WO2021172787A1 - Core-shell compound, photosensitive resin composition comprising same, photosensitive resin film, color filter, and cmos image sensor - Google Patents

Abstract

Provided are a core-shell compound, a photosensitive resin composition comprising same, a photosensitive resin film prepared using the photosensitive resin composition, a color filter comprising the photosensitive resin film, and a CMOS image sensor comprising the color filter.

Description

Core-shell compound, photosensitive resin composition containing same, photosensitive resin film, color filter and CMOS image sensor

The present disclosure relates to a core-shell compound, a photosensitive resin composition including the same, a photosensitive resin film prepared using the photosensitive resin composition, a color filter including the photosensitive resin film, and a CMOS image sensor including the color filter.

With the recent development of the computer industry and the communication industry, the demand for image sensors with improved performance is increasing in various fields such as digital cameras, camcorders, PCS (Personal Communication System), game devices, security cameras, and medical micro cameras. Image sensors include a charge coupled device (CCD) and a CMOS image sensor, where the CMOS image sensor (hereinafter referred to as CIS) has a simple driving method and the signal processing circuit can be integrated into a single chip, resulting in miniaturization of the product. is possible In addition, it has the advantage of being easy to apply to products with limited battery capacity due to very low power consumption. The use of CIS is rapidly increasing as high resolution can be realized along with technology development.

Due to the CIS-related technology trends, the number of pixels and the size are decreasing for realizing high quality and miniaturization of devices. Among the photosensitive resin compositions for CIS having green, red, and blue color filters, in general, a green pixel has transmittance that must be satisfied at a specific wavelength or a specific wavelength range.

However, in the case of the green photosensitive resin composition for CIS developed so far, the transmittance at 540 nm and the transmittance at 600 nm to 640 nm were not simultaneously satisfied, so the color mixing problem was not improved. .

One embodiment is to provide a core-shell compound constituting a green pixel in a color filter for CIS.

Another embodiment is to provide a photosensitive resin composition comprising the compound.

Another embodiment is to provide a photosensitive resin film prepared using the photosensitive resin composition.

Another embodiment is to provide a color filter including the photosensitive resin film.

Another embodiment is to provide a CIS including the color filter.

One embodiment of the present invention provides a core-shell compound comprising a core represented by the following formula (1) and a shell surrounding the core and represented by the following formula (2).

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

R ¹ to R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group,

R ² and R ⁴ may each independently exist or fuse with each other to form a fused ring,

R ³ and R ⁵ are each independently present or may be fused with each other to form a fused ring,

L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

The core represented by Formula 1 may be represented by Formula 1-1 below.

[Formula 1-1]

In Formula 1-1,

R ¹ to R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group,

R ² and R ⁴ may each independently exist or fuse with each other to form a fused ring,

R ³ and R ⁵ may each independently exist or may be fused with each other to form a fused ring.

The core represented by Formula 1-1 may be represented by Formula 1-1-1 or Formula 1-1-2.

[Formula 1-1-1]

[Formula 1-1-2]

In Formulas 1-1-1 and 1-1-2,

R ¹ to R ³ and R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 an alkoxy group or a substituted or unsubstituted C6 to C20 aryl group.

Wherein R ¹ may be a substituted or unsubstituted C1 to C20 alkoxy group.

R ² may be a substituted or unsubstituted C3 to C20 cycloalkyl group, for example, a C3 to C20 cycloalkyl group substituted with an alkoxy group.

R ³ may be a substituted or unsubstituted C6 to C20 aryl group, for example, a C6 to C20 aryl group substituted with one or more alkyl groups.

R ⁶ may be a hydrogen atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C20 alkoxy group.

The core represented by Formula 1 may have a maximum absorption wavelength in the range of 610 nm to 640 nm.

The shell represented by Formula 2 may be represented by Formula 2-1 below.

[Formula 2-1]

The core-shell compound may be represented by any one of the following Chemical Formulas A to I.

[Formula A]

[Formula B]

[Formula C]

[Formula D]

[Formula E]

[Formula F]

[Formula G]

[Formula H]

[Formula I]

The core-shell compound may be a green dye.

Another embodiment provides a photosensitive resin composition including the core-shell compound.

The photosensitive resin composition may have a transmittance of 90% or more at 540 nm, and a transmittance of 10% or less at 600 nm to 640 nm.

The photosensitive resin composition may have a transmittance of 5% or less at 450 nm.

The photosensitive resin composition may be for a CMOS image sensor.

Another embodiment provides a photosensitive resin film prepared using the photosensitive resin composition.

Another embodiment provides a color filter including the photosensitive resin film.

