TWI809326B - Phthalocyanine-based compound, photosensitive resin composition, photosensitive resin layer, color filter and display device - Google Patents

Abstract

Provided are a phthalocyanine-based compound exhibiting the shortest wavelength of a full width at half maximum with respect to the maximum absorption wavelength in a range of 600 nm to 620 nm, a photosensitive resin composition including the same, a photosensitive resin layer produced using the photosensitive resin composition, a color filter including the photosensitive resin layer, and a display device including the color filter. The compound has excellent green spectral characteristics, a high molar extinction coefficient, and excellent solubility in an organic solvent.

Description

Phthalocyanine compound, photosensitive resin composition, photosensitive resin layer, color filter, and display device

The present disclosure relates to a phthalocyanine-based compound, a photosensitive resin composition containing the compound, a photosensitive resin layer, a color filter and a display device. [Cross Reference to Related Application]

This application claims Korean Patent Application No. 10-2019-0135770 filed at KIPO on October 29, 2019 and Korean Patent Application No. 10 filed at KIPO on Aug. 19, 2020 10-2020-0104060, the entire contents of which are incorporated herein by reference.

Among many types of displays, liquid crystal display devices have advantages in brightness, thinness, low cost, low operating power consumption, and improved adhesion to integrated circuits, and have been more widely used in laptops, monitors, and TV screen. The liquid crystal display device comprises: 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 and an ITO pixel electrode are formed, and the active circuit part includes Liquid crystal layer, thin film transistor and capacitor layer. Each picture is formed by sequentially stacking a plurality of color filters (generally, formed from three primary colors such as red (R), green (G) and blue (B)) in a predetermined order in the pixel area. A color filter is formed, and a black matrix layer is arranged in a predetermined pattern on a transparent substrate to form boundaries between pixels.

The pigment dispersion method, which is a method of forming a color filter, provides a colored film by repeating a series of processes such as coating a photopolymerizable composition containing a colorant on a transparent base containing a black matrix, making the formed pattern Expose to light, remove unexposed portions with solvent, and allow heat to cure. A photosensitive resin composition for producing a color filter according to a pigment dispersion method generally includes an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, other additives, and the like. The pigment dispersion method is effectively applied to produce LCDs, such as mobile phones, laptops, monitors, and TVs. However, photosensitive resin compositions for color filters are recently required to have improved properties and excellent pattern profiles for the pigment dispersion method. In particular, demand for colorants suitable for image sensors requiring high color reproducibility as well as high brightness and high contrast characteristics has grown.

An image sensor is the part of the image sensor that generates an image in a display device such as a cell phone camera, digital still camera (DSC), and the like, and can be classified as a charge coupled device (CCD) Image sensors and complementary metal oxide semiconductor (CMOS) image sensors.

Since a charge-coupled device (CCD) image sensor uses a photosensitive resin layer for a color filter that requires a film thickness of about 1.5 μm or less, the photosensitive resin composition should preparation, and thus have problems with insufficient adhesion to the substrate or insufficient curing due to reduced sensitivity, significant reduction in pattern formability (eg loss of color due to dye elution in exposed areas), and the like.

Therefore, efforts have been made to develop photosensitive resin compositions for color filters that satisfy reliability such as brightness, chemical resistance, etc. while achieving high color and are therefore suitable for image sensors.

An embodiment provides a compound capable of realizing a high definition color filter.

Another embodiment provides a photosensitive resin composition comprising the compound.

Another embodiment provides a photosensitive resin layer produced using the photosensitive resin composition.

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

Another embodiment provides a display device including the color filter.

One embodiment of the present invention provides a phthalocyanine compound exhibiting a shortest wavelength of a full width at half maximum (FWHM) relative to a maximum absorption wavelength within a range of about 600 nm to about 620 nm.

The phthalocyanine compound may be represented by Chemical Formula 1.

[chemical formula 1] In Chemical Formula 1, R ¹ to R ⁴ are independently hydrogen atoms, R ⁵ to R ⁸ are independently hydrogen atoms or halogen atoms, and R ⁹ to R ¹⁶ are independently halogen atoms or represented by Chemical Formula 2.

[chemical formula 2] Wherein, in Chemical Formula 2, R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

Chemical Formula 2 may be represented by one of Chemical Formula 2-1 to Chemical Formula 2-4. [chemical formula 2-1] [chemical formula 2-2] [chemical formula 2-3] [chemical formula 2-4] In Chemical Formula 2-1 to Chemical Formula 2-4, R ¹⁸ and R ¹⁹ are independently substituted or unsubstituted C1 to C20 alkyl groups, R ²⁰ to R ²² are independently hydrogen atoms or substituted or unsubstituted C1 to C20 alkyl, and L ¹ is a substituted or unsubstituted C1 to C20 alkylene. One of R ⁹ to R ¹⁶ may be represented by Chemical Formula 2. "One of ^R9 to ^R12 " or "one of ^R13 to ^R16 " may be represented by Chemical Formula 2. One of "R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ " can be represented by Chemical Formula 2. "Two of R ⁹ to R ¹⁶ " can be represented by Chemical Formula 2. "One of R ⁹ to R ¹² " and "one of R ¹³ to R ¹⁶ " can be represented by Chemical Formula 2. "One of R ¹⁰ and R ¹¹ " and "one of R ¹⁴ and R ¹⁵ " can be represented by Chemical Formula 2.

The compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-20. [chemical formula 1-1] [chemical formula 1-2] [chemical formula 1-3] [chemical formula 1-4] [chemical formula 1-5] [chemical formula 1-6] [chemical formula 1-7] [chemical formula 1-8] [chemical formula 1-9] [chemical formula 1-10] [chemical formula 1-11] [chemical formula 1-12] [chemical formula 1-13] [chemical formula 1-14] [chemical formula 1-15] [chemical formula 1-16] [chemical formula 1-17] [chemical formula 1-18] [chemical formula 1-19] [chemical formula 1-20] .

The compound can be a green dye.

Another embodiment provides a photosensitive resin composition comprising the compound.

Based on the total amount of the photosensitive resin composition, the content of the compound may be about 1% by weight to about 40% by weight.

The photosensitive resin composition may further include an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

The photosensitive resin composition may further contain a pigment.

The photosensitive resin composition may further include a compound represented by Chemical Formula 3.

[chemical formula 3] In chemical formula 3, R ²³ and R ²⁴ are independently hydroxyl or substituted or unsubstituted C1 to C20 alkyl, and n1 and n2 are independently integers from 0 to 5, provided that 3 ≤ n1+n2 ≤ 5.

Another embodiment provides a photosensitive resin layer produced using the photosensitive resin composition.

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

Another embodiment provides a display device including the color filter.

Other embodiments of the invention are included in the following detailed description.

The compound according to an embodiment has excellent green spectral characteristics, a high molar extinction coefficient, and excellent solubility in organic solvents, and thus can be used as a dye for a green photosensitive resin composition for a color filter, and thus, passes A photosensitive resin layer and a color filter produced using the photosensitive resin composition including the dye may have excellent brightness and contrast.

Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto and the present invention is defined by the scope of the invention claims.

As used herein, when no specific definition is otherwise provided, the term "substituted" means substituted with a substituent selected from the group consisting of halogen (F, Br, Cl or I), hydroxyl, nitro, cyano, Amino (NH ₂ , NH(R ²⁰⁰ ) or N(R ²⁰¹ )(R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different, and are independently C1 to C10 alkyl), formamidinyl, hydrazine substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alicyclic organic group , a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

As used herein, when no specific definition is otherwise provided, the term "alkyl" refers to C1 to C20 alkyl and specifically C1 to C15 alkyl, and the term "cycloalkyl" refers to C3 to C20 cycloalkane and specifically C3 to C18 cycloalkyl, the term "alkoxy" refers to C1 to C20 alkoxy and specifically C1 to C18 alkoxy, the term "aryl" refers to C6 to C20 aromatic and specifically C6 to C18 aryl, the term "alkenyl" refers to C2 to C20 alkenyl and specifically C2 to C18 alkenyl, the term "alkylene" refers to C1 to C20 alkylene and Specifically a C1 to C18 alkylene group, and the term "arylylene" refers to a C6 to C20 arylylene group and specifically a C6 to C16 arylylene group.

