Photosensitive resin composition, color filter and manufacturing method thereof, and liquid crystal display device

Abstract

X, M are as stated in a specification and claims respectively. This invention also provides a manufacturing method of a color filter comprising forming a pixel layer using said photosensitive resin composition, a color filter produced by said manufacturing method, and a liquid crystal display device comprises said color filter. Through said xanthene-based colorant (A-1) and said compound (E) having a structure represented by formula (V), this invention can make said photosensitive resin composition has good storage filtration stability with high finesse.

Description

[Technical Field]

[0001] This invention relates to a resin composition, a color filter, and a liquid crystal display, particularly to a photosensitive resin composition, a color filter, a method for manufacturing the same, and a liquid crystal display. [Previous Technology]

[0002] Currently, color filters are widely used in color LCD displays, color fax machines, color cameras, and other application fields. Among them, as the market demand for color LCD displays continues to expand, the manufacturing technology of color filters is also becoming more diversified, including methods such as dyeing, printing, electroplating, and dispersion. Among these, dispersion is the mainstream method for manufacturing color filters.

[0003] This dispersion method involves first dispersing the colorant in a photosensitive resin to form a photosensitive resin composition, then coating the photosensitive resin composition onto a glass substrate, and subjecting it to exposure and development steps to transform the photosensitive resin composition into a pixel layer with a specific pattern. After repeating the above coating, exposure, and development processes three times, the red (R) pixel layer, green (G) pixel layer, and blue (B) pixel layer of the color filter are obtained. Generally, to further improve the contrast of the color filter, a black matrix (or light-blocking layer) is placed between the aforementioned pixel layers.

[0004] Quality requirements for photosensitive resin compositions for color filters include contrast and brightness, but in recent years, the importance of quality items such as filterability and the presence of crystalline foreign matter has also increased. In the manufacturing of photosensitive resin compositions for color filters, the final process includes a filtration procedure. However, if large particles remain after filtration, the filter screen must be replaced frequently, significantly reducing the filtration speed. Furthermore, there is a problem that the post-baking process in the color filter manufacturing process can generate crystalline foreign matter.

[0005] In addition, in recent years, with the miniaturization of pixels in liquid crystal display devices, the pore size of filter screens has become smaller in order to remove finer foreign objects. Therefore, a very high level of filtration performance is required. At the same time, it is also necessary to avoid the problem of deterioration of filtration stability after long-term storage.

[0006] Therefore, how to improve the high precision and long-term filtration stability of photosensitive resin compositions is a problem that technicians in this field urgently need to solve. [Summary of the Invention]

[0007] Therefore, the first object of the present invention is to provide a photosensitive resin composition having good high fineness and long-term filtration stability.

[0008] Therefore, the photosensitive resin composition of the present invention comprises a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), a compound (E) having a structure as shown in formula (V), and a solvent (F). The colorant (A) comprises a triphenylmethane-based colorant (A-1). Formula (V)

[0009] In this formula (V), R 24, R 25, R 26 and R 27 each independently represent a hydrogen atom, alkyl, hydroxyl or amino group, X represents an aliphatic hydrocarbon group with 1 to 5 carbon atoms or an aromatic hydrocarbon group with 6 to 10 carbon atoms, and M represents a hydrogen atom, alkali metal, ammonium group or organic ammonium group.

[0010] Furthermore, a second objective of the present invention is to provide a method for manufacturing a color filter.

[0011] Therefore, the method for manufacturing a color filter of the present invention includes forming a pixel layer using the photosensitive resin composition described above.

[0012] Furthermore, a third objective of the present invention is to provide a color filter.

[0013] Therefore, the color filter of the present invention is manufactured by the color filter manufacturing method described above.

[0014] Furthermore, a fourth objective of the present invention is to provide a liquid crystal display.

[0015] Thus, the liquid crystal display of the present invention includes a color filter as described above.

[0016] The advantage of the present invention is that by using a colorant (A) including the triphenylmethane-based colorant (A-1) and a compound (E) having the structure shown in formula (V), the photosensitive resin composition has good high fineness and long-term filtration stability.

Implementation Method

[0017] 《Photosensitive Resin Composition》

[0018] The present invention provides a photosensitive resin composition comprising a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), a compound (E) having a structure as shown in formula (V), and a solvent (F). Furthermore, in some embodiments of the present invention, the photosensitive resin composition may selectively include an additive (G).

[0019] The various components in the photosensitive resin composition used in the present invention will be described in detail below.

[0020] In the following text, "solid component of photosensitive resin composition" refers to the component other than the solvent (F); "total weight of solid component of photosensitive resin composition" refers to the total weight of the component other than the solvent (F).

[0021] In the following text, acrylic acid and / or methacrylic acid are referred to as (meth)acrylic acid, and acrylates and / or methacrylates are referred to as (meth)acrylate; similarly, acrylonitrile and / or methacrylic acid are referred to as (meth)acrylamide; acrylamide and / or methacrylamide are referred to as (meth)acrylamide.

[0022] 〈Coloring Agent (A)〉

[0023] The colorant (A) includes a triphenylmethane-based colorant (A-1). Furthermore, in some embodiments of the present invention, the colorant (A) may also include other colorants (A-2) besides the triphenylmethane-based colorant (A-1).

[0024] 〔Triphenylmethane-based colorant (A-1)〕

[0025] In some embodiments of the present invention, the triphenylmethane colorant (A-1) has at least one selected from the group consisting of triphenylmethane colorant (A-1-1), triphenylmethane colorant (A-1-2), and triphenylmethane colorant (A-1-3).

[0026] [Triphenylmethane-based colorant (A-1-1)]

[0027] The triphenylmethane-based colorant (A-1-1) has the structure shown in formula (I-1). In formula (I-1), 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 with a saturated aliphatic hydrocarbon group at least at the end directly bonded to N, or an aromatic group having such an aliphatic hydrocarbon group. The carbon chain of the aliphatic hydrocarbon group may contain at least one of an oxygen atom, a sulfur atom, and a nitrogen atom. The carbon chain of the aromatic group may contain at least one of an oxygen atom, a sulfur atom, and a nitrogen atom. R1, R2, R3, R4, and R5 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. R2 and R3 may bond to each other to form a ring structure, and R4 and R5 may bond to each other to form a ring structure. Multiple R1, R2, R3, R4, and R5 may be the same or different. Ar 1 represents a substituted or unsubstituted divalent aromatic group, and multiple Ar 1s can be the same or different. p represents an integer greater than 2.

[0028] In formula (I-1), the p-valent organic group represented by A has a carbon atom directly bonded to a nitrogen atom (N) that does not have a π bond. This organic group represents an aliphatic hydrocarbon group with a saturated aliphatic hydrocarbon group at the end directly bonded to N, or an aromatic group containing such an aliphatic hydrocarbon group. The carbon chain of the aliphatic hydrocarbon group may contain oxygen (O), sulfur (S), and nitrogen (N), and the carbon chain of the aromatic group may also contain O, S, and N. Since the carbon atom directly bonded to N does not have a π bond, the color characteristics such as hue or transmittance of the cationic chromogenic site are not affected by the bonding group, i.e., A, or other chromogenic sites, and can maintain the same color as the monomer.

[0029] In formula (I-1), the aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at least at the end directly bonded to N can be any of straight-chain, branched, or cyclic, provided that the carbon atom at the end directly bonded to N does not have a π bond. The carbon atoms other than the terminal carbon atoms can have unsaturated bonds and can have substituents. The carbon chain of the substituent can contain O, S, or N. For example, the carbon chain of the substituent can contain carbonyl, carboxyl, oxycarbonyl, amide, etc., and the hydrogen atom can be substituted with a halogen atom, etc.

[0030] Furthermore, in the A of formula (I-1), the aromatic group having the aliphatic hydrocarbon group can be listed as a monocyclic or polycyclic aromatic group having at least a saturated aliphatic hydrocarbon group at the end directly bonded to N, which may have substituents or be a heterocycle containing O, S, and N.

[0031] In the A of formula (I-1), from the viewpoint of the strength of the skeleton, it is preferable that the A contains a cyclic aliphatic hydrocarbon group or an aromatic group.

[0032] In the A of formula (I-1), from the viewpoint of the strength of the skeleton, it is preferable that the cyclic aliphatic hydrocarbon group of A is 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 polycyclic structure. Examples of bridged alicyclic hydrocarbon groups include norbornane, bicyclic [2.2.2]octane, and adamantane. Preferably, the bridged alicyclic hydrocarbon group is norbornane. Furthermore, the aromatic group can be a group containing a benzene ring or a naphthyl ring. Preferably, the aromatic group is a group containing a benzene ring. For example, when A is a divalent organic group, examples include straight-chain, branched, or cyclic alkyl groups with 1 to 20 carbon atoms, or aromatic groups such as xylylene substituted with two alkyl groups with 1 to 20 carbon atoms.

[0033] In formula (I-1), the valence p is the number of chromogenic cationic sites constituting the cation, and p represents an integer of 2 or more. In this colorant, from the viewpoint of heat resistance, it is preferable that the valence p of the cation is 2 or more, and more preferably, the valence p of the cation is 3 or more. There is no particular upper limit to p, but from the viewpoint of ease of manufacture, it is preferable that p is 4 or less, and more preferably, p is 3 or less.

[0034] In formula (I-1), R1, R2, R3, R4 and R5 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0035] In formula (I-1), the alkyl groups in R1, R2, R3, R4, and R5 are not particularly limited, and can include straight-chain alkyl groups or branched alkyl groups having 1 to 20 carbon atoms. Preferably, the alkyl group is a straight-chain alkyl group or branched alkyl group having 1 to 8 carbon atoms, and more preferably, the alkyl group is a straight-chain alkyl group or branched alkyl group having 1 to 5 carbon atoms. From the viewpoint of pixel brightness, it is particularly preferred that the alkyl groups in R1, R2, R3, R4, and R5 are ethyl or methyl. The substituents that the alkyl group may have are not particularly limited, and can include aryl, halogen atoms, hydroxyl, etc., and substituted alkyl groups can include aralkyl groups such as benzyl groups.

[0036] In formula (I-1), there are no particular restrictions on the aryl groups in R1, R2, R3, R4 and R5, and examples include phenyl, naphthyl, etc. There are no particular restrictions on the substituents that the aryl group may have, and examples include alkyl, halogen atoms, etc.

[0037] The phrase “R2 and R3 can bond with each other to form a ring structure, and R4 and R5 can bond with each other to form a ring structure” means that “R2 and R3 can bond with each other through nitrogen atoms to form a ring structure, and R4 and R5 can bond with each other through nitrogen atoms to form a ring structure”. There are no particular restrictions on the ring structure, and examples include pyrrolidine ring, piperidine ring, or morpholine ring.

[0038] In formula (I-1), from the viewpoint of chemical stability, it is preferable that R1, R2, R3, R4 and R5 are each independently represented by an alkyl group having 1 to 5 carbon atoms, or that R2 and R3 are bonded to each other to form a ring structure, and that R4 and R5 are bonded to each other to form a ring structure, wherein the ring structure may be pyrrolidine ring, piperidine ring or morpholine ring.

[0039] In formula (I-1), R1, R2, R3, R4, and R5 can each independently form the above-described structure; that is, the plurality of R1, R2, R3, R4, and R5 can each be the same or different. Preferably, from the viewpoint of color purity, R1 is a hydrogen atom. More preferably, from the viewpoint of ease of manufacture and raw material supply, R2, R3, R4, and R5 are all the same.

[0040] In formula (I-1), there is no particular restriction on whether the divalent aromatic group in Ar 1 is substituted or unsubstituted, and the plurality of Ar 1s can be the same or different. The aromatic group in Ar 1 can be the same as those listed in the aromatic group of A.

