TW202122499A - 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 compoun, a photosensitive resin composition containing the compound, a photosensitive resin layer, a color filter, and a display device. [Cross references to related applications]

This application claims to protect the Korean Patent Application No. 10-2019-0135770 filed at the Korean Intellectual Property Office on October 29, 2019 and the Korean Patent Application No. 10-2019-0135770 filed at the Korean Intellectual Property Office on August 19, 2020. The priority and rights of No. 10-2020-0104060, the entire content of the patent application is incorporated herein by reference.

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

The pigment dispersion method (which is a method of forming a color filter) provides a color film by repeating a series of processes, such as coating a photopolymerizable composition containing a colorant on a transparent substrate containing a black matrix, and making the formed pattern Expose to light, remove unexposed parts with solvent, and thermally cure. The photosensitive resin composition used to produce a color filter according to the pigment dispersion method usually contains a 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, laptop computers, monitors, and TVs. However, for pigment dispersion methods, photosensitive resin compositions for color filters are recently required to have improved performance and excellent pattern profile. Specifically, there is an increasing demand for colorants suitable for image sensors that require high color reproducibility and high brightness and high contrast characteristics.

The image sensor is the part of the image sensor that generates images in display devices such as mobile phone cameras, digital still cameras (DSC), and the like, and can be classified into charge coupled devices (CCD) Image sensors and complementary metal oxide semiconductor (CMOS) image sensors.

Since the charge-coupled device (CCD) image sensor uses a photosensitive resin layer for a color filter (which requires a film thickness of less than or equal to about 1.5 microns), the photosensitive resin composition should contain a large amount of colorant. It is prepared, and therefore has the problem of insufficient adhesion to the substrate or insufficient curing due to reduced sensitivity, significant decrease in pattern formability (for example, color loss due to the elution of dye in the exposed area), and the like.

Therefore, continuous efforts are being made to develop photosensitive resin compositions for color filters that satisfy reliability (for example, brightness, chemical resistance, etc.) while realizing high colors and 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 containing 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.

An embodiment of the present invention provides a phthalocyanine compound that exhibits the shortest wavelength at full width at half maximum (FWHM) relative to the maximum absorption wavelength in the range of about 600 nanometers to about 620 nanometers.

The phthalocyanine compound can be represented by Chemical Formula 1.

在化學式1中， R¹ 到R⁴ 獨立地為氫原子， R⁵ 到R⁸ 獨立地為氫原子或鹵素原子，且 R⁹ 到R¹⁶ 獨立地為鹵素原子或由化學式2表示。[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 are represented by Chemical Formula 2.

其中，在化學式2中， R¹⁷ 為經取代或未經取代的C1到C20烷基或經取代或未經取代的C6到C20芳基。[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.

[化學式2-2]

[化學式2-3]

[化學式2-4]

在化學式2-1至化學式2-4中， R¹⁸ 和R¹⁹ 獨立地為經取代或未經取代的C1到C20烷基， R²⁰ 到R²² 獨立地為氫原子或經取代或未經取代的C1到C20烷基，且 L¹ 為經取代或未經取代的C1到C20伸烷基。 R⁹ 到R¹⁶ 中的一個可由化學式2表示。 「R⁹ 到R¹² 中的一個」或「R¹³ 到R¹⁶ 中的一個」可由化學式2表示。 「R¹⁰ 、R¹¹ 、R¹⁴ 以及R¹⁵ 」中的一個可由化學式2表示。 「R⁹ 到R¹⁶ 中的兩個」可由化學式2表示。 「R⁹ 到R¹² 中的一個」和「R¹³ 到R¹⁶ 中的一個」可由化學式2表示。 「R¹⁰ 和R¹¹ 中的一個」和「R¹⁴ 和R¹⁵ 中的一個」可由化學式2表示。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, and R ²⁰ to R ^{22 are} independently hydrogen atoms or substituted or unsubstituted A C1 to C20 alkyl group, and L ¹ is a substituted or unsubstituted C1 to C20 alkylene group. One of R ⁹ to R ¹⁶ can be represented by Chemical Formula 2. "One of R ⁹ to R ¹² " or "One of R ¹³ to R ¹⁶ " can 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.

[化學式1-2]

[化學式1-3]

[化學式1-4]

[化學式1-5]

[化學式1-6]

[化學式1-7]

[化學式1-8]

[化學式1-9]

[化學式1-10]

[化學式1-11]

[化學式1-12]

[化學式1-13]

[化學式1-14]

[化學式1-15]

[化學式1-16]

[化學式1-17]

[化學式1-18]

[化學式1-19]

[化學式1-20]

。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 may be a green dye.

Another embodiment provides a photosensitive resin composition containing the compound.

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

The photosensitive resin composition may further include a 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.

在化學式3中， R²³ 和R²⁴ 獨立地為羥基或經取代或未經取代的C1到C20烷基，且 n1和n2獨立地為0到5的整數，限制條件為3 ≤ n1+n2 ≤ 5。[Chemical formula 3]

In Chemical Formula 3, R ²³ and R ^{24 are} independently a hydroxyl group or a substituted or unsubstituted C1 to C20 alkyl group, and n1 and n2 are independently an integer from 0 to 5, and the restriction condition is 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 present invention are included in the following specific embodiments.

The compound according to one embodiment has excellent green spectral characteristics, high molar extinction coefficient, and excellent solubility in organic solvents, and therefore can be used as a dye for green photosensitive resin compositions for color filters, and therefore, through The photosensitive resin layer and color filter produced using the photosensitive resin composition containing the dye can 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 patent application for invention.

