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

Abstract

To provide a novel asymmetric diketopyrrolopyrrole compound, which enables the formation of a photosensitive coloring composition giving a cured product with excellent adhesiveness.SOLUTION: Provided is an asymmetric diketopyrrolopyrrole compound represented by the following formula 2.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] Color filters are essential components of solid-state imaging devices or image display devices. In some cases, noise occurs in solid-state imaging devices and image display devices due to the reflection of visible light. To prevent this, a light-shielding film is provided in the solid-state imaging device or image display device to suppress the generation of noise. As a method for producing such a color filter or a light-shielding film, a method is known in which a colored photosensitive composition layer is formed using a colored photosensitive composition containing a colorant, a polymerizable compound, a photopolymerization initiator, and an alkali-soluble resin, and the colored photosensitive composition layer is exposed and developed to form a pattern. As conventional colored photosensitive compositions or photosensitive compositions, those described in Patent Documents 1 to 3 are known.

[0003] Patent Document 1: JP 2013-182230 A Patent Document 2: International Publication No. 2018 / 159541 Patent Document 3: Special Publication No. 2011-523433 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present disclosure is to provide a colored photosensitive composition that provides a cured product with excellent adhesion. Another problem to be solved by the embodiments of the present disclosure is to provide a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state imaging device or an image display device including the color filter. Still another problem to be solved by the embodiments according to the present disclosure is to provide a novel asymmetric diketopyrrolopyrrole compound. [Means for solving the problem]

[0005] Means for solving the above problems include the following aspects. <1> The colored photosensitive composition contains a pigment and a diketopyrrolopyrrole compound A represented by the following formula 1, and the molar content of the diketopyrrolopyrrole compound A represented by the following formula 1 in the colored photosensitive composition is m A The molar content of the diketopyrrolopyrrole compound B represented by the following formula 1 is m B In this case, m A / (m A +m B ) is 10 mol % to 100 mol %, and the content of the pigment is 35 mass % or more based on the total solid content in the colored photosensitive composition.

[0006] [ka]

[0007] 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 or basic functional group, and each R 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 may be the same or different, and each R independently represents a hydrogen atom or a monovalent substituent.

[0008] <2> The diketopyrrolopyrrole compound A includes an asymmetric diketopyrrolopyrrole compound represented by the following formula 2: <1> 2. The colored photosensitive composition according to claim 1 .

[0009] [ka]

[0010] In formula 2, A 2 each independently represents a monovalent organic group having an acidic functional group or a basic functional group; B 2 each independently represents a monovalent organic group having no acidic functional group or no basic functional 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; A 2 and C 2 and the phenyl group to which B is bonded 2 is a different group from the phenyl group to which it is bonded.

[0011] <3> The above m A / (m A +m B ) is more than 90 mol % and is 100 mol % or less. <1> or <2> 2. The colored photosensitive composition according to claim 1 . <4> Above A 1 is a monovalent organic group having a basic functional group <1> 2. The colored photosensitive composition according to claim 1 . <5> The pigment contains a diketopyrrolopyrrole pigment other than the compound represented by formula 1. <4> 10. The colored photosensitive composition according to claim 9 . <6> The pigment contains a diketopyrrolopyrrole red pigment other than the compound represented by formula 1. <1> ~ <5> 10. The colored photosensitive composition according to claim 9 . <7> The pigment contains a diaryldiketopyrrolopyrrole red pigment having an electron donating group on an aromatic ring other than the compound represented by formula 1. <1> ~ <6> 10. The colored photosensitive composition according to claim 9 . <8> The content of the pigment is 50% by mass or more based on the total solid content in the colored photosensitive composition. <1> ~ <7> 10. The colored photosensitive composition according to claim 9 . <9> The content M of the pigment in the colored photosensitive composition Pand the content M of the diketopyrrolopyrrole compound A. A The mass ratio of P / M A =95 / 5~50 / 50 <1> ~ <8> 10. The colored photosensitive composition according to claim 9 . <10> Further comprising resin <1> ~ <9> 10. The colored photosensitive composition according to claim 9 . <11> The resin includes a resin having an acidic functional group. <10> 2. The colored photosensitive composition according to claim 1 . <12> Further comprising a polymerizable compound and a photopolymerization initiator. <1> ~ <11> 10. The colored photosensitive composition according to claim 9 . <13> <1> ~ <12> 2. A cured product obtained by curing the colored curable composition according to claim 1. <14> <13> A color filter comprising the cured product according to claim 1. <15> <14> A solid-state imaging device having the color filter according to claim 1. <16> <14> An image display device comprising the color filter according to claim 1. <17> An asymmetric diketopyrrolopyrrole compound represented by the following formula 3.

[0012] [ka]

[0013] 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 or no basic functional group, C 2 each independently represents a monovalent organic group having no acidic functional group or no basic functional group; 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 3each independently represents an alkylene group; n2 represents an integer of 0 to 5; n3 represents an integer of 0 to 4; each independently represents 0 or 1; n5 represents an integer of 1 to 5; 3 and C 2 and the phenyl group to which B is bonded 2 is a different group from the phenyl group to which L is bonded. 1 is an ether bond, B 2 is an electron donating group having neither an acidic functional group nor a basic functional group, and n2 represents an integer of 1 to 5. Effect of the Invention

[0014] According to an embodiment of the present disclosure, there is provided a colored photosensitive composition that provides a cured product with excellent adhesion. Further, another embodiment according to the present disclosure provides a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state imaging device or an image display device including the color filter. Furthermore, according to still another embodiment of the present disclosure, there is provided a novel asymmetric diketopyrrolopyrrole compound. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] The contents of the present disclosure will be described in detail below. The following description of the components may be based on a representative embodiment of the present disclosure, but the present disclosure is not limited to such an embodiment. In the present disclosure, the use of "to" indicating a numerical range means that the numerical values ​​before and after it are included as the lower limit and upper limit. In the numerical ranges described in the present disclosure in stages, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. In addition, in the numerical ranges described in the present disclosure, the upper or lower limit value of the numerical range may be replaced with a value shown in the examples. Furthermore, in the present disclosure, when a plurality of substances corresponding to each component are present in the composition, the amount of each component in the composition means the total amount of the corresponding substances present in the composition, unless otherwise specified. In addition, in the description of groups (atomic groups) in the present disclosure, descriptions that do not indicate whether they are substituted or unsubstituted include those that have no substituents as well as those that have a substituent. For example, an "alkyl group" includes not only an alkyl group that has no substituents (unsubstituted alkyl groups) but also an alkyl group that has a substituent (substituted alkyl groups). In this disclosure, 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. In the present disclosure, "(meth)acrylic" is a term used as a concept that includes both acrylic and methacrylic, and "(meth)acryloyl" is a term used as a concept that includes both acryloyl and methacryloyl. In addition, in the present disclosure, the term "process" refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the intended purpose of the process is achieved. In the present disclosure, the term "total solid content" refers to the total mass of the components excluding the solvent from the entire composition of the composition. Also, as described above, the term "solid content" refers to the components excluding the solvent, and may be, for example, solid or liquid at 25°C. In the present disclosure, "mass %" and "weight %" are synonymous, and "parts by mass" and "parts by weight" are synonymous. Furthermore, in the present disclosure, combinations of two or more preferred embodiments are more preferred embodiments. In addition, unless otherwise specified, the weight average molecular weight (Mw) and number average molecular weight (Mn) in the present disclosure are molecular weights detected by a gel permeation chromatography (GPC) analyzer using columns of TSKgel GMHxL, TSKgel G4000HxL, or TSKgel G2000HxL (all product names manufactured by Tosoh Corporation) in a solvent of THF (tetrahydrofuran) and a differential refractometer, and converted using polystyrene as a standard substance. In this specification, a pigment means a compound that is poorly soluble in a solvent. In this specification, a dye means a compound that is easily soluble in a solvent. The present disclosure will be described in detail below.

[0016] (Colored photosensitive composition) The colored photosensitive composition according to the present disclosure contains a pigment and a diketopyrrolopyrrole compound A represented by the following formula 1, and the molar content of the diketopyrrolopyrrole compound A represented by the following formula 1 in the colored photosensitive composition is m A The molar content of the diketopyrrolopyrrole compound B represented by the following formula 1 is m B In this case, m A / (m A +m B ) is 10 mol % to 100 mol %, and the content of the pigment is 35 mass % or more based on the total solid content in the colored photosensitive composition.

[0017] [ka]

[0018] 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 or basic functional group, and each R independently represents a hydrogen atom or a monovalent substituent. Diketopyrrolopyrrole Compound B:A 1 and B. 1represents a monovalent organic group having an acidic or basic functional group; A 1 and B 1 may be the same or different, and each R independently represents a hydrogen atom or a monovalent substituent.

[0019] In recent years, the number of pixels in image sensors has increased, and patterns have become finer and thinner. Accordingly, the pigment concentration in color filters has been relatively increased, and the amount of curable components has been reduced. As a result of detailed studies, the present inventors have found that in conventional colored photosensitive compositions in which the pigment content is 35 mass % or more relative to the total solid content in the colored photosensitive composition, the adhesiveness of the resulting cured product to a substrate or the like may be insufficient. As a result of extensive investigations, the present inventors have found that by employing the above-mentioned configuration, the resulting cured product has excellent adhesion. The content of the pigment is 35% by mass or more based on the total solid content in the colored photosensitive composition, and the colored photosensitive composition contains the diketopyrrolopyrrole compound A represented by the above formula 1, and the molar content of the diketopyrrolopyrrole compound A represented by the following formula 1 in the colored photosensitive composition is m A The molar content of the diketopyrrolopyrrole compound B represented by the following formula 1 is m B In this case, m A / (m A +m B ) is 10 mol % to 100 mol %, even in the case of a colored photosensitive composition having a high pigment concentration as described above, when the diketopyrrolopyrrole compound A is adsorbed on the pigment surface and a pigment particle-asymmetric diketopyrrolopyrrole compound A structure is formed, the acidic functional group or basic functional group is more likely to be arranged on the side opposite to the pigment side compared to a symmetric diketopyrrolopyrrole compound, and is more likely to interact with other components such as a dispersant. Thus, the diketopyrrolopyrrole ring structure provides excellent adsorption to the pigment, and the diketopyrrolopyrrole compound A is more likely to be arranged on the surface of the pigment particle, so that the pigment particle and the diketopyrrolopyrrole compound A can be easily arranged on the surface of the pigment particle. It is presumed that this improves the interaction between the diketopyrrolopyrrole compound A and the interaction between other components and the diketopyrrolopyrrole compound A, resulting in excellent adhesion of the obtained cured product (hereinafter also simply referred to as "adhesion").

[0020] <Diketopyrrolopyrrole Compounds A and B> The colored photosensitive composition according to the present disclosure contains the diketopyrrolopyrrole compound A represented by the above formula 1, and the molar content of the diketopyrrolopyrrole compound A represented by the above formula 1 in the colored photosensitive composition is m A The molar content of the diketopyrrolopyrrole compound B represented by the above formula 1 is m B In this case, m A / (m A +m B ) is 10 mol % to 100 mol %. In the present disclosure, the pigment is a pigment other than the diketopyrrolopyrrole compounds A and B represented by the above formula 1.

[0021] In this disclosure, A / (m A +m B From the viewpoints of adhesion and storage stability, the value of is preferably 50 mol % to 100 mol %, more preferably 80 mol % to 100 mol %, and particularly preferably more than 90 mol % and 100 mol % or less.

[0022] Furthermore, in the colored photosensitive composition according to the present disclosure, the content of the isomer having the highest content among the diketopyrrolopyrrole compounds A represented by the above formula 1 is m AA In this case, the above m AA / m A From the viewpoints of adhesion and storage stability, the value is preferably 80 mol % to 100 mol %, more preferably 90 mol % to 100 mol %, and particularly preferably 95 mol % to 100 mol %.

[0023] A in Equation 1 1 and B. 1In terms of adhesion and storage stability, the acidic functional group in is preferably a sulfo group, a salt of a sulfo group, a carboxy group, a phosphoric acid functional group, a hydroxy group, or a boric acid functional group, and more preferably a sulfo group, a salt of a sulfo group, or a carboxy group. From the viewpoints of adhesion and storage stability, the counter ion of the salt of a sulfo 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.

[0024] A in Equation 1 1 and B. 1 From the viewpoints of adhesion and storage stability, the basic functional group in is preferably a group having a nitrogen atom, and 1A R 2A or a heterocyclic group containing a nitrogen atom is more preferred, and a piperidinyl group, a morpholinyl group or a -NR 1A R 2A More preferably, -NR 1A R 2A It is particularly preferred that: -NR 1A R 2A R in 1A and R 2A are each independently preferably 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. R 1A and R 2AThe alkyl group in the formula (I) 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. R 1A and R 2A The aryl group and the heteroaryl group in the formula (I) 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.

[0025] Also, -NR 1A R 2A R in 1A and R 2A may be bonded to form a ring. It is preferable that the ring is a 5-membered ring or a 6-membered ring, and it is more preferable that the ring is a 6-membered ring. R 1A and R 2A The ring formed by bonding with is R 1A and R 2A In addition to the nitrogen atom to which is bonded, the ring may have a heteroatom as a ring member, and may also 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.

[0026] 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.

[0027] Among them, A of the above diketopyrrolopyrrole compound A 1 From the viewpoints of adhesion and storage stability, is preferably a monovalent organic group having a basic functional group. In addition, A of the diketopyrrolopyrrole compound B1 and B. 1 From the viewpoints of adhesion and storage stability, is preferably a monovalent organic group having a basic functional group.

[0028] Furthermore, in formula 1, each R is preferably 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, from the viewpoints of adhesion and storage stability.

[0029] In addition, B of the above diketopyrrolopyrrole compound A 1 From the viewpoints of adhesion and storage stability, is preferably an aryl group which may have a substituent, and more preferably a phenyl group which may have a substituent. B of the above diketopyrrolopyrrole compound A 1 In terms of adhesion and storage stability, the substituents which the aryl group and the phenyl group in the formula (I) may have include, for example, an alkyl group, an alkoxy group, a phthalimidoalkyl 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 is preferable, an alkyl group, a phenyl group, a naphthyl group, an alkoxy group, or a halogen atom is more preferable, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a halogen atom is further preferable, and a methyl group, a methoxy group, or a chlorine atom is particularly preferable. R 11 ~R 19 each independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group. The above-mentioned substituents may further have a substituent.

[0030] A of the above diketopyrrolopyrrole compound A 1 The number of carbon atoms in the alkyl group is preferably 8 to 80, more preferably 9 to 60, and particularly preferably 9 to 40, from the viewpoints of adhesion and storage stability. B of the above diketopyrrolopyrrole compound A 1 The number of carbon atoms in the alkyl group is preferably 6 to 80, more preferably 6 to 60, and particularly preferably 6 to 40, from the viewpoints of adhesion and storage stability. In addition, A of the diketopyrrolopyrrole compound B 1 and B. 1 From the viewpoints of adhesion and storage stability, the molecular weight is preferably 8 to 80, more preferably 9 to 60, and particularly preferably 9 to 40.

[0031] From the viewpoints of adhesion and storage stability, the diketopyrrolopyrrole compound A preferably contains an asymmetric diketopyrrolopyrrole compound represented by the following formula 2.

[0032] [ka]

[0033] In formula 2, A 2 each independently represents a monovalent organic group having an acidic functional group or a basic functional group; B 2 each independently represents a monovalent organic group having no acidic functional group or no basic functional 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; A 2 and C 2 and the phenyl group to which B is bonded 2 is a different group from the phenyl group to which it is bonded.

