Compound, photosensitive resin composition containing the same, photosensitive resin film, color filter, and CMOS image sensor

Abstract

The present invention provides a compound represented by a specific chemical formula, a photosensitive resin composition including the compound, a photosensitive resin film manufactured using the photosensitive resin composition, a color filter including the photosensitive resin film, and a CMOS image sensor including the color filter.

Description

[Technical field]

[0001] The present disclosure relates to a compound, a photosensitive resin composition containing the compound, a photosensitive resin film produced using the photosensitive resin composition, a color filter including the photosensitive resin film, and a CMOS image sensor including the color filter. [Background technology]

[0002] A liquid crystal display device, which is one type of display device, has advantages such as light weight, thinness, low cost, low power consumption, and excellent connectivity with integrated circuits, and is being used in a wide range of notebook computers, monitors, and TV images. Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, and an upper substrate on which an active circuit part consisting of a liquid crystal layer, a thin film transistor, and a storage capacitor layer, and an ITO pixel electrode are formed. The color filter has a structure in which a black matrix layer formed in a predetermined pattern on a transparent substrate to block light from the boundary between pixels, and a pixel part in which a plurality of colors, usually the three primary colors of red (R), green (G), and blue (B) are arranged in a predetermined order to form each pixel, are sequentially stacked.

[0003] The pigment dispersion method, which is one of the methods for realizing color filters, is a method in which a photopolymerizable composition containing a colorant is coated on a transparent substrate provided with a black matrix, a pattern to be formed is exposed, and the non-exposed area is removed with a solvent and thermally cured, and a series of processes are repeated to form a colored thin film. The photosensitive resin composition used for manufacturing color filters using the pigment dispersion method generally consists of an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method having the above characteristics is actively applied to the manufacture of LCDs such as mobile phones, notebook computers, monitors, and TVs. However, recently, even photosensitive resin compositions for color filters using the pigment dispersion method, which has various advantages, are required to have not only excellent pattern characteristics but also further improved performance. In particular, there is a gradually increasing demand for colorants that can be applied to image sensors, which require high color reproduction rate as well as high brightness and high brightness / darkness ratio characteristics.

[0004] Image sensors are image capturing device components that generate images on display devices such as mobile phone cameras and DSCs (digital still cameras). They can be broadly classified into charge coupled device (CCD) image sensors and complementary metal oxide semiconductor (CMOS) image sensors according to their manufacturing process and application method.

[0005] Photosensitive resin films for color filters used in solid-state imaging devices are required to have a thickness of 1.5 μm or less, so a large amount of dye must be added to the photosensitive resin composition. This can result in problems such as reduced sensitivity, insufficient adhesion to the substrate, insufficient curing, or a significant decrease in pattern formability, such as the dye eluting and fading even in exposed areas.

[0006] Therefore, efforts are being made to develop a photosensitive resin composition for a color filter that can be applied to an image sensor and that can realize high color quality while satisfying reliability such as brightness and chemical resistance. Summary of the Invention [Problem to be solved by the invention]

[0007] One embodiment is directed to providing compounds that can provide color filters with improved brightness, light-to-dark ratio, and reliability.

[0008] Another embodiment is to provide a photosensitive resin composition comprising the compound.

[0009] Another embodiment provides a photosensitive resin film produced using the photosensitive resin composition.

[0010] Another embodiment provides a color filter including the photosensitive resin film.

[0011] Yet another embodiment provides a CMOS image sensor including the color filter. [Means for solving the problem]

[0012] One embodiment of the present invention provides a compound represented by the following Chemical Formula 1:

[0013] [ka]

[0014] In the above chemical formula 1, R 1 ~R 6 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, R 1 ~R3 One of them is represented by the following chemical formula 2, and the other two are different: R 4 ~R 6 One of them is represented by the following chemical formula 2, and the other two are different: L 1 is a substituted or unsubstituted alkylene group having 3 to 10 carbon atoms,

[0015] [ka]

[0016] In the above chemical formula 2, L 2 is a substituted or unsubstituted alkylene group having 2 to 20 carbon atoms.

[0017] In the above formula 1, R 1 ~R 3 One of them may be represented by the above chemical formula 2, and the remaining two may be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0018] In the above formula 1, R 1 is represented by the above formula 2, R 2 and R 3 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0019] In the above formula 1, R 3 is represented by the above formula 2, R 1 and R 2 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0020] In the above formula 1, R 4 ~R 6 One of them may be represented by the above chemical formula 2, and the remaining two may be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0021] In the above formula 1, R 4 is represented by the above formula 2, R 5 and R 6 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0022] In the above formula 1, R 6 is represented by the above formula 2, R 4 and R 5 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0023] The compound represented by Chemical Formula 1 can be represented by any one of Chemical Formulas 1-1 to 1-5 below.

[0024] [ka]

[0025] The compound may be a red dye.

[0026] Another embodiment provides a photosensitive resin composition comprising the compound.