[0041] In formula (I-1), preferably, Ar 1 is an aromatic group with 6 to 20 carbon atoms, either substituted or unsubstituted; more preferably, Ar 1 is an aromatic group containing a condensed polycyclic carbocyclic ring, either substituted or unsubstituted, with 10 to 14 carbon atoms. From the viewpoint of simple structure and low raw material cost, Ar 1 is preferably an enylphenyl or enylnaphthyl.

[0042] In this formula (I-1), multiple R1, R2, R3, R4, R5 and Ar1 exist within one molecule and can be the same or different. By combining the R1, R2, R3, R4, R5 and Ar1, the desired color can be adjusted.

[0043] The structure shown in formula (I-1) is a cation with a valence of 2 or higher, which can be paired with an anion with a valence of 2 or higher. The anion is, for example, B q-.

[0044] It is worth noting that when the compound represented by formula (I-1) is in a state containing an anion and a cation with a valence of divalent or higher, the structure represented by formula (I-1) (i.e., the cation) and the Bq- (i.e., the anion) can form a condensed aggregate. Here, the anion and cation are not simply ionicly bonded one molecule to one molecule, but rather form a molecular assembly by assembling multiple molecules through ionic bonds. Therefore, the apparent molecular weight of this condensed aggregate is higher than that of conventional lake pigments. Generally, it is speculated that the formation of this molecular assembly increases the cohesive force of the condensed aggregate formed by the structure represented by formula (I-1) (i.e., the cation) and the Bq- (i.e., the anion) in the solid state, and reduces thermal motion, thereby inhibiting the dissociation of ion pairs or the decomposition of the cation portion, making it more difficult to fade than conventional lake pigments.

[0045] In some embodiments of the present invention, provided that the structure shown in formula (I-1) is a cation with a valence of 2 or higher combined with the anion of B q-, the molecular assembly can be represented, for example, as the structure shown in formula (I-1-1). Formula (I-1-1) In formula (I-1-1), A, Ar 1, R 1, R 2, R 3, R 4, R 5 and p are the same as in formula (I-1), and will not be described again here. B q- represents an anion. r and s each independently represent an integer of 1 or more.

[0046] In formula (I-1-1), r represents the number of cations, and s represents the number of anions in the molecular assembly. Both r and s independently represent an integer of 1 or more. When r represents 2 or more, the multiple cations in the molecular assembly can be used individually or in combination of 2 or more. Similarly, when s is 2 or more, the multiple anions in the molecular assembly can be used individually or in combination of 2 or more.

[0047] Furthermore, in formula (I-1-1), the B q- (i.e., anion) is not particularly limited and can be an organic anion or an inorganic anion. Here, "organic anion" refers to an anion containing at least one carbon atom. "Inorganic anion" refers to an anion that does not contain a carbon atom. In this embodiment, from the viewpoint of pixel brightness, it is preferable that the B q- is an inorganic anion.

[0048] In some embodiments of the present invention, when B q- is an organic anion, its structure is not particularly limited, and examples such as those described in International Publication No. 2012 / 144520 can be cited.

[0049] From the viewpoint of the stability of the colorant, it is preferable that the Bq- is an organic anion having two or more monovalent anionic substituents in one molecule. Specific examples of such anionic substituents include, for example, acetylinic acid groups (i.e., sulfonate anions) such as -SO₂N-SO₂CH₃, -SO₂N-COCH₃, -SO₂N-SO₂CF₃, -SO₂N-COCF₃, -CF₂SO₂N-SO₂CH₃, -CF₂SO₂N-COCH₃, -CF₂SO₂N-SO₂CF₃, -CF₂SO₂N-COCF₃, -SO₃-, -CF₂SO₃-, -PO₃²⁻, -COO-, -CF₂PO₃²⁻, and -CF₂COO-. From the viewpoint that high acidity effectively stabilizes the cation and maintains the color, the anionic substituent is preferably an imine group, -SO3-, or -CF2SO3-, and more preferably, -SO3- (sulfonic acid group). In the case of multiple substituted anionic substituents, the same substituent or different substituents may be used.

[0050] On the other hand, when B q- is an inorganic anion, its structure is not particularly limited, and examples include anions of oxyacids with a valence of 2 or higher [e.g., phosphate ions, sulfate ions, chromate ions, tungstate ions (WO4 2-), molybdate ions (MoO4 2-), etc.], multiple acid anions formed by the condensation of multiple oxyacids, halogen anions, or mixtures thereof.

[0051] The multiple acid anion can be exemplified by heteropolyacid anion (MyO2z) q- or heteropolyacid anion (XMyO2z) q-. In the above ionic formula, M represents a polyatom, X represents a heteroatom, y represents the composition ratio of the polyatom, and z 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 X include silicon (Si), phosphorus (P), arsenic (As), sulfur (S), iron (Fe), and cobalt (Co). Furthermore, both heteropolyacid anions and heteropolyacid anions may contain para-cations such as Na+ or H+.

[0052] In terms of pixel brightness, preferably, Bq- is a heteropolyacid anion containing at least one of molybdenum (Mo) and tungsten (W), and more preferably, Bq- is a heteropolyacid anion containing at least the q-valent of tungsten. When the Bq- of the present invention is a heteropolyacid anion containing at least one of molybdenum (Mo) and tungsten (W), the high fineness and time-filtration stability of the photosensitive resin composition are even better.

[0053] The multiple acid anions containing at least one of molybdenum (Mo) and tungsten (W) can be, for example, tungstate ion [W 10O 32] 4-, molybdate ion [Mo 6O 19] 2-, phosphotungstate ion [PW 12O 40] 3-, silicotttate ion [SiW 12O 40] 4-, phosphotungstate ion [PMo 12O 40] 3-, phosphotungstate ion [PW 12-aMo aO 40] 3-, H 3 [PW 2-bMo bO 7] 4-, etc., which belong to heterogeneous multiple acid anions.

[0054] In the multiple acid anion containing at least one of molybdenum (Mo) and tungsten (W), there is no particular limitation on the molar ratio of tungsten to molybdenum. From the viewpoint of pixel brightness, it is preferable that the molar ratio of tungsten to molybdenum is between 100:0 and 90:10.

[0055] In some embodiments of the present invention, Bq- represents the aceimine group (i.e., sulfonate anion), halide anion, or the multiple acid anion mentioned above.

[0056] In some embodiments of the present invention, preferably, the Bq- is chloride ion, [PW 12O 4O] 3-, [PW 11.76Mo 0.24O 4O] 3-, or a combination thereof.

[0057] Furthermore, there are no particular limitations on the method of preparing the structure shown in formula (I-1) and the compound shown in formula (I-1-1), for example, it can be prepared with reference to International Publication No. 2012 / 144520.

[0058] Specific examples of the compounds represented by formula (I-1-1) may include at least one of compounds (1) to (22). Each of compounds (1) to (22) contains a cation and a heterologous multiple acid anion.

[0059] In some embodiments of the present invention, preferably, specific examples of the compound represented by formula (I-1-1) include at least one of compound (2), compound (21), and compound (22).

[0060] Compound(1)Compound(2)Compound(3)Compound(4)Compound(5)Compound(6)Compound(7)Compound(8)Compound(9)Compound(10)Compound(11)Compound(12)Compound(13)Compound(14)Compound(15)Compound(16)Compound(17)Compound(18)Compound(19)Compound(20)Compound(21)Compound(22)

[0061] [Triphenylmethane-based colorant (A-1-2)]

[0062] The triphenylmethane-based colorant (A-1-2) has a structure as shown in formula (I-2). In formula (I-2), R6, R7, R8, R9, R10 and R11 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group; R12, R13 and R14 each independently represent an alkyl group having 1 to 8 carbon atoms, or a chlorine atom; t and u each independently represent an integer from 0 to 4; v represents an integer from 0 to 6; wherein t, u and v are not simultaneously 0.

[0063] In this formula (I-2), there are no particular restrictions on the alkyl groups with 1 to 8 carbons in R6, R7, R8, R9, R10 and R11. Specific examples include straight-chain saturated hydrocarbon groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl; isopropyl, isobutyl, secondary butyl, tertiary butyl, isopentyl, methylpentyl, ethylbutyl, methylhexyl, ethylpentyl, propylbutyl, (methylethyl)butyl, (methylethyl)(methyl)propyl, methylheptyl, ethylhexyl, propylpentyl, (methylethyl)pentyl, butylbutyl, dimethylpropyl, dimethylbutyl, (ethyl)(methyl)propyl, dimethylpentyl, (ethyl)(methyl)butyl, dimethylhexyl, (ethyl)(methyl)pentyl, (propyl)(methyl)butyl, (methylethyl)(methyl)butyl and diethylbutyl. In some embodiments of the present invention, preferably, R6, R7, R8, R9, R10 and R11 are each independently an alkyl group having 1 to 4 carbon atoms; more preferably, R6, R7, R8, R9, R10 and R11 are each independently methyl or ethyl.

[0064] In formula (I-2), specific examples of cycloalkyl groups having 3 to 8 carbon atoms in R6, R7, R8, R9, R10, and R11 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. In some embodiments of the present invention, preferably, R6, R7, R8, R9, R10, and R11 are each independently a cycloalkyl group having 4 to 6 carbon atoms; more preferably, R6, R7, R8, R9, R10, and R11 are cyclohexyl.

[0065] In formula (I-2), the aryl groups in R6, R7, R8, R9, R10, and R11 can be aryl groups having 6 to 14 carbon atoms; preferably, the aryl group can be an aryl group having 6 to 10 carbon atoms. The aryl groups in R6, R7, R8, R9, R10, and R11 can be aromatic hydrocarbon cyclic groups or aromatic heterocyclic groups. The aromatic ring in the aromatic hydrocarbon cyclic group can be a monocyclic or fused ring. Specific examples of the aromatic hydrocarbon cyclic group include benzene rings, naphthalene rings, pentalene rings, indene rings, azulene rings, and heptalene rings having one free valence. The aromatic heterocycle can be a monocyclic or fused ring.Specific examples of aromatic heterocycles in this aromatic heterocyclic group include those with one free valence: furan ring, thiophene ring, pyrrole ring, 2H-pyran ring, 4H-thiopyran ring, pyridine ring, 1,3-oxazole ring, isoxazole ring, 1,3-thiazole ring, isothiazole ring, imidazole ring, pyrazole ring, furazane ring, pyrazine ring, pyrimidine ring, pyridazine ring, 1,3,5-triazine ring, benzofuran ring, 2-benzofuran ring, and benzothiophene ring. The rings include 2-benzothiophene ring, 1H-pyrrolidine ring, indole ring, isoindole ring, indolizine ring, 2H-1-benzopyran ring, 1H-2-benzopyran ring, quinoline ring, isoquinoline ring, 4H-quinolidine ring, benzimidazole ring, 1H-indazole ring, quinoxaline ring, quinazoline ring, cinnoline ring, phthalazine ring, 1,8-naphthyridine ring, purine ring, and pteridine ring. In some embodiments of the present invention, in formula (I-2), preferably, R6, R7, R8, R9, R10 and R11 are phenyl.

[0066] In formula (I-2), the alkyl groups having 1 to 8 carbon atoms, the cycloalkyl groups having 3 to 8 carbon atoms, and the aryl groups in R6, R7, R8, R9, R10, and R11 may be substituents including alkoxy groups having 1 to 6 carbon atoms, halogen atoms, trifluoromethyl groups, or cyano groups. Furthermore, the cycloalkyl and aryl groups may also be substituted with alkyl groups having 1 to 6 carbon atoms. Moreover, there are no particular restrictions on the position and number of substituents; when there are two or more substituents, these substituents may be the same or different.

