JP2015052779A - Colored photosensitive resin composition, cured film, color filter, method for manufacturing color filter, solid-state imaging element, and image display device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a colored photosensitive resin composition excellent in stability in preventing color irregularity or roughness with lapse of time and excellent in pattern forming property after PCD (post-coating delay), and a cured film, a color filter, a method for manufacturing a color filter, a solid-state imaging element, and an image display device.SOLUTION: The colored photosensitive resin composition comprises: (A) a pigment; (B) a basic dye derivative; (C) a phosphoric acid-based dispersant expressed by general formula (II) below; (D) a resin prepared by copolymerizing a compound (x) expressed by general formula (IV) below and a compound (y) having an ethylenic unsaturated double bond; (E) a photopolymerization initiator; and (F) a polymerizable compound.

Description

  The present invention relates to a colored photosensitive resin composition suitable for producing a color filter used for a liquid crystal display element (LCD), a solid-state imaging element (CCD, CMOS, etc.), and a colored region produced by the above composition. The present invention relates to a color filter having a color filter, a solid-state imaging device having the color filter, and an image display device such as an organic LED liquid crystal display device.

In recent years, with the development of personal computers, particularly large-screen liquid crystal televisions, the demand for liquid crystal displays (LCD), especially color liquid crystal displays, has been increasing. The spread of organic EL displays is also awaited due to the demand for higher image quality. On the other hand, with the widespread use of digital cameras and camera-equipped mobile phones, the demand for solid-state imaging devices such as CCD image sensors has greatly increased.
Color filters are used as key devices for these displays and optical elements, and the demand for cost reduction is increasing along with the demand for higher image quality. Such a color filter is usually provided with a coloring pattern of three primary colors of red (R), green (G), and blue (B), and in a display device or an image sensor, light passing therethrough is divided into three primary colors. It plays a role to draw.

The colorant used in the color filter is commonly required to have the following characteristics.
In other words, it has optical characteristics that are favorable for color reproducibility, optical scattering such as light scattering that causes a decrease in contrast of a liquid crystal display, and unevenness in optical density that causes color unevenness and roughness of a solid-state imaging device. There is a need for a high degree of fastness, such as heat resistance, light resistance, moisture resistance, and the like, a large molar extinction coefficient, and a thin film.
For this reason, it is common to use a pigment as a colorant.

  When forming a color filter used in a liquid crystal display device (LCD), a solid-state imaging device (CCD, CMOS, etc.) and an organic LED liquid crystal display device, following the step of applying a colored photosensitive resin composition on a substrate, In general, a pattern exposure step and a development step using an alkali developer are performed. At this time, after the step of applying the colored photosensitive resin composition, there may be a case in which the holding is performed for several days before the exposure / development step is performed. Such placement after application is generally called PCD (Post Coating Delay). In the color filter manufacturing process, it is more efficient to store the substrate coated with the colored photosensitive resin composition and perform the next exposure / development process together as soon as the exposure / development apparatus is available. This is because there are cases.

Due to the above-described background, the colored photosensitive resin composition is required not to cause a problem in the formation of a colored pattern even after PCD. Specifically, FIG. 1 is a schematic view of a colored pattern 1 formed when the colored photosensitive resin composition is applied on a substrate and then immediately exposed and developed, and observed from above the substrate. Here, the coloring pattern is formed in a rectangular shape. The colored photosensitive resin composition is required to retain such a rectangular pattern even after PCD.
However, depending on the type of the colored photosensitive resin composition, as shown in FIG. 2, the colored pattern 1 after PCD may be greatly collapsed.

For example, Patent Document 1 and Patent Document 2 describe a photosensitive coloring composition containing a resin containing an acrylic monomer having a specific structure as a copolymerization component.
Patent Document 3 and Patent Document 4 describe pigment compositions containing a triazine ring-containing basic compound having a specific structure and a phosphoric acid dispersant having a specific structure.

JP 2004-101728 A JP 2007-212654 A JP 2007-231106 A JP 2007-231107 A

  Patent Document 1 and Patent Document 2 describe that a colored composition having excellent dispersion stability can be obtained by using a resin having an acrylic monomer having a specific structure as a copolymerization component. There was room for further improvement in terms of color unevenness and roughness over time. This is because, in the colored photosensitive resin composition as described in Patent Document 1 and Patent Document 2, adsorption of the dispersion resin to the pigment particles is unstable, This is presumably because the dispersion resin adsorbed on the pigment particle surface was detached from the pigment particle surface. For this reason, it is presumed that the pigment particles cause secondary agglomeration in the process of aging the composition for a long time, the pigment particle size becomes coarse, and the roughness of the color filter after the aging is deteriorated.

  Patent Document 3 and Patent Document 4 describe that a pigment composition excellent in dispersion stability and the like can be obtained by using a triazine ring-containing basic compound having a specific structure and a phosphoric acid dispersant having a specific structure. Has been. However, Patent Documents 3 and 4 still have room for further improvement in terms of color unevenness (zara) when used as a color filter, stability over time, and pattern formation after PCD. This is because, in a colored photosensitive resin composition obtained from a pigment composition containing a phosphoric acid dispersant having a specific structure as described in Patent Documents 3 and 4, each component constituting the composition This is probably because the compatibility was poor, and some of the components that formed the coating film in the process of leaving after coating (PCD) caused phase separation, and the colored pattern obtained by subsequent exposure and development was greatly destroyed.

  The present invention solves such a problem, and uses a colored photosensitive resin composition excellent in color unevenness, roughness stability over time, and pattern formation after PCD, and the colored photosensitive resin composition described above. The present invention relates to a cured film, a color filter, a method for manufacturing a color filter, a solid-state imaging device, and an image display device.

一般式（ＩＩ）中、Ｒ³は数平均分子量４００〜３００００のポリエステル構造を表し、ｙは１または２を表す；ｙが２の場合、複数のＲ³は、それぞれ、同一であっても異なっていてもよい；
一般式（ＩＶ）中、Ｒ⁴は水素原子またはメチル基を表し、Ｒ⁵は炭素数２または３のアルキレン基を表し、Ｒ⁶は水素原子またはベンゼン環を含んでいても良い炭素数１〜２０のアルキル基を表し、ｎは１〜１５の整数を表す；ｎが２以上の場合、複数のＲ⁵は、それぞれ、同一であってもよく、異なっていてもよい。
＜２＞上記（Ｂ）塩基性色素誘導体が、アミノ基を有する化合物である、＜１＞に記載の着色感光性樹脂組成物。
＜３＞上記（Ａ）顔料が、赤色顔料、緑色顔料および黄色顔料からなる群から選ばれる、＜１＞または＜２＞に記載の着色感光性樹脂組成物。
＜４＞上記一般式（ＩＩ）中、上記Ｒ³で表されるポリエステル構造の数平均分子量が１９００〜１００００である、＜１＞〜＜３＞のいずれかに記載の着色感光性樹脂組成物。
＜５＞上記一般式（ＩＩ）中、上記Ｒ³で表されるポリエステル構造が２種以上の異なるラクトンモノマーを開環重合して得られるポリエステル構造である、＜１＞〜＜４＞のいずれかに記載の着色感光性樹脂組成物。
＜６＞さらに、（Ｇ）側鎖に重合性二重結合を有する樹脂を含む、＜１＞〜＜５＞のいずれかに記載の着色感光性樹脂組成物。
＜７＞上記（Ｇ）側鎖に重合性二重結合を有する樹脂が、２〜６の水酸基を有する重合性モノマー（ｐ）と、他の重合性モノマー（ｑ）との共重合体（ａ）に、水酸基と反応可能な官能基とエチレン性不飽和二重結合を有する化合物（ｂ）を反応させてなる樹脂である、＜６＞に記載の着色感光性樹脂組成物。
＜８＞上記（Ｄ）一般式（ＩＶ）で表される化合物（ｘ）とエチレン性不飽和二重結合を有する化合物（ｙ）を共重合してなる樹脂の含有量が、上記（Ａ）顔料１００質量部に対して５〜８０質量部である、＜１＞〜＜７＞のいずれかに記載の着色感光性樹脂組成物。
＜９＞上記着色感光性樹脂組成物が、上記（Ａ）顔料、上記（Ｂ）塩基性色素誘導体、および上記（Ｃ）一般式（ＩＩ）で表されるリン酸系分散剤を分散させた後、上記（Ｄ）一般式（ＩＶ）で表される化合物（ｘ）とエチレン性不飽和二重結合を有する化合物（ｙ）を共重合してなる樹脂を配合してなる、＜１＞〜＜８＞のいずれかに記載の着色感光性樹脂組成物。
＜１０＞カラーフィルタの着色領域形成に用いられる＜１＞〜＜９＞のいずれかに記載の着色感光性樹脂組成物。
＜１１＞＜１＞〜＜１０＞のいずれかに記載の着色感光性樹脂組成物を硬化してなる硬化膜。
＜１２＞＜１＞〜＜１０＞のいずれかに記載の着色感光性樹脂組成物を支持体上に適用して着色感光性組成物層を形成する工程と、上記着色感光性組成物層をパターン状に露光する工程と、未露光部を現像除去して着色パターンを形成する工程とを含むカラーフィルタの製造方法。
＜１３＞＜１＞〜＜１０＞のいずれかに記載の着色感光性樹脂組成物を支持体上に適用して着色感光性組成物層を形成する工程、
上記着色感光性組成物層上にフォトレジスト層を形成する工程、
露光および現像することにより上記フォトレジスト層をパターニングしてレジストパターンを得る工程、および
上記レジストパターンをエッチングマスクとして上記着色感光性組成物層をドライエッチングする工程を含む、カラーフィルタの製造方法。
＜１４＞＜１１＞に記載の硬化膜を有するカラーフィルタ。
＜１５＞＜１２＞または＜１３＞に記載のカラーフィルタの製造方法によって製造したカラーフィルタ。
＜１６＞＜１４＞または＜１５＞に記載のカラーフィルタを有する固体撮像素子。
＜１７＞＜１４＞または＜１５＞に記載のカラーフィルタを有する画像表示装置。 As a result of detailed studies, the present inventors have found that the above-described problems can be solved by using a predetermined phosphoric acid dispersant and a predetermined resin binder.
Specifically, the above problem has been solved by the following means <1>, preferably by <2> to <17>.
<1> (A) pigment, (B) basic dye derivative, (C) phosphoric acid dispersant represented by the following general formula (II), (D) compound represented by the following general formula (IV) ( a colored photosensitive resin composition containing a resin obtained by copolymerizing x) and a compound (y) having an ethylenically unsaturated double bond, (E) a photopolymerization initiator, and (F) a polymerizable compound;

In the general formula (II), R ³ represents a polyester structure having a number average molecular weight of 400 to 30,000, y represents 1 or 2, and when y is 2, a plurality of R ³ may be the same or different. May be;
In the general formula (IV), R ⁴ represents a hydrogen atom or a methyl group, R ⁵ represents an alkylene group having 2 or 3 carbon atoms, R ⁶ represents a hydrogen atom or a benzene ring which may contain a benzene ring. 20 represents an alkyl group, and n represents an integer of 1 to 15; when n is 2 or more, a plurality of R ^{5 s} may be the same or different.
<2> The colored photosensitive resin composition according to <1>, wherein the (B) basic dye derivative is a compound having an amino group.
<3> The colored photosensitive resin composition according to <1> or <2>, wherein the (A) pigment is selected from the group consisting of a red pigment, a green pigment, and a yellow pigment.
<4> The colored photosensitive resin composition according to any one of <1> to <3>, wherein the number average molecular weight of the polyester structure represented by R ³ is 1900 to 10000 in the general formula (II). .
<5> In any one of <1> to <4>, in the general formula (II), the polyester structure represented by R ³ is a polyester structure obtained by ring-opening polymerization of two or more different lactone monomers. A colored photosensitive resin composition according to claim 1.
<6> The colored photosensitive resin composition according to any one of <1> to <5>, further comprising (G) a resin having a polymerizable double bond in the side chain.
<7> A copolymer (a) of a polymerizable monomer (p) having 2 to 6 hydroxyl groups and another polymerizable monomer (q), wherein the resin having a polymerizable double bond in the side chain (G) ) And a functional group capable of reacting with a hydroxyl group and a compound (b) having an ethylenically unsaturated double bond, the colored photosensitive resin composition according to <6>.
<8> The content of the resin obtained by copolymerizing the compound (x) represented by the general formula (IV) and the compound (y) having an ethylenically unsaturated double bond is the above (A). The colored photosensitive resin composition according to any one of <1> to <7>, which is 5 to 80 parts by mass with respect to 100 parts by mass of the pigment.
<9> The colored photosensitive resin composition has dispersed therein the (A) pigment, the (B) basic dye derivative, and the (C) phosphoric acid dispersant represented by the general formula (II). Thereafter, (D) a compound obtained by copolymerizing the compound (x) represented by the general formula (IV) and the compound (y) having an ethylenically unsaturated double bond, <1> to <8> The colored photosensitive resin composition according to any one of the above.
<10> The colored photosensitive resin composition according to any one of <1> to <9>, which is used for forming a colored region of a color filter.
<11> A cured film obtained by curing the colored photosensitive resin composition according to any one of <1> to <10>.
<12> A step of forming a colored photosensitive composition layer by applying the colored photosensitive resin composition according to any one of <1> to <10> on a support, and the above colored photosensitive composition layer. A method for producing a color filter comprising a step of exposing in a pattern and a step of developing and removing unexposed portions to form a colored pattern.
<13> a step of forming a colored photosensitive composition layer by applying the colored photosensitive resin composition according to any one of <1> to <10> on a support;
Forming a photoresist layer on the colored photosensitive composition layer,
A method for producing a color filter, comprising: a step of patterning the photoresist layer by exposure and development to obtain a resist pattern; and a step of dry etching the colored photosensitive composition layer using the resist pattern as an etching mask.
<14> A color filter having the cured film according to <11>.
<15> A color filter manufactured by the method for manufacturing a color filter according to <12> or <13>.
<16> A solid-state imaging device having the color filter according to <14> or <15>.
<17> An image display device having the color filter according to <14> or <15>.

  According to the present invention, a colored photosensitive resin composition having excellent color unevenness (zara) and stability over time, and pattern formation after PCD, and a cured film and a color filter using the colored photosensitive resin composition It has become possible to provide a method for manufacturing a color filter, a solid-state imaging device, and an image display device.

It is the schematic diagram which observed the coloring pattern formed when it exposes and develops immediately after apply | coating a colored photosensitive resin composition on a board | substrate from the board | substrate upper direction. It is the schematic diagram which observed the coloring pattern formed when apply | coating a colored photosensitive resin composition on a board | substrate and performing exposure and image development after PCD from the board | substrate upper direction.

Hereinafter, the contents of the present invention will be described in detail. In the present specification, “to” is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value. The organic EL element in the present invention refers to an organic electroluminescence element.
In this specification, the total solid content refers to the total mass of components excluding the solvent from the total composition of the colored photosensitive resin composition.

In the description of the group (atomic group) in this specification, the description which does not describe substitution and unsubstituted includes the thing which has a substituent with the thing which does not have 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 addition, “radiation” in the present specification means, for example, an emission line spectrum of a mercury lamp, far ultraviolet rays represented by excimer laser, extreme ultraviolet rays (EUV light), X-rays, electron beams, and the like. In the present invention, light means actinic rays or radiation. Unless otherwise specified, “exposure” in this specification is not only exposure with far-ultraviolet rays such as mercury lamps and excimer lasers, X-rays, EUV light, but also drawing with particle beams such as electron beams and ion beams. Are also included in the exposure.

In this specification, “(meth) acrylate” represents both and / or acrylate and methacrylate, “(meth) acryl” represents both and / or acryl and “(meth) acrylic” ) "Acryloyl" represents both and / or acryloyl and methacryloyl.
In the present specification, “monomer” and “monomer” are synonymous. The monomer in this specification is distinguished from an oligomer and a polymer, and refers to a compound having a weight average molecular weight of 2,000 or less. In the present specification, the polymerizable compound means a compound having a polymerizable functional group, and may be a monomer or a polymer. The polymerizable functional group refers to a group that participates in a polymerization reaction.
The weight average molecular weight and the number average molecular weight can be determined by gel permeation chromatography (GPC).

  In the present specification, Me in the chemical formula represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, and Ph represents a phenyl group.

In this specification, the term “process” is not limited to an independent process, and is included in the term if the intended action of the process is achieved even when it cannot be clearly distinguished from other processes. .
The present invention has been made in view of the above situation, and an object thereof is to provide a coloring composition having excellent color characteristics.
In this specification, a weight average molecular weight and a number average molecular weight are defined as a polystyrene conversion value by GPC measurement. In this specification, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are, for example, HLC-8220 (manufactured by Tosoh Corporation), and TSKgel Super AWM-H (manufactured by Tosoh Corporation, 6) as a column. 0.0 mm ID × 15.0 cm can be determined by using a 10 mmol / L lithium bromide NMP (N-methylpyrrolidinone) solution as the eluent.

一般式（ＩＩ）中、Ｒ³は数平均分子量４００〜３００００のポリエステル構造を表し、ｙは１または２を表す。ｙが２の場合、複数のＲ³は、それぞれ、同一であっても異なっていてもよい。
一般式（ＩＶ）中、Ｒ⁴は水素原子またはメチル基を表し、Ｒ⁵は炭素数２または３のアルキレン基を表し、Ｒ⁶は水素原子またはベンゼン環を含んでいても良い炭素数１〜２０のアルキル基を表し、ｎは１〜１５の整数を表す。ｎが２以上の場合、複数のＲ⁵は、それぞれ、同一であってもよく、異なっていてもよい。 <Colored photosensitive resin composition>
The colored photosensitive resin composition of the present invention (hereinafter sometimes referred to as “the composition of the present invention” or “colored composition”) is composed of (A) a pigment, (B) a basic dye derivative, and (C) the following general A phosphoric acid dispersant represented by formula (II), (D) a compound (x) represented by the following general formula (IV) and a compound (y) having an ethylenically unsaturated double bond; And (E) a photopolymerization initiator, and (F) a polymerizable compound.

In the general formula (II), R ³ represents a polyester structure having a number average molecular weight of 400 to 30,000, and y represents 1 or 2. When y is 2, the plurality of R ³ may be the same or different.
In the general formula (IV), R ⁴ represents a hydrogen atom or a methyl group, R ⁵ represents an alkylene group having 2 or 3 carbon atoms, R ⁶ represents a hydrogen atom or a benzene ring which may contain a benzene ring. 20 represents an alkyl group, and n represents an integer of 1 to 15. When n is 2 or more, the plurality of R ⁵ may be the same or different.

By using the composition of the present invention, the color unevenness (zara), the stability over time, and the pattern forming property after PCD are excellent. The reason why such an effect of the present invention can be obtained is not clear, but the following reason is estimated.
(C) a phosphoric acid dispersant represented by the general formula (II), (D) a compound (x) represented by the general formula (IV), and a compound (y) having an ethylenically unsaturated double bond. When used in combination with a resin obtained by copolymerization, (C) the phosphoric acid dispersant represented by the general formula (II) strongly adsorbs the dispersing agent to the pigment particles, and the roughness of the composition increases with time. It is presumed that the effect of suppressing the deterioration was obtained. Further, (D) a resin obtained by copolymerizing the compound (x) represented by the general formula (IV) and the compound (y) having an ethylenically unsaturated double bond functions as a compatibilizing agent, It is presumed that the constituent components were prevented from causing phase separation in the process of leaving (PCD) after coating. As a result, the present invention is considered to be excellent in color unevenness (roughness) and roughness over time, and further in pattern formation after PCD.
Hereinafter, the composition of the present invention will be described in detail.

<< (A) Pigment >>
The composition of the present invention has (A) a pigment. The pigment used in the present invention is preferably selected from the group consisting of a red pigment, a green pigment and a yellow pigment, and various conventionally known inorganic pigments or organic pigments can be used. The pigment preferably has a high transmittance.

  Examples of inorganic pigments include metal compounds represented by metal oxides, metal complex salts, and the like. Specifically, black pigments such as carbon black and titanium black, iron, cobalt, aluminum, cadmium, lead, copper, Mention may be made of metal oxides such as titanium, magnesium, chromium, zinc and antimony, and composite oxides of the above metals.

As an organic pigment, for example,
C. I. Pigment yellow 11,24,31,53,83,93,99,108,109,110,138,139,147,150,151,154,155,167,180,185,199;
C. I. Pigment orange 36, 38, 43, 71;
C. I. Pigment red 81,105,122,149,150,155,171,175,176,177,209,220,224,242,254,255,264,270;
C. I. Pigment violet 19, 23, 32, 39;
C. I. Pigment Blue 1, 2, 15, 15: 1, 15: 3, 15: 6, 16, 22, 60, 66;
C. I. Pigment green 7, 36, 37, 58;
C. I. Pigment brown 25, 28;
C. I. Pigment black 1; and the like.

  Examples of the pigment that can be preferably used in the present invention include the following. However, the present invention is not limited to these.

C. I. Pigment Yellow 11, 24, 108, 109, 110, 138, 139, 150, 151, 154, 167, 180, 185
C. I. Pigment orange 36, 71,
C. I. Pigment Red 122, 150, 171, 175, 177, 209, 224, 242, 254, 255, 264
C. I. Pigment violet 19, 23, 32,
C. I. Pigment Blue 15: 1, 15: 3, 15: 6, 16, 22, 60, 66,
C. I. Pigment green 7, 36, 37, 58;
C. I. Pigment Black 1

  These organic pigments can be used alone or in various combinations in order to adjust the spectrum and increase the color purity. Specific examples of the above combinations are shown below. For example, as a red pigment, an anthraquinone pigment, a perylene pigment, a diketopyrrolopyrrole pigment alone or at least one of them, a disazo yellow pigment, an isoindoline yellow pigment, a quinophthalone yellow pigment or a perylene red pigment , Etc. can be used. For example, as an anthraquinone pigment, C.I. I. Pigment red 177, and perylene pigments include C.I. I. Pigment red 155, C.I. I. Pigment Red 224, and diketopyrrolopyrrole pigments include C.I. I. Pigment Red 254, and C.I. I. Mixing with Pigment Yellow 139 is preferred. The mass ratio of the red pigment to the yellow pigment is preferably 100: 5 to 100: 50. When the ratio is 100: 4 or less, it is difficult to suppress the light transmittance from 400 nm to 500 nm. When the ratio is 100: 51 or more, the main wavelength tends to be closer to the short wavelength, and the color resolution may not be improved. In particular, the mass ratio is optimally in the range of 100: 10 to 100: 30. In the case of a combination of red pigments, it can be adjusted in accordance with the required spectrum.

  As the green pigment, a halogenated phthalocyanine pigment can be used alone, or a mixture thereof with a disazo yellow pigment, a quinophthalone yellow pigment, an azomethine yellow pigment or an isoindoline yellow pigment can be used. For example, C.I. I. Pigment Green 7, 36, 37, 58 and C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 180 or C.I. I. Mixing with Pigment Yellow 185 is preferred. The mass ratio of the green pigment to the yellow pigment is preferably 100: 5 to 100: 150. The mass ratio is particularly preferably in the range of 100: 30 to 100: 120.

  As the blue pigment, a phthalocyanine pigment can be used alone, or a mixture thereof with a dioxazine purple pigment can be used. For example, C.I. I. Pigment blue 15: 6 and C.I. I. Mixing with pigment violet 23 is preferred. The mass ratio of the blue pigment and the violet pigment is preferably 100: 0 to 100: 100, more preferably 100: 10 or less.

