TW202302769A - Photosensitive resin composition, photosensitive resin layer including the same, color filter, and electronic device - Google Patents

Abstract

Provided are a photosensitive resin composition, a photosensitive resin layer manufactured using the same, a color filter including the photosensitive resin layer, and an electronic device including the color filter. The photosensitive resin composition includes a colorant, wherein the colorant includes a dye represented by Chemical Formula 1, a core-shell structured dye, and a phthalocyanine-based dye. (In Chemical Formula 1, each substituent is as defined in the specification.).

Description

Photosensitive resin composition, photosensitive resin layer using same, color filter, and electronic device

[Cross Reference to Related Application]

This application claims priority and benefit from Korean Patent Application No. 10-2021-0087302 filed with the Korean Intellectual Property Office on July 2, 2021, the entire contents of which are incorporated herein by reference.

The present invention relates to a photosensitive resin composition, a photosensitive resin layer using the photosensitive resin layer, a color filter including the photosensitive resin layer, and an electronic device including the color filter.

Among many types of displays, liquid crystal display devices have advantages in brightness, thinness, low cost, low operating power consumption, and improved adhesion to integrated circuits, and have been more widely used in laptops, monitors, and TV screen. The liquid crystal display device includes: a lower substrate on which a black matrix, a color filter, and an ITO graphic element electrode are formed; and an upper substrate on which a starting circuit portion including a liquid crystal layer, a thin film transistor, and a capacitor layer and ITO pixel electrode. Each image is formed by sequentially stacking a plurality of color filters (generally, formed of a plurality of colors, usually three primary colors of red (R), green (G) and blue (B)) in a predetermined order. A color filter is formed in the picture element area, and a black matrix layer is placed in a predetermined pattern on the transparent substrate to form a boundary between the picture elements.

The pigment dispersion method, which is one of the methods of forming a color filter, provides a colored film by repeating a series of processes such as coating a photopolymerizable composition containing a colorant on a transparent base containing a black matrix , exposing the formed pattern to light, removing unexposed portions with a solvent, and thermally curing. A color photosensitive resin composition for manufacturing a color filter according to a pigment dispersion method generally includes an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. Pigment dispersion methods are actively applied to manufacture LCDs for mobile phones, laptops, monitors, and TVs. However, photosensitive resin compositions for color filters of the pigment dispersion method have recently been required to have improved performance and excellent pattern characteristics. Specifically, higher color reproducibility and higher luminance and higher contrast ratio features are urgently required.

The image sensor is a component for capturing images in a mobile phone camera or a digital still camera (DSC). Depending on the manufacturing process and application method, image sensors can be classified into charge-coupled device (CCD) image sensors and complementary metal oxide semiconductor (CMOS) image sensors. detector. A color imaging device for a charge-coupled device image sensor or a complementary metal-oxide-semiconductor image sensor comprising color filters each having filter segments that mix the primary colors of red, green, and blue, and The colors are separated. Current color filters installed in color imaging devices have a pattern size of 2 micrometers or less, which is 1/100 to 1/200 of that of conventional color filter patterns for LCDs. Therefore, increasing resolution and reducing pattern residue are important factors in determining device performance.

A color filter manufactured by using a pigment-type photosensitive resin composition has limitations in brightness and contrast ratio due to fineness of the pigment. In addition, color imaging devices for image sensors require smaller dispersed particle sizes to form fine patterns. In order to meet the requirements, attempts have been made to obtain a color filter with improved brightness and contrast ratio by introducing a non-particle-forming dye instead of a pigment to prepare a photosensitive resin composition suitable for the dye. However, dyes have poor durability to pigments, such as light fastness and heat resistance, etc., and thus brightness may decrease.

One embodiment provides a photosensitive resin composition capable of increasing color purity by minimizing the content of a colorant while ensuring durability.

Another embodiment provides a photosensitive resin layer manufactured using a photosensitive resin composition.

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

Another embodiment provides an electronic device including a color filter.

One embodiment provides a photosensitive resin composition comprising a colorant,

在化學式1中， X為氧原子或硫原子， L ¹為單鍵或經取代或未經取代的C1到C20伸烷基，且 R ¹到R ⁴各自獨立地為氫原子、經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20環烷基或經取代或未經取代的C6到C20芳基。 Wherein the colorant includes dyes represented by Chemical Formula 1, core-shell structure dyes and phthalocyanine dyes. [chemical formula 1]

In Chemical Formula 1, X is an oxygen atom or a sulfur atom, L ¹ is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, and R ¹ to R ⁴ are each independently a hydrogen atom, substituted or unsubstituted A substituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group.

在化學式L-1中， R ⁵和R ⁶各自獨立地為氫原子或經鹵素取代或未經取代的C1到C20烷基。 L ¹ may be represented by Chemical Formula L-1. [chemical formula L-1]

In the chemical formula L-1, R ⁵ and R ⁶ are each independently a hydrogen atom or a halogen-substituted or unsubstituted C1 to C20 alkyl group.

[化學式1-2]

[化學式1-3]

The dye represented by Chemical Formula 1 may be represented by any one of Chemical Formula 1-1 to Chemical Formula 1-3. [chemical formula 1-1]

[chemical formula 1-2]

[chemical formula 1-3]

The dye represented by Chemical Formula 1 may be contained in an amount greater than that of the core-shell structure dye, and the dye represented by Chemical Formula 1 may be contained in an amount greater than that of the phthalocyanine-based dye.

The phthalocyanine-based dye may be included in an amount greater than that of the core-shell structure dye.

The dye represented by Chemical Formula 1 may be contained in an amount greater than the content of the core-shell structure dye and the content of the phthalocyanine dye.

在化學式2中， R ⁷到R ¹⁰各自獨立地為經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20環烷基或經取代或未經取代的C6到C20芳基， [化學式3]

在化學式3中， R ¹¹為氫原子、鹵素原子、經取代或未經取代的C1到C20烷基或*-C(=O)OR ¹⁶（R ¹⁶為經取代或未經取代的C1到C20烷基）， R ¹²到R ¹⁵各自獨立地為氫原子、鹵素原子或經取代或未經取代的C1到C20烷基， m為1到10的整數， n為1到3的整數，且 L ²和L ³各自獨立地為單鍵或經取代或未經取代的C1到C10伸烷基。 The core-shell structure dye may be composed of a core represented by Chemical Formula 2 and a shell represented by Chemical Formula 3. [chemical formula 2]

In Chemical Formula 2, R ⁷ to R ¹⁰ are each independently substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C20 cycloalkyl or substituted or unsubstituted C6 to C20 C20 aryl, [chemical formula 3]

In Chemical Formula 3, R ¹¹ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is a substituted or unsubstituted C1 to C20 Alkyl), R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group, m is an integer from 1 to 10, n is an integer from 1 to 3, and L ² and L ³ are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

The core represented by Chemical Formula 2 may have a length of 1 nm to 3 nm.

The core represented by Chemical Formula 2 may have a maximum absorption peak at a wavelength of 530 nm to 680 nm.

[化學式2-2]

[化學式2-3]

[化學式2-4]

[化學式2-5]

[化學式2-6]

The core represented by Chemical Formula 2 may be represented by any one of Chemical Formula 2-1 to Chemical Formula 2-6. [chemical formula 2-1]

[chemical formula 2-2]

[chemical formula 2-3]

[chemical formula 2-4]

[chemical formula 2-5]

[chemical formula 2-6]

在化學式3-1中， R ¹¹為氫原子、鹵素原子、經取代或未經取代的C1到C20烷基或*-C(=O)OR ¹⁶（R ¹⁶為經取代或未經取代的C1到C20烷基）， R ¹²到R ¹⁵各自獨立地為氫原子、鹵素原子或經取代或未經取代的C1到C20烷基，且 n為1到3的整數。 The shell represented by Chemical Formula 3 may be represented by Chemical Formula 3-1. [chemical formula 3-1]

In Chemical Formula 3-1, R ¹¹ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl), R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl, and n is an integer of 1 to 3.

