JP2012173319A - Red colored composition for color filter, and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a red colored composition for a color filter capable of manufacturing a color filter with excellent dispersibility, good flowability, high contrast ratio and enhanced brightness, and to provide a color filter using the red colored composition.SOLUTION: The red colored composition for a color filter is a coloring composition containing a pigment including a diketopyrrolopyrrole red pigment (A), a dye derivative (B), a resin (C), and a solvent (D). The dye derivative (B) contains a quinophthalone dye derivative [B1] represented by general formula (1) and a thiazine indigo dye derivative [B2] represented by general formula (4). The color filter includes a red filter segment made of the red colored composition for a color filter.

Description

  The present invention relates to a colored composition for a color filter used for manufacturing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like, and a color filter including a filter segment formed using the same. is there.

  The color liquid crystal display device controls the amount of light passing through the second polarizing plate by controlling the degree of polarization of the light that has passed through the first polarizing plate by the liquid crystal layer sandwiched between the two polarizing plates. This is a display device that performs display by using a twisted nematic (TN) type liquid crystal. The liquid crystal display device can perform color display by providing a color filter between two polarizing plates. Therefore, liquid crystal display devices are being developed for use in televisions and personal computer monitors.

  Other typical liquid crystal display devices include an in-plane switching (IPS) method in which a pair of electrodes is provided on one substrate and electrolysis is applied in a direction parallel to the substrate, negative dielectric anisotropy Vertical alignment (VA) method for vertically aligning nematic liquid crystal with optical properties, and Optical Convencence Bend (OCB) method in which the optical axes of uniaxial retardation films are orthogonal to each other to perform optical compensation Etc., and each has been put to practical use.

  In general, the color filter is a red filter layer (R), green filter layer (G) and blue filter layer (B) formed on the surface of a transparent substrate such as glass, or a complementary color of red, green and blue. Corresponding fine band (striped) filter segments (pixels) composed of a cyan filter layer (C), a magenta filter layer (M), and a yellow color filter layer (Y) are arranged in parallel or crossing each other. Or fine filter segments arranged in a constant vertical and horizontal arrangement. The filter segments are as fine as several microns to several hundreds of microns, and are regularly arranged in a predetermined arrangement for each hue.

  On the color filter used in the color liquid crystal display device, a transparent electrode for driving the liquid crystal is generally formed by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is formed thereon. Has been. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, it is necessary to perform the formation process at a high temperature of generally 200 ° C. or higher, preferably 230 ° C. or higher.

  Quality items required for the color filter include brightness and contrast ratio. When a color filter with a low contrast ratio is used, the degree of polarization controlled by the liquid crystal is disturbed, and when light must be blocked (OFF state), light must leak or be transmitted (ON) In other words, the transmitted light is attenuated in the state), resulting in a blurred screen. Therefore, in order to realize a high-quality liquid crystal display device, high contrast is indispensable.

  If a color filter with low brightness is used, the light transmittance is low, resulting in a dark screen. In order to obtain a bright screen, it is necessary to increase the number of backlights as light sources. For this reason, from the viewpoint of suppressing an increase in power consumption, increasing the brightness of color filters has become a trend. Furthermore, as described above, since the color liquid crystal device has been used for televisions, personal computer monitors, and the like, the demand for high reliability and high lightness and contrast for color filters has also increased.

  The color filter production method includes a dyeing method using a dye or a salt-forming dye as a colorant, a dye dispersion method, a pigment dispersion method using a pigment as a colorant, a printing method, and an electrodeposition method. Among these, the dyeing method or the dyeing and dispersing method has a drawback that the heat resistance and light resistance are slightly inferior because the colorant is a dye. Therefore, a pigment having excellent heat resistance and light resistance is used as a colorant for the color filter, and a pigment dispersion method is often used as a manufacturing method because of the accuracy and stability of the forming method.

  In the pigment dispersion method, a color resist is formed by mixing and blending a photosensitive agent or an additive into a resin in which pigment particles as a colorant are dispersed in a resin, and this color resist is applied onto a substrate by a coating device such as a spin coater. In this method, a color filter is produced by forming a coating film by the above, performing selective exposure through a mask with an aligner or a stepper, patterning by alkali development and thermosetting, and repeating this operation.

In general, the pigment particles are subjected to a micronization treatment and a pigment dispersion in which the micronized pigment is brought close to the primary particles as much as possible is used to suppress light scattering by the pigment and achieve high contrast. In addition, since the transparency of the dispersion is improved, the spectral spectrum of the dispersion has high transmittance, and high brightness is realized. By using this dispersion as a color resist, a color filter having a high contrast ratio and high brightness can be obtained.

  Conventionally, the red filter segment constituting the color filter includes C.I., which is an anthraquinone pigment. I. Pigment Red 177 has been used. This pigment can be easily miniaturized by mechanical treatment, and the finer pigment can be dispersed relatively easily, which is useful for increasing the contrast ratio (for example, patents). Reference 1). However, there is a limit to the brightness improvement in terms of spectral characteristics.

  Recently, in place of anthraquinone red pigments, C.I. I. Diketopyrrolopyrrole red pigments such as Pigment Red 254 are often used. This pigment is C.I. I. The transmission spectrum near 600 nm is closer to the short wavelength side than Pigment Red 177, and the absorption of the red bright line of the backlight is less, so that the transparency is high and the brightness can be improved. (For example, refer to Patent Document 2 and Patent Document 3).

  However, diketopyrrolopyrrole red pigments can be easily refined by mechanical treatment, but the cohesive force is strong, so that dispersion of the pigment becomes difficult as the degree of refinement progresses. By using a diketopyrrolopyrrole pigment derivative, the pigment dispersion can be improved, but it causes a decrease in lightness, so it is difficult to achieve both high dispersibility and high lightness.

Japanese Patent Laid-Open No. 10-148712 Japanese Patent Laid-Open No. 11-231516 JP 2002-328217 A

  An object of the present invention is to provide a red coloring composition for a color filter, which is excellent in dispersibility and fluidity, and capable of producing a color filter having a high contrast ratio and high brightness, and a color filter using the same. To do.

  The present inventors have found that the above-mentioned problems can be solved by using a dye derivative having a specific dye skeleton in combination with a diketopyrrolopyrrole red pigment.

That is, the present invention is a colored composition containing a pigment (A) containing a diketopyrrolopyrrole red pigment, a dye derivative (B), a resin (C), and a solvent (D),
The color filter, wherein the dye derivative (B) includes a quinophthalone dye derivative [B1] represented by the general formula (1) and a thiazineindigo dye derivative [B2] represented by the general formula (4) The present invention relates to a red coloring composition.
General formula (1)

［一般式（１）中、Ｑは置換基を有していてもよいキノフタロン残基を表し、
Ｘ₁は、−ＮＲ’ＳＯ₂−、−ＳＯ₂ＮＲ’−、−ＣＯＮＲ’−、−ＣＨ₂ＮＲ’ＣＯＣＨ₂ＮＲ’−または−ＮＲ’ＣＯ−から選ばれる基を表し、Ｘ₂は置換基を有していてもよく炭素数が２０以下のアリーレン基または置換基を有していてもよく炭素数が２０以下の複素芳香環から選ばれる基を表し（これらの基は、−ＮＲ’−、−Ｏ−、−ＳＯ₂−または−ＣＯ−から選ばれる２価の連結基で相互に結合されていてもよい。）、Ｘ₃は、−ＮＲ’−または−Ｏ−を表し、（ただし、Ｒ’は、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表す。）、ＡおよびＢは、それぞれ独立に、下記一般式（２）もしくは一般式（３）で表される基、−Ｏ−（ＣＨ₂）ｎ−Ｒ₁、−ＯＲ₂、−ＮＲ₃Ｒ₄、−Ｃｌ、−Ｆまたは−Ｘ₃−Ｘ₂−Ｘ₁−Ｑから選ばれる基を表し（Ｒ₁は置換されていてもよい含窒素複素環残基を表し、Ｒ₂、Ｒ₃、Ｒ₄は、それぞれ独立に、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表し、ｎは０〜２０の整数を表す。）ＡおよびＢのいずれか一方は、下記一般式（２）もしくは（３）で表される基、−Ｏ−（ＣＨ₂）ｎ−Ｒ₈、−ＯＲ₉または−ＮＲ₁₀Ｒ₁₁であり、ｔは１〜３の整数を表す。］
一般式（２）

[In general formula (1), Q represents a quinophthalone residue which may have a substituent,
X _{1 is, -NR'SO 2 -, - SO 2} NR '-, - CONR' -, - CH 2 NR'COCH 2 NR'- or -NR'CO- represents a group selected from, X ₂ is substituted Represents a group selected from an arylene group having 20 or less carbon atoms, or an arylene group having a carbon number of 20 or less or a heteroaromatic ring having 20 or less carbon atoms (these groups are represented by —NR ′ And may be bonded to each other by a divalent linking group selected from —, —O—, —SO ₂ — or —CO—.), X ₃ represents —NR′— or —O—, ( However, R ′ may have a hydrogen atom, a substituent, may have an alkyl group having 20 or less carbon atoms, may have a substituent, and has an alkenyl group or substituent having 20 or less carbon atoms. And represents an aryl group having 20 or less carbon atoms), A and B are each independently represented by the following general formula (2). Groups properly represented by the general formula _{(3), -O- (CH 2} ) n-R 1, -OR 2, -NR 3 R 4, -Cl, -F , or -X ₃ -X ₂ -X ₁ -R represents a group selected from -Q (R ₁ represents an optionally substituted nitrogen-containing heterocyclic residue, and R ₂ , R ₃ , and R ₄ each independently have a hydrogen atom or a substituent. May represent an alkyl group having 20 or less carbon atoms, may have a substituent, may have an alkenyl group having 20 or less carbon atoms, or may have a substituent, and represents an aryl group having 20 or less carbon atoms, n represents an integer of 0 to 20.) is one of a and B, groups represented by the following general formula (2) or _{(3), -O- (CH 2} ) n-R 8, -OR ₉ or —NR ₁₀ R ₁₁ , and t represents an integer of 1 to 3. ]
General formula (2)