As used herein, when no specific definition is provided otherwise, the term "substituted" refers to substitution by 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 ), where R ²⁰⁰ , R ²⁰¹ and R ^{202 are the} same or different, and are independently C1 to C10 alkyl groups), formamidino, hydrazine Group, hydrazone group, carboxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted alicyclic organic group , Substituted or unsubstituted aryl groups and substituted or unsubstituted heterocyclic groups.

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, and the term “aryl” refers to C6 to C20 aryl 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, it is a C1 to C18 alkylene group, and the term "arylene" refers to a C6 to C20 arylene group and specifically a C6 to C16 arylene group.

As used herein, when specific definitions are not otherwise provided, "(meth)acrylate" means "acrylate" and "methacrylate", and "(meth)acrylic acid" means "acrylic acid" and "Methacrylate".

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

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

As used herein, when a specific definition is not otherwise provided, "*" indicates the point where the same or different atoms or chemical formulas are linked.

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

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 size of the pigment, the demand for improvement in brightness and contrast continues to increase. Therefore, continuous 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, the demand for photosensitive resin compositions suitable for charge coupled devices (CCD), complementary metal oxide semiconductor image sensors, or the like other than conventional display devices such as LCDs has rapidly increased. However, conventional photosensitive resin compositions using dyes as main colorants may not achieve high colors when applied to image sensors, and hardly provide high-definition color filters. The reason why high color cannot be achieved is that the pattern size of the color filter mounted on a charge coupled device (CCD) is about 1/100 times to about 1/200 times smaller than the pattern size of a conventional color filter used for LCD .

Therefore, the inventors of the present invention have developed a dye compound used in a photosensitive resin composition for a color filter after a long-term study, which can limit the phthalocyanine compound's 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, so that the compound can be easily applied to a size that is about 100 times to about 200 times smaller than the color filter pattern used for LCD The pattern to increase the resolution but reduce the residue.

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

Have a full width at half maximum (FWHM) relative to the maximum absorption wavelength in the range of about 600 nanometers to about 620 nanometers (e.g., about 610 nanometers to about 620 nanometers, and for example, about 611 nanometers to about 616 nanometers). ) The shortest wavelength phthalocyanine compound may not only exhibit excellent solubility for organic solvents (compared to the shortest wavelength phthalocyanine compound having the full width at half maximum (FWHM) relative to the maximum absorption wavelength outside the range Compound), and also improve the brightness and chemical resistance of a photosensitive resin composition containing the phthalocyanine-based compound as a colorant, and particularly realize high color (reducing Gx in CIE color coordinates (Gx, Gy)).

For example, a phthalocyanine-based compound exhibiting the shortest wavelength of FWHM with respect to the maximum absorption wavelength in the range of about 600 nm to about 620 nm can be represented by Chemical Formula 1.

在化學式1中， R¹ 到R⁴ 獨立地為氫原子， R⁵ 到R⁸ 獨立地為氫原子或鹵素原子，且 R⁹ 到R¹⁶ 獨立地為鹵素原子或由化學式2表示， [化學式2]

其中，在化學式2中， R¹⁷ 為經取代或未經取代的C1到C20烷基或經取代或未經取代的C6到C20芳基。[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 are 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 high molar extinction coefficient. In addition, since the compound represented by Chemical Formula 1 must include at least one substituent represented by Chemical Formula 2, it can exhibit excellent solubility in organic solvents and excellent brightness and chemical resistance when applied to color filters.

For example, when the compound represented by Chemical Formula 1 does not include any substituent represented by Chemical Formula 2, the solubility, brightness, and chemical resistance to organic solvents may be greatly reduced, and therefore the compound may not be used for color It is a coloring agent in the photosensitive resin composition of the filter, and it may be extremely difficult to realize a high color reproduction image sensor.

The substituent represented by Chemical Formula 2 is "aryloxy having one or two alkyl groups as substituents" or "alkoxy having one or two alkyl groups as substituents", and in the aryloxy group, the alkyl group The group is substituted at the ortho position and/or the 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 realize a green pixel for a color filter.

[化學式2-2]

[化學式2-3]

[化學式2-4]

在化學式2-1至化學式2-4中， R¹⁸ 和R¹⁹ 獨立地為經取代或未經取代的C1到C20烷基， R²⁰ 到R²² 獨立地為氫原子或經取代或未經取代的C1到C20烷基，且 L¹ 為經取代或未經取代的C1到C20伸烷基。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, and R ²⁰ to R ^{22 are} independently hydrogen atoms or substituted or unsubstituted A C1 to C20 alkyl group, and L ¹ is a substituted or unsubstituted C1 to C20 alkylene group.

In Chemical Formula 2-2 and Chemical Formula 2-3, at ^{least one of R 18} and R ¹⁹ is a non-linear (branched) alkyl group such as tert-butyl instead of a linear alkyl group such as methyl, ethyl, and N-butyl), the compound is more ideal 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, the developability can be further improved.

In addition, the phthalocyanine-based compound represented by Chemical Formula 1 contains four hydrogen atoms and at least 4 halogen atoms, and the solubility to organic solvents can be further improved due to these structural characteristics. Specifically, the phthalocyanine-based compound represented by Chemical Formula 1 includes four benzene rings in a core structure, the benzene ring being: i) a benzene ring having ^{groups represented by R 1} to R ⁴ ; ii) having The benzene ring of the group represented by R ⁵ to R ^{8 ; iii) the benzene ring having the group represented by R 9} to R ¹² ; and iv) the benzene ring having the group represented ^{by R 13} to R ^{16, wherein} Among the four benzene rings, the benzene ring containing the substituent represented by Chemical Formula 2 contains three groups of all halogen atoms except the substituent represented by Chemical Formula 2, but benzene does not contain the substituent represented by Chemical Formula 2 The ring may 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) relative to the maximum absorption wavelength in the range of about 600 nm to about 620 nm, and further improve the solubility of the compound in organic solvents. And therefore help to improve brightness and ensure process characteristics.