As used herein, when no specific definition is otherwise provided, "(meth)acrylate" means "acrylate" and "methacrylate", and "(meth)acrylic" means "acrylic" and "Methacrylate".

As used herein, when no definition is otherwise provided, the term "combining" means mixing or copolymerizing. In addition, "copolymerization" means block copolymerization to random copolymerization, and "copolymer" means block copolymer to random copolymer.

In the chemical formulas in this specification, unless a specific definition is otherwise provided, when a chemical bond is not drawn at a position that should be given, hydrogen is bonded at the position.

As used herein, when no specific definition is otherwise provided, "*" indicates a point where the same or different atoms or chemical formulas are bonded.

An embodiment provides a phthalocyanine compound exhibiting a shortest wavelength of FWHM relative to a wavelength of maximum absorption in the range of about 600 nm to about 620 nm.

Since a color filter formed of a photosensitive resin composition using a pigment as a colorant has limitations on brightness and contrast due to the particle diameter of the pigment, demands for improving brightness and contrast continue to increase. Therefore, efforts have been made to prepare photosensitive resin compositions suitable for dyes by introducing dyes that do not form particles instead of pigments and thus realize color filters with improved brightness and contrast, and therefore, use dyes instead of pigments as the main coloring The photosensitive resin composition of the agent has some effects in improving brightness and contrast.

On the other hand, in recent years, demand for photosensitive resin compositions suitable for charge-coupled devices (CCDs), complementary metal-oxide-semiconductor image sensors, or the like other than conventional display devices such as LCDs has rapidly increased. However, a conventional photosensitive resin composition using a dye as a main colorant may not be able to achieve high color when applied to an image sensor, and hardly provide a high-definition color filter. The reason why high color cannot be achieved is that the pattern size of a color filter mounted on a charge-coupled device (CCD) is about 1/100 times to about 1/200 times smaller than that of a conventional color filter used for LCDs .

Therefore, the inventors of the present invention have developed a dye compound used in a photosensitive resin composition for a color filter after long-term research, which can be used by limiting the phthalocyanine compound relative to a specific wavelength range. The shortest wavelength of the full width at half maximum (FWHM) of each maximum absorption wavelength to achieve high color, allowing the compound to be easily applied with a size about 100 times to about 200 times smaller than color filter patterns used for LCDs pattern to increase resolution but reduce residue.

The shortest wavelength with respect to the full width at half maximum (FWHM) of the maximum absorption wavelength indicates the wavelength having the minimum value (a) among the energy width (Δλ) of the maximum absorption wavelength (b) in the absorption spectrum of a specific phthalocyanine compound. (Refer to Figure 1)

Having a full width at half maximum (FWHM) relative to a wavelength of maximum absorption in the range of about 600 nm to about 620 nm (eg, about 610 nm to about 620 nm, and eg, about 611 nm to about 616 nm) ) of the shortest wavelength phthalocyanines may not only exhibit excellent solubility for organic solvents (compared to the shortest wavelength of the phthalocyanines having the full width at half maximum (FWHM) relative to the maximum absorption wavelength outside the stated range compound), and also improve the brightness and chemical resistance of the photosensitive resin composition including the phthalocyanine compound as a colorant, and especially achieve high color (reduce Gx in CIE color coordinates (Gx, Gy)).

For example, a phthalocyanine compound exhibiting a shortest wavelength relative to a FWHM of a maximum absorption wavelength in a range of about 600 nm to about 620 nm may be represented by Chemical Formula 1.

[chemical formula 1] In Chemical Formula 1, R ¹ to R ⁴ are independently hydrogen atoms, R ⁵ to R ⁸ are independently hydrogen atoms or halogen atoms, and R ⁹ to R ¹⁶ are independently halogen atoms or represented by Chemical Formula 2, [Chemical Formula 2 ] Wherein, in Chemical Formula 2, R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

The compound represented by Chemical Formula 1 has excellent green spectral characteristics and a high molar extinction coefficient. In addition, since the compound represented by Chemical Formula 1 must contain at least one substituent represented by Chemical Formula 2, excellent solubility in organic solvents and excellent brightness and chemical resistance in the case of application to color filters may be exhibited.

For example, when the compound represented by Chemical Formula 1 does not include any substituent represented by Chemical Formula 2, the solubility to organic solvents, brightness, and chemical resistance may be greatly reduced, and thus the compound may not be used as a color compound. Colorants in the photosensitive resin composition of optical filters, and may be extremely difficult to achieve high color rendition image sensors.

The substituent represented by Chemical Formula 2 is "an aryloxy group having one or two alkyl groups as substituents" or "an alkoxy group having one or two alkyl groups as substituents", and in the aryloxy group, the alkyl group The group is substituted at the ortho and/or para position, and brightness and chemical resistance can be further improved. For example, when the alkyl group is substituted at the meta position, it may be difficult to achieve a green pixel for a color filter.

For example, Chemical Formula 2 may be represented by one of Chemical Formula 2-1 to Chemical Formula 2-4, but is not limited thereto. [chemical formula 2-1] [chemical formula 2-2] [chemical formula 2-3] [chemical formula 2-4] In Chemical Formula 2-1 to Chemical Formula 2-4, R ¹⁸ and R ¹⁹ are independently substituted or unsubstituted C1 to C20 alkyl groups, R ²⁰ to R ²² are independently hydrogen atoms or substituted or unsubstituted C1 to C20 alkyl, and L ¹ is a substituted or unsubstituted C1 to C20 alkylene.

In Chemical Formula 2-2 and Chemical Formula 2-3, at least one of R ¹⁸ and R ¹⁹ is a non-linear (branched chain) alkyl such as tert-butyl instead of a straight chain alkyl (such as methyl, ethyl and n-butyl), the compound is more desirable in terms of brightness and chemical resistance. In Chemical Formula 2-4, when at least one of R ²⁰ to R ²² is a substituted or unsubstituted C1 to C20 alkyl group, it may be more desirable in terms of brightness and chemical resistance.

For example, when the substituent represented by Chemical Formula 2 is represented by Chemical Formula 2-4, developability may be further improved.

In addition, the phthalocyanine compound represented by Chemical Formula 1 contains four hydrogen atoms and at least 4 halogen atoms, and the solubility to an organic solvent may be further improved due to these structural characteristics. Specifically, the phthalocyanine compound represented by Chemical Formula 1 includes four benzene rings in a core structure, the benzene rings being: i) a benzene ring having groups represented by R ¹ to R ⁴ ; ii) having A benzene ring of a group represented by R ⁵ to R ⁸ ; iii) a benzene ring of a group represented by R ⁹ to R ¹² ; and iv) a benzene ring of a group represented by R ¹³ to R ¹⁶ , wherein The benzene ring containing the substituent represented by Chemical Formula 2 among the four benzene rings contains three groups of all halogen atoms except the substituent represented by Chemical Formula 2, but does not contain the benzene group represented by Chemical Formula 2 The ring can contain all four groups of hydrogen atoms or halogen atoms. Therefore, its structural characteristics can easily obtain the shortest wavelength of the full width at half maximum (FWHM) with respect to the maximum absorption wavelength in the range of about 600 nm to about 620 nm, and further improve the solubility of the compound to organic solvents And thus contribute to improving brightness and securing process characteristics.

In particular, when the phthalocyanine compound exhibiting the shortest wavelength with respect to the FWHM of the maximum absorption wavelength in the range of about 600 nm to about 620 nm does not have the structure represented by Chemical Formula 1, the phthalocyanine compound is included The brightness and chemical resistance of the photosensitive resin composition as a colorant may be greatly reduced, or high color may not be achieved. Accordingly, the phthalocyanine compound according to an embodiment may desirably exhibit the shortest wavelength of FWHM with respect to the maximum absorption wavelength in the range of about 600 nm to about 620 nm, while having the structure represented by Chemical Formula 1.

For example, one or two of R ⁹ to R ¹⁶ may be represented by Chemical Formula 2. When one or two of R ⁹ to R ¹⁶ are not represented by Chemical Formula 2, a problem of decrease in luminance may occur.

For example, "one of R ⁹ to R ¹² " and/or "one of R ¹³ to R ¹⁶ " can be represented by Chemical Formula 2.

For example, “one of R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ ” can be represented by Chemical Formula 2.

For example, "one of R ¹⁰ and R ¹¹ " and "one of R ¹⁴ and R ¹⁵ " can be represented by Chemical Formula 2.

