WO2020189461A1

WO2020189461A1 - Photosensitive coloring composition, cured product, color filter, solid-state imaging element and image display device

Info

Publication number: WO2020189461A1
Application number: PCT/JP2020/010668
Authority: WO
Inventors: 雅臣牧野; 泰弘澤村; 宏明出井
Original assignee: 富士フイルム株式会社
Priority date: 2019-03-18
Filing date: 2020-03-11
Publication date: 2020-09-24
Also published as: JPWO2020189461A1; TW202104279A; JP7163481B2

Abstract

A photosensitive coloring composition which contains a compound A that has a polymerizable group and a lowest unoccupied molecular orbital energy level LUMO of less than -3.5 eV, a coloring agent, a polymerizable compound and a photopolymerization initiator; a photosensitive coloring composition which contains a compound A that has a polymerizable group and at least one structure that is selected from the group consisting of a quinone structure, a dithiolene structure, a naphthalene diimide structure, a perylene diimide structure, a pyrazinoquinoxaline structure and a fullerene structure, a coloring agent, a polymerizable compound and a photopolymerization initiator; a cured product of either of the above-described photosensitive coloring compositions; a color filter which comprises the above-described cured product; and a solid-state imaging element and an image display device, each of which is provided with the above-described color filter.

Description

Colored photosensitive composition, cured product, color filter, solid-state image sensor and image display device

The present disclosure relates to a colored photosensitive composition, a cured product, a color filter, a solid-state image sensor, and an image display device.

Color filters are indispensable components for solid-state image sensors and image display devices. The solid-state image sensor and the image display device may generate noise due to the reflection of visible light. Therefore, it is also practiced to provide a light-shielding film on the solid-state image sensor or the image display device to suppress the generation of noise.
As a method for producing such a color filter or a light-shielding film, a colored composition layer is formed by using a colored photosensitive composition containing a colorant, a polymerizable compound, a photopolymerization initiator, and an alkali-soluble resin. A method of exposing and developing this coloring composition layer to form a pattern is known.
As the conventional photosensitive composition or coloring composition, those described in Patent Documents 1 to 3 are known.

Patent Document 1: Japanese Patent Application Laid-Open No. 2017-129774 Patent Document 2: Japanese Patent Application Laid-Open No. 2016-775739 Patent Document 3: International Publication No. 2013/018705

An object to be solved by the embodiment according to the present disclosure is to provide a colored photosensitive composition having excellent weight loss inhibitory property of the obtained cured product.
Further, another problem to be solved by the embodiment according to the present disclosure is a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state image sensor or an image display device including the color filter. Is to provide.

Means for solving the above problems include the following aspects.
<1> A colored photosensitive composition containing a compound A having a polymerizable group and an energy level LUMO of the lowest empty orbit of less than −3.5 eV, a colorant, a polymerizable compound, and a photopolymerization initiator. ..
<2> At least one structure having a polymerizable group and selected from the group consisting of a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene diimide structure, a perylene imide structure, a pyrazinoquinoxaline structure, and a fullerene structure. A colored photosensitive composition containing compound A, a colorant, a polymerizable compound, and a photopolymerization initiator.
<3> The compound A is a compound having at least one structure selected from the group consisting of a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene diimide structure, a perylene diimide structure, a pyrazinenoquinoxaline structure, and a fullerene structure. The colored photosensitive composition according to <1>.
<4> The colored photosensitive composition according to <1> or <2>, wherein the polymerizable group contained in the compound A is a radically polymerizable group or a cationically polymerizable group.
<5> The colored photosensitive composition according to <4>, wherein the radically polymerizable group is an acrylic group, a methacryl group, a vinyl group, or an allyl group.
<6> The colored photosensitive composition according to <4>, wherein the cationically polymerizable group is an epoxy group, an oxetanyl group, or an allyl group.
<7> The colored photosensitive composition according to any one of <1> to <6>, wherein the compound A has two or more polymerizable groups in one molecule.
<8> The colored photosensitive composition according to any one of the above <1> to <7>, wherein the compound A is a compound represented by any of the following formulas (1A) to (1C).

In formulas (1A) to (1C), R ¹ is independently a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a hydroxy group, an acyl group, an acyloxy group, a nitro group, or a cyano group. the ^expressed, the C a ~ ^{C C} each independently represent a ring structure, ^{Y 1} is independently a single bond, an oxygen atom, a sulfur atom, NR ^N, carbonyl group, -OC (= O) -, - C (= O) O -, - C (= O) NH -, - OC (= O) -NH -, - Ani - Cat + -, or, -Cat ⁺ Ani ^{- -} represents, ^{R N} are each independently , Hydrogen atom, alkyl group, or aryl group, Ani ⁻ represents an anionic structure, Cat ⁺ represents a cation structure, L ¹ represents a single bond or a divalent linking group, respectively, and A ¹ Represents the above-mentioned polymerizable group, X ¹ and X ² independently represent an oxygen atom, a sulfur atom, or a group represented by the following formula (1X), n represents an integer of 1 or more, and m. each independently, 0 or more and represents the maximum number of substitution positions on R ¹ can bind ring, p is 0 or 1.

In the formula (1X), R ² and R ³ independently represent an electron-attracting group, and the wavy line portion represents a bonding position with the ring structure.

<9> The colored photosensitive composition according to any one of <1> to <8>, wherein the compound A is a compound represented by the following formula (2) or formula (3).

In the formula (2), R ²¹ to R ²⁴ are independently halogen atoms, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, acyl groups, acyloxy groups, hydroxy groups, amino groups, nitro groups and amide groups. , Or, representing a group having the above-mentioned polymerizable group, R ²¹ and R ²² , or R ²³ and R ²⁴ may be linked to each other to form a ring, and at least one of R ²¹ to R ²⁴ may be formed. , A group having a polymerizable group.
In the formula (3), R ³¹ to R ³⁴ independently represent a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, an acyloxy group, a hydroxy group, an amino group, a nitro group and an amide group. , Or a group having a polymerizable group, and R ³¹ and R ³² , or R ³³ and R ³⁴ may be linked to each other to form a ring, and at least one of R ³¹ to R ³⁴ is It is a group having a polymerizable group.

<10> The colored photosensitivity according to any one of <1> to <9>, wherein the energy level HOMO of the highest occupied orbital of the compound A is more than -7.0 eV and less than -5.5 eV. Composition.
<11> The colored photosensitive composition according to any one of <1> to <10>, wherein the energy level LUMO of the lowest empty orbit of the compound A is more than -5.0 eV and less than -3.5 eV. object.
<12> The colored photosensitive composition according to any one of <1> to <11>, wherein the colorant contains a phthalocyanine pigment.
<13> The colored photosensitive composition according to any one of <1> to <12>, wherein the photopolymerization initiator contains an oxime compound.
<14> The colored photosensitive composition according to any one of <1> to <13>, which further contains a polymer dispersant.
<15> The colored photosensitive composition according to any one of <1> to <14>, which further contains an alkali-soluble resin.
<16> A cured product obtained by curing the colored photosensitive composition according to any one of <1> to <15> above.
<17> A color filter comprising the cured product according to <16> above.
<18> A solid-state image sensor having the color filter according to <17> above.
<19> An image display device having the color filter according to <17> above.

According to the embodiment according to the present disclosure, there is provided a colored photosensitive composition having excellent weight loss inhibitory property of the obtained cured product.
Further, according to another embodiment according to the present disclosure, a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state image sensor or an image display device including the color filter is provided.

The contents of the present disclosure will be described in detail below. The description of the constituents described below may be based on the representative embodiments of the present disclosure, but the present disclosure is not limited to such embodiments.
In the present disclosure, "-" indicating a numerical range is used to mean that the numerical values described before and after the numerical range are included as the lower limit value and the upper limit value.
In the numerical range described stepwise in the present disclosure, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of another numerical range described stepwise. .. Further, in the numerical range described in the present disclosure, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
Further, in the present disclosure, the amount of each component in the composition is the total amount of the plurality of applicable substances present in the composition unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition. Means.
Further, in the notation of a group (atomic group) in the present disclosure, the notation that does not describe substitution or non-substitution includes those having no substituent as well as those having a substituent. For example, the "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
In the present disclosure, unless otherwise specified, "Me" is a methyl group, "Et" is an ethyl group, "Pr" is a propyl group, "Bu" is a butyl group, and "Ph" is a phenyl group. , Represent each.
In the present disclosure, "(meth) acrylic" is a term used in a concept that includes both acrylic and methacrylic, and "(meth) acryloyl" is a term that is used as a concept that includes both acryloyl and methacryloyl. is there.
Further, in the present disclosure, the term "process" is included in this term as long as the intended purpose of the process is achieved, not only in an independent process but also in the case where it cannot be clearly distinguished from other processes. Is done.
In the present disclosure, the "total solid content" refers to the total mass of the components excluding the solvent from the total composition of the composition. Further, the "solid content" is a component excluding the solvent as described above, and may be, for example, a solid or a liquid at 25 ° C.

Further, in the present disclosure, "% by mass" and "% by weight" are synonymous, and "parts by mass" and "parts by weight" are synonymous.
Further, in the present disclosure, a combination of two or more preferred embodiments is a more preferred embodiment.
Further, unless otherwise specified, the weight average molecular weight (Mw) and the number average molecular weight (Mn) in the present disclosure use columns of TSKgel GMHxL, TSKgel G4000HxL, and TSKgel G2000HxL (all are trade names manufactured by THF Co., Ltd.). The molecular weight is detected by the solvent THF (tetrahydrofuran) and the differential refraction meter by the gel permeation chromatography (GPC) analyzer, and is converted by using polystyrene as a standard substance.
Hereinafter, the present disclosure will be described in detail.

(Colored photosensitive composition)
A first aspect of the colored photosensitive composition according to the present disclosure is compound A, a colorant, a polymerizable compound, which has a polymerizable group and has an energy level LUMO of the lowest empty orbit of less than −3.5 eV. A colored photosensitive composition containing a photopolymerization initiator.
The second aspect of the colored photosensitive composition according to the present disclosure is that it has a polymerizable group and has a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene diimide structure, a perylene imide structure, a pyrazinenoquinoxaline structure, and a structure. , A colored photosensitive composition containing compound A having at least one structure selected from the group consisting of a fullerene structure, a colorant, a polymerizable compound, and a photopolymerization initiator.
In the present specification, unless otherwise specified, the term "colored photosensitive composition according to the present disclosure" refers to both the first aspect and the second aspect.

In recent years, as the number of pixels of an image sensor has increased, the pattern has become finer and thinner. Along with this, while the pigment concentration in the color filter is relatively increased and the curable component is reduced, film reduction suppression, that is, weight reduction suppression in the obtained cured product is required.
By using the colored photosensitive composition according to the present disclosure, a cured product having excellent weight loss inhibitory properties can be obtained.
By containing the above-mentioned compound A, the balance between the polymerization rate and the polymerization terminating ability is excellent, the residual amount of the low molecular weight component is reduced, and the volatility of the above-mentioned compound A itself is small, so that the weight reduction of the obtained cured product is suppressed. It is presumed to have excellent properties (inhibitory of film loss).

Further, it is considered that the colored photosensitive composition according to the present disclosure tends to be excellent in sensitivity by containing the above-mentioned compound A.
Further, the colored photosensitive composition according to the present disclosure has an excellent balance between the polymerization rate and the polymerization terminating ability by containing the above compound A, the residual amount of low molecular weight components is reduced, and at the time of curing It is presumed that the compound A itself can be immobilized in the film, the exposed shape is easily maintained, and the linearity of the obtained pattern is also excellent.

The details of each component contained in the colored photosensitive composition according to the present disclosure will be described below. In the first and second aspects described above, the overlapping components are the same, and so are the preferred embodiments.

<Compound A>
Compound A in the first aspect of the colored photosensitive composition according to the present disclosure has a polymerizable group and has an energy level LUMO of the lowest empty orbit of less than −3.5 eV.
Further, the compound A in the second aspect of the colored photosensitive composition according to the present disclosure has a polymerizable group and has a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene diimide structure, a perylene imide structure, and a pyrazinoquinoxaline. It has a structure and at least one structure selected from the group consisting of fullerene structures.
In the present specification, unless otherwise specified, the term "Compound A" refers to both Compound A in the first aspect and Compound A in the second aspect.

-Energy level LUMO of the lowest empty orbit of compound A-
The energy level LUMO (simply referred to as “LUMO”) of the lowest empty orbit of Compound A in the first aspect of the colored photosensitive composition according to the present disclosure is less than −3.5 eV, and the weight loss inhibitory property. From the viewpoint of pattern linearity and sensitivity, it is preferably less than -3.7 eV, and particularly preferably less than -3.9 eV.
The LUMO of Compound A in the second aspect of the colored photosensitive composition according to the present disclosure is preferably less than −3.5 eV from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity, preferably -3. It is more preferably less than .7 eV, and particularly preferably less than -3.9 eV.
Further, the lower limit of LUMO in Compound A is preferably more than −5.0 eV, more preferably -4.8 eV or more, and more preferably −4.8 eV or more, from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. It is particularly preferably 4.5 eV or more.

The LUMO of Compound A and the energy level HOMO of the highest occupied orbit (also simply referred to as "HOMO") in the present disclosure shall be measured according to the following method.
The HOMO of each compound is measured as follows.
The ionization potential of each 5 mg of each compound is measured by an atmospheric photoelectron spectrometer (AC-3, manufactured by RIKEN Keiki Co., Ltd.), and the value is defined as HOMO.
20 mg of each compound was dissolved in 200 mL of toluene, and toluene was added to 2 mL of this solution to make 50 mL. Regarding the absorbance of the prepared solution, an ultraviolet-visible near-infrared (UV-Vis-NIR) spectrophotometer (model number: Cary5000, Agilent Measurement is performed in the wavelength range of 200 nm to 800 nm using (manufactured by Technology), the absorption edge at the wavelength of 400 nm to 700 nm is calculated, and the value is defined as the S0-S1 transition energy gap (HOMO-LUMO energy difference ΔE). LUMO is calculated by the following formula.
LUMO = HOMO + ΔE

-Energy level HOMO of the highest occupied orbit of compound A-
The energy level HOMO of the highest occupied orbital of Compound A is preferably -7.5 eV or more and -5.0 eV or less, preferably -7.0 eV, from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. It is more preferably more than -5.5 eV, and particularly preferably -6.8 eV or more and -6.0 eV or less.

-HOMO-LUMO energy difference ΔE- of compound A
The HOMO-LUMO energy difference ΔE (LUMO value-HOMO value) of Compound A is preferably 1.0 eV or more and 4.0 eV or less from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. It is more preferably 1.0 eV or more and 3.0 eV or less, further preferably 1.2 eV or more and 2.8 eV or less, and particularly preferably 1.5 eV or more and 2.6 eV or less.

-Polymerizable group of compound A-
The polymerizable group of Compound A is not particularly limited and may be a known polymerizable group, but from the viewpoint of weight loss inhibitory property, pattern linearity and sensitivity, a radical polymerizable group or a cationically polymerizable group can be used. It is preferably a group, more preferably a radically polymerizable group.