Another embodiment provides a CMOS image sensor including the color filter.

The specific details of other aspects of the invention are included in the detailed description below.

The photosensitive resin composition including the core-shell compound according to the exemplary embodiment may form a green pixel, thereby providing a color filter for a CMOS image sensor having high transmittance.

1 is a graph of absorbance according to wavelength of green dyes (Synthesis Example 1 and Comparative Synthesis Example 1) used in Examples 1 and 2;

2 is a graph of transmittance according to wavelength of the photosensitive resin composition according to Example 1, Comparative Example 1, and Comparative Example 2;

Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereto, and the present invention is only defined by the scope of the claims to be described later.

Unless otherwise specified herein, "substituted" to "substituted" means that at least one hydrogen atom in the functional group of the present invention is a halogen atom (F, Br, Cl or I), a hydroxyl 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 from each other, and each independently a C1 to C10 alkyl group), an amidino group, A hydrazine group, a hydrazone group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group, and It means substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group.

Unless otherwise specified herein, "alkyl group" means a C1 to C20 alkyl group, specifically means a C1 to C15 alkyl group, and "cycloalkyl group" means a C3 to C20 cycloalkyl group, specifically C3 to C18 cycloalkyl group, "alkoxy group" means a C1 to C20 alkoxy group, specifically means a C1 to C18 alkoxy group, "aryl group" means a C6 to C20 aryl group, specifically C6 to refers to a C18 aryl group, “alkenyl group” refers to a C2 to C20 alkenyl group, specifically refers to a C2 to C18 alkenyl group, and “alkylene group” refers to a C1 to C20 alkylene group, specifically C1 to C18 alkylene group, "arylene group" means C6 to C20 arylene group, specifically, C6 to C16 arylene group.

Unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" is "acrylic acid" and "methacrylic acid" It means both are possible.

Unless otherwise defined herein, "combination" means mixing or copolymerization. In addition, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymerization or random copolymerization.

Unless otherwise defined in the chemical formulas in the present specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded to the position.

In addition, unless otherwise defined in the present specification, "*" means a moiety connected to the same or different atoms or chemical formulas.

One embodiment provides a core-shell compound comprising a core represented by the following formula (1) and a shell surrounding the core and represented by the following formula (2).

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

R ¹ to R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group,

R ² and R ⁴ may each independently exist or fuse with each other to form a fused ring,

R ³ and R ⁵ are each independently present or may be fused with each other to form a fused ring,

L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

When the light transmittance of 10% or less is satisfied at any wavelength within the range of 600 nm to 640 nm in the transmission spectrum of the green pixel, crosstalk can be improved and a high-transmission photosensitive resin composition for CIS can be implemented, and thus high-quality images can be obtained. can be implemented

Accordingly, efforts are being made to realize a high-transmission photosensitive resin composition for CIS by using a squarylium-based dye that does not have different absorption in the short wavelength region and can selectively absorb the desired wavelength region by minimizing the absorption reference half maximum width. A satisfactory level of composition has not been implemented. Accordingly, the inventors of the present invention prepared a photosensitive resin composition for CIS using an asymmetric squarylium-based dye having a specific structure as described above and measured the transmission spectrum. It was confirmed that the condition of the light transmittance of 90% or more at any wavelength within the range, for example, the light transmittance at a wavelength of 540 nm and the condition of the light transmittance of 10% or less at any wavelength within the wavelength range of 600 nm to 640 nm) was satisfied.

Furthermore, when the asymmetric squarylium-based compound having a specific structure as described above has a maximum absorption wavelength at 610 nm to 640 nm, the transmittance in the long wavelength region (600 nm to 640 nm) is further improved (10% or less) It was confirmed.

For example, the core represented by Formula 1 may be represented by Formula 1-1 below.

[Formula 1-1]

In Formula 1-1,

R ¹ to R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group,

R ² and R ⁴ may each independently exist or fuse with each other to form a fused ring,

R ³ and R ⁵ may each independently exist or may be fused with each other to form a fused ring.

For example, the core represented by Formula 1-1 may be represented by Formula 1-1-1 or Formula 1-1-2.

[Formula 1-1-1]

[Formula 1-1-2]

In Formulas 1-1-1 and 1-1-2,

R ¹ to R ³ and R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 an alkoxy group or a substituted or unsubstituted C6 to C20 aryl group.

For example, R ¹ may be a substituted or unsubstituted C1 to C20 alkoxy group.

For example, R ² may be a substituted or unsubstituted C3 to C20 cycloalkyl group, for example, a C3 to C20 cycloalkyl group substituted with an alkoxy group.