For example, the compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-20, but is not limited thereto. [chemical formula 1-1] [chemical formula 1-2] [chemical formula 1-3] [chemical formula 1-4] [chemical formula 1-5] [chemical formula 1-6] [chemical formula 1-7] [chemical formula 1-8] [chemical formula 1-9] [chemical formula 1-10] [chemical formula 1-11] [chemical formula 1-12] [chemical formula 1-13] [chemical formula 1-14] [chemical formula 1-15] [chemical formula 1-16] [chemical formula 1-17] [chemical formula 1-18] [chemical formula 1-19] [chemical formula 1-20] .

For example, since the phthalocyanine compound represented by Chemical Formula 1 contains at least one substituent represented by Chemical Formula 2, clearer color can be achieved even in a smaller amount, and can be produced by using the compound as a colorant A display device with improved color characteristics such as brightness, contrast, etc. For example, the compound can be a colorant, such as a dye (eg, a green dye), such as a dye that has a maximum transmission in the wavelength range of about 445 nm to about 560 nm.

In general, dyes are the most expensive among the components used in color filters. Consequently, expensive dyes may need to be used more to achieve desired effects, such as high brightness, high contrast or the like, and thus increase unit production costs. However, when the compound according to an embodiment is used as a dye in a color filter, the compound can achieve excellent color characteristics such as high brightness, high contrast, etc. even when used in a small amount, and reduces unit production cost.

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

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

The compound according to an embodiment may serve as a colorant such as a dye (eg, green dye) in a photosensitive resin composition, and thus may exhibit excellent color characteristics.

Based on the total amount of the photosensitive resin composition, the content of the compound according to one embodiment may be from about 1% by weight to about 40% by weight, such as from about 10% by weight to about 40% by weight, such as from about 20% by weight to about 40% by weight. % by weight, such as from about 1% to about 30% by weight, such as from about 1% to about 20% by weight, such as from about 1% to about 10% by weight. When the compound according to the example is contained within the above range, color reproduction and contrast are improved.

The photosensitive resin composition may further include pigments, such as yellow pigments, green pigments or combinations thereof.

The yellow pigment may be C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, etc. in the color index, which may be used alone or in admixture of two or more.

The green pigment may be C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59, etc. in the color index, which may be used alone or in admixture of two or more.

For example, the pigment can be included in the photosensitive resin composition in the form of a pigment dispersion.

The pigment dispersion liquid may contain a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.

Based on the total amount of the pigment dispersion, the content of the solid pigment may be from about 1% by weight to about 20% by weight, such as from about 8% by weight to about 20% by weight, such as from about 8% by weight to about 15% by weight, such as about 10% by weight. % by weight to about 20% by weight, such as about 10% by weight to about 15% by weight.

The dispersant may be a nonionic dispersant, anionic dispersant, cationic dispersant, or the like. Specific examples of the dispersant may be polyglycol and its ester, polyoxyalkylene, polyol ester alkylene oxide addition product, alcohol alkylene oxide addition product, sulfonate, sulfonate, carboxylate, carboxylate , Alkylamide alkylene oxide addition products, alkylamines, etc. These may be used alone or in admixture of two or more.

Commercially available examples of the dispersant may 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.; EFKA-47 manufactured by EFKA Chemicals Co. , EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc.; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse manufactured by Zeneka Co. 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc.; or PB711 or PB821 manufactured by Ajinomoto Inc.

Based on the total amount of the photosensitive resin composition, the content of the dispersant may be about 1% by weight to about 20% by weight. When the dispersant within the range is included, dispersion of the photosensitive resin composition is improved due to proper viscosity, and optical and biochemical quality can be maintained.

The solvent used to form the pigment dispersion may be ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like.

Based on the total amount of the photosensitive resin composition, the content of the pigment dispersion may be about 10% by weight to about 20% by weight, such as about 12% by weight to about 18% by weight. When the pigment dispersion liquid within the range is contained, a process margin can be desirably secured, and color reproducibility and contrast can be improved.

The binder resin may be an acryl-based resin.

The acryl-based resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer (which can be copolymerized with the first ethylenically unsaturated monomer), and contains at least one acryl Resins based on repeating units.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group. Examples of the monomer include (meth)acrylic acid, maleic acid, itaconic acid, fumaric acid, or combinations thereof.

Based on the total amount of the acryl-based binder resin, the content of the first ethylenically unsaturated monomer may be about 5% by weight to about 50% by weight, such as about 10% by weight to about 40% by weight.

The second ethylenically unsaturated monomer can be an aromatic vinyl compound, such as styrene, α-methylstyrene, vinyl toluene, vinyl benzyl methyl ether, etc.; an unsaturated carboxylic acid ester compound, such as (methyl styrene Base) methyl acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzene (meth) acrylate Methyl ester, cyclohexyl (meth)acrylate, phenyl (meth)acrylate, etc.; unsaturated aminoalkyl carboxylate compounds, such as 2-aminoethyl (meth)acrylate, 2-aminoethyl (meth)acrylate Dimethylaminoethyl ester, etc.; vinyl carboxylate compounds, such as vinyl acetate, vinyl benzoate, etc.; unsaturated glycidyl carboxylate compounds, such as glycidyl (meth)acrylate, etc.; vinyl cyanide compounds , such as (meth)acrylonitrile, etc.; unsaturated amide compounds, such as (meth)acrylamide, etc.; and the like. These may be used alone or in admixture of two or more.

Specific examples of the acrylic resin may be (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid/methacrylate Benzyl acrylate/2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc., but not limited thereto. These may be used alone or in admixture of two or more.

For example, the binder resin may further include epoxy resin and acrylic resin.

The weight average molecular weight of the binder resin may be from about 3,000 g/mol to about 150,000 g/mol, such as from about 5,000 g/mol to about 50,000 g/mol, such as from about 20,000 g/mol to about 30,000 g/mol. mole. When the binder resin has a weight average molecular weight within the range, the photosensitive resin composition has good physical and chemical properties, proper viscosity, and close contact with the substrate during production of the color filter.

The acid value of the binder resin may be about 15 mg KOH/g to about 60 mg KOH/g, for example, about 20 mg KOH/g to about 50 mg KOH/g. When the acid value of the binder resin is within the above range, resolution of pixel patterns may be improved.

Based on the total amount of the photosensitive resin composition, the content of the binder resin may be about 1 wt % to about 20 wt %, such as about 1 wt % to about 15 wt % or about 1 wt % to about 10 wt %. When the binder resin is contained within the above range, developability may be improved and excellent surface smoothness may be improved due to improved crosslinking during production of the color filter.

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

Due to the ethylenically unsaturated double bond, the photopolymerizable compound can cause sufficient polymerization during exposure during pattern formation and form a pattern having excellent heat resistance, light resistance, and chemical resistance.

Specific examples of the photopolymerizable compound may be ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, Acrylates, 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 monomethacrylate Ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tri(meth)acryloxyethyl phosphate, novolac epoxy (meth)acrylate, etc.

Commercially available examples of the photopolymerizable compound may be as follows. Monofunctional (meth)acrylates may include Aronix M-101 ^® , M-111 ^® , M-114 ^® (Toagosei Chemistry Industry Co., Ltd.); KAYARAD TC-110S ^® , TC-120S ^® (Nippon Kayaku Co., Ltd.); V-158 ^® , V-2311 ^® (Osaka Organic Chemical Ind., Ltd.), etc. Examples of difunctional (meth)acrylates may include Aronix M-210 ^® , M-240 ^® , M-6200 ^® (Toa Gosei Chemical Industry Co., Ltd.); KAYARAD HDDA ^® , HX-220 ^® , R-604 ^® ( Nippon Kayaku Co., Ltd.); V-260 ^® , V-312 ^® , V-335 HP ^® (Osaka Organic Chemical Industry Co., Ltd.), etc. Examples of trifunctional (meth)acrylates may include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-7100 ^® , M-8030 ^® , M-8060 ^® (Toya Synthetic Chemical Industry Co., Ltd.); KAYARAD TMPTA ^® , DPCA-20 ^® , DPCA-30 ^® , DPCA-60 ^® , DPCA-120 ^® (Nippon Kayaku Co., Ltd.); V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® (Osaka Yuki Kayaku Kogyo Co. Ltd.), etc. These can be used alone or as a mixture of two or more Form use.

