Photosensitive colored resin composition, color filter, and image display device

Abstract

The invention provides a photosensitive colored resin composition, a color filter and an image display device, which can improve the color filter yield on the premise that high solid content is considered and the relative total VOC reduction rate in the production process of forming the color filter by the photosensitive colored resin composition is improved at the same time. A colored layer (pattern) prepared from the photosensitive colored resin composition has good brightness and pattern properties. The photosensitive colored resin composition includes a colorant (A) including a dibenzopiperin-based colorant (A-1) represented by formula (I), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E), in which the content of solid content is 18-25 wt% based on 100 wt% of the total weight of the photosensitive colored resin composition.

Description

TECHNICAL FIELD

[0001] The present application relates to a resin composition, a filter, and a display device, and particularly to a photosensitive colored resin composition, a color filter, and an image display device. BACKGROUND

[0002] Image display devices using a color filter can be exemplified by (i) a color liquid crystal display device including a combination of a backlight as a light source, a liquid crystal as an optical shutter, and a color filter having a color adjustment function (a color conversion function, a color separation function, a color correction function, etc.), and (ii) a color organic electroluminescence (EL) display device including a combination of a synthetic white organic electroluminescence (EL) light source and a color filter having a color adjustment function (a color conversion function, a color separation function, a color correction function, etc.). The color filter can also be used for image sensors such as a complementary metal-oxide-semiconductor (CMOS) and a charge-coupled device (CCD).

[0003] Currently, a method for manufacturing a color filter is known as an electro-deposition method, a printing method, and a photolithography method. The electro-deposition method is a method in which a transparent electrode having a predetermined pattern is formed in advance, and a resin containing a pigment is ionized by applying a voltage to be dissolved or dispersed in a solvent to form a pattern. The printing method is a printing method such as offset printing using an ink containing a thermosetting resin or an ultraviolet hardening resin. The photolithography method is a method of using a photosensitive colored resin composition in which a coloring agent such as a pigment or a dye is dispersed or dissolved in a photoresist material. In recent years, the photolithography method is a mainstream method for manufacturing a color filter. The photolithography method is a method of using a photosensitive colored resin composition in which a coloring agent such as a pigment or a dye is dispersed or dissolved in a photoresist material.

[0004] In the case of forming a color filter using the photolithography method, for example, after forming a coating film of a negative photosensitive colored resin composition on a substrate, the coating film is subjected to ultraviolet exposure through a photomask having a predetermined opening pattern, and then, by development, the unexposed portion is dissolved and removed to form a pattern (for example, Patent Document 1).

[0005] In today's society, the importance of ESG (environmental protection (E), social responsibility (S), and corporate governance (G)) issues is increasing, especially the safety of substances that people come into contact with in their daily lives, such as food safety and living environment safety. With the increasing global demand for environmental protection, the emission requirements for volatile organic compounds (VOC) in the chemical and electronic industries are becoming increasingly stringent, and the amount of emissions is strictly regulated. Green environmental protection technology to reduce VOC emissions during the manufacturing process is one of the current major issues. In the production process of color filters, volatile organic compounds can diffuse into the air, which may have negative effects on operators and the environment.

[0006] However, although a manufacturing method for increasing the overall solid content of a photosensitive colored resin composition for color filters to reduce VOC emissions has been developed, this manufacturing method also causes problems such as a decrease in light transmittance of the colored layer (pattern) and pattern abnormalities.

[0007] [Patent Literature]

[0008] [Patent Literature 1] JP H02-144502-A

[0009] Therefore, how to simultaneously consider high solid content and relatively high total VOC reduction rate in the production process of photosensitive colored resin compositions for color filters, while still maintaining good brightness and pattern properties of the colored layer (pattern) is an important issue today. SUMMARY

[0010] The present application provides a photosensitive colored resin composition, a color filter, and an image display device, which can simultaneously consider high solid content and relatively high total VOC reduction rate in the production process of photosensitive colored resin compositions for color filters, while still maintaining good brightness and pattern properties of the colored layer (pattern) formed by the photosensitive colored resin composition.

[0011] The present application provides a photosensitive colored resin composition, comprising: a colorant (A) comprising a dibenzophenanthrene-based colorant (A-1) represented by formula (I), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E), wherein the content of the solid content is 18 wt% to 25 wt% based on the total weight of the photosensitive colored resin composition being 100 wt%.

[0012]

[0013] In formula (I), R 1 , R 2 , R3 , and R 4 each independently represents a hydrogen atom,

[0014] a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20,

[0015] a substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 20,

[0016] a substituted or unsubstituted aromatic hydrocarbon group having a carbon number of 6 to 20, or

[0017] a substituted or unsubstituted heterocyclic group having a carbon number of 2 to 20, or

[0018] R 1 , and R 2 , or R 3 , and R 4 may also be bonded to each other to form a ring;

[0019] R 5 , R 6 , R 7 , R 8 , and R 9 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, -SO3 - , -SO3H, -SO3M, a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20,

[0020] a substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 20,

[0021] a substituted or unsubstituted linear or branched alkoxy group having a carbon number of 1 to 20,

[0022] a substituted or unsubstituted cycloalkoxy group having a carbon number of 3 to 20, or

[0023] a substituted or unsubstituted linear or branched alkenyl group having a carbon number of 2 to 20, or

[0024] R 5 , and R 6 , R 6 , and R 7 , R 7 , and R 8 , or R 8 , and R 9 may also be bonded to each other to form a ring;

[0025] M represents an alkali metal atom;

[0026] R 11 , R 12 , and R 13each independently represents a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20,

[0027] a substituted or unsubstituted linear or branched alkoxy group having a carbon number of 1 to 20,

[0028] a substituted or unsubstituted aromatic hydrocarbon group having a carbon number of 6 to 20,

[0029] a substituted or unsubstituted heterocyclic group having a carbon number of 2 to 20, or

[0030] a polyether structure,

[0031] and at least one of R 11 , R 12 , and R 13 is a polyether structure;

[0032] n represents a positive integer of 1 to 4.

[0033] In one embodiment of the present application, the content of the solid component is 18% by weight to 23% by weight, based on 100% by weight of the total weight of the photosensitive colored resin composition.

[0034] In one embodiment of the present application, the content of the solid component is 18% by weight to 22% by weight, based on 100% by weight of the total weight of the photosensitive colored resin composition.

[0035] In one embodiment of the present application, at least two -SO3 - in the above-described formula (I) are present, and R 9 is -SO3 - , and R 7 is a hydrogen atom or -SO3 - .

[0036] In one embodiment of the present application, in the above-described formula (I), R 11 , R 12 , and R 13 each independently represent a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20, or a polyether structure, and at least one of R 11 , R 12 , and R 13 is a polyether structure.

[0037] In one embodiment of the present application, the diphenalpiperazine-based colorant (A-1) is 0.01% by weight to 25% by weight, based on 100% by weight of the total weight of the solid component of the photosensitive colored resin composition.

[0038] In one embodiment of the present application, the colorant (A) is 1 to 85% by weight, the alkali-soluble resin (B) is 2.5 to 70% by weight, the photopolymerizable compound (C) is 2.5 to 75% by weight, and the photoinitiator (D) is 0.1 to 30% by weight, based on the total weight of the solid components of the photosensitive colored resin composition being 100% by weight.

[0039] The present application provides a color filter made of the photosensitive colored resin composition as described above.

[0040] The present application provides an image display device including the color filter as described above.

[0041] Based on the above, the present application provides a photosensitive colored resin composition, a color filter, and an image display device, which, by limiting the colorant (A) to include a dibenzophenanthroline-based colorant (A-1) represented by formula (I), and limiting the content of the solid components to 18 to 25% by weight, can achieve a colored layer (pattern) made of the photosensitive colored resin composition having good brightness and pattern properties while simultaneously taking into account high solid components and a relative total VOC reduction rate improvement in the production process of the color filter made of the photosensitive colored resin composition, thereby achieving an environmentally friendly effect.

[0042] In order to make the above features and advantages of the present application more apparent, specific examples are provided below and described in detail as follows. BRIEF DESCRIPTION OF DRAWINGS

[0043] Figure 1 is a cross-sectional view of a liquid crystal display device according to one embodiment.

[0044] BRIEF DESCRIPTION OF DRAWINGS

[0045] 10: Liquid crystal display device

[0046] 11: First transparent substrate

[0047] 12: TFT (thin film transistor) array

[0048] 13: Transparent electrode layer

[0049] 14: First alignment layer

[0050] 15: First polarizing plate

[0051] 21: Second transparent substrate

[0052] 22: Color filter

[0053] 23: Second transparent electrode layer

[0054] 24: Second alignment layer

[0055] 25: second polarizing plate

[0056] LC: liquid crystal

[0057] 30: backlight unit

[0058] 31: white LED light source DETAILED DESCRIPTION

[0059] <Photosensitive colored resin composition>

[0060] The present embodiment provides a photosensitive colored resin composition, comprising: a colorant (A) comprising a diphenylporphyrin-based colorant (A-1), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E). In addition, the photosensitive colored resin composition of the present embodiment can optionally comprise an additive (F).

[0061] In the present embodiment, the content of the solid component is 18% to 25% by weight, preferably 18% to 23% by weight, and more preferably 18% to 22% by weight, based on the total weight of the photosensitive colored resin composition being 100% by weight.

[0062] In the present embodiment, the "solid component" of the photosensitive colored resin composition is the component other than the solvent (E); and the "total weight of the solid component of the photosensitive colored resin composition" is the total weight of the component other than the solvent (E).

[0063] In the present embodiment, (meth)acrylic acid represents acrylic acid and / or methacrylic acid, and (meth)acrylate represents acrylate and / or methacrylate.

[0064] On the premise that the colorant (A) comprises the diphenylporphyrin-based colorant (A-1) represented by the following formula (I), when the content of the solid component is controlled in the range of 18% to 25% by weight, the photosensitive colored resin composition can have a colored layer (pattern) produced therefrom with good brightness and pattern properties, while giving consideration to both high solid content and the improvement of the relative total VOC reduction rate in the production process of the photosensitive colored resin composition for forming a color filter.

[0065] On the contrary, on the premise that the colorant (A) comprises the diphenylporphyrin-based colorant (A-1) represented by the following formula (I), when the content of the solid component of the photosensitive colored resin composition is less than 18% by weight, the photosensitive colored resin composition does not have the effect of reducing the total VOC.

[0066] When the content of the solid component is more than 25% by weight, the brightness of the colored layer (pattern) produced from the photosensitive colored resin composition is poor, the pattern properties are poor, and the overall display quality of the image display device produced from the color filter is poor.

[0067] When the photosensitive colored resin composition does not include the dibenzofuran-based colorant (A-1) represented by the following formula (I), the brightness of the colored layer (pattern) produced from the photosensitive colored resin composition is poor, the pattern properties are poor, and the overall display quality of the image display device produced from the color filter is poor.

[0068] When the content of the solid component is 18% to 23% by weight based on the total weight of the photosensitive colored resin composition being 100% by weight, the brightness of the colored layer (pattern) produced from the photosensitive colored resin composition is better, and the pattern properties are better.

[0069] When the content of the solid component is 18% to 22% by weight based on the total weight of the photosensitive colored resin composition being 100% by weight, the brightness of the colored layer (pattern) produced from the photosensitive colored resin composition is better, and the pattern properties are better.

[0070] The following will describe each component of the photosensitive colored resin composition used in the present embodiment in detail:

[0071] Colorant (A)

[0072] The colorant (A) of the present embodiment includes a dibenzofuran-based colorant (A-1). In addition, the colorant (A) can include another colorant (A-2) other than the dibenzofuran-based colorant (A-1).

[0073] Dibenzofuran-based colorant (A-1)

[0074] In the present embodiment, the dibenzofuran-based colorant (A-1) has a structure represented by formula (I).

[0075]

[0076] In formula (I), R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom,

[0077] a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20,

[0078] a substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 20,

[0079] a substituted or unsubstituted aromatic hydrocarbon group having a carbon number of 6 to 20, or

[0080] a substituted or unsubstituted heterocyclic group having a carbon number of 2 to 20, or

[0081] R 1 , or R 2 , or R 3 , or R 4 may also be bonded to each other to form a ring;

[0082] R 5 , R 6 , R 7 , R 8 , and R 9 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, -SO3 - , -SO3H, -SO3M, a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20,

[0083] a substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 20,

[0084] a substituted or unsubstituted linear or branched alkoxy group having a carbon number of 1 to 20,

[0085] a substituted or unsubstituted cycloalkoxy group having a carbon number of 3 to 20, or

[0086] a substituted or unsubstituted linear or branched alkenyl group having a carbon number of 2 to 20, or

[0087] R 5 , R 6 , R 6 , R 7 , R 7 , R 8 , or R 8 , or R 9 may also be bonded to each other to form a ring;

[0088] M represents an alkali metal atom;

[0089] R 11 , R 12 , and R 13 each independently represent a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20,

[0090] a substituted or unsubstituted linear or branched alkoxy group having a carbon number of 1 to 20,

[0091] a substituted or unsubstituted aromatic hydrocarbon group having a carbon number of 6 to 20,

[0092] Substituted or unsubstituted heterocyclic groups with 2 to 20 carbon atoms, or

[0093] Polyether structure,

[0094] And R 11 R 12 and R 13 At least one of them has a polyether structure;

[0095] n represents a positive integer from 1 to 4.

[0096] In equation (I), R is... 1 R 2 R 3 and R 4 The term "substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms in straight or branched form" can be specifically exemplified by: straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, and isooctyl.

[0097] In equation (I), R is... 1 R 2 R 3 and R 4 The term "substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms" can specifically include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and other cycloalkyl groups.

[0098] In equation (I), R is... 1 R 2 R 3 and R 4 The terms "substituted or unsubstituted aromatic hydrocarbon groups with 6 to 20 carbon atoms" or "substituted or unsubstituted heterocyclic groups with 2 to 20 carbon atoms" can specifically include: phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, triphenyl, perylene, indene, fluorenyl, pyridyl, pyrimidinyl, triyl, pyrroloyl, imidazolyl, pyrazolyl, triazolyl, quinolinyl, isoquinolinyl, naphthidyl, indolyl, benzimidazolyl, carbazolyl, carbazolyl, acridineyl, phenolinyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, etc.