  Further, as the black pigment, carbon, titanium black, iron oxide, titanium oxide alone or a mixture thereof is used. When these are used in combination, a combination of carbon and titanium black is preferable, and the mass ratio of carbon and titanium black in that case is preferably in the range of 100: 0 to 100: 60.

Moreover, as a pigment in this invention, it is also possible to use the azo pigment represented by the following general formula (A2), its tautomer, salts or hydrates thereof.
General formula (A2)

In General Formula (A2), G represents a hydrogen atom, an aliphatic group, an aryl group, or a heterocyclic group, and R ¹ represents an amino group, an aliphatic oxy group, or an aliphatic group that may have a substituent. Represents a group, an aryl group, or a heterocyclic group, and R ² represents a substituent.
A represents a heterocyclic ring having at least one atom selected from a nitrogen atom, an oxygen atom, and a sulfur atom.
m represents an integer of 0 to 5, and n represents an integer of 1 to 4.
When n = 2, it represents a dimer via R ¹ , R ² , A or G.
When n = 3, it represents a trimer via R ¹ , R ² , A or G.
When n = 4, it represents a tetramer via R ¹ , R ² , A or G.
General formula (A2) does not have an ionic hydrophilic group.

In general formula (A2), A preferably represents any of the following general formulas (A-1) to (A-32). In the general formulas (A-1) to (A-32), R ^{51 to} R ⁵⁹ each independently represent a hydrogen atom or a substituent, and adjacent substituents are bonded to each other to form a 5- to 6-membered ring. May be. * Represents a bonding position with the azo group of the general formula (A2).

By having a specific structure represented by the general formula (A2), the azo pigment exhibits excellent characteristics in color characteristics such as coloring power and hue, and also has excellent durability such as light resistance and ozone resistance. Characteristics can be shown. For example, a red pattern of a color filter formed using the colored composition of the present invention containing an azo pigment represented by the general formula (A2) exhibits better spectral characteristics as red. Here, “spectral characteristics favorable as red” refers to at least one of the following properties, for example. The spectral characteristics satisfying all the following three properties are particularly excellent.
-The transmittance in the wavelength region of 650 nm to 750 nm is high.
-The transmittance curve rises sharply in the wavelength region of 540 nm or more.
-The transmittance | permeability in a wavelength range (especially 350 nm-400 nm) below 540 nm is low.

  The substituent in the present invention may be any group that can be substituted, for example, an aliphatic group, an aryl group, a heterocyclic group, an acyl group, an acyloxy group, an acylamino group, an aliphatic oxy group, an aryloxy group, a heterocyclic ring. Oxy group, aliphatic oxycarbonyl group, aryloxycarbonyl group, heterocyclic oxycarbonyl group, carbamoyl group, aliphatic sulfonyl group, arylsulfonyl group, heterocyclic sulfonyl group, aliphatic sulfonyloxy group, arylsulfonyloxy group, heterocyclic ring Sulfonyloxy group, sulfamoyl group, aliphatic sulfonamido group, arylsulfonamido group, heterocyclic sulfonamido group, amino group, aliphatic amino group, arylamino group, heterocyclic amino group, aliphatic oxycarbonylamino group, aryloxy Carbonylamino group, heterocyclic oxy Carbonylamino group, aliphatic sulfinyl group, arylsulfinyl group, aliphatic thio group, arylthio group, hydroxy group, cyano group, sulfo group, carboxy group, aliphatic oxyamino group, aryloxyamino group, carbamoylamino group, sulfa Examples include a moylamino group, a halogen atom, a sulfamoylcarbamoyl group, a carbamoylsulfamoyl group, a dialiphatic oxyphosphinyl group, a diaryloxyphosphinyl group. Hereinafter, the “group described in the section of the substituent” refers to the above substituent.

The aliphatic group represented by G may have a substituent, and may be saturated or unsaturated.
Preferred examples of the substituent that the aliphatic group represented by G may have include a hydroxy group, an aliphatic oxy group, a carbamoyl group, an aliphatic oxycarbonyl group, an aliphatic thio group, an amino group, and an aliphatic amino group. An acylamino group and a carbamoylamino group.
The aliphatic group represented by G is preferably an aliphatic group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl, ethyl, cyclohexyl, etc. Can be mentioned.

  In the general formula (A2), the aryl group represented by G may be condensed, may have a substituent, and may be substituted. As long as it is a group that can be substituted with the groups described in the above, preferred substituents include nitro groups, halogen atoms, aliphatic oxy groups, carbamoyl groups, aliphatic oxycarbonyl groups, aliphatic thio groups, amino groups, An aliphatic amino group, an acylamino group, and a carbamoylamino group; The aryl group represented by G is preferably an aryl group having 6 to 12 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms, such as phenyl, 4-nitrophenyl, 4-acetylamino. Phenyl, 4-methanesulfonylphenyl and the like.

In general formula (A2), the heterocyclic group represented by G may have a substituent, may be saturated or unsaturated, and may be condensed. The group that may be substituted may be any group as long as it is a group that can be substituted with the groups described in the above-mentioned substituent group. Preferred substituents include halogen atoms, hydroxy groups, aliphatic oxy groups, carbamoyl groups, An aliphatic oxycarbonyl group, an aliphatic thio group, an amino group, an aliphatic amino group, an acylamino group, and a carbamoylamino group; The heterocyclic group represented by G is preferably a heterocyclic group bonded with carbon atoms having 2 to 12 carbon atoms in total, more preferably 5 to 6 having 2 to 10 carbon atoms bonded with carbon atoms. A membered heterocycle, such as 2-tetrahydrofuryl, 2-pyrimidyl and the like.
G is preferably a hydrogen atom. This is because it is easy to form an intramolecular hydrogen bond or an intramolecular cross hydrogen bond.

The amino group represented by R ¹ may have a substituent, and the group that may be substituted may be any of the groups described in the above-mentioned substituent group and may be substituted. Any substituent may be used, and preferred examples of the substituent include an aliphatic group, an aryl group, and a heterocyclic group.
These substituents may further have a substituent, and the substituent is preferably a substituent having an aliphatic group, a hydroxy group, an amide bond, an ether bond, an oxycarbonyl bond, a thioether bond, and the like. A substituent having a bond between a hetero atom and a hydrogen atom is more preferable from the viewpoint of facilitating intermolecular interaction such as intermolecular hydrogen bonding.
The amino group represented by R ¹ is preferably an unsubstituted amino group, an alkylamino group having 1 to 10 carbon atoms in total, a dialkylamino group having 2 to 10 carbon atoms in total (a dialkyl group is bonded to each other, 5 An arylamino group having 6 to 12 carbon atoms in total or a saturated or unsaturated heterocyclic amino group having 2 to 12 carbon atoms in total. More preferably, an unsubstituted amino group, an alkylamino group having 1 to 8 carbon atoms in total, a dialkylamino group having 2 to 8 carbon atoms in total, an arylamino group having 6 to 10 carbon atoms in total, Heterocyclic amino group having 2 to 12 carbon atoms which may be saturated or unsaturated, such as methylamino, N, N-dimethylamino, N-phenylamino, N- (2-pyrimidyl) Amino and the like.
More preferably, it is an arylamino group having 6 to 13 carbon atoms in total and a heterocyclic amino group having 2 to 12 carbon atoms which may be saturated or unsaturated.
When R ¹ is an arylamino group, the substituent on the aryl group preferably has a substituent at the para position from the bonding position with the amino group, and most preferably has a substituent only at the para position. As the substituent, any group can be used as long as it can be substituted with the group described in the above-mentioned substituent group. Preferably, it is a fatty acid having 1 to 7 carbon atoms in total, more preferably 1 to 4 carbon atoms in total. Group (for example, methyl, ethyl, allyl, (i) -propyl, (t) -butyl, etc.), aliphatic oxy group having 1 to 7 carbon atoms (for example, methoxy, ethoxy, (i) -propyloxy, allyloxy) Etc.), halogen atoms (for example, fluorine, chlorine, bromine, etc.), carbamoyl groups having 1 to 7 carbon atoms (for example, carbamoyl, N-phenylcarbamoyl, N-methylcarbamoyl, etc.), 1 to 7 carbon atoms in total Preferably, a ureido group having 1 to 4 carbon atoms in total (for example, ureido, N-methylureido, N, N-dimethylureido, N-4-pyridylureido, N-phenylureido, etc.), A heterocyclic group condensed with an aryl group having 1 to 7 carbon atoms in total (for example, imidazolone), a hydroxy group, an aliphatic thio group having 1 to 7 carbon atoms in total, more preferably 1 to 4 carbon atoms in total; (For example, methylthio, ethylthio, (i) -propylthio, allylthio, (t) -butylthio and the like), an acylamino group having 2 to 7 total carbon atoms, more preferably 2 to 4 total carbon atoms (for example, acetamino, propionylamino, Pivaloylamino, benzoylamino, etc.), an aliphatic oxycarbonylamino group having 2 to 4 total carbon atoms, more preferably 2 to 4 carbon atoms (for example, methoxycarbonylamino, propyloxycarbonylamino, etc.), 2 carbon atoms in total To 7, more preferably an aliphatic oxycarbonyl group having 2 to 4 carbon atoms in total (eg methoxycarbonyl, ethoxy Carbonyl, etc.), an acyl group having 2 to 7 total carbon atoms, more preferably 2 to 4 total carbon atoms (either an aliphatic carbonyl group, an arylcarbonyl group, a heterocyclic carbonyl group, The group may have a substituent, and the group that may be substituted may be any group as long as it is a group that can be substituted with the groups described in the above-mentioned substituent group, preferably the total number of carbon atoms. An acyl group having 2 to 7 carbon atoms, more preferably an acyl group having 2 to 4 carbon atoms in total, and examples thereof include acetyl, propanoyl, benzoyl, 3-pyridinecarbonyl, and the like.
When the substituent on the aryl group of the arylamino group is substituted from the bonding position with the amino group to the para position, the substituent is located at the end of the molecule, so intermolecular interactions such as intermolecular hydrogen bonding are likely to occur. Because of this, the hue becomes sharper. When the substituent on the aryl group further has a substituent, a substituent having an aliphatic group, a hydroxy group, an amide bond, an ether bond, an oxycarbonyl bond, a thioether bond or the like is preferable, and a bond between a hetero atom and a hydrogen atom is formed. The substituent which it has is more preferable from the viewpoint of facilitating intermolecular interaction such as intermolecular hydrogen bonding.
When R ¹ is a heterocyclic amino group, the substituent may be any group that can be substituted with the group described in the above-mentioned substituent group, and preferably the same substituent as in the case of the arylamino group. However, when the substituent on the heterocyclic group further has a substituent, a substituent having an aliphatic group, a hydroxy group, an amide bond, an ether bond, an oxycarbonyl bond, a thioether bond, or the like is preferable. A substituent having a hydrogen atom bond is more preferable from the viewpoint of facilitating intermolecular interaction such as intermolecular hydrogen bonding.

More preferred substituents when R ¹ is an arylamino group or a heterocyclic amino group include an aliphatic group, an aliphatic oxy group, a halogen atom, a carbamoyl group, a heterocyclic ring condensed with an aryl group, and an aliphatic oxycarbonyl group It is. More preferably, the substituent is preferably an aliphatic group having 1 to 4 carbon atoms, an aliphatic oxy group having 1 to 4 carbon atoms, a halogen atom, a nitro group, a carbamoyl group having 1 to 4 carbon atoms, or a total carbon atom. It is an aliphatic oxycarbonyl group having 2 to 4 atoms.

The aliphatic oxy group represented by R ¹ may have a substituent, and the substituent is any of the groups described in the above-mentioned substituent group and can be substituted. Of these, preferred substituents are a hydroxy group, an aliphatic oxy group, a carbamoyl group, an aliphatic oxycarbonyl group, an aliphatic thio group, an amino group, an aliphatic amino group, an acylamino group, and a carbamoylamino group. The aliphatic oxy group for R ₁ is preferably an alkoxy group having 1 to 8 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, such as methoxy, ethoxy, (t) -Butoxy, methoxyethoxy, carbamoylmethoxy and the like.

The aliphatic group represented by R ¹ may have a substituent, and the substituent may be any group as long as it is a group described in the above-mentioned substituent group and can be substituted. Preferred substituents are a hydroxy group, an aliphatic oxy group, a carbamoyl group, an aliphatic oxycarbonyl group, an aliphatic thio group, an amino group, an aliphatic amino group, an acylamino group, and a carbamoylamino group. The aliphatic group for R ¹ is preferably an alkyl group having 1 to 8 carbon atoms in total, and more preferably an alkyl group having 1 to 4 carbon atoms in total.

The aryl group represented by R ¹ may have a substituent, and the substituent may be any group as long as it is a group described in the above-mentioned substituent section and can be substituted. Preferable substituents include an aliphatic group, an aliphatic oxy group, a halogen atom, a carbamoyl group, a heterocyclic ring condensed with an aryl group, and an aliphatic oxycarbonyl group. The aryl group for R ₁ is preferably an aryl group having 6 to 12 carbon atoms in total, more preferably an aryl group having 6 to 10 carbon atoms in total, such as phenyl, 4-methylphenyl, 3- Examples include chlorophenyl.

The heterocyclic group represented by R ¹ may be a saturated heterocyclic ring or an unsaturated heterocyclic group, and may have a substituent. Examples of the substituent include the substituents described above. Any group can be used as long as it is a group that can be substituted, and preferred substituents include aliphatic groups, aliphatic oxy groups, carbamoyl groups, heterocycles condensed with hetero groups, and aliphatic oxy groups. It is a carbonyl group. The heterocyclic group of R ₁ is preferably a heterocyclic group having 2 to 10 carbon atoms in total, more preferably a 5- to 6-membered non-aromatic group bonded by a nitrogen atom having 2 to 8 carbon atoms in total. Examples of the heterocyclic group include 1-piperidyl, 4-morpholinyl, 1-quinoyl, 2-pyrimidyl, 4-pyridyl, and the like.

R ¹ is preferably an amino group, an aliphatic oxy group, or a 5- to 6-membered non-aromatic heterocyclic group bonded by a nitrogen atom, more preferably an amino group, an aliphatic oxy group, or still more preferably. Is an amino group.
R ¹ is preferably an amino group.

The substituent represented by R ² may be any group that can be substituted with the groups described in the above-mentioned substituent group, and is preferably an aliphatic group, an aryl group, a heterocyclic group, an aliphatic oxycarbonyl group. Group, carboxy group, carbamoyl group, acylamino group, sulfonamido group, carbamoylamino group, sulfamoyl group, aliphatic oxy group, aliphatic thio group, cyano group, halogen atom, more preferably aliphatic oxycarbonyl group, A carbamoyl group, an acylamino group, a carbamoylamino group, an aliphatic oxy group, and a halogen atom are preferable, and an aliphatic oxy group is particularly preferable.
When these substituents further have a substituent, a substituent having an aliphatic group, a hydroxy group, an amide bond, an ether bond, an oxycarbonyl bond, a thioether bond, or the like is preferable, and a substituent having a heteroatom-hydrogen atom bond is preferable. The group is more preferable from the viewpoint of facilitating intermolecular interaction such as intermolecular hydrogen bonding.

m is preferably 0 to 3, more preferably 0 to 1, and even more preferably 0.
n is preferably 1 or 2.

The aliphatic group represented by R ² may have a substituent, may be saturated or unsaturated, and the group that may be substituted includes the above-mentioned substituent group. Any group can be used as long as it is a substitutable group. The aliphatic group for R ² is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl, ethyl, i-propyl, cyclohexyl, t-butyl etc. are mentioned.

The aryl group represented by R ² may have a substituent, and the group that may be substituted is any group that can be substituted with the groups described in the above-mentioned substituents section. Good. The aryl group of R ² is preferably an aryl group having 6 to 12 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms, such as phenyl, 3-methoxyphenyl, 4-carbamoylphenyl. Etc.

The heterocyclic group represented by R ² may have a substituent, may be saturated or unsaturated, may be condensed, and may be substituted. Can be any group as long as it is a group that can be substituted with the groups described in the section of the substituent. The heterocyclic group for R ² is preferably a heterocyclic group having 2 to 16 carbon atoms in total, more preferably a 5 to 6-membered heterocyclic group having 2 to 12 carbon atoms in total, such as 1- Examples include pyrrolidinyl, 4-morpholinyl, 2-pyridyl, 1-pyrrolyl, 1-imidazolyl, 1-benzoimidazolyl and the like.

The aliphatic oxycarbonyl group represented by R ² may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituents Any group can be used as long as it is a substitutable group among the groups described in the section. The aliphatic oxycarbonyl group for R ² is preferably an alkoxycarbonyl group having 1 to 8 carbon atoms in total, more preferably an alkoxycarbonyl group having 1 to 6 carbon atoms in total, such as methoxycarbonyl or i-propyl. Examples include oxycarbonyl, carbamoylmethoxycarbonyl and the like.

The carbamoyl group represented by R ² may have a substituent, and as the group which may be substituted, any group can be used as long as it can be substituted with the groups described in the above-mentioned substituents section. Of these, an aliphatic group, an aryl group, a heterocyclic group and the like are preferable. The carbamoyl group for R ₂ is preferably a carbamoyl group, an alkylcarbamoyl group having 2 to 9 carbon atoms, a dialkylcarbamoyl group having 3 to 10 carbon atoms, an arylcarbamoyl group having 7 to 13 carbon atoms, or a total carbon atom. A heterocyclic carbamoyl group having 3 to 12 atoms, more preferably a carbamoyl group, an alkylcarbamoyl group having 2 to 7 carbon atoms, a dialkylcarbamoyl group having 3 to 6 carbon atoms, and 7 to 11 carbon atoms. Arylcarbamoyl group, a heterocyclic carbamoyl group having 3 to 10 carbon atoms in total, for example, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, phenylcarbamoyl, 4-pyridinecarbamoyl, and the like.

The acylamino group represented by R ² may have a substituent, may be aliphatic, aromatic, heterocyclic, or may be substituted. Can be any group as long as it is a group that can be substituted with the groups described in the section of the substituent. The acylamino group for R ² is preferably an acylamino group having 2 to 12 carbon atoms in total, more preferably an acylamino group having 1 to 8 carbon atoms in total, and still more preferably an alkyl having 1 to 8 carbon atoms in total. Examples of the carbonylamino group include acetylamino, benzoylamino, 2-pyridinecarbonylamino, propanoylamino and the like.

The sulfonamide group represented by R ² may have a substituent, and may be aliphatic, aromatic, or heterocyclic. As the group which may be substituted, any group may be used as long as it is a group which can be substituted with the groups described in the above-mentioned substituent group. The sulfonamide group of R ² is preferably a sulfonamide group having 1 to 12 carbon atoms, more preferably a sulfonamide group having 1 to 8 carbon atoms, and still more preferably 1 to 1 carbon atoms. 8 alkylsulfonamide groups such as methanesulfonamide, benzenesulfonamide, 2-pyridinesulfonamide and the like.

The carbamoylamino group represented by R ² may have a substituent, and as the group that may be substituted, any group can be used as long as it is a group that can be substituted with the groups described in the above-mentioned substituents section. Of these, an aliphatic group, an aryl group, a heterocyclic group and the like are preferable. The carbamoylamino group for R ² is preferably a carbamoylamino group, an alkylcarbamoylamino group having 2 to 9 carbon atoms in total, a dialkylcarbamoylamino group having 3 to 10 carbon atoms in total, or an arylcarbamoyl group having 7 to 13 carbon atoms in total. An amino group, a heterocyclic carbamoylamino group having 3 to 12 carbon atoms in total, more preferably a carbamoylamino group, an alkylcarbamoylamino group having 2 to 7 carbon atoms in total, and a dialkylcarbamoylamino group having 3 to 6 carbon atoms in total. Group, an arylcarbamoylamino group having 7 to 11 carbon atoms in total, and a heterocyclic carbamoylamino group having 3 to 10 carbon atoms in total, such as carbamoylamino, methylcarbamoylamino, N, N-dimethylcarbamoylamino, phenylcarbamoyl Amino, 4-pyridinecarbamo Arylamino and the like.

The sulfamoyl group represented by R ² may have a substituent, and the group which may be substituted may be any group as long as it can be substituted with the groups described in the above-mentioned substituents section. Of these, an aliphatic group, an aryl group, a heterocyclic group and the like are preferable. The sulfamoyl group of R ² is preferably a sulfamoyl group, an alkylsulfamoyl group having 1 to 9 carbon atoms in total, a dialkylsulfamoyl group having 2 to 10 carbon atoms in total, an arylsulfur group having 7 to 13 carbon atoms in total. A famoyl group and a heterocyclic sulfamoyl group having 2 to 12 carbon atoms, more preferably a sulfamoyl group, an alkylsulfamoyl group having 1 to 7 carbon atoms, and a dialkylsulfamo group having 3 to 6 carbon atoms. A moyl group, an arylsulfamoyl group having 6 to 11 carbon atoms in total, and a heterocyclic sulfamoyl group having 2 to 10 carbon atoms in total, such as sulfamoyl, methylsulfamoyl, N, N-dimethylsulfamoyl, Examples thereof include phenylsulfamoyl and 4-pyridinesulfamoyl.

The aliphatic oxy group represented by R ² may have a substituent, may be saturated or unsaturated, and the group that may be substituted includes Any group can be used as long as it is a substitutable group. The aliphatic oxy group for R ² is preferably an alkoxy group having 1 to 8 carbon atoms in total, more preferably an alkoxy group having 1 to 6 carbon atoms in total, such as methoxy, ethoxy, i-propyloxy, Examples include cyclohexyloxy and methoxyethoxy.

The aliphatic thio group represented by R ² may have a substituent, may be saturated or unsaturated, and may be substituted. Any group can be used as long as it is a substitutable group. The aliphatic thio group for R ² is preferably an alkylthio group having 1 to 8 carbon atoms, more preferably an alkylthio group having 1 to 6 carbon atoms, such as methylthio, ethylthio, carbamoylmethylthio, t- Examples include butylthio.

The halogen atom represented by R ² is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom. In view of the effect of the present invention, R ² is preferably an aliphatic oxycarbonyl group or a carbamoyl group. In view of the effect of the present invention, m is preferably 0 or 1, and more preferably 0.

  General formulas (A-1) to (A-32) represented by A will be described. The site represented by the general formulas (A-1) to (A-32) preferably has 2 to 15 carbon atoms in total, and more preferably 2 to 12 carbon atoms in total.

As the substituent represented by R ^{51 to} R ⁵⁴ , any group may be used as long as it is a group that can be substituted with the groups described in the above-mentioned substituent group. As the substituent for R ^{51 to} R ^54, an aliphatic group, an aryl group, a heterocyclic group, an aliphatic oxycarbonyl group, a carbamoyl group, an acylamino group, a sulfonamide group, an aliphatic oxy group, an aliphatic thio group, cyano More preferably an aliphatic group, an aliphatic oxycarbonyl group, a carbamoyl group, an aliphatic oxy group, a cyano group, or the like.

R ^{51 to} R ⁵⁴ are hydrogen atoms, aliphatic groups, aryl groups, heterocyclic groups, aliphatic oxycarbonyl groups, carbamoyl groups, acylamino groups, sulfonamido groups, aliphatic oxy groups, aliphatic groups in terms of the effects of the present invention. A thio group, a cyano group, and the like are preferable, and a hydrogen atom, an aliphatic group, an aliphatic oxycarbonyl group, a carbamoyl group, an aliphatic oxy group, and a cyano group are more preferable.