[0027] The compound may be contained in an amount of 7% by weight to 16% by weight based on the total amount of solids constituting the photosensitive resin composition.

[0028] The photosensitive resin composition may further include a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

[0029] The photosensitive resin composition may further contain a pigment.

[0030] The photosensitive resin composition may further include malonic acid; 3-amino-1,2-propanediol; a leveling agent; a fluorine-based surfactant; or a combination thereof.

[0031] The photosensitive resin composition may be for a CMOS image sensor.

[0032] Another embodiment provides a photosensitive resin film produced using the photosensitive resin composition.

[0033] In still another embodiment, there is provided a color filter including the photosensitive resin film.

[0034] Yet another embodiment provides a CMOS image sensor including the color filter.

[0035] Other specific aspects of the present invention are included in the following detailed description. Effect of the Invention

[0036] The compound according to one embodiment has excellent red spectral characteristics and can be used as a dye when preparing a photosensitive resin composition for a red color filter. A photosensitive resin film prepared using the photosensitive resin composition containing the dye, a color filter including the same, and a CMOS image sensor can have excellent brightness, light-dark ratio, durability, and high reliability. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0037] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, preferred embodiments of the present invention will be described in detail, but they are given by way of example only and are not intended to limit the present invention, which is defined only by the scope of the claims set forth below.

[0038] Unless otherwise specified in this specification, "substituted" or "substituted" means that one or more hydrogen atoms in the functional group of the present invention are replaced with a halogen atom (F, Cl, Br, or I), a hydroxy group, a nitro group, a cyano group, an amino group (NH, NH(R 200) or N(R 201 )(R 202 ), where R 200 , R 201 , and R 202 are the same or different and each independently represents an alkyl group having 1 to 10 carbon atoms), 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 a substituted or unsubstituted heterocyclic group.

[0039] Unless otherwise specified in this specification, the term "alkyl group" means an alkyl group having 1 to 20 carbon atoms, specifically an alkyl group having 1 to 15 carbon atoms, the term "cycloalkyl group" means a cycloalkyl group having 3 to 20 carbon atoms, specifically an cycloalkyl group having 3 to 18 carbon atoms, the term "alkoxy group" means an alkoxy group having 1 to 20 carbon atoms, specifically an alkoxy group having 1 to 18 carbon atoms, the term "aryl group" means an aryl group having 6 to 20 carbon atoms, specifically an aryl group having 6 to 18 carbon atoms, the term "alkenyl group" means an alkenyl group having 2 to 20 carbon atoms, specifically an alkenyl group having 2 to 18 carbon atoms, the term "alkylene group" means an alkylene group having 1 to 20 carbon atoms, specifically an alkylene group having 1 to 18 carbon atoms, and the term "arylene group" means an arylene group having 6 to 20 carbon atoms, specifically an arylene group having 6 to 16 carbon atoms.

[0040] Unless otherwise specified in this specification, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" means that both "acrylic acid" and "methacrylic acid" are possible.

[0041] Unless otherwise defined herein, "combination" means a mixture or copolymerization, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymerization or random copolymerization.

[0042] Unless otherwise defined in a chemical formula herein, when a chemical bond is not drawn at a position where a chemical bond should be drawn, it means that a hydrogen atom is bonded to said position.

[0043] Additionally, unless otherwise defined in this specification, "*" means a moiety connected to the same or different atoms or chemical formulae.

[0044] One embodiment provides a compound represented by the following formula 1:

[0045] [ka]

[0046] In the above chemical formula 1, R 1 ~R 6 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, R 1 ~R 3 One of them is represented by the following chemical formula 2, and the other two are different: R 4 ~R 6 One of them is represented by the following chemical formula 2, and the other two are different: L 1 is a substituted or unsubstituted alkylene group having 3 to 10 carbon atoms,

[0047] [ka]

[0048] In the above chemical formula 2, L2 is a substituted or unsubstituted alkylene group having 2 to 20 carbon atoms.

[0049] In color filters manufactured from photosensitive resin compositions using pigments as colorants, there are limitations on brightness and light-to-dark ratio due to the size of pigment particles, so the need for improving brightness and light-to-dark ratio has been continuously raised. To achieve this, efforts have been made to realize color filters with improved brightness and light-to-dark ratio by introducing non-particle dyes instead of pigments and manufacturing photosensitive resin compositions suitable for dyes, and these efforts have shown some effect in improving brightness and light-to-dark ratio in the case of photosensitive resin compositions using dyes instead of pigments as the main colorant.

[0050] Meanwhile, there has been a rapid increase in demand for photosensitive resin compositions that can be applied to solid-state image sensors and complementary metal oxide semiconductor image sensors in addition to conventional display devices such as LCDs, but in the case of photosensitive resin compositions using conventional dyes as the main colorant, a new problem has emerged in that it is impossible to realize high color when applied to the image sensors, and it is very difficult to manufacture high-definition color filters. The reason why high color cannot be realized as described above is believed to be that the pattern size of the color filter attached to the solid-state image sensor is very small, about 1 / 100 to 1 / 200 times the size of the color filter pattern for conventional LCDs.