The photopolymerizable compound can be treated with an anhydride to improve developability.

Based on the total amount of the photosensitive resin composition, the content of the photopolymerizable compound may be about 1% by weight to about 15% by weight, such as about 1% by weight to about 10% by weight. When the photopolymerizable compound is contained within the range, the photopolymerizable compound is sufficiently cured and has excellent reliability during exposure during pattern formation, and developability of an alkaline developer can be improved.

The photopolymerization initiator can be a photopolymerization initiator commonly used in photosensitive resin compositions, such as acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, Oxime compounds or combinations thereof.

Examples of acetophenones can be 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-tert-butyl Trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4- (Methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. .

Examples of benzophenones may be benzophenone, benzoyl benzoate, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4, 4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichloro Benzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.

Examples of thioxanthone compounds may be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone , 2-chlorothioxanthone, etc.

Examples of benzoin-based compounds may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.

Examples of triazines can be 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-(naphthol 1- base)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthol 1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-sunflower-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, etc. .

Examples of oxime compounds may be O-acyl oxime compounds, 2-(O-benzoyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1- (O-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-oxazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxygen Amino-1-phenylpropan-1-one, etc. Specific examples of O-acyl oximes may be 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-benzene base)-butan-1-one, 1-(4-phenylthiophenyl)-butane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylthiophenyl Base)-octane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylthiophenyl)-octane-1-one oxime-O-acetate, 1- (4-Phenylthiophenyl)-butan-1-one oxime-O-acetate, etc.

In addition to the above compounds, the photopolymerization initiator may further include oxazole compounds, diketone compounds, borate-based compounds, diazo-based compounds, imidazole-based compounds, biimidazole-based compounds, fluorene-based compounds, and the like.

The photopolymerization initiator can be used together with a photosensitizer capable of causing a chemical reaction by absorbing light and becoming excited and then transferring its energy.

Examples of the photosensitizer may be tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, dipentaerythritol tetra-3-mercaptopropionate, and the like.

Based on the total amount of the photosensitive resin composition, the content of the photopolymerization initiator may be about 0.01% by weight to about 10% by weight, such as about 0.1% by weight to about 5% by weight. When the photopolymerization initiator is contained within the range, excellent reliability can be ensured due to sufficient curing during exposure during pattern formation, and the pattern can have excellent resolution and close contact properties as well as excellent heat resistance, Light resistance and chemical resistance, and can prevent decrease in transmittance due to non-reactive initiator.

The solvent is a material that has compatibility with, but does not react with, the compound, the pigment, the binder resin, the photopolymerizable compound, and the photopolymerization initiator according to an embodiment.

Examples of solvents may include alcohols such as methanol, ethanol, etc.; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran, etc.; glycol ethers such as ethylene glycol monomethyl ether, ethyl Glycol monoethyl ether, etc.; Ethyl glycol acetate, such as methyl glycol acetate, ethyl glycol acetate, diethyl glycol acetate, etc.; carbitol, such as methyl ethyl carbit Alcohol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether, etc.; propylene glycol alkane Ether acetates, such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, etc.; aromatic hydrocarbons, such as toluene, xylene, etc.; ketones, such as methyl ethyl ketone, cyclohexanone, 4-hydroxy -4-methyl-2-pentanone, methyl-n-acetone, methyl-n-butanone, methyl-n-pentanone, 2-heptanone, etc.; saturated alicyclic monocarboxylic acid alkyl esters, such as acetic acid Ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactate esters, such as methyl lactate, ethyl lactate, etc.; alkyl oxyacetates, such as methyl oxyacetate, ethyl oxyacetate, oxy Butyl acetate, etc.; alkyl alkoxyacetate, such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.; Alkyl 3-oxypropionate, such as methyl 3-oxypropionate, ethyl 3-oxypropionate, etc.; Alkyl 3-alkoxypropionate, such as methyl 3-methoxypropionate Esters, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; alkyl 2-oxypropionate, such as 2-oxypropionate Methyl ester, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.; alkyl 2-alkoxypropionate, such as methyl 2-methoxypropionate, 2-methoxypropionate Ethyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-oxy-2-methylpropionate, such as 2-oxy-2-methylpropionate Methyl esters, ethyl 2-oxy-2-methylpropionate, etc.; alkyl monooxymonocarboxylates of alkyl 2-alkoxy-2-methylpropionates, such as 2-methoxy -Methyl 2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc.; esters, such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate , ethyl hydroxy acetate, methyl 2-hydroxy-3-methyl butyrate, etc.; keto esters, such as ethyl pyruvate, etc. In addition, high boiling point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformaniline, N-methylacetamide, N,N-di Methylacetamide, N-Methylpyrrolidone, Dimethylsulfoxide, Benzyl Ethyl Ether, Dihexyl Ether, Acetyl Acetone, 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, Phenyl Ethylene glycol acetate, etc.

In consideration of miscibility and reactivity, glycol ethers, such as ethylene glycol monoethyl ether, etc.; glycol alkyl ether acetates, such as ethyl glycol acetate, etc.; esters, such as propionic acid 2 - hydroxyethyl esters, etc.; carbitols, such as diethylene glycol monomethyl ether, etc.; propylene glycol alkyl ether acetates, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, etc.; and/or ketones, such as Cyclohexanone etc.

The solvent may be included in a balance of, for example, about 30% by weight to about 80% by weight based on the total amount of the photosensitive resin composition. When the solvent within the range is included, the photosensitive resin composition may have an appropriate viscosity, and thus improve handling during production of color filters.

The photosensitive resin composition may further include a compound represented by Chemical Formula 3.

[chemical formula 3] In Chemical Formula 3, R ²³ and R ²⁴ are independently hydroxyl or substituted or unsubstituted C1 to C20 alkyl, L ² to L ⁴ are independently substituted or unsubstituted C1 to C20 alkylene, And n1 and n2 are independently integers from 0 to 5, and the restriction is 3 ≤ n1+n2 ≤ 5.

For example, the compound represented by Chemical Formula 3 may act as an antioxidant.

For example, in Chemical Formula 3, R ²³ may be an alkyl-substituted C1 to C20 alkyl group, R ²⁴ may be a hydroxyl group, n1 may be an integer of 2, and n2 may be an integer of 1.

The photosensitive resin composition according to another embodiment may further include an epoxy compound in order to improve the intimate contact property with the substrate.

Examples of epoxy compounds may include phenol novolac epoxy compounds, tetramethylbiphenyl epoxy compounds, bisphenol A epoxy compounds, alicyclic epoxy compounds, or combinations thereof.

Based on 100 parts by weight of the photosensitive resin composition, the epoxy compound may comprise about 0.01 to about 20 parts by weight, such as about 0.1 to about 10 parts by weight. When the epoxy compound within the range is contained, intimate contact properties, storage properties, and the like may be improved.

In addition, the photosensitive resin composition may further include a silane coupling agent having reactive substituents such as carboxyl, methacryl, isocyanate, epoxy, etc., so as to improve its adhesion to the substrate.

Examples of silane coupling agents may include trimethoxysilyl benzoic acid, γ-methacrylpropoxytrimethoxysilane, vinyltriacetyloxysilane, vinyltrimethoxysilane, γ-isocyanate propyl Triethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, etc. These may be used alone or in admixture of two or more.

Based on 100 parts by weight of the photosensitive resin composition, the silane coupling agent may be included in an amount of about 0.01 parts by weight to about 10 parts by weight. When the silane coupling agent within the range is included, intimate contact properties, storage properties, and the like can be improved.

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

Examples of surfactants may include fluorene-based surfactants such as BM- ^1000® and BM- ^1100® (BM Chemie Inc.; MEGAFACE F 142D ^® , F 172 ^® , F 173 ^® and F 183 ^® (Dainippon Ink Kagaku Kogyo Co., Ltd.); FULORAD FC-135 ^® , FULORAD FC-170C ^® , FULORAD FC-430 ^® and FULORAD FC-431 ^® (Sumitomo 3M Co., Ltd.)); SURFLON S-112 ^® , SURFLON S-113 ^® , SURFLON S-131 ^® , SURFLON S-141 ^® and SURFLON S-145 ^® (ASAHI Glass Co., Ltd. )); and SH-28PA ^® , SH-190 ^® , SH-193 ^® , SZ-6032 ^® and SF-8428 ^® etc. (Toray Silicone Co., Ltd.).