[0034] A in Equation 2 2A preferred embodiment of the acidic functional group and the basic functional group in the above formula 1 is 1 The preferred embodiments are the same as those of the acidic functional group and the basic functional group in the above. A in Equation 2 2 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, from the viewpoints of adhesion and storage stability. A in Equation 2 2 The number of carbon atoms is preferably 2 to 60, more preferably 3 to 40, and particularly preferably 9 to 20.

[0035] In addition, A in Equation 2 2 is preferably -XYZ from the viewpoints of adhesion and storage stability. X is a single bond, -CH2-, -(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 represents NH-, q represents an integer from 0 to 10; 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, Y represents a single bond, an optionally substituted hydrocarbon group, an optionally substituted arylene group, or an optionally substituted heteroaromatic ring, and these groups are represented by -NR 101 may be bonded to each other via a divalent linking group selected from -, -O-, -SO2-, or CO-; Z represents a group represented by any one of the following formulas (Z1) to (Z6):

[0036] [ka]

[0037] R 301 and R 302 each independently represents an optionally substituted saturated or unsaturated alkyl group, or an optionally substituted heterocycle containing a nitrogen, oxygen or sulfur atom; R 303 , R 304 , R 305 and R 306 each independently represents a hydrogen atom, an optionally substituted saturated or unsaturated alkyl group, or an optionally substituted aryl group; R 307 represents an optionally substituted saturated or unsaturated alkyl group or an optionally substituted aryl group, R 308 and R 309 each independently represents a group represented by the following formula (Z7) or formula (Z8), -O-(CH2) o -R 350 , -OR 351 , -NR 352 R 353 , -Cl or -F; R 308 and R 309 is a group represented by the following formula (Z7) or formula (Z8), -O-(CH2) o -R 350 , -OR 351 , or -NR 352 R 353 where o represents an integer of 1 to 8; R 350 represents a heterocyclic residue which may have a substituent, R351 ~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; Each M independently represents a metal ion. R 310 ~R 313 each independently represents a hydrogen atom, an optionally substituted saturated or unsaturated alkyl group, or an optionally substituted aryl group; R 314 ~R 318 each independently represents a hydrogen atom, an alkoxyl group, an amino group, a sulfo group, a carboxyl group, or a phosphoric acid functional group,

[0038] [ka]

[0039] Z 1 Ha-NR 370 represents -, -CONH- or -O-; 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, These groups are -NR 370 may be bonded to each other via a divalent linking group selected from the group consisting of -, -O-, -SO2-, and CO-; 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, 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 R 360 and R 361 and together represent a heterocycle which may have a substituent containing a further nitrogen, oxygen or sulfur atom,

[0040] [ka]

[0041] Z 3 is a single bond connecting the triazine ring to 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 -SO2NR 380 - represents 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; 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; 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, The wavy lines indicate the bond positions with other structures.

[0042] Among these, from the viewpoints of adhesion and storage stability, X is preferably -CH2-O-, -CH2-, -O-, -S-, -CH2-S-, -CH2-NHSO2-, or -NHSO2-. From the viewpoints 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. Furthermore, from the viewpoints 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).

[0043] In addition, A in Eq. 2 From the viewpoints of adhesion and storage stability, is preferably -alkylene group-acidic functional group or basic functional group, -heteroatom-containing linking group-alkylene group-acidic functional group or basic functional group, or -alkylene group-heteroatom-containing linking group-alkylene group-acidic functional group or basic functional group, and more preferably -alkylene group-acidic functional group or basic functional group, or -heteroatom-containing linking group-alkylene group-acidic functional group or basic functional group. From the viewpoints 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. More preferred. From the viewpoints 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, even more preferably an ether bond or a sulfonamide bond, and particularly preferably an ether bond.

[0044] B in Equation 2 2 and C 2 each independently represents an alkyl group, an alkoxy group, a phthalimidoalkyl 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 , -NR18 COR 19 is preferable, an alkyl group, a phenyl group, a naphthyl group, an alkoxy group, or a halogen atom is more preferable, 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 is further preferable, and a methyl group, a methoxy group, a phenyl group, a chlorine atom, or a bromine atom is particularly preferable. R 11 ~R 19 each independently represents an alkyl group having 1 to 20 carbon atoms or a phenyl group. Also, the above B 2 and C 2 The alkyl group, alkoxy group, phthalimidoalkyl group, acyl group, halogen group, phenyl group, naphthyl group, cyano group, trifluoromethyl group, alkoxycarbonyl group and alkylthio group in the formula (I) may have a substituent. The substituents include an alkyl group, an alkoxy group, a phthalimidoalkyl 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 Examples include:

[0045] Also, B in Eq. 2 and C 2 Each of the carbon atoms independently preferably has 0 to 60, more preferably 0 to 20, and particularly preferably 0 to 8.

[0046] In formula 2, n1 is preferably 1 or 2, and more preferably 1, from the viewpoints of adhesion and storage stability. In formula 2, n2 is preferably an integer of 0 to 2, and more preferably 0 or 1, from the viewpoints of adhesion and storage stability. In formula 2, n3 is preferably 0 or 1, and more preferably 0, from the viewpoints of adhesion and storage stability. In addition, A in Equation 2 2 , B 2 and C 2 The bonding position of is not particularly limited, but from the viewpoint of adhesion and storage stability, at least A is preferably bonded to the para position of the diketopyrrolopyrrole ring in the benzene ring of formula 2. 2 It is preferred that the compound has the formula: Furthermore, when n2 is 1 or more, from the viewpoint of adhesion and storage stability, at least B is preferably present at the para position relative to the bonding position of the diketopyrrolopyrrole ring in the benzene ring of formula 2. 2 It is preferred that the compound has the formula:

[0047] From the viewpoints of adhesion and storage stability, the diketopyrrolopyrrole compound A more preferably contains an asymmetric diketopyrrolopyrrole compound represented by the following formula 3.

[0048] [ka]

[0049] 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 or no basic functional group, C 2 each independently represents a monovalent organic group having no acidic functional group or no basic functional group; 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; each independently represents 0 or 1; n5 represents an integer of 1 to 5; 3 and C 2 and the phenyl group to which B is bonded 2is a different group from the phenyl group to which L is bonded. 1 is an ether bond, B 2 is an electron donating group having neither an acidic functional group nor a basic functional group, and n2 represents an integer of 1 to 5.

[0050] A in Equation 3 3 A preferred embodiment of the acidic functional group and the basic functional group in the above formula 1 is 1 The preferred embodiments are the same as those of the acidic functional group and the basic functional group in the above. B in Equation 3 2 , C 2 , n2 and n3 are each the same as B in the above formula 2, except as described below. 2 , C 2 , n2 and n3, and preferred embodiments are also the same. L in Equation 3 1 From the viewpoint of storage stability, it is preferably a single bond, and from the viewpoint of adhesion, it is preferably an ether bond. Also, L 1 is an ether bond, B 2 From the viewpoint of adhesion, 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. Furthermore, L 1 When n2 is 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. L in Equation 3 2 are each independently, from the viewpoints of adhesion and storage stability, 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. X in Equation 3 1From the viewpoints of adhesion and storage stability, is preferably an ether bond, a sulfonamide bond, or a urea bond, more preferably an ether bond or a sulfonamide bond, and particularly preferably an ether bond. L in Equation 3 3 are each independently, from the viewpoints of adhesion and storage stability, 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. In terms of adhesion and storage stability, n4 in formula 3 is preferably 0. In formula 3, n5 is preferably 1 or 2, and more preferably 1, from the viewpoints of adhesion and storage stability.

[0051] From the viewpoints of adhesion and storage stability, the molecular weight of the diketopyrrolopyrrole compound A is preferably 1,200 or less, more preferably 800 or less, even more preferably 600 or less, and particularly preferably 340 or more and 600 or less.

[0052] The colored photosensitive composition according to the present disclosure may contain the above diketopyrrolopyrrole compound A alone or in combination of two or more kinds. The colored photosensitive composition according to the present disclosure may not contain the diketopyrrolopyrrole compound B, may contain one type alone, or may contain two or more types. The content of the diketopyrrolopyrrole compound A in the colored photosensitive composition according to the present disclosure is, from the viewpoints of adhesion and storage stability, 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. Moreover, from the viewpoints of adhesion and storage stability, the total content of the diketopyrrolopyrrole compounds A and B in the colored photosensitive composition according to the present disclosure 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.

[0053] 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 of M P / M A = 95 / 5 to 50 / 50 is preferable, 94.9 / 5.1 to 55 / 45 is more preferable, 94.5 / 5.5 to 64 / 36 is further preferable, and 94 / 6 to 82 / 18 is particularly preferable.

[0054] Specific examples of the diketopyrrolopyrrole compound A include DPP-1 to DPP-26, but the diketopyrrolopyrrole compound A is not limited thereto.

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] -Method for producing diketopyrrolopyrrole compound A- The method for producing the diketopyrrolopyrrole compound A is not particularly limited, and can be produced by referring to a known method, for example, a method of deriving from a pigment, a method of condensing two or more kinds of cyano compounds, and a method of condensing a cyano compound with a ketopyrrole compound. In particular, a cyano compound and a 3-alkoxycarbonyl-5-ketopyrrole compound can be condensed in the presence of a base to produce an asymmetric diketopyrrolopyrrole compound.

[0061] -Method of adding diketopyrrolopyrrole compounds A and B- The method of adding the diketopyrrolopyrrole compounds A and B to the colored photosensitive composition is not particularly limited, and known methods of addition and mixing can be used. For example, the compound A is mixed with the pigment in advance (dry or wet) and dried to form a composite pigment containing the diketopyrrolopyrrole compound A, or the compound A is added during pigment milling, or the compound B is added together with a dispersion medium during pigment dispersion, or the compound B is added to a pigment dispersion liquid.

[0062] <Pigments> The colored photosensitive composition according to the present disclosure comprises a pigment. The pigment in the present disclosure is a pigment other than the diketopyrrolopyrrole compounds A and B represented by the above formula 1 (also referred to as "compounds represented by formula 1"). The pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment. In addition, the pigment may be a material in which a part of an inorganic pigment or an organic-inorganic pigment is replaced with an organic chromophore. By replacing an inorganic pigment or an organic-inorganic pigment with an organic chromophore, it becomes easier to design the hue. The colored photosensitive composition according to the present disclosure can be preferably used as a colored photosensitive composition for forming colored pixels in a color filter. Examples of the colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Among them, red pixels are preferred.

[0063] The average primary particle diameter 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 even more preferably 100 nm or less. If the average primary particle diameter of the pigment is within the above range, the dispersion stability of the pigment in the colored photosensitive composition is good. In the present disclosure, the primary particle diameter of the pigment can be obtained by observing the primary particles of the pigment with a transmission electron microscope and obtaining an image photograph. Specifically, the projected area of ​​the primary particles of the pigment is obtained, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment. In the present disclosure, the average primary particle diameter is the arithmetic average value of the primary particle diameters of 400 primary particles of the pigment. In addition, the primary particles of the pigment refer to independent particles without aggregation.

[0064] The amount of the pigment that dissolves 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.

[0065] Examples of organic pigments 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. Among these, from the viewpoints of adhesion and storage stability, the pigment preferably contains a diketopyrrolopyrrole pigment other than the compound represented by Formula 1, more preferably contains a diketopyrrolopyrrole red pigment other than the compound represented by Formula 1, even more preferably contains a diaryldiketopyrrolopyrrole red pigment other than the compound represented by Formula 1, and particularly preferably contains a diaryldiketopyrrolopyrrole red pigment having an electron-donating group on an aromatic ring other than the compound represented by Formula 1. Specific examples of organic pigments include the following:

[0066] Color Index (CI) Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,125,126,127,128,129,137,13 8,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214,215,228,231,232 (methine type), 233 (quinoline type), 234 (amino ketone type), 235 (amino ketone type), 236 (amino ketone type), etc. (above, yellow pigments), 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. (orange pigments) CIPigment 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. (above, red pigments), CI Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64 (phthalocyanine type), 65 (phthalocyanine type), 66 (phthalocyanine type), etc. (above, green pigments), CI Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60 (triarylmethane type), 61 (xanthene type), etc. (purple pigments) 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 type), 88 (methine type), etc. (all blue pigments).

[0067] As a red pigment, at least one compound having the structure described in JP 2017-201384 A is It is also possible to use a diketopyrrolopyrrole compound substituted with a bromine atom, a diketopyrrolopyrrole compound described in paragraphs 0016 to 0022 of Japanese Patent No. 6248838, a diketopyrrolopyrrole compound described in International Publication No. 2012 / 102399, a diketopyrrolopyrrole compound described in International Publication No. 2012 / 117965, a naphthol azo compound described in JP-A-2012-229344, a red pigment described in Japanese Patent No. 6516119, a red pigment described in Japanese Patent No. 6525101, etc. In addition, as the red pigment, a compound having a structure in which an aromatic ring group in which a group in which an oxygen atom, a sulfur atom, or a nitrogen atom is bonded to an aromatic ring is introduced and bonded to a diketopyrrolopyrrole skeleton can also be used. As the red pigment, from the viewpoints of color and light fastness, preferred examples 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. Furthermore, from the viewpoint of color tone, it is preferable to use CI Pigment Red 254 and CI Pigment Red 272 in combination as pigments. From the standpoint of color, 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, even more preferably 1.2:1 to 1:1.2, and particularly preferably 1.2:1 to 1:1. From the viewpoint of color, the pigment preferably contains a red pigment and a yellow pigment. Furthermore, from the viewpoint of color tone, the mass ratio of the red pigment to the yellow pigment is preferably red pigment content:yellow pigment content=1:1 to 5:1, and more preferably 1.5:1 to 3:1.

[0068] Further, as yellow pigments, compounds described in JP-A-2017-201003, compounds described in JP-A-2017-197719, compounds described in paragraphs 0011 to 0062 and 0137 to 0276 of JP-A-2017-171912, compounds described in paragraphs 0010 to 0062 and 0138 to 0295 of JP-A-2017-171913, compounds described in paragraphs 0011 to 0062 and 0139 to 0190 of JP-A-2017-171914, compounds described in paragraphs 0010 to 0065 and 0142 to 0222 of JP-A-2017-171915, compounds described in paragraphs 0010 to 0065 and 0142 to 0222 of JP-A-2013, Quinophthalone compounds described in paragraphs 0011 to 0034 of JP-A-054339, quinophthalone compounds described in paragraphs 0013 to 0058 of JP-A-2014-026228, isoindoline compounds described in JP-A-2018-062644, quinophthalone compounds described in JP-A-2018-203798, quinophthalone compounds described in JP-A-2018-062578, quinophthalone compounds described in JP-A-6432076, quinophthalone compounds described in JP-A-2018-155881, quinophthalone compounds described in JP-A-2018-111757 quinophthalone compounds, quinophthalone compounds described in JP 2018-040835 A, quinophthalone compounds described in JP 2017-197640 A, quinophthalone compounds described in JP 2016-145282 A, quinophthalone compounds described in JP 2014-085565 A, quinophthalone compounds described in JP 2014-021139 A, quinophthalone compounds described in JP 2013-209614 A, quinophthalone compounds described in JP 2013-209435 A, quinophthalone compounds described in JP 2013-181015 A, JP 20 Quinophthalone compounds described in JP 2013-061622 A, quinophthalone compounds described in JP 2013-032486 A, quinophthalone compounds described in JP 2012-226110 A, quinophthalone compounds described in JP 2008-074987 A, quinophthalone compounds described in JP 2008-081565 A, quinophthalone compounds described in JP 2008-074986 A, quinophthalone compounds described in JP 2008-074985 A, quinophthalone compounds described in JP 2008-050420 A, JP 2008-031281 A Quinophthalone compounds described in the publication, quinophthalone compounds described in JP-B-48-032765, quinophthalone compounds described in JP-A-2019-008014, quinophthalone compounds described in JP-A-6607427, methine dyes described in JP-A-2019-073695, methine dyes described in JP-A-2019-073696, methine dyes described in JP-A-2019-073697, methine dyes described in JP-A-2019-073698, compounds described in Korean Patent Publication No. 10-2014-0034963, compounds described in JP-A-2017-095706, compounds described in Taiwan Patent Application Publication No. 201920495, compounds described in Japanese Patent No. 6607427, and the like can also be used. Moreover, polymerized versions of these compounds are also preferably used from the viewpoint of improving color value. As the yellow pigment, from the viewpoints of color tone and light resistance, CI Pigment Yellow 139 and CI Pigment Yellow 185 are preferred.