[0051] Therefore, after a long period of research, the inventors of the present invention have developed a dye compound to be used in a photosensitive resin composition for color filters, which is easily applicable to patterns having a size 100 to 200 times smaller than the size of conventional color filter patterns for LCDs, by modifying the structure of a xanthene compound as shown in Chemical Formula 1, and which has improved resolution, reduced residues, and excellent developability compared to conventional photosensitive resin compositions.

[0052] For example, the compound represented by Chemical Formula 1 has a dimer structure linked to a substituted or unsubstituted alkylene group having 3 to 10 carbon atoms, and has only one substituent represented by Chemical Formula 2 on each side of the dimer structure, and therefore is significantly different from xanthene compounds of other structures in that it has excellent solubility in organic solvents and the brightness and chemical resistance of a photosensitive resin composition containing the compound as a colorant are also excellent. That is, the compound according to one embodiment is able to provide a photosensitive resin composition having excellent red spectral characteristics and a high molar absorption coefficient compared to conventional xanthene compounds by specifically controlling the structure of the xanthene compound, and thus having improved color characteristics such as brightness and light-dark ratio, and chemical resistance.

[0053] For example, in the above Chemical Formula 1, L 1 may be a substituted or unsubstituted alkylene group having 3 to 10 carbon atoms, for example, a substituted or unsubstituted alkylene group having 3 to 8 carbon atoms, for example, a substituted or unsubstituted alkylene group having 3 to 6 carbon atoms. 1 Even if L is an alkylene, it is important to control its length in terms of color properties and chemical resistance. 1 When L is a substituted or unsubstituted ethylene group (having 2 carbon atoms), the length of the linking group forming the dimer structure may be too short, resulting in poor color properties (especially brightness) and chemical resistance. 1 When is a substituted or unsubstituted alkylene group having 11 carbon atoms, the length of the linking group forming the dimer structure is too long, so that the chemical resistance is poor and the color properties may also be poor.

[0054] For example, in the above Chemical Formula 1, R 1 ~R 3 One of them may be represented by the above Chemical Formula 2, and the remaining two may be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. In this case, the compound represented by the above Chemical Formula 1 can be used as a colorant in a photosensitive resin composition for a color filter, and it is also easy to realize an image sensor with high color reproduction.

[0055] For example, in the above Chemical Formula 1, R 1 is represented by the above formula 2, R 2 and R 3 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. For example, in the above Chemical Formula 1, R 3 is represented by the above formula 2, R 1 and R 2 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. 1 ~R 3 When the definition is as above, it is easy to realize a red pixel, and the solubility in an organic solvent can be further improved, which is advantageous in terms of improving brightness and ensuring process characteristics.

[0056] For example, in the above Chemical Formula 1, R 4 ~R 6 One of the groups may be represented by the above-mentioned chemical formula 2, and the remaining two groups may be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. For example, in the above-mentioned chemical formula 1, R 4 is represented by the above formula 2, R 5 and R 6 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. For example, in the above Chemical Formula 1, R 6 is represented by the above formula 2, R 4 and R 5 may each independently be an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. 4 ~R 6 When the definition is as above, it is easy to realize a red pixel, and the solubility in an organic solvent can be further improved, which is advantageous in terms of improving brightness and ensuring process characteristics.

[0057] Above all, even if the xanthene-based compound is of the same series, if it does not have the structure represented by Chemical Formula 1, the brightness and chemical resistance of a photosensitive resin composition containing such a xanthene-based compound as a colorant is significantly reduced or high color cannot be achieved. That is, the xanthene-based compound according to one embodiment is different from conventional xanthene-based compounds in terms of structure and spectroscopy in that it has the structure represented by Chemical Formula 1.

[0058] For example, the compound represented by Chemical Formula 1 can be represented by any one of Chemical Formulas 1-1 to 1-5 below, but is not necessarily limited thereto.

[0059] [ka]

[0060] For example, the compound represented by Formula 1 can express a brighter color even in a small amount, and when used as a colorant, it can be used to manufacture a display device having excellent color characteristics such as luminance and contrast ratio. For example, the compound may be a colorant, for example, a dye, for example, a red dye.

[0061] Generally, dyes are the most expensive components used in color filters. Therefore, in order to achieve a desired effect, such as high brightness or high contrast ratio, a larger amount of expensive dye must be used, which increases the production cost. However, when the compound according to an embodiment is used as a dye in a color filter, excellent color characteristics such as high brightness and high contrast ratio can be achieved even in a small amount, thereby reducing the production cost.

[0062] According to another embodiment, there is provided a photosensitive resin composition comprising the compound according to the above embodiment.

[0063] For example, the photosensitive resin composition may include the compound according to the embodiment, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

[0064] The compound according to one embodiment can act as a colorant, for example a dye, such as a red dye, in a photosensitive resin composition to provide excellent color properties.