In particular, even when the phthalocyanine compound exhibiting the shortest wavelength of FWHM with respect to the maximum absorption wavelength in the range of about 600 nanometers to about 620 nanometers 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. Therefore, the phthalocyanine compound according to an embodiment may ideally exhibit the shortest wavelength of FWHM relative to the maximum absorption wavelength in the range of about 600 nm to about 620 nm, and at the same time have 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 decreased brightness 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.

[化學式1-2]

[化學式1-3]

[化學式1-4]

[化學式1-5]

[化學式1-6]

[化學式1-7]

[化學式1-8]

[化學式1-9]

[化學式1-10]

[化學式1-11]

[化學式1-12]

[化學式1-13]

[化學式1-14]

[化學式1-15]

[化學式1-16]

[化學式1-17]

[化學式1-18]

[化學式1-19]

[化學式1-20]

。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-based compound represented by Chemical Formula 1 includes at least one substituent represented by Chemical Formula 2, a clearer color can be achieved even in a smaller amount, and can be manufactured by using the compound as a colorant Display devices with improved color characteristics (such as brightness, contrast, etc.). For example, the compound may be a coloring agent, such as a dye (such as a green dye), such as a dye having a maximum transmittance in the wavelength range of about 445 nanometers to about 560 nanometers.

Generally speaking, dyes are the most expensive among the components used in color filters. Therefore, 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 realize excellent color characteristics, such as high brightness, high contrast, etc., even when used in a small amount, and reduce Unit production cost.

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

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

The compound according to an embodiment may serve as a colorant, such as a dye (for example, a green dye) in the 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 an embodiment may be about 1% by weight to about 40% by weight, for example, about 10% by weight to about 40% by weight, for example, about 20% by weight to about 40% by weight. % By weight, for example, about 1% by weight to about 30% by weight, for example, about 1% by weight to about 20% by weight, for example, about 1% by weight to about 10% by weight. When the compound according to the embodiment is included in the above range, color reproduction and contrast are improved.

The photosensitive resin composition may further include a pigment, such as a yellow pigment, a green pigment, or a combination 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 the form of a mixture of two or more than two.

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 can be used alone or in the form of a mixture of two or more than two.

For example, the pigment may be contained in the photosensitive resin composition in the form of a pigment dispersion liquid.

The pigment dispersion liquid may include a solid pigment, a solvent, and a dispersant that uniformly disperses the pigment in the solvent.

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

The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant, and the like. Specific examples of the dispersant can be polyglycol and its ester, polyoxyalkylene, polyol ester alkylene oxide addition product, alcohol alkylene oxide addition product, sulfonate, sulfonate, carboxylate, carboxylate , Alkyl amine alkylene oxide addition products, alkyl amines, etc. These can be used alone or in the form of a mixture of two or more.

Commercially available examples of dispersants may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, manufactured by BYK Co., Ltd. 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.

The content of the dispersant may be about 1% by weight to about 20% by weight based on the total amount of the photosensitive resin composition. When the dispersant in the above range is included, the dispersion of the photosensitive resin composition is improved due to the proper viscosity, and the 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, for example, about 12% by weight to about 18% by weight. When the pigment dispersion liquid is included in the range, it is desirable to ensure a process margin and improve color reproducibility and contrast.

The binder resin may be an acryl-based resin.

The acryl-based resin is a copolymer of a first ethylenic unsaturated monomer and a second ethylenic unsaturated monomer (which can be copolymerized with the first ethylenic unsaturated monomer), and contains at least one propylene The base type repeating unit of the resin.

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 a combination thereof.

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

The second ethylenically unsaturated monomer may 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 (formaldehyde Base) methyl acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (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 Dimethylamino ethyl ester, etc.; carboxylic acid vinyl ester compounds, such as vinyl acetate, vinyl benzoate, etc.; unsaturated glycidyl carboxylic acid ester 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 can be used alone or in the form of a mixture of two or more.

Specific examples of acryl-based resins may be (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid/formaldehyde Benzyl acrylate/2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc., but not limited thereto. These can be used alone or in the form of a mixture of two or more.

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

The weight average molecular weight of the binder resin may be about 3,000 g/mole to about 150,000 g/mole, for example, about 5,000 g/mole to about 50,000 g/mole, for example, about 20,000 g/mole to about 30,000 g/mole. Mol. 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 the 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, the resolution of the pixel pattern can be improved.

Based on the total amount of the photosensitive resin composition, the content of the binder resin may be about 1% by weight to about 20% by weight, for example, about 1% by weight to about 15% by weight or about 1% by weight to about 10% by weight. When the binder resin in the above range is included, due to the improved crosslinking during the production of the color filter, the developability can be improved and the excellent surface smoothness can be improved.

The photopolymerizable compound may be a monofunctional or multifunctional 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 the exposure period in the pattern formation process 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, 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 Ester, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy (meth)acrylate, ethylene glycol monomethyl Base ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tri(meth)acryloxyethyl phosphate, novolac epoxy (meth)acrylate, etc.

Commercial examples of the photopolymerizable compound may be as follows. Monofunctional (meth)acrylate 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 bifunctional (meth)acrylates may include Aronix M-210 ^® , M-240 ^® , M-6200 ^® (Toa Synthetic 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 ^® (East Asia 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 in a mixture of two or more Form use.

