TWI903486B - Photosensitive colored resin composition, color filter, and image display device - Google Patents

Abstract

A photosensitive colored resin composition, a color filter, and an image crystal display device are provided. The photosensitive colored resin composition includes a colorant (A) including a xanthene-based colorant (A-1) represented by a formula (I), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E), wherein based on 100% by weight of the photosensitive colored resin composition, the solid content is 18% to 25% by weight.

Description

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

This invention relates to a resin composition, a filter, and a display device, and more particularly to a photosensitive colored resin composition, a color filter, and an image display device.

Image display devices using color filters include (i) color liquid crystal displays, which combine a backlight serving as a light source, a liquid crystal serving as an optical shutter, and a color filter with color adjustment functions (color conversion, color separation, and color correction, etc.); and (ii) color organic electroluminescent (EL) displays, which combine a synthetic white organic electroluminescent (EL) light source and a color filter with color adjustment functions (color conversion, color separation, and color correction, etc.). Color filters can also be used in image sensors such as complementary metal-oxide-semiconductor (CMOS) and charge-coupled devices (CCD).

Currently, known methods for manufacturing color filters include electro-deposition, printing, and photolithography. Electro-deposition involves pre-forming transparent electrodes with a predetermined pattern; then, by applying voltage, the pigment-containing resin dissolved or dispersed in a solvent is ionized to form the pattern. Printing involves offset printing using inks containing thermosetting or UV-curing resins. Photolithography uses photosensitive resin compositions in which pigments or dyes are dispersed or dissolved in a photoresist material. In recent years, photolithography has become the mainstream method for manufacturing color filters. Photolithography involves dispersing or dissolving pigments or dyes in a photoresist material, using a photosensitive resin composition.

When forming a color filter using a photolithography process, for example, after forming a coating of a negative photosensitive pigmented resin composition on a substrate, the coating is exposed to ultraviolet light through a photomask with a predetermined opening pattern. Then, the unexposed areas are dissolved and removed by developing to form the pattern (e.g., Patent 1).

Today, society is increasingly focused on ESG (Environmental, Social, and Governance) issues, especially the safety of substances closely related to and frequently encountered in daily life, such as food safety and environmental safety. With continuously rising global environmental requirements, the chemical and electronics industries are facing increasingly stringent emission standards for volatile organic compounds (VOCs) and are subject to strict monitoring of emissions. Green and environmentally friendly technologies to reduce VOC emissions during manufacturing processes are currently a major issue. Furthermore, during the color filter manufacturing process, volatile organic compounds can diffuse into the air, raising concerns about potential negative impacts on workers and the environment.

However, while manufacturing methods have been developed to increase the overall solid content of photosensitive color resins used in color filters to reduce VOC emissions, these methods also lead to problems such as reduced light transmittance of the colored layer (pattern) and pattern abnormalities.

[Patent Documents]

[Patent Document 1] JP H02-144502-A

Therefore, how to simultaneously improve the relative total VOC reduction rate in the production process of color filters with high solids content and photosensitive color resin components, while still maintaining good brightness and pattern properties of the colored layer (pattern), is an important issue today.

This invention provides a photosensitive color resin composition, a color filter, and an image display device. While simultaneously maintaining high solids content and improving the relative total VOC reduction rate in the production process of the color filter formed from the photosensitive color resin composition, the color layer (pattern) produced by the photosensitive color resin composition exhibits good brightness and pattern properties.

This invention provides a photosensitive coloring resin composition, comprising: a colorant (A) including a dibenzopiperanone colorant (A-1) represented by formula (I), an alkaline soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E), wherein the solid content is 18% to 25% by weight, based on 100% by weight of the photosensitive coloring resin composition.

In formula (I), ^R1 , ^R2 , ^R3 , and ^R4 each independently represent a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group with 2 to 20 carbon atoms. Alternatively, ^R1 and ^R2 , or ^R3 and ^R4, may be bonded together to form a ring. ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, _-SO3- , ^-SO3H , _{or -SO3} M, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, or a substituted or unsubstituted linear or branched alkenyl group having 2 to 20 carbon atoms, or ^R5 and ^R6 , ^R6 and ^R7 , ^R7 and ^R8 , or ^R8 and ^R9 may also be bonded to each other to form a ring; M represents an alkali metal atom; ^R11 , ^R12 , and R ¹³ Each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or a polyether structure, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure; n represents a positive integer from 1 to 4, and formula (I) contains at least two _-SO3- ^.

In one embodiment of the present invention, the solid content is 18% to 23% by weight, based on 100% by weight of the photosensitive coloring resin composition.

In one embodiment of the present invention, the solid content is 18% to 22% by weight, based on 100% by weight of the photosensitive coloring resin composition.

In one embodiment of the present invention, ^{R9 is} _-SO3- and ^R7 is ^a hydrogen atom or _-SO3- .

In one embodiment of the present invention, in formula (I) above, ^R11 , ^R12 , and ^R13 each independently represent a linear or branched alkyl or polyether structure having 1 to 20 carbon atoms, whether substituted or unsubstituted, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure.

In one embodiment of the invention, the dibenzopiperanone colorant (A-1) comprises 0.01% to 25% by weight of the total solid components based on the photosensitive coloring resin composition, calculated as 100% by weight.

In one embodiment of the present invention, based on a total weight percentage of 100% by weight of the solid components of the photosensitive tinted resin composition, the tinting agent (A) comprises 1% to 85% by weight, the alkali-soluble resin (B) comprises 2.5% to 70% by weight, the photopolymerizable compound (C) comprises 2.5% to 75% by weight, and the photoinitiator (D) comprises 0.1% to 30% by weight.

This invention provides a color filter made from the photosensitive tinted resin composition as described above.

This invention provides an image display device, including the color filter as described above.

Based on the above, the present invention provides a photosensitive color resin composition, a color filter, and an image display device. By limiting the colorant (A) to include dibenzopyran-based colorants (A-1) as shown in formula (I), and limiting the solid content to 18% to 25% by weight, the invention achieves a balance between high solid content and a relatively high total VOC reduction rate in the production process of the color filter formed from the photosensitive color resin composition. Furthermore, the colored layer (pattern) produced by the photosensitive color resin composition exhibits excellent brightness and pattern properties, thereby achieving an environmentally friendly effect.

To make the above-mentioned features and advantages of this invention more apparent and understandable, specific embodiments are provided below, along with detailed explanations.

10: LCD display device

11: First transparent substrate

12: TFT (Thin Film Transistor) Array

13: Transparent Electrode Layer

14: First Orientation Layer

15: First polarizing plate

21: Second transparent substrate

22: Color Filter

23: Second transparent electrode layer

24: Second Orientation Layer

25: Second polarizing plate

LC: liquid crystal

30: Backlight Unit

31: White LED light source

Figure 1 is a cross-sectional view of a liquid crystal display device according to an embodiment.

<Photosensitive pigment resin composition>

This embodiment provides a photosensitive coloring resin composition comprising: a colorant (A) including a dibenzopiperanone-based colorant (A-1), an alkaline-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E). Furthermore, the photosensitive coloring resin composition of this embodiment may optionally include an additive (F).

In this embodiment, based on 100% by weight of the photosensitive dyeing resin composition, the solid content is 18% to 25% by weight, preferably 18% to 23% by weight, and even more preferably 18% to 22% by weight.

In this article, the "solid component" of the photosensitive pigment resin composition refers to the components excluding the solvent (E); the "total weight of the solid component of the photosensitive pigment resin composition" refers to the total weight of the components excluding the solvent (E).

In this document, acrylic acid and/or methacrylic acid are referred to as (meth)acrylic acid, and acrylates and/or methacrylates are referred to as (meth)acrylates.

Provided that the colorant (A) includes a dibenzopiperanone-based colorant (A-1) as shown in formula (I) below, and when the solid content is controlled within the range of 18% to 25% by weight, the photosensitive coloring resin composition can simultaneously achieve high solid content and a relatively high total VOC reduction rate in the production process of color filters formed by the photosensitive coloring resin composition. Furthermore, the colored layer (pattern) produced by the photosensitive coloring resin composition exhibits good brightness and pattern properties.

Conversely, provided that the colorant (A) includes a dibenzopiperanone colorant (A-1) as shown in formula (I) below, when the solid content of the photosensitive coloring resin composition is less than 18% by weight, the photosensitive coloring resin composition does not have the effect of reducing the relative total VOC.

Provided that the colorant (A) includes a dibenzopiperanone-based colorant (A-1) as shown in formula (I), when the solid content of the photosensitive coloring resin composition is greater than 25% by weight, the brightness and pattern properties of the colored layer (pattern) produced by the photosensitive coloring resin composition are poor, resulting in poor overall display quality of the image display device produced by the color filter.

Furthermore, when the photosensitive coloring resin composition does not include the dibenzopiperanone colorant (A-1) shown in formula (I) below, the brightness and pattern properties of the colored layer (pattern) produced by the photosensitive coloring resin composition are poor, resulting in poor overall display quality of the image display device produced by the color filter.

When the solid content is 18% to 23% by weight (based on 100% by weight of the photosensitive pigment composition), the pigmented layer (pattern) produced by the photosensitive pigment composition exhibits better brightness and pattern quality.

When the solid content is 18% to 22% by weight (based on 100% by weight of the photosensitive coloring resin composition), the coloring layer (pattern) produced by the photosensitive coloring resin composition exhibits better brightness and pattern properties.

The components of the photosensitive tinted resin composition used in this embodiment will be described in detail below:

Colorant (A)

The colorant (A) of this embodiment includes a dibenzopiperanone colorant (A-1). Furthermore, the colorant (A) may also include other colorants (A-2) besides the dibenzopiperanone colorant (A-1).

Dibenzopiperanone colorants (A-1)

In this embodiment, the dibenzopiperanone colorant (A-1) has the structure shown in formula (I).

In formula (I), ^R1 , ^R2 , ^R3 , and ^R4 each independently represent a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group with 2 to 20 carbon atoms. Alternatively, ^R1 and ^R2 , or ^R3 and ^R4, may be bonded together to form a ring. ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, _-SO3- , ^-SO3H , _{or -SO3} M, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, or a substituted or unsubstituted linear or branched alkenyl group having 2 to 20 carbon atoms, or ^R5 and ^R6 , ^R6 and ^R7 , ^R7 and ^R8 , or ^R8 and ^R9 may also be bonded to each other to form a ring; M represents an alkali metal atom; ^R11 , ^R12 , and R ¹³ Each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or a polyether structure, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure; n represents a positive integer from 1 to 4, and formula (I) contains at least two _-SO3- ^.

In formula (I), "substituted or unsubstituted linear or branched alkyl groups with 1 to 20 carbon atoms" as represented by ^R1 , ^R2 , ^R3 , and ^R4 can specifically include: linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; and branched alkyl groups such as isopropyl, isobutyl, dibutyl, tributyl, and isooctyl.

In formula (I), "substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms" represented by ^R1 , ^R2 , ^R3 , and ^R4 can specifically include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and other cycloalkyl groups.

In equation (I), ^R1 , ^R2 , ^R3 , and R... The "substituted or unsubstituted aromatic hydrocarbons with 6 to 20 carbon atoms" or "substituted or unsubstituted heterocyclic groups with 2 to 20 carbon atoms" referred to in section ⁴ can specifically include: phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, triphenyl, peryl, indyl, fumonisyl, pyridyl, triyl, pyrroloyl, imidazolyl, pyrazolyl, triazolyl, quinolinyl, isoquinolinyl, naphthinyl, indolyl, benzimidazolyl, carbazolyl, carbazolyl, acridineyl, phenolinyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, etc.

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

In formula (I), the "substituents" in the "substituted linear or branched alkyl groups with 1 to 20 carbon atoms" represented by ^R1 , ^R2 , ^R3 , and ^R4 can specifically include halogen atoms such as fluorine, chlorine, bromine, and iodine; _-SO3- ; ^-SO3H ; _-SO3M ; cycloalkyl groups with 3 to ₁₉ carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl; linear alkoxy groups with 1 to 19 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, and decoxy; isopropoxy, isobutoxy, dibutoxy, and tributoxy. Branched alkoxy groups with 3-19 carbon atoms, such as isooctoxy; cycloalkoxy groups with 3-19 carbon atoms, such as cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexyloxy; aromatic hydrocarbons or condensed polycyclic aromatic groups with 6-19 carbon atoms, such as phenyl, naphthyl, biphenyl, anthracene group, phenanthrenyl group, pyrenyl group, triphenylene group, indole, and fumonisinyl; pyridyl, pyrimidinyl, triazinyl, pyrroleyl, imidazolyl, pyrazolyl, triazolyl, quinolinyl, isoquinolinyl, naphthidyl, indoleyl, benzimidazolyl, carbazole, and carbolinyl. (group), acridine, phenolinyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, and other heterocyclic groups with 2 to 19 carbon atoms. The "M" above represents an alkali metal atom, such as a lithium atom, sodium atom, or potassium atom.