［一般式（２）中、Ｙ₁は−ＮＲ’−または−Ｏ−を表し、Ｙ₂は、置換基を有していてもよく炭素数が２０以下のアルキレン基、置換基を有していてもよく炭素数が２０以下のアルケニレン基または置換基を有していてもよく炭素数が２０以下のアリーレン基から選ばれる基を表し（これらの基は、−ＮＲ’−、−Ｏ−、−ＳＯ₂−または−ＣＯ−から選ばれる２価の連結基で相互に結合されていてもよい。ただし、Ｒ’は、一般式（１）で定義されたものを表す。）、Ｒ₅およびＲ₆は、それぞれ独立に、置換基を有していてもよく炭素数が２０以下のアルキル基または置換基を有していてもよく炭素数が２０以下のアルケニル基を表す（Ｒ₅とＲ₆が一体となって、更なる窒素原子、酸素原子または硫黄原子を含み置換されていてもよい複素環構造を形成してもよい。）。］
一般式（３）

[In General Formula (2), Y ₁ represents —NR′— or —O—, and Y ₂ may have a substituent, an alkylene group having 20 or less carbon atoms, or a substituent. Or a group selected from an alkenylene group having 20 or less carbon atoms or an arylene group having 20 or less carbon atoms which may have a substituent (these groups are represented by —NR′—, —O—, And may be bonded to each other by a divalent linking group selected from —SO ₂ — or —CO—, wherein R ′ represents the one defined by the general formula (1)), R ₅ and R ₆ each independently has a substituent, may have an alkyl group having 20 or less carbon atoms, or may have a substituent and may represent an alkenyl group having 20 or less carbon atoms (R ₅ and R ₆ together, a further nitrogen atom, an oxygen atom or containing a sulfur atom optionally substituted heterocyclic May be formed in the concrete.). ]
General formula (3)

［一般式（３）中、Ｚ₁は、トリアジン環と窒素原子を結ぶ単結合、−ＮＲ’−、−ＮＲ’−Ｇ−ＣＯ−、−ＮＲ’−Ｇ−ＣＯＮＲ’’−、−ＮＲ’−Ｇ−ＳＯ₂−、−ＮＲ’−Ｇ−ＳＯ₂ＮＲ’’−、−Ｏ−Ｇ−ＣＯ−、−Ｏ−Ｇ−ＣＯＮＲ’−、−Ｏ−Ｇ−ＳＯ₂−、または−Ｏ−Ｇ−ＳＯ₂ＮＲ’−を表し（Ｇは、置換基を有していてもよく炭素数が２０以下のアルキレン基、置換基を有していてもよく炭素数が２０以下のアルケニレン基または置換基を有していてもよく炭素数が２０以下のアリーレン基を表し、Ｒ’およびＲ’’は、それぞれ独立に、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表す。）、Ｒ₇、Ｒ₈、Ｒ₉、Ｒ₁₀は、それぞれ独立に、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表し、Ｒ₁₁は、置換基を有していてもよく炭素数が２０以下のアルキル基または置換基を有していてもよく炭素数が２０以下のアルケニル基を表す。）。］
一般式（４）

[In General Formula (3), Z ₁ represents a single bond connecting a triazine ring and a nitrogen atom, —NR′—, —NR′—G—CO—, —NR′—G—CONR ″ —, —NR ′. —G—SO ₂ —, —NR′—G—SO ₂ NR ″ —, —O—G—CO—, —O—G—CONR′—, —O—G—SO ₂ —, or —O—. G—SO ₂ NR′— (G represents an alkylene group which may have a substituent and which has 20 or less carbon atoms, an alkenylene group which may have a substituent and which has 20 or less carbon atoms, or a substituent; An arylene group having 20 or less carbon atoms which may have a group, and R ′ and R ″ each independently have a hydrogen atom or a substituent and may have an alkyl group having 20 or less carbon atoms. An alkenyl group having 20 or less carbon atoms or a substituent, which may have a group or a substituent, or an aryl group having 20 or less carbon atoms ), R ₇ , R ₈ , R ₉ , and R ₁₀ may each independently have a hydrogen atom, a substituent, or an alkyl group having 20 or less carbon atoms, or a substituent. An alkenyl group having a carbon number of 20 or less or an aryl group having a carbon number of 20 or less which may have a substituent, and R ₁₁ may have a substituent and an alkyl group having a carbon number of 20 or less; Alternatively, it may have a substituent and represents an alkenyl group having 20 or less carbon atoms. ). ]
General formula (4)

［一般式（４）において、Ｒ₁₂及びＲ₁₃は、それぞれ独立に、−（Ｅ）_p基以外の置換基を有していてもよい、芳香族または脂肪族炭素環または複素環を形成するために必要な基を表す。Ｅは、独立に、下記一般式（５）または下記一般式（６）を表す。ｑは、１〜６の整数を表す。］
一般式（５）

[In General Formula (4), R ₁₂ and R ₁₃ each independently form an aromatic or aliphatic carbocycle or heterocycle which may have a substituent other _than- (E) _p group. Represents a group necessary for the purpose. E independently represents the following general formula (5) or the following general formula (6). q represents the integer of 1-6. ]
General formula (5)

一般式（６）

General formula (6)

［一般式（５）において、Ｒ₁₄及びＲ₁₅は、それぞれ独立に、置換基を有していてもよい炭素数１〜３０のアルキル基または置換基を有していてもよい炭素数２〜３０のアルケニル基を表し、Ｒ₁₄及びＲ₁₅は窒素、酸素または硫黄原子を含む置換されてもよい複素環を形成していてもよい。Ｘは、−Ｓ−、−Ｏ−、−ＳＯ₂−、−ＣＯ−、−ＳＯ₂ＮＲ−、−ＮＲＳＯ₂−、−ＣＯＮＲ−、−ＣＨ₂ＮＲＣＯＣＨ₂ＮＲ−または−（ＣＨ₂）_mＮＨ−を表す（但し、ｍは、１〜１０の整数を表す。Ｒは、独立に、水素原子、置換基を有していてもよい炭素数１〜２０のアルキル基、置換基を有していてもよい炭素数２〜２０のアルケニル基または置換基を有していてもよい炭素数６〜２０のアリール基を表す）。ａは、０または１を表す。Ｙは、置換基を有していてもよい炭素数１〜２０のアルキレン基、置換基を有していてもよい炭素数２〜２０のアルケニレン基、置換基を有していてもよい炭素数６〜２０のアリーレン基または窒素、酸素または硫黄原子を含む置換されていてもよい複素環を表す（これらの基は、二つ以上組合せてもよく、−ＮＲ−、−Ｏ−、−ＳＯ₂−、−ＣＯ−または−ＣＯＮＨ−から選ばれる２価の連結基で互いに結合していてもよい。ここで、Ｒは上記定義の通りである。）。ｂは、０または１を表す。一般式（６）において、Ｒ₁₆〜Ｒ₁₉は、それぞれ独立に、置換基を有していてもよい炭素数１〜３０のアルキル基または置換基を有していてもよい炭素数２〜３０のアルケニル基または置換基を有していてもよい炭素数６〜２０のアリール基を表す。Ｒ₂₀は、水素原子、置換基を有していてもよい炭素数１〜２０のアルキル基または置換基を有していてもよい炭素数２〜２０のアルケニル基を表す。Ｚは、−ＣＨ₂ＮＲ’ＣＯＣＨ₂ＮＲ’−、−ＣＨ₂ＮＲ’ＣＯＣＨ₂ＮＲ’−Ｇ−、−ＮＲ’−、−ＮＲ’−Ｇ−ＣＯ−、−ＮＲ’−Ｇ−ＣＯＮＲ’−、−ＮＲ’−Ｇ−ＳＯ₂−、−ＮＲ’−Ｇ−ＳＯ₂ＮＲ’−、−Ｏ−Ｇ−ＣＯ−、−Ｏ−Ｇ−ＣＯＮＲ’−、−ＳＯ₂−、−Ｏ−Ｇ−ＳＯ₂−、または−Ｏ−Ｇ−ＳＯ₂ＮＲ’−を表す（Ｇは、置換基を有していてもよい炭素数１〜２０のアルキレン基、置換基を有していてもよい炭素数２〜２０のアルケニレン基または置換基を有していてもよい炭素数６〜２０のアリーレン基を表し、Ｒ’は、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表す。）。ｄは、０または１を表す。］

[In General Formula (5), R ₁₄ and R ₁₅ are each independently an alkyl group having 1 to 30 carbon atoms which may have a substituent or an optionally substituted alkyl group having 2 to 2 carbon atoms. 30 represents an alkenyl group, and R ₁₄ and R ₁₅ may form an optionally substituted heterocyclic ring containing a nitrogen, oxygen or sulfur atom. X is, -S -, - O -, - SO 2 -, - CO -, - SO 2 NR -, - NRSO 2 -, - CONR -, - CH 2 NRCOCH 2 NR- , or - (CH _{2) m} NH -(Wherein m represents an integer of 1 to 10. R independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent. An alkenyl group having 2 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent). a represents 0 or 1; Y is an optionally substituted alkylene group having 1 to 20 carbon atoms, an optionally substituted alkenylene group having 2 to 20 carbon atoms, and an optionally substituted carbon number. 6-20 arylene group or a nitrogen, oxygen or (these groups representing a heterocyclic ring which may be substituted containing a sulfur atom may be combined two or more, -NR -, - O -, - SO 2 And may be bonded to each other through a divalent linking group selected from-, -CO- and -CONH-, wherein R is as defined above. b represents 0 or 1. In General Formula (6), R _{16 to} R ₁₉ are each independently an alkyl group having 1 to 30 carbon atoms which may have a substituent, or 2 to 30 carbon atoms which may have a substituent. An alkenyl group or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ₂₀ represents a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkenyl group having 2 to 20 carbon atoms. Z _{is, -CH 2 NR'COCH 2 NR '-} , - CH 2 NR'COCH 2 NR'-G -, - NR' -, - NR'-G-CO -, - NR'-G-CONR'- _{, -NR'-G-SO 2 -} , - NR'-G-SO 2 NR '-, - O-G-CO -, - O-G-CONR' -, - SO 2 -, - O-G- Represents SO ₂ — or —O—G—SO ₂ NR′— (G represents an alkylene group having 1 to 20 carbon atoms which may have a substituent, and the carbon number which may have a substituent. Represents a 2-20 alkenylene group or an arylene group having 6 to 20 carbon atoms which may have a substituent, and R ′ represents a hydrogen atom, an optionally substituted alkyl having 20 or less carbon atoms. A alkenyl group having 20 or less carbon atoms or a substituent, which may have a group or a substituent, or an aryl group having 20 or less carbon atoms. d represents 0 or 1. ]

