JP6975579B2 - A colored photosensitive resin composition, a color filter, and an image display device provided with the color filter. - Google Patents

Description

The present invention relates to a colored photosensitive resin composition, a color filter, and an image display device provided with the same.

Color filters are widely used in image sensors, liquid crystal displays, and the like, and their application range is rapidly expanding. Color filters used in color liquid crystal displays and image pickup devices are usually spin-coated with a colored photosensitive resin composition containing colorants corresponding to each of the red, green, and blue colors on a substrate on which a black matrix pattern is formed. The coating film formed by heating and drying (hereinafter, also referred to as pre-baking) is exposed and developed, and further heat-cured (hereinafter, also referred to as post-baking) as necessary. It is manufactured by repeating the operation for each color to form pixels of each color.

The colored photosensitive resin composition is a photosensitive resin composition that is colored by containing a colorant, and is useful as a material for forming a coloring pattern constituting a color filter. Here, the color filter is an optical element built in a color liquid crystal display device and used to colorize a displayed image, or built in an image pickup element and used to obtain a color image.

Further, in order to save power in a color liquid crystal display, a color filter having higher brightness is required. Generally, the thinner the film thickness of a color filter, the higher the brightness tends to be. At this time, in order to secure a high degree of color reproduction, it is necessary to realize a high pigment concentration. However, increasing the concentration of the pigment lowers the storage stability and coatability of the resist composition, which makes it difficult to manufacture a color filter having sufficient performance.

The application of dyes is being studied to achieve these. However, in general, there are many problems that the reliability and the contrast are lowered as compared with the case where the pigment is applied.

Republic of Korea Publication No. 10-2015-0101934 relates to a coloring composition containing a colorant and a polymerizable compound, and is heat-resistant by containing a polymer having a portion where the colorant emits fluorescence and a portion where the colorant absorbs the corresponding fluorescence. It is possible to provide a coloring composition having excellent properties and suitable for forming a high-contrast colored cured film.

Republic of Korea Publication No. 10-2014-0115990 is a coloring composition containing a colorant containing at least one compound selected from the group consisting of a xanthene compound, a polymethine compound, a coumarin compound and a perylene compound, a binder resin and a polymerizable compound. The present invention relates to a coloring composition further containing a transition metal compound, and can provide a coloring composition preferable for forming a colored cured film having high contrast.

However, the above-mentioned prior art may be disadvantageous in brightness and reliability due to the color peculiar to the transition metal or anthraquinone.

Republic of Korea Published Patent No. 10-2015-0101934 (2015.09.04. JSR Corporation) Republic of Korea Published Patent No. 10-2014-0115990 (2014.10.01. JSR Corporation)

The present invention is for solving the above-mentioned problems, and by including a compound represented by a specific chemical formula, it is highly reliable and highly reliable when applied to a color filter and an image display device equipped with the color filter. An object of the present invention is to provide a colored photosensitive resin composition exhibiting contrast characteristics.

The colored photosensitive resin composition according to an embodiment of the present invention for achieving the above object is characterized by containing a compound represented by the following chemical formula 1.

[Chemical formula 1]

As described above, the colored photosensitive resin composition according to the present invention contains a compound represented by a specific chemical formula, so that it is highly reliable without reducing the brightness when applied to a color filter and an image display device provided with the color filter. It has the effect of exhibiting sex and high contrast characteristics.

The color filter produced by the colored photosensitive resin composition and the image display device including the color filter have an excellent effect of sensitivity.

Hereinafter, the present invention will be described in detail.

<Colored photosensitive resin composition>
The colored photosensitive resin composition according to the present invention contains a compound represented by the following chemical formula 1.

At this time, since the compound having the structure of the following chemical formula 1 is hardly absorbed in the visible light region (380 to 780 nm), by expressing white color, when applied to a color filter and an image display device equipped with the color filter, a transmission spectrum is obtained. It is possible to exhibit high reliability and high contrast characteristics without giving a decrease in brightness due to the influence of.

前記化学式１において、
（Ｘ^＋）は下記の化学式２〜化学式４で表現され、
ｎは１〜１０であり、
（Ｙ）^ｍ−はタングステン、モリブデン、ケイ素およびリンからなる群から選択される少なくとも１個の元素と酸素原子を有する陰イオン化合物である。 [Chemical formula 1]

In the chemical formula 1,
(X ⁺ ) is expressed by the following chemical formulas 2 to 4 and
n is 1 to 10
(Y) ^m- is an anionic compound having at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and an oxygen atom.

On the other hand, when the anionic compound is a heteropolyacid or an anion of an isopolyacid containing tungsten as an essential element, it contains anions of phosphotungsten acid, silicotungsten acid and a tungsten-based isopolyic acid, for example, kegin-type lintungsten. Acid ion α- [PW ₁₂ O ₄₀ ] _3- , Dawson type phosphotungsten acid ion α- [P ₂ W ₁₈ O ₆₂ ] ^6- , β- [P ₂ W ₁₈ O ₆₂ ] ^6- , Kegin type kaetung acid Ions α- [SiW ₁₂ O ₄₀ ] ^4- , β- [SiW ₁₂ O ₄₀ ] ^4- , γ- [SiW ₁₂ O ₄₀ ] ^4- , and [P ₂ W ₁₇ O ₆₁ ] ^10- , [P ₂ W ₁₅ O ₅₆ ] ^12- , [H ₂ P ₂ W ₁₂ O ₄₈ ] ^12- , [NaP ₅ W ₃₀ O ₁₁₀ ] ^14- , α- [SiW ₉ O ₃₄ ] ^10- , γ- [SiW ₁₀ O ₃₆ ] ^8- , α- [SiW ₁₁ O ₃₉ ] ^8- , β- [SiW ₁₁ O ₃₉ ] ^8- , [W ₆ O ₁₉ ] ^2- , [W ₁₀ O ₃₂ ] ^4- , [WO ₄ ] ^2- and It can be a mixture of these.