These "substituents" may be singular or multiple, and when multiple are present, they may be identical or different. Furthermore, these "substituents" may also have the substituents exemplified above.

In formula (I), the "substituents" represented by ^R1 , ^R2 , ^R3 , and ^R4 , which are "substituted cycloalkyl groups with 3 to 20 carbon atoms", "substituted aromatic hydrocarbon groups with 6 to 20 carbon atoms", or "substituted heterocyclic groups with 2 to 20 carbon atoms", can specifically include: halogen atoms such as fluorine, chlorine, bromine, and iodine; _-SO3- ; ^-SO3H _{; -SO3} M; methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and other straight-chain alkyl groups with 1 to 14 carbons; isopropyl, isobutyl, dibutyl, tributyl, isooctyl, and other branched alkyl groups with 3 to 14 carbons; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, and other cycloalkyl groups with 3 to 14 carbons; methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, and other straight-chain alkoxy groups with 1 to 14 carbons; isopropoxy, isobutoxy, dibutoxy, tributoxy, isooctoxy, and other branched alkoxy groups with 3 to 14 carbons. Cycloalkoxy groups with 3 to 14 carbon atoms, such as cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexyloxy; aromatic hydrocarbons or condensed polycyclic aromatic groups with 6 to 14 carbon atoms, such as phenyl, naphthyl, biphenyl, anthracene, phenanthryl, indyl, and fumonisin; and heterocyclic groups with 2 to 14 carbon atoms, such as pyridyl, pyrimidinyl, triazinyl, pyrroleyl, imidazolyl, pyrazolyl, triazolyl, quinolinyl, isoquinolinyl, naphthinyl, indolyl, benzimidazolyl, carbazolyl, carbazolyl, acridineyl, phenolinyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, oxazolyl, benzooxazolyl, thiazolyl, and benzothiazolyl. The "M" above represents an alkali metal atom, such as a lithium atom, a sodium atom, or a potassium atom.

These "substituents" may be singular or multiple, and when multiple are present, they may be identical or different. Furthermore, these "substituents" may also have the substituents exemplified above.

In Equation (I), the combination of ^R1 and ^R2 and the combination of ^R3 and ^R4 can be the same or different. In Equation (I), ^R1 and ^R2 , or ^R3 and ^R4, can also be bonded to each other to form a loop. In this case, the loop formed is preferably a 5-member loop or a 6-member loop, and more preferably a 5-member loop. ^R1 and ^R2 , and ^R3 and ^R4, can form loops in two pairs or in any pair.

In formula (I), the "halogen atoms" represented by ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 can include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.

In formula (I), ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 represent "substituted or unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms", "substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms", "substituted or unsubstituted linear or branched alkoxy groups having 1 to 20 carbon atoms", "substituted or unsubstituted cycloalkoxy groups having 3 to 20 carbon atoms", or "substituted or unsubstituted cycloalkoxy groups having 2 to 20 carbon atoms". The phrase "a straight-chain or branched alkenyl group of 0" includes "an alkyl group having 1 to 20 carbon atoms that is either straight-chain or branched,""a cycloalkyl group having 3 to 20 carbon atoms,""an alkoxy group having 1 to 20 carbon atoms that is either straight-chain or branched,""a cycloalkoxy group having 3 to 20 carbon atoms," or "an alkenyl group having 2 to 20 carbon atoms that is either straight-chain or branched." Specifically, examples include: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, etc. Alkyl groups such as alkyl, octyl, nonyl, and decyl; branched alkyl groups such as isopropyl, isobutyl, dibutyl, tributyl, and isooctyl; cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl; straight-chain alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, and decoxy; and isopropyl... Branched alkoxy groups such as oxy, isobutoxy, dibutoxy, terbutoxy, and isooctoxy; cycloalkoxy groups such as cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexoxy; and straight-chain or branched alkenyl groups formed by bonding multiple of vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 1-pentenyl, 1-hexenyl, isopropenyl, isobutenyl, or such alkenyl groups.

In formula (I), the "substituents" represented by ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 , namely "substituted alkyl groups having 1 to 20 carbon atoms in a straight-chain or branched manner,""substituted cycloalkyl groups having 3 to 20 carbon atoms,""substituted alkoxy groups having 1 to 20 carbon atoms in a straight-chain or branched manner,""substituted cycloalkoxy groups having 3 to 20 carbon atoms," or "substituted alkenyl groups having 2 to 20 carbon atoms in a straight-chain or branched manner," can specifically include: halogen atoms such as fluorine, chlorine, bromine, and iodine; _-SO3- ; ^-SO3H _{; -SO3} M; cycloalkyl groups with 3-17 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, and cyclooctyl; linear alkoxy groups with 1-17 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, and decoxy; branched alkoxy groups with 1-17 carbon atoms, such as isopropoxy, isobutoxy, dibutoxy, tributoxy, and isooctoxy; cycloalkoxy groups with 3-17 carbon atoms, such as cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexoxy; aromatic hydrocarbons with 6-18 carbon atoms, such as phenyl, naphthyl, biphenyl, and anthracene, or condensed polycyclic aromatic groups with 6-17 carbon atoms. The "M" in the above examples represents an alkali metal atom, such as a lithium atom, sodium atom, or potassium atom.

These "substituents" may be singular or multiple, and when multiple are present, they may be identical or different. Furthermore, these "substituents" may also have the substituents exemplified above.

In equation (I), adjacent bases of ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 can also be bonded to each other to form a ring. Specifically, ^R5 and ^R6 , ^R6 and ^R7 , ^R7 and ^R8 , or ^R8 and ^R9 can also be bonded to each other to form a ring. The ring formed in this case is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring.

In one embodiment, ^{R9 is} _-SO3- and ^R7 is ^a hydrogen atom or _-SO3- .

In formula (I), ^the terms " ^substituted or unsubstituted ^linear or branched alkyl groups having 1 to 20 carbon atoms,""substituted or unsubstituted linear or branched alkoxy groups having 1 to 20 carbon atoms," and "substituted or unsubstituted aromatic hydrocarbon groups having 6 to 20 carbon atoms," representing "substituted or unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms,""substituted or unsubstituted aromatic hydrocarbon groups having 6 to 20 carbon atoms," specifically include: methyl, ethyl, propyl, ... Straight-chain alkyl groups such as butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; branched alkyl groups such as isopropyl, isobutyl, dibutyl, tributyl, and isooctyl; straight-chain alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, and decoxy; branched alkoxy groups such as isopropoxy, isobutoxy, dibutoxy, tributoxy, and isooctoxy; and aromatic hydrocarbons such as phenyl, naphthyl, anthracene, phenanthryl, pyrene, and biphenyl.

In one embodiment, in formula (I) above, ^R11 , ^R12 , and ^R13 each independently represent a linear or branched alkyl or polyether structure with 1 to 20 carbon atoms, whether substituted or unsubstituted, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure.

As a "polyether structure," _it is obtained by polymerizing one of the monomers, ethylene oxide, propylene oxide, or butane oxide, to obtain polyoxyethylene ether structures (*-( _CH₂CH₂O ) _qH ) (which can also be represented as "*-(EO) _{qH "} ), polyoxypropylene ether structures (*-( _{CH₂CH₂CH₂O} ) _qH , *-( _CH₂CH ( _CH₃ )O) _qH , *-(CH( _CH₃ ) _CH₂O ) _{qH ) ( where} *-( _{CH₂CH₂CH₂O} ) _qH can also be represented as _" *-(PO) _qH "), _and polyoxybutylene ether structures (*-( _{CH₂CH₂CH₂CH₂O ) qH} , *- _{( CH₂CH₂CH} ( _CH₃ ) _O ) _qH , *-( ... ₃ ) CH ₂ O) _q H, *-(CH(CH ₃ )CH ₂ CH ₂ O) _q H (where CH ₂ CH ₂ CH ₂ CH ₂ O) _q H can also be represented as "*-(BO) _q H"), with hydroxyl group as the end and * as the bonding position with ammonium group (nitrogen cation); or further, copolymers obtained by using two or three of the aforementioned polyoxyethylene ether, polyoxypropylene ether, and polyoxybutylene ether as reaction raw materials, with hydroxyl group as the end and * as the bonding position with ammonium group (nitrogen cation). This includes regular copolymers and random copolymers. Specifically, examples include *-(EO) _₂H , *-(EO) _₃H , *-(EO) _₄H , *-(EO)₅H, *-(EO) _₆H , *-(EO) _₷ H, *-(EO) _₈H , *-(EO)₹H, *-(EO) _₁₀H , *-(PO) _₂H , *-(PO) _₃H , *-(PO) _₄H , *-(PO)₅H, *-(PO) _₆H , *-(PO)₷H, *-(PO) _₈H , *-(PO) _₹ H, *-(PO) _₁₀H , *-(PO) _₂₂H , *-(BO)₂H, *-(BO) _₃H , *-(BO) _₄H , *-(BO) _₅H , *-(BO) _₆H , *-(BO)₷H, *-(BO)₂H, *-(BO) _₂H , *-(BO) _₃H , *-(BO) _₄H , *-(BO) _₅H , *-(BO)₆H, *-(BO) _₇H , *-(BO)� ... _8H , *-(BO) _9H , *-(BO) _10H , *-(EO) ₂ (PO) _2H , *-(EO) ₂ (PO) ₂ (EO)2H, *-(PO) ₅ (EO) _3H , *-(EO)(PO) ₅ (EO) _3H , *-(PO) ₁₀ (EO) _8H , *- ₍ EO)(BO) ₆ (EO) _10H , *-(EO) ₄ (PO) _5H , ( _CH2CH ( _CH3 )O) ₄ (EO) _8H , etc. In the above, EO is ethoxylated, PO is propoxylated, and BO is butoxylated. The number of units for BO, EO, and PO are average values.

In formula (I), "M" represents an alkali metal atom, specifically such as a lithium atom, sodium atom, or potassium atom.

In formula (I), ^R1 , ^R2 , ^R3 , and ^R4 are preferably each independently representing a hydrogen atom, a linear or branched alkyl group with 1 to 10 carbon atoms (substituted or unsubstituted), a cycloalkyl group with 5 to 12 carbon atoms (substituted or unsubstituted), or an aromatic hydrocarbon group with 6 to 12 carbon atoms (substituted or unsubstituted). When ^R1 , ^R2 , ^R3 , and ^R4 are the above-mentioned groups, the brightness of the colored layer (pattern) made from the photosensitive colored resin composition can be further improved.

In formula (I), ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 are preferably each independently representing a hydrogen atom, a halogen atom, _-SO3- , ^-SO3H , _-SO3M , _a linear or branched alkyl group having 1 to 10 carbon atoms with substituents, or a linear or branched alkoxy group having 1 to 10 carbon atoms, whether substituted or unsubstituted. When ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 are the above-mentioned groups, the brightness of the colored layer (pattern) obtained from the photosensitive colored resin composition can be further improved.

In formula (I), preferably there are at least two _-SO3- ^atoms , and R9 ^is _-SO3- , and _R7 is a hydrogen atom or _-SO3- ^. When formula (I) preferably has at least two _-SO3- ^atoms , _{and R9 is} ^-SO3- _, and _R7 is a hydrogen atom or _-SO3- , the brightness of the colored layer (pattern ⁾ made from the photosensitive colored resin composition can be further improved.

In formula (I), ^R11 , ^R12 , and ^R13 preferably each represent a linear or branched alkyl or polyether structure with 1 to 20 substituted or unsubstituted atoms, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure. When ^R11 , ^{R12 ,} and ^R13 are the above-mentioned groups, the brightness of the colored layer (pattern) made from ^{the photosensitive} colored resin composition can be further improved.

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

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), the total amount ^of _-SO₃⁻ is at least 2. For example, when the total amount ^of _-SO₃⁻ is 2, n is 1; when the total amount of _-SO₃⁻ is ³ , n is 2.

The dibenzopiperanoid pigment of this embodiment, represented by formula (I), 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 a sulfonic acid group as a base metal salt. Furthermore, when the precipitated dibenzopiperanoid pigment adheres stubbornly and hinders stirring, an organic solvent can be mixed in to eliminate or alleviate this situation. As an organic solvent, there are no particular limitations as long as the corresponding dibenzopiperanone pigments have 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.

Dibenzopyran pigments (A-1) contain both anions and ammonium ions of dibenzopyran pigments.

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.

Ammonium ions can be listed as 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.

