JP2016074773A - Coloring composition, colored cured film, and display element and solid state image sensor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a coloring composition suitable for forming a thin film of a colored cured film with high brightness.SOLUTION: A coloring composition comprises (A) a colorant comprising C.I.Pigment Red 170, (B) binder resin, and (C) polymerizable compound, where the content of C.I.Pigment Red 170 is 15 mass% or more and 90 mass% or less relative to the total content of the colorant.SELECTED DRAWING: None

Description

  The present invention relates to a colored composition, a colored cured film, a display element, and a solid-state image sensor. More specifically, the present invention relates to a transmissive or reflective color liquid crystal display element, solid-state image sensor, organic EL display element, electronic paper, and the like. The present invention relates to a colored composition used for forming a colored cured film to be used, a colored cured film formed using the colored composition, and a display element and a solid-state imaging device including the colored cured film.

  In producing a color filter using a colored radiation-sensitive composition, a pigment-dispersed colored radiation-sensitive composition is applied on a substrate and dried, and then the dried coating film is irradiated with radiation in a desired pattern shape. There is known a method (for example, see Patent Documents 1 and 2) in which pixels of three primary colors of red, green, and blue are arranged on a substrate by irradiation (hereinafter referred to as “exposure”) and development. In addition, a method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (see, for example, Patent Document 3) is also known. Furthermore, a method for obtaining pixels of each color by an ink jet method using a pigment-dispersed colored resin composition is also known (for example, see Patent Document 4).

  Examples of the colorant used for forming the red pixel of the color filter include C.I. I. Pigment red 254 and C.I. I. Pigment Red 177 is widely used. It is known that a red pixel excellent in luminance can be formed by using these pigments (see, for example, Patent Documents 5 to 9).

JP-A-2-144502 JP-A-3-53201 JP-A-6-35188 JP 2000-310706 A Japanese Patent No. 3911875 Japanese Patent No. 4218999 JP 2007-124202 A JP 2007-133131 A JP 2010-048927 A

  However, in response to the recent demand for producing a colored cured film having higher brightness with a thinner film, C.I. I. Pigment red 254 and C.I. I. At present, it is not possible to sufficiently meet such a demand only by using Pigment Red 177. For this reason, there is a strong demand for the development of a coloring composition suitable for forming a colored cured film having high brightness with a thinner film.

  Accordingly, an object of the present invention is to provide a colored composition suitable for forming a colored cured film having a high luminance with a thinner film. Furthermore, the subject of this invention is providing the display element and solid-state image sensor which comprise the colored cured film formed using the said coloring composition, and this colored cured film.

  As a result of intensive studies, the present inventors have determined that C.I. I. It has been found that the above problem can be solved by using Pigment Red 170.

That is, the present invention relates to (A) C.I. I. A coloring composition containing Pigment Red 170, (B) a binder resin, and (C) a polymerizable compound,
C. I. The present invention provides a colored composition in which the content ratio of Pigment Red 170 is 15% by mass or more and 90% by mass or less with respect to the total colorant.

The present invention also provides C.I. I. Pigment Red 170,
C. I. The present invention provides a colored cured film in which the content ratio of Pigment Red 170 is 15% by mass or more and 90% by mass or less with respect to all the colorants, and a display element and a solid-state imaging device including the colored cured film. Here, the “colored cured film” means each color pixel used for a display element or a solid-state imaging element.

By using the colored composition of the present invention, it is possible not only to form a colored cured film having high luminance with a thinner film, but also to form a colored cured film having excellent color separation properties.
Therefore, the colored composition of the present invention can be used very suitably for the production of solid-state imaging devices such as color liquid crystal display devices, organic EL display devices, display devices such as electronic paper, and CMOS image sensors.

Hereinafter, the present invention will be described in detail.
Coloring composition will be described in detail components of the colored composition of the present invention.

-(A) Colorant-
The coloring composition of the present invention includes C.I. I. It is essential to include CI Pigment Red 170. The colored cured film formed using the colored composition of the present invention is suitable for a color filter of a display element or a solid-state image sensor, and particularly for a red cured film of a color filter used for an organic EL display element or a solid-state image sensor. Suitable for formation.

  The coloring composition of the present invention includes C.I. I. Although it is essential that the content ratio of CI Pigment Red 170 is 15% by mass or more and 90% by mass or less with respect to all the colorants, C.I. I. It is preferable that the content ratio of the pigment red 170 is as follows.

For example, when the colored composition of the present invention is used for forming a red cured film of a color filter used in an organic EL display element, C.I. I. The content ratio of Pigment Red 170 is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 40% by mass or more, from the viewpoint of forming a thinner red cured film with respect to all colorants. Preferably, 50% by mass or more is still more preferable, and from the viewpoint of forming a red cured film having high brightness, 85% by mass or less is preferable, 80% by mass or less is more preferable, and 77% by mass or less is more preferable.
In addition, when the colored composition of the present invention is used for forming a red cured film of a color filter used in a solid-state imaging device, C.I. I. The content ratio of Pigment Red 170 is preferably 20% by mass or more, more preferably 25% by mass or more, and more preferably 35% by mass or more from the viewpoint of producing a solid-state imaging device having good color separation with respect to all colorants. More preferably, from the viewpoint of dispersibility of the pigment, 85% by mass or less is preferable, 80% by mass or less is more preferable, and 70% by mass or less is still more preferable.

The coloring composition of the present invention includes C.I. I. A red colorant other than CI Pigment Red 170 may be contained.
Such red colorants include C.I. I. Examples thereof include red pigments other than pigment red 170 and red dyes. C. I. Examples of red pigments other than CI Pigment Red 170 include compounds classified as pigments in Color Index (CI; issued by The Society of Dyers and Colorists), that is, the following Color Index (CI. ) Can be listed.

C. I. Pigment red 1, C.I. I. Pigment red 2, C.I. I. Pigment red 5, C.I. I. Pigment red 17, C.I. I. Pigment red 31, C.I. I. Pigment red 32, C.I. I. Pigment red 41, C.I. I. Pigment red 48: 1, C.I. I. Pigment red 48: 2, C.I. I. Pigment red 48: 3, C.I. I. Pigment red 48: 4, C.I. I. Pigment red 48: 5, C.I. I. Pigment red 49, C.I. I. Pigment red 49: 1, C.I. I. Pigment red 49: 2, C.I. I. Pigment red 49: 3, C.I. I. Pigment red 52: 1, C.I. I. Pigment red 52: 2, C.I. I. Pigment red 53: 1, C.I. I. Pigment red 54, C.I. I. Pigment red 57: 1, C.I. I. Pigment red 58, C.I. I. Pigment red 58: 1, C.I. I. Pigment red 58: 2, C.I. I. Pigment red 58: 3, C.I. I. Pigment red 58: 4, C.I. I. Pigment red 60: 1, C.I. I. Pigment red 63, C.I. I. Pigment red 63: 1, C.I. I. Pigment red 63: 2, C.I. I. Pigment red 63: 3, C.I. I. Pigment red 64: 1, C.I. I. Pigment red 68, C.I. I. Pigment red 81, C.I. I. Pigment red 81: 1, C.I. I. Pigment red 122, C.I. I. Pigment red 123, C.I. I. Pigment red 144, C.I. I. Pigment red 149, C.I. I. Pigment red 166, C.I. I. Pigment red 168, C.I. I. Pigment red 171, C.I. I. Pigment red 175, C.I. I. Pigment red 176, C.I. I. Pigment red 177, C.I. I. Pigment red 178, C.I. I. Pigment red 179, C.I. I. Pigment red 180, C.I. I. Pigment red 185, C.I. I. Pigment red 187, C.I. I. Pigment red 200, C.I. I. Pigment red 202, C.I. I. Pigment red 206, C.I. I. Pigment red 207, C.I. I. Pigment red 209, C.I. I. Pigment red 214, C.I. I. Pigment red 220, C.I. I. Pigment red 221, C.I. I. Pigment red 224, C.I. I. Pigment red 237, C.I. I. Pigment red 239, C.I. I. Pigment red 242, C.I. I. Pigment red 243, C.I. I. Pigment red 247, C.I. I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. Pigment red 262, C.I. I. Pigment Red 272, etc. I. Red pigments other than Pigment Red 170.