[0065] The compound according to one embodiment may be contained in an amount of 5% by weight to 20% by weight, for example, 6% by weight to 19% by weight, for example, 7% by weight to 18% by weight, for example, 7% by weight to 17% by weight, for example, 7% by weight to 16% by weight, based on the total weight of solids constituting the photosensitive resin composition. When the compound according to one embodiment is contained in the above range, the color reproduction ratio and the brightness ratio become excellent.

[0066] The photosensitive resin composition may further include a pigment, such as a yellow pigment, a red pigment, or a combination thereof.

[0067] The yellow pigment includes CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, etc. in the Color Index, which may be used alone or in combination of two or more kinds.

[0068] The red pigment may be a perylene pigment, anthraquinone pigment, azo pigment, diazo pigment, quinacridone pigment, anthracene pigment, etc. Specific examples of the red pigment include perylene pigment, quinacridone pigment, naphthol AS, shikomine pigment, anthraquinone (sudan I, II, III, R), vis azo, benzopyran, etc.

[0069] The pigment may be contained in the photosensitive resin composition in the form of a pigment dispersion.

[0070] The pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.

[0071] The solid pigment may be contained in an amount of 1 wt% to 20 wt%, for example, 8 wt% to 20 wt%, for example, 8 wt% to 15 wt%, for example, 10 wt% to 20 wt%, for example, 10 wt% to 15 wt%, relative to the total amount of the pigment dispersion.

[0072] The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant, etc. Specific examples of the dispersant include polyalkylene glycol and its ester, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylate, carboxylate, alkylamide alkylene oxide adduct, alkylamine, etc., which may be used alone or in combination of two or more.

[0073] Examples of commercially available products of the dispersant include 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., from BYK; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc., from EFKA Chemical; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc; or Ajinomoto's PB711, PB821, etc.

[0074] The dispersant may be included in an amount of 1% by weight to 20% by weight based on the total weight of the pigment dispersion. When the dispersant is included in the above range, it is possible to maintain an appropriate viscosity and excellent dispersibility of the photosensitive resin composition, thereby maintaining optical, physical, and chemical qualities when applied to a product.

[0075] Examples of the solvent that can be used to form the pigment dispersion include ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, and propylene glycol methyl ether.

[0076] 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 to ensure process margins, and the color reproduction rate and the brightness ratio are excellent.

[0077] The binder resin may be an acrylic resin.

[0078] The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing one or more acrylic repeating units.

[0079] The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxy groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

[0080] 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.

[0081] Examples of the second ethylenically unsaturated monomer include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyl toluene, and vinylbenzyl methyl ether; unsaturated carboxylic acid ester compounds such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, and phenyl (meth)acrylate; unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; cyanide vinyl compounds such as (meth)acrylonitrile; and unsaturated amide compounds such as (meth)acrylamide. These may be used alone or in combination of two or more.

[0082] 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 methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc., but are not limited thereto, and these may be used alone or in combination of two or more kinds.

[0083] For example, the binder resin may further include an epoxy resin in addition to the acrylic resin.

[0084] The weight average molecular weight of the binder resin may be 3,000 g / mol to 150,000 g / mol, for example, 5,000 g / mol to 50,000 g / mol, for example, 20,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the binder resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, an appropriate viscosity, and excellent adhesion to a substrate during production of a color filter.

[0085] 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.

[0086] The binder resin may be included in an amount of 1% by weight to 20% by weight, for example, 1% by weight to 15% by weight, for example, 1% by weight to 10% by weight, based on the total amount of the photosensitive resin composition. When the binder resin is included in the above range, excellent developability and improved crosslinking properties can be obtained during the production of a color filter, resulting in excellent surface smoothness.

[0087] The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

[0088] The photopolymerizable compound has the ethylenically unsaturated double bond, and thus can undergo sufficient polymerization upon exposure in the pattern formation step, thereby forming a pattern having excellent heat resistance, light resistance, and chemical resistance.

[0089] 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, ) acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy(meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(meth)acryloyloxyethyl phosphate, novolac epoxy(meth)acrylate, and the like.