[0067] In formula (I-2), R12, R13, and R14 each independently represent an alkyl group or a chlorine atom having 1 to 8 carbon atoms. In some embodiments of the present invention, preferably, R12, R13, and R14 each independently represent an alkyl group or a chlorine atom having 1 to 4 carbon atoms; more preferably, R12, R13, and R14 each independently represent an alkyl group having 1 to 4 carbon atoms; and even more preferably, R12, R13, and R14 each independently represent a methyl or ethyl group.

[0068] In formula (I-2), t and u each independently represent an integer from 0 to 4; in some embodiments of the present invention, preferably, t and u each independently represent an integer from 0 to 2; v represents an integer from 0 to 6; in some embodiments of the present invention, preferably, v represents 0 or 1; wherein t, u, and v are not simultaneously 0. In some embodiments of the present invention, preferably, the combination of t, u, and v includes a combination of t=1, u=0, v=0, t=0, u=0, v=1, t=2, u=0, v=0, t=1, u=1, v=0, and t=1, u=1, v=1; more preferably, the combination of t, u, and v includes a combination of t=1, u=0, v=0, t=0, u=0, v=1, and t=1, u=1, v=0.

[0069] The structure shown in formula (I-2) is a cationic chromophore of triarylmethane, and examples include the chromophores a3 and a6 in compound group a and the chromophore b3 in compound group b. In some embodiments of the present invention, preferably, the cationic chromophore of the triarylmethane is the chromophore a3.

[0070] [Compound group a](a1),(a2),(a3),(a4),(a5),(a6)

[0071] [Compound Group b](b1),(b2),(b3),(b4),(b5),(b6),(b7),(b8)

[0072] Furthermore, the structure shown in formula (I-2) is a cation, which can be paired with an anion of 2 valence or higher. The anion is, for example, Bq-, wherein the Bq- is the same as the Bq- described in the triphenylmethane colorant (A-1-1), and will not be described again here.

[0073] [Triphenylmethane-based colorant (A-1-3)]

[0074] The triphenylmethane-based colorant (A-1-3) has a structure as shown in formula (I-3). In formula (I-3), R15, R16, R17, R18, R19 and R20 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group; R21, R22 and R23 each independently represent an alkyl group having 1 to 8 carbon atoms, or a chlorine atom; and f, g and h each independently represent an integer from 0 to 4.

[0075] In formula (I-3), the specific examples of substituted or unsubstituted alkyl groups having 1 to 8 carbon atoms in R15, R16, R17, R18, R19 and R20 and their substituents are the same as the specific examples of substituted or unsubstituted alkyl groups having 1 to 8 carbon atoms in R6, R7, R8, R9, R10 and R11 in formula (I-2) and their substituents, and will not be described again here.

[0076] In formula (I-3), the specific examples of substituted or unsubstituted cycloalkyl groups having 3 to 8 carbon atoms in R15, R16, R17, R18, R19 and R20 and their substituents are the same as the specific examples of substituted or unsubstituted cycloalkyl groups having 3 to 8 carbon atoms in R6, R7, R8, R9, R10 and R11 in formula (I-2) and their substituents, and will not be described again here.

[0077] In formula (I-3), the specific examples of substituted or unsubstituted aryl groups in R15, R16, R17, R18, R19 and R20 and their substituents are the same as the specific examples of substituted or unsubstituted aryl groups in R6, R7, R8, R9, R10 and R11 in formula (I-2), and will not be described again here.

[0078] In formula (I-3), the specific examples of alkyl groups having 1 to 8 carbons in R 21, R 22 and R 23 are the same as the specific examples of alkyl groups having 1 to 8 carbons in R 6, R 7, R 8, R 9, R 10 and R 11 in formula (I-2), and will not be repeated here.

[0079] In formula (I-3), f, g, and h each independently represent an integer from 0 to 4; in some embodiments of the present invention, preferably, f, g, and h each independently represent an integer from 0 to 2; more preferably, f, g, and h each independently represent 0 or 1. In some embodiments of the present invention, preferably, the combination of f, g, and h includes a combination of f=0, g=0, h=0, f=1, g=0, h=0, f=2, g=0, h=0, f=1, g=1, h=0, and f=1, g=1, h=1; more preferably, the combination of f, g, and h includes f=1, g=0, h=0; even more preferably, the combination of f, g, and h includes f=1, g=1, h=0.

[0080] The structure shown in formula (I-3) is a cationic chromophore of triarylmethane, and examples include chromophores a1, a2, a4, a5 in compound group a and b1, b2, b4, b6, b7 in compound group b. In some embodiments of the present invention, preferably, the cationic chromophore of the triarylmethane is the chromophore shown in a5 or b7.

[0081] Furthermore, the structure shown in formula (I-3) is a cation, which can be paired with an anion of 2 valence or higher. The anion is, for example, Bq-, wherein the Bq- is the same as the Bq- described in the triphenylmethane colorant (A-1-1), and will not be described again here.

[0082] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the triphenylmethane colorant (A-1) ranges from 0.5 wt% to 60 wt%; preferably, the content of the triphenylmethane colorant (A-1) ranges from 1 wt% to 55 wt%; more preferably, the content of the triphenylmethane colorant (A-1) ranges from 5 wt% to 50 wt%.

[0083] When the photosensitive resin composition does not contain the triphenylmethane-based colorant (A-1), the high fineness and time-filtration stability of the photosensitive resin composition are poor.

[0084] 〔Other colorants (A-2)〕

[0085] In some embodiments of the present invention, the colorant (A) may further include other colorants (A-2). The other colorant (A-2) may be an inorganic pigment, an organic pigment, a dye, or a combination thereof.

[0086] The inorganic pigment may be a metal compound such as a metal oxide or a metal salt. Among them, the inorganic pigment may be an oxide 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), a composite oxide of the aforementioned metals, a metal salt, or a combination thereof.

[0087] Specific examples of this organic pigment include CI pigment yellow 1, 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 61, 65, 71, 73, 74, 81, 83, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 126, 127, 128, 129, 138, 139, 150, 151, 152, 153, 154, 155, 156, 166 167, 168, 175; CI Pigment Orange l, 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 61, 63, 64, 71, 73; CI Pigment Red l, 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:l, 48:2, 48:3, 48:4, 49:l, 49:2, 50:1, 52:l, 53:l, 57, 57 : l, 57: 2, 58: 2, 58: 4, 60: l, 63: l, 63: 2, 64: l, 81: l, 83, 88, 90: l, 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; CI pigment violet 1, 14, 19, 23, 29, 32, 33, 36, 37, 38, 39, 40, 50; CI pigment blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 16, 21, 22, 60, 61, 64, 66; CI pigment green 7, 36, 37, 42, 58; CI pigment brown 23, 25, 28; CI pigment black 1, 7; or combinations thereof.

[0088] The dye includes, but is not limited to, azo dyes, anthraquinone dyes, phthalocyanine dyes, quinone imine dyes, quinoline dyes, nitro dyes, or combinations thereof.

[0089] The azo dyes include, but are not limited to, 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.

[0090] The anthraquinone dyes include, but are not limited to, Batblue 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.

[0091] The phthalocyanine dyes include, but are not limited to, Basic Blue 5, Direct Blue 86, or combinations thereof.

[0092] The quinone imine dyes include, but are not limited to, CI Basic Blue 3, CI Basic Blue 9, or combinations thereof.

[0093] The quinoline dyes include, but are not limited to, CI Solvent Yellow 33, CI Acid Yellow 3, CI Disperse Yellow 64, or combinations thereof.

[0094] The nitro dyes include, but are not limited to, Acid Yellow 1, Acid Orange 3, Disperse Yellow 42, or combinations thereof.

[0095] This other colorant (A-2) can be used alone or in combination.

[0096] In some embodiments of the present invention, preferably, the other colorant (A-2) is CI Pigment Blue 15:4, CI Pigment Blue 15:6, or a combination thereof.

[0097] In some embodiments of the present invention, the average particle size of the other colorant (A-2) may be from 10 nm to 200 nm, preferably from 20 nm to 150 nm, and more preferably from 30 nm to 130 nm.

[0098] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the other colorant (A-2) can range from 0 wt% to 40 wt%, preferably from 0 wt% to 35 wt%, and more preferably from 0 wt% to 30 wt%.

[0099] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the colorant (A) can range from 0.5 wt% to 60 wt%, preferably from 1 wt% to 55 wt%, and more preferably from 5 wt% to 50 wt%.

[0100] In the photosensitive resin composition of the present invention, preferably, the colorant (A) is used by dispersing it in a solvent using a dispersant. In some embodiments of the present invention, the dispersant may be appropriately selected from conventional dispersants. Examples of dispersants include cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, polysiloxane surfactants, fluorinated surfactants, and combinations thereof. The dispersants listed above may be non-polymeric or polymeric dispersants. From the viewpoint of uniform and fine dispersion, it is preferable that the dispersant is a polymeric dispersant.

[0101] The polymeric dispersant may include (co)polymers of unsaturated carboxylic acid esters such as polyacrylates; (partial) amine salts, (partial) ammonium salts or (partial) alkylamine salts of (co)polymers of unsaturated carboxylic acids such as polyacrylic 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; long-chain polyamide phosphates; polyethylimide derivatives [i.e., amides or bases thereof obtained by reacting poly(lower alkylimide) with polyesters containing free carboxyl groups]; polyallylamine derivatives [i.e., reaction products obtained by reacting polyallylamine with one or more compounds selected from polyesters containing free carboxyl groups, polyamides, or cocondensates of esters and amides (polyesteramides)], or combinations thereof.

[0102] From the viewpoint of being able to better disperse the colorant (A) and having good dispersion stability, in some embodiments of the present invention, the polymeric dispersant is preferably a polymeric dispersant containing nitrogen atoms in the main chain or side chain and having an amine valence.

[0103] Specific examples of polymeric dispersants containing nitrogen atoms in the main chain or side chain are listed below.

[0104] Commercially available products of (partial) amine salts, (partial) ammonium salts, or (partial) alkylamine salts of the (co)polymer of polyacrylic acid and other unsaturated carboxylic acids include Disperbyk 2000 and Disperbyk 2001 [all manufactured by BYK-Chemie].

[0105] Commercially available products of this type of polyurethane include Disperbyk 161 [manufactured by BYK-Chemie].

[0106] Commercially available unsaturated polyamides include Disperbyk 101 and Disperbyk 130 [manufactured by BYK-Chemie].

[0107] Commercially available products of this polyallylamine derivative include Ajisper PB821, Ajisper PB822, Ajisper PB824, and Ajisper PB827 [manufactured by Ajinomoto Fine-Techno].

[0108] Commercially available products of this poly(ethylene imine) derivative include Solsperse 33500 [manufactured by Lubrizol Corporation, Japan], etc.

[0109] Other commercially available dispersants include Dysperbyk 116, Dysperbyk 140, Dysperbyk 160, Dysperbyk 162, Dysperbyk 163, Dysperbyk 164, Dysperbyk 166, Dysperbyk 167, Dysperbyk 168, Dysperbyk 170, Dysperbyk 171, Dysperbyk 174, Dysperbyk 182, Dysperbyk 2050 [all manufactured by BYK-Chemie]; EFKA4046, EFKA4047 [all manufactured by EFKA Chemicals Co.]; Solsperse 12000, Solsperse Solsperse 13250, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 24000SC, Solsperse 27000, Solsperse 28000, Solsperse 32000, Solsperse 33500, Solsperse 35200, Solsperse 37500 [all manufactured by Lubrizol, Japan]; Ajisper PB711, Ajisper 823, Ajisper 880 [all manufactured by Ajinomoto Fine-Techno], etc.

[0110] There is no particular limitation on the amount of this dispersant used, and it can be adjusted appropriately according to needs.

[0111] 〈Alkali-soluble resin (B)〉

[0112] The alkali-soluble resin (B) of the present invention may include a first alkali-soluble resin (B-1). In addition, in some embodiments of the present invention, the alkali-soluble resin (B) may further include a second alkali-soluble resin (B-2).