  In addition, a red pigment represented by the following formula (1) can also be used.

Examples of red dyes include xanthene compounds, triarylmethane compounds, cyanine compounds, anthraquinone compounds, and dipyrromethene compounds. Specifically, the compound classified into the dye | dye (Dye) in the color index (CI; The Society of Dyers and Colorists company) can be illustrated.

Among them, C.I. I. Examples of red colorants other than CI Pigment Red 170 include C.I. I. Pigment red 254, C.I. I. Pigment Red 264, a diketopyrrolopyrrole pigment such as a red pigment represented by the above formula (1), C.I. I. Pigment red 166, C.I. I. Pigment red 177, C.I. I. Pigment red 224, C.I. I. Pigment Red 242 is preferred, and more preferred embodiments are as follows.
That is, when the colored composition of the present invention is used for forming a red cured film of a color filter used in an organic EL display element, C.I. I. Examples of red colorants other than CI Pigment Red 170 include C.I. I. Pigment Red 177 and diketopyrrolopyrrole pigment are more preferable. I. Pigment red 177, C.I. I. Pigment Red 254 is more preferable.
In addition, when the colored composition of the present invention is used for forming a red cured film of a color filter used in a solid-state imaging device, C.I. I. Examples of red colorants other than CI Pigment Red 170 include C.I. I. Pigment Red 242, and diketopyrrolopyrrole pigments are more preferable. I. Pigment red 242, C.I. I. Pigment Red 254 is more preferable.

The coloring composition of the present invention is C.I. I. When a red colorant other than CI Pigment Red 170 is contained, C.I. I. The content ratio of Pigment Red 170 is preferably set as follows.
When the colored composition of the present invention is used for forming a red cured film of a color filter used in an organic EL display element, C.I. I. The content ratio of Pigment Red 170 is preferably 20% by mass or more, more preferably 30% by mass or more, and more preferably 40% by mass or more from the viewpoint of forming a thinner cured red film with respect to the all red colorant. From the viewpoint of forming a high-brightness red cured film, it is preferably 90% by mass or less, more preferably 85% by mass or less, and still more preferably 80% by mass or less.
In addition, when the colored composition of the present invention is used for forming a red cured film of a color filter used in a solid-state imaging device, C.I. I. The content ratio of Pigment Red 170 is preferably 20% by mass or more, more preferably 30% by mass or more, still more preferably 40% by mass or more, still more preferably 45% by mass or more, and 99% by mass with respect to the all red colorant. % By mass or less is preferable, 95% by mass or less is more preferable, and 90% by mass or less is still more preferable. With such an embodiment, a solid-state imaging device with good color separation can be manufactured.

The colored composition of the present invention preferably further contains a yellow colorant.
Examples of such yellow colorants include yellow pigments and yellow dyes. Examples of yellow pigments include C.I. I. Pigment yellow 12, C.I. I. Pigment yellow 13, C.I. I. Pigment yellow 14, C.I. I. Pigment yellow 17, C.I. I. Pigment yellow 20, C.I. I. Pigment yellow 24, C.I. I. Pigment yellow 31, C.I. I. Pigment yellow 55, C.I. I. Pigment yellow 61, C.I. I. Pigment yellow 61: 1, C.I. I. Pigment yellow 62, C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 93, C.I. I. Pigment yellow 100, C.I. I. Pigment yellow 104, C.I. I. Pigment yellow 109, C.I. I. Pigment yellow 110, C.I. I. Pigment yellow 129, C.I. I. Pigment yellow 133, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 153, C.I. I. Pigment yellow 154, C.I. I. Pigment yellow 155, C.I. I. Pigment yellow 166, C.I. I. Pigment yellow 168, C.I. I. Pigment yellow 169, C.I. I. Pigment yellow 180, C.I. I. Pigment yellow 183, C.I. I. Pigment yellow 185, C.I. I. Pigment yellow 191, C.I. I. Pigment yellow 191: 1, C.I. I. Pigment yellow 206, C.I. I. Pigment yellow 209, C.I. I. Pigment yellow 209: 1, C.I. I. Pigment yellow 211, C.I. I. Pigment yellow 212, C.I. I. And CI Pigment Yellow 215.
As the yellow dye, a known dye exhibiting a yellow color, such as an anthraquinone dye, an azo dye, or a pyridone azo dye, can be used. Specifically, the compound classified into the dye | dye (Dye) in the color index (CI; The Society of Dyers and Colorists company) can be illustrated.

Among these, the following colorants are preferable as the yellow colorant.
When the colored composition of the present invention is used for forming a red cured film of a color filter used in an organic EL display element, C.I. I. Pigment yellow 139, C.I. I. Isoindoline pigments such as C.I. Pigment Yellow 185; I. Pigment yellow 129, C.I. I. Pigment yellow 138, C.I. I. Pigment Yellow 150 is preferable, and isoindoline pigment is more preferable. Among isoindoline pigments, C.I. I. Pigment Yellow 139 is more preferable.
When the colored composition of the present invention is used for forming a red cured film of a color filter used in a solid-state image sensor, examples of the yellow colorant include C.I. I. Pigment yellow 139, C.I. I. An isoindoline pigment such as CI Pigment Yellow 185 is preferable. I. Pigment Yellow 185 is more preferable.

When the coloring composition of this invention contains a yellow coloring agent, it is preferable to make the content rate of a yellow coloring agent into the following aspect.
For example, when the colored composition of the present invention is used for forming a red cured film of a color filter used in an organic EL display element, the content ratio of the yellow colorant is preferably more than 0% by mass with respect to the total colorant, 2 mass% or more is more preferable, 3 mass% or more is further preferable, and 30 mass% or less is preferable, 20 mass% or less is more preferable, and 10 mass% or less is still more preferable. According to such an embodiment, a colored cured film with high luminance can be formed with a thinner film.
Moreover, when using the coloring composition of this invention for formation of the red cured film of the color filter used for a solid-state image sensor, as for the content rate of a yellow coloring agent, more than 0 mass% is preferable with respect to all coloring agents, 5 More preferably 10% by weight or more, still more preferably 15% by weight or more, further preferably 40% by weight or less, more preferably 30% by weight or less, still more preferably 25% by weight or less, and further 20% by weight. % Or less is even more preferable. With such an embodiment, a solid-state imaging device with good color separation can be manufactured.

  The coloring composition of the present invention may contain other colorants other than those described above to the extent that the effects of the present invention are not affected. Specific examples include organic pigments, lake pigments, and dyes classified as pigments in the color index (CI; issued by The Society of Dyers and Colorists).

The coloring composition of this invention is used suitably for formation of a red cured film.
Especially, the organic EL display element which has a high-intensity red pixel is producible with a thin film by using for formation of the red cured film of the color filter used for an organic EL display element. Further, by using it for forming a red cured film of a color filter used in a solid-state image sensor, a solid-state image sensor having red pixels with good color separation can be produced with a thin film.

When using the coloring composition of this invention for formation of the red cured film of the color filter used for an organic EL display element, (A) As a coloring agent, C.I. I. Pigment red 170, C.I. I. Pigment red 254 and C.I. I. Pigment Red 177 or C.I. I. Pigment red 170, C.I. I. It preferably contains CI Pigment Red 254 and a yellow colorant.
(A) As a colorant, C.I. I. Pigment red 170, C.I. I. Pigment red 254 and C.I. I. When the pigment red 177 is included, it may further contain a yellow colorant, but from the viewpoint of forming a high-brightness red cured film, the content of the yellow colorant is preferably 10% by mass or less based on the total colorant. 6 mass% or less is more preferable.
Further, (A) As a colorant, C.I. I. Pigment red 170, C.I. I. When the pigment red 254 and the yellow colorant are included, other red colorants may be further included. However, from the viewpoint of forming a colored cured film having a high luminance with a thinner film, the content ratio of the other red colorants is all 10 mass% or less is preferable with respect to a coloring agent, and 5 mass% or less is more preferable. Note that C.I. I. Pigment red 170, C.I. I. Examples of the yellow colorant when CI Pigment Red 254 and a yellow colorant are included include C.I. I. Pigment yellow 139, C.I. I. Pigment Yellow 150 is preferable, and C.I. I. Pigment Yellow 139 is more preferable.