As the radically polymerizable group, an ethylenically unsaturated group is preferable. Preferable examples of the ethylenically unsaturated group include an acrylic group, a methacryl group, a vinyl group, a maleimide group, and an allyl group.
Among these, the radically polymerizable groups include (meth) acryloxy group, (meth) acrylamide group, vinyl ester group, vinyl ether group, and styryl group (vinylphenyl) from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. Group), maleimide group, or (meth) allyl group is preferable.
It is more preferably a (meth) acryloxy group, a vinyl ester group, a vinyl ether group, or a styryl group (vinylphenyl group), and even more preferably a (meth) acryloxy group or a styryl group (vinylphenyl group). , (Meta) acryloxy group is particularly preferable, and acryloxy group is most preferable.

The cationically polymerizable group is preferably a cyclic ether group, a cyclic imino ether group, or an ethylenically unsaturated group, and is an epoxy group or an oxetanyl group from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. , Or a (meth) allyl group, more preferably an epoxy group.

Compound A preferably has two or more polymerizable groups in one molecule from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. The upper limit of the number of polymerizable groups in the compound A1 molecule is not particularly limited, but is preferably 6 or less, and more preferably 4 or less.

-Weight average molecular weight of Compound A Mw-
The weight average molecular weight Mw of Compound A is preferably 50 or more, more preferably 150 or more, still more preferably 200 or more, from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. , 300 or more is particularly preferable, and 400 or more is most preferable. The lower limit of Mw of compound A is not particularly limited, but is preferably less than 1,500, and more preferably 1,000 or less.
The molecular weight of compound A preferably has a distribution. Mw / Mn is preferably 1.01 or more, more preferably 1.05 or more, further preferably 1.1 or more, and particularly preferably 1.1 or more and 2.0 or less.

-Chemical structure of compound A-
Compound A in the second aspect of the colored photosensitive composition according to the present disclosure is selected from the group consisting of a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene diimide structure, a perylene imide structure, a pyrazinoquinoxaline structure, and a fullerene structure. From the viewpoint of weight loss inhibitory property, pattern linearity, sensitivity, and availability, it is preferable to have a quinone structure or a quinodimethane structure, and a quinone structure or a tetracyanoquinodimethane. It is more preferable to have a structure, and it is particularly preferable to have a tetracyanoquinodimethane structure.
The compound A in the first aspect of the colored photosensitive composition according to the present disclosure has a quinone structure, a quinodimethane structure, a dithiorene structure, and a naphthalene diimide from the viewpoints of weight loss inhibitory property, pattern linearity, sensitivity, and availability. It preferably has at least one structure selected from the group consisting of a structure, a perylene imide structure, a pyrazinoquinoxaline structure, and a fullerene structure, more preferably a quinone structure or a quinodimethane structure, and a quinone structure or a tetracyanoquinodimethane. It is more preferable to have a quinodimethane structure, and particularly preferably to have a tetracyanoquinodimethane structure.

From the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity, the compound A is preferably a compound represented by any of the following formulas (1A) to (1C), and the following formula (1A) or The compound represented by the formula (1B) is more preferable, and the compound represented by the following formula (1A) is particularly preferable.

In formulas (1A) to (1C), R ¹ is independently a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a hydroxy group, an acyl group, an acyloxy group, a nitro group, or a cyano group. the ^expressed, the C a ~ ^{C C} each independently represent a ring structure, ^{Y 1} is independently a single bond, an oxygen atom, a sulfur atom, NR ^N, carbonyl group, -OC (= O) -, - C (= O) O -, - C (= O) NH -, - OC (= O) -NH -, - Ani - Cat + -, or, -Cat ⁺ Ani ^{- -} represents, ^{R N} are each independently , Hydrogen atom, alkyl group, or aryl group, Ani ⁻ represents an anionic structure, Cat ⁺ represents a cation structure, L ¹ represents a single bond or a divalent linking group, respectively, and A ¹ Represents the group having the above polymerizable group, X ¹ and X ² each independently represent an oxygen atom, a sulfur atom, or a group represented by the following formula (1X), and n represents an integer of 1 or more. , m is independently 0 or more and represents the maximum number of substitution positions on R ¹ can bind ring, p is 0 or 1.

R ¹ in the formulas (1A) to (1C) is preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an acyloxy group, a nitro group, or a cyano group, and is preferably a fluorine atom or a chlorine atom. , Alkoxy group or cyano group is more preferable, and fluorine atom, nitro group, methoxy group or cyano group is particularly preferable.
It is preferable that m in the formulas (1A) to (1C) is an integer of 0 to 3 independently.
Above all, from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity, m in the formula (1A) is preferably an integer of 0 to 2, and preferably an integer of 1 or 2.
Above all, from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity, m in the formula (1B) is preferably an integer of 0 to 2, and preferably an integer of 0 or 1.
Above all, from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity, m in the formula (1C) is preferably an integer of 0 to 2.
C ^A to C ^C in the formulas (1A) to (1C) are preferably independently having a benzene ring structure or a naphthalene ring structure, and more preferably a benzene ring structure.
Each Y ¹ in the formula (1A) ~ formula (1C) is independently an oxygen atom, a sulfur atom, or is preferably NR ^N, oxygen atom, or, more preferably a sulfur atom, an oxygen atom It is particularly preferable to have.
Are each R ^N independently in Formula (1A) ~ formula (1C), a hydrogen atom, or, preferably an alkyl group, a hydrogen atom, or, more preferably a methyl group, is a hydrogen atom Especially preferable.
Ani ⁻ in the formulas (1A) to (1C) preferably has a carboxylic acid anion structure or a sulfonic acid anion structure.
Cat ⁺ in the formulas (1A) to (1C) preferably has a quaternary ammonium cation structure.
L ¹ in the formulas (1A) to (1C) is preferably a divalent linking group independently, and more preferably an alkylene group, an alkyleneoxyalkylene group, or a polyalkyleneoxyalkylene group. It is more preferably an alkylene group and particularly preferably an ethylene group.

Examples of the electron-attracting group in the formula (1X) include a group represented by -C (= O) OR ^1X (R ^1X represents an alkyl group), a cyano group, a nitro group, a trifluoromethyl group and the like. Be done.
R ² and R ³ in the above formula (1X) are preferably cyano groups or alkoxycarbonyl groups, respectively, and are particularly preferably cyano groups.
Further, it is preferable that R ² and R ³ in the above formula (1X) have the same group.

It is preferable that X ¹ and X ² in the formulas (1A) to (1C) are independently oxygen atoms or groups represented by the above formula (1X), and are oxygen atoms or R ² and R. ³ is more preferably a group represented by the above formula represents a cyano group (1X), and particularly preferably R ² and R ³ is a group represented by the formula is a cyano group (1X).
A ¹ in the formulas (1A) to (1C) is preferably a radically polymerizable group or a cationically polymerizable group from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity, and is preferably a radically polymerizable group. It is more preferably an acrylic group, a methacryl group, a vinyl group, or an allyl group, and it is more preferably a (meth) acryloxy group, a (meth) acrylamide group, a vinyl ester group, a vinyl ether group, or a styryl group (vinylphenyl). Group) or (meth) allyl group is more preferred, and (meth) acryloxy group, vinyl ester group, vinyl ether group, or styryl group (vinylphenyl group) is more preferable, and (meth) acryloxy group, or , A styryl group (vinylphenyl group) is more preferable, a (meth) acryloxy group is particularly preferable, and an acryloxy group is most preferable.
It is preferable that p in the formulas (1A) to (1C) is 1.

N in the formulas (1A) to (1C) is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and particularly preferably 1 or 2.

The above formulas (1A) to (1C) are preferably compounds represented by the following formulas (2) or (3) from the viewpoints of weight loss inhibitory property, pattern linearity, and sensitivity.

Compound A is preferably a compound represented by the following formula (2) or formula (3) from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity.

In the formula (2), R ²¹ to R ²⁴ are independently halogen atoms, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, acyl groups, acyloxy groups, hydroxy groups, amino groups, nitro groups and amide groups. , Or a group having a polymerizable group, and R ²¹ and R ²² or R ²³ and R ²⁴ may be independently linked to each other to form a ring, and at least R ²¹ to R ²⁴ may be formed. One is a group having a polymerizable group.
In the formula (3), R ³¹ to R ³⁴ independently represent a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, an acyloxy group, a hydroxy group, an amino group, a nitro group and an amide group. , Or a group having a polymerizable group, and R ³¹ and R ³² , or R ³³ and R ³⁴ may be independently linked to each other to form a ring, and at least R ³¹ to R ³⁴ may be formed. One is a group having a polymerizable group.

R ²¹ to R ²⁴ and R ³¹ to R ³⁴ in the formula (2) or the formula (3) are independently halogen atoms, alkyl groups, aryl groups, alkoxy groups, acyloxy groups, nitro groups, or cyano groups. It is preferably a fluorine atom, a chlorine atom, an alkoxy group, or a cyano group, and particularly preferably a fluorine atom, a nitro group, a methoxy group, or a cyano group.
The polymerizable group in the formula (2) or the formula (3) has the same meaning as the polymerizable group in the above formulas (1A) to (1C), and the preferred embodiment is also the same.
In formula (2) or formula (3), R ²¹ and R ²² , or R ²³ and R ²⁴ , or R ³¹ and R ³² , or R ³³ and R ³⁴ are independently connected to each other to form a ring. When it is formed, the ring to be formed preferably has a benzene ring structure or a naphthalene ring structure, and more preferably a benzene ring structure.
The formula (2) or formula (3) preferably has two or more polymerizable groups in one molecule from the viewpoint of weight loss inhibitory property, pattern linearity, and sensitivity. The upper limit of the number of polymerizable groups in the formula (2) or the formula (3) is not particularly limited, but is preferably 6 or less, and more preferably 4 or less.

-solubility-
The solubility of compound A in the solvent used at 25 ° C. is preferably less than 0.5 g / mL, more preferably less than 0.1 g / mL, from the viewpoint of suppressing leaching from the obtained pattern. It is preferably less than 0.05 g / mL, especially preferably less than 0.05 g / mL. The lower limit of the solubility is not particularly limited, and is preferably 0.001 g / mL or more.
The solubility of Compound A in propylene glycol monomethyl ether acetate (PGMEA) at 25 ° C. is preferably less than 0.5 g / mL, preferably 0.1 g / mL, from the viewpoint of suppressing leaching from the obtained pattern. It is more preferably less than mL, and particularly preferably less than 0.05 g / mL. The lower limit of the solubility in PGMEA is not particularly limited, and is preferably 0.001 g / mL or more.

-Content-
The colored photosensitive composition according to the present disclosure may contain one compound A alone or two or more compounds A.
The content of compound A in the colored photosensitive composition according to the present disclosure is 0.01% by mass with respect to the total mass of the colorant from the viewpoints of weight loss inhibitory property, pattern linearity, sensitivity, and spectral characteristics. It is preferably about 20% by mass, more preferably 0.05% by mass to 10% by mass, and particularly preferably 0.1% by mass to 5% by mass.

Hereinafter, A-1 to A-32, which are specific examples of Compound A, will be shown, but the present invention is not limited thereto.

-Method for producing compound A-
The method for producing the compound A is not particularly limited, and the compound A can be produced by referring to a known method.

-Method of adding compound A-
The method for adding the compound A to the colored photosensitive composition is not particularly limited, and a known addition method and a known mixing method can be used. For example, a method of mixing (dry or wet) with a pigment in advance and using it as a dried compound A-containing composite pigment, adding it at the time of pigment milling, adding it with a dispersion medium at the time of pigment dispersion, or adding it to a pigment dispersion liquid. Etc. are preferably mentioned.

<Colorant>
The colored photosensitive composition according to the present disclosure contains a colorant.
Examples of the colorant include pigments and dyes, but pigments are preferable.
Examples of pigments include white pigments, black pigments, chromatic pigments, and near-infrared absorbing pigments. In the present disclosure, the white pigment includes not only pure white but also a light gray (for example, grayish white, light gray, etc.) pigment close to white. Further, the pigment may be either an inorganic pigment or an organic pigment. Further, as the pigment, an inorganic pigment or a material in which a part of the organic-inorganic pigment is replaced with an organic chromophore can be used. Hue design can be facilitated by replacing inorganic pigments and organic-inorganic pigments with organic chromophores. Further, the pigment preferably has a maximum absorption wavelength in the wavelength range of 400 nm to 2,000 nm, and more preferably has a maximum absorption wavelength in the wavelength range of 400 nm to 700 nm.
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 pixel include a red pixel, a green pixel, a blue pixel, a magenta color pixel, a cyan color pixel, a yellow color pixel, and the like. Among them, green pixels are preferably mentioned.

The average primary particle size of the pigment used in the present disclosure is preferably 1 nm to 200 nm. The lower limit is more preferably 5 nm or more, and particularly preferably 10 nm or more. The upper limit is more preferably 180 nm or less, further preferably 150 nm or less, and even more preferably 100 nm or less. When the average primary particle size of the pigment is in the above range, the dispersibility of the pigment in the colored photosensitive composition is good. In the present disclosure, the primary particle size of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. 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. Further, the average primary particle diameter in the present disclosure is an arithmetic mean value of the primary particle diameter for the primary particles of 400 pigments. Further, the primary particles of the pigment refer to independent particles without aggregation.

In addition, the colored photosensitive composition according to the present disclosure preferably contains a green colorant as a colorant, and more preferably contains a green colorant and a yellow colorant, from the viewpoint of more exerting the effects in the present disclosure. ..
Further, the colorant preferably contains a phthalocyanine pigment, and more preferably contains a green phthalocyanine pigment, from the viewpoint of sensitivity and spectral characteristics.

-Green colorant-
As the green colorant, known ones can be used. For example, phthalocyanine compounds such as Color Index (CI) Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64 (phthalocyanine), 65 (phthalocyanine), 66 (phthalocyanine) Can be mentioned.
Further, as a green colorant, zinc halide has an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms. A phthalocyanine compound can also be used. Specific examples thereof include the compound described in International Publication No. 2015/118720, the compound described in Chinese Patent Application Publication No. 1069090227, a phthalocyanine compound having a phosphate ester as a ligand, and Japanese Patent Application Laid-Open No. 2019-038958. The compounds described in the above can also be used.
Further, as the green pigment, the green pigment described in JP-A-2019-8014 or JP-A-2018-180023 may be used.

The green colorant may be used alone or in combination of two or more.
The content of the green colorant in the total solid content of the colored photosensitive composition is preferably 10% by mass to 80% by mass. The lower limit is more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is more preferably 70% by mass or less, and particularly preferably 60% by mass or less.

-Yellow colorant-
Examples of the yellow colorant include azo compounds, quinophthalone compounds, isoindolinone compounds, isoindoline compounds, anthraquinone compounds and the like. Of these, an isoindoline compound is preferable because it is easy to form a film having spectral characteristics suitable for green pixels.

As the yellow pigment, the color index (CI) Pigment Yellow (hereinafter, also simply referred to as “PY”) 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, 118,119,120,123,125,126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166 167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214,215, Directly linked quinophthalone dimer described in Publication No. 2013/098836), 231,232 (methine type), 233 (quinoline type), 234 (aminoketone type), 235 (aminoketone type), 236 (aminoketone type), etc. Can be mentioned.