[0113] 〔First Alkali-Soluble Resin (B-1)〕

[0114] The first alkali-soluble resin (B-1) of the present invention is obtained by copolymerization of an ethylene unsaturated monomer (b-1-1) containing a carboxylic acid group and other copolymerizable ethylene unsaturated monomers (b-1-2).

[0115] The carboxylic acid-containing vinyl unsaturated monomer (b-1-1) can be used alone or in combination, and the carboxylic acid-containing vinyl unsaturated monomer includes, but is 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, citraconic acid, and citraconic anhydride; and unsaturated polycarboxylic acids (anhydrides) with three or more carboxylic acid groups. In some embodiments of the present invention, preferably, the carboxylic acid-containing vinyl unsaturated monomer is acrylic acid, methacrylic acid, 2-acryloxysuccinate, 2-methacryloxysuccinate, or a combination thereof; more preferably, the carboxylic acid-containing vinyl unsaturated monomer is 2-acryloxysuccinate, 2-methacryloxysuccinate, or a combination thereof.

[0116] In some embodiments of the present invention, the total amount of the carboxylic acid-containing vinyl unsaturated monomer (b-1-1) and the other copolymerizable vinyl unsaturated monomer (b-1-2) used in the first alkali-soluble resin (B-1) is 100 parts by weight, the amount of the carboxylic acid-containing vinyl unsaturated monomer (b-1-1) used is 10 to 90 parts by weight, preferably, the amount of the carboxylic acid-containing vinyl unsaturated monomer (b-1-1) used is 15 to 85 parts by weight, and more preferably, the amount of the carboxylic acid-containing vinyl unsaturated monomer (b-1-1) used is 20 to 80 parts by weight.

[0117] The other copolymerizable vinyl unsaturated monomer (b-1-2) can be used alone or in combination, and the other copolymerizable vinyl unsaturated monomer (b-1-2) includes, but is not limited to, aromatic vinyl compounds such as styrene (SM), α-methylstyrene, vinyltoluene, p-chlorostyrene, and methoxystyrene; N-phenylmaleimide (PMI). Maleimides including nitrogen-o-hydroxyphenylmaleimides, nitrogen-m-hydroxyphenylmaleimides, nitrogen-p-hydroxyphenylmaleimides, nitrogen-o-methylphenylmaleimides, nitrogen-m-methylphenylmaleimides, nitrogen-p-methylphenylmaleimides, nitrogen-o-methoxyphenylmaleimides, nitrogen-m-methoxyphenylmaleimides, nitrogen-p-methoxyphenylmaleimides, and nitrogen-cyclohexylmaleimides; methyl acrylate (methyl Acrylate (MA), methyl methacrylate, ethyl methacrylate, ethyl methacrylate, n-propyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, isobutyl methacrylate, dibutyl methacrylate, dibutyl methacrylate, tert-butyl methacrylate, tert-butyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl methacrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, allyl acrylate, allyl methacrylate, benzyl methacrylate, benzyl methacrylate (benzyl) Unsaturated carboxylic acid esters such as methacrylate (BzMA), phenyl acrylate, phenyl methacrylate, triethylene glycol methoxyacrylate, triethylene glycol methoxyacrylate, dodecyl methacrylate, tetradecyl methacrylate, hexadecyl methacrylate, octadecyl methacrylate, eicosyl methacrylate, dodecyl methacrylate, dicyclopentenyloxyethyl acrylate (DCPOA); unsaturated amino esters such as acrylate-nitrogen, nitrogen-dimethylaminoethyl acrylate, methacrylate-nitrogen, nitrogen-dimethylaminoethyl acrylate, acrylate-nitrogen, nitrogen-diethylaminopropyl acrylate, methacrylate-nitrogen, nitrogen-dimethylaminopropyl acrylate, acrylate-nitrogen, nitrogen-dibutylaminopropyl acrylate, nitrogen-isobutylaminoethyl methacrylate; unsaturated carboxylic acid glycidyl esters such as acrylate and methacrylate glycidyl acrylate; and carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, and vinyl butyrate.Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl glycidyl ether, and methyl allyl glycidyl 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-hydroxyethylmethacrylonitrile; aliphatic conjugated dienes such as 1,3-butadiene, isoprene, and chlorobutadiene; or combinations thereof.

[0118] In some embodiments of the present invention, preferably, the other copolymerizable vinyl unsaturated monomer (b-1-2) includes styrene, N-phenylmaleimide, methyl acrylate, methyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, phenyl acrylate, phenyl methacrylate, dicyclopentenyl ethyl acrylate, or combinations thereof.

[0119] In some embodiments of the present invention, the total amount of the carboxylic acid-containing vinyl unsaturated monomer (b-1-1) and the other copolymerizable vinyl unsaturated monomer (b-1-2) used in the first alkali-soluble resin (B-1) is 100 parts by weight, and the amount of the other copolymerizable vinyl unsaturated monomer (b-1-2) used is from 10 parts by weight to 90 parts by weight. Preferably, the amount of the other copolymerizable vinyl unsaturated monomer (b-1-2) used is from 15 parts by weight to 85 parts by weight. More preferably, the amount of the other copolymerizable vinyl unsaturated monomer (b-1-2) used is from 20 parts by weight to 80 parts by weight.

[0120] There are no particular limitations on the preparation method of the first alkali-soluble resin (B-1), and an appropriate polymerization method can be selected according to requirements. Solution polymerization is an example of such a polymerization method. In addition to the required monomer, the reaction solution of the alkali-soluble resin (B) may also include a solvent, an initiator, 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 n-propyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, etc.; ethylene glycol methyl ether acetate, ethylene glycol ethyl ether acetate, propylene glycol methyl ether acetate (propylene glycol methyl ether ether) Acetate (PGMEA), propylene glycol ethyl ether acetate, and other (poly)alkylene glycol monoalkyl ether acetates; diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, and other ethers; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; lactic acid alkyl esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, and 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, 2-methoxybutyrate, etc.; aromatic hydrocarbons such as toluene and xylene; acetamides such as nitrogen-methylpyrrolidone, nitrogen, nitrogen-dimethylacetamide, or nitrogen, nitrogen-dimethylacetamide, etc. In some embodiments of the present invention, preferably, the solvent is propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, or a combination 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.

[0121] The initiator is generally a free radical polymerization initiator, specifically, for example: azo compounds such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis-2-methylbutyronitrile (AMBN); and peroxide compounds such as benzoyl peroxide.

[0122] This first alkali-soluble resin (B-1) can be used alone or in combination with other resins.

[0123] In some embodiments of the present invention, the first alkali-soluble resin (B-1) has a polystyrene equivalent number average molecular weight of 1,000 to 35,000 as determined by gel permeation chromatography (GPC), preferably, the polystyrene equivalent number average molecular weight is 3,000 to 30,000, and more preferably, the polystyrene equivalent number average molecular weight is 5,000 to 25,000.

[0124] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the first alkali-soluble resin (B-1) can range from 1 wt% to 60 wt%, preferably from 2 wt% to 55 wt%, and more preferably from 3 wt% to 50 wt%.

[0125] 〔Second Alkali-Soluble Resin (B-2)〕

[0126] The second alkali-soluble resin (B-2) of the present invention is obtained by polymerization of a mixture, wherein the mixture comprises 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 selectively comprise a carboxylic anhydride compound (b-2-3) and / or an epoxy-containing compound (b-2-4).

[0127] The epoxy 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 that "the epoxy 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) below and a compound having the structure shown in formula (III-2) below coexist as an epoxy compound (b-2-1). Specifically, the epoxy compound (b-2-1) having at least two epoxy groups is, for example, having a structure as shown in formula (III-1) below.

[0128] Formula (III-1) In this 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 may each be the same or different.

[0129] The epoxy 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 fluorine compound obtained by reacting a bisphenol fluorine compound with an epihalohydrin.

[0130] Specific examples of this bisphenol fluorene type compound may include, but are not limited to: 9,9-bis(4-hydroxyphenyl)fluorine, 9,9-bis(4-hydroxy-3-methylphenyl)fluorine, 9,9-bis(4-hydroxy-3-chlorophenyl)fluorine, 9,9-bis(4-hydroxy-3-bromophenyl)fluorine, and 9,9-bis(4-hydroxy-3-fluorophenyl)fluorine. fluorine, 9,9-bis(4-hydroxy-3-methoxyphenyl)fluorine, 9,9-bis(4-hydroxy-3,5-dimethylphenyl)fluorine, 9,9-bis(4-hydroxy-3,5-dimethylphenyl)fluorine, 9,9-bis(4-hydroxy-3,5-dichlorophenyl)fluorine, 9,9-bis(4-hydroxy-3,5-dibromophenyl)fluorine, or combinations thereof.

[0131] The epihalohydrin may include, but is not limited to, 3-chloro-1,2-epoxypropane, 3-bromo-1,2-epoxypropane, or combinations thereof.

[0132] The epoxy-containing bisphenol fluorene compounds obtained by reacting bisphenol fluorene compounds with halogenated propylene oxides 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, EG-210; (3) products manufactured by SMS Technology Co., Ltd., such as SMS-F9PhPG, SMS-F9CrG, SMS-F914PG; or combinations thereof.

[0133] Secondly, the epoxy compound (b-2-1) having at least two epoxy groups may also have a structure as shown in the following formula (III-2).

[0134] Formula (III-2) In this 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 may be the same or different; g represents an integer from 0 to 10.

[0135] The epoxy 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 a halopropane in the presence of an alkali metal hydroxide.

[0136] Equation (III-2-1) In this equation (III-2-1), the definitions of R 5c to R 18c and g are the same as those in this equation (III-2), and will not be repeated here.

[0137] Furthermore, the 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, thereby forming a compound having the structure of formula (III-2-1). Then, by adding an excess of halogenated propylene oxide to perform a dehydrohalogenation reaction, the epoxy compound (b-2-1) having at least two epoxy groups as shown in formula (III-2) is obtained.

[0138] Formula (III-2-2) In this formula (III-2-2), R19c and R20c 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 R19c and R20c may be the same or different; T1 and T2 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 T1 and T2 may be the same or different.

[0139] In some embodiments of the present invention, preferably, the aforementioned halogen atom is chlorine or bromine, the aforementioned alkyl group may be, for example, methyl, ethyl or tert-butyl, and the aforementioned alkoxy group may be, for example, methoxy or ethoxy.

[0140] Specific examples of this phenol 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. This phenol can generally be used alone or in combination.

[0141] In some embodiments of the present invention, the amount of the compound having the (III-2-2) structure used is 1 mol, the amount of the phenol used is 0.5 mol to 20 mol, preferably, the amount of the phenol used is 2 mol to 15 mol.

[0142] Specific examples of the acid catalyst may include, but are not limited to, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, oxalic acid, boron trifluoride, anhydrous aluminum chloride, zinc chloride, etc. In some embodiments of the present invention, preferably, the acid catalyst is p-toluenesulfonic acid, sulfuric acid, or hydrochloric acid. The acid catalyst can be used alone or in combination.

[0143] In addition, although there is no particular limitation on the amount of acid catalyst used, the amount of the compound having the (III-2-2) structure is 100% by weight (wt%), and preferably, the amount of acid catalyst used is 0.1 wt% to 30 wt%.

[0144] This condensation reaction can be carried out in the absence of a solvent or in the presence of an organic solvent. Specific examples of such organic solvents include, but are not limited to, toluene, xylene, or methyl isobutyl ketone. Multiple organic solvents can be used alone or in combination.

[0145] In some embodiments of the present invention, the total amount of the compound having the (III-2-2) structure 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.