前記化学式２において、
Ｚは炭素、窒素、硫黄、リンまたはヨードであり、
Ｒ_１、Ｒ_２、Ｒ_３およびＲ_４は水素や、ハロゲン原子、炭素数１〜３０の１価または２価で置換または非置換された炭化水素基であり、
前記炭化水素基を構成する−ＣＨ_２−は炭素が酸素原子、硫黄原子、アミノ基またはカルボニル基に転換されるか、前記炭化水素基に含まれた水素原子はハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基に転換されるか、エポキシ、アクリレートの反応基を含むか；
アルキル、ハロゲン、ＣＮ、ＯＲ_１６、ＳＲ_１７、カルボニル基、スルホン酸基およびＮＲ_１８Ｒ_１９からなるグループから選択された一つ以上の置換基によって置換され得るフェニルまたは芳香族炭化水素から選択されるものであり得、
Ｒ_１６、Ｒ_１７、Ｒ_１８およびＲ_１９は水素や、ハロゲン原子、炭素数１〜３０の１価または２価の炭化水素基であり、
前記炭化水素基を構成する−ＣＨ_２−は炭素が酸素原子、硫黄原子、アミノ基またはカルボニル基に転換されるか、前記炭化水素基に含まれた水素原子はハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基に転換されるか、エポキシ、アクリレートの反応基を含むか；
炭素数１〜３０のアルケニルであるか、ハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基のグループから選択された一つ以上の置換基を含んだフェニルまたは芳香族炭化水素基を含み、
Ｒ_１およびＲ_４は結合して５〜７員環の窒素含有ヘテロ環を形成するか、シクロアルキルであり得る。
ｎは０〜５である。 [Chemical formula 2]

In the chemical formula 2,
Z is carbon, nitrogen, sulfur, phosphorus or iodine,
R ₁ , R ₂ , R ₃ and R ₄ are hydrogen, halogen atoms, monovalent or divalently substituted hydrocarbon groups having 1 to 30 carbon atoms, and are substituted or unsubstituted hydrocarbon groups.
_{In -CH 2-} constituting the hydrocarbon group, carbon is converted into an oxygen atom, a sulfur atom, an amino group or a carbonyl group, or the hydrogen atom contained in the hydrocarbon group is a halogen atom, a cyano group or a nitro group. , Conversion to carbonyl group, sulfonic acid group, -SO ₃ M-CO ₂ M, hydroxy group, formyl group or amino group, or containing epoxy, acrylate reactive groups;
Selected from phenyl or aromatic hydrocarbons that can be substituted with one or more substituents selected from the group consisting of alkyl, halogen, CN, OR ₁₆ , SR ₁₇ , carbonyl group, sulfonic acid group and NR ₁₈ R _19. Can be a thing,
R ₁₆ , R ₁₇ , R ₁₈ and R ₁₉ are hydrogen, halogen atoms, and monovalent or divalent hydrocarbon groups having 1 to 30 carbon atoms.
_{In -CH 2-} constituting the hydrocarbon group, carbon is converted into an oxygen atom, a sulfur atom, an amino group or a carbonyl group, or the hydrogen atom contained in the hydrocarbon group is a halogen atom, a cyano group or a nitro group. , Conversion to carbonyl group, sulfonic acid group, -SO ₃ M-CO ₂ M, hydroxy group, formyl group or amino group, or containing epoxy, acrylate reactive groups;
Or an alkenyl of 1 to 30 carbon atoms, a halogen atom, a cyano group, a nitro group, a carbonyl group, a sulfonic acid _{group, -SO 3 M-CO 2 M} , hydroxy group, selected from the group of a formyl group or an amino group Contains phenyl or aromatic hydrocarbon groups containing one or more substituents,
R ₁ and R ₄ can be combined to form a 5-7 membered nitrogen-containing heterocycle or can be cycloalkyl.
n is 0 to 5.

The specific compound of the chemical formula 2 can be expressed as follows.

