KR101857147B1 - Novel compound,photosensitive resin composition comprising the same and color filter - Google Patents
Novel compound,photosensitive resin composition comprising the same and color filter Download PDFInfo
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- KR101857147B1 KR101857147B1 KR1020150149638A KR20150149638A KR101857147B1 KR 101857147 B1 KR101857147 B1 KR 101857147B1 KR 1020150149638 A KR1020150149638 A KR 1020150149638A KR 20150149638 A KR20150149638 A KR 20150149638A KR 101857147 B1 KR101857147 B1 KR 101857147B1
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- QVIAMKXOQGCYCV-UHFFFAOYSA-N CC(C)CCCN Chemical compound CC(C)CCCN QVIAMKXOQGCYCV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/061—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having halogen atoms linked directly to the Pc skeleton
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
Abstract
There is provided a compound represented by the following Chemical Formula 1, a photosensitive resin composition containing the same, and a color filter manufactured using the photosensitive resin composition.
[Chemical Formula 1]
(Wherein each substituent is as defined in the specification).
Description
The present invention relates to a novel compound, a photosensitive resin composition containing the same, and a color filter.
In a color filter made of a pigment type photosensitive resin composition, there is a limit of luminance and contrast ratio resulting from the pigment particle size. Further, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to meet such a demand, attempts have been made to fabricate a photosensitive resin composition in which a dye that does not form particles is introduced instead of a pigment, thereby realizing a color filter having improved color characteristics such as brightness and contrast ratio.
Therefore, it is necessary to study a compound suitable as a dye used in the production of a photosensitive resin composition.
One embodiment is to provide a novel compound.
Another embodiment is to provide a photosensitive resin composition comprising the above compound.
Another embodiment is to provide a color filter manufactured using the photosensitive resin composition.
An embodiment of the present invention provides a compound represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 to R 16 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, 2,
L 1 and L 2 each independently represent an oxygen atom, a sulfur atom or * -O (C = O) - *
At least one of R 1 to R 14 is represented by the following formula (2)
(2)
In Formula 2,
R 17 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
L 3 is an oxygen atom, a sulfur atom or * -O (C = O) - *.
And R 15 and R 16 are each independently any one of substituents represented by the following formulas (3-1) to (3-4).
[Formula 3-1]
[Formula 3-2]
[Formula 3-3]
[Chemical Formula 3-4]
In the above Formulas 3-1 to 3-4,
L 4 to L 7 are each independently a single bond or a substituted or unsubstituted C 1 to C 5 alkylene group.
At least one of R 1 to R 4 and at least one of R 7 to R 10 may be represented by the general formula (2).
At least one of R 1 to R 4 , at least one of R 7 to R 10 , and at least one of R 11 to R 14 may be represented by the formula (2).
At least one of R 1 to R 4 , at least one of R 7 to R 10 , and at least two of R 11 to R 14 may be represented by the formula (2).
At least two of R 1 to R 4 , at least two of R 7 to R 10 , and at least two of R 11 to R 14 may be represented by the formula (2).
R 17 may be any one of substituents represented by the following formulas (6-1) to (6-8).
[Formula 6-1]
[Formula 6-2]
[Formula 6-3]
[Formula 6-4]
[Formula 6-5]
[Formula 6-6]
[Formula 6-7]
[Formula 6-8]
The compound represented by Formula 1 may be any one selected from the group consisting of compounds represented by Chemical Formulas 7 to 15 below.
(7)
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
The compound may be a green dye.
The green dye may have a maximum transmittance in a wavelength range of 445 nm to 560 nm.
Another embodiment provides a photosensitive resin composition comprising the above compound.
Another embodiment provides a color filter manufactured using the photosensitive resin composition.
Other aspects of the present invention are included in the following detailed description.
The compound according to one embodiment has excellent green spectroscopic characteristics and a high molar extinction coefficient and is excellent in solubility in an organic solvent and can be used as a dye in the production of a photosensitive resin composition for a green color filter. Excellent brightness and contrast ratio can be obtained.
Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.
Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group NH 2, NH (R 200), or N (R 201) (R 202), wherein R 200, R 201 and R 202 are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, And a substituted or unsubstituted heterocyclic group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group.
Unless otherwise specified in the specification, "alkyl group" means C1 to C20 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C20 cycloalkyl group, specifically C3 Refers to a C1 to C20 alkoxy group, specifically, a C1 to C18 alkoxy group, and an " aryl group " means a C6 to C20 aryl group, specifically, a C6 to C20 aryl group, Refers to a C 2 to C 20 alkenyl group, specifically, a C 2 to C 18 alkenyl group, and the "alkylene group" refers to a C 1 to C 20 alkylene group, specifically, a C1 Refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.
(Meth) acrylate " refers to both " acrylic acid " and " methacrylic acid " It means both are possible.
As used herein, unless otherwise defined, " combination " means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.
Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.
In addition, unless otherwise defined herein, " * " means the same or different atom or moiety connected to the formula.
An embodiment provides a compound represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 to R 16 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, 2,
L 1 and L 2 each independently represent an oxygen atom, a sulfur atom or * -O (C = O) - *
At least one of R 1 to R 14 is represented by the following formula (2)
(2)
In Formula 2,
R 17 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
L 3 is an oxygen atom, a sulfur atom or * -O (C = O) - *.
The compound represented by Formula 1 has excellent green spectroscopic characteristics and a high molar extinction coefficient. Furthermore, the compound represented by the formula (1) may include a substituent represented by the formula (2) and / or the following formula (3-1) to (3-4) at a specific position, and thus may have a good solubility in an organic solvent.
In the general formula (1), R 1 to R 14 may not all be hydrogen atoms. For example, each of R 1 to R 16 may independently be a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituent represented by the general formula (2).
When any one of R 1 to R 14 is a hydrogen atom, as compared to the case wherein both R 1 to R 14 are not hydrogen atoms, it is to be the solubility and the luminance decreases.
The substituted C1 to C20 alkyl group may include an isopropyl group or a t-butyl group at the terminal. When the terminal of the alkyl group contains an isopropyl group or a t-butyl group, solubility in an organic solvent increases and brightness is excellent.
And R 15 and R 16 are each independently any one of substituents represented by the following formulas (3-1) to (3-4).
[Formula 3-1]
[Formula 3-2]
[Formula 3-3]
[Chemical Formula 3-4]
In the above Formulas 3-1 to 3-4,
L 4 to L 7 are each independently a single bond or a substituted or unsubstituted C 1 to C 5 alkylene group.
At least one of R 1 to R 4 and at least one of R 7 to R 10 may be represented by the general formula (2).
At least one of R 1 to R 4 , at least one of R 7 to R 10 , and at least one of R 11 to R 14 may be represented by the formula (2).
At least one of R 1 to R 4 , at least one of R 7 to R 10 , and at least two of R 11 to R 14 may be represented by the formula (2).
At least two of R 1 to R 4 , at least two of R 7 to R 10 , and at least two of R 11 to R 14 may be represented by the formula (2).
In Formula 1, R 1 , R 4 , R 7 , R 10 , R 11, and R 14 may not be simultaneously substituted or unsubstituted alkoxy groups. When R 1 , R 4 , R 7 , R 10 , R 11 and R 14 are simultaneously substituted or unsubstituted alkoxy groups in the general formula (1), the transmittance is lowered and the luminance is lowered.
R 17 may be any one of substituents represented by the following formulas (6-1) to (6-8).
[Formula 6-1]
[Formula 6-2]
[Formula 6-3]
[Formula 6-4]
[Formula 6-5]
[Formula 6-6]
[Formula 6-7]
[Formula 6-8]
The compound represented by Formula 1 may be any one selected from the group consisting of compounds represented by Chemical Formulas 7 to 15 below.
(7)
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
Since the compound according to one embodiment contains the substituent represented by the general formula (2) and / or the general formulas (3-1) to (3-4) at a specific position, it is possible to express a clearer color in a small amount, It is possible to manufacture a display device having excellent color characteristics such as brightness and contrast ratio. For example, the compound may be a colorant such as a dye, such as a green dye, e.g., a dye having a maximum transmittance in the wavelength range of 445 nm to 560 nm.