The surfactant may be used in an amount of about 0.001 parts by weight to about 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included within the range, excellent wetting and coating uniformity on the glass substrate may be ensured, but no contamination may be generated.

In addition, the photosensitive resin composition may contain predetermined amounts of other additives such as antioxidants, stabilizers, etc. unless the additives degrade the properties of the photosensitive resin composition.

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

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

The process includes: coating the photosensitive resin composition on the support substrate by spin coating, slit coating, inkjet printing and other methods; drying the coated positive photosensitive resin composition to form a photosensitive resin composition film; exposing the positive photosensitive resin composition film; developing the exposed positive photosensitive resin composition film in an alkaline aqueous solution to obtain a photosensitive resin layer; and heat-treating the photosensitive resin layer. Patterning process conditions are well known in the related art and are not described in detail in this specification.

Hereinafter, the present invention is explained in more detail with reference to examples, however, these examples are not construed as limiting the scope of the present invention in any sense. ( Synthesis of Compounds ) Synthesis Example 1 : Synthesis of Compounds Represented by Chemical Formula 1-1

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-isopropyl-phenol (2.56 g), K ₂ CO ₃ (3.9 g) and N,N-dimethylformaldehyde Amide (25ml) was placed in a 100ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2-isopropyl-phenoxy)-3,5,6-trichloro-phthalonitrile.

4-(2-Isopropyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 0.73 g), phthalonitrile (0.35 g), 1,8-diazabicycloundec-7-ene (2.08 g) and 1-pentenol (15 g) were placed in a 100 ml flask and Heat to 90°C to dissolve the solid, add zinc acetate (0.50 g), and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum-dried to obtain the compound represented by Chemical Formula 1-1.

[chemical formula 1-1] Maldi-tof MS: 1190.69 m/z Synthesis Example 2 : Synthesis of compounds represented by Chemical Formula 1-2

4-(2-Isopropyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 2.91 g), phthalonitrile (0.70 g), 1,8-diazabicycloundec-7-ene (4.16 g) and 1-pentenol (30 g) were placed in a 100 ml flask and Heat to 90°C to dissolve the solids, add zinc acetate (1.00 g), and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-2.

[chemical formula 1-2] Maldi-tof MS: 1090.96 m/z Synthesis Example 3 : Synthesis of compounds represented by Chemical Formula 1-3

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-tert-butyl-phenol (2.83 g), K ₂ CO ₃ (3.9 g) and N,N-dimethylformaldehyde Amide (25ml) was placed in a 100ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile.

4-(2-tert-Butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 0.70 g), phthalonitrile (0.34 g), 1,8-diazabicycloundec-7-ene (2.01 g) and 1-pentenol (15 g) were placed in a 100 ml flask and Heat to 90°C to dissolve the solid, add zinc acetate (0.48 g), and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-3.

[chemical formula 1-3] Maldi-tof MS: 1218.75 m/z Synthesis Example 4 : Synthesis of compounds represented by Chemical Formula 1-4

4-(2-tert-Butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 2.80 g), phthalonitrile (0.67 g), 1,8-diazabicycloundec-7-ene (4.01 g) and 1-pentenol (30 g) were placed in a 100 ml flask and Heat to 90°C to dissolve the solid, add zinc acetate (0.97 g), and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-4.

[chemical formula 1-4] Maldi-tof MS: 1104.98 m/z Synthesis Example 5 : Synthesis of compounds represented by Chemical Formula 1-5

3,4,5,6-tetrachlorophthalonitrile (5 g), p-cresol (2.83 g), K ₂ CO ₃ (3.9 g) and N,N-dimethylformamide (25 ml) was placed in a 100 ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2-methyl-phenoxy)-3,5,6-trichloro-phthalonitrile.

4-(2-Methyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile (0.79 g), phthalonitrile (0.38 g), 1,8-diazabicycloundec-7-ene (2.26 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated To 90°C to dissolve the solid, add zinc acetate (0.54 g) and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-5.

[chemical formula 1-5] Maldi-tof MS: 1134.58 m/z Synthesis Example 6 : Synthesis of compounds represented by Chemical Formula 1-6

3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-dimethylphenol (2.30 g), K ₂ CO ₃ (3.9 g) and N,N-dimethyl Formamide (25ml) was placed in a 100ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2,6-dimethyl-phenoxy)-3,5,6-trichloro-phthalonitrile.

4-(2,6-Dimethyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile Nitrile (0.76 g), phthalonitrile (0.36 g), 1,8-diazabicycloundec-7-ene (2.17 g) and 1-pentenol (15 g) were placed in a 100 ml flask medium and heated to 90°C to dissolve the solids, zinc acetate (0.52 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-6.

[chemical formula 1-6] Maldi-tof MS: 1162.64 m/z Synthesis Example 7 : Synthesis of compounds represented by Chemical Formula 1-7

4-(2,6-Dimethyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile Nitrile (3.03 g), phthalonitrile (0.73 g), 1,8-diazabicycloundec-7-ene (4.33 g) and 1-pentenol (30 g) were placed in a 100 ml flask medium and heated to 90°C to dissolve the solids, zinc acetate (1.04 g) was added, and the resultant stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-7.

[chemical formula 1-7] Maldi-tof MS: 1076.93 m/z Synthesis Example 8 : Synthesis of compounds represented by Chemical Formula 1-8

3,4,5,6-tetrachlorophthalonitrile (5 g), 2,4-di-tert-butylphenol (3.9 g), K ₂ CO ₃ (3.9 g) and N,N-di Methylformamide (25 ml) was placed in a 100 ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2,4-di-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile.

4-(2,4-Di-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachloro-phthalonitrile Dicarbonitrile (0.70 g), phthalonitrile (0.34 g), 1,8-diazabicycloundec-7-ene (2.01 g) and 1-pentenol (15 g) were placed in 100 ml in a flask and heated to 90°C to dissolve the solids, zinc acetate (0.48 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-8.

[chemical formula 1-8] Maldi-tof MS: 1330.96 m/z Synthesis Example 9 : Synthesis of compounds represented by Chemical Formula 1-9

4-(2,4-Di-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachloro-phthalonitrile Dicarbonitrile (2.80 g), phthalonitrile (0.68 g), 1,8-diazabicycloundec-7-ene (4.01 g) and 1-pentenol (15 g) were placed in 100 ml in a flask and heated to 90°C to dissolve the solids, zinc acetate (0.97 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-9.

[chemical formula 1-9] Maldi-tof MS: 1161.09 m/z Synthesis Example 10 : Synthesis of compounds represented by Chemical Formula 1-10

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-tert-butyl-4-cresol (3.09 g), K ₂ CO ₃ (3.9 g) and N,N-di Methylformamide (25 ml) was placed in a 100 ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2-tert-butyl-4-methylphenoxy)-3,5,6-trichloro-phthalonitrile.

4-(2-tert-butyl-4-methylphenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile Dicarbonitrile (0.68 g), phthalonitrile (0.33 g), 1,8-diazabicycloundec-7-ene (1.9 g) and 1-pentenol (15 g) were placed in 100 ml in a flask and heated to 90°C to dissolve the solids, zinc acetate (0.47 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-10.

[chemical formula 1-10] Maldi-tof MS: 1246.80 m/z Synthesis Example 11 : Synthesis of compounds represented by Chemical Formula 1-11

4-(2-tert-Butyl-4-methylphenoxy)-3,5,6-trichloro-phthalonitrile (2 g), phthalonitrile (0.65 g), 1, 8-Diazabicycloundec-7-ene (1.9 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solids, zinc acetate (0.47 g) was added , and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-11.

[chemical formula 1-11] Maldi-tof MS: 1109.03 m/z Synthesis Example 12 : Synthesis of compounds represented by Chemical Formula 1-12

3,4,5,6-tetrachlorophthalonitrile (5 g), 2,2-dimethyl-1-propanol (1.66 g), diazabicyclounde-7-ene (4.29 g) and N,N-dimethylformamide (25 ml) were placed in a 100 ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2,2-dimethyl-1-propoxy)-3,5,6-trichloro-phthalonitrile.