As the substituent represented by R ⁵⁵ , any group can be used as long as it is a group that can be substituted with the groups described in the above-mentioned substituent group. The substituent for R ⁵⁵ is preferably an aliphatic group, an aryl group, a heterocyclic group, etc., more preferably an aromatic group, an aryl group, or an aromatic group containing a nitrogen atom adjacent to the binding site with the nitrogen atom. It is a 5-6 membered heterocyclic group.

From the viewpoint of the effect of the present invention, R ⁵⁵ is preferably an aliphatic group, an aryl group, or a heterocyclic group, and an aromatic group containing an aromatic group, an aryl group, or an aromatic group containing a nitrogen atom adjacent to the bonding site with the nitrogen atom. The group is more preferably a 5- to 6-membered heterocyclic group, and more preferably an aromatic 5- to 6-membered heterocyclic group containing a nitrogen atom adjacent to the binding site with the nitrogen atom. ^R55 is an aromatic 5- to 6-membered heterocyclic group containing a nitrogen atom adjacent to the binding site with the nitrogen atom, so that not only the intermolecular interaction of the dye molecule but also the intramolecular interaction is firmly formed. It becomes easy to do. This makes it easy to construct a pigment having a stable molecular arrangement, which is preferable in terms of showing good hue and high fastness (light resistance, gas, heat, water, etc.).
In terms of the effects of the present invention, the aromatic 5- to 6-membered heterocyclic group containing a nitrogen atom adjacent to the binding site with the nitrogen atom, which is preferable as R ⁵⁵ , may have a substituent, As the group which may be substituted, any group may be used as long as it is a group which can be substituted with the groups described in the above-mentioned substituent group. Preferred substituents are a hydroxy group, an aliphatic oxy group, a carbamoyl group, an aliphatic oxycarbonyl group, an aliphatic thio group, an amino group, an aliphatic amino group, an acylamino group, and a carbamoylamino group, which is a saturated heterocyclic ring. It may be an unsaturated heterocyclic ring or a condensed heterocyclic ring, and is preferably an aromatic group containing a nitrogen atom at a position adjacent to a binding site with a nitrogen atom having 2 to 12 carbon atoms in total. It is a 6-membered heterocyclic group, and more preferably an aromatic 5- to 6-membered heterocyclic group containing a nitrogen atom at a position adjacent to a binding site with a nitrogen atom having 2 to 10 carbon atoms in total. For example, 2-thiazolyl, 2-benzothiazolyl, 2-oxazolyl, 2-benzoxazolyl, 2-pyridyl, 2-pyrazinyl, 3-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-imidazolyl, 2-benzimidazolyl, 2-triazinyl and the like can be mentioned, and these heterocyclic groups may have a tautomeric structure together with a substituent.

In terms of the effects of the present invention, the aryl group preferable as R ⁵⁵ may have a substituent, and the group which may be substituted may be substituted with the groups described in the above-mentioned substituent group. As long as it is a group, preferred substituents are hydroxy group, nitro group, aliphatic group, aliphatic oxy group, carbamoyl group, aliphatic oxycarbonyl group, aliphatic thio group, amino group, aliphatic amino group An acylamino group and a carbamoylamino group. The aryl group of R ₅₅ is preferably an aryl group having 6 to 12 carbon atoms in total, more preferably an aryl group having 6 to 10 carbon atoms in total, such as phenyl, 3-methoxyphenyl, 4-carbamoylphenyl. The phenyl group is preferable.
In view of the effects of the present invention, the aliphatic group preferable as R ⁵⁵ may have a substituent, and the group which may be substituted is the group described in the above-mentioned substituent group. Any possible group may be used, and preferred substituents include a hydroxy group, a nitro group, an aliphatic oxy group, a carbamoyl group, an aliphatic oxycarbonyl group, an aliphatic thio group, an amino group, an aliphatic amino group, and an acylamino group. , A carbamoylamino group. The aliphatic group for R ₅₅ is preferably an alkyl group having 1 to 6 carbon atoms in total, more preferably an aliphatic group having 1 to 4 carbon atoms in total, such as methyl, ethyl, methoxyethyl, carbamoylmethyl. And a methyl group is preferable.

In general formula (A2), R ⁵⁵ is preferably any one of the following (Y-1) to (Y-13), and is a 6-membered ring in order to make it easy to take an intramolecular hydrogen bond structure. More preferably, it is any of the following (Y-1) to (Y-6), and any of the following (Y-1), (Y-3), (Y-4), (Y-6) Some cases are more preferable, and the following (Y-1) or (Y-4) is particularly preferable. * In the general formulas (Y-1) to (Y-13) represents a bonding site with the N atom of the pyrazole ring. Y ^{1 to} Y ¹¹ represent a hydrogen atom or a substituent. (Y-13)
G ₁₁ represents a nonmetallic atom group that can form a 5- to 6-membered heterocycle, and the heterocycle represented by G ¹¹ may be unsubstituted or substituted, The ring may be monocyclic or condensed. Formulas (Y-1) to (Y-13) may have tautomeric structures together with substituents.

The substituent represented by Y ^{1 to} Y ¹¹ may be any group as long as it is a group that can be substituted with the groups described in the above-mentioned substituent group. As the substituent for Y ^{1 to} Y ^11, an aliphatic group, an aryl group, a heterocyclic group, an aliphatic oxycarbonyl group, a carbamoyl group, an acylamino group, a sulfonamide group, an aliphatic oxy group, an aliphatic thio group, cyano More preferably an aliphatic group, an aliphatic oxy group, an aliphatic thio group, a cyano group, or the like. In Y ^{1 to} Y ¹¹ , two adjacent substituents may form a 5- to 6-membered ring.
Y ¹ to Y ¹¹ are hydrogen atoms, aliphatic groups, aryl groups, heterocyclic groups, aliphatic oxycarbonyl groups, carbamoyl groups, acylamino groups, sulfonamido groups, aliphatic oxy groups, aliphatics in terms of the effects of the present invention. A thio group, a cyano group, and the like are preferable, and a hydrogen atom, an aliphatic group, an aliphatic oxycarbonyl group, a carbamoyl group, an aliphatic oxy group, and a cyano group are more preferable.
In view of the effect of the present invention, A in the general formula (A2) is preferably a 5-membered heterocyclic ring from the viewpoint of hue, more preferably a nitrogen-containing or sulfur-containing 5-membered heterocyclic ring. A 5-membered heterocycle containing 2 or more atoms is more preferred.

As the substituent represented by R ^{56 to} R ⁵⁷ and R ⁵⁹ , any group can be used as long as it is a group that can be substituted with the groups described in the above-mentioned substituent group. As the substituents for R ^{56 to} R ⁵⁷ and R ^59, an aliphatic group, an aryl group, a heterocyclic group, an aliphatic oxycarbonyl group, a carbamoyl group, an acylamino group, a sulfonamide group, an aliphatic oxy group, an aliphatic thio group are preferable. Group, cyano group and the like, more preferably aliphatic group, aliphatic oxy group, aliphatic thio group, cyano group and the like.

In terms of the effects of the present invention, R ^{56 to} R ⁵⁷ and R ⁵⁹ are aliphatic group, aryl group, heterocyclic group, aliphatic oxycarbonyl group, carbamoyl group, acylamino group, sulfonamide group, aliphatic oxy group, aliphatic group. The group is preferably an aliphatic thio group, a cyano group or the like, and more preferably an aliphatic group, an aliphatic oxy group, an aliphatic thio group, or a cyano group.

As the substituent represented by R ⁵⁸ , any group can be used as long as it is a group that can be substituted with the groups described in the above-mentioned substituent group. In view of the effects of the present invention, R ⁵⁸ is preferably a heterocyclic group or an electron-withdrawing group having a Hammett's substituent constant σp value of 0.2 or more, and an σp value of 0.3 or more. It is preferably an attractive group. The upper limit is an electron withdrawing group having a σp value of 1.0 or less.

Specific examples of R ⁵⁸ which is an electron withdrawing group having a σp value of 0.2 or more include acyl group, acyloxy group, carbamoyl group, alkyloxycarbonyl group, aryloxycarbonyl group, cyano group, nitro group, dialkylphospho Group, diarylphosphono group, diarylphosphinyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, sulfonyloxy group, acylthio group, sulfamoyl group, thiocyanate group, thiocarbonyl group, alkyl halide Groups, halogenated alkoxy groups, halogenated aryloxy groups, halogenated alkylamino groups, halogenated alkylthio groups, aryl groups substituted with other electron-withdrawing groups having a σp value of 0.20 or more, heterocyclic groups, Halogen atom, azo group, or selenocyane Group.
In view of the effects of the present invention, R ⁵⁸ is preferably (Y-1) to (Y-13) as described above, and a 6-membered ring described below is used in order to easily form an intramolecular hydrogen bond structure. More preferably, it is any one of (Y-1) to (Y-6), and any one of (Y-1), (Y-3), (Y-4), and (Y-6). The case is more preferable, and the case of (Y-1) or (Y-4) is particularly preferable.
Among the heterocyclic rings of (A-1) to (A-32) cited as A in the general formula (A2), if the atom adjacent to the carbon atom bonded to the azo group is a heteroatom, light fastness The heat fastness tends to be high, and it is preferable to use a pigment having such a structural feature for a color filter because a color filter exhibiting high contrast can be obtained.

In terms of the effects of the present invention, the azo pigment represented by formula (A2) is a saturated heterocyclic group in which G is a hydrogen atom and R ¹ is bonded with an amino group or a nitrogen atom, and m Is 0 or 1, and m is 1, R ² is an aliphatic oxycarbonyl group, a carbamoyl group, or an aliphatic oxy group, and A is (A-1), (A-10) Any one of (A-17), (A-20) to (A-23), (A-27), (A-28), (A-30) to (A-32), and n Is preferably 1 or 2.
More preferably, when G is a hydrogen atom, R ¹ is an amino group or a saturated heterocyclic group bonded with a nitrogen atom, m is 0 or 1, and m is 1, then R ₂ Is an aliphatic oxycarbonyl group, carbamoyl group, or aliphatic oxy group, and A is (A-1), (A-10), (A-11), (A-13) to (A-17). ), (A-20), (A-22) to (A-23), (A-27), (A-28), (A-30) to (A-32), This is a case where n is 1 or 2.
More preferably, G is a hydrogen atom, R ¹ is an amino group or a saturated heterocyclic group bonded with a nitrogen atom, m is 0, and A is (A-10), (A -11), (A-13) to (A-17), (A-20), (A-22) to (A-23), (A-27), (A-28), (A-30) ) To (A-32), where n is 1 or 2.
Particularly preferably, G is a hydrogen atom, R ¹ is an amino group, m is 0, and A is (A-16) to (A-17), (A-20), ( A-28) or (A-32) wherein n is 1 or 2 is particularly preferred, G is a hydrogen atom, R ₁ is an amino group, and m is 0. In this case, A is (A-16) and n is 1 or 2.

In terms of the effects of the present invention, the azo pigment represented by the general formula (A2) is more preferably an azo pigment represented by the following general formula (A3).
The azo pigment represented by the general formula (A3) forms a cross-hydrogen bond between Z or R ⁵⁵ and the hydroxy group of the naphthalene ring and the azo group to increase the planarity of the pigment structure, and the intramolecular and intermolecular interactions. As a result, light fastness, heat fastness, solvent resistance and the like are greatly improved.

  Hereinafter, the azo pigment represented by formula (A3), a tautomer thereof, a salt or a hydrate thereof will be described in detail.

General formula (A3)

In the general formula (A3), R ²¹ , R ²² , R ⁵⁵ , R ⁵⁹ , m, and n are R ¹ , R ² , R ⁵⁵ , R ⁵⁹ , m, and n defined in the general formula (A2), respectively. It is synonymous with n. Z represents an electron withdrawing group having a Hammett's σp value of 0.2 or more. In the case of n = 2, it represents a dimer through R ²¹ , R ²² , R ⁵⁵ , R ⁵⁹ or Z. When n = 3, it represents a trimer via R ²¹ , R ²² , R ⁵⁵ , R ⁵⁹ or Z. When n = 4, it represents a tetramer through R ²¹ , R ²² , R ⁵⁵ , R ⁵⁹ or Z. General formula (A3) does not have an ionic hydrophilic group.

Examples of the substituent having a Hammett σp value represented by Z of 0.2 or more include the groups described in the description of R ^{58 in} the general formula (A2).

Preferred substituents and ranges of R ²¹ , R ²² , R ⁵⁵ , R ⁵⁹ , m, and n of the azo pigment represented by the general formula (A3) are R ¹ , R ² , R ⁵⁵ , Same as R ⁵⁹ , m and n.
From the viewpoint of the effects of the present invention, Z is preferably an acyl group, a carbamoyl group, an alkyloxycarbonyl group, a cyano group, an alkylsulfonyl group, or a sulfamoyl group, more preferably a carbamoyl group, an alkyloxycarbonyl group, or a cyano group. Particularly preferred is the group.

In terms of the effects of the present invention, in the azo pigment represented by the general formula (A3), R ²¹ is an amino group which may have a substituent, m is 0 or 1, and m is In the case of 1, R ²² is an aliphatic oxycarbonyl group, carbamoyl group, or aliphatic oxy group, and R ⁵⁵ is an aromatic 5- to 6-membered heterocyclic group containing a nitrogen atom adjacent to the binding site R ⁵⁹ is a hydrogen atom or an aliphatic group, Z is an acyl group, a carbamoyl group, an alkyloxycarbonyl group, a cyano group, an alkylsulfonyl group, or a sulfamoyl group, and n is 1 or 2 Some cases are preferred.
More preferably, R ²¹ is an amino group which may have a substituent, m is 0, and R ⁵⁵ is any one of (Y-1) to (Y-13), , R ⁵⁹ is a hydrogen atom or an aliphatic group, Z is a carbamoyl group, an alkyloxycarbonyl group, or a cyano group, and n is 1 or 2.
More preferably, R ²¹ is an amino group which may have a substituent, m is 0, and R ⁵⁵ is any one of (Y-1) to (Y-6), , R ⁵⁹ is a hydrogen atom or an aliphatic group, Z is a carbamoyl group, an alkyloxycarbonyl group, or a cyano group, and n is 1 or 2.
Particularly preferably, R ²¹ is an amino group which may have a substituent, m is 0, and R ⁵⁵ is (Y-1), (Y-4), or (Y-6). And R ⁵⁹ is a hydrogen atom, Z is a cyano group, and n is 1 or 2.

  In terms of the effects of the present invention, the azo pigment represented by the general formula (A2) or the general formula (A3) preferably has “total carbon number / number of azo groups” of 40 or less, and 30 or less. It is more preferable. In terms of the effects of the present invention, the azo pigment represented by the general formula (A2) or the general formula (A3) preferably has “molecular weight / number of azo groups” of 700 or less. In view of the effect of the present invention, the azo pigment represented by the general formula (A2) or the general formula (A3) is preferably not substituted with an ionic substituent such as a sulfo group or a carboxy group.

In another embodiment, the azo compound represented by the general formula (A2) is A in (A-1) to (A-9), (A-11) to (A-13), (A-17). ), (A-20) to (A-23), (A-27), (A-28), (A-30) to (A-32), preferably (A-11) to (A A-13), (A-17), (A-20) to (A-23), (A-27), (A-28), (A-30) to (A-32). More preferably, (A-17), (A-20), (A-22) to (A-23), (A-27), (A-28), (A-31), (A-32) Is more preferable, (A-20), (A-28), (A-32) are more preferable, and (A-20) is particularly preferable. More preferably, R ⁵⁶ in (A-20) is R ⁵⁹ .

The present invention includes in its scope tautomers of the azo pigments represented by formula (A2) or formula (A3). The general formula (A2) or the general formula (A3) is shown in the form of an extreme structural formula among several tautomers that can be taken in terms of chemical structure. It may be used as a mixture containing a plurality of tautomers.
For example, the azo pigment represented by the general formula (A2) may be an azo-hydrazone tautomer represented by the following general formula (A1 ′).
The present invention includes within its scope the pigment represented by the following general formula (A1 ′), which is a tautomer of the azo pigment represented by the general formula (A2).

Formula (A1 ')

In general formula (A1 ′), G, R ¹ , R ² , m, n, and A have the same meanings as G, R ¹ , R ² , m, and n in general formula (A2), respectively.

  Among the azo pigments represented by the general formula (A2), examples of the general formulas of particularly preferable azo pigments as described above include azo pigments represented by the following general formulas (A4-1) to (A4-4). Can be mentioned. The azo pigment represented by the general formula (A2) is preferably an azo pigment represented by the following general formulas (A4-1) to (A4-4).

  Hereinafter, the azo pigments represented by formulas (A4-1) to (A4-4), tautomers thereof, salts or hydrates thereof will be described in detail.

In formula (A4-1) ~ (A4-4), R 1, R 2, m, and n, respectively, is generally R ¹ in formula ^{(A2), R 2, m} , and n synonymous . X represents a carbon atom or a nitrogen atom, Ax forms an aromatic 5- to 6-membered heterocyclic group with X and an adjacent carbon atom, and Bx forms an aromatic 5- to 6-membered heterocyclic group with an adjacent carbon atom Specifically, it represents a corresponding one of (A-1) to (A-32) defined by A in the general formula (A2). Yx represents what the heterocyclic group formed together with the nitrogen atom and adjacent carbon atom, the appropriate one of the heterocyclic groups defined R ⁵⁵ in the general formula (A2). R ²³ represents a substituent corresponding to a group obtained by removing the carbonyl group from the corresponding substituent among the substituents such as R ⁵¹ , R ⁵⁴ , R ⁵⁷ , and R ⁵⁸ defined in the general formula (A2). R ′ ¹ represents a corresponding substituent obtained by removing —NH— from the amino group of R ¹ defined by the general formula (A2).

Many tautomers can be considered in the azo pigments represented by the general formulas (A2), (A3), and (A4-1) to (A4-4).
In the present invention, the azo pigment represented by formula (A2) preferably has a substituent that forms an intramolecular hydrogen bond or an intramolecular cross-hydrogen bond. It is more preferable to have at least one substituent that forms an intramolecular hydrogen bond, and it is particularly preferable to have at least one substituent that forms an intramolecular cross-hydrogen bond.

Factors in which this structure is preferable include, as shown by the general formulas (A4-1) to (A4-4), a nitrogen atom constituting a heterocyclic group contained in the azo pigment structure, a hydrogen atom of the hydroxy group of the naphthalene substituent, and Oxygen atom, nitrogen atom of azo group or its tautomer hydrazone group, carbonyl group substituted for azo component contained in azo pigment structure, hydrogen atom and oxygen atom of hydroxy group of naphthalene substituent, and azo It is mentioned that the nitrogen atom of the hydrazone group which is a group or a tautomer thereof easily forms a cross-hydrogen bond in the molecule.
As a result, the planarity of the molecule is increased, the intramolecular / intermolecular interaction is further improved, and the crystallinity of the azo pigment represented by the general formula (A4-1) to the general formula (A4-4) is increased ( It is more preferable because it is easy to form a higher order structure), and the required performance as a pigment is greatly improved in light fastness, heat stability, wet heat stability, water resistance, gas resistance and / or solvent resistance. An example.
Also from this viewpoint, the azo pigment represented by the general formula (A2) is preferably a pigment represented by the general formula (A3) or (A4-1) to (A4-4). ), (A4-1) or (A4-2) is more preferred, and azo pigments represented by formula (A3) are particularly preferred.

  As specific examples of the azo pigment used in the present invention, for example, the compounds described in paragraphs 0094 to 0116 of JP2011-162760A can be referred to, and the contents thereof are incorporated in the present specification.

  The pigment in the present invention is selected from the following general formula (1A), general formula (1B), and quinophthalone compounds represented by the general formula (1C) (hereinafter sometimes referred to as “specific quinophthalone compounds”). It is also possible to use one or more pigments. By using a quinophthalone compound, it has high brightness and a high contrast ratio, excellent coloring power, and excellent effects for reducing the viscosity of the colored composition for color filters.

一般式（１Ｂ）

一般式（１Ｃ）

一般式（１Ａ）〜（１Ｃ）中、Ｒ¹⁴〜Ｒ²⁸、Ｒ²⁹〜Ｒ⁴³、Ｒ⁴⁴〜Ｒ⁶⁰は、それぞれ独立して、水素原子、ハロゲン原子、置換基を有してもよいアルキル基、置換基を有してもよいアルコキシ基、置換基を有してもよいアリール基、−ＳＯ₃Ｈ；−ＣＯＯＨ；およびこれら酸性基の１価〜３価の金属塩；アルキルアンモニウム塩、置換基を有してもよいフタルイミドメチル基、または置換基を有してもよいスルファモイル基を示す。 General formula (1A)

General formula (1B)

General formula (1C)

In general formulas (1A) to (1C), R ^{14 to} R ²⁸ , R ^{29 to} R ⁴³ , and R ^{44 to} R ⁶⁰ are each independently a hydrogen atom, a halogen atom, or an alkyl which may have a substituent. group, an optionally substituted alkoxy group, an optionally substituted aryl group, -SO ₃ H; -COOH; and monovalent to trivalent metal salt thereof acidic groups; alkylammonium salts, A phthalimidomethyl group which may have a substituent or a sulfamoyl group which may have a substituent is shown.

  Here, examples of the halogen atom include fluorine, chlorine, bromine, and iodine.

  Examples of the alkyl group which may have a substituent include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, neopentyl, n-hexyl, and n-octyl. Group, stearyl group, linear or branched alkyl group such as 2-ethylhexyl group, trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4- Examples thereof include alkyl groups having a substituent such as a methoxybenzyl group, a 4-nitrobenzyl group and a 2,4-dichlorobenzyl group.

  Examples of the alkoxy group which may have a substituent include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutyloxy group, a tert-butyloxy group, a neopentyloxy group, and 2,3. -In addition to linear or branched alkoxy groups such as dimethyl-3-pentoxy, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group, trichloromethoxy group, trifluoromethoxy group, 2 2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group, 2,2-ditrifluoromethylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group And alkoxy groups having a substituent such as a benzyloxy group.

  In addition, examples of the aryl group which may have a substituent include an aryl group such as a phenyl group, a naphthyl group, an anthranyl group, a p-methylphenyl group, a p-bromophenyl group, a p-nitrophenyl group, a p- Methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4 , 5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthraquinonyl group and other aryl groups having a substituent.

Examples of acidic groups include —SO ₃ H and —COOH, and monovalent to trivalent metal salts of these acidic groups include sodium salts, potassium salts, magnesium salts, calcium salts, iron salts, and aluminum salts. Etc. In addition, as the alkyl ammonium salt of acidic group, quaternary alkyl such as ammonium salt of long-chain monoalkylamine such as octylamine, laurylamine, stearylamine, palmityltrimethylammonium, dilauryldimethylammonium, distearyldimethylammonium salt, etc. An ammonium salt is mentioned.

The “substituent” in the phthalimidomethyl group (C ₆ H ₄ (CO) ₂ N—CH ₂ —) which may have a substituent and the sulfamoyl group (H ₂ NSO ₂ —) which may have a substituent "Includes the above halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, and the like.

Furthermore, in the quinophthalone compound, the low viscosity of the dispersion is such that R ^{14 to} R ²⁸ , R ^{29 to} R ⁴³ , and R ^{44 to} R ⁶⁰ in the general formulas (1A) to (1C) are hydrogen atoms or halogen atoms. From the viewpoint of making it more preferable.

  Specific examples of the quinophthalone compound include the following quinophthalone compounds (a) to (r), but the present invention is not limited thereto.