In general, dyes are the most expensive component of the components used in color filters. Therefore, in order to achieve a desired effect, for example, a high luminance and a high contrast ratio, it is necessary to use more expensive dye, so that the production cost has to be increased. However, when the compound according to one embodiment is used as a dye in a color filter, excellent color characteristics such as high luminance and high contrast ratio can be achieved even in a small amount, and production cost can be reduced.
According to another embodiment, there is provided a photosensitive resin composition comprising the compound according to one embodiment.
For example, the photosensitive resin composition may include a compound according to one embodiment, a pigment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
The compound according to one embodiment acts as a coloring agent such as a dye, for example, a green dye in the photosensitive resin composition, and can exhibit excellent color characteristics.
The compound according to one embodiment may be included in an amount of 1 wt% to 10 wt%, for example, 3 wt% to 7 wt% based on the total amount of the photosensitive resin composition. When the compound according to one embodiment is included in the above range, the color reproducibility and the contrast ratio are excellent .
The pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.
The pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.
The solid pigment may be present in the pigment dispersion in an amount ranging from 1% to 20%, such as 8% to 20%, such as 8% to 15%, such as 10% to 20% 15% by weight.
As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent and the like can be used. Specific examples of the dispersing agent include polyalkylene glycols and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, and alkylamines. These may be used singly or in combination of two or more.
DISPERBYK-161, DISPERBYK-160, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-160, DISPERBYK-130, DISPERBYK- -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400 and EFKA-450 of EFKA Chemical Co., Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711 and PB821.
The dispersing agent may be contained in an amount of 1 to 20% by weight based on the total amount of the pigment dispersion. When the dispersing agent is contained within the above range, the dispersibility of the photosensitive resin composition can be maintained because an appropriate viscosity can be maintained, so that optical, physical and chemical quality can be maintained when the product is applied.
As the solvent for forming the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether and the like can be used.
The pigment dispersion may be contained in an amount of 10% by weight to 20% by weight, for example, 12% by weight to 18% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion is contained within the above range, it is advantageous in securing a process margin and excellent color reproduction ratio and contrast ratio.
The alkali-soluble resin may be an acrylic resin.
The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and is a resin containing at least one acrylic repeating unit.
The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, 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.
The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl 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; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly or in combination of two or more.
Specific examples of the acrylic binder resin include (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate / 2- Acrylate copolymer, a (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, and the like, but not limited thereto, and they may be used alone or in combination have.
The weight-average molecular weight of the alkali-soluble resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 20,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the alkali-soluble resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, is suitable in viscosity, and has excellent adhesion with a substrate in the production of a color filter.
The acid value of the alkali-soluble resin may be from 15 mgKOH / g to 60 mgKOH / g, for example, from 20 mgKOH / g to 50 mgKOH / g. When the acid value of the alkali-soluble resin is within the above range, the resolution of the pixel pattern is excellent.
The alkali-soluble resin may be contained in an amount of 1% by weight to 30% by weight, for example, 1% by weight to 20% by weight based on the total amount of the photosensitive resin composition. When the alkali-soluble resin is contained within the above-mentioned range, the color filter is excellent in developability in the production of a color filter, and the cross-linkability is improved, whereby excellent surface smoothness can be obtained.
The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.
By having the ethylenically unsaturated double bond, the photopolymerizable compound can form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern formation step.
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, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, (Meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethacrylate (Meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate and the like.
Examples of commercially available products of photopolymerizable compounds are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ®, the same M-111 ®, the same M-114 ®; KAYARAD TC-110S ® and TC-120S ® from Nihon Kayaku Co., Ltd.; Osaka yukki the like Kagaku Kogyo (main)社of V-158 ®, V-2311 ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ®, copper or the like M-240 ®, the same M-6200 ®; KAYARAD HDDA ® , HX-220 ® and R-604 ® from Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of 社V-260 ®, V- 312 ®, V-335 HP ®. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ®, the same M-400 ®, the same M-405 ®, the same M-450 ®, Dong M -710 ® , copper M-8030 ® , copper M-8060 ® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ®, copper DPCA-20 ®, ® copper -30, -60 ® copper, copper ® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ®, copper ® -300, -360 ® copper, copper -GPT ®, copper -3PA ®, and the like copper -400 ®. These products may be used alone or in combination of two or more.