前記化学式３において、
Ｌは炭素または窒素であり、
Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_９およびＲ_１０は水素や、ハロゲン原子、炭素数１〜３０の１価または２価で置換または非置換された炭化水素基であり、
前記炭化水素基を構成する−ＣＨ_２−は炭素が酸素原子、硫黄原子、アミノ基またはカルボニル基に転換されるか、前記炭化水素基に含まれた水素原子はハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基に転換されるか、エポキシ、アクリレートの反応基を含むか；
アルキル、ハロゲン、ＣＮ、ＯＲ_１６、ＳＲ_１７、カルボニル基、スルホン酸基およびＮＲ_１８Ｒ_１９からなるグループから選択された一つ以上の置換基によって置換され得るフェニルまたは芳香族炭化水素から選択されるものであり得、
Ｒ_１６、Ｒ_１７、Ｒ_１８およびＲ_１９は水素や、ハロゲン原子、炭素数１〜３０の１価または２価の炭化水素基であり、
前記炭化水素基を構成する−ＣＨ_２−は炭素が酸素原子、硫黄原子、アミノ基またはカルボニル基に転換されるか、前記炭化水素基に含まれた水素原子はハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基に転換されるか、エポキシ、アクリレートの反応基を含むか；
炭素数１〜３０のアルケニルであるか、ハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基のグループから選択された一つ以上の置換基を含んだフェニルまたは芳香族炭化水素基を含み、
Ｒ_６およびＲ_７は結合して５〜７員環の窒素含有ヘテロ環を形成するか、シクロアルキルであり得、
ｎは０〜５である。 [Chemical formula 3]

In the chemical formula 3,
L is carbon or nitrogen,
R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are hydrogen, halogen atoms, monovalent or divalently substituted hydrocarbon groups having 1 to 30 carbon atoms, and are substituted or unsubstituted hydrocarbon groups.
_{In -CH 2-} constituting the hydrocarbon group, carbon is converted into an oxygen atom, a sulfur atom, an amino group or a carbonyl group, or the hydrogen atom contained in the hydrocarbon group is a halogen atom, a cyano group or a nitro group. , Conversion to carbonyl group, sulfonic acid group, -SO ₃ M-CO ₂ M, hydroxy group, formyl group or amino group, or containing epoxy, acrylate reactive groups;
Selected from phenyl or aromatic hydrocarbons that can be substituted with one or more substituents selected from the group consisting of alkyl, halogen, CN, OR ₁₆ , SR ₁₇ , carbonyl group, sulfonic acid group and NR ₁₈ R _19. Can be a thing,
R ₁₆ , R ₁₇ , R ₁₈ and R ₁₉ are hydrogen, halogen atoms, and monovalent or divalent hydrocarbon groups having 1 to 30 carbon atoms.
_{In -CH 2-} constituting the hydrocarbon group, carbon is converted into an oxygen atom, a sulfur atom, an amino group or a carbonyl group, or the hydrogen atom contained in the hydrocarbon group is a halogen atom, a cyano group or a nitro group. , Conversion to carbonyl group, sulfonic acid group, -SO ₃ M-CO ₂ M, hydroxy group, formyl group or amino group, or containing epoxy, acrylate reactive groups;
Or an alkenyl of 1 to 30 carbon atoms, a halogen atom, a cyano group, a nitro group, a carbonyl group, a sulfonic acid _{group, -SO 3 M-CO 2 M} , hydroxy group, selected from the group of a formyl group or an amino group Contains phenyl or aromatic hydrocarbon groups containing one or more substituents,
R ₆ and R ₇ can be combined to form a 5-7 membered nitrogen-containing heterocycle or can be cycloalkyl.
n is 0 to 5.

The specific compound of the chemical formula 3 can be expressed as follows.

前記化学式４において、
Ｌは炭素、窒素または硫黄であり、
Ｒ_１１、Ｒ_１２、Ｒ_１３、Ｒ_１４およびＲ_１５は水素や、ハロゲン原子、炭素数１〜３０の１価または２価で置換または非置換された炭化水素基であり、
前記炭化水素基を構成する−ＣＨ_２−は炭素が酸素原子、硫黄原子、アミノ基またはカルボニル基に転換されるか、前記炭化水素基に含まれた水素原子はハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基に転換されるか、エポキシ、アクリレートの反応基を含むか；
アルキル、ハロゲン、ＣＮ、ＯＲ_１６、ＳＲ_１７、カルボニル基、スルホン酸基およびＮＲ_１８Ｒ_１９からなるグループから選択された一つ以上の置換基によって置換され得るフェニルまたは芳香族炭化水素から選択されるものであり得、
Ｒ_１６、Ｒ_１７、Ｒ_１８およびＲ_１９は水素や、ハロゲン原子、炭素数１〜３０の１価または２価の炭化水素基であり、
前記炭化水素基を構成する−ＣＨ_２−は炭素が酸素原子、硫黄原子、アミノ基またはカルボニル基に転換されるか、前記炭化水素基に含まれた水素原子はハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基に転換されるか、エポキシ、アクリレートの反応基を含むか；
炭素数１〜３０のアルケニルであるか、ハロゲン原子、シアノ基、ニトロ基、カルボニル基、スルホン酸基、−ＳＯ_３Ｍ−ＣＯ_２Ｍ、ヒドロキシ基、ホルミル基またはアミノ基のグループから選択された一つ以上の置換基を含んだフェニルまたは芳香族炭化水素基を含み、
Ｒ_１４およびＲ_１５は結合して５〜７員環の窒素含有ヘテロ環を形成するか、シクロアルキルであり得、
ｎは０〜５である。 [Chemical formula 4]