[0069] In addition, as the green pigment, a halogenated zinc phthalocyanine pigment 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. In addition, as the green pigment, compounds described in Chinese Patent Application Publication No. 106909027, phthalocyanine compounds having a phosphoric acid ester as a ligand described in International Publication No. 2012 / 102395, phthalocyanine compounds described in JP-A-2019-008014, phthalocyanine compounds described in JP-A-2018-180023, compounds described in JP-A-2019-038958, and the like can also be used.

[0070] In addition, an aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue pigment. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.

[0071] In addition, the pigment used in the present disclosure is preferably a pigment having a specific X-ray diffraction pattern by CuKα radiation.Specific examples thereof include the phthalocyanine pigment described in Japanese Patent No. 6561862, the diketopyrrolopyrrole pigment described in Japanese Patent No. 6413872, and the azo pigment (CI Pigment Red 269) described in Japanese Patent No. 6281345.

[0072] The content of the pigment is 35% by mass or more based on the total solid content in the colored photosensitive composition, and from the viewpoints 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.

[0073] <Resin> The colored photosensitive composition according to the present disclosure preferably contains a resin. The resin is blended, for example, for dispersing particles such as pigments in the colored photosensitive composition or for use as a binder. Note that a resin used mainly for dispersing particles such as pigments is also called a dispersant. However, such uses of the resin are merely examples, and the resin may be used for purposes other than these uses.

[0074] 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, and particularly preferably 500,000 or less. The lower limit is more preferably 4,000 or more, and particularly preferably 5,000 or more.

[0075] Examples of the resin include (meth)acrylic resin, enethiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, and styrene resin. One of these resins may be used alone, or two or more may be mixed and used. In addition, the resins described in paragraphs 0041 to 0060 of JP2017-206689A, the resins described in paragraphs 0022 to 007 of JP2018-010856A, the resins described in JP2017-057265A, the resins described in JP2017-032685A, the resins described in JP2017-075248A, and the resins described in JP2017-066240A may also be used.

[0076] The colored photosensitive composition according to the present disclosure preferably contains a resin having an acidic functional group as a resin. According to this embodiment, the developability of the colored photosensitive composition can be improved, and pixels having excellent rectangularity can be easily formed. Examples of the acidic functional group include a carboxy group, a phosphoric acid functional group, a sulfo group, and a phenolic hydroxy group, and the carboxy group is preferred. The resin having an acidic functional group can be used, for example, as an alkali-soluble resin. In addition, the colored photosensitive composition according to the present disclosure has the above-mentioned A from the viewpoints of adhesion and storage stability. 1 It is preferable that the compound contains a diketopyrrolopyrrole compound represented by formula (1) in which R is a monovalent organic group having a basic functional group, and a resin having an acidic functional group.

[0077] The resin having an acidic functional group preferably contains a repeating unit having an acidic functional group on a side chain, and more preferably contains 5 mol% to 70 mol% of the repeating units having an acidic functional group on a side chain of all the repeating units of the resin. The upper limit of the content of the repeating units having an acidic functional group on a side chain is preferably 50 mol% or less, and more preferably 30 mol% or less. The lower limit of the content of the repeating units having an acidic functional group on a side chain is preferably 10 mol% or more, and more preferably 20 mol% or more.

[0078] It is also preferable that the resin having an acidic functional group contains a repeating unit derived from a monomer component containing at least one monomer selected from the group consisting of a compound represented by the following formula (ED1) and a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimers").

[0079] [ka]

[0080] In formula (ED1), R 1 and R 2 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.

[0081] [ka]

[0082] In formula (ED2), R represents a hydrogen atom or an organic group having a carbon number of 1 to 30. For details of formula (ED2), the disclosure of JP-A-2010-168539 can be referred to, the contents of which are incorporated herein by reference.

[0083] Specific examples of ether dimers can be found in, for example, paragraph 0317 of JP2013-029760A, the contents of which are incorporated herein by reference.

[0084] The resin used in the present disclosure also preferably contains a repeating unit derived from a compound represented by the following formula (X):

[0085] [ka]

[0086] 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.

[0087] For the resin having an acidic functional group, the description in paragraphs 0558 to 0571 of JP 2012-208494 A (corresponding to paragraphs 0685 to 0700 of U.S. Patent Application Publication No. 2012 / 0235099 A) and the description in paragraphs 0076 to 0099 of JP 2012-198408 A can be referred to, the contents of which are incorporated herein by reference. In addition, the resin having an acidic functional group can be a commercially available product.

[0088] 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 more, and particularly preferably 50 mgKOH / g or more. The upper limit is more preferably 400 mgKOH / g or less, further preferably 300 mgKOH / g or less, and particularly preferably 200 mgKOH / g or less. The weight average molecular weight (Mw) of the resin having an acidic functional group is preferably 5,000 to 100,000. The number average molecular weight (Mn) of the resin having an acidic functional group is preferably 1,000 to 30,000.

[0089] The method for introducing an acidic functional group into the resin is not particularly limited, but may be, for example, the method described in Japanese Patent No. 6349629. Furthermore, examples of methods for introducing acidic functional groups into resins include a method in which an acid anhydride is reacted with a hydroxy group generated by a ring-opening reaction of an epoxy group in a dispersant (particularly a dispersant having an ethylenically unsaturated group) or an alkali-soluble resin to introduce an acid group.

[0090] In the present disclosure, it is preferable to use a resin having a basic functional group as the resin. According to this embodiment, the developability of the colored photosensitive composition can be improved, and pixels having excellent rectangularity can be easily formed. Examples of the basic functional group include an amino group and a heteroaryl group having a nitrogen atom, and an amino group is preferable, and a tertiary amino group is more preferable. The resin having a basic functional group can be used, for example, as an alkali-soluble resin.

[0091] 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, even more 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, and the number average molecular weight (Mn) of the resin having an amino group is preferably 1,000 to 20,000.

[0092] The colored photosensitive composition according to the present disclosure may also contain a resin as a dispersant. Examples of dispersants include acidic dispersants (acidic resins) and basic dispersants (basic 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 basic functional groups. The acidic dispersant (acidic resin) is preferably a resin in which the amount of acidic functional groups is 70 mol% or more when the total amount of the amount of the acidic functional groups and the amount of the basic functional groups is 100 mol%, and more preferably a resin substantially composed of only acidic functional groups. The acidic functional groups of the acidic dispersant (acidic resin) are preferably carboxy groups. 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. The basic dispersant (basic resin) refers to a resin in which the amount of basic functional groups is greater than the amount of acidic functional groups. The basic dispersant (basic resin) is preferably a resin having a basic functional group content of more than 50 mol % when the total amount of the acidic functional group and the basic functional group is taken as 100 mol %. The basic functional group of the basic dispersant is preferably an amino group.

[0093] The resin used as the dispersant preferably contains a repeating unit having an acidic functional group. By containing a repeating unit having an acidic functional group in the resin used as the dispersant, the generation of development residues can be further suppressed when forming a pattern by photolithography.

[0094] The resin used as the dispersant is preferably a graft resin. For details of the graft resin, refer to paragraphs 0025 to 0094 of JP2012-255128A, the contents of which are incorporated herein by reference.

[0095] The resin used as the dispersant is preferably a polyimine-based dispersant containing nitrogen atoms in at least one of the main chain and the side chain. The polyimine-based dispersant is preferably a resin having a main chain with a partial structure having a functional group with a pKa of 14 or less, a side chain with an atomic number of 40 to 10,000, and having a basic nitrogen atom in at least one of the main chain and the side chain. There is no particular limitation on the basic nitrogen atom as long as it is a nitrogen atom that exhibits basicity. For the polyimine-based dispersant, the description in paragraphs 0102 to 0166 of JP 2012-255128 A can be referred to, and the contents thereof are incorporated herein.

[0096] The resin used as the dispersant is preferably a resin having a structure in which a plurality of polymer chains are bonded to a core portion. Examples of such resins include dendrimers (including star-shaped polymers). Specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962A.

[0097] Moreover, the above-mentioned resin having an acidic functional group (alkali-soluble resin) can also be used as a dispersant.

[0098] The resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in a side chain. The content of the repeating unit having an ethylenically unsaturated bond-containing group in a side chain is preferably 10 mol % or more, more preferably 10 mol % to 80 mol %, and even more preferably 20 mol % to 70 mol %, of all the repeating units of the resin.

[0099] As the dispersant, a resin having an aromatic carboxy group (hereinafter referred to as "resin B") is preferable. It is often mentioned. In the resin B, the aromatic carboxy group may be included in the main chain of the repeating unit, or may be included in the side chain of the repeating unit. For the reason that the developability and color fading are excellent, the aromatic carboxy group is preferably included in the main chain of the repeating unit. Although the details are unclear, it is presumed that the presence of the aromatic carboxy group near the main chain further improves these properties. In this specification, the aromatic carboxy group refers to a group having a structure in which one or more carboxyl groups are bonded to an aromatic ring. In the aromatic carboxy group, the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.

[0100] Resin B used in the present disclosure 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).

[0101] [ka]

[0102] In formula (b-1), Ar 1 represents a group containing an aromatic carboxyl group, L 1 represents -COO- or -CONH-; L 2 represents a divalent linking group. In formula (b-10), Ar 10 represents a group containing an aromatic carboxyl group, L 11 represents -COO- or -CONH-; L 12 represents a trivalent linking group, P 10 represents a polymer chain.

[0103] First, formula (b-1) will be described. In formula (b-1), Ar 1 Aromatic carbamates represented by Examples of the group containing a carboxy 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.

[0104] [ka]

[0105] In the above formula, Q 1 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).

[0106] [ka]

[0107] Specific examples of aromatic tricarboxylic anhydrides include benzenetricarboxylic anhydride (1,2,3-benzenetricarboxylic anhydride, trimellitic anhydride [1,2,4-benzenetricarboxylic anhydride], etc.), naphthalenetricarboxylic anhydride (1,2,4-naphthalenetricarboxylic anhydride, 1,4,5-naphthalenetricarboxylic anhydride, 2,3,6-naphthalenetricarboxylic anhydride, 1,2,8-naphthalenetricarboxylic anhydride, etc.), 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 acid anhydrides include pyromellitic dianhydride, ethylene glycol ditrimellitic anhydride ester, propylene glycol ditrimellitic anhydride ester, butylene glycol ditrimellitic anhydride ester, 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride, 3,3',4,4'-biphenylsulfone tetracarboxylic acid dianhydride, 1,4,5,8-naphthalene tetracarboxylic acid dianhydride, 2,3,6,7-naphthalene tetracarboxylic acid dianhydride, 3,3',4,4'-biphenyl ether tetracarboxylic acid dianhydride, 3,3',4,4'-dimethyldiphenylsilane tetracarboxylic acid dianhydride, 3,3',4,4'-tetraphenylsilane tetracarboxylic acid dianhydride, 1,2,3,4-furan tetracarboxylic acid dianhydride, 4,4'-bis(3,4-dicarbamic acid dianhydride), 1,2,3,4-furan tetracarboxylic acid 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'-perfluoroisopropylidenediphthalic dianhydride, 3,3',4,4'-biphenyltetracarboxylic 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, bis(triphenylphthalic acid)-4,4'-diphenylmethane dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 9,9-bis[4-(3,4-dicarbo. xyphenoxy)phenyl]fluorene dianhydride, 3,4-dicarboxy-1,2,3, Examples thereof include 4-tetrahydro-1-naphthalene succinic dianhydride and 3,4-dicarboxy-1,2,3,4-tetrahydro-6-methyl-1-naphthalene succinic dianhydride.

[0108] Ar 1 Specific examples of the aromatic carboxyl group-containing group represented by formula (Ar-1) include Examples of the groups include a group represented by the formula (Ar-1), a group represented by the formula (Ar-2), and a group represented by the formula (Ar-3).

[0109] [ka]

[0110] In formula (Ar-1), n1 represents an integer of 1 to 4, preferably an integer of 1 or 2, and more preferably 2. In formula (Ar-2), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and further preferably 2. In formula (Ar-3), n3 and n4 each independently represent an integer of 0 to 4, and are preferably an integer of 0 to 2, more preferably 1 or 2, and further preferably 1. However, at least one of n3 and n4 is an integer of 1 or greater. In formula (Ac-3), Q 1 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).

[0111] In formula (b-1), L 1 represents -COO- or -CONH-, and preferably represents -COO-.

[0112] In formula (b-1), L 2 Examples of the divalent linking group represented by include an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group combining two or more of these. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The alkylene group may be linear, branched, or cyclic. The number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group. L 2 The divalent linking group represented by is -OL 2aIt is preferable that L is a group represented by -O-. 2a Examples of the alkylene group include an alkylene group; an arylene group; a group obtained by combining an alkylene group with an arylene group; and a group obtained by combining at least one selected from an alkylene group and an arylene group with at least one selected from the group consisting of -O-, -CO-, -COO-, -OCO-, -NH-, and -S-. The number of carbon atoms in the alkylene group is preferably 1 to 30, 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 a substituent. Examples of the substituent include a hydroxyl group.

[0113] Next, formula (b-10) will be described. In formula (b-10), Ar 10 The aromatic carboxyl group-containing group represented by the formula (b-1) is Ar 1 The same definition and preferred range are also the same.

[0114] In formula (b-10), L 11 represents -COO- or -CONH-, and preferably represents -COO-.

[0115] In formula (b-10), L 12 Examples of the trivalent linking group represented by include a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group combining two or more of these. Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. 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 linear, branched, or 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 a hydroxy group. L 12 The trivalent linking group represented by is preferably a group represented by the following formula (L12-1), and more preferably a group represented by formula (L12-2).

[0116] [ka]

[0117] L 12a and L 12b each independently represents a trivalent linking group; X 1 represents S, and *1 represents L in formula (b-10). 11 *2 represents the bond position with P in formula (b-10). 10 represents the bonding position with

[0118] L 12a and L 12b Examples of the trivalent linking group represented by the formula (I) include a hydrocarbon group; and a group formed by combining a hydrocarbon group with at least one selected from the group consisting of -O-, -CO-, -COO-, -OCO-, -NH-, and -S-.

[0119] In formula (b-10), P 10 represents a polymer chain. P 10 The polymer chain represented by the formula (I) preferably has at least one repeating unit selected from a poly(meth)acrylic repeating unit, a polyether repeating unit, a polyester repeating unit, and a polyol repeating unit. 10 The weight average molecular weight of is preferably 500 to 20,000. The lower limit is more preferably 500 or more, and particularly preferably 1,000 or more. The upper limit is more preferably 10,000 or less, further preferably 5,000 or less, and particularly preferably 3,000 or less. 10 If the weight average molecular weight is within the above range, the pigment has good dispersibility in the composition. 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.

