Photosensitive resin composition, photosensitive resin film produced using the same, color filter, and display device
The photosensitive resin composition, featuring a phthalocyanine-based dispersion aid, addresses the challenges of color reproducibility and light/dark ratio in color filters by enhancing pigment dispersibility and stability, resulting in improved performance for liquid crystal display devices.
Patent Information
- Application Number
- JP2023148239
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2022-11-02
- Filing Date
- 2023-09-13
- Publication Date
- 2025-05-16
- Estimated Expiration
- 2043-09-13
AI Technical Summary
Existing photosensitive resin compositions for color filters used in liquid crystal display devices face challenges in achieving high color reproducibility and light/dark ratio while maintaining high dispersibility and dispersion stability of pigments.
A photosensitive resin composition comprising a pigment, a dispersant, and a dispersion aid represented by a specific chemical formula, which includes a phthalocyanine-based maternal nucleus with asymmetrically substituted carboxy groups, enhancing dispersibility and dispersion stability while improving coloring power and light/dark ratio.
The composition provides a color filter with excellent coloring power and light/dark ratio, along with high dispersibility and dispersion stability, leading to improved performance in liquid crystal display devices.
Smart Images

Figure 0007678854000001 
Figure 0007678854000002 
Figure 0007678854000003
Abstract
Description
[Technical field]
[0001] The present disclosure relates to a photosensitive resin composition, a photosensitive resin film produced using the same, and a color filter. [Background technology]
[0002] Liquid crystal display devices, which are one type of display device, have advantages such as light weight, thin shape, low cost, low power consumption, excellent connectivity with integrated circuits, etc., and are being used in a wide range of applications such as notebook computers, monitors, and TV images. Such liquid crystal display devices include a lower substrate on which a black matrix, color filters, and ITO pixel electrodes are formed, an active circuit section consisting of a liquid crystal layer, a thin film transistor, and a storage capacitor layer, and an upper substrate on which ITO pixel electrodes are formed.
[0003] A color filter is provided on a black matrix layer formed in a predetermined pattern on a transparent substrate to shield the boundaries between pixels, and a plurality of colors (usually the three primary colors of red (R), green (G), and blue (B)) are laminated on a pixel portion arranged in a predetermined order to form each pixel. The pigment dispersion method, which is one of the methods for producing a color filter, is a method in which a photopolymerizable composition containing a colorant is coated on a transparent substrate provided with a black matrix, and a pattern of the desired shape is exposed to light, and then the non-exposed area is removed with a solvent and the exposed area is thermally cured, and a series of steps are repeated to form a colored thin film (photosensitive resin film). The photosensitive resin composition (pigment-type photosensitive resin composition) used in the production of color filters by the pigment dispersion method generally consists of an alkali-soluble resin, a photopolymerization monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method having the above characteristics is frequently applied to the production of LCDs used in mobile phones, notebook computers, monitors, TVs, etc.
[0004] However, in recent years, photosensitive resin compositions for color filters, to which the pigment dispersion method having various advantages is applied, are being required to have not only excellent pattern characteristics but also more improved performance, and in particular, there is an urgent need for high color reproduction rate as well as brightness / darkness ratio characteristics. Summary of the Invention [Problem to be solved by the invention]
[0005] An object of one embodiment is to provide a photosensitive resin composition that provides a color filter having excellent coloring power and light-dark ratio while having high dispersibility and dispersion stability.An object of another embodiment is to provide a photosensitive resin film produced using the photosensitive resin composition.An object of yet another embodiment is to provide a color filter including the photosensitive resin film. [Means for solving the problem]
[0006] One embodiment provides a photosensitive resin composition comprising (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, (D) a binder resin, and (E) a solvent, wherein the colorant comprises a pigment, a dispersant, and a dispersion aid represented by the following chemical formula 1: [Chemical formula 1]
[0007] [ka]
[0008] In formula 1, M is Cu or Zn, and R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group; R 41 ~R 44are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group; R 41 ~R 44 At least one of R is a C1 to C20 alkoxy group substituted with a carboxy group. 11 ~R 14 may all be hydrogen atoms or all be halogen atoms. 21 ~R 24 Any one of R may be a substituted or unsubstituted C1 to C20 alkyl group, and the rest may all be hydrogen atoms. 31 ~R 34 may all be hydrogen atoms. 41 ~R 44 Any one of the following may be a substituent represented by any one of the following chemical formulas 2 to 4, and the rest may all be hydrogen atoms or all halogen atoms. [Chemical formula 2]
[0009] [ka]
[0010] In formula 2, R 51 ~R 55 are each independently a hydrogen atom, a halogen atom, a carboxyl group, or a substituent represented by the following chemical formula 5, and R 51 ~R 55 At least one of the groups is a carboxy group or a substituent represented by the following chemical formula 5. [Chemical formula 3]
[0011] [ka]
[0012] [ka]
[0013] [Chemical formula 4] In formulas 3 and 4, L 1 ~L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene. [Chemical formula 5]
[0014] [ka]
[0015] In formula 5, R 61 ~R 65 are each independently a hydrogen atom, a halogen atom, or a carboxy group; R 61 ~R 65 At least one of R is a carboxy group. 51 ~R 55 Two of R may be a carboxy group or a substituent represented by chemical formula 5, and the rest may all be hydrogen atoms or all halogen atoms. 61 ~R 65 Two of the L groups may be carboxy groups, and the rest may all be hydrogen atoms or halogen atoms. 1 may be a substituted or unsubstituted C1-C10 alkylene. 2 and L 3 may each independently be a substituted or unsubstituted C1 to C10 alkylene. The dispersion aid represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3. [Chemical formula 1-1]
[0016] [ka]
[0017] [Chemical formula 1-2]
[0018] [ka]
[0019] [Chemical formula 1-3]
[0020] [ka]
[0021] In formulas 1-1 to 1-3, M is Cu or Zn, and R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 , R 42 and R 44 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group; R 51 ~R 55 R are each independently a hydrogen atom, a halogen atom, a carboxyl group, or a substituent represented by the following chemical formula 5. 51 ~R 55 At least one of L is a carboxy group or a substituent represented by the following chemical formula 5: 1 ~L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene. [Chemical formula 5]
[0022] [ka]
[0023] In formula 5, R 61 ~R 65 are each independently a hydrogen atom, a halogen atom, or a carboxy group; R 61 ~R 65 At least one of the groups is a carboxy group.
[0024] The dispersing aid represented by Formula 1 may be selected from the group consisting of: [Chemical formula 1-1-1]
[0025] [ka]
[0026] [Chemical formula 1-1-2]
[0027]
change
[0028] [Chemical formula 1-1-3]
[0029]
change
[0030] [Chemical formula 1-1-4]
[0031]
change
[0032] [Chemical formula 1-1-5]
[0033]
change
[0034] [Chemical formula 1-1-6]
[0035]
change
[0036] [Chemical formula 1-1-7]
[0037]
change
[0038] [Chemical formula 1-1-8]
[0039]
change
[0040] [Chemical formula 1-1-9]
[0041]
change
[0042] [Chemical formula 1-1-10]
[0043]
change
[0044]
change
[0045] [Chemical formula 1-2-1] [Chemical formula 1-2-2]
[0046]
change
[0047] [Chemical formula 1-2-3]
[0048]
change
[0049] [Chemical formula 1-2-4]
[0050]
change
[0051] [Chemical formula 1-2-5]
[0052]
change
[0053] [Chemical formula 1-2-6]
[0054]
change
[0055] [Chemical formula 1-2-7]
[0056]
change
[0057] [Chemical formula 1-2-8]
[0058]
change
[0059] [Chemical formula 1-2-9]
[0060]
change
[0061] [Chemical formula 1-2-10]
[0062]
change
[0063] [Chemical formula 1-3-1]
[0064]
change
[0065] [Chemical formula 1-3-2]
[0066]
change
[0067] [Chemical formula 1-3-3]
[0068]
change
[0069] [Chemical formula 1-3-4]
[0070]
change
[0071] [Chemical formula 1-3-5]
[0072]
change
[0073] [Chemical formula 1-3-6]
[0074]
change
[0075] [Chemical formula 1-3-7]
[0076]
change
[0077] [Chemical formula 1-3-8]
[0078]
change
[0079] [Chemical formula 1-3-9]
[0080]
change
[0081] [Chemical formula 1-3-10]
[0082]
change
[0083] [Chemical formula 1-4-1]
[0084]
change
[0085] [Chemical formula 1-4-2]
[0086]
change
[0087] [Chemical formula 1-4-3]
[0088]
change
[0089] [Chemical formula 1-4-4]
[0090]
change
[0091] [Chemical formula 1-4-5]
[0092]
change
[0093] [Chemical formula 1-4-6]
[0094]
change
[0095] [Chemical formula 1-4-7]
[0096]
change
[0097] [Chemical formula 1-4-8]
[0098]
change
[0099] [Chemical formula 1-4-9]
[0100]
change
[0101] [Chemical formula 1-4-10]
[0102]
change
[0103] [Chemical formula 1-5-1]
[0104]
change
[0105] [Chemical formula 1-5-2]
[0106]
change
[0107] [Chemical formula 1-5-3]
[0108]
change
[0109] [Chemical formula 1-5-4]
[0110]
change
[0111] [Chemical formula 1-5-5]
[0112]
change
[0113] [Chemical formula 1-5-6]
[0114]
change
[0115] [Chemical formula 1-5-7]
[0116]
change
[0117] [Chemical formula 1-5-8]
[0118]
change
[0119] [Chemical formula 1-5-9]
[0120]
change
[0121] [Chemical formula 1-5-10]
[0122]
change
[0123] The dispersion auxiliary represented by Chemical Formula 1 may have a maximum absorption wavelength of 450 nm to 495 nm. The dispersion auxiliary represented by Chemical Formula 1 may be contained in an amount of 0.5 wt % to 6 wt % based on the total amount of the photosensitive resin composition. The weight ratio of the dispersion auxiliary represented by Chemical Formula 1 to the pigment may be 1:20 to 1:70.