The photopolymerizable compound may be treated with acid 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, for example, about 1% by weight to about 10% by weight. When the photopolymerizable compound is included in the range, the photopolymerizable compound is sufficiently cured during exposure during the pattern formation process and has excellent reliability, and the developability of the alkaline developer can be improved.

The photopolymerization initiator may 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 acetophenone compounds 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 benzophenone compounds can be benzophenone, benzophenone benzoate, methyl benzoylbenzoate, 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 can be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone , 2-Chlorothioxanthone and so on.

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

Examples of triazine compounds may 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- Yl)-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 can be O-oxime compounds, 2-(O-benzyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1- (O-acetoxime)-1-[9-ethyl-6-(2-methylbenzyl)-9H-oxazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxygen Amino-1-phenylpropan-1-one and so on. Specific examples of O-oxime compounds can be 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-benzene Yl)-butan-1-one, 1-(4-phenylthiophenyl)-butane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylthiobenzene) Yl)-octane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylthiophenyl)-octan-1-one oxime-O-acetate, 1- (4-Phenylthiophenyl)-butan-1-one oxime-O-acetate and the like.

In addition to the compounds, the photopolymerization initiator may further include azole-based compounds, diketone-based compounds, boric acid-based compounds, diazonium-based compounds, imidazole-based compounds, biimidazole-based compounds, fluorene-based compounds, and the like.

The photopolymerization initiator may 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 photosensitizers 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, for example, about 0.1% by weight to about 5% by weight. When the photopolymerization initiator is included in the range, since it is fully cured during the exposure in the pattern formation process, excellent reliability can be ensured, and the pattern can have excellent resolution and close contact properties as well as excellent heat resistance, Light resistance and chemical resistance, and because of the non-reaction initiator, the transmittance can be prevented from decreasing.

The solvent is a material that is compatible with but does not react with the compound, pigment, binder resin, photopolymerizable compound, and 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, methyl phenyl ether, tetrahydrofuran, etc.; glycol ethers, such as ethylene glycol monomethyl ether, ethyl alcohol, etc. Glycol monoethyl ether, etc.; ethylene glycol ethyl acetate, such as methyl glycol ethyl acetate, ethyl glycol ethyl acetate, diethyl glycol ethyl acetate, etc.; carbitol, such as methyl ethyl carbitol Alcohol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, etc.; propylene glycol Base ether acetate, 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-hydroxyl -4-methyl-2-pentanone, methyl-n-acetone, methyl-n-butanone, methyl-n-pentanone, 2-heptanone, etc.; saturated alicyclic monocarboxylic acid alkyl ester, such as acetic acid Ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactate esters, such as methyl lactate, ethyl lactate, etc.; alkyl oxyacetate, such as methyl oxyacetate, ethyl oxyacetate, oxy Butyl acetate, etc.; Alkyl alkoxy acetate, 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 Ester, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; 2-oxypropionic acid alkyl ester, such as 2-oxypropionic acid Methyl ester, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.; alkyl 2-alkoxypropionate, such as methyl 2-methoxypropionate, 2-methoxypropionate Ethyl ester, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-oxy-2-methylpropionate, such as 2-oxy-2-methylpropionic acid Methyl ester, ethyl 2-oxy-2-methylpropionate, etc.; monooxymonocarboxylic acid alkyl ester of 2-alkoxy-2-methylpropionate, such as 2-methoxy Methyl-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc.; esters, such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate , Hydroxy ethyl acetate, 2-hydroxy-3-methyl butyrate, etc.; keto acid esters, such as ethyl pyruvate and the like. In addition, high-boiling solvents can also be used, such as N-methylformamide, N,N-dimethylformamide, N-methylformaniline, N-methylacetamide, N,N-di Methyl acetamide, N-methylpyrrolidone, dimethyl sulfide, benzyl ethyl ether, dihexyl ether, acetone, isophorone (isophorone), caproic acid, caprylic acid, 1-octanol, 1- Nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, 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 ethyl acetate, etc.; esters, such as propionic acid 2 -Hydroxyethyl, etc.; Carbitol, such as diethylene glycol monomethyl ether, etc.; Propylene glycol alkyl ether acetate, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, etc.; and/or ketones, such as Cyclohexanone and so on.

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

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

在化學式3中， R²³ 和R²⁴ 獨立地為羥基或經取代或未經取代的C1到C20烷基， L² 到L⁴ 獨立地為經取代或未經取代的C1到C20伸烷基，且 n1和n2獨立地為0到5的整數，限制條件為3 ≤ n1+n2 ≤ 5。[Chemical formula 3]

In Chemical Formula 3, R ²³ and R ^{24 are} independently a hydroxyl group or a substituted or unsubstituted C1 to C20 alkyl group, L ² to L ^{4 are} independently a substituted or unsubstituted C1 to C20 alkylene group, And n1 and n2 are independently integers from 0 to 5, and the restriction condition is 3 ≤ n1+n2 ≤ 5.

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

For example, in Chemical Formula 3, R ²³ may be a C1 to C20 alkyl group substituted with an 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 close contact properties with the substrate.

Examples of the epoxy compound may include a phenol novolak epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol A epoxy compound, an alicyclic epoxy compound, or a combination thereof.

Based on 100 parts by weight of the photosensitive resin composition, the epoxy compound may be included in an amount of about 0.01 parts by weight to about 20 parts by weight, for example, about 0.1 parts by weight to about 10 parts by weight. When the epoxy compound within the range is included, close contact properties, storage properties, and the like can be improved.