For example, R ³ may be a substituted or unsubstituted C6 to C20 aryl group, for example, a C6 to C20 aryl group substituted with one or more alkyl groups.

For example, R ⁶ may be a hydrogen atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C20 alkoxy group.

For example, the core represented by Formula 1 may have a maximum absorption wavelength in the range of 610 nm to 640 nm. Even if it is a dye compound having excellent solubility in organic solvents of 10% or more, if it does not have a maximum absorption wavelength at 610 nm to 640 nm, it may be unsuitable for use as a green photosensitive resin composition for high transmission type CIS.

The shell represented by Formula 2 may be represented by Formula 2-1 below.

[Formula 2-1]

For example, the core-shell compound may be represented by any one of the following Chemical Formulas A to I, but is not necessarily limited thereto.

[Formula A]

[Formula B]

[Formula C]

[Formula D]

[Formula E]

[Formula F]

[Formula G]

[Formula H]

[Formula I]

For example, the core-shell compound may be a green dye.

According to another embodiment, there is provided a photosensitive resin composition including the core-shell compound according to the embodiment.

For example, the photosensitive resin composition may have a transmittance of 90% or more at 540 nm, a transmittance of 10% or less at 600 nm to 640 nm, and a transmittance of 5% or less at 450 nm, a green color for high transmission type CIS It may be suitable for filter implementation. That is, the photosensitive resin composition may be for a high-transmission CMOS image sensor.

The photosensitive resin composition may further include the core-shell compound, a binder resin, a photopolymerizable compound, a photoinitiator, and a solvent.

The core-shell compound according to an 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 core-shell compound according to an embodiment is included in the above range, color gamut and contrast ratio are excellent .

The photosensitive resin composition may further include a pigment, such as a yellow pigment, a green pigment, or a combination thereof.

The yellow pigment has C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150 etc. are mentioned, These can be used individually or in mixture of 2 or more types.

The green pigment has C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59 etc. are mentioned, These can be used individually or in mixture of 2 or more types.

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 dispersing agent for uniformly dispersing the pigment in the solvent.

The solid content of the pigment is 1% to 20% by weight, such as 8% to 20% by weight, such as 8% to 15% by weight, such as 10% to 20% by weight, such as 10% to 20% by weight, based on the total amount of the pigment dispersion. It may be included in 15% by weight.

As the dispersant, a nonionic dispersant, an anionic dispersant, a cationic dispersant, and the like may be used. Specific examples of the dispersant include polyalkylene glycol and its esters, polyoxyalkylene, polyalcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more.

Examples of commercially available products of the dispersant include BYK's DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, etc.; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc. from EFKA Chemicals; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000, etc. from Zeneka; or Ajinomoto's PB711 and PB821.

The dispersant may be included in an amount of 1 wt% to 20 wt% based on the total amount of the pigment dispersion. When the dispersant is included within the above range, it is possible to maintain an appropriate viscosity and thus the photosensitive resin composition has excellent dispersibility, thereby maintaining optical, physical and chemical quality when applying the product.

As a 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 may be used.

The pigment dispersion may be included in an amount of 10 wt% to 20 wt%, for example 12 wt% to 18 wt%, based on the total amount of the photosensitive resin composition. When the pigment dispersion is included within the above range, it is advantageous to secure a process margin, and the color reproducibility and contrast ratio are excellent.

The binder resin may be an acrylic binder resin.

The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin including one or more acrylic repeating units.

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 wt% to 50 wt%, for example 10 wt% to 40 wt%, based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene or vinylbenzylmethyl ether; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (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 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 a vinyl benzoate; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; Vinyl cyanide compounds, such as (meth)acrylonitrile; unsaturated amide compounds such as (meth)acrylamide; and the like, and these may be used alone 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-hydroxyethyl meth acrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, and the like, but are not limited thereto, and these may be used alone or in combination of two or more. have.

The weight average molecular weight of the binder resin may be 3,000 g/mol to 150,000 g/mol, such as 5,000 g/mol to 50,000 g/mol, such as 20,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the binder resin is within the above range, physical and chemical properties of the photosensitive resin composition are excellent, the viscosity is appropriate, and the adhesion to the substrate is excellent in manufacturing the color filter.

The acid value of the binder resin may be 15 mgKOH/g to 60 mgKOH/g, for example, 20 mgKOH/g to 50 mgKOH/g　. When the acid value of the binder resin is within the above range, the resolution of the pixel pattern is excellent.