[化學式3-1-2]

[化學式3-1-3]

在化學式3-1-1到化學式3-1-3中， R ¹²到R ¹⁵各自獨立地為氫原子、鹵素原子或經取代或未經取代的C1到C20烷基，且 R ¹⁷和R ¹⁸各自獨立地為鹵素原子、經取代或未經取代的C1到C20烷基或*-C(=O)OR ¹⁶（R ¹⁶為經取代或未經取代的C1到C20烷基）。 The shell represented by Chemical Formula 3 may be represented by any one of Chemical Formula 3-1-1 to Chemical Formula 3-1-3. [Chemical formula 3-1-1]

[Chemical formula 3-1-2]

[chemical formula 3-1-3]

In Chemical Formula 3-1-1 to Chemical Formula 3-1-3, R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁷ and R ¹⁸ Each is independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl group).

The shell represented by Chemical Formula 3 may have a cage width of 6.5 Å to 7.5 Å.

[化學式3-B]

[化學式3-C]

[化學式3-D]

[化學式3-E]

The shell represented by Chemical Formula 3 may be represented by any one of Chemical Formula 3-A to Chemical Formula 3-E. [chemical formula 3-A]

[chemical formula 3-B]

[chemical formula 3-C]

[chemical formula 3-D]

[chemical formula 3-E]

Core-shell dyes can contain a core and a shell in a 1:1 molar ratio.

在化學式4中， R ¹⁰¹到R ¹¹⁶各自獨立地為氫原子、鹵素原子、經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20烷氧基、經取代或未經取代的C6到C20芳基或經取代或未經取代的C6到C20芳氧基， 前提為，R ¹⁰¹到R ¹⁰⁴中的至少一個、R ¹⁰⁵到R ¹⁰⁸中的至少一個以及R ¹⁰⁹到R ¹¹²中的至少一個各自獨立地由化學式5表示，且 R ¹¹³到R ¹¹⁶中的至少一個為鹵素原子或由化學式5表示， [化學式5]

在化學式5中， R ¹¹⁷和R ¹¹⁸各自獨立地為鹵素原子、經C1到C10烷基取代的C1到C20烷基、經取代或未經取代的C3到C20環烷基或經取代或未經取代的C6到C20芳基，且 n1和n2各自獨立地為0到5的整數，前提為1 ≤ n1+n2 ≤ 5。 Phthalocyanine-based dyes may be represented by Chemical Formula 4. [chemical formula 4]

In Chemical Formula 4, R ¹⁰¹ to R ¹¹⁶ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, a substituted or Unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, provided that at least one of R ¹⁰¹ to R ¹⁰⁴ , at least one of R ¹⁰⁵ to R ¹⁰⁸ and R ¹⁰⁹ to At least one of R ¹¹² is each independently represented by Chemical Formula 5, and at least one of R ¹¹³ to R ¹¹⁶ is a halogen atom or represented by Chemical Formula 5, [Chemical Formula 5]

In Chemical Formula 5, R ¹¹⁷ and R ¹¹⁸ are each independently a halogen atom, a C1 to C10 alkyl substituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, or a substituted or unsubstituted Substituted C6 to C20 aryl, and n1 and n2 are each independently an integer from 0 to 5, provided that 1 ≤ n1+n2 ≤ 5.

[化學式5-2]

[化學式5-3]

[化學式5-4]

Chemical Formula 5 may be represented by any one of Chemical Formula 5-1 to Chemical Formula 5-4. [chemical formula 5-1]

[chemical formula 5-2]

[chemical formula 5-3]

[chemical formula 5-4]

The colorant may further contain pigments.

The colorant may be included in an amount of 1% by weight to 15% by weight based on the total amount of the photosensitive resin composition.

The photosensitive resin composition may further include a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

Based on the total amount of the photosensitive resin composition, the photosensitive resin composition may include 1% by weight to 15% by weight of a colorant; 1% by weight to 20% by weight of a binder resin; 1% by weight to 20% by weight of a photosensitive resin. a polymerizable monomer; 0.1% by weight to 10% by weight of a photopolymerization initiator; and the remaining solvent.

The photosensitive resin composition may further contain malonic acid, 3-amino-1,2-propanediol, silane coupling agents with vinyl or (meth)acryloxy groups, leveling agents, surfactants, free radicals A polymerization initiator or a combination thereof.

Another embodiment provides a photosensitive resin layer manufactured using a photosensitive resin composition.

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

Another embodiment provides an electronic device including a color filter.

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

The photosensitive resin composition according to the embodiment may have increased color purity of a green region by mixing and using three different types of dyes, and may additionally secure durability, which is one of representative problems using dyes.

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 claims.

As used herein, when no specific definition is otherwise provided, "substituted" means that at least one hydrogen of a compound is replaced by a substituent selected from the group consisting of halogen atoms (F, Cl, Br, I), hydroxyl, C1 to C20 Alkoxy, nitro, cyano, amino, imino, azido, amidino, hydrazino, hydrazino, carbonyl, carbamoyl, thiol, ester, ether, carboxyl or their salts , sulfonic acid or its salt, phosphoric acid or its salt, C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C30 aryl, C3 to C20 cycloalkyl, C3 to C20 cycloalkenyl , C3 to C20 cycloalkynyl, C2 to C20 heterocycloalkyl, C2 to C20 heterocycloalkenyl, C2 to C20 heterocycloalkynyl, or combinations thereof.

As used herein, when no specific definition is otherwise provided, "heterocycloalkyl", "heterocycloalkenyl", "heterocycloalkynyl" and "heterocycloalkylene" mean the At least one heteroatom of N, O, S or P exists in the cyclic group of radical, cycloalkynyl and cycloalkylene.

As used herein, "(meth)acrylate" refers to both "acrylate" and "methacrylate" when no specific definition is otherwise provided.

As used herein, when no specific definition is otherwise provided, the term "combining" means mixing or copolymerizing.

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

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

在化學式1中， X為氧原子或硫原子， L ¹為單鍵或經取代或未經取代的C1到C20伸烷基，且 R ¹到R ⁴各自獨立地為氫原子、經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20環烷基或經取代或未經取代的C6到C20芳基。 The photosensitive resin composition according to the embodiment includes a colorant, wherein the colorant includes a dye represented by Chemical Formula 1, a core-shell structure dye, and a phthalocyanine dye. [chemical formula 1]

In Chemical Formula 1, X is an oxygen atom or a sulfur atom, L ¹ is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, and R ¹ to R ⁴ are each independently a hydrogen atom, substituted or unsubstituted A substituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group.

A CMOS image sensor refers to a non-memory semiconductor that converts an image received by a camera into a digital signal and is manufactured through the same CMOS semiconductor process as DRAM. CMOS image sensors have a picture element aggregation structure of color filters, photodiodes, amplifiers, etc., and in order to realize high-definition and ultra-thin camera modules, it is crucial to secure color filter technology. Color filter technology requires high-resolution and high-sensitivity materials, both of which can be met by cutting specific wavelengths that control the properties and sensitivity of negative photoresists.

In order to cut a specific wavelength, a conventional technique of controlling the wavelength by selecting the most similar pigment to increase the ratio has been used, but the content of the colorant in the photoresist increases and thus lowers the processability and reliability, mainly not applicable to the actual process or meet the desired characteristics.

The present invention relates to a photosensitive resin composition which improves the above problems and has desired cutting properties. Specifically, the photosensitive resin composition of the present invention can cut the blue-green region between blue and green by adjusting and cutting the wavelength of the dye represented by Chemical Formula 1, and also apply a dye having a core-shell structure to cut green The yellow area between blue and green to increase the color purity of green. In addition, two types of dyes can be used with phthalocyanine dyes to ensure durability. Also, the combination of the three types of dyes can reduce the use of colorants.

In other words, the photosensitive resin composition according to the embodiment can secure processability and reliability in a thin thickness through combination of specific dyes by using a small amount of colorant, and thus is optimally used as a processing material for LCD and CIS To increase the color gamut without reducing the transmittance, which may not be much different from conventional technology.