  Moreover, when using the coloring composition of this invention for formation of the red cured film of the color filter used for a solid-state image sensor, (A) As a coloring agent, C.I. I. It is preferable that Pigment Red 170 is contained in an amount of 30% by mass or more based on the total red colorant, and a yellow colorant is included in an amount of 5 to 30% by mass based on the total colorant. Furthermore, C.I. I. It is preferable that Pigment Red 170 is contained in an amount of 40% by mass or more based on the total red colorant, and a yellow colorant is included in an amount of 15 to 25% by mass based on the total colorant.

  In the present invention, C.I. I. Pigment Red 170 and other pigments optionally mixed may be used after being purified by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof. Further, these pigments may be used by modifying the particle surface with a resin, if desired. Examples of the resin that modifies the particle surface of the pigment include vehicle resins described in JP-A No. 2001-108817, and various commercially available resins for dispersing pigments. The organic pigment may be used after the primary particles are refined by so-called salt milling. As a salt milling method, for example, a method disclosed in Japanese Patent Laid-Open No. 8-179111 can be employed.

In the present invention, C.I. I. In addition to Pigment Red 170 and other colorants that are optionally mixed, at least one selected from known dispersing agents and dispersing aids may also be included.
Known dispersants include, for example, urethane dispersants, polyethylene imine dispersants, polyoxyethylene alkyl ether dispersants, polyoxyethylene alkyl phenyl ether dispersants, polyethylene glycol diester dispersants, sorbitan fatty acid ester dispersants. Dispersants, polyester-based dispersants, (meth) acrylic-based dispersants and the like can be mentioned. Examples of commercially available products include Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN22102 (above, Big Chemie BYK))) and other (meth) acrylic dispersants, Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-17 , Dispersbyk-182 (above, manufactured by BYK Corporation), urethane dispersants such as Solsperse 76500 (manufactured by Lubrizol Corporation), and polyethyleneimine dispersions such as Solsperse 24000 (manufactured by Lubrizol Corporation) Other than polyester dispersants such as the additives, Azisper PB821, Azisper PB822, Azisper PB880, Azisper PB881 (Ajinomoto Fine Techno Co., Ltd.), BYK-LPN21324 (Bikchemy (BYK) Co.) it can.

In this invention, a dispersing agent can be used individually or in mixture of 2 or more types.
In the present invention, the content of the dispersant is preferably 5 to 300 parts by mass, more preferably 10 to 200 parts by mass, and still more preferably 15 to 100 parts by mass with respect to 100 parts by mass of the (A) colorant. -50 mass parts is still more preferable.

  Examples of the dispersion aid include pigment derivatives. Specific examples of the pigment derivative include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivative of quinophthalone.

  (A) The content of the colorant is usually 5 to 70% by mass, preferably 10 to 60% by mass, more preferably in the solid content of the colored composition, from the viewpoint of forming a pixel having high luminance and excellent coloring power. Is 15 to 55% by mass, and 20 to 50% by mass is particularly preferable. Here, solid content is components other than the solvent mentioned later.

-(B) Binder resin-
Although it does not specifically limit as (B) binder resin in this invention, It is preferable that it is resin which has acidic functional groups, such as a carboxyl group and a phenolic hydroxyl group. Among them, a polymer having a carboxyl group (hereinafter also referred to as “carboxyl group-containing polymer”) is preferable. For example, an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter referred to as “unsaturated monomer”). And a copolymer of another copolymerizable ethylenically unsaturated monomer (hereinafter also referred to as “unsaturated monomer (b2)”). .

Examples of the unsaturated monomer (b1) include (meth) acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], ω-carboxypolycaprolactone mono (meta ) Acrylate, p-vinylbenzoic acid and the like.
These unsaturated monomers (b1) can be used alone or in admixture of two or more.

Moreover, as said unsaturated monomer (b2), for example,
N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide;
Aromatic vinyl compounds such as styrene, α-methylstyrene, p-hydroxystyrene, p-hydroxy-α-methylstyrene, p-vinylbenzylglycidyl ether, acenaphthylene;

Methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, polyethylene glycol (polymerization degree 2 10) methyl ether (meth) acrylate, polypropylene glycol (polymerization degree 2 to 10) methyl ether (meth) acrylate, polyethylene glycol (polymerization degree 2 to 10) mono (meth) acrylate, polypropylene glycol (polymerization degree 2 to 10) mono (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6] decan-8-yl (meth) acrylate, dicyclopentenyl (meth) acrylate Glycerol mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, ethylene oxide modified (meth) acrylate of paracumylphenol, glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, 3-[( (Meth) acrylic acid esters such as (meth) acryloyloxymethyl] oxetane, 3-[(meth) acryloyloxymethyl] -3-ethyloxetane;

Vinyl ethers such as cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, 3- (vinyloxymethyl) -3-ethyloxetane ;
Examples thereof include a macromonomer having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, and polysiloxane.
These unsaturated monomers (b2) can be used alone or in admixture of two or more.

  In the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably 5 to 50% by mass. More preferably, it is 10 to 40% by mass. By copolymerizing the unsaturated monomer (b1) in such a range, a colored composition excellent in alkali developability and storage stability can be obtained.

  Specific examples of the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2) include, for example, JP-A-7-140654, JP-A-8-259876, and JP-A-10-31308. No. 10, JP-A-10-300902, JP-A-11-174224, JP-A-11-258415, JP-A-2000-56118, JP-A-2004-101728, etc. Coalescence can be mentioned.

  In the present invention, for example, JP-A-5-19467, JP-A-6-230212, JP-A-7-207211, JP-A-9-325494, JP-A-11-140144, As disclosed in Kaikai 2008-181095 and the like, a carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acryloyl group in the side chain can also be used as a binder resin.

  The binder resin in the present invention has a polystyrene-equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran), usually 1,000 to 100,000, preferably Is 3,000 to 50,000. By setting it as such an aspect, the remaining-film rate of a film, a pattern shape, heat resistance, an electrical property, and the resolution can be improved further, and generation | occurrence | production of the dry foreign material at the time of application | coating can be suppressed at a high level.

  Further, the ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the binder resin in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3. .0. In addition, Mn here says the number average molecular weight of polystyrene conversion measured by GPC (elution solvent: tetrahydrofuran).

  The binder resin in the present invention can be produced by a known method. For example, it is disclosed in JP2003-222717A, JP2006-259680A, International Publication No. 2007/029871, etc. The structure, Mw, and Mw / Mn can be controlled by the method.

  In this invention, binder resin can be used individually or in mixture of 2 or more types.

  In the present invention, the content of the binder resin is usually 5 to 1,000 parts by mass, preferably 10 to 500 parts by mass, and more preferably 20 to 150 parts by mass with respect to 100 parts by mass of the colorant (A). . By setting it as such an aspect, in addition to the further improvement of coloring power and a brightness | luminance, alkali developability, the storage stability of a coloring composition, pattern shape, and chromaticity characteristic can be improved.

-(C) Polymerizable compound-
In the present invention, the polymerizable compound refers to a compound having two or more polymerizable groups. Examples of the polymerizable group include an ethylenically unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group. In the present invention, the polymerizable compound is preferably a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups.

  Specific examples of the compound having two or more (meth) acryloyl groups include a polyfunctional (meth) acrylate obtained by reacting an aliphatic polyhydroxy compound and (meth) acrylic acid, a polyfunctional (meta) modified with caprolactone. ) Acrylate, alkylene oxide modified polyfunctional (meth) acrylate, polyfunctional urethane (meth) acrylate obtained by reacting hydroxyl-functional (meth) acrylate and polyfunctional isocyanate, hydroxyl-functional (meth) acrylate and acid anhydride The polyfunctional (meth) acrylate which has a carboxyl group obtained by making a product react can be mentioned.