In the chemical formula 4,
L is carbon, nitrogen or sulfur,
R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ and R ₁₅ are hydrogen, halogen atoms, monovalent or divalently substituted hydrocarbon groups having 1 to 30 carbon atoms, and are substituted or unsubstituted hydrocarbon groups.
_{In -CH 2-} constituting the hydrocarbon group, carbon is converted into an oxygen atom, a sulfur atom, an amino group or a carbonyl group, or the hydrogen atom contained in the hydrocarbon group is a halogen atom, a cyano group or a nitro group. , Conversion to carbonyl group, sulfonic acid group, -SO ₃ M-CO ₂ M, hydroxy group, formyl group or amino group, or containing epoxy, acrylate reactive groups;
Selected from phenyl or aromatic hydrocarbons that can be substituted with one or more substituents selected from the group consisting of alkyl, halogen, CN, OR ₁₆ , SR ₁₇ , carbonyl group, sulfonic acid group and NR ₁₈ R _19. Can be a thing,
R ₁₆ , R ₁₇ , R ₁₈ and R ₁₉ are hydrogen, halogen atoms, and monovalent or divalent hydrocarbon groups having 1 to 30 carbon atoms.
_{In -CH 2-} constituting the hydrocarbon group, carbon is converted into an oxygen atom, a sulfur atom, an amino group or a carbonyl group, or the hydrogen atom contained in the hydrocarbon group is a halogen atom, a cyano group or a nitro group. , Conversion to carbonyl group, sulfonic acid group, -SO ₃ M-CO ₂ M, hydroxy group, formyl group or amino group, or containing epoxy, acrylate reactive groups;
Or an alkenyl of 1 to 30 carbon atoms, a halogen atom, a cyano group, a nitro group, a carbonyl group, a sulfonic acid _{group, -SO 3 M-CO 2 M} , hydroxy group, selected from the group of a formyl group or an amino group Contains phenyl or aromatic hydrocarbon groups containing one or more substituents,
R ₁₄ and R ₁₅ can be combined to form a 5-7 membered nitrogen-containing heterocycle or can be cycloalkyl.
n is 0 to 5.

The specific compound of the chemical formula 4 can be expressed as follows.

Further, the colored photosensitive resin composition according to the present invention may further contain one or more of a colorant, a binder resin, a photopolymerizable compound, a photopolymerization initiator and a solvent.

The colorants include dyes and color pigments.

The dyes are used in Color Index [The Society of Dyers and Colorists Publishing] as Solvent, Acid, Basic, reactive, Direct, and Disperse. ) Or dyes classified as Vat. More specifically, the dyes having the following Color Intex (CI) numbers can be mentioned, but the dyes are not limited thereto.

C. I. Solvent Yellow 25, 79, 81, 82, 83, 89;
C. I. Acid Yellow 7, 23, 25, 42, 65, 76;
C. I. Reactive Yellow 2,76,116;
C. I. Direct Yellow 4, 28, 44, 86, 132;
C. I. Disperse Yellow 54, 76;
C. I. Solvent Orange 41, 54, 56, 99;
C. I. Acid Orange 56, 74, 95, 108, 149, 162;
C. I. Reactive orange 16;
C. I. Direct Orange 26;
C. I. Solvent Red 24,49,90,91,118,119,122,124,125,127,130,132,160,218;
C. I. Acid Red 73, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 102;
C. I. Solvent Green 1, 5;
C. I. Acid Green 3, 5, 9, 25, 28;
C. I. Basic green 1;
C. I. Bat green 1 etc.

Further, the coloring pigment is not particularly limited, and a known coloring pigment can be used, and examples thereof include coloring pigments classified as pigments in the Color Index (The Society of Dyers and Colorists Publishing).

Examples of the coloring pigment include C.I. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 269, etc. Pigment; C.I. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 16, 60 and other blue pigments; C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet pigments; C.I. I. Pigment Orange 13,31,38,41,42,43,51,55,59,61,64,65,71,73 and other orange pigments; I. Pigment Green 7, 19, 21, 26, 36, 58, 59 and the like can be mentioned. Examples of the coloring pigment include C.I. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet pigments; C.I. I. Pigment Green 7, 36, 58, 59 and other green pigments are preferred, with C.I. I. Pigment Blue 15: 3, 15: 6, C.I. I. Pigment Violet 23 and C.I. I. Pigment Greens 7 and 58 are more preferred, and C.I. I. Pigment Blue 15: 6 and C.I. I. Pigment Green 7 is even more preferred. By including the coloring pigment, it is easy to optimize the transmission spectrum, and the light resistance and chemical resistance of the color filter are improved.

Colored pigments are atomized by rosin treatment, surface treatment using a pigment derivative having an acidic group or a basic group introduced, graft treatment to the pigment surface with a polymer compound, or sulfuric acid atomization method, if necessary. Treatment, cleaning treatment with an organic solvent or water for removing impurities, removal treatment with an ion exchange method for ionic impurities, or the like may be performed.

The binder resin usually has reactivity and alkali solubility due to the action of light and heat, and acts as a dispersion medium for a coloring material.

Examples of the binder resin include a carboxyl group-containing monomer and a copolymer with another monomer copolymerizable with this monomer. Examples of the carboxyl group-containing monomer include unsaturated carboxylic acids such as unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, and unsaturated polycarboxylic acids having one or more carboxyl groups among molecules such as unsaturated dicarboxylic acids and unsaturated tricarboxylic acids. Acids and the like can be mentioned.