In the present invention, the total content of the quinophthalone dye derivative [B1] represented by the general formula (1) and the thiazineindigo dye derivative [B2] represented by the general formula (4) is the pigment (A) 100. It is 25-43 weight part with respect to a weight part, It is related with the said red coloring composition for color filters characterized by the above-mentioned.
In the present invention, the content of the quinophthalone dye derivative [B1] represented by the general formula (1) is 13 to 20 parts by weight with respect to 100 parts by weight of the pigment (A). The present invention relates to a red coloring composition for a filter.
The present invention further relates to the red coloring composition for a color filter, further comprising an active energy ray-curable monomer and a photopolymerization initiator.
The present invention also relates to a color filter comprising a red filter segment formed from the red coloring composition for a color filter.

  The red coloring composition for a color filter of the present invention is excellent in dispersibility and fluidity by using a specific pigment derivative, and can maintain higher brightness. Therefore, a color filter having a high contrast ratio and a high brightness can be provided by using the red coloring composition for a color filter of the present invention.

It is an example of the emission spectrum of the used backlight.

  Hereinafter, the present invention will be described in detail. First, various components of the red coloring composition for a color filter of the present invention will be described.

[Pigment (A)]
The red coloring composition for color filters of the present invention contains a diketopyrrolopyrrole red pigment as the main pigment as the pigment (A). As a representative example, C.I. I. Pigment Red 254, C.I. I. Pigment Red 255, 264, 272 and the like. Among them, C.I. I. Pigment Red 254 is suitable because it has the highest transparency when reproducing red chromaticity conforming to the EBU standard, which is one of the television broadcasting standards, in combination with the red bright line of the three-wavelength cold cathode tube backlight. It is.

As the pigment (A) used in the present invention, not only diketopyrrolopyrrole red pigments but also other red pigments, orange pigments and yellow pigments can be used in combination for color adjustment and complementary purposes.
For example, as red pigments other than diketopyrrolopyrrole, C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 81: 4, 146, 168, 177, 178, 179, 184, 185, 187, 200, 202, 208, 210, 246, 270, 279 and the like.

  Examples of yellow pigments include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180 181, 182, 185, 187, 188, 193, 194, 198, 199, 213, 214 and the like.

  Examples of the orange pigment include C.I. I. Pigment Orange 36, 43, 51, 55, 59, 61, 71, 73 and the like.

  In addition, an inorganic pigment can be contained in order to ensure good coatability, sensitivity, developability and the like while balancing saturation and lightness. Inorganic pigments include titanium oxide, barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red rose (red iron oxide (III)), cadmium red, ultramarine blue, bitumen, chromium oxide green, cobalt green, amber, titanium Examples thereof include black, synthetic iron black, and carbon black. An inorganic pigment is used individually or in combination of 2 or more types. The inorganic pigment can be used in an amount of 0.1 to 10% by weight in 100% by weight of the pigment (A).

  Further, the red composition for a color filter of the present invention may contain a dye within a range that does not reduce heat resistance for color matching. The dye can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the pigment (A).

(Miniaturization of pigment)
The pigment that can be used in combination with the colored composition of the present invention is preferably one that has been refined by salt milling. The primary particle diameter of the pigment is preferably 20 nm or more because of good dispersion in the colorant carrier. Moreover, since it can form a filter segment with a high contrast ratio, it is preferably 100 nm or less. A particularly preferable range is a range of 25 to 85 nm. The primary particle diameter of the pigment was measured by directly measuring the size of the primary particle from an electron micrograph of the pigment using a TEM (transmission electron microscope). Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the pigment particles. Next, with respect to 100 or more pigment particles, the volume of each particle is obtained by approximating it with a cube of the obtained particle size, and the volume average particle size is defined as the average primary particle size.

  Salt milling is a process in which a mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent is heated using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or sand mill. After kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt serves as a crushing aid, and the pigment is crushed using the high hardness of the inorganic salt during salt milling. By optimizing the conditions for salt milling the pigment, it is possible to obtain a pigment having a sharp particle size distribution with a very fine primary particle diameter and a wide distribution range.

  As the water-soluble inorganic salt, sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of cost. The water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by weight, and most preferably 300 to 1000 parts by weight, based on 100 parts by weight of the pigment, from both the processing efficiency and the production efficiency.

  The water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent is easily evaporated. For example, 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, Liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol and the like are used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, and most preferably 50 to 500 parts by weight, based on 100 parts by weight of the pigment.

  When the salt is milled, a resin may be added as necessary. The type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. The resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the organic solvent. It is preferable that the usage-amount of resin is 5-200 weight part with respect to 100 weight part of pigments.

[Dye derivative (B)]
The red coloring composition for a color filter of the present invention comprises at least two kinds of a quinophthalone dye derivative [B1] represented by the general formula (1) and a thiazineindigo dye derivative [B2] represented by the general formula (4). It is characterized by containing.

  The quinophthalone dye derivative [B1] represented by the general formula (1) is a compound in which a functional group having a high pigment dispersion ability is introduced into an excellent quinophthalone skeleton as an anchor. Compared with the case where an agent is used, the dispersibility of the organic pigment in the pigment carrier is improved, and the contrast ratio of the filter segment is increased.

  The thiazine indigo dye derivative [B2] has a structure similar to that of the diketopyrrolopyrrole dye derivative, and further has functional groups capable of hydrogen bonding (═O, ═NH). Since the diketopyrrolopyrrole pigment derivative has the same chemical structure as the diketopyrrolopyrrole red pigment, it has a strong adsorptive power on the surface and has the effect of stabilizing the dispersion and suppressing crystal precipitation due to high-temperature treatment. Therefore, the same effect on the diketopyrrolopyrrole red pigment as the diketopyrrolopyrrole pigment derivative is exhibited.

Furthermore, the quinophthalone dye derivative [B1] represented by the general formula (1) and the thiazine indigo dye derivative [B2] represented by the general formula (4) are yellower than the diketopyrrolopyrrole dye derivative. Therefore, the influence of the diketopyrrolopyrrole red pigment on the decrease in transparency due to the increase in the blending amount is less than that of the diketopyrrolopyrrole dye derivative. Therefore, it is effective for maintaining high brightness.
General formula (1)

［一般式（１）中、Ｑは置換基を有していてもよいキノフタロン残基を表し、
Ｘ₁は、−ＮＲ’ＳＯ₂−、−ＳＯ₂ＮＲ’−、−ＣＯＮＲ’−、−ＣＨ₂ＮＲ’ＣＯＣＨ₂ＮＲ’−または−ＮＲ’ＣＯ−から選ばれる基を表し、Ｘ₂は置換基を有していてもよく炭素数が２０以下のアリーレン基または置換基を有していてもよく炭素数が２０以下の複素芳香環から選ばれる基を表し（これらの基は、−ＮＲ’−、−Ｏ−、−ＳＯ₂−または−ＣＯ−から選ばれる２価の連結基で相互に結合されていてもよい。）、Ｘ₃は、−ＮＲ’−または−Ｏ−を表し、（ただし、Ｒ’は、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表す。）、ＡおよびＢは、それぞれ独立に、下記一般式（２）もしくは一般式（３）で表される基、−Ｏ−（ＣＨ₂）ｎ−Ｒ₁、−ＯＲ₂、−ＮＲ₃Ｒ₄、−Ｃｌ、−Ｆまたは−Ｘ₃−Ｘ₂−Ｘ₁−Ｑから選ばれる基を表し（Ｒ₁は置換されていてもよい含窒素複素環残基を表し、Ｒ₂、Ｒ₃、Ｒ₄は、それぞれ独立に、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表し、ｎは０〜２０の整数を表す。）ＡおよびＢのいずれか一方は、下記一般式（２）もしくは（３）で表される基、−Ｏ−（ＣＨ₂）ｎ−Ｒ₈、−ＯＲ₉または−ＮＲ₁₀Ｒ₁₁であり、
ｔは１〜３の整数を表す。］
一般式（２）

[In general formula (1), Q represents a quinophthalone residue which may have a substituent,
X _{1 is, -NR'SO 2 -, - SO 2} NR '-, - CONR' -, - CH 2 NR'COCH 2 NR'- or -NR'CO- represents a group selected from, X ₂ is substituted Represents a group selected from an arylene group having 20 or less carbon atoms, or an arylene group having a carbon number of 20 or less or a heteroaromatic ring having 20 or less carbon atoms (these groups are represented by —NR ′ And may be bonded to each other by a divalent linking group selected from —, —O—, —SO ₂ — or —CO—.), X ₃ represents —NR′— or —O—, ( However, R ′ may have a hydrogen atom, a substituent, may have an alkyl group having 20 or less carbon atoms, may have a substituent, and has an alkenyl group or substituent having 20 or less carbon atoms. And represents an aryl group having 20 or less carbon atoms), A and B are each independently represented by the following general formula (2). Groups properly represented by the general formula _{(3), -O- (CH 2} ) n-R 1, -OR 2, -NR 3 R 4, -Cl, -F or -X ₃ -X ₂ -X ₁ -R represents a group selected from -Q (R ₁ represents an optionally substituted nitrogen-containing heterocyclic residue, and R ₂ , R ₃ , and R ₄ each independently have a hydrogen atom or a substituent. May represent an alkyl group having 20 or less carbon atoms, may have a substituent, may have an alkenyl group having 20 or less carbon atoms, or may have a substituent, and represents an aryl group having 20 or less carbon atoms, n represents an integer of 0 to 20.) is one of a and B, groups represented by the following general formula (2) or _{(3), -O- (CH 2} ) n-R 8, -OR ₉ or -NR ₁₀ R ₁₁ ,
t represents an integer of 1 to 3. ]
General formula (2)