[0099] In this embodiment, "aromatic hydrocarbon group" refers to a group containing a monocyclic aromatic hydrocarbon group or a polycyclic condensed polycyclic aromatic group. Also, in this embodiment, "heterocyclic group" refers to a monocyclic or polycyclic heterocyclic group, representing a nitrogen-, oxygen-, or sulfur-containing heterocycle, which may be aromatic or non-aromatic.

[0100] In the formula (I), the "substituted linear or branched alkyl group having a carbon number of 1 to 20" represented by R 1 , R 2 , R 3 , and R 4 may specifically include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a -SO3 - group; a -SO3H group; a -SO3M group; a cyclic alkyl group having a carbon number of 3 to 19 such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cyclooctyl group; a linear alkoxy group having a carbon number of 1 to 19 such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, or a decyloxy group; a branched alkoxy group having a carbon number of 3 to 19 such as an isopropoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, or an isooctyloxy group; a cyclic alkoxy group having a carbon number of 3 to 19 such as a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, or a cyclohexyloxy group; an aromatic hydrocarbon group having a carbon number of 6 to 19 such as a phenyl group, a naphthyl group, a biphenyl group, an anthracen group, a phenanthrenyl group, a pyrenyl group, a triphenylene group, an indenyl group, or a fluorenyl group; or a condensed polycyclic aromatic group; a heterocyclic group having a carbon number of 2 to 19 such as a pyridyl group, a pyrimidinyl group, a triazinyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a quinolyl group, an isoquinolyl group, a naphthrydinyl group, an indolyl group, a benzimidazolyl group, a carbazolyl group, a carbolinyl group, an acridinyl group, an oxazinyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thienyl group, a benzothienyl group, a dibenzothienyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, or a benzothiazolyl group. The "M" represents an alkali metal atom such as a lithium atom, a sodium atom, or a potassium atom.

[0101] The "substituent" can include only one or a plurality of substituents, and in the case of including a plurality of substituents, the substituents can be the same or different. Furthermore, the "substituent" can further have the above-mentioned substituents.

[0102] In the formula (I), the "substituted cyclic alkyl group having a carbon number of 3 to 20", "substituted aromatic hydrocarbon group having a carbon number of 6 to 20", or "substituted heterocyclic group having a carbon number of 2 to 20" represented by R 1 , R 2 , R 3 , and R 4 may specifically include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a -SO3 -; -SO3H; -SO3M; methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and the like alkyl groups having 1 to 14 carbon atoms; isopropyl, isobutyl, sec-butyl, t-butyl, isooctyl, and the like branched alkyl groups having 3 to 14 carbon atoms; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, and the like cyclic alkyl groups having 3 to 14 carbon atoms; methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, and the like alkoxy groups having 1 to 14 carbon atoms; isopropoxy, isobutoxy, sec-butoxy, t-butoxy, isooctyloxy, and the like branched alkoxy groups having 3 to 14 carbon atoms; cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, and the like cyclic alkoxy groups having 3 to 14 carbon atoms; phenyl, naphthyl, biphenyl, anthryl, phenanthryl, indenyl, fluorenyl, and the like aromatic hydrocarbon groups having 6 to 14 carbon atoms or condensed polycyclic aromatic groups; pyridyl, pyrimidyl, triazinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, quinolyl, isoquinolyl, naphthrydinyl, indolyl, benzimidazolyl, carbazolyl, carbolinyl, acridyl, phenarsenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, and the like heterocyclic groups having 2 to 14 carbon atoms. The above "M" represents an alkali metal atom such as a lithium atom, a sodium atom, or a potassium atom, and the like.

[0103] The "substituent" can include only one, or can include a plurality, and in the case of including a plurality, can be the same as or different from each other. Also, the "substituent" can further have the above-mentioned exemplified substituent.

[0104] In formula (I), R 1 and R 2 may be the same as or different from each other. In formula (I), R 3 and R 4 may be the same as or different from each other. In formula (I), R 1 and R 2 may be the same as or different from each other. In formula (I), R 3 and R 4 may be the same as or different from each other. In formula (I), R 1 and R 2 may be the same as or different from each other, and R 3 and R 4 may be the same as or different from each other.

[0105] In formula (I), R 5 , R 6 , R 7 , R 8 , and R 9 representing "halogen atoms" can include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

[0106] In the formula (I), "a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms" represented by R 5 , R 6 , R 7 , R 8 , and R 9 may be exemplified by, specifically, a linear alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, and the like; a branched alkyl group such as an isopropyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an isooctyl group, and the like; a cycloalkyl group such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and the like; and the like.

[0107] In the formula (I), "a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms" represented by R 5 , R 6 , R 7 , R 8 , and R 9 may be exemplified by, specifically, a linear alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, and the like; a branched alkyl group such as an isopropyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an isooctyl group, and the like; a cycloalkyl group such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and the like; and the like. --SO3H; -SO3M; a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and the like, a cyclic alkyl group having 3 to 17 carbons; a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, and the like, a linear alkoxy group having 1 to 17 carbons; an isopropoxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an isooctyloxy group, and the like, a branched alkoxy group having 1 to 17 carbons; a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like, a cyclic alkoxy group having 3 to 17 carbons; a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, and the like, an aromatic hydrocarbon group having 6 to 18 carbons or a condensed polycyclic aromatic group having 6 to 17 carbons, and the like. The above "M" represents an alkali metal atom such as a lithium atom, a sodium atom, or a potassium atom, and the like.

[0108] The "substituent" can include only one, or can include a plurality of substituents, and in the case of including a plurality of substituents, the substituents can be the same as or different from each other. Further, the "substituent" can further have the above-described exemplified substituent.

[0109] In the formula (I), in R 5 , R 6 , R 7 , R 8 , and R 9 , adjacent groups can be bonded to each other to form a ring. Specifically, R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , or R 8 and R 9 may be bonded to each other to form a ring. As the ring formed in this case, a 5-membered ring or a 6-membered ring is preferred, and a 6-membered ring is more preferred.

[0110] In one embodiment, at least two -SO3 - groups exist in the above-described formula (I), and R 9 is a -SO3 - group, and R 7 is a hydrogen atom or a -SO3 - group.

[0111] In the formula (I), as R 11 , R 12 , and R 13The "linear or branched alkyl group having 1 to 20 carbon atoms" in the "substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms", "substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms", and "aromatic hydrocarbon group having 6 to 20 carbon atoms" in the "substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms", "linear or branched alkoxy group having 1 to 20 carbon atoms", and "aromatic hydrocarbon group having 6 to 20 carbon atoms" in the "substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms", "substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms", and "aromatic hydrocarbon group having 6 to 20 carbon atoms" in the above-mentioned formula (I) is specifically exemplified by a linear alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group; a branched alkyl group such as an isopropyl group, an isobutyl group, a sec-butyl group, a t-butyl group, and an isooctyl group; a linear alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, and a decyloxy group; a branched alkoxy group such as an isopropoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, and an isooctyloxy group; and an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, and a terphenyl group.

[0112] In one embodiment, in the above-mentioned formula (I), R 11 , R 12 , and R 13 each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, or a polyether structure, and at least one of R 11 , R 12 , and R 13 is a polyether structure.

[0113] As the "polyether structure", a polyoxyethylene ether structure (*-(CH2CH2O) q H) (which can also be represented by "*-(EO) q H"), a polyoxypropylene ether structure (*-(CH2CH2CH2O) q H, *-(CH2CH(CH3)O) q H, *-(CH(CH3)CH2O) q H) (wherein *-(CH2CH2CH2O) q H can also be represented by "*-(PO) q H"), a polyoxybutylene ether structure (*-(CH2CH2CH2CH2O) q H, *-(CH2CH2CH(CH3)O) q H, *-(CH2CH(CH3)CH2O) q H, *-(CH(CH3)CH2CH2O) q H) (wherein CH2CH2CH2CH2O) q H can also be represented by "*-(BO)q H, * -(PO)2H, * -(PO)3H, * -(PO)4H, * -(PO)5H, * -(PO)6H, * -(PO)7H, * -(PO)8H, * -(PO)9H, * -(PO) 10 H, * -(PO)2H, * -(PO)3H, * -(PO)4H, * -(PO)5H, * -(PO)6H, * -(PO)7H, * -(PO)8H, * -(PO)9H, * -(PO) 10 H, * -(PO)2H, * -(PO)3H, * -(PO)4H, * -(PO)5H, * -(PO)6H, * -(PO)7H, * -(PO)8H, * -(PO)9H, * -(PO) 10 H, * -(PO)2H, * -(PO)3H, * -(PO)4H, * -(PO)5H, * -(PO)6H, * -(PO)7H, * -(PO)8H, * -(PO)9H, * -(PO) 10 H, * -(PO)2H, * -(PO)3H, * -(PO)4H, * -(PO)5H, * -(PO)6H, * -(PO)7H, * -(PO)8H, * -(PO)9H, * -(PO) 10 H, * -(PO)2H, * -(PO)3H, * -(PO)4H, * -(PO)5H, * -(PO)6H, * -(PO)7H, * -(PO)8H, * -(PO)9H, * -(PO)

[0114] In formula (I), "M" represents an alkali metal atom, and examples include a lithium atom, a sodium atom, and a potassium atom.

[0115] In formula (I), R 1 , R 2 , R 3 , and R 4 , each independently represent a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 12 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms. 1 , R 2 , R 3 , and R 4 , when R 1 , R 2 , R 3 , and R 4 are the above groups, the brightness of the colored layer (pattern) formed from the photosensitive colored resin composition can be further improved.

[0116] In formula (I), R 5R 6 R 7 R 8 and R 9 Preferably, each of the hydrogen atom, halogen atom, and -SO3 is independently represented. - -SO3H, -SO3M, a straight-chain or branched alkyl group having 1 to 10 carbon atoms with a substituent, or a substituted or unsubstituted straight-chain or branched alkoxy group having 1 to 10 carbon atoms. When R 5 R 6 R 7 R 8 and R 9 When the above-mentioned groups are present, the brightness of the colored layer (pattern) obtained by the photosensitive coloring resin composition can be further improved.

[0117] In formula (I), it is preferable that at least two -SO3 groups are present. - And R9 is -SO3 - And R7 is a hydrogen atom or -SO3 - When equation (I) preferably contains at least two -SO3 groups. - And R9 is -SO3 - And R7 is a hydrogen atom or -SO3 - At the same time, the brightness of the colored layer (pattern) prepared by the photosensitive coloring resin composition can be further improved.

[0118] In equation (I), R is... 11 R 12 and R 13 R is preferred. 11 R 12 and R 13 Each independently represents a straight-chain or branched alkyl or polyether structure with 1 to 20 atoms, whether substituted or unsubstituted, and R 11 R 12 and R 13 At least one of them is a polyether structure. When R 11 R 12 and R 13 When the above-mentioned groups are present, the brightness of the colored layer (pattern) obtained by the photosensitive coloring resin composition can be further improved.

[0119] In formula (I), "M" represents an alkali metal atom, preferably a lithium atom, a sodium atom, or a potassium atom, more preferably a lithium atom or a sodium atom, and most preferably a sodium atom.

[0120] In formula (I), n represents a positive integer from 1 to 4. Furthermore, the compound represented by formula (I) is electrically neutral as a whole. Specifically, in formula (I), -SO3 - The total quantity is at least 2. For example, when -SO3- When the total quantity is 2, n is 1; when -SO3 - When the total number is 3, n is 2.

[0121] The dibenzopiperanoid pigment represented by formula (I) in this embodiment can be synthesized, for example, by a known method such as counter ion exchange. Specifically, it can be synthesized by adding an aqueous solution of a salt composed of an amine compound and an acid to an aqueous solution of a dye with an alkali metal sulfonic acid group. Furthermore, when the precipitated dibenzopiperanoid pigment stubbornly adheres and hinders stirring, an organic solvent can be mixed in to eliminate or mitigate this situation. As an organic solvent, there are no particular limitations as long as the corresponding dibenzopiperanoid pigment has sufficient solubility; examples include: aromatic hydrocarbons such as toluene and xylene; ketones such as acetone, 2-butanone, 2-pentanone, and 3-pentanone; esters such as ethyl acetate and butyl acetate; and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, pentanol, and hexanol.

[0122] Dibenzopiperanoid colorants (A-1) contain anions and ammonium ions of dibenzopiperanoid pigments.

[0123] Anions of dibenzopiperanoid pigments can be listed as anions shown in formulas (Ib-1) to (Ib-41) below, but this embodiment is not limited to these anions.

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] Ammonium ions can be listed as those shown in formulas (Ic-1) to (Ic-23) below, but this embodiment is not limited to these ammonium ions. In formulas (Ic-1) to (Ib-23), EO is ethoxy, PO is propoxy, and BO is butoxy.

[0132]

[0133]

[0134]

[0135] Specific examples of the dibenzofuran-based colorant (A-1) are preferably a dibenzofuran-based colorant consisting of formula (Ib-28) and formula (Ic-1), a dibenzofuran-based colorant consisting of formula (Ib-40) and formula (Ic-2), a dibenzofuran-based colorant consisting of formula (Ib-25) and formula (Ic-4), a dibenzofuran-based colorant consisting of formula (Ib-40) and formula (Ic-5), a dibenzofuran-based colorant consisting of formula (Ib-7) and formula (Ic-16), a dibenzofuran-based colorant consisting of formula (Ib-5) and formula (Ic-7), a dibenzofuran-based colorant consisting of formula (Ib-41) and formula (Ic-16), or a combination thereof.

[0136] The above-described dibenzofuran-based colorant can be used alone or in a mixture of a plurality of kinds.

[0137] In the present embodiment, when the content of the solid component of the photosensitive colored resin composition is 18 to 25% by weight and the colorant (A) includes the dibenzofuran-based colorant (A-1) represented by formula (I), the relative total VOC reduction rate is improved in the production process of the color filter formed from the photosensitive colored resin composition, and the colored layer (pattern) produced from the photosensitive colored resin composition has good brightness and pattern properties.