Here, examples of the unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid. Examples of the unsaturated dicarboxylic acid include maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid. The unsaturated polyvalent carboxylic acid can be an acid anhydride, and specific examples thereof include maleic acid anhydride, itaconic acid anhydride, and citraconic acid anhydride.

The unsaturated polyvalent carboxylic acid can be a mono (2-methacryloyloxyalkyl) ester thereof, for example, succinic acid mono (2-acryloyloxyethyl), succinic acid mono (2-methacryloyloxyethyl), phthalic acid mono (2-methacryloyloxyethyl). 2-acryloyloxyethyl), monophthalate (2-methacryloyloxyethyl) and the like can be mentioned. The unsaturated polyvalent carboxylic acid can be a mono (meth) acrylate of the dicarboxypolymer at both ends, and examples thereof include ω-carboxypolycaprolactone monoacrylate and ω-carboxypolycaprolactone monomethacrylate. These carboxyl group-containing monomers can be used alone or in admixture of two or more. Examples of other monomers copolymerizable with the carboxyl group-containing monomer include styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, and o-. Methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzylmethyl ether, p-vinylbenzylmethyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p- Aromatic vinyl compounds such as vinylbenzyl glycidyl ether and inden; methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, i-propyl methacrylate, n- Butyl acrylate, n-butyl methacrylate, i-butyl acrylate, i-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-Hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4- Hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, 2-phenoxyethyl Acrylate, 2-phenoxyethyl methacrylate, methoxydiethylene glycol acrylate, methoxydiethylene glycol methacrylate, methoxytriethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate , Isobornyl acrylate, Isobornyl methacrylate, Dicyclopentadienyl acrylate, Dicyclopentadiethyl methacrylate, Adamantyl (meth) acrylate, Norbornyl (meth) acrylate, 2-Hydroxy-3-phenoxypropyl acrylate, 2-hydroxy -3-Saturated carboxylic acid esters such as phenoxypropyl methacrylate, glycerol monoacrylate, glycerol monomethacrylate; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2 -Aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl acrylate, 3-dimethylaminopropyl methacrylate Unsaturated carboxylic acid aminoalkyl esters such as; unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate; vinyl methyl ether , Vinyl ethyl ethers, unsaturated ethers such as allylglycidyl ethers; vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, vinylidene cyanide; acrylamide, methacrylicamide, α-chloroacrylamide, N-2- Unsaturated amides such as hydroxyethyl acrylamide and N-2-hydroxyethyl methacrylate; maleimide, benzylmaleimide, N-phenylmaleimide. Unsaturated imides such as N-cyclohexylmaleimide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene, chloroprene; and polystyrene, polymethylacrylate, polymethylmethacrylate, poly-n-butylacrylate, poly Examples thereof include -n-butyl methacrylate and macromonomers having a monoacryloyl group or a monomethacryloyl group at the end of the polymer molecular chain of polysiloxane. Each of these monomers can be used alone or in combination of two or more. In particular, bulky monomers such as a monomer having a norbornyl skeleton, a monomer having an adamantan skeleton, and a monomer having a rosin skeleton as other monomers copolymerizable with the carboxyl group-containing monomer. Is preferable because it tends to lower the specific dielectric constant value.

The binder resin of the present invention preferably has an acid value in the range of 20 to 200 (KOHmg / g). When the acid value is in the above range, the solubility in the developer is improved, the non-exposed portion is easily dissolved and the sensitivity is increased, and as a result, the pattern of the exposed portion remains during development and the residual film ratio. It is preferable because it improves (film remaining ratio). Here, the acid value is a value measured by the amount of potassium hydroxide (mg) required to neutralize 1 g of the acrylic polymer, and is usually obtained by titration using an aqueous potassium hydroxide solution. be able to.

Further, the polystyrene-equivalent weight average molecular weight (hereinafter, simply referred to as “weight average molecular weight”) measured by gel permeation chromatography (GPC; using tetrahydrofuran as an elution solvent) is 3,000 to 200,000, preferably 5,000. A binder resin having a molecular weight of 100,000 is preferable. When the molecular weight is in the above range, the hardness of the coating film is improved, the residual film ratio is high, the solubility of the non-exposed portion in the developing solution is excellent, and the resolution tends to be improved, which is preferable.

The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the binder resin is preferably 1.5 to 6.0, more preferably 1.8 to 4.0. When the molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] is within the above range, the developability may be excellent.

The content of the binder resin of the present invention is preferably 1 to 60% by weight based on the total solid content by weight in the colored photosensitive resin composition. When the content of the binder resin is within the above range, the solubility in the developing solution is sufficient, so that no development residue is generated on the substrate of the non-pixel portion, and the film of the pixel portion of the exposed portion is reduced during development. Since it does not occur, the non-pixel portion tends to have good dropout.

The photopolymerizable compound is a compound that can be polymerized by the action of light and a photopolymerization initiator described later, and examples thereof include a monofunctional monomer, a bifunctional monomer, and other polyfunctional monomers.

Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone and the like. Can be done.

Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di (meth) acrylate. , Bis (acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di (meth) acrylate and the like.

Specific examples of other polyfunctional monomers include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol penta (meth) acrylate. Examples thereof include pentaerythritol hexa (meth) acrylate. Of these, polyfunctional monomers having two or more functionalities are preferably used.