[0124] The pigment may include a green pigment, a yellow pigment, or a combination thereof.
[0125] The photosensitive resin composition can contain, relative to the total amount of the photosensitive resin composition, (A) 0.5 wt % to 15 wt % of a colorant, (B) 0.1 wt % to 10 wt % of a photopolymerizable compound, (C) 0.1 wt % to 10 wt % of a photopolymerization initiator, (D) 0.5 wt % to 15 wt % of a binder resin, and (E) a remaining amount of solvent.
[0126] Another embodiment provides a photosensitive resin film produced using the photosensitive resin composition. The photosensitive resin film may be a color negative photoresist.
[0127] In another embodiment, a color filter including the photosensitive resin film is provided. In another embodiment, a display device including the color filter is provided. Specific details of other aspects of the present invention are included in the following detailed description. Effect of the Invention
[0128] The photosensitive resin composition according to an embodiment can provide a color filter having excellent coloring power and a contrast ratio while having high dispersibility and dispersion stability. Therefore, by using the photosensitive resin composition according to an embodiment, an excellent color filter and a display device can be provided. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0129] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, preferred embodiments of the present invention will be described in detail by way of example only, without however limiting the present invention, which is defined only by the scope of the claims that follow.
[0130] Unless otherwise specified in this specification, "substituted" means that at least one hydrogen atom in the compound is substituted with a substituent selected from the group consisting of a halogen atom (F, Cl, Br, I), a hydroxy group, a C1-C20 alkoxy group, a nitro group, a cyano group, an amino group, an imino group, an azide group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 aryl group, a C3-C20 cycloalkyl group, a C3-C20 cycloalkenyl group, a C8-C20 cycloalkynyl group, a C2-C20 heterocycloalkyl group, a C2-C20 heterocycloalkenyl group, a C2-C20 heterocycloalkynyl group, or a combination thereof.
[0131] Unless otherwise specified in this specification, the terms "heterocycloalkyl group," "heterocycloalkenyl group," "heterocycloalkynyl group," and "heterocycloalkylene group" mean that at least one N, O, S, or P heteroatom is present in the ring system of a cycloalkyl, cycloalkenyl, cycloalkynyl, and cycloalkylene, respectively.
[0132] Unless otherwise specified in this specification, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible.
[0133] Unless otherwise defined herein, "combination" means blending or copolymerization, "copolymerization" means block copolymerization and random copolymerization, and "copolymer" means block copolymerization and random copolymerization.
[0134] Unless otherwise defined in a chemical formula in this specification, when no chemical bond is drawn at a position where a chemical bond should be drawn, this means that a hydrogen atom is bonded at that position.
[0135] Unless otherwise defined herein, "*" means a moiety linked to the same or different atom or chemical formula.
[0136] Unless otherwise defined herein, "particle size" means the diameter of a particle, which may be the Z-average particle diameter as measured by dynamic light scattering. (Photosensitive resin composition) One embodiment provides a photosensitive resin composition comprising (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, (D) a binder resin, and (E) a solvent, wherein the colorant comprises a pigment, a dispersant, and a dispersion aid represented by the following chemical formula 1: [Chemical formula 1]
[0137] [ka]
[0138] In formula 1, M is Cu or Zn, and R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group; R 41 ~R 44 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group; R 41 ~R 44 At least one of them is a C1 to C20 alkoxy group substituted with a carboxy group. (A) Colorant The photosensitive resin composition of one embodiment is a pigment-type photosensitive resin composition, and the colorant includes a pigment. In a color filter manufactured using the pigment-type photosensitive resin composition, there is a limit to the brightness and the light-to-dark ratio due to the particle size of the pigment. In addition, in order to be applied to an image sensor, a resin composition consisting of smaller particles is required to form a fine pattern. To achieve this, it is necessary to realize a compound that promotes the dispersion of the pigment and prevents re-aggregation, and a composition using the same.
[0139] The dispersion aid represented by Chemical Formula 1 has a phthalocyanine mother nucleus and a carboxy group asymmetrically substituted on the phthalocyanine mother nucleus. The phthalocyanine mother nucleus interacts with the pigment, and the carboxy group asymmetrically substituted on the phthalocyanine mother nucleus interacts with the dispersant or dispersion resin. Therefore, the dispersion aid represented by Chemical Formula 1 has the function of assisting the dispersant in the photosensitive resin composition to increase the dispersibility and dispersion safety of the pigment. Furthermore, the phthalocyanine mother nucleus expresses a blue color. Therefore, the dispersion aid represented by Chemical Formula 1 has the function of cooperating with the colorant in the photosensitive resin composition to increase the coloring power.
[0140] That is, the dispersion auxiliary represented by Chemical Formula 1 not only assists the dispersant to improve the dispersibility and dispersion safety of the pigment, but also assists the colorant to improve the coloring power. Therefore, when a photosensitive resin composition containing the dispersion auxiliary represented by Chemical Formula 1 is used in a color filter and a display device, the coloring power (color reproduction rate) and brightness ratio can be improved.
[0141] R 11 ~R 14 may each independently be a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group. For example, R 11 ~R 14 may all be hydrogen atoms or all be halogen atoms. Here, the halogen atoms may be chlorine atoms. R 21 ~R 24may each independently be a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group. 21 ~R 24 may all be hydrogen atoms. 21 ~R 24 Any one of R may be a substituted or unsubstituted C1 to C20 alkyl group, and the rest may all be hydrogen atoms. For example, R 21 ~R 24 One or two of R may be a branched C4 alkyl group (e.g., a tert-butyl group), and the rest may all be hydrogen atoms. 21 ~R 24 Compared to when all are hydrogen atoms, R 21 ~R 24 When one or two of R are branched C4 alkyl groups, the solubility of the dispersing aid represented by formula 1 in the solvent is improved. 21 ~R 24 The number of branched C4 alkyl groups in may depend on the number of N-containing substituents (A) in the dispersing aid represented by formula 1. If there is one N-containing substituent (A) in the dispersing aid represented by formula 1, then R 21 ~R 24 In addition, if the dispersing agent represented by formula 1 has two N-containing substituents (A), R 21 ~R 24 Of these, two branched C4 alkyl groups may be present. 21 ~R 24 If the number of branched C4 alkyl groups is three or more, the chemical resistance of the dispersion aid represented by Chemical Formula 1 may be reduced. 31 ~R 34 may each independently be a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group. For example, R 31 ~R 34 may all be hydrogen atoms.
[0142] The carboxy group asymmetrically substituted on the phthalocyanine-based mother nucleus is a "C1-C20 alkoxy group substituted at the end with one or more carboxy groups." In addition, the number of carboxy groups asymmetrically substituted on the phthalocyanine-based mother nucleus is one or more. This will be explained in detail next.