The binder resin may be included in an amount of 1 wt% to 30 wt%, for example 1 wt% to 20 wt%, based on the total amount of the photosensitive resin composition. When the binder resin is included within the above range, excellent developability and improved crosslinking properties can be obtained when manufacturing a color filter, thereby obtaining excellent surface smoothness.

The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

Since the photopolymerizable compound has the ethylenically unsaturated double bond, it is possible to form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure to light in the pattern forming process.

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, 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, trimethylol propane tri ( and meth)acrylate, tris(meth)acryloyloxyethyl phosphate, and novolac epoxy (meth)acrylate.

Examples of commercially available products of the photopolymerizable compound are as follows. Examples of the monofunctional ester of (meth)acrylic acid include Aronix M-101 ^® , M-111 ^® , M-114 ^® by Toagosei Chemical Co., Ltd.; Nihon Kayaku Co., Ltd.'s KAYARAD TC-110S ^® , Copper TC-120S ^®, etc.; ^{V-158 ®} and V-2311 ^{® of} Osaka Yuki Chemical High School Co., Ltd. are mentioned. Examples of the bifunctional ester of (meth)acrylic acid, Toagosei Chemical Co., Ltd. Aronix M-210 ^® , copper M-240 ^® , copper M-6200 ^® and the like; Nihon Kayaku Co., Ltd.'s KAYARAD HDDA ^® , Copper HX-220 ^® , Copper R-604 ^®, etc.; ^{and V-260 ®} , V-312 ^® , V-335 HP ^{® of} Osaka Yuki Chemical High School Co., Ltd. and the like. Examples of the trifunctional ester of (meth)acrylic acid, Toagosei Chemical Co., Ltd. Aronix M-309 ^® , Copper M-400 ^® , Copper M-405 ^® , Copper M-450 ^® , Copper M -710 ^® , copper M-8030 ^® , copper M-8060 ^® etc; Nihon Kayaku Co., Ltd.'s KAYARAD TMPTA ^® , Copper DPCA-20 ^® , Copper-30 ^® , Copper-60 ^® , Copper-120 ^® etc.; ^{V-295 ®} , Dong-300 ^® , Dong-360 ^® , Dong-GPT ^® , Dong-3PA ^® , Dong-400 ^® etc. from Osaka Yuki Kayaku High School Co., Ltd. are mentioned. These products may be used alone or in combination of two or more.

The photopolymerizable compound may be used after treatment with an acid anhydride in order to provide better developability.

The photopolymerizable compound may be included in an amount of 1 wt% to 15 wt%, for example 5 wt% to 10 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the above range, curing occurs sufficiently during exposure in the pattern forming process to provide excellent reliability and excellent developability in an alkaline developer.

The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, 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

Examples of the acetophenone-based compound include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. are mentioned.

Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4 '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc. are mentioned.

Examples of the thioxanthone-based compound include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone etc. are mentioned.

Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyldimethyl ketal.

Examples of the triazine-based compound 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-(naphtho-1-yl)-4, 6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-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, etc. are mentioned.

Examples of the oxime-based compound include an O-acyloxime-based compound, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, and 1-(o-acetyloxime). )-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one etc. can be used. Specific examples of the O-acyloxime compound include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane- 1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione2 -oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime-O- Acetate etc. are mentioned.

As the photopolymerization initiator, a carbazole-based compound, a diketone-based compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, a biimidazole-based compound, or a fluorene-based compound may be used in addition to the above compound.

The photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light to enter an excited state and then transferring the energy.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like. can be heard

The photopolymerization initiator may be included in an amount of 0.01 wt% to 10 wt%, for example 0.1 wt% to 5 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, curing occurs sufficiently during exposure in the pattern formation process to obtain excellent reliability, and the pattern has excellent heat resistance, light resistance and chemical resistance, and also has excellent resolution and adhesion. A decrease in transmittance can be prevented.

As the solvent, materials having compatibility with but not reacting with the core-shell compound, pigment, binder resin, photopolymerizable compound, and photoinitiator according to the embodiment may be used.

Examples of the solvent include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl 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 methylethyl 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; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-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; Alkoxy acetate alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxypropionic acid alkyl esters, such as 3-oxy methyl propionate and 3-oxy ethyl propionate; 3-alkoxy propionic acid alkyl esters, such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate, and 3-ethoxy methyl propionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; 2-alkoxy propionic acid alkyl esters, such as 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-ethoxy ethyl propionate, and 2-ethoxy methyl propionate; 2-oxy-2-methyl propionic acid esters such as 2-oxy-2-methyl methyl propionate and 2-oxy-2-methyl ethyl propionate; 2-methoxy-2-methyl methyl propionate; 2-ethoxy-2- monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl propionate alkyls such as ethyl methyl propionate; esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, ethyl hydroxyacetate, and 2-hydroxy-3-methyl methyl butanoate; Ketonic acid esters such as ethyl pyruvate, and the like, and N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, and 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, benzoic acid and high boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among these, in consideration of compatibility and reactivity, glycol ethers, such as ethylene glycol monoethyl ether, are preferable; 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; and/or ketones such as cyclohexanone may be used.