在化學式L-1中， R ⁵和R ⁶各自獨立地為氫原子或經鹵素取代或未經取代的C1到C20烷基。 For example, in Chemical Formula 1, L1 may be represented by Chemical Formula L-1. [chemical formula L-1]

In the chemical formula L-1, R ⁵ and R ⁶ are each independently a hydrogen atom or a halogen-substituted or unsubstituted C1 to C20 alkyl group.

[化學式1-2]

[化學式1-3]

For example, the dye represented by Chemical Formula 1 may be represented by any one of Chemical Formula 1-1 to Chemical Formula 1-3, but is not limited thereto. [chemical formula 1-1]

[chemical formula 1-2]

[chemical formula 1-3]

For example, the dye represented by Chemical Formula 1 may be contained in an amount greater than that of the core-shell structure dye, and the dye represented by Chemical Formula 1 may be contained in an amount greater than that of the phthalocyanine dye. In this case, both color purity and durability can be ensured.

In addition, the phthalocyanine-based dye may be contained in an amount greater than that of the core-shell structure dye. Specifically, the dye represented by Chemical Formula 1 may be included in an amount greater than the amount of the phthalocyanine dye, the phthalocyanine dye may be included in an amount greater than the amount of the core-shell dye, and may be greater than the core-shell dye and the phthalocyanine dye. The amount of the mixed content contains the dye represented by Chemical Formula 1. In this case, it may be more advantageous to ensure color purity and durability at the same time.

在化學式2中， R ⁷到R ¹⁰各自獨立地為經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20環烷基或經取代或未經取代的C6到C20芳基， [化學式3]

在化學式3中， R ¹¹為氫原子、鹵素原子、經取代或未經取代的C1到C20烷基或*-C(=O)OR ¹⁶（R ¹⁶為經取代或未經取代的C1到C20烷基）， R ¹²到R ¹⁵各自獨立地為氫原子、鹵素原子或經取代或未經取代的C1到C20烷基， m為1到10的整數， n為1到3的整數，且 L ²和L ³各自獨立地為單鍵或經取代或未經取代的C1到C10伸烷基。 For example, a core-shell dye may be composed of a core represented by Chemical Formula 2 and a shell represented by Chemical Formula 3. [chemical formula 2]

In Chemical Formula 2, R ⁷ to R ¹⁰ are each independently substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C20 cycloalkyl or substituted or unsubstituted C6 to C20 C20 aryl, [chemical formula 3]

In Chemical Formula 3, R ¹¹ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is a substituted or unsubstituted C1 to C20 Alkyl), R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group, m is an integer from 1 to 10, n is an integer from 1 to 3, and L ² and L ³ are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

For example, the core-shell structure dye may comprise a non-covalent bond, that is, a hydrogen between an oxygen atom of the compound represented by Chemical Formula 2 and a hydrogen atom forming a bond with a nitrogen atom of the shell represented by Chemical Formula 3 key.

The compound represented by Chemical Formula 2 has excellent green spectral characteristics and a high molar extinction coefficient, and thus can be used as a green dye, but has the effect of deteriorating brightness due to less durability than pigments during baking after forming a color resist. question. In an embodiment, since the shell represented by Chemical Formula 3 can form a core-shell structure with the core represented by the compound represented by Chemical Formula 2, the core-shell structure compound can improve durability of a color filter applied as a colorant, Realizes color filters with high brightness and high contrast.

Specifically, the core-shell structure dye has a structure in which the compound represented by Chemical Formula 2 is a core and a shell surrounding the core, wherein the shell is a macrocyclic compound represented by Chemical Formula 3 and may form a coating while surrounding the core. Such a structure (ie, a structure in which the compound represented by Chemical Formula 2 exists inside the ring represented by Chemical Formula 3) can improve the durability of the core-shell structure dye, realizing a color filter with high brightness and high contrast.

For example, in Chemical Formula 3, L ² and L ³ may each independently be a substituted or unsubstituted C1 to C10 alkylene group. In this case, solubility is improved, and a structure in which a shell surrounds the compound represented by Chemical Formula 2 is easily formed.

For example, in Chemical Formula 2, R ⁷ and R ⁹ may each independently be a substituted or unsubstituted C1 to C20 alkyl or a substituted or unsubstituted C3 to C20 cycloalkyl, and R ⁸ and Each R ¹⁰ can be independently a substituted or unsubstituted C6 to C20 aryl.

For example, R ⁷ and R ⁹ may each independently be 'C1 to C20 alkyl substituted or unsubstituted by C1 to C10 alkoxy' or 'C3 unsubstituted or substituted by C1 to C10 alkoxy to C20 cycloalkyl', and R ⁸ and R ¹⁰ may each independently be 'C6 to C20 aryl substituted or unsubstituted by C1 to C10 alkoxy'.

For example, the C1 to C10 alkoxy group may be an unsubstituted C1 to C10 alkoxy group or a C1 to C6 alkoxy group substituted with a C1 to C4 alkyl group.

As shown in the following scheme, the compound represented by Chemical Formula 2 has three resonance structures, but in this specification, only one resonance structure is drawn for the compound represented by Chemical Formula 2 for convenience. That is, the compound represented by Chemical Formula 2 may be represented by any one of the three resonance structures. [plan]

[化學式2-2]

[化學式2-3]

[化學式2-4]

[化學式2-5]

[化學式2-6]

For example, the core may be represented by any one of Chemical Formula 2-1 to Chemical Formula 2-6, but not necessarily limited thereto. [chemical formula 2-1]

[chemical formula 2-2]

[chemical formula 2-3]

[chemical formula 2-4]

[chemical formula 2-5]

[chemical formula 2-6]

For example, when the compounds represented by Chemical Formula 2-1 to Chemical Formula 2-6 are used in a photosensitive resin composition (for example, as a dye), the solubility of the solvent to be described later may be greater than or equal to 5, such as 5 to 10 . Solubility can be obtained from the amount (grams) of dye (compound) dissolved in 100 grams of solvent. When the compound (for example, a dye) has a solubility within the range, it is ensured that it is compatible with other components in the photosensitive resin composition (that is, a binder resin, a photopolymerizable monomer, and a photopolymerization initiator to be described later). ) compatibility and coloring properties, and prevents the precipitation of dyes.

For example, the compounds represented by Chemical Formula 2-1 to Chemical Formula 2-6 may have improved heat resistance. That is, the thermal decomposition temperature measured using a thermogravimetric analyzer (thermogravimetric analyzer; TGA) may be greater than or equal to 200°C, for example, 200°C to 300°C.

The compound represented by Chemical Formula 2 contained in or composed of the core may have a length of 1 nm to 3 nm, for example, 1.5 nm to 2 nm. When the compound represented by Chemical Formula 2 has a length within the range, a core-shell structure may be easily formed. In other words, the compound represented by Chemical Formula 2 has a length within the range and thus can easily form a structure in which a shell that is a macrocyclic compound represented by Chemical Formula 3 surrounds the compound represented by Chemical Formula 2. When a compound having a length outside the range is used, a structure in which the shell does not surround the core compound may not be obtained, and durability may not be improved.

For example, the core-shell compound may have a maximum absorption peak at a wavelength of 530 nm to 680 nm. A core-shell structure dye having spectral characteristics is used, for example, as a green dye and thus can provide a photosensitive resin composition for a color filter having high brightness and high contrast.

For example, a core-shell compound may comprise a core and a shell in a 1:1 molar ratio. When the core and the shell are present in the molar ratio, the coating (shell) surrounding the core can be preferably formed.

在化學式3-1中， R ¹¹為氫原子、鹵素原子、經取代或未經取代的C1到C20烷基或*-C(=O)OR ¹⁶（R ¹⁶為經取代或未經取代的C1到C20烷基）， R ¹²到R ¹⁵各自獨立地為氫原子、鹵素原子或經取代或未經取代的C1到C20烷基，且 n為1到3的整數。 For example, the shell represented by Chemical Formula 3 may be represented by Chemical Formula 3-1. [chemical formula 3-1]

In Chemical Formula 3-1, R ¹¹ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl), R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl, and n is an integer of 1 to 3.