［一般式（２）中、Ｙ₁は−ＮＲ’−または−Ｏ−を表し、Ｙ₂は、置換基を有していてもよく炭素数が２０以下のアルキレン基、置換基を有していてもよく炭素数が２０以下のアルケニレン基または置換基を有していてもよく炭素数が２０以下のアリーレン基から選ばれる基を表し（これらの基は、−ＮＲ’−、−Ｏ−、−ＳＯ₂−または−ＣＯ−から選ばれる２価の連結基で相互に結合されていてもよい。ただし、Ｒ’は、一般式（１）で定義されたものを表す。）、Ｒ₅およびＲ₆は、それぞれ独立に、置換基を有していてもよく炭素数が２０以下のアルキル基または置換基を有していてもよく炭素数が２０以下のアルケニル基を表す（Ｒ₅とＲ₆が一体となって、更なる窒素原子、酸素原子または硫黄原子を含み置換されていてもよい複素環構造を形成してもよい。）。］
一般式（３）

[In General Formula (2), Y ₁ represents —NR′— or —O—, and Y ₂ may have a substituent, an alkylene group having 20 or less carbon atoms, or a substituent. Or a group selected from an alkenylene group having 20 or less carbon atoms or an arylene group having 20 or less carbon atoms which may have a substituent (these groups are represented by —NR′—, —O—, And may be bonded to each other by a divalent linking group selected from —SO ₂ — or —CO—, wherein R ′ represents the one defined by the general formula (1)), R ₅ and R ₆ each independently has a substituent, may have an alkyl group having 20 or less carbon atoms, or may have a substituent and may represent an alkenyl group having 20 or less carbon atoms (R ₅ and R ₆ together, a further nitrogen atom, an oxygen atom or containing a sulfur atom optionally substituted heterocyclic May be formed in the concrete.). ]
General formula (3)

［一般式（３）中、Ｚ₁は、トリアジン環と窒素原子を結ぶ単結合、−ＮＲ’−、−ＮＲ’−Ｇ−ＣＯ−、−ＮＲ’−Ｇ−ＣＯＮＲ’’−、−ＮＲ’−Ｇ−ＳＯ₂−、−ＮＲ’−Ｇ−ＳＯ₂ＮＲ’’−、−Ｏ−Ｇ−ＣＯ−、−Ｏ−Ｇ−ＣＯＮＲ’−、−Ｏ−Ｇ−ＳＯ₂−、または−Ｏ−Ｇ−ＳＯ₂ＮＲ’−を表し（Ｇは、置換基を有していてもよく炭素数が２０以下のアルキレン基、置換基を有していてもよく炭素数が２０以下のアルケニレン基または置換基を有していてもよく炭素数が２０以下のアリーレン基を表し、Ｒ’およびＲ’’は、それぞれ独立に、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表す。）、Ｒ₇、Ｒ₈、Ｒ₉、Ｒ₁₀は、それぞれ独立に、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表し、Ｒ₁₁は、置換基を有していてもよく炭素数が２０以下のアルキル基または置換基を有していてもよく炭素数が２０以下のアルケニル基を表す。）。］
一般式（４）

[In General Formula (3), Z ₁ represents a single bond connecting a triazine ring and a nitrogen atom, —NR′—, —NR′—G—CO—, —NR′—G—CONR ″ —, —NR ′. —G—SO ₂ —, —NR′—G—SO ₂ NR ″ —, —O—G—CO—, —O—G—CONR′—, —O—G—SO ₂ —, or —O—. G—SO ₂ NR′— (G represents an alkylene group which may have a substituent and which has 20 or less carbon atoms, an alkenylene group which may have a substituent and which has 20 or less carbon atoms, or a substituent; An arylene group having 20 or less carbon atoms which may have a group, and R ′ and R ″ each independently have a hydrogen atom or a substituent and may have an alkyl group having 20 or less carbon atoms. An alkenyl group having 20 or less carbon atoms or a substituent, which may have a group or a substituent, or an aryl group having 20 or less carbon atoms ), R ₇ , R ₈ , R ₉ , and R ₁₀ may each independently have a hydrogen atom, a substituent, or an alkyl group having 20 or less carbon atoms, or a substituent. An alkenyl group having a carbon number of 20 or less or an aryl group having a carbon number of 20 or less which may have a substituent, and R ₁₁ may have a substituent and an alkyl group having a carbon number of 20 or less; Alternatively, it may have a substituent and represents an alkenyl group having 20 or less carbon atoms. ). ]
General formula (4)

［一般式（４）において、Ｒ₁₂及びＲ₁₃は、それぞれ独立に、−（Ｅ）_p基以外の置換基を有していてもよい、芳香族または脂肪族炭素環または複素環を形成するために必要な基を表す。Ｅは、独立に、下記一般式（５）または下記一般式（６）を表す。ｑは、１〜６の整数を表す。］
一般式（５）

[In General Formula (4), R ₁₂ and R ₁₃ each independently form an aromatic or aliphatic carbocycle or heterocycle which may have a substituent other _than- (E) _p group. Represents a group necessary for the purpose. E independently represents the following general formula (5) or the following general formula (6). q represents the integer of 1-6. ]
General formula (5)

一般式（６）

General formula (6)

［一般式（５）において、Ｒ₁₄及びＲ₁₅は、それぞれ独立に、置換基を有していてもよい炭素数１〜３０のアルキル基または置換基を有していてもよい炭素数２〜３０のアルケニル基を表し、Ｒ₁₄及びＲ₁₅は窒素、酸素または硫黄原子を含む置換されてもよい複素環を形成していてもよい。Ｘは、−Ｓ−、−Ｏ−、−ＳＯ₂−、−ＣＯ−、−ＳＯ₂ＮＲ−、−ＮＲＳＯ₂−、−ＣＯＮＲ−、−ＣＨ₂ＮＲＣＯＣＨ₂ＮＲ−または−（ＣＨ₂）_mＮＨ−を表す（但し、ｍは、１〜１０の整数を表す。Ｒは、独立に、水素原子、置換基を有していてもよい炭素数１〜２０のアルキル基、置換基を有していてもよい炭素数２〜２０のアルケニル基または置換基を有していてもよい炭素数６〜２０のアリール基を表す）。ａは、０または１を表す。Ｙは、置換基を有していてもよい炭素数１〜２０のアルキレン基、置換基を有していてもよい炭素数２〜２０のアルケニレン基、置換基を有していてもよい炭素数６〜２０のアリーレン基または窒素、酸素または硫黄原子を含む置換されていてもよい複素環を表す（これらの基は、二つ以上組合せてもよく、−ＮＲ−、−Ｏ−、−ＳＯ₂−、−ＣＯ−または−ＣＯＮＨ−から選ばれる２価の連結基で互いに結合していてもよい。ここで、Ｒは上記定義の通りである。）。ｂは、０または１を表す。一般式（６）において、Ｒ₁₆〜Ｒ₁₉は、それぞれ独立に、置換基を有していてもよい炭素数１〜３０のアルキル基または置換基を有していてもよい炭素数２〜３０のアルケニル基または置換基を有していてもよい炭素数６〜２０のアリール基を表す。Ｒ₂₀は、水素原子、置換基を有していてもよい炭素数１〜２０のアルキル基または置換基を有していてもよい炭素数２〜２０のアルケニル基を表す。Ｚは、−ＣＨ₂ＮＲ’ＣＯＣＨ₂ＮＲ’−、−ＣＨ₂ＮＲ’ＣＯＣＨ₂ＮＲ’−Ｇ−、−ＮＲ’−、−ＮＲ’−Ｇ−ＣＯ−、−ＮＲ’−Ｇ−ＣＯＮＲ’−、−ＮＲ’−Ｇ−ＳＯ₂−、−ＮＲ’−Ｇ−ＳＯ₂ＮＲ’−、−Ｏ−Ｇ−ＣＯ−、−Ｏ−Ｇ−ＣＯＮＲ’−、−ＳＯ₂−、−Ｏ−Ｇ−ＳＯ₂−、または−Ｏ−Ｇ−ＳＯ₂ＮＲ’−を表す（Ｇは、置換基を有していてもよい炭素数１〜２０のアルキレン基、置換基を有していてもよい炭素数２〜２０のアルケニレン基または置換基を有していてもよい炭素数６〜２０のアリーレン基を表し、Ｒ’は、水素原子、置換基を有していてもよく炭素数が２０以下のアルキル基、置換基を有していてもよく炭素数が２０以下のアルケニル基または置換基を有していてもよく炭素数が２０以下のアリール基を表す。）。ｄは、０または１を表す。］