Further, as the yellow pigment, the pigment described in JP-A-2017-201003 and the pigment described in JP-A-2017-197719 can be used. Further, as the yellow pigment, at least one anion selected from the group consisting of an azo compound represented by the following formula (Y) and an azo compound having a tautomeric structure thereof, two or more kinds of metal ions, and a melamine compound. A metal azo pigment containing the above can also be used.

In formula (Y), ^RY1 and ^RY2 independently represent -OH or -NR ^Y5 ^RY6 , and ^RY3 and ^RY4 independently represent = O or = NR ^Y7 , respectively, ^RY5 to R. ^Y7 independently represents a hydrogen atom or an alkyl group.
The number of carbon atoms of the alkyl group represented by ^RY5 to ^RY7 is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. The alkyl group may be linear, branched or cyclic, and is preferably linear or branched, more preferably linear. The alkyl group may have a substituent. Preferred examples of the substituent include a halogen atom, a hydroxy group, an alkoxy group, a cyano group and an amino group.

Regarding the above-mentioned metal azo pigments, paragraphs 0011 to 0062, 0137 to 0276 of JP-A-2017-171912, paragraphs 0010 to 0062, 0138-0295, JP-A-2017-171914 of JP-A-2017-171913, The description of paragraphs 0011 to 0062, 0139 to 0190, and paragraphs 0010 to 0065 and 0142 to 0222 of JP-A-2017-171915 can be referred to, and these contents are incorporated in the present specification.

Further, as the yellow pigment, a quinophthalone dimer represented by the following formula (Q) can also be preferably used. Further, the quinophthalone dimer described in Japanese Patent No. 6443711 can also be preferably used.

In the formula (Q), X ₁ to X ₁₆ independently represent a hydrogen atom or a halogen atom, and Z represents an alkylene group having 1 to 3 carbon atoms.

As yellow pigments, JP-A-2018-203798, JP-A-2018-62578, Patent No. 6432077, Patent No. 6432076, JP-A-2018-155881, JP-A-2018-11757, JP-A. 2018-40835, 2017-197640, 2016-145282, 2014-85565, 2014-21139, 2013-209614, 2013- 209435, 2013-181015, 2013-61622, 2013-54339, 2013-32486, 2012-226110, 2008-74987 Japanese Patent Application Laid-Open No. 2008-81565, Japanese Patent Application Laid-Open No. 2008-79486, Japanese Patent Application Laid-Open No. 2008-74985, Japanese Patent Application Laid-Open No. 2008-50420, Japanese Patent Application Laid-Open No. 2008-31281, or Japanese Patent Application Laid-Open No. 48-32765. The quinophthalone pigments described in the publication can also be preferably used.

Further, as the yellow colorant, the quinophthalone compounds described in paragraphs 0011 to 0034 of JP2013-54339, the quinophthalone compounds described in paragraphs 0013 to 0058 of JP2014-26228, and JP-A-2019-8014. , The quinophthalone compound described in Japanese Patent No. 6607427, the compound described in Korean Publication No. 10-2014-0034963, the compound described in JP-A-2017-0950706, Taiwan Patent Application Publication No. 201920495. The compound described in Japanese Patent Application Laid-Open No. 6607427, the compound described in Japanese Patent Publication No. 6607427, and the like can also be used.
Further, as the yellow colorant, the compound described in JP-A-2018-62644 can also be used. In addition, this compound can also be used as a pigment derivative.
Further, as described in JP-A-2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.

The yellow colorant may be used alone or in combination of two or more.
The content of the yellow colorant in the colored photosensitive composition according to the present disclosure is preferably 10 parts by mass to 100 parts by mass with respect to 100 parts by mass of the green colorant. The upper limit is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, and further preferably 50 parts by mass or less. The lower limit is preferably 12.5 parts by mass or more, more preferably 14 parts by mass or more, and further preferably 16 parts by mass or more.
Further, when the colored photosensitive composition according to the present disclosure is green, the mass ratio of the green colorant to the yellow colorant is determined from the viewpoint of sensitivity and spectral characteristics: green colorant: yellow colorant = 100: 0. It is preferably from 50:50, more preferably from 95: 5 to 60:40, and particularly preferably from 90:10 to 70:30.

Examples of chromatic colorants other than green and yellow include the following.

C. I. Pigment Orange 2,5,13,16,17: 1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73, etc. (The above is orange pigment),
C. I. Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48: 1,48: 2,48: 3,48: 4, 49,49: 1,49: 2,52: 1,52: 2,53: 1,57: 1,60: 1,63: 1,66,67,81: 1,81: 2,81: 3, 83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184 185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,270,272,279,294 (xanthene system) , Organo Ultramarine, Bruish Red), 295 (monoazo type), 296 (diazo type), 297 (aminoketone type), etc. (above, red pigment),
C. I. Pigment Violet 1,19,23,27,32,37,42,60 (triarylmethane type), 61 (xanthene type), etc. (above, purple pigment),
C. I. Pigment Blue 1,2,15,15: 1,15: 2,15: 3,15: 4,15: 6,16,22,60,64,66,79,80,87 (monoazo system), 88 ( Methine type) etc. (above, blue pigment).

An aluminum phthalocyanine compound having a phosphorus atom can also be used as the blue pigment. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP2012-247591A and paragraphs 0047 of JP2011-157478A.

As the red pigment, a diketopyrrolopyrrole pigment in which at least one bromine atom is substituted in the structure described in JP-A-2017-2013384, and a diketopyrrolopyrrole-based pigment described in paragraphs 0016 to 0022 of Patent No. 6248838. Pigments, diketopyrrolopyrrole compounds described in WO2012 / 102399, diketopyrrolopyrrole compounds described in WO2012 / 117965, naphtholazo compounds described in JP2012-229344, patent No. The red pigment described in Japanese Patent No. 6516119, the red pigment described in Japanese Patent No. 6525101, and the like can also be used. Further, as the red pigment, a compound having a structure in which an aromatic ring group having an oxygen atom, a sulfur atom or a nitrogen atom bonded to the aromatic ring is bonded to a diketopyrrolopyrrole skeleton can also be used. it can. As such a compound, a compound represented by the formula (DPP1) is preferable, and a compound represented by the formula (DPP2) is more preferable.

In the above formula, R ¹¹ and R ¹³ each independently represent a substituent, R ¹² and R ¹⁴ each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group, and n ¹¹ and n ¹³ are independent of each other. , X ¹² and X ¹⁴ independently represent an oxygen atom, a sulfur atom or a nitrogen atom, and when X ¹² is an oxygen atom or a sulfur atom, m12 represents 1 and X. ^{When 12} is a nitrogen atom, m12 represents 2, m14 represents 1 when X ¹⁴ is an oxygen atom or a sulfur atom, and m14 represents 2 when X ¹⁴ is a nitrogen atom. The substituents represented by R ¹¹ and R ¹³ include an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryloxycarbonyl group, an amide group, a cyano group, a nitro group and a trifluoro group. Preferred specific examples include a methyl group, a sulfoxide group, and a sulfo group.

White pigments include titanium oxide, strontium titanate, barium titanate, zinc oxide, magnesium oxide, zirconium oxide, aluminum oxide, barium sulfate, silica, talc, mica, aluminum hydroxide, calcium silicate, aluminum silicate, hollow. Examples include resin particles and zinc sulfide. The white pigment is preferably particles having a titanium atom, and more preferably titanium oxide. Further, the white pigment is preferably particles having a refractive index of 2.10 or more with respect to light having a wavelength of 589 nm. The above-mentioned refractive index is preferably 2.10 to 3.00, and more preferably 2.50 to 2.75.

In addition, as the white pigment, titanium oxide described in "Titanium oxide physical properties and applied technology, by Manabu Kiyono, pp. 13-45, published on June 25, 1991, published by Gihodo Publishing" can also be used.

The white pigment is not limited to a single inorganic substance, but particles compounded with another material may be used. For example, particles having vacancies or other materials inside, particles in which a large number of inorganic particles are attached to core particles, core particles composed of core particles composed of polymer particles, and shell composite particles composed of a shell layer composed of inorganic nanoparticles are used. Is preferable. As the core and shell composite particles composed of the core particles composed of the polymer particles and the shell layer composed of the inorganic nanoparticles, for example, the description in paragraphs 0012 to 0042 of JP2015-047520 can be referred to. The contents are incorporated herein by reference.

Hollow inorganic particles can also be used as the white pigment. Hollow inorganic particles are inorganic particles having a structure having cavities inside, and are inorganic particles having cavities surrounded by an outer shell. Examples of the hollow inorganic particles include the hollow inorganic particles described in JP-A-2011-075786, International Publication No. 2013/061621, JP-A-2015-164881, and the like, and the contents thereof are incorporated in the present specification. Is done.

The black pigment is not particularly limited, and known ones can be used. For example, carbon black, titanium black, graphite and the like can be mentioned, with carbon black and titanium black being preferable, and titanium black being more preferable. Titanium black is black particles containing a titanium atom, and low-order titanium oxide or titanium oxynitride is preferable. The surface of titanium black can be modified as needed for the purpose of improving dispersibility and suppressing cohesion. For example, it is possible to coat the surface of titanium black with silicon oxide, titanium oxide, germanium oxide, aluminum oxide, magnesium oxide, or zirconium oxide. Further, it is also possible to treat with a water-repellent substance as shown in Japanese Patent Application Laid-Open No. 2007-302836. Examples of the black pigment include Color Index (CI) Pigment Black 1, 7 and the like. Titanium black preferably has a small primary particle size and an average primary particle size of each particle. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles and having a content ratio of Si atoms and Ti atoms in the dispersion adjusted to a range of 0.20 to 0.50 can be mentioned. Regarding the above dispersion, the description in paragraphs 0020 to 0105 of JP2012-169556A can be referred to, and the content thereof is incorporated in the present specification. Examples of commercially available titanium black products include titanium black 10S, 12S, 13R, 13M, 13M-C, 13RN, 13MT (trade name: manufactured by Mitsubishi Materials Corporation), Tilac D ( Product name: Ako Kasei Co., Ltd.)

Further, as the pigment used in the present disclosure, a pigment having an X-ray diffraction pattern by a specific CuKα ray is preferably mentioned. Specifically, for example, the phthalocyanine pigment described in Japanese Patent No. 6561862, the diketopyrrolopyrrole pigment described in Japanese Patent No. 6413872, and the azo pigment described in Japanese Patent No. 6281345 (CI Pigment Red269). And so on.

There are no particular restrictions on the dye, and known dyes can be used. Pyrazole azo compound, anilino azo compound, triarylmethane compound, anthraquinone compound, anthrapyridone compound, benzylidene compound, oxonol compound, pyrazorotriazole azo compound, pyridone azo compound, cyanine compound, phenothiazine compound, pyrolopyrazole azomethine compound, xanthene compound, phthalocyanine compound , Bentopylan compounds, indigo compounds, pyromethene compounds.

Further, as other colorants, a thiazole compound described in JP2012-158649A, an azo compound described in JP2011-184493, an azo compound described in JP2011-145540, and JP-A-2019. The methine dye described in JP-A-073695, the methine dye described in JP-A-2019-073696, the methine dye described in JP-A-2019-073697, and the methine dye described in JP-A-2019-073698 are used. You can also do it.

A dye multimer can also be used in the colored photosensitive composition according to the present disclosure. The dye multimer is preferably a dye that is used by dissolving it in a solvent. In addition, the dye multimers may form particles. When the dye multimer is a particle, it is usually used in a state of being dispersed in a solvent. The dye multimer in the particle state can be obtained by, for example, emulsion polymerization, and specific examples thereof include the compounds and production methods 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 plurality of dye structures contained in one molecule may have 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, further preferably 20,000 or less. Dye multimers are described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, International Publication No. 2016/031442, and the like. Compounds can also be used.

-Colorant content-
The colored photosensitive composition according to the present disclosure may contain one kind of colorant alone or two or more kinds.
The content of the colorant in the total solid content of the colored photosensitive composition is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more. It is particularly preferably 30% by mass or more, and most preferably 40% by mass or more. The upper limit of the content of the colorant is preferably 80% by mass or less, more preferably 70% by mass or less, and further preferably 60% by mass or less.

<Polymerizable compound>
The colored photosensitive composition according to the present disclosure contains a polymerizable compound. The polymerizable compound is a compound other than compound A.
The polymerizable compound is preferably 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.
The polymerizable compound may be in any chemical form such as a monomer, a prepolymer or an oligomer, but a monomer is preferable. The molecular weight of the polymerizable compound is preferably 100 to 3,000. The upper limit is more preferably 2,000 or less, further preferably 1,500 or less, and particularly preferably 1,000 or less. The lower limit is more preferably 150 or more, and even more preferably 250 or more.

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 3 to 6 ethylenically unsaturated groups. It is more preferable that the compound contains two compounds. Further, the polymerizable compound is preferably a (meth) acrylate compound having 3 to 15 functionalities, and more preferably a (meth) acrylate compound having 3 to 6 functionalities. Specific examples of the polymerizable compound include paragraphs 0905 to 0108 of JP2009-288705A, paragraphs 0227 of JP2013-209760A, paragraphs 0254 to 0257 of JP2008-292970, and Japanese Patent Application Laid-Open No. 2013-. It is described in paragraphs 0034 to 0038 of Japanese Patent Application Laid-Open No. 253224, paragraphs 0477 of Japanese Patent Application Laid-Open No. 2012-208494, Japanese Patent Application Laid-Open No. 2017-048367, Japanese Patent No. 6057891, Japanese Patent No. 6031807, and Japanese Patent Application Laid-Open No. 2017-194662. These compounds are incorporated herein by reference.

The ethylenically unsaturated base value (hereinafter, also referred to as C = C value) of the polymerizable compound is 2 mmol / g to 14 mmol from the viewpoint of storage stability of the composition and color loss resistance of the obtained film. It is preferably / g. The lower limit is more preferably 3 mmol / g or more, further preferably 4 mmol / g or more, and particularly preferably 5 mmol / g or more. The upper limit is more preferably 12 mmol / g or less, further preferably 10 mmol / g or less, and particularly preferably 8 mmol / g or less. The C = C value of the polymerizable compound is a value calculated by dividing the number of ethylenically unsaturated groups contained in one molecule of the polymerizable compound by the molecular weight of the polymerizable compound.

As polymerizable compounds, dipentaerythritol triacrylate (commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (commercially available KAYARAD D-320; Nihon Kayaku Co., Ltd.) ), Dipentaerythritol penta (meth) acrylate (commercially available KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (commercially available KAYARAD DPHA; Nippon Kayaku) NK ester A-DPH-12E manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and a structure in which these (meth) acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues. (For example, SR454, SR499 commercially available from Sartmer) are preferred. As polymerizable compounds, diglycerin EO (ethylene oxide) modified (meth) acrylate (commercially available M-460; manufactured by Toa Synthetic Co., Ltd.), pentaerythritol tetraacrylate (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), NK ester A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nihon Kayaku Co., Ltd.), Aronix TO-2349 (Toa Synthetic Co., Ltd.) ), NK Oligo UA-7200 (Shin Nakamura Chemical Industry Co., Ltd.), 8UH-1006, 8UH-1012 (Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (Kyoeisha Chemical Co., Ltd.), etc. Can also be used.