For example, in Chemical Formula 3-1, R ¹¹ may be a hydrogen atom, and R ¹² to R ¹⁵ may each independently be a hydrogen atom or a substituted or halogen atom.

For example, in Chemical Formula 3-1, R ¹¹ may be a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is substituted or unsubstituted C1 to C20 alkyl), and R ¹² to R ¹⁵ can each independently be a hydrogen atom.

For example, R ¹¹ may be a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl group) , and at least one of R ¹² to R ¹⁵ is a substituted or unsubstituted C1 to C20 alkyl group.

[化學式3-1-2]

[化學式3-1-3]

在化學式3-1-1到化學式3-1-3中， R ¹²到R ¹⁵各自獨立地為氫原子、鹵素原子或經取代或未經取代的C1到C20烷基，且 R ¹⁷和R ¹⁸各自獨立地為鹵素原子、經取代或未經取代的C1到C20烷基或*-C(=O)OR ¹⁶（R ¹⁶為經取代或未經取代的C1到C20烷基）。 For example, the shell represented by Chemical Formula 3 may be represented by any one of Chemical Formula 3-1-1 to Chemical Formula 3-1-3. [Chemical formula 3-1-1]

[Chemical formula 3-1-2]

[chemical formula 3-1-3]

In Chemical Formula 3-1-1 to Chemical Formula 3-1-3, R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁷ and R ¹⁸ Each is independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ (R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl group).

For example, the shell may have a cage width of 6.5 Angstroms to 7.5 Angstroms and a volume of 10 Angstroms to 16 Angstroms. The cage width refers to the internal distance of the shell in the present invention, for example, the distance between two different phenylene groups in which two methylene groups are bonded in the shell represented by Chemical Formula 3 (see FIG. 1 ). When the shell has a cage width within the range, a core-shell dye having a structure surrounding an aromatic acid cyanine compound can be obtained, and thus when the core-shell dye is used as a colorant of a photosensitive resin composition, it is possible to implement Color filters with improved durability and high brightness.

[化學式3-B]

[化學式3-C]

[化學式3-D]

[化學式3-E]

For example, the shell may be represented by any one of Chemical Formula 3-A to Chemical Formula 3-E, but not necessarily limited thereto. [chemical formula 3-A]

[chemical formula 3-B]

[chemical formula 3-C]

[chemical formula 3-D]

[chemical formula 3-E]

[化學式A-2]

For example, the core-shell dye may be represented by Chemical Formula A-1 or Chemical Formula A-2, but not necessarily limited thereto. [Chemical formula A-1]

[Chemical formula A-2]

Core-shell dyes can be used alone as green dyes, and can also be mixed with auxiliary dyes.

Auxiliary dyes can be triarylmethane dyes, anthraquinone dyes, benzylidene dyes, cyanine dyes, phthalocyanine dyes, azaporphyrin-based dyes, indigo dyes, xanthenes Dyes, pyridone azo-based dyes, etc.

在化學式4中， R ¹⁰¹到R ¹¹⁶各自獨立地為氫原子、鹵素原子、經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20烷氧基、經取代或未經取代的C6到C20芳基或經取代或未經取代的C6到C20芳氧基， 前提為，R ¹⁰¹到R ¹⁰⁴中的至少一個、R ¹⁰⁵到R ¹⁰⁸中的至少一個以及R ¹⁰⁹到R ¹¹²中的至少一個各自獨立地由化學式5表示，且 R ¹¹³到R ¹¹⁶中的至少一個為鹵素原子或由化學式5表示， [化學式5]

其中，在化學式5中， R ¹¹⁷和R ¹¹⁸各自獨立地為鹵素原子、經C1到C10烷基取代的C1到C20烷基、經取代或未經取代的C3到C20環烷基或經取代或未經取代的C6到C20芳基，且 n1和n2各自獨立地為0到5的整數，前提為1 ≤ n1+n2 ≤ 5。 For example, a phthalocyanine-based dye may be represented by Chemical Formula 4. [chemical formula 4]

In Chemical Formula 4, R ¹⁰¹ to R ¹¹⁶ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, a substituted or Unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, provided that at least one of R ¹⁰¹ to R ¹⁰⁴ , at least one of R ¹⁰⁵ to R ¹⁰⁸ and R ¹⁰⁹ to At least one of R ¹¹² is each independently represented by Chemical Formula 5, and at least one of R ¹¹³ to R ¹¹⁶ is a halogen atom or represented by Chemical Formula 5, [Chemical Formula 5]

Wherein, in Chemical Formula 5, R ¹¹⁷ and R ¹¹⁸ are each independently a halogen atom, a C1 to C20 alkyl group substituted by a C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or Unsubstituted C6 to C20 aryl, and n1 and n2 are each independently an integer from 0 to 5, provided that 1 ≤ n1+n2 ≤ 5.

[化學式5-2]

[化學式5-3]

[化學式5-4]

For example, Chemical Formula 5 may be represented by any one of Chemical Formula 5-1 to Chemical Formula 5-4. [chemical formula 5-1]

[chemical formula 5-2]

[chemical formula 5-3]

[chemical formula 5-4]

[化學式7]

[化學式8]

For example, the phthalocyanine-based dye may be represented by any one of Chemical Formula 6 to Chemical Formula 8, but is not necessarily limited thereto. [chemical formula 6]

[chemical formula 7]

[chemical formula 8]

The colorant may further contain pigments.

The pigments may be red pigments, green pigments, blue pigments, yellow pigments, black pigments, and the like.

Red Pigment 254, C.I. Red Pigment 255, C.I. Red Pigment 264, C.I. Red Pigment 270, C.I. Red Pigment 272, C.I. Red Pigment 177, C.I. Red Pigment 89, and the like. Examples of the green pigment may be C.I. Green Pigment 7, C.I. Green Pigment 36, C.I. Green Pigment 58, C.I. Green Pigment 59, and the like. Examples of blue pigments may be copper phthalocyanine pigments such as C.I. Blue Pigment 15:6, C.I. Blue Pigment 15, C.I. Blue Pigment 15:1, C.I. Blue Pigment 15:2, C.I. Blue Pigment 15:3 , C.I. Blue Pigment 15:4, C.I. Blue Pigment 15:5, C.I. Blue Pigment 16, etc. Examples of yellow pigments may be isoindoline pigments such as C.I. Yellow Pigment 139 and the like; quinoline yellow pigments such as C.I. Yellow Pigment 138 and the like; nickel complex pigments such as C.I. Yellow Pigment 150 and the like. Examples of black pigments may be aniline black, perylene black, titanium black, carbon black, and the like. Pigments may be used alone or in admixture of two or more and are not limited thereto.

The pigment may be contained in the photosensitive resin composition for a color filter in the state of a pigment dispersion liquid. Pigment dispersions can be composed of pigments and solvents, dispersants, dispersing resins, and the like.

The solvent can be ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc., and ideally propylene glycol methyl ether acetate ester.

The dispersant contributes to the uniform dispersion of the pigment, and may contain a nonionic dispersant, an anionic dispersant, or a cationic dispersant. Specific examples may be polyalkylene glycol or its ester, polyoxyalkylene, polyol ester alkylene oxide adduct, alcohol alkylene oxide addition product, sulfonate, sulfonate, carboxylate, carboxylic acid Salt, alkylamide alkylene oxide adduct, alkylamine, and may be used alone or in admixture of two or more.

The dispersion resin may be an acrylic resin containing a carboxyl group, and improves the stability of the pigment dispersion liquid and the pattern property of the graphic element.

However, the colorant in the photosensitive resin composition according to the embodiment may be composed of the above three types of dyes alone, and deterioration in durability may not occur, compared to the case where a pigment is additionally included. That is, when the colorant is composed of three types of dyes alone without using a pigment, the amount of the colorant used can be greatly reduced, so that workability and reliability can be ensured even at a thin thickness sex.