4-(2,2-Dimethyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile Dicarbonitrile (0.84g), phthalonitrile (0.40g), 1,8-diazabicycloundec-7-ene (2.40g) and 1-pentenol (15g) in 100ml in a flask and heated to 90°C to dissolve the solids, zinc acetate (0.58 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-12.

[chemical formula 1-12] Maldi-tof MS: 1094.60 m/z Synthesis Example 13 : Synthesis of compounds represented by Chemical Formula 1-13

4-(2,2-Dimethyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (1 g), 3,4,5,6-tetrachlorophthalonitrile Dicarbonitrile (1.67g), phthalonitrile (0.40g), 1,8-diazabicycloundec-7-ene (2.40g) and 1-pentenol (15g) in 100ml in a flask and heated to 90°C to dissolve the solids, zinc acetate (0.58 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-13.

[chemical formula 1-13] Maldi-tof MS: 1042.91 m/z Synthesis Example 14 : Synthesis of compounds represented by Chemical Formula 1-14

4-(2,2-Dimethyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (2 g), phthalonitrile (0.81 g), 1, 8-Diazabicycloundec-7-ene (2.40 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solids, zinc acetate (0.58 g) was added , and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-14.

[chemical formula 1-14] Maldi-tof MS: 956.84 m/z Synthesis Example 15 : Synthesis of compounds represented by Chemical Formula 1-15

3,4,5,6-tetrachlorophthalonitrile (5 g), 3-methyl-1-butanol (1.66 g), diazabicyclounde-7-ene (4.29 g) and N,N-Dimethylformamide (25 ml) was placed in a 100 ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(3-methyl-1-butoxy)-3,5,6-trichloro-phthalonitrile.

4-(3-Methyl-1-butoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile (0.84 g), phthalonitrile (0.40 g), 1,8-diazabicycloundec-7-ene (2.40 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solid, zinc acetate (0.58 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-15.

[chemical formula 1-15] Maldi-tof MS: 1094.60 m/z Synthesis Example 16 : Synthesis of compounds represented by Chemical Formula 1-16

4-(3-Methyl-1-butoxy)-3,5,6-trichloro-phthalonitrile (1 g), 3,4,5,6-tetrachlorophthalonitrile (1.67 g), phthalonitrile (0.40 g), 1,8-diazabicycloundec-7-ene (2.40 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solid, zinc acetate (0.58 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-16.

[chemical formula 1-16] Maldi-tof MS: 1042.91 m/z Synthesis Example 17 : Synthesis of compounds represented by Chemical Formula 1-17

4-(3-Methyl-1-butoxy)-3,5,6-trichloro-phthalonitrile (2 g), phthalonitrile (0.81 g), 1,8-di Azabicycloundec-7-ene (2.40 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solids, zinc acetate (0.58 g) was added, and stirred The resultant was simultaneously heated to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-17.

[chemical formula 1-17] Maldi-tof MS: 956.84 m/z Synthesis Example 18 : Synthesis of compounds represented by Chemical Formula 1-18

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-methyl-1-propanol (1.39 g), diazabicycloundec-7-ene (4.29 g) and N,N-Dimethylformamide (25 ml) was placed in a 100 ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(3-methyl-1-butoxy)-3,5,6-trichloro-phthalonitrile.

4-(2-Methyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile (0.88 g), phthalonitrile (0.42 g), 1,8-diazabicycloundec-7-ene (2.52 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solid, zinc acetate (0.61 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-18.

[chemical formula 1-18] Maldi-tof MS: 1066.55 m/z Synthesis Example 19 : Synthesis of compounds represented by Chemical Formula 1-19

4-(2-Methyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (1 g), 3,4,5,6-tetrachlorophthalonitrile (1.76 g), phthalonitrile (0.42 g), 1,8-diazabicycloundec-7-ene (2.52 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solid, zinc acetate (0.61 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-19.

[chemical formula 1-19] Maldi-tof MS: 1028.89 m/z Synthesis Example 20 : Synthesis of compounds represented by Chemical Formula 1-20

4-(2-Methyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (2 g), phthalonitrile (0.85 g), 1,8-di Azabicycloundec-7-ene (2.52 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solids, zinc acetate (0.61 g) was added, and stirred The resultant was simultaneously heated to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-20.

[chemical formula 1-20] Maldi-tof MS: 928.78 m/z Synthesis Example 21 : Synthesis of compounds represented by Chemical Formula 1-21

4-(2,4-Di-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), phthalonitrile (2.03 g), 1, 8-Diazabicycloundec-7-ene (4.01 g) and 1-pentenol (15 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solids, zinc acetate (0.97 g) was added , and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-21.

[chemical formula 1-21] Maldi-tof MS: 885.56 m/z Comparative Synthesis Example 1 : Synthesis of a compound represented by Chemical Formula C-1

4-(2-sec-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g), 1,8-diazabicyclounde-7-ene (0.30 g), 1-pentenol (7 g) and zinc acetate (0.12 g) were placed in a 100 ml flask and stirred while heating at 140°C. When the reaction was complete, the resultant was concentrated and purified by column chromatography. The purified liquid was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula C-1.

[Chemical Formula C-1] Maldi-tof MS: 1584.04 m/z Comparative Synthesis Example 2 : Synthesis of a compound represented by Chemical Formula C-2

3,4,5,6-tetrachlorophthalonitrile (5 g), 2,4-di-tert-butylphenol (2.75 g), K ₂ CO ₃ (3.9 g) and N,N-di Methylformamide (25 ml) was placed in a 100 ml flask and then stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated to obtain a solid. The obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 3,4,6-trichloro-5-(2,4-dimethyl-phenoxy) - Phthalonitrile.

3,4,6-Trichloro-5-(2,4-di-tert-butyl-phenoxy)-phthalonitrile (1 g), 1,8-diazabicycloundec-7 -ene (1.08 g) and 1-pentenol (14 g) were placed in a 100 ml flask and heated to 90 °C to dissolve the solids, zinc acetate (0.26 g) was added, and the resultant was stirred while heating to 140 °C . When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula C-2.

[Chemical formula C-2] Maldi-tof MS: 1808.47 m/z Comparative Synthesis Example 3 : Synthesis of a compound represented by Chemical Formula C-3

3,4,5,6-tetrachlorophthalonitrile (5 g), 2,4-dimethoxyphenol (3.47 g), K ₂ CO ₃ (3.9 g) and N,N-dimethyl Methylformamide (25 ml) was placed in a 100 ml flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated to obtain a solid. The obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 3,4,6-trichloro-5-(2,4-dimethoxy-phenoxy )-phthalonitrile.

3,4,6-Trichloro-5-(2,4-dimethoxy-phenoxy)-phthalonitrile (2 g), 1,8-diazabicycloundec-7- Alkene (0.99 g) and 1-pentenol (14 g) were placed in a 100 ml flask and heated to 90°C to dissolve the solids, zinc acetate (0.24 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula C-3.

[Chemical formula C-3] Maldi-tof MS: 1591.80 m/z Comparative Synthesis Example 4 : Synthesis of a compound represented by Chemical Formula C-4

4-(2,4-dimethoxy-phenoxy)-3,5,6-trichloro-phthalonitrile (0.7 g), 3,4,5,6 -Tetrachlorophthalonitrile (1.45 g), 1,8-diazabicycloundec-7-ene (1.38 g) and 1-pentenol (14 g) were placed in a 100 ml flask and heated To 90°C to dissolve the solid, add zinc acetate (0.33 g) and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula C-4.

[chemical formula C-4] Maldi-tof MS: 1237.54 m/z Comparative Synthesis Example 5 : Synthesis of a compound represented by Chemical Formula C-5

4-(2-tert-Butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 0.70 g), 4,5-dichlorophthalonitrile (0.52 g), 1,8-diazabicycloundec-7-ene (2.01 g) and 1-pentenol (15 g) in In a 100 ml flask and heated to 90°C to dissolve the solid, zinc acetate (0.48 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula C-5.

[chemical formula C-5] Maldi-tof MS: 1287.63 m/z Comparative Synthesis Example 6 : Synthesis of a compound represented by Chemical Formula C-6

4-(2-tert-Butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 0.70g), 4-dichlorophthalonitrile (0.43g), 1,8-diazabicycloundec-7-ene (2.01g) and 1-pentenol (15g) in 100ml in a flask and heated to 90°C to dissolve the solids, zinc acetate (0.48 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula C-6.