[0143] R 41 ~R 44 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group; R 41 ~R 43 At least one of R may be a C1 to C20 alkoxy group substituted with a carboxy group. 41 ~R 44 Any one of the following may be a substituent represented by any one of the following chemical formulas 2 to 4, and the rest may all be hydrogen atoms or all halogen atoms. [Chemical formula 2]
[0144] [ka]
[0145] In formula 2, R 51 ~R 55 are each independently a hydrogen atom, a halogen atom, a carboxyl group, or a substituent represented by the following chemical formula 5, R 51 ~R 55 At least one of the groups is a carboxy group or a substituent represented by the following chemical formula 5. [Chemical formula 3]
[0146] [ka]
[0147] [Chemical formula 4]
[0148] [ka]
[0149] In formulas 3 and 4, L 1 ~L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene. [Chemical formula 5]
[0150] [ka]
[0151] In formula 5, R 61 ~R 65 are each independently a hydrogen atom, a halogen atom, or a carboxy group; R 61 ~R 65 At least one of R is a carboxy group. 51 ~R 55 Two of R may be a carboxy group or a substituent represented by chemical formula 5, and the rest may all be hydrogen atoms or all be halogen atoms. 61 ~R 65 Two of the L may be carboxy groups, and the rest may all be hydrogen atoms or all may be atoms. 1 is a substituted or unsubstituted C1-C10 alkylene, e.g., *-CH 2 -* or *-CH 2 -C(CH 3 ) 2 -* is also acceptable. 2 and L 3 are each independently a substituted or unsubstituted C1 to C10 alkylene, for example, *-CH 2 -* is also fine.
[0152] The dispersion aid represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3. [Chemical formula 1-1]
[0153] [ka]
[0154] [Chemical formula 1-2]
[0155] [ka]
[0156] [Chemical formula 1-3]
[0157] [ka]
[0158] In formulas 1-1 to 1-3, M is Cu or Zn, and R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 , R 42 and R 44 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group; R 51 ~R 55 are each independently a hydrogen atom, a halogen atom, a carboxyl group, or a substituent represented by the following chemical formula 5, R 51 ~R 55 At least one of L is a carboxy group or a substituent represented by the following chemical formula 5: 1 ~L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene. [Chemical formula 5]
[0159] [ka]
[0160] In formula 5, R 61 ~R 65 are each independently a hydrogen atom, a halogen atom, or a carboxy group; R 61 ~R 65 At least one of the groups is a carboxy group.
[0161] In Chemical Formulae 1-1 to 1-3 and Chemical Formula 5, the specific explanations regarding each substituent are as described above.
[0162] Representative examples of the dispersion aid represented by Chemical Formula 1 are as follows: [Chemical formula 1-1-1]
[0163] [ka]
[0164] [Chemical formula 1-1-2]
[0165] [ka]
[0166] [Chemical formula 1-1-3]
[0167] [ka]
[0168] [Chemical formula 1-1-4]
[0169] [ka]
[0170] [Chemical formula 1-1-5]
[0171] [ka]
[0172] [Chemical formula 1-1-6]
[0173] [ka]
[0174] [Chemical formula 1-1-7]
[0175]
change
[0176] [Chemical formula 1-1-8]
[0177]
change
[0178] [Chemical formula 1-1-9]
[0179]
change
[0180] [Chemical formula 1-1-10]
[0181]
change
[0182] [Chemical formula 1-2-1]
[0183]
change
[0184] [Chemical formula 1-2-2]
[0185]
change
[0186] [Chemical formula 1-2-3]
[0187]
change
[0188] [Chemical formula 1-2-4]
[0189]
change
[0190] [Chemical formula 1-2-5]
[0191]
change
[0192] [Chemical formula 1-2-6]
[0193]
change
[0194] [Chemical formula 1-2-7]
[0195]
change
[0196] [Chemical formula 1-2-8]
[0197]
change
[0198] [Chemical formula 1-2-9]
[0199]
change
[0200] [Chemical formula 1-2-10]
[0201]
change
[0202] [Chemical formula 1-3-1]
[0203]
change
[0204] [Chemical formula 1-3-2]
[0205]
change
[0206] [Chemical formula 1-3-3]
[0207]
change
[0208] [Chemical formula 1-3-4]
[0209]
change
[0210] [Chemical formula 1-3-5]
[0211]
change
[0212] [Chemical formula 1-3-6]
[0213]
change
[0214] [Chemical formula 1-3-7]
[0215]
change
[0216] [Chemical formula 1-3-8]
[0217]
change
[0218] [Chemical formula 1-3-9]
[0219]
change
[0220] [Chemical formula 1-3-10]
[0221]
change
[0222] [Chemical formula 1-4-1]
[0223]
change
[0224] [Chemical formula 1-4-2]
[0225]
change
[0226] [Chemical formula 1-4-3]
[0227]
change
[0228] [Chemical formula 1-4-4]
[0229]
change
[0230] [Chemical formula 1-4-5]
[0231]
change
[0232] [Chemical formula 1-4-6]
[0233]
change
[0234] [Chemical formula 1-4-7]
[0235]
change
[0236] [Chemical formula 1-4-8]
[0237]
change
[0238] [Chemical formula 1-4-9]
[0239]
change
[0240] [Chemical formula 1-4-10]
[0241]
change
[0242] [Chemical formula 1-5-1]
[0243]
change
[0244] [Chemical formula 1-5-2]
[0245]
change
[0246] [Chemical formula 1-5-3]
[0247]
change
[0248] [Chemical formula 1-5-4]
[0249]
change
[0250] [Chemical formula 1-5-5]
[0251]
change
[0252] [Chemical formula 1-5-6]
[0253]
change
[0254] [Chemical formula 1-5-7]
[0255]
change
[0256] [Chemical formula 1-5-8]
[0257]
change
[0258] [Chemical formula 1-5-9]
[0259] [ka]
[0260] [Chemical formula 1-5-10]
[0261] [ka]
[0262] As described above, the dispersion assistant represented by Chemical Formula 1 has a phthalocyanine-based mother nucleus that exhibits blue color, and can further improve the coloring power and the light-dark ratio of the photosensitive resin composition. Specifically, the dispersion assistant represented by Chemical Formula 1 has a maximum absorption wavelength (λ max ) may be 450 nm to 495 nm. The dispersion auxiliary represented by Chemical Formula 1 may be contained in an amount of 0.5 wt % to 6 wt %, specifically 1 wt % to 5 wt %, for example 2 wt % to 3 wt %, based on the total amount of the photosensitive resin composition. The weight ratio of the dispersion auxiliary represented by Chemical Formula 1 to the pigment may be 1:20 to 1:70, specifically 1:30 to 1:60, for example 1:40 to 1:50. Within each of the above ranges, the coloring power and light-dark ratio of the resulting color filter can be improved while improving the dispersibility and dispersion safety of the photosensitive resin composition according to one embodiment.
[0263] The colorant may include a pigment, and examples of the pigment include green pigment, blue pigment, red pigment, purple pigment, yellow pigment, black pigment, etc. Red pigments include CI Red Pigment 254, CI Red Pigment 255, CI Red Pigment 264, CI Red Pigment 270, CI Red Pigment 272, CI Red Pigment 177, CI Red Pigment 89, etc. in the Color Index, which may be used alone or in combination of two or more kinds, but are not necessarily limited thereto.
[0264] The purple pigment may be, in the Color Index, CI Violet Pigment 23 (V.23), CI Violet Pigment 29, Dioxazine Violet, Fast Violet B, Methyl Violet Lake, Indanthrene Brilliant Violet, or the like, which may be used alone or in combination of two or more kinds, but is not necessarily limited thereto.
[0265] The green pigment may be, for example, CI Green Pigment 7, CI Green Pigment 36, CI Green Pigment 58, or CI Green Pigment 59 in the Color Index, and may be used alone or in combination of two or more of these, but is not necessarily limited thereto.
[0266] The blue pigment may be a copper phthalocyanine pigment such as CI Blue Pigment 15:6, CI Blue Pigment 15, CI Blue Pigment 15:1, CI Blue Pigment 15:2, CI Blue Pigment 15:3, CI Blue Pigment 15:4, CI Blue Pigment 15:5, CI Blue Pigment 15:6, CI Blue Pigment 16, etc., which may be used alone or in combination of two or more kinds, but is not necessarily limited thereto.