  Here, examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; and 3 such as glycerin, trimethylolpropane, pentaerythritol, and dipentaerythritol. Mention may be made of aliphatic polyhydroxy compounds having a valence higher than that. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and glycerol diester. A methacrylate etc. can be mentioned. Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. Examples of acid anhydrides include succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, dibasic acid anhydrides such as hexahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic acid. Examples thereof include dianhydrides and tetrabasic acid dianhydrides such as benzophenone tetracarboxylic dianhydride.

  Examples of the caprolactone-modified polyfunctional (meth) acrylate include compounds described in paragraphs [0015] to [0018] of JP-A No. 11-44955. The alkylene oxide-modified polyfunctional (meth) acrylate is at least one selected from bisphenol A di (meth) acrylate modified with at least one selected from ethylene oxide and propylene oxide, ethylene oxide and propylene oxide. Modified with at least one selected from trimethylolpropane tri (meth) acrylate, ethylene oxide and propylene oxide modified with at least one selected from modified isocyanuric acid tri (meth) acrylate, ethylene oxide and propylene oxide Pen modified with at least one selected from pentaerythritol tri (meth) acrylate, ethylene oxide and propylene oxide. Dipentaerythritol modified with at least one selected from dipentaerythritol penta (meth) acrylate, ethylene oxide and propylene oxide modified with at least one selected from taerythritol tetra (meth) acrylate, ethylene oxide and propylene oxide Examples include hexa (meth) acrylate.

  Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure. The melamine structure and the benzoguanamine structure refer to a chemical structure having one or more triazine rings or phenyl-substituted triazine rings as a basic skeleton, and is a concept including melamine, benzoguanamine or a condensate thereof. Specific examples of the compound having two or more N-alkoxymethylamino groups include N, N, N ′, N ′, N ″, N ″ -hexa (alkoxymethyl) melamine, N, N, N ′. , N′-tetra (alkoxymethyl) benzoguanamine, N, N, N ′, N′-tetra (alkoxymethyl) glycoluril and the like.

Among these polymerizable compounds, polyfunctional (meth) acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth) acrylic acid, caprolactone-modified polyfunctional (meth) acrylates, polyfunctional urethanes (Meth) acrylate, polyfunctional (meth) acrylate having a carboxyl group, N, N, N ′, N ′, N ″, N ″ -hexa (alkoxymethyl) melamine, N, N, N ′, N ′ -Tetra (alkoxymethyl) benzoguanamine is preferred. Among the polyfunctional (meth) acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth) acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, dipenta Among polyfunctional (meth) acrylates having a carboxyl group, erythritol hexaacrylate is obtained by reacting pentaerythritol triacrylate and succinic anhydride, and reacting dipentaerythritol pentaacrylate and succinic anhydride. The compound is particularly preferable in that the strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and background stains and film residues are hardly generated on the unexposed substrate and the light shielding layer.
In this invention, (C) polymeric compound can be used individually or in mixture of 2 or more types.

  The content of the polymerizable compound (C) in the present invention is preferably 10 to 1,000 parts by weight, more preferably 15 to 500 parts by weight, with respect to 100 parts by weight of the (A) colorant. Is preferred. By adopting such an embodiment, curability and alkali developability are further improved, and in addition to further improvement in coloring power and brightness, background stains, film residue, etc. on the unexposed substrate or on the light shielding layer Occurrence can be suppressed at a high level.

-(D) Photopolymerization initiator-
The coloring composition of the present invention can contain a photopolymerization initiator. Thereby, radiation sensitivity can be provided to a coloring composition. The photopolymerization initiator used in the present invention is a compound that generates an active species capable of initiating polymerization of the polymerizable compound by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray.

  Examples of such photopolymerization initiators include thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, α-diketone compounds, polynuclear quinone compounds, A diazo compound, an imide sulfonate compound, etc. can be mentioned.

  In this invention, a photoinitiator can be used individually or in mixture of 2 or more types. The photopolymerization initiator is preferably at least one selected from the group consisting of a thioxanthone compound, an acetophenone compound, a biimidazole compound, a triazine compound, and an O-acyloxime compound.

  Among the preferred photopolymerization initiators in the present invention, specific examples of the thioxanthone compound include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2, 4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone and the like can be mentioned.

  Specific examples of the acetophenone compound include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4- And morpholinophenyl) butan-1-one and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

  Specific examples of the biimidazole compound include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′- Bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 Examples include ', 5,5'-tetraphenyl-1,2'-biimidazole.

  In addition, when using a biimidazole compound as a photoinitiator, using a hydrogen donor together is preferable at the point which can improve a sensitivity. The term “hydrogen donor” as used herein means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure. Examples of the hydrogen donor include mercaptan hydrogen donors such as 2-mercaptobenzothiazole and 2-mercaptobenzoxazole, 4,4′-bis (dimethylamino) benzophenone, and 4,4′-bis (diethylamino) benzophenone. Mention may be made of amine hydrogen donors. In the present invention, hydrogen donors can be used alone or in admixture of two or more, but one or more mercaptan hydrogen donors and one or more amine hydrogen donors are used in combination. Is preferable in that the sensitivity can be further improved.

  Specific examples of the triazine compound include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2- (5-Methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloromethyl) ) -S-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxyphenyl) Ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-eth Triazine compounds having a halomethyl group such as cistyryl) -4,6-bis (trichloromethyl) -s-triazine and 2- (4-n-butoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine Can be mentioned.

  Specific examples of the O-acyloxime compound include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), ethanone, 1- [9-ethyl- 6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- (2-methyl-4-tetrahydrofuranylmethoxybenzoyl) ) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- {2-methyl-4- (2,2-dimethyl-1,3- And dioxolanyl) methoxybenzoyl} -9H-carbazol-3-yl]-, 1- (O-acetyloxime). As commercially available O-acyloxime compounds, NCI-831, NCI-930 (above, manufactured by ADEKA Corporation), DFI-020, DFI-091 (above, manufactured by Daito Chemix Corporation), and the like can also be used. .

  In this invention, when using photoinitiators other than biimidazole compounds, such as an acetophenone compound, a sensitizer can also be used together. Examples of such a sensitizer include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, and 4-dimethyl. Ethyl aminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4-diethylaminobenzoyl) coumarin, 4- (diethylamino) chalcone, etc. Can be mentioned.

  In the present invention, the content of the (D) photopolymerization initiator is preferably 0.01 to 120 parts by mass, more preferably 1 to 100 parts by mass, with respect to 100 parts by mass of the (C) polymerizable compound. 50 parts by mass is more preferable. By setting it as such an aspect, sclerosis | hardenability and a film characteristic can be improved more and coloring power and a brightness | luminance can be improved further.

-(E) Solvent-
The colored composition of the present invention contains the above components (A) to (C) and other components that are optionally added, but is usually prepared as a liquid composition by blending a solvent.
(E) As a solvent, as long as (A)-(C) component and other components which comprise a coloring composition are disperse | distributed or melt | dissolved, and it does not react with these components, but has moderate volatility. Can be appropriately selected and used.

Among such solvents, for example
Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n- Butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, di Propylene glycol mono Chirueteru, dipropylene glycol mono -n- propyl ether, dipropylene glycol mono -n- butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl (poly) alkylene glycol monoalkyl ethers such as ether;

Lactic acid alkyl esters such as methyl lactate and ethyl lactate;
(Cyclo) alkyl alcohols such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol, cyclohexanol;
Keto alcohols such as diacetone alcohol;

Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, (Poly) alkylene glycol monoalkyl ether acetates such as 3-methyl-3-methoxybutyl acetate;
Other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran;
Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone;

Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate;
Alkoxycarboxylic esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, 3-methyl-3-methoxybutylpropionate ;
Ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-butyric acid Other esters such as -propyl, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate;
Aromatic hydrocarbons such as toluene and xylene;
Examples include amides or lactams such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone.

  Of these solvents, (poly) alkylene glycol monoalkyl ethers, lactic acid alkyl esters, (poly) alkylene glycol monoalkyl ether acetates, and other ethers from the viewpoints of solubility, pigment dispersibility, coatability, etc. , Ketones, diacetates, alkoxycarboxylic acid esters, and other esters are preferred, especially propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether Acetate, 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-hept Non, 3-heptanone, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3- Methyl-3-methoxybutylpropionate, n-butyl acetate, i-butyl acetate, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate, Ethyl pyruvate and the like are preferable.