一般式（１）中、Ａ¹〜Ａ¹⁶は、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、置換基を有してもよいアルキル基、または置換基を有してもよいアリール基を表す。Ｒ¹およびＲ²は、それぞれ独立して、水素原子、ヒドロキシ基、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、または−ＯＲ³を表し、Ｒ¹とＲ²とが互いに結合して環を形成しても良い。Ｒ³は、置換基を有してもよいアルキル基、または置換基を有してもよいアリール基である。 Further, as the pigment in the present invention, a phthalocyanine dye represented by the following general formula (1) (hereinafter sometimes referred to as “specific phthalocyanine dye”) can also be used.
General formula (1)

In general formula (1), A ^{1 to} A ¹⁶ are each independently a hydrogen atom, a halogen atom, a nitro group, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Represents. R ¹ and R ² are each independently hydrogen atom, hydroxy group, an optionally substituted alkyl group, an optionally substituted aryl group, or an -OR ^3, and R ¹ R ² may be bonded to each other to form a ring. R ³ is an alkyl group which may have a substituent or an aryl group which may have a substituent.

  Specific examples of the specific phthalocyanine dye that can be used in the present invention are listed below, but the present invention is not limited thereto.

（式（２）中、ＡおよびＢは、それぞれ独立して、水素原子、フッ素原子、ヨウ素原子、シアノ基、炭素数１〜１２のアルキル基、置換基を有してもよいフェニル基、−ＣＦ₃、−ＯＲ¹、−ＳＲ²、−Ｎ（Ｒ³）Ｒ⁴、−ＣＯＯＲ⁵、−ＣＯＮＨ₂、−ＣＯＮＨＲ⁶、−ＣＯＮ（Ｒ⁷）Ｒ⁸、−ＳＯ₂ＮＨ₂、−ＳＯ₂ＮＨＲ⁹、または、−ＳＯ₂Ｎ（Ｒ¹⁰）Ｒ¹¹であり、Ｒ¹〜Ｒ¹¹は、それぞれ独立して、炭素数１〜１２のアルキル基、置換基を有してもよいフェニル基、または、置換基を有してもよいアラルキル基である。ただし、ＡおよびＢが同時に水素原子になることはない。） As the pigment in the present invention, a diketopyrrolopyrrole pigment represented by the following formula (2) can also be used.

(In Formula (2), A and B are each independently a hydrogen atom, a fluorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group,- _{^{CF 3, -OR 1, -SR 2}} , -N (R 3) R 4, -COOR 5, -CONH 2, -CONHR 6, -CON (R 7) R 8, -SO 2 NH 2, -SO 2 NHR ⁹ or —SO ₂ N (R ¹⁰ ) R ¹¹ , wherein R ^{1 to} R ¹¹ are each independently an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group, Or an aralkyl group which may have a substituent, provided that A and B do not simultaneously become hydrogen atoms.)

Among the specific heterodiketopyrrolopyrrole pigments represented by the formula (2) used for the pigment in the present invention, the formula (2-1), the formula (2-2), the formula (2-3), the formula (2) -4) is preferable from the viewpoints of brightness, contrast, and crystal precipitation suppression effect. Further, R ^{6 to} R ⁸ in the formulas (2-3) and (2-4) are an alkyl group having 4 or more carbon atoms, or a phenyl group which may have a substituent. From the point of view, it is preferable. The reason why these are effective in increasing contrast and suppressing crystal precipitation is because of the steric hindrance effect due to bulky substituents such as carboamide groups, phenyl groups, and t-butyl groups having an alkyl group having 4 or more carbon atoms. This is thought to be due to the suppression of aggregation. Moreover, since the specific hetero diketopyrrolopyrrole pigment having a carboamide group, a phenyl group, or a t-butyl group has excellent color characteristics, the excellent lightness of the brominated diketopyrrolopyrrole pigment is not impaired.

（式（２−３）および式（２−４）中、Ｒ⁶〜Ｒ⁸は、それぞれ独立して、炭素数１〜１２のアルキル基、または置換基を有してもよいフェニル基である。）

(In Formula (2-3) and Formula (2-4), R ^{6 to} R ⁸ are each independently an alkyl group having 1 to 12 carbon atoms or an optionally substituted phenyl group. .)

  Specific examples of the specific heterodiketopyrrolopyrrole pigment of the formula (2) that can be used in the present invention are listed below, but are not limited thereto.

When used for a color filter, the primary particle size of the pigment is preferably 100 nm or less from the viewpoint of color unevenness and contrast, and is preferably 5 nm or more from the viewpoint of dispersion stability. The primary particle size of the pigment is more preferably 5 to 75 nm, further preferably 5 to 55 nm, and particularly preferably 5 to 35 nm. The specific dispersion resin according to the present invention can exert particularly good effects in combination with a pigment having a primary particle size in the range of 5 to 35 nm.
The primary particle size of the pigment can be measured by a known method such as an electron microscope.

The pigment is preferably a pigment selected from anthraquinone pigments, diketopyrrolopyrrole pigments, phthalocyanine pigments, quinophthalone pigments, isoindoline pigments, azomethine pigments, and dioxazine pigments. In particular, C.I. I. Pigment red 122, C.I. I. Pigment red 177 (anthraquinone pigment), C.I. I. Pigment red 254 (diketopyrrolopyrrole pigment), C.I. I. Pigment green 7, 36, 58, C.I. I. Pigment Blue 15: 6 (phthalocyanine pigment), C.I. I. Pigment yellow 138 (quinophthalone pigment), C.I. I. Pigment yellow 139,185 (isoindoline pigment), C.I. I. Pigment yellow 150 (azomethine pigment), C.I. I. Pigment violet 23 (a dioxazine pigment) is most preferable.
Moreover, the composition of this invention may contain well-known dyes other than (A) pigment. For example, JP-A 64-90403, JP-A-64-91102, JP-A-1-94301, JP-A-6-11614, Toho 2592207, U.S. Pat. No. 4,808,501, U.S. Pat. No. 5, U.S. Pat. No. 505950, JP-A-5-333207, JP-A-6-35183, JP-A-6-51115, JP-A-6-194828, and the like. Can be used. The chemical structure includes pyrazole azo, pyromethene, anilinoazo, triphenylmethane, anthraquinone, benzylidene, oxonol, pyrazolotriazole azo, pyridone azo, cyanine, phenothiazine, pyrrolopyrazole azomethine, etc. Dyes can be used.
A dye multimer may be used as the dye. Examples of the dye multimer include compounds described in JP2011-213925A and JP2013-041097A.

The content of the pigment in the composition of the present invention is preferably 10% by mass to 70% by mass, more preferably 20%, based on all components (solid content) excluding the solvent contained in the colored photosensitive resin composition. It is mass%-60 mass%, More preferably, it is 30 mass%-60 mass%.
Only one kind of pigment may be contained in the composition of the present invention, or two or more kinds thereof may be contained. When two or more types are included, the total amount is preferably within the above range.

<< (B) Basic dye derivative >>
The composition of the present invention has (B) a basic dye derivative. The basic dye derivative is a compound having a structure in which a part of the pigment is substituted with a basic group.

As pigments for constituting basic dye derivatives, quinoline pigments, benzimidazolone pigments, isoindoline pigments, diketopyrrolopyrrole pigments, azo pigments, phthalocyanine pigments, anthraquinone pigments, quinacridone pigments , Dioxazine pigments, perinone pigments, perylene pigments, thioindigo pigments, isoindolinone pigments, quinophthalone pigments, selenium pigments, metal complex pigments, and the like.
The basic dye derivative is preferably a quinoline-based, benzimidazolone-based, or isoindoline-based basic dye derivative, and more preferably a benzimidazolone-based basic dye derivative.

Specifically, the compound described in JP-A-60-88185, the compound described in JP-A-2000-239554, and the pigment mother nucleus structure and amino group in the molecule described in JP-A-2009-86375. And the like, and the contents thereof are incorporated herein.
The basic group possessed by the basic dye derivative is preferably an amino group.
Among these, the basic dye derivative is preferably a dye derivative represented by the following general formula (P1) or general formula (I).

一般式（Ｐ１）中、Ａは、Ｘ−Ｙとともにアゾ顔料を形成しうる成分を表す。上記Ａは、ジアゾニウム化合物とカップリングしてアゾ顔料を形成しうる化合物であれば、任意に選択することができる。以下に、上記Ａの具体例を示すが、本発明はこれらの具体例に何ら限定されるものではない。

In general formula (P1), A represents a component capable of forming an azo pigment together with XY. A can be arbitrarily selected as long as it is a compound capable of coupling with a diazonium compound to form an azo pigment. Specific examples of A above are shown below, but the present invention is not limited to these specific examples.

  In the general formula (P1), X is selected from a single bond (meaning that Y is directly connected to -N = N-) or a divalent linking group represented by the following structural formula. Represents a group.

上記一般式（Ｐ１）中、Ｙは、下記一般式（Ｐ２）で表される基を表す。

In the general formula (P1), Y represents a group represented by the following general formula (P2).

In general formula (P2), Z represents a lower alkylene group. Z is represented as — (CH ₂ ) _b —, wherein _b represents an integer of 1 to 5, preferably 2 or 3. In formula (P2), —NR ₂ represents a lower alkylamino group or a 5- to 6-membered saturated heterocyclic ring containing a nitrogen atom. The -NR _2, when a lower alkyl amino group is represented as _{-N (C n H 2n + 1} ) 2, n represents an integer of 1 to 4, preferably represents 1 or 2. On the other hand, when —NR ₂ represents a 5- to 6-membered saturated heterocycle containing a nitrogen atom, a heterocycle represented by the following structural formula is preferable.

Z and —NR ₂ in the general formula (P2) may each have a lower alkyl group or an alkoxy group as a substituent. In the general formula (P2), a represents 1 or 2, preferably 2.

  Specific examples (specific examples 1 to 22) of the compound represented by the general formula (P1) are shown below, but the present invention is not limited to these specific examples.

一般式（Ｉ）中、Ｄｙｅはｎ価の有機色素残基を表し、Ｘは単結合、−ＣＯＮＨ−Ｙ²−、−ＳＯ₂ＮＨ−Ｙ²−または−ＣＨ₂ＮＨＣＯＣＨ₂ＮＨ−Ｙ²−（Ｙ²は置換基を有していても良いアルキレン基またはアリーレン基を表す。）を表し、Ｙ¹は−ＮＨ−または−Ｏ−を表し、Ｚは、ｎが１を表す場合は水酸基、アルコキシ基、下記一般式（ＩＩＩ）で表される基、または−ＮＨ−Ｘ−Ｄｙｅ（Ｘは一般式（Ｉ）中のＸと同義である）を表し、ｎが２〜４の整数を表す場合はそれぞれ水酸基、アルコキシ基、または下記一般式（ＩＩＩ）で表される基を表し、Ｒ¹およびＲ²はそれぞれ、置換基を有していても良いアルキル基を表し、Ｒ¹とＲ²が互いに結合して窒素原子を含むヘテロ環を形成してもよい。ｍは１〜６の整数を表し、ｎは１〜４の整数を表す。ｎが２以上の場合、複数のＸ、Ｙ¹、Ｒ¹、およびＲ²は、それぞれ、同一であってもよく、異なっていてもよい。

一般式（ＩＩＩ）中、Ｙ³は−ＮＨ−または−Ｏ−を表す。Ｒ¹およびＲ²はそれぞれ、置換基を有していても良いアルキル基を表し、Ｒ¹とＲ²が互いに結合して窒素原子を含むヘテロ環を形成してもよい。ｍは１〜６の整数を表す。 Formula (I)

In general formula (I), Dye represents an n-valent organic dye residue, X represents a single bond, —CONH—Y ² —, —SO ₂ NH—Y ² — or —CH ₂ NHCOCH ₂ NH—Y ² —. (Y ² represents an optionally substituted alkylene group or arylene group), Y ¹ represents —NH— or —O—, Z represents a hydroxyl group when n represents 1, Represents an alkoxy group, a group represented by the following general formula (III), or -NH-X-Dye (X is the same as X in the general formula (I)), and n represents an integer of 2 to 4. Each represents a hydroxyl group, an alkoxy group, or a group represented by the following general formula (III), R ¹ and R ² each represents an alkyl group which may have a substituent, and R ¹ and R ² May combine with each other to form a heterocycle containing a nitrogen atom. m represents an integer of 1 to 6, and n represents an integer of 1 to 4. When n is 2 or more, the plurality of X, Y ¹ , R ¹ , and R ² may be the same or different.

In general formula (III), Y ³ represents —NH— or —O—. R ¹ and R ² each represents an alkyl group which may have a substituent, and R ¹ and R ² may be bonded to each other to form a heterocyclic ring containing a nitrogen atom. m represents an integer of 1 to 6.

Dye represents an n-valent organic dye residue. Examples of the organic dye residue include a chromogenic group in the pigment as described above, a similar structure, or a partial structure. Specifically, a skeleton having an azo group, a skeleton having a urea structure, a skeleton having an amide structure, Examples include a structure containing one or more partial structures selected from a skeleton having a cyclic amide structure, an aromatic ring having a heteroatom-containing 5-membered ring, and an aromatic ring having a heteroatom-containing 6-membered ring, and Dye Is a substituent containing these organic dye residues.
The dye preferably has a pigment mother nucleus structure, or a pigment mother nucleus structure and an aromatic ring, a nitrogen-containing aromatic ring, an oxygen-containing aromatic ring, or a sulfur-containing aromatic ring, and the amino group has a pigment mother nucleus structure, an aromatic ring It is bonded directly or via a linking group to any of the ring, nitrogen-containing aromatic ring, oxygen-containing aromatic ring and sulfur-containing aromatic ring. Specifically, quinoline residue, benzimidazolone residue, isoindoline residue, diketopyrrolopyrrole residue, azo residue, phthalocyanine residue, anthraquinone residue, quinacridone residue , Dioxazine residues, perinone residues, perylene residues, thioindigo residues, isoindolinone residues, quinophthalone residues, selenium residues, metal complex residues and the like.

Specific examples of the organic dye residue represented by Dye include a copper phthalocyanine residue and the following organic dye residues. In the formula, * represents a binding site with X in the general formula (I).

  Among these, a monoazo dye having a benzimidazolone skeleton is preferable.

X represents a single bond, —CONH—Y ² —, —SO ₂ NH—Y ² — or —CH ₂ NHCOCH ₂ NH—Y ² —, and preferably a single bond.
Y ² represents an alkylene group or an arylene group which may have a substituent. As said alkylene group, a C1-C10 alkylene group is preferable, a C1-C6 alkylene group is more preferable, and a C1-C3 alkylene group is further more preferable. Specific examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group. The alkylene group may have a substituent, and examples of the substituent include the groups described in the section of the substituent.
As said arylene group, a C6-C20 arylene group is preferable and a C6-C10 arylene group is more preferable. Specific examples include a phenylene group, a naphthylene group, and an anthracenylene group.
The alkylene group and the arylene group may have a substituent, and examples of the substituent include the groups described in the section of the substituent.

Y ¹ represents —NH— or —O—, preferably —NH—.

R ¹ and R ² each represents an alkyl group which may have a substituent, and R ¹ and R ² may be bonded to each other to form a heterocyclic ring containing a nitrogen atom.
As said alkyl group, a C1-C10 alkyl group is preferable and a C1-C6 alkyl group is more preferable. Specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, and an n-octyl group. The alkyl group may have a substituent, and examples of the substituent include the groups described above in the section of the substituent.
R ¹ and R ² preferably represent an alkyl group which may have the same substituent.

m represents the integer of 1-6, 1-4 are preferable and 1-3 are more preferable.
n represents an integer of 1 to 4, preferably 1 to 3, and more preferably 1 or 2.

Z represents a hydroxyl group, an alkoxy group, a group represented by the general formula (III), or —NH—X-Dye (where X is the same as X in the general formula (I)) when n represents 1. In the case where n represents an integer of 2 to 4, each represents a hydroxyl group, an alkoxy group, or a group represented by the above general formula (III).
When n represents 1, Z is preferably a group represented by the above general formula (III) or -NH-X-Dye, and more preferably a group represented by the above general formula (III).
When n represents an integer of 2 to 4, Z is preferably a group represented by the general formula (III).

In the general formula (III), Y ³ represents -NH- or -O-, -NH- are preferred. Y ³ preferably represents the same group as Y ¹ in formula (I).

R ¹ and R ² are in the formula (III), represents an optionally substituted alkyl group has the same meaning as R ¹ and R ² in formula (I), and preferred ranges are also the same . R ¹ and R ² in the general formula (III) preferably represent an alkyl group which may have the same substituent. Moreover, it is preferable that R < ¹ > and R < ² > in general formula (III) represent the alkyl group which may have the same substituent as R < ¹ > and R < ² > in general formula (I).

  m represents the integer of 1-6, 1-4 are preferable and 1-3 are more preferable. m preferably represents the same integer as m in formula (I).

  Specific examples of the basic dye derivative used in the present invention are shown below, but the present invention is not limited thereto.

The content of the basic dye derivative (B) in the present invention is preferably 0.5% by mass or more and 40% by mass or less, and preferably 1% by mass or more and 15% by mass or less with respect to the total solid content. More preferred.
Moreover, it is preferable that content of (B) basic pigment derivative is 0.5 mass part or more and 50 mass parts or less with respect to 100 mass parts of (A) pigment, and 1 mass part or more and 25 mass parts or less. It is more preferable that
Only 1 type may be contained in the composition of this invention, and 2 or more types may be contained for the basic pigment derivative. When two or more types are included, the total amount is preferably within the above range.

<< (C) Phosphoric Dispersant Represented by Formula (II) >>
The composition of the present invention has (C) a phosphoric acid-based dispersant represented by the general formula (II). By containing the phosphoric acid-based dispersant, the dispersant is strongly adsorbed to the pigment particles, and it becomes possible to suppress the deterioration of the roughness accompanying the aging of the composition. In addition, when the pigment composition described in Patent Document 3 and Patent Document 4 is used as it is in a colored photosensitive resin composition, the component (C) is poorly compatible with other components, and the roughness over time is slightly large. Although the pattern formability after PCD was very poor, in the present invention, this point is solved by using it together with the component (D).

一般式（ＩＩ）中、Ｒ³は数平均分子量４００〜３００００のポリエステル構造を表し、ｙは１または２を表す。ｙが２の場合、複数のＲ³は、それぞれ、同一であっても異なっていてもよい。 Formula (II)

In the general formula (II), R ³ represents a polyester structure having a number average molecular weight of 400 to 30,000, and y represents 1 or 2. When y is 2, the plurality of R ³ may be the same or different.

R ³ represents a polyester structure having a number average molecular weight of 400 to 30,000, and when y is 2, the plurality of R ³ may be the same or different. The number average molecular weight of the polyester structure is more preferably 1900 to 10000, still more preferably 400 to 3000, and particularly preferably 2000 to 3000. If it is less than 400, it cannot be used because it lacks pigment dispersibility.

  Examples of the polyester structure include polyester structures having a polyester group obtained by ring-opening polymerization of a lactone monomer, a styrene group, an acryloyl group, a cyanoacryloyl group, a methacryloyl group, a vinyl ether group, and the like. The resulting polyester group is preferred.

In the phosphate dispersant represented by the general formula (II), R ³ may be a single type of phosphate ester, or a plurality of types of phosphate esters composed of different R ³ may be used. Moreover, the phosphoric acid type | system | group dispersing agent of y = 1 may be individual, and the mixture of the phosphoric acid type dispersing agent of y = 1 and the phosphoric acid type dispersing agent of y = 2 may be sufficient.
When the phosphoric acid ester represented by the general formula (II) has an abundance ratio of the phosphoric acid dispersant having y = 1 and the phosphoric acid dispersant having y = 2 is 100: 0 to 100: 30, the pigment dispersibility Is preferable.

In addition, it is preferable that R ³ of the phosphoric acid dispersant represented by the general formula (II) has a polyester structure having a number average molecular weight of 400 to 10,000 because the pigment dispersibility is good. More preferably, it is 400-3000.
Furthermore, when the phosphoric acid dispersant R ³ represented by the general formula (II) has a polyester structure obtained by ring-opening polymerization of two or more different lactone monomers, the effect of the present invention is improved. Very preferred.

Furthermore, R ³ of the phosphoric acid dispersant represented by the general formula (II) is preferably represented by the following general formula (11).
Formula (11)
R ¹² —O—R ¹³ — (O—R ¹⁴ ) _S
(Wherein R ¹² represents an alkylene group, R ¹³ represents a trihydric or higher polyhydric alcohol structure, R ¹⁴ represents an acryloyl group, a cyanoacryloyl group, or a methacryloyl group, and s represents 2 or more.)

R ¹² is preferably an alkylene group having 8 or less carbon atoms. Further, from the viewpoint of pigment dispersibility, s is preferably 2 or more. In this case, R ¹⁴ may be a different group. As for s, 2-5 are still more preferable, and 2 is especially preferable.

Examples of the trihydric or higher polyhydric alcohol used in R ¹³ include glycerin, propyl alcohol, pentaerythritol, and dipentaerythritol. Particularly preferred are those having 3 to 6 valences.

  The acid value of the phosphoric acid dispersant is preferably 10 to 300 mgKOH / g, more preferably 30 to 200 mgKOH / g, and still more preferably 40 to 150 mgKOH / g.

  The phosphoric acid dispersant can be produced by a known method. For example, the description in paragraphs 0037 to 0051 of JP-A-2007-231107 can be referred to, and the contents thereof are incorporated herein.

The content of the phosphoric acid dispersant in the composition of the present invention is preferably 1 to 30% by mass, more preferably 2 to 20% by mass, and further preferably 4 to 15% by mass with respect to the total solid content. It is.
Moreover, it is preferable that it is 5-60 mass parts with respect to 100 mass parts of (A) pigment, and, as for content of (C) phosphoric acid type dispersing agent, it is more preferable that it is 9-40 mass parts.
Only 1 type of phosphoric acid type dispersing agent may be contained in the composition of this invention, and may be contained 2 or more types. When two or more types are included, the total amount is preferably within the above range.
In addition to the above, other dispersants may be included, and dispersants described in JP-A-2013-073104, 0338 to 0333 may also be included, the contents of which are incorporated herein.

<< (D) Resin formed by copolymerizing compound (x) represented by general formula (IV) and compound (y) having an ethylenically unsaturated double bond >>
The composition of the present invention comprises (D) a resin obtained by copolymerizing a compound (x) represented by the general formula (IV) and a compound (y) having an ethylenically unsaturated double bond (hereinafter referred to as a specific resin binder). Also called). In Patent Document 1 and Patent Document 2, the component (D) worked as a so-called dispersant. On the other hand, in this invention, (D) component acts as a compatibilizing agent. The reason for this is estimated as follows. That is, the component (C) (phosphoric acid dispersant) of the present invention easily aggregates and crystallizes the polyester residues, and other components (for example, (E) polymerization initiator and (F) constituting the composition). There was a tendency that only the component (C) aggregated and crystallized due to phase separation from the polymerizable compound. When the component (D) is added here, the sterically bulky aromatic ring moiety contained in the component (D) (the moiety represented by -Ph-R ⁶ of the compound (x) represented by the general formula (IV)) ) Enters the polyester residue part of the component (C) and prevents aggregation and crystallization of the polyester residues, and as a result, the effect of suppressing the phase separation of the component (C) is inferred. Is done.
Moreover, when the pigment composition described in the said patent document 3 and the patent document 4 is used for a colored photosensitive resin composition as it is, as above-mentioned, (C) other than a phosphoric acid type dispersing agent comprising a composition However, in the present invention, by blending the component (D), this point is eliminated, and each component constituting the composition is in the process of leaving (PCD) after coating. It is possible to effectively suppress phase separation.