The photopolymerizable compound may be treated with an acid anhydride so as to give better developing properties.
The photopolymerizable compound may be contained in an amount of 1 wt% to 15 wt%, for example, 5 wt% to 10 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained within the above-mentioned range, the pattern forming process sufficiently cures upon exposure to light, which is excellent in reliability and developability in an alkaline developer.
The photopolymerization initiator is an initiator generally used in a photosensitive resin composition, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, a oxime compound, Can be used.
Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone, p-butyldichloroacetophenone, 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.
Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.
Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho- Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho-1-yl) (Trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like.
Examples of the oxime compounds include O-acyloxime compounds, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Etc. may be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- -Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O- Acetate and the like.
The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.
The photopolymerization initiator may be used in combination with a photosensitizer that generates a chemical reaction by absorbing light to be in an excited state and transferring its energy.
Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like .
The photopolymerization initiator may be included in an amount of 0.01 wt% to 10 wt%, for example, 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, the photopolymerization initiator is sufficiently cured upon exposure in the pattern formation step to obtain excellent reliability, and the pattern is excellent in heat resistance, light resistance, chemical resistance, resolution and adhesion, It is possible to prevent the transmittance from being lowered.
The solvent may be a compound, a pigment, an alkali-soluble resin, a photopolymerizable compound, and a compound having compatibility with a photopolymerization initiator but not reacting with the compound according to one embodiment.
Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl 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 methylethylcarbitol, diethylcarbitol, 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 methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; 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; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Ketone acid esters such as ethyl pyruvate, and the like, and also include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, And high boiling solvents such as ethyl acetate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.
Among them, glycol ethers such as ethylene glycol monoethyl ether and the like are preferably used in consideration of compatibility and reactivity; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.
The solvent may be contained in an amount of 30% by weight to 80% 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 an appropriate viscosity, and thus the processability in the production of the color filter is excellent.
The photosensitive resin composition according to another embodiment may further include an epoxy compound to improve adhesion with the substrate.
Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.
The epoxy compound may be contained in an amount of 0.01 to 20 parts by weight, for example, 0.1 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the above range, the adhesiveness and storage stability are excellent.
The photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group or an epoxy group in order to improve the adhesiveness to the substrate.
Examples of the silane coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatepropyltriethoxysilane,? -Glycidoxine (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc. These may be used alone or in combination of two or more.
The silane coupling agent may be contained in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is contained within the above range, the adhesion and storage stability are excellent.
The above-mentioned photosensitive resin composition may further contain a surfactant for improving coatability and preventing defect formation if necessary.
Examples of the surfactants include, BM Chemie BM-1000 ® of社, BM-1100 ®, and the like; Mechacup F 142D ® , copper F 172 ® , copper F 173 ® , copper F 183 ® and the like manufactured by Dainippon Ink & Chemicals Incorporated; Sumitomo M. (Note)社Pro rod FC-135 ®, the same FC-170C ®, copper FC-430 ®, the same FC-431 ®, and the like; Asahi Grass Co., Saffron S-112 ® of社, such S-113 ®, the same S-131 ®, the same S-141 ®, the same S-145 ®, and the like; Toray silicone (Note)社SH-28PA ®, copper -190 ®, may be used copper ® -193, fluorine-based surfactants and commercially available under the name, such as SZ-6032 ®, SF-8428 ®.
The surfactant may be used in an amount of 0.001 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the above range, uniformity of coating is ensured, no staining occurs, and wetting of the glass substrate is excellent.
The photosensitive resin composition may contain a certain amount of other additives such as an antioxidant and a stabilizer within a range that does not impair the physical properties.
According to another embodiment, there is provided a color filter manufactured using the photosensitive resin composition according to one embodiment.
The pattern forming process in the color filter is as follows.
Applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.
EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following Examples are only the preferred embodiments of the present invention, and the present invention is not limited to the following Examples.
(Synthesis of Compound)
Synthetic example 1: Synthesis of compound represented by formula (7)
(1) To a 100 mL flask was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.0 g), sodium sulfite (4.2 g), diethyl ether (25 mL) and distilled water (3.0 mL) Lt; / RTI > for 30 minutes. Thereafter, extraction with ether is carried out three times, and vacuum drying is performed to obtain the following precursor A.
[Precursor A]
(2) To a 100 mL flask is added the precursor A (2.4 g), 1-bromo-2-methyl propane (4.3 g), K 2 CO 3 (5.9 g) and DMF (20 mL) After completion of the reaction, the product is purified by column chromatography to obtain the following precursor B.
[Precursor B]
(3) A 100 mL flask was charged with 4,5-dichloro-3,6-diisobutoxyphthalonitrile (0.35 g), Zinc acetate (0.047 g), Isoamyl alcohol (2.5 g) and 1,8-Diazabicyclo [5.4.0] undec- ene (0.12 g) is added and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid is filtered and vacuum dried to obtain a compound represented by the following general formula (7).
(7)
MALDI-TOF MS, m / z Calcd . For 1431.80 m / z
Synthetic example 2: Synthesis of Compound Represented by Formula 8
4,5-dichloro-3,6-diisobutoxyphthalonitrile (0.11 g), 4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile (0.387 g), Zinc acetate (0.0592 g) Isoamyl alcohol (3.48 g) and 1,8-Diazabicyclo [5.4.0] undec-7-ene (0.147 g) are charged and refluxed with heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and vacuum dried to obtain a compound represented by the following general formula (8).
[Chemical Formula 8]
MALDI-TOF MS, m / z Calcd . For 1607.91 m / z
Synthetic example 3: Synthesis of Compound Represented by Formula 9
4,5-dichloro-3,6-diisobutoxyphthalonitrile (0.19 g), 4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile (0.223 g), Zinc acetate (0.051 g) Isoamyl alcohol (2.89 g) and 1,8-Diazabicyclo [5.4.0] undec-7-ene (0.127 g) are charged and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and vacuum-dried to obtain a compound represented by the following formula (9)
[Chemical Formula 9]
MALDI-TOF MS, m / z Calcd . For 1548.10 m / z
Synthetic example 4: Synthesis of Compound Represented by Formula 10
4,5-dichloro-3,6-diisobutoxyphthalonitrile (0.19 g), 3,4,6-Trichloro-5- (4-methyl-pentyloxy) phthalonitrile (0.185 g), Zinc acetate (0.051 g) Isoamyl alcohol (2.89 g) and 1,8-Diazabicyclo [5.4.0] undec-7-ene (0.127 g) are charged and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and dried in vacuo to obtain a compound represented by the following general formula (10).
[Chemical formula 10]
MALDI-TOF MS, m / z Calcd . For 1397.08 m / z
Synthetic example 5: Synthesis of Compound Represented by Formula 11
4,5-dichloro-3,6-diisobutoxyphthalonitrile (0.2 g), 4- (2-tert-Butyl-phenoxy) -3,5,6-trichloro-phthalonitrile (0.223 g), Zinc acetate ), Isoamyl alcohol (2.96 g) and 1,8-diazabicyclo [5.4.0] undec-7-ene (0.134 g) are charged and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and vacuum dried to obtain a compound represented by the following general formula (11).
(11)
MALDI-TOF MS, m / z Calcd . For 1508.19 m / z
Synthetic example 6: Synthesis of the compound represented by the formula (12)
4,5-Dichloro-3,6-bis- (naphthalen-2-ylsulfanyl) -phthalonitrile (0.165 g) and 4- (2-tert-Butyl-phenoxy) -3,5,6-trichloro-phthalonitrile (0.367 g), Zinc acetate (0.059 g), Isoamyl alcohol (3.34 g) and 1,8-Diazabicyclo [5.4.0] undec-7-ene (0.147 g). After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and vacuum dried to obtain a compound represented by the following general formula (12).