[0267] The yellow pigment may be, in the color index, an isoindoline pigment such as CI Yellow Pigment 185 or CI Yellow Pigment 139, a quinophthalone pigment such as CI Yellow Pigment 138, or a nickel complex pigment such as CI Yellow Pigment 150, and may be used alone or in combination of two or more of these, but is not necessarily limited thereto.
[0268] The black pigment may be, but is not limited to, aniline black, perylene black, titanium black, carbon black, etc., which may be used alone or in combination of two or more kinds, in the color index.
[0269] The pigments may be used alone or in combination of two or more thereof. For example, the pigment may be a green pigment, a yellow pigment, or a mixture thereof.
[0270] The dispersant promotes uniform dispersion of the pigment in the dispersion liquid, and nonionic, anionic or cationic dispersants can be used. Specifically, polyalkylene glycol or its ester, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylate, carboxylate, alkylamide alkylene oxide adduct, alkylamine, etc. can be used, and these can be used alone or in combination of two or more kinds.
[0271] The pigment may be contained in the photosensitive resin composition for color filters in a dispersed state. Such a pigment dispersion may further contain a dispersion solvent, a dispersion resin, etc., in addition to the pigment, the dispersant, and the dispersion assistant. The solid pigment excluding the solvent may be contained in an amount of 5% by weight to 20% by weight, for example 8% by weight to 15% by weight, based on the total amount of the pigment dispersion.
[0272] As the solvent for the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc. can be used, and among these, propylene glycol methyl ether acetate can be preferably used.
[0273] The dispersing resin can be an acrylic resin containing a carboxy group, which can not only improve the stability of the pigment dispersion liquid, but also improve the patterning of the pixels.
[0274] The colorant may further include a dye in addition to a pigment, and in this case, the resin composition of an embodiment may be a hybrid type composition. In addition, the dye may include, but is not limited to, a metal complex dye.
[0275] As the metal complex dye, a compound having a maximum absorbance in the wavelength region of 200 nm to 650 nm can be used, and as long as the compound has an absorbance in the above range in order to match the color coordinates with the combination of dyes, any color metal complex dye that is soluble in an organic solvent can be used. Specifically, the metal complex dye can be a green dye having a maximum absorbance in the wavelength region of 530 nm to 680 nm, a yellow dye having a maximum absorbance in the wavelength region of 200 nm to 400 nm, an orange dye having a maximum absorbance in the wavelength region of 300 nm to 500 nm, a red dye having a maximum absorbance in the wavelength region of 500 nm to 650 nm, or a combination thereof.
[0276] As the metal complex dye, a direct dye, an acid dye, a basic dye, an acid mordant dye, a sulfur dye, a reduction dye, an azoic dye, a disperse dye, a reactive dye, an oxidation dye, an oil-soluble dye, an azo dye, an anthraquinone dye, an indigo dye, a carbonium ion dye, a phthalocyanine dye, a nitro dye, a quinoline dye, a cyanine dye, a polymethine dye, or a combination thereof can be used.
[0277] The metal complex dye may contain at least one metal ion selected from the group consisting of Mg, Ni, Cu, Co, Zn, Cr, Pt, Pd and Fe.
[0278] Metal complex dyes include CI Solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Acid Green 2, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Acid Green 3, 4, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Acid Green ...5, 5, 6, Dyes, CI Direct Dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, CI Basic Dyes such as CI Basic Green 1, CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, A complex of at least one selected from the group consisting of CI mordant dyes such as CI Pigment Green 7, 36, 58, green pigments such as CI Pigment Green 7, 36, 58, solvent yellow 19, solvent yellow 21, solvent yellow 25, solvent yellow 79, solvent yellow 82, solvent yellow 88, solvent orange 45, solvent orange 54, solvent orange 62, solvent orange 99, solvent red 8, solvent red 32, solvent red 109, solvent red 112, solvent red 119, solvent red 124, solvent red 160, solvent red 132 and solvent red 218 and the above metal ion can be used.
[0279] The dye containing a metal complex may have a solubility of 5 or more in the solvent used in the photosensitive resin composition according to one embodiment, i.e., the solvent described below, specifically, may be 5 to 10. The solubility can be obtained as the amount (g) of the dye dissolved in 100 g of the solvent. When the solubility of the dye containing a metal complex is within the above range, it is possible to ensure compatibility with other components constituting the photosensitive resin composition according to one embodiment and the coloring power of the color filter, and it is possible to prevent precipitation of the dye.
[0280] As the solvent, for example, propylene glycol monomethyl ether acetate, ethyl lactate, ethylene glycol ethyl acetate, cyclohexanone, 3-methoxy-1-butanol, or a combination thereof can be used. By having the above-mentioned specific range, it can be used as a color filter for LCD, LED, etc. that expresses high brightness and high brightness / dark ratio at the desired color coordinates.
[0281] The dye containing a metal complex may be contained in an amount of 0.01% by weight to 1% by weight, for example, 0.01% by weight to 0.5% by weight, based on the total amount of the photosensitive resin composition. When the dye containing a metal complex is used in this range, a color filter for LCD, LED, etc. that exhibits high brightness and light-dark ratio at the desired color coordinates can be formed.
[0282] When dyes and pigments are mixed and used, they can be mixed at a weight ratio of 0.1:99.9 to 99.9:0.1, specifically 1:9 to 9:1. By mixing dyes and pigments within this weight ratio range, it is possible to control the chemical resistance and maximum absorption wavelength within appropriate ranges, and form color filters for LCDs, LEDs, etc. that exhibit high brightness and light-dark ratio at the desired color coordinates.
[0283] The colorant may be contained in an amount of 5% by weight to 50% by weight, specifically 6% by weight to 40% by weight, for example 7% by weight to 30% by weight, based on the solid content, relative to the total amount of the photosensitive resin composition. When the colorant is contained within the above range, an excellent coloring effect can be obtained, and the photosensitive resin composition can exhibit excellent developability. (B) Photopolymerizable compound As the photopolymerizable compound, a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond can be used. By having an ethylenically unsaturated double bond, the photopolymerizable compound can be sufficiently polymerized upon exposure in the pattern formation process to form a pattern having excellent heat resistance, light resistance, and chemical resistance. Specific examples of the photopolymerizable compound include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and the like. acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy(meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(meth)acryloyloxyethyl phosphate, novolac epoxy(meth)acrylate, and the like.
[0284] Examples of commercially available products of photopolymerizable compounds are as follows. Examples of monofunctional esters of (meth)acrylic acid include ARONIX (registered trademark) M-101, M-111, M-114, etc., manufactured by Toagosei Chemical Industry Co., Ltd., KAYARAD (registered trademark) TC-110S, TC-120S, etc., manufactured by Nippon Kayaku Co., Ltd., and V-158, V-2311, etc., manufactured by Osaka Organic Chemical Industry Co., Ltd. Examples of bifunctional esters of (meth)acrylic acid include ARONIX (registered trademark) M-210, M-240, M-6200, etc., manufactured by Toagosei Chemical Industry Co., Ltd., KAYARAD (registered trademark) HDDA, HX-220, R-604, etc., manufactured by Nippon Kayaku Co., Ltd., and V-260, V-312, V-335HP, etc., manufactured by Osaka Organic Chemical Industry Co., Ltd. Examples of trifunctional esters of (meth)acrylic acid include ARONIX (registered trademark) M-309, M-400, M-405, M-450, M-710, M-8030, and M-8060 manufactured by Toagosei Chemical Industry Co., Ltd., KAYARAD (registered trademark) TMPTA, DPCA-20, -30, -60, and -120 manufactured by Nippon Kayaku Co., Ltd., and V-295, -300, -360, -GPT, -3PA, and -400 manufactured by Osaka Organic Chemical Industry Co., Ltd. The above products can be used alone or in combination of two or more kinds.
[0285] The photopolymerizable compound can also be used after being treated with an acid anhydride in order to impart better developability.
[0286] The photopolymerizable compound may be contained in an amount of 0.1% by weight to 20% by weight, specifically 1% by weight to 15% by weight, for example 2% by weight to 13% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained within the upper range, curing occurs sufficiently upon exposure in the pattern formation process, the obtained color filter has excellent reliability, and the photosensitive resin composition shows excellent developability in an alkaline developer. (C) Photopolymerization initiator The photopolymerization initiator is an initiator generally used in photosensitive resin compositions, and for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, or a combination thereof can be used.