[chemical formula C-6] Maldi-tof MS: 1253.19 m/z Evaluation 1 : Measure the shortest wavelength of the full width at half maximum ( FWHM ) relative to the maximum absorption wavelength

The compounds according to Synthesis Example 1 to Synthesis Example 21 and Comparative Synthesis Example 1 to Comparative Synthesis Example 6 were prepared at a concentration of 0.005% by weight using a dilution solvent (PGMEA). Absorption spectra of each of the phthalocyanine compounds according to Synthesis Example 1 to Synthesis Example 21 and Comparative Synthesis Example 1 to Comparative Synthesis Example 6 were obtained, and the results are shown in Table 1 (UV-1800, SHIMADZU).

[Table 1] The shortest wavelength (nm) relative to the full width at half maximum (FWHM) of the wavelength of maximum absorption Synthetic Example 1 616 Synthetic example 2 617 Synthetic Example 3 618 Synthetic Example 4 617 Synthetic Example 5 618 Synthetic Example 6 618 Synthetic Example 7 618 Synthetic Example 8 616 Synthetic Example 9 618 Synthetic Example 10 616 Synthetic Example 11 611 Synthetic Example 12 617 Synthetic Example 13 618 Synthetic Example 14 611 Synthetic Example 15 617 Synthetic Example 16 618 Synthetic Example 17 611 Synthetic Example 18 617 Synthetic Example 19 618 Synthetic Example 20 611 Synthetic Example 21 608 Comparative Synthesis Example 1 628 Comparative Synthesis Example 2 624 Comparative Synthesis Example 3 623 Comparative Synthesis Example 4 626 Comparative Synthesis Example 5 625 Comparative Synthesis Example 6 623 Assessment 2 : Solubility Measurements

The solubility of the compounds according to Synthesis Example 1 to Synthesis Example 21 and Comparative Synthesis Example 1 to Comparative Synthesis Example 6 was measured by adding a dilution solvent (PGMEA) to 0.5 g of each compound and stirring at 25° C. at 100 revolutions The mixture (MIXROTAR VMR-5, Iuchi eiei Dou Co.) was stirred separately for one hour per minute, and the results are shown in Table 2. Solubility Evaluation Criteria Based on the total amount of diluting solvent, greater than or equal to 10% by weight of the compound (solute) dissolved: ○ Based on the total amount of the diluted solvent, less than 10% by weight of the compound (solute) dissolved: X

[Table 2] (Unit: weight %) Solubility Synthetic Example 1 ○ Synthetic example 2 ○ Synthetic Example 3 ○ Synthetic Example 4 ○ Synthetic Example 5 ○ Synthetic Example 6 ○ Synthetic Example 7 ○ Synthetic Example 8 ○ Synthetic Example 9 ○ Synthetic Example 10 ○ Synthetic Example 11 ○ Synthetic Example 12 ○ Synthetic Example 13 ○ Synthetic Example 14 ○ Synthetic Example 15 ○ Synthetic Example 16 ○ Synthetic Example 17 ○ Synthetic Example 18 ○ Synthetic Example 19 ○ Synthetic Example 20 ○ Synthetic Example 21 x Comparative Synthesis Example 1 x Comparative Synthesis Example 2 x Comparative Synthesis Example 3 x Comparative Synthesis Example 4 x Comparative Synthesis Example 5 x Comparative Synthesis Example 6 x

Referring to Table 2, compared with the compounds according to Synthesis Example 21 and Comparative Synthesis Example 1 to Comparative Synthesis Example 6, the compounds of Synthesis Example 1 to Synthesis Example 20 (compounds according to an example) exhibit excellent solubility to organic solvents, And therefore has excellent color characteristics when used in photosensitive resin compositions and the like. (Synthetic photosensitive resin composition) Example 1

Components mentioned below were mixed in the compositions shown in Table 3 to Table 5 to prepare each photosensitive resin composition according to Example 1 to Example 21 and Comparative Example 1 to Comparative Example 6.

Specifically, a photopolymerization initiator was dissolved in a solvent, the solution was stirred at room temperature for 2 hours, a binder resin and a photopolymerizable monomer were added thereto, and the mixture was stirred at room temperature for 2 hours. Subsequently, the compound (dye) and pigment (pigment dispersion liquid) prepared in Synthesis Example were added to the reactant as a colorant, and the mixture was stirred at room temperature for one hour. Next, an antioxidant and a leveling agent were added, and the product was filtered three times to remove impurities, thereby preparing each photosensitive resin composition.

[Table 3] (Unit: weight %) example 1 2 3 4 5 6 7 8 9 10 binder resin EHPE-3150 (DAICEL, epoxy) 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 NPR-5216 (Miwon, acryl-based) 7.91 7.91 7.91 7.91 7.91 7.91 7.91 7.91 7.91 7.91 photopolymerizable monomer GM66G0P (QPPC) 4.92 4.92 4.92 4.92 4.92 4.92 4.92 4.92 4.92 4.92 Miramer 2200 (US source) 0.37 0.37 0.37 0.37 0.37 0.37 0.37 0.37 0.37 0.37 Photopolymerization initiator SPI-03 (Samyang Corporation) 0.78 0.78 0.78 0.78 0.78 0.78 0.78 0.78 0.78 0.78 IRG369 (BASF) 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 Antioxidants AO-80 (ADEKA) 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 pigment G58 pigment dispersion (Sanyo (SANYO), AG1623) 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Y138 Pigment Dispersion (ENF, EC-1200Y) 17.79 17.79 17.79 17.79 17.79 17.79 17.79 17.79 17.79 17.79 dye 30.22 (synthesis example 1) 30.22 (synthesis example 2) 30.22 (synthesis example 3) 30.22 (synthesis example 4) 30.22 (synthesis example 5) 30.22 (synthesis example 6) 30.22 (synthesis example 7) 30.22 (synthesis example 8) 30.22 (synthesis example 9) 30.22 (synthesis example 10) solvent PGMEA (Daicel) 34.50 34.50 34.50 34.50 34.50 34.50 34.50 34.50 34.50 34.50 leveling agent F554 (DIC) 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 total 100.00 100.00 100.00 100.00 100.00 100.00 100.00 100.00 100.00 100.00

[Table 4] (Unit: weight %) example 11 12 13 14 15 16 17 18 19 20 binder resin EHPE-3150 (Daicel, epoxy) 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 NPR-5216 (American source, acryl-based) 7.91 7.91 7.91 7.91 7.91 7.91 7.91 7.91 7.91 7.91 photopolymerizable monomer GM66G0P (QPPC) 4.92 4.92 4.92 4.92 4.92 4.92 4.92 4.92 4.92 4.92 Miramer 2200 (US source) 0.37 0.37 0.37 0.37 0.37 0.37 0.37 0.37 0.37 0.37 Photopolymerization initiator SPI-03 (Sanyang Company) 0.78 0.78 0.78 0.78 0.78 0.78 0.78 0.78 0.78 0.78 IRG369 (BASF) 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 Antioxidants AO-80 (Adico) 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 pigment G58 pigment dispersion (Sanyo, AG1623) 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Y138 Pigment Dispersion (ENF, EC-1200Y) 17.79 17.79 17.79 17.79 17.79 17.79 17.79 17.79 17.79 17.79 dye 30.22 (synthesis example 11) 30.22 (synthesis example 12) 30.22 (synthesis example 13) 30.22 (synthesis example 14) 30.22 (synthesis example 15) 30.22 (synthesis example 16) 30.22 (synthesis example 17) 30.22 (synthesis example 18) 30.22 (synthesis example 19) 30.22 (synthesis example 20) solvent PGMEA (Daicel) 34.50 34.50 34.50 34.50 34.50 34.50 34.50 34.50 34.50 34.50 leveling agent F554 (DIC) 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 total 100.00 100.00 100.00 100.00 100.00 100.00 100.00 100.00 100.00 100.00

