 1.5 parts by mass

[0599] Polymerizable compound 4: 0.7 parts by mass

[0600] Photopolymerization initiator 1: 0.8 parts by mass

[0601] Surfactant 1: 4.2 parts by mass

[0602] PGMEA: 45.8 parts by mass

[0603] The raw materials used for the Green composition, the Red composition, and the Blue composition are shown below.

[0604] Green pigment dispersion

[0605] A mixture of 6.4 parts by mass of CI Pigment Green 36, 5.3 parts by mass of CI Pigment Yellow 150, 5.2 parts by mass of a dispersant (DISPERBYK-161, manufactured by BYK Chemie GmbH), and 83.1 parts by mass of PGMEA was mixed and dispersed for 3 hours using a bead mill (zirconia microbeads, 0.3 mm diameter) to prepare a pigment dispersion. The dispersion was then further dispersed at 2,000 kg / cm using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) equipped with a pressure reducing mechanism. 3 The dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of . This dispersion treatment was repeated 10 times to obtain a Green pigment dispersion.

[0606] Blue pigment dispersion

[0607] A mixture of 9.7 parts by mass of CI Pigment Blue 15:6, 2.4 parts by mass of CI Pigment Violet 23, 5.5 parts by mass of a dispersant (DISPERBYK-161, manufactured by BYK Chemie GmbH), and 82.4 parts by mass of PGMEA was mixed and dispersed for 3 hours using a bead mill (zirconia beads 0.3 mm in diameter) to prepare a pigment dispersion. The dispersion was then further concentrated using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) equipped with a pressure reducing mechanism at 2,000 kg / cm 3 The dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of 1000 rpm. This dispersion treatment was repeated 10 times to obtain a blue pigment dispersion.

[0608] Polymerizable compound 1: KAYARAD DPHA (a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate, manufactured by Nippon Kayaku Co., Ltd.)

[0609] Polymerizable compound 4: a compound having the following structure

[0610] [Chemical Formula 39]

[0611]

[0612] Resin 4: Resin having the following structure (acid value: 70 mgKOH / g, Mw = 11,000, ratios in each structural unit are molar ratios.)

[0613] [Chemical Formula 40]

[0614]

[0615] Photopolymerization initiator 1: IRGACUREOXE01 (1-[4-(phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyloxime), manufactured by BASF)

[0616] Surfactant 1: 1 mass % PGMEA solution of the following mixture (Mw=14,000): In the following formula, the unit of % (62% and 38%) expressing the ratio of the structural unit is mass %.

[0617] [Chemical Formula 41]

[0618]

[0619] The disclosure of Japanese Patent Application No. 2020-030706 filed on February 26, 2020 is incorporated herein by reference in its entirety.

[0620] All documents, patent applications, and technical standards described in this specification are incorporated herein by reference to the same extent as if each document, patent application, or technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A colored photosensitive composition comprising: pigments; and A diketopyrrolopyrrole compound A represented by the following formula 1, The molar content of the diketopyrrolopyrrole compound A represented by the following formula 1 in the colored photosensitive composition is defined as m A , the molar content of the diketopyrrolopyrrole compound B represented by the following formula 1 is set to m B When, m A / (m A +m B ) is 10 mol% to 100 mol%, The content of the pigment is 35% by mass or more relative to the total solid content in the colored photosensitive composition. In formula 1, Diketopyrrolopyrrole compound A:A 1 represents a monovalent organic group having an acidic or basic functional group, B 1 represents a monovalent organic group having no acidic functional group and no basic functional group, R each independently represents a hydrogen atom or a monovalent substituent, Diketopyrrolopyrrole compound B:A 1 and B 1 represents a monovalent organic group having an acidic or basic functional group, A 1 and B 1 are the same or different, and R each independently represents a hydrogen atom or a monovalent substituent, The diketopyrrolopyrrole compound A comprises an asymmetric diketopyrrolopyrrole compound represented by the following formula 2: In formula 2, A 2 Each independently represents a monovalent organic group having a basic functional group, B 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, C 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, n1 represents an integer of 1 to 5, n2 represents an integer of 0 to 5, and n3 represents an integer of 0 to 4. 2 and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups.

2. The colored photosensitive composition according to claim 1, wherein The m A / (m A +m B ) is greater than 90 mol % and less than 100 mol %.

3. The colored photosensitive composition according to claim 1 or 2, wherein The pigment includes a diketopyrrolopyrrole pigment other than the compound represented by Formula 1.

4. The colored photosensitive composition according to claim 1 or 2, wherein The pigment includes a diketopyrrolopyrrole red pigment other than the compound represented by Formula 1.

5. The colored photosensitive composition according to claim 1 or 2, wherein The pigment includes a diaryldiketopyrrolopyrrole red pigment having an electron-donating group on an aromatic ring other than the compound represented by Formula 1.

6. The colored photosensitive composition according to claim 1 or 2, wherein The content of the pigment is 50% by mass or more relative to the total solid content in the colored photosensitive composition.

7. The colored photosensitive composition according to claim 1 or 2, wherein The content M of the pigment in the colored photosensitive composition P and the content M of the diketopyrrolopyrrole compound A A The mass ratio is M P / M A =95 / 5~50 / 50. 8 . The colored photosensitive composition according to claim 1 , further comprising a resin.

9. The colored photosensitive composition according to claim 8, wherein The resin includes a resin having an acidic functional group. 10 . The colored photosensitive composition according to claim 1 , further comprising a polymerizable compound and a photopolymerization initiator. 11 . A cured product obtained by curing the colored photosensitive composition according to claim 1 . 12 . A color filter comprising the cured product according to claim 11 . 13 . A solid-state imaging element comprising the color filter according to claim 12 . 14 . An image display device comprising the color filter according to claim 12 .

15. An asymmetric diketopyrrolopyrrole compound represented by the following formula 3: In formula 3, A 3 Each independently represents a basic functional group, B 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, C 2 Each independently represents a monovalent organic group having no acidic functional group and no basic functional group, X 1 Each independently represents an ether bond, a thioether bond, a sulfonamide bond or a urea bond, L 1 Each independently represents a single bond or an ether bond, L 2 and L 3 Each independently represents an alkylene group, n2 represents an integer of 0 to 5, n3 represents an integer of 0 to 4, n4 independently represents 0 or 1, n5 represents an integer of 1 to 5, and the terminal has A 3 The group and C 2 The bonded phenyl group and B 2 The bonded phenyl groups are different groups, L 1 In the case of an ether bond, B 2 It is an electron-donating group having no acidic functional group and no basic functional group, and n2 represents an integer of 1-5.

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