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

Examples of the silane coupling agent may include trimethoxysilyl benzoic acid, gamma-methacryloylpropoxytrimethoxysilane, vinyl triethoxysilane, vinyl trimethoxysilane, gamma-isocyanate propyl Triethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, etc. These can be used alone or in the form of a mixture 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 is included in the range, close contact properties, storage properties, and the like can be improved.

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

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.) 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 ^® (Toray Silicone Co., Ltd.).

The surfactant can 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 in the range, excellent wetting and coating uniformity on the glass substrate can be ensured, but contamination may not be generated.

In addition, unless the additives degrade the properties of the photosensitive resin composition, the photosensitive resin composition may contain a predetermined amount of other additives, such as antioxidants, stabilizers, and the like.

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

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

The manufacturing process includes: coating the photosensitive resin composition on the support substrate by spin coating, slit coating, inkjet printing, etc.; 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. The patterning process conditions are well-known in the related art and will not be described in detail in this specification.

Hereinafter, the present invention is explained in more detail with reference to examples, however, these examples are not interpreted in any meaning as limiting the scope of the present invention. ( Synthesis of Compound ) Synthesis Example 1 : Synthesis of a compound represented by Chemical Formula 1-1

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

Combine 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) are 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-1.

Maldi-tof MS : 1190.69 m/z合成實例 2 ：合成由化學式 1-2 表示的化合物 [Chemical formula 1-1]

Maldi-tof MS: 1190.69 m/z Synthesis Example 2 : Synthesis of a compound represented by Chemical Formula 1-2

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

Maldi-tof MS : 1090.96 m/z合成實例 3 ：合成由化學式 1-3 表示的化合物 [Chemical formula 1-2]

Maldi-tof MS: 1090.96 m/z Synthesis Example 3 : Synthesis of the compound represented by Chemical Formula 1-3

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

Combine 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) are 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-3.

Maldi-tof MS : 1218.75 m/z合成實例 4 ：合成由化學式 1-4 表示的化合物 [Chemical formula 1-3]

Maldi-tof MS: 1218.75 m/z Synthesis Example 4 : Synthesis of the compound represented by Chemical Formula 1-4

Combine 4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 2.80g), phthalonitrile (0.67g), 1,8-diazabicycloundec-7-ene (4.01g) and 1-pentenol (30g) are placed in a 100ml 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-4.

Maldi-tof MS : 1104.98 m/z合成實例 5 ：合成由化學式 1-5 表示的化合物 [Chemical formula 1-4]

Maldi-tof MS: 1104.98 m/z Synthesis Example 5 : Synthesis of the compound represented by Chemical Formula 1-5

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

Combine 4-(2-methyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2g), 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) are placed in a 100 ml flask and heated To 90°C to dissolve the solid, zinc acetate (0.54 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-5.

Maldi-tof MS : 1134.58 m/z合成實例 6 ：合成由化學式 1-6 表示的化合物 [Chemical formula 1-5]

Maldi-tof MS: 1134.58 m/z Synthesis Example 6 : Synthesis of compounds represented by chemical formula 1-6

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

Combine 4-(2,6-dimethyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2g), 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) are placed in a 100 ml flask Neutralize and heat to 90°C to dissolve the solid, add zinc acetate (0.52 g), and stir the result while heating to 140°C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-6.

Maldi-tof MS : 1162.64 m/z合成實例 7 ：合成由化學式 1-7 表示的化合物 [Chemical formula 1-6]

Maldi-tof MS: 1162.64 m/z Synthesis Example 7 : Synthesis of the compound represented by chemical formula 1-7

Combine 4-(2,6-dimethyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2g), 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) are placed in a 100 ml flask Neutralize and heat to 90°C to dissolve the solid, add zinc acetate (1.04 g), and stir the result while heating to 140°C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-7.

Maldi-tof MS : 1076.93 m/z合成實例 8 ：合成由化學式 1-8 表示的化合物 [Chemical formula 1-7]

Maldi-tof MS: 1076.93 m/z Synthesis Example 8 : Synthesis of the compound represented by chemical formula 1-8

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

Combine 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) are placed in 100 ml In the 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-8.

Maldi-tof MS : 1330.96 m/z合成實例 9 ：合成由化學式 1-9 表示的化合物 [Chemical formula 1-8]

Maldi-tof MS: 1330.96 m/z Synthesis Example 9 : Synthesis of the compound represented by chemical formula 1-9

Combine 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) are placed in 100 ml In the 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-9.

Maldi-tof MS : 1161.09 m/z合成實例 10 ：合成由化學式 1-10 表示的化合物 [Chemical formula 1-9]

Maldi-tof MS: 1161.09 m/z Synthesis Example 10 : Synthesis of a compound represented by chemical formula 1-10

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

Combine 4-(2-tert-butyl-4-methylphenoxy)-3,5,6-trichloro-phthalonitrile (2g), 3,4,5,6-tetrachloro-phthalonitrile Dicarbonitrile (0.68g), phthalonitrile (0.33g), 1,8-diazabicycloundec-7-ene (1.9g) and 1-pentenol (15g) are placed in 100ml In the 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-10.

Maldi-tof MS : 1246.80 m/z合成實例 11 ：合成由化學式 1-11 表示的化合物 [Chemical formula 1-10]

Maldi-tof MS: 1246.80 m/z Synthesis Example 11 : Synthesis of a compound represented by chemical formula 1-11

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

Maldi-tof MS : 1109.03 m/z合成實例 12 ：合成由化學式 1-12 表示的化合物 [Chemical formula 1-11]

Maldi-tof MS: 1109.03 m/z Synthesis Example 12 : Synthesis of the compound represented by Chemical Formula 1-12

Combine 3,4,5,6-tetrachlorophthalonitrile (5g), 2,2-dimethyl-1-propanol (1.66g), diazabicycloundec-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 is complete, ethyl acetate (EA) is used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was vacuum dried to obtain 4-(2,2-dimethyl-1-propoxy)-3,5,6-trichloro-phthalonitrile.