[0120] In formula (b-10), P 10 The polymer chain represented by formula (P-1) is preferably a polymer chain containing repeating units represented by formulas (P-1) to (P-5) below, and more preferably a polymer chain containing a repeating unit represented by formula (P-5).

[0121] [ka]

[0122] In the above formula, R P1 and R P2 Each of R represents an alkylene group. P1 and R P2 The alkylene group represented by the formula (I) 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 even more preferably a linear or branched alkylene group having 3 to 12 carbon atoms. In the above formula, R P3 represents a hydrogen atom or a methyl group. 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 is preferably a single bond. P2 Examples of the divalent linking group represented by the formula (I) include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group 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. R P4represents a hydrogen atom or a substituent. Examples of the substituent include 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 alkylthioether group, an arylthioether group, a heteroarylthioether group, a (meth)acryloyl group, an oxetanyl group, and a blocked isocyanate group. In the present disclosure, the blocked isocyanate group is a group capable of generating an isocyanate group by heat, and a preferred example of the blocked isocyanate group is a group in which a blocking agent and an isocyanate group are reacted to protect the isocyanate group. Examples of the blocking agent include an oxime compound, a lactam compound, a phenol compound, an alcohol compound, an amine compound, an active methylene compound, a pyrazole compound, a mercaptan compound, an imidazole compound, and an imide compound. Examples of the blocking agent include the compounds described in paragraphs 0115 to 0117 of JP 2017-067930 A, the contents of which are incorporated herein by reference. Moreover, the blocked isocyanate group is preferably a group capable of generating an isocyanate group by heat at 90°C to 260°C.

[0123] P 10 The polymer chain represented by the formula (I) preferably has at least one group selected from the group consisting of a (meth)acryloyl group, an oxetanyl group, a blocked isocyanate group, and a t-butyl group (hereinafter also referred to as "functional group A"). It is more preferable that the functional group A is at least one group selected from the group consisting of a (meth)acryloyl group, an oxetanyl group, and a blocked isocyanate group. When the polymer chain contains the functional group A, it is easy to form a film having excellent solvent resistance. In particular, when the polymer chain contains at least one group selected from a (meth)acryloyl group, an oxetanyl group, and a blocked isocyanate group, the above effect is remarkable. In addition, the functional group When A has a t-butyl group, it is preferable to include a compound having an epoxy group or an oxetanyl group in the composition.When the functional group A has a blocked isocyanate group, it is preferable to include a compound having a hydroxy group in the composition.

[0124] Also, P10 The polymer chain represented by P 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 in the side chain among all repeating units constituting the polymer is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more. The upper limit can be set to 100% by mass, and is preferably 90% by mass or less, and more preferably 60% by mass or less.

[0125] Also, P 10 It is also preferable that the polymer chain represented by has a repeating unit containing an acidic functional group. Examples of the acidic functional group include a carboxy group, a phosphoric acid functional group, a sulfo group, and a phenolic hydroxy group. According to this embodiment, the dispersibility of the pigment in the composition can be further improved. Furthermore, the developability can also be further improved. The proportion of the repeating unit containing an acidic functional group is preferably 1% by mass to 30% by mass, more preferably 2% by mass to 20% by mass, and even more preferably 3% by mass to 10% by mass.

[0126] Resin B can be produced by reacting at least one acid anhydride selected from the group consisting of aromatic tetracarboxylic anhydrides and aromatic tricarboxylic anhydrides with a hydroxyl group-containing compound. Examples of aromatic tetracarboxylic anhydrides and aromatic tricarboxylic anhydrides include those mentioned above. The hydroxyl group-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. It is also preferable to use a compound having two hydroxyl groups and one thiol group in the molecule as the hydroxyl group-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-ethanediol, 3-mercapto-1,2-propanediol (thioglycerin), 2-mercapto-1,2-propanediol, 2-mercapto-2-methyl-1,3-propanediol, 2-mercapto-2-ethyl-1,3-propanediol, 1-mercapto-2,2-propanediol, 2-mercaptoethyl-2-methyl-1,3-propanediol, or 2-mercaptoethyl-2-ethyl-1,3-propanediol. Other hydroxyl group-containing compounds include those described in paragraphs 0084 to 0095 of JP 2018-101039 A, the contents of which are incorporated herein by reference.

[0127] The molar ratio of the acid anhydride group in the acid anhydride to the hydroxy group in the hydroxy group-containing compound (acid anhydride group / hydroxy group) is preferably 0.5 to 1.5.

[0128] Moreover, the resin containing the repeating unit represented by the above formula (b-10) can be synthesized by the following synthesis methods (1) and (2), or the like.

[0129] [Synthesis method (1)] This method comprises the steps of: radically polymerizing a polymerizable monomer having an ethylenically unsaturated group in the presence of a hydroxyl group-containing thiol compound (preferably a compound having two hydroxyl groups and one thiol group in the molecule) to synthesize a vinyl polymer having two hydroxyl groups at one terminal region; and reacting this synthesized vinyl polymer with one or more aromatic acid anhydrides selected from the group consisting of aromatic tetracarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides.

[0130] [Synthesis method (2)] Hydroxy group-containing compound (preferably containing two hydroxy groups and one thiol group in the molecule) (a compound having the above formula (I)) is reacted with one or more aromatic acid anhydrides selected from the group consisting of aromatic tetracarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides, and then, in the presence of the resulting reactant, a polymerizable monomer having an ethylenically unsaturated group is radically polymerized. In the synthesis method (2), after the polymerizable monomer having a hydroxyl group is radically polymerized, it may be further reacted with a compound having an isocyanate group (for example, a compound having an isocyanate group and the above-mentioned functional group A). ​​This produces a polymer chain P 10 A functional group A can be introduced into

[0131] Resin B can also be synthesized according to the method described in paragraphs 0120 to 0138 of JP2018-101039A.

[0132] 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, even more preferably 20,000 or less, and particularly preferably 15,000 or less. The lower limit is more preferably 4,000 or more, even more preferably 6,000 or more, and particularly preferably 7,000 or more. When the weight average molecular weight of resin B is within the above range, the effects of the present disclosure can be more significantly obtained. In addition, the storage stability of the colored photosensitive composition can be improved.

[0133] Dispersants are also available as commercially available products, and specific examples thereof include the DISPERBYK series (e.g., DISPERBYK-111, 161, etc.) manufactured by BYKChemie and the Solsperse series (e.g., Solsperse 76500, etc.) manufactured by Lubrizol Japan Co., Ltd. In addition, pigment dispersants described in paragraphs 0041 to 0130 of JP-A-2014-130338 can also be used, the contents of which are incorporated herein by reference. The resins described as dispersants above can also be used for purposes other than dispersants. For example, they can also be used as binders.

[0134] When the colored photosensitive composition according to the present disclosure contains a resin, the content of the resin in the total solid content of the colored photosensitive composition is preferably 5% by mass 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, even more preferably 35% by mass or less, and particularly preferably 30% by mass or less. In addition, the content of the resin having an acidic functional group (alkali-soluble resin) in the total solid content of the colored photosensitive composition is preferably 5% by mass 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, even more preferably 35% by mass or less, and particularly preferably 30% by mass or less. In addition, the content of the resin having an acidic functional group (alkali-soluble resin) in the total amount of resin is preferably 30% by mass or more, more preferably 50% by mass or more, more preferably 70% by mass or more, and particularly preferably 80% by mass or more, because excellent developability is easily obtained. The upper limit can be 100% by mass, 95% by mass, or 90% by mass or less. In the colored photosensitive composition according to the present disclosure, only one type of resin may be used, or two or more types may be used in combination. When two or more types are used in combination, the total amount thereof is preferably within the above range.

[0135] <Pigment derivatives> The colored photosensitive composition according to the present disclosure may contain a pigment derivative. Note that the "pigment derivative" in the present disclosure is a pigment derivative other than the diketopyrrolopyrrole compounds A and B represented by the above formula 1. Examples of the pigment derivative include compounds having a structure in which a portion of a chromophore is substituted with an acidic functional group or a basic functional group. Examples of the chromophore constituting the pigment derivative include a quinoline skeleton, a benzimidazolone skeleton, a diketopyrrolopyrrole skeleton, an azo skeleton, a phthalocyanine skeleton, an anthraquinone skeleton, a quinacridone skeleton, a dioxazine skeleton, a perinone skeleton, a perylene skeleton, a thioindigo skeleton, an isoindoline skeleton, an isoindolinone skeleton, a quinophthalone skeleton, Examples of the acidic functional group include a sulfo group, a carboxy group, a phosphoric acid functional group, and salts thereof. Examples of the atom or atomic group constituting the salt include an alkali metal ion (Li + , Na + , K + etc.) , alkaline earth metal ions (Ca 2+ , Mg 2+ Examples of the basic functional group include an amino group, a pyridinyl group and its salts, an ammonium group salt, and a phthalimidomethyl group. Examples of the atom or atomic group constituting the salt include a hydroxide ion, a halogen ion, a carboxylate ion, a sulfonate ion, and a phenoxide ion.

[0136] As the pigment derivative, a pigment derivative with excellent visible transparency (hereinafter also referred to as a transparent pigment derivative) can be used. The maximum molar absorption coefficient (εmax) of the transparent pigment derivative in the wavelength range of 400 nm to 700 nm is 3,000 L·mol -1 ·cm -1 It is preferable that the concentration is less than 1,000 L·mol -1·cm -1 It is more preferable that it is less than 100 L·mol -1 ·cm -1 The lower limit of εmax is, for example, 1 L mol -1 ·cm -1 is greater than or equal to 10 L mol -1 ·cm -1 More than that is fine.

[0137] Specific examples of pigment derivatives include those described in JP-A-56-118462, JP-A-63-264674, JP-A-01-217077, JP-A-03-009961, JP-A-03-026767, JP-A-03-153780, JP-A-03-045662, JP-A-04-285669, JP-A-06-145546, JP-A-06-212088, JP-A-06-240158, JP-A-10-030063, JP-A-10-195326, paragraphs 0086 to 0098 of International Publication No. 2011 / 024896, and the like. Examples of the compounds described in paragraphs 0063 to 0094 of International Publication No. 2012 / 102399, paragraph 0082 of International Publication No. 2017 / 038252, paragraph 0171 of JP 2015-151530 A, paragraphs 0162 to 0183 of JP 2011-252065 A, JP 2003-081972 A, Japanese Patent No. 5299151 A, JP 2015-172732 A, JP 2014-199308 A, JP 2014-085562 A, JP 2014-035351 A, JP 2008-081565 A, and JP 2019-109512 A are mentioned.

[0138] The content of the pigment derivative is preferably 1 to 30 parts by mass, and more preferably 3 to 20 parts by mass, relative to 100 parts by mass of the pigment. Only one type of pigment derivative may be used, or two or more types may be used in combination.

[0139] <Polymerizable compound> The colored photosensitive composition according to the present disclosure preferably contains a polymerizable compound. As the polymerizable compound, a known compound capable of being crosslinked by a radical, an acid, or heat can be used. In the present disclosure, the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated group. Examples of the ethylenically unsaturated group include a vinyl group, a (meth)allyl group, and a (meth)acryloyl group. The polymerizable compound used in the present disclosure is preferably a radically polymerizable compound.

[0140] The polymerizable compound may be in any chemical form such as a monomer, a prepolymer, or an 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.

[0141] The polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated groups, more preferably a compound containing 3 to 15 ethylenically unsaturated groups, and even more preferably a compound containing 3 to 6 ethylenically unsaturated groups. The polymerizable compound is preferably a trifunctional to 15-functional (meth)acrylate compound, and more preferably a trifunctional to 6-functional (meth)acrylate compound. Specific examples of the polymerizable compound include compounds described in paragraphs 0095 to 0108 of JP 2009-288705 A, paragraph 0227 of JP 2013-029760 A, paragraphs 0254 to 0257 of JP 2008-292970 A, paragraphs 0034 to 0038 of JP 2013-253224 A, paragraph 0477 of JP 2012-208494 A, JP 2017-048367 A, Japanese Patent No. 6057891, and Japanese Patent No. 6031807, the contents of which are incorporated herein by reference.

[0142] Preferred polymerizable compounds include dipentaerythritol triacrylate (commercially available product: KAYARAD D-330, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (commercially available product: KAYARAD D-320, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product: KAYARAD D-310, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products: KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd., and 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 (e.g., SR454 and SR499, commercially available from Sartomer). In addition, examples of the polymerizable compound that can be used include diglycerol EO (ethylene oxide) modified (meth)acrylate (commercially available product is 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.), and light acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.).

[0143] As the polymerizable compound, it is also preferable to use a trifunctional (meth)acrylate compound such as trimethylolpropane tri(meth)acrylate, trimethylolpropane propyleneoxy-modified tri(meth)acrylate, trimethylolpropane ethyleneoxy-modified tri(meth)acrylate, isocyanuric acid ethyleneoxy-modified tri(meth)acrylate, or pentaerythritol tri(meth)acrylate. 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 Toagosei Co., Ltd.), NK Ester A9300, 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.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, and PET-30 (manufactured by Nippon Kayaku Co., Ltd.).

[0144] 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 colored photosensitive composition in the unexposed area can be easily removed during development, and the occurrence of development residues can be suppressed. Examples of the acidic functional group include a carboxy group, a sulfo group, and a phosphoric acid functional group, and a carboxy group is preferred. Examples of commercially available polymerizable compounds having an acidic functional group include Aronix M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.). Preferred polymerizable compounds having an acidic functional group include The preferable acid value 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 terms of production and handling.

[0145] As the polymerizable compound, a polymerizable compound having a caprolactone structure can also be used. Polymerizable compounds having a caprolactone structure are commercially available as the KAYARAD DPCA series from Nippon Kayaku Co., Ltd., and examples thereof include DPCA-20, DPCA-30, DPCA-60, and DPCA-120.

[0146] 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 even more preferably a trifunctional to hexafunctional (meth)acrylate compound having 4 to 20 ethyleneoxy groups. Examples of commercially available polymerizable compounds having an alkyleneoxy group include SR-494, a tetrafunctional (meth)acrylate having four ethyleneoxy groups manufactured by Sartomer, and KAYARAD TPA-330, a trifunctional (meth)acrylate having three isobutyleneoxy groups.

[0147] 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).

[0148] It is also preferable to use a polymerizable compound that does not substantially contain environmentally regulated substances such as toluene. Examples of commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).

[0149] As the polymerizable compound, it is also preferable to use urethane acrylates described in JP-B-48-041708, JP-A-51-037193, JP-B-02-032293, and JP-B-02-016765, urethane compounds having an ethylene oxide skeleton described in JP-B-58-049860, JP-B-56-017654, JP-B-62-039417, and JP-B-62-039418, and polymerizable compounds having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-01-105238. In addition, 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 as the polymerizable compound.

[0150] When the colored photosensitive composition according to the present disclosure contains a polymerizable compound, the content of the polymerizable compound in the total solid content of the colored photosensitive composition is preferably 0.1% by mass to 50% by mass. The lower limit is more preferably 0.5% by mass or more, and even more preferably 1% by mass or more. The upper limit is more preferably 45% by mass or less, and even more preferably 40% by mass or less.