一般式（ＩＶ）中、Ｒ⁴は水素原子またはメチル基を表し、Ｒ⁵は炭素数２または３のアルキレン基を表し、Ｒ⁶は水素原子またはベンゼン環を含んでいても良い炭素数１〜２０のアルキル基を表し、ｎは１〜１５の整数を表す。ｎが２以上の場合、複数のＲ⁵は同一であってもよく、異なっていてもよい。 Formula (IV)

In the general formula (IV), R ⁴ represents a hydrogen atom or a methyl group, R ⁵ represents an alkylene group having 2 or 3 carbon atoms, R ⁶ represents a hydrogen atom or a benzene ring which may contain a benzene ring. 20 represents an alkyl group, and n represents an integer of 1 to 15. When n is 2 or more, the plurality of R ⁵ may be the same or different.

R ⁶ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may contain a benzene ring. The alkyl group represented by R ⁶ is an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms. Examples of the alkyl group represented by R ⁶ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group.
Examples of the alkyl group containing a benzene ring represented by R ⁶ include 1-phenylethyl group, 1-phenylpropyl group, 1-phenylbutyl group, 1-phenylpentyl group, 1-phenylhexyl group, 1-phenylheptyl. Group, 1-phenyloctyl group, 1-phenylnonyl group, 1-phenyldecyl group, benzyl group, 2-phenyl (iso) propyl group and the like.
Among these, a benzyl group and a 2-phenyl (iso) propyl group are preferable.

  Compound (x) includes phenol ethylene oxide (EO) modified (meth) acrylate, paracumylphenol EO or propylene oxide (PO) modified (meth) acrylate, nonylphenol EO modified (meth) acrylate, nonylphenol PO modified (Meth) acrylate etc. are mentioned. Of these compounds, EO or PO-modified (meth) acrylate of paracumylphenol is particularly preferable for sufficiently obtaining a function as a compatibilizing agent for the resin (D).

  As the compound (y) having an ethylenically unsaturated double bond, (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, (iso) propyl (meth) acrylate, (iso) butyl (meth) Acrylate, (iso) pentyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, glycidyl (meth) acrylate, isobornyl (meth) ) Acrylate, acid phosphooxyethyl (meth) acrylate, acid phosphooxypropyl (meth) acrylate, 3-chloro-2-acid phosphooxyethyl (meth) acrylate, acid phosphooxypolyethylene glycol (Meth) acrylate.

  The ratio of the compound (x) in the (D) resin in the present invention is 0.1 to 50% by mass, more preferably 10 to 35% by mass. When the proportion of the compound (x) is less than 10% by mass, the effect of the resin (D) as a compatibilizer is lowered, and when it is less than 0.1% by mass, the effect of the resin (D) as a compatibilizer is further increased. Since it falls, it is not preferable. On the other hand, when the amount is more than 35% by mass, the hydrophobicity increases, and the developability of the colored photosensitive resin composition may be lowered or a residue may be caused. Compatibility with other components in the composition may be significantly reduced, and precipitation of monomers and photopolymerization initiators may occur.

The weight average molecular weight (Mw) of (D) resin (copolymer) in this invention becomes like this. Preferably it is 5000-100000, More preferably, it is 10000-50000.

  Moreover, in order to improve the sensitivity of a colored photosensitive resin composition, the ethylenic double bond is introduce | transduced into the side chain of (D) resin (copolymer) in this invention, and a monomer or resin reacts. Can do. Specifically, when the resin has a reactive functional group such as a hydroxyl group, the functional group that reacts with the reactive functional group such as glycidyl (meth) acrylate, 2- (meth) acryloyloxyisocyanate and the ethylenic group. An ethylenic double bond is introduced into the side chain by reacting a compound having a saturated group.

  (D) The resin can be produced by a known method. For example, the description in paragraphs 0041 to 0045 of JP-A No. 2004-101728 can be referred to, and the contents thereof are incorporated herein.

The content of the (D) resin in the composition of the present invention is preferably 1 to 50% by mass, more preferably 3 to 40% by mass, and further preferably 5 to 30% by mass with respect to the total solid content. is there.
Moreover, it is preferable that it is 5-80 mass parts with respect to 100 mass parts of (A) pigment, and, as for content of (D) resin, it is more preferable that it is 10-70 mass parts. (D) By making content of resin into 5-80 mass parts with respect to 100 mass parts of (A) pigments, (D) resin functions effectively as a compatibilizer, not as a dispersant. The effect of the present invention is excellent.
(D) 1 type of resin may be contained in the composition of this invention, and may be contained 2 or more types. When two or more types are included, the total amount is preferably within the above range.

<(E) Photopolymerization initiator>
The composition of this invention contains a photoinitiator from a viewpoint of the further sensitivity improvement.
The photopolymerization initiator is not particularly limited as long as it has the ability to initiate polymerization of a polymerizable compound described later, and can be appropriately selected from known photopolymerization initiators. For example, those having photosensitivity to visible light from the ultraviolet region are preferable. Further, it may be an activator that generates some action with a photoexcited sensitizer and generates an active radical, or may be an initiator that initiates cationic polymerization according to the type of monomer.
The photopolymerization initiator preferably contains at least one compound having a molecular extinction coefficient of at least about 50 within a range of about 300 nm to 800 nm (more preferably 330 nm to 500 nm).

  Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (for example, those having a triazine skeleton, those having an oxadiazole skeleton, etc.), acylphosphine compounds such as acylphosphine oxide, hexaarylbiimidazole, oxime. Examples include oxime compounds such as derivatives, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ketoxime ethers, aminoacetophenone compounds, and hydroxyacetophenones.

  From the viewpoint of exposure sensitivity, trihalomethyltriazine compounds, benzyldimethylketal compounds, α-hydroxyketone compounds, α-aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, triarylimidazole dimers, oniums Compounds selected from the group consisting of compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds and derivatives thereof, cyclopentadiene-benzene-iron complexes and salts thereof, halomethyloxadiazole compounds, and 3-aryl substituted coumarin compounds are preferred.

A commercially available product can be used as the trihalomethyltriazine compound, for example, TAZ-107 (manufactured by Midori Chemical Co., Ltd.) can also be used.
In particular, when the composition of the present invention is used for the production of a color filter included in a solid-state imaging device, it is necessary to form a fine pattern with a sharp shape. It is important that it be developed. From such a viewpoint, it is particularly preferable to use an oxime compound as the photopolymerization initiator. In particular, when a fine pattern is formed in a solid-state imaging device, stepper exposure is used for curing exposure, but this exposure machine may be damaged by halogen, and the amount of photopolymerization initiator added must be kept low. Therefore, in view of these points, it is most preferable to use an oxime compound as the photopolymerization initiator (E) to form a fine pattern such as a solid-state imaging device.

  As the halogenated hydrocarbon derivative having the triazine skeleton, the ketone compound, and the photopolymerization initiator other than the above, the compounds described in paragraphs 0074 to 0077 of JP2013-077009A can be referred to. The contents are incorporated herein.

As the photopolymerization initiator, hydroxyacetophenone compounds, aminoacetophenone compounds, and acylphosphine compounds can also be suitably used. More specifically, for example, aminoacetophenone initiators described in JP-A-10-291969 and acylphosphine oxide initiators described in Japanese Patent No. 4225898 can also be used.
As the hydroxyacetophenone-based initiator, IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, IRGACURE-127 (trade names: all manufactured by BASF) can be used. As the aminoacetophenone-based initiator, commercially available products IRGACURE-907, IRGACURE-369, IRGACURE-379, IRGACURE-OXE379 (trade names: all manufactured by BASF) can be used. As the aminoacetophenone-based initiator, a compound described in JP-A-2009-191179 in which an absorption wavelength is matched with a long-wave light source such as 365 nm or 405 nm can also be used. As the acylphosphine-based initiator, commercially available products such as IRGACURE-819 and DAROCUR-TPO (trade names: both manufactured by BASF) can be used.

More preferred examples of the photopolymerization initiator include oxime compounds. Specific examples of the oxime compound include compounds described in JP-A No. 2001-233842, compounds described in JP-A No. 2000-80068, and compounds described in JP-A No. 2006-342166. Examples of the oxime compound include J.M. C. S. Perkin II (1979) pp. 1653-1660), J.M. C. S. Perkin II (1979) pp. 156-162, Journal of Photopolymer Science and Technology (1995) pp. 202-232, compounds described in JP-A No. 2000-66385, compounds described in JP-A No. 2000-80068, JP-T 2004-534797, JP-A No. 2006-342166, and the like.
IRGACURE-OXE01 (manufactured by BASF), IRGACURE-OXE02 (manufactured by BASF), and TR-PBG-304 (manufactured by Changzhou Powerful New Materials Co., Ltd.) are also suitably used as commercial products.

  As an oxime compound such as an oxime derivative suitably used as a photopolymerization initiator in the present invention, the compounds described in paragraphs 0080 to 0116 of JP2013-077009A can be referred to, and the contents thereof are described in the present specification. Incorporated into.

  The oxime compound has a maximum absorption wavelength in a wavelength region of 350 nm to 500 nm, preferably has an absorption wavelength in a wavelength region of 360 nm to 480 nm, and particularly preferably has high absorbance at 365 nm and 455 nm.

From the viewpoint of sensitivity, the molar extinction coefficient at 365 nm or 405 nm of the oxime compound is preferably 1,000 to 300,000, more preferably 2,000 to 300,000, and 5,000 to 200,000. 000 is particularly preferred.
The molar extinction coefficient of the compound can be measured using a known method. Specifically, for example, in an ultraviolet-visible spectrophotometer (Varian Inc., Carry-5 spctrophotometer), using an ethyl acetate solvent, It is preferable to measure at a concentration of 0.01 g / L.

  You may use the photoinitiator used for this invention in combination of 2 or more type as needed.

  When (E) a photopolymerization initiator is contained in the composition of the present invention, the content of (E) the photopolymerization initiator is 0.1% by mass or more and 50% by mass or less based on the total solid content of the composition. More preferably, it is 0.5 mass% or more and 30 mass% or less, More preferably, it is 1 mass% or more and 20 mass% or less. Within this range, better sensitivity and pattern formability can be obtained.

<< (F) polymerizable compound >>
The composition of the present invention contains (F) a polymerizable compound. In the present invention, known polymerizable compounds that can be cross-linked by radicals, acids, and heat can be used, and examples thereof include polymerizable compounds containing an ethylenically unsaturated bond, cyclic ether (epoxy, oxetane), methylol and the like. . (F) The polymerizable compound is preferably selected from compounds having at least one terminal ethylenically unsaturated bond, preferably two or more, from the viewpoint of sensitivity. Among them, a polyfunctional polymerizable compound having 4 or more functional groups is preferable, and a polyfunctional polymerizable compound having 5 or more functional groups is more preferable.

  Such a compound group is widely known in the industrial field, and can be used without any particular limitation in the present invention. These may be in any chemical form such as, for example, monomers, prepolymers, ie dimers, trimers and oligomers or mixtures thereof and oligomers thereof. The polymeric compound in this invention may be used individually by 1 type, and may use 2 or more types together.

More specifically, examples of monomers and prepolymers thereof include unsaturated carboxylic acids (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), esters thereof, amides, And multimers thereof, preferably esters of unsaturated carboxylic acids and aliphatic polyhydric alcohol compounds, amides of unsaturated carboxylic acids and aliphatic polyhydric amine compounds, and multimers thereof. is there. In addition, addition reaction products of monofunctional or polyfunctional isocyanates or epoxies with unsaturated carboxylic acid esters or amides having a nucleophilic substituent such as hydroxy group, amino group, mercapto group, monofunctional or polyfunctional. A dehydration condensation reaction product with a functional carboxylic acid is also preferably used. In addition, an addition reaction product of an unsaturated carboxylic acid ester or amide having an electrophilic substituent such as an isocyanate group or an epoxy group with a monofunctional or polyfunctional alcohol, amine, or thiol, and a halogen group A substitution reaction product of an unsaturated carboxylic acid ester or amide having a detachable substituent such as a tosyloxy group and a monofunctional or polyfunctional alcohol, amine or thiol is also suitable. As another example, it is also possible to use a compound group in which an unsaturated phosphonic acid, a vinylbenzene derivative such as styrene, vinyl ether, allyl ether or the like is used instead of the unsaturated carboxylic acid.
As these specific compounds, the compounds described in paragraphs [0095] to [0108] of JP-A-2009-288705 can also be suitably used in the present invention.

  Further, as the polymerizable compound, a compound having an ethylenically unsaturated group having a boiling point of 100 ° C. or higher under normal pressure and having at least one addition-polymerizable ethylene group is also preferable. As an example thereof, the compound described in paragraph 0124 of JP2013-077009A can be referred to, the contents of which are incorporated herein.

  Moreover, as a compound having a boiling point of 100 ° C. or higher under normal pressure and having at least one addition-polymerizable ethylenically unsaturated group, paragraph numbers [0254] to [0257] of JP-A-2008-292970 are disclosed. Also suitable are the compounds described in.

  In addition to the above, radical polymerizable monomers represented by general formulas (MO-1) to (MO-5) described in paragraphs 0126 to 0129 of JP2013-077009A can be referred to, and the contents thereof are described in the present specification. Incorporated into.

  Moreover, the compound which (meth) acrylate-ized after adding ethylene oxide and propylene oxide to the said polyfunctional alcohol described with the specific example as general formula (1) and (2) in Unexamined-Japanese-Patent No. 10-62986 is also, It can be used as the polymerizable compound.

  Among these, as the polymerizable compound, dipentaerythritol triacrylate (KAYARAD D-330 as a commercial product; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (KAYARAD D-320 as a commercial product; Nippon Kayaku) Dipentaerythritol penta (meth) acrylate (manufactured by Co., Ltd.) (as a commercial product, KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (as a commercial product, KAYARAD DPHA; Nippon Kayaku Co., Ltd.) A company-made, A-DPH-12E; made by Shin-Nakamura Chemical Co., Ltd.) and a structure in which these (meth) acryloyl groups are mediated by ethylene glycol and propylene glycol residues are preferred. These oligomer types can also be used. Preferred embodiments of the polymerizable compound are shown below.

  The polymerizable compound is a polyfunctional monomer and may have an acid group such as a carboxy group, a sulfonic acid group, or a phosphoric acid group. If the ethylenic compound has an unreacted carboxy group as in the case of a mixture as described above, this can be used as it is. Non-aromatic carboxylic acid anhydrides may be reacted to introduce acid groups. In this case, specific examples of the non-aromatic carboxylic acid anhydride used include tetrahydrophthalic anhydride, alkylated tetrahydrophthalic anhydride, hexahydrophthalic anhydride, alkylated hexahydrophthalic anhydride, succinic anhydride, anhydrous Maleic acid is mentioned.

  In the present invention, the monomer having an acid group is an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and a non-aromatic carboxylic acid anhydride is reacted with an unreacted hydroxy group of the aliphatic polyhydroxy compound. A polyfunctional monomer having an acid group is preferable, and in this ester, the aliphatic polyhydroxy compound is pentaerythritol and / or dipentaerythritol. Examples of commercially available products include M-510 and M-520 as polybasic acid-modified acrylic oligomers manufactured by Toagosei Co., Ltd.

These monomers may be used alone, but since it is difficult to use a single compound in production, two or more kinds may be mixed and used. Moreover, you may use together the polyfunctional monomer which does not have an acid group as a monomer, and the polyfunctional monomer which has an acid group as needed.
A preferable acid value of the polyfunctional monomer having an acid group is 0.1 mgKOH / g to 40 mgKOH / g, and particularly preferably 5 mgKOH / g to 30 mgKOH / g. If the acid value of the polyfunctional monomer is too low, the developing dissolution properties are lowered, and if it is too high, the production and handling are difficult, the photopolymerization performance is lowered, and the curability such as the surface smoothness of the pixel is deteriorated. Accordingly, when two or more polyfunctional monomers having different acid groups are used in combination, or when a polyfunctional monomer having no acid group is used in combination, the acid groups as the entire polyfunctional monomer should be adjusted so as to fall within the above range. Is preferred.

Moreover, it is also a preferable aspect to contain a polyfunctional monomer having a caprolactone structure as the polymerizable monomer.
The polyfunctional monomer having a caprolactone structure is not particularly limited as long as it has a caprolactone structure in the molecule. For example, trimethylolethane, ditrimethylolethane, trimethylolpropane, ditrimethylolpropane, penta Ε-caprolactone modified polyfunctionality obtained by esterifying polyhydric alcohol such as erythritol, dipentaerythritol, tripentaerythritol, glycerin, diglycerol, trimethylolmelamine, (meth) acrylic acid and ε-caprolactone ( Mention may be made of (meth) acrylates. In particular, compounds described in paragraphs 0135 to 0153 of JP2013-077009A can be referred to, and the contents thereof are incorporated herein.

  Examples of such commercially available polymerizable compounds include SR-494, which is a tetrafunctional acrylate having four ethyleneoxy chains manufactured by Sartomer, and six pentyleneoxy chains manufactured by Nippon Kayaku Co., Ltd. 6 Examples thereof include DPCA-60, which is a functional acrylate, and TPA-330, which is a trifunctional acrylate having three isobutyleneoxy chains.

Examples of the polymerizable compound include urethane acrylates as described in JP-B-48-41708, JP-A-51-37193, JP-B-2-32293, and JP-B-2-16765. And urethane compounds having an ethylene oxide skeleton described in JP-B-58-49860, JP-B-56-17654, JP-B-62-39417, and JP-B-62-39418 are also suitable. Further, as the polymerizable compound, addition polymerization having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-1-105238 is used. By using curable compounds, it is possible to obtain a curable composition having an extremely excellent photosensitive speed.
Commercially available products of the above polymerizable compounds include urethane oligomers UAS-10, UAB-140 (manufactured by Sanyo Kokusaku Pulp Co., Ltd.), UA-7200 "(manufactured by Shin-Nakamura Chemical Co., Ltd., DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA -306H, UA-306T, UA-306I, AH-600, T-600, AI-600 (manufactured by Kyoeisha), trimethylolpropane triacrylate (commercially available products are A-TMPT; manufactured by Shin-Nakamura Chemical Co., Ltd.), etc. Can be mentioned.

  Examples of the cyclic ether (epoxy, oxetane) include those having an epoxy group such as JER-827, JER-828, JER-834, JER-1001, JER-1002, and JER-1003 as bisphenol A type epoxy resins. , JER-1055, JER-1007, JER-1009, JER-1010 (above, manufactured by Japan Epoxy Resin Co., Ltd.), EPICLON 860, EPICLON 1050, EPICLON 1051, EPICLON 1055 (above, manufactured by DIC Corporation), etc., and bisphenol F As a type epoxy resin, JER-806, JER-807, JER-4004, JER-4005, JER-4007, JER-4010 (above, manufactured by Japan Epoxy Resins Co., Ltd.), EPICLON830 EPICLON 835 (above, manufactured by DIC Corporation), LCE-21, RE-602S (above, manufactured by Nippon Kayaku Co., Ltd.), etc., and phenol novolac type epoxy resins such as JER-152, JER-154, JER- 157S70, JER-157S65 (above, manufactured by Japan Epoxy Resin Co., Ltd.), EPICLON N-740, EPICLON N-770, EPICLON N-775 (above, manufactured by DIC Corporation), etc., and a cresol novolac type epoxy resin EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, EPICLON N-695 (above, manufactured by DIC Corporation), EOCN-1020 ( that's all Nippon Kayaku Co., Ltd.), ADEKA RESIN EP-4080S, EP-4085S, EP-4088S (above, manufactured by ADEKA) Celoxide 2021P, Celoxide 2081, Celoxide 2083, Celoxide 2085, EHPE-3150 (1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol), EPOLEEAD PB 3600, PB 4700 (above, Daicel Chemical) Kogyo Co., Ltd.), Denacol EX-211L, EX-212L, EX-214L, EX-216L, EX-321L, EX-850L (above, manufactured by Nagase ChemteX Corporation), ADEKA RESIN EP-4000S, the same EP-4003S, EP-4010S, EP-4011S (above, manufactured by ADEKA Corporation), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, EPPN-502 (above, manufactured by ADEKA Corporation) ), JER-1031S (manufactured by Japan Epoxy Resin Co., Ltd.) and the like. Such a polymerizable compound is suitable for forming a pattern by a dry etching method.

About these polymeric compounds, the details of usage methods, such as the structure, single use, combined use, and addition amount, can be arbitrarily set according to the final performance design of the colored photosensitive resin composition. For example, from the viewpoint of sensitivity, a structure having a high unsaturated group content per molecule is preferable, and in many cases, a bifunctional or higher functionality is preferable. Further, from the viewpoint of increasing the strength of the cured film formed from the colored photosensitive resin composition, those having three or more functional groups are preferable, and further, different functional groups / different polymerizable groups (for example, acrylic ester, methacrylate ester, styrene). It is also effective to adjust both sensitivity and strength by using a compound of a vinyl compound or a vinyl ether compound). Furthermore, in combination with tri- or more functional polymerizable compounds having different ethylene oxide chain lengths, the developability of the colored photosensitive resin composition can be adjusted, and an excellent pattern forming ability can be obtained. preferable.
In addition, the selection of the polymerizable compound is also possible with respect to the compatibility and dispersibility with other components (for example, a photopolymerization initiator, a dispersion, an alkali-soluble resin, etc.) contained in the colored photosensitive resin composition. The method of use is an important factor. For example, compatibility may be improved by using a low-purity compound or using two or more kinds in combination. In addition, a specific structure may be selected from the viewpoint of improving adhesion to a hard surface such as a support.

  The content of the polymerizable compound (F) in the composition of the present invention is preferably 0.1% by mass to 90% by mass, and preferably 1.0% by mass to the total solid content in the colored photosensitive resin composition. 50 mass% is further more preferable, and 2.0 mass%-30 mass% is especially preferable.

<< other ingredients >>
In addition to the components described above, the composition of the present invention is a range that does not impair the effects of the present invention. May be included.

-(G) Resin having a polymerizable double bond in the side chain-
In the present invention, if necessary, a resin having a polymerizable double bond in the side chain (G) (hereinafter also referred to as “(G) resin”) may be contained. (G) By further containing a resin having a polymerizable double bond in the side chain, the composition of the present invention can be cured more effectively. The polymerizable double bond is preferably (meth) acrylate.

  (G) The resin having a polymerizable double bond in the side chain is not particularly limited as long as it has a polymerizable double bond in the side chain, but the polymerizable monomer having 2 to 6 hydroxyl groups (p) And a copolymer (a) with other polymerizable monomer (q), a resin obtained by reacting a functional group capable of reacting with a hydroxyl group and a compound (b) having an ethylenically unsaturated double bond Is preferred.

  (G) The polymerizable monomer (p) having 2 to 6 hydroxyl groups constituting the resin having a polymerizable double bond in the side chain has 2 to 6 hydroxyl groups and an ethylenically unsaturated double bond. For example, a monomer represented by the following general formula (1) can be used.