Combine 4-(2,2-dimethyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (2g), 3,4,5,6-tetrachloro-phthalonitrile Dicarbonitrile (0.84g), phthalonitrile (0.40g), 1,8-diazabicycloundec-7-ene (2.40g) and 1-pentenol (15g) are placed in 100ml In the 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-12.

Maldi-tof MS : 1094.60 m/z合成實例 13 ：合成由化學式 1-13 表示的化合物 [Chemical formula 1-12]

Maldi-tof MS: 1094.60 m/z Synthesis Example 13 : Synthesis of a compound represented by chemical formula 1-13

Combine 4-(2,2-dimethyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (1g), 3,4,5,6-tetrachloro-phthalonitrile Dicarbonitrile (1.67g), phthalonitrile (0.40g), 1,8-diazabicycloundec-7-ene (2.40g) and 1-pentenol (15g) are placed in 100ml In the 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-13.

Maldi-tof MS : 1042.91 m/z合成實例 14 ：合成由化學式 1-14 表示的化合物 [Chemical formula 1-13]

Maldi-tof MS: 1042.91 m/z Synthesis Example 14 : Synthesis of compound represented by chemical formula 1-14

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

Maldi-tof MS : 956.84 m/z合成實例 15 ： 合成由化學式 1-15 表示的化合物 [Chemical formula 1-14]

Maldi-tof MS: 956.84 m/z Synthesis Example 15 : Synthesis of a compound represented by chemical formula 1-15

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

Combine 4-(3-methyl-1-butoxy)-3,5,6-trichloro-phthalonitrile (2g), 3,4,5,6-tetrachlorophthalonitrile (0.84g), phthalonitrile (0.40g), 1,8-diazabicycloundec-7-ene (2.40g) and 1-pentenol (15g) in a 100ml flask And it was 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-15.

Maldi-tof MS : 1094.60 m/z合成實例 16 ：合成由化學式 1-16 表示的化合物 [Chemical formula 1-15]

Maldi-tof MS: 1094.60 m/z Synthesis Example 16 : Synthesis of the compound represented by Chemical Formula 1-16

Combine 4-(3-methyl-1-butoxy)-3,5,6-trichloro-phthalonitrile (1g), 3,4,5,6-tetrachlorophthalonitrile (1.67g), phthalonitrile (0.40g), 1,8-diazabicycloundec-7-ene (2.40g) and 1-pentenol (15g) in a 100ml flask And it was 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-16.

Maldi-tof MS : 1042.91 m/z合成實例 17 ：合成由化學式 1-17 表示的化合物 [Chemical formula 1-16]

Maldi-tof MS: 1042.91 m/z Synthesis Example 17 : Synthesis of compound represented by chemical formula 1-17

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

Maldi-tof MS : 956.84 m/z合成實例 18 ：合成由化學式 1-18 表示的化合物 [Chemical formula 1-17]

Maldi-tof MS: 956.84 m/z Synthesis Example 18 : Synthesis of the compound represented by Chemical Formula 1-18

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

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

Maldi-tof MS : 1066.55 m/z合成實例 19 ：合成由化學式 1-19 表示的化合物 [Chemical formula 1-18]

Maldi-tof MS: 1066.55 m/z Synthesis Example 19 : Synthesis of a compound represented by chemical formula 1-19

Combine 4-(2-methyl-1-propoxy)-3,5,6-trichloro-phthalonitrile (1g), 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) in a 100 ml flask It was heated to 90°C to dissolve the solid, zinc acetate (0.61 g) was added, and the resultant was heated to 140°C while stirring. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-19.

Maldi-tof MS : 1028.89 m/z合成實例 20 ：合成由化學式 1-20 表示的化合物 [Chemical formula 1-19]

Maldi-tof MS: 1028.89 m/z Synthesis Example 20 : Synthesis of a compound represented by chemical formula 1-20

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

Maldi-tof MS : 928.78 m/z合成實例 21 ：合成由化學式 1-21 表示的化合物 [Chemical formula 1-20]

Maldi-tof MS: 928.78 m/z Synthesis Example 21 : Synthesis of a compound represented by Chemical Formula 1-21

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

Maldi-tof MS : 885.56 m/z比較合成實例 1 ：合成由化學式 C-1 表示的化合物 [Chemical formula 1-21]

Maldi-tof MS: 885.56 m/z Comparative Synthesis Example 1 : Synthesis of the compound represented by the chemical formula C-1

Combine 4-(2-sec-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g), 1,8-diazabicycloundec-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 is complete, the resultant is concentrated and purified by column chromatography. The purified liquid was concentrated to obtain a solid. The crystalline solid was vacuum dried to obtain the compound represented by Chemical Formula C-1.

Maldi-tof MS : 1584.04 m/z比較合成實例 2 ：合成由化學式 C-2 表示的化合物 [Chemical formula C-1]

Maldi-tof MS: 1584.04 m/z Comparative Synthesis Example 2 : Synthesis of the compound represented by the chemical formula C-2

Combine 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-bis Methylformamide (25 mL) was placed in a 100 mL flask and then stirred while heating at 70°C. When the reaction is complete, ethyl acetate (EA) is 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.