[0090] 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 (registered trademark), M-111 (registered trademark), M-114 (registered trademark), etc., manufactured by Toagosei Co., Ltd.; KAYARAD TC-110S (registered trademark), TC-120S (registered trademark), etc., manufactured by Nippon Kayaku Co., Ltd.; V-158 (registered trademark), V-2311 (registered trademark), etc., manufactured by Osaka Organic Chemical Industry Co., Ltd. Examples of the bifunctional ester of (meth)acrylic acid include Aronix M-210 (registered trademark), M-240 (registered trademark), M-6200 (registered trademark), etc., manufactured by Toagosei Co., Ltd.; KAYARAD HDDA (registered trademark), HX-220 (registered trademark), R-604 (registered trademark), etc., manufactured by Nippon Kayaku Co., Ltd.; and V-260 (registered trademark), V-312 (registered trademark), V-335HP (registered trademark), etc., manufactured by Osaka Organic Chemical Industry Ltd. Examples of the trifunctional ester of (meth)acrylic acid include ARONIX M-309 (registered trademark), M-400 (registered trademark), M-405 (registered trademark), M-450 (registered trademark), M-710 (registered trademark), M-8030 (registered trademark), M-8060 (registered trademark), etc., manufactured by Toagosei Co., Ltd.; KAYARAD TMPTA (registered trademark), DPCA-20 (registered trademark), DPCA-30 (registered trademark), DPCA-60 (registered trademark), DPCA-120 (registered trademark), etc., manufactured by Nippon Kayaku Co., Ltd.; V-295 (registered trademark), V-300 (registered trademark), V-360 (registered trademark), V-GPT (registered trademark), V-3PA (registered trademark), V-400 (registered trademark), etc., manufactured by Osaka Organic Chemical Industry Co., Ltd. The above products can be used alone or in combination of two or more kinds.

[0091] The photopolymerizable compound can also be used after being treated with an acid anhydride in order to impart better developability.

[0092] The photopolymerizable compound may be contained in an amount of 1% by weight to 15% by weight, for example, 1% by weight to 10% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained within the above range, curing upon exposure occurs sufficiently in the pattern formation step, resulting in excellent reliability and excellent developability in an alkaline developer.

[0093] The photopolymerization initiator is an initiator commonly used in photosensitive resin compositions, and may be, 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.

[0094] Examples of the acetophenone-based compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one.

[0095] Examples of the benzophenone-based compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

[0096] Examples of the thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.

[0097] Examples of the benzoin-based compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0098] 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, azine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, and the like.

[0099] Examples of the oxime-based compound include O-acyloxime-based compounds, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, and O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one. Specific examples of the O-acyloxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butan-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-one oxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate.

[0100] In addition to the above compounds, the photopolymerization initiator may be 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, a fluorene-based compound, or the like.

[0101] The photoinitiator may be used in conjunction with a photosensitizer, which absorbs light, becomes excited, and then transfers the energy to initiate a chemical reaction.

[0102] Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, and dipentaerythritol tetrakis-3-mercaptopropionate.

[0103] The photopolymerization initiator may be included in an amount of 0.01% by weight to 10% by weight, for example, 0.1% by weight to 5% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included in the above range, curing upon exposure occurs sufficiently in the pattern formation process, so that excellent reliability can be obtained, and the pattern has excellent heat resistance, light resistance, and chemical resistance, excellent resolution and adhesion, and a decrease in transmittance due to unreacted initiator can be prevented.

[0104] The solvent may be a material that is compatible with but does not react with the compound according to one embodiment, the pigment, the binder resin, the photopolymerizable compound, and the photopolymerization initiator.

[0105] Examples of the solvent include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methyl phenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; methyl ethyl ketone, cyclohexanone, 4-hydroxy-4 ketones such as methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactate 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-oxy-2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; 2-hydroxypropionic acid ethyl, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyethyl acetate, 2-hydroxypropionic acid ethyl ... esters such as methyl oxy-3-methylbutanoate; ketone acid esters such as ethyl pyruvate; and high boiling point solvents such as 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, ethyl benzoate, diethyl oxalate, diethyl maleate, gamma-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

[0106] Of these, taking into consideration compatibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether; 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 can be used.

[0107] The solvent may be contained in an amount of, for example, 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 has excellent processability during production of a color filter.

[0108] The photosensitive resin composition according to another embodiment may further include other additives, such as malonic acid; 3-amino-1,2-propanediol; a silane coupling agent; a leveling agent; a fluorine-based surfactant; a radical polymerization initiator; or a combination thereof, in order to prevent stains or spots during application, improve leveling performance, and prevent the generation of residues due to undevelopment.

[0109] Examples of the silane coupling agent include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-epoxycyclohexyl)ethyltrimethoxysilane, and the like. These can be used alone or in combination of two or more kinds. Examples of the fluorine-based surfactant include BM-1000 (registered trademark) and BM-1100 (registered trademark) manufactured by BM Chemie; Megafac F 142D (registered trademark), Megafac F 172 (registered trademark), Megafac F 173 (registered trademark), Megafac F 172D (registered trademark), Megafac F 173D ... 183 (registered trademark), etc.; Fluorad FC-135 (registered trademark), FC-170C (registered trademark), FC-430 (registered trademark), FC-431 (registered trademark), etc., manufactured by Sumitomo 3M Limited; Surflon S-112 (registered trademark), S-113 (registered trademark), S-131 (registered trademark), S-141 (registered trademark), S-145 (registered trademark), etc., manufactured by Asahi Glass Co., Ltd.; and commercially available products such as SH-28PA (registered trademark), -190 (registered trademark), -193 (registered trademark), SZ-6032 (registered trademark), and SF-8428 (registered trademark), manufactured by Toray Silicon Co., Ltd.

[0110] The content of the additives can be easily adjusted depending on the desired physical properties.