  In this invention, a solvent can be used individually or in mixture of 2 or more types.

  (E) Although content of a solvent is not specifically limited, The quantity from which the total density | concentration of each component except the solvent of the coloring composition becomes 5-50 mass% is preferable, and it is 10-40 mass%. Is more preferred. By setting it as such an aspect, the coloring agent dispersion liquid with favorable dispersibility and stability and the coloring composition with favorable coating property and stability can be obtained.

-Additives-
The coloring composition of this invention can also contain a various additive as needed.
Examples of additives include fillers such as glass and alumina; polymer compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylates); surfactants such as fluorosurfactants and silicon surfactants; vinyl Trimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxy Silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyl Dimethoxysilane, 3-chloropropi Adhesion promoters such as trimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane; 2,2-thiobis (4-methyl-6-tert-butylphenol), 2,6-di- t-butylphenol, pentaerythritol tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], 3,9-bis [2- [3- (3-t-butyl-4-hydroxy) -5-methylphenyl) -propionyloxy] -1,1-dimethylethyl] -2,4,8,10-tetraoxa-spiro [5 · 5] undecane, thiodiethylenebis [3- (3,5-di- antioxidants such as t-butyl-4-hydroxyphenyl) propionate]; 2- (3-t-butyl-5-methyl-2-hydroxy Nyl) -5-chlorobenzotriazole, alkoxybenzophenones, etc .; anti-aggregation agents such as sodium polyacrylate; malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, 2-aminoethanol 3-amino-1-propanol, 5-amino-1-pentanol, 3-amino-1,2-propanediol, 2-amino-1,3-propanediol, 4-amino-1,2-butanediol Residue improving agents such as succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ω-carboxypolycaprolactone mono (meth) acrylate, etc. An improving agent etc. can be mentioned.

  The coloring composition of the present invention can be prepared by an appropriate method. Examples of the preparation method include (A) to (C) components together with (E) a solvent and other components optionally added. , Can be prepared by mixing. Among them, C.I. I. Pigment Red 170-containing (A) colorant is mixed in (E) solvent in the presence of a dispersant, optionally with (B) a part of binder resin, for example, using a bead mill, roll mill or the like. Disperse to obtain a pigment dispersion, and then to this pigment dispersion, (C) a polymerizable compound and, if necessary, (B) a binder resin, (D) a photopolymerization initiator, an additional (E) solvent, A method in which other components are added and mixed is preferred.

Colored cured film and method for forming the same The colored cured film of the present invention comprises C.I. I. Pigment Red 170, C.I. I. The content ratio of Pigment Red 170 is 15% by mass or more and 90% by mass or less with respect to the total colorant, and can be formed using the colored composition of the present invention. As the colored cured film of the present invention, for example, there is a red cured film used for a color filter constituting a display element or a solid-state imaging element.

Hereinafter, a colored cured film used for a color filter and a method for forming the same will be described.
As a method for forming the colored cured film constituting the color filter, the following method is first exemplified. First, a light shielding layer (black matrix) is formed on the surface of the substrate so as to divide a portion where pixels are formed, if necessary. Next, for example, after applying a red liquid composition of the radiation-sensitive colored composition of the present invention on the substrate, pre-baking is performed to evaporate the solvent, thereby forming a coating film. Subsequently, after exposing this coating film through a photomask, it develops using an alkali developing solution, and the unexposed part of a coating film is dissolved and removed. Thereafter, post-baking is performed to form a pixel array in which red pixel patterns (colored cured films) are arranged in a predetermined arrangement.

  Subsequently, using each radiation sensitive coloring composition of green or blue, application of each radiation sensitive coloring composition, pre-baking, exposure, development, and post-baking are performed in the same manner as described above to obtain a green pixel array and blue color. Are sequentially formed on the same substrate. Thereby, a color filter in which pixel arrays of the three primary colors of red, green and blue are arranged on the substrate is obtained. However, in the present invention, the order of forming pixels of each color is not limited to the above.

  A black matrix can be formed by forming a metal thin film such as chromium formed by sputtering or vapor deposition into a desired pattern using a photolithographic method. It can also be formed in the same manner as in the case of forming the above-mentioned pixel by using the coloring composition.

Examples of the substrate used when forming the colored cured film include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.
In addition, these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired.

  When applying the radiation-sensitive coloring composition to the substrate, an appropriate coating method such as spraying, roll coating, spin coating (spin coating), slit die coating (slit coating), bar coating, etc. In particular, it is preferable to employ a spin coating method or a slit die coating method.

  Pre-baking is usually performed by combining vacuum drying and heat drying. The drying under reduced pressure is usually performed until the pressure reaches 50 to 200 Pa. Moreover, the conditions of heat drying are 70-110 degreeC normally for about 1 to 10 minutes.

  The coating thickness in the case of forming a cured film of a color filter used in the organic EL display element is usually 0.6 to 8 μm, preferably 1.2 to 5 μm, as the film thickness after drying. Moreover, the coating thickness in the case of setting it as the cured film of the color filter used for a solid-state image sensor is 0.3-5 micrometers normally as a film thickness after drying, Preferably it is 0.5-2 micrometers.

  Examples of the radiation light source used when forming at least one selected from the pixel and the black matrix include, for example, a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, and a low pressure. Examples thereof include a lamp light source such as a mercury lamp, and a laser light source such as an argon ion laser, a YAG laser, a XeCl excimer laser, and a nitrogen laser. An ultraviolet LED can also be used as the exposure light source. The wavelength is preferably radiation in the range of 190 to 450 nm.

In general, the exposure dose of radiation is preferably 10 to 10,000 J / m ² .
Examples of the alkali developer include sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7-. An aqueous solution of undecene, 1,5-diazabicyclo- [4.3.0] -5-nonene or the like is preferable.

For example, an appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline developer. In addition, it is usually washed with water after alkali development.
As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied. The development conditions are preferably 5 to 300 seconds at room temperature.

The post-baking conditions are usually 180 to 280 ° C. and about 10 to 60 minutes.
The film thickness of the pixel thus formed is usually 0.3 to 8 μm, preferably 0.5 to 5 μm.

  Further, as a second method for forming a colored cured film constituting a color filter, a method for obtaining pixels of each color by an ink jet method disclosed in JP-A-7-318723, JP-A-2000-310706, etc. Can be adopted. In this method, first, a partition having a light shielding function is formed on the surface of the substrate. Next, for example, a red liquid composition of the thermosetting coloring composition of the present invention is discharged into the formed partition wall by an inkjet apparatus, and then prebaked to evaporate the solvent. Next, this coating film is exposed as necessary and then cured by post-baking to form a red pixel pattern.

  Subsequently, using each thermosetting coloring composition of green or blue, a green pixel pattern and a blue pixel pattern are sequentially formed on the same substrate in the same manner as described above. Thereby, a color filter in which pixel patterns of the three primary colors of red, green and blue are arranged on the substrate is obtained. However, in the present invention, the order of forming pixels of each color is not limited to the above.

In addition, since the partition plays not only a light shielding function but also a function for preventing the color mixing of the thermosetting coloring compositions discharged in the respective sections, it is compared with the black matrix used in the first method described above. The film thickness is thick. Therefore, a partition is normally formed using a black radiation sensitive composition.
The substrate used for forming the colored cured film, the light source of radiation, and the pre-baking and post-baking methods and conditions are the same as in the first method described above. In this way, the film thickness of the pixel formed by the ink jet method is approximately the same as the height of the partition wall.

  A protective film is formed on the pixel pattern thus obtained as necessary, and then a transparent conductive film is formed by sputtering. After forming the transparent conductive film, a spacer can be further formed to form a color filter. The spacer is usually formed using a radiation-sensitive composition, but may be a light-shielding spacer (black spacer). In this case, a colored radiation-sensitive composition in which a black colorant is dispersed is used.