[0146] After the condensation reaction is completed, a neutralization treatment or a water washing treatment can be performed. The neutralization treatment involves adjusting the pH value of the post-reaction solution to pH 3 to pH 7, with pH 5 to pH 7 being preferred. The water washing treatment can be performed using a neutralizing agent, which is an alkaline substance. Specific examples of such neutralizing agents include: alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; organic amines such as diethylene triamine, triethylene tetramine, aniline, and phenylene diamine; and ammonia and sodium dihydrogen phosphate. The water washing treatment can be performed using conventional methods, for example, by adding an aqueous solution containing the neutralizing agent to the post-reaction solution and repeatedly extracting. After the neutralization or washing process, the unreacted phenols and solvents are removed by distillation and concentration under reduced pressure to obtain a compound with the structure of formula (III-2-1).

[0147] Specific examples of the 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 dehydrohalogenation reaction, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide may be added. The operating temperature of the dehydrohalogenation reaction is from 20°C to 120°C, and the operating time ranges from 1 hour to 10 hours.

[0148] In some embodiments of the present invention, the alkali metal hydroxide added in the dehydrohalogenation reaction may also be an aqueous solution thereof. In a specific example of the present invention, while the aqueous solution of the alkali metal hydroxide is continuously added to the dehydrohalogenation reaction system, water and propylene oxide halide can be continuously distilled off under reduced pressure or normal pressure, thereby separating and removing water, and propylene oxide halide can be continuously refluxed back into the reaction system.

[0149] In some embodiments of the present invention, before the dehydrohalogenation reaction is carried out, a quaternary ammonium salt such as tetramethyl ammonium chloride, tetramethyl ammonium bromide, or trimethyl benzyl ammonium chloride may be added as a catalyst, and the reaction is carried out at 50°C to 150°C for 1 to 5 hours. Then, the alkali metal hydroxide or its aqueous solution is added, and the reaction is carried out at 20°C to 120°C for 1 to 10 hours to carry out the dehydrohalogenation reaction.

[0150] In some embodiments of the present invention, based on the total equivalent of hydroxyl groups in the compound having the structure of formula (III-2-1) being 1 equivalent, the amount of propylene halide used can be from 1 equivalent to 20 equivalents, preferably from 2 equivalents to 10 equivalents. In some embodiments of the present invention, based on the total equivalent of hydroxyl groups in the compound having the structure of formula (III-2-1) being 1 equivalent, the amount of alkali metal hydroxide added in the dehydrohalogenation reaction can be from 0.8 equivalents to 15 equivalents, preferably from 0.9 equivalents to 11 equivalents.

[0151] Furthermore, in order to facilitate the dehydrohalogenation reaction, in addition to 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% propylene oxide, the amount of alcohol used can be from 2 wt% to 20 wt%, preferably from 4 wt% to 15 wt%. In the example of using an aprotic polar solvent, based on a total amount of 100 wt% propylene oxide, the amount of the aprotic polar solvent used can be from 5 wt% to 100 wt%, preferably from 10 wt% to 90 wt%.

[0152] After the dehydrohalogenation reaction is completed, a water washing treatment may be selectively performed. Then, the halogenated propylene oxide, the alcohol, and the aprotic polar solvent 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.

[0153] In some embodiments of the present invention, to avoid the formation of epoxy compounds containing hydrolytically decomposable halogens, the solution after the dehydrohalogenation reaction can be added to solvents such as toluene and methyl isobutyl ketone, and aqueous solutions of alkali metal hydroxides such as sodium hydroxide and potassium hydroxide can be added to perform a second dehydrohalogenation reaction. In this dehydrohalogenation reaction, based on the total equivalent of hydroxyl groups in the compound having the structure of formula (III-2-1) being 1 equivalent, the amount of alkali metal hydroxide used is 0.01 mol to 0.3 mol, preferably 0.05 mol to 0.2 mol. Furthermore, the operating temperature range of this dehydrohalogenation reaction is 50°C to 120°C, and the operating time range is 0.5 hours to 2 hours.

[0154] After the dehydrohalogenation reaction is completed, salts are removed by steps such as filtration and washing with water. Alternatively, solvents such as toluene and methyl isobutyl ketone can be distilled off by heating under reduced pressure 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 as shown in formula (III-2) may include, but is not limited to, products manufactured by Nippon Kayaku Co. Ltd. under trade names such as NC-3000, NC-3000H, NC-3000S, and NC-3000P.

[0155] The 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 (1) to (3) below: (1) acrylic acid, methacrylic acid, 2-methacryloyloxyethylbutanedioic acid, 2-methacryloyloxyethylbutanedioic acid, 2-methacryloyloxyethylhexahydrophthalic acid, 2-methacryloyloxyethylmaleic acid, 2-methacryloyloxypropylmaleic acid, 2-methacryloyloxybutylmaleic acid, 2-methacryloyloxypropylbutanedioic acid, 2-methacryloyloxypropylbutanedioic acid, 2-methacryloyloxypropylbutanedioic acid, 2-methacryloyloxypropyltetrahydrophthalic acid, 2-methacryloyloxypropylphthalic acid, 2-methacryloyloxypropyltetrahydrophthalic acid, 2-methacryloyloxypropylphthalic acid, 2-methacryloyloxypropyltetrahydrophthalic acid, (1) Acryloxybutyl phthalic acid, or 2-methylacrylic acid acryloxybutylhydrophthalic 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 half-ester compound obtained by reacting a hydroxyl-containing (meth)acrylate with a carboxylic anhydride compound, 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 trimethyl acrylate, 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 described again here.

[0156] The mixture of the second alkali-soluble resin (B-2) may selectively include the carboxylic anhydride compound (b-2-3) and / or the epoxy-containing compound (b-2-4). The carboxylic anhydride compound (b-2-3) may be selected from the group consisting of (1) to (2) below: (1) dicarboxylic anhydride compounds such as butanedioic anhydride, maleic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyl endo-methylene tetrahydrophthalic anhydride, chlorendic anhydride, glutaric anhydride, or 1,3-dioxoisobenzofuran-5-carboxylic anhydride; and (2) benzophenone tetracarboxylic anhydride. dianhydride (BTDA), bisphenyltetracarboxylic dianhydride, or bisphenyl ether tetracarboxylic dianhydride, are tetracarboxylic anhydride compounds.

[0157] The epoxy-containing compound (b-2-4) is, for example, selected from glycidyl methacrylate, 3,4-epoxycyclohexyl methacrylate, glycidyl ether compounds containing unsaturated groups, unsaturated compounds containing epoxy groups, or any combination thereof. The glycidyl ether compounds containing unsaturated groups include, but are not limited to, compounds under trade names Denacol EX-111, EX-121 Denacol, Denacol EX-141, Denacol EX-145, Denacol EX-146, Denacol EX-171, Denacol EX-192, etc. (these are products of Nagase Chemical Industry Co., Ltd.).

[0158] In some embodiments of the present invention, the second alkali-soluble resin (B-2) can be prepared by polymerizing an epoxy compound (b-2-1) having at least two epoxy groups as shown in formula (III-1) 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 adding the carboxylic anhydride compound (b-2-3) for further reaction. Based on the total hydroxyl equivalent of the hydroxyl-containing reaction product being 1 equivalent, preferably, the equivalent of the anhydride groups contained in the carboxylic anhydride compound (b-2-3) is 0.4 equivalents to 1 equivalent; more preferably, the equivalent of the anhydride groups contained in the carboxylic anhydride compound (b-2-3) is 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 acid anhydrides and tetracarboxylic acid anhydrides as the carboxylic acid anhydride compounds (b-2-3), preferably, the molar ratio of the dicarboxylic acid anhydride compound to the tetracarboxylic acid anhydride compound is 1 / 99 to 90 / 10, more preferably, the molar ratio of the dicarboxylic acid anhydride compound to the tetracarboxylic acid anhydride compound is 5 / 95 to 80 / 20. Furthermore, the operating temperature range of the above reaction is, for example, from 50°C to 130°C.

[0159] In some embodiments of the present invention, the second alkali-soluble resin (B-2) can be prepared by reacting an epoxy compound (b-2-1) having at least two epoxy groups as shown in formula (III-2) 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, and then by adding the carboxylic anhydride compound (b-2-3) and / or the epoxy-containing compound (b-2-4) to carry out a polymerization reaction. Based on the total equivalent of epoxy groups on the epoxy compound (b-2-1) having at least two epoxy groups as shown in formula (III-2) being 1 equivalent, preferably, the acid equivalent of the compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group is 0.8 to 1.5 equivalents, more preferably, the acid equivalent of the compound (b-2-2) having at least one carboxylic acid group and at least one vinyl unsaturated group is 0.9 to 1.1 equivalents. Based on the total amount of hydroxyl groups in the hydroxyl-containing reaction product being 100 moles (mol%), preferably, the amount of the carboxylic anhydride compound (b-2-3) used is 10 mol% to 100 mol%, more preferably, the amount of the carboxylic anhydride compound (b-2-3) used is 20 mol% to 100 mol%, particularly preferably, the amount of the carboxylic anhydride compound (b-2-3) used is 30 mol% to 100 mol.

[0160] In preparing the second alkali-soluble resin (B-2), an alkaline compound is usually added to the reaction solution as a reaction catalyst to accelerate the reaction. This reaction catalyst can be used alone or in combination, and includes, but is not limited to, triphenylphosphine, triphenyl stibine, trimethylamine, triethanolamine, tetramethyl ammonium chloride, and benzyltriethyl ammonium chloride. In some embodiments of the present invention, the total amount of the epoxy 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. Preferably, the amount of the reaction catalyst used is from 0.01 parts by weight to 10 parts by weight, and more preferably, the amount of the reaction catalyst used is from 0.3 parts by weight to 5 parts by weight.

[0161] In some embodiments of the present invention, a polymerization inhibitor is typically added to the reaction solution to control the degree of polymerization. This polymerization inhibitor may include, but is not limited to, methoxyphenol, methylhydroquinone, hydroquinone, 2,6-di-t-butyl-p-cresol, or phenothiazine. Generally, the polymerization inhibitor can be used alone or in combination. Based on a total amount of 100 parts by weight of the epoxy 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, preferably, the amount of the polymerization inhibitor used is from 0.01 parts by weight to 10 parts by weight, and more preferably, the amount of the polymerization inhibitor used is from 0.1 parts by weight to 5 parts by weight.

[0162] In some embodiments of the present invention, when preparing the second alkali-soluble resin (B-2), a polymerization reaction solvent may be used if necessary. Specific examples of solvents for this polymerization reaction 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; cyrrolizidine compounds such as cellosolve or butyl cellosolve; carbitol compounds such as carbitol or butyl carbitol; propylene glycol monomethyl ether and other propylene glycol alkyl ethers; polypropylene glycol alkyl ethers such as di(propylene glycol) methyl ether; acetate compounds such as ethyl acetate, butyl acetate, ethylene glycol monoethyl ether acetate, or propylene glycol methyl ether acetate; and ethyl lactate. The solvents used in this polymerization reaction are alkyl lactates such as butyl lactate or butyl lactate; or dialkyl glycol ethers; or ethyl 3-ethoxypropionate. Various solvents can generally be used alone or in combination. Furthermore, preferably, the acid value of the second alkali-soluble resin (B-2) is from 50 mg KOH / g to 200 mg KOH / g; more preferably, the acid value of the second alkali-soluble resin (B-2) is from 60 mg KOH / g to 150 mg KOH / g.

[0163] In some embodiments of the present invention, the second alkali-soluble resin (B-2) has a polystyrene equivalent molecular weight of 500 to 10,000 as determined by a colloid permeation chromatography instrument; more preferably, the polystyrene equivalent molecular weight is 800 to 8,000; and even more preferably, the polystyrene equivalent molecular weight is 1,000 to 6,000.

[0164] The second alkali-soluble resin (B-2) can be used alone or in combination with other resins.