The solvent may be included in a balance, for example, 30 wt% to 80 wt%, based on the total amount of the photosensitive resin composition. When the solvent is included within the above range, since the photosensitive resin composition has an appropriate viscosity, processability in manufacturing the color filter is excellent.

The photosensitive resin composition according to another embodiment may further include an epoxy compound to improve adhesion with a substrate.

Examples of the epoxy compound include a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol A-type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The epoxy compound may be included in an amount of 0.01 parts by weight to 20 parts by weight, for example, 0.1 parts by weight to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is included within the above range, adhesion and storage properties are excellent.

In addition, 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, and an epoxy group in order to improve adhesion to the substrate.

Examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ isocyanate propyl triethoxysilane, γ glycidoxy propyl tri Methoxysilane, β-epoxycyclohexyl)ethyltrimethoxysilane, etc. are mentioned, and these can be used individually or in mixture of 2 or more types.

The silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is included within the above range, adhesion and storage properties are excellent.

In addition, the photosensitive resin composition may further include a surfactant to improve coating properties and prevent defect formation, if necessary.

Examples of the surfactant include BM-1000 ^® , BM-1100 ^® and the like by BM Chemie; ^{Mecha Pack F 142D ®} , F 172 ^® , F 173 ^® , F 183 ^® etc. manufactured by Dai Nippon Inky Chemical Co., Ltd.; Sumitomo 3M Co., Ltd.'s Prorad FC-135 ^® , FC-170C ^® , FC-430 ^® , FC-431 ^®, etc.; Asahi Grass Co., Ltd.'s Saffron S-112 ^® , Copper S-113 ^® , Copper S-131 ^® , Copper S-141 ^® , Copper S-145 ^®, etc.; 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 parts by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included within the above range, coating uniformity is secured, staining does not occur, and wettability to a glass substrate is excellent.

In addition, a certain amount of other additives such as antioxidants and stabilizers may be added to the photosensitive resin composition within a range that does not impair physical properties.

According to another embodiment, there is provided a color filter manufactured using the photosensitive resin composition according to the embodiment.

The pattern forming process in the color filter is as follows.

applying the photosensitive resin composition onto 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 prepare a photosensitive resin film; and heat-treating the photosensitive resin film. Since the process conditions and the like are well known in the art, detailed descriptions thereof will be omitted herein.

Another embodiment provides a CMOS image sensor including the color filter.

Hereinafter, the present invention will be described in more detail with reference to examples, but the following examples are only preferred examples of the present invention, and the present invention is not limited to the following examples.

(synthesis of compounds)

Synthesis Example 1: Synthesis of a compound represented by Formula A

3-{4-[(2,4-Dimethyl-phenyl)-(2-methoxy-cyclohexyl)-amino]-phenyl}-4-hydroxy-cyclobut-3-ene-1,2-dione (60 mmol), 1-[4-(2-Ethyl-hexyloxy)-phenyl]-1H-indole (60 mmol) was added to toluene (200 mL) and butanol (200 mL), refluxed, and the resulting water was removed with a Dean-stark distillation apparatus. do. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (A).

[Formula A]

Maldi-tof MS: 1243.5 m/z

Synthesis Example 2: Synthesis of a compound represented by Formula B

3-{4-[(2,4-Dimethyl-phenyl)-(2-methoxy-cyclohexyl)-amino]-phenyl}-4-hydroxy-cyclobut-3-ene-1,2-dione (60 mmol), 1-[4-(2-Ethyl-hexyloxy)-phenyl]-6-methoxy-1H-indole (60 mmol) was added to toluene (200 mL) and butanol (200 mL), refluxed, and the resulting water was dean-stark removed by distillation. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (B).

[Formula B]

Maldi-tof MS: 1273.58 m/z

Synthesis Example 3: Synthesis of a compound represented by Formula C

3-{4-[(2,4-Dimethyl-phenyl)-(2-methoxy-cyclohexyl)-amino]-phenyl}-4-hydroxy-cyclobut-3-ene-1,2-dione (60 mmol), 1-[4-(2-Ethyl-hexyloxy)-phenyl]-1H-indole-6-carbonitrile (60 mmol) was added to toluene (200 mL) and butanol (200 mL), refluxed, and the resulting water was dean-stark removed by distillation. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (C).