Further, as the polymerizable compound, trimethylolpropane tri (meth) acrylate, trimethylolpropane propyleneoxy-modified tri (meth) acrylate, trimethylolpropane ethyleneoxy-modified tri (meth) acrylate, and isocyanurate ethyleneoxy-modified tri (meth) acrylate. It is also preferable to use a trifunctional (meth) acrylate compound such as pentaerythritol trimethylolpropane (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, and M-305. , M-303, M-452, 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, TMPT (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) And so on.

As the polymerizable compound, a compound having an isocyanurate skeleton can also be used. By using a polymerizable compound having an isocyanurate skeleton, the solvent resistance of the obtained membrane can be improved. Specific examples of the polymerizable compound having an isocyanurate skeleton include tris isocyanurate (2-acryloyloxyethyl), ε-caprolactone-modified tris- (2-acryloyloxyethyl) isocyanurate, and the like. Commercially available products include Funkrill FA-731A (manufactured by Hitachi Chemical Co., Ltd.), NK Ester A9300, A93001CL, A9300-3CL (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), and Aronix M-315 (Toagosei Co., Ltd.) Co., Ltd.) and the like.

As the polymerizable compound, a compound having an acid group can also be used. By using a polymerizable compound having an acid group, the polymerizable compound in the unexposed portion can be easily removed during development, and the generation of development residue can be suppressed. Examples of the acid group include a carboxy group, a sulfo group, a phosphoric acid group and the like, and a carboxy group is preferable. Examples of commercially available products of the polymerizable compound having an acid group include Aronix M-305, M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.). The preferable acid value of the polymerizable compound having an acid group is 0.1 mgKOH / g to 40 mgKOH / g, and more preferably 5 mgKOH / g to 30 mgKOH / g. When the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when it is 40 mgKOH / g or less, it is advantageous in production and handling.

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

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 having 4 to 20 ethyleneoxy groups 3 to 3 to A hexafunctional (meth) acrylate compound is more preferred. Commercially available products of the polymerizable compound having an alkyleneoxy group include SR-494, which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartomer, and a trifunctional (meth) having three isobutyleneoxy groups. Examples thereof include KAYARAD TPA-330, which is an acrylate.

As the polymerizable compound, a polymerizable compound having a fluorene skeleton can also be used. Examples of commercially available products of the polymerizable compound having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).

As the polymerizable compound, it is also preferable to use a compound that does not substantially contain an environmentally regulated substance 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.).
The term "substantially free" in the present disclosure means that the content of the colored photosensitive composition in the total solid content is 0.1% by mass or less, and 0.05% by mass or less. Is preferable, and it is more preferable that it is not contained.

Examples of the polymerizable compound include urethane acrylates as described in JP-A-48-041708, JP-A-51-0371993, JP-A-02-032293, and JP-A-02-016765. Urethane compounds having an ethylene oxide-based skeleton described in Japanese Patent Publication No. 58-049860, Japanese Patent Publication No. 56-017654, Japanese Patent Publication No. 62-039417, and Japanese Patent Publication No. 62-039418 are also suitable. Further, it is also preferable to use a polymerizable compound 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. The polymerizable compounds are UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, Commercially available products such as T-600, AI-600, and LINK-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) can also be used.

The content of the polymerizable compound 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, further preferably 1% by mass or more, particularly preferably 3% by mass or more, and most preferably 5% by mass or more. The upper limit is more preferably 25% by mass or less, further preferably 20% by mass or less, and particularly preferably 15% by mass or less. The polymerizable compound may be used alone or in combination of two or more. When two or more types are used in combination, the total of them is preferably in the above range.

Further, the total content of the resin and the polymerizable compound described later in the total solid content of the colored photosensitive composition is preferably 10% by mass to 50% by mass. The lower limit is preferably 15% by mass or more, more preferably 20% by mass or more, and further preferably 25% by mass or more. The upper limit is preferably 45% by mass or less, more preferably 40% by mass or less, and further preferably 35% by mass or less.

Further, the content of the polymerizable compound is preferably 10 parts by mass to 2,000 parts by mass with respect to 100 parts by mass of the photopolymerization initiator. The upper limit is preferably 1,800 parts by mass or less, and more preferably 1500 parts by mass or less. The lower limit is preferably 30 parts by mass or more, and more preferably 50 parts by mass or more.

<Photopolymerization initiator>
The colored photosensitive composition according to the present disclosure contains a photopolymerization initiator.
The photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable. The photopolymerization initiator is preferably a photoradical polymerization initiator.

Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, α-hydroxyketone compounds, α-aminoketone compounds and the like. From the viewpoint of exposure sensitivity, the photopolymerization initiator includes trihalomethyltriazine compound, benzyldimethylketal compound, α-hydroxyketone compound, α-aminoketone compound, acylphosphine compound, phosphine oxide compound, metallocene compound, oxime compound, and triarylimidazole. It is preferably a dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxaziazole compound and a 3-aryl substituted coumarin compound, and an oxime compound and an α-hydroxyketone compound. , Α-Aminoketone compound, and acylphosphine compound are more preferable, and an oxime compound is further preferable. Examples of the photopolymerization initiator include compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, MATERIAL STAGE 37-60p, vol. 19, No. 3. Peroxide-based photopolymerization initiator described in 2019, photopolymerization initiator described in International Publication No. 2018/221177, photopolymerization initiator described in International Publication No. 2018/110179, JP-A-2019-043864 Examples of the photopolymerization initiator described in JP-A, the photopolymerization initiator described in JP-A-2019-044030, and the organic peroxide described in JP-A-2019-167313 are described in the present specification. Be incorporated.

Examples of commercially available α-hydroxyketone compounds include IRGACURE 184, DAROCUR 1173, IRGACURE 500, IRGACURE 2959, and IRGACURE 127 (all manufactured by BASF). Examples of commercially available α-aminoketone compounds include IRGACURE 907, IRGACURE 369, IRGACURE 379, and IRGACURE 379EG (all manufactured by BASF). Examples of commercially available acylphosphine compounds include IRGACURE 819 and DAROCUR-TPO (all manufactured by BASF).

Examples of the oxime compound include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-080068, the compounds described in JP-A-2006-342166, and J. Am. C. S. The compound according to Perkin II (1979, pp. 1653-1660), J. Mol. C. S. The compound described in Perkin II (1979, pp. 156-162), the compound described in Journal of Photopolymer Science and Technology (1995, pp. 202-232), the compound described in JP-A-2000-066385. Compounds described in JP-A-2000-080068, compounds described in JP-A-2004-534977, compounds described in JP-A-2006-342166, compounds described in JP-A-2017-019766, Patent No. 6065596, the compound described in International Publication No. 2015/152153, the compound described in International Publication No. 2017/051680, the compound described in JP-A-2017-198865, the compound described in International Publication No. 2017/164127. Examples thereof include the compounds described in paragraphs 0025 to 0038 of the issue, and the compounds described in International Publication No. 2013/167515. Specific examples of the oxime compound include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminovtan-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one. Commercially available products include IRGACURE-OXE01, IRGACURE-OXE02, IRGACURE-OXE03, IRGACURE-OXE04 (above, manufactured by BASF), TR-PBG-304 (manufactured by Joshu Powerful Electronics New Materials Co., Ltd.), and ADEKA PTOMER N-1919. (A photopolymerization initiator 2) manufactured by ADEKA Corporation and described in JP2012-014502A. Further, as the oxime compound, it is also preferable to use a compound having no coloring property or a compound having high transparency and being hard to discolor. Examples of commercially available products include ADEKA ARKULS NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA Corporation).

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 JP-A-2014-137466.

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

In the present disclosure, an oxime compound having a fluorine atom can also be used as the photopolymerization initiator. Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, the compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471. Compound (C-3) and the like.

As the photopolymerization initiator, an oxime compound having a nitro group can be used. The oxime compound having a nitro group is also preferably a dimer. Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A, paragraphs 0008 to 0012 and 0070 to 0079 of JP2014-137466, and Patents 4223071. Examples thereof include the compounds described in paragraphs 0007 to 0025 of Japanese Patent Publication No. Adeca Arcurus NCI-831 (manufactured by ADEKA Corporation).

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

As the photopolymerization initiator, an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used. Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.

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

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

As the photopolymerization initiator, a bifunctional or trifunctional or higher 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. Further, when a compound having an asymmetric structure is used, the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the colored photosensitive composition with time is improved. Can be done. Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include JP-A-2010-527339, JP-A-2011-524436, International Publication No. 2015/004565, and JP-A-2016-532675. The dimer of the oxime compound described in paragraphs 0407 to 0412 of the above, paragraphs 0039 to 0055 of International Publication No. 2017/033680, the compound (E) and the compound (E) described in Japanese Patent Publication No. 2013-522445. G), Cmpd1 to 7 described in International Publication No. 2016/034963, Oxime ester photoinitiator described in paragraph 0007 of JP-A-2017-523465, paragraph of JP-A-2017-167399. Photoinitiators described in 0020 to 0033, photopolymerization initiators (A) described in paragraphs 0017 to 0026 of JP-A-2017-151342, oxime ester light described in Japanese Patent No. 6469669. Initiators and the like can be mentioned.

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.
Only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.

<Resin>
The colored photosensitive composition according to the present disclosure preferably contains a resin. The resin is blended, for example, for the purpose of dispersing particles such as pigments in the composition and for the purpose of a binder. A resin mainly used for dispersing particles such as pigments is also referred to as a dispersant. However, such an application of the resin is an example, and it can be used for a purpose other than such an application.
The resin preferably contains a polymer dispersant described later.
Further, the resin preferably contains an alkali-soluble resin described later.

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.

Examples of the resin 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, and polyamideimide resin. , Polyolefin resin, cyclic olefin resin, polyester resin, styrene resin and the like. One of these resins may be used alone, or two or more thereof may be mixed and used. Further, the resin described in paragraphs 0041 to 0060 of JP-A-2017-206689 and the resin described in paragraphs 0153 to 0167 of JP-A-2018-173660 can also be used.

It is preferable to use a resin having an acid group as the resin. According to this aspect, the developability of the colored photosensitive composition can be improved, and it is easy to form pixels having excellent rectangularity. Examples of the acid group include a carboxy group, a phosphoric acid group, a sulfo group, a phenolic hydroxy group and the like, and a carboxy group is preferable. The resin having an acid group can be suitably used as, for example, an alkali-soluble resin.

The resin having an acid group preferably contains a structural unit having an acid group in the side chain, and more preferably contains 5 mol% to 70 mol% of the structural units having an acid group in the side chain in all the structural units of the resin. .. The upper limit of the content of the repeating unit having an acid group in the side chain is more preferably 50 mol% or less, and particularly preferably 30 mol% or less. The lower limit of the content of the structural unit having an acid group in the side chain is more preferably 10 mol% or more, and particularly preferably 20 mol% or more. In the present disclosure, when the content of the constituent unit is expressed in mol%, the constituent unit shall be synonymous with the monomer unit.

The colored photosensitive composition according to the present disclosure may also contain a resin (polymer dispersant) as a dispersant. Examples of the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin). Here, the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups. The acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%, and is substantially an acid. A resin consisting only of groups is more preferable. The acid group contained in the acidic dispersant (acidic resin) is preferably a carboxy group. The acid value of the acidic dispersant (acidic resin) is preferably 40 mgKOH / g to 105 mgKOH / g, more preferably 50 mgKOH / g to 105 mgKOH / g, and even more preferably 60 mgKOH / g to 105 mgKOH / g. Further, the basic dispersant (basic resin) represents a resin in which the amount of basic groups is larger than the amount of acid groups. The basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%. The basic group contained in the basic dispersant is preferably an amino group.

The resin used as the dispersant preferably contains a structural unit having an acid group. Since the resin used as the dispersant contains a repeating unit having an acid group, the generation of development residue can be further suppressed when the pattern is formed by the photolithography method.

The resin used as the dispersant is also preferably a graft resin. For details of the graft resin, the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.

It is also preferable that the resin used as the dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain. The polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain. The resin to have is preferable. The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity. Regarding the polyimine-based dispersant, the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.

The resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core portion. Examples of such resins include dendrimers (including star-shaped polymers). Specific examples of the dendrimer include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
Further, the above-mentioned resin having an acid group (alkali-soluble resin) can also be used as a dispersant.

It is also preferable that the resin used as the dispersant is a resin containing a structural unit having an ethylenically unsaturated group in the side chain. The content of the structural unit having an ethylenically unsaturated group in the side chain is preferably 10 mol% or more, more preferably 10 mol% to 80 mol%, and 20 mol% in all the structural units of the resin. It is more preferably ~ 70 mol%.

Further, as the resin used as the dispersant, a resin having a structural unit represented by the following formula D1 can be preferably used.

In the formula D1, R ^D1 to R ^D3 independently represent a hydrogen atom or an alkyl group, X ^D1 represents a -COO-, -CONR- or an arylene group, and R is a hydrogen atom, an alkyl group or an aryl group. the ^{stands, R D4} represents a divalent linking ^{group, L D1} represents a group represented by the following formula D2 or formula ^{D3, R D5} represents (nd + 1) -valent linking ^{group, X D2} is , Oxygen atom or -NR ^DA- , R ^DA represents a hydrogen atom, an alkyl group or an aryl group, and nd represents an integer of 1 or more.

In formulas D2 and D3, X ^D3 represents an oxygen atom or -NH-, X ^D4 represents an oxygen atom or -COO-, and R ^e1 to ^{Re 3} independently represent a hydrogen atom or an alkyl group. , R ^e1 to R ^e3 may be bonded to each other to form a ring structure, and * represents a bonding position with another structure.

The structural unit represented by the formula 1 preferably includes the structure shown below, but it goes without saying that the structural unit is not limited to these.

Note that m represents an integer of 2 or more, and n represents an integer of 1 or more.

Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie (for example, DISPERBYK-111, 161 etc.) and sparse sparse series manufactured by Nippon Lubrizol Co., Ltd. For example, Solsparse 76500) and the like. Further, the pigment dispersant described in paragraphs 0041 to 0130 of JP2014-130338A can also be used, and the contents thereof are incorporated in the present specification. The resin described as the dispersant can also be used for purposes other than the dispersant. For example, it can also be used as a binder.

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, further preferably 35% by mass or less, and particularly preferably 30% by mass or less. The content of the resin having an acid 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, further preferably 35% by mass or less, and particularly preferably 30% by mass or less. Further, the content of the resin having an acid group (alkali-soluble resin) in the total amount of the resin is preferably 30% by mass or more, more preferably 50% by mass or more, and more preferably 70% by mass because excellent developability can be easily obtained. The above is more preferable, and 80% by mass or more is particularly preferable. The upper limit can be 100% by mass, 95% by mass, or 90% by mass or less.

<Pigment derivative>
The colored photosensitive composition according to the present disclosure may contain a pigment derivative. According to this aspect, the storage stability of the colored photosensitive composition can be further improved. As the pigment derivative, a part of the pigment is a group having an acid group, a basic group, a salt structure, or a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene diimide structure, a perylene diimide structure, a pyrazinenoquinoxaline structure or a fullerene. Examples thereof include compounds having a structure substituted with a group having at least one structure selected from the group consisting of structures.
As the pigment derivative, a compound represented by the formula (B1) is preferable.