Specific examples of dibenzopiperanan colorants (A-1) are preferably dibenzopiperanan colorants composed of formulas (Ib-28) and (Ic-1), dibenzopiperanan colorants composed of formulas (Ib-40) and (Ic-2), dibenzopiperanan colorants composed of formulas (Ib-25) and (Ic-4), and dibenzopiperanan colorants composed of formulas (Ib-40) and (Ic-2). Dibenzo-piperanone colorants composed of formula (Ib-7) and formula (Ic-16), dibenzo-piperanone colorants composed of formula (Ib-5) and formula (Ic-7), dibenzo-piperanone colorants composed of formula (Ib-41) and formula (Ic-16), or combinations thereof.

The above-mentioned dibenzopiperanan colorants can be used alone or in combination.

In this embodiment, when the solid content of the photosensitive coloring resin composition is 18% to 25% by weight and the colorant (A) includes the dibenzopiperanone colorant (A-1) shown in formula (I), the relative total VOC reduction rate is increased during the production process of the color filter formed by the photosensitive coloring resin composition, and the colored layer (pattern) produced by the photosensitive coloring resin composition has good brightness and pattern properties.

Conversely, when the colorant (A) does not include the dibenzopiperanone-based colorant (A-1) shown in formula (I), the brightness and pattern quality of the colored layer (pattern) made from the photosensitive colored resin composition are poor, resulting in poor overall display quality of the image display device made from the color filter.

Based on a total weight percentage of 100% by weight of the solid components of the photosensitive coloring resin composition, the dibenzopiperanone colorant (A-1) can be from 0.01% to 25% by weight, more preferably from 0.05% to 15% by weight, and even more preferably from 0.1% to 10% by weight.

Other colorants (A-2)

The photosensitive tinted resin composition of this embodiment may further include other tinting agents (A-2) besides the dibenzopiperanone tinting agent (A-1). The other tinting agents (A-2) may include at least one of the group consisting of the pigment shown in formula (II) (A-2-1), other pigments (A-2-2), and other dyes (A-2-3).

The pigment shown in formula (II) (A-2-1)

Pigment (A-2-1) is the compound represented by formula (II).

In formula (II), A represents a p-valent organic group, wherein the carbon atom in the organic group directly bonded to N does not have a π bond. The organic group represents an aliphatic hydrocarbon group having at least a saturated aliphatic hydrocarbon at the end directly bonded to N, or an aromatic group having said aliphatic hydrocarbon. The carbon chain of the aliphatic hydrocarbon group may contain O, S, and N, and the carbon chain of the aromatic group may contain ^O , S, and N. B ^q- represents a heteropoly acid anion with a q valent. ^R1 , ^R2 , ^R3 , ^R4 , and ^R5 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group, wherein at least one of R2, ^R3 , ^R4 , and ^R5 is a substituted or unsubstituted alkyl group, and ^R2 and R... ^R1 , ^R2 , ^R3 , R4, and ^R5 can bond with each other to form a ring structure. Multiple R1, ^R2 , ^R3 , ^R4 , and ^R5 can be the same or different. ^R6 and ^R7 each independently represent substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, halogen atom, or cyano group. Ar represents substituted or unsubstituted divalent aromatic group. Multiple Ar can be the same or different. p and q represent integers greater than 2. r and s represent integers greater than 1. v represents 0 or 1. When v represents 0, there is no bond. t and u each independently represent integers greater than 0 and less than 4. t+v and u+v are integers greater than 0 and less than 4.

In formula (II), the p-valent organic group represented by A, directly bonded to the carbon atom of the nitrogen atom (N), does not have a π bond. The organic group represents an aliphatic hydrocarbon group with at least a saturated aliphatic hydrocarbon group at the end directly bonded to N, or an aromatic group containing the aliphatic hydrocarbon group. The carbon chain of the aliphatic hydrocarbon group may contain oxygen (O), sulfur (S), and nitrogen (N), while the carbon chain of the aromatic group may contain O, S, and N. Because the carbon atom directly bonded to N does not have a π bond, the color properties of the cationically emitting chromophore, such as hue or transmittance, are not affected by the bonding group A or other chromophores, and can maintain the same color as the monomer.

In formula (II), A contains an aliphatic hydrocarbon group with a saturated aliphatic hydrocarbon at least at the end directly bonded to N. This aliphatic hydrocarbon group can be linear, branched, or cyclic, provided the carbon atom at the end directly bonded to N does not have a π bond. The carbon chain containing the substituents can contain O, S, or N. For example, the carbon chain containing the substituents can contain carbonyl, carboxyl, oxycarbonyl, or amide groups. The hydrogen atom can be substituted with a halogen atom, etc.

Furthermore, in formula (II), A, the aromatic group having the aliphatic hydrocarbon group can be a monocyclic or polycyclic aromatic group having an aliphatic hydrocarbon group with at least one saturated aliphatic hydrocarbon group at the end directly bonded to N, which may have substituents or be a heterocyclic group containing O, S, or N.

In formula (II), A is preferably composed of a cyclic aliphatic hydrocarbon or aromatic group, from the viewpoint of skeletal strength.

In formula (II), from the viewpoint of the strength of the skeleton, the cyclic aliphatic hydrocarbon group A is preferably a bridged alicyclic hydrocarbon group. A bridged alicyclic hydrocarbon group refers to a polycyclic aliphatic hydrocarbon group that has a cross-linking structure within an aliphatic ring and has a multi-ring structure. Examples of bridged alicyclic hydrocarbon groups include norbornane, bicyclic [2.2.2]octane, and adamantane. Norbornane is preferred as a bridged alicyclic hydrocarbon group. Furthermore, aromatic groups may include those containing benzene rings or naphthyl rings, with those containing benzene rings being preferred. For example, when A is a divalent organic group, examples include linear, branched, or cyclic alkyl groups with 1 to 20 carbon atoms, or aromatic groups with 1 to 20 carbon atoms such as xylylene, which are substituted with two aromatic groups.

In formula (II), A, the valence p is the number of chromogenic cation sites constituting the cation, and p represents an integer greater than or equal to 2. In this pigment, from the viewpoint of heat resistance, the valence p of the cation is preferably 2 or higher, and more preferably 3 or higher. There is no particular upper limit to p, but from the viewpoint of ease of manufacture, p is preferably 4 or lower, and more preferably 3 or lower.

^R1 , ^R2 , ^R3 , ^R4 , and ^R5 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group, wherein at least one of ^R2 , ^R3 , ^R4 , and ^R5 is a substituted or unsubstituted alkyl group. Preferably, ^R2 , ^R3 , ^R4 , and ^R5 are each independently representing a substituted or unsubstituted alkyl group. When ^R2 , ^R3 , ^R4 , and ^R5 each independently represent a substituted or unsubstituted alkyl group, the pattern produced by the photosensitive colored resin composition has a better post-baking film residue rate.

There are no particular limitations on the alkyl groups in ^R1 , ^R2 , ^R3 , ^R4 , and ^R5 . Examples include straight-chain or branched alkyl groups with 1 to 20 carbon atoms, preferably straight-chain or branched alkyl groups with 1 to 8 carbon atoms, more preferably straight-chain or branched alkyl groups with 1 to 5 carbon atoms, and especially preferably ethyl or methyl. There are no particular limitations on the substituents that the alkyl groups may have, and examples include halogen atoms, hydroxyl groups, and alkoxy groups.

From the perspective of chemical stability, ^R1 , ^R2 , ^R3 , ^R4 , and ^R5 are preferably alkyl groups that each independently represent a hydrogen atom and have 1 to 5 carbon atoms, or ^R2 and ^R3 are bonded together to form a ring structure, and ^R4 and ^R5 are bonded together to form a ring structure, wherein the ring structure may be a pyrrolidine ring, a piperidine ring, or a morpholino ring.

^R1 , ^R2 , ^R3 , ^R4 , and ^R5 can each form the above structure independently. That is to say, multiple ^R1 , ^R2 , ^R3 , ^R4 , and ^R5 can be the same or different.

^R6 and ^R7 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a halogen atom, or a cyano group. There are no particular limitations on the substituted or unsubstituted alkyl group in ^R6 and ^R7 , but it is preferably a straight-chain or branched alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, propyl, and butyl, and these groups can be straight-chain or branched. There are no particular limitations on the substituents that may be present in the alkyl group, and examples include aryl, halogen atom, hydroxyl, alkoxy, or combinations thereof.

Furthermore, there are no particular restrictions on whether the alkoxy groups in ^R6 and ^R7 are substituted or unsubstituted, but they are preferably straight-chain or branched alkoxy groups with 1 to 8 carbon atoms, and more preferably alkoxy groups with 1 to 4 carbon atoms. Examples of alkoxy groups with 1 to 4 carbon atoms include methoxy, ethoxy, propoxy, and butoxy, wherein these groups can be straight-chain or branched. There are no particular restrictions on the substituents that may be present in the alkoxy group, and examples include aryl, halogen, hydroxyl, and alkoxy groups.

The halogen atoms of ^R6 and ^R7 can include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, or combinations thereof.

The substitution numbers of ^R6 and ^R7 , that is, t and u, each independently represent integers greater than 0 and less than 4, preferably greater than 0 and less than 2, and more preferably greater than 0 and less than 1. t+v and u+v are integers greater than 0 and less than 4. When there are two or more t and u, the multiple t and u can be the same or different.

Furthermore, since no bond exists when v represents 0, the compound shown in formula (II) has a triarylmethane skeleton. ^R6 and ^R7 can substitute at any site of the triarylmethane skeleton or an aromatic ring having a resonance structure within the skeleton, preferably at the meta position based on the substitution ^position of the amino group indicated by ^-NR2R3 or ^{-NR4R5 .}

There are no particular restrictions on whether the divalent aromatic groups in Ar are substituted or unsubstituted; multiple Ars can be the same or different. The aromatic groups in Ar can be assumed to be the same as those listed in the aromatic groups of A.

Ar is preferably an aromatic group with 6 to 20 carbon atoms, either substituted or unsubstituted; more preferably, it is an aromatic group containing a condensed polycyclic carbon ring, either substituted or unsubstituted. From the viewpoint of simple structure and low raw material cost, it is more preferably an enantylphenyl or enantenayl group.

Within a single molecule, there are multiple ^R1 , ^R2 , ^R3 , ^R4 , ^R5 , ^R6 , and ^R7 , and Ar can be the same or different. The desired color can be adjusted by combining ^R1 , ^R2 , ^R3 , ^R4 , ^R5 , ^R6 , and ^R7 with Ar.

In the compound shown in formula (II), from the viewpoint of high luminosity and excellent heat resistance, B ^q- represents a heteroacid anion with a q valence. A heteroacid anion can be represented as (Y ₁ M _e O _f ) ^q- . In the above ionic formula, M represents a polyatom, Y represents a heteroatom, e represents the composition ratio of the polyatom, and f represents the composition ratio of oxygen atoms. Examples of polyatoms M include molybdenum (Mo), tungsten (W), vanadium (V), titanium (Ti), or niobium (Nb). Examples of heteroatoms Y include silicon (Si), phosphorus (P), arsenic (As), sulfur (S), iron (Fe), and cobalt (Co).

In B ^q- , the heterologous multiple acid anion preferably contains at least one of molybdenum (Mo) and tungsten (W), and more preferably is a heterologous multiple acid anion containing at least the q valence of tungsten.

In equation (II), r represents the number of cations, and s represents the number of anions. Both r and s are integers greater than or equal to 1. When r is greater than or equal to 2, the multiple cations in equation (II) can be used individually or in combination. Similarly, when s is greater than or equal to 2, the multiple anions in equation (II) can be used individually or in combination.

In formula (II), v represents an integer of 0 or 1. When v represents 0, no bond exists, and the main structure of formula (II) is a triarylmethane skeleton. When v represents 1, the main structure of formula (II) is a xanthene skeleton. Multiple v values can be the same or different. The compound shown in formula (II) preferably contains a triarylmethane skeleton.

Furthermore, the compound shown in formula (II) can be prepared, for example, by referring to International Publication No. 2012/144520.

The above pigment (A-2-1) can be used alone or in combination with other pigments.

Specific examples of compounds represented by formula (II) may include at least one of compounds (II-1) to (II-20). Each of compounds (II-1) to (II-20) comprises a cation and a heterospecific multiple acid anion.

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

Compound (II-1)

Other pigments (A-2-2)

In this embodiment, the colorant (A) may further include other pigments (A-2-2). Other pigments (A-2-2) may be inorganic pigments, organic pigments, or combinations thereof.