（式中、Ｒ¹及びＲ⁴はそれぞれ水素原子、炭素数１〜５の置換されてもよいアルキル基を表し、Ｒ²は炭素数１〜４のアルキレン基を表し、Ｒ³は炭素数１〜４のアルキレン基、または単結合を表し、ｎは２以上６以下の整数を表す。）
上記一般式（１）で示されるモノマーとしては、エチレン性不飽和二重結合を有する多価アルコールのモノエステルなどが挙げられるが、好ましいのはグリセロールモノ（メタ）アクリレートである。 General formula (1)

(In the formula, R ¹ and R ⁴ each represent a hydrogen atom and an optionally substituted alkyl group having 1 to 5 carbon atoms, R ² represents an alkylene group having 1 to 4 carbon atoms, and R ³ represents 1 carbon atom. -4 represents an alkylene group or a single bond, and n represents an integer of 2 to 6.
Examples of the monomer represented by the general formula (1) include monoesters of polyhydric alcohols having an ethylenically unsaturated double bond, and glycerol mono (meth) acrylate is preferred.

  The other polymerizable monomer (q) is a polymerizable monomer copolymerizable with the polymerizable monomer (p) having 2 to 6 hydroxyl groups. For example, (meth) acrylic acid, methyl (meth) acrylate, ethyl ( (Meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl ( (Meth) acrylic acid such as (meth) acrylate, phenoxyethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, etc. Stealth; N-vinylpyrrolidone; styrene and its derivatives, styrenes such as α-methylstyrene; acrylamides such as (meth) acrylamide, methylol (meth) acrylamide, alkoxymethylol (meth) acrylamide, diacetone (meth) acrylamide; Examples include (meth) acrylonitrile, other vinyl compounds such as ethylene, propylene, butylene, vinyl chloride, and vinyl acetate, and macromonomers such as polymethyl methacrylate macromonomer and polystyrene macromonomer. These monomers can be used individually by 1 type or in mixture of 2 or more types.

  The copolymerization ratio of the polymerizable monomer (p) having 2 to 6 hydroxyl groups and the other polymerizable monomer (q) is preferably 5 to 95% by mass: 95 to 5% by mass, 70% by mass: More preferably, it is 70 to 30% by mass. When the copolymerization ratio of the polymerizable monomer (p) is less than 5% by mass, the number of ethylenically unsaturated double bonds that can be introduced is small, and the double bond equivalent (double bond equivalent defined by the following formula) The numerical value becomes large and sufficient sensitivity cannot be obtained. When the copolymerization ratio of the polymerizable monomer (p) exceeds 95% by mass, it becomes possible to introduce many ethylenically unsaturated double bonds, but the ratio of the polymerizable monomer (q) becomes low. It is difficult to maintain physical properties such as dispersion stability, solubility, and chemical resistance.

  Production of a copolymer (a) of a polymerizable monomer (p) having 2 to 6 hydroxyl groups and another polymerizable monomer (q) can be produced by a known method. No. 156930, paragraph 0013 can be referred to, the contents of which are incorporated herein.

(G) The resin having a polymerizable double bond in the side chain is obtained by reacting the copolymer (a) with a functional group capable of reacting with a hydroxyl group and a compound (b) having an ethylenically unsaturated double bond. Is obtained. Examples of the functional group capable of reacting with a hydroxyl group of the compound (b) having a functional group capable of reacting with a hydroxyl group and an ethylenically unsaturated double bond include an isocyanate group and a carboxy group. Groups are preferred.
Specific examples of the compound having an isocyanate group and an ethylenically unsaturated double bond include 2-acryloylethyl isocyanate and 2-methacryloylethyl isocyanate. Specific examples of the compound having a carboxy group and an ethylenically unsaturated double bond include acrylic acid, methacrylic acid, and maleic anhydride.

The amount of ethylenically unsaturated double bonds introduced into the copolymer (a) via a hydroxyl group is indicated by the “double bond equivalent” of the resulting resin. The double bond equivalent is a measure of the amount of double bonds contained in the molecule. If the photosensitive resin has the same molecular weight, the smaller the double bond equivalent value, the more the amount of double bonds introduced. Become more.
[Double bond equivalent] = [molecular weight of repeating structural unit] / [number of double bonds in repeating structural unit]
The double bond equivalent of the (G) resin in the present invention is preferably 200 to 2,000, and more preferably 300 to 900. (G) When the double bond equivalent of the resin is less than 200, the ratio of the polymerizable monomer (p) for introducing the ethylenically unsaturated double bond is high, and a sufficient amount of polymerization to maintain various properties Monomer (q) cannot be copolymerized. When it exceeds 2,000, sufficient sensitivity cannot be obtained because the number of ethylenically unsaturated double bonds is small.
Moreover, the weight average molecular weight (Mw) of the above (G) resin is preferably 2000 to 200000, more preferably 5000 to 50000, from the viewpoint of good dispersibility of the composition of the present invention.

  The reaction between the copolymer (a), the functional group capable of reacting with a hydroxyl group and the compound (b) having an ethylenically unsaturated double bond can be carried out by a known method, for example, JP-A-2005-156930. Reference can be made to the description of paragraph 0016 of the publication, the contents of which are incorporated herein.

The content of the resin having a polymerizable double bond in the side chain (G) in the composition of the present invention is preferably from 0.1 to 50 mass%, more preferably from 0.3 to 40, based on the total solid content. It is mass%, More preferably, it is 0.5-30 mass%.
(G) 1 type of resin which has a polymerizable double bond in a side chain may be contained in the composition of this invention, and may be contained 2 or more types. When two or more types are included, the total amount is preferably within the above range.

-Alkali-soluble resin-
The composition of the present invention may further contain an alkali-soluble resin as a binder. In addition, the component contained in the composition of this invention as an dispersing agent component is not contained in alkali-soluble resin here.

  The alkali-soluble resin is a linear organic polymer, and promotes at least one alkali-solubility in a molecule (preferably a molecule having an acrylic copolymer or a styrene copolymer as a main chain). It can be suitably selected from alkali-soluble resins having a group. From the viewpoint of heat resistance, polyhydroxystyrene resins, polysiloxane resins, acrylic resins, acrylamide resins, and acryl / acrylamide copolymer resins are preferable. From the viewpoint of development control, acrylic resins and acrylamide resins are preferable. Resins and acrylic / acrylamide copolymer resins are preferred.

  As the alkali-soluble resin, for example, an alkali-soluble resin described in paragraphs 0179 to 0208 of JP2013-077009A can be referred to, and the contents thereof are incorporated in the present specification.

In addition, as the alkali-soluble resin, paragraphs 0558 to 0571 of JP2012-208494A (corresponding to [0685] to [0700] of the corresponding US Patent Application Publication No. 2012/0235099) can be referred to, and these can be referred to. Is incorporated herein by reference.
Furthermore, the copolymer (B) described in paragraph Nos. 0029 to 0063 described in JP 2012-32767 A and the alkali-soluble resin used in Examples, paragraph Nos. 0088 of JP 2012-208474 A The binder resin described in 0098 and the binder resin used in Examples, the binder resin described in Paragraph Nos. 0022 to 0032 of JP 2012-137531 B, and the binder resin used in Examples, No. 024934, paragraph numbers 0132 to 0143 described in paragraphs 0132 to 0143 and the binder resins used in the examples, JP 2011-242752A paragraphs 0092 to 0098 and the binder resins used in the examples, Paragraph No. of Kokai 2012-032770 It preferred to use a binder resin according to 030-0072. These contents are incorporated herein.

The acid value of the alkali-soluble resin is preferably 30 mgKOH / g to 200 mgKOH / g, more preferably 50 mgKOH / g to 150 mgKOH / g, and most preferably 70 mgKOH / g to 120 mgKOH / g.
Further, the weight average molecular weight (Mw) of the alkali-soluble resin is preferably 2,000 to 50,000, more preferably 5,000 to 30,000, and most preferably 7,000 to 20,000.

When the alkali-soluble resin is contained in the coloring composition, the content of the alkali-soluble resin in the coloring composition is preferably 1% by mass to 15% by mass, more preferably based on the total solid content of the coloring composition. Is 2% by mass to 12% by mass, and particularly preferably 3% by mass to 10% by mass.
The composition of the present invention may contain only one kind of alkali-soluble resin, or may contain two or more kinds. When two or more types are included, the total amount is preferably within the above range.

-Organic solvent-
The composition of the present invention may contain an organic solvent.
The organic solvent is basically not particularly limited as long as the solubility of each component and the coating property of the colored photosensitive resin composition are satisfied. Is preferably selected in consideration of safety and safety. One type of organic solvent may be sufficient and two or more types may be contained.

  Examples of organic solvents include esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, and oxyacetic acid. Alkyl (e.g., methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (e.g., methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate)), 3-oxypropionic acid alkyl esters ( Examples: methyl 3-oxypropionate, ethyl 3-oxypropionate, etc. (for example, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, etc.)) 2-oxypropion Alkyl esters (eg, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc. (eg, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate) , Methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate)), methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate (for example, 2-methoxy-2-methylpropionic acid) Methyl, ethyl 2-ethoxy-2-methylpropionate, etc.), methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate and the like, and Examples of ethers include die Lenglycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene Glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, etc., and ketones, for example, methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc., and aromatic hydrocarbons, for example, toluene, xylene, Siku A preferred example is lopentanone.

  It is also preferable to mix two or more of these organic solvents from the viewpoints of solubility of the ultraviolet absorber and the alkali-soluble resin, improvement of the coated surface, and the like. In this case, particularly preferably, the above-mentioned methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl It is a mixed solution composed of two or more selected from carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, and propylene glycol methyl ether acetate.

  The content of the organic solvent in the composition is preferably such that the total solid concentration of the composition is 5% by mass to 80% by mass from the viewpoint of applicability, and further 5% by mass to 60% by mass. Preferably, 10% by mass to 50% by mass is particularly preferable.

-Crosslinking agent-
It is also possible to supplement the composition of the present invention with a crosslinking agent to further increase the hardness of a cured film obtained by curing the composition.
The crosslinking agent is not particularly limited as long as the film can be cured by a crosslinking reaction. For example, at least selected from (a) an epoxy resin, (b) a methylol group, an alkoxymethyl group, and an acyloxymethyl group. Substituted with at least one substituent selected from a melamine compound, a guanamine compound, a glycoluril compound or a urea compound, (c) a methylol group, an alkoxymethyl group, and an acyloxymethyl group, which is substituted with one substituent; Phenol compounds, naphthol compounds or hydroxyanthracene compounds. Of these, polyfunctional epoxy resins are preferred.
The details of paragraphs 0134 to 0147 of JP-A No. 2004-295116 can be referred to for details such as specific examples of the crosslinking agent.
When the crosslinking agent is contained in the composition of the present invention, the blending amount of the crosslinking agent is not particularly defined, but is preferably 2 to 30% by mass, more preferably 3 to 20% by mass based on the total solid content of the composition. preferable.
The composition of the present invention may contain only one type of cross-linking agent, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.

-Polymerization inhibitor-
In the composition of the present invention, it is desirable to add a small amount of a polymerization inhibitor in order to prevent unnecessary thermal polymerization of the polymerizable compound during the production or storage of the composition.
Examples of the polymerization inhibitor that can be used in the present invention include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4′-thiobis (3-methyl-6- tert-butylphenol), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), N-nitrosophenylhydroxyamine primary cerium salt and the like.
When a polymerization inhibitor is contained in the composition of the present invention, the addition amount of the polymerization inhibitor is preferably about 0.01% by mass to about 5% by mass with respect to the mass of the entire composition.
The composition of the present invention may contain only one type of polymerization inhibitor, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.

-Surfactant-
Various surfactants may be added to the composition of the present invention from the viewpoint of further improving coatability. In the present invention, by blending the surfactant, when the above component (C) and component (D) are combined, the effect of the present invention that is excellent in PCD resistance can be more effectively exhibited. The following mechanism is presumed as the reason. That is, as described above, the reason why the composition of the present invention is excellent in PCD resistance is, as described above, a sterically bulky aromatic ring moiety contained in the component (D) (-of the compound (x) represented by the general formula (IV)). The portion represented by Ph-R ⁶ ) enters the polyester residue portion of component (C) and prevents the polyester residues from aggregating and crystallizing, resulting in phase separation of component (C). This is considered to be suppressed. When a surfactant is added here, a surfactant effect acts between the three-dimensionally bulky aromatic ring part contained in the component (D) and the polyester residue part of the component (C), and the three-dimensional structure of the component (D). It is presumed that the bulky part smoothly enters the polyester residue part of the component (C).
As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.

In particular, since the composition of the present invention contains a fluorosurfactant, the liquid properties (particularly fluidity) when prepared as a coating liquid are further improved. Sex can be improved more.
That is, when a film is formed using a coating liquid to which a composition containing a fluorosurfactant is applied, the wettability to the coated surface is reduced by reducing the interfacial tension between the coated surface and the coating liquid. Is improved, and the coating property to the coated surface is improved. For this reason, even when a thin film of about several μm is formed with a small amount of liquid, it is effective in that it is possible to more suitably form a film having a uniform thickness with small thickness unevenness.

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

  Examples of the fluorosurfactant include Megafac F171, F172, F173, F176, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, F780, F781 (above DIC Corporation), Florard FC430, FC431, FC171 (above, Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC1068, SC-381, SC-383, S393, and KH-40 (above, manufactured by Asahi Glass Co., Ltd.).

  Specific examples of the nonionic surfactant include glycerol, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (for example, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene Stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester (Pluronic L10, L31, L61, L62 manufactured by BASF, 10R5, 17R2, 25R2, Tetronic 304, 701, 704, 901, 904, 150R1), Rusupasu 20000 (Lubrizol Japan Co., Ltd.), and the like.

  Specific examples of the cationic surfactant include phthalocyanine derivatives (trade name: EFKA-745, manufactured by Morishita Sangyo Co., Ltd.), organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth) acrylic acid ( Co) polymer polyflow no. 75, no. 90, no. 95 (manufactured by Kyoeisha Chemical Co., Ltd.), W001 (manufactured by Yusho Co., Ltd.) and the like.

  Specific examples of the anionic surfactant include W004, W005, W017 (manufactured by Yusho Co., Ltd.) and the like.

Examples of the silicone surfactant include “Toray Silicone DC3PA”, “Toray Silicone SH7PA”, “Toray Silicone DC11PA”, “Tore Silicone SH21PA”, “Tore Silicone SH28PA”, “Toray Silicone” manufactured by Toray Dow Corning Co., Ltd. “Silicone SH29PA”, “Toresilicone SH30PA”, “Toresilicone SH8400”, “TSF-4440”, “TSF-4300”, “TSF-4445”, “TSF-4460”, “TSF” manufactured by Momentive Performance Materials, Inc. -4552 "," KP341 "," KF6001 "," KF6002 "manufactured by Shin-Etsu Silicone Co., Ltd.," BYK307 "," BYK323 "," BYK330 "manufactured by Big Chemie.
Only one type of surfactant may be used, or two or more types may be combined.
When the composition of the present invention contains a surfactant, the addition amount of the surfactant is preferably 0.001% by mass to 2.0% by mass, more preferably 0.001% by mass with respect to the total mass of the composition. It is 005 mass%-1.0 mass%.
The composition of the present invention may contain only one type of surfactant or two or more types of surfactant. When two or more types are included, the total amount is preferably within the above range.

-Other additives-
Various additives, for example, fillers, adhesion promoters, antioxidants, ultraviolet absorbers, anti-aggregation agents, and the like can be blended with the composition of the present invention as necessary. Examples of these additives include those described in paragraphs 0155 to 0156 of JP-A No. 2004-295116.
The composition of the present invention may contain a sensitizer and a light stabilizer described in paragraph 0078 of JP-A No. 2004-295116, and a thermal polymerization inhibitor described in paragraph 0081 of the same publication.
Specifically, the following compounds are preferably used as the ultraviolet absorber.

--Organic carboxylic acid, organic carboxylic anhydride--
The composition of the present invention may contain an organic carboxylic acid having a molecular weight of 1000 or less and / or an organic carboxylic acid anhydride.
Specific examples of the organic carboxylic acid compound include aliphatic carboxylic acids and aromatic carboxylic acids. Examples of aliphatic carboxylic acids include monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, glycolic acid, acrylic acid, methacrylic acid, oxalic acid, malonic acid, succinic acid, Examples thereof include dicarboxylic acids such as glutaric acid, adipic acid, pimelic acid, cyclohexanedicarboxylic acid, cyclohexenedicarboxylic acid, itaconic acid, citraconic acid, maleic acid and fumaric acid, and tricarboxylic acids such as tricarbaryl acid and aconitic acid. Examples of the aromatic carboxylic acid include carboxylic acids in which a carboxy group is directly bonded to a phenyl group such as benzoic acid and phthalic acid, and carboxylic acids in which a carboxy group is bonded to the phenyl group through a carbon bond. Among these, those having a molecular weight of 600 or less, particularly a molecular weight of 50 to 500, specifically maleic acid, malonic acid, succinic acid, and itaconic acid are preferred.

  Examples of organic carboxylic acid anhydrides include aliphatic carboxylic acid anhydrides and aromatic carboxylic acid anhydrides. Specific examples include acetic anhydride, trichloroacetic anhydride, trifluoroacetic anhydride, and tetrahydrophthalic anhydride. Succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, glutaric anhydride, 1,2-cyclohexene dicarboxylic anhydride, n-octadecyl succinic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, etc. An aliphatic carboxylic acid anhydride is mentioned. Examples of the aromatic carboxylic acid anhydride include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, and naphthalic anhydride. Among these, those having a molecular weight of 600 or less, particularly a molecular weight of 50 to 500, specifically, maleic anhydride, succinic anhydride, citraconic anhydride, and itaconic anhydride are preferable.

When the composition of the present invention contains an organic carboxylic acid and an organic carboxylic anhydride, the amount of these organic carboxylic acid and / or organic carboxylic anhydride is usually 0.01 to 10 mass in the total solid content. %, Preferably 0.03 to 5% by mass, more preferably 0.05 to 3% by mass.
By adding these organic carboxylic acids and / or organic carboxylic acid anhydrides having a molecular weight of 1000 or less, it is possible to further reduce the remaining undissolved material of the composition while maintaining high pattern adhesion.

<Preparation method of colored photosensitive resin composition>
The composition of the present invention is prepared by mixing the aforementioned components.
In preparing the composition, the components constituting the composition may be combined at once, or may be sequentially combined after each component is dissolved and dispersed in a solvent. In addition, there are no particular restrictions on the charging order and working conditions when blending. For example, the composition may be prepared by dissolving and dispersing all components in a solvent at the same time. If necessary, each component may be suitably used as two or more solutions / dispersions at the time of use (at the time of application). ) May be mixed to prepare a composition.
Among them, in the present invention, (A) a pigment, (B) a basic dye derivative, and (C) a phosphoric acid dispersant represented by the general formula (II) are dispersed, and then (D) the general formula (IV) It is preferable to blend a resin obtained by copolymerizing the compound (x) represented by () and the compound (y) having an ethylenically unsaturated double bond.
The composition prepared as described above is preferably used after being filtered using a filter having a pore size of 0.01 μm to 3.0 μm, more preferably a pore size of about 0.05 μm to 0.5 μm. be able to.

  Since the composition of this invention can form the cured film excellent in heat resistance and a color characteristic, it is used suitably in order to form the coloring pattern (colored photosensitive composition layer) of a color filter. In addition, the composition of the present invention is preferably used for forming a colored pattern such as a color filter used in a solid-state imaging device (for example, CCD, CMOS, etc.) or an image display device such as a liquid crystal display device (LCD). it can. Furthermore, it can be suitably used as a production application for printing ink, inkjet ink, paint, and the like. In particular, a color filter for a solid-state imaging device such as a CCD and a CMOS can be suitably used as a production application.

<Curing film, pattern forming method, color filter, and color filter manufacturing method>
Next, the cured film, the pattern forming method, and the color filter in the present invention will be described in detail.

In the pattern forming method of the present invention, the colored photosensitive resin composition of the present invention is applied onto a support to form a colored photosensitive composition layer (hereinafter also referred to as “colored composition layer”). A composition layer forming step; an exposure step of exposing the colored composition layer in a pattern; and a pattern forming step of developing and removing an unexposed portion to form a colored pattern.
The pattern forming method of the present invention can be suitably applied to the formation of a colored pattern (pixel) included in a color filter.

  The support for forming a pattern by the pattern forming method of the present invention is not particularly limited as long as it is a support applicable to pattern formation in addition to a plate-like object such as a substrate.

  Hereinafter, although each process in the pattern formation method of this invention is demonstrated in detail through the manufacturing method of the color filter for solid-state image sensors, this invention is not limited to this method.

The method for producing a color filter of the present invention applies the pattern forming method of the present invention, and includes a step of forming a colored pattern on a support using the pattern forming method of the present invention.
That is, the method for producing a color filter of the present invention applies the pattern forming method of the present invention, and forms the colored photosensitive composition layer by applying the colored photosensitive composition of the present invention on a support. It includes a step, a step of exposing the colored photosensitive composition layer in a pattern, and a step of developing and removing the unexposed portion to form a colored pattern.
Furthermore, you may provide the process (prebaking process) of baking a colored composition layer, and the process (post-baking process) of baking the developed coloring pattern as needed. Hereinafter, these steps may be collectively referred to as a pattern forming step.
The color filter of the present invention can be suitably obtained by the above production method.
Hereinafter, the color filter for the solid-state imaging device may be simply referred to as “color filter”.

  Each step in the pattern forming method of the present invention will be described in detail below through the color filter manufacturing method of the present invention.

<Step of forming a colored photosensitive composition layer>
In the step of forming the colored photosensitive composition layer, the colored photosensitive composition layer is formed on the support by applying the composition of the present invention.

As a support that can be used in this step, for example, a solid-state imaging in which an imaging element (light-receiving element) such as a CCD (Charge Coupled Device) or a CMOS (Complementary Metal-Oxide Semiconductor) is provided on a substrate (for example, a silicon substrate). An element substrate can be used.
The colored pattern in the present invention may be formed on the imaging element forming surface side (front surface) of the solid-state imaging element substrate, or may be formed on the imaging element non-forming surface side (back surface).
A light shielding film may be provided between the colored patterns in the solid-state image sensor or on the back surface of the substrate for the solid-state image sensor.
Further, if necessary, an undercoat layer may be provided on the support for improving adhesion with the upper layer, preventing diffusion of substances, or flattening the substrate surface.

  As a method for applying the composition of the present invention on the support, various coating methods such as slit coating, ink jet method, spin coating, cast coating, roll coating, and screen printing can be applied.

  The colored photosensitive composition layer coated on the support can be dried (prebaked) at a temperature of 50 ° C. to 140 ° C. for 10 seconds to 300 seconds using a hot plate, oven, or the like.

<< Step of Exposing Colored Photosensitive Composition Layer to Pattern (When Forming Pattern by Photolithographic Method) >>
-Exposure process-
In the exposure step, the colored photosensitive composition layer formed in the colored photosensitive composition layer forming step is subjected to pattern exposure through a mask having a predetermined mask pattern using an exposure apparatus such as a stepper, for example. Thereby, a cured film is obtained.
As radiation (light) that can be used for exposure, ultraviolet rays such as g-line and i-line are particularly preferable (particularly preferably i-line). Irradiation dose (exposure dose) is more preferably 30mJ / cm ² ~1500mJ / cm ² is preferably ^{50mJ / cm 2 ~1000mJ / cm 2} , 80mJ / cm 2 ~500mJ / cm 2 being most preferred.

The thickness of the cured film is preferably 1.0 μm or less, more preferably 0.1 μm to 0.9 μm, and still more preferably 0.2 μm to 0.8 μm.
It is preferable to set the film thickness to 1.0 μm or less because high resolution and high adhesion can be obtained.
In addition, in this step, a cured film having a thin film thickness of 0.7 μm or less can also be suitably formed, and the obtained cured film is developed in a pattern forming process described later, thereby forming a thin film. Although it exists, the coloring pattern excellent in developability, surface roughness suppression, and pattern shape can be obtained.