Based on the total amount of the photosensitive resin composition, coloring can be contained in an amount of 1% to 15% by weight, such as 1% by weight to 10% by weight, such as 1% by weight to 5% by weight, such as 1% by weight to 3% by weight. agent. When a colorant within the above range is used, higher brightness and contrast can be exhibited in desired color coordinates.

The photosensitive resin composition according to the embodiment may further include a binder resin.

The binder resin may be a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin including at least one acrylic acid repeating unit (acrylic binder resin).

The first ethylenically unsaturated monomer may be an ethylenically unsaturated monomer including one or more carboxyl groups, and specific examples thereof may include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or combinations thereof .

The first ethylenically unsaturated monomer may be included in an amount of 5% to 50% by weight, for example, 10% to 40% by weight, based on the total amount of the alkali-soluble resin.

The second ethylenically unsaturated monomer may include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene and vinylbenzyl methyl ether; unsaturated carboxylic acid ester compounds such as (methyl ) methyl acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, (meth) acrylic acid Benzyl ester, cyclohexyl (meth)acrylate, and phenyl (meth)acrylate; aminoalkyl unsaturated carboxylic acid ester compounds such as 2-aminoethyl (meth)acrylate and 2-aminoethyl (meth)acrylate - Dimethylaminoethyl esters; vinyl carboxylic acid compounds such as vinyl acetate and vinyl benzoate; glycidyl unsaturated carboxylic acid compounds such as glycidyl (meth)acrylate; vinyl cyanide compounds such as (meth)acrylonitrile; unsaturated amide compounds such as (meth)acrylamide, etc., and these may be used alone or in combination of two or more.

Specific examples of the binder resin may be methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, methacrylic acid/benzyl methacrylate/methacrylic acid-2 -hydroxyethyl ester copolymer, methacrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc., but the present invention is not limited to these. These may be used alone or in admixture of two or more.

The binder resin may have a weight average molecular weight of 3,000 g/mol to 150,000 g/mol, eg, 5,000 g/mol to 50,000 g/mol, eg, 20,000 g/mol to 30,000 g/mol. When the binder resin has a weight average molecular weight within the range, the composition can have excellent close contact properties with the substrate, good physical and chemical properties, and appropriate viscosity.

The binder resin may have an acid value of 15 mg KOH/g to 60 mg KOH/g, for example 20 mg KOH/g to 50 mg KOH/g. When the binder resin has an acid value within the range, it can bring excellent picture resolution.

The adhesive resin may further include epoxy adhesive resin and acrylic adhesive resin.

The epoxy-based binder resin is a monomer or oligomer polymerizable by heating, and may contain a compound having a carbon-carbon unsaturated bond and a carbon-carbon ring bond.

The epoxy adhesive resin may further include bisphenol A epoxy resin, bisphenol F epoxy resin, phenol novolac epoxy resin, cycloaliphatic epoxy resin and aliphatic polyglycidyl ether.

Currently available products of the epoxy adhesive resin may include YX4000, YX4000H, YL6121H, YL6640 or YL6677 of Yuka Shell Epoxy Co., Ltd.; cresol novolac Type epoxy resins, such as EOCN-102, EOCN-103S, EOCN-104S, EOCN-1020, EOCN-1025, and EOCN-1027 from Nippon Kayaku Co., Ltd. EPIKOTE 180S75 from Oxygen Resin Co., Ltd.; bisphenol A epoxy resins, such as EPIKOTE 1001, EPIKOTE 1002, EPIKOTE 1003, EPIKOTE 1004, EPIKOTE 1007, EPIKOTE 1009, EPIKOTE 1010 and EPIKOTE 828 from Oily Shell Epoxy Co., Ltd.; Bisphenol F type epoxy resin, such as EPIKOTE 807 and EPIKOTE 834 from Yuka Shell Epoxy Co., Ltd.; phenol novolac type epoxy resin, such as EPIKOTE 152, EPIKOTE 154 or EPIKOTE from Yuka Shell Epoxy Co., Ltd 157H65 and EPPN 201 and EPPN 202 of Nippon Kayaku Co., Ltd.; other cyclic aliphatic epoxy resins, such as CY175, CY177 and CY179 of CIBA-GEIGY A.G, and U.C.C. ), ERL-4234, ERL-4299, ERL-4221 and ERL-4206, Shodyne 509 of Showa Denko K.K., ARALDITE CY-182, CY-192 and CY- 184. Epichron 200 and Epichron 400 from Dainippon Ink and Chemicals, Inc., EPIKOTE 871, EPIKOTE 872 and EP1032H60 from Oily Shell Epoxy Co., Ltd., Celanese Coatings Co., Ltd. Coatings Co., Ltd.)’s ED-5661 and ED-5662; aliphatic polyglycidyl ethers, such as EPIKOTE 190P and EPIKOTE 191P from Yuhua Shell Epoxy Co., Ltd., Kyoesha Yushi Co., Ltd. ., Ltd.), Epolite 100MF from Nippon Yushi Co., Ltd. piol TMP etc.

The binder resin may be included in an amount of 1% to 20% by weight, for example, 1% to 15% by weight, based on the total amount of the photosensitive resin composition. When the binder resin is contained within the above range, developability is improved when manufacturing a color filter, and cross-linking properties are improved for excellent surface smoothness.

The photosensitive resin composition according to the embodiment may further include a photopolymerizable monomer.

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

Since the photopolymerizable monomer has an ethylenically unsaturated double bond, a pattern having improved heat resistance, light resistance, and chemical resistance may be formed by causing sufficient polymerization during exposure to light during pattern formation.

Specific examples of photopolymerizable monomers may be ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, ) 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 Acrylates, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy(meth)acrylate, ethylene glycol mono Methyl ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tri(meth)acryloxyethyl phosphate, novolak epoxy (meth)acrylate, etc.

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

The photopolymerizable monomer may be treated with an acid anhydride to improve developability.

The photopolymerizable monomer may be included in an amount of 1% by weight to 20% by weight, or for example, 1% by weight to 15% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer in the above range is contained, pattern characteristics and developability may be improved in manufacturing a color filter.

The photosensitive resin composition according to the embodiment may further include a photoinitiator.

The photopolymerization initiator may include acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, oxime-based compounds, and the like.

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

Examples of benzophenone compounds may be benzophenone, benzoyl benzoate, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated diphenyl Methanone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.

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

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

Examples of triazines can be 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3',4 '-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl) base)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis( Trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine , 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthol-yl)-4,6-bis(tri Chloromethyl)-s-triazine, 2-4-trichloromethyl(4'-methoxystyryl)-6-triazine, etc.

Examples of oxime compounds can be 2-(o-benzoyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime)-1 -[9-Ethyl-6-(2-methylbenzoyl)-9H-xazol-3-yl]ethanone and the like.

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

The photopolymerization initiator may be included in an amount of 0.1% by weight to 10% by weight, or, for example, 0.1% by weight to 5% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, photopolymerization is sufficiently generated during exposure in a pattern forming process for manufacturing a color filter, thereby improving sensitivity and improving transmittance.

The photosensitive resin composition according to the embodiment may further include a solvent.