[0151] The total content of the polymerizable compound and the resin in the total solid content of the colored photosensitive composition is preferably 10% by mass to 65% by mass from the viewpoints of curability, developability and film formability. The lower limit is more preferably 15% by mass or more, even more 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, even more preferably 50% by mass or less, and particularly preferably 40% by mass or less. In addition, the resin is preferably used in an amount of 30% by mass to 100 parts by mass of the polymerizable compound. The content is preferably 0 to 300 parts by mass. 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.

[0152] In the colored photosensitive composition according to the present disclosure, the polymerizable compound may be used alone or in combination with two or more kinds. When two or more kinds are used, the total amount thereof is preferably within the above range.

[0153] <Photopolymerization initiator> The colored photosensitive composition according to the present disclosure preferably contains a photopolymerization initiator. In particular, when the colored photosensitive composition according to the present disclosure contains a polymerizable compound, the colored photosensitive composition according to the present disclosure preferably further contains a photopolymerization initiator. The photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible light region is preferred. The photopolymerization initiator is preferably a photoradical polymerization initiator.

[0154] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α-hydroxyketone compounds, and α-aminoketone compounds. From the viewpoint of exposure sensitivity, the photopolymerization initiator is preferably a compound selected from the group consisting of a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an α-hydroxyketone compound, an α-aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a triarylimidazole dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, and a 3-aryl substituted coumarin compound, more preferably a compound selected from the group consisting of an oxime compound, an α-hydroxyketone compound, an α-aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound. Further, as the photopolymerization initiator, the compounds described in paragraphs 0065 to 0111 of JP 2014-130173 A and JP Patent No. 6301489 A, the peroxide-based photopolymerization initiator described in MATERIAL STAGE 37 to 60p, vol. 19, No. 3, 2019, the photopolymerization initiator described in WO 2018 / 221177 A, the photopolymerization initiator described in WO 2018 / 110179 A, ​​the photopolymerization initiator described in JP 2019-043864 A, the photopolymerization initiator described in JP 2019-044030 A, and the organic peroxide described in JP 2019-167313 A can be mentioned, the contents of which are incorporated herein by reference.

[0155] Commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (manufactured by BASF), etc. Commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins BV), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by BASF), etc. Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (both manufactured by IGM Resins BV), Irgacure 819, Irgacure TPO (both manufactured by BASF), and the like.

[0156] 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 J.C.S. Perkin II (1979, pp. 1653-1660), compounds described in J.C.S. Perkin II (1979, pp. 156-162), and compounds described in Journal of Photopolymer Science. and Technology (1995, pp. 202-232), compounds described in JP-A-2000-066385, compounds described in JP-A-2000-080068, compounds described in JP-T-2004-534797, compounds described in JP-A-2006-342166, compounds described in JP-A-2017-019766, compounds described in Japanese Patent No. 6065596, compounds described in WO 2015 / 152153, compounds described in WO 2017 / 051680, compounds described in JP-A-2017-198865, compounds described in paragraphs 0025 to 0038 of WO 2017 / 164127, compounds described in WO 2013 / 167515, and the like. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, and 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one. Examples of commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, and Irgacure OXE04 (all manufactured by BASF), TR-PBG-304 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), and Adeka Optomer N-1919 (manufactured by ADEKA Corporation, photopolymerization initiator 2 described in JP 2012-014052 A). In addition, it is also preferable to use a compound that is not colorable or a compound that is highly transparent and does not easily discolor as the oxime compound. Examples of commercially available products include Adeka Arcles NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA Corporation).

[0157] 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 the compounds described in JP2014-137466A.

[0158] As the photopolymerization initiator, an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is replaced with a naphthalene ring can also be used. Specific examples of such oxime compounds include the compounds described in WO 2013 / 083505.

[0159] 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.

[0160] As the photopolymerization initiator, an oxime compound having a nitro group can be used. It is also preferable that the oxime compound having a nitro group is a dimer. Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP 2013-114249 A, paragraphs 0008 to 0012, and 0070 to 0079 of JP 2014-137466 A, the compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071 A, and Adeka Arcles NCI-831 (manufactured by ADEKA Corporation).

[0161] As the photopolymerization initiator, an oxime compound having a benzofuran skeleton can also be used. A specific example is OE-01 described in International Publication No. 2015 / 036910. ~OE-75 is an example.

[0162] As the photopolymerization initiator, an oxime compound in which a substituent having a hydroxyl group is bonded to a carbazole skeleton can also be used. Examples of such photopolymerization initiators include the compounds described in WO 2019 / 088055.

[0163] Specific examples of oxime compounds preferably used in the present disclosure are shown below, but the present disclosure is not limited thereto.

[0164] [ka]

[0165] [ka]

[0166] The oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 nm to 500 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 nm to 480 nm. From the viewpoint of sensitivity, the molar absorption coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably 1,000 to 300,000, even more preferably 2,000 to 300,000, and particularly preferably 5,000 to 200,000. The molar absorption coefficient of the compound can be measured using a known method. For example, a spectrophotometer (Varian Cary-5 spec It is preferable to measure the concentration of ethyl acetate at 0.01 g / L using a trophotometer.

[0167] As the photopolymerization initiator, a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used. By using such a photoradical polymerization initiator, two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained. In addition, when a compound with an asymmetric structure is used, the crystallinity is reduced and the solubility in a solvent or the like is improved, so that precipitation is less likely to occur over time, and the stability over time of the colored photosensitive composition can be improved. Specific examples of bifunctional or trifunctional or higher functional photoradical polymerization initiators include dimers of oxime compounds described in JP-T-2010-527339, JP-T-2011-524436, WO-2015 / 004565, paragraphs 0407 to 0412 of JP-T-2016-532675, and paragraphs 0039 to 0055 of WO-2017 / 033680; compounds (E) and (G) described in JP-T-2013-522445; Examples of the photoinitiator include Cmpd1 to 7 described in JP 2016 / 034963 A, the oxime ester photoinitiator described in paragraph 0007 of JP 2017-523465 A, the photoinitiator described in paragraphs 0020 to 0033 of JP 2017-167399 A, the photopolymerization initiator (A) described in paragraphs 0017 to 0026 of JP 2017-151342 A, and the oxime ester photoinitiator described in Japanese Patent No. 6,469,669 A.

[0168] When the colored photosensitive composition according to the present disclosure contains a photopolymerization initiator, the content of the photopolymerization initiator in the total solid content of the colored photosensitive composition is preferably 0.1% by mass 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 according to the present disclosure, only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.

[0169] <Compounds having a cyclic ether group> The colored photosensitive composition according to the present disclosure 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 a compound having one or more epoxy groups in one molecule, and a compound having two or more epoxy groups is preferred. The epoxy group is preferably 1 to 100 in one molecule. The upper limit of the epoxy group may be, for example, 10 or less, or 5 or less. The lower limit of the epoxy group is preferably 2 or more. As the compound having an epoxy group, the compounds described in paragraphs 0034 to 0036 of JP 2013-011869 A, paragraphs 0147 to 0156 of JP 2014-043556 A, paragraphs 0085 to 0092 of JP 2014-089408 A, and the compounds described in JP 2017-179172 A can also be used. The contents of these are incorporated herein by reference.

[0170] The compound having an epoxy group may be either 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 (macromolecule) (e.g., a molecular weight of 1,000 or more, and in the case of a polymer, 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.

[0171] As the compound having an epoxy group, an epoxy resin can be preferably used. Examples of the epoxy resin include epoxy resins which are glycidyl ethers of phenolic compounds, epoxy resins which 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 and other silicon compounds, copolymers of polymerizable unsaturated compounds having epoxy groups and other polymerizable unsaturated compounds, etc. The epoxy equivalent of the epoxy resin is preferably 310g / eq to 3,300g / eq, more preferably 310g / eq to 1,700g / eq, and even more preferably 310g / eq to 1,000g / eq.

[0172] Examples of commercially available compounds having a cyclic ether group include EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC Corporation), 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 NOF Corporation, epoxy group-containing polymers).

[0173] When the colored photosensitive composition according to the present disclosure contains a compound having a cyclic ether group, the content of the compound having a cyclic ether group in the total solid content of the colored photosensitive composition is preferably 0.1% by mass 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 according to the present disclosure, only one type of compound having a cyclic ether group may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.

[0174] <Silane coupling agent> The colored photosensitive composition according to the present disclosure may contain a silane coupling agent. According to this aspect, the adhesion of the obtained film to the support can be further improved. In the present disclosure, the silane coupling agent means a silane compound having a hydrolyzable group and a functional group other than the hydrolyzable group. In addition, the hydrolyzable group means a substituent that is directly bonded to a silicon atom and can generate a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. In addition, examples of functional groups other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, and an amino group, a (meth)acryloyl group, and an epoxy group are preferable. Specific examples of the silane coupling agent include N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane (Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N-β-aminoethyl-γ-aminopropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N-β-aminoethyl-γ-aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd., trade name KBE-602), γ-aminopropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., trade name KBM-903), γ-aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloxypropylmethyldimethoxysilane (Shin-Etsu Chemical Co., Ltd., trade name KBM-502), and 3-methacryloxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., trade name KBM-503). Specific examples of the silane coupling agent include the compounds described in paragraphs 0018 to 0036 of JP-A No. 2009-288703 and the compounds described in paragraphs 0056 to 0066 of JP-A No. 2009-242604, the contents of which are incorporated herein by reference.

[0175] When the colored photosensitive composition according to the present disclosure contains a silane coupling agent, The content of the silane coupling agent in the total solid content of the composition is preferably 0.1% by mass 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 according to the present disclosure, only one type of silane coupling agent may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.

[0176] <Organic solvent> The colored photosensitive composition according to the present disclosure preferably contains an organic solvent. Examples of the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For details, see paragraph 0223 of International Publication No. 2015 / 166779, the contents of which are incorporated herein by reference. In addition, ester-based solvents substituted with a cyclic alkyl group and ketone-based solvents substituted with a cyclic alkyl group can also be preferably used. Specific examples of organic solvents include polyethylene glycol monomethyl ether, dichloromethane, 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-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, etc. However, aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be reduced for environmental reasons (for example, the amount of the organic solvent may be 50 mass ppm (parts per million) or less, 10 mass ppm or less, or 1 mass ppm or less).

[0177] In the present disclosure, it is preferable to use an organic solvent with a low metal content, and the metal content of the organic solvent is preferably 10 mass ppb (parts per billion) or less, for example. If necessary, an organic solvent with a mass ppt (parts per trillion) level may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (The Chemical Daily, November 13, 2015).

[0178] Methods for removing impurities such as metals from organic solvents include, for example, distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter. The filter used for filtration has a filter pore size of preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The filter material is preferably polytetrafluoroethylene, polyethylene, or nylon.

[0179] The organic solvent may contain isomers (compounds having the same number of atoms but different structures). In addition, the organic solvent may contain only one type of isomer or multiple types of isomers.

[0180] In the present disclosure, the peroxide content in the organic solvent is preferably 0.8 mmol / L or less, and more preferably contains substantially no peroxide.

[0181] The content of the organic solvent in the colored photosensitive composition is preferably from 20% by mass to 95% by mass, more preferably from 30% by mass to 90% by mass, and further preferably from 40% by mass to 90% by mass.

[0182] In addition, from the viewpoint of environmental regulations, the colored photosensitive composition according to the present disclosure preferably does not substantially contain any environmentally restricted substances. In the present disclosure, "substantially does not contain any environmentally restricted substances" means that the content of the environmentally restricted substances in the colored photosensitive composition is 50 ppm by mass or less. The concentration is 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 substances are subject to REACH (Registration Evaluation Authorization and Restriction of CHemicals) regulations, PRTR (Pollutant Release and The substances are registered as environmentally regulated substances under the Transfer Register (EPA) Act, Volatile Organic Compounds (VOC) regulations, etc., and the amount of use and the handling method are strictly regulated. These compounds may be used as solvents when producing each component used in the colored photosensitive composition according to the present disclosure, and may be mixed into the colored photosensitive composition as a residual solvent. It is preferable to reduce these substances as much as possible from the viewpoint of human safety and environmental consideration. Examples of methods for reducing environmentally regulated substances include a method in which the system is heated or depressurized to a temperature above the boiling point of the environmentally regulated substance, and the environmentally regulated substance is distilled off from the system to reduce the amount. In addition, when a small amount of environmentally regulated substance is distilled off, it is also useful to perform azeotropy with a solvent having a boiling point equivalent to the corresponding solvent in order to increase efficiency. In addition, when a compound having radical polymerizability is contained, a polymerization inhibitor or the like may be added and distilled off under reduced pressure in order to suppress crosslinking between molecules caused by the progress of a radical polymerization reaction during distillation under reduced pressure. These distillation methods can be used at any stage, such as the stage of the raw materials, the stage of the product obtained by reacting the raw materials (for example, a resin solution or a polyfunctional monomer solution after polymerization), or the stage of a colored photosensitive composition prepared by mixing these compounds.

[0183] <Polymerization inhibitor> The colored photosensitive composition according to the present disclosure 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-t-butylphenol), and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among these, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solid content of the colored photosensitive composition is preferably 0.0001% by mass to 5% by mass.

[0184] <Surfactant> The colored photosensitive composition according to the present disclosure may contain a surfactant. As the surfactant, various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants may be used. As the surfactant, the surfactants described in paragraphs 0238 to 0245 of WO 2015 / 166779 may be mentioned, the contents of which are incorporated herein by reference.

[0185] In the present disclosure, the surfactant is preferably a fluorosurfactant. By including a fluorosurfactant in the colored photosensitive composition, the liquid properties (particularly, fluidity) can be further improved, and the liquid saving property can be further improved. In addition, a film with less unevenness in thickness can be formed.

[0186] The fluorine content in the fluorine-based surfactant is preferably 3% by mass to 40% by mass, more preferably 5% by mass to 30% by mass, and particularly preferably 7% by mass to 25% by mass. A fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of the thickness of the coating film and liquid saving, and also has good solubility in the colored photosensitive composition.

[0187] Examples of fluorine-based surfactants include those described in paragraphs 0060 to 0064 of JP 2014-041318 A (corresponding paragraphs 0060 to 0064 of WO 2014 / 017669 A). and the surfactants described in paragraphs

[0117] to

[0132] of JP-A No. 2011-132503, the contents of which are incorporated herein by reference. Commercially available fluorine-based surfactants include, for example, Megafac 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 Corporation), and PolyFox. Examples include PF636, PF656, PF6320, PF6520, and PF7002 (all manufactured by OMNOVA).

[0188] In addition, the fluorosurfactant may be an acrylic compound that has a molecular structure with a functional group containing a fluorine atom, and when heat is applied, the functional group containing the fluorine atom is broken and the fluorine atom volatilizes. Examples of such fluorosurfactants include the Megafac DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Business Daily (February 23, 2016)), such as Megafac DS-21.

[0189] In addition, it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorine-based surfactant. For such a fluorine-based surfactant, the description in JP 2016-216602 A can be referred to, and the contents of this specification are incorporated herein.

[0190] The fluorosurfactant may be a block polymer. For example, the compounds described in JP-A-2011-089090 may be mentioned. As the fluorosurfactant, a fluorine-containing polymer compound containing a repeating unit derived from a (meth)acrylate compound having a fluorine atom and a repeating unit derived from a (meth)acrylate compound having two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy groups, propyleneoxy groups) may also be preferably used. In addition, the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorosurfactant used in the present disclosure.

[0191] [ka]

[0192] The weight average molecular weight of the above compound is preferably 3,000 to 50,000, for example, 14,000. In the above compound, % indicating the proportion of repeating units is mol %.