The photopolymerizable compound is preferably contained in an amount of 5 to 50% by weight, more preferably 7 to 45% by weight, based on the total solid content in the colored photosensitive resin composition. When the content of the photopolymerizable compound is within the above range, the strength and smoothness of the pixel portion can be improved.

The photopolymerization initiator is not limited, but is one or more compounds selected from the group consisting of triazine compounds, acetophenone compounds, non-imidazole compounds and oxime compounds. The photosensitive resin composition containing the photopolymerization initiator has high sensitivity, and the pixel pixels formed by using this composition have good strength and patternability of the pixel portions.

In addition, when a photopolymerization initiator is used in combination with a photopolymerization initiator, the photosensitive resin composition containing them becomes more sensitive, and the productivity when forming a color filter using this composition is improved. preferable.

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-methoxy). Naftil) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) ) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4- Bis (trichloromethyl) -6- [2- (fran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2) -Methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine, etc. Can be mentioned.

Examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl]-. 2-Methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1-( Examples thereof include an oligomer of 4-morpholinophenyl) butane-1-one and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one.

Examples of the non-imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenyl non-imidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4', 5,5'-tetraphenyl non-imidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) non-imidazole, 2,2'-bis (2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) non-imidazole 2-Chlorophenyl) -4,4', 5,5'-tetra (trialkoxyphenyl) non-imidazole, imidazole compounds in which the phenyl group at the 4,4', 5,5' position is replaced by a carboalkoxy group, etc. Can be mentioned. Of these, 2,2'bis (2-chlorophenyl) -4,4', 5,5'-tetraphenyl non-imidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4', 5, 5'-Tetraphenyl non-imidazole is preferably used.

Further, other photopolymerization initiators usually used in this field may be further included as long as the effects of the present invention are not impaired. Examples of other photopolymerization initiators include benzoin-based compounds, benzophenone-based compounds, thioxanthone-based compounds, and anthracene-based compounds. These can be used alone or in combination of two or more.

Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether. Examples of the benzophenone compound include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl). ) Benzophenone, 2,4,6-trimethylbenzophenone, 4,4'-di (N, N'-dimethylamino) -benzophenone and the like. Examples of the thioxanthone compound include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like. Examples of the anthracene-based compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, and 2-ethyl-9,10-diethoxyanthracene. .. In addition, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 10-butyl-2-chloroacrydone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, methylphenylglycoxylate, titanosen compounds, etc. It can be mentioned as another photopolymerization initiator.

Further, as the photopolymerization initiator that can be used in combination with the photopolymerization initiator in the present invention, one or more compounds selected from the group consisting of amine compounds, carboxylic acid compounds and the like can be preferably used.

Specific examples of amine compounds among photopolymerization initiation aids include aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, and 4-. Isoamyl dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler ketone), 4 , 4'-Aromatic amine compounds such as bis (diethylamino) benzophenone can be mentioned. As the amine compound, an aromatic amine compound is preferably used.
The carboxylic acid compound is, for example, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthio. Examples include aromatic heteroacetates such as acetoic acid, dichlorophenylthioacetate, N-phenylglycine, phenoxyacetate, nabutylthioacetate, N-naphthylglycine and naphthoxyacetate.

In the photosensitive resin composition of the present invention, the content of the photopolymerization initiator is preferably 0.1 to 20% by weight based on the total solid content by weight of the photosensitive resin composition, and is preferably 1 to 10% by weight. It is more preferable that it is contained in. When the amount of the photopolymerization initiator used is within the above range, the photosensitive resin composition is highly sensitive, and the strength of the pixel portion and the smoothness on the surface of the pixel portion are excellent.

The amount of the photopolymerization initiation aid used is preferably 0.1 to 20% by weight, more preferably 1 to 10% by weight, based on the above criteria. When the amount of the photopolymerization initiation assisting agent used is within the above range, the sensitivity efficiency of the photosensitive resin composition is further increased, and the productivity of the color filter formed by using this composition can be improved.

The solvent is not particularly limited, and various organic solvents used in the field of colored photosensitive resin compositions can be used.

Specific examples include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol. Diethylene glycol dialkyl ethers such as dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate and methoxy. Alkylene glycol alkyl ether acetates such as pentylacetate, aromatic hydrocarbons such as benzene, toluene, xylene, methethylene, ketones such as methylethylketone, acetone, methylamylketone, methylisobutylketone, cyclohexanone, ethanol, propanol, butanol, Examples thereof include alcohols such as hexanol, cyclohexanol, ethylene glycol and glycerin, esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as γ-butyrolactone.

In terms of coatability and drying property, the solvent may preferably be an organic solvent having a boiling point of 100 to 200 ° C., and more preferably alkylene glycol alkyl ether acetates, ketones, 3-. Esters such as ethyl ethoxypropionate and methyl 3-methoxypropionate can be mentioned, and more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, 3-methoxy. Examples thereof include methyl propionate. Each of these solvents can be used alone or in combination of two or more.

The content of the solvent in the colored photosensitive resin composition of the present invention is preferably 60 to 90% by weight, more preferably 70 to 85% by weight, based on the total weight% of the colored photosensitive resin composition. preferable. When the content of the solvent is within the above range, the coatability becomes good when applied by a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater), or an inkjet. obtain.

The colored photosensitive resin composition of the present invention may further contain an antioxidant, which may be used alone or in combination of two or more.