[0111] For example, the photosensitive resin composition may be for a CMOS image sensor.

[0112] According to another embodiment, there is provided a photosensitive resin film manufactured using the photosensitive resin composition according to the above embodiment.

[0113] According to another embodiment, there is provided a color filter including the photosensitive resin film.

[0114] The process of forming a pattern in the color filter is as follows.

[0115] The process includes a step of applying the photosensitive resin composition onto a supporting substrate by spin coating, slit coating, inkjet printing, etc., a step of drying the applied photosensitive resin composition to form a photosensitive resin composition film, a step of exposing the photosensitive resin composition film, a step of developing the exposed photosensitive resin composition film with an alkaline aqueous solution to produce a photosensitive resin film, and a step of heat-treating the photosensitive resin film. The conditions of the above steps are well known in the art, and therefore will not be described in detail here.

[0116] According to another embodiment, there is provided a CMOS image sensor including the color filter.

[0117] The present invention will be described in more detail below with reference to examples. However, the following examples are merely preferred examples of the present invention and the present invention is not limited to the following examples. EXAMPLES

[0118] (Synthesis of Compounds) (Synthesis of intermediate 1)

[0119] [ka]

[0120] 32g of compound A (CAS No. 77545-45-0) was added to a reactor and dissolved in 300g of 2-propanol. 19.1g of 2,6-dimethylaniline was added and stirred at 80°C for 8 hours. The reaction mixture was cooled and 2L of water was added to generate a precipitate. The resulting precipitate was suction filtered and washed with additional water. The filtered product was dried to obtain 31g of intermediate 1 (80% yield).

[0121] (Synthesis of intermediate 2)

[0122] [ka]

[0123] 10g of intermediate 1 was placed in a reactor, followed by 30g of dimethylformamide and 1.65g of N,N'-Diethyl-1,6-diaminohexane, and then stirred at 120°C for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane, and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to obtain 8.69g of intermediate 2 (81% yield).

[0124] Synthesis Example 1: Synthesis of compound represented by chemical formula 1-1 3.0g of intermediate 2 was added to a reactor, followed by 5g of dimethylformamide, 1.8g of N-(3-Bromopropyl)phthalimide, 0.9g of K2CO3, and 0.11g of KI, and then the mixture was heated to 95℃ and stirred for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to finally obtain 3g (72% yield) of the compound represented by the following chemical formula 1-1.

[0125] [ka]

[0126] Synthesis Example 2: Synthesis of compound represented by chemical formula 1-2 A compound represented by the following formula 1-2 was obtained in the same manner as in Synthesis Example 1, except that 1.9 g of N-(4-Bromobutyl)phthalimide was used instead of 1.8 g of N-(3-Bromopropyl)phthalimide.

[0127] [ka]

[0128] Synthesis Example 3: Synthesis of compound represented by chemical formula 1-3 The compound represented by the following formula 1-1 was synthesized in the same manner as in Synthesis Example 1, except that 1.7 g of N-(2-Bromoethyl)phthalimide was used instead of 1.8 g of N-(3-Bromopropyl)phthalimide. 3 A compound represented by the formula:

[0129] [ka]

[0130] Synthesis Example 4: Synthesis of compound represented by chemical formula 1-4 32g of compound A (CAS No. 77545-45-0) was added to a reactor and dissolved in 300g of 2-propanol. 16.9g of o-Toluidine was added and stirred at 80°C for 8 hours. The reaction mixture was cooled and 2L of water was added to generate a precipitate. The resulting precipitate was suction filtered and washed with additional water. The filtered product was dried to obtain 31g of intermediate 3 (80% yield).

[0131] [ka]

[0132] 10g of intermediate 3 was placed in a reactor, followed by 30g of dimethylformamide and 1.70g of N,N'-Diethyl-1,6-diaminohexane, and then stirred at 120℃ for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane, and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to obtain 8.95g of intermediate 4 (81% yield).

[0133] [ka]

[0134] 3.0g of intermediate 4 was added to a reactor, followed by 5g of dimethylformamide, 1.7g of N-(3-Bromopropyl)phthalimide, 0.9g of K2CO3, and 0.11g of KI, and then the mixture was heated to 95℃ and stirred for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried, and finally 2.98g (72% yield) of the compound represented by the following chemical formula 1-4 was obtained.

[0135] [ka]

[0136] Synthesis Example 5: Synthesis of Compound Represented by Chemical Formula 1-5 10g of intermediate 1 was added to a reactor, followed by 30g of dimethylformamide and 0.98g of N,N'-Dimethyl-1,3-propanediamine, and then stirred at 120°C for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane, and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to obtain 7.72g of intermediate 5 (75% yield).

[0137] [ka]

[0138] 3.0g of intermediate 5 was added to a reactor, followed by 5g of dimethylformamide, 1.8g of N-(3-Bromopropyl)phthalimide, 0.9g of K2CO3, and 0.11g of KI, and then the mixture was heated to 95℃ and stirred for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to finally obtain 2.07g (50% yield) of the compound represented by the following chemical formula 1-5.