[0193] In addition, the fluorine-based surfactant may be a fluorine-containing polymer having an ethylenically unsaturated group in the side chain. Specific examples include the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP 2010-164965 A, such as Megafac RS-101, RS-102, RS-718K, and RS-72-K manufactured by DIC Corporation. In addition, the fluorine-based surfactant may be the compounds described in paragraphs 0015 to 0090 of JP 2015-117327 A. Compounds described in 0158 can also be used.

[0194] Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, and their ethoxylates and propoxylates (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, and sorbitan fat. Acid esters, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (manufactured by BASF), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Lubrizol Japan Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), Paionin D-6112, D-6112-W, D-6315 (manufactured by Takemoto Oil Co., Ltd.), Olfine E1010, Surfynol 104, 400, 440 (manufactured by Nissin Chemical Industry Co., Ltd.), and the like.

[0195] Examples of silicone surfactants include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (all manufactured by Toray Dow Corning Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all manufactured by Momentive Performance Materials, Inc.), KP-341, KF-6001, KF-6002 (all manufactured by Shin-Etsu Silicone Co., Ltd.), BYK307, BYK323, BYK330 (all manufactured by BYK-Chemie).

[0196] The content of the surfactant in the total solid content of the colored photosensitive composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% by mass to 3.0% by mass. In the colored photosensitive composition according to the present disclosure, only one type of surfactant may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.

[0197] <Ultraviolet absorbing agent> The colored photosensitive composition according to the present disclosure may contain an ultraviolet absorber. Examples of ultraviolet absorbers that can be used include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, and triazine compounds. For details, compounds described in paragraphs 0052-0072 of JP 2012-208374 A, paragraphs 0317-0334 of JP 2013-068814 A, and paragraphs 0061-0080 of JP 2016-162946 A are included, the contents of which are incorporated herein by reference. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Chemical Co., Ltd.). Examples of benzotriazole compounds include the MYUA series (The Chemical Daily, February 1, 2016) manufactured by Miyoshi Oil & Fat Co., Ltd. Moreover, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used as the ultraviolet absorbing agent.

[0198] The content of the ultraviolet absorbent in the total solid content of the colored photosensitive composition is preferably 0.01% by mass to 10% by mass, more preferably 0.01% by mass to 5% by mass. In the colored photosensitive composition according to the present disclosure, only one type of ultraviolet absorbent may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.

[0199] <Antioxidants> The colored photosensitive composition according to the present disclosure 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. Examples of preferred phenolic compounds include hindered phenolic compounds. Compounds having a substituent at the site (ortho position) adjacent to the phenolic hydroxy group are preferred. As the aforementioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred. In addition, as the antioxidant, a compound having a phenolic group and a phosphite group in the same molecule is also preferred. As the antioxidant, a phosphorus-based antioxidant may also be suitably used. Examples of phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, and ethyl bis(2,4-di-tert-butyl-6-methylphenyl)phosphite. Examples of commercially available antioxidants include Adeka STAB AO-20, Adeka STAB AO-30, Adeka STAB AO-40, Adeka STAB AO-50, Adeka STAB AO-50F, Adeka STAB AO-60, Adeka STAB AO-60G, Adeka STAB AO-80, and Adeka STAB AO-330 (all manufactured by ADEKA Corporation). In addition, the antioxidant may be a compound described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, a compound described in Korean Patent Publication No. 10-2019-0059371, or the like.

[0200] The content of the antioxidant in the total solid content of the colored photosensitive composition is preferably 0.01% by mass to 20% by mass, and more preferably 0.3% by mass to 15% by mass. In the colored photosensitive composition according to the present disclosure, only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.

[0201] <Other ingredients> The colored photosensitive composition according to the present disclosure may contain, as necessary, a sensitizer, a curing accelerator, a filler, a heat curing accelerator, a plasticizer, and other auxiliaries (for example, conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling accelerators, fragrances, surface tension adjusters, chain transfer agents, etc.). By appropriately incorporating these components, it is possible to adjust properties such as film properties. For these components, for example, the description in paragraphs 0183 and after of JP-A-2012-003225 (corresponding to paragraph 0237 of the specification of US Patent Application Publication No. 2013 / 0034812) and the description in paragraphs 0101 to 0104, 0107 to 0109, etc. of JP-A-2008-250074 can be referred to, and the contents of these are incorporated herein. In addition, the colored composition according to the present disclosure may contain, as necessary, a latent antioxidant. Examples of latent antioxidants include compounds in which the site functioning as an antioxidant is protected with a protecting group, and the protecting group is removed by heating at 100°C to 250°C or at 80°C to 200°C in the presence of an acid / base catalyst, thereby functioning as an antioxidant. Examples of latent antioxidants include compounds described in International Publication No. 2014 / 021023, International Publication No. 2017 / 030005, and JP-A-2017-008219. Examples of commercially available latent antioxidants include Adeka Arcles GPA-5001 (manufactured by ADEKA Corporation). In addition, as described in JP-A-2018-155881, CI Pigment Yellow 129 may be added for the purpose of improving weather resistance.

[0202] The colored photosensitive composition according to the present disclosure may contain a metal oxide in order 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 has a core-shell structure. In this case, the core portion may be hollow.

[0203] The colored photosensitive composition according to the present disclosure may also include a light resistance improver. Examples of the light resistance improver include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, the compounds described in paragraphs 0036 to 0037 and 0049 to 0052 of JP-A-2017-129774, 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 paragraphs 0025 to 0039 of JP-A-2017-186546. JP-A-2015-025116, JP-A-2012-145604, JP-A-2012-103475, JP-A-2012-103475, JP-A-2012-103475, JP-A-2011-257591, JP-A-2011-257591, JP-A-2011-191483, JP-A-2011-145668, JP-A-2011-145668, JP-A-2011-253174 ...7591,

[0204] In the colored photosensitive composition according to the present disclosure, the content of free metal that is not bonded or coordinated to a pigment or the like is preferably 100 ppm or less, more preferably 50 ppm or less, even more preferably 10 ppm or less, and particularly preferably substantially free. According to this embodiment, effects such as stabilization of pigment dispersibility (suppression of aggregation), improvement of spectral characteristics due to improved dispersibility, stabilization of curable components, suppression of conductivity fluctuation due to elution of metal atoms and metal ions, and improvement of display characteristics can be expected. In addition, the effects described in JP 2012-153796 A, JP 2000-345085 A, JP 2005-200560 A, JP 08-043620 A, JP 2004-145078 A, JP 2014-119487 A, JP 2010-083997 A, JP 2017-090930 A, JP 2018-025612 A, JP 2018-025797 A, JP 2017-155228 A, JP 2018-036521 A, etc. can be obtained. The types 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, Bi, etc. In addition, the colored photosensitive composition according to the present disclosure preferably has a content of free halogens not bonded or coordinated with pigments or the like of 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 anions thereof. Methods for reducing free metals and halogens in the colored photosensitive composition include washing with ion-exchanged water, filtration, ultrafiltration, purification with ion-exchange resin, and the like.

[0205] The colored photosensitive composition according to the present disclosure may contain a dye. As the dye, known dyes can be used. The dye is not particularly limited, and examples thereof include pyrazole azo compounds, anilino azo compounds, triarylmethane compounds, anthraquinone compounds, anthrapyridone compounds, benzylidene compounds, oxonol compounds, pyrazolotriazole azo compounds, pyridone azo compounds, cyanine compounds, phenothiazine compounds, pyrrolopyrazole azomethine compounds, xanthene compounds, phthalocyanine compounds, benzopyran compounds, indigo compounds, and pyrromethene compounds. In addition, as the dye, the methine dyes described in JP-A-2019-073695, the methine dyes described in JP-A-2019-073696, the methine dyes described in JP-A-2019-073697, and the methine dyes described in JP-A-2019-073698 can also be used. can. The colored photosensitive composition according to the present disclosure may also use a dye multimer. The dye multimer is preferably a dye dissolved in a solvent for use. The dye multimer may also form particles. When the dye multimer is in the form of particles, it is usually used in a state of being dispersed in a solvent. The dye multimer in a particulate state can be obtained, for example, by emulsion polymerization, and specific examples of the compounds and manufacturing methods described in JP-A-2015-214682 include those described in JP-A-2015-214682. The dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less. The multiple dye structures in one molecule may be the same dye structure or different dye structures. The weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000. The lower limit is more preferably 3,000 or more, and even more preferably 6,000 or more. The upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less. As the dye multimer, compounds described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, WO 2016 / 031442, and the like can also be used. The content of the dye is preferably less than the content of the pigment.

[0206] The colored photosensitive compositions according to this disclosure are also preferably substantially free of terephthalic acid esters.

[0207] The water content of the colored photosensitive composition according to the present disclosure 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.

[0208] The colored photosensitive composition according to the present disclosure can be used with its viscosity adjusted for the purpose of adjusting the film surface state (flatness, etc.), adjusting the film thickness, etc. The value of the viscosity can be appropriately selected as necessary, and is preferably 0.3 mPa·s to 50 mPa·s, and more preferably 0.5 mPa·s to 20 mPa·s at 23°C. The viscosity can be measured, for example, using a viscometer RE85L (rotor: 1°34'×R24, measurement range 0.6 to 1,200 mPa·s) manufactured by Toki Sangyo Co., Ltd., with the temperature adjusted to 23°C.

[0209] When the colored photosensitive composition according to the present disclosure is used as a color filter for a liquid crystal display device, the voltage holding ratio of the liquid crystal display element having 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, and typical means include the use of a material with high purity (e.g., reduction of ionic impurities) and control of 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 JP2011-008004A and paragraphs 0123 to 0129 of JP2012-224847A.

[0210] <Containment Container> The container for storing the colored photosensitive composition according to the present disclosure is not particularly limited, and a known container can be used. In addition, it is also preferable to use a multi-layer bottle whose inner wall is made of six types of six-layer resin or a bottle with a seven-layer structure of six types of resin as the container, in order to suppress the incorporation of impurities into the raw materials or the colored photosensitive composition. Examples of such containers include the container described in JP-A-2015-123351. In addition, it is also preferable that the inner wall of the colored photosensitive composition is made of glass or stainless steel, in order to prevent metal elution from the inner wall of the container, increase the storage stability of the composition, and suppress the deterioration of the components. The storage conditions for the colored photosensitive composition according to the present disclosure are not particularly limited, and a conventionally known method can be used. In addition, the method described in JP-A-2016-180058 can also be used. .

[0211] <Method for preparing colored photosensitive composition> The colored photosensitive composition according to the present disclosure can be prepared by mixing the above-mentioned components. When preparing the colored photosensitive composition, all the components may be simultaneously dissolved and / or dispersed in a solvent to prepare the colored photosensitive composition, or, if necessary, each component may be appropriately prepared as two or more solutions or dispersions, which are mixed at the time of use (at the time of application) to prepare the colored photosensitive composition.

[0212] In addition, it is also preferable to include a process for dispersing the pigment when preparing the colored photosensitive composition. In the process for dispersing the pigment, examples of mechanical forces used for dispersing the pigment include compression, squeezing, impact, shear, and cavitation. Specific examples of these processes include a bead mill, a sand mill, a roll mill, a ball mill, a paint shaker, a microfluidizer, a high-speed impeller, a sand grinder, a flow jet mixer, high-pressure wet atomization, and ultrasonic dispersion. In addition, in the grinding of the pigment in a sand mill (bead mill), it is preferable to use beads with a small diameter, increase the bead packing rate, and perform the treatment under conditions that increase the grinding efficiency. In addition, it is preferable to remove coarse particles by filtration, centrifugation, or the like after the grinding treatment. In addition, the process and dispersing machine for dispersing the pigment may be suitably used as described in "Dispersion Technology Encyclopedia, published by Joho Kiko Co., Ltd., July 15, 2005" or "Dispersion Technology and Industrial Applications Focused on Suspension (Solid / Liquid Dispersion System) - Comprehensive Data Collection, published by Management Development Center Publishing Department, October 10, 1978" and in paragraph 0022 of JP2015-157893A. In addition, in the process for dispersing the pigment, a salt milling process may be performed to refine the particles. For the materials, equipment, processing conditions, etc. used in the salt milling process, the descriptions in, for example, JP2015-194521A and JP2012-046629A may be referred to.

[0213] In preparing the colored photosensitive composition, it is preferable to filter the colored photosensitive composition with a filter for the purpose of removing foreign matter and reducing defects. As the filter, any filter that has been used for filtering purposes can be used without any particular limitation. For example, there are filters using 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 and ultra-high-molecular-weight polyolefin resins). Among these materials, polypropylene (including high-density polypropylene) and nylon are preferred.

[0214] 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. When the pore size of the filter is within the above range, fine foreign matter can be removed more reliably. The nominal value of the filter manufacturer can be referred to for the pore size value of the filter. Various filters provided by Nippon Pall Corporation (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Nippon Integris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), Kitz Microfilter Co., Ltd., etc. can be used.

[0215] It is also preferable to use a fibrous filter medium as the filter. Examples of fibrous filter medium include polypropylene fiber, nylon fiber, glass fiber, etc. Commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by ROKI TECHNO CO., LTD.

[0216] 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. The above may be performed. Filters having different pore sizes within the above range may be combined. Filtration with the first filter may be performed only on the dispersion liquid, and filtration with the second filter may be performed after mixing with other components.

[0217] (cured product) The cured product according to the present disclosure is a cured product obtained by curing the colored photosensitive composition according to the present disclosure. The cured product according to the present disclosure can be suitably used for color filters, etc. Specifically, it can be suitably used as a colored layer (pixel) of a color filter, and more specifically, it can be suitably used as a red colored layer (red pixel) of a color filter. The cured product according to the present disclosure is preferably a film-like cured product, and its film thickness can be appropriately adjusted according to the 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.

[0218] (Color filter) Next, the color filter according to the present disclosure will be described. The color filter according to the present disclosure includes the cured product according to the present disclosure described above. More preferably, the color filter has the cured film according to the present disclosure as a pixel. The color filter according to the present disclosure can be used in solid-state imaging devices such as CCD (charge-coupled device) and CMOS (complementary metal-oxide semiconductor), image display devices, and the like.

[0219] In the color filter according to the present disclosure, the thickness of the film according to the present disclosure can be appropriately adjusted according to the purpose. The 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 thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0220] In the color filter according to the present disclosure, the pixel width is preferably 0.5 μm to 20.0 μm. The lower limit is more preferably 1.0 μm or more, and particularly preferably 2.0 μm or more. The upper limit is more preferably 15.0 μm or less, and particularly preferably 10.0 μm or less. The pixel Young's modulus is preferably 0.5 GPa to 20 GPa, and more preferably 2.5 GPa to 15 GPa.

[0221] Each pixel included in the color filter according to the present disclosure 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 even more preferably 15 nm or less. Although the lower limit is not specified, it is preferably 0.1 nm or more, for example. The surface roughness of the pixel can be measured, for example, using an AFM (atomic force microscope) Dimension3100 manufactured by Veeco. In addition, the contact angle of water on the pixel can be set to an appropriate preferred value, but is 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 Interface Science Co., Ltd.). In addition, the volume resistance value of the pixel is preferably high. Specifically, the volume resistance value of the pixel is 10 9 It is preferable that the resistance is Ω·cm or more. 0 11 It is more preferable that the resistivity is Ω·cm or more. There is no upper limit, but for example, 10 14 The volume resistance of the pixel can be measured, for example, by using an ultra-high resistance meter 5410 (manufactured by Advantest Corporation).