In formula (B1), P represents a dye structure, L represents a single bond or a linking group, X represents an acid group, a basic group, a group having a salt structure or a phthalimide methyl group, and m is an integer of 1 or more. , N represents an integer of 1 or more, and when m is 2 or more, the plurality of Ls and Xs may be different from each other, and when n is 2 or more, the plurality of Xs may be different from each other.

The pigment structure represented by P includes a pyrolopyrrolop pigment structure, a diketopyrrolopyrrole pigment structure, a quinacridone pigment structure, an anthraquinone pigment structure, a dianthraquinone pigment structure, a benzoisoindole pigment structure, a thiazineindigo pigment structure, an azo pigment structure, and a quinophthalone. Examples thereof include pigment structure, phthalocyanine pigment structure, naphthalocyanine pigment structure, dioxazine pigment structure, perylene pigment structure, perinone pigment structure, benzoimidazolone pigment structure, benzothiazole pigment structure, benzoimidazole pigment structure and benzoxazole pigment structure.

Examples of the linking group represented by L include a hydrocarbon group, a heterocyclic group, -NR-, -SO _2- , -S-, -O-, -CO-, or a group consisting of a combination thereof. R represents a hydrogen atom, an alkyl group or an aryl group.

Examples of the acid group represented by X include a carboxy group, a sulfo group, a carboxylic acid amide group, a sulfonic acid amide group, and an imic acid group. As the carboxylic acid amide group, a group represented by -NHCOR ^X1 is preferable. The sulfonic acid amide _group, preferably a group represented by _-NHSO ^{2 R X2.} As the imidic acid group, a group represented by -SO ₂ NHSO ₂ R ^X3 , -CONHSO ₂ R ^X4 , -CONHCOR ^X5 or -SO ₂ NHCOR ^X6 is preferable. ^RX1 to ^RX6 independently represent a hydrocarbon group or a heterocyclic group. Hydrocarbon group and heterocyclic group R ^{X1 ~} R ^X6 represents may further have a substituent. As a further substituent, a halogen atom is preferable, and a fluorine atom is more preferable. Examples of the basic group represented by X include an amino group. Examples of the salt structure represented by X include the above-mentioned salts of acid groups or basic groups.

Examples of the pigment derivative include compounds having the following structures. In addition, Japanese Patent Application Laid-Open No. 56-118462, Japanese Patent Application Laid-Open No. 63-264674, Japanese Patent Application Laid-Open No. 1-2170777, Japanese Patent Application Laid-Open No. 3-9961, Japanese Patent Application Laid-Open No. 3-26767, Japanese Patent Application Laid-Open No. 3-153780. Japanese Patent Application Laid-Open No. 3-455662, Japanese Patent Application Laid-Open No. 4-285669, Japanese Patent Application Laid-Open No. 6-145546, Japanese Patent Application Laid-Open No. 6-21208, Japanese Patent Application Laid-Open No. 6-241588, Japanese Patent Application Laid-Open No. 10-30063, The compounds described in JP-A-10-195326, paragraphs 0083 to 098 of International Publication No. 2011/024896, paragraphs 0063 to 0094 of International Publication No. 2012/102399, paragraphs 0083 of International Publication No. 2017/038252, etc. It can also be used and these contents are incorporated herein by reference.
Further, as pigment derivatives, JP-A-2015-172732 (metal salt of a quinophthalone compound having a sulfo group), JP-A-2014-199308, JP-A-2014-85562, JP-A-2014-35351, Alternatively, the compounds described in JP-A-2008-81565 can also be used, and their contents are incorporated in the present specification.

The content of the pigment derivative in the total solid content of the colored photosensitive composition is preferably 0.3% by mass to 20% by mass. The lower limit is more preferably 0.6% by mass or more, and particularly preferably 0.9% by mass or more. The upper limit is more preferably 15% by mass or less, further preferably 12.5% by mass or less, and particularly preferably 10% by mass or less.
The content of the pigment derivative is preferably 1 part by mass to 30 parts by mass with respect to 100 parts by mass of the pigment. The lower limit is more preferably 2 parts by mass or more, and particularly preferably 3 parts by mass or more. The upper limit is more preferably 25 parts by mass or less, further preferably 20 parts by mass or less, and particularly preferably 15 parts by mass or less.
Only one kind of pigment derivative may be used, or two or more kinds may be used in combination. When two or more types are used in combination, the total amount thereof is preferably in the above range.

<Compound 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 preferable. It is preferable to have 1 to 100 epoxy groups 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 two or more. Examples of the compound having an epoxy group are described in paragraphs 0034 to 0036 of JP2013-011869A, paragraphs 0147 to 0156 of JP2014-043556, and paragraphs 0085 to 0092 of JP2014-089408. Compounds, compounds described in JP-A-2017-179172 can also be used. These contents are incorporated in the present specification.

The compound having an epoxy group may be a low molecular weight compound (preferably less than 2,000 molecular weight, more preferably less than 1,000 molecular weight) or a macromolecule (for example, a polymer having a molecular weight of 1,000 or more and a polymer). Has 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 preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.

As the compound having an epoxy group, an epoxy resin can be preferably used. Examples of the epoxy resin include an epoxy resin which is a glycidyl etherified product of a phenol compound, an epoxy resin which is a glycidyl etherified product of various novolak resins, an alicyclic epoxy resin, an aliphatic epoxy resin, a heterocyclic epoxy resin, and a glycidyl ester type. Epoxy resin, glycidylamine-based epoxy resin, epoxy resin obtained by glycidylizing halogenated phenols, condensate of silicon compound having an epoxy group and other silicon compounds, polymerizable unsaturated compound having an epoxy group and other Examples thereof include a copolymer with another polymerizable unsaturated compound. The epoxy equivalent of the epoxy resin is preferably 310 g / eq to 3,300 g / eq, more preferably 310 g / eq to 1,700 g / eq, and more preferably 310 g / eq to 1,000 g / eq. Is more preferable.

Commercially available products of compounds having a cyclic ether group include, for example, EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC Corporation), Marproof G-0150M, G-0105SA, G-0130SP, G. Examples thereof include -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF CORPORATION, epoxy group-containing polymer).

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 0.1% by mass to 20% by mass. Mass% is preferred. 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. The compound having a cyclic ether group may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount thereof is within the above range.

<Near infrared absorber>
The colored photosensitive composition according to the present disclosure may further contain a near infrared absorber. The near-infrared absorber is preferably a compound having a maximum absorption wavelength in the range of more than 700 nm and 1800 nm or less. Also, near infrared absorber, that the ratio ^A 1 / ^{A 2} between the absorbance ^{A 2} in the absorbance ^{A 1} and the maximum absorption wavelength in the wavelength 500nm is preferably 0.08 or less, 0.04 or less More preferred.

Near-infrared absorbers include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonor compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyromethene compounds, Examples thereof include azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, metal oxides, and metal boroides. Examples of the pyrrolopyrrole compound include the compounds described in paragraphs 0016 to 0058 of JP2009-263614, the compounds described in paragraphs 0037 to 0052 of JP2011-68831, and paragraphs 0010 of International Publication No. 2015/166783. Examples thereof include the compounds described in ~ 0033. Examples of the squarylium compound include the compounds described in paragraphs 0044 to 0049 of JP2011-208101A, the compounds described in paragraphs 0060 to 0061 of Patent No. 6065169A, and paragraphs 0040 of International Publication No. 2016/181987. Compounds, compounds described in JP-A-2015-176046, compounds described in paragraph 0072 of International Publication No. 2016/190162, compounds described in paragraphs 0196-0228 of JP-A-2016-74649, JP-A-2017- The compound described in paragraph 0124 of Japanese Patent Application Laid-Open No. 67963, the compound described in International Publication No. 2017/135359, the compound described in JP-A-2017-1149956, the compound described in Japanese Patent Application Laid-Open No. 61979940, the compound described in International Publication No. 2016/120166. Examples thereof include the compounds described in the item. Examples of the cyanine compound include the compounds described in paragraphs 0044 to 0045 of JP2009-108267A, the compounds described in paragraphs 0026 to 0030 of JP2002-194040, and the compounds described in JP2015-172004. , The compound described in JP-A-2015-172102, the compound described in JP-A-2008-88426, the compound described in paragraph 0090 of International Publication No. 2016/190162, and the like. Examples of the croconium compound include the compounds described in JP-A-2017-82029. Examples of the iminium compound include the compounds described in JP-A-2008-528706, the compounds described in JP-A-2012-012399, the compounds described in JP-A-2007-92060, and International Publication No. 2018/043564. The compounds described in paragraphs 0048 to 0063 of the above are mentioned. Examples of the phthalocyanine compound include the compound described in paragraphs 093 of JP2012-77153, the oxytitanium phthalocyanine described in JP2006-343631, and the compound described in paragraphs 0013 to 0029 of JP2013-195480. Can be mentioned. Examples of the naphthalocyanine compound include the compounds described in paragraph 093 of JP2012-77153A. Examples of the metal oxide include indium tin oxide, antimonthine oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide. For details of tungsten oxide, paragraph 0080 of JP-A-2016-006476 can be referred to, and the contents thereof are incorporated in the present specification. Examples of the metal boride include lanthanum hexaboride. Examples of commercially available lanthanum hexaboride products include LaB _6- F (manufactured by Nippon Shinkinzoku Co., Ltd.). Further, as the metal boride, the compound described in International Publication No. 2017/119394 can also be used. Examples of commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hightech Co., Ltd.).

Further, as the near-infrared absorber, the squarylium compound described in JP-A-2017-197437, the squarylium compound described in paragraphs 0090 to 0107 of International Publication No. 2017/213047, and JP-A-2018-054760. Pyrrole ring-containing compounds described in paragraphs 0019 to 0075, pyrrole ring-containing compounds described in paragraphs 0078 to 0082 of JP-A-2018-040955, and pyrrole ring-containing compounds described in paragraphs 0043-0069 of JP-A-2018-002773. Compounds, squarylium compounds having an aromatic ring at the amide α position described in paragraphs 0024 to 0086 of JP-A-2018-041047, amide-linked squarylium compounds described in JP-A-2017-179131, JP-A-2017-141215. A compound having a pyrrole bis-type squalylium skeleton or a croconium skeleton described in JP-A, a dihydrocarbazole bis-type squalylium compound described in JP-A-2017-082029, an asymmetry described in paragraphs 0027-0114 of JP-A-2017-068120. A type compound, a pyrrole ring-containing compound (carbazole type) described in JP-A-2017-066963, a phthalocyanine compound described in Patent No. 6251530, and the like can also be used.

When the colored photosensitive composition according to the present disclosure contains a near-infrared absorber, the content of the near-infrared absorber in the total solid content of the colored photosensitive composition is preferably 1% by mass or more. It is more preferably mass% or more, and particularly preferably 10 mass% or more. The upper limit is not particularly limited, but is preferably 70% by mass or less, more preferably 65% by mass or less, and further preferably 60% by mass or less.
In addition, the colored photosensitive composition according to the present disclosure may be substantially free of a near-infrared absorber. When the colored photosensitive composition according to the present disclosure does not substantially contain a near-infrared absorber, the content of the near-infrared absorber in the total solid content of the colored photosensitive composition according to the present disclosure is 0.1% by mass. It is preferably less than or equal to, more preferably 0.05% by mass or less, and particularly preferably not contained.

<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. The silane coupling agent means a silane compound having a hydrolyzable group and other functional groups. Further, the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form 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, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of the functional group 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 and an isocyanate group. , Phenyl group and the like, preferably an amino group, a (meth) acryloyl group and an epoxy group. Specific examples of the silane coupling agent include the compounds described in paragraphs 0018 to 0036 of JP2009-288703A and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A, and the contents thereof. Is incorporated herein.

The content of the silane coupling agent in the total solid content of the colored photosensitive 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. The silane coupling agent may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.

<Organic solvent>
The colored photosensitive composition according to the present disclosure may contain an organic solvent. The organic solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the colored photosensitive composition. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like. For these details, paragraph 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein by reference. Further, an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used. Specific examples of the organic solvent 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 and the like. However, aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 mass ppm (parts) with respect to the total amount of organic solvent. Per milion) or less, 10 mass ppm or less, or 1 mass ppm or less).

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

Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter. The filter pore diameter of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The filter material is preferably polytetrafluoroethylene, polyethylene or nylon.

The organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.

The content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.

The content of the organic solvent in the colored photosensitive composition is preferably 10% by mass to 95% by mass, more preferably 20% by mass to 90% by mass, and 30% by mass to 90% by mass. Is even more preferable.

Further, it is preferable that the colored photosensitive composition according to the present disclosure does not substantially contain an environmentally regulated substance from the viewpoint of environmental regulation. In the present disclosure, substantially no environmentally regulated substance means that the content of the environmentally regulated substance in the coloring composition is 50 mass ppm or less, and preferably 30 mass ppm or less. It is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less. Examples of the environmentally regulated substance include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene. These are registered as environmentally regulated substances under the REACH (Registration Evaluation Authorization and Restriction of Chemicals) regulations, the PRTR (Pollutant Release and Transfer Register) law, and the VOC (Volatile Organic Compounds) regulations, and are used and handled. The method is strictly regulated. These compounds may be used as a solvent when producing each component used in the colored photosensitive composition according to the present disclosure, and may be mixed in the colored photosensitive composition as a residual solvent. From the viewpoint of human safety and consideration for the environment, it is preferable to reduce these substances as much as possible. Examples of the method for reducing the environmentally regulated substance include a method of heating or depressurizing the inside of the system to raise the boiling point of the environmentally regulated substance to the boiling point or higher and distilling off the environmentally regulated substance from the system to reduce the amount of the environmentally regulated substance. Further, when distilling off a small amount of an environmentally regulated substance, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to improve efficiency. When a compound having radical polymerization property is contained, a polymerization inhibitor or the like is added and distilled under reduced pressure in order to prevent the radical polymerization reaction from proceeding and cross-linking between molecules during distillation under reduced pressure. You may. These distillation methods are performed at the stage of the raw material, the stage of the product obtained by reacting the raw materials (for example, a resin solution after polymerization or a polyfunctional monomer solution), or a colored photosensitive composition prepared by mixing these compounds. It is possible at any stage such as a stage.

<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), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, primary cerium salt, etc.). Of these, p-methoxyphenol is preferable. The content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001% by mass to 5% by mass.

<Surfactant>
The colored photosensitive composition according to the present disclosure may contain a surfactant. As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicon-based surfactant can be used. Regarding surfactants, paragraphs 0238 to 0245 of International Publication No. 2015/166779 and paragraphs 0253 to 0260 of JP-A-2018-173660 can be referred to, and the contents thereof are incorporated in the present specification.
The surfactant is preferably a fluorine-based surfactant. By containing a fluorine-based surfactant in the colored photosensitive composition, the liquid characteristics (particularly, fluidity) can be further improved, and the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.

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. The surfactant may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.