[Table 5] (Unit: weight %) example comparative example twenty one 1 2 3 4 5 6 binder resin EHPE-3150 (Daicel, epoxy) 0.27 0.27 0.27 0.27 0.27 0.27 0.27 NPR-5216 (American source, acryl-based) 7.91 7.91 7.91 7.91 7.91 7.91 7.91 photopolymerizable monomer GM66G0P (QPPC) 4.92 4.92 4.92 4.92 4.92 4.92 4.92 Miramer 2200 (US source) 0.37 0.37 0.37 0.37 0.37 0.37 0.37 Photopolymerization initiator SPI-03 (Sanyang Company) 0.78 0.78 0.78 0.78 0.78 0.78 0.78 IRG369 (BASF) 0.01 0.01 0.01 0.01 0.01 0.01 0.01 Antioxidants AO-80 (Adico) 0.01 0.01 0.01 0.01 0.01 0.01 0.01 pigment G58 pigment dispersion (Sanyo AG1623) 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Y138 Pigment Dispersion (ENF, EC-1200Y) 17.79 17.79 17.79 17.79 17.79 17.79 17.79 dye 30.22 (synthesis example 21) 30.22 (comparative synthesis example 1) 30.22 (comparative synthesis example 2) 30.22 (compare synthetic example 3) 30.22 (compare synthetic example 4) 30.22 (compare synthetic example 5) 30.22 (compare synthetic example 6) solvent PGMEA (Daicel) 34.50 34.50 34.50 34.50 34.50 34.50 34.50 leveling agent F554 (DIC) 0.20 0.20 0.20 0.20 0.20 0.20 0.20 total 100.00 100.00 100.00 100.00 100.00 100.00 100.00 Evaluation 3 : Color coordinates, brightness, chemical resistance, developability, and surface wrinkle

The photosensitive resin compositions according to Examples 1 to 21 and Comparative Examples 1 to 6 were respectively coated on a 1 mm thick degreased glass substrate to a thickness of 1 μm to 3 μm and then dried on a 90° C. hot plate For 2 minutes, a film is obtained. The film was exposed by using a high pressure mercury lamp with a dominant wavelength of 365 nm. Subsequently, the film was dried in a forced convection drying oven at 230° C. for 20 minutes to obtain a sample. For the pixel layer, a spectrophotometer (MCPD3000, Otsuka Electronic Co., Ltd.) was used to evaluate the C illuminant reference color purity, and the CIE color coordinate reference was used to calculate the brightness (Y), and the results were shown in Table 6.

Also, after measuring the initial thickness of the sample obtained by exposure and drying (photoresist layer), the sample was left standing in NMP solvent at 25°C for 10 minutes, washed with ultrapure water for 30 seconds, and passed through compressed air blow dry. Subsequently, a spectrophotometer was used to measure its del(E*) and thus evaluate chemical resistance, and the results are shown in Table 6.

After coating and exposure, the samples were checked for developability by using a developing machine (Scientific Vacuum Systems (SVS) company, KOH dilute solution), and the results are shown in Table 6.

After drying the developed substrates in a forced convection drying oven at 230° C. for 20 minutes, the surface wrinkles of the obtained samples were examined using a scanning electron microscope, and the results are shown in Table 6.

Criteria for evaluating chemical resistance del(E*) less than 3: ○ del(E*) greater than or equal to 3: X

Standard BP for evaluating developability is less than 60 seconds: ○ BP is greater than or equal to 60 seconds: X

Criteria for evaluating surface wrinkles Wrinkles are not observed on the patterned surface when observed with a scanning electron microscope: ○ Wrinkles are observed on the patterned surface when observed with a scanning electron microscope: X

[Table 6] CIE color coordinates (Gx, Gy) brightness(%) chemical resistance Developability surface wrinkle Example 1 0.255, 0.560 61.7 ○ o o Example 2 0.254, 0.560 61.8 ○ o o Example 3 0.255, 0.560 61.4 ○ o o Example 4 0.256, 0.560 61.5 ○ o o Example 5 0.254, 0.560 61.6 ○ o o Example 6 0.253, 0.560 61.7 ○ o o Example 7 0.255, 0.560 61.3 ○ o o Example 8 0.254, 0.560 61.9 ○ o o Example 9 0.252, 0.560 61.8 ○ o o Example 10 0.253, 0.560 61.6 ○ o o Example 11 0.254, 0.560 61.4 ○ o o Example 12 0.255, 0.560 61.2 ○ o o Example 13 0.253, 0.560 61.1 ○ o o Example 14 0.254, 0.560 61.3 ○ o o Example 15 0.255, 0.560 61.4 ○ o o Example 16 0.250, 0.560 61.8 ○ o o Example 17 0.251, 0.560 61.3 ○ o o Example 18 0.254, 0.560 61.2 ○ o o Example 19 0.255, 0.560 61.3 ○ o o Example 20 0.253, 0.560 61.5 ○ o o Example 21 0.253, 0.560 59.7 x x x Comparative example 1 0.274, 0.560 60.1 x x x Comparative example 2 0.273, 0.560 60.0 x o x Comparative example 3 0.272, 0.560 58.8 x x x Comparative example 4 0.276, 0.560 59.8 x x o Comparative Example 5 0.275, 0.560 59.1 x x x Comparative example 6 0.275, 0.560 58.1 x x x

Referring to Table 6, the photosensitive resin compositions using the compounds according to Examples 1 to 20 of Examples as dyes reproduced high color compared to the photosensitive resin compositions not containing the compounds according to Comparative Examples 1 to 6 And exhibits excellent brightness and chemical resistance at the same time, and thus provides a high-definition display with excellent color characteristics while being easily applied to image sensors and the like. The photosensitive resin composition of Example 21 reproduces high color, but its brightness, chemical resistance, developability, surface wrinkle characteristics and the like (compared with the brightness, chemical resistance of the photosensitive resin compositions of Examples 1 to 20 , developability, surface wrinkle characteristics, and the like) are greatly reduced.

While the invention has been described in connection with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, the invention is intended to cover the spirit and scope of the invention contained within the claims Various modifications and equivalent arrangements within .

none.

FIG. 1 is a graph for explaining the full width at half maximum (FWHM) of a compound with respect to the maximum absorption wavelength and the shortest wavelength of the FWHM.

Claims (15)

A phthalocyanine compound exhibiting the shortest wavelength with respect to the full width at half maximum with respect to the maximum absorption wavelength in the range of 600 nm to 620 nm, wherein the phthalocyanine compound is represented by Chemical Formula 1:

Wherein, in Chemical Formula 1, R ¹ to R ⁴ are independently hydrogen atoms, R ⁵ to R ⁸ are independently hydrogen atoms or halogen atoms, and R ⁹ to R ¹⁶ are independently halogen atoms or represented by Chemical Formula 2-4 , and at least one of R ⁹ to R ¹⁶ is represented by chemical formula 2-4,

Wherein, in Chemical Formula 2-4, R ²⁰ to R ²² are independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, and L ¹ is a substituted or unsubstituted C1 to C20 alkylene group . The phthalocyanine compound according to claim 1, wherein one of R ⁹ to R ¹² or one of R ¹³ to R ¹⁶ is represented by chemical formula 2-4. The phthalocyanine compound according to claim 2, wherein one of R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ is represented by chemical formula 2-4. The phthalocyanine compound according to claim 1, wherein two of R ⁹ to R ¹⁶ are represented by chemical formula 2-4. The phthalocyanine compound as described in claim item 4, wherein one of R ⁹ to R ¹² and one of R ¹³ to R ¹⁶ are represented by chemical formula 2-4. The phthalocyanine compound as described in claim item 5, wherein one of R ¹⁰ and R ¹¹ and one of R ¹⁴ and R ¹⁵ are represented by chemical formula 2-4. The phthalocyanine compound as described in Claim 1, wherein the compound represented by Chemical Formula 1 is represented by one of Chemical Formula 1-12 to Chemical Formula 1-20:

[chemical formula 1-13]

[chemical formula 1-16]

[chemical formula 1-19]

The phthalocyanine compound as described in claim 1, wherein the phthalocyanine compound is a green dye. A photosensitive resin composition, including the compound described in claim 1. The photosensitive resin composition according to claim 9, wherein the content of the compound is 1% to 40% by weight based on the total amount of the photosensitive resin composition. The photosensitive resin composition according to claim 9, wherein the photosensitive resin composition further includes a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The photosensitive resin composition according to claim 11, wherein the photosensitive resin composition further includes a pigment. A photosensitive resin layer produced using the photosensitive resin composition described in Claim 9. A color filter comprising the photosensitive resin layer as claimed in claim 13. A display device comprising the color filter as claimed in claim 14.

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