[In General Formula (5), R ₁₄ and R ₁₅ are each independently an alkyl group having 1 to 30 carbon atoms which may have a substituent or an optionally substituted alkyl group having 2 to 2 carbon atoms. 30 represents an alkenyl group, and R ₁₄ and R ₁₅ may form an optionally substituted heterocyclic ring containing a nitrogen, oxygen or sulfur atom. X is, -S -, - O -, - SO 2 -, - CO -, - SO 2 NR -, - NRSO 2 -, - CONR -, - CH 2 NRCOCH 2 NR- , or - (CH _{2) m} NH -(Wherein m represents an integer of 1 to 10. R independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent. An alkenyl group having 2 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent). a represents 0 or 1; Y is an optionally substituted alkylene group having 1 to 20 carbon atoms, an optionally substituted alkenylene group having 2 to 20 carbon atoms, and an optionally substituted carbon number. 6-20 arylene group or a nitrogen, oxygen or (these groups representing a heterocyclic ring which may be substituted containing a sulfur atom may be combined two or more, -NR -, - O -, - SO 2 And may be bonded to each other through a divalent linking group selected from-, -CO- and -CONH-, wherein R is as defined above. b represents 0 or 1. In General Formula (6), R _{16 to} R ₁₉ are each independently an alkyl group having 1 to 30 carbon atoms which may have a substituent, or 2 to 30 carbon atoms which may have a substituent. An alkenyl group or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ₂₀ represents a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkenyl group having 2 to 20 carbon atoms. Z _{is, -CH 2 NR'COCH 2 NR '-} , - CH 2 NR'COCH 2 NR'-G -, - NR' -, - NR'-G-CO -, - NR'-G-CONR'- _{, -NR'-G-SO 2 -} , - NR'-G-SO 2 NR '-, - O-G-CO -, - O-G-CONR' -, - SO 2 -, - O-G- Represents SO ₂ — or —O—G—SO ₂ NR′— (G represents an alkylene group having 1 to 20 carbon atoms which may have a substituent, and the carbon number which may have a substituent. Represents a 2-20 alkenylene group or an arylene group having 6 to 20 carbon atoms which may have a substituent, and R ′ represents a hydrogen atom, an optionally substituted alkyl having 20 or less carbon atoms. A alkenyl group having 20 or less carbon atoms or a substituent, which may have a group or a substituent, or an aryl group having 20 or less carbon atoms. d represents 0 or 1. ]

  In the red coloring composition for a color filter of the present invention, the total content of the quinophthalone dye derivative [B1] represented by the general formula (1) and the thiazineindigo dye derivative [B2] represented by the general formula (4) is The pigment (A) is preferably 9 to 67 parts by weight, more preferably 25 to 43 parts by weight, based on 100 parts by weight. When the content is less than 9 parts by weight, the pigment derivative is insufficient because the pigment derivative is insufficient, and the viscosity increase and the contrast ratio may be lowered. On the other hand, when it exceeds 67 parts by weight, the effect of suppressing crystal precipitation due to the high-temperature treatment of the diketopyrrolopyrrole red pigment is increased, but the viscosity increase and lightness due to the excess dye derivative may be decreased.

  In the present invention, the content of the quinophthalone dye derivative [B1] represented by the general formula (1) is preferably 4 to 33 parts by weight with respect to 100 parts by weight of the pigment (A), and more preferably 13 to It is preferably 20 parts by weight. When the content is less than 4 parts by weight, the pigment derivative is insufficient because the pigment derivative is insufficient, and the viscosity increase and the contrast ratio may be lowered. On the other hand, when the amount exceeds 33 parts by weight, the transparency of the diketopyrrolopyrrole red pigment is affected, and the lightness may decrease.

[Resin (C)]
The resin (C) is for dispersing the pigment (A), and examples thereof include a thermoplastic resin and a thermosetting resin. The resin (C) is preferably a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Moreover, when using with the form of an alkali image development type colored resist material, it is preferable to use the alkali-soluble vinyl resin which copolymerized the acidic group containing ethylenically unsaturated monomer. In order to further improve the photosensitivity, an energy ray curable resin having an ethylenically unsaturated active double bond can also be used.

  In order to disperse or dissolve the pigment (A) preferably, the weight average molecular weight (Mw) of the resin (C) is preferably in the range of 10,000 to 100,000, more preferably in the range of 10,000 to 80,000. It is. The number average molecular weight (Mn) is preferably in the range of 5,000 to 50,000, and the value of Mw / Mn is preferably 10 or less.

  From the viewpoint of dispersibility, stability, developability, and heat resistance of the pigment (A), a carboxyl group that functions as a pigment adsorbing group and an alkali-soluble group during development, an aliphatic group that functions as an affinity group for a colorant carrier and a solvent The balance between the group and the aromatic group is important for the dispersibility, penetrability, developability, and durability of the pigment, and it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g. When the acid value is less than 20 mgKOH / g, the solubility in the developing solution is poor and it is difficult to form a fine pattern. If it exceeds 300 mgKOH / g, no fine pattern remains.

  The resin (B) is preferably used in an amount of 30 parts by weight or more with respect to 100 parts by weight of the pigment (A) because the film formability and various resistances are good, and the colorant concentration is high, and good color characteristics. Is preferably used in an amount of 500 parts by weight or less.

(Thermoplastic resin)
Examples of the thermoplastic resin include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane resin. Polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like.

  Examples of the vinyl-based alkali-soluble resin copolymerized with an acidic group-containing ethylenically unsaturated monomer include resins having an acidic group such as a carboxyl group or a sulfone group. Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer. Among these, at least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.

  Examples of the active energy ray-curable resin having an ethylenically unsaturated double bond include resins into which an ethylenically unsaturated double bond has been introduced by the following methods (i) and (ii).

[Method (i)]
As the method (i), for example, a side chain epoxy group of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having an epoxy group and one or more other monomers is used. Addition reaction of a carboxyl group of an unsaturated monobasic acid having an ethylenically unsaturated double bond, and further reacting a polybasic acid anhydride with the generated hydroxyl group to convert an ethylenically unsaturated double bond and a carboxyl group. There is a way to introduce.

Examples of the ethylenically unsaturated monomer having an epoxy group include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, and 2-glycidoxyethyl (meth).
An acrylate, 3,4 epoxy butyl (meth) acrylate, and 3,4 epoxy cyclohexyl (meth) acrylate are mentioned, These may be used independently or may use 2 or more types together. From the viewpoint of reactivity with the unsaturated monobasic acid in the next step, glycidyl (meth)
Acrylate is preferred.

Examples of unsaturated monobasic acids include (meth) acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, α-haloalkyl of (meth) acrylic acid, alkoxyl, halogen, nitro, cyano substituted products, etc. Monocarboxylic acid etc. are mentioned, These may be used independently or may use 2 or more types together.

Examples of the polybasic acid anhydride include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride and the like.
More than one type may be used together. If necessary, use a tricarboxylic anhydride such as trimellitic anhydride or a tetracarboxylic dianhydride such as pyromellitic dianhydride to increase the number of carboxyl groups. The group can be hydrolyzed. Moreover, when an etrahydrophthalic anhydride or maleic anhydride having an ethylenically unsaturated double bond is used as the polybasic acid anhydride, the ethylenically unsaturated double bonds can be further increased.

  As a method similar to the method (i), for example, a side chain of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having a carboxyl group and one or more other monomers. There is a method in which an ethylenically unsaturated monomer having an epoxy group is added to a part of a carboxyl group to introduce an ethylenically unsaturated double bond and a carboxyl group.

[Method (ii)]
As the method (ii), an ethylenically unsaturated monomer having a hydroxyl group is used, and an unsaturated monobasic acid monomer having another carboxyl group or another monomer is copolymerized. There is a method of reacting the isocyanate group of an ethylenically unsaturated monomer having an isocyanate group with the side chain hydroxyl group of the obtained copolymer.

Examples of the ethylenically unsaturated monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3
-Or 4-hydroxybutyl (meth) acrylate, glycerol (meth) acrylate, or hydroxyalkyl (meth) acrylates such as cyclohexanedimethanol mono (meth) acrylate, and these may be used alone or in two types The above may be used in combination. Further, polyether mono (meth) acrylate obtained by addition polymerization of ethylene oxide, propylene oxide, and / or butylene oxide to the above hydroxyalkyl (meth) acrylate, (poly) γ-valerolactone, (poly) ε-caprolactone And / or (poly) 12-hydroxystearic acid added (poly) ester mono (meth) acrylate can also be used. From the viewpoint of suppressing foreign matter on the coating film, 2-hydroxyethyl (meth) acrylate or glycerol (meth) acrylate is preferable.

Examples of the ethylenically unsaturated monomer having an isocyanate group include 2- (meth) acryloyloxyethyl isocyanate, 1,1-bis [(meth) acryloyloxy] ethyl isocyanate, and the like. In addition, two or more types can be used in combination.

(Thermosetting resin)
Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins.

[Solvent (D)]
In the coloring composition of the present invention, the pigment (A) is sufficiently dispersed and permeated in the colorant carrier, and applied to a glass substrate or the like so that the dry film thickness is 0.2 to 5 μm. In order to make it easy to form the segment, a solvent (D) can be contained.
Examples of the solvent (D) include benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2 -Heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl- 1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m- Diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N-dimethylphenol Muamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert -Butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene Glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropylene Ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol Monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene Glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl Ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl Ketone, methyl cyclohexanol, acetic acid n- amyl acetate n- butyl, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic esters, butyl lactate and the like.

  Among them, since the dispersibility of the pigment (A) of the present invention is good, glycol acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, benzyl It is preferable to use aromatic alcohols such as alcohol and ketones such as cyclohexanone.

  A solvent (D) can be used individually by 1 type or in mixture of 2 or more types. Further, the solvent is preferably used in an amount of 800 to 4000 parts by weight with respect to 100 parts by weight of the pigment (A) because the colored composition can be adjusted to an appropriate viscosity to form a desired filter segment having a uniform film thickness.

[Method for producing colored composition]
The red coloring composition for a color filter of the present invention comprises a pigment (A) containing a diketopyrrolopyrrole red pigment and another pigment, a quinophthalone dye derivative [B1] represented by the general formula (1) and a general formula It can be produced by dispersing in a colorant carrier comprising the thiazineindigo dye derivative [B2] (B) shown in (4), the resin (C), and the solvent (D) (pigment dispersion) body). In the case of producing by dispersing, it can be produced by finely dispersing using various dispersing means such as a three roll mill, a two roll mill, a sand mill, a kneader, or an attritor.

  When the red coloring composition for color filter of the present invention is used as a solvent developing type or alkali developing type photosensitive coloring composition (resist material), the active energy ray-curable monomer (E) and the pigment dispersion are used. It can be adjusted by mixing the photopolymerization initiator (F) and, if necessary, resin (C), solvent (D), other dispersion aids, additives and the like.