Combine 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 solid, zinc acetate (0.26 g) was added, and the resultant was stirred while heating to 140°C . When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by the chemical formula C-2.

Maldi-tof MS : 1808.47 m/z比較合成實例 3 ：合成由化學式 C-3 表示的化合物 [Chemical formula C-2]

Maldi-tof MS: 1808.47 m/z Comparative Synthesis Example 3 : Synthesis of the compound represented by the chemical formula C-3

Combine 3,4,5,6-tetrachlorophthalonitrile (5g), 2,4-dimethoxyphenol (3.47g), K ₂ CO ₃ (3.9g) and N,N-dimethyl Methylformamide (25 ml) was placed in a 100 ml flask and stirred while heating at 70°C. When the reaction is complete, ethyl acetate (EA) is 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 in vacuum to obtain 3,4,6-trichloro-5-(2,4-dimethoxy-phenoxy )-Phthalonitrile.

Combine 3,4,6-trichloro-5-(2,4-dimethoxy-phenoxy)-phthalonitrile (2g), 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 solid, zinc acetate (0.24 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula C-3.

Maldi-tof MS : 1591.80 m/z比較合成實例 4 ：合成由化學式 C-4 表示的化合物 [Chemical formula C-3]

Maldi-tof MS: 1591.80 m/z Comparative Synthesis Example 4 : Synthesis of the compound represented by the chemical formula C-4

The 4-(2,4-dimethoxy-phenoxy)-3,5,6-trichloro-phthalonitrile (0.7 g) of Example 1-2, 3,4,5,6 -Tetrachlorophthalonitrile (1.45g), 1,8-diazabicycloundec-7-ene (1.38g) and 1-pentenol (14g) are placed in a 100ml flask and heated To 90°C to dissolve the solid, zinc acetate (0.33 g) was added, and the resultant was stirred while heating to 140°C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by the chemical formula C-4.

Maldi-tof MS : 1237.54 m/z比較合成實例 5 ：合成由化學式 C-5 表示的化合物 [Chemical formula C-4]

Maldi-tof MS: 1237.54 m/z Comparative Synthesis Example 5 : Synthesis of the compound represented by the chemical formula C-5

Combine 4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 0.70g), 4,5-dichlorophthalonitrile (0.52g), 1,8-diazabicycloundec-7-ene (2.01g) and 1-pentenol (15g) are placed In a 100 ml 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by the chemical formula C-5.

Maldi-tof MS : 1287.63 m/z比較合成實例 6 ：合成由化學式 C-6 表示的化合物 [Chemical formula C-5]

Maldi-tof MS: 1287.63 m/z Comparative Synthesis Example 6 : Synthesis of the compound represented by Chemical Formula C-6

Combine 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 the 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 completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried in vacuum. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to and dissolved in the purified solid, and methanol is added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula C-6.

Maldi-tof MS : 1253.19 m/z評估 1 ：測量相對於最大吸收波長的半峰全寬（ FWHM ）的最短波長 [Chemical formula C-6]

Maldi-tof MS: 1253.19 m/z Evaluation 1 : The shortest wavelength that measures the full width at half maximum ( FWHM) relative to the maximum absorption wavelength

A dilution solvent (PGMEA) was used to prepare the compounds according to Synthesis Example 1 to Synthesis Example 21 and Comparative Synthesis Example 1 to Comparative Synthesis Example 6 at a concentration of 0.005% by weight. The absorption spectra of each of the phthalocyanine-based 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) of the full width at half maximum (FWHM) relative to the maximum absorption wavelength Synthesis Example 1 616 Synthesis example 2 617 Synthesis Example 3 618 Synthesis Example 4 617 Synthesis Example 5 618 Synthesis Example 6 618 Synthesis Example 7 618 Synthesis Example 8 616 Synthesis Example 9 618 Synthesis Example 10 616 Synthesis Example 11 611 Synthesis Example 12 617 Synthesis Example 13 618 Synthesis Example 14 611 Synthesis Example 15 617 Synthesis Example 16 618 Synthesis Example 17 611 Synthesis Example 18 617 Synthesis Example 19 618 Synthesis Example 20 611 Synthesis 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 Evaluation 2 : Solubility measurement

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 performing 100 revolutions at 25°C The mixture (MIXROTAR VMR-5, Iuchi eiei Dou Co.) was separately stirred for one hour per minute, and the results are shown in Table 2. Solubility Evaluation Criteria Based on the total amount of the dilution solvent, 10% by weight or more of the compound (solute) is dissolved: ○ Based on the total amount of the dilution solvent, the compound (solute) less than 10% by weight is dissolved: X

[Table 2] (Unit: wt%) Solubility Synthesis Example 1 ○ Synthesis example 2 ○ Synthesis Example 3 ○ Synthesis Example 4 ○ Synthesis Example 5 ○ Synthesis Example 6 ○ Synthesis Example 7 ○ Synthesis Example 8 ○ Synthesis Example 9 ○ Synthesis Example 10 ○ Synthesis Example 11 ○ Synthesis Example 12 ○ Synthesis Example 13 ○ Synthesis Example 14 ○ Synthesis Example 15 ○ Synthesis Example 16 ○ Synthesis Example 17 ○ Synthesis Example 18 ○ Synthesis Example 19 ○ Synthesis Example 20 ○ Synthesis 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 to 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 one embodiment) exhibit excellent solubility in organic solvents, And therefore, it has excellent color characteristics when used in photosensitive resin compositions and the like. (Synthetic photosensitive resin composition) Example 1

The components mentioned below were mixed in the compositions shown in Tables 3 to 5 to prepare each photosensitive resin composition according to Examples 1 to 21 and Comparative Examples 1 to 6.