Inorganic pigments can be metal oxides, metal ferrite salts, and other metal compounds. Among them, inorganic pigments can include oxides of metals such as iron (Fe), cobalt (Co), aluminum (Al), cadmium (Cd), lead (Pb), copper (Cu), titanium (Ti), magnesium (Mg), chromium (Cr), zinc (Zn), and antimony (Sb), as well as composite oxides of the aforementioned metals, metal ferrite salts, or combinations thereof.

Specific examples of organic pigments 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, 16 8, 175; C.I. Orange 1, 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 61, 63, 64, 71, 73; C.I. 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 Purple 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.

The other pigments mentioned above (A-2-2) can be used alone or in combination.

Other preferred pigments (A-2-2) are C.I. Pigment Blue 15:4, C.I. Pigment Blue 15:6, or combinations thereof.

The average particle size of other pigments (A-2-2) can be from 10 nm to 200 nm, preferably from 20 nm to 150 nm, and even more preferably from 30 nm to 130 nm.

Other dyes (A-2-3)

Other dyes (A-2-3) include, but are not limited to, azo dyes, anthraquinone dyes, phthalocyanine dyes, quinone imine dyes, quinoline dyes, nitro dyes, or combinations thereof.

Azo dyes include, but are 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 combinations thereof.

Anthraquinone dyes include, but are not limited to, C.I. Badblue 4, Acid Blue 40, Acid Green 25, Reactive Blue 19, Reactive Blue 49, Disperse Red 60, Disperse Blue 56, Disperse Blue 60, or combinations thereof.

Phthalocyanine dyes include, but are not limited to, C.I. Basic Blue 5, etc.

Quinone imine dyes include, but are not limited to, C.I. Basic Blue 3, C.I. Basic Blue 9, or combinations thereof.

Quinoline dyes C.I. Solvent Yellow 33, C.I. Acid Yellow 3, C.I. Disperse Yellow 64, or combinations thereof.

Nitro dyes include, but are not limited to, C.I. Acid Yellow 1, Acid Orange 3, Disperse Yellow 42, or combinations thereof.

The other dyes mentioned above (A-2-3) can be used alone or in combination.

Other dyes (A-2-3) preferably include C.I. Acid Red 37, C.I. Acid Blue 29, or combinations thereof.

Other preferred colorants (A-2) include compounds (II-1), compounds (II-2), C.I. Pigment Blue 15:6, or combinations thereof.

The total weight of the solid components based on the photosensitive coloring resin composition is 100% by weight, and the other coloring agent (A-2) can be from 1% to 60% by weight, preferably from 2.5% to 45% by weight, and even more preferably from 5% to 35% by weight.

Based on a total weight percentage of 100% by weight of the solid components of the photosensitive coloring resin composition, the colorant (A) can be from 1% to 85% by weight, more preferably from 2.5% to 60% by weight, and even more preferably from 5% to 45% by weight.

In the photosensitive tinted resin composition of this embodiment, the tinting agent (A) is preferably used by dispersing it in a solvent using a dispersant. In this embodiment, the dispersant can be appropriately selected from conventional dispersants. Dispersants may include cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, polysiloxane surfactants, fluorinated surfactants, and combinations thereof. The dispersants listed above can be non-polymeric or polymeric. From the viewpoint of uniform and fine dispersion, polymeric dispersants are preferred.

Polymer dispersants 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 acid esters such as polyacrylic acid; (co)polymers of hydroxyl-containing unsaturated carboxylic acid esters such as hydroxyl-containing polyacrylates or modified products of the above compounds; polyurethane esters; unsaturated polyamides; polysiloxanes; and long-chain dispersants. Polyamine phosphates; polyethylimide derivatives (acetylamines or their bases obtained by reacting poly(lower alkylimides) with polyesters containing free carboxyl groups); polyallylamine derivatives (reaction products obtained by reacting polyallylamine with one or more compounds selected from polyesters containing free carboxyl groups, polyamines, or cocondensates of esters and acetylamines (polyester-acetylamines)); or combinations thereof.

From the viewpoint of effectively dispersing the aforementioned colorant (A) and exhibiting good dispersion stability, the polymeric dispersant is preferably a polymeric dispersant containing nitrogen atoms in the main chain or side chains and possessing an amine valence.

Specific examples of polymeric dispersants containing nitrogen atoms in the main chain or side chains are listed below.

Commercially available examples of (partial)amine salts, (partial)ammonium salts, or (partial)alkylamine salts of (co)polymers of unsaturated carboxylic acids such as polyacrylic acid include Disperbyk 2000 and Disperbyk 2001 (both manufactured by BYK-Chemie).

Commercially available polyurethane products include Disperbyk 161 (manufactured by BYK-Chemie).

Commercially available unsaturated polyamides include Disperbyk 101 and Disperbyk 130 (manufactured by BYK-Chemie).

Commercially available polyallylamine derivatives include Ajisper PB821, Ajisper PB822, Ajisper PB824, and Ajisper PB827 (manufactured by Ajinomoto Fine-Techno).

Commercially available poly(ethylene imine) derivatives include Solsperse 33500 (manufactured by Lubrizol Corporation, Japan).

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, and Dysperbyk 2050 (all manufactured by BYK-Chemie); EFKA 4046 and 4047 (all manufactured by EFKA Chemicals Co.); and Solsperse 12000 and Solsperse... Solsperse 13250, 13940, 17000, 20000, 24000GR, 24000SC, 27000, 28000, 32000, 33500, 35200, 37500 (all manufactured by Lubrizol, Japan); Ajisper PB711, 823, 880 (all manufactured by Ajinomoto Fine-Techno), etc.

There are no particular restrictions on the amount of dispersant used; it can be adjusted appropriately according to needs.

Alkali-soluble resin (B) First base-soluble resin (B)

The first alkali-soluble resin (B-1) of this embodiment is obtained by copolymerization of a carboxylic acid-containing ethylene unsaturated monomer (b-1-1) with other copolymerizable ethylene unsaturated monomers (b-1-2).

Carboxylic acid-containing ethylene unsaturated monomers (b-1-1) can be used alone or in combination, and carboxylic acid-containing ethylene unsaturated monomers include, but are not limited to, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid (MAA), butenoic acid, α-chloroacrylic acid, ethylacrylic acid, cinnamic acid, 2-acryloyloxysuccinate, or 2-methacryloyloxyethyl succinate monoester (HOMS); unsaturated dicarboxylic acids (anhydrides) such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, leuconic acid, and leuconic anhydride; and unsaturated polycarboxylic acids (anhydrides) with three or more carboxylic acid groups. Preferred carboxylic acid-containing vinyl unsaturated monomers include acrylic acid, methacrylic acid, 2-acryloxyethylbutyrate, 2-methacryloxyethylbutyrate, or combinations thereof. More preferably, 2-acryloxyethylbutyrate, 2-methacryloxyethylbutyrate, or combinations thereof are vinyl unsaturated monomers containing carboxylic acid groups.

In this embodiment, the amount of the carboxylic acid-containing ethylene unsaturated monomer (b-1-1) based on the first alkali-soluble resin (B-1) and other copolymerizable ethylene unsaturated monomers (b-1-2) used is 100 parts by weight, and the amount of the carboxylic acid-containing ethylene unsaturated monomer (b-1-1) used is 10 to 90 parts by weight, preferably 15 to 85 parts by weight, and more preferably 20 to 80 parts by weight.

Other copolymerizable ethylene unsaturated monomers (b-1-2) can be used alone or in combination, and these other copolymerizable ethylene unsaturated monomers (b-1-2) include, but are not limited to, aromatic vinyl compounds such as styrene (SM), α-methylstyrene, vinyltoluene, p-chlorostyrene, and methoxystyrene; N-phenylmaleimide (PMI), N-ortho- Maleimides including hydroxyphenylmaleimides, nitrogen-m-hydroxyphenylmaleimides, nitrogen-p-hydroxyphenylmaleimides, nitrogen-ortho-methylphenylmaleimides, nitrogen-m-methylphenylmaleimides, nitrogen-p-methylphenylmaleimides, nitrogen-ortho-methoxyphenylmaleimides, nitrogen-m-methoxyphenylmaleimides, nitrogen-p-methoxyphenylmaleimides, and nitrogen-cyclohexylmaleimides; methyl acrylate (methyl Acrylate (MA), methyl methacrylate, ethyl methacrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, dibutyl acrylate, dibutyl methacrylate, tributyl acrylate, tributyl methacrylate, 2-hydroxyethyl acrylate, 2-methacrylate Hydroxyethyl acrylate, 2-Hydropropyl acrylate, 2-Hydropropyl methacrylate, 3-Hydropropyl acrylate, 3-Hydropropyl methacrylate, 2-Hydrobutyl acrylate, 2-Hydrobutyl methacrylate, 2-Hydrobutyl methacrylate, 3-Hydrobutyl acrylate, 3-Hydrobutyl methacrylate, 4-Hydrobutyl acrylate, 4-Hydrobutyl methacrylate, Allyl acrylate, Allyl methacrylate, Benzyl acrylate, Benzyl methacrylate (BzMA), Phenyl acrylate, Phenyl methacrylate, Triethylene glycol methoxyacrylate, Triethylene glycol methoxyacrylate, Dodecyl methacrylate, Tetradecyl methacrylate, Hexadecyl methacrylate, Octadecyl methacrylate, Eicosyl methacrylate, Docosyl methacrylate, Dicyclopentenyloxyethyl acrylate Unsaturated carboxylic acid esters such as acrylate (DCPOA); acrylates such as nitrogen-, nitrogen-dimethylaminoethyl acrylate, nitrogen-, nitrogen-dimethylaminoethyl methacrylate, nitrogen-, nitrogen-diethylaminopropyl acrylate, nitrogen-, nitrogen-dimethylaminopropyl methacrylate, nitrogen-, nitrogen-dibutylaminopropyl acrylate, and nitrogen-isobutylaminoethyl methacrylate; unsaturated carboxylic acid epoxypropyl esters such as glycidyl acrylate and glycidyl methacrylate; vinyl acetate and vinyl propionate. Vinyl carboxylic acid esters such as vinyl butyrate; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl epoxypropyl ether, and methyl allyl epoxypropyl ether; nitrified vinyl compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide; unsaturated amides such as acrylamide, methacrylonitrile, α-chloroacrylonitrile, N-hydroxyethylacrylonitrile, and N-hydroxyethylmethylacrylonitrile; aliphatic conjugated dienes such as 1,3-butadiene, isoprene, and chlorobutadiene; or combinations thereof.

Other copolymerizable vinyl unsaturated monomers (b-1-2) preferably include styrene, N-phenylmaleimide, methyl acrylate, methyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, methyl methacrylate, bis(cyclopentenyl) ethyl acrylate, or combinations thereof.

In this embodiment, the amount of the carboxylic acid-containing ethylene unsaturated monomer (b-1-1) based on the first alkali-soluble resin (B-1) and other copolymerizable ethylene unsaturated monomers (b-1-2) used is 100 parts by weight, and the amount of the other copolymerizable ethylene unsaturated monomers (b-1-2) used is 10 to 90 parts by weight, preferably 15 to 85 parts by weight, and more preferably 20 to 80 parts by weight.

There are no particular restrictions on the preparation method of the first alkali-soluble resin (B-1), and an appropriate polymerization method can be selected according to the requirements. Solution polymerization is one example of a polymerization method. In addition to the required monomer, the reaction solution of the alkali-soluble resin (B) may also include solvents, initiators, etc. The solvent can be used alone or in combination, and the solvent includes, but is not limited to, (poly)alkylene glycol monoalkyl ethers 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 n-propyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, and dipropylene glycol ethyl ether; ethylene glycol methyl ether acetate, ethylene glycol ethyl ether acetate, and propylene glycol methyl ether acetate. Acetate (abbreviated as PGMEA), propylene glycol ethyl ether acetate, etc. (poly)alkylene glycol monoalkyl ether acetates; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, etc.; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc.; lactic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, etc.; methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate (ethyl) Other esters including 3-ethoxypropionate (EEP), ethyl ethoxylate, ethyl hydroxylate, methyl 2-hydroxy-3-methylbutyrate, 3-methyl-3-methoxybutylacetate, 3-methyl-3-methoxybutylpropionate, 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, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-methoxybutyrate, etc.; aromatic hydrocarbons such as toluene and xylene; amides such as nitrogen-methylpyrrolidone, nitrogen, nitrogen-dimethylformamide, or nitrogen, nitrogen-dimethylacetamide, etc. The solvent preferably includes propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, or combinations thereof. The (poly)alkylene glycol monoalkyl ethers refer to alkylene glycol monoalkyl ethers or polyalkylene glycol monoalkyl ethers. The (poly)alkylene glycol monoalkyl ether acetates refer to alkylene glycol monoalkyl ether acetates or polyalkylene glycol monoalkyl ether acetates.