[Formula C]

Maldi-tof MS: 1268.73 m/z

Synthesis Example 4: Synthesis of the compound represented by Formula D

3-{4-[(2,4-Dimethyl-phenyl)-(2-methoxy-cyclohexyl)-amino]-phenyl}-4-hydroxy-cyclobut-3-ene-1,2-dione (60 mmol), 1-[4-(2-Ethyl-hexyloxy)-phenyl]-6-fluoro-1H-indole (60 mmol) was added to toluene (200 mL) and butanol (200 mL), refluxed, and the resulting water was dean-stark removed by distillation. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (D).

[Formula D]

Maldi-tof MS: 1261.73 m/z

Synthesis Example 5: Synthesis of the compound represented by Formula E

3-[4-((2,4-Dimethyl-phenyl)-{2-[2-(2-methoxy-ethoxy)-ethoxy]-cyclohexyl}-amino)-phenyl]-4-hydroxy-cyclobut-3- ene-1,2-dione (60 mmol), 6-Fluoro-1-(4-methoxy-phenyl)-1H-indole (60 mmol) was added to toluene (200 mL) and butanol (200 mL) and refluxed to produce The water is removed with a Dean-stark distillation apparatus. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (E).

[Formula E]

Maldi-tof MS: 1251.75 m/z

Synthesis Example 6: Synthesis of a compound represented by Formula F

3-Hydroxy-4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-cyclobut-3-ene-1,2-dione ( 60 mmol), 6-Fluoro-1-(4-methoxy-phenyl)-1H-indole (60 mmol) was added to toluene (200 mL) and butanol (200 mL) and refluxed, and the resulting water was distilled in a Dean-stark distillation apparatus. removed with After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (F).

[Formula F]

Maldi-tof MS: 1027.49 m/z

Synthesis Example 7: Synthesis of a compound represented by Formula G

3-[4-((2,4-Dimethyl-phenyl)-{2-[2-(2-methoxy-ethoxy)-ethoxy]-cyclohexyl}-amino)-phenyl]-4-hydroxy-cyclobut-3- ene-1,2-dione (60 mmol), 4-Indol-1-yl-benzonitrile (60 mmol) was put in toluene (200 mL) and butanol (200 mL) and refluxed, and the resulting water was purified by a Dean-stark distillation apparatus. removed with After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (G).

[Formula G]

Maldi-tof MS: 1242.54 m/z

Synthesis Example 8: Synthesis of a compound represented by Formula H

3-[4-((2,4-Dimethyl-phenyl)-{2-[2-(2-methoxy-ethoxy)-ethoxy]-cyclohexyl}-amino)-phenyl]-4-hydroxy-cyclobut-3- ene-1,2-dione (60 mmol), 1-(4-Fluoro-phenyl)-1H-indole (60 mmol) was added to toluene (200 mL) and butanol (200 mL) and refluxed to dean the resulting water. -Stark is removed by distillation apparatus. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (H).

[Formula H]

Maldi-tof MS: 1221.67 m/z

Synthesis Example 9: Synthesis of the compound represented by Formula I

3-[4-((2,4-Dimethyl-phenyl)-{2-[2-(2-methoxy-ethoxy)-ethoxy]-cyclohexyl}-amino)-phenyl]-4-hydroxy-cyclobut-3- Add ene-1,2-dione (60 mmol), 1-[4-(2-Ethyl-hexyloxy)-phenyl]-1H-indole (60 mmol) to toluene (200 mL) and butanol (200 mL) and reflux The resulting water is removed with a Dean-stark distillation apparatus. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula (I).

[Formula I]

Maldi-tof MS: 1331.81 m/z

Comparative Synthesis Example 1: Synthesis of a compound represented by Formula C-1

Propionic acid 2-{(2-cyano-ethyl)-[4-(2-hydroxy-3,4-dioxo-cyclobut-1-enyl)-phenyl]-amino}-ethyl ester (60 mmol), 1-( 2-Ethyl-hexyl)-1H-indole (60 mmol) is added to toluene (200 mL) and butanol (200 mL), refluxed, and the resulting water is removed using a Dean-stark distillation apparatus. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squarylium compound. After dissolving this compound (5 mmol) in 600 mL of chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform, and then added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following Chemical Formula C-1.