[0139] [ka]

[0140] Comparative Synthesis Example 1: Synthesis of compound represented by formula C-1

[0141] [ka]

[0142] 32 g of compound A (CAS No. 77545-45-0) was placed in a reactor and dissolved in 300 g of N-Methylpyrrolidone (NMP). -Methylenebis(2,6-dimethylaniline)After adding 8.03g of toluene, the mixture was stirred at 150°C for 4 hours. The reaction mixture was cooled and 2L of water was added to generate a precipitate. The precipitate was suction filtered and washed with additional water. The filtered product was dried to obtain 16.29g (52% yield) of intermediate 6.

[0143] [ka]

[0144] 10g of intermediate 6 was added to a reactor, followed by 30g of N-Methylpyrrolidone (NMP) and 2.93g of 2,6-dimethylaniline, and then stirred at 150°C for 5 hours. 100g of dichloromethane was added to the reactant and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane, and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to obtain 5.03g of intermediate 7 (43% yield).

[0145] 3.0g of intermediate 7 was added to a reactor, followed by 5g of dimethylformamide, 2.11g of 1-iodopropane, and 1.71g of K2CO3, and then the mixture was heated to 95℃ and stirred for 12 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to finally obtain 0.97g (30% yield) of the compound represented by the following chemical formula C-1.

[0146] [ka]

[0147] Comparative Synthesis Example 2: Synthesis of the compound represented by the chemical formula C-2 3.0g of intermediate 7 was added to a reactor, followed by 5g of dimethylformamide, 3.32g of N-(3-Bromopropyl)phthalimide, 1.71g of K2CO3, and 0.21g of KI, and then the mixture was heated to 95℃ and stirred for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to finally obtain 2.04g (42% yield) of the compound represented by the following chemical formula C-2.

[0148] [ka]

[0149] Comparative Synthesis Example 3: Synthesis of the compound represented by the chemical formula C-3

[0150] [ka]

[0151] 110g of the intermediate was placed in a reactor, followed by 30g of dimethylformamide and 0.85g of N,N'-Dimethylethylenediamine, and then stirred at 120°C for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane, and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to obtain 6.5g of intermediate 8 (64% yield). 3.0g of intermediate 8 was added to a reactor, followed by 5g of dimethylformamide, 1.94g of N-(3-Bromopropyl)phthalimide, 1.0g of K2CO3, and 0.12g of KI, and then the mixture was stirred for 8 hours while heating at 95℃. 100g of dichloromethane was added to the reaction mixture and washed with water. The organic layer obtained was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane and then added dropwise to 100g of normal hexane to cause precipitation. The precipitate obtained was suction filtered and further washed. The filtered product was dried to finally obtain 1.73g (42% yield) of the compound represented by the following chemical formula C-3.

[0152] [ka]

[0153] Comparative Synthesis Example 4: Synthesis of the compound represented by the chemical formula C-4

[0154] [ka]

[0155] 10g of intermediate 1 was placed in a reactor, followed by 30g of dimethylformamide and 2.33g of N,N'-Dimethylundecanediamine, and then stirred at 120°C for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane, and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to obtain 9.61g of intermediate 9 (84% yield).

[0156] 3.0g of intermediate 9 was added to a reactor, followed by 5g of dimethylformamide, 1.72g of N-(3-Bromopropyl)phthalimide, 0.89g of K2CO3, and 0.11g of KI, and then the mixture was heated to 95℃ and stirred for 8 hours. 100g of dichloromethane was added to the reaction mixture and washed with water. The resulting organic layer was filtered through silica and then distilled under reduced pressure. The distilled mixture was dissolved in 10g of dichloromethane and then added dropwise to 100g of normal hexane to cause precipitation. The resulting precipitate was suction filtered and further washed. The filtered product was dried to finally obtain 3.00g (75% yield) of the compound represented by the following chemical formula C-4.

[0157] [ka]

[0158] Comparative Synthesis Example 5: Synthesis of the compound represented by the formula C-5 The same procedure as in Synthesis Example 1 was carried out, except that N-(1-Bromomethyl)phthalimide was used instead of N-(3-Bromopropyl)phthalimide in Synthesis Example 1, to obtain 3.00 g (75% yield) of a compound represented by the following formula C-5.

[0159] [ka]

[0160] (evaluation) Evaluation 1: Solubility measurement A dilution solvent (PGMEA) was added to 0.5 g of each of the compounds of Synthesis Examples 1 to 5 and Comparative Synthesis Examples 1 to 5, and the solution was stirred at 25° C. rpm for 1 hour using a mix rotor (MIXROTAR VMR-5, iuchi Co., Ltd.). The solubility of each compound was confirmed as shown in the following table. 1 As shown in.