Initiators are generally free radical polymerization initiators, specifically such as azo compounds like 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), and 2,2'-azobis-2-methylbutyronitrile (AMBN); and peroxide compounds like benzoyl peroxide.

The aforementioned first-base soluble resin (B-1) can be used alone or in combination with other resins.

Furthermore, the average molecular weight of the polystyrene-converted polystyrene in the aforementioned first alkali-soluble resin (B-1), as determined by gel permeation chromatography (GPC), is between 1,000 and 35,000, preferably between 3,000 and 30,000, and even more preferably between 5,000 and 25,000.

In this embodiment, the amount of 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.

Second alkali-soluble resin (B-2)

The second alkali-soluble resin (B-2) of this embodiment is prepared by polymerizing a mixture comprising an epoxy compound (b-2-1) having at least two epoxy groups and a compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group. In addition, the mixture may optionally comprise a carboxylic anhydride compound (b-2-3) and/or an epoxy-containing compound (b-2-4).

The epoxide compound (b-2-1) having at least two epoxy groups may have a structure as shown in formula (III-1) or formula (III-2) below. Here, the statement "the epoxide compound (b-2-1) may have a structure as shown in formula (III-1) or formula (III-2) below" also covers the case where a compound having the structure shown in formula (III-1) and a compound having the structure shown in formula (III-2) below coexist as an epoxide compound (b-2-1). Specifically, the aforementioned epoxide compound (b-2-1) having at least two epoxy groups, for example, has a structure as shown in formula (III-1) below:

In formula (III-1), ^R1c , ^R2c , ^R3c and ^R4c each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an aromatic group having 6 to 12 carbon atoms, or an aralkyl group having 6 to 12 carbon atoms. ^R1c , ^R2c , ^R3c and ^R4c can each be the same or different.

The aforementioned epoxide compound (b-2-1) of formula (III-1) having at least two epoxy groups may include, but is not limited to, an epoxy-containing bisphenol fluorene compound obtained by reacting a bisphenol fluorene compound with epihalohydrin.

Specific examples of the aforementioned bisphenol fluorene compounds may include, but are not limited to: 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-chlorophenyl)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, and 9,9-bis(4-hydroxy-3-fluorophenyl)fluorene. 4-Hydroxyl-3-methoxyphenyl)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-dichlorophenyl)fluorene, or combinations thereof.

The aforementioned epihalohydrin may include, but is not limited to, 3-chloro-1,2-epoxypropane (epichlorohydrin), 3-bromo-1,2-epoxypropane (epibromohydrin), or combinations thereof.

The epoxy-containing bisphenol fluorene compounds obtained by reacting bisphenol fluorene compounds with halogenated propylene oxide include, but are not limited to: (1) products manufactured by Nippon Steel Chemical Co., Ltd., such as ESF-300; (2) products manufactured by Osaka Gas Co., Ltd., such as PG-100 and EG-210; (3) products manufactured by S.M.S Technology Co., Ltd., such as SMS-F9PhPG, SMS-F9CrG, and SMS-F914PG; or combinations thereof.

Secondly, the epoxide compound (b-2-1) having at least two epoxy groups may also have a structure as shown in the following formula (III-2):

In formula (III-2), ^R5c to ^R18c each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an aromatic group having 6 to 15 carbon atoms, and ^R5c to ^R18c can be the same or different; g represents an integer from 0 to 10.

The aforementioned epoxide compound (b-2-1) of formula (III-2) having at least two epoxy groups is obtained, for example, by reacting a compound having the structure of formula (III-2-1) with halogenated propylene oxide in the presence of an alkali metal hydroxide.

In equation (III-2-1), the definitions of R ^5c to R ^18c and g are ^the same as those in equation (III-2 ⁾ , and will not be repeated here.

Furthermore, the aforementioned epoxy compound (b-2-1) of formula (III-2) having at least two epoxy groups is, for example, formed by a condensation reaction of a compound having the structure of formula (III-2-2) with a phenol in the presence of an acid catalyst, resulting in a compound having the structure of formula (III-2-1). Then, by adding excess halogenated propylene oxide to carry out a dehydrohalogenation reaction, the epoxy compound (b-2-1) of formula (III-2) is obtained.

In formula (III-2-2), R ^19c and R ^20c each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an aromatic group having 6 to 15 carbon atoms, and R ^19c and R ^20c may be the same or different; T ¹ and T ² each independently represent a halogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, and T ¹ and T ² may be the same or different.

The aforementioned halogen atom is preferably chlorine or bromine, the aforementioned alkyl group may be, for example, methyl, ethyl, or tributyl, and the aforementioned alkoxy group may be, for example, methoxy or ethoxy.

Specific examples of the aforementioned phenols may 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. These phenols can generally be used alone or in combination.

The compound having the structure (III-2-2) described above is used in an amount of 1 mol, and the phenol is used in an amount of 0.5 to 20 mol, with 2 to 15 mol being preferred.

Specific examples of the aforementioned acid catalysts may include, but are not limited to, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, oxalic acid, boron trifluoride, anhydrous aluminum chloride, and zinc chloride, among which p-toluenesulfonic acid, sulfuric acid, or hydrochloric acid are preferred. The aforementioned acid catalysts may be used alone or in combination.

Furthermore, while there are no particular restrictions on the amount of the acid catalyst used, based on the fact that the amount of the compound having the formula (III-2-2) is 100% by weight (wt%), the amount of acid catalyst used is preferably 0.1 wt% to 30 wt%.

The condensation reaction described above can be carried out in the absence of a solvent or in the presence of an organic solvent. Specific examples of the organic solvents mentioned above include, but are not limited to, toluene, xylene, or methyl isobutyl ketone. These organic solvents can be used alone or in combination.

The total amount of the compound having the structure of formula (III-2-2) and the phenol used is 100 wt%, and the amount of the organic solvent used is 50 wt% to 300 wt%, preferably 100 wt% to 250 wt%. Furthermore, the operating temperature of the condensation reaction is 40°C to 180°C, and the operating time of the condensation reaction is 1 hour to 8 hours.

After the above condensation reaction is completed, neutralization or washing can be performed. The neutralization process involves adjusting the pH of the resulting solution to between pH 3 and pH 7, with pH 5 to pH 7 being preferred. The above-mentioned washing treatment can be carried out using a neutralizing agent, which is an alkaline substance. Specific examples include: alkaline metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; organic amines such as diethylenetriamine, triethylenetetramine, aniline, and phenylene diamine; and ammonia and sodium dihydrogen phosphate. The above-mentioned washing treatment can be carried out using conventional methods, for example, by adding an aqueous solution containing the neutralizing agent to the solution after the reaction and repeatedly performing extraction. After neutralization or washing, unreacted phenols and solvents are removed by depressurization and heating, followed by concentration to obtain a compound with the structure (III-2-1).

Specific examples of the aforementioned halogenated propylene oxide may include, but are not limited to, 3-chloro-1,2-epoxypropane, 3-bromo-1,2-epoxypropane, or combinations thereof. Before or during the aforementioned dehalogenation reaction, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide may be added. The operating temperature for the aforementioned dehalogenation reaction is between 20°C and 120°C, and the operating time ranges from 1 hour to 10 hours.

In this embodiment, the alkali metal hydroxides added in the above-mentioned dehalogenation reaction can also be aqueous solutions of the alkali metal hydroxides. In this specific embodiment, while the aqueous solution of the alkali metal hydroxides is continuously added to the dehalogenation reaction system, water and halogenated propylene oxide can be continuously distilled off under reduced or normal pressure, thereby separating and removing water, and simultaneously allowing the halogenated propylene oxide to be continuously refluxed back into the reaction system.

Before the above-mentioned dehalogenation reaction, quaternary ammonium salts such as tetramethyl ammonium chloride, tetramethyl ammonium bromide, and trimethyl benzyl ammonium chloride can be added as catalysts, and the reaction is carried out at 50°C to 150°C for 1 to 5 hours. Then, alkali metal hydroxides or their aqueous solutions are added, and the reaction is carried out at 20°C to 120°C for 1 to 10 hours to proceed with the dehalogenation reaction.

The total hydroxyl equivalent in the compound having the structure of formula (III-2-1) is 1 equivalent, and the amount of the halogenated propylene oxide used can be from 1 equivalent to 20 equivalents, preferably from 2 equivalents to 10 equivalents. The total hydroxyl equivalent in the compound having the structure of formula (III-2-1) is 1 equivalent, and the amount of alkali metal hydroxide added in the dehalogenation reaction can be from 0.8 equivalents to 15 equivalents, preferably from 0.9 equivalents to 11 equivalents.

In addition, to ensure the smooth progress of the above-mentioned dehalogenation reaction, besides adding alcohols such as methanol and ethanol, aprotic polar solvents such as dimethyl sulfone and dimethyl sulfoxide can also be added. When using alcohols, based on a total amount of 100 wt% halogenated propylene oxide, the amount of alcohol used can be 2 wt% to 20 wt%, preferably 4 wt% to 15 wt%. In the example of using an aprotic polar solvent, based on a total amount of 100 wt% halogenated propylene oxide, the amount of aprotic polar solvent used can be 5 wt% to 100 wt%, with 10 wt% to 90 wt% being preferred.

After the dehalogenation reaction is complete, selective water washing can be performed. Then, halogenated propylene oxide, alcohols, and aprotic polar solvents are removed by heating and depressurization. This heating and depressurization is carried out, for example, at a temperature of 110°C to 250°C and a pressure of 1.3 kPa (10 mmHg) or less.

To avoid the formation of hydrolytically degradable halogens in the epoxy resin, the solution after the dehalogenation reaction can be added to solvents such as toluene or methyl isobutyl ketone, followed by aqueous solutions of alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and then the dehalogenation reaction can be carried out again. In the dehalogenation reaction, the total equivalent of hydroxyl groups in the compound having the structure of formula (III-2-1) is 1 equivalent, and the amount of alkali metal hydroxide used is 0.01 mol to 0.3 mol, with 0.05 mol to 0.2 mol being preferred. Furthermore, the operating temperature range for the aforementioned dehalogenation reaction is 50°C to 120°C, and the operating time ranges from 0.5 hours to 2 hours.

After the dehalogenation reaction is completed, salts are removed by filtration and washing. Alternatively, solvents such as toluene and methyl isobutyl ketone can be extracted by heating and depressurization to obtain an epoxy compound (b-2-1) having at least two epoxy groups, as shown in formula (III-2). The epoxy compound (b-2-1) having at least two epoxy groups of formula (III-2) can include, but is not limited to, products manufactured by Nippon Kayaku Co., Ltd., such as those traded under the names NC-3000, NC-3000H, NC-3000S, and NC-3000P.

The aforementioned compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group is, for example, selected from the group consisting of the following (1) to (3): (1) acrylic acid, methacrylic acid, 2-methacryloyloxyethylbutanedioic acid, 2-methacryloyloxybutylbutanedioic acid, 2-methacryloyloxyethylhexahydrophthalic acid, 2-methacryloyloxyethylmaleic acid, 2-methacryloyloxypropylmaleic acid, 2-methacryloyloxybutylmaleic acid, 2-methacryloyloxypropylbutanedio ... (1) hydroxyl tetrahydrophthalic acid, 2-methacryloxypropylphthalic acid, 2-methacryloxybutylphthalic acid, or 2-methacryloxybutylhydrophthalic acid; (2) a compound obtained by reacting a hydroxyl-containing (meth)acrylate with a dicarboxylic acid compound, wherein the dicarboxylic acid compound includes, but is not limited to, adipic acid, succinic acid, maleic acid, and phthalic acid; (3) a compound obtained by reacting a hydroxyl-containing (meth)acrylate with a carboxylic anhydride. The half-ester compound obtained from the reaction of the compounds, wherein the hydroxyl-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, etc. Furthermore, the carboxylic anhydride compound described herein may be the same as the carboxylic anhydride compound (b-2-3) contained in the mixture of the second alkali-soluble resin (B-2) described below, and therefore will not be elaborated further here.

The mixture of the second alkali-soluble resin (B-2) may selectively include a carboxylic anhydride compound (b-2-3) and/or an epoxy-containing compound (b-2-4). The above-mentioned carboxylic anhydride compound (b-2-3) may be selected from the group consisting of the following (1) to (2): (1) butanedioic anhydride, maleic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, methyl hexahydrophthalic anhydride, methyl endo-methylene tetrahydrophthalic anhydride, chlorendic anhydride, glutaric anhydride or 1,3-dioxoisobenzofuran-5-carboxylic anhydride. (1) Dicarboxylic anhydride compounds such as benzophenone tetracarboxylic dianhydride (BTDA), bisphenyltetracarboxylic dianhydride, or bisphenyl ether tetracarboxylic dianhydride, etc.

