KR102124126B1 - Novel compound, photosensitive resin composition including the same and color filter - Google Patents

Abstract

(상기 화학식 1에서, 각 치환기는 명세서에 정의된 바와 같다.)A compound represented by the following Chemical Formula 1, a photosensitive resin composition comprising the compound, and a color filter manufactured using the photosensitive resin composition are provided.
[Formula 1]

(In Formula 1, each substituent is as defined in the specification.)

Description

New compound, photosensitive resin composition and color filter comprising the same {NOVEL COMPOUND, PHOTOSENSITIVE RESIN COMPOSITION INCLUDING THE SAME AND COLOR FILTER}

The present description relates to a novel compound, a photosensitive resin composition comprising the same, and a color filter.

The liquid crystal display device, which is one of the display devices, has advantages such as light weight, thinness, low cost, low power consumption, and excellent adhesion to integrated circuits, and thus the range of its use is expanding for notebook computers, monitors, and TV images. Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, an active circuit portion composed of a liquid crystal layer, a thin film transistor, and a power storage capacitor layer, and an upper substrate on which an ITO pixel electrode is formed. The color filter includes a black matrix layer formed in a predetermined pattern on a transparent substrate to shield a boundary between pixels, and a plurality of colors (typically red (R), green (G), and blue (B) to form each pixel. ) Has a structure in which the pixel parts arranged in three order) are sequentially stacked. The pigment dispersion method, which is one of the methods for implementing a color filter, coats a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix, exposes the pattern of the desired shape, and removes the unexposed area with a solvent. It is a method of forming a colored thin film by repeating a series of heat curing processes. The colored photosensitive resin composition used for manufacturing the color filter according to the pigment dispersion method is generally made of an alkali-soluble resin, a photopolymerization monomer, a photopolymerization initiator, a solvent and other additives, and further includes an epoxy resin or the like. The pigment dispersion method as described above is actively applied to manufacture LCDs such as mobile phones, notebook computers, monitors, and TVs. However, in recent years, even in the photosensitive resin composition for a color filter using a pigment dispersion method having various advantages, it is difficult to refine the powder, and even if dispersed, various additives are necessary because the dispersion state must be stable in the dispersion, and the process is also It is very demanding, and furthermore, since the pigment dispersion must maintain an optimal quality, storage and transportation conditions are difficult. In addition, in a color filter made of a pigment-type photosensitive resin composition, there are limitations in brightness and contrast ratio resulting from pigment particle size. Accordingly, there is a need to develop dyes having heat resistance and chemical resistance similar to pigments instead of pigments.

One embodiment is to provide a compound having excellent solubility in an organic solvent, and having excellent fluorescence control and spectral consistency as it has a dimer form connected with a functional linking group.

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

Another embodiment is to provide a color filter manufactured using the photosensitive resin composition.

One embodiment provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

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

L ¹ is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, *-OC(=O)NH-*, *- O(C=O)-*, *-NR ^X -* or a combination thereof, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group,

X is represented by the following formula (X-1) or formula (X-2).

[Formula X-1]

[Formula X-2]

L ¹ may be represented by the following Chemical Formula 2.

[Formula 2]

In Chemical Formula 2,

L ² to L ⁶ are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, *-OC(=O)NH-*, *-O( C=O)-* or *-NR ^X -*, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group, provided that L ² to L ⁶ are not all single bonds.

L ¹ may be a substituted or unsubstituted C1 to C20 alkylene group.

L ¹ may be represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

L ⁷ to L ⁹ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, or a combination thereof.

Each of L ⁷ to L ⁹ may be independently substituted or unsubstituted C1 to C10 alkylene group, or represented by the following Chemical Formula 3-1 or the following Chemical Formula 3-2.

[Formula 3-1]

[Formula 3-2]

In Chemical Formulas 3-1 and 3-2,

L ^a to L ^c are each independently a substituted or unsubstituted C1 to C5 alkylene group.

The L ¹ may be represented by the following formula (4).

[Formula 4]

In Chemical Formula 4,

L ¹⁰ to L ¹² are each independently a substituted or unsubstituted C1 to C10 alkylene group.

L ¹ may be represented by the following Chemical Formula 5.

[Formula 5]

In Chemical Formula 5,

L ¹³ and L ¹⁴ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

R ^x is a substituted or unsubstituted C1 to C10 alkyl group.

At least one of R ¹ to R ⁴ may be represented by the following Chemical Formula 6-1 or Chemical Formula 6-2.

[Formula 6-1]

[Formula 6-2]

In Chemical Formulas 6-1 and 6-2,

R ⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L ¹⁵ and L ¹⁶ are each independently a substituted or unsubstituted C1 to C10 alkylene group.

The compound represented by Formula 1 may be represented by any one of the following Formulas 7 to 21.

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

The compound represented by Chemical Formula 1 may have a maximum absorbance in a wavelength range of 500 nm or 600 nm.

Another embodiment provides a photosensitive resin composition comprising the compound as a dye.

The dye may be a red dye or a blue dye.

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

The binder resin may include acrylic binder resin, cardo-based binder resin, or a combination thereof.

The photosensitive resin composition may further include a pigment.

The photosensitive resin composition further comprises a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, or a combination of malonic acid, 3-amino-1,2-propanediol, vinyl group, or (meth)acryloxy group. It can contain.