[Chemical Formula 12]
MALDI-TOF MS, m / z Calcd . For 1719.90 m / z
Synthetic example 7: Synthesis of Compound Represented by Formula 13
To a 25 mL flask was added 2,2-Dimethyl-propionic acid 2,3-dichloro-5,6-dicyano-4- (2,2-dimethyl-propionyloxy) -phenyl ester (0.278 g), 4- (Biphenyl- ) -3,5,6-trichloro-phthalonitrile (0.28 g), Zinc acetate (0.064 g), Isoamyl alcohol (3.57 g) and 1,8-Diazabicyclo [5.4.0] undec- And reflux while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and vacuum dried to obtain a compound represented by the following general formula (13).
[Chemical Formula 13]
MALDI-TOF MS, m / z Calcd . For 1684.10 m / z
Synthetic example 8: Synthesis of Compound Represented by Formula 14
3-methyl-butyric acid 2,3-dichloro-5,6-dicyano-4- (3-methyl-butyryloxy) -phenyl ester (0.221 g), 4- (Biphenyl- 5-trichloro-phthalonitrile (0.223 g), Zinc acetate (0.051 g), Isoamyl alcohol (2.89 g) and 1,8-Diazabicyclo [5.4.0] undec-7-ene Reflux. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and vacuum-dried to obtain a compound represented by the following general formula (14)
[Chemical Formula 14]
MALDI-TOF MS, m / z Calcd . For 1660.30 m / z
Synthetic example 9: Synthesis of compound represented by formula (15)
Benzo [d] thiazol-2-ylthio) -4,5-dichlorophthalonitrile (0.17 g), 4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile 0.387 g), Zinc acetate (0.0592 g), Isoamyl alcohol (3.48 g) and 1,8-Diazabicyclo [5.4.0] undec-7-ene (0.147 g) were charged and refluxed under heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to obtain a solid. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. The crystallized solid was filtered and vacuum dried to obtain a compound represented by the following formula (15).
[Chemical Formula 15]
MALDI-TOF MS, m / z Calcd . For 1922.81 m / z
compare Synthetic example 1: Synthesis of compound represented by formula (23)
3,4,6-Trichloro-5-phenoxyphthalonitrile (0.81 g), 1,8-Diazabicycloundec-7-ene (0.7 g) and 1-pentanol (15 mL) were placed in a 100 mL flask, , 6-Trichloro-5-phenoxy-phthalonitrile. After that, zinc acetate (0.115 g) was added and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, and hexane was added to crystallize it. At this time, the obtained solid was filtered and vacuum dried to obtain a compound represented by the following formula (23).
(23)
MALDI-TOF MS, m / z Calcd . For 1364.80 m / z
compare Synthetic example 2: Synthesis of Compound Represented by Formula 24
1,6-trichloro-5- (pentyloxy) phthalonitrile (1.0 g), 1,8-Diazabicycloundec-7-ene (0.96 g) and 1-pentanol (20 mL) were placed in a 100 mL flask, (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile. Then, zinc acetate (0.14 g) was added and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, and hexane was added to crystallize it. At this time, the obtained solid was filtered and vacuum dried to obtain a compound represented by the following chemical formula (24).
≪ EMI ID =
MALDI-TOF MS, m / z Calcd . For 1335.70 m / z
(Synthesis of photosensitive resin composition)
Example One
The photosensitive resin composition according to Example 1 was prepared by mixing the following components in the compositions shown in Table 1 below.
Specifically, a photopolymerization initiator was dissolved in a solvent, and the mixture was stirred at room temperature for 2 hours. Then, an alkali-soluble resin and a photopolymerizable compound were added thereto, followed by stirring at room temperature for 2 hours. Next, the obtained reaction product was added with the compound (compound represented by the formula (7)) and the pigment (in the form of a pigment dispersion) prepared in Synthesis Example 1 as a colorant and stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.
Molecular weight (Mw) = 22,000 g / mol
(A): methacrylic acid
(B): benzyl methacrylate
Example 2
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 2 (the compound of Formula 8) was used in place of the compound of Synthesis Example 1 (the compound of Formula 7).