[0138] Conversely, when the colorant (A) does not include the dibenzofuran-based colorant (A-1) represented by formula (I), the brightness and pattern properties of the colored layer (pattern) produced from the photosensitive colored resin composition are not good, and further the overall display quality of the image display device produced from the color filter is not good.

[0139] The dibenzofuran-based colorant (A-1) can be 0.01 to 25% by weight, preferably 0.05 to 15% by weight, and more preferably 0.1 to 10% by weight, based on the total weight of the solid component of the photosensitive colored resin composition being 100% by weight.

[0140] Other colorants (A-2)

[0141] The photosensitive colored resin composition of the present embodiment can further include other colorants (A-2) in addition to the dibenzofuran-based colorant (A-1). The other colorants (A-2) can include at least one of the group consisting of pigments (A-2-1) represented by formula (II), other pigments (A-2-2), and other dyes (A-2-3).

[0142] Pigments (A-2-1) represented by formula (II)

[0143] The pigments (A-2-1) are compounds represented by formula (II).

[0144]

[0145] in formula (II),

[0146] A represents a p-valent organic group, wherein the carbon atom directly bonded to N in the organic group does not have a π bond, the organic group represents an aliphatic hydrocarbon group having at least a saturated aliphatic hydrocarbon group at the end directly bonded to N, or an aromatic group having the aliphatic hydrocarbon group, the carbon chain of the aliphatic hydrocarbon group can contain O, S, N, and the carbon chain of the aromatic group can contain O, S, N;

[0147] B q- represents a q-valent heteropoly acid anion;

[0148] R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group, wherein R 2 , R 3 , R 4 , and R 5 each independently represent a substituted or unsubstituted alkyl group, R 2 and R 3 may be bonded to each other to form a ring structure, R 4 and R 5 may be bonded to each other to form a ring structure, and a plurality of R 1 , R 2 , R 3 , R 4 , and R 5 each can be the same or different;

[0149] R 6 and R 7 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a halogen atom, or a cyano group;

[0150] Ar represents a substituted or unsubstituted 2-valent aromatic group, and a plurality of Ar each can be the same or different;

[0151] p and q represent an integer of 2 or more;

[0152] r and s represent an integer of 1 or more;

[0153] v represents 0 or 1, and when v represents 0, a bond is not present;

[0154] t and u each independently represent an integer of 0 or more and 4 or less;

[0155] t and u are each an integer of 0 or more and 4 or less.

[0156] The carbon atom to which the p-valent organic group represented by A in formula (II) is directly bonded to the nitrogen atom (N) is a carbon atom having no π-bond, and the organic group represents an aliphatic hydrocarbon group having at least a saturated aliphatic hydrocarbon group at the terminal directly bonded to N, or an aromatic group having the aliphatic hydrocarbon group, wherein the carbon chain of the aliphatic hydrocarbon group can contain an oxygen atom (O), a sulfur atom (S), a nitrogen atom (N), and the carbon chain of the aromatic group can also contain O, S, and N. Since the carbon atom directly bonded to N has no π-bond, the color tone or the color characteristics such as the transmittance possessed by the cationic chromophore site are not affected by the bonding group A or other chromophore sites, and the same color as the monomer can be maintained.

[0157] In A of formula (II), the aliphatic hydrocarbon group having at least a saturated aliphatic hydrocarbon group at the terminal directly bonded to N can be any one of a straight chain, a branched chain, or a cyclic, as long as the carbon atom at the terminal directly bonded to N has no π-bond, and the carbon atom other than the terminal can have an unsaturated bond, can have a substituent, and the carbon chain of the substituent can contain O, S, and N. The carbon chain of the substituent can contain, for example, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amido group, or the like, and a hydrogen atom can be substituted with a halogen atom or the like.

[0158] Further, in A of formula (II), the aromatic group having the aliphatic hydrocarbon group can include a monocyclic or polycyclic aromatic group having at least a saturated aliphatic hydrocarbon group at the terminal directly bonded to N, which can have a substituent, and can be a heterocycle containing O, S, and N.

[0159] In A of formula (II), from the viewpoint of the rigidity of the skeleton, A is preferably an aliphatic hydrocarbon group or an aromatic group containing a ring.

[0160] In A of formula (II), from the viewpoint of the rigidity of the skeleton, the cyclic aliphatic hydrocarbon group as A is preferably a bridged aliphatic cyclic hydrocarbon group. The bridged aliphatic cyclic hydrocarbon group refers to a polycyclic aliphatic hydrocarbon group having a crosslinked structure within an aliphatic ring, having a polycyclic structure. The bridged aliphatic cyclic hydrocarbon group can include norbornane, bicyclo[2.2.2]octane, adamantane, and the like. The bridged aliphatic cyclic hydrocarbon group is preferably norbornane. Further, the aromatic group can include a group containing a benzene ring, a naphthalene ring, and is preferably a group containing a benzene ring. For example, in the case where A is a divalent organic group, a straight chain, a branched chain, or a cyclic alkylene group having a carbon number of 1 to 20, or an aromatic group having a carbon number of 1 to 20 in which an alkylene group such as xylene is substituted by two groups, and the like can be included.

[0161] In A of formula (II), the valence number p is the number of chromophoric cationic sites constituting the cation, and p represents an integer of 2 or more. In terms of heat resistance, the valence number p of the cation is preferably 2 or more, and more preferably 3 or more. The upper limit of p is not particularly limited, and in terms of ease of production, p is preferably an integer of 4 or less, and more preferably 3 or less.

[0162] R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group, wherein R 2 , R 3 , R 4 , and R 5 are each independently a substituted or unsubstituted alkyl group. Also, R 2 , R 3 , R 4 , and R 5 are preferably each independently a substituted or unsubstituted alkyl group. When R 2 , R 3 , R 4 , and R 5 each independently represent a substituted or unsubstituted alkyl group, the pattern produced from the photosensitive colored resin composition has a better post-baking residue rate.

[0163] R 1 , R 2 , R 3 , R 4 , and R 5 The alkyl group in R 1 , R 2 , R 3 , R 4 , and R 5 is not particularly limited, and examples include linear or branched alkyl groups having 1 to 20 carbon atoms, and preferably linear or branched alkyl groups having 1 to 8 carbon atoms, and more preferably linear or branched alkyl groups having 1 to 5 carbon atoms, and particularly preferably ethyl or methyl groups. The substituent group that the alkyl group can have is not particularly limited, and examples include halogen atoms, hydroxyl groups, and alkoxy groups.

[0164] In terms of chemical stability, R 1 , R 2 , R 3 , R 4 , and R 5 are preferably each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or R 2 and R 3 are bonded to each other to form a ring structure, and R 4 and R 5 are bonded to each other to form a ring structure, wherein the ring structure can include a pyrrolidine ring, a piperidine ring, or a morpholine ring.

[0165] R1 R 2 R 3 R 4 R 5 may each independently form the above-mentioned configuration, that is, a plurality of R 1 R 2 R 3 R 4 R 5 may each be the same or different.

[0166] R 6 R 7 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a halogen atom, or a cyano group. The substituted or unsubstituted alkyl group in R 6 R 7 is not particularly limited, and is preferably a linear or branched alkyl group having a carbon number of 1 to 8, more preferably an alkyl group having a carbon number of 1 to 4. The alkyl group having a carbon number of 1 to 4 can include a methyl group, an ethyl group, a propyl group, and a butyl group, which can be linear or branched. The substituent group that can be present in the alkyl group is not particularly limited, and can include an aryl group, a halogen atom, a hydroxyl group, an alkoxy group, or a combination thereof.

[0167] Further, the substituted or unsubstituted alkoxy group in R 6 R 7 is not particularly limited, and is preferably a linear or branched alkoxy group having a carbon number of 1 to 8, more preferably an alkoxy group having a carbon number of 1 to 4. The alkoxy group having a carbon number of 1 to 4 can include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, which can be linear or branched. The substituent group that can be present in the alkoxy group is not particularly limited, and can include an aryl group, a halogen atom, a hydroxyl group, an alkoxy group, or a combination thereof.

[0168] The halogen atom in R 6 R 7 may include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a combination thereof.

[0169] The number of substitutions in R 6 R 7 each independently represents an integer of 0 or more and 4 or less, preferably 0 or more and 2 or less, more preferably 0 or more and 1 or less. t + v and u + v are integers of 0 or more and 4 or less. When t and u are each two or more, the plurality of t and u can each be the same or different.

[0170] Further, when v represents 0, there is no bond, and the compound represented by formula (II) has a triarylmethane skeleton. In this case, R 6 R 7Any of the positions of the aromatic ring which can be substituted in the triarylmethane skeleton, or which has a resonance structure within the skeleton, can be substituted, and preferably the substitution is made at the meta position with respect to the amine group represented by -NR 2 R 3 or -NR 4 R 5 The substitution position of the amine group represented by -NR

[0171] The substituted or unsubstituted bivalent aromatic group in Ar is not particularly limited, and a plurality of Ar can each be the same or different. The aromatic group in Ar can be the same as the aromatic groups listed for A.

[0172] Ar is preferably a substituted or unsubstituted aromatic group having a carbon number of 6 to 20, and more preferably a substituted or unsubstituted condensed polycyclic carbocyclic aromatic group having a carbon number of 10 to 14. Of these, a phenylene group or a naphthylene group is more preferable from the viewpoint of simple structure and low cost of raw materials.

[0173] A plurality of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 may be present in one molecule. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 , and Ar can be the same or different. By combining R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 , and Ar, the desired color can be adjusted.

[0174] In the compound represented by formula (II), B q- represents a heteromultivalent acid anion of q valence. The heteromultivalent acid anion can be represented as (Y1M e O f ) q- In the above ion formula, M represents a polyatomic group, Y represents a heteroatom, e represents the composition ratio of the polyatomic group, and f represents the composition ratio of the oxygen atom. The polyatomic group M can include molybdenum (Mo), tungsten (W), vanadium (V), titanium (Ti), or niobium (Nb), etc. Also, the heteroatom Y can include silicon (Si), phosphorus (P), arsenic (As), sulfur (S), iron (Fe), and cobalt (Co), etc.

[0175] wherein B q- , the heteromultivalent acid anion preferably contains at least one of molybdenum (Mo) and tungsten (W), and more preferably a heteromultivalent acid anion of q valence containing at least tungsten.

[0176] r in formula (II) is the number of cations, and s represents the number of anions. r and s represent an integer of 1 or more. In the case where r represents 2 or more, the plurality of cations in formula (II) can be used singly or in a mixture of a plurality of kinds. Also, in the case where s is 2 or more, the plurality of anions in formula (II) can be used singly or in a mixture of a plurality of kinds.

[0177] v in formula (II) represents an integer of 0 or 1. When v represents 0, there is no bond, and the main skeleton of formula (II) is a triarylmethane skeleton. When v represents 1, the main skeleton of formula (II) is a xanthene skeleton. The plurality of v can each be the same or different. Among the compounds represented by formula (II), those containing a triarylmethane skeleton are preferred.

[0178] Also, the compound represented by formula (II) can be produced, for example, with reference to the specification of International Publication No. 2012 / 144520.

[0179] The above-mentioned pigment (A-2-1) can be used singly or in a mixture of a plurality of kinds.

[0180] Specific examples of the compound represented by formula (II) can include at least one of compounds (II-1) to (II-20). Each of compounds (II-1) to (II-20) contains one cation and one heteromultivalent acid anion.

[0181] The compound represented by formula (II) is preferably at least one of the compounds represented by compounds (II-1) to (II-4), (II-6) to (II-7), (II-10) to (II-11), (II-14), and (II-17).

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] Other pigments (A-2-2)

[0189] In the present embodiment, the colorant (A) can further include other pigments (A-2-2). The other pigments (A-2-2) can be inorganic pigments, organic pigments, or a combination thereof.

[0190] The inorganic pigments can be metal oxides, metal complex salts, or the like metal compounds. Among them, the inorganic pigments can include oxides of iron (Fe), cobalt (Co), aluminum (Al), cadmium (Cd), lead (Pb), copper (Cu), titanium (Ti), magnesium (Mg), chromium (Cr), zinc (Zn), antimony (Sb), or the like metal, composite oxides of the aforementioned metals, metal complex salts, or a combination thereof.

[0191] Specific examples of organic pigments can include C.I. Pigment Yellow 1, 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 61, 65, 71, 73, 74, 81, 83, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 126, 127, 128, 129, 138, 139, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 175; C.I. Pigment Orange 1, 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 61, 63, 64, 71, 73; C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 30, 31, 32, 37, 38, 40, 41, 42, 48:1, 48:2, 48:3, 48:4, 49:1, 49:2, 50:1, 52:1, 53:1, 57, 57:1, 57:2, 58:2, 58:4, 60:1, 63:1, 63:2, 64:1, 81:1, 83, 88, 90:1, 97, 101, 102, 104, 105, 106, 108, 112, 113, 114, 122, 123, 144, 146, 149, 150, 151, 155, 166, 168, 170, 171, 172, 174, 175, 176, 177, 178, 179, 180, 185, 187, 188, 190, 193, 194, 202, 206, 207, 208, 209, 215, 216, 220, 224, 226, 242, 243, 245, 254, 255, 264, 265; C.I. Pigment Violet 1, 14, 19, 23, 29, 32, 33, 36, 37, 38, 39, 40, 50; C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 16, 21, 22, 60, 61, 64, 66; C.I. Pigment Green 7, 36, 37, 42, 58; C.I. Pigment Brown 23, 25, 28; C.I. Pigment Black 1, 7; or combinations thereof.

[0192] The other pigments (A-2-2) described above can be used alone or in a mixture of a plurality of kinds.

[0193] The other pigments (A-2-2) are preferably C.I. Pigment Blue 15:4, C.I. Pigment Blue 15:6, or a combination thereof.

[0194] The average particle diameter of the other pigment (A-2-2) can be 10 nm to 200 nm, preferably 20 nm to 150 nm, more preferably 30 nm to 130 nm.

[0195] The other dye (A-2-3)

[0196] The other dye (A-2-3) includes, but is not limited to, an azo-based dye, an anthraquinone-based dye, a phthalocyanine-based dye, a quinonimine-based dye, a quinoline-based dye, a nitro-based dye, or a combination thereof.