The aforementioned epoxy-containing compounds (b-2-4) are, for example, selected from glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, glycidyl ether compounds containing unsaturated groups, epoxy-containing unsaturated compounds, or any combination thereof. The aforementioned glycidyl ether compounds containing unsaturated groups include, but are not limited to, compounds with trade names Denacol EX-111, EX-121 Denacol, Denacol EX-141, Denacol EX-145, Denacol EX-146, Denacol EX-171, Denacol EX-192, etc. (all products of Nagase Kasei Corporation).

The aforementioned second alkali-soluble resin (B-2) can be prepared by polymerizing an epoxy compound (b-2-1) of formula (III-1) having at least two epoxy groups with a compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group to form a hydroxyl-containing reaction product, followed by the addition of a carboxylic anhydride compound (b-2-3) for further reaction. The total hydroxyl equivalent of the above-mentioned hydroxyl-containing reaction product is 1 equivalent, and the equivalent of the anhydride groups 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. When multiple carboxylic anhydride compounds (b-2-3) are used, they can be added sequentially or simultaneously during the reaction. When using dicarboxylic anhydride and tetracarboxylic anhydride compounds as the carboxylic anhydride compounds (b-2-3), the molar ratio of the dicarboxylic anhydride to the tetracarboxylic anhydride is preferably 1/99 to 90/10, more preferably 5/95 to 80/20. Furthermore, the operating temperature range for the above reaction is, for example, 50°C to 130°C.

The aforementioned second alkali-soluble resin (B-2) can be prepared by reacting an epoxy compound (b-2-1) of formula (III-2) having at least two epoxy groups with a compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group to form a hydroxyl-containing reaction product, followed by polymerization by adding a carboxylic anhydride compound (b-2-3) and/or an epoxy-containing compound (b-2-4). The total equivalent of epoxy groups on the epoxy compound (b-2-1) of formula (III-2) having at least two epoxy groups is 1 equivalent, and the acid equivalent of the compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group is preferably 0.8 equivalents to 1.5 equivalents, more preferably 0.9 equivalents to 1.1 equivalents. Based on the fact that the total hydroxyl content of the above-mentioned hydroxyl-containing reaction product is 100 mole percent (mol%), the amount of carboxylic anhydride compound (b-2-3) used is preferably 10 mol% to 100 mol%, more preferably 20 mol% to 100 mol%, and most preferably 30 mol% to 100 mol%.

In the preparation of the aforementioned second alkali-soluble resin (B-2), an alkaline compound is typically added to the reaction solution as a reaction catalyst to accelerate the reaction. The reaction catalyst can be used alone or in combination, and includes, but is not limited to, triphenylphosphine, triphenyl stibine, triethylamine, triethanolamine, tetramethyl ammonium chloride, and benzyltriethyl ammonium chloride. The total amount of the above-mentioned epoxide compound (b-2-1) having at least two epoxy groups and the compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group is 100 parts by weight, and the amount of the reaction catalyst is preferably 0.01 to 10 parts by weight, more preferably 0.3 to 5 parts by weight.

In addition, to control the degree of polymerization, a polymerization inhibitor is usually added to the reaction solution. Such polymerization inhibitors may include, but are not limited to, methoxyphenol, methylhydroquinone, hydroquinone, 2,6-di-t-butyl-p-cresol, or phenothiazine. Generally, these polymerization inhibitors can be used alone or in combination. Based on 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 vinyl unsaturated group (b-2-2), the total amount used is 100 parts by weight, and the amount of polymerization inhibitor used is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight.

When preparing the second alkali-soluble resin (B-2), a polymerization reaction solvent may be used if necessary. Specific examples of solvents used in the aforementioned polymerization reactions include: alcohols such as ethanol, propanol, isopropanol, butanol, isobutanol, 2-butanol, hexanol, or ethylene glycol; ketones such as methyl ethyl ketone or cyclohexanone; aromatic hydrocarbons such as toluene or xylene; cyrosol 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; polypropylene glycol alkyl ether compounds such as di(propylene glycol)methyl ether; ethyl acetate, butyl acetate, ethylene glycol monoethyl ether acetate, or propylene glycol methyl ether acetate. Acetate esters such as acetate; alkyl lactate esters such as ethyl lactate or butyl lactate; or dialkyl glycol ethers; or ethyl 3-ethoxypropionate. The above-mentioned polymerization solvents can generally be used alone or in combination. Furthermore, the acid value of the second alkali-soluble resin (B-2) is preferably from 50 mg KOH/g to 200 mg KOH/g, more preferably from 60 mg KOH/g to 150 mg KOH/g.

Furthermore, the average molecular weight of the second alkali-soluble resin (B-2), as determined by colloidal osmosis chromatography, is 500 to 10,000, preferably 800 to 8,000, and even more preferably 1,000 to 6,000.

The aforementioned second alkali-soluble resin (B-2) can be used alone or in combination with other resins.

In this embodiment, the amount of the alkali-soluble resin (B) used is 100 parts by weight, and the amount of the second alkali-soluble resin (B-2) used is 0 to 90 parts by weight, preferably 10 to 80 parts by weight, and more preferably 20 to 70 parts by weight.

Based on a total weight percentage of 100% by weight of the solid components of the photosensitive coloring resin composition, the alkali-soluble resin (B) may be from 2.5% to 70% by weight, more preferably from 5% to 60% by weight, and even more preferably from 10% to 50% by weight.

Photopolymerizable compounds (C)

The photopolymerizable compound (C) of this embodiment may include unsaturated compounds having at least one ethylene unsaturated group and unsaturated compounds having at least two ethylene unsaturated groups.

Specific examples of the unsaturated compounds having at least one vinyl unsaturated group may include, but are not limited to, acrylamide, acrylonitrile, methacryloylonitrile, 7-amino-3,7-dimethyloctyl acrylate, 7-amino-3,7-dimethyloctyl methacrylate, isobutoxymethacrylamide, isobutoxymethylmethacrylamide, isoborneoloxyethyl acrylate, isoborneoloxyethyl methacrylate, isoborneol acrylate, isoborneol methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate. Ethyl diethylene glycol acrylate, ethyl diethylene glycol methacrylate, tert-octyl acrylamide, tert-octyl methacrylamide, diacetone acrylamide, diacetone methacrylamide, dimethyl amino acrylate, dimethyl amino methacrylate, dodecyl acrylate, dodecyl methacrylate, dicyclopentenyl oxyethyl acrylate, dicyclopentenyl oxyethyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, N,N-dimethyl acrylamide, N,N-dimethyl methacrylamide, tetrachlorophenyl acrylate, methyl methacrylate Tetrachlorophenyl acrylate, 2-Tetrachlorophenoxyethyl acrylate, 2-Tetrachlorophenoxyethyl methacrylate, Tetrahydrofurfuryl acrylate, Tetrahydrofurfuryl methacrylate, Tetrabromophenyl acrylate, Tetrabromophenyl methacrylate, 2-Tetrabromophenoxyethyl acrylate, 2-Tetrabromophenoxyethyl methacrylate, 2-Trichlorophenoxyethyl acrylate, 2-Trichlorophenoxyethyl methacrylate, Tribromophenyl acrylate, Tribromophenyl methacrylate, 2-Tribromophenoxyethyl acrylate, 2-Tribromophenoxyethyl methacrylate, Acrylic acid 2-Hydroxyethyl acrylate, 2-Hydroxyethyl methacrylate, 2-Hydroxypropyl acrylate, 2-Hydroxypropyl methacrylate, vinylcaprolactone, N-vinylcortyrolone, phenoxyethyl acrylate, phenoxyethyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, polyethylene monoacrylate, polyethylene monomethacrylate, polyethylene monoacrylate, propylene monoacrylate, propylene monomethacrylate, borneol acrylate, borneol methacrylate, or combinations thereof. Among them, unsaturated compounds having at least one vinyl unsaturated group may be used alone or in combination.

Specific examples of the unsaturated compounds having at least two vinyl unsaturated groups may 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)isocyanate diacrylate, and tri(2-hydroxyethyl)isocyanate dimethacrylate. Acrylic esters, tri(2-hydroxyethyl) isocyanate triacrylate, tri(2-hydroxyethyl) isocyanate trimethacrylate, caprolactone-modified tri(2-hydroxyethyl) isocyanate triacrylate, caprolactone-modified tri(2-hydroxyethyl) isocyanate trimethacrylate, trihydroxymethylpropyl triacrylate, trihydroxymethylpropyl trimethacrylate, ethoxylated (hereinafter referred to as EO)-modified trihydroxy acrylate Methylpropyl ester, EO-modified trihydroxymethylpropyl methacrylate, propoxylated (hereinafter referred to as PO)-modified trihydroxymethylpropyl methacrylate, PO-modified trihydroxymethylpropyl methacrylate, 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 hexaacrylate (DPHA), dipentaerythritol hexamethacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol tetramethacrylate, dipentaerythritol tetramethacrylate, caprolactone-modified dipentaerythritol hexamethacrylate, caprolactone-modified dipentaerythritol hexamethacrylate, caprolactone-modified dipentaerythritol pentamethacrylate, caprolactone-modified dipentaerythritol pentamethacrylate, ditrihydroxymethylpropyl tetraacrylate, ditrihydroxymethylpropyl tetramethacrylate, EO-modified bisphenol A diacrylate, EO-modified bisphenol A dimethacrylate, PO-modified bisphenol A diacrylate, DPHA dimeth ... Phenolic 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 glyceryl tripropionate, EO-modified bisphenol F diacrylate, EO-modified bisphenol F dimethacrylate, phenolic polyglycerol ether acrylate, phenolic polyglycerol ether methacrylate, products manufactured by Toa Synthetic Co., Ltd. of Japan and with model number TO-1382, or products manufactured by Nippon Kayaku Co., Ltd. and with model number KAYARAD. Commercial products such as DPCA-12, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, or KAYARAD DPCA-120. The unsaturated compounds having at least two vinyl unsaturated groups can be used alone or in combination.

Specific examples of the photopolymerizable compound (C) preferably include trimethylolpropionic acid triacrylate, EO-modified trimethylolpropionic acid trimethacrylate, EO-modified trimethylolpropionic acid triacrylate, PO-modified trimethylolpropionic acid triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol tetraacrylate, caprolactone-modified dipentaerythritol hexaacrylate, ditrimethylolpropionic acid tetraacrylate, PO-modified glyceryl tripropionate, KAYARAD DPCA-12, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60 or KAYARAD DPCA-120, or combinations thereof.

Specific examples of the photopolymerizable compound (C) are more preferably dipentaerythritol hexaacrylate, dipentaerythritol tetraacrylate, EO-modified trimethylolpropene trimethacrylate, or combinations thereof.

The aforementioned photopolymerizable compound (C) can be used alone or in combination.

The photopolymerizable compound (C) comprises, by weight of 100% by weight, 2.5% to 75% by weight, more preferably 5% to 60% by weight, and even more preferably 10% to 50% by weight, of the total solid component of the photosensitive tinted resin composition.

Photoinitiator (D)

The photoinitiator (D) in this embodiment can be a free radical type photoinitiator.

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

Acetophenone compounds are 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-morpholinophenyl)-1-butanone, or combinations thereof.

Diimidazole compounds are selected from 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-fluorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(o-methylphenyl)-4,4',5,5'-tetraphenylbiimidazole. 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(p-methoxyphenyl)-4,4’,5,5’-tetraphenyl-biimidazole (e.g., zole), 2,2’-bis(2,2’,4,4’-tetramethoxyphenyl)-4,4’,5,5’-tetraphenylbiimidazole, 2,2’-bis(2-chlorophenyl)-4,4’,5,5’-tetraphenylbiimidazole, 2,2’-bis(2-chlorophenyl)-4,4’,5,5’-tetraphenylbiimidazole, 2,2’-bis(2,4-dichlorophenyl)-4,4’,5,5’-tetraphenylbiimidazole, or combinations thereof.)

Acetome compounds are selected from ethanecones, such as 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-substituted]-,1-(oxoacetyl oxime), for example, the product CGI-242 manufactured by Ciba Specialty Chemicals, with the structure shown in formula (IV-1) below, and 1-[4-(phenylthio)phenyl]-octane-1,2-dione 2-(O-benzoyloxime), for example, Ciba Specialty Chemicals. The product CGI-124, manufactured by Chemicals Co., Ltd., has the structure shown in formula (IV-2) below; ethaneone, 1-[9-ethyl-6-(2-chloro-4-benzyl-thio-benzoyl)-9-hydro-carbazole-3-substituted]-, 1-(oxoacetyl oxime), for example, manufactured by Asahi Denka Co., Ltd., has the structure shown in formula (IV-3) below; or combinations thereof.