[0222] Furthermore, the color filter according to the present disclosure may have a protective layer on the surface of the film according to the present disclosure. By providing a protective layer, various functions such as oxygen blocking, low reflectance, hydrophilicity / hydrophobicity, and blocking of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted. The thickness of the protective layer is preferably 0.01 μm to 10 μm, and more preferably 0.1 μm to 5 μm. Methods for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent, a method of forming the protective layer by chemical vapor deposition, and the like. Examples of the protective layer include a method of bonding a molded resin with an adhesive, and a method of pasting a molded resin with an adhesive. The components constituting the protective layer include (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, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine resin, polycarbonate resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al2O3, Mo, SiO2, and Si2N4, and two or more of these components may be contained. For example, in the case of a protective layer intended for blocking oxygen, the protective layer preferably contains a polyol resin, SiO2, and Si2N4. In the case of a protective layer intended to reduce reflection, the protective layer preferably contains a (meth)acrylic resin and a fluorine resin.

[0223] When the protective layer is formed by applying a resin composition, known methods such as spin coating, casting, screen printing, and inkjet can be used as the method for applying the resin composition. Known organic solvents (e.g., propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.) can be used as the organic solvent contained in the resin composition. When the protective layer is formed by chemical vapor deposition, known chemical vapor deposition methods (thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition) can be used as the chemical vapor deposition.

[0224] The protective layer may contain additives such as organic particles, inorganic particles, absorbents of light of a specific wavelength (e.g., ultraviolet rays, near infrared rays, etc.), refractive index adjusters, antioxidants, adhesives, and surfactants, as necessary. Examples of organic particles and inorganic particles include polymer particles (e.g., 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, silica, calcium carbonate, and barium sulfate. Known absorbents can be used as absorbents of light of a specific wavelength. The content of these additives can be appropriately adjusted, but is preferably 0.1% by mass to 70% by mass, and more preferably 1% by mass to 60% by mass, based on the total mass of the protective layer.

[0225] In addition, as the protective layer, the protective layers described in paragraphs 0073 to 0092 of JP2017-151176A can also be used.

[0226] The color filter may have a base layer. The base layer may be formed, for example, using a composition obtained by removing the colorant from the coloring composition according to the present disclosure. The surface contact angle of the base layer is preferably 20° to 70° when measured with diiodomethane. Also, it is preferably 30° to 80° when measured with water. If the surface contact angle of the base layer is within the above range, the resin composition has good wettability. The surface contact angle of the base layer can be adjusted, for example, by adding a surfactant.

[0227] <Manufacturing method for color filters> Next, a method for producing a color filter using the colored photosensitive composition according to the present disclosure will be described. The color filter can be produced through a step of forming a colored photosensitive composition layer on a support using the colored photosensitive composition according to the present disclosure described above, and a step of forming a pattern on the colored photosensitive composition layer by a photolithography method or a dry etching method. The colored photosensitive composition according to the present disclosure can also suppress the generation of development residues, so it is particularly effective in the case of producing a color filter by forming a pattern on the colored photosensitive composition layer by a photolithography method.

[0228] -Photolithography method- First, a case of manufacturing a color filter by forming a pattern by photolithography will be described. This manufacturing method preferably includes a step of forming a colored photosensitive composition layer on a support using the colored photosensitive composition according to the present disclosure, a step of exposing the colored photosensitive composition layer in a pattern, and a step of developing and removing the unexposed part of the colored photosensitive composition layer to form a pattern (pixel). If necessary, a step of baking the colored photosensitive composition layer (pre-baking step) and a step of baking the developed pattern (pixel) (post-baking step) may be provided.

[0229] In the step of forming a colored photosensitive composition layer, a colored photosensitive composition layer is formed on a support using the colored photosensitive composition according to the present disclosure. The support is not particularly limited and can be appropriately selected depending on the application. For example, a glass substrate, a silicon substrate, etc. can be mentioned, and a silicon substrate is preferable. In addition, a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate. In addition, a black matrix that isolates each pixel may be formed on the silicon substrate. In addition, a base layer may be provided on the silicon substrate to improve adhesion with the upper layer, prevent diffusion of substances, or flatten the substrate surface. The base layer may be formed using a composition obtained by removing the colorant from the colored photosensitive composition described herein, or a composition containing the resin, polymerizable compound, surfactant, etc. described herein.

[0230] The colored photosensitive composition can be applied by any known method, including, for example, a dropping method (drop casting), a slit coating method, a spray method, a roll coating method, a rotary coating method (spin coating), a casting coating method, a slit and spin method, a pre-wetting method (for example, a method described in JP-A-2009-145395), various printing methods such as ejection printing such as inkjet (for example, on-demand method, piezo method, thermal method) and nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, and metal mask printing, a transfer method using a mold, and a nanoimprint method. The application method in inkjet is not particularly limited, and examples thereof include the method shown in "Expanding and Usable Inkjet - Infinite Possibilities Seen in Patents -, published in February 2005, Sumibe Techno Research" (particularly pages 115 to 133), and the methods described in JP 2003-262716 A, JP 2003-185831 A, JP 2003-261827 A, JP 2012-126830 A, JP 2006-169325 A, etc. In addition, for the application method of the colored photosensitive composition, the descriptions in WO 2017 / 030174 A and WO 2017 / 018419 A can be referred to, and the contents of these are incorporated herein.

[0231] The colored photosensitive composition layer formed on the support may be dried (prebaked). When the film is produced by a low-temperature process, prebaking may not be performed. When prebaking is performed, the prebaking temperature is preferably 150° C. or lower, more preferably 120° C. or lower, and even more preferably 110° C. or lower. The lower limit can be, for example, 50° C. or higher, and can also be 80° C. or higher. The prebaking time is preferably 10 seconds to 300 seconds, more preferably 40 seconds to 250 seconds, and even more preferably 80 seconds to 220 seconds. Prebaking can be performed using a hot plate, an oven, or the like.

[0232] <<Exposure process>> Next, the colored photosensitive composition layer is exposed to light in a pattern (exposure step). For example, the colored photosensitive composition layer can be exposed to light in a pattern by using a stepper exposure machine or a scanner exposure machine through a mask having a predetermined mask pattern. This allows the exposed portion to be cured.

[0233] Examples of radiation (light) that can be used for exposure include g-line and i-line. 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 line (wavelength 248 nm) and ArF line (wavelength 193 nm), with KrF line (wavelength 248 nm) being preferred. Long-wave light sources with wavelengths of 300 nm or more can also be used.

[0234] In addition, the exposure may be performed by irradiating the light continuously or by irradiating the light in pulses (pulse exposure). Pulse exposure is an exposure method in which light irradiation and pauses are repeated in a short cycle (for example, on the order of milliseconds or less).

[0235] The irradiation amount (exposure amount) is, for example, 0.03 J / cm 2 ~2.5J / cm 2 is preferred, and 0.05 J / cm 2 ~1.0J / cm 2 is more preferable. The oxygen concentration during exposure can be appropriately selected. In addition to exposure in air, exposure may be performed in a low-oxygen atmosphere with an oxygen concentration of 19 volume% or less (e.g., 15 volume%, 5 volume%, or substantially oxygen-free), or in a high-oxygen atmosphere with an oxygen concentration of more than 21 volume% (e.g., 22 volume%, 30 volume%, or 50 volume%). The exposure illuminance can be appropriately set, and is preferably 1,000 W / m 2 ~100,000W / m 2 (For example, 5,000 W / m 2 , 15,000W / m 2 , or 35,000 W / m 2The oxygen concentration and exposure illuminance may be appropriately combined. For example, the oxygen concentration is 10% by volume and the illuminance is 10,000 W / m 2 , oxygen concentration 35% by volume, illuminance 20,000 W / m 2 etc.

[0236] Next, the unexposed parts of the colored photosensitive composition layer are developed and removed to form a pattern (pixels). The unexposed parts of the colored composition layer can be developed and removed using a developer. As a result, the colored photosensitive composition layer in the unexposed parts in the exposure step is dissolved into the developer, and only the photocured parts remain. The developer is preferably an organic alkaline developer that does not cause damage to the underlying elements or circuits. 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 order to improve the removability of residues, the process of shaking off the developer every 60 seconds and supplying new developer may be repeated several times.

[0237] Examples of the developer include organic solvents and alkaline developers, and alkaline developers are preferably used. As the alkaline developer, an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferred. Examples of the alkaline agent include organic alkaline compounds such as 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, and 1,8-diazabicyclo[5.4.0]-7-undecene, and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate, and sodium metasilicate. As the alkaline agent, compounds with a large molecular weight are preferred in terms of the environment and safety. 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. The developer may further contain a surfactant. Examples of the surfactant include the above-mentioned surfactants, and nonionic surfactants are preferred. From the viewpoint of convenience of transportation and storage, the developer may be once produced as a concentrated solution and diluted to a required concentration when used. The dilution ratio is not particularly limited, but can be set, for example, in the range of 1.5 to 100 times. It is also preferred to wash (rinse) with pure water after development. Rinsing is performed by supplying a rinse liquid to the developed colored photosensitive composition layer while rotating the support on which the developed colored photosensitive composition layer is formed. It is also preferable to move the nozzle for ejecting the rinse liquid from the center of the support to the peripheral portion of the support. In this case, the nozzle may be moved while gradually decreasing the moving speed when moving the nozzle from the center of the support to the peripheral portion. By performing rinsing in this manner, the in-plane variation of the rinse can be suppressed. The same effect can also be obtained by gradually decreasing the rotation speed of the support while moving the nozzle from the center of the support to the peripheral portion.

[0238] After development and drying, it is preferable to perform additional exposure treatment or heating treatment (post-baking). Additional exposure treatment and post-baking are curing treatments after development to complete curing. The heating temperature in post-baking is, for example, preferably 100°C to 240°C, more preferably 200°C to 240°C. Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to heat the developed film to the above conditions. When additional exposure treatment is performed, it is preferable that the light used for exposure has a wavelength of 400 nm or less. The additional exposure treatment may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.

[0239] -Dry etching method- Next, a case where a pattern is formed by a dry etching method to manufacture a color filter will be described. The pattern formation by the dry etching method preferably includes a step of forming a colored photosensitive composition layer on a support using the colored photosensitive composition according to the present disclosure, curing the entire colored photosensitive composition layer to form a cured layer, a step of forming a photoresist layer on the cured layer, a step of exposing the photoresist layer in a pattern shape and developing it to form a resist pattern, and a step of dry etching the cured layer using an etching gas with the resist pattern as a mask. In the formation of the photoresist layer, it is preferable to further perform a pre-bake treatment. In particular, as a process for forming the photoresist layer, a form in which a heat treatment after exposure and a heat treatment after development (post-bake treatment) are performed is desirable. For the pattern formation by the dry etching method, the description in paragraphs 0010 to 0067 of JP 2013-064993 A can be referred to, and the contents thereof are incorporated herein.

[0240] (Solid-state imaging element) The solid-state imaging device according to the present disclosure preferably has the cured product according to the present disclosure and the color filter according to the present disclosure described above. The configuration of the solid-state imaging device according to the present disclosure is not particularly limited as long as it has the film according to the present disclosure and functions as a solid-state imaging device, and examples thereof include the following configurations.

[0241] The substrate has a plurality of photodiodes constituting a light receiving area of ​​a solid-state imaging device (such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal oxide semiconductor) image sensor) and a transfer electrode made of polysilicon or the like, a light shielding film having an opening only for the light receiving portion of the photodiode on the photodiode and the transfer electrode, a device protection film made of silicon nitride or the like formed on the light shielding film so as to cover the entire light shielding film and the light receiving portion of the photodiode, and a color filter on the device protection film. Furthermore, the device protection film may have a light collecting means (e.g., a microlens, etc., the same applies below) on the device protection film and below the color filter (on the side closer to the substrate), or a light collecting means on the color filter. The color filter may have a structure in which each colored pixel is embedded in a space partitioned by partitions, for example, in a lattice shape. In this case, it is preferable that the partitions have 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. An imaging device including the solid-state imaging element according to the present invention can be used not only in digital cameras and electronic devices having an imaging function (such as mobile phones), but also in vehicle-mounted cameras and surveillance cameras. In addition, as described in JP 2019-211559 A, the solid-state imaging element according to the present disclosure may have an ultraviolet absorbing layer (UV cut filter) in the structure of the solid-state imaging element, thereby improving the light resistance of the color filter.

[0242] (Image display device) The image display device according to the present disclosure preferably has the cured product according to the present disclosure and the color filter according to the present disclosure. Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device. The definition of the image display device and details of each image display device are described in, for example, "Electronic Display Devices" (written by Akio Sasaki, published by Kogyo Chosakai Co., Ltd. in 1990) and "Display Devices" (written by Junsho Ibuki, published by Sangyo Tosho Co., Ltd. in 1989). In addition, the liquid crystal display device is described in, for example, "Next Generation Liquid Crystal Display Technology" (edited by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994). There is no particular limitation on the liquid crystal display device to which the present disclosure can be applied, and the present disclosure can be applied to various types of liquid crystal display devices described in the above "Next Generation Liquid Crystal Display Technology".

[0243] (Asymmetric diketopyrrolopyrrole compound) The asymmetric diketopyrrolopyrrole compound according to the present disclosure is an asymmetric diketopyrrolopyrrole compound represented by the following formula 2, and is preferably an asymmetric diketopyrrolopyrrole compound represented by the following formula 3.

[0244] [ka]

[0245] In formula 2, A 2 each independently represents a monovalent organic group having an acidic functional group or a basic functional group; B 2 each independently represents a monovalent organic group; C 2 each independently represents a monovalent organic group having no acidic 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; A 2 and C 2 and the phenyl group to which B is bonded 2 is a different group from the phenyl group to which it is bonded.

[0246] [ka]

[0247] 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 or no basic functional group, C 2 each independently represents a monovalent organic group having no acidic functional group or no basic functional group; 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; each independently represents 0 or 1; n5 represents an integer of 1 to 5; 3 and C 2 and the phenyl group to which B is bonded 2 is a different group from the phenyl group to which L is bonded. 1 is an ether bond, B 2 is an electron donating group having neither an acidic functional group nor a basic functional group, and n2 represents an integer of 1 to 5.

[0248] Preferred embodiments of the asymmetric diketopyrrolopyrrole compound of the present disclosure represented by formula 2 and formula 3 are the same as the preferred embodiments of the colored photosensitive composition of the present disclosure represented by formula 2 and formula 3 described above. EXAMPLES

[0249] The present disclosure will be described in detail below with reference to examples, but the present disclosure is not limited to these examples. In the present examples, "%" and "parts" mean "% by mass" and "parts by mass", respectively, unless otherwise specified. In addition, in polymer compounds, unless otherwise specified, the molecular weight is the weight average molecular weight (Mw), and the ratio of the constitutional units is the mole percentage. The weight average molecular weight (Mw) is a value measured in terms of polystyrene by gel permeation chromatography (GPC). It should be noted that DPP-1 to 26 used in the examples are the same compounds as the above-mentioned DPP-1 to 26, respectively.

[0250] <Synthesis Example 1: DPP-1 synthesis> In a nitrogen-substituted three-neck flask, 160 parts of tert-amyl alcohol, 34 parts of compound A-1, and 54 parts of sodium tert-pentoxide were added, and the mixture was heated to 110°C and stirred. Then, 40 parts of the compound B-1 described below, which was synthesized by the method described in Tetrahedron, 58 (2002) 5547-5565, was added. After reacting at 120°C for 4 hours, the mixture was cooled to 70°C, and 320 parts of methanol and 400 parts of water were added, followed by filtration and washing with methanol to obtain 39 parts of asymmetric diketopyrrolopyrrole compound DPP-1.