(Dispersing aid)
When dispersing the colorant in the colorant carrier, a dispersion aid such as a resin-type dispersant and a surfactant can be used in addition to the pigment derivative. The dispersion aid is excellent in dispersion of the colorant and has a large effect of preventing reaggregation of the colorant after dispersion. Therefore, a dispersion composition is used to disperse the colorant in the colorant carrier using the dispersion aid. When used, a color filter having a high spectral transmittance can be obtained.

(Resin type dispersant)
The resin-type dispersant has a colorant-affinity part having the property of adsorbing to the colorant and a part compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant to the colorant carrier. It works to stabilize. Specific examples of resin-type dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts. , Polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester, modified products thereof, amides formed by reaction of poly (lower alkyleneimine) and polyester having a free carboxyl group, and salts thereof Oil-soluble dispersants such as, (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc. Resin, water-soluble polymer, polyester, modified poly Acrylate-based, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, it can be used alone or in admixture of two or more.

  Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, and 170 manufactured by Big Chemie Japan. 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155 or Anti-Terra-U, 203, 204, or BYK- P104, P104S, 220S, 6919, or SOLPERSE-3000, 9000, 13000, 13240, 13650, 13940, 1600 manufactured by Nihon Lubrizol Corporation, such as Lactimon, Lactimon-WS, or Bykumen. 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc. EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, manufactured by Japan 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 75 4,1101,120,150,1501,1502,1503, etc., Ajinomoto Fine-Techno Co., Ltd. of AJISPER PA111, PB711, PB821, PB822, PB824, and the like.

(Surfactant)
Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these may be used alone or in admixture of two or more, but are not necessarily limited thereto.

  When adding a resin-type dispersant and a surfactant, the amount is preferably 0.1 to 55 parts by weight, more preferably 0.1 to 45 parts by weight with respect to 100 parts by weight of the pigment (A). When the blending amount of the resin-type dispersant and the surfactant is less than 0.1 parts by weight, it is difficult to obtain the added effect. When the blending amount is more than 55 parts by weight, the dispersion is affected by an excessive dispersant. May affect.

  The coloring composition of the present invention can be used as a photosensitive coloring composition (resist material) for a color filter by further adding an active energy ray-curable monomer (E) and a photopolymerization initiator (F). .

[Active energy ray-curable monomer (E)]
The active energy ray-curable monomer (E) used in the present invention includes monomers or oligomers that are cured by ultraviolet rays or heat to form a resin, and these are used alone or in combination of two or more. be able to. The blending amount of the monomer is preferably 5 to 400 parts by weight with respect to 100 parts by weight of the pigment (A), and more preferably 10 to 300 parts by weight from the viewpoint of photocurability and developability.

  Examples of monomers and oligomers that are cured by ultraviolet rays or heat to produce a resin include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, Cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) ) Acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglycidyl -Terdi (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodeca Nyl (meth) acrylate, ester acrylate, methylolated melamine (meth) acrylate ester, epoxy (meth) acrylate, urethane acrylate and other acrylic esters and methacrylate esters, (meth) acrylic acid, styrene, vinyl acetate, Hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl (Meth) acrylamide, N-vinylformamide, acrylonitrile and the like can be mentioned, but are not necessarily limited thereto.

[Photopolymerization initiator (F)]
In the red coloring composition for color filter of the present invention, when the composition is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method, a photopolymerization initiator or the like is added to a solvent developing type or an alkali developing type. It can be adjusted in the form of a colored resist material. The amount of the photopolymerization initiator used is preferably 5 to 200 parts by weight with respect to 100 parts by weight of the pigment (A), and 10 to 150 parts by weight from the viewpoint of photocurability and developability. It is more preferable.

As the photopolymerization initiator (F), 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl Acetophenone compounds such as 1- [4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; Benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether Or benzoin compounds such as benzyldimethyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, or 3,3 Benzophenone compounds such as', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, or 2,4- Thioxanthone compounds such as diethylthioxanthone; 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-me Xylphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloro Methyl) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2 -(4-Methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, or 2,4-trichloromethyl- Triazine compounds such as (4′-methoxystyryl) -6-triazine; 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxy) )], Or oxime ester compounds such as O- (acetyl) -N- (1-phenyl-2-oxo-2- (4′-methoxy-naphthyl) ethylidene) hydroxylamine; bis (2,4,6- Phosphine compounds such as trimethylbenzoyl) phenylphosphine oxide or 2,4,6-trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone and ethylanthraquinone; borate compounds; carbazole A imidazole compound; a titanocene compound, or the like.
These photopolymerization initiators (F) can be used alone or in combination of two or more in any ratio as required.

[Sensitizer]
Furthermore, the coloring composition for a color filter of the present invention can contain a sensitizer.
Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, Trapirazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine Derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, or Michler's ketone derivatives, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl Anthraquinone, 4,4'-diethylisophthalophenone, 3,3 ', or 4,4'-tetra (t-butylperoxycarbonyl) benzopheno And 4,4′-diethylaminobenzophenone.

  More specifically, edited by Shin Okawara et al., “Dye Handbook” (1986, Kodansha), edited by Shin Okawara et al., “Chemistry of Functional Dye” (1981, CMC), edited by Tadasaburo Ikemori et al. Examples include, but are not limited to, sensitizers described in "Special Functional Materials" (1986, CMC). In addition, a sensitizer that absorbs light from the ultraviolet region to the near infrared region can also be contained.

  Two or more kinds of sensitizers may be used in any ratio as required. The blending amount when using the sensitizer is preferably 3 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator (F) contained in the colored composition, and is photocurable and developable. From the viewpoint, it is more preferably 5 to 50 parts by weight.

[Amine compound]
Moreover, the coloring composition of this invention can be made to contain the amine compound which has a function which reduces the dissolved oxygen.
Such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.

(Leveling agent)
In order to improve the leveling property of the composition on the transparent substrate, it is preferable to add a leveling agent to the colored composition of the present invention. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by Big Chemie. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination. In general, the leveling agent content is preferably 0.003 to 0.5% by weight based on the total weight of the coloring composition (100% by weight).

  Particularly preferred as a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, having a hydrophilic group but low solubility in water, and when added to a coloring composition, It has the characteristics of low surface tension reduction ability, and it is useful to have good wettability to the glass plate despite its low surface tension reduction ability. Those that can sufficiently suppress the chargeability can be preferably used. As a leveling agent having such preferable characteristics, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.

  In addition, the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used. Dimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ. -2207, but is not limited thereto.

  An anionic, cationic, nonionic or amphoteric surfactant can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.

  Anionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include esters.

  Examples of the chaotic surfactant that is supplementarily added to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts. Nonionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate And amphoteric surfactants such as alkyl dimethylamino acetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.

[Curing agent, curing accelerator]
Moreover, in order to assist hardening of a thermosetting resin, the coloring composition of this invention may contain the hardening | curing agent, the hardening accelerator, etc. as needed. As the curing agent, phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Among these, a compound having two or more phenolic hydroxyl groups in one molecule and an amine curing agent are preferable. Examples of the curing accelerator include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl). -N, N-dimethylbenzylamine etc.), quaternary ammonium salt compounds (eg triethylbenzylammonium chloride etc.), blocked isocyanate compounds (eg dimethylamine etc.), imidazole derivative bicyclic amidine compounds and salts thereof (eg Imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2- D Ru-4-methylimidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), guanamine compounds (eg, melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (eg, 2,4-diamino-6) -Methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine isocyanuric acid adduct, 2,4-diamino-6 Methacryloyloxyethyl-S-triazine / isocyanuric acid adduct, etc.) can be used. These may be used alone or in combination of two or more. As content of the said hardening accelerator, 0.01-15 weight part is preferable with respect to 100 weight part of thermosetting resins.

[Other additive components]
The colored composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity of the composition over time. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.

  Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and methyl ethers thereof, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Organic phosphines, phosphites and the like can be mentioned. The storage stabilizer can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the pigment (A).

  Examples of the adhesion improver include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (amino Ethyl) γ-aminopropyltrie Xisilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-phenyl Examples include silane coupling agents such as aminosilanes such as -γ-aminopropyltriethoxysilane, and thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight with respect to 100 parts by weight of the pigment (A).

[Removal of coarse particles]
The coloring composition of the present invention is mixed with coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm or more and coarse particles by means of centrifugation, sintered filter, membrane filter or the like. It is preferable to remove dust. Thus, it is preferable that the coloring composition for color filters substantially does not contain particles of 0.5 μm or more. More preferably, it is 0.3 μm or less.

[Color filter]
Next, the color filter of the present invention will be described. The color filter of the present invention comprises at least one red filter segment, at least one green filter segment, and at least one blue filter segment, and the at least one red filter segment is for the color filter of the present invention. It is formed using a coloring composition.

  The green filter segment can be formed using a normal green coloring composition. The green coloring composition can be replaced with, for example, C.I. I. Pigment Green 7, 10, 36, 37, 58, and the like. Green coloring compositions include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180 , 181, 182, 185, 187, 188, 193, 194, 198, 199, 213, 214 and the like can be used in combination.

  Moreover, a blue filter segment can be formed using a normal blue coloring composition. The blue coloring composition can be prepared by, for example, C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, and the like. Blue coloring compositions include C.I. I. Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, and other purple pigments can be used in combination.

[Production method of color filter]
The color filter of the present invention can be produced by a printing method or a photolithography method.

(Printing method)
The formation of the filter segment by the printing method can be patterned simply by repeating the printing and drying of the coloring composition prepared as the printing ink. Therefore, the color filter manufacturing method is low in cost and excellent in mass productivity. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.

(Photolithography method)
When forming a filter segment by a photolithography method, a colored composition prepared as a solvent development type or alkali development type colored resist is applied to a transparent substrate by a coating method such as spray coating, spin coating, slit coating, or roll coating. Application is performed so that the dry film thickness is 0.2 to 5 μm. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.

  In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.

  In order to increase the UV exposure sensitivity, after coating and drying the colored resist, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.

  The color filter of the present invention can be produced by an electrodeposition method, a transfer method or the like in addition to the above method, but the color filter coloring composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. . The transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and this filter segment is transferred to a desired substrate.