[0197] The azo-based dye includes, but is not limited to, C.I. Acid Yellow 11, Acid Orange 7, Acid Red 37, Acid Red 180, Acid Blue 29, Direct Red 28, Direct Red 83, Direct Yellow 12, Direct Orange 26, Direct Green 28, Direct Green 59, Reactive Yellow 2, Reactive Red 17, Reactive Red 120, Reactive Black 5, Disperse Orange 5, Disperse Red 58, Disperse Blue 165, Basic Blue 41, Basic Red 18, Mordant Red 7, Mordant Yellow 5, Mordant Black 7, or a combination thereof.

[0198] The anthraquinone-based dye includes, but is not limited to, C.I. Bat blue 4, Acid Blue 40, Acid Green 25, Reactive Blue 19, Reactive Blue 49, Disperse Red 60, Disperse Blue 56, Disperse Blue 60, or a combination thereof.

[0199] The phthalocyanine-based dye includes, but is not limited to, C.I. Basic Blue 5, and the like.

[0200] The quinonimine-based dye includes, but is not limited to, C.I. Basic Blue 3, C.I. Basic Blue 9, or a combination thereof.

[0201] The quinoline-based dye C.I. Solvent Yellow 33, C.I. Acid Yellow 3, C.I. Disperse Yellow 64, or a combination thereof.

[0202] The nitro-based dye includes, but is not limited to, C.I. Acid Yellow 1, Acid Orange 3, Disperse Yellow 42, or a combination thereof.

[0203] The above other dye (A-2-3) can be used alone or in a mixture of a plurality of kinds.

[0204] The other dye (A-2-3) is preferably includes C.I. Acid Red 37, C.I. Acid Blue 29, or a combination thereof.

[0205] The other colorant (A-2) is preferably includes compound (II-1), compound (II-2), C.I. Pigment Blue 15:6, or a combination thereof.

[0206] The other colorant (A-2) can be 1 to 60% by weight, preferably 2.5 to 45% by weight, and more preferably 5 to 35% by weight, based on the total weight of the solid content of the photosensitive colored resin composition being 100% by weight.

[0207] The colorant (A) can be 1 to 85% by weight, preferably 2.5 to 60% by weight, and more preferably 5 to 45% by weight, based on the total weight of the solid content of the photosensitive colored resin composition being 100% by weight.

[0208] In the photosensitive colored resin composition of the present embodiment, the colorant (A) is preferably used by being dispersed in a solvent with a dispersant. In the present embodiment, the dispersant can be appropriately selected from among known dispersants. The dispersant can include a cationic surfactant, an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, a polysiloxane surfactant, a fluorine-based surfactant, or the like, or a combination thereof. The above-listed dispersants can be either non-polymeric dispersants or polymeric dispersants. From the viewpoint of being able to uniformly and finely disperse, the surfactant is preferably a polymeric dispersant.

[0209] The polymeric dispersant can include (co)polymers of unsaturated carboxylic acid esters such as polyacrylates; (partial) amine salts, (partial) ammonium salts, or (partial) alkylamine salts of (co)polymers of unsaturated carboxylic acids such as polyacrylic acids; (co)polymers of hydroxyl-containing unsaturated carboxylic acid esters such as hydroxyl-containing polyacrylates, or modified products of the above compounds; polyurethanes; unsaturated polyamides; polysiloxanes; long-chain polyaminoamide phosphates; polyalkyleneimine derivatives (amides obtained by the reaction of poly(lower alkyleneimine) with a polyol containing a free carboxyl group, or the bases thereof); polyallylamine derivatives (reaction products obtained by reacting polyallylamine with one or more compounds selected from among a polyol containing a free carboxyl group, a polyamide, or a co-condensate of an ester and an amide (polyester amide)); or the like, or a combination thereof.

[0210] From the viewpoint of being able to better disperse the above colorant (A) and having good dispersion stability, the polymeric dispersant is preferably a polymeric dispersant containing a nitrogen atom in the main chain or side chain and having an amine value.

[0211] Specific examples of the polymeric dispersant containing a nitrogen atom in the main chain or side chain can include the following.

[0212] Commercially available products of the (partial) amine salts, (partial) ammonium salts, or (partial) alkylamine salts of (co)polymers of unsaturated carboxylic acids such as polyacrylic acids can include Disperbyk 2000, Disperbyk 2001 (all manufactured by BYK-Chemie), and the like.

[0213] Examples of commercially available products of the polyurethane type include Disperbyk 161 (manufactured by BYK-Chemie Co.).

[0214] Examples of commercially available products of the unsaturated polyamide type include Disperbyk 101, Disperbyk 130 (manufactured by BYK-Chemie Co.).

[0215] Examples of commercially available products of the polyallylamine derivative type include Ajisper PB821, Ajisper PB822, Ajisper PB824, Ajisper PB827 (manufactured by Ajinomoto Fine-Techno Co.).

[0216] Examples of commercially available products of the polyethyleneimine derivative type include Solsperse 33500 (manufactured by Lubrizol Co.).

[0217] Examples of other commercially available dispersants include Dysperbyk 116, Dysperbyk 140, Dysperbyk 160, Dysperbyk 162, Dysperbyk 163, Dysperbyk 164, Dysperbyk 166, Dysperbyk 167, Dysperbyk 168, Dysperbyk 170, Dysperbyk 171, Dysperbyk 174, Dysperbyk 182, Dysperbyk 2050 (all manufactured by BYK-Chemie Co.); EFKA 4046, EFKA 4047 (all manufactured by EFKA Chemicals Co.); Solsperse 12000, Solsperse 13250, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 24000SC, Solsperse 27000, Solsperse 28000, Solsperse 32000, Solsperse 33500, Solsperse 35200, Solsperse 37500 (all manufactured by Lubrizol Co.); Ajisper PB711, Ajisper 823, Ajisper 880 (all manufactured by Ajinomoto Fine-Techno Co.); and the like.

[0218] The amount of the dispersant used is not particularly limited and can be appropriately adjusted as needed.

[0219] Alkali-soluble resin (B)

[0220] First alkali-soluble resin (B)

[0221] The first alkali-soluble resin (B-1) of the present embodiment is obtained by copolymerizing a carboxyl group-containing ethylenically unsaturated monomer (b-1-1) and other copolymerizable ethylenically unsaturated monomers (b-1-2).

[0222] The carboxyl group-containing ethylenically unsaturated monomer (b-1-1) can be used alone or in a mixture, and includes, but is not limited to, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid (MAA), crotonic acid, α-chlorocrotonic acid, ethylacrylic acid, cinnamic acid, 2-acryloyloxyethyl succinate, or 2-methacryloyloxyethyl succinate (HOMS); unsaturated dicarboxylic acids (anhydrides) such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, and citraconic anhydride; and unsaturated polycarboxylic acids (anhydrides) having three or more carboxyl groups. The carboxyl group-containing ethylenically unsaturated monomer is preferably one or a combination of acrylic acid, methacrylic acid, 2-acryloyloxyethyl succinate, 2-methacryloyloxyethyl succinate, or the like. The carboxyl group-containing ethylenically unsaturated monomer is more preferably 2-acryloyloxyethyl succinate, 2-methacryloyloxyethyl succinate, or a combination thereof.

[0223] In the present embodiment, the amount of the carboxyl group-containing ethylenically unsaturated monomer (b-1-1) and the other copolymerizable ethylenically unsaturated monomers (b-1-2) based on the first alkali-soluble resin (B-1) is 100 parts by weight, the amount of the carboxyl group-containing ethylenically unsaturated monomer (b-1-1) is 10 to 90 parts by weight, preferably 15 to 85 parts by weight, and more preferably 20 to 80 parts by weight.

[0224] The other copolymerizable ethylenically unsaturated monomers (b-1-2) can be used alone or in combination, and include, but are not limited to, aromatic vinyl compounds such as styrene (SM), α-methylstyrene, vinyltoluene, p-chlorostyrene, methoxystyrene, and the like; maleimides such as N-phenylmaleimide (PMI), N-o-hydroxyphenylmaleimide, N-m-hydroxyphenylmaleimide, N-p-hydroxyphenylmaleimide, N-o-methylphenylmaleimide, N-m-methylphenylmaleimide, N-p-methylphenylmaleimide, N-o-methoxyphenylmaleimide, N-m-methoxyphenylmaleimide, N-p-methoxyphenylmaleimide, N-cyclohexylmaleimide, and the like; unsaturated carboxylic acid esters such as methyl acrylate (MA), methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl 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 (BzMA), phenyl acrylate, phenyl methacrylate, triethylene glycol methoxy acrylate, triethylene glycol methoxy methacrylate, dodecyl methacrylate, tetradecyl methacrylate, hexadecyl methacrylate, octadecyl methacrylate, eicosyl methacrylate, docosyl methacrylate, dicyclopentenyloxyethyl acrylate (DCPOA), and the like; unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate, glycidyl methacrylate, and the like; aminoalkyl (meth)acrylates such as aminoethyl (meth)acrylate, aminopropyl (meth)acrylate, aminobutyl (meth)acrylate, and the like; unsaturated carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, and the like; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl glycidyl ether, methallyl glycidyl ether, and the like;nitrile compounds of acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, vinylidene cyanide; unsaturated amides of acrylamide, methacrylamide, α-chloroacrylamide, N-hydroxyethyl acrylamide, N-hydroxyethyl methacrylamide; aliphatic conjugated dienes of 1,3-butadiene, isoprene, chlorinated butadiene; or combinations thereof.

[0225] The other copolymerizable ethylenically unsaturated monomer (b-1-2) is preferably selected from the group consisting of styrene, N-phenylmaleimide, methyl acrylate, methyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate, benzyl methacrylate, dicyclopentenyloxyethyl acrylate, and combinations thereof.

[0226] In the present embodiment, the use amount of the carboxylic acid group-containing ethylenically unsaturated monomer (b-1-1) based on the first alkali-soluble resin (B-1) is 100 parts by weight, and the use amount of the other copolymerizable ethylenically unsaturated monomer (b-1-2) is 10 to 90 parts by weight, preferably 15 to 85 parts by weight, and more preferably 20 to 80 parts by weight.

[0227] The method of preparing the first alkali-soluble resin (B-1) is not particularly limited, and an appropriate polymerization method can be selected as desired. The polymerization method can include solution polymerization. In the reaction solution of the alkali-soluble resin (B), in addition to the desired monomer, a solvent, an initiator, and the like can be included. The solvent can be used alone or in combination, and the solvent includes, but is not limited to, (poly)alkylene glycol monoalkyl ether such as ethylene glycol methyl ether, ethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol n-propyl ether, diethylene glycol n-butyl ether, triethylene glycol methyl ether, triethylene glycol ethyl ether, propylene glycol methyl ether, propylene glycol ethyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol ethyl ether, and the like; (poly)alkylene glycol monoalkyl ether acetate such as ethylene glycol methyl ether acetate, ethylene glycol ethyl ether acetate, propylene glycol methyl ether acetate (PGMEA), propylene glycol ethyl ether acetate, and the like; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, and the like; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, and the like; alkyl lactate such as 2-hydroxypropionic acid methyl ester, 2-hydroxypropionic acid ethyl ester, and the like; other esters such as 2-hydroxy-2-methylpropionic acid methyl ester, 2-hydroxy-2-methylpropionic acid ethyl ester, 3-methoxypropionic acid methyl ester, 3-methoxypropionic acid ethyl ester, 3-ethoxypropionic acid methyl ester, 3-ethoxypropionic acid ethyl ester (EEP), ethoxyacetic acid ethyl ester, hydroxyacetic acid ethyl ester, 2-hydroxy-3-methylbutyric acid methyl ester, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl acetate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, pyruvic acid methyl ester, pyruvic acid ethyl ester, pyruvic acid n-propyl ester, acetoacetic acid methyl ester, acetoacetic acid ethyl ester, 2-methoxybutyric acid ethyl ester, and the like; aromatic hydrocarbons such as toluene, xylene, and the like; amides such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, and the like; and the like. The solvent is preferably propylene glycol methyl ether acetate, 3-ethoxypropionic acid ethyl ester, or a combination thereof. The (poly)alkylene glycol monoalkyl ether refers to an alkylene glycol monoalkyl ether or a polyalkylene glycol monoalkyl ether. The (poly)alkylene glycol monoalkyl ether acetate refers to an alkylene glycol monoalkyl ether acetate or a polyalkylene glycol monoalkyl ether acetate.

[0228] The initiator is generally a radical polymerization initiator, and specific examples include azo compounds such as 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis-2-methylbutyronitrile (AMBN), and the like; and peroxide compounds such as dibenzoyl peroxide.

[0229] The above-described first alkali-soluble resin (B-1) can be used alone or in a mixture of a plurality of types.

[0230] In addition, the above-described first alkali-soluble resin (B-1) has a number average molecular weight of 1,000 to 35,000, preferably 3,000 to 30,000, and more preferably 5,000 to 25,000, as measured by gel permeation chromatography (GPC) in terms of polystyrene.

[0231] In the present embodiment, the amount of the alkali-soluble resin (B) used is 100 parts by weight, and the amount of the first alkali-soluble resin (B-1) used is 10 to 100 parts by weight, preferably 20 to 90 parts by weight, and more preferably 30 to 80 parts by weight.

[0232] Second alkali-soluble resin (B-2)

[0233] The second alkali-soluble resin (B-2) of the present embodiment is produced by polymerization of a mixture containing an epoxy compound having at least two epoxy groups (b-2-1) and a compound having at least one carboxylic acid group and at least one ethylenically unsaturated group (b-2-2). In addition to the above, the mixture can optionally contain a carboxylic anhydride compound (b-2-3) and / or an epoxy group-containing compound (b-2-4).

[0234] The epoxy compound having at least two epoxy groups (b-2-1) can have a structure represented by the following Formula (III-1) or the following Formula (III-2). Here, the statement "the epoxy compound (b-2-1) can have a structure represented by the following Formula (III-1) or the following Formula (III-2)" also encompasses the case where a compound having a structure represented by the following Formula (III-1) and a compound having a structure represented by the following Formula (III-2) are present together as the epoxy compound (b-2-1). Specifically, the aforementioned epoxy compound having at least two epoxy groups (b-2-1) is, for example, a compound having a structure represented by the following Formula (III-1):

[0235]

[0236] In formula (III-1),

[0237] R 1c , R 2c , R 3c , and R 4c each represent a hydrogen atom, a halogen atom, an alkyl group having a carbon number of 1 to 5, an alkoxy group having a carbon number of 1 to 5, an aromatic group having a carbon number of 6 to 12, or an aralkyl group having a carbon number of 6 to 12, R 1c , R 2c , R 3c , and R 4c each can be the same or different.