[Formula C-1]

Maldi-tof MS: 1088.48 m/z

Evaluation 1: Measurement of maximum absorption wavelength

The compound according to Synthesis Example 1 and Synthesis Example 9 to Comparative Synthesis Example 1 was prepared at a concentration of 0.001wt% using a diluting solvent (ANONE), according to Synthesis Example 1 and Synthesis Example 9 to Comparative Synthesis Example 1. Absorption spectra were obtained for each of the core-shell compounds, and the results are shown in Table 1 and FIG. 1 below. (UV-1800, SHIMADZU)

(Unit: nm)

	maximum absorption wavelength
Synthesis Example 1	620
Synthesis Example 2	625
Synthesis Example 3	618
Synthesis Example 4	619
Synthesis Example 5	620
Synthesis Example 6	625
Synthesis Example 7	621
Synthesis Example 8	617
Synthesis Example 9	620
Comparative Synthesis Example 1	596

Evaluation 2: Determination of solubility

To 0.5 g of the compound according to Synthesis Examples 1 to 9 and Comparative Synthesis Example 1, a diluting solvent (PGMEA) was respectively added, and the solution was mixed with a mixing rotor (iuchi Co., Ltd., MIXROTAR VMR-5) at 25°C rpm 1 After stirring for an hour, the results of confirming the solubility of each compound are shown in Table 2 below.

Solubility evaluation criteria

Compound (solute) dissolved at least 10% by weight based on the total amount of diluent: ○

Less than 10% by weight of the compound (solute) dissolved with respect to the total amount of the diluent: X

	Solubility
Synthesis Example 1	○
Synthesis Example 2	○
Synthesis Example 3	○
Synthesis Example 4	○
Synthesis Example 5	○
Synthesis Example 6	○
Synthesis Example 7	○
Synthesis Example 8	○
Synthesis Example 9	○
Comparative Synthesis Example 1	○

From Table 2, it can be seen that both the compounds of Synthesis Examples 1 to 9 and the compounds of Comparative Synthesis Example 1 have excellent solubility.

(Synthesis of photosensitive resin composition)

Example 1

A photosensitive resin composition according to Example 1 was prepared by mixing the components mentioned below in the composition shown in Table 3 below.

Specifically, a photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 2 hours, and then a binder resin and a photopolymerizable compound were added thereto and stirred at room temperature for 2 hours. Then, the compound prepared in Synthesis Example 1 (compound represented by Formula A) and pigment (in the form of a pigment dispersion) as a colorant were added to the obtained reactant and stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

(Unit: % by weight)

Ingredients			content
coloring agent	dyes	Compound of Synthesis Example 1	5.0
	pigment dispersion	C.I. green pigment 58	15.0
binder resin		(A)/(B)=15/85(w/w), Molecular Weight (Mw) = 22,000 g/mol (A): methacrylic acid (B): benzyl methacrylate	3.5
photopolymerizable compound		Dipentaerythritol Hexaacrylate (DPHA)	8.0
photopolymerization initiator		1,2-octanedione	1.0
		2-Dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one	0.5
menstruum		cyclohexanone	37.0
		PGMEA (Propylene Glycol Monomethyl Ether Acetate)	30.0
Total			100.00

Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 2 (compound represented by Formula B) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 3 (compound represented by Formula C) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 4 (compound represented by Formula D) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Example 5

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 5 (compound represented by Formula E) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Example 6

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 6 (compound represented by Formula F) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Example 7

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 7 (compound represented by Formula G) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Example 8

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 8 (compound represented by Formula H) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Example 9

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 9 (compound represented by Formula I) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A).

Comparative Example 1

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 1 (compound represented by Formula A) was not used as a colorant.

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 1 (compound represented by Formula C-1) was used instead of the compound of Synthesis Example 1 (compound represented by Formula A) .

Evaluation 3: Measurement of color coordinates, luminance and contrast ratio

The photosensitive resin compositions prepared in Examples 1 to 9, Comparative Examples 1 and 2 were coated on a glass substrate having a thickness of 1 mm to a thickness of 1 μm to 3 μm on a degreasing-washed glass substrate, and a hot plate at 90° C. A coating film was obtained by drying on the bed for 2 minutes. Subsequently, the coating film was exposed using a high-pressure mercury lamp having a dominant wavelength of 365 nm. After that, the sample was obtained by drying for 5 minutes in a hot air circulation drying furnace at 200°C. The transmittance of the sample was measured at wavelengths of 450 nm, 540 nm and 620 nm using a spectrophotometer (MCPD3000, Otsuka electronic), and the results are shown in Table 4 and FIG. 2 below.