[0287] Examples of acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one.
[0288] Examples of benzophenone-based compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
[0289] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.
[0290] Examples of the benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
[0291] Examples of triazine compounds include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, and the like.
[0292] Examples of oxime compounds that can be used include O-acyloxime compounds, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, and O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one.
[0293] Specific examples of O-acyloxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-one oxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate.
[0294] As the photopolymerization initiator, in addition to the above compounds, carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, non-imidazole compounds, fluorene compounds, etc. can be used. The photopolymerization initiator can also be used together with a photosensitizer that absorbs light to become excited and then transfers the energy to the photopolymerization initiator to cause a chemical reaction. Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, and dipentaerythritol tetrakis-3-mercaptopropionate. The photopolymerization initiator may be contained in an amount of 0.1% by weight to 5% by weight, for example 1% by weight to 3% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is within the above range, sufficient curing occurs upon exposure in the pattern formation process, and as a result, the obtained color filter can have excellent reliability, the pattern has excellent heat resistance, light resistance and chemical resistance, and also has excellent resolution and adhesion, and can prevent a decrease in transmittance due to unreacted initiator. (D) Binder resin The binder resin may include an acrylic resin. The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing one or more acrylic repeating units. The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxy groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof. The first ethylenically unsaturated monomer may be included in an amount of 5% by weight to 50% by weight, for example 10% by weight to 40% by weight, based on the total amount of the acrylic binder resin. Examples of the second ethylenically unsaturated monomer include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyl toluene, and vinyl benzyl methyl ether; unsaturated carboxylic acid ester compounds such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, and phenyl (meth)acrylate; unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; cyanide vinyl compounds such as (meth)acrylonitrile; and unsaturated amide compounds such as (meth)acrylamide. These can be used alone or in combination of two or more.
[0295] Specific examples of acrylic resins include (meth)acrylic acid / benzyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene copolymer, (meth)acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc., but are not limited thereto, and these can be used alone or in combination of two or more kinds.
[0296] The binder resin may include an epoxy-based binder resin. The binder resin may further include an epoxy-based binder resin to improve the heat resistance of the color filter. Examples of the epoxy-based binder resin include, but are not limited to, phenol novolac epoxy resin, tetramethylbiphenyl epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, alicyclic epoxy resin, and combinations thereof. Furthermore, the binder resin including the epoxy-based binder resin ensures the dispersion stability of colorants such as pigments described below, and at the same time, promotes the formation of pixels with a desired resolution during the development process.
[0297] The epoxy-based binder resin may be included in an amount of 1% by weight to 10% by weight, for example 5% by weight to 10% by weight, based on the total amount of the binder resin. When the epoxy-based binder resin is included in the above range, the residual film rate and chemical resistance of the color filter are significantly improved. The epoxy equivalent weight of the epoxy-based binder resin may be 150 g / eq to 200 g / eq. When an epoxy-based binder resin having an epoxy equivalent within the above range is included in the binder resin, there is an advantageous effect on improving the hardening degree of the pattern of the formed color filter and on the fixation of the colorant in the structure in which the pattern is formed.
[0298] The binder resin can be dissolved in a solvent described below in the form of a solid content to constitute a photosensitive resin composition. In this case, the binder resin in the form of a solid content may be about 0.1% by weight to 30% by weight, for example, 20% by weight to 30% by weight, based on the total amount of the binder resin solution dissolved in the solvent. The binder resin may be contained in an amount of 0.1% by weight to 20% by weight, specifically 0.5% by weight to 15% by weight, for example, 1% by weight to 10% by weight, based on the solid content, based on the total amount of the photosensitive resin composition. When the binder resin is contained within the above range, excellent developability is obtained during the production of a color filter, and crosslinking during exposure is improved, so that the color filter can obtain excellent surface smoothness. (E) SolventAs the solvent, a substance that is compatible with the colorant, binder resin, photopolymerizable compound, and photopolymerization initiator but does not react with them can be used. Examples of the solvent include alcohols such as methanol and ethanol, ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methyl phenyl ether, and tetrahydrofuran, glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether, cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate, carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether, propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate, aromatic hydrocarbons such as toluene and xylene, methyl ethyl ketone, cyclohexanone, 4-hydroxy-4- Ketones such as methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactic acid esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate;Examples of the monooxymonocarboxylic acid alkyl esters include 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyethyl acetate, and methyl 2-hydroxy-3-methylbutanoate; and ketone acid esters such as ethyl pyruvate. Further, high boiling point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate may be mentioned.
[0299] Among these, taking into consideration compatibility and reactivity, the solvent may be propylene glycol monomethyl ether acetate, n-butyl acetate, ethylene glycol dimethyl ether, or a combination thereof.
[0300] The solvent may be contained in an amount of, for example, 70% by weight to 90% by weight, for example, 80% by weight to 90% by weight, based on the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has excellent coatability and a coating film with excellent flatness can be obtained. (F) Other additives The photosensitive resin composition may further contain at least one additive selected from malonic acid, 3-amino-1,2-propanediol, a coupling agent containing a vinyl group or a (meth)acryloxy group, a leveling agent, a surfactant, and a radical polymerization initiator in order to prevent stains or spots during application, improve leveling performance, and prevent the generation of residues due to undevelopment. The additives can be easily adjusted according to the desired physical properties.
[0301] The coupling agent may be a silane coupling agent, and examples of the silane coupling agent include trimethoxysilylbenzoic acid, γ methacryloxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ isocyanate propyl triethoxysilane, γ glycidoxypropyl trimethoxysilane, β epoxy cyclohexyl) ethyl trimethoxysilane, etc., which can be used alone or in combination of two or more. Specifically, the silane coupling agent can be used in an amount of 0.01 to 1 part by weight per 100 parts by weight of the photosensitive resin composition.
[0302] In addition, the photosensitive resin composition for color filters may further contain a surfactant, for example, a fluorine-based surfactant, if necessary. Examples of fluorine-based surfactants include, but are not limited to, F-482, F-484, and F-478 manufactured by DIC Corporation. The surfactant is preferably contained in an amount of 0.01% by weight to 5% by weight, more preferably 0.01% by weight to 2% by weight, based on the total amount of the photosensitive resin composition. If the surfactant is out of the above range, it is not preferable because a problem of foreign matter being generated after development may occur. In addition, the photosensitive resin composition may contain a certain amount of other additives, such as antioxidants and stabilizers, within a range that does not impair the physical properties of the composition. (Photosensitive resin films, color filters, and display devices) According to another embodiment, a photosensitive resin film is provided that is manufactured using the photosensitive resin composition according to the embodiment. The photosensitive resin film according to the embodiment is roughly divided into a color positive photoresist composition and a color negative photoresist composition. The photosensitive resin film according to the embodiment may be a color negative photoresist. This has the advantage that the use of a negative photoresist does not cause coloring due to the photoresist, and the negative photoresist has a relatively higher photosensitivity than the positive photoresist.
[0303] According to another embodiment, a color filter is provided that is manufactured using the above-mentioned photosensitive resin composition. The method for manufacturing the color filter of the embodiment is as follows. The above-mentioned photosensitive resin composition is applied to a glass substrate, for example, to a thickness of 0.5 um to 10 um, using a suitable method such as spin coating, roller coating, or spray coating, to form a photosensitive resin composition layer. Next, the substrate on which the photosensitive resin composition layer is formed is irradiated with light to form a pattern required for the color filter. The light used for irradiation can be UV, electron beam, or X-ray, and for example, UV in the range of 190 nm to 450 nm, specifically 200 nm to 400 nm, can be irradiated. The light irradiation can also be performed using a photoresist mask. After performing the light irradiation process, the photosensitive resin composition layer irradiated with light is treated with a developer. At this time, the non-exposed portion of the photosensitive resin composition layer is dissolved to form a pattern required for the color filter. By repeating this process for the number of required colors, a color filter having a desired pattern can be obtained. Furthermore, if the image pattern obtained by development in this step is cured by heating again or by exposure to actinic radiation, the crack resistance, solvent resistance, etc. of the resulting color filter can be improved.