[0238] The epoxy compound having at least two epoxy groups of the aforementioned formula (III-1) (b-2-1) can include an epoxy group-containing bisphenol fluorene compound obtained by reacting a bisphenol fluorene compound with epihalohydrin, but is not limited thereto.

[0239] Specific examples of the aforementioned bisphenol fluorene compound can include, but are not limited to, 9,9-bis(4-hydroxy phenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-chlorophenyl)fluorene, 9,9-bis(4-hydroxy-3-bromophenyl)fluorene, 9,9-bis(4-hydroxy-3-fluorophenyl)fluorene, 9,9-bis(4-hydroxy-3-methoxyphenyl)fluorene, 9,9-bis(4-hydroxy-3,5-dimethylphenyl)fluorene, 9,9-bis(4-hydroxy-3,5-dichlorophenyl)fluorene, 9,9-bis(4-hydroxy-3,5-dibromophenyl)fluorene, or a combination thereof.

[0240] The aforementioned epihalohydrin can include, but is not limited to, 3-chloro-1,2-epichlorohydrin, 3-bromo-1,2-epibromohydrin, or a combination thereof.

[0241] The aforementioned epoxy-containing bisphenol fluorene compound obtained by reacting a bisphenol fluorene compound with an epihalohydrin includes, but is not limited to, (1) a product manufactured by Nippon Steel Chemical Co., Ltd., such as ESF-300, etc.; (2) a product manufactured by Osaka Gas Co., Ltd., such as PG-100, EG-210, etc.; (3) a product manufactured by S.M.S Technology Co., Ltd., such as SMS-F9PhPG, SMS-F9CrG, SMS-F914PG; or a combination thereof.

[0242] Secondly, the aforementioned epoxy compound having at least two epoxy groups (b-2-1) can also have a structure as shown in the following Formula (III-2):

[0243]

[0244] In Formula (III-2), R 5c to R 18c each independently represents a hydrogen atom, a halogen atom, an alkyl group having a carbon number of 1 to 8, or an aromatic group having a carbon number of 6 to 15, R 5c to R 18c each can be the same or different;

[0245] g represents an integer of 0 to 10.

[0246] The aforementioned epoxy compound having at least two epoxy groups (b-2-1) of Formula (III-2) is obtained, for example, by reacting a compound having the following Formula (III-2-1) with an epihalohydrin in the presence of an alkali metal hydroxide.

[0247]

[0248] In Formula (III-2-1), R 5c to R 18c and the definitions of g are the same as those of R 5c to R 18c and g in Formula (III-2), and are not repeated here.

[0249] Further, the epoxy compound (b-2-1) having at least two epoxy groups of the aforementioned formula (III-2) is formed, for example, by condensation reaction of a compound having the following formula (III-2-2) with a phenol in the presence of an acid catalyst, followed by dehydrohalogenation by adding an excess of halogenated propylene oxide to obtain the epoxy compound (b-2-1) having at least two epoxy groups as shown in formula (III-2).

[0250]

[0251] In formula (III-2-2), R 19c and R 20c each independently represents a hydrogen atom, a halogen atom, an alkyl group having a carbon number of 1 to 8, or an aromatic group having a carbon number of 6 to 15, and R 19c and R 20c each can be the same or different;

[0252] T 1 and T 2 each independently represents a halogen atom, an alkyl group having a carbon number of 1 to 6, or an alkoxy group having a carbon number of 1 to 6, and T 1 and T 2 each can be the same or different.

[0253] The aforementioned halogen atom is preferably chlorine or bromine, the aforementioned alkyl group can be, for example, a methyl group, an ethyl group, or a t-butyl group, and the aforementioned alkoxy group can be, for example, a methoxy group or an ethoxy group.

[0254] Specific examples of the aforementioned phenol can include, but are not limited to, phenol, cresol, ethylphenol, n-propylphenol, isobutylphenol, t-butylphenol, octylphenol, nonylphenol, xylenol, methylbutylphenol, di-t-butylphenol, vinylphenol, propenylphenol, ethinylphenol, cyclopentylphenol, cyclohexylphenol, or cyclohexylcresol, and the like. The aforementioned phenol can be used alone or in a mixture of a plurality of kinds.

[0255] The amount of the phenol compound used is preferably 2 to 15 moles based on 1 mole of the compound having the structure of formula (III-2-2).

[0256] Specific examples of the acid catalyst include, but are not limited to, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, oxalic acid, boron trifluoride, anhydrous aluminium chloride, zinc chloride, and the like, with p-toluenesulfonic acid, sulfuric acid, or hydrochloric acid being preferred. The acid catalyst can be used alone or in a mixture of two or more.

[0257] The amount of the acid catalyst used is not particularly limited, but is preferably 0.1 to 30 wt% based on 100 wt% of the compound having the structure of formula (III-2-2).

[0258] The condensation reaction can be carried out in the absence of a solvent or in the presence of an organic solvent. Specific examples of the organic solvent include, but are not limited to, toluene, xylene, methylisobutyl ketone, and the like. The organic solvent can be used alone or in a mixture of two or more.

[0259] The amount of the organic solvent used is preferably 50 to 300 wt% based on 100 wt% of the total amount of the compound having the structure of formula (III-2-2) and the phenol compound, with 100 to 250 wt% being more preferred. The condensation reaction is carried out at a temperature of 40 to 180°C for 1 to 8 hours.

[0260] After the condensation reaction described above is completed, a neutralization treatment or a water washing treatment can be performed. The neutralization treatment is a treatment in which the pH of the solution after the reaction is adjusted to a pH of 3 to 7, and preferably a pH of 5 to 7. The water washing treatment can be performed using a neutralizing agent, which is a basic substance, and specific examples thereof include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; organic amines such as diethylene triamine, triethylene tetramine, aniline, and phenylene diamine; and ammonia and sodium dihydrogen phosphate. The water washing treatment can be performed by a known method, for example, by repeatedly performing extraction by adding an aqueous solution containing the neutralizing agent to the solution after the reaction. After the neutralization treatment or the water washing treatment, the unreacted phenol and the solvent are distilled off by a reduced pressure heating treatment, and then concentrated, to obtain a compound having the structure of formula (III-2-1).

[0261] Specific examples of the halogenated propylene oxide include, but are not limited to, 3-chloro-1,2-epoxypropane, 3-bromo-1,2-epoxypropane, or a combination thereof. Before the dehydrohalogenation reaction described above is performed, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide can be added in advance or during the reaction. The dehydrohalogenation reaction is performed at a temperature of 20°C to 120°C for 1 hour to 10 hours.

[0262] In this embodiment, the alkali metal hydroxide added in the dehydrohalogenation reaction described above can also be used as an aqueous solution. In this embodiment, while the aqueous solution of the alkali metal hydroxide is continuously added to the dehydrohalogenation reaction system, water and the halogenated propylene oxide can be continuously distilled off under reduced pressure or normal pressure, thereby separating and removing the water, and the halogenated propylene oxide can be continuously refluxed into the reaction system.

[0263] Before the above dehydrohalogenation reaction, a quaternary ammonium salt such as tetramethyl ammonium chloride, tetramethyl ammonium bromide, trimethylbenzyl ammonium chloride, or the like can be added as a catalyst, and the reaction can be carried out at 50°C to 150°C for 1 hour to 5 hours, and then an alkali metal hydroxide or an aqueous solution thereof can be added and the reaction can be carried out at 20°C to 120°C for 1 hour to 10 hours to perform the dehydrohalogenation reaction.

[0264] The amount of the above halogenated propylene oxide used can be 1 equivalent to 20 equivalents, preferably 2 equivalents to 10 equivalents, based on 1 equivalent of the total amount of the hydroxyl groups in the compound having the structure of formula (III-2-1). The amount of the alkali metal hydroxide added in the above dehydrohalogenation reaction can be 0.8 equivalents to 15 equivalents, preferably 0.9 equivalents to 11 equivalents, based on 1 equivalent of the total amount of the hydroxyl groups in the compound having the structure of formula (III-2-1).

[0265] In addition, in order to smoothly perform the above dehydrohalogenation reaction, in addition to an alcohol such as methanol or ethanol, a polar solvent such as dimethyl sulfone or dimethyl sulfoxide can be added and the reaction can be performed. In the case where an alcohol is used, the amount of the alcohol used can be 2 wt% to 20 wt%, preferably 4 wt% to 15 wt%, based on 100 wt% of the total amount of the halogenated propylene oxide. In the case where a polar solvent is used, the amount of the polar solvent used can be 5 wt% to 100 wt%, preferably 10 wt% to 90 wt%, based on 100 wt% of the total amount of the halogenated propylene oxide.

[0266] After the dehydrohalogenation reaction is completed, a water washing process can be optionally performed. Thereafter, the halogenated propylene oxide, the alcohol, and the polar solvent can be removed by heating under reduced pressure. The above heating under reduced pressure can be performed at a temperature of 110°C to 250°C and a pressure of 1.3 kPa (10 mmHg) or less.

[0267] To avoid the formation of the epoxy resin containing hydrolyzable halogen, the solution after the dehydrohalogenation reaction can be added to a solvent such as toluene, methyl isobutyl ketone, etc., and an aqueous alkali metal hydroxide solution such as sodium hydroxide, potassium hydroxide, etc., is added, and the dehydrohalogenation reaction is performed again. In the dehydrohalogenation reaction, based on 1 equivalent of the total amount of the hydroxyl groups in the compound having the structure of formula (III-2-1) described above, the amount of the alkali metal hydroxide used is 0.01 to 0.3 moles, and preferably 0.05 to 0.2 moles. In addition, the operation temperature range of the dehydrohalogenation reaction described above is 50 to 120°C, and the operation time range thereof is 0.5 to 2 hours.

[0268] After the completion of the dehydrohalogenation reaction, salts are removed by filtration, water washing, etc. In addition, the solvent such as toluene, methyl isobutyl ketone, etc., can be distilled off by heating under reduced pressure, and an epoxy compound (b-2-1) having at least two epoxy groups shown in formula (III-2) can be obtained. The epoxy compound (b-2-1) having at least two epoxy groups shown in formula (III-2) described above can include, but is not limited to, products manufactured by Nippon Kayaku Co. Ltd. under the trade names of NC-3000, NC-3000H, NC-3000S, and NC-3000P, etc.

[0269] The aforementioned compound (b-2-2) having at least one carboxylic acid group and at least one ethylenic unsaturated group is, for example, selected from the group consisting of (1) acrylic acid, methacrylic acid, 2-methacryloyloxyethyl butanedioic acid, 2-methacryloyloxybutyl butanedioic acid, 2-methacryloyloxyethyl adipic acid, 2-methacryloyloxybutyl adipic acid, 2-methacryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl maleic acid, 2-methacryloyloxypropyl maleic acid, 2-methacryloyloxybutyl maleic acid, 2-methacryloyloxypropyl butanedioic acid, 2-methacryloyloxypropyl adipic acid, 2-methacryloyloxypropyl tetrahydrophthalic acid, 2-methacryloyloxypropyl phthalic acid, 2-methacryloyloxybutyl phthalic acid, or 2-methacryloyloxybutyl hydrogenphthalic acid; (2) a compound obtained by reacting a hydroxyl group-containing (meth)acrylate with a dibasic acid compound, wherein the dibasic acid compound includes, but is not limited to, adipic acid, succinic acid, maleic acid, phthalic acid; (3) a half-ester compound obtained by reacting a hydroxyl group-containing (meth)acrylate with a carboxylic anhydride compound, wherein the hydroxyl group-containing (meth)acrylate includes, but is not limited to, (2-hydroxyethyl) acrylate, (2-hydroxyethyl) methacrylate, (2-hydroxypropyl) acrylate, (2-hydroxypropyl) methacrylate, (4-hydroxybutyl) acrylate, (4-hydroxybutyl) methacrylate, or pentaerythritol trimethacrylate, and the like. In addition, the carboxylic anhydride compound (b-2-3) contained in the mixture of the second alkali-soluble resin (B-2) described hereinafter can be the same as the carboxylic anhydride compound (b-2-2) described here, and thus will not be described again.

[0270] The mixture of the above-mentioned second alkali-soluble resin (B-2) can more optionally contain a carboxylic anhydride compound (b-2-3) and / or an epoxy group-containing compound (b-2-4). The above-mentioned carboxylic anhydride compound (b-2-3) can be selected from the group consisting of (1) butanedioic anhydride, maleic anhydride, Itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylendo-methylene tetrahydro phthalic anhydride, chlorendic anhydride, glutaric anhydride, or 1,3-dioxoisobenzofuran-5-carboxylic anhydride, and the like, a dibasic carboxylic anhydride compound; and (2) benzophenone tetracarboxylic dianhydride (BTDA), bisphenyl tetracarboxylic dianhydride, or bisphenyl ether tetracarboxylic dianhydride, and the like, a tetrabasic carboxylic anhydride compound.

[0271] The above-mentioned epoxy group-containing compound (b-2-4) is, for example, selected from the group consisting of glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, an unsaturated group-containing glycidyl ether compound, an epoxy group-containing unsaturated compound, or any combination of the above. The aforementioned unsaturated group-containing glycidyl ether compound includes, but is not limited to, compounds with trade names of Denacol EX-111, EX-121 Denacol, Denacol EX-141, Denacol EX-145, Denacol EX-146, Denacol EX-171, Denacol EX-192, and the like (all of which are products of NAGASE & CO., LTD.).