(unit: %)

	Transmittance at 450 nm	Transmittance at 540 nm	Transmittance at 620 nm
Example 1	4.1	91.6	5.7
Example 2	4.1	93.8	4.3
Example 3	4.1	90.7	6.2
Example 4	4.1	91.2	6.0
Example 5	4.1	91.6	5.7
Example 6	4.1	93.8	4.3
Example 7	4.1	92.1	5.4
Example 8	4.1	90.3	6.5
Example 9	4.1	91.6	5.7
Comparative Example 1	4.1	95.3	34.5
Comparative Example 2	4.1	81.0	12.4

From Table 4, the photosensitive resin composition of Examples 1 to 9 including the core-shell compound according to an embodiment as a dye compared with the photosensitive resin composition of Comparative Examples 1 and 2 not including the compound Thus, the transmittance at 450 nm is 5% or less, the transmittance at 540 nm is 90% or more, and the transmittance is 10% or less at 620 nm. You can check that it is possible. (In Comparative Example 2, the transmittance at 540 nm is 90% or less, which is a transmittance that is not applicable to a general green photosensitive resin composition for CIS. In addition, the transmittance at 450 nm is 5% or less, and the transmittance at 540 nm is 90% or more When the condition is satisfied and the transmittance at 620 nm is as low as 10% or less, color mixing is possible, and ultimately, it is possible to manufacture a high transmittance type CIS green color filter.)

Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the appended claims, the detailed description of the invention, and the accompanying drawings. It goes without saying that it falls within the scope of the invention.

Claims (20)

1. A core represented by the following formula (1) and

   A core-shell compound surrounding the core and consisting of a shell represented by the following formula (2):

   [Formula 1]

   

   [Formula 2]

   

   In Formula 1 and Formula 2,

   R ¹ to R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group,

   R ² and R ⁴ may each independently exist or fuse with each other to form a fused ring,

   R ³ and R ⁵ are each independently present or may be fused with each other to form a fused ring,

   L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.
2. According to claim 1,

   The core represented by Formula 1 is a compound represented by Formula 1-1:

   [Formula 1-1]

   

   In Formula 1-1,

   R ¹ to R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group,

   R ² and R ⁴ may each independently exist or fuse with each other to form a fused ring,

   R ³ and R ⁵ may each independently exist or may be fused with each other to form a fused ring.
3. 3. The method of claim 2,

   The core represented by Formula 1-1 is a compound represented by Formula 1-1-1 or Formula 1-1-2:

   [Formula 1-1-1]

   

   [Formula 1-1-2]

   

   In Formulas 1-1-1 and 1-1-2,

   R ¹ to R ³ and R ⁶ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 an alkoxy group or a substituted or unsubstituted C6 to C20 aryl group.
4. According to claim 1,

   wherein R ¹ is a substituted or unsubstituted C1 to C20 alkoxy group.
5. 5. The method of claim 4,

   wherein R ² is a substituted or unsubstituted C3 to C20 cycloalkyl group.
6. 6. The method of claim 5,

   wherein R ² is a C3 to C20 cycloalkyl group substituted with an alkoxy group.
7. 5. The method of claim 4,

   wherein R ³ is a substituted or unsubstituted C6 to C20 aryl group.
8. 8. The method of claim 7,

   wherein R ³ is a C6 to C20 aryl group substituted with one or more alkyl groups.
9. According to claim 1,

   wherein R ⁶ is a hydrogen atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C20 alkoxy group.
10. According to claim 1,

    The core represented by Formula 1 is a compound having a maximum absorption wavelength at 610 nm to 640 nm.
11. According to claim 1,

    The shell represented by Formula 2 is a compound represented by Formula 2-1 below.

    [Formula 2-1]

    
12. According to claim 1,

    The core-shell compound is a compound represented by any one of Formulas A to I.

    [Formula A]

    

    [Formula B]

    

    [Formula C]

    

    [Formula D]

    

    [Formula E]

    

    [Formula F]

    

    [Formula G]

    

    [Formula H]

    

    [Formula I]

    
13. According to claim 1,

    The compound is a green dye.
14. The photosensitive resin composition containing the compound of any one of Claims 1-13.
15. 15. The method of claim 14,

    The photosensitive resin composition has a transmittance of 90% or more at 540 nm, and a transmittance of 10% or less at 600 nm to 640 nm.
16. 16. The method of claim 15,

    The photosensitive resin composition has a transmittance of 5% or less at 450 nm.
17. 16. The method of claim 15,

    The photosensitive resin composition is a photosensitive resin composition for a CMOS image sensor.
18. A photosensitive resin film produced using the photosensitive resin composition of claim 14 .
19. A color filter comprising the photosensitive resin film of claim 18 .
20. A CMOS image sensor comprising the color filter of claim 19 .

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