These antioxidants can be one selected from the group consisting of benzotriazole-based light stabilizers, triazine-based light stabilizers, benzophenone-based, Halls light stabilizers, and combinations thereof, but are limited thereto. It's not something.

<Color filter>
The present invention provides a color filter containing a coloring pattern produced by the colored photosensitive resin composition. That is, the present invention includes a color filter produced by using the colored photosensitive resin composition. The color filter of the present invention includes a substrate and a coloring pattern produced on the substrate with the colored photosensitive resin composition of the present invention. The substrate is a transparent material, and a material having sufficient strength and bearing capacity for the stability of the color filter can be used. Preferably, glass having excellent chemical stability and high strength can be used. Further septa can be formed between each tinted pattern and a black matrix may be added.

As the method for manufacturing the color filter, a usual method widely known in the art can be used.

<Image display device>
The present invention also provides an image display device including the color filter. Specific examples of the image display device include a liquid crystal display (liquid crystal display device; LCD), an organic EL display (organic EL display device), a liquid crystal projector, a display device for a game machine, a display device for a mobile terminal such as a mobile phone, and a digital display device. Display devices such as a camera display device and a car navigation display device can be mentioned, but the present invention is not limited thereto.

The image display device of the present invention may be manufactured by a method generally known in the technical field of the present invention, except that the image display device of the present invention is provided with the color filter.

Hereinafter, the present invention will be described in more detail through examples. However, the following examples are for more specific explanation of the present invention, and the scope of the present invention is not limited by the following examples. The following examples may be appropriately modified or modified by those skilled in the art within the scope of the present invention. In addition, "%" and "part" indicating the content below are based on weight unless otherwise specified.

Synthesis example 1
A solution in which 30 g of methanol was added to 2 g of Dodecylpyridinium chloride and completely dissolved, and 6 g of Phosphotungstic acid hydrate (Aldrich, P4006) was dissolved in 25 g of water. Slowly drip. After dropping, the mixture is stirred at 25 to 50 ° C. for 4 hours, and then the precipitate is filtered and washed with water. After filtration, it was dried in a vacuum oven at 50 ° C. for 12 hours to obtain 8.5 g of the following chemical formula A-1. (Synthesized with reference to Eur. J. Inorg. Chem. 2014, 21-35.)

[Chemical formula A-1]

Synthesis example 2
Using Tetrapropylammonium Hydroxide (TCI, product number T0171) instead of Dodecylpyridinium chloride, chemical formula A-2 7.3 g was obtained in the same manner as in Synthesis Example 1. ..
[Chemical formula A-2]

Synthesis Example 3: Alkaline-soluble resin B Synthetic stirrer, thermometer reflux cooling tube, dropping lot and nitrogen introduction tube in a flask equipped with 100 g of propylene glycol monomethyl ether acetate, 100 g of propylene glycol monomethyl ether, and the atmosphere in the flask is nitrogen from air. Azobisisobutyronitrile 8.2 g, monomethacrylate of tricyclodecane skeleton (FA-513M manufactured by Hitachi Chemical Co., Ltd.) 3.1 g, 2-ethylhexyl acrylate 55.2 g, 4-methylstyrene 5. 9 g, 85.2 g of glycidyl methacrylate and 6.0 g of n-dodecanothiol are added. Then, the temperature of the reaction solution was raised to 80 ° C. with stirring, and the reaction was carried out for 4 hours.

After lowering the temperature of the reaction solution to room temperature and replacing the atmosphere of the flask from nitrogen to air, 0.2 g of triethylamine, 0.1 g of 4-methoxyphenol and 43.2 g of acrylic acid were added together with 136 g of propylene glycol monomethyl ether acetate from the dropping lot. After dropping over 2 hours, the reaction was carried out at 100 ° C. for 6 hours. After that, the temperature of the reaction solution was lowered to room temperature, 6.0 g of succinic acid anhydride was added, and the reaction was carried out at 80 ° C. for 6 hours.

The acid value of the solid content of the alkali-soluble resin thus synthesized was 36.2 mgKOH / g, the weight average molecular weight Mw measured by GPC was about 7,540, and the Tg was -12 ° C.

The measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the alkali-soluble resin was carried out under the following conditions using the GPC method, and the ratio of the weight average molecular weight and the number average molecular weight obtained at this time was calculated. The molecular weight distribution (Mw / Mn) was used.
Equipment: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG4000HXL + TSK-GELG2000HXL (series connection)
Column temperature: 40 ° C
Moving bed solvent: Tetrahydrofuran Flow rate: 1.0 ml / min Injection amount: 50 μl
Detector: RI
Measurement sample concentration: 0.6% by weight (solvent = tetrahydrofuran)
Calibration standard: TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500 (manufactured by Tosoh Corporation)

Examples 1 to 3 and Comparative Example 1: Production of a colored photosensitive resin composition

Color Filter (Glass Substrate) Production Example A color filter was produced using the colored photosensitive resin compositions produced in Examples 1 to 3 and Comparative Example 1. That is, each of the colored photosensitive resin compositions was applied onto a glass substrate by a spin coating method, and then placed on a heating plate and maintained at a temperature of 100 ° C. for 3 minutes to form a thin film. Subsequently, a test photomask having a pattern that changes the transmittance stepwise in the range of 1 to 100% and a line / space pattern of 1 μm to 50 μm is placed on the thin film, and the distance from the test photomask is 100 μm. And irradiated with ultraviolet rays. ^{At this time, the light source of ultraviolet rays was irradiated with an illuminance of 100 mJ / cm 2} using a 1 KW high-pressure mercury lamp containing all g, h, and i rays, and no special optical filter was used. The thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution developing solution having a pH of 10.5 for 2 minutes for development. The glass plate covered with this thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 220 ° C. for 1 hour to produce a color filter. The film thickness of the color filter produced above was 2.0 μm.