[0272] The aforementioned second alkali-soluble resin (B-2) can be produced by reacting an epoxy compound (b-2-1) having at least two epoxy groups of formula (III-1) with a compound (b-2-2) having at least one carboxylic acid group and at least one ethylenic unsaturated group to form a reaction product containing a hydroxyl group, followed by further adding a carboxylic anhydride compound (b-2-3) and reacting. The equivalent amount of the acid anhydride group contained in the carboxylic anhydride compound (b-2-3) is preferably 0.4 equivalents to 1 equivalent, more preferably 0.75 equivalents to 1 equivalent, based on 1 equivalent of the total equivalent amount of the hydroxyl group of the aforementioned reaction product containing a hydroxyl group. When a plurality of carboxylic anhydride compounds (b-2-3) are used, they can be added sequentially or simultaneously in the reaction. When a dibasic carboxylic anhydride compound and a tetrabasic carboxylic anhydride compound are used as the carboxylic anhydride compound (b-2-3), the molar ratio of the dibasic carboxylic anhydride compound to the tetrabasic carboxylic anhydride compound is preferably 1 / 99 to 90 / 10, more preferably 5 / 95 to 80 / 20. In addition, the operating temperature range of the aforementioned reaction is, for example, in the range of 50°C to 130°C.

[0273] The aforementioned second alkali-soluble resin (B-2) can be produced by reacting an epoxy compound (b-2-1) having at least two epoxy groups of formula (III-1) with a compound (b-2-2) having at least one carboxylic acid group and at least one ethylenic unsaturated group to form a reaction product containing a hydroxyl group, followed by further adding a carboxylic anhydride compound (b-2-3) and reacting. The equivalent amount of the acid anhydride group contained in the carboxylic anhydride compound (b-2-3) is preferably 0.4 equivalents to 1 equivalent, more preferably 0.75 equivalents to 1 equivalent, based on 1 equivalent of the total equivalent amount of the hydroxyl group of the aforementioned reaction product containing a hydroxyl group. When a plurality of carboxylic anhydride compounds (b-2-3) are used, they can be added sequentially or simultaneously in the reaction. When a dibasic carboxylic anhydride compound and a tetrabasic carboxylic anhydride compound are used as the carboxylic anhydride compound (b-2-3), the molar ratio of the dibasic carboxylic anhydride compound to the tetrabasic carboxylic anhydride compound is preferably 1 / 99 to 90 / 10, more preferably 5 / 95 to 80 / 20. In addition, the operating temperature range of the aforementioned reaction is, for example, in the range of 50°C to 130°C.

[0274] In the preparation of the above-mentioned second alkali-soluble resin (B-2), in order to accelerate the reaction, a basic compound is usually added to the reaction solution as a reaction catalyst. The above-mentioned reaction catalyst can be used alone or in combination, and the above-mentioned reaction catalyst includes, but is not limited to, triphenyl phosphine, triphenyl stibine, triethylamine, triethanolamine, tetramethyl ammonium chloride, benzyltriethyl ammonium chloride, and the like. Based on the total amount of the above-mentioned epoxy compound having at least two epoxy groups (b-2-1) and the compound having at least one carboxylic acid group and at least one ethylenically unsaturated group (b-2-2) being 100 parts by weight, the amount of the reaction catalyst used is preferably 0.01 to 10 parts by weight, more preferably 0.3 to 5 parts by weight.

[0275] In addition, in order to control the degree of polymerization, a polymerization inhibitor is usually also added to the reaction solution. The above-mentioned polymerization inhibitor can include, but is not limited to, methoxyphenol, methylhydroquinone, hydroquinone, 2,6-di-t-butyl-p-cresol, or phenothiazine, and the like. In general, the above-mentioned polymerization inhibitor can be used alone or in combination. Based on the total amount of the above-mentioned epoxy compound having at least two epoxy groups (b-2-1) and the compound having at least one carboxylic acid group and at least one ethylenically unsaturated group (b-2-2) being 100 parts by weight, the amount of the polymerization inhibitor used is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight.

[0276] In the production of the second alkali-soluble resin (B-2), a polymerization reaction solvent can be used as necessary. As specific examples of the above polymerization reaction solvent, there can be mentioned, for example, alcohol compounds such as ethanol, propanol, isopropanol, butanol, isobutanol, 2-butanol, hexanol or ethylene glycol; ketone compounds such as methyl ethyl ketone or cyclohexanone; aromatic hydrocarbon compounds such as toluene or xylene; cellosolve compounds such as cellosolve or butyl cellosolve; carbitol compounds such as carbitol or butyl carbitol; propylene glycol alkyl ether compounds such as propylene glycol monomethyl ether; poly(propylene glycol) alkyl ether compounds such as di(propylene glycol) methyl ether; acetate compounds such as ethyl acetate, butyl acetate, ethylene glycol monoethyl ether acetate or propylene glycol methyl ether acetate; alkyl lactate compounds such as ethyl lactate or butyl lactate; or dialkyl glycol ethers; or ethyl 3-ethoxypropionate. The above polymerization reaction solvent can generally be used alone or in a mixture of a plurality of kinds. In addition, the acid value of the above second alkali-soluble resin (B-2) is preferably from 50 mgKOH / g to 200 mgKOH / g, more preferably from 60 mgKOH / g to 150 mgKOH / g.

[0277] In addition, the number average molecular weight of the above second alkali-soluble resin (B-2) in terms of polystyrene as measured by a gel permeation chromatograph is from 500 to 10,000, preferably from 800 to 8,000, more preferably from 1,000 to 6,000.

[0278] The above second alkali-soluble resin (B-2) can be used alone or in a mixture of a plurality of kinds.

[0279] In the present embodiment, the use amount of the alkali-soluble resin (B) is 100 parts by weight, and the use amount of the second alkali-soluble resin (B-2) is from 0 to 90 parts by weight, preferably from 10 to 80 parts by weight, more preferably from 20 to 70 parts by weight.

[0280] The alkali-soluble resin (B) can be 2.5 to 70% by weight, preferably 5 to 60% by weight, and more preferably 10 to 50% by weight, based on the total weight of the solid content of the photosensitive colored resin composition being 100% by weight.

[0281] The photopolymerizable compound (C)

[0282] The photopolymerizable compound (C) of the present embodiment can include an unsaturated compound having at least one ethylenic unsaturated group and an unsaturated compound having at least two ethylenic unsaturated groups.

[0283] Specific examples of the unsaturated compound having at least one ethylenic unsaturated group can include, but are not limited to, acrylamide, acryloyl morpholine, methacryloyl morpholine, 7-amino-3,7-dimethyloctyl acrylate, 7-amino-3,7-dimethyloctyl methacrylate, isobutyloxy methyl acrylamide, isobutyloxy methyl methacrylamide, isobutyloxy ethyl acrylate, isobutyloxy ethyl methacrylate, isobutyl acrylate, isobutyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, ethyldiglycol acrylate, ethyldiglycol methacrylate, t-octyl acrylamide, t-octyl methacrylamide, diacetonacrylamide, diacetonamethacrylamide, dimethylamino acrylate, dimethylamino methacrylate, dodecyl acrylate, dodecyl methacrylate, dicyclopentenyloxy ethyl acrylate, dicyclopentenyloxy ethyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, N,N-dimethyl acrylamide, N,N-dimethyl methacrylamide, tetrachlorophenyl acrylate, tetrachlorophenyl methacrylate, 2-tetrachlorophenoxy ethyl acrylate, 2-tetrachlorophenoxy ethyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, tetrabromophenyl acrylate, tetrabromophenyl methacrylate, 2-tetrabromophenoxy ethyl acrylate, 2-tetrabromophenoxy ethyl methacrylate, 2-trichlorophenoxy ethyl acrylate, 2-trichlorophenoxy ethyl methacrylate, tribromophenyl acrylate, tribromophenyl methacrylate, 2-tribromophenoxy ethyl acrylate, 2-tribromophenoxy ethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, vinyl caprolactam, N-vinyl piperidone, phenoxy ethyl acrylate, phenoxy ethyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, polyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monoacrylate, polypropylene glycol monomethacrylate, isobornyl acrylate, isobornyl methacrylate, or a combination thereof. Among them, the unsaturated compound having at least one ethylenic unsaturated group can be used alone or in a mixture of a plurality of kinds.

[0284] Specific examples of the above unsaturated compound having at least two ethylenically unsaturated groups can include, but are not limited to, ethylene glycol diacrylate, ethylene glycol dimethacrylate, dicyclopentenyl diacrylate, dicyclopentenyl dimethacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, tri(2-hydroxyethyl) isocyanurate diacrylate, tri(2-hydroxyethyl) isocyanurate dimethacrylate, tri(2-hydroxyethyl) isocyanurate triacrylate, tri(2-hydroxyethyl) isocyanurate trimethacrylate, caprolactone-modified tri(2-hydroxyethyl) isocyanurate triacrylate, caprolactone-modified tri(2-hydroxyethyl) isocyanurate trimethacrylate, trihydroxymethylpropyl triacrylate, trihydroxymethylpropyl trimethacrylate, ethyleneoxy (hereinafter referred to as EO)-modified trihydroxymethylpropyl triacrylate, EO-modified trihydroxymethylpropyl trimethacrylate, propyleneoxy (hereinafter referred to as PO)-modified trihydroxymethylpropyl triacrylate, PO-modified trihydroxymethylpropyl trimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, polyester diacrylate, polyester dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, dipentaerythritol hexaacrylate (DPHA), dipentaerythritol hexamethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol tetraacrylate, dipentaerythritol tetramethacrylate, caprolactone-modified dipentaerythritol hexaacrylate, caprolactone-modified dipentaerythritol hexamethacrylate, caprolactone-modified dipentaerythritol pentaacrylate, caprolactone-modified dipentaerythritol pentamethacrylate, ditrimethylolpropane tetraacrylate, ditrimethylolpropane tetramethacrylate, EO-modified bisphenol A diacrylate, EO-modified bisphenol A dimethacrylate, PO-modified bisphenol A diacrylate, PO-modified bisphenol A dimethacrylate, EO-modified hydrogenated bisphenol A diacrylate, EO-modified hydrogenated bisphenol A dimethacrylate, PO-modified hydrogenated bisphenol A diacrylate, PO-modified hydrogenated bisphenol A dimethacrylate, PO-modified glycerol tripropionate, EO-modified bisphenol F diacrylate, EO-modified bisphenol F dimethacrylate, phenol novolac polyglycidyl ether acrylate, phenol novolac polyglycidyl ether methacrylate, a product manufactured by Toagosei Co., Ltd., Japan, and having a product number of TO-1382, or a product manufactured by Nippon Kayaku Co., Ltd., Japan, and having a product number of KAYARAD DPCA-12, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, or KAYARAD DPCA-120, or the like. Of these, the unsaturated compound having at least two ethylenic unsaturated groups can be used alone or in a mixture of a plurality of kinds.

[0285] Specific examples of the photopolymerizable compound (C) are preferably trihydroxymethylpropyl triacrylate, EO-modified trihydroxymethylpropyl trimethacrylate, EO-modified trihydroxymethylpropyl triacrylate, PO-modified trihydroxymethylpropyl triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol tetraacrylate, caprolactone-modified dipentaerythritol hexaacrylate, ditrimethylolpropane tetraacrylate, PO-modified glycerol tripropionate, KAYARAD DPCA-12, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, or KAYARAD DPCA-120, or a combination thereof.

[0286] More preferably, specific examples of the photopolymerizable compound (C) are dipentaerythritol hexaacrylate, dipentaerythritol tetraacrylate, EO-modified trimethylolpropionic acid trimethacrylate, or combinations thereof.

[0287] The above-mentioned photopolymerizable compound (C) can be used alone or in combination.

[0288] Based on the total weight of the solid components of the photosensitive coloring resin composition, the photopolymerizable compound (C) may be 2.5% to 75% by weight, preferably 5% to 60% by weight, and more preferably 10% to 50% by weight, based on 100% by weight.

[0289] Photoinitiator (D)

[0290] The photoinitiator (D) in this embodiment can be a free radical photoinitiator.

[0291] Photoinitiators (D) may include acetophenone compounds, biimidazole compounds, acyl oxime compounds, or combinations thereof.

[0292] The acetophenone family of compounds is selected from p-dimethylamino-acetophenone, α,α'-dimethoxyazoxy-acetophenone, 2,2'-dimethyl-2-phenyl-acetophenone, p-methoxy-acetophenone, 2-methyl-1-(4-methylthiophenyl)-2-morpholino-1-propanone, 2-benzyl-2-N,N-di-methylamino-1-(4-morpholino-phenyl)-1-butanone, or combinations thereof.

[0293] The diimidazole compound is selected from 2,2'-bis(o-chlorophenyl)-4,4',5,5'- tetraphenyl-biimidazole, 2,2'-bis(o-fluorophenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'- bis(o-methylphenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'-bis(o-methoxyphenyl)-4,4',5,5'- tetraphenyl-biimidazole, 2,2'-bis(o-ethylphenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'- bis(p-methoxyphenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'-bis(2,2',4,4'- tetramethoxyphenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'- tetraphenyl-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-biimidazole, or a combination thereof.

[0294] The acyl oxime-based compound is selected from the group consisting of Ethanone, 1 -[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1 -(O-acetyl oxime) (CGI-242 manufactured by Ciba Specialty Chemicals), 1 -[4-(benzoyl)phenyl]-heptane-1,2-dione 2-(O-benzoyloxime) (CGI-124 manufactured by Ciba Specialty Chemicals), Ethanone, 1 -[9-ethyl-6-(2-cholro-4-benzyl-thio-benzoyl)-9H-carbazole-3-yl]-, 1 -(O-acetyl oxime) (manufactured by Asahi Chemical), or a combination thereof.

[0295]

[0296] In one embodiment, the photoinitiator (D) can further include thioxanthone, 2,4-diethyl-thioxanthanone, thioxanthone-4-sulfone, benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, and the like benzophenone-based compounds; benzil, acetyl, and the like α-diketone-based compounds; benzoin and the like acyloin-based compounds; benzoinmethylether, benzoin ethylether, benzoinisopropyl ether, and the like acyloin ether-based compounds; 2,4,6-trimethyl-benzoyl-diphenyl-phosphineoxide, bis-(2,6-dimethoxy-benzoyl)-2,4,4-trimethyl-benzyl-phosphineoxide, and the like acylphosphineoxide-based compounds; anthraquinone, 1,4-naphthoquinone, and the like quinone-based compounds; phenacyl chloride, tribromomethyl-phenylsulfone, tris(trichloromethyl)-s-triazine, and the like halides; and di-tertbutylperoxide and the like peroxides. Among them, the benzophenone-based compounds are preferred, and 4,4'-bis(diethylamino)benzophenone is most preferred.