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples of the present invention. However, the present invention is not limited to the following examples unless it exceeds the gist.
In the examples, “parts” and “%” represent “parts by weight” and “% by weight”, respectively.

  First, a pigment derivative used in Examples and Comparative Examples, an acrylic resin solution, a finer pigment, a green, yellow, blue, and purple pigment dispersion used in color filter production, and a green and blue resist material The manufacturing method will be described.

  Moreover, the fineness of the pigment was evaluated by the specific surface area of the pigment particles. The specific surface area was measured with an automatic vapor adsorption amount measuring apparatus (“BELSORP18” manufactured by Nippon Bell Co., Ltd.) using the BET method of nitrogen adsorption.

  Moreover, the polymerization average molecular weight (Mw) of the acrylic resin was measured by using TSKgel column (manufactured by Tosoh Corporation) and GPC (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector using THF as a developing solvent. It is a weight average molecular weight (Mw) in terms of polystyrene.

<Dye derivative>
Table 1 shows dye derivatives used in Examples and Comparative Examples. These pigment derivatives can be produced by the methods described in, for example, JP-A-3-26767, JP-B-1-34268, JP-B-5-72943, JP-A-2007-314785, and the like. .

<Method for producing acrylic resin solution>
(Preparation of acrylic resin solution)
A reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, and a stirrer was charged with 70.0 parts of cyclohexanone, heated to 80 ° C., and the inside of the reaction vessel was purged with nitrogen. 13.3 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, 4.3 parts of methacrylic acid, 7.4 parts of paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.), A mixture of 0.4 part of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain an acrylic resin solution having a weight average molecular weight of 26000. After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content. The methoxypropyl acetate was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight. Addition to prepare an acrylic resin solution.

<Production method of fine pigment>
(Preparation of red fine pigment)
Diketopyrrolopyrrole red pigment C.I. I. 200 parts of Pigment Red 254 (“IRGAZIN RED 2030” manufactured by Ciba Japan), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. Next, the kneaded product is poured into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight. 190 parts of red fine pigment 1 were obtained. The specific surface area of the red fine pigment was 65 m ² / g.

(Preparation of yellow fine pigment)
Nickel complex yellow pigment C.I. I. Pigment Yellow 150 (“E-4GN” manufactured by LANXESS, specific surface area 100 m ² / g) 200 parts, 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) at 6 ° C. Kneaded for hours. Next, the kneaded product is poured into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight. 190 parts of a yellow fine pigment 1 were obtained. The specific surface area of the yellow fine pigment was 90 m ² / g.

(Production of green fine pigment)
Phthalocyanine green pigment C.I. I. 200 parts of Pigment Green 36 (“Lionol Green 6YK” manufactured by Toyo Ink Manufacturing Co., Ltd.), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. . Next, the kneaded product is poured into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight. 190 parts of a green fine pigment were obtained. The specific surface area of the green fine pigment was 75 m ² / g.

(Preparation of blue fine pigment)
Phthalocyanine blue pigment C.I. I. Pigment Blue 15: 6 (“LIONOL BLUE ES” manufactured by Toyo Ink Manufacturing Co., Ltd.) 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. did. Next, the kneaded product is poured into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight. 190 parts of blue fine pigment 1 were obtained. The specific surface area of the blue fine pigment was 80 m ² / g.

(Production of purple fine pigment)
Dioxazine-based purple pigment C.I. I. Pigment Violet 23 (Toyo Ink Mfg. Co., Ltd. “LIONOGEN VIOLEET RL” 75 m ² / g) 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho), 6 at 80 ° C. Kneaded for hours. Next, the kneaded product is poured into 8 liters of warm water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight. 190 parts of purple fine pigment 1 were obtained. The specific surface area of the purple fine pigment was 95 m ² / g.

<Method for producing green, yellow, blue and purple pigment dispersion>
(Preparation of green pigment dispersion (GP-1))
The following mixture was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then 5.0 μm. And a green pigment dispersion (GP-1) was produced.
Green fine pigment: 11.0 parts (CI Pigment Green 36)
Acrylic resin solution: 40.0 parts propylene glycol monomethyl ether acetate (PGMAC): 48.0 parts Resin type dispersant: 1.0 part ("EFKA4300" manufactured by Ciba Japan)

(Preparation of yellow pigment dispersion (YP-1))
A yellow pigment dispersion (YP-1) was produced in the same manner as the green pigment dispersion (GP-1) except that the green fine pigment was changed to a yellow fine pigment (CI Pigment Yellow 150).

(Preparation of blue pigment dispersion (BP-1))
A blue pigment dispersion (BP-1) was prepared in the same manner as the green pigment dispersion (GP-1) except that the green fine pigment was changed to a blue fine pigment (CI Pigment Blue 15: 6). .

(Preparation of purple pigment dispersion (VP-1))
A purple pigment dispersion (VP-1) was prepared in the same manner as the green pigment dispersion (GP-1) except that the green fine pigment was changed to a purple fine pigment (CI Pigment Violet 23).

<Method for producing green and blue resist materials>
(Preparation of green resist material)
The following mixture was stirred and mixed to be uniform and then filtered through a 1.0 μm filter to obtain a green resist material (G-1).
Green pigment dispersion (GP-1): 35.0 parts Yellow pigment dispersion (YP-1): 9.8 parts Acrylic resin solution: 23.2 parts Trimethylolpropane triacrylate: 1.7 parts (Shin Nakamura Chemical "NK Ester ATMPT")
-2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one: 0.5 part (“Irgacure 907” manufactured by Ciba Japan)
Propylene glycol monomethyl ether acetate: 29.8 parts

(Preparation of blue resist material)
The following mixture was stirred and mixed to be uniform and then filtered through a 1.0 μm filter to obtain a blue resist material (B-1).
Blue pigment dispersion (BP-1): 42.0 parts Purple pigment dispersion (VP-1): 2.8 parts Acrylic resin solution prepared earlier: 23.2 parts Trimethylolpropane triacrylate: 1.7 parts (“NK ESTER ATMPT” manufactured by Shin-Nakamura Chemical Co., Ltd.)
-2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one: 0.5 part (“Irgacure 907” manufactured by Ciba Japan)
Propylene glycol monomethyl ether acetate: 29.8 parts

[Examples 1 to 10, Comparative Examples 1 to 9]
(Preparation of red pigment dispersion (RP-1 to 19))
First, a mixture having a composition (weight ratio) shown in Table 2 was stirred and mixed so as to be uniform, and then using Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm. For 5 hours, and then filtered through a 5.0 μm filter to prepare pigment dispersions (RP-1 to 19). In the table, the parts by weight of the dye derivative with respect to 100 parts by weight of the pigment (A) in each pigment dispersion are also shown.

(* 1) Content of pigment derivative [B1] + [B2] (parts by weight);
Total content of the quinophthalone dye derivative [B1] represented by the general formula (1) and the thiazineindigo dye derivative [B2] represented by the general formula (4) with respect to 100 parts by weight of the pigment (A) (* 2) Content of derivative [B1] (parts by weight);
Content of quinophthalone dye derivative [B1] represented by general formula (1) with respect to 100 parts by weight of pigment (A)

(Example 1; red resist material (R-1))
The following mixture was stirred and mixed to be uniform and then filtered through a 1.0 μm filter to obtain a red resist material (R-1).
-Red pigment dispersion (RP-1): 40.0 parts-Yellow pigment dispersion (YP-1): 4.8 parts-Previously prepared acrylic resin solution: 23.2 parts-Trimethylolpropane triacrylate: 1.7 parts (“NK ESTER ATMPT” manufactured by Shin-Nakamura Chemical Co., Ltd.)
-2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one: 0.5 part (“Irgacure 907” manufactured by Ciba Japan)
Propylene glycol monomethyl ether acetate: 29.8 parts

(Examples 2 to 10, Comparative Examples 1 to 9; red resist material (R-2 to R-19))
As shown in Table 3, except that the red pigment dispersion (RP-1) was changed to red pigment dispersions (RP-2) to (RP-19), it was the same as the red resist material (R-1). Red resist materials (R-2) to (R-19) were obtained.

[Evaluation of resist material (R-1 to 19)]
The color characteristics (brightness) and contrast ratio of the obtained red resist materials (R-1 to 19) were evaluated by the following methods.

(Evaluation of color characteristics)
A resist material was applied on a glass substrate so that x = 0.650 using a C light source, and the substrate was heated at 230 ° C. for 20 minutes. Thereafter, the brightness of the obtained substrate was measured with a microspectrophotometer (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.).

(Evaluation of contrast ratio)
A polarizing plate was placed on both sides of the substrate on which the red colored film was formed, and the ratio of luminance (Lp) when the polarizing plate was parallel and luminance (Lc) when it was orthogonal, Lp / Lc was calculated as the contrast ratio. The luminance was measured using a color luminance meter (“BM-5A” manufactured by Topcon Corporation) under the condition of a 2 ° visual field.
Table 3 shows the evaluation results for the chromaticity and contrast ratio of the resist material.

  As shown in Table 3, the red colored composition and the red colored film of the present invention containing the quinophthalone dye derivative [B1] and the thiazineindigo dye derivative [B2] have high values in brightness and contrast ratio. It can be seen that this is an excellent characteristic.

  In particular, in Examples 1, 3, 5, and 6, since the contents of the quinophthalone dye derivative [B1] and the thiazineindigo dye derivative [B2] are optimum amounts, the brightness is 21.0 or more and the contrast ratio is 4500 or more. And showed very good value.

  On the other hand, the red colored composition and the red colored film obtained in Comparative Examples 1 to 6 and Comparative Examples 8 to 9 containing either the quinophthalone dye derivative [B1] or the thiazineindigo dye derivative [B2]. Thus, it can be seen that the characteristic balance is poor, and high brightness and high contrast ratio cannot be achieved at the same time. In Comparative Example 7, although the contrast ratio shows a high value, since it contains a diketopyrrolopyrrole pigment derivative, the brightness is poor.

[Examples 11 to 20, Comparative Examples 10 to 18]
A color filter was produced using the obtained resist material.