In one embodiment, the photoinitiator (D) may further include benzophenone compounds such as thioxanthone, 2,4-diethyl-thioxanthanone, thioxanthone-4-sulfone, benzophenone, 4,4’-bis(dimethylamino)benzophenone, and 4,4’-bis(diethylamino)benzophenone; α-diketone compounds such as benzil and acetyl; acyloin compounds such as benzoin; and benzoin methyl ether. Keto-alcohol ethers such as methyl ether, benzoin ethyl ether, and benzoin isopropyl ether; acylphosphine oxides such as 2,4,6-trimethyl-benzoyl-diphenyl-phosphine oxide and bis-(2,6-dimethoxy-benzoyl)-2,4,4-trimethyl-benzyl-phosphine oxide; quinones such as anthraquinone and 1,4-naphthoquinone; and phenacyl methyl chloride. Halides of compounds such as chloride, tribromomethyl-phenylsulfone, and tris(trichloromethyl)-s-triazine; and peroxides such as di-tertbutylperoxide. Among these, benzophenone compounds are preferred, especially 4,4'-bis(diethylamine)benzophenone.

Preferred photoinitiators (D) include 1-[4-(phenylthio)phenyl]-octane-1,2-dione 2-(O-benzoyl oxime) (e.g., CGI-124 manufactured by Ciba Specialty Chemicals), 2,2’-bis(2,4-dichlorophenyl)-4,4’,5,5’-tetraphenyldiimidazole, 4,4’-bis(diethylamine)benzophenone, or combinations thereof.

The aforementioned photoinitiator (D) can be used alone or in combination.

The photoinitiator (D) comprises, by weight of 100% by weight, a photoinitiator (D) of 0.1% to 30% by weight, preferably 0.5% to 20% by weight, and more preferably 1% to 15% by weight, of the total solid components of the photosensitive stained resin composition.

Solvent (E)

The preparation of the photosensitive tinted resin composition of this embodiment typically involves first dissolving all components except the tinting agent (A) in a solvent (E) to prepare a liquid composition, and then adding the tinting agent (A) and mixing thoroughly. The solvent (E) must be selected to dissolve the alkali-soluble resin (B), the photopolymerizable compound (C), and the photoinitiator (D), and must not react with these components and must have suitable volatility. Furthermore, when adding the tinting agent (A) and/or the additive (F), the solvent (E) must be selected to dissolve both the tinting agent (A) and/or the additive (F), and must not react with these components and must have suitable volatility.

Furthermore, solvent (E) may be the same as the solvent used in the preparation of the alkali-soluble resin (B), and will not be described further here. Solvents may be used alone or in combination. Solvent (E) is preferably composed of propylene glycol methyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, or combinations thereof.

The solvent (E) content is 75% to 82% by weight, more preferably 76% to 82% by weight, and even more preferably 78% to 82% by weight, based on 100% by weight of the photosensitive pigment composition.

Additive (F)

In this embodiment, the photosensitive tinted resin composition also includes additives (F), such as fillers, polymers other than alkali-soluble resins (B), adhesion promoters, antioxidants, UV absorbers, anti-aggregating agents, etc.

Fillers may include glass, aluminum, or combinations thereof.

Examples of polymeric compounds include polyvinyl alcohol, polyethylene glycol monoalkyl ethers, polyfluoroacrylates, or combinations thereof.

Adhesion promoters may include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-epoxypropanolpropyltrimethoxysilane, 3-epoxypropanolpropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methpropenoloxypropyltrimethoxysilane, 3-thiolpropyltrimethoxysilane, or combinations thereof.

Antioxidants include 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-di-tert-butylphenol, or combinations thereof.

Examples of ultraviolet absorbers include 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorophenyl azidophenone, alkoxybenzophenone, or combinations thereof.

Anti-aggregating agents include sodium polyacrylate.

The above-mentioned additive (F) can be used alone or in combination.

The additive (F) mentioned above is preferably 3-thiol-propyltrimethoxysilane, 2,2-thiobis(4-methyl-6-tert-butylphenol), or a combination thereof.

Based on a total weight percentage of 100% by weight of the solid components of the photosensitive coloring resin composition, the additive (F) can be from 0.001% by weight to 15% by weight, more preferably from 0.005% by weight to 10% by weight, and even more preferably from 0.01% by weight to 5% by weight.

<Preparation Method of Photosensitive Pigmented Resin Composition>

The preparation method of the photosensitive tinted resin composition in this embodiment is not particularly limited. Specifically, the preparation method of the photosensitive tinted resin composition can be listed as follows: (1) First, a tinting agent (A) is added to a solvent (E) to prepare a tinting agent dispersion. Then, an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and an additive (F) as needed are added to the tinting agent dispersion and mixed. (2) A method in which the tinting agent (A), the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), and an additive (F) as needed are simultaneously added to a solvent (E) and mixed. (3) First, a method in which an alkaline-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and an additive (F) as needed are added to a solvent (E) and mixed, followed by the addition of a colorant (A) and dispersion; and (4) a method in which a colorant dispersion is prepared by first adding a colorant (A) and a portion of the alkaline-soluble resin (B) to a solvent (E), followed by adding another portion of the alkaline-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), and an additive (F) as needed to the colorant dispersion and mixing.

It should be noted that the above examples illustrate methods for dispersing colorant (A). When using a colorant (A) with high solubility, a preparation process can be adopted in which the colorant (A) is pre-dissolved in solvent (E); or a preparation process can be adopted in which the colorant (A) is dissolved in solvent (E) simultaneously with other components.

Of these methods, those described in (1) and (4) are preferred in terms of effectively preventing the aggregation of colorant (A) and ensuring uniform dispersion.

Methods for uniformly dispersing/mixing the components include using a mixer and/or a disperser. Dispersers include twin-roll mills, three-roll mills, ball mills, vibrating ball mills, paint conditioners, continuous disc bead mills, and continuous ring bead mills. The preferred dispersion conditions for bead mills are a bead diameter of 0.03 mm to 2.00 mm, more preferably 0.10 mm to 1.0 mm.

<Color Filter>

This embodiment provides a color filter made of the photosensitive tinted resin composition as described above.

Specifically, the color filter of this embodiment includes a substrate (also called a transparent substrate) and filter segments made of a photosensitive colored resin composition. The color filter can have red, green, and blue filter segments by appropriately selecting the type of colorant (A) used. Furthermore, the filter segments in the color filter of this embodiment may further include magenta, cyan, and yellow filter segments. Alternatively, a reflective substrate can be used instead of a transparent substrate. Examples of transparent substrates include glass substrates. Specific examples of reflective substrates include substrates using aluminum electrodes or metal thin films as reflective surfaces. Furthermore, transparent electrodes such as ITO films can also be formed on the substrate.

<Manufacturing Method of Color Filters>

The color filter of this embodiment includes a filter segment made of a photosensitive colored resin composition, wherein the color filter is preferably formed on a substrate. More preferably, a black matrix is first formed on a substrate (also called a transparent substrate), and then the filter segment made of the photosensitive colored resin composition is formed to manufacture the color filter. Alternatively, a thin-film transistor (TFT) can be pre-formed on the substrate before forming the black matrix.

Specific examples of black matrices include chromium, chromium/chromium oxide multilayer films, inorganic films such as titanium nitride, and resin films with dispersed opacifiers.

In one embodiment, the filter segment can be formed using a photolithography process.

In photolithography, for example, a photosensitive resin composition containing a specific colorant is coated onto a transparent substrate to form a film with a dry film thickness of approximately 0.2 to 5 μm. Next, the obtained film (hereinafter referred to as the first film) is exposed (irradiated) through a photomask with a predetermined pattern. Then, the exposed first film is developed by immersion in a solvent or alkaline developer or by spraying a developer, and uncured portions are removed to obtain the predetermined pattern. This step is repeated using a photosensitive resin composition with a different colorant to produce a color filter with filter segments of various colors. Furthermore, a second film (oxygen barrier film) can be formed on the first film using polyvinyl alcohol or water-soluble acrylic resin before exposure. When a second film is formed, the first film does not come into contact with oxygen, thereby improving exposure sensitivity. Furthermore, the color filter can be heated to cure any uncured polymeric compounds in the filter segments.

Specific examples of coating devices include spraying, swirl coating, narrow-slit coating, and roller coating. A drying step can be performed during coating. Drying devices can include, for example, hot air furnaces and infrared heaters.

Specific examples of alkaline developers include inorganic bases such as sodium carbonate and sodium hydroxide; and organic bases such as dimethylbenzylamine and triethanolamine. Furthermore, antifoaming agents and/or surfactants may be added to the developer.

Image display device

This embodiment provides an image display device, including the color filter as described above.

The image display device in this embodiment is, for example, a liquid crystal display (LCD).

First, a color filter made of the aforementioned photosensitive colored resin composition and a substrate equipped with a thin-film transistor (TFT) are arranged facing each other, with a gap (cell gap) between them. Next, an adhesive is used to bond the color filter to the periphery of the substrate, leaving injection holes. Then, liquid crystal is injected into the substrate surface and into the gaps created by the adhesive through the injection holes, and the injection holes are sealed to form a liquid crystal layer. Finally, a polarizing film and/or a retardation film are attached to the substrate. In this way, a liquid crystal display element can be formed.

Next, a light source is disposed on one side of the liquid crystal display element to form a liquid crystal display device. Specific examples of the light source include cold cathode fluorescent lamps (CCFLs) and white LEDs. The liquid crystal used above, i.e., liquid crystal compounds or liquid crystal compositions, is not particularly limited here, but any type of liquid crystal compound or liquid crystal composition can be used.

Liquid crystal display devices are not particularly limited; for example, they can be used in liquid crystal display modes that employ color rendering, such as Twisted Nematic (TN), Super Twisted Nematic (STN), In-Plane Switching (IPS), Vertical Alignment (VA), and Optically Compensated Birefringence (OCB) panels.

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

Figure 1 is a cross-sectional view of a liquid crystal display device 10 according to an embodiment. The liquid crystal display device 10 shown in Figure 1 includes a pair of spaced-apart and opposite first transparent substrates 11 and second transparent substrates 21, with a liquid crystal LC sealed between the first transparent substrate 11 and the second transparent substrate 21. The sides of the first transparent substrate 11 and the second transparent substrate 21 closest to the liquid crystal LC are defined as inner surfaces, and the sides of the first transparent substrate 11 and the second transparent substrate 21 furthest from the liquid crystal LC are defined as outer surfaces.

Liquid crystal LCs are aligned according to their driving modes, such as TN, STN, IPS, VA, and OCB.

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 disposed on the first transparent electrode layer 13. Furthermore, a first polarizing plate 15 is disposed on the outer surface of the transparent substrate 11.

On the other hand, the color filter 22 of this 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).

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

Next, the backlight unit 30 is disposed below the first polarizing plate 15. Furthermore, a white LED light source 31 is disposed on one side of the backlight unit 30. The white LED light source 31 includes a light source in which a fluorescent filter is formed on the surface of a blue LED, and a light source containing a phosphor within the blue LED resin package.

The image display device of this embodiment may include liquid crystal displays, organic electroluminescent displays, quantum dot displays, electronic paper, and head-mounted displays, etc.

The present invention will be further illustrated by the following experimental examples; however, it should be understood that these examples are for illustrative purposes only and should not be construed as limiting the implementation of the present invention.

Example of synthesis of alkali-soluble resin (B) Synthetic Example b-1

One part by weight of 2,2'-azobisisobutyronitrile, 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 paraben methacrylate, and 30 parts by weight of N-phenylmaleimide were placed in a round-bottom flask equipped with a stirrer and a condenser. The flask was filled with nitrogen gas, and then the mixture was slowly stirred and heated to 80°C to ensure homogeneous mixing of the reactants and polymerization for 4 hours. The temperature was then raised to 100°C, and 0.5 parts by weight of 2,2'-azobisisobutyronitrile were added, followed by polymerization for 1 hour to obtain a reaction solution. This reaction solution was poured into 1500 mL of water to precipitate the polymer, which was then filtered. Next, it was placed in a vacuum oven and dried at 60°C to obtain the first alkali-soluble resin of Synthetic Example b-1.

Synthetic Example b-2

Two parts by weight of 2,2'-azobisisobutyronitrile, 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 paraben methacrylate were placed in a round-bottom flask equipped with a stirrer and a condenser. The flask was filled with nitrogen gas, and then the mixture was slowly stirred and heated to 80°C to ensure homogeneous mixing of the reactants. Polymerization was carried out for 3 hours. Afterward, the temperature was raised to 100°C, and 0.5 parts by weight of 2,2'-azobisisobutyronitrile were added, followed by polymerization for 1 hour. The resulting reaction solution was then poured into 1500 mL of water to precipitate the polymer, which was then filtered. Next, it was placed in a vacuum oven and dried at 60°C to obtain the first alkali-soluble resin of Synthetic Example b-2.