[0165] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the second alkali-soluble resin (B-2) can range from 1 wt% to 60 wt%, preferably from 2 wt% to 55 wt%, and more preferably from 3 wt% to 50 wt%.

[0166] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the alkali-soluble resin (B) can range from 1 wt% to 60 wt%, preferably from 2 wt% to 55 wt%, and more preferably from 3 wt% to 50 wt%.

[0167] 〈Photopolymerizable Compound (C)〉

[0168] The photopolymerizable compound (C) of the present invention may include unsaturated compounds having at least one ethylene unsaturated group and unsaturated compounds having at least two ethylene unsaturated groups.

[0169] Specific examples of the unsaturated compound having at least one vinyl unsaturated group may include, but are not limited to, acrylamide, acrylmorpholine, methacrylomorpholine, 7-amino-3,7-dimethyloctyl acrylate, 7-amino-3,7-dimethyloctyl methacrylate, isobutoxymethacrylamide, isobutoxymethacrylamide, isobornyloxyethyl acrylate, isobornyloxyethyl methacrylate, isobornyl acrylate, isobornyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate Ethylhexyl acrylate, ethyl diethylene glycol acrylate, ethyl diethylene glycol methacrylate, tert-octyl acrylamide, tert-octyl methacrylamide, diacetone acrylamide, diacetone methacrylamide, dimethylamino acrylate, dimethylamino methacrylate, dodecyl acrylate, dodecyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, tetrachlorophenyl acrylate, methyl... 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 2-Hydroxyethyl acrylate, 2-Hydroxyethyl methacrylate, 2-Hydroxypropyl acrylate, 2-Hydroxypropyl methacrylate, vinylcaprolactone, N-vinylpyrrolidone, phenoxyethyl acrylate, phenoxyethyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, polyethylene monoacrylate, polyethylene monomethacrylate, propylene monoacrylate, polypropylene monomethacrylate, borneol acrylate, borneol methacrylate, or combinations thereof. The unsaturated compound having at least one vinyl unsaturated group can be used alone or in combination.

[0170] Specific examples of the unsaturated compound 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, tri(2-hydroxyethyl) isocyanate dimethacrylate, tri(2-hydroxyethyl) isocyanate triacrylate, tri(2-hydroxyethyl) isocyanate trimethacrylate, caprolactone-modified tri(2-hydroxyethyl) isocyanate triacrylate, and caprolactone-modified tri(2-hydroxyethyl) isocyanate triacrylate. (2-Hydroxyethyl) isocyanate trimethacrylate, trimethylolpropionic acid triacrylate, trimethylolpropionic acid trimethacrylate, ethylene oxide (hereinafter referred to as EO) modified trimethylolpropionic acid triacrylate, EO modified trimethylolpropionic acid trimethacrylate, propylene oxide (hereinafter referred to as PO) modified trimethylolpropionic acid triacrylate, PO modified trimethylolpropionic acid trimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-Hexanediol dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, polyester diacrylate, polyester dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, dipentaerythritol hexaacrylate 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. Bisphenol A diacrylate, PO modified bisphenol A dimethacrylate, EO modified hydrogenated bisphenol A diacrylate, EO modified hydrogenated bisphenol A dimethacrylate, PO modified hydrogenated bisphenol A diacrylate, PO modified hydrogenated bisphenol A dimethacrylate, PO modified glyceryl tripropionate, EO modified bisphenol F diacrylate, EO modified bisphenol F dimethacrylate, phenolic polyglycidyl ether acrylate, phenolic polyglycidyl ether methacrylate, products manufactured by Toa Synthetic Co., Ltd. of Japan with model number TO-1382, or products manufactured by Nippon Kayaku Co., Ltd. with model numbers KAYARAD DPCA-12, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60 or KAYARAD DPCA-120, etc. The unsaturated compound having at least two ethylene unsaturated groups can be used alone or in combination.

[0171] In some embodiments of the present invention, preferably, specific examples of the photopolymerizable compound (C) include trimethylolpropionic acid triacrylate, EO-modified trimethylolpropionic acid triacrylate, 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.

[0172] In some embodiments of the present invention, more preferably, the specific examples of the photopolymerizable compound (C) are dipentaerythritol hexaacrylate, dipentaerythritol tetraacrylate, or combinations thereof.

[0173] This photopolymerizable compound (C) can be used alone or in combination.

[0174] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the photopolymerizable compound (C) can range from 5 wt% to 60 wt%, preferably from 8 wt% to 55 wt%, and more preferably from 10 wt% to 50 wt%.

[0175] 〈Photoinitiator (D)〉

[0176] The photoinitiator (D) of the present invention can be a free radical type photoinitiator.

[0177] The photoinitiator (D) may include acetophenone, biimidazole, acyl oxime, or combinations thereof.

[0178] The acetophenone compound is selected from p-dimethylamino-acetophenone, α,α'-dimethoxyazoxy-acetophenone, 2,2'-dimethyl-2-phenyl-acetophenone, p-methoxy-acetophenone, 2-methyl-1-(4-methylthiophenyl)-2-morpholino-1-propanone, 2-benzyl-2-N,N-di-methylamino-1-(4-morpholinophenyl)-1-butanone, or combinations thereof.

[0179] The diimidazole compound is 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. [iimidazole], 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'-tetraphenylbiimidazole, 2,2'-bis(2,2',4,4'-tetramethoxyphenyl)-4,4',5,5'-tetraphenylbiimidazole [-biimidazole], 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-biimidazole, or combinations thereof.

[0180] This acetoxime compound is selected from ethaneone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-substituted]-, 1-(oxoacetoxime){Ethanone,1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-,1-(O-acetyl oxime), for example, the product CGI-242 manufactured by Ciba Specialty Chemicals, with the structure shown in formula (IV-1) below}, 1-[4-(phenylthio)phenyl]-octane-1,2-dione 2-(O-benzoyl oxime){1-[4-(benzoyl)phenyl]-heptane-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)-9H-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. Formula (IV-1) Formula (IV-2) Formula (IV-3)

[0181] In some embodiments of the present invention, 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 benzyl and acetyl; acyloin compounds such as benzoin; benzoin methyl ether and benzoin ethyl ether. Keto-ethanol ethers such as 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; phenacyl chloride, tribromomethyl-phenylsulfone, and tris(trichloromethyl)-s-triazine. Halides such as triazine; and peroxides such as di-tertbutylperoxide. Preferably, the photoinitiator (D) may further include benzophenone compounds, and more preferably, the photoinitiator (D) may further include 4,4'-bis(diethylamine)benzophenone.

[0182] In some embodiments of the present invention, preferably, the photoinitiator (D) comprises 1-[4-(phenylthio)phenyl]-octane-1,2-dione 2-(O-benzoyl oxime) [e.g., the product manufactured by Ciba Specialty Chemicals under the trade name CGI-124].

[0183] This photoinitiator (D) can be used alone or in combination with other agents.

[0184] In some embodiments of the present invention, based on the total weight of the solid components of the photosensitive resin composition being 100 wt%, the content of the photoinitiator (D) can range from 0.1 wt% to 15 wt%, preferably from 0.5 wt% to 13 wt%, and more preferably from 1 wt% to 10 wt%.

[0185] 〈Compound (E) having the structure shown in formula (V)〉

[0186] In the compound (E) of the present invention having the structure shown in formula (V), the structure shown in formula (V) is as follows. Formula (V)

[0187] In formula (V), R24, R25, R26, and R27 each independently represent a hydrogen atom, an alkyl group, a hydroxyl group, or an amino group; X represents an aliphatic hydrocarbon group with 1 to 5 carbon atoms or an aromatic hydrocarbon group with 6 to 10 carbon atoms; and M represents a hydrogen atom, an alkali metal group, an ammonium group, or an organoammonium group. Examples of alkyl groups with 1 to 5 carbon atoms in R24, R25, R26, and R27 include methyl, ethyl, propyl, isopropyl, butyl, dibutyl, isobutyl, tributyl, and pentyl. Examples of aliphatic hydrocarbon groups with 1 to 5 carbon atoms in X include methyl, ethyl, propyl, isopropyl, pentyl, vinyl, and propenyl. Examples of aromatic hydrocarbon groups with 6 to 10 carbon atoms include phenyl, tolyl, xylyl, 2,6-dimethylphenyl, and tetramethylphenyl. Examples of alkali metals in M ​​include lithium, sodium, and potassium; examples of organic ammonium groups include monomethylammonium, dimethylammonium, trimethylammonium, triethylammonium, etc., which are alkylammonium groups with 1 to 6 carbon atoms, as well as monoethanolammonium, diethanolammonium, triethanolammonium, triisopropanolammonium, etc., which are alkanolammonium groups with 1 to 9 carbon atoms.

[0188] In some embodiments of the present invention, specific examples of the compound (E) having the structure shown in formula (V) may be selected from at least one of compounds (V-1) to (V-13). However, it should be noted that the compound (E) having the structure shown in formula (V) is not limited thereto. (V-1), (V-2), (V-3), (V-4), (V-5), (V-6), (V-7), (V-8), (V-9), (V-10), (V-11), (V-12), (V-13)

[0189] The compound (E) having the structure shown in formula (V) can be used alone or in combination.

[0190] In some embodiments of the present invention, based on a total weight of 100 wt% of the solid components of the photosensitive resin composition, the content of the compound (E) having the structure shown in formula (V) ranges from 0.1 wt% to 10 wt%, preferably from 0.2 wt% to 8 wt%, and more preferably from 0.3 wt% to 5 wt%.

[0191] When the X of the compound (E) having the structure shown in formula (V) is an aliphatic hydrocarbon group with 1 to 5 carbon atoms, the high fineness and time-filtration stability of the photosensitive resin composition are better.

[0192] When M in the compound (E) having the structure shown in formula (V) represents a hydrogen atom, an ammonium group or an organic ammonium group, the high fineness and time-filtration stability of the photosensitive resin composition are better.

[0193] When the photosensitive resin composition does not contain the compound (E) having the structure shown in formula (V), the high fineness of the photosensitive resin composition is poor after filtration.

[0194] 〈Solvent (F)〉

[0195] The preparation of the photosensitive resin composition of the present invention generally involves first dissolving all components other than the colorant (A) in the solvent (F) to form a liquid composition, and then adding the colorant (A) and mixing uniformly. The solvent (F) must be selected to dissolve the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), and the compound (E) having the structure shown in formula (V), and must not react with these components and have appropriate volatility. Furthermore, when an additive (G) is added, the solvent (F) must be selected to dissolve the additive (G), and must not react with these components and have appropriate volatility.

[0196] In some embodiments of the present invention, the solvent (F) may be the same as the solvent used to prepare the alkali-soluble resin (B), which will not be repeated here. Furthermore, the solvent (F) may be used alone or in combination. Preferably, the solvent (F) includes propylene glycol methyl ether acetate, ethyl 3-ethoxypropionate, or a combination thereof.

[0197] In some embodiments of the present invention, based on the total weight of the photosensitive resin composition of 100 wt%, the content of the solvent (F) can range from 55 wt% to 95 wt%, preferably from 60 wt% to 95 wt%, and more preferably from 70 wt% to 95 wt%.

[0198] 〈Additives (G)〉

[0199] In some embodiments of the present invention, the photosensitive resin composition further includes additives (G), such as fillers, polymers other than the alkali-soluble resin (B), adhesion promoters, antioxidants, ultraviolet absorbers, anti-aggregating agents, etc.

[0200] The filler may include glass, aluminum, or combinations thereof.

[0201] The polymeric compound may include polyvinyl alcohol, polyethylene glycol monoalkyl ether, polyfluoroacrylate, or combinations thereof.

[0202] The adhesion promoter 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.

[0203] The antioxidant may include 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-di-tert-butylphenol, or combinations thereof.