<<< Process for forming colored pattern >>>
Next, by performing an alkali development treatment, the colored photosensitive composition layer of the light non-irradiated portion in the exposure step is eluted in the alkaline aqueous solution, and only the photocured portion remains.
The developer is preferably an organic alkali developer that does not cause damage to the underlying image sensor or circuit. The development temperature is usually 20 ° C. to 30 ° C., and the development time is conventionally 20 seconds to 90 seconds. In order to remove the residue more, in recent years, it may be carried out for 120 seconds to 180 seconds. Furthermore, in order to further improve residue removability, the process of shaking off the developer every 60 seconds and further supplying a new developer may be repeated several times.

Examples of the alkaline agent used in the developer include ammonia water, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide. And organic alkaline compounds such as choline, pyrrole, piperidine, 1,8-diazabicyclo- [5,4,0] -7-undecene, and the concentration of these alkaline agents is 0.001% by mass to 10% by mass, An alkaline aqueous solution diluted with pure water so as to be preferably 0.01% by mass to 1% by mass is preferably used as the developer.
In addition, an inorganic alkali may be used for the developer, and as the inorganic alkali, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium oxalate, sodium metaoxalate and the like are preferable.
In the case where a developer composed of such an alkaline aqueous solution is used, it is generally washed (rinsed) with pure water after development.

Next, it is preferable to perform heat treatment (post-bake) after drying. If a multicolor coloring pattern is to be formed, a cured film can be produced by sequentially repeating the above steps for each color. Thereby, a color filter is obtained.
The post-baking is a heat treatment after development for complete curing, and a heat curing treatment is usually performed at 100 ° C. to 240 ° C., preferably 200 ° C. to 240 ° C.
This post-bake treatment is performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), a high-frequency heater or the like so that the coating film after development is in the above condition. be able to.

<< Step of Forming Photoresist Layer, Step of Obtaining Resist Pattern, and Step of Dry Etching (When Pattern is Formed by Dry Etching Method) >>
Dry etching can be performed using an etching gas with the patterned photoresist layer as a mask. Specifically, a positive or negative radiation sensitive composition is applied onto the colored layer and dried to form a photoresist layer. In the formation of the photoresist layer, it is preferable to further perform a pre-bake treatment. In particular, as a process for forming the photoresist layer, a mode in which heat treatment after exposure (PEB) and heat treatment after development (post-bake treatment) are desirable.

As the photoresist, for example, a positive type radiation sensitive composition is used. The positive-type radiation-sensitive composition includes a positive-type photoresist that is sensitive to radiation such as ultraviolet rays (g-rays, h-rays, i-rays), deep ultraviolet rays including excimer lasers, electron beams, ion beams, and X-rays. A positive resist composition suitable for use can be used. Of the radiation, g-line, h-line and i-line are preferable, and i-line is preferable.
Specifically, as the positive radiation sensitive composition, a composition containing a quinonediazide compound and an alkali-soluble resin is preferable. A positive radiation-sensitive composition containing a quinonediazide compound and an alkali-soluble resin indicates that a quinonediazide group is decomposed by irradiation with light having a wavelength of 500 nm or less to produce a carboxy group, resulting in alkali-solubility from an alkali-insoluble state. It is what you use. Since this positive photoresist has remarkably excellent resolution, it is used for manufacturing integrated circuits such as ICs and LSIs. Examples of the quinonediazide compound include a naphthoquinonediazide compound. Examples of commercially available products include FHi622BC (manufactured by FUJIFILM Electronics Materials).

  The thickness of the photoresist layer is preferably 0.1 to 3 μm, preferably 0.2 to 2.5 μm, and more preferably 0.3 to 2 μm. The formation of the photoresist layer by coating can be suitably performed using the coating method for the colored layer described above.

  Next, by exposing and developing the photoresist layer, a resist pattern (patterned photoresist layer) provided with a group of resist through holes is formed. The formation of the resist pattern is not particularly limited, and can be performed by appropriately optimizing a conventionally known photolithography technique. By providing a resist through hole group in the photoresist layer by exposure and development, a resist pattern as an etching mask used in the next etching is provided on the colored layer.

  The exposure of the photoresist layer is performed by exposing the positive-type or negative-type radiation-sensitive composition with g-line, h-line, i-line, etc., preferably i-line, through a predetermined mask pattern. Can do. After the exposure, the photoresist is removed in accordance with a region where a colored pattern is to be formed by developing with a developer.

  Any developer can be used as long as it dissolves the exposed portion of the positive resist and the uncured portion of the negative resist without affecting the colored layer containing the colorant. Combinations of solvents and alkaline aqueous solutions can be used. As the alkaline aqueous solution, an alkaline aqueous solution prepared by dissolving an alkaline compound so as to have a concentration of 0.001 to 10% by mass, preferably 0.01 to 5% by mass is suitable. Examples of alkaline compounds include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium oxalate, sodium metasuccinate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, Examples include pyrrole, piperidine, and 1,8-diazabicyclo [5.4.0] -7-undecene. In addition, when alkaline aqueous solution is used as a developing solution, generally a washing process is performed with water after development.

  Next, using the resist pattern as an etching mask, patterning is performed by dry etching so that the through hole group is formed in the colored layer. Thereby, a colored pattern is formed. The through hole group is provided in a checkered pattern in the colored layer. Therefore, the first colored pattern in which the through hole group is provided in the colored layer has a plurality of square-shaped first colored pixels in a checkered pattern.

Dry etching is preferably performed in the following manner from the viewpoint of forming a pattern cross section closer to a rectangle and reducing damage to the support.
Using a mixed gas of fluorine-based gas and oxygen gas (O ₂ ), the first stage etching is performed up to a region (depth) where the support is not exposed, and after this first stage etching, nitrogen gas ( N ₂ ) and oxygen gas (O ₂ ), and a second stage etching is preferably performed to the vicinity of the region (depth) where the support is exposed, and over-etching is performed after the support is exposed. The form containing these is preferable. Hereinafter, a specific method of dry etching and the first stage etching, second stage etching, and over-etching will be described.

Dry etching is performed by obtaining etching conditions in advance by the following method.
(1) The etching rate (nm / min) in the first stage etching and the etching rate (nm / min) in the second stage etching are calculated respectively. (2) The time for etching the desired thickness in the first stage etching and the time for etching the desired thickness in the second stage etching are respectively calculated. (3) The first stage etching is performed according to the etching time calculated in (2) above. (4) The second stage etching is performed according to the etching time calculated in (2) above. Alternatively, the etching time may be determined by endpoint detection, and the second stage etching may be performed according to the determined etching time. (5) Overetching time is calculated with respect to the total time of (3) and (4) above, and overetching is performed.

The mixed gas used in the first stage etching step preferably contains a fluorine-based gas and an oxygen gas (O ₂ ) from the viewpoint of processing the organic material that is the film to be etched into a rectangular shape. In addition, the first stage etching process can avoid damage to the support by etching to a region where the support is not exposed. The second etching step and the over-etching step are performed in the first etching step after etching to a region where the support is not exposed by the mixed gas of fluorine-based gas and oxygen gas. From the viewpoint of avoidance, it is preferable to perform the etching process using a mixed gas of nitrogen gas and oxygen gas.

  It is important to determine the ratio between the etching amount in the first stage etching process and the etching amount in the second stage etching process so as not to impair the rectangularity due to the etching process in the first stage etching process. It is. The latter ratio in the total etching amount (the sum of the etching amount in the first-stage etching process and the etching amount in the second-stage etching process) is preferably in the range of more than 0% and not more than 50%. 10 to 20% is more preferable. The etching amount is an amount calculated from the difference between the remaining film thickness to be etched and the film thickness before etching.

  Etching preferably includes an over-etching process. The overetching process is preferably performed by setting an overetching ratio. Moreover, it is preferable to calculate the overetching ratio from the etching process time to be performed first. The over-etching ratio can be arbitrarily set, but it is preferably 30% or less of the etching processing time in the etching process, and 5 to 25% in terms of maintaining the etching resistance of the photoresist and the rectangularity of the pattern to be etched. Is more preferable, and 10 to 15% is particularly preferable.

  Next, the resist pattern (that is, the etching mask) remaining after the etching is removed. The removal of the resist pattern preferably includes a step of applying a stripping solution or a solvent on the resist pattern so that the resist pattern can be removed, and a step of removing the resist pattern using cleaning water.

  Examples of the step of applying a stripping solution or solvent on the resist pattern so that the resist pattern can be removed include, for example, a step of applying a stripping solution or solvent on at least the resist pattern and stagnating for a predetermined time to perform paddle development Can be mentioned. Although there is no restriction | limiting in particular as time to make stripping solution or a solvent stagnant, It is preferable that it is several dozen seconds to several minutes.

  Examples of the process of removing the resist pattern using the cleaning water include a process of removing the resist pattern by spraying the cleaning water onto the resist pattern from a spray type or shower type spray nozzle. As the washing water, pure water can be preferably used. Further, examples of the injection nozzle include an injection nozzle in which the entire support is included in the injection range, and an injection nozzle that is a movable injection nozzle and in which the movable range includes the entire support. When the spray nozzle is movable, the resist pattern is more effectively removed by moving the support pattern from the center of the support to the end of the support more than twice during the process of removing the resist pattern and spraying the cleaning water. be able to.

  The stripping solution generally contains an organic solvent, but may further contain an inorganic solvent. Examples of organic solvents include 1) hydrocarbon compounds, 2) halogenated hydrocarbon compounds, 3) alcohol compounds, 4) ether or acetal compounds, 5) ketones or aldehyde compounds, and 6) ester compounds. 7) polyhydric alcohol compounds, 8) carboxylic acids or acid anhydride compounds thereof, 9) phenol compounds, 10) nitrogen compounds, 11) sulfur compounds, and 12) fluorine compounds. The stripping solution preferably contains a nitrogen-containing compound, and more preferably contains an acyclic nitrogen-containing compound and a cyclic nitrogen-containing compound.

The acyclic nitrogen-containing compound is preferably an acyclic nitrogen-containing compound having a hydroxyl group. Specifically, for example, monoisopropanolamine, diisopropanolamine, triisopropanolamine, N-ethylethanolamine, N, N-dibutylethanolamine, N-butylethanolamine, monoethanolamine, diethanolamine, triethanolamine, etc. Preferred are monoethanolamine, diethanolamine and triethanolamine, and more preferred is monoethanolamine (H ₂ NCH ₂ CH ₂ OH). Examples of the cyclic nitrogen-containing compound include isoquinoline, imidazole, N-ethylmorpholine, ε-caprolactam, quinoline, 1,3-dimethyl-2-imidazolidinone, α-picoline, β-picoline, γ-picoline, 2- Preferred examples include pipecoline, 3-pipecoline, 4-pipecoline, piperazine, piperidine, pyrazine, pyridine, pyrrolidine, N-methyl-2-pyrrolidone, N-phenylmorpholine, 2,4-lutidine, 2,6-lutidine and the like. Are N-methyl-2-pyrrolidone and N-ethylmorpholine, more preferably N-methyl-2-pyrrolidone (NMP).

  The stripping solution preferably contains an acyclic nitrogen-containing compound and a cyclic nitrogen-containing compound. Among these, as the acyclic nitrogen-containing compound, at least one selected from monoethanolamine, diethanolamine, and triethanolamine, and cyclic The nitrogen-containing compound preferably contains at least one selected from N-methyl-2-pyrrolidone and N-ethylmorpholine, and more preferably contains monoethanolamine and N-methyl-2-pyrrolidone.

  When removing with a stripping solution, it is sufficient that the resist pattern formed on the first colored pattern is removed, and deposits (deposits) as etching products are attached to the side walls of the first colored pattern. Even in such a case, the deposit may not be completely removed. A deposit means an etching product deposited and deposited on the side wall of a colored layer.

  As the stripping solution, the content of the non-cyclic nitrogen-containing compound is 9 parts by weight or more and 11 parts by weight or less with respect to 100 parts by weight of the stripping solution, and the content of the cyclic nitrogen-containing compound is 100 parts by weight of the stripping solution. On the other hand, what is 65 to 70 mass parts is desirable. Further, the stripping solution is preferably obtained by diluting a mixture of an acyclic nitrogen-containing compound and a cyclic nitrogen-containing compound with pure water.

  In addition, the manufacturing method of this invention may have a well-known process as a manufacturing method of the color filter for solid-state image sensors as processes other than the above as needed. For example, after performing the above-mentioned colored photosensitive composition layer forming step, exposure step and pattern forming step, a curing step of curing the formed colored pattern by heating and / or exposure may be included as necessary. .

Further, when the composition according to the present invention is used, for example, clogging of a nozzle or a piping part of a coating apparatus discharge part, contamination due to adhesion, sedimentation, or drying of a colored composition or pigment in the coating machine may occur. . Therefore, in order to efficiently clean the contamination caused by the composition of the present invention, it is preferable to use the solvent related to the present composition as the cleaning liquid. JP-A-7-128867, JP-A-7-146562, JP-A-8-278737, JP-A-2000-273370, JP-A-2006-85140, JP-A-2006-291191, The cleaning liquids described in JP2007-2101A, JP2007-2102A, JP2007-281523A, and the like can also be suitably used for cleaning and removing the composition according to the present invention.
Of the above, alkylene glycol monoalkyl ether carboxylates and alkylene glycol monoalkyl ethers are preferred.
These solvents may be used alone or in combination of two or more. When mixing 2 or more types, it is preferable to mix the solvent which has a hydroxyl group, and the solvent which does not have a hydroxyl group. The mass ratio of the solvent having a hydroxyl group and the solvent having no hydroxyl group is from 1/99 to 99/1, preferably from 10/90 to 90/10, and more preferably from 20/80 to 80/20. In a mixed solvent of propylene glycol monomethyl ether acetate (PGMEA) and propylene glycol monomethyl ether (PGME), the ratio is particularly preferably 60/40. In addition, in order to improve the permeability of the cleaning liquid with respect to contaminants, a surfactant related to the present composition described above may be added to the cleaning liquid.

Since the color filter of the present invention uses the composition of the present invention, the exposure can be performed with excellent exposure margin, and the formed colored pattern (colored pixel) is excellent in pattern shape, and the pattern surface is rough and developed. Since the residue in the portion is suppressed, the color characteristics are excellent.
The color filter of the present invention can be suitably used for a solid-state imaging device such as a CCD or CMOS, and is particularly suitable for a CCD or CMOS having a high resolution exceeding 1 million pixels. The color filter for a solid-state imaging device of the present invention can be used as a color filter disposed between, for example, a light receiving portion of each pixel constituting a CCD or CMOS and a microlens for condensing light.

In addition, as a film thickness of the coloring pattern (color pixel) in the color filter of this invention, 2.0 micrometers or less are preferable, 1.0 micrometer or less is more preferable, and 0.7 micrometer or less is further more preferable.
Further, the size (pattern width) of the colored pattern (colored pixel) is preferably 2.5 μm or less, more preferably 2.0 μm or less, and particularly preferably 1.7 μm or less.

[Solid-state imaging device]
The solid-state imaging device of the present invention includes the above-described color filter of the present invention. The configuration of the solid-state imaging device of the present invention is a configuration provided with the color filter according to the present invention, and is not particularly limited as long as it is a configuration that functions as a solid-state imaging device. .

A transfer electrode made of a plurality of photodiodes and polysilicon constituting a light receiving area of a solid-state imaging device (CCD image sensor, CMOS image sensor, etc.) is provided on a support, and the photodiode and the transfer electrode are provided on the support. A light-shielding film made of tungsten or the like having an opening only in the light-receiving portion of the photodiode, and a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire surface of the light-shielding film and the photodiode light-receiving portion. It is the structure which has the color filter for solid-state image sensors of this invention on a device protective film.
Further, a configuration having light collecting means (for example, a microlens, etc., the same shall apply hereinafter) on the device protective layer and under the color filter (on the side close to the support), or a structure having the light collecting means on the color filter Etc.

[Image display device]
The color filter of the present invention can be used not only for the solid-state imaging device but also for image display devices such as liquid crystal display devices and organic EL display devices, and is particularly suitable for use in liquid crystal display devices. The liquid crystal display device provided with the color filter of the present invention can display a high-quality image with a good display image color and excellent display characteristics.

  For the definition of display devices and details of each display device, refer to, for example, “Electronic Display Devices (Akio Sasaki, published by Industrial Research Institute 1990)”, “Display Devices (Junaki Ibuki, Industrial Books Co., Ltd.) Issued in the first year). The liquid crystal display device is described in, for example, “Next-generation liquid crystal display technology (edited by Tatsuo Uchida, published by Kogyo Kenkyukai 1994)”. The liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the “next generation liquid crystal display technology”.

The color filter of the present invention may be used in a color TFT liquid crystal display device. The color TFT liquid crystal display device is described in, for example, “Color TFT liquid crystal display (issued in 1996 by Kyoritsu Publishing Co., Ltd.)”. Furthermore, the present invention is applied to a liquid crystal display device with a wide viewing angle such as a horizontal electric field driving method such as IPS and a pixel division method such as MVA, STN, TN, VA, OCS, FFS, and R-OCB. it can.
In addition, the color filter in the present invention can be used for a bright and high-definition COA (Color-filter On Array) system. In the case of a COA type liquid crystal display device, the required characteristics for the color filter layer require the required characteristics for the interlayer insulating film, that is, the low dielectric constant and the resistance to the stripping solution, in addition to the normal required characteristics as described above. Sometimes. In the color filter of the present invention, since a dye multimer excellent in hue is used, the color purity, light transmittance, etc. are good and the color pattern (pixel) is excellent in hue, so the resolution is high and the long-term durability is excellent. A COA type liquid crystal display device can be provided. In order to satisfy the required characteristics of a low dielectric constant, a resin film may be provided on the color filter layer.
These image display methods are described, for example, on page 43 of "EL, PDP, LCD display-Technology and latest trends in the market (issued by Toray Research Center Research Division 2001)".

In addition to the color filter of the present invention, the liquid crystal display device provided with the color filter of the present invention includes various members such as an electrode substrate, a polarizing film, a retardation film, a backlight, a spacer, and a viewing angle guarantee film. The color filter of the present invention can be applied to a liquid crystal display device composed of these known members. Regarding these components, for example, “'94 Liquid Crystal Display Peripheral Materials / Chemicals Market (Kentaro Shima CMC 1994)”, “2003 Liquid Crystal Related Markets Current Status and Future Prospects (Volume 2)” Fuji Chimera Research Institute, Ltd., published in 2003) ”.
Regarding the backlight, SID meeting Digest 1380 (2005) (A. Konno et.al), Monthly Display December 2005, pages 18-24 (Yasuhiro Shima), pages 25-30 (Takaaki Yagi), etc. Have been described.

  When the color filter of the present invention is used in a liquid crystal display device, a high contrast can be realized when combined with a conventionally known three-wavelength tube of a cold cathode tube, and further, red, green and blue LED light sources (RGB-LED). By using as a backlight, a liquid crystal display device having high luminance and high color purity and good color reproducibility can be provided.

  The present invention will be described more specifically with reference to the following examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. Unless otherwise specified, “%” and “parts” are based on mass.

<Synthesis of (C) Phosphate Dispersant>
(Synthesis Example 1)
In a reaction vessel equipped with a cooling tube, a nitrogen gas inlet tube, and a stirrer in a three-necked round bottom flask, 18.6 g of lauryl alcohol (manufactured by Nacalai Tesque), 57.1 g of ε-caprolactone monomer (manufactured by Wako Pure Chemical Industries, Ltd.) Then, 0.06 g of tetrabutyl titanate (manufactured by Tokyo Chemical Industry Co., Ltd.) was charged, and the inside of the reaction vessel was replaced with nitrogen gas, and then heated and stirred at 120 ° C. for 3 hours. The disappearance of the lactone monomer was confirmed by ¹ H-NMR. The reaction solution was cooled to room temperature, mixed with 8.45 g of polyphosphoric acid having an orthophosphoric acid content of 116%, gradually heated, heated and stirred at 80 ° C. for 6 hours, R in the general formula (II) A phosphoric acid dispersant (C-1) having a number average molecular weight of ³ of 760 and an abundance ratio of y = 1 and y = 2 of 100: 12 was obtained. The acid value of the obtained phosphoric acid dispersant was 166.

(Synthesis Examples 2 to 4)
The phosphoric acid dispersant (C--) was prepared in the same manner as in Synthesis Example 1 except that the type and amount of monoalcohol used and the type and amount of lactone monomer used were changed as shown in Table 1 below. 2) to (C-4) were obtained.

In Table 1 above, the number average molecular weight of R ³ indicates the number average molecular weight in the general formula (II).

<(D) Synthesis of specific resin binder>
(Synthesis Example 5)
In a separable four-necked flask, a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, and a stirrer is charged with propylene glycol monomethyl ether acetate and heated to 80 ° C. while introducing nitrogen gas into the reaction vessel, At the same temperature, 123.3 g of benzyl methacrylate, 17.2 g of methacrylic acid, 31.0 g of paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.), 10.0 g of azobisisobutyronitrile The mixture was added dropwise over 2 hours to conduct a polymerization reaction.
After cooling the obtained resin solution to room temperature, about 3 g was sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. Acetate was added to obtain a resin binder (D-1) solution.

<Synthesis of resin binder 1>
(Synthesis Example 6)
In a separable four-necked flask, a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, and a stirrer is charged with propylene glycol monomethyl ether acetate and heated to 100 ° C. while introducing nitrogen gas into the reaction vessel, At the same temperature, a mixture of 123.3 g of benzyl methacrylate, 25.8 g of methacrylic acid, and 10.0 g of azobisisobutyronitrile was dropped from the dropping tube over 1 hour to carry out a polymerization reaction.
After cooling the obtained resin solution to room temperature, about 3 g was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and propylene glycol so that the nonvolatile content was 40% by mass in the previously synthesized resin solution. Acetate was added to obtain a resin binder 1 solution.

<(G) Synthesis of resin>
(Synthesis Example 7)
In a separable four-necked flask, a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, and a stirrer is charged with propylene glycol monomethyl ether acetate and heated to 80 ° C. while introducing nitrogen gas into the reaction vessel, At the same temperature, a mixture of 123.3 g of benzyl methacrylate, 17.2 g of methacrylic acid, 14.6 g of glycerol monomethacrylate, and 10.0 g of azobisisobutyronitrile was dropped over 2 hours from the dropping tube to carry out a polymerization reaction.
A mixture of 23.3 g of 2-methacryloylethyl isocyanate (“Karenz MOI” manufactured by Showa Denko KK), 0.3 g of dibutyltin laurate and 90 g of cyclohexanone was added dropwise to the obtained resin solution at 70 ° C. over 3 hours. did.
After cooling the obtained resin solution to room temperature, about 3 g was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and propylene glycol so that the nonvolatile content was 40% by mass in the previously synthesized resin solution. Acetate was added to obtain a resin binder (G-1) solution.

<Production of red pigment dispersion composition>
A mixture having the following composition was uniformly stirred and mixed, and then mixed and dispersed for 3 hours by a bead mill to prepare a red pigment dispersion composition (R-a).
Diketopyrrolopyrrole red pigment (CI Pigment Red254)
8.3 parts by mass Isoindoline yellow pigment (CI Pigment Yellow 139)
3.7 parts by mass Pigment derivative represented by the following chemical formula (B-1) 1.5 parts by mass Phosphoric acid dispersant (C-1) 1.2 parts by mass Resin binder (D-1) 5.3 parts by mass (Non-volatile content)
80.0 parts by mass of propylene glycol monomethyl ether acetate (PGMEA)

  The red pigment dispersion compositions (Rb) to (Rp) were prepared in the same manner as the preparation of the red pigment dispersion composition (Ra) described above except that the composition was changed to the composition shown in Table 2 below. ) Was prepared.