<UV absorber>
The colored photosensitive composition according to the present disclosure may contain an ultraviolet absorber. As the ultraviolet absorber, a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indol compound, a triazine compound and the like can be used. For details thereof, the description of paragraphs 0052 to 0072 of JP2012-208374A, paragraphs 0317 to 0334 of JP2013-68814, and paragraphs 0061 to 0080 of JP2016-162946 can be referred to. These contents are incorporated herein by reference. Specific examples of the ultraviolet absorber include compounds having the following structures. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Chemical Co., Ltd.). Examples of the benzotriazole compound include the MYUA series (The Chemical Daily, February 1, 2016) manufactured by Miyoshi Oil & Fat Co., Ltd. Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.

The content of the ultraviolet absorber 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. Only one kind of ultraviolet absorber may be used, or two or more kinds may be used. When two or more types are used, the total amount is preferably in the above range.

<Antioxidant>
The colored photosensitive composition according to the present disclosure may contain an antioxidant. Examples of the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like. As the phenol compound, any phenol compound known as a phenolic antioxidant can be used. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable. As the above-mentioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable. Further, as the antioxidant, a compound having a phenol group and a phosphite ester group in the same molecule is also preferable. Further, as the antioxidant, a phosphorus-based antioxidant can also be preferably used. As a phosphorus-based antioxidant, tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosfepine-6 -Il] Oxy] Ethyl] amine, Tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosfepin-2-yl] ) Oxy] ethyl] amine, ethylbis phosphite (2,4-di-tert-butyl-6-methylphenyl) and the like. Commercially available antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (above, manufactured by ADEKA Corporation) and the like. Further, as the antioxidant, the compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, the compounds described in Japanese Patent No. 10-2019-0059371, and the like can also be used.

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. 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 is preferably in the above range.

<Other ingredients>
The colored photosensitive composition according to the present disclosure is, if necessary, a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer and other auxiliary agents (for example, conductive particles, a filler, a defoamer). It may contain a foaming agent, a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension adjusting agent, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical properties can be adjusted. These components are described in, for example, paragraphs 0183 and later of JP2012-003225A (paragraph 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs 0101 to JP2008-250074. The descriptions of 0104, 0107 to 0109, etc. can be taken into consideration, and these contents are incorporated in the present specification. In addition, the colored photosensitive composition according to the present disclosure may contain a latent antioxidant, if necessary. The latent antioxidant is a compound in which the part that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 ° C. to 200 ° C. in the presence of an acid / base catalyst. Examples thereof include compounds in which the protecting group is eliminated by the action and the function functions as an antioxidant. Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219. Examples of commercially available products include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation) and the like.

In addition, the colored photosensitive composition according to the present disclosure may contain a metal oxide in order to adjust the refractive index of the obtained film. Examples of the metal oxide include TiO ₂ , ZrO ₂ , Al ₂ O ₃ , SiO _{2 and the} like. The primary particle size of the metal oxide is preferably 1 nm to 100 nm, more preferably 3 nm to 70 nm, and particularly preferably 5 nm to 50 nm. The metal oxide may have a core-shell structure, and at this time, the core portion may be hollow.

Further, the colored photosensitive composition according to the present disclosure may contain a light resistance improving agent. Examples of the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029-0034 of JP-A-2017-146350, and paragraphs of JP-A-2017-129774. The compounds described in 0036 to 0037 and 0049 to 0052, the compounds described in paragraphs 0031 to 0034 and 0058 to 0059 of JP-A-2017-129674, and paragraphs 0036-0037 and 0051-0054 of JP-A-2017-122803. The compound described, the compound described in paragraphs 0025 to 0039 of WO17 / 164127, the compound described in paragraphs 0034 to 0047 of JP2017-186546A, paragraphs 0019 to 0041 of JP2015-25116A. , The compounds described in paragraphs 0101 to 0125 of JP2012-145604, the compounds described in paragraphs 0018 to 0021 of JP2012-103475A, paragraphs 0015 to JP2011-257591A. The compound described in 0018, the compound described in paragraphs 0017 to 0021 of JP-A-2011-191483, the compound described in paragraphs 0108 to 0116 of JP-A-2011-145668, paragraph 0103 of JP-A-2011-253174. Examples thereof include the compounds described in 0153.

The viscosity (25 ° C.) of the colored photosensitive composition according to the present disclosure is preferably 1 mPa · s to 100 mPa · s, for example, when a film is formed by coating. The lower limit is more preferably 2 mPa · s or more, and further preferably 3 mPa · s or more. The upper limit is more preferably 50 mPa · s or less, further preferably 30 mPa · s or less, and particularly preferably 15 mPa · s or less.

The colored photosensitive composition according to the present disclosure preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less, and 10 ppm or less, which is not bonded or coordinated with a pigment or the like. Is more preferable, and it is particularly preferable that the content is substantially not contained. According to this aspect, JP-A-2012-153996, JP-A-2000-34585, JP-A-2005-200560, JP-A-8-43620, JP-A-2004-145878, JP-A-2014- 119487, 2010-083997, 2017-090930, 2018-025612, 2018-025797, 2017-155228, 2018-36521. The effects described in the publications and the like can be obtained. Examples of the types of free metals include Na, K, Ca, Sc, Ti, Mn, Cu, Zn, Fe, Cr, Fe, Co, Mg, Al, Ti, Sn, Zn, Zr, Ga, Ge, etc. Examples thereof include Ag, Au, Pt, Cs and Bi. Further, in the colored photosensitive composition according to the present disclosure, the content of free halogen that is not bonded or coordinated with a pigment or the like is preferably 100 ppm or less, more preferably 50 ppm or less, and 10 ppm or less. It is more preferable that it is present, and it is particularly preferable that it is not substantially contained. Examples of the method for reducing free metals and halogens in the coloring composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with an ion-exchange resin.

It is also preferable that the colored photosensitive composition according to the present disclosure does not substantially contain a terephthalic acid ester.

<Container>
The container for the colored photosensitive composition according to the present disclosure is not particularly limited, and a known container can be used. In addition, as a storage container, a multi-layer bottle composed of 6 types and 6 layers of resin and 6 types of resin have a 7-layer structure for the purpose of suppressing impurities from being mixed into raw materials and colored photosensitive compositions. It is also preferable to use a bottle of plastic. Examples of such a container include the container described in JP-A-2015-123351.

<Method for preparing colored photosensitive composition>
The colored photosensitive composition according to the present disclosure can be prepared by mixing the above-mentioned components. In preparing the colored photosensitive composition, all the components may be simultaneously dissolved and / or dispersed in an organic solvent to prepare the colored photosensitive composition, and if necessary, two or more components may be appropriately added. A colored photosensitive composition may be prepared by preparing a solution or a dispersion and mixing them at the time of use (at the time of application).

Further, it is preferable to include a process of dispersing the pigment in the preparation of the colored photosensitive composition. In the process of dispersing the pigment, the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like. Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like. Further, in the pulverization of the pigment in the sand mill (bead mill), it is preferable to use beads having a small diameter and to process the pigment under the condition that the pulverization efficiency is increased by increasing the filling rate of the beads. Further, it is preferable to remove coarse particles by filtration, centrifugation or the like after the pulverization treatment. In addition, the process and disperser for dispersing pigments are "Dispersion Technology Taizen, published by Information Organization Co., Ltd., July 15, 2005" and "Dispersion technology and industrial application centered on suspension (solid / liquid dispersion system)". The process and disperser described in paragraph 0022 of Japanese Patent Application Laid-Open No. 2015-157893, "Practical Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be preferably used. Further, in the process of dispersing the pigment, the particles may be miniaturized in the salt milling step. For the materials, equipment, processing conditions, etc. used in the salt milling step, for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.

In preparing the colored photosensitive composition, it is preferable to filter the colored photosensitive composition with a filter for the purpose of removing foreign substances and reducing defects. As the filter, any filter conventionally used for filtration or the like can be used without particular limitation. For example, fluororesins such as polytetrafluoroethylene (PTFE), polyamide resins such as nylon (eg, nylon-6, nylon-6,6), and polyolefin resins such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight). A filter using a material such as (including the polyolefin resin of) is mentioned. Among these materials, polypropylene (including high-density polypropylene) and nylon are preferable.

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. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably. For the pore size value of the filter, the nominal value of the filter manufacturer can be referred to. As the filter, various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (formerly Japan Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc. can be used. it can.

It is also preferable to use a fibrous filter medium as the filter. Examples of the fibrous filter medium include polypropylene fiber, nylon fiber, glass fiber and the like. Examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Loki Techno Co., Ltd.

When using a filter, different filters (for example, a first filter and a second filter) may be combined. At that time, the filtration with each filter may be performed only once or twice or more. Further, filters having different pore diameters may be combined within the above-mentioned range. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration with the second filter may be performed.

(Hardened 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 a color filter or the like. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more specifically, it can be preferably used as a green colored layer (green pixel) of a color filter.
The cured product according to the present disclosure is preferably a film-like cured product, and the film thickness thereof can be appropriately adjusted according to the intended purpose. For example, the film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and further preferably 0.3 μm or more.

(Color filter)
The color filter according to the present disclosure includes the cured product according to the present disclosure described above. More preferably, the pixel of the color filter has a cured product according to the present disclosure. The color filter according to the present disclosure can be used for a solid-state image sensor such as a CCD (charge coupling element) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.

The color filter according to the present disclosure may further have pixels (hereinafter, also referred to as other pixels) different from the cured product (pixels) according to the present disclosure. Examples of other pixels include red pixels, blue pixels, yellow pixels, cyan pixels, magenta pixels, transparent pixels, black pixels, near-infrared transmission filter pixels, and the like.

In the color filter according to the present disclosure, the film thickness of the film made of the cured product according to the present disclosure can be appropriately adjusted according to the purpose. The film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and further preferably 0.3 μm or more.

The color filter according to the present disclosure preferably has a pixel width of 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. Further, the Young's modulus of the pixel (the cured product according to the present disclosure) is preferably 0.5 GPa to 20 GPa, more preferably 2.5 GPa to 15 GPa.

It is preferable that each pixel included in the color filter according to the present disclosure has high flatness. Specifically, the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less. The lower limit is not specified, but it is preferably 0.1 nm or more, for example. The surface roughness of the pixels can be measured using, for example, AFM (Atomic Force Microscope) Measurement 3100 manufactured by Veeco. Further, the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 ° to 110 °. The contact angle can be measured using, for example, a contact angle meter CV-DT · A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, it is preferred that the volume resistivity value of the pixel is 10 ⁹ Ω · cm or more, and more preferably 10 ¹¹ Ω · cm or more. The upper limit is not specified, but it is preferably 10 ¹⁴ Ω · cm or less, for example. The volume resistance value of the pixel can be measured using, for example, an ultra-high resistance meter 5410 (manufactured by Advantest).

Further, the color filter according to the present disclosure may be provided with a protective layer on the surface of the cured product according to the present disclosure. By providing the protective layer, various functions such as oxygen blocking, low reflection, prohydrophobicity, and shielding 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, more preferably 0.1 μm to 5 μm. Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, and a method of attaching the molded resin with an adhesive. The components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and 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 Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al ₂ O ₃ , Mo, SiO ₂ , Si ₂ N _{4, and the} like, and two or more of these components may be contained, for example. In the case of a protective layer for the purpose of blocking oxygen, the protective layer preferably contains a polyol resin, SiO ₂ , and Si ₂ N ₄ . Further, in the case of a protective layer for the purpose of reducing reflection, the protective layer preferably contains a (meth) acrylic resin or a fluororesin.

When the resin composition is applied to form the protective layer, a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition. As the organic solvent contained in the resin composition, a known organic solvent (for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.) can be used. When the protective layer is formed by a chemical vapor deposition method, the chemical vapor deposition method is a known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). Can be used

The protective layer contains organic / inorganic particles, an absorbent of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, and other additives, if necessary. You may. Examples of organic / inorganic particles include polymer particles (eg, silicone resin particles, polystyrene particles, melamine resin microparticles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and oxynitride. Examples thereof include titanium, magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like. A known absorber can be used as the absorber having a specific wavelength. Examples of the ultraviolet absorber and the near-infrared absorber include the above-mentioned materials. The content of these additives can be adjusted as appropriate, but is preferably 0.1% by mass to 70% by mass, more preferably 1% by mass to 60% by mass, based on the total weight of the protective layer.
Further, as the protective layer, the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.

<Manufacturing method of color filter>
The color filter according to the present disclosure includes 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 colored photosensitive composition by a photolithography method or a dry etching method. It can be manufactured through a step of forming a pattern on a material layer.

-Photolithography-
Pattern formation by the photolithography method includes a step of forming a colored photosensitive composition layer on a support using the colored photosensitive composition according to the present disclosure, and a step of exposing the colored photosensitive composition layer in a pattern. It is preferable to include a step of developing and removing an unexposed portion 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 (pixels) (post-baking step) may be provided.

In the step of forming the colored photosensitive composition layer, the colored photosensitive composition layer according to the present disclosure is used to form the colored photosensitive composition layer on the support. The support is not particularly limited and may be appropriately selected depending on the intended use. For example, a glass substrate, a silicon substrate, and the like can be mentioned, and a silicon substrate is preferable. Further, a charge coupling element (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate. In addition, a black matrix that separates each pixel may be formed on the silicon substrate. Further, the silicon substrate may be provided with an undercoat layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.

A known method can be used as a method for applying the colored photosensitive composition. 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-wet method (for example, JP-A-2009-145395). Methods described in the publication); Inkjet (for example, on-demand method, piezo method, thermal method), ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc. Various printing methods; transfer method using a mold or the like; nanoimprint method and the like can be mentioned. The method of application to an inkjet is not particularly limited, and for example, the method shown in "Expandable / Usable Inkjet-Infinite Possibilities Seen in Patents-, Published in February 2005, Sumi Betechno Research" (especially from page 115) 133), and the methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Regarding the method of applying the colored photosensitive composition, the description of International Publication No. 2017/030174 and International Publication No. 2017/018419 can be referred to, and these contents are incorporated in the present specification.

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, or 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. Pre-baking can be performed on a hot plate, an oven, or the like.

Next, the colored photosensitive composition layer is exposed in a pattern (exposure step). For example, the colored photosensitive composition layer can be exposed in a pattern by exposing it through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.

Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm), ArF line (wavelength 193 nm), and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.

Further, at the time of exposure, light may be continuously irradiated for exposure, or pulsed irradiation may be performed for exposure (pulse exposure). The pulse exposure is an exposure method of a method in which light irradiation and pause are repeated in a short cycle (for example, millisecond level or less). In the case of pulse exposure, the pulse width is preferably 100 nanoseconds (ns) or less, more preferably 50 nanoseconds or less, and even more preferably 30 nanoseconds or less. The lower limit of the pulse width is not particularly limited, but may be 1 femtosecond (fs) or more, and may be 10 femtoseconds or more. The frequency is preferably 1 kHz or higher, more preferably 2 kHz or higher, and even more preferably 4 kHz or higher. The upper limit of the frequency is preferably 50 kHz or less, more preferably 20 kHz or less, and further preferably 10 kHz or less. Maximum instantaneous intensity is preferably 50,000,000 W / m ² or more, more preferably 100 million W / m ² or more, more preferably 200 million W / m ² or more. The upper limit of the maximum instantaneous intensity is preferably 1000000000 W / m ² or less, more preferably 800 million W / m ² or less, and more preferably 500 million W / m ² or less. The pulse width is the time during which light is irradiated in the pulse period. The frequency is the number of pulse cycles per second. Further, the maximum instantaneous illuminance is the average illuminance within the time during which the light is irradiated in the pulse period. The pulse cycle is a cycle in which light irradiation and pause in pulse exposure are one cycle.