1. 1. Viscosity increase rate of pigment dispersion The initial viscosity (kinematic viscosity) A (mPa · s) of each pigment dispersion immediately after being produced in Examples 1 to 3 and Comparative Example 1 was measured.

Next, the pigment dispersions of Examples 1 to 3 and Comparative Example 1 were left to stand in an environment of 25 ° C. for 1 day immediately after production, and then the viscosity (kinematic viscosity) B (mPa) of each pigment dispersion after standing was left. -S) was measured. The viscosity (kinematic viscosity) of the pigment dispersion was measured in an environment of 25 degrees using an E-type viscometer (trade name: RE-01, product of Donggi Sangyo Co., Ltd.) in accordance with JIS Z8809. .. The thickening rate was calculated by the following formula.

Viscosity thickening rate = (viscosity B after standing) / (initial viscosity A).

The results are shown in Table 2 below, and the initial viscosities of Examples 1 to 3 are shown as relative values when the initial viscosity of the pigment dispersion of Comparative Example 1 is set to the standard (100), and the results are shown in Table 2. ..

2. 2. Measurement of Luminance (Y) The luminance (Y) of the colored glass plates of Examples 1 to 3 and Comparative Example 1 obtained above was measured as follows. A colored glass plate was set in a spectrophotometer (trade name: CM-3700d, a product of Konica Minolta Sensing Co., Ltd.), and the transmitted chromaticity on the X, Y, and Z coordinate axes at a C light source of 2 degrees (°) was measured. .. The Y value at this time was adopted as the luminance (Y). The results are shown in Table 2 below.

In Table 2 below, the luminance values of Examples 1 to 3 are represented by relative values when the luminance of the colored glass plate obtained by using the pigment dispersion of Comparative Example 1 is set as the standard (100), and the results are shown in Table 2. Represented in.

3. 3. Contrast measurement The contrast of the colored glass plate (color filter) after post-baking of Examples 1 to 3 and Comparative Example 1 was measured using a contrast measuring device. Contrast measuring devices include color luminance meter (trade name: LS-100, product of Konica Minolta Sensing Co., Ltd.), lamp (trade name: HF-SL-100WLCG, product of Johnton Sangyo Co., Ltd.) and polarizing plate (trade name: POLAX). -38S, Luceo Products Co., Ltd.).

A polarizing plate was installed on the backlight so that the distance between the polarizing plate (POLAX-38S) and the colored glass plate was 1 mm.

A rotatable polarizing plate was installed on top of it. After confirming that the brightness of the backlight is sufficiently stable, adjust the rotatable polarizing plate installed at the top to the position of the cross Nicol to measure the brightness of the colored glass plate, and then rotate it 90 degrees in parallel. The brightness of the colored glass plate was measured at the position of. The ratio (%) of the two was determined as the contrast.

The results are shown in Table 2 below, and the contrast values of Examples 1 to 3 are shown as relative values when the contrast of the colored glass plate obtained by using the pigment dispersion of Comparative Example 1 is set as the standard (100). The results are shown in Table 2.

4. Heat resistance measurement The heat resistance was evaluated by measuring the color change value (ΔEab) after heating at 230 ° C. for 120 minutes. ΔEab is a value required by the following saturation formula by the CIE 1976 (L ^* , a ^* , b ^{*) spatial color system.} The results are shown in Table 2. (New Color Science Handbook edited by the Japan Color Society (1985) p.266).

△ E ^* ab = {(△ L ^* ) ² + (△ a ^* ) ² + (△ b ^* ) ² } ^1/2

[Heat resistance evaluation criteria]
○: △ ^E * ab value: 3 or less △: △ ^E * ab value: 3 to 10 or less ×: △ ^E * ab value: 10 exceeded

As shown in Table 2, it can be confirmed that the colored photosensitive resin compositions of Examples 1 to 3 in which the compositions are mixed according to the present invention can provide a heat-resistant and high-contrast color filter. ..

Claims (5)

A colored photosensitive resin composition containing a compound represented by the following chemical formula 1:
[Chemical formula 1]

(In the above chemical formula 1,
(X ⁺⁾ is either a compound that will be expressed by the following chemical formula,
n is 1 to 10
(Y) ^m-is an anion compound having a tungsten emission elemental oxygen atom).

The colored photosensitive resin according to claim 1, wherein the colored photosensitive resin composition further contains one or more of a colorant, a binder resin, a photopolymerizable compound, a photopolymerization initiator and a solvent. Composition. The colored photosensitive resin composition according to claim 1, wherein the colored photosensitive resin composition further contains an antioxidant. A color filter produced by the colored photosensitive resin composition according to any one of claims 1 to 3. An image display device comprising the color filter according to claim 4.