  Since the color filter including the colored cured film of the present invention thus formed has extremely high luminance, contrast, and coloring power, a color liquid crystal display element, a color imaging tube element, a color sensor, an organic EL display element, and electronic paper It is extremely useful for such as.

Display element The display element of the present invention comprises the colored cured film of the present invention. Examples of the display element include a color liquid crystal display element, an organic EL display element, and electronic paper.
The color liquid crystal display element provided with the colored cured film of the present invention may be a transmissive type or a reflective type, and can take an appropriate structure. For example, the color filter is formed on a substrate different from the driving substrate on which the thin film transistor (TFT) is arranged, and the driving substrate and the substrate on which the color filter is formed are opposed to each other with a liquid crystal layer interposed therebetween. Further, a substrate in which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate in which an ITO (tin-doped indium oxide) electrode is formed are a liquid crystal layer. It is also possible to adopt a structure that is opposed to each other. The latter structure has the advantage that the aperture ratio can be remarkably improved, and a bright and high-definition liquid crystal display element can be obtained. When the latter structure is adopted, the black matrix and the black spacer may be formed on either the substrate side on which the color filter is formed or the substrate side on which the ITO electrode is formed.

  The color liquid crystal display element including the colored cured film of the present invention can include a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). As the white LED, for example, a white LED that obtains white light by color mixing by combining a red LED, a green LED, and a blue LED, a white LED that obtains white light by color mixing by combining a blue LED, a red LED, and a green phosphor, and a blue LED White LED that obtains white light by mixing colors, red LED and green light emitting phosphor, white LED that obtains white light by mixing colors of blue LED and YAG phosphor, blue LED, orange light emitting phosphor and green light emitting fluorescence A white LED that obtains white light by color mixing by combining the body, a white LED that obtains white light by color mixing by combining an ultraviolet LED, a red light emitting phosphor, a green light emitting phosphor, and a blue light emitting phosphor can be exemplified.

  The color liquid crystal display element having the colored cured film of the present invention includes TN (Twisted Nematic) type, STN (Super Twisted Nematic) type, IPS (In-Plane Switching) type, VA (Vertical Alignment) type, OCB (Optical). An appropriate liquid crystal mode such as a Compensated Birefringence type is applicable.

Moreover, the organic EL display element provided with the colored cured film of the present invention can take an appropriate structure, and examples thereof include a structure disclosed in JP-A-11-307242.
Moreover, the electronic paper provided with the colored cured film of the present invention can take an appropriate structure, and examples thereof include a structure disclosed in Japanese Patent Application Laid-Open No. 2007-41169.

Solid-state image sensor The solid-state image sensor of the present invention comprises the colored cured film of the present invention. In addition, the solid-state imaging device of the present invention can take an appropriate structure. For example, as one embodiment, by using the colored composition of the present invention to form a colored pixel (colored cured film) on a semiconductor substrate such as a CMOS substrate by the same operation as described above, particularly color separation is performed. It is possible to manufacture a solid-state imaging device having excellent properties.

  Hereinafter, the embodiment of the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples.

<Synthesis of binder resin>
Synthesis example 1
A flask equipped with a condenser and a stirrer was charged with 132 parts by mass of propylene glycol monomethyl ether acetate and purged with nitrogen. After heating to 90 ° C., 40 parts by mass of propylene glycol monomethyl ether acetate, 40 parts by mass of dicyclopentanyl acrylate (Hitachi Chemical Co., Ltd., trade name: FA-513AS), 60 parts by mass of glycidyl methacrylate, 2,2′-azo A mixed solution of 7 parts by mass of bisvaleronitrile and 28 parts by mass of propylene glycol monomethyl ether acetate was added dropwise over 2 hours. After completion of the dropwise addition, this temperature was maintained and polymerization was further continued for 1 hour, and then the reaction was completed at 100 ° C. for 1 hour. Next, 36.35 parts by mass of methacrylic acid, 2.04 parts by mass of tetrabutylammonium bromide and 0.35 parts by mass of 4-methoxyphenol were added, and an addition reaction was performed at 110 ° C. for 5 hours. Furthermore, 19.9 parts by mass of maleic anhydride (manufactured by Wako Pure Chemical Industries, Ltd.) was charged, and an addition reaction was performed at 100 ° C. for 4 hours to obtain a binder resin solution (solid content concentration: 40% by mass). The obtained binder resin had Mw of 9,700 and Mn of 4,300. This binder resin solution is referred to as “binder resin solution (B-1)”.

Synthesis example 2
A flask equipped with a condenser and a stirrer was charged with 3 parts by mass of 2,2′-azobisisobutyronitrile and 100 parts by mass of propylene glycol monomethyl ether acetate, and subsequently 12 parts by mass of N-phenylmaleimide, 10 parts by mass of styrene, Methacrylic acid 20 parts by mass, 2-hydroxyethyl methacrylate 15 parts by mass, 2-ethylhexyl methacrylate 29 parts by mass, benzyl methacrylate 14 parts by mass and pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by Sakai Chemical Industry Co., Ltd.) 5 A mass part was charged and the atmosphere was replaced with nitrogen. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 80 ° C., and this temperature was maintained for 3 hours for polymerization. Thereafter, the temperature of the reaction solution was raised to 100 ° C., and polymerization was further performed for 1 hour.
After cooling to room temperature, propylene glycol monomethyl ether acetate was added so that the solid content concentration was 40% by mass, thereby obtaining a binder resin solution (solid content concentration 33.3% by mass). The obtained binder resin had Mw of 9,700 and Mn of 5,700. This binder resin solution is referred to as “binder resin (B-2) solution”.

<Synthesis of dispersant>
Synthesis example 3
A block having a repeating unit derived from dimethylaminoethyl methacrylate, butyl methacrylate, PME-200 (manufactured by NOF Corporation, methoxypolyethylene glycol monomethacrylate, with reference to Example 1 of WO 2011/129078 pamphlet) EO polymerization degree≈4) and a block copolymer comprising a B block having a repeating unit derived from methacrylic acid (the copolymerization ratio of each repeating unit is dimethylaminoethyl methacrylate / butyl methacrylate / PME-200 / methacrylic acid = 22 / 47/26/5 and Mw is 10,000). This block copolymer is referred to as “dispersant (1)”.

<Preparation of colorant dispersion>
Preparation Example 1
As a coloring agent, C.I. I. Pigment Red 170 in an amount of 3.92 parts by mass, C.I. I. Pigment Red 254 is 3.64 parts by mass and C.I. I. Pigment Red 177 4.44 parts by mass, BYK-LPN22102 (manufactured by BYK Corporation (BYK)) as a dispersant, 13 parts by mass of solid content = 40% by mass, and binder resin solution (B-2) 12 as binder resin Using a part by mass (solid content concentration: 33.3% by mass) and 64 parts by mass of propylene glycol monomethyl ether acetate as a solvent, the mixture was mixed and dispersed by a bead mill for 12 hours to prepare a colorant dispersion (R1).

Preparation Examples 2-8
In Preparation Example 1, colorant dispersions (R2) to (R8) were prepared by changing the type and amount of each component as shown in Table 1.

In Table 1, each component is as follows.
R170: C.I. I. Pigment Red 170
R254: C.I. I. Pigment Red 254
R177: C.I. I. Pigment Red 177
Y139: C.I. I. Pigment Yellow 139
Y150: C.I. I. Pigment Yellow 150
LPN22102: BYK-LPN22102 ((meth) acrylic dispersant, manufactured by BYK (BYK)), solid content = 40% by mass)
PGMEA: Propylene glycol monomethyl ether acetate

<Preparation and evaluation of coloring composition>
Example 1
46.7 parts by mass of the colorant dispersion (R1), 2.3 parts by mass of the binder resin solution (B-1) as the binder resin and 5.1 parts by mass of the binder resin solution (B-2), dipenta as the polymerizable compound 5.1 parts by mass of a mixture of erythritol hexaacrylate and dipentaerythritol pentaacrylate (manufactured by Nippon Kayaku Co., Ltd., trade name KAYARAD DPHA), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) as a photopolymerization initiator ) Butan-1-one (product name Irgacure 369, manufactured by Ciba Specialty Chemicals Co., Ltd.) 1.0 part by mass, mega-fac F-554 (manufactured by DIC Corporation) as a fluorosurfactant, 0.05 part by mass, And propylene glycol monomethyl ether acetate as a solvent is mixed, solid content concentration 20 quality An amount% colored composition (RS-1) was prepared. In addition, the coloring agent density | concentration in coloring composition (RS-1) is 30 mass%.