[0297] The photoinitiator (D) is preferably exemplified by 1-[4-(phenylthio)phenyl]- octane-1,2-dione 2-(O-benzoyl oxime) (for example, a product manufactured by Ciba Specialty Chemicals under the trade name of CGI-124), 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-2,2'-biimidazole, 4,4'-bis(diethylamino)benzophenone, or a combination thereof.

[0298] The above-mentioned photoinitiator (D) can be used alone or in combination of a plurality of kinds.

[0299] The photoinitiator (D) is preferably 0.1 to 30% by weight, more preferably 0.5 to 20% by weight, and even more preferably 1 to 15% by weight, based on the total weight of the photosensitive colored resin composition as 100% by weight.

[0300] Solvent (E)

[0301] The photosensitive colored resin composition of the present embodiment is prepared by dissolving each component except for the colorant (A) in the solvent (E) to prepare a liquid composition, and then adding the colorant (A) and uniformly mixing. The solvent (E) is selected so as to dissolve the alkali-soluble resin (B), the photopolymerizable compound (C), and the photoinitiator (D), and so as not to react with these components and to have an appropriate volatility. In addition, when the colorant (A) and / or the additive (F) are added, the solvent (E) is selected so as to dissolve the colorant (A) and / or the additive (F), and so as not to react with these components and to have an appropriate volatility.

[0302] In addition, the solvent (E) can be the same as the solvent used for preparing the alkali-soluble resin (B), which is not described herein. The solvent can be used alone or in combination of a plurality of kinds. The solvent (E) is preferably exemplified by propylene glycol methyl ether acetate, cyclohexanone, 3-ethoxypropyl acetate, or a combination thereof.

[0303] The content of the solvent (E) is preferably 75 to 82% by weight, more preferably 76 to 82% by weight, and even more preferably 78 to 82% by weight, based on the total weight of the photosensitive colored resin composition as 100% by weight.

[0304] Additive (F)

[0305] In the present embodiment, the photosensitive colored resin composition further includes an additive (F), such as a filler, a high-molecular compound other than the alkali-soluble resin (B), an adhesion promoter, an antioxidant, an ultraviolet absorber, an anti-aggregation agent, and the like.

[0306] The filler is exemplified by glass, aluminum, or a combination thereof.

[0307] The high molecular compound can include polyvinyl alcohol, polyethylene glycol monoalkyl ether, polyfluoropropyl acrylate, or a combination thereof.

[0308] The adhesion promoter can include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, or a combination thereof.

[0309] The antioxidant can include 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-di-tert-butylphenol, or a combination thereof.

[0310] The ultraviolet absorber can include 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorophenyl azide, alkoxyphenone, or a combination thereof.

[0311] The anti-coagulation agent can include sodium polyacrylate.

[0312] The additive (F) described above can be used alone or in combination.

[0313] The additive (F) described above is preferably 3-mercaptopropyltrimethoxysilane, 2,2-thiobis(4-methyl-6-tert-butylphenol), or a combination thereof.

[0314] The additive (F) can be 0.001 to 15% by weight, preferably 0.005 to 10% by weight, and more preferably 0.01 to 5% by weight, based on the total weight of the solid components of the photosensitive colored resin composition as 100% by weight.

[0315] <Method of preparing the photosensitive colored resin composition>

[0316] The method of preparing the photosensitive colored resin composition of the present embodiment is not particularly limited. Specifically, the method of preparing the photosensitive colored resin composition can include:

[0317] (1) a method in which the colorant (A) is first added to the solvent (E) to prepare a colorant dispersion liquid, and then the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), and the additive (F) used as necessary are added to the colorant dispersion liquid and mixed; (2) a method in which the colorant (A), the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), and the additive (F) used as necessary are simultaneously added to the solvent (E) and mixed;

[0318] (3) a method in which the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), and the additive (F) used as necessary are first added to the solvent (E) and mixed, and then the colorant (A) is added and dispersed;

[0319] and (4) a method in which the colorant (A) and a part of the alkali-soluble resin (B) are first added to the solvent (E) to prepare a colorant dispersion liquid, and then the other part of the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), and the additive (F) used as necessary are added to the colorant dispersion liquid and mixed, and the like.

[0320] Note that in the above examples, methods of dispersing the colorant (A) are listed, and when a colorant (A) having high solubility is used, a preparation procedure in which the colorant (A) is dissolved in the solvent (E) in advance, or a preparation procedure in which the colorant (A) is dissolved in the solvent (E) at the same time as the other components can be employed.

[0321] Among these methods, the methods of (1) and (4) above are preferable from the viewpoint of effectively preventing the colorant (A) from aggregating and uniformly dispersing.

[0322] The method of uniformly dispersing / mixing the components can employ mixing and / or dispersing treatment using a stirrer and / or a disperser. The disperser can include roll mills such as two-roll mills and three-roll mills, ball mills such as a ball mill and a vibration ball mill, paint conditioners, continuous disk-type bead mills, and continuous ring-type bead mills. The bead mill dispersing conditions are preferably such that the bead diameter used is 0.03 mm to 2.00 mm, more preferably 0.10 mm to 1.0 mm.

[0323] <color filter>

[0324] The present embodiment provides a color filter produced from the photosensitive colored resin composition as described above.

[0325] In particular, the color filter of the present embodiment includes a substrate (also referred to as a transparent substrate) and filter segments made of the photosensitive colored resin composition. The color filter can have red filter segments, green filter segments, and blue filter segments by appropriately selecting the kind of colorant (A) used. In addition, the color filter of the present embodiment can further include magenta filter segments, cyan filter segments, and yellow filter segments. In addition, a reflective substrate can be used instead of the transparent substrate. Examples of the transparent substrate include a glass substrate. Specific examples of the reflective substrate include a substrate using an aluminum electrode or a metal thin film as a reflective surface. In addition, a transparent electrode such as an ITO film can be formed on the substrate.

[0326] <Method for manufacturing color filter>

[0327] The color filter of the present embodiment includes filter segments made of the photosensitive colored resin composition, and the color filter is preferably formed on a substrate. It is also preferable to form a black matrix on a substrate (also referred to as a transparent substrate) first, and then form filter segments made of the photosensitive colored resin composition to produce the color filter. In addition, the black matrix can be formed after a thin film transistor (TFT) is formed on the substrate.

[0328] Specific examples of the black matrix include chromium, a multilayer film of chromium / chromium oxide, an inorganic film of titanium nitride, and a resin film in which a light-shielding agent is dispersed.

[0329] In one embodiment, the filter segments can be formed by a lithography process.

[0330] In the lithography process, for example, the photosensitive colored resin composition containing a colorant of a specific color is applied to a transparent substrate to form a film having a dry film thickness of about 0.2 to 5 μm. Next, the obtained film (hereinafter referred to as a first film) is exposed (irradiated with light) through a photomask having a predetermined pattern. Then, the exposed first film is developed by immersing in a solvent or an alkaline developer or spraying a developer, and the uncured portion is removed to obtain a predetermined pattern. This process is similarly performed by using a photosensitive colored resin composition having a colorant of another color to produce a color filter having filter segments of each color. In addition, a second film (oxygen barrier film) can be formed on the first film using polyvinyl alcohol or a water-soluble acrylic resin before exposure. In the case where the second film is formed, the first film is not in contact with oxygen, thereby improving the exposure sensitivity. In addition, the color filter can be heated to cure the uncured polymeric compound in the filter segments.

[0331] Specific examples of the coating device include spraying, spin coating, slit coating, and roll coating. A drying process can be performed at the time of coating. Examples of the drying device include a hot air furnace, an infrared heater, and the like.

[0332] Specific examples of the alkali developer include inorganic bases such as sodium carbonate and sodium hydroxide; and organic bases such as dimethylbenzylamine and triethanolamine. In addition, a defoaming agent and / or a surfactant can be added to the developer.

[0333] <Image display device>

[0334] The present embodiment provides an image display device including the color filter described above.

[0335] The image display device of the present embodiment is, for example, a liquid crystal display device.

[0336] First, the color filter produced from the photosensitive colored resin composition described above and a substrate provided with a thin film transistor (TFT) are arranged in opposition to each other, and a gap (cell gap) is provided between the two. Next, the peripheral portions of the color filter and the substrate are bonded with an adhesive, leaving an injection hole. Then, liquid crystal is injected into the gap between the substrate surface and the gap partitioned by the adhesive from the injection hole, and the injection hole is sealed to form a liquid crystal layer. Finally, a polarizing film and / or a phase difference film are attached to the substrate. In this way, a liquid crystal display module is formed.

[0337] Next, a light source is provided on one side of the liquid crystal display module to form a liquid crystal display device. Specific examples of the light source include a cold cathode fluorescent lamp (CCFL) and a white LED. The liquid crystal used here, i.e., the liquid crystal compound or the liquid crystal composition, is not particularly limited, and any liquid crystal compound and liquid crystal composition can be used.

[0338] The liquid crystal display device is not particularly limited and can be applied, for example, to a twisted nematic (TN) type, a super twisted nematic (STN) type, an in plane switching (IPS) panel, a vertical alignment (VA) type panel, and an optically compensated birefringence mode (OCB) type panel, and the like, which are liquid crystal display modes using color filters for coloring.

[0339] The color filter of the present embodiment can be used for applications other than liquid crystal display devices, such as solid image sensors, organic electroluminescence (EL) display devices, quantum dot display devices, electronic paper, and head-mounted displays, and the like.

[0340] Figure 1is a cross-sectional view of a liquid crystal display device 10 according to an embodiment. Figure 1 The liquid crystal display device 10 shown includes a pair of first and second transparent substrates 11 and 21 spaced apart from and facing each other, and liquid crystal LC is sealed between the first and second transparent substrates 11 and 21. The side of the first and second transparent substrates 11 and 21 close to the liquid crystal LC is defined as an inner surface, and the side of the first and second transparent substrates 11 and 21 away from the liquid crystal LC is defined as an outer surface, respectively.

[0341] The liquid crystal LC is aligned in response to a driving mode such as TN, STN, IPS, VA, and OCB.

[0342] A TFT (Thin Film Transistor) array 12 is formed on the inner surface of the first transparent substrate 11, and a first transparent electrode layer 13 made of, for example, ITO is formed thereon. A first alignment layer 14 is provided on the first transparent electrode layer 13. Further, a first polarizing plate 15 is provided on the outer surface of the transparent substrate 11.

[0343] On the other hand, a color filter 22 according to the present embodiment is formed on the inner surface of the second transparent substrate 21. The color filter 22 includes a red filter segment (not shown), a green filter segment (not shown), and a blue filter segment (not shown), and these filter segments are separated by a black matrix (not shown).

[0344] A transparent protective film (not shown) is formed as needed to cover the color filter 22, and a second transparent electrode layer 23 made of, for example, ITO is formed on the color filter 22, and a second alignment layer 24 is formed to cover the second transparent electrode layer 23. Further, a second polarizing plate 25 is formed on the outer surface of the second transparent substrate 21.

[0345] Further, a backlight unit 30 is provided below the first polarizing plate 15. Further, a white LED light source 31 is provided on one side of the backlight unit 30. The white LED light source 31 includes a light source in which a phosphor filter is formed on the surface of a blue LED, and a light source in which a phosphor is contained in a resin package of a blue LED.

[0346] The image display device according to the present embodiment can include a liquid crystal display device, an organic electroluminescent display device, a quantum dot display device, electronic paper, a head-mounted display, and the like.

[0347] The present application will be further illustrated with the following experimental examples, but it should be understood that these experimental examples are only illustrative and should not be interpreted as limiting the practice of the present application.

[0348] Synthesis Example of Alkali-soluble Resin (B)

[0349] Synthesis Example B-1

[0350] One part by weight of 2,2'-azobisisobutylonitrile, 240 parts by weight of propylene glycol methyl ether acetate, 20 parts by weight of methacrylic acid, 15 parts by weight of styrene, 35 parts by weight of phenyl methacrylate, and 30 parts by weight of nitrogen-phenyl maleimide were placed in a round bottom flask equipped with a stirrer and a condenser, and the inside of the flask was filled with nitrogen, after which, the reaction mixture was uniformly mixed and polymerization was performed at 80°C for 4 hours while slowly stirring. Thereafter, it was further heated to 100°C, and 0.5 parts by weight of 2,2'-azobisisobutylonitrile was added to perform polymerization for 1 hour, and a reaction solution was obtained. The reaction solution was poured into 1500 ml of water to precipitate the polymer, and the polymer was filtered. Subsequently, it was placed in a vacuum oven and dried at 60°C, and a first alkali-soluble resin of Synthesis Example B-1 was obtained.

[0351] Synthesis Example B-2

[0352] Two parts by weight of 2,2'-azobisisobutylonitrile, 300 parts by weight of dipropylene glycol methyl ether, 15 parts by weight of methacrylic acid, 15 parts by weight of 2-hydroxyethyl acrylate, and 70 parts by weight of phenyl methacrylate were placed in a round bottom flask equipped with a stirrer and a condenser, and the inside of the flask was filled with nitrogen, after which, the reaction mixture was uniformly mixed and polymerization was performed at 80°C for 3 hours while slowly stirring. Thereafter, it was further heated to 100°C, and 0.5 parts by weight of 2,2'-azobisisobutylonitrile was added to perform polymerization for 1 hour, and a reaction solution was obtained. The reaction solution was poured into 1500 ml of water to precipitate the polymer, and the polymer was filtered. Subsequently, it was placed in a vacuum oven and dried at 60°C, and a first alkali-soluble resin of Synthesis Example B-2 was obtained.