[0204] The ultraviolet absorber may include 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorophenyl azide, alkoxyphenyl ketone, or combinations thereof.

[0205] Anti-agglomerating agents include sodium polyacrylate.

[0206] This additive (G) can be used alone or in combination.

[0207] In some embodiments of the present invention, preferably, the additive (G) is 3-thiol-propyltrimethoxysilane, 2,2-thiobis(4-methyl-6-tert-butylphenol), or a combination thereof.

[0208] In some embodiments of the present invention, based on the total weight of the photosensitive resin composition being 100 wt%, the content of the additive (G) can be greater than 0 wt% and less than 10 wt%, preferably, the content of the additive (G) is greater than 0 wt% and less than 7 wt%, and more preferably, the content of the additive (G) is greater than 0 wt% and less than 5 wt%.

[0209] Preparation Method of Photosensitive Resin Composition

[0210] The preparation method of the photosensitive resin composition of the present invention is not particularly limited. Specifically, the preparation method of the photosensitive resin composition can be exemplified by: (1) First, adding the colorant (A) to the solvent (F) to prepare a colorant dispersion, and then adding the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), the compound (E) having the structure shown in formula (V), and the additive (G) as needed to the colorant dispersion and mixing them; (2) Adding the colorant (A), the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), the compound (E) having the structure shown in formula (V), and the additive (G) as needed to the solvent (F) and mixing them; (3) First First, a method in which the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), the compound (E) having the structure shown in formula (V), and the additive (G) used as needed are added to the solvent (F) and mixed, and then the colorant (A) is added and dispersed; and (4) a method in which the colorant (A) and a portion of the alkali-soluble resin (B) are added to the solvent (F) to prepare a colorant dispersion, and then another portion of the alkali-soluble resin (B), the photopolymerizable compound (C), the photoinitiator (D), the compound (E) having the structure shown in formula (V), and the additive (G) used as needed are added to the colorant dispersion and mixed, etc.

[0211] In view of the above methods, it is preferable to prepare the photosensitive resin composition by the methods (1) and (4) above, so as to effectively prevent the colorant from agglomerating and disperse it evenly.

[0212] Methods for uniformly dispersing / mixing the components include using a mixer and / or a disperser for mixing and / or dispersion. Examples of dispersers include roller mills such as two-roll mills and three-roll mills, ball mills, vibratory ball mills, paint conditioners, continuous disc bead mills, and continuous ring bead mills. Preferably, the dispersion conditions of the bead mill are that the bead diameter used is from 0.03 mm to 2.00 mm; more preferably, the dispersion conditions of the bead mill are that the bead diameter used is from 0.10 mm to 1.0 mm.

[0213] Preparation Method of Color Filters

[0214] The method for manufacturing the color filter of the present invention includes forming a pixel layer using a photosensitive resin composition as described above. Specifically, the photosensitive resin composition, mixed in a solution state, is coated onto a substrate using coating methods such as rotary coating, cast coating, inkjet coating, or roller coating. After coating, most of the solvent is removed by vacuum drying, and then the solvent is removed by pre-bake to form a pre-baked coating film. The conditions for vacuum drying and pre-baking vary depending on the type and ratio of each component. Typically, vacuum drying is performed at a pressure of 0 mmHg to 200 mmHg for 1 to 60 seconds, and pre-baking is performed at a temperature of 70°C to 110°C for 1 to 15 minutes. After pre-baking, the pre-baked coating is exposed under a specified mask and developed by immersing it in a developer at 23±2°C for 15 seconds to 5 minutes to remove unwanted portions and form a pixel layer. The light used for this exposure is preferably ultraviolet light such as g-lines, h-lines, and i-lines, and the ultraviolet light device can be a (ultra) high-pressure mercury lamp or a metal halide lamp.

[0215] Specific examples of such substrates include: alkali-free glass, soda-lime glass, hard glass (Pyles glass), quartz glass, sodium glass, or substrates with a transparent conductive film attached to such glass for liquid crystal display devices; or substrates for photoelectric conversion devices such as solid-state imaging devices (e.g., silicon substrates). Such substrates generally first form a black matrix that isolates each pixel layer.

[0216] Furthermore, the developer is specifically an alkaline aqueous solution composed of at least one of the following alkaline compounds: sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, sodium silicate, sodium methyl silicate, ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, guanidine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc., wherein the concentration of the alkaline compound in the alkaline aqueous solution is generally from 0.001 wt% to 10 wt%; preferably, the concentration of the alkaline compound in the alkaline aqueous solution is from 0.005 wt% to 5 wt%; more preferably, the concentration of the alkaline compound in the alkaline aqueous solution is from 0.01 wt% to 1 wt%.

[0217] In some embodiments of the present invention, preferably, the developing solution is an alkaline aqueous solution composed of sodium carbonate.

[0218] When using the developer solution made of this alkaline aqueous solution, it is generally washed with water after development, and then the pixel layer is dried with compressed air or compressed nitrogen.

[0219] The substrate with the pixel layer, after being air-dried, is heated at a temperature of 100°C to 280°C for 1 to 15 minutes using a heating device such as a hot plate or oven to remove volatile components from the pixel layer and to allow unreacted vinyl unsaturated double bonds in the pixel layer to undergo a thermosetting reaction. The same steps are repeated three times on predetermined pixels using photosensitive resin compositions of various colors (mainly including red, green, and blue) to obtain red, green, and blue pixel layers.

[0220] Next, an ITO (indium tin oxide) vapor deposition film is formed on the pixel layer under vacuum at a temperature of 220°C to 250°C. If necessary, the ITO vapor deposition film is etched and wired, and then polyimide for liquid crystal alignment film is coated, followed by heat treatment, so that it can be used as a color filter for liquid crystal display.

[0221] Furthermore, the liquid crystal alignment film used above is used to restrict the alignment of liquid crystal molecules. It is not particularly limited here, and any inorganic or organic material can be used. As for the technology for forming the liquid crystal alignment film, it is well known to those skilled in the art and is not the focus of this invention, so it will not be described in detail here.

[0222] Liquid Crystal Display Device

[0223] The liquid crystal display device of the present invention includes a color filter substrate containing a color filter manufactured using the color filter manufacturing method described above; and a driving substrate on which a thin film transistor (TFT) is disposed. The liquid crystal display device of the present invention is formed by intervening a gap (cell gap) between the color filter substrate and the driving substrate and arranging them opposite each other, bonding a sealant around the opposing surfaces of the color filter substrate and the driving substrate, filling and injecting liquid crystal into the gap defined by the sealant on the opposing surfaces of the color filter substrate and the driving substrate, and sealing the injection hole to form a liquid crystal cell. Then, a polarizing plate is bonded to the outer surface of the liquid crystal cell, that is, to the other side surfaces of each substrate constituting the liquid crystal cell, to obtain the liquid crystal display device.

[0224] As for the liquid crystal used above, that is, liquid crystal compound or liquid crystal composition, there is no particular limitation here, but any kind of liquid crystal compound and liquid crystal composition may be used.

[0225] The present invention will be further illustrated by the following experimental examples, but it should be understood that these experimental examples are for illustrative purposes only and should not be construed as limiting the implementation of the present invention.

[0226] [Synthesis Example 1] First base soluble resin (B-1)

[0227] 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 benzyl methacrylate, and 30 parts by weight of nitrogen-phenylmaleimide were placed in a round-bottom flask equipped with a stirrer and a condenser, and the flask was filled with nitrogen gas. Then, the mixture was slowly stirred and heated to 80°C to ensure uniform mixing of the reactants and to carry out the polymerization reaction for 4 hours. After that, the temperature was raised to 100°C, and 0.5 parts by weight of 2,2'-azobisisobutyronitrile was added. After polymerization for 1 hour, the first alkali-soluble resin (B-1) of Synthesis Example 1 was obtained.

[0228] [Synthesis Example 2] First base soluble resin (B-1)

[0229] 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 benzyl methacrylate were placed in a round-bottom flask equipped with a stirrer and a condenser. The flask was filled with nitrogen gas. Then, the mixture was slowly stirred and heated to 80°C to ensure uniform mixing of the reactants and to carry out the polymerization reaction for 3 hours. Afterward, the temperature was raised to 100°C, and 0.5 parts by weight of 2,2'-azobisisobutyronitrile was added. After polymerization for 1 hour, the first alkali-soluble resin (B-1) of Synthesis Example 2 was obtained.

[0230] [Example 1] Photosensitive resin composition

[0231] First, 32.4 parts by weight of compound (22) [i.e. colorant (A1-1)], 400 parts by weight of propylene glycol methyl ether acetate [PGMEA, manufactured by Daicel-Allnex], and 2.0 parts by weight of zirconia beads with a particle size of 2 mm were placed in a 30 ml wide-mouth bottle. After pre-pulverizing using a paint shaker (PCMH-C50M, manufactured by Asada Tetsugang) for 1 hour, the solution in the wide-mouth bottle was transferred to another 30 ml wide-mouth bottle, and 2.0 parts by weight of zirconia beads with a particle size of 0.1 mm were added. The solution was shaken using a paint shaker for 20 hours to obtain the colorant dispersion of Example 1.

[0232] Next, 432.4 parts by weight of the colorant dispersion [which contains 32.4 parts by weight of the compound (22) and 400 parts by weight of the propylene glycol methyl ether acetate], 45 parts by weight of the first alkali-soluble resin (B-1) of Synthesis Example 1 [i.e., alkali-soluble resin (B-1)], 20 parts by weight of dipentaerythritol hexaacrylate [i.e., photopolymerizable compound (C-1)], and 2.5 parts by weight of 1-[4-(phenylthio)] [Phenyl]-octane-1,2-dione 2-(O-benzoyl oxime) [i.e., photoinitiator (D-1)] and 0.1 parts by weight of compound (V-1) [i.e., compound (E-1) having the structure shown in formula (V)] are added to a mixed solvent containing 600 parts by weight of propylene glycol methyl ether acetate [i.e., solvent (F-1)] and 200 parts by weight of ethyl 3-ethoxypropionate [i.e., solvent (F-2)], and stirred evenly with a shaking type stirrer to obtain the photosensitive resin composition of Example 1.

[0233] The photosensitive resin composition of Example 1 was evaluated using the evaluation method described below, and the results are shown in Table 1.

[0234] [Examples 2 to 10 and Comparative Examples 1 to 3] Photosensitive resin composition

[0235] The photosensitive resin compositions of Examples 2 to 10 and Comparative Examples 1 to 3 were prepared in a manner similar to that of Example 1, except that the types and amounts of the components in the photosensitive resin compositions were changed. Examples 2 to 10 and Comparative Examples 1 to 3 are shown in Tables 1 to 3. The corresponding components in Tables 1 to 3 are shown in Table 4. The obtained photosensitive resin compositions were evaluated using the evaluation methods described below, and the results for Examples 2 to 10 and Comparative Examples 1 to 3 are shown in Tables 1 to 3, respectively.

[0236] [Evaluation Items]

[0237] The following description uses the photosensitive resin composition of Example 1 as an example. The other photosensitive resin compositions of Examples 2 to 10 and Comparative Examples 1 to 3 are carried out in the same manner.

[0238] High-precision filtration stability over time: Immediately after preparation, 10g of the photosensitive resin composition of Example 1 was taken and pressurized with nitrogen gas at a pressure of 0.3MPa to pass the photosensitive resin composition of Example 1 through a filter membrane (pore size: 0.2μm, model: 39115221, manufactured by ADVANTEC). The amount of filtrate obtained after passing through the filter membrane was measured to obtain a weight (f1). In addition, after the preparation of the photosensitive resin composition of Example 1 was completed, the photosensitive resin composition of Example 1 was stored at 5°C for 1 month, and the amount of filtrate obtained after passing through the filter membrane after 1 month of storage was measured using the same test method described above to obtain a weight (f2). Next, "(f2) / (f1)×100%" was calculated as the time-lapse filtration ratio (F) of the photosensitive resin composition of Example 1, and the high-precision time-lapse filtration stability of the photosensitive resin composition of Example 1 was evaluated according to the following criteria: ◎: F≧99%; ○: 97%≦F<99%; △: 95%≦F<97%; ╳: F<95%.