[0304] According to another embodiment, there is provided a display device including the color filter described above. The display device may be a liquid crystal display device, a CMOS image sensor, or the like. EXAMPLES
[0305] The present invention will be described in more detail below with reference to examples. However, the following examples are merely preferred examples of the present invention, and the present invention is not limited to the following examples. Synthesis Example 1: Compound represented by formula 1-1-4 (1) Synthesis of intermediate 1-1
[0306] [ka]
[0307] In a 250 mL flask, add dimethyl 5-hydroxyisophthalate (10 g), 3,4,5,6-tetrachlorophthalonitrile (12.7 g), and K 2 CO 3 (13.2 g) and N,N-dimethylformamide (DMF) (100 mL) were added, and the resulting mixture was stirred while being heated at 70° C. After the reaction was completed, the reaction mixture was extracted with ethyl acetate (EA). The organic layer was concentrated, and the residue was purified by column chromatography. After purification, the product was dried in vacuum to obtain intermediate 1-1. (2) Synthesis of intermediate 1-2
[0308] [ka]
[0309] Intermediate 1-1 (2 g), phthalonitrile (1.17 g), 4-tert-butylphthalonitrile (0.84 g), 1,8-diazobicyclo[5.4.0]-7-undecene (2.77 g) and 1-pentanol (15 g) were added to a 100 mL flask, and the mixture was heated at 90°C to dissolve the solid components. Then, zinc acetate (0.83 g) was added, and the reaction mixture was stirred while being heated at 140°C. After the reaction was completed, the precipitated solid was filtered, washed with methanol, and dried in vacuum. The dried solid was purified by column chromatography. The solid obtained after purification was dissolved in methylene chloride, and then recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain intermediate 1-2. (3) Preparation of the compound represented by formula 1-1-4 Intermediate 2-2 (1.0 g), NaOH (0.34 g), and ethanol (10 mL) were added to a 100 mL flask connected to a condenser, and the reaction mixture was stirred while being heated at 80 °C under a nitrogen atmosphere. After the reaction was completed, an aqueous HCl solution was added to the reaction mixture to adjust the pH to 5-6, and then the mixture was extracted with methylene chloride. The extracted organic layer was diluted with MgSO 4 The mixture was dehydrated at 400° C. and concentrated. The obtained solid was dissolved in methylene chloride, and then recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain a compound represented by the following chemical formula 1-1-4. Maldi-tof MS: 918 m / z. [Chemical formula 1-1-4]
[0310] [ka]
[0311] Synthesis Example 2: Compound represented by formula 1-2-4 (1) Synthesis of intermediate 2-1
[0312] [ka]
[0313] In a 250 mL flask, add 3,5-bis[3,5-bis(methoxycarbonyl)phenoxymethyl]phenol (20.0 g), 3,4,5,6-tetrachlorophthalonitrile (9.88 g), and K 2 CO 3 (10.27 g) and DMF (150 mL) were added, and the reaction mixture was stirred while being heated at 70° C. After the reaction was completed, extraction was performed with EA, and the organic layer was concentrated, and the residue was purified by column chromatography. After purification, the obtained solid was dried in vacuum to obtain intermediate 1-1. (2) Synthesis of intermediate 2-2
[0314] [ka]
[0315] Intermediate 2-1 (4 g), phthalonitrile (1.33 g), 4-tert-butylphthalonitrile (0.96 g), 1,8-diazobicyclo[5.4.0]-7-undecene (3.17 g) and 1-pentanol (15 g) were added to a 100 mL flask, and the reaction mixture was heated at 90 ° C to dissolve the solid, and then zinc acetate (0.96 g) was added, and the reaction mixture was stirred while being heated at 140 ° C. After the reaction was completed, the precipitated solid was filtered, washed with methanol, and dried in vacuum. The dried solid was purified by column chromatography. The solid obtained after purification was dissolved in methylene chloride, and then recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain intermediate 2-2. (3) Preparation of the compound represented by formula 1-2-4 Intermediate 2-2 (1.0 g), NaOH (0.50 g), and ethanol (10 mL) were added to a 100 mL flask connected to a condenser, and the reaction mixture was stirred while being heated at 80 °C in a nitrogen atmosphere. After the reaction was completed, an aqueous HCl solution was added to adjust the pH of the reaction mixture to 5-6, and the mixture was extracted with methylene chloride. The extracted organic layer was diluted with MgSO 4The solid was dissolved in methylene chloride, and then recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain a compound represented by the following chemical formula 1-2-4. Maldi-tof MS: 1218 m / z. [Chemical formula 1-2-4]
[0316] [ka]
[0317] Synthesis Example 3: Compound represented by formula 1-3-4 (1) Synthesis of intermediate 3-1
[0318] [ka]
[0319] In a 250 mL flask, add diethyl 3-hydroxyglutarate (10 g), 3,4,5,6-tetrachlorophthalonitrile (13.0 g), and K 2 CO 3 (13.5 g) and DMF (100 mL) were added, and the reaction mixture was stirred while being heated at 70° C. After the reaction was completed, extraction was performed with EA, and the organic layer was concentrated, and the residue was purified by column chromatography. After purification, the obtained solid was dried in vacuum to obtain intermediate 3-1. (2) Synthesis of intermediate 3-2
[0320] [ka]
[0321] In a 100 mL flask, intermediate 3-1 (2 g), phthalonitrile (1.18 g), 4-tert-butylphthalonitrile (0.85 g), 1,8-diazobicyclo[5.4.0]-7-undecene (2.81 g) and 1-pentanol (15 g) were added, and the reaction mixture was heated at 90° C. to dissolve the solid. Then, zinc acetate (0.85 g) was added, and the reaction mixture was stirred while being heated at 140° C. After the reaction was completed, the precipitated solid was filtered, washed with methanol, and dried in vacuum. The dried solid was purified by column chromatography. The solid obtained after purification was dissolved in methylene chloride, and recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain intermediate 3-2. (3) Preparation of the compound represented by formula 1-3-4 Intermediate 2-2 (1.0 g), NaOH (0.34 g), and ethanol (10 mL) were added to a 100 mL flask equipped with a condenser, and the reaction mixture was stirred under a nitrogen atmosphere while being heated at 80°C. After the reaction was completed, an aqueous HCl solution was added to adjust the pH of the reaction mixture to 5-6, and the mixture was then extracted with methylene chloride. The extracted organic layer was diluted with MgSO 4 The solid was dissolved in methylene chloride and then recrystallized by adding methanol. The crystallized solid was filtered and dried in vacuum to obtain the compound represented by the following chemical formula 1-3-4. Maldi-tof MS: 883 m / z. [Chemical formula 1-3-4]
[0322] [ka]
[0323] Synthesis Example 4: Compound represented by formula 1-4-1 (1) Synthesis of intermediate 4-1
[0324] [ka]
[0325] In a 250 mL flask, add methyl hydroxypivalate (10 g), 4-nitrophthalonitrile (13.1 g), and K2 CO 3 (20.9 g) and DMF (100 mL) were added, and the reaction mixture was stirred while being heated at 70° C. After the reaction was completed, EA was extracted, and the organic layer was concentrated, and the residue was purified by column chromatography (. After purification, the obtained solid was dried in vacuum to obtain intermediate 4-1. (2) Synthesis of intermediate 3-2
[0326] [ka]
[0327] Intermediate 4-1 (2 g), phthalonitrile (2.98 g), 1,8-diazobicyclo[5.4.0]-7-undecene (4.72 g) and 1-pentanol (15 g) were added to a 100 mL flask, and the reaction mixture was heated at 90°C to dissolve the solid. Then, zinc acetate (1.42 g) was added, and the reaction mixture was stirred while being heated at 140°C. After the reaction was completed, the precipitate was filtered, washed with methanol, and dried in vacuum. The dried solid was purified by column chromatography. The solid obtained after purification was dissolved in methylene chloride, and recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain intermediate 3-2. (3) Preparation of the compound represented by formula 1-4-1 Intermediate 4-2 (2.0 g), NaOH (0.43 g), and ethanol (20 mL) were added to a 100 mL flask equipped with a condenser, and the reaction mixture was stirred under a nitrogen atmosphere while being heated at 80°C. After the reaction was completed, an aqueous HCl solution was added to adjust the pH of the reaction mixture to 5-6, and the mixture was extracted with methylene chloride. The extracted organic layer was diluted with MgSO 4 The solid was dissolved in methylene chloride, and then recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain a compound represented by the following chemical formula 1-4-1. Maldi-tof MS: 694 m / z [Chemical formula 1-4-1]