Examples 1 to 11 and Comparative Examples 1 to 5

Examples 1 to 11 and Comparative Examples 1 to 5 of the photosensitive tinted resin composition are described below:

Implementation Example 1 a. Preparation of photosensitive tinted resin components

First, place 5 parts by weight of dibenzopiperanone colorant (a1-5), 20 parts by weight of other colorant (a2-1), 12.5 parts by weight of Ajisper PB821 (manufactured by Ajinomoto Fine-Techno) (as a dispersant), and propylene glycol methyl ether acetate into a wide-mouth bottle. Acetate (PGMEA, manufactured by Daicel-Allnex) was used in a mixture of 150 parts by weight and 562.5 parts by weight of 2mm zirconium oxide beads. After pre-crushing using a coating oscillator (PCMH-C50M, Asada Tetsugan), the solution was transferred to another wide-mouth bottle. Then, 562.5 parts by weight of 0.1mm zirconium oxide beads were added. The mixture was vibrated using the coating oscillator for 20 hours and then filtered through a 5.0μm filter to obtain a colorant dispersion with a solid content of 20%.

Next, 187.5 parts by weight of the above-mentioned colorant dispersion (containing 5 parts by weight of dibenzopiperanol colorant (a1-5) and 20 parts by weight of other colorant (a2-1), 20 parts by weight of the first alkali soluble resin of synthetic example b-1 (hereinafter referred to as b-1), 37.9 parts by weight of dipentaerythritol hexaacrylate (hereinafter referred to as c-1), and 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-thiolpropyltrimethoxysilane (hereinafter referred to as f-1) are added to 300 parts by weight of PGMEA (hereinafter referred to as e-1), and stirred evenly with a shaking stirrer to obtain the photosensitive tinting resin composition of Example 1, the solid content of which is 20.0% by weight.

b. Creation of patterns (which can serve as the color layer for color filters)

The photosensitive tinting resin composition of Example 1 was coated onto a 100mm×100mm glass substrate by rotary coating. First, it underwent depressurization drying at 100mmHg for 30 seconds, followed by pre-baking at 90°C for 2 minutes to form a 2.4μm thick pre-baked coating. The pre-baked coating was then irradiated with ultraviolet light (Canon PLA-501F exposure machine) at a light intensity of 100mJ/ ^cm² , immersed in a 23°C developer for 1 minute, washed with pure water, and then baked at 200°C for 20 minutes to form a 2.0μm thick pattern on the glass substrate (which can be used as a tinting layer for a color filter).

The pattern of Embodiment 1 was evaluated using the evaluation method described later, and the results are shown in Table 1.

Examples 2 to 11, Comparative Examples 1 to 5

The photosensitive tinted resin compositions and tinted layers (color filters) of Examples 2 to 11 and Comparative Examples 1 to 5 were prepared using the same steps as in Example 1, with the difference being: variations in the types and amounts of components in the photosensitive tinted resin compositions, as well as the content of solid components. Examples 2 to 11 are shown in Table 1, and Comparative Examples 1 to 5 are shown in Table 2. The components corresponding to the numbers in Tables 1 and 2 are shown in Table 3. The prepared photosensitive tinted resin compositions were evaluated using the evaluation method described later, and the results for Examples 2 to 11 and Comparative Examples 1 to 5 are shown in Tables 1 and 2, respectively.

control group Preparation of photosensitive stained resin composition

First, in a wide-mouth bottle, 5 parts by weight of dibenzopiperanone colorant (a’-1), 20 parts by weight of other colorants (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 with a particle size of 2 mm were placed. After pre-pulverization using a paint oscillator (PCMH-C50M, Asada Tetsugan), the solution was transferred to another wide-mouth bottle, and 562.5 parts by weight of zirconia beads with a particle size of 0.1 mm were added. The solution was then vibrated using a paint oscillator for 20 hours, and finally filtered through a 5.0 μm filter to obtain a colorant dispersion of the control example, with a solid content of 20%.

Next, 187.5 parts by weight of the above-mentioned colorant dispersion (containing 5 parts by weight of dibenzopiperanone colorant (a’-1) and 20 parts by weight of other colorants (a2-3)), 20 parts by weight of b-1, 37.9 parts by weight of c-1, 7 parts by weight of d-1, and 0.1 parts by weight of f-1 were added to 487 parts by weight of e-1, and stirred evenly with a shaking stirrer to produce a comparative example of a photosensitive colorant resin composition with a solid content of 15.0% by weight.

[Evaluation Method] [1] Relative total VOC reduction rate

First, the first experimental procedure for the control group was performed to obtain the total VOC content X (ppm). Specifically, the photosensitive tinted resin composition of the control example was coated onto a 100mm × 100mm glass substrate using a spin coating method. After covering the coating with a transparent cover having openable and closable holes, it was heated at 90°C. After 60 minutes, a coating with a dry film thickness of 2.4μm was formed. After the heating treatment, a handheld VOC meter (model Tiger ppm; manufactured by Ion Science) was simultaneously inserted into the holes to measure the VOC content _X1 (ppm). After repeating the above procedure for 5 rounds, VOC contents _X2 to _X5 were obtained respectively. Finally, _X1 to _X5 were summed to obtain the total VOC content X (ppm).

Next, the second experimental procedure of the experimental group was conducted to obtain the total VOC content Y (ppm). The photosensitive tinted resin compositions of the embodiments and comparative examples were coated onto 100mm × 100mm glass substrates by spin coating. Then, they were heated under the same conditions and steps as the first experimental procedure of the control group to form a coating with a dry film thickness of 2.4μm. After the heating treatment, VOC measurement was performed simultaneously. After repeating the process for a total of 5 rounds, the VOC contents _Y1 to _Y5 were obtained respectively. Finally, _Y1 to _Y5 were summed to obtain another total VOC content Y (ppm).

Calculate the relative total VOC reduction rate using the following formula. A higher relative total VOC reduction rate indicates a greater effect in reducing total VOC levels. Furthermore, when Y > X, it indicates no benefit in reducing VOCs; in this case, the calculation is not performed, and the evaluation result is ×.

Relative total VOC reduction rate (%) = (X-Y)/X×100 (%)

○: Relative total VOC reduction rate > 19.5%

×: Relative total VOC reduction rate ≤ 19.5%

[2] Brightness

Under light source C, the luminance (Y value) of the chromatic layer was measured using a colorimeter (model MCPD, manufactured by Otsuka Denko) with a 2-degree field of view. A higher Y value indicates higher luminance. The Y value was evaluated according to the following criteria: ◎: Y value ≥ 15; ○: 13 ≤ Y value < 15; △: 11 ≤ Y value < 13; ×: Y value < 11.

[3] Pattern properties

The pattern properties of the filter fragments were confirmed using a scanning electron microscope (SEM) (model S-3000H, manufactured by Hitachi High Tech). Specifically, SEM images of the 100μm wide stripe pattern were captured, and the gradient angle (the angle between the glass substrate and the pattern) of the stripe pattern cross-section was evaluated using a protractor according to the following criteria.

◎：55° < gradient angle ≦70°

○: 45° < gradient angle ≤ 55°

△: 35° < gradient angle ≤ 45°

×: Gradient angle ≤ 35° or gradient angle > 70°

<Evaluation Results>

As shown in Tables 1 and 2, when the colorant (A) includes the dibenzopiperanone-based colorant (A-1) represented by Formula (I), and when the solid content is controlled within the range of 18% to 25% by weight (Examples 1 to 11), the photosensitive coloring resin composition can simultaneously achieve high solid content and a higher relative total VOC reduction rate in the production process of forming color filters. Furthermore, the colored layer (pattern) produced by the photosensitive coloring resin composition exhibits good brightness and pattern properties.

Conversely, when the solid content of the photosensitive tinted resin composition is less than 18% by weight (Comparative Examples 3 and 5), the photosensitive tinted resin composition does not have a relative reduction effect on total VOCs.

Furthermore, provided that the colorant (A) includes the dibenzopiperanone-based colorant (A-1) shown in formula (I), when the solid content of the photosensitive coloring resin composition is greater than 25% by weight (Comparative Example 4), the brightness and pattern properties of the colored layer (pattern) produced by the photosensitive coloring resin composition are poor.

Furthermore, when the photosensitive coloring resin composition does not include the dibenzopiperanone colorant (A-1) shown in Formula (I) (Comparative Examples 1 and 2), the brightness and pattern properties of the colored layer (pattern) produced by the photosensitive coloring resin composition are poor.

Furthermore, when the solid content is 18% to 22% by weight (Examples 1 to 5) based on 100% by weight of the photosensitive coloring resin composition, the pattern properties of the colored layer (pattern) produced by the photosensitive coloring resin composition are even better.

Furthermore, when formula (I) preferably contains at least ^two _-SO3- , and _R9 ^is _-SO3- , and _R7 is a hydrogen atom or _-SO3- (Examples 1 to 3, 6 ^and 7), the brightness of the colored layer (pattern) made from the photosensitive colored resin composition can be further improved.

Furthermore, when ^R11 , ^R12 , and ^R13 each independently represent a linear or branched alkyl or polyether structure with 1 to 20 substituted or unsubstituted atoms, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure (Examples 1 to 3, 8, and 9), the brightness of the colored layer (pattern) made from the photosensitive colored resin composition can be further improved.

In summary, this embodiment provides a photosensitive color resin composition, a color filter, and an image display device. By limiting the colorant (A) to include dibenzopiperanone colorants (A-1) as shown in Formula (I) and limiting the solid content to 18% to 25% by weight, it achieves good brightness and pattern properties of the colored layer (pattern) while simultaneously considering high solid content and increased total VOC reduction rate in the production process of the color filter formed by the photosensitive color resin composition, thus achieving an environmentally friendly effect.

Claims (9)

A photosensitive coloring resin composition includes: a colorant (A), including a dibenzopiperanone colorant (A-1) represented by formula (I); an alkaline soluble resin (B); a photopolymerizable compound (C); a photoinitiator (D); and a solvent (E), wherein the solid content is 18% to 25% by weight, based on 100% by weight of the photosensitive coloring resin composition. In Formula (I), ^R1 , ^R2 , ^R3 , and ^R4 each independently represent a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms. Alternatively, ^R1 and ^R2 , or ^R3 and ^R4, may be bonded together to form a ring. ^R5 , ^R6 , ^R7 , ^R8 , and ^R9 each independently represent a hydrogen atom, a halogen atom, a hydroxyl _{group, -SO3-, -SO3H ,} ^-SO3M _, and... The alkyl group may be a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 carbon atoms, or a substituted or unsubstituted linear or branched alkenyl group having 2 to 20 carbon atoms, or ^R5 and ^R6 , ^R6 and ^R7 , ^R7 and ^R8 , or ^R8 and ^R9 may be bonded together to form a ring; M represents an alkali metal atom; ^R11 , ^R12 , and ^R13 each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms. The formula (I) contains a linear or branched alkoxy group with 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon with 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group with 2 to 20 carbon atoms, or a polyether structure, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure; n represents a positive integer from 1 to 4, ^and at least two _-SO3- are present in the formula. The photosensitive coloring resin composition as described in claim 1, wherein the content of solid components is 18% to 23% by weight, based on 100% by weight of the photosensitive coloring resin composition. The photosensitive coloring resin composition as described in claim 1, wherein the content of solid components is 18% to 22% by weight, based on 100% by weight of the photosensitive coloring resin composition. ^The photosensitive tinted resin composition as described in claim 1, wherein ^{R9 is} _-SO3- and ^R7 is a hydrogen atom or _-SO3- . The photosensitive tinted resin composition as described in claim 1, wherein in formula (I), ^R11 , ^R12 , and ^R13 each independently represent a linear or branched alkyl or polyether structure having 1 to 20 carbon atoms, whether substituted or unsubstituted, and at least one of ^R11 , ^R12 , and ^R13 is a polyether structure. The photosensitive coloring resin composition as claimed in claim 1, wherein the total weight of the solid components based on the photosensitive coloring resin composition is 100% by weight, and the dibenzopiperanone colorant (A-1) is from 0.01% to 25% by weight. The photosensitive tinted resin composition as claimed in claim 1, wherein the total weight of the solid components based on the photosensitive tinted resin composition is 100% by weight, the tinting agent (A) is 1% to 85% by weight, the alkaline 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. A color filter made of a photosensitive tinted resin composition as described in any one of claims 1 to 7. An image display device includes a color filter as described in claim 8.