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

[Table 3] (Unit: wt%) Instance 1 2 3 4 5 6 7 8 9 10 Adhesive resin EHPE-3150 (DAICEL, epoxy type) 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 NPR-5216 (Miwon, acrylic 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, 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 (big celluloid) 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: wt%) Instance 11 12 13 14 15 16 17 18 19 20 Adhesive resin EHPE-3150 (Dacellulite, epoxy type) 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 0.27 NPR-5216 (Meiyuan, Acrylic) 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 (Adike) 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 (big celluloid) 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: wt%) Instance Comparative example twenty one 1 2 3 4 5 6 Adhesive resin EHPE-3150 (Dacellulite, epoxy type) 0.27 0.27 0.27 0.27 0.27 0.27 0.27 NPR-5216 (Meiyuan, Acrylic) 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 (Adike) 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 (Comparative Synthesis Example 3) 30.22 (Comparative Synthesis Example 4) 30.22 (Comparative Synthesis Example 5) 30.22 (Comparative Synthesis Example 6) Solvent PGMEA (big celluloid) 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 wrinkles

The photosensitive resin compositions according to Examples 1 to 21 and Comparative Examples 1 to 6 were respectively coated on a 1 mm thick glass substrate to remove oil stains to a thickness of 1 μm to 3 μm and then dried on a hot plate at 90°C. In 2 minutes, a film was obtained. The film is 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 light source reference color purity, and the CIE color coordinate reference was used to calculate the brightness (Y), and the results were displayed In Table 6.

In addition, after measuring the initial thickness of the sample obtained by exposure and drying (photoresist layer), the sample was allowed to stand in the 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 therefore the chemical resistance was evaluated, and the results are shown in Table 6.

After coating and exposure, the developability of the sample was checked by using a developing machine (Scientific Vacuum Systems (Scientific Vacuum Systems, SVS) company, KOH diluted solution), and the results are shown in Table 6.

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

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

The 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 No wrinkles are observed on the pattern surface when observed with a scanning electron microscope: ○ Wrinkles are observed on the pattern surface when observed with a scanning electron microscope: X

[Table 6] CIE color coordinates (Gx, Gy) brightness(%) Chemical resistance Developability Surface folds 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, compared to the photosensitive resin composition not containing the compound according to Comparative Examples 1 to 6, the photosensitive resin composition using the compounds according to Examples 1 to 20 of the Examples as dyes reproduces high color It also presents excellent brightness and chemical resistance at the same time, and therefore provides a high-definition display with excellent color characteristics when it is 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 to the brightness and chemical resistance of the photosensitive resin composition of Examples 1 to 20) , Developability, surface wrinkle characteristics and the like) are greatly reduced.

Although the present invention has been described in conjunction with what is currently regarded as practical exemplary embodiments, it should be understood that the present invention is not limited to the disclosed embodiments, but on the contrary, the present invention is intended to cover the spirit and scope of the patent application Various modifications and equivalent arrangements within.

no.

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

Claims (19)

A phthalocyanine compound that exhibits the shortest wavelength of the full width at half maximum relative to the maximum absorption wavelength in the range of 600 nm to 620 nm. The phthalocyanine-based compound according to claim 1, wherein the phthalocyanine-based compound is represented by Chemical Formula 1: [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 are 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 phthalocyanine compound according to claim 2, wherein Chemical Formula 2 is 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]

Wherein, 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, and R ²⁰ to R ^{22 are} independently hydrogen atoms or substituted or unsubstituted A substituted C1 to C20 alkyl group, and L ¹ is a substituted or unsubstituted C1 to C20 alkylene group. The phthalocyanine compound as described in claim 2, wherein one of R ⁹ to R ¹⁶ is represented by chemical formula 2. The phthalocyanine compound as described in claim 4, wherein one of R ⁹ to R ¹² or one of R ¹³ to R ¹⁶ is represented by Chemical Formula 2. The phthalocyanine compound according to claim 5, wherein one of R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ is represented by Chemical Formula 2. The phthalocyanine compound as described in claim 2, wherein two of R ⁹ to R ¹⁶ are represented by chemical formula 2. The phthalocyanine compound according to claim 7, wherein one of R ⁹ to R ¹² and one of R ¹³ to R ¹⁶ are represented by Chemical Formula 2. The phthalocyanine compound according to claim 8, wherein one of R ¹⁰ and R ¹¹ and one of R ¹⁴ and R ¹⁵ are represented by Chemical Formula 2. The phthalocyanine compound according to claim 2, wherein the compound represented by Chemical Formula 1 is 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 phthalocyanine compound according to claim 1, wherein the phthalocyanine compound is a green dye. A photosensitive resin composition comprising the compound according to claim 1. The photosensitive resin composition according to claim 12, wherein the content of the compound is 1% by weight to 40% by weight based on the total amount of the photosensitive resin composition. The photosensitive resin composition according to claim 12, 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 14, wherein the photosensitive resin composition further includes a pigment. The photosensitive resin composition according to claim 14, wherein the photosensitive resin composition further includes a compound represented by Chemical Formula 3: [Chemical Formula 3]

Wherein, in the chemical formula 3, R ²³ and R ^{24 are} independently a hydroxyl group or a substituted or unsubstituted C1 to C20 alkyl group, and n1 and n2 are independently an integer from 0 to 5, and the restriction condition is 3 ≤ n1+ n2 ≤ 5. A photosensitive resin layer produced using the photosensitive resin composition according to claim 12. A color filter comprising the photosensitive resin layer according to claim 17. A display device includes the color filter according to claim 18.

Images