Evaluation of Film Thickness and Luminance Colored composition (RS-1) was applied on a glass substrate using a spin coater, and then pre-baked on a hot plate at 90 ° C. for 1 minute to form a coating film. The same operation was performed by changing the rotation speed of the spin coater to form three coating films having different film thicknesses.
Next, after cooling these substrates to room temperature, the coating film on the substrates was exposed to radiation containing each wavelength of 365 nm, 405 nm, and 436 nm at 600 J / m ² without using a high pressure mercury lamp. Exposed in quantity. After that, shower development was performed on these substrates by discharging a developer composed of 0.04% potassium hydroxide aqueous solution at 23 ° C. at a development pressure of 1 kgf / cm ² (nozzle diameter 1 mm). Thereafter, these substrates were washed with ultrapure water, air-dried, and then post-baked in a clean oven at 230 ° C. for 20 minutes to produce a red cured film.
Using the color analyzer (MCPD2000 manufactured by Otsuka Electronics Co., Ltd.), the chromaticity coordinates (x, y) and the stimulus value in the CIE color system with a C light source and a 2-degree visual field for the obtained three red cured films (Y) was measured. From the measurement result, the stimulus value (Y) when the chromaticity coordinate value x = 0.607 was obtained. The evaluation results are shown in Table 3.
It can be said that the greater the stimulus value (Y), the higher the luminance, and the thinner the film thickness, the greater the coloring power of the colorant.

Examples 2-6 and Comparative Examples 1-2
In Example 1, the type and amount of each component were changed as shown in Table 2, and propylene glycol monomethyl ether acetate was mixed so that the solid content concentration was 20% by mass. 2) to (RS-8) were prepared. In the colored compositions (RS-2) to (RS-8), the colorant concentration is 30% by mass.
Next, the colored composition was evaluated in the same manner as in Example 1 except that the colored compositions (RS-2) to (RS-8) were used instead of the colored composition (RS-1). The evaluation results are shown in Table 3.

<Production of color filter>
Example 11
The green composition (GS-1) described later is applied on a glass substrate on which a black matrix is formed using a slit coater, and then prebaked on a hot plate at 90 ° C. for 2 minutes to form a coating film. did. Next, after the substrate on which the coating film is formed is cooled to room temperature, radiation containing each wavelength of 365 nm, 405 nm, and 436 nm is applied to the coating film through a striped photomask using a high-pressure mercury lamp at 1,000 J / m. The exposure amount was ² . Thereafter, after alkali development, the substrate was washed with ultrapure water and further post-baked at 230 ° C. for 20 minutes to form a green striped colored layer having a thickness of 2.0 μm on the substrate.
Next, a red striped colored layer having a thickness of 1.75 μm was formed next to the green striped colored layer using the colored composition (RS-1) by the same method. Further, a blue striped colored layer having a thickness of 2.0 μm adjacent to the green and red colored layers was similarly formed using the blue composition (BS-1) described later. The film thickness of 1.75 μm of the red cured film corresponds to the film thickness when the chromaticity coordinate value x = 0.607 obtained in Example 1.
Next, a protective film was formed using a photocurable resin composition on a colored layer composed of three colors of red, green, and blue. In this way, a color filter substrate was produced.

The green composition (GS-1) was prepared by the following method.
As a coloring agent, C.I. I. 8.7 parts by mass of CI Pigment Green 7; I. Pigment Yellow 185 (4.3 parts by mass), BYK-LPN22102 (manufactured by BYK Corporation) as a dispersant (12.5 parts by mass (solid content concentration = 40% by mass)), and binder resin solution (B-2) (12) 0.5 parts by mass, 52.0 parts by mass of propylene glycol monomethyl ether acetate and 10.0 parts by mass of propylene glycol monoethyl ether as a solvent were mixed and dispersed by a bead mill to prepare a green colorant dispersion.
820 parts by mass of the green pigment dispersion prepared above, 100 parts by mass of the binder resin solution (B-2) as the binder resin, and a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate as the polymerizable compound (Nippon Kayaku Co., Ltd.) 70 parts by mass, trade name KAYARAD MAX-3510), 6 parts by mass of NCI-930 (manufactured by ADEKA) as a photopolymerization initiator, and Emulgen A-60 (manufactured by Kao Corporation) as a nonionic surfactant 4 parts by mass of a 5% by mass solution of propylene glycol monomethyl ether acetate and 105 parts by mass of ethyl 3-ethoxypropionate and 650 parts by mass of 3-methoxybutyl acetate as a solvent were mixed to give a liquid green composition (GS-1) Was prepared.

The blue composition (BS-1) was prepared by the following method.
As a coloring agent, C.I. I. Pigment Blue 15: 6 (12.1 parts by mass) and dye (1) described below (0.9 parts by mass), and BYK-LPN21116 (by Big Chemy (BYK)) as a dispersant (10.5 parts by mass (solid content concentration) = 40% by mass), 12.5 parts by mass of the binder resin solution (B-1), 42.5 parts by mass of propylene glycol monomethyl ether acetate, 1.5 parts by mass of propylene glycol monomethyl ether and 21.0 parts by mass of ethyl lactate as a solvent. A blue colorant dispersion was prepared by mixing and dispersing with a bead mill.
330 parts by weight of the blue colorant dispersion prepared above, 160 parts by weight of the binder resin solution (B-2) as the binder resin, and a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate as the polymerizable compound (Nippon Kayaku) Product name KAYARAD (registered trademark) MAX-3510) 70 parts by mass, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (BASF) as a photopolymerization initiator Manufactured by trade name Irgacure (registered trademark) 369) 15 parts by mass, 2,4-diethylthioxanthone 5 parts by mass, nonionic surfactant Emulgen A-60 (manufactured by Kao Corporation) 5% by mass solution of propylene glycol monomethyl ether acetate 10 parts by mass and 3-ethoxypropyl as solvent A liquid blue composition (BS-1) was prepared by mixing 380 parts by mass of ethyl lopionate, 400 parts by mass of methoxybutyl acetate and 125 parts by mass of propylene glycol monomethyl ether acetate.
The dye (1) is compound No. 1 synthesized according to Synthesis Example 1 of JP2012-083552A. 1 and C.I. I. It is a salt of a cationic triarylmethane chromophore derived from Basic Blue 7 and a bistrifluoromethanesulfonylimide anion.

<Production and Evaluation of Organic EL Display Device>
With reference to Example 2 of JP-T-2010-527108, an organic EL device emitting white light was produced. The emission spectrum of the obtained organic EL device showed maximum emission peaks in the blue region (near 460 nm), the green region (near 570 nm), the yellow region (near 610 nm) and the red region (near 660 nm). This organic EL element and the color filter were bonded together to produce an organic EL display element.
When a voltage was applied between both electrodes of the obtained organic EL display element and the color filter was irradiated with light, a vivid color tone was exhibited.

Examples 12-16
In Example 11, a color filter was prepared in the same manner as in Example 1 except that the colored compositions (RS-2) to (RS-8) were used instead of the colored composition (RS-1), and then An organic EL display element was produced. However, each film thickness of the red stripe-shaped colored layer was set to the film thickness shown in Table 3 when the chromaticity coordinate value x = 0.607 obtained in Examples 2 to 6. And when voltage was applied between the both electrodes of the obtained organic EL display element and the color filter was irradiated with light, the organic EL display elements of Examples 12 to 16 exhibited vivid colors.