Example 11 Color Filter (CF-1)
A black matrix is patterned on a glass substrate, and red resist material (R-1) is applied to the substrate with a spin coater in a C light source (hereinafter also used for green and blue) x = 0.650, y = 0. The film was applied to a film thickness of 330 to form a colored film. The coating was irradiated with 300 mJ / cm ² of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp. Next, spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water. The substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed. By the same method, the green resist material is made to have a film thickness such that x = 0.300 and y = 0.600, and the blue resist material is so made that x = 0.150 and y = 0.06. Each was applied to form a green filter segment and a blue filter segment to obtain a color filter (CF-1).

(Production of liquid crystal display device)
A transparent ITO electrode layer was formed on the obtained color filter, and a polyimide alignment layer was formed thereon. A polarizing plate was formed on the other surface of this glass substrate. On the other hand, a TFT array and a pixel electrode were formed on one surface of another (second) glass substrate, and a polarizing plate was formed on the other surface. The two glass substrates prepared in this way are arranged facing each other so that the electrode layers face each other, and are aligned using spacer beads while keeping the distance between the two substrates constant, and an opening for injecting a liquid crystal composition The periphery was sealed with a sealant so as to leave After injecting the liquid crystal composition from the opening, the opening was sealed. The liquid crystal display device thus produced was combined with a backlight unit to obtain a liquid crystal panel.

(Examples 12 to 20, Comparative Examples 10 to 18: Color filter (CF-2 to 19))
Hereinafter, a color filter (CF-2 to 19) and a liquid crystal display device were produced in the same manner as the color filter (CF-1) except that the resist material was changed to the resist material shown in Table 4.

[Evaluation of color filters (CF-1 to 19)]
Thereafter, in the obtained liquid crystal display device, a light source is emitted to display a color image, and the brightness of the red, green, and blue filter segment portions is measured with a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) The brightness of white display in the color filter was obtained from the obtained brightness. The results are shown in Table 4.

High brightness was obtained for any color filter comprising a red filter segment formed from the red coloring composition for color filters of the present invention.

  From the above, by using the quinophthalone dye derivative [B1] and the thiazineindigo dye derivative [B2] of the present invention, a red coloring composition for a color filter excellent in both color characteristics (brightness) and contrast ratio, It became possible to obtain a color filter.

Claims (5)

A coloring composition containing a pigment (A) containing a diketopyrrolopyrrole red pigment, a dye derivative (B), a resin (C), and a solvent (D),
The color filter, wherein the dye derivative (B) includes a quinophthalone dye derivative [B1] represented by the general formula (1) and a thiazineindigo dye derivative [B2] represented by the general formula (4) Red coloring composition.
General formula (1)

[In general formula (1), Q represents a quinophthalone residue which may have a substituent,
X _{1 is, -NR'SO 2 -, - SO 2} NR '-, - CONR' -, - CH 2 NR'COCH 2 NR'- or -NR'CO- represents a group selected from, X ₂ is substituted Represents a group selected from an arylene group having 20 or less carbon atoms, or an arylene group having a carbon number of 20 or less or a heteroaromatic ring having 20 or less carbon atoms (these groups are represented by —NR ′ And may be bonded to each other by a divalent linking group selected from —, —O—, —SO ₂ — or —CO—.), X ₃ represents —NR′— or —O—, ( However, R ′ may have a hydrogen atom, a substituent, may have an alkyl group having 20 or less carbon atoms, may have a substituent, and has an alkenyl group or substituent having 20 or less carbon atoms. And represents an aryl group having 20 or less carbon atoms), A and B are each independently represented by the following general formula (2). Groups properly represented by the general formula _{(3), -O- (CH 2} ) n-R 1, -OR 2, -NR 3 R 4, -Cl, -F , or -X ₃ -X ₂ -X ₁ -R represents a group selected from -Q (R ₁ represents an optionally substituted nitrogen-containing heterocyclic residue, and R ₂ , R ₃ , and R ₄ each independently have a hydrogen atom or a substituent. May represent an alkyl group having 20 or less carbon atoms, may have a substituent, may have an alkenyl group having 20 or less carbon atoms, or may have a substituent, and represents an aryl group having 20 or less carbon atoms, n represents an integer of 0 to 20.) is one of a and B, groups represented by the following general formula (2) or _{(3), -O- (CH 2} ) n-R 8, -OR ₉ or —NR ₁₀ R ₁₁ , and t represents an integer of 1 to 3. ]
General formula (2)

[In General Formula (2), Y ₁ represents —NR′— or —O—, and Y ₂ may have a substituent, an alkylene group having 20 or less carbon atoms, or a substituent. Or a group selected from an alkenylene group having 20 or less carbon atoms or an arylene group having 20 or less carbon atoms which may have a substituent (these groups are represented by —NR′—, —O—, And may be bonded to each other by a divalent linking group selected from —SO ₂ — or —CO—, wherein R ′ represents the one defined by the general formula (1)), R ₅ and R ₆ each independently has a substituent, may have an alkyl group having 20 or less carbon atoms, or may have a substituent and may represent an alkenyl group having 20 or less carbon atoms (R ₅ and R ₆ together, a further nitrogen atom, an oxygen atom or containing a sulfur atom optionally substituted heterocyclic May be formed in the concrete.). ]
General formula (3)

[In General Formula (3), Z ₁ represents a single bond connecting a triazine ring and a nitrogen atom, —NR′—, —NR′—G—CO—, —NR′—G—CONR ″ —, —NR ′. —G—SO ₂ —, —NR′—G—SO ₂ NR ″ —, —O—G—CO—, —O—G—CONR′—, —O—G—SO ₂ —, or —O—. G—SO ₂ NR′— (G represents an alkylene group which may have a substituent and which has 20 or less carbon atoms, an alkenylene group which may have a substituent and which has 20 or less carbon atoms, or a substituent; An arylene group having 20 or less carbon atoms which may have a group, and R ′ and R ″ each independently have a hydrogen atom or a substituent and may have an alkyl group having 20 or less carbon atoms. An alkenyl group having 20 or less carbon atoms or a substituent, which may have a group or a substituent, or an aryl group having 20 or less carbon atoms ), R ₇ , R ₈ , R ₉ , and R ₁₀ may each independently have a hydrogen atom, a substituent, or an alkyl group having 20 or less carbon atoms, or a substituent. An alkenyl group having a carbon number of 20 or less or an aryl group having a carbon number of 20 or less which may have a substituent, and R ₁₁ may have a substituent and an alkyl group having a carbon number of 20 or less; Alternatively, it may have a substituent and represents an alkenyl group having 20 or less carbon atoms. ). ]
General formula (4)

[In General Formula (4), R ₁₂ and R ₁₃ each independently form an aromatic or aliphatic carbocycle or heterocycle which may have a substituent other _than- (E) _p group. Represents a group necessary for the purpose. E independently represents the following general formula (5) or the following general formula (6). q represents the integer of 1-6. ]
General formula (5)

General formula (6)

[In General Formula (5), R ₁₄ and R ₁₅ are each independently an alkyl group having 1 to 30 carbon atoms which may have a substituent or an optionally substituted alkyl group having 2 to 2 carbon atoms. 30 represents an alkenyl group, and R ₁₄ and R ₁₅ may form an optionally substituted heterocyclic ring containing a nitrogen, oxygen or sulfur atom. X is, -S -, - O -, - SO 2 -, - CO -, - SO 2 NR -, - NRSO 2 -, - CONR -, - CH 2 NRCOCH 2 NR- , or - (CH _{2) m} NH -(Wherein m represents an integer of 1 to 10. R independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent. An alkenyl group having 2 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent). a represents 0 or 1; Y is an optionally substituted alkylene group having 1 to 20 carbon atoms, an optionally substituted alkenylene group having 2 to 20 carbon atoms, and an optionally substituted carbon number. 6-20 arylene group or a nitrogen, oxygen or (these groups representing a heterocyclic ring which may be substituted containing a sulfur atom may be combined two or more, -NR -, - O -, - SO 2 And may be bonded to each other through a divalent linking group selected from-, -CO- and -CONH-, wherein R is as defined above. b represents 0 or 1. In General Formula (6), R _{16 to} R ₁₉ are each independently an alkyl group having 1 to 30 carbon atoms which may have a substituent, or 2 to 30 carbon atoms which may have a substituent. An alkenyl group or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ₂₀ represents a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkenyl group having 2 to 20 carbon atoms. Z _{is, -CH 2 NR'COCH 2 NR '-} , - CH 2 NR'COCH 2 NR'-G -, - NR' -, - NR'-G-CO -, - NR'-G-CONR'- _{, -NR'-G-SO 2 -} , - NR'-G-SO 2 NR '-, - O-G-CO -, - O-G-CONR' -, - SO 2 -, - O-G- Represents SO ₂ — or —O—G—SO ₂ NR′— (G represents an alkylene group having 1 to 20 carbon atoms which may have a substituent, and the carbon number which may have a substituent. Represents a 2-20 alkenylene group or an arylene group having 6 to 20 carbon atoms which may have a substituent, and R ′ represents a hydrogen atom, an optionally substituted alkyl having 20 or less carbon atoms. A alkenyl group having 20 or less carbon atoms or a substituent, which may have a group or a substituent, or an aryl group having 20 or less carbon atoms. d represents 0 or 1. ]   The total content of the quinophthalone dye derivative [B1] represented by the general formula (1) and the thiazineindigo dye derivative [B2] represented by the general formula (4) is 25 with respect to 100 parts by weight of the pigment (A). The red coloring composition for a color filter according to claim 1, characterized in that it is ˜43 parts by weight.   The content of the quinophthalone dye derivative [B1] represented by the general formula (1) is 13 to 20 parts by weight with respect to 100 parts by weight of the pigment (A). A red coloring composition for a color filter.   The red coloring composition for a color filter according to any one of claims 1 to 3, further comprising an active energy ray-curable monomer (E) and a photopolymerization initiator (F).   A color filter comprising a red filter segment formed from the red coloring composition for a color filter according to claim 1.

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