Irradiation dose (exposure dose) is ^preferably 0.03J / cm 2 ~ 2.5J / cm 2, 0.05J / cm 2 ~ 1.0J / cm 2 is more preferable. The oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment), or may be exposed in a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume. The exposure illuminance can be set as appropriate, preferably 1,000 W / m ² to 100,000 W / m ² (for example, 5,000 W / m ² , 15,000 W / m ² , or 35, It can be selected from the range of 000 W / m ² ). Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10,000 W / ^{m 2} at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20,000W / ^{m 2.}

Next, the unexposed portion of the colored photosensitive composition layer is developed and removed to form a pattern (pixel). Development and removal of the unexposed portion of the coloring composition layer can be performed using a developing solution. As a result, the colored photosensitive composition layer in the unexposed portion in the exposure step is eluted in the developing solution, and only the photocured portion remains. As the developing solution, an organic alkaline developing solution that does not cause damage to the underlying elements and circuits is preferable. The temperature of the developing solution is preferably 20 ° C. to 30 ° C. The development time is preferably 20 seconds to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developing solution every 60 seconds and further supplying a new developing solution may be repeated several times.

The developer is preferably an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water. Examples of the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide. , Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic substances. Examples thereof include alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate. As the alkaline agent, a compound having a large molecular weight is preferable in terms of 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. In addition, the developer may further contain a surfactant. Examples of the surfactant include the above-mentioned surfactants, and nonionic surfactants are preferable. From the viewpoint of convenience of transfer and storage, the developer may be once produced as a concentrated solution and diluted to a concentration required for use. The dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Further, it is preferable that the rinsing is performed by supplying the rinsing 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 discharging the rinse liquid from the central portion of the support to the peripheral edge of the support. At this time, when moving the nozzle from the central portion of the support to the peripheral portion, the nozzle may be moved while gradually reducing the moving speed. By rinsing in this way, in-plane variation of rinsing can be suppressed. Further, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the central portion to the peripheral portion of the support.

It is preferable to perform additional exposure treatment or heat treatment (post-baking) after development and drying. Additional exposure treatment and post-baking are post-development curing treatments to complete the curing. The heating temperature in the post-baking is preferably 100 ° C. to 240 ° C., more preferably 200 ° C. to 240 ° C. Post-baking can be performed on the developed film in a continuous or batch manner by using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high frequency heater so as to meet the above conditions. .. When the additional exposure process is performed, the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 201701122130.

-Dry etching method-
In the pattern formation by the dry etching method, a colored photosensitive composition layer is formed on the support using the colored photosensitive composition according to the present disclosure, and the entire colored photosensitive composition layer is cured to obtain a cured product. A step of forming a layer, a step of forming a photoresist layer on the cured product layer, a step of exposing the photoresist layer in a pattern and then developing to form a resist pattern, and using this resist pattern as a mask. It is preferable to include a step of dry etching the cured product layer with an etching gas. In forming the photoresist layer, it is preferable to further perform a prebaking treatment. In particular, as a process for forming the photoresist layer, it is desirable to carry out a heat treatment after exposure and a heat treatment (post-baking treatment) after development. Regarding the pattern formation by the dry etching method, the description in paragraphs 0010 to 0067 of JP2013-064993A can be referred to, and this content is incorporated in the present specification.

(Solid image sensor)
It is preferable that the solid-state image sensor according to the present disclosure includes the cured product according to the present disclosure and has the color filter according to the present disclosure. The configuration of the solid-state image sensor according to the present disclosure is not particularly limited as long as it includes the cured product according to the present disclosure and functions as a solid-state image sensor, and examples thereof include the following configurations.

On the substrate, there are a plurality of photodiodes constituting the light receiving area of a solid-state image sensor (CCD (charge coupling element) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and a transfer electrode made of polysilicon or the like. A device protective film made of silicon nitride or the like formed on the photodiode and the transfer electrode so as to have a light-shielding film in which only the light-receiving part of the photodiode is opened, and to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. The configuration has a color filter on the device protective film. Further, a configuration having a condensing means (for example, a microlens or the like; the same applies hereinafter) on the device protective film under the color filter (near the substrate), a configuration having a condensing means on the color filter, and the like There may be. Further, the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern. In this case, the partition wall preferably has a low refractive index for each colored pixel. Examples of the imaging device having such a structure include the devices described in JP-A-2012-227478, JP-A-2014-179757, and International Publication No. 2018/043654. The image pickup device provided with the solid-state image pickup device according to the present disclosure can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones, etc.), but also for in-vehicle cameras and surveillance cameras.
Further, as described in Japanese Patent Application Laid-Open No. 2019-21159, the solid-state image sensor according to the present disclosure is provided with an ultraviolet absorbing layer (UV cut filter) in the structure of the solid-state image sensor to withstand the light of a color filter. The sex may be improved.

(Image display device)
It is preferable that the image display device according to the present disclosure includes the cured product according to the present disclosure and has 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. For details on the definition of image display devices and details of each image display device, see, for example, "Electronic Display Device (Akio Sasaki, Kogyo Chosakai Co., Ltd., published in 1990)", "Display Device (by Junaki Ibuki, Industrial Books) Co., Ltd. (issued in 1989) ”. Further, the liquid crystal display device is described in, for example, "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)". The liquid crystal display device is not particularly limited, and examples thereof include various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".

Hereinafter, the present disclosure will be described in detail with reference to Examples, but the present disclosure is not limited thereto.
In this embodiment, "%" and "parts" mean "mass%" and "parts by mass", respectively, unless otherwise specified. In the polymer compound, the molecular weight is the weight average molecular weight (Mw), and the ratio of the constituent units is the molar percentage, except for those specified specifically.
The weight average molecular weight (Mw) is a value measured as a polystyrene-equivalent value by a gel permeation chromatography (GPC) method.

<Synthesis method of A-18>
-Monomer synthesis process-
In a three-necked flask, 12.4 g of dimethoxyphenol and 13.5 g of dibromoethanol were dissolved in 100 mL of acetone. 27.6 g of potassium carbonate was added, and the mixture was heated under reflux at 60 ° C. for 4 hours. The obtained reaction solution was extracted with ethyl acetate, washed with water, and then the organic layer was dried over magnesium sulfate. The solvent was distilled off to obtain 14.9 g (yield 89%) of 2- (4-methoxyphenoxy) ethane-1-ol.

In a three-necked flask, 8.4 g of 2- (4-methoxyphenoxy) ethane-1-ol was dissolved in 100 mL of methanol and cooled to 0 ° C. To this, 40 g of iodine monochloride was added, and the mixture was stirred at 70 ° C. for 4 hours. The solid was cooled to 0 ° C. again and the precipitated solid was collected by filtration. Reslurry purification with methanol gave 15.2 g (yield 74%) of 2- (2,5-diiodo-4-methoxyphenoxy) ethane-1-ol.

5.3 g of 2- (2,5-diiodo-4-methoxyphenoxy) ethane-1-ol was added to a three-necked flask and dissolved in tetrahydrofuran. After replacing the inside of the flask with nitrogen, 13.5 g of sodium methoxide, 0.5 g of diphenylphosphinopherocene and 0.2 g of palladium acetate were added. Then, 17.3 g of marron nitrile was added dropwise at room temperature (25 ° C., the same applies hereinafter) over 30 minutes. After completion of the dropping, the mixture was heated and stirred at 65 ° C. for 8 hours, and then the reaction solution was dropped into a 1N (= 1 mol / L) hydrochloric acid aqueous solution cooled to 0 ° C. for crystallization. The obtained solid was collected by filtration to give 4.4 g (yield 60%) of 2,2'-(2- (2-hydroxyethoxy) -5-methoxy-1,4-phenylene) dimarononitrile.

2.2 g of 2,2'-(2- (2-hydroxyethoxy) -5-methoxy-1,4-phenylene) dimarononitrile was charged into a three-necked flask and dispersed in 50 mL of acetonitrile and 5 mL of pure water. This was cooled to 0 ° C., 2.0 g of bromine was added, and the mixture was reacted at room temperature for 4 hours. The obtained solid is collected by filtration and washed with pure water to turn 2,2'-(2- (2-hydroxyethoxy) -5-methoxycyclohexa-2,5-diene-1,4-diylidene) dimarononitrile in red. 2.0 g was obtained as a solid. (Yield 98%)

1.0 g of 2,2'-(2- (2-hydroxyethoxy) -5-methoxycyclohexa-2,5-diene-1,4-diylidene) dimarononitrile in a three-necked flask is N, N'-dimethylacetamide. 0.5 g of pyridine was added. After replacing the inside of the flask with nitrogen, the flask was cooled to 0 ° C., 0.5 g of acrylic acid chloride was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was crystallized from pure water cooled to 0 ° C., and the obtained powder was recrystallized from diisopropyl ether to 2-((3,6-bis (dicyanomethylene) -4-methoxycyclohexa-1,4. -Diene-1-yl) oxy) ethyl acrylate (A-18) was obtained as 0.56 g (yield 68%) of a red solid.

<Synthesis method of A-1 to A-17 and A-19 to A-39>
For A-1 to A-17 and A-19 to A-39, the same conditions were used except for changing the components corresponding to A-18 described above.

<Oxidizing agent HOMO-LUMO>
The oxidizing agent HOMO-LUMO was measured according to the following method and evaluated according to the following evaluation criteria. The evaluation results are shown in the column of Table 1.
The HOMO of each compound was measured as follows.
The ionization potential of each 5 mg of each compound was measured by an atmospheric photoelectron spectrometer (AC-3, manufactured by RIKEN Keiki Co., Ltd.), and the value was taken as HOMO.
Each 20 mg compound was dissolved in 200 mL of toluene, and toluene was added to 2 mL of this solution to prepare 50 mL. The absorbance of this solution was measured using a Cary5000 UV-Vis-NIR spectrophotometer (manufactured by Azilent Technology) in the wavelength range of 200 nm to 800 nm, the absorption edge at a wavelength of 400 nm to 700 nm was calculated, and the value was S0. The −S1 transition energy gap (HOMO-LUMO energy difference: ΔE) was used. LUMO was calculated by the following formula.
LUMO = HOMO + ΔE

<Preparation of green dispersion G-1>
Pigments (G pigment (green pigment PG36): 8.29 parts by mass, Y pigment (yellow pigment PY185): 2.07 parts by mass), the following pigment derivative S-1: 0.5 parts by mass, and the following dispersant P -1 30% by mass PGMEA (propylene glycol monomethyl ether acetate) solution: After mixing 30 parts by mass and 71.92 parts by mass of PGMEA, add 230 parts by mass of zirconia beads having a diameter of 0.3 mm to make a paint shaker. The mixture was subjected to a dispersion treatment for 5 hours, and the beads were separated by filtration to produce a green dispersion liquid G-1.

<Preparation of green dispersions G-2 to G-12>
Green dispersions G-2 to G-12 were produced in the same manner as in the preparation of the green dispersion G-1, except that the components and contents shown in Table 2 were changed.
In Table 2, the description such as "PG36 PG58 (50/50)" means that PG36 and PG58 were used so as to have a mass ratio of 50:50.

The details of the abbreviations shown in Table 2 are shown below.

<Green pigment (G pigment)>
PG36: C.I. I. Pigment Green 36
PG58: C.I. I. Pigment Green 58
PG7: C.I. I. Pigment Green 7

<Yellow pigment (Y pigment)>
PY150: C.I. I. Pigment Yellow 150
PY185: C.I. I. Pigment Yellow 185

Pigment derivatives S-1 to S-3: The following compounds

Dispersant P-1: A 30 mass% propylene glycol monomethyl ether acrylate (PGMEA) solution of a resin having the following structure. The numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units. Mw: 20,000.

Dispersant P-2: A 30% by mass PGMEA solution of a resin having the following structure. The numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units. Mw: 28,000. In the formula, r = 15, s = 63, t = 5, u = 17, n = 9.

Dispersant P-3: A 30% by mass PGMEA solution of a resin having the following structure. The numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units. Mw: 22,000.

<Preparation of green dispersion G-13>
A green dispersion G-13 was prepared in the same manner as in the preparation of the green dispersion G-1, except that 71.92 parts by mass of propylene glycol monomethyl ether (PGME) was used instead of 71.92 parts by mass of PGMEA.

<Preparation of green dispersion G-14>
A green dispersion G-14 was prepared in the same manner as in the preparation of the green dispersion G-1, except that 71.92 parts by mass of cyclohexanone (ANON) was used instead of 71.92 parts by mass of PGMEA.

<Preparation of red dispersion R-1>
C. I. Pigment Red 254 at 9.6 parts by mass, C.I. I. A mixed solution containing 4.3 parts by mass of Pigment Yellow 139, 6.8 parts by mass of a dispersant (DISPERBYK-161, manufactured by BYK Chemie), and 79.3 parts by mass of PGMEA was added to a bead mill (zirconia beads 0. 3 mm diameter) was further mixed and dispersed for 3 hours. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm ³ . This dispersion treatment was repeated 10 times to obtain a red (Red) dispersion liquid R-1.

<Preparation of blue dispersion B-1>
C. I. Pigment Blue 15: 6 at 9.7 parts by mass, C.I. I. A bead mill (zirconia beads 0. 3 mm diameter) was further mixed and dispersed for 3 hours. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm ³ . This dispersion treatment was repeated 10 times to obtain a blue dispersion liquid B-1.

(Examples 1 to 58 and Comparative Examples 1 to 3)
<Preparation of colored photosensitive composition>
The following raw materials were mixed to produce a colored photosensitive composition.
-Compound A or comparative compound shown in Table 3 or Table 4: Amount shown in Table 3 or Table 4-Dispersion solution shown in Table 3 or Table 4: 39.4 parts by mass-Resin D1: 0.58 parts by mass .. Resin with the following structure. The numerical value added to the main chain is the molar ratio. Mw = 11,000.

-Polymerizable compound E1 (KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd.): 0.54 parts by mass-Photopolymerization initiator shown in Table 3 or Table 4: Amount shown in Table 3 or Table-Surfactant H1: 4.17 parts by mass. A 1% by mass PGMEA solution of the following mixture (Mw = 14,000). In the following formula,% indicating the ratio of the constituent units is mol%. Further, a, b and c each represent the number of repetitions of each structural unit.

-P-methoxyphenol: 0.0006 parts by mass-PGMEA: 7.66 parts by mass

-Polymerizable compound E1: KAYARAD DPHA (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate, manufactured by Nippon Kayaku Co., Ltd.)