[0239] Table 1 Unit: parts by weight Example 1 2 3 4 5 Colorant (A) A1-1 32.4 -- -- -- -- A1-2 -- 32.5 -- -- -- A1-3 -- -- 37.5 -- -- A1-4 -- -- -- 35.5 -- A1-5 -- -- -- -- 34.5 A2-1 -- -- -- -- -- A2-2 -- -- -- -- -- Alkali-soluble resin (B) B-1 45 44 35 40 35 B-2 -- -- -- -- -- Photopolymerizable compounds (C) C-1 20 -- 20 17 -- C-2 -- 20 -- -- 20 Photoinitiator (D) D-1 2.5 2.5 2.5 2.5 2.5 Compound (E) having the structure shown in formula (V) E-1 0.1 -- -- -- -- E-2 -- 1 -- -- -- E-3 -- -- 5 -- -- E-4 -- -- -- 5 -- E-5 -- -- -- -- 8 E-6 -- -- -- -- -- Solvent (F) F-1 1000 1000 1000 1000 1000 F-2 200 200 200 200 200 High-precision, long-term filtration stability ◎ ◎ ○ ○ △ Note: "--" indicates that it has not been added.

[0240] Table 2 Unit: parts by weight Example 6 7 8 9 10 Colorant (A) A1-1 22.5 -- -- -- -- A1-2 10 33.5 -- -- -- A1-3 -- -- 42.5 -- -- A1-4 -- -- -- 32.5 39.5 A1-5 -- -- -- -- -- A2-1 -- -- -- -- -- A2-2 -- -- -- -- -- Alkali-soluble resin (B) B-1 -- -- -- -- -- B-2 35 43 33 42 33 Photopolymerizable compounds (C) C-1 20 -- 20 20 -- C-2 -- 20 -- -- 20 Photoinitiator (D) D-1 2.5 2.5 2.5 2.5 2.5 Compound (E) having the structure shown in formula (V) E-1 -- -- -- -- -- E-2 -- 1 -- -- -- E-3 -- -- 2 -- -- E-4 -- -- -- 3 -- E-5 -- -- -- -- -- E-6 10 -- -- -- 5 Solvent (F) F-1 1000 1000 1000 1000 1000 F-2 200 200 200 200 200 High-precision, long-term filtration stability ◎ ◎ ○ ○ ◎ Note: "--" indicates that it has not been added.

[0241] Table 3 Unit: parts by weight Comparative example 1 2 3 Colorant (A) A1-1 32.5 -- -- A1-2 -- -- -- A1-3 -- -- -- A1-4 -- -- -- A1-5 -- -- -- A2-1 -- 33.5 -- A2-2 -- -- 39.5 Alkali-soluble resin (B) B-1 45 -- -- B-2 -- 43 43 Photopolymerizable compounds (C) C-1 20 -- -- C-2 -- 20 20 Photoinitiator (D) D-1 2.5 2.5 2.5 Compound (E) having the structure shown in formula (V) E-1 -- -- -- E-2 -- 1 -- E-3 -- -- -- E-4 -- -- -- E-5 -- -- -- E-6 -- -- 5 Solvent (F) F-1 1000 1000 1000 F-2 200 200 200 High-precision, long-term filtration stability ╳ ╳ ╳ Note: "--" indicates that it has not been added.

[0242] Table 4 serial number Compound name / structure A1-1 Compound (22) A1-2 Compound (2) A1-3 A1-4 A1-5 A2-1 CI Pigment Blue 15:6 A2-2 Direct Blue 86 B-1 Synthetic Example 1: First Base-Soluble Resin (B-1) B-2 Synthetic Example 2: First Base-Soluble Resin (B-1) C-1 Dipentaerythritol hexaacrylate C-2 Dipentaerythritol tetraacrylate D-1 1-[4-(phenylthio)phenyl]-octane-1,2-dione 2-(O-benzoyloxime){1-[4-(benzoyl)phenyl]-heptane-1,2-dione 2-(O-benzoyloxime), for example, the product CGI-124 manufactured by Ciba Specialty Chemicals. Formula (IV-2) E-1 (V-1) E-2 (V-6) E-3 (V-10) E-4 (V-11) E-5 (V-12) E-6 (V-13) F-1 Propylene glycol methyl ether acetate F-2 Ethyl 3-ethoxypropionate

[0243] Referring to Tables 1 to 2, the photosensitive resin compositions of Examples 1 to 10, by using the colorant (A) including the triphenylmethane-based colorant (A-1) and the compound (E) having the structure shown in Formula (V), have a time filtration ratio (F) of 95% or more, thereby exhibiting good high-fineness time filtration stability.

[0244] On the other hand, the photosensitive resin compositions of Examples 1 to 4 and 6 to 10 further use the triphenylmethane-based colorant (A-1) having a heterogeneous multiple acid anion containing at least one of molybdenum and tungsten. Therefore, the time-lapse filtration ratio (F) of the photosensitive resin compositions of Examples 1 to 4 and 6 to 10 is 97% or more, thereby exhibiting better high-fineness time-lapse filtration stability. Furthermore, the compound (E) with the structure shown in Formula (V) used in the photosensitive resin compositions of Examples 1, 2, 6, 7 and 10, by having X in Formula (V) represent an aliphatic hydrocarbon group with 1 to 5 carbon atoms and M represent a hydrogen atom, an ammonium group or an organic ammonium group, therefore, the time-lapse filtration ratio (F) of the photosensitive resin compositions of Examples 1, 2, 6, 7 and 10 is 99% or more, thereby exhibiting better high-fineness time-lapse filtration stability.

[0245] Referring to Table 3, in contrast to Comparative Examples 1 to 3, the photosensitive resin composition of Comparative Example 1 does not contain the compound (E) having the structure shown in Formula (V). Therefore, the time filtration ratio (F) of the photosensitive resin composition of Comparative Example 1 is less than 95%, resulting in poor high-fineness time filtration stability. The photosensitive resin compositions of Comparative Examples 2 and 3 do not contain the colorant (A) including the triphenylmethane-based colorant (A-1). Therefore, the time filtration ratio (F) of the photosensitive resin compositions of Comparative Examples 2 and 3 is less than 95%, resulting in poor high-fineness time filtration stability.

[0246] In summary, the photosensitive resin composition of the present invention uses the colorant (A) including the triphenylmethane-based colorant (A-1) and the compound (E) having the structure shown in formula (V). Therefore, the time filtration ratio (F) of the photosensitive resin composition is more than 95%, thereby having good high-fineness time filtration stability, and thus the purpose of the present invention can be effectively achieved.

[0247] However, the above description is only an embodiment of the present invention and should not be construed as limiting the scope of the present invention. Any simple equivalent changes and modifications made in accordance with the scope of the patent application and the contents of the patent specification shall still fall within the scope of the patent of the present invention.

Claims

1. A photosensitive resin composition comprising: a colorant (A), including a triphenylmethane-based colorant (A-1); an alkali-soluble resin (B); a photopolymerizable compound (C); a photoinitiator (D); a compound (E) having a structure as shown in formula (V); and a solvent (F); in formula (V), R24, R25, R26, and R27 each independently represent a hydrogen atom, an alkyl group, a hydroxyl group, or an amino group, X represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and M represents a hydrogen atom, an alkali metal group, an ammonium group, or an organoammonium group; wherein, Based on a total solid weight of 100 wt% of the photosensitive resin composition, the content of the colorant (A) ranges from 0.5 wt% to 60 wt%, the content of the triphenylmethane-based colorant (A-1) ranges from 0.5 wt% to 60 wt%, the content of the alkali-soluble resin (B) ranges from 1 wt% to 60 wt%, the content of the photopolymerizable compound (C) ranges from 5 wt% to 60 wt%, the content of the photoinitiator (D) ranges from 0.1 wt% to 15 wt%, and the content of the compound (E) having the structure shown in formula (V) ranges from 0.1 wt% to 10 wt%.

2. The photosensitive resin composition as claimed in claim 1, wherein, In formula (V), X represents an aliphatic hydrocarbon group with 1 to 5 carbon atoms.

3. The photosensitive resin composition as claimed in claim 1, wherein, In formula (V), M represents a hydrogen atom, an ammonium group, or an organic ammonium group.

4. The photosensitive resin composition as claimed in claim 1, wherein, The triphenylmethane-based colorant (A-1) has heterogeneous multiple acid anions containing at least one of molybdenum and tungsten.

5. The photosensitive resin composition as claimed in claim 1, wherein, The triphenylmethane-based colorant (A-1) is selected from at least one of the group consisting of triphenylmethane-based colorants (A-1-1) having the structure shown in formula (I-1), triphenylmethane-based colorants (A-1-2) having the structure shown in formula (I-2), and triphenylmethane-based colorants (A-1-3) having the structure shown in formula (I-3). In formula (I-1), 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, and the organic group represents an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at least at the end directly bonded to N, or an aromatic group having the aliphatic hydrocarbon group. The carbon chain of the aliphatic hydrocarbon group may contain at least one of an oxygen atom, a sulfur atom, and a nitrogen atom, and the carbon chain of the aromatic group may contain at least one of an oxygen atom, a sulfur atom, and a nitrogen atom. R1, R2, R3, R4, and R5 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, wherein R2 and R3 can be bonded to each other to form a ring structure, and R4 and R5 can be bonded to each other to form a ring structure. Multiple R1, R2, R3, R4, and R5 can be the same or different. Ar1 represents a substituted or unsubstituted divalent aromatic group, and multiple Ar1 can be the same or different. p represents an integer greater than 2. In formula (I-2), R6, R7, R8, R9, R10, and R11 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group. R12, R13, and R14 each independently represent an alkyl group having 1 to 8 carbon atoms, or a chlorine atom. t and u each independently represent an integer from 0 to 4. v represents an integer from 0 to 6, where t, u, and v are not simultaneously 0; In formula (I-3), R15, R16, R17, R18, R19, and R20 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group; R21, R22, and R23 each independently represent an alkyl group having 1 to 8 carbon atoms, or a chlorine atom; and f, g, and h each independently represent an integer from 0 to 4.

6. The photosensitive resin composition as claimed in claim 1, wherein, The triphenylmethane-based colorant (A-1) comprises a triphenylmethane-based colorant having a structure as shown in formula (I-1-1), where 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, and the organic group represents an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at least at the end directly bonded to N, or an aromatic group having the aliphatic hydrocarbon group. The carbon chain of the aliphatic hydrocarbon group may contain at least one of an oxygen atom, a sulfur atom, and a nitrogen atom, and the carbon chain of the aromatic group may contain at least one of an oxygen atom, a sulfur atom, and a nitrogen atom. R1, R2, R3, R4, and R5 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. R2 and R3 can bond to each other to form a ring structure, and R4 and R5 can bond to each other to form a ring structure. Multiple R1, R2, R3, R4, and R5 can be the same or different. Ar1 represents a substituted or unsubstituted divalent aromatic group. Multiple Ar1 can be the same or different. Bq- represents an anion. p represents an integer greater than 2. r and s each independently represent an integer greater than 1.

7. A method for manufacturing a color filter, comprising: forming a pixel layer using a photosensitive resin composition as described in any one of claims 1 to 6.

8. A color filter, which is manufactured by the method for manufacturing a color filter as described in claim 7.

9. A liquid crystal display comprising: a color filter as described in claim 8.