Example 3
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 3 (the compound of Formula 9) was used in place of the compound of Synthesis Example 1 (the compound of Formula 7).
Example 4
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 4 (the compound of Formula 10) was used in place of the compound of Synthesis Example 1 (the compound of Formula 7).
Example 5
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 5 (the compound of Formula 11) was used instead of the compound of Synthesis Example 1 (the compound of Formula 7).
Example 6
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 6 (the compound of Formula 12) was used in place of the compound of Synthesis Example 1 (the compound of Formula 7).
Example 7
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 7 (the compound of Formula 13) was used in place of the compound of Synthesis Example 1 (the compound of Formula 7).
Example 8
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 8 (the compound of Formula 14) was used in place of the compound of Synthesis Example 1 (the compound of Formula 7).
Example 9
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 9 (the compound of Formula 15) was used instead of the compound of Synthesis Example 1 (the compound of Formula 7).
Comparative Example One
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Comparative Synthesis Example 1 (the compound of Formula 23) was used instead of the compound of Synthesis Example 1 (the compound of Formula 7).
Comparative Example 2
A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Comparative Synthesis Example 2 (the compound represented by the formula (24)) was used instead of the compound of Synthesis Example 1 (the compound represented by the formula (7)).
evaluation: Color coordinates , Luminance, and contrast ratio
The photosensitive resin composition prepared in Examples 1 to 9, Comparative Example 1 and Comparative Example 2 was coated on a 1 mm thick glass substrate having a thickness of 1 to 3 占 퐉, For 2 minutes to obtain a coating film. Subsequently, the coating film was exposed using a high-pressure mercury lamp having a main wavelength of 365 nm. Thereafter, the sheet was dried in a hot-air circulation type drying oven at 200 ° C for 5 minutes to obtain a photosensitive resin film. The color coordinates (x, y), luminance (Y), and contrast ratio were measured using a spectrophotometer (MCPD3000, Otsuka electronic Co.)
From Table 2, it can be seen that the photosensitive resin compositions of Examples 1 to 9 containing the compound according to one embodiment as a dye have better color characteristics than those of the photosensitive resin compositions of Comparative Examples 1 and 2, Can be confirmed.
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And it goes without saying that the invention belongs to the scope of the invention.
Claims (13)
[Chemical Formula 1]
In Formula 1,
R 1 to R 16 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, 2,
L 1 and L 2 each independently represent an oxygen atom, a sulfur atom or * -O (C = O) - *
At least one of R 1 to R 14 is represented by the following formula (2)
(2)
In Formula 2,
R 17 is any one of substituents represented by the following formulas (6-1) to (6-8)
[Formula 6-1]
[Formula 6-2]
[Formula 6-3]
[Formula 6-4]
[Formula 6-5]
[Formula 6-6]
[Formula 6-7]
[Formula 6-8]
L 3 is an oxygen atom, a sulfur atom or * -O (C = O) - *.
Wherein R 15 and R 16 are each independently any one of substituents represented by the following formulas (3-1) to (3-4):
[Formula 3-1]
[Formula 3-2]
[Formula 3-3]
[Chemical Formula 3-4]
In the above Formulas 3-1 to 3-4,
L 4 to L 7 are each independently a single bond or a substituted or unsubstituted C 1 to C 5 alkylene group.
At least one of R 1 to R 4 and at least one of R 7 to R 10 is represented by the formula (2).
At least one of R 1 to R 4 , at least one of R 7 to R 10 , and at least one of R 11 to R 14 is a compound represented by the general formula (2).
At least one of R 1 to R 4 , at least one of R 7 to R 10 , and at least two of R 11 to R 14 is represented by the formula (2).
At least two of R 1 to R 4 , at least two of R 7 to R 10 , and at least two of R 11 to R 14 are represented by the formula (2).
Wherein the compound represented by Formula 1 is any one selected from the group consisting of compounds represented by Chemical Formulas 7 to 15:
(7)
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
Wherein said compound is a green dye.
Wherein the green dye has a maximum transmittance in a wavelength range of 445 nm to 560 nm.
The photosensitive resin composition further comprises a pigment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
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