[0353] Examples 1 to 11 and Comparative Examples 1 to 5

[0354] Examples 1 to 11 and Comparative Examples 1 to 5 of the photosensitive colored resin composition are described below:

[0355] Example 1

[0356] a. Preparation of the photosensitive colored resin composition

[0357] First, 5 parts by weight of the dibenzophenanthrene-based colorant (a1-5), 20 parts by weight of the other colorant (a2-1), 12.5 parts by weight of Ajisper PB821 (manufactured by Ajinomoto Fine-Techno) (as a dispersant), 150 parts by weight of propylene glycol methyl ether acetate (PGMEA, manufactured by Daicel-Allnex), and 562.5 parts by weight of zirconia beads having a particle diameter of 2 mm were placed in a wide-mouth bottle, and after preliminary pulverization for 1 hour using a paint shaker (PCMH-C50M, manufactured by Hata Iron Works), the solution was transferred to another wide-mouth bottle, 562.5 parts by mass of zirconia beads having a particle diameter of 0.1 mm were added, and after vibration for 20 hours using a paint shaker, filtration was performed through a filter having a pore size of 5.0 μm to obtain a colorant dispersion liquid having a solid content of 20%.

[0358] Next, 187.5 parts by weight of the above colorant dispersion liquid (containing 5 parts by weight of the dibenzophenanthrene-based colorant (a1-5) and 20 parts by weight of the other colorant (a2-1)), 20 parts by weight of the first alkali-soluble resin of Synthesis Example b-1 (hereinafter referred to as b-1), 37.9 parts by weight of dipentaerythritol hexaacrylate (hereinafter referred to as c-1), 7 parts by weight of 1-[4-(phenylthio)phenyl]-octane-1,2-dione 2-(O-benzoyl oxime) (trade name: OXE-01, manufactured by BASF) (hereinafter referred to as d-1), and 0.1 parts by weight of 3-mercapto propyl trimethoxysilane (hereinafter referred to as f-1) were added to 300 parts by weight of PGMEA (hereinafter referred to as e-1), and after uniform stirring with a shaking type stirrer, a photosensitive colored resin composition of Example 1 was obtained, having a solid content of 20.0% by weight.

[0359] b. Production of a pattern (color layer for a color filter)

[0360] The photosensitive colored resin composition of Example 1 was applied to a glass substrate having a size of 100 mm x 100 mm by spin coating, and after preliminary drying at a pressure of 100 mmHg for 30 seconds, a preliminary baking step was performed at a temperature of 90°C for 2 minutes to form a preliminary baked coating film having a thickness of 2.4 μm. The preliminary baked coating film was then exposed to ultraviolet light (exposure machine: Canon PLA-501F) at 100 mJ / cm2, and after development with 2.38% by weight of an aqueous ammonium fluoride solution, a pattern was formed. 2After the pre-baking coating film was irradiated with an amount of light, the film was immersed in a developing solution at 23°C for 1 minute, washed with pure water, and then post-baked at 200°C for 20 minutes to form a pattern (which can be used as a colored layer of a color filter) on a glass substrate with a film thickness of 2.0 μm.

[0361] The pattern of Example 1 thus obtained was evaluated in the following manner, and the results are shown in Table 1.

[0362] Examples 2 to 11 and Comparative Examples 1 to 5

[0363] The photosensitive colored resin compositions and colored layers (color filters) of Examples 2 to 11 and Comparative Examples 1 to 5 were produced in the same manner as in Example 1, except that the types and amounts of the components of the photosensitive colored resin compositions and the content of the solid components were changed. The components corresponding to the symbols in Tables 1 and 2 are shown in Table 3. The photosensitive colored resin compositions thus obtained were evaluated in the following manner, and the results of Examples 2 to 11 and Comparative Examples 1 to 5 are shown in Tables 1 and 2, respectively.

[0364] Control group

[0365] Production of photosensitive colored resin composition

[0366] First, 5 parts by weight of the diphenyl furan-based colorant (a'-l), 20 parts by weight of the other colorant (a2-3), 12.5 parts by weight of Ajisper PB821 (as a dispersant), 150 parts by weight of PGMEA, and 562.5 parts by weight of zirconia beads having a particle size of 2 mm were placed in a jar, and the solution was subjected to preliminary pulverization for 1 hour using a paint shaker (PCMH-C50M, Asada Iron Works). The solution was then transferred to another jar, 562.5 parts by weight of zirconia beads having a particle size of 0.1 mm were added, and the solution was shaken for 20 hours using a paint shaker. The solution was then filtered through a filter having a pore size of 5.0 μm to obtain a colorant dispersion liquid of the control example, which had a solid content of 20%.

[0367] Next, 187.5 parts by weight of the colorant dispersion liquid (which contained 5 parts by weight of the diphenyl furan-based colorant (a'-l) and 20 parts by weight of the other colorant (a2-3)), 20 parts by weight of b-l, 37.9 parts by weight of c-l, 7 parts by weight of d-l, and 0.1 parts by weight of f-l were added to 487 parts by weight of e-l, and the mixture was stirred uniformly using a shaking type stirrer to produce a photosensitive colored resin composition of the control example, which had a solid content of 15.0% by weight.

[0368] [Table 1]

[0369]

[0370] [Table 2]

[0371]

[0372] [Table 3]

[0373]

[0374]

[0375]

[0376]

[0377] [evaluation method]

[0378] [1] Relative total VOC reduction rate

[0379] First, the first experimental procedure of the control group was performed to obtain the total VOC amount X (ppm). Specifically, the photosensitive colored resin composition of the control example was applied to a 100 mm x 100 mm glass substrate in a spin coating manner, and a transparent cover having an openable and closable hole was covered over the coating film, and then heat treatment at 90°C was performed. After 60 minutes, a coating film having a dry film thickness of 2.4 μm was formed. After the heat treatment, a handheld VOC meter (model Tiger ppm; manufactured by Ion Science) was inserted into the hole simultaneously to measure the VOC amount, and the VOC amount X1 (ppm) was obtained. After repeating the above operation for a total of 5 times, the VOC amounts X2 to X5 were obtained, respectively, and finally the total VOC amount X (ppm) was obtained by adding X1 to X5.

[0380] Next, the second experimental procedure of the experimental group was performed to obtain the total VOC amount Y (ppm). The photosensitive colored resin compositions of the examples and the comparative examples were applied to a 100 mm x 100 mm glass substrate in a spin coating manner. Then, heat treatment was performed under the same conditions and procedures as the first experimental procedure of the control group to form a coating film having a dry film thickness of 2.4 μm. After the heat treatment, VOC measurement was performed simultaneously, and after repeating the operation for a total of 5 times, the VOC amounts Y1 to Y5 were obtained, respectively, and finally the other total VOC amount Y (ppm) was obtained by adding Y1 to Y5.

[0381] The relative total VOC reduction rate was calculated according to the following formula. The larger the value of the relative total VOC reduction rate, the higher the effect of reducing the total VOC amount. In addition, when Y > X, that is, it does not have the effect of reducing VOC, the calculation of the following formula is not performed, and the evaluation result is x.

[0382] Relative total VOC reduction rate (%) = (X - Y) / X x 100 (%)

[0383] O: Relative total VOC reduction rate > 19.5%

[0384] X: Relative total VOC reduction rate ≦ 19.5%

[0385] [2] Brightness

[0386] The brightness Y value of the colored layer was measured using a colorimeter (Model MCPD, manufactured by Otsuka Electronics Co., Ltd.) under a C light source with a 2-degree field of view, and a larger Y value indicated a higher brightness, and the Y value was evaluated according to the following criteria:

[0387] : Y value ≧ 15;

[0388] O: 13 ≦ Y value < 15;

[0389] : 11 ≦ Y value < 13;

[0390] X: Y value < 11.

[0391] [3] Pattern property

[0392] The pattern property of the optical filter piece was confirmed using a scanning electron microscope (SEM) (Model S-3000H, manufactured by Hitachi High Tech). Specifically, an SEM image of the stripe pattern with a width of 100 μm was taken, and the gradient angle of the cross section of the stripe pattern (the included angle between the glass substrate and the pattern) was evaluated using a protractor according to the following criteria.

[0393] : 55° < gradient angle ≦ 70°

[0394] O: 45° < gradient angle ≦ 55°

[0395] : 35° < gradient angle ≦ 45°

[0396] X: gradient angle ≦ 35° or gradient angle > 70°

[0397] <Results of evaluation>

[0398] As shown in Table 1 and Table 2, when the content of the solid component is controlled in the range of 18 to 25% by weight (Examples 1 to 11) under the condition that the colorant (A) includes the dibenzofuran-based colorant (A-1) represented by Formula (I), the photosensitive colored resin composition can have a colored layer (pattern) with good brightness and pattern properties while giving consideration to high solid content and improvement of the relative total VOC reduction rate in the production process of the color filter formed of the photosensitive colored resin composition.

[0399] On the contrary, when the content of the solid component of the photosensitive colored resin composition is less than 18% by weight (Comparative Examples 3 and 5), the photosensitive colored resin composition does not have the effect of relative total VOC reduction.

[0400] Also, when the content of the solid component of the photosensitive colored resin composition is more than 25% by weight (Comparative Example 4) under the condition that the colorant (A) includes the dibenzofuran-based colorant (A-1) represented by Formula (I), the colored layer (pattern) formed of the photosensitive colored resin composition has poor brightness and pattern properties.

[0401] Also, when the photosensitive colored resin composition does not include the dibenzofuran-based colorant (A-1) represented by Formula (I) (Comparative Examples 1 and 2), the colored layer (pattern) formed of the photosensitive colored resin composition has poor brightness and pattern properties.

[0402] Also, when the content of the solid component is 18 to 22% by weight based on the total weight of the photosensitive colored resin composition being 100% by weight (Examples 1 to 5), the pattern properties of the colored layer (pattern) formed of the photosensitive colored resin composition are better.

[0403] Also, when Formula (I) preferably has at least two -SO3 - , and R9 is -SO3 - , and R7 is a hydrogen atom or -SO3 - (Examples 1 to 3, Example 6, and Example 7), the brightness of the colored layer (pattern) formed of the photosensitive colored resin composition can be further improved.

[0404] In addition, when R 11 , R 12 , and R 13 each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 20 atoms, a polyether structure, and R 11 , R 12 , and R 13When at least one of the polyether structures (Examples 1 to 3, Example 8, Example 9) is present, the brightness of the colored layer (pattern) formed from the photosensitive colored resin composition can be further improved.

[0405] As described above, the present embodiment provides a photosensitive colored resin composition, a color filter, and an image display device, which, by limiting the colorant (A) to include a dibenzophuran-based colorant (A-1) represented by Formula (I), and limiting the content of the solid component to 18 to 25 wt%, can achieve good colored layer (pattern) brightness and pattern properties while simultaneously taking into account high solid content and a relative total VOC reduction rate improvement in the production process of the photosensitive colored resin composition forming the color filter, thereby achieving an environmentally friendly effect.

Claims

1. A photosensitive colored resin composition, comprising: a colorant (A) including a dibenzofuran-based colorant (A-1) represented by formula (I); an alkali-soluble resin (B); a photopolymerizable compound (C); a photoinitiator (D); and a solvent (E), wherein the content of solid components is 18 to 25% by weight based on the total weight of the photosensitive colored resin composition being 100% by weight, In formula (I), R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 to 20 which is substituted or unsubstituted, a cycloalkyl group having a carbon number of 3 to 20 which is substituted or unsubstituted, an aromatic hydrocarbon group having a carbon number of 6 to 20 which is substituted or unsubstituted, or a heterocyclic group having a carbon number of 2 to 20 which is substituted or unsubstituted, or R 1 with R 2 , or R 3 with R 4 may also be bonded to one another to form a ring; R 5 , R 6 , R 7 , R 8 , and R 9 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a -SO3 - , -SO3H, -SO3M, a linear or branched alkyl group having a carbon number of 1 to 20 which is substituted or unsubstituted, a cycloalkyl group having a carbon number of 3 to 20 which is substituted or unsubstituted, a linear or branched alkoxy group having a carbon number of 1 to 20 which is substituted or unsubstituted, a cycloalkoxy group having a carbon number of 3 to 20 which is substituted or unsubstituted, or a linear or branched alkenyl group having a carbon number of 2 to 20 which is substituted or unsubstituted, or R 5 with R 6 , R 6 with R 7 , R 7 with R 8 , or R 8 with R 9 may also be bonded to each other to form a ring; M represents an alkali metal atom; R 11 , R 12 , and R 13 each independently represent a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20, a linear or branched alkoxy group having a carbon number of 1 to 20 which is substituted or unsubstituted, an aromatic hydrocarbon group having a carbon number of 6 to 20 which is substituted or unsubstituted, a heterocyclic group having a carbon number of 2 to 20 which is substituted or unsubstituted, or a polyether structure, and R 11 , R 12 , and R 13 is a polyether structure; n represents a positive integer of 1 to 4.

2. The photosensitive colored resin composition according to claim 1, wherein the content of solid components is 18 to 23% by weight based on the total weight of the photosensitive colored resin composition being 100% by weight.

3. The photosensitive colored resin composition according to claim 1, wherein the content of solid components is 18 to 22% by weight based on the total weight of the photosensitive colored resin composition being 100% by weight.

4. The photosensitive colored resin composition according to claim 1, wherein at least two -SO3 - , and R 9 is a hydrogen atom or -SO3 - , and R 7 is a hydrogen atom or -SO3 - .

5. The photosensitive colored resin composition according to claim 1, wherein In formula (I), R 11 , R 12 , and R 13 each independently represent a substituted or unsubstituted linear or branched alkyl group having a carbon number of 1 to 20, or a polyether structure, and at least one of R 11 , R 12 , and R 13 is a polyether structure.

6. The photosensitive colored resin composition according to claim 1, wherein the dibenzofuran-based colorant (A-1) is 0.01 to 25% by weight based on the total weight of the solid components of the photosensitive colored resin composition being 100% by weight.

7. The photosensitive colored resin composition according to claim 1, wherein the colorant (A) is 1 to 85% by weight based on the total weight of the solid components of the photosensitive colored resin composition being 100% by weight, the alkali-soluble resin (B) is 2.5 to 70% by weight based on the total weight of the solid components of the photosensitive colored resin composition being 100% by weight, the photopolymerizable compound (C) is 2.5 to 75% by weight based on the total weight of the solid components of the photosensitive colored resin composition being 100% by weight, the photoinitiator (D) is 0.1 to 30% by weight based on the total weight of the solid components of the photosensitive colored resin composition being 100% by weight.

8. A color filter produced from the photosensitive colored resin composition according to any one of claims 1 to 7.

9. An image display device including the color filter according to claim 8. ​

Images