<Formation of cured film>
The obtained colored photosensitive composition was spin-coated on a glass substrate so that the film thickness after post-baking was 0.6 μm, dried on a hot plate at 100 ° C. for 120 seconds, and then hot at 200 ° C. A cured film was formed by heat treatment (post-baking) for 300 seconds using a plate.
The following evaluation was performed using the obtained colored photosensitive composition or a cured film. The evaluation results are shown in Table 3 or Table 4.

<Evaluation of weight loss inhibitory property (membrane loss inhibitory property)>
The film thickness after exposure and the film thickness after post-baking in the formation of the cured film were measured with a stylus type film thickness meter, and the amount of change in film thickness was evaluated according to the following evaluation criteria from the difference. It can be said that the smaller the amount of change in film thickness, the more the film loss is suppressed, and the evaluation criteria A, B or C are preferable.
-Evaluation criteria-
A: The amount of change in film thickness was less than 1%.
B: The amount of change in film thickness was 1% or more and less than 2%.
C: The amount of change in film thickness was 2% or more and less than 5%.
D: The amount of change in film thickness was 5% or more and less than 10%.
E: The amount of change in film thickness was 10% or more.

<Evaluation of pattern linearity>
In each Example or Comparative Example, the colored photosensitive composition was applied by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a composition layer having a film thickness of 0.5 μm. An i-line stepper FPA-3000i5 + (manufactured by Canon Inc.) was used for this composition layer, and the i-line was exposed to 100 mJ / cm ² through a photomask in which a 300 μm line and space pattern was formed. Irradiated in quantity. 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. Then, it was rinsed with water in a spin shower, and further washed with pure water. Then, the water droplets were blown off with high-pressure air, the silicon wafer was naturally dried, and then post-baked at 220 ° C. for 300 seconds using a hot plate to form a pattern.
Using an optical microscope MT-3600LW (manufactured by FLOVEL), the line width of the obtained pattern was measured at 255 points. 3σ (three times the standard deviation) of the above 255 data was calculated and evaluated according to the following evaluation criteria. Evaluation criteria A, B or C are preferable.
-Evaluation criteria-
A: The linear width of 300 μm, 3σ, was less than 1 μm.
B: The linear width of 300 μm, 3σ, was 1 μm or more and less than 2 μm.
C: The linear width of 300 μm, 3σ, was 2 μm or more and less than 5 μm.
D: The linear width of 300 μm, 3σ, was 5 μm or more and less than 10 μm.
E: The linear width of 300 μm, 3σ, was 10 μm or more.

<Sensitivity>
CT-4000 (manufactured by Fujifilm Electronics Materials Co., Ltd.) is applied on a silicon wafer by the spin coating method so that the film thickness is 0.1 μm, and heated at 220 ° C. for 1 hour using a hot plate. Formed a stratum. The colored photosensitive composition obtained on the silicon wafer with the base layer is applied by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a composition layer having a film thickness of 0.5 μm. Got For this composition layer, an i-line stepper FPA-3000i5 + (manufactured by Canon Inc.) was used, and square pixels having a side of 0.6 μm were arranged in a 4 mm × 3 mm region on the substrate via a mask pattern. , irradiated with light of a wavelength of 365 nm, was exposed at 50 mJ / cm ² intervals at exposure ^{50mJ / cm 2 ~ 2,000mJ / 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. Then, it was rinsed with water in a spin shower, and further washed with pure water. Then, the water droplets were blown off with high-pressure air, the silicon wafer was naturally dried, and then post-baked at 220 ° C. for 300 seconds using a hot plate to form a pattern.
The optimum exposure amount (mJ / cm ² ) for resolving the coloring pattern (0.6 μm square pixel pattern) was determined, and this was used as the sensitivity. Evaluation criteria A, B or C are preferable.
-Evaluation criteria-
A: The optimum exposure amount was less than 50 mJ / cm ² .
B: The optimum exposure amount was 50 mJ / cm ² or more and less than 100 mJ / cm ² .
C: The optimum exposure amount was 100 mJ / cm ² or more and less than 200 mJ / cm ² .
D: The optimum exposure amount was 200 mJ / cm ² or more and less than 500 mJ / cm ² .
E: The optimum exposure amount was 500 mJ / cm ² or more.

(Example 59)
Same as in Example 1 except that the polymerizable compound E2 (KAYARAD TMPTA, manufactured by Nippon Kayaku Co., Ltd., trimethylolpropane triacrylate) was used instead of the polymerizable compound E1 (DPHA) in Example 1. , A colored photosensitive composition and a cured film were prepared. Moreover, it was evaluated in the same manner as in Example 1.

(Example 60)
Colored photosensitive composition in the same manner as in Example 1 except that 0.32 parts by weight of the polymerizable compound E1 (DPHA) was used instead of 0.54 parts by mass of the polymerizable compound E1 (DPHA) in Example 1. A compound and a cured film were prepared. Moreover, it was evaluated in the same manner as in Example 1.

(Example 61)
Colored photosensitive in the same manner as in Example 1 except that a mixture of the polymerizable compound E1 and the polymerizable compound E4 in a mass ratio of 50/50 was used instead of the polymerizable compound E1 (DPHA) in Example 1. A composition and a cured film were prepared. Moreover, it was evaluated in the same manner as in Example 1.

-Polymerizable compound E4: A compound having the following structure

Details of abbreviations other than those described above in Table 3 or Table 4 are shown below.

-Comparative compound A'-1: dichlorodicyanobenzoquinone-A'-2: 6,13-pentacenequinone

<Photopolymerization initiator>
F-1: IRGACURE 369 (manufactured by BASF) (molar extinction coefficient at 365 nm 800 L · mol ^-1 · cm ^-1 )
F-2: IRGACURE 819 (manufactured by BASF) (molar extinction coefficient at 365 nm 500 L · mol ^-1 · cm ^-1 )
F-3: IRGACURE 907 (manufactured by BASF) (molar extinction coefficient at 365 nm 1,100 L · mol ^-1 · cm ^-1 )
F-4: IRGACURE OXE01 (manufactured by BASF) (molar extinction coefficient at 365 nm 1,500 L · mol ^-1 · cm ^-1 )
F-5: IRGACURE OXE02 (manufactured by BASF) (molar extinction coefficient at 365 nm 3,500 L · mol ^-1 · cm ^-1 )
F-6: A compound having the following structure

Note that F-1 to F-3 are not oxime compounds, and F-4 to F-6 are oxime compounds.

(Example 101-Example 161)
The Green composition was applied onto a silicon wafer by a spin coating method so that the film thickness after film formation was 1.0 μm. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), exposure was performed at 1,000 mJ / cm ² through a mask with a 2 μm square dot pattern. Then, paddle development was carried out at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Then, it was rinsed with a spin shower and further washed with pure water. The Green composition was then patterned on a silicon wafer by heating at 200 ° C. for 5 minutes using a hot plate. Similarly, the Red composition and the Blue composition were sequentially patterned to form red, green and blue coloring patterns (Bayer patterns).
In Examples 101 to 140 and Examples 153 to 161, the colored photosensitive compositions prepared in Examples 1 to 40 or 53 to 61 are used as the Green composition. used.
In Examples 141 to 146, the colored photosensitive compositions prepared in Examples 41 to 46 were used as the Red composition.
In Examples 147 to 152, the colored photosensitive compositions prepared in Examples 47 to 52 were used as the Blue composition.
Examples of Examples 101 to 161 in which a solid-state image sensor was formed using the colored photosensitive compositions prepared in Examples 1 to 61 as a Green composition, a Red composition, or a Blue composition, respectively. Each is applicable.
The Red composition and the Blue composition will be described later.
The Bayer pattern is a red element, two green elements, and one blue element, as disclosed in US Pat. No. 3,971,065. ) This is a pattern in which a 2 × 2 array of color filter elements having an element is repeated.
The obtained color filter was incorporated into a solid-state image sensor according to a known method. Regardless of which of the colored photosensitive compositions obtained in Examples 1 to 61 is used, the solid-state image sensor is excellent in weight reduction inhibitory property (film loss inhibitory property) in the cured film, and is suitable for image recognition. It was confirmed that a solid-state image sensor with the ability was obtained.

The Green composition, Red composition, and Blue composition other than the above-mentioned colored photosensitive composition used in Examples 101 to 161 are as follows.

-Red composition-
The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 μm to prepare a Red composition.
Red pigment dispersion: 51.7 parts by mass Resin 4 (40% by mass PGMEA solution): 0.6 parts by mass Polymerizable compound 4: 0.6 parts by mass Photopolymerization initiator 1: 0.3 parts by mass Surfactant 1 : 4.2 parts by mass PGMEA: 42.6 parts by mass

-Blue composition-
The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 μm 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 Photoinitiator 1 : 0.8 parts by mass Surfactant 1: 4.2 parts by mass PGMEA: 45.8 parts by mass

The raw materials used for the Red composition and the Blue composition are as follows.

-Red pigment dispersion C. I. Pigment Red 254 at 9.6 parts by mass, C.I. I. A mixed solution consisting of 4.3 parts by mass of Pigment Yellow 139, 6.8 parts by mass of a dispersant (DISPERBYK-161, manufactured by BYK Chemie), and 79.3 parts by mass of PGMEA was used in a bead mill (zirconia beads 0.3 mm diameter). ) Was mixed and dispersed for 3 hours to prepare a pigment dispersion. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm ³ . This dispersion treatment was repeated 10 times to obtain a Red pigment dispersion.

-Blue pigment dispersion C. I. Pigment Blue 15: 6 at 9.7 parts by mass, C.I. I. A mixed solution consisting of 2.4 parts by mass of Pigment Violet 23, 5.5 parts of dispersant (Disperbyk-161, manufactured by BYK Chemie), and 82.4 parts of PGMEA was prepared by a bead mill (zirconia beads 0.3 mm diameter). A pigment dispersion was prepared by time mixing and dispersion. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm ³ . This dispersion treatment was repeated 10 times to obtain a Blue pigment dispersion.

-Polymerizable compound 1: KAYARAD DPHA (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate, manufactured by Nippon Kayaku Co., Ltd.)
-Polymerizable compound 4: The following structure

Resin 4: The following structure (acid value: 70 mgKOH / g, Mw = 11,000, the subscripts in parentheses indicating each structural unit represent the content ratio (molar ratio) of each structural unit.

-Photopolymerization initiator 1: IRGACURE-OXE01 (1- [4- (phenylthio) phenyl] -1,2-octanedione-2- (o-benzoyl oxime), manufactured by BASF)

Surfactant 1: 1 mass% PGMEA solution of the following mixture (Mw = 14,000). In the following formula, the unit of% (62% and 38%) indicating the ratio of the constituent units is mass%.

The disclosure of Japanese Patent Application No. 2019-05018, filed March 18, 2019, is incorporated herein by reference in its entirety.
All documents, patent applications, and technical standards described herein are to the same extent as if the individual documents, patent applications, and technical standards were specifically and individually stated to be incorporated by reference. Is incorporated herein by reference.

Claims

Compound A, which has a polymerizable group and has an energy level LUMO of the lowest empty orbit of less than -3.5 eV.
Colorant,
Polymerizable compounds and
A colored photosensitive composition containing a photopolymerization initiator.
A compound having a polymerizable group and having at least one structure selected from the group consisting of a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene imide structure, a perylene imide structure, a pyrazine quinoxaline structure, and a fullerene structure. A,
Colorant,
Polymerizable compounds and
A colored photosensitive composition containing a photopolymerization initiator.
Claim that the compound A is a compound having at least one structure selected from the group consisting of a quinone structure, a quinodimethane structure, a dithiolene structure, a naphthalene diimide structure, a perylene diimide structure, a pyrazinoquinoxaline structure, and a fullerene structure. The colored photosensitive composition according to 1.
The colored photosensitive composition according to claim 1 or 2, wherein the polymerizable group contained in the compound A is a radically polymerizable group or a cationically polymerizable group.
The colored photosensitive composition according to claim 4, wherein the radically polymerizable group is an acrylic group, a methacryl group, a vinyl group, a maleimide group, or an allyl group.
The colored photosensitive composition according to claim 4, wherein the cationically polymerizable group is an epoxy group, an oxetanyl group, or an allyl group.
The colored photosensitive composition according to any one of claims 1 to 6, wherein the compound A has two or more polymerizable groups in one molecule.
The colored photosensitive composition according to any one of claims 1 to 7, wherein the compound A is a compound represented by any of the following formulas (1A) to (1C).

In formulas (1A) to (1C), R 1 is independently a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a hydroxy group, an acyl group, an acyloxy group, a nitro group, or a cyano group. the expressed, the C a ~ C C each independently represent a ring structure, Y 1 is independently a single bond, an oxygen atom, a sulfur atom, NR N, carbonyl group, -OC (= O) -, - C (= O) O -, - C (= O) NH -, - OC (= O) -NH -, - Ani - Cat + -, or, -Cat + Ani - - represents, R N are each independently , Hydrogen atom, alkyl group, or aryl group, Ani − represents an anionic structure, Cat + represents a cation structure, L 1 represents a single bond or a divalent linking group, respectively, and A 1 Represents the above-mentioned polymerizable group, X 1 and X 2 independently represent an oxygen atom, a sulfur atom, or a group represented by the following formula (1X), n represents an integer of 1 or more, and m. each independently, 0 or more and represents the maximum number of substitution positions on R 1 can bind ring, p is 0 or 1.

In the formula (1X), R 2 and R 3 independently represent an electron-attracting group, and the wavy line portion represents a bonding position with the ring structure.
The colored photosensitive composition according to any one of claims 1 to 8, wherein the compound A is a compound represented by the following formula (2) or formula (3).

In the formula (2), R 21 to R 24 are independently halogen atoms, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, acyl groups, acyloxy groups, hydroxy groups, amino groups, nitro groups and amide groups. , Or the group having a polymerizable group, and R 21 and R 22 , or R 23 and R 24 may be linked to each other to form a ring, and at least one of R 21 to R 24 may be formed. , A group having a polymerizable group.
In the formula (3), R 31 to R 34 independently represent a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, an acyloxy group, a hydroxy group, an amino group, a nitro group and an amide group. , Or a group having a polymerizable group, and R 31 and R 32 , or R 33 and R 34 may be linked to each other to form a ring, and at least one of R 31 to R 34 is It is a group having a polymerizable group.
The colored photosensitive composition according to any one of claims 1 to 9, wherein the energy level HOMO of the highest occupied orbital of the compound A is more than -7.0 eV and less than -5.5 eV.
The colored photosensitive composition according to any one of claims 1 to 10, wherein the energy level LUMO of the lowest empty orbit of the compound A is more than -5.0 eV and less than -3.5 eV.
The colored photosensitive composition according to any one of claims 1 to 11, wherein the colorant contains a phthalocyanine pigment.
The colored photosensitive composition according to any one of claims 1 to 12, wherein the photopolymerization initiator contains an oxime compound.
The colored photosensitive composition according to any one of claims 1 to 13, further comprising a polymer dispersant.
The colored photosensitive composition according to any one of claims 1 to 14, further comprising an alkali-soluble resin.
A cured product obtained by curing the colored photosensitive composition according to any one of claims 1 to 15.
A color filter comprising the cured product according to claim 16.
A solid-state image sensor having the color filter according to claim 17.
An image display device having the color filter according to claim 17.