The solvent is not particularly limited, but specifically, for example, alcohols such as methanol, ethanol, etc.; ethers, such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran, etc.; glycol ethers, such as Ethylene glycol methyl ether, ethylene glycol ethyl ether, propylene glycol methyl ether, etc.; cellosolve acetate, such as cellosolve methyl acetate, cellosolve ethyl acetate, cellosolve diethyl acetate, etc.; carbitol , such as methyl ethyl carbitol, 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 alkyl ether acetate, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, etc.; aromatic hydrocarbons, such as toluene, xylene, etc.; ketones, such as methyl ethyl ketone , cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl n-butyl ketone, methyl-n-amyl ketone, 2-heptanone, etc.; saturated fat Alkyl monocarboxylates, such as ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; alkyl lactates, such as methyl lactate, ethyl lactate, etc.; alkyl glycolates, such as methyl glycolate, glycolic acid Ethyl, butyl glycolate, etc.; alkoxyalkyl acetates, such as methoxymethyl acetate, methoxyethyl acetate, methoxybutyl acetate, ethoxymethyl acetate, ethoxyethyl acetate Esters, etc.; Alkyl 3-hydroxypropionate, such as methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, etc.; Alkyl 3-alkoxypropionate, such as methyl 3-methoxypropionate, Ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; alkyl 2-hydroxypropionate, such as methyl 2-hydroxypropionate, 2- Ethyl hydroxypropionate, 2-hydroxypropyl propionate, etc.; alkyl 2-alkoxypropionate, such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, 2-ethoxy Ethyl propionate, methyl 2-ethoxy propionate, etc.; alkyl 2-hydroxy-2-methyl propionate, such as methyl 2-hydroxy-2-methyl propionate, 2-hydroxy-2- Ethyl methyl propionate, etc.; 2-alkoxy-2-methyl propionate alkyl, such as 2-methoxy-2-methyl propionate, 2-ethoxy-2-methyl propionate Ethyl acetate, etc.; esters, such as 2-hydroxyethyl propionate, 2-hydroxy-2-methylethyl propionate, hydroxyethyl acetate, methyl 2-hydroxy-3-methylbutyrate, etc.; or ketones esters, such as ethyl pyruvate, etc., and may additionally be N-methylformamide, N,N-dimethylformamide, N-methylformamide, N-methylacetamide, N , N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone (isophorone), caproic acid, octanoic acid, 1-octyl Alcohol, 1-Nonanol, Benzyl Alcohol, Benzyl Acetate, Ethyl Benzoate, Diethyl Oxalate, Diethyl Maleate, γ-Butyrolactone, Ethyl Carbonate, Propyl Carbonate, Cellosolve phenyl acetate, and they may be used alone or in admixture of two or more.

In consideration of compatibility and reactivity, it is ideal to use: glycol ethers, such as ethylene glycol monoethyl ether, etc.; glycol alkyl ether acetates, such as ethylene glycol ethyl ether, ethyl acetate, etc.; esters, such as propylene glycol 2-hydroxyethyl acid, etc.; diethylene glycol, such as diethylene glycol monomethyl ether, etc.; propylene glycol alkyl ether acetate, such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, etc.

Based on the total amount of the photosensitive resin composition, the solvent may be included in the remainder, and specifically, 35% by weight to 90% by weight. When the solvent is contained within the above range, the photosensitive resin composition has excellent applicability and can maintain excellent flatness in a film having a thickness of 3 micrometers or more.

The photosensitive resin composition may further contain other additives, such as malonic acid; 3-amino-1,2-propanediol; silane coupling agent containing vinyl or (meth)acryloxy; leveling agent; fluorine Surfactants; radical polymerization initiators to prevent staining or spotting during coating, to adjust leveling, or to prevent pattern residue due to non-development.

The photosensitive resin composition may further include epoxy compounds to improve the close contact property with the substrate.

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

The amount of additive used can be controlled depending on the desired properties.

Another embodiment provides a photosensitive resin layer manufactured using the aforementioned photosensitive resin composition.

Another embodiment provides a color filter manufactured using a photosensitive resin composition. The method of manufacturing the color filter is as follows.

The sensitization of color filters will be performed on a bare glass substrate or on a glass substrate coated with a protective layer (SiN _x ) with a thickness of 500 angstroms to 1500 angstroms using an appropriate method such as spin coating, slit coating, etc. The permanent resin composition is coated to have a thickness of 3.1 μm to 3.4 μm. After coating, the composition is irradiated with light to form a desired pattern for the color filter. After the light is irradiated, the coating is treated with an alkaline developer and its non-irradiated areas can be dissolved, thereby forming the pattern for the color filter. Depending on the desired number of R, G, and B colors, this process is repeated to produce a color filter with a desired pattern.

In addition, the image pattern obtained by development is cured by heat treatment, actinic ray irradiation, or the like, thereby improving crack resistance, solvent resistance, and the like.

Another embodiment provides an electronic device including a color filter, such as a display device, a camera, and the like.

Hereinafter, the present invention is shown in more detail with reference to examples. However, these examples should not be construed as limiting the scope of the invention in any sense.

( preparation of dyes )

( Preparation example 1 : Prepared by the chemical formula 1-1 indicated compound )

8.15 mmoles of 7-(diethylamino)-2-oxo-2H-benzopyran-3-carbaldehyde, 4.08 mmoles of 2,2-bis(3-amino-4-hydroxyphenyl)hexa Fluoropropane and 163 mmol of sodium acetate were dissolved in 40 mL of acetic acid, and then stirred at 90° C. for 10 hours. Subsequently, 200 ml of water were added to the reaction mixture. The precipitate produced therein was filtered and dissolved in dichloromethane, and then washed with water through a separatory funnel.

Maldi-tof MS：816 m/z The dichloromethane layer recovered from the separatory funnel was dried with MgSO ₄ and purified through silica gel column chromatography to obtain the compound represented by Chemical Formula 1-1. [chemical formula 1-1]

Maldi-tof MS: 816 m/z

( Preparation example 2 : Prepared by the chemical formula 1-2 indicated compound )

Maldi-tof MS：1024 m/z The compound represented by Chemical Formula 1-2 was obtained in the same manner as in Preparation Example 1, except that 7-(4-(2-isobutyl-2,4-dimethylphenyl)amino)-2 -Oxo-2H-benzopyran-3-carbaldehyde in place of 7-(diethylamino)-2-oxo-2H-benzopyran-3-carbaldehyde. [chemical formula 1-2]

Maldi-tof MS: 1024 m/z

( Preparation example 3 : Prepared by the chemical formula 1-3 indicated compound )

Maldi-tof MS：1008 m/z The compound represented by Chemical Formula 1-3 was obtained in the same manner as in Preparation Example 1, except that 7-(4-diphenylamino)-2-oxo-2H-benzopyran-3-carbaldehyde was used Instead of 7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde. [chemical formula 1-3]

Maldi-tof MS: 1008 m/z

( Preparation example 4 : Prepared by the chemical formula 1-4 indicated compound )

Add 2,4-dimethyldiphenylamine (10 mol), 1,2-epoxycyclohexane (12 mol) and sodium hydride (12 mol) to N,N-dimethylformamide , and then stirred at 90 °C for 24 hours. Then, 15 mmol of iodomethyl was additionally added thereto, and then stirred for 3 hours.

Subsequently, ethyl acetate was added to the solution and then washed with water twice to extract an organic layer. The extracted organic layer was distilled under reduced pressure and separated by column chromatography, thereby obtaining the compound of Intermediate 1.

Intermediate 1 (60 mmol), 3,4-dihydroxy-3-cyclobutyne-1,2-dione (30 mmol) in toluene (200 mL) and butanol (200 mL) and then reflux, and the resulting water was removed with a Dean-stark distillation apparatus. After stirring for 12 hours, the green reaction product was distilled under reduced pressure and purified by column chromatography to obtain the compound of Intermediate 2.