[0328] [ka]
[0329] Synthesis Example 5: Compound represented by formula 1-5-3 (1) Synthesis of intermediate 5-1
[0330] [ka]
[0331] In a 250 mL flask, add methyl glycolate (10 g), 4-nitrophthalonitrile (19.2 g), and K 2 CO 3 (30.7 g) and DMF (100 mL) were added, and the reaction mixture was stirred while being heated at 70° C. After the reaction was completed, extraction was performed with EA. The organic layer was concentrated, and the residue was purified by column chromatography. After purification, the obtained solid was dried in vacuum to obtain intermediate 5-1. (2) Synthesis of intermediate 5-2
[0332] [ka]
[0333] In a 100 mL flask, intermediate 5-1 (2 g), phthalonitrile (2.37 g), 4-tert-butylphthalonitrile (1.70 g), 1,8-diazobicyclo[5.4.0]-7-undecene (5.63 g) and 1-pentanol (15 g) were added, and the reaction mixture was heated at 90° C. to dissolve the solid. Then, zinc acetate (1.70 g) was added, and the reaction mixture was stirred while being heated at 140° C. After the reaction was completed, the precipitated solid was filtered, washed with methanol, and dried in vacuum. The dried solid was purified by column chromatography. The solid obtained after purification was dissolved in methylene chloride, and recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain intermediate 5-2. (3) Preparation of the compound represented by formula 1-5-3 Intermediate 5-2 (2.0 g), NaOH (0.44 g), and ethanol (10 mL) were added to a 100 mL flask equipped with a condenser, and the reaction mixture was stirred while being heated at 80°C under a nitrogen atmosphere. After the reaction was completed, an aqueous HCl solution was added to adjust the pH of the reaction mixture to 5-6, and the mixture was then extracted with methylene chloride. The extracted organic layer was diluted with MgSO 4 The solid was dissolved in methylene chloride, and recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain a compound represented by the following chemical formula 1-5-3. Maldi-tof MS: 656 m / z. [Chemical formula 1-5-3]
[0334] [ka]
[0335] Comparative synthesis example 1 (1) Synthesis of intermediate A-1
[0336] [ka]
[0337] In a 250 mL flask, add phenol (5 g), 3,4,5,6-tetrachlorophthalonitrile (14.1 g), and K 2 CO 3 (14.7 g) and DMF (100 mL) were added, and the reaction mixture was stirred while being heated at 70° C. After the reaction was completed, extraction was performed with EA, the organic layer was concentrated, and the residue was purified by column chromatography. The purified solid was dried in vacuum to obtain intermediate A-1. (2) Preparation of the compound represented by formula A In a 100 mL flask, intermediate A-1 (2 g), phthalonitrile (2.32 g), 4-tert-butylphthalonitrile (1.67 g), 1,8-diazobicyclo[5.4.0]-7-undecene (5.63 g) and 1-pentanol (15 g) were added, and the reaction mixture was heated at 90°C to dissolve the solid, and then zinc acetate (1.67 g) was added, and the reaction mixture was stirred while being heated at 140°C. After the reaction was completed, the precipitate was filtered, washed with methanol, and dried in vacuum. The dried solid was purified by column chromatography. The solid obtained after purification was dissolved in methylene chloride, and recrystallized by adding methanol. The recrystallized solid was filtered and dried in vacuum to obtain chemical formula A. Maldi-tof MS: 834 m / z. [Chemical formula A]
[0338] [ka]
[0339] Manufacturing of green pigment dispersion The components were mixed according to the compositions shown in Tables 1 to 3 below to produce green pigment dispersions of Production Examples 1 to 10 and Production Comparative Examples 1 and 2. Specifically, a green pigment, a dispersant, a dispersion aid, and a solvent were mixed, and 300 parts of zirconia beads (diameter: 0.4 μm) were added per 100 parts by weight of the resulting mixture, which was then subjected to vibration dispersion for 3 hours using a paint shaker, and the zirconia beads were removed using a filter to obtain a green pigment dispersion.
[0340] [Table 1]
[0341] [Table 2]
[0342] [Table 3]
[0343] The substances used in Tables 1 to 3 are as follows:
[0344] Green pigment: CIPIGMENT Green 58 (G58) Dispersant: BYK-LPN6919 (manufacturer: BYK) Dispersing aid: each compound of Synthesis Examples 1 to 5 and Comparative Synthesis Example 1 Solvent: Propylene glycol monomethyl ether acetate (PGMEA) Manufacturing of yellow pigment dispersion 12.0 parts by weight of a yellow pigment (CIPIGMENT Yellow 138), 3.0 parts by weight of a dispersant (BYK-LPN6919, manufacturer: BYK), and 85.0 parts by weight of a solvent (PGMEA) were mixed, and 300 parts by weight of zirconia beads (diameter: 0.4 μm) were added based on 100 parts by weight of the resulting mixture. The mixture was then subjected to vibration dispersion for 3 hours using a paint shaker, and the zirconia beads were removed using a filter to obtain a yellow pigment dispersion. Production of photosensitive resin composition The components were mixed according to the compositions shown in the following Tables 4 to 6 to produce photosensitive resin compositions of Examples 1 to 10 and Comparative Examples 1 and 2. Specifically, a green pigment dispersion, a yellow pigment dispersion, a photopolymerizable monomer, a photopolymerization initiator, a binder resin, and a solvent were mixed to produce the photosensitive colored resin compositions.
[0345] [Table 4]
[0346] [Table 5]
[0347] [Table 6]
[0348] The substances used in Tables 4 to 6 are as follows: (A) Colorant Green pigment dispersion: green pigment dispersions of Production Examples 1 to 10 and Production Comparative Examples 1 and 2 Yellow pigment dispersion (B) Photopolymerizable monomer Dipentaerythritol hexaacrylate (DPHA, Manufacturer: Nippon Kayaku) (C) Photopolymerization initiator C-1: 1,2-octanedione C-2: 2-Dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one (D) Binder resin Resin (Mw=22,000) in which benzyl methacrylate and methacrylic acid are copolymerized in a ratio of 85:15 (E) Solvent Propylene glycol monomethyl ether acetate (PGMEA) Evaluation example 1: Dispersibility and dispersion stability A dynamic light scattering analyzer was used to measure the particle size of the solid content contained in each of the photosensitive resin compositions of Examples 1 to 10 and Comparative Examples 1 and 2, and the results are shown in Table 7 below. In addition, the viscosity of each of the photosensitive resin compositions of Examples 1 to 10 and Comparative Examples 1 and 2 was evaluated at 5 rpm (the rpm at which the torque value is 50 to 100%) and 25°C before and after storage at 23°C for one week, using a Brookfield DV-II Pro viscometer and a CPE-52 Spindle, and the results are shown in Table 7 below.
[0349] [Table 7]
[0350] According to Table 7, it can be seen that the photosensitive resin compositions of Examples 1 to 10 have smaller differences in viscosity as well as in particle size of the solid content before and after storage for one week, compared to the photosensitive resin compositions of Comparative Examples 1 and 2. Evaluation example 2: Color strength and contrast Each of the photosensitive resin compositions of Examples 1 to 10 and Comparative Examples 1 and 2 was applied to a thickness of 1 to 3 μm on a degreased and washed glass substrate having a thickness of 1 mm, and dried on a hot plate at 90° C. for 2 minutes to obtain a coating film. The coating film was then exposed to light using a high-pressure mercury lamp having a dominant wavelength of 365 nm, and then dried in a hot air circulation drying oven at 200° C. for 5 minutes to obtain a color filter specimen. The color coordinates (x, y), luminance (Y) and brightness ratio of the color filter specimen were measured using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the results are shown in Tables 8 to 10 below.
[0351] [Table 8]
[0352] [Table 9]
[0353] [Table 10]
[0354] It can be seen from Tables 8 to 10 that the color filter samples of Examples 1 to 10 have improved coloring strength and contrast ratio compared to the color filter samples of Comparative Examples 1 and 2. In other words, by using the dispersion assistant represented by Chemical Formula 1, a photosensitive resin composition can be provided that provides a color filter having high pigment dispersibility and dispersion stability, as well as excellent coloring strength and contrast ratio.
[0355] Although Examples 1 to 10 are shown here as representative examples, it is also possible to appropriately adjust each component within the scope of one embodiment and control dispersibility, dispersion stability, coloring strength, brightness ratio, etc. to the desired levels.