[0161] Solubility Evaluation Criteria The compound (solute) dissolves at 10% by weight or more relative to the total amount of dilution solvent: Yes Compound (solute) dissolves at less than 10% by weight relative to the total amount of dilution solvent: X

[0162] [Table 1]

[0163] From Table 1 above, it can be seen that the compounds of Synthesis Examples 1 to 5 according to an embodiment have better solubility in organic solvents than the compounds of Comparative Synthesis Examples 1 to 5, and can exhibit excellent color properties when used in photosensitive resin compositions and the like.

[0164] (Synthesis of Photosensitive Resin Composition) Examples 1 to 5 and Comparative Examples 1 to 5 The components mentioned below were mixed in the compositions shown in Table 2 below to prepare photosensitive resin compositions according to Examples 1 to 5 and Comparative Examples 1 to 5.

[0165] 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 monomer were added thereto and stirred at room temperature for 2 hours. Next, the compound (dye) and pigment (pigment dispersion form) prepared in the above Synthesis Example were added as colorants to the obtained reaction product and stirred at room temperature for 1 hour (in the case of dye, 10 wt % was added based on the total solid content). Next, an antioxidant and a leveling agent were added, and the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

[0166] [Table 2]

[0167] Evaluation 2: Color coordinates, brightness and chemical resistance The photosensitive resin compositions prepared in Examples 1 to 5 and Comparative Examples 1 to 5 were applied to a thickness of 1 μm to 3 μm on a degreased and washed glass substrate having a thickness of 1 mm, and dried on a hot plate at 90° C. for 2 minutes to obtain a coating film. The coating film was then exposed to light using a high-pressure mercury lamp having a 365 nm wavelength. After that, the sample was dried in a hot air circulation drying oven at 200° C. for 5 minutes to obtain a sample. The pixel layer was evaluated for color purity using a C light source standard using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the luminance and brightness ratio were calculated based on the CIE color coordinates, and are shown in Table 3 below.

[0168] In addition, the initial thickness of the sample (photoresist film) obtained by the exposure and drying was measured, and then it was left in NMP solvent at 25°C for 10 minutes, washed with ultrapure water for 30 seconds, and dried by blowing with compressed air. Then, the del(E*) value was measured using the spectrophotometer to confirm the chemical resistance, and the results are shown in Table 3 below.

[0169] Chemical resistance evaluation criteria del(E*) is less than 3: del(E*) is 3 or more: X

[0170] [Table 3]

[0171] From Table 3 above, it can be seen that the photosensitive resin compositions of Examples 1 to 5 containing the compound according to an embodiment as a dye have superior luminance, light-dark ratio, and chemical resistance compared to the photosensitive resin compositions of Comparative Examples 1 to 5 not containing the compound, and can be easily applied to image sensors, etc., to manufacture high-definition display devices with excellent color characteristics.

[0172] Although the above describes a preferred embodiment of the present invention, the present invention is not limited thereto, and can be embodied in various modified forms within the scope of the claims, the detailed description of the invention, and the accompanying drawings, which of course also fall within the scope of the present invention.

Claims

1. A compound represented by the following chemical formula 1: [Formula 1] In the above chemical formula 1, One of R 1 and R 2 is represented by the following chemical formula 2, and the other of R 1 and R 2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, R 3 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; One of R 4 and R 5 is represented by the following chemical formula 2, and the other of R 4 and R 5 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; R 6 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; L １ is a substituted or unsubstituted alkylene group having 3 to 10 carbon atoms, [Case 2] In the above chemical formula 2, L ２ is a substituted or unsubstituted alkylene group having 2 to 20 carbon atoms.

2. The compound according to claim 1, wherein R 3 is an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

3. The R １ is represented by Chemical Formula 2, and R 2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; 2. The compound according to claim 1, wherein R 3 is an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

4. The compound according to claim 1, wherein R 6 is an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

5. The R ４ is represented by Chemical Formula 2, R 5 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, The compound according to claim 1, wherein R 6 is an unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

6. The compound represented by the formula 1 is the compound according to claim 1, which is represented by any one of the following formulas 1-1 to 1-5. [C3]

7. The compound of claim 1 , wherein the compound is a red dye.

8. A photosensitive resin composition comprising the compound according to any one of claims 1 to 7.

9. The photosensitive resin composition according to claim 8, wherein the compound is contained in an amount of 7% by weight to 16% by weight based on the total amount of solids constituting the photosensitive resin composition.

10. The photosensitive resin composition according to claim 8 , further comprising a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

11. The photosensitive resin composition according to claim 8 , further comprising a pigment.

12. The photosensitive resin composition according to claim 8, further comprising: malonic acid; 3-amino-1,2-propanediol; a leveling agent; a fluorosurfactant; or a combination thereof.

13. The photosensitive resin composition according to claim 8, which is for a CMOS image sensor.

14. A photosensitive resin film produced by using the photosensitive resin composition of claim 8.

15. A color filter comprising the photosensitive resin film of claim 14.

16. 16. A CMOS image sensor comprising the color filter of claim 15.

Images