Maldi-tof MS：1231 m/z After intermediate 2 (5 mmol) was dissolved in 600 ml of chloroform solvent, triethylamine (50 mmol) was added thereto, and then 2,6-pyridinedicarbonyl dichloride (20 mmol ear) and p-xylylenediamine (20 mmol) were dissolved in 60 ml of chloroform, respectively, and then added dropwise thereto simultaneously at room temperature for 5 hours. After 12 hours, the obtained mixture was distilled under reduced pressure, and separated by column chromatography, thereby obtaining a compound represented by Chemical Formula A-1. [Chemical formula A-1]

Maldi-tof MS: 1231 m/z

( Preparation example 5 : Prepared by the chemical formula 1-5 indicated compound )

Maldi-tof MS：1375 m/z The same synthesis as above was carried out up to intermediate 2 of formula A-1. After intermediate 2 (5 mmol) was dissolved in 600 ml of chloroform solvent, triethylamine (50 mmol) was added thereto, and then 2,6-pyridinedicarbonyl dichloride (20 mmol ear) and tetrafluoro-p-xylylenediamine (20 mmol) were respectively dissolved in 60 ml of chloroform and added dropwise thereto simultaneously at room temperature for 5 hours. After 12 hours, the obtained mixture was subjected to distillation under reduced pressure, and separated by column chromatography, thereby obtaining a compound represented by Chemical Formula A-2. [Chemical formula A-2]

Maldi-tof MS: 1375 m/z

( Preparation example 6 : Prepared by the chemical formula 1-6 indicated compound )

3,4,5,6-tetrachlorophthalonitrile (5 g), 2,4-di-tert-butylphenol (3.8 g), K ₂ CO ₃ (3.898 g) and N,N-dimethyl Methylformamide (50 mL) was placed in a 100 mL flask and then stirred at 70°C. When the reaction was complete, after extraction with ethyl acetate (EA), the liquid column purified by EA/hexane column chromatography was concentrated to obtain a solid, and the solid was vacuum-dried to obtain 3,5,6 - Trichloro-4-(2,4-di-tert-butylphenoxy)-phthalonitrile.

Maldi-tof MS：1809 m/z 3,5,6-Trichloro-4-(2,4-di-tert-butylphenoxy)-phthalonitrile (1.45 g), 1,8-diazabicycloundec-7 -ene (0.38 g) and 1-pentenol (7 g) were placed in a 100 ml flask and heated at 90° C., and after the solid was dissolved, zinc acetate (0.15 g) was added thereto, and then stirred while Continue heating to 140°C. When the reaction was complete, the precipitate was filtered with MeOH and dried in vacuo. The dried solid was purified by column chromatography. A small amount of dichloromethane was added to the obtained solid, and after dissolving the solid therein, methanol was added thereto for crystallization. The obtained solid was filtered and vacuum-dried, thereby obtaining a compound represented by Chemical Formula 6. [chemical formula 6]

Maldi-tof MS: 1809 m/z

( Preparation example 7 : Prepared by the chemical formula 1-7 indicated compound )

3,4,5,6-Tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.21 g), K ₂ CO ₃ (3.9 g) and acetone (25 mL) were placed in a 100 mL flask and then stirred while heating at 70 °C. When the reaction was complete, the resultant was filtered and washed with acetone, and the solid obtained by distilling the liquid therefrom was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to obtain 4-(bis phen-2-yloxy)-3,5,6-trichloro-phthalonitrile.

Maldi-tof MS：1650 m/z 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (1.6 g), 3,4,6-trichloro-5-(2,6-di Chloro-phenoxy)-phthalonitrile (1.5 g), 1,8-diazabicyclounde-7-ene (1.74 g) and 1-pentenol (14 g) in a 100 ml flask and heated at 90°C, and after the solid was dissolved, zinc acetate (0.34 g) was added thereto, and then stirring was performed while heating at 140°C. When the reaction was complete, the precipitate was confirmed with methanol, filtered, dried in vacuo, and purified by column chromatography. Subsequently, an appropriate amount of dichloromethane was added to the purified solid, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried in vacuum, thereby obtaining the compound represented by Chemical Formula 7. [chemical formula 7]

Maldi-tof MS: 1650 m/z

( Preparation example 8 : Prepared by the chemical formula 1-8 indicated compound )

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-cyclohexylphenol (3.3143 g), K ₂ CO ₃ (3.898 g) and N,N-dimethylformamide (50 mL) was placed in a 100 mL flask and then stirred while heating at 70°C. When the reaction was complete, after extraction with ethyl acetate (EA), the liquid purified by EA/hexane column chromatography was concentrated, and the solid obtained therefrom was vacuum-dried to obtain 3,5,6-trichloro- Compounds of 4-(2-cyclohexylphenoxy)-phthalonitrile.

Maldi-tof MS：1548 m/z In a 100 ml flask, mix 3,5,6-trichloro-4-(2-cyclohexylphenoxy)-phthalonitrile (1.5 g), 3,4,5,6-tetrachlorophthalonitrile Dicarbonitrile (0.33 g), 1,8-diazabicycloundec-7-ene (1.3 g) and 1-pentenol (15 ml) were heated at 90°C, and after the solid was dissolved, Zinc acetate (0.23 g) was added, and then stirred with continuous heating at 140°C. When the reaction was complete, the precipitate was filtered with MeOH and dried in vacuo, and the dried solid was purified by column chromatography. Subsequently, a small amount of dichloromethane was added to the purified solid to dissolve it, and methanol was added thereto to conduct crystallization. The obtained solid was filtered and vacuum-dried, thereby obtaining a compound represented by Chemical Formula 8. [chemical formula 8]

Maldi-tof MS: 1548 m/z

( Preparation of photosensitive resin composition )

The specifications of the components used to prepare the photosensitive resin composition are as follows. (A) colorant (dye) (A1) Dye prepared in Preparation Example 1 (represented by Chemical Formula 1-1) (A2) Dye prepared in Preparation Example 2 (represented by Chemical Formula 1-2) (A3) Dye prepared in Preparation Example 3 (represented by Chemical Formula 1-3) (A4) Dye prepared in Preparation Example 4 (represented by Chemical Formula A-1) (A5) Dye prepared in Preparation Example 5 (represented by formula A-2) (A6) The dye prepared in Preparation Example 6 (represented by Chemical Formula 6) (A7) The dye prepared in Preparation Example 7 (represented by Chemical Formula 7) (A8) The dye prepared in Preparation Example 8 (represented by Chemical Formula 8) (pigment) (A9) C.I. Green Pigment 58 (SANYO) (A10) C.I. Yellow Pigment 138 (Sanyo) (B) Binder resin (B1) Acrylic adhesive resin (RY25, Showa Denko (SHOWA DENKO)) (B2) Epoxy adhesive resin (EHPE3150, Daicel (DAICEL)) (C) Photopolymerizable monomer Dipentaerythritol hexaacrylate (Nippon Kayaku Co., Ltd.) (D) Photopolymerization initiator SPI-03 (Samyang Corp.) (E) Solvent Propylene Glycol Monomethyl Ether Acetate (PGMEA)

example 1 to instance 6 and comparative example 1 to comparative example 4

Each of the photosensitive resin compositions was prepared by mixing the components in the compositions shown in Table 1. Specifically, a photopolymerization initiator was dissolved in a solvent and then stirred at room temperature for 2 hours, a colorant was added thereto and then stirred for 30 minutes, and a binder resin and a photopolymerizable monomer were added thereto and then Stir at room temperature for 2 hours. The obtained solution was filtered three times to remove impurities, and each photosensitive resin composition was prepared.

(Table 1)

(unit weight%) example comparative example 1 2 3 4 5 6 1 2 3 4 (A) colorant A1 1.1 - - - - - - - 1.1 - A2 - 1.1 - - - - - - - - A3 - - 1.1 1.1 1.1 1.1 - - - - A4 0.2 0.2 0.2 - - - - 0.2 - - A5 - - - 0.2 0.2 0.2 - - - - A6 - - - - - 0.5 - - - - A7 0.5 0.5 0.5 0.5 - - 0.5 - - - A8 - - - - 0.5 - - - - - A9 - - - - - - 21.1 21.4 20.5 21.6 A10 12.1 12.1 12.1 12.1 12.1 12.1 7.0 7.0 7.0 7.0 (B) Binder resin B1 8.0 8.0 8.0 8.0 8.0 8.0 8.0 8.0 8.0 8.0 B2 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 (C) Photopolymerizable monomer 7.3 7.3 7.3 7.3 7.3 7.3 7.3 7.3 7.3 7.3 (D) Photopolymerization initiator 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 (E) Solvent 70.1 70.1 70.1 70.1 70.1 70.1 55.9 55.9 55.9 55.9

(Evaluate)

Evaluation : Assessing Reliability

The photosensitive resin compositions according to Examples 1 to 6 and Comparative Examples 1 to 4 were coated on a 1 mm thick degreased and cleaned glass substrate to a thickness of 1 micron to 3 microns, and dried on a hot plate at 90°C 2 minutes to obtain a thin film. Subsequently, the film was exposed using a high-pressure mercury lamp having a dominant wavelength of 365 nm, dried in an oven at 200° C. for 60 hours, and then the thickness and transmittance were measured using a contact type measuring instrument (Tenco) and an MCPS measuring instrument, and The results are shown in Table 2.