[0356] Although the above describes a preferred embodiment of the present invention, the present invention is not limited thereto, and can be embodied in various modified forms within the scope of the claims, the detailed description of the invention, and the accompanying drawings, which of course also fall within the scope of the present invention.
Claims
1. (A) a colorant, (B) photopolymerizable compound, (C) a photopolymerization initiator, (D) a binder resin, and (E) a solvent, The colorant is a photosensitive resin composition including a pigment, a dispersant, and a dispersion assistant represented by the following Chemical Formula 1: [Chemical formula 1] 【Chemistry 1】 In Formula 1, M is Cu or Zn; R 11 ~R 14 , R 21 ~R 24 , and R 31 ~R 34 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group; R 41 ~R 44 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group or aryloxy group; R 41 ~R 44 at least one of which is a C1 to C20 alkoxy group or aryloxy group substituted with a carboxy group.
2. R 11 ~R 14 The photosensitive resin composition according to claim 1 , wherein all of are hydrogen atoms or all of are halogen atoms.
3. R 21 ~R 24 The photosensitive resin composition according to claim 1, wherein any one of the above is a substituted or unsubstituted C1 to C20 alkyl group.
4. R 31 ~R 34 The photosensitive resin composition according to claim 1 , wherein all of are hydrogen atoms.
5. R 41 ~R 44 Any one of the above is a substituent represented by any one of the following chemical formulas 2 to 4: [Chemical formula 2] 【Chemistry 2】 In the above formula 2, R 51 ~R 55 are each independently a hydrogen atom, a halogen atom, a carboxy group, or a substituent represented by the following chemical formula 5, R 51 ~R 55 At least one of the groups is a carboxy group or a substituent represented by the following chemical formula 5: [Chemical formula 3] 【Chemistry 3】 [Chemical formula 4] 【Chemistry 4】 In Formulae 3 and 4, L 1 ~L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene; [Chemical formula 5] 【Chemistry 5】 In Formula 5, R 61 ~R 65 are each independently a hydrogen atom, a halogen atom, or a carboxy group; R 61 ~R 65 At least one of the groups is a carboxy group. The photosensitive resin composition according to claim 1 .
6. R 51 ~R 55 The photosensitive resin composition according to claim 5 , wherein two of the above are a carboxy group or a substituent represented by Chemical Formula 5.
7. R 61 ~R 65 The photosensitive resin composition according to claim 5 , wherein two of the groups are carboxy groups.
8. L 1 is a substituted or unsubstituted C1 to C10 alkylene.
9. L 2 and L 3 are each independently a substituted or unsubstituted C1 to C10 alkylene.
10. The dispersion aid represented by Formula 1 is represented by any one of Formulas 1-1 to 1-3 below: [Chemical formula 1-1] 【Chemistry 6】 [Chemical formula 1-2] 【Chemistry 7】 [Chemical formula 1-3] 【Chemistry 8】 In the formulas 1-1 to 1-3, M is Cu or Zn; 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 , R 42 and R 44 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, or a substituted or unsubstituted C1 to C20 alkyl group; R 51 ~R 55 are each independently a hydrogen atom, a halogen atom, a carboxy group, or a substituent represented by the following chemical formula 5, R 51 ~R 55 At least one of L is a carboxy group or a substituent represented by the following chemical formula 5: 1 ~L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene, A is a carboxyl group, [Chemical formula 5] 【Chemistry 9】 In Formula 5, R 61 ~R 65 are each independently a hydrogen atom, a halogen atom, or a carboxy group; R 61 ~R 65 The photosensitive resin composition according to claim 1 , wherein at least one of the groups is a carboxy group.
11. The photosensitive resin composition according to claim 1, wherein the dispersion aid represented by Chemical Formula 1 is selected from the group consisting of: [Chemical formula 1-1-1] 【Chemistry 10】 [Chemical formula 1-1-2] 【Chemistry 11】 [Chemical formula 1-1-3] 【Chemistry 12】 [Chemical formula 1-1-4] 【Chemistry 13】 [Chemical formula 1-1-5] 【Chemistry 14】 [Chemical formula 1-1-6] 【Chemistry 15】 [Chemical formula 1-1-7] 【Chemistry 16】 [Chemical formula 1-1-8] 【Chemistry 17】 [Chemical formula 1-1-9] 【Chemistry 18】 [Chemical formula 1-1-10] 【Chemistry 19】 [Chemical formula 1-2-1] 【Chemistry 20】 [Chemical formula 1-2-2] 【Chemistry 21】 [Chemical formula 1-2-3] 【Chemical 22】 [Chemical formula 1-2-4] 【Chemistry 23】 [Chemical formula 1-2-5] 【Chemistry 24】 [Chemical formula 1-2-6] 【Chemistry 25】 [Chemical formula 1-2-7] 【Chemistry 26】 [Chemical formula 1-2-8] 【Chemistry 27】 [Chemical formula 1-2-9] 【Chemistry 28】 [Chemical formula 1-2-10] 【Chemical 29】 [Chemical formula 1-3-1] 【Chemistry 30】 [Chemical formula 1-3-2] 【Chemistry 31】 [Chemical formula 1-3-3] 【Chemistry 32】 [Chemical formula 1-3-4] 【Chemical 33】 [Chemical formula 1-3-5] 【Chemical 34】 [Chemical formula 1-3-6] 【Chemistry 35】 [Chemical formula 1-3-7] 【Chemical 36】 [Chemical formula 1-3-8] 【Chemical 37】 [Chemical formula 1-3-9] 【Chemical 38】 [Chemical formula 1-3-10] 【Chemical 39】 [Chemical formula 1-4-1] 【Chemistry 40】 [Chemical formula 1-4-2] 【Chemistry 41】 [Chemical formula 1-4-3] 【Chemistry 42】 [Chemical formula 1-4-4] 【Chemistry 43】 [Chemical formula 1-4-5] 【Chemistry 44】 [Chemical formula 1-4-6] 【Chemistry 45】 [Chemical formula 1-4-7] 【Chemistry 46】 [Chemical formula 1-4-8] 【Chemistry 47】 [Chemical formula 1-4-9] 【Chemistry 48】 [Chemical formula 1-4-10] 【Chemistry 49】 [Chemical formula 1-5-1] 【Chemistry 50】 [Chemical formula 1-5-2] 【Chemistry 51】 [Chemical formula 1-5-3] 【Chemistry 52】 [Chemical formula 1-5-4] 【Chemistry 53】 [Chemical formula 1-5-5] 【Chemical Formula 54】 [Chemical formula 1-5-6] 【Chemistry 55】 [Chemical formula 1-5-7] 【Chemistry 56】 [Chemical formula 1-5-8] 【Chemistry 57】 [Chemical formula 1-5-9] 【Chemistry 58】 [Chemical formula 1-5-10] 【Chemistry 59】 。
12. 2. The photosensitive resin composition according to claim 1, wherein the dispersion assistant represented by Chemical Formula 1 has a maximum absorption wavelength of 450 nm to 495 nm.
13. 2. The photosensitive resin composition according to claim 1, wherein the dispersion assistant represented by Chemical Formula 1 is contained in an amount of 0.5% by weight to 6% by weight based on the total amount of the photosensitive resin composition.
14. 2. The photosensitive resin composition according to claim 1, wherein the weight ratio of the dispersion aid represented by Chemical Formula 1 to the pigment is 1:20 to 1:
70.
15. The photosensitive resin composition of claim 1 , wherein the pigment comprises a green pigment, a yellow pigment, or a combination thereof.
16. The photosensitive resin composition contains, relative to the total amount of the photosensitive resin composition, 0.5% by weight to 15% by weight of the colorant (A); 0.1% by weight to 10% by weight of the photopolymerizable compound (B); 0.1% by weight to 10% by weight of the (C) photopolymerization initiator, 0.5% by weight to 15% by weight of the binder resin (D), and Including the (E) residual amount of solvent The photosensitive resin composition according to claim 1 .
17. A photosensitive resin film produced by utilizing the photosensitive resin composition according to any one of claims 1 to 16.
18. The photosensitive resin composition of claim 1, which is a color negative photoresist.
19. A color filter comprising the photosensitive resin film according to claim 17.
20. 20. A display device comprising the color filter of claim 19.
Citation Information
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