<Preparation and evaluation of colored cured film for solid-state imaging device>
Preparation Example 100
(Preparation of composition for forming undercoat film)
After the atmosphere in the flask was replaced with nitrogen, 200 parts by mass of a methyl-3-methoxypropionate solution in which 0.6 parts by mass of 2,2′-azobisisobutyronitrile was dissolved was charged. Subsequently, 37.5 parts by mass of tert-butyl methacrylate and 62.5 parts by mass of glycidyl methacrylate were charged, stirred, and heated at 70 ° C. for 6 hours. After cooling, a resin solution containing a polymer was obtained.
Next, after diluting 33.3 parts by mass (containing 10 parts of the polymer) of this resin solution, 31.9 parts by mass of methyl-3-methoxypropionate, and 3.4 parts by mass of propylene glycol monomethyl ether. , 0.3 parts by mass of trimellitic acid, 0.5 parts by mass of 3-glycidoxypropyltrimethoxysilane, and 0.005 parts by mass of the trade name “FC-4432” (manufactured by Sumitomo 3M Limited) Then, a composition for forming a base film was prepared.

<Preparation of colorant dispersion>
Preparation Example 101
As a coloring agent, C.I. I. Pigment Red 170 in an amount of 8.80 parts by mass, C.I. I. Pigment Yellow 185 (2.20 parts by mass), Dispersant (1) (solid concentration = 40% by mass) as a dispersant, 7.25 parts by mass, and C.I. I. 0.80 part by mass of a sulfonic acid derivative of Pigment Yellow 138, 8.71 parts by mass of a binder resin solution (B-2) (solid content concentration: 33.3% by mass) as a binder resin, and propylene glycol monomethyl ether acetate 72 as a solvent Using 24 parts by mass, a bead mill was used for mixing and dispersing for 12 hours to prepare a colorant dispersion (R101).

Preparation Examples 102 to 107
In Preparation Example 1, colorant dispersions (R102) to (R107) were prepared by changing the type and amount of each component as shown in Table 4.

In Table 4, each component is as follows.
Y185: C.I. I. Pigment Yellow 185
R242: C.I. I. Pigment Red 242
Dispersing aid A: C.I. I. Pigment yellow 138 sulfonic acid derivative

Example 101
59.09 parts by mass of the colorant dispersion (R101), 0.77 parts by mass of the binder resin solution (B-2) (solid content concentration of 33.3% by mass) as the binder resin, and Kayrad DPEA-12 as the polymerizable compound (Nippon Kayaku Co., Ltd., ethylene oxide modified dipentaerythritol hexaacrylate) 1.72 parts by mass, 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- ( O-benzoyl oxime) (Ciba Specialty Chemicals Co., Ltd., Irgacure OXE01) 0.62 parts by mass, 1% by mass of propylene glycol monomethyl ether acetate of Megafac F-554 (manufactured by DIC Corporation) as a fluorosurfactant 0.25 parts by weight of the solution and propylene glycol monomethyl ether Ether acetate was mixed to obtain a colored composition (RS-101) having a solid concentration of 13% by mass. In addition, the coloring agent density | concentration in a coloring composition (RS-101) is 50 mass%.

Evaluation of Transmittance A colored composition (RS-101) was applied on a glass substrate by a spin coating method, and then heated at 100 ° C. for 180 seconds to form a coating film. Subsequently, the entire surface of the coating film on the substrate was exposed (exposure amount of 1,000 mJ / cm ² at a wavelength of 365 nm). Next, the coating film was brought into contact with an aqueous solution containing 0.05% by mass of tetramethylammonium hydroxide for 15 seconds, and then the coating film was washed with water. Then, the glass wafer which has a colored cured film with a film thickness of 0.8 micrometer was obtained by heating for 300 second with a 200 degreeC hotplate.
Using a spectrophotometer (manufactured by JASCO Corporation, V-7300), the transmittance (% T) of the glass wafer having the colored cured film was measured, and the transmittance at the following measurement points was determined. The results are shown in Table 6. However, the transmittance | permeability of Table 6 is a value compared with a glass substrate.

Evaluation method Measurement point 1: Transmittance at 450 nm. If it is 5% or less, purple to blue light can be efficiently shielded. It is more preferable if it is 3% or less.
Measurement point 2: transmittance at 500 nm. If it is 5% or less, blue to green light can be efficiently shielded. It is more preferable if it is 3% or less.
Measurement point 3: transmittance at 560 nm. If it is 5% or less, green light can be efficiently shielded. It is more preferable if it is 3% or less.
Measurement point 4: transmittance at 580 nm. If it is 30% or less, yellow light can be efficiently shielded. It is more preferable if it is 20% or less.
Measurement point 5: transmittance at 630 nm. If it is 80% or more, red light can be efficiently transmitted. It is more preferable if it is 85% or more.

  If it is a red cured film that satisfies all the evaluation criteria at the measurement points 1 to 5, it can be said that it is a red cured film for a solid-state imaging device with good color separation. Moreover, if it is a red cured film which satisfy | fills the more preferable evaluation criteria in the measurement points 1-5, it can be said that especially color separation property is favorable.

Evaluation of Pattern Shape and Residue A colored composition (RS-101) was applied on a silicon wafer by spin coating, and then heated at 100 ° C. for 180 seconds to form a coating film. Exposure was performed by reduced projection exposure (manufactured by Nikon Corporation, NSR-2005i10D, exposure amount of 1,000 mJ / cm ² at a wavelength of 365 nm) through a mask. Next, the coating film was developed by bringing it into contact with an aqueous solution containing 0.05% by mass of tetramethylammonium hydroxide for 15 seconds. Next, the silicon wafer having the developed coating film was heated on a hot plate at 200 ° C. for 300 seconds to obtain a silicon wafer having a square colored cured film having a side of 3 μm.
The resolution of the colored composition (RS-101) was evaluated by observing the silicon wafer with an electron microscope. The evaluation criteria are as follows, and the results are shown in Table 6.

Evaluation criteria ○: The cross-sectional shape of the pattern is rectangular, and no residue is observed between the patterns.
(Triangle | delta): The cross-sectional shape of a pattern is not a rectangle, or a residue is recognized between patterns.
X: The cross-sectional shape of a pattern is not a rectangle, and a residue is recognized between patterns.

Examples 102-104 and Comparative Examples 101-103
In Example 101, the type and amount of each component were changed as shown in Table 5 to prepare colored compositions (RS-102) to (RS-107). All of the colored compositions (RS-102) to (RS-107) have a solid content concentration of 13% by mass and a colorant concentration of 50% by mass.
Next, evaluation was performed in the same manner as in Example 101 except that the colored compositions (RS-102) to (RS-107) were used instead of the colored composition (RS-101). The evaluation results are shown in Table 6.

Claims (11)

(A) C.I. I. A coloring composition containing Pigment Red 170, (B) a binder resin, and (C) a polymerizable compound,
C. I. The coloring composition whose content rate of pigment red 170 is 15 to 90 mass% with respect to all the coloring agents.   The coloring composition according to claim 1, which is for forming a red cured film of a color filter used in an organic EL display element.   Further, (A) C.I. I. A red colorant other than CI Pigment Red 170; I. The coloring composition of Claim 2 whose content rate of pigment red 170 is 20 mass% or more and 90 mass% or less with respect to all the red colorants.   (A) C.I. I. Pigment red 177 and C.I. I. The coloring composition according to claim 3, comprising at least one selected from the group consisting of CI Pigment Red 254.   Furthermore, (A) The coloring composition of any one of Claims 2-4 which contains an isoindoline pigment as a coloring agent.   The coloring composition according to claim 1, which is for forming a red cured film of a color filter used in a solid-state imaging device.   Further, (A) C.I. I. A red colorant other than CI Pigment Red 170; I. The coloring composition of Claim 6 whose content rate of pigment red 170 is 20 mass% or more and 99 mass% or less with respect to all the red colorants.   (A) C.I. I. Pigment red 242 and C.I. I. The coloring composition according to claim 7, comprising at least one selected from the group consisting of CI Pigment Red 254. C. I. Pigment Red 170,
C. I. A colored cured film in which the content ratio of Pigment Red 170 is 15% by mass or more and 90% by mass or less with respect to all the colorants.   A display device comprising the colored cured film according to claim 9.   A solid-state imaging device comprising the colored cured film according to claim 10.