[0251] <Synthesis Examples 2 to 20, 22, 23, 25 and 26: Synthesis of DPP-2 to 20, 22, 23, 25 and 26> As shown in Table 1, DPP-2 to 20, 22 and 23 were each prepared in the same manner as in Synthesis Example 1 above, except that the raw materials Compound A-1 and Compound B-1 were changed.

[0252] <Synthesis Example 21: Synthesis of DPP-21> After synthesis in the same manner as in Synthesis Example 1, 10 parts of DPP precursor was added to 100 parts of acetic acid. After adding 15 parts of 25% by mass hydrogen bromide-acetic acid solution, the mixture was heated to 50°C and stirred for 3 hours. The mixture was cooled to 25°C, filtered and washed with acetonitrile to obtain 6 parts of asymmetric diketopyrrolopyrrole compound DPP-21.

[0253] <Synthesis Example 24: Synthesis of DPP-24> After synthesis in the same manner as in Synthesis Example 1, 10 parts of 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 reacting at 120°C for 12 hours, the mixture was cooled to 50°C, and 100 parts of methanol and 300 parts of water were added and filtered. The obtained filtrate was added to 100 parts of acetic acid, and 15 parts of 25% by mass hydrogen bromide-acetic acid solution were added, and the mixture was 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 asymmetric diketopyrrolopyrrole compound DPP-24.

[0254] In addition, some of the obtained diketopyrrolopyrrole compounds were 1 The H-NMR measurement data is shown below. DPP-1: 1 H-NMR(DMSO-d6)δ(ppm)=0.99,2.40,2.48,3.60,7.39,7.50,11.24. 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 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 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 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 DPP-10: 1 H-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 DPP-11: 1H-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 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

[0255] [Table 1]

[0256] Compounds A-1 to A-18 and compounds B-1 to B-5 listed in Table 1 are shown below.

[0257] [ka]

[0258] [ka]

[0259] [ka]

[0260] [ka]

[0261] <Preparation of Pigment Composition> A mixture of the resin, pigment, DPP (diketopyrrolopyrrole compound), solvent and other components shown in Table 2 or Table 3 in the ratios shown in Table 2 or Table 3 was mixed and dispersed for 3 hours using a bead mill (zirconia beads 0.3 mm in diameter). After that, the mixture was mixed at 2,000 kg / cm using a high-pressure disperser NANO-3000-10 with a pressure reduction mechanism (manufactured by Nippon BEE Co., Ltd.). 3The dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of 1000 g / min. This dispersion treatment was repeated 10 times to obtain each pigment composition.

[0262] [Table 2]

[0263] [Table 3]

[0264] In Tables 2 and 3, the "ratio of red pigment to derivative" represents the value (mass ratio) of the content of 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. Details of the compounds listed in Tables 2 and 3 are shown below.

[0265] PR272: CI Pigment Red272 PR254: CI Pigment Red254 PY139: CI Pigment Yellow 139 PY185: CI Pigment Yellow 185 PY150: CI Pigment Yellow 150 PY138: CI Pigment Yellow 138 PO71: CI Pigment Orange 71 PGMEA: Propylene glycol monomethyl ether acetate SY-1: The following compound

[0266] [ka]

[0267] PB-1: The following compound, solid content 30 mass%, PGMEA solution, Mw 16,000, solid acid value 55 mgKOH / g PB-2: The following compound, solid content 30 mass%, PGMEA solution, Mw 8,000, solid acid value 53 mgKOH / g PB-3: The following compound, solid content 30 mass%, PGMEA solution, Mw 15,000, solid acid value 70 mg KOH / g PB-4: PB-1 with a different acid value, solid content acid value 40mgKOH / g PB-5: PB-1 with a different acid value, solid content acid value 70mgKOH / g PA-1: The following compound, solid content 30% by mass, PGMEA solution, Mw: 23,000, solid content acid value 30 mgKOH / g

[0268] [ka]

[0269] DPP-C1: the following diketopyrrolopyrrole compound (note that the above diketopyrrolopyrrole compound A is not included): DPP-C2: the following diketopyrrolopyrrole compound

[0270] [ka]

[0271] (Examples 1 to 82 and Comparative Examples 1 and 2) <Preparation of Colored Photosensitive Composition> The following components were mixed to prepare a colored photosensitive composition. Note that the pigment dispersion, resin, polymerizable compound, photopolymerization initiator, and solvent used were those shown in Table 4 or Table 5. Pigment composition described in Table 4 or Table 5: the amount described in Table 4 or Table 5 Resin listed in Table 4 or Table 5: Amount listed in Table 4 or Table 5 Polymerizable compound shown in Table 4 or Table 5: Amount shown in Table 4 or Table 5 Photopolymerization initiator described in Table 4 or Table 5: the amount described in Table 4 or Table 5 Surfactant (a 1 mass% solution of the following compound (the proportion of repeating units means mol %. Mw: 14,000) in PGMEA (propylene glycol monomethyl ether acetate): 1 mass part p-Methoxyphenol: 0.01 parts by weight Solvent listed in Table 4 or Table 5: Amount listed in Table 4 or Table 5

[0272] [ka]

[0273] [Table 4]

[0274] [Table 5]

[0275] 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. RP-34 can be used not only for red pixels but also for orange pixels. Compounds listed in Tables 4 and 5 other than those mentioned above are shown below. -resin- PB-6: Solid content 30% by mass, PGMEA solution, Mw: 30,000, solid acid value 30 mg KOH / g PB-7: Solid content 30% by mass, PGMEA solution, Mw: 11,000, solid content acid value 70mgKOH / g

[0276] [ka]

[0277] -Polymerizable compound- M-1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.) M-2: NK Ester A-TMMT (Shin-Nakamura Chemical Co., Ltd.) M-3: Dipentaerythritol hexaacrylate

[0278] -Photopolymerization initiator- I-1 to I-10: The following compounds

[0279] [ka]

[0280] -solvent- S-1: Propylene glycol monomethyl ether acetate (PGMEA) S-2: Cyclohexanone

[0281] <Evaluation method> -Adhesion evaluation- Each colored photosensitive composition was applied by spin coating onto an 8-inch (20.32 cm) silicon wafer so that the film thickness after post-baking would be 0.5 μm. Then, the wafer was pre-baked at 100° C. for 2 minutes using a hot plate. Next, the wafer was exposed to 200 mJ / cm 2 of light using an i-line stepper exposure system FPA-3000i5+ (Canon Inc.) through a mask having a Bayer pattern that forms a predetermined pixel (pattern) size. 2 The mask used had a Bayer pattern with pixel 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. Next, paddle development was performed at 23° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). After that, rinsing was performed by a spin shower using pure water. Next, a pattern (pixel) was formed by heating (post-baking) at 200° C. for 5 minutes using a hot plate. Using a high-resolution FEB length measuring 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, and the smallest pattern size at which a pattern was formed without peeling was taken as the minimum contact line width. The smaller the minimum contact line width, the better the adhesion. [Evaluation Criteria] A: The minimum contact line width is 1.2 μm square or less. B: The minimum contact line width is greater than 1.2 μm square and less than or equal to 1.3 μm square. C: The minimum contact line width is greater than 1.3 μm square and less than or equal to 1.4 μm square. D: The minimum contact line width is greater than 1.4 μm square and less than or equal to 1.6 μm square. E: The minimum contact line width is greater than 1.6 μm square.

[0282] -Storage stability evaluation- The viscosity of the colored photosensitive composition obtained above was measured using "RE-85L" manufactured by Toki Sangyo Co., Ltd., and the colored photosensitive composition was left to stand at 45°C for 3 days, and the viscosity was measured again. The storage stability was evaluated based on the viscosity difference (ΔVis) before and after standing according to the following evaluation criteria. The smaller the viscosity difference (ΔVis) value, the better the storage stability. The viscosity of the colored photosensitive composition was measured at a temperature adjusted to 25°C. The evaluation criteria were as follows. did. [Evaluation Criteria] A: ΔVis is 0.5 mPa s or less. B: ΔVis is greater than 0.5 mPa·s and less than 2.0 mPa·s. C: ΔVis is greater than 2.0 mPa·s.

[0283] -Developability evaluation- CT-4000 (manufactured by Fujifilm Electronic Materials Co., Ltd.) was applied to a silicon wafer by spin coating to a film thickness of 0.1 μm, and heated at 220° C. for 1 hour using a hot plate to form an undercoat layer. Each curable composition was applied to the silicon wafer with the undercoat 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. An i-line stepper FPA-3000i5+ (manufactured by Canon Inc.) was used to apply a 365 nm sieve to this composition layer through a mask pattern in which square pixels with sides of 1.1 μm were arranged in an area of ​​4 mm×3 mm on the substrate. The exposure was 200 mJ / cm 2 The composition layer after exposure was paddle-developed at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. Thereafter, the composition layer was rinsed with water using a spin shower, and then washed with pure water. Thereafter, the water droplets were blown off with high-pressure air, and the silicon wafer was naturally dried, and then post-baked at 200°C for 300 seconds using a hot plate to form a pattern. The developability was evaluated by observing the presence or absence of residuals between the patterns. The area outside the pattern formation area (unexposed area) was observed with a scanning electron microscope (SEM) (magnification 10,000 times), and residues with a diameter of 0.1 μm or more per 5 μm × 5 μm area (1 area) of the unexposed area were counted and evaluated according to the following evaluation criteria. A: Absolutely no residue per area. B: The number of residues per area is less than 10. C: The number of residues per area is 10 or more and less than 20. D: The number of residues per area is greater than or equal to 20 and less than 30.

[0284] [Table 6]

[0285] As shown in Table 6 above, the colored photosensitive compositions of Examples 1 to 82 were superior in adhesion to the resulting cured products as compared with the colored photosensitive compositions of Comparative Examples 1 and 2. Furthermore, as shown in Table 6 above, the colored photosensitive compositions in Examples 1 to 82 were also excellent in storage stability and developability.

[0286] (Examples 101 to 154, and Examples 156 to 182) The Green composition was applied onto a silicon wafer by spin coating so that the film thickness after formation would be 1.0 μm. Then, the wafer was heated at 100° C. for 2 minutes using a hot plate. Then, an i-line stepper exposure system FPA-3000i5+ (Canon Inc.) was used to expose the wafer at 1,000 mJ / cm 2 The film was exposed to light through a mask with a 2 μm square dot pattern. Then, paddle development was performed at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). After that, rinsing was performed with a spin shower and further washed 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 colored patterns (Bayer patterns). In Examples 101 to 154 and Examples 156 to 182, the colored photosensitive compositions prepared in Examples 1 to 54 and Examples 56 to 82 were used as the Red compositions. Other than the above colored photosensitive composition, the Green composition and the Blue composition will be described later. The Bayer pattern is a repeated 2 x 2 array of color filter elements, each having one red element, two green elements, and one blue element, as disclosed in U.S. Pat. No. 3,971,065. The obtained color filter was incorporated into a solid-state imaging device according to a known method. It was confirmed that the solid-state imaging device had excellent adhesion in the cured film and favorable image recognition ability, regardless of whether any of the colored photosensitive compositions obtained in Examples 1 to 76 was used.

[0287] The green compositions and blue compositions other than the above colored photosensitive compositions used in Examples 101 to 154 and Examples 156 to 182 are as follows.

[0288] -Green composition- The following components were mixed and stirred, and then filtered through a nylon filter having a pore size of 0.45 μm (manufactured by Nippon Pall Co., Ltd.) to prepare a Green composition. Green pigment dispersion: 73.7 parts by mass Resin 4 (40% by mass PGMEA solution): 0.3 parts by mass Polymerizable compound 1: 1.2 parts by mass Photopolymerization initiator 1: 0.6 parts by weight Surfactant 1: 4.2 parts by weight Ultraviolet absorber (UV-503, manufactured by Daito Chemical Co., Ltd.): 0.5 parts by mass PGMEA: 19.5 parts by mass

[0289] -Blue composition- The following components were mixed and stirred, and then filtered through a nylon filter having a pore size of 0.45 μm (manufactured by Nippon Pall Co., Ltd.) to prepare a Blue composition. Blue pigment dispersion: 44.9 parts by mass Resin 4 (40% by mass PGMEA solution): 2.1 parts by mass Polymerizable compound 1: 1.5 parts by mass Polymerizable compound 4: 0.7 parts by mass Photopolymerization initiator 1: 0.8 parts by weight Surfactant 1: 4.2 parts by weight PGMEA: 45.8 parts by mass

[0290] The raw materials used in the Green, Red, and Blue compositions are as follows:

[0291] ·Green pigment dispersion 6.4 parts by weight of CI Pigment Green 36, CI Pigment A mixture of 5.3 parts by mass of Yellow 150, 5.2 parts by mass of a dispersant (DISPERBYK-161, manufactured by BYK Chemie), and 83.1 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. Thereafter, the mixture was mixed and dispersed at 2,000 kg / cm using a high-pressure disperser NANO-3000-10 equipped with a pressure reducing mechanism (manufactured by Japan BEE Co., Ltd.). 3 The dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of 1000 g / min. This dispersion treatment was repeated 10 times to obtain a green pigment dispersion.

[0292] ·Blue pigment dispersion 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 of a dispersant (DISPERBYK-161, manufactured by BYK Chemie), and 82.4 parts of PGMEA was mixed and dispersed for 3 hours using a bead mill (zirconia beads, 0.3 mm diameter) to prepare a pigment dispersion. Then, the mixture was mixed at 2,000 kg / cm using a high-pressure disperser NANO-3000-10 equipped with a pressure reducing mechanism (manufactured by Nippon BEE Co., Ltd.). 3 The dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of 1000 g / min. This dispersion treatment was repeated 10 times to obtain a blue pigment dispersion.

[0293] Polymerizable compound 1: KAYARAD DPHA (a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate, manufactured by Nippon Kayaku Co., Ltd.) Polymerizable compound 4: a compound having the following structure

[0294] [ka]

[0295] Resin 4: Resin having the following structure (acid value: 70 mg KOH / g, Mw=11,000, the ratio of each structural unit is a molar ratio.)

[0296] [ka]

[0297] Photopolymerization initiator 1: IRGACUREOXE01 (1-[4-(phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyloxime), manufactured by BASF)

[0298] Surfactant 1: 1 mass % PGMEA solution of the following mixture (Mw = 14,000). In the following formula, the units of % (62% and 38%) indicating the proportion of the constituent units are % by mass.

[0299] [ka]

[0300] The disclosure of Japanese Patent Application No. 2020-030706, filed on February 26, 2020, is incorporated herein by reference in its entirety. All publications, patent applications, and technical standards mentioned in this specification are herein incorporated by reference to the same extent as if each individual publication, patent application, or technical standard was specifically and individually indicated to be incorporated by reference.

Claims

[Claim 1] An asymmetric diketopyrrolopyrrole compound represented by the following formula 2: 【Chemistry 1】 In the formula 2, the A ２ are each independently -X-Y-Z, where X represents -O- or -S-; 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, and these groups are each independently selected from the group represented by -NR １０１ -, -O-, -SO ２ - or CO-, 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, Z is a group represented by the following formula (Z1), ２ each independently represents a monovalent organic group having no acidic functional group or no basic functional group, 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 1 to 5; n3 represents an integer of 0 to 4; A ２ and C ２ The phenyl group to which B is bonded ２ is a different group from the phenyl group to which it is bonded. 【Chemistry 2】 In formula (Z1), R ３０１ and R ３０２ each independently represents an optionally substituted saturated or unsaturated alkyl group, or an optionally substituted heterocycle containing a nitrogen, oxygen or sulfur atom.

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