In Table 2 above, each symbol means the following compound.
PR254: diketopyrrolopyrrole red pigment (CI Pigment Red254)
PY139: Isoindoline yellow pigment (CI Pigment Yellow 139)
PR177 ... anthraquinone red pigment (CI Pigment Red177)
PR122: quinacridone red pigment (CI Pigment Red122)
PO71 ... diketopyrrolopyrrole orange pigment (CI Pigment Orange 71)

Red-a: azo-based red pigment Red-a having the following structural formula

Dye derivative (B-2): Compound having the following structural formula

Dye derivative (B-3): Compound having the following structural formula

Dye derivative (B-4): Compound having the following structural formula

<Preparation of green pigment dispersion composition>
A mixture having the following composition was stirred and mixed uniformly, and then mixed and dispersed for 3 hours by a bead mill to prepare a green pigment dispersion composition (G-a).
Halogenated copper phthalocyanine green pigment (CI Pigment Green 36)
11.4 parts by mass Isoindoline-based yellow pigment (CI Pigment Yellow 139)
3.4 parts by mass Pigment derivative represented by the following chemical formula (B-1) 2.0 parts by mass Phosphoric acid dispersant (C-1) 1.6 parts by mass Resin binder (D-1) 6.9 parts by mass (Non-volatile content)
Propylene glycol monomethyl ether acetate (PGMEA)
50.7 parts by mass Cyclohexanone 24.0 parts by mass

  The green pigment dispersion compositions (Gb) to (Go) are the same as the preparation of the green pigment dispersion composition (Ga) described above except that the composition is changed to the composition shown in Table 3 below. Was prepared.

In Table 3 above, each symbol means the following compound.
PG7: Chlorinated copper phthalocyanine green pigment (CI Pigment Green 7)
PG36: Copper halide phthalocyanine green pigment (CI Pigment Green 36)
PG58: zinc halide phthalocyanine green pigment (CI Pigment Green 58)
PY139: Isoindoline yellow pigment (CI Pigment Yellow 139)
PY150 ... Nickel azo yellow pigment (CI Pigment Yellow 150) PY185 ... Isoindoline yellow pigment (CI Pigment Yellow 185)

Dye derivative (B-5): Compound having the following structural formula

<Preparation of yellow pigment dispersion composition>
A mixture having the following composition was uniformly stirred and mixed, and then mixed and dispersed by a bead mill for 3 hours to prepare a yellow pigment dispersion composition (Ya).
Isoindoline yellow pigment (CI Pigment Yellow 139)
14.2 parts by mass Pigment derivative represented by the following chemical formula (B-1) 1.6 parts by mass Phosphoric acid dispersant (C-1) 3.5 parts by mass Resin binder (D-1) 5.7 parts by mass (Non-volatile content)
Propylene glycol monomethyl ether acetate (PGMEA)
58.0 parts by mass Cyclohexanone 17.0 parts by mass

<Preparation of blue pigment dispersion composition>
A mixture having the following composition was uniformly stirred and mixed, and then mixed and dispersed for 3 hours by a bead mill to prepare a blue pigment dispersion composition (Ba).
Copper phthalocyanine blue pigment (CI Pigment Blue 15: 6)
8.4 parts by mass Dioxazine-based purple pigment (CI Pigment Violet 23)
4.3 parts by mass Pigment derivative represented by the following chemical formula (B-6) 1.3 parts by mass Phosphoric acid dispersant (C-1) 2.1 parts by mass Resin binder (D-1) 3.5 parts by mass (Non-volatile content)
Propylene glycol monomethyl ether acetate (PGMEA)
50.7 parts by mass Cyclohexanone 29.7 parts by mass

  Blue pigment dispersion compositions (Bb) to (Bg) were prepared in the same manner as in the preparation of the blue pigment dispersion composition (Ba) except that the composition was changed to the composition shown in Table 4 below. Was prepared.

In Table 4 above, each symbol means the following compound.
PB15: 6 ... Copper phthalocyanine-based blue pigment (CI Pigment Blue 15: 6)
PV23 ... dioxazine-based purple pigment (CI Pigment Violet 23)

Dye derivative (B-7): Compound having the following structural formula

<Preparation of red photosensitive resin composition>
A red photosensitive resin composition (RR-a) was prepared by uniformly stirring and mixing a mixture having the following composition.
Red pigment dispersion composition (Ra) 50.0 parts by mass Resin binder 1 2.6 parts by mass (as 40% by mass resin solution)
Photopolymerization initiator (E-1) 0.3 parts by mass Ethylenically unsaturated compound (F-1) 0.7 parts by mass Fluorine-based surfactant 4.2 parts by mass (propylene glycol monomethyl ether having a nonvolatile content of 1% by mass) As acetate solution)
p-Methoxyphenol 0.0003 parts by mass Propylene glycol monomethyl ether acetate (PGMEA)
42.2 parts by mass

Photopolymerization initiator (E-1): 1.2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)] (manufactured by BASF, IRGACURE OXE01)
Ethylenically unsaturated compound (F-1): ethylene oxide-modified product of dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A-DPH-12E)
Fluorosurfactant: (Dainippon Ink Co., Ltd., MegaFuck F-781F)

  The red photosensitive resin compositions (RR-b) to (RR-) were prepared in the same manner as the preparation of the red photosensitive resin composition (RR-a) except that the composition was changed to the composition shown in Table 5 below. v) was prepared.

<Evaluation>
(Evaluation of pattern formation after PCD)
(1) Preparation of transparent resist solution A (negative type)
The following components were mixed and dissolved to prepare a transparent resist solution A.
Propylene glycol monomethyl ether acetate 5.20 parts Cyclohexanone 52.60 parts Binder 30.50 parts (benzyl methacrylate / methacrylic acid / -2-hydroxyethyl methacrylate copolymer molar ratio = 60: 20: 20, average Molecular weight 30200 (polystyrene conversion, 41% cyclohexanone solution)
Dipentaerythritol hexaacrylate 10.20 parts Polymerization inhibitor (p-methoxyphenol) 0.006 parts Fluorosurfactant (DIC, F-475) 0.80 parts Photopolymerization initiator: 4-Benzoxolane-2,6-bis (trichloromethyl) -s-triazine (Midori Chemical Co., Ltd., TAZ-107) 0.58 parts

(2) Production of glass substrate with undercoat layer A glass substrate (Corning 1737) was ultrasonically washed with 0.5% NaOH water, and then washed with water and dehydrated (200 ° C./20 minutes). Next, the transparent resist solution A obtained in the above (1) is applied onto the washed glass substrate using a spin coater so that the film thickness after drying becomes 2 μm, and is heated and dried at 220 ° C. for 1 hour to undercoat. A glass substrate with an undercoat layer was prepared by forming a layer.

(3) Exposure and development of colored photosensitive resin composition (colored pattern formation)
The film thickness after drying the red photosensitive resin compositions (RR-a) to (RR-v) obtained above on the undercoat layer of the glass substrate with an undercoat layer obtained in (2) above is 0.6 μm. Two substrates were prepared using a spin coater and pre-baked at 100 ° C. for 120 seconds.
One of the above substrates uses an i-line stepper exposure apparatus FPA-i5 + (manufactured by Canon Inc.) immediately after the application of the red photosensitive resin composition, and the coating film has a wavelength of 365 nm and a line width of 1.1 μm. The mask was irradiated with an optimal exposure amount to form a checkered pattern having a side length of 1.1 μm. After the exposure, development was performed using a developer CD-2000 (manufactured by Fuji Film Electronics Materials Co., Ltd.) at 25 ° C. for 40 seconds. Then, after rinsing with running water for 30 seconds, spray drying was performed to obtain a colored pattern.
Next, after applying the red photosensitive resin composition, the other of the substrates was left in a clean room at room temperature for 72 hours (PCD), and then a colored pattern was obtained by the same method as described above.
The two types of colored patterns obtained in this way are observed with an SEM, and are obtained by performing exposure and development immediately after coating (without PCD) and after exposure and development after PCD. The shape was compared with the colored pattern and evaluated according to the following criteria.
A: The shape of the colored pattern after PCD does not change at all compared to the shape of the colored pattern without PCD. B: There is no problem with the shape of the colored pattern after PCD, but there is no problem. C: Color after PCD The shape of the pattern is broken and there is a problem D: The shape of the colored pattern after PCD is greatly broken. The PCD evaluation results are summarized in Table 5 below.

(Evaluation of Zara (color unevenness))
The red photosensitive resin compositions (RR-a) to (RR-v) obtained above were applied onto a glass substrate using a spin coater so that the film thickness after drying was 0.6 μm, and 100 ° C. And pre-baking for 120 seconds to obtain a colored coating film 1.
Further, after the red photosensitive resin compositions (RR-a) to (RR-v) obtained as described above are aged at room temperature for 6 months, the film thickness after drying on the glass substrate becomes 0.6 μm. As described above, coating was performed using a spin coater and prebaked at 100 ° C. for 120 seconds to obtain a colored coating film 2.
Each colored coating obtained was placed between the observation lens and the light source of the optical microscope, irradiated with light toward the observation lens, and transmitted through an optical microscope in which a digital camera with a magnification of 1000 was installed. The light state was observed. The digital camera installed in the optical microscope is equipped with a CCD with 1.28 million pixels, and the surface of the colored coating film in the transmitted light state was photographed with the digital camera. The photographed image was stored as digitally converted data (digital image) in an 8-bit bitmap format.
The colored coating surface was photographed for 20 arbitrarily selected areas. In addition, the digitally converted data was stored by digitizing the captured image as a density distribution of 256 gradations from 0 to 255 for each of the three primary colors of RGB.
Next, the stored digital image was divided into a grid shape so that one grid size corresponds to 0.5 μm square on the actual substrate, and the luminance in one section was averaged. In this example, since a 1.times.820,000 pixel digital camera took an image with a magnification of 1000 times, 0.5 μm on the actual substrate was 0.5 mm on the photographed image, and the image size on the display was 452 mm × 352 mm. Therefore, the total number of sections in one area was 636416.
For all the sections in each region, an arbitrary luminance and the average luminance of all adjacent sections adjacent to it were measured. A section having a difference of 5 or more from the average brightness of adjacent sections was recognized as a significant difference section, and the average total number of significant difference sections in all regions was calculated. The smaller this value is, the smaller the density difference from the adjacent section, the smaller the roughness, and the better the characteristics as a color filter.
The average total number of textures of the colored coating film 1 is the value of the texture immediately after the preparation, the average total number of textures of the colored film 2 is the value of the texture after 6 months of room temperature, and further from the value of the texture immediately after the preparation to the room temperature of 6 months. Table 5 below shows the rate of increase in the texture over time.

In Table 5 above, each symbol means the following compound.
Photopolymerization initiator (E-2): Ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (0-acetyloxime) (manufactured by BASF) , IRGACURE OXE02)
Photopolymerization initiator (E-3): 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (manufactured by BASF, IRGACURE 379)
Ethylenically unsaturated compound (F-2): Mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD DPHA)
Ethylenically unsaturated compound (F-3): trimethylolpropane triacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., A-TMPT)

UV absorber: Compound of the following structural formula

From the results shown in Table 5 above, the red photosensitive resin compositions (RR-r) and (RR-t) of Comparative Example 1 and Comparative Example 3 are (C) phosphorus which is an essential component in the composition of the present invention. Although it contains an acid-based dispersant, (D) it does not contain a resin having a specific structure, so that it is greatly inferior in pattern formation after PCD, and it has been found that the increase in zara over time is somewhat large. The red photosensitive resin compositions (RR-s) and (RR-u) of Comparative Example 2 and Comparative Example 4 contain (D) a resin having a specific structure, which is an essential component in the composition of the present invention. (C) Since the phosphoric acid-based dispersant was not included, the time-dependent increase in Zara was very large, and there was room for improvement in pattern formation after PCD.
On the other hand, for example, the red photosensitive resin composition (RR-a) of the present invention shown in Example 1 is an essential component for the composition of the present invention (C) a phosphoric acid-based dispersant, and (D). It has been found that since a resin having a specific structure is contained, an increase in the roughness over time is suppressed, and the pattern formability after PCD is greatly improved.
Moreover, it turned out that Examples 6-20 using resin (G-1) which has a polymerizable double bond in a side chain as (G) resin binder have the increase rate of Zara suppressed more.
It turned out that Examples 12 and 19 using the phosphoric acid-based dispersant (C-3) are more excellent in pattern formation after PCD than Examples using other phosphoric acid-based dispersants.
(D) Example 5 using the pigment dispersion composition (Rc) '' in which the content of the resin having a specific structure exceeds 80 parts by mass with respect to 100 parts by mass of the (A) pigment is Although the increase rate and the pattern forming property after PCD were superior to those of the comparative examples, it was found that they were slightly inferior to the other examples.
As shown in Example 4, (A) a pigment, (B) a basic dye derivative, and (C) a phosphoric acid-based dispersant are dispersed to obtain a red pigment dispersion composition, and then (D) a resin is blended Thus, it was found that by preparing the red photosensitive resin composition, the increase in zara over time was further suppressed, and the pattern formability after PCD was further improved.

<Preparation of green photosensitive resin composition>
A green photosensitive resin composition (GR-a) was prepared by uniformly stirring and mixing a mixture having the following composition.
Green pigment dispersion composition (G-a) 50.7 parts by mass Resin binder 1 4.7 parts by mass (as 40% by mass resin solution)
0.5 parts by mass of the photopolymerization initiator (E-1) 4.9 parts by mass of the ethylenically unsaturated compound (F-1) Fluorosurfactant (manufactured by Dainippon Ink Co., Ltd., Megafac F-781F)
4.2 parts by mass (as a propylene glycol monomethyl ether acetate solution having a nonvolatile content of 1% by mass)
Ultraviolet absorber (the above-mentioned compound) 0.3 part by mass p-methoxyphenol 0.0003 part by mass Propylene glycol monomethyl ether acetate (PGMEA)
34.7 parts by mass

  The green photosensitive resin compositions (GR-b) to (GR-u) were prepared in the same manner as the preparation of the green photosensitive resin composition (GR-a) described above except that the content of the composition was changed to the contents of Table 6. Was prepared.

  The green photosensitive resin compositions (GR-a) to (GR-u) thus obtained were subjected to the same method as in Example 1, immediately after preparation, and after the lapse of 6 months at room temperature and the pattern formation after PCD. Was evaluated. The results are summarized in Table 6 below.

From the results shown in Table 6 above, the green photosensitive resin compositions (GR-r) and (GR-t) of Comparative Examples 5 and 7 are essential components in the composition of the present invention. Although it contains a dispersant, (D) it does not contain a resin having a specific structure, it is greatly inferior in pattern formation after PCD, and the time-dependent increase in roughness is also somewhat large. In addition, the green photosensitive resin compositions (GR-s) and (GR-u) of Comparative Examples 6 and 8 include (D) a resin binder having a specific structure, which is an essential component in the composition of the present invention. (C) Since it does not contain a phosphoric acid-based dispersant, the time-dependent increase in Zara is very large, and there is room for improvement in pattern formation after PCD.
On the other hand, for example, the green photosensitive resin composition (GR-a) of the present invention shown in Example 21 is (C) a phosphoric acid dispersant which is an essential component for the composition of the present invention, and (D). It has been found that since a resin having a specific structure is contained, an increase in the roughness over time is suppressed, and the pattern formability after PCD is greatly improved.
Moreover, it turned out that Examples 29-39 using resin (G-1) which has a polymerizable double bond in a side chain as (G) resin binder have suppressed the increase rate of Zara more.
It turned out that Examples 32 and 39 using a phosphoric acid type dispersing agent (C-3) are excellent in pattern formation after PCD than an example using other phosphoric acid type dispersing agents.
(D) Example 25 using the pigment dispersion composition (Gc) '' in which the resin content exceeds 80 parts by mass with respect to 100 parts by mass of (A) pigment, Although the pattern formability after PCD was better than that of the comparative example, it was found that it was slightly inferior to the other examples.
As shown in Example 24, after (A) a pigment, (B) a basic dye derivative, and (C) a phosphoric acid dispersant are dispersed, (D) a resin is blended to obtain a colored photosensitive resin composition. It was found that the increase in zara over time was further suppressed by the preparation, and the pattern forming property after PCD was further improved.

<Preparation of blue photosensitive resin composition>
A blue photosensitive resin composition (BR-a) was prepared by uniformly stirring and mixing a mixture having the following composition.
Blue pigment dispersion composition (Ba) 54.9 parts by mass Resin binder 1 2.7 parts by mass (as 40% by mass resin solution)
1.4 parts by mass of the photopolymerization initiator (E-1) 2.8 parts by mass of the ethylenically unsaturated compound (F-1) Fluorine-based surfactant (Megafac F-781F, manufactured by Dainippon Ink Co., Ltd.)
4.2 parts by mass (as a propylene glycol monomethyl ether acetate solution having a nonvolatile content of 1% by mass)
p-Methoxyphenol 0.0003 parts by mass Propylene glycol monomethyl ether acetate (PGMEA)
34.0 parts by mass

  The blue photosensitive resin compositions (BR-b) to (BR-) were prepared in the same manner as in the preparation of the blue photosensitive resin composition (BR-a) except that the composition contents were changed to the contents shown in Table 7 below. m) was adjusted.

  The obtained blue photosensitive resin compositions (BR-a) to (BR-m) were subjected to the same method as in Example 1, immediately after preparation, and after the lapse of 6 months at room temperature and the pattern forming property after PCD. Was evaluated. The results are summarized in Table 7 below.

From the results shown in Table 7, the blue photosensitive resin composition (BR-l) of Comparative Example 9 contains (C) a phosphoric acid dispersant, which is an essential component for the composition of the present invention. ) Since a resin binder having a specific structure is not included, the pattern formability after PCD is greatly inferior, and the time-dependent increase in roughness is slightly large. Moreover, although the blue photosensitive resin composition (BR-m) of the comparative example 10 contains the resin of (D) specific structure which is an essential component in the composition of this invention, (C) phosphoric acid type dispersing agent is included. Since it does not contain, the increase with time is very large, and there is room for improvement in pattern formation after PCD.
On the other hand, for example, the blue photosensitive resin composition (BR-a) of the present invention shown in Example 40 is an essential component for the composition of the present invention (C) a phosphoric acid-based dispersant, and (D). Since the resin binder having a specific structure is included, increase in roughness after 6 months at room temperature is suppressed, and it can be seen that the pattern formability after PCD is greatly improved.
Moreover, it turned out that the increase rate of Zara is further suppressed in Examples 45-52 using (G) resin (G-1) which has a polymerizable double bond in a side chain as a resin binder.
It turned out that Example 43 and 51 using a phosphoric acid type dispersing agent (C-3) are excellent in the pattern formation property after PCD rather than the Example using another phosphoric acid type dispersing agent.
(D) Example 44 using the pigment dispersion composition (Rc) '' in which the resin content exceeds 80 parts by mass with respect to 100 parts by mass of (A) pigment, Although the pattern formability after PCD was better than that of the comparative example, it was found that it was slightly inferior to the other examples.
As shown in Example 43, (A) a pigment, (B) a basic dye derivative, and (C) a phosphoric acid dispersant are dispersed, and then (D) a resin is blended to obtain a colored photosensitive resin composition. It was found that the increase in zara over time was further suppressed by the preparation, and the pattern forming property after PCD was further improved.

In each of the above examples, (B) the dye derivative was replaced with an equivalent amount of Compound 7 (transcribed below) described in paragraph 0223 of JP2011-162760A, and the others were performed in the same manner. It was confirmed that can be formed.

Claims (17)

(A) a pigment, (B) a basic dye derivative, (C) a phosphoric acid dispersant represented by the following general formula (II), and (D) a compound (x) represented by the following general formula (IV): A colored photosensitive resin composition containing a resin obtained by copolymerizing a compound (y) having an ethylenically unsaturated double bond, (E) a photopolymerization initiator, and (F) a polymerizable compound;

In the general formula (II), R ³ represents a polyester structure having a number average molecular weight of 400 to 30,000, y represents 1 or 2, and when y is 2, a plurality of R ³ may be the same or different. May be;
In the general formula (IV), R ⁴ represents a hydrogen atom or a methyl group, R ⁵ represents an alkylene group having 2 or 3 carbon atoms, R ⁶ represents a hydrogen atom or a benzene ring which may contain a benzene ring. 20 represents an alkyl group, and n represents an integer of 1 to 15; when n is 2 or more, a plurality of R ^{5 s} may be the same or different. The colored photosensitive resin composition according to claim 1, wherein the (B) basic dye derivative is a compound having an amino group. The colored photosensitive resin composition according to claim 1 or 2, wherein the (A) pigment is selected from the group consisting of a red pigment, a green pigment, and a yellow pigment. Wherein in formula (II), the number average molecular weight of the polyester structure represented by R ³ is from 1,900 to 10,000, colored photosensitive resin composition according to any one of claims 1 to 3. 5. The polyester structure represented by R ³ in the general formula (II) is a polyester structure obtained by ring-opening polymerization of two or more different lactone monomers. Colored photosensitive resin composition. Furthermore, the coloring photosensitive resin composition of any one of Claims 1-5 containing resin which has a polymerizable double bond in a side chain (G). The (G) resin having a polymerizable double bond in the side chain is a copolymer (a) of a polymerizable monomer (p) having 2 to 6 hydroxyl groups and another polymerizable monomer (q), The colored photosensitive resin composition according to claim 6, which is a resin obtained by reacting a functional group capable of reacting with a hydroxyl group and a compound (b) having an ethylenically unsaturated double bond. The content of the resin obtained by copolymerizing the compound (x) represented by the general formula (D) and the compound (y) having an ethylenically unsaturated double bond is 100 masses of the pigment (A). The colored photosensitive resin composition of any one of Claims 1-7 which is 5-80 mass parts with respect to a part. After the colored photosensitive resin composition has dispersed the (A) pigment, the (B) basic dye derivative, and the (C) phosphoric acid-based dispersant represented by the general formula (II), (D) Any one of Claims 1-8 formed by mix | blending the resin formed by copolymerizing the compound (x) represented by general formula (IV), and the compound (y) which has an ethylenically unsaturated double bond. The colored photosensitive resin composition according to item 1. The colored photosensitive resin composition according to claim 1, which is used for forming a colored region of a color filter. The cured film formed by hardening | curing the colored photosensitive resin composition of any one of Claims 1-10. Applying the colored photosensitive resin composition according to any one of claims 1 to 10 on a support to form a colored photosensitive composition layer, and forming the colored photosensitive composition layer into a pattern A method for producing a color filter, comprising a step of exposing and a step of developing and removing an unexposed portion to form a colored pattern. Applying the colored photosensitive resin composition according to any one of claims 1 to 10 on a support to form a colored photosensitive composition layer;
Forming a photoresist layer on the colored photosensitive composition layer;
A method for producing a color filter, comprising: a step of patterning the photoresist layer by exposure and development to obtain a resist pattern; and a step of dry etching the colored photosensitive composition layer using the resist pattern as an etching mask. A color filter having the cured film according to claim 11. A color filter manufactured by the method for manufacturing a color filter according to claim 12 or 13. A solid-state imaging device comprising the color filter according to claim 14. An image display device comprising the color filter according to claim 14.

Images