(Table 2) Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Thickness (nm) (under Gy0.566) 2.21 2.13 2.01 1.94 1.87 2..03 3.63 3.55 2.89 >5.00 Transmittance (%) (under Gy0.566) 104 104 104 103 102 103.8 100 100.5 98.8 <80

Referring to Table 2, it can be easily expected that the photosensitive resin compositions according to Examples have improved transmittance even at a thin thickness, so that processability and reliability are improved, and the color gamut is also improved because there is no difference in transmittance. reduced and improved.

While the invention has been described in connection with what are presently regarded as practical example embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, the invention is intended to cover all aspects included within the spirit and scope of the patent application. Various modifications and equivalent arrangements. Therefore, the foregoing embodiments should be understood as illustrative but not restrictive of the present invention in any way.

none.

FIG. 1 is a view illustrating a cage width of a shell represented by Chemical Formula 3-E.

Claims (25)

A photosensitive resin composition, including a colorant, wherein the colorant includes a dye represented by Chemical Formula 1, a core-shell structure dye, and a phthalocyanine dye: [Chemical Formula 1]

Wherein, in Chemical Formula 1, X is an oxygen atom or a sulfur atom, L ¹ is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, and R ¹ to R ⁴ are each independently a hydrogen atom, substituted Or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted C6 to C20 aryl. The photosensitive resin composition as described in claim item 1, wherein L ¹ is represented by chemical formula L-1: [chemical formula L-1]

Wherein, in the chemical formula L-1, R ⁵ and R ⁶ are each independently a hydrogen atom or a halogen-substituted or unsubstituted C1 to C20 alkyl group. The photosensitive resin composition according to claim 1, wherein the dye represented by Chemical Formula 1 is represented by any one of Chemical Formula 1-1 to Chemical Formula 1-3: [Chemical Formula 1-1]

[chemical formula 1-2]

[chemical formula 1-3]

. The photosensitive resin composition as described in Claim 1, wherein the dye represented by Chemical Formula 1 is included in an amount greater than the amount of the core-shell dye, and The dye represented by Chemical Formula 1 is included in an amount greater than that of the phthalocyanine-based dye. The photosensitive resin composition as described in claim 4, wherein The phthalocyanine-based dye is included in an amount greater than that of the core-shell dye. The photosensitive resin composition as described in Claim 1, wherein The dye represented by Chemical Formula 1 is contained in an amount greater than a mixed content of the core-shell structure dye and the phthalocyanine-based dye. The photosensitive resin composition as claimed in claim 1, wherein the core-shell dye is composed of a core represented by Chemical Formula 2 and a shell represented by Chemical Formula 3: [Chemical Formula 2]

Wherein, in Chemical Formula 2, R ⁷ to R ¹⁰ are each independently substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C20 aryl, [chemical formula 3]

Wherein, in Chemical Formula 3, R ¹¹ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ , wherein R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl, R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl, m is an integer from 1 to 10, n is an integer from 1 to 3, And L ² and L ³ are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group. The photosensitive resin composition as described in claim item 7, wherein The core represented by Chemical Formula 2 has a length of 1 nm to 3 nm. The photosensitive resin composition as described in claim item 7, wherein The core represented by Chemical Formula 2 has a maximum absorption peak at a wavelength of 530 nm to 680 nm. The photosensitive resin composition according to claim 7, wherein the core represented by Chemical Formula 2 is represented by any one of Chemical Formula 2-1 to Chemical Formula 2-6: [Chemical Formula 2-1]

[chemical formula 2-2]

[chemical formula 2-3]

[chemical formula 2-4]

[chemical formula 2-5]

[chemical formula 2-6]

. The photosensitive resin composition according to claim 7, wherein the shell represented by Chemical Formula 3 is represented by Chemical Formula 3-1: [Chemical Formula 3-1]

Wherein, in Chemical Formula 3-1, R ¹¹ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ , wherein R ¹⁶ is a substituted or unsubstituted Substituted C1 to C20 alkyl, R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl, and n is an integer of 1 to 3. The photosensitive resin composition according to claim 7, wherein the shell represented by Chemical Formula 3 is represented by any one of Chemical Formula 3-1-1 to Chemical Formula 3-1-3: [Chemical Formula 3-1-1]

[Chemical formula 3-1-2]

[chemical formula 3-1-3]

Wherein, in Chemical Formula 3-1-1 to Chemical Formula 3-1-3, R ¹² to R ¹⁵ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁷ and R ¹⁸ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group or *-C(=O)OR ¹⁶ , wherein R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl group. The photosensitive resin composition as described in claim item 7, wherein The shell represented by Chemical Formula 3 has a cage width of 6.5 angstroms to 7.5 angstroms. The photosensitive resin composition according to claim 7, wherein the shell represented by Chemical Formula 3 is represented by any one of Chemical Formula 3-A to Chemical Formula 3-E: [Chemical Formula 3-A]

[chemical formula 3-B]

[chemical formula 3-C]

[chemical formula 3-D]

[chemical formula 3-E]

. The photosensitive resin composition as described in Claim 1, wherein The core-shell dye contains a core and a shell in a 1:1 molar ratio. The photosensitive resin composition as claimed in item 1, wherein the phthalocyanine dye is represented by chemical formula 4: [chemical formula 4]

Wherein, in Chemical Formula 4, R ¹⁰¹ to R ¹¹⁶ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, a substituted or unsubstituted C3 to C20 alkoxy group, Substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, provided that at least one of R ¹⁰¹ to R ¹⁰⁴ , at least one of R ¹⁰⁵ to R ¹⁰⁸ and R At least one of ¹⁰⁹ to R ¹¹² is independently represented by Chemical Formula 5, and at least one of R ¹¹³ to R ¹¹⁶ is a halogen atom or represented by Chemical Formula 5, [Chemical Formula 5]

Wherein, in Chemical Formula 5, R ¹¹⁷ and R ¹¹⁸ are each independently a halogen atom, a C1 to C20 alkyl group substituted by a C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or Unsubstituted C6 to C20 aryl, and n1 and n2 are each independently an integer from 0 to 5, provided that 1 ≤ n1+n2 ≤ 5. The photosensitive resin composition as described in Claim 16, wherein Chemical Formula 5 is represented by Chemical Formula 5-1 to Chemical Formula 5-4: [Chemical Formula 5-1]

[chemical formula 5-2]

[chemical formula 5-3]

[chemical formula 5-4]

. The photosensitive resin composition as described in Claim 1, wherein The colorant further includes a pigment. The photosensitive resin composition as described in Claim 1, wherein The colorant is included in an amount of 1% by weight to 15% by weight based on the total amount of the photosensitive resin composition. The photosensitive resin composition as described in Claim 1, wherein The photosensitive resin composition further includes a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent. The photosensitive resin composition as described in claim 20, wherein According to the total amount of the photosensitive resin composition, The photosensitive resin composition comprises: 1% to 15% by weight of said colorant; 1% to 20% by weight of said binder resin; 1% to 20% by weight of said photopolymerizable monomer; 0.1% by weight to 10% by weight of the photopolymerization initiator; and the rest of the solvents. The photosensitive resin composition as described in claim 20, wherein The photosensitive resin composition further includes malonic acid, 3-amino-1,2-propanediol, silane coupling agents with vinyl or (meth)acryloxy groups, leveling agents, surfactants, free based polymerization initiators or combinations thereof. A photosensitive resin layer manufactured using the photosensitive resin composition described in any one of claim 1 to claim 22. A color filter, comprising the photosensitive resin layer described in claim 23. An electronic device, comprising the color filter described in claim 24.

Images