Another embodiment provides a color filter manufactured using the photosensitive resin composition.

Other details of aspects of the present invention are included in the detailed description below.

The compound according to one embodiment has excellent solubility in an organic solvent, has excellent fluorescence control and spectral consistency, and uses a photosensitive resin composition containing a colorant containing the component as a component, and has excellent luminance, contrast, and the like color. Filters can be prepared.

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

Unless otherwise specified in the present specification, "substituted" to "substituted" means that at least one hydrogen atom in the functional group of the present invention is a halogen atom (F, Br, Cl or I), a hydroxyl group, a nitro group, a cyano group, an amino group ( NH ₂ , NH(R ²⁰⁰ ) or N(R ²⁰¹ )(R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different from each other, each independently being a C1 to C10 alkyl group), amidino group, 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 group, And substituted or unsubstituted heterocyclic groups.

Unless otherwise specified in the present specification, "alkyl group" means a C1 to C20 alkyl group, specifically means a C1 to C15 alkyl group, and "cycloalkyl group" means a C3 to C20 cycloalkyl group, specifically C3 To C18 means a cycloalkyl group, "alkoxy group" means a C1 to C20 alkoxy group, specifically means a C1 to C18 alkoxy group, and "aryl group" means a C6 to C20 aryl group, specifically C6 to C18 aryl group means, "alkenyl group" means C2 to C20 alkenyl group, specifically means C2 to C18 alkenyl group, and "alkylene group" means C1 to C20 alkylene group, specifically C1 To C18 alkylene group, and "arylene group" means a C6 to C20 arylene group, specifically, a C6 to C16 arylene group.

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

In the present specification, unless otherwise defined, "combination" means mixing or copolymerization. In addition, "copolymerization" means block copolymerization to random copolymerization, and "copolymer" means block copolymer to random copolymerization.

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

In the present specification, the cardo-based resin means a resin in which at least one functional group selected from the group consisting of the following Chemical Formulas 17-1 to 17-11 is included in the backbone in the resin.

Unless otherwise defined, the term “ethylenically unsaturated double bond” means “carbon-carbon double bond”, and the ethylenically unsaturated monomer means a monomer containing the ethylenically unsaturated double bond.

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

One embodiment provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

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

L ¹ is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, *-OC(=O)NH-*, *- O(C=O)-*, *-NR ^X -* or a combination thereof, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group,

X is represented by the following formula (X-1) or formula (X-2).

[Formula X-1]

[Formula X-2]

As described above, in a color filter made of a pigment-type photosensitive resin composition, there are limitations in luminance and contrast ratio resulting from pigment particle size. In addition, in the case of a color imaging element for an image sensor, a smaller dispersion particle size is required to form a fine pattern. In order to meet these demands, attempts have been made to implement a color filter with improved brightness and contrast ratio by preparing a photosensitive resin composition suitable for dyes by introducing dyes that do not form particles instead of pigments.

In general, the xanthene-based compound has a separate charge, and the photosensitive resin composition containing the same has low solubility in an organic solvent such as PGMEA, and has poor heat resistance and chemical resistance, and thus has limitations in use as a colorant in the photosensitive resin composition. However, the compound according to one embodiment, that is, the compound represented by Chemical Formula 1 may improve solubility in an organic solvent, and further has a dimer form connected with a functional linking group, and thus has excellent fluorescence control and spectral consistency, and includes it. A color filter having improved brightness and contrast ratio can be manufactured using a photosensitive resin composition.

For example, L ¹ may be represented by Formula 2 below.

[Formula 2]

In Chemical Formula 2,

L ² to L ⁶ are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, *-OC(=O)NH-*, *-O( C=O)-* or *-NR ^X -*, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group, provided that L ² to L ⁶ are not all single bonds.

For example, L ¹ may be a substituted or unsubstituted C1 to C20 alkylene group.

For example, L ¹ may be represented by Chemical Formula 3 below.

[Formula 3]

In Chemical Formula 3,

L ⁷ to L ⁹ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, or a combination thereof.

For example, the L ⁷ to L ⁹ may be each independently substituted or unsubstituted C1 to C10 alkylene group, represented by the following formula 3-1 or the following formula 3-2.

[Formula 3-1]

[Formula 3-2]

In Chemical Formulas 3-1 and 3-2,

L ^a to L ^c are each independently a substituted or unsubstituted C1 to C5 alkylene group.

For example, L ¹ may be represented by Formula 4 below.

[Formula 4]

In Chemical Formula 4,

L ¹⁰ to L ¹² are each independently a substituted or unsubstituted C1 to C10 alkylene group.

For example, L ¹ may be represented by Chemical Formula 5 below.

[Formula 5]

In Chemical Formula 5,

L ¹³ and L ¹⁴ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

R ^x is a substituted or unsubstituted C1 to C10 alkyl group.

For example, at least one of R ¹ to R ⁴ may be represented by the following Chemical Formula 6-1 or Chemical Formula 6-2.

[Formula 6-1]

[Formula 6-2]

In Chemical Formulas 6-1 and 6-2,

R ⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L ¹⁵ and L ¹⁶ are each independently a substituted or unsubstituted C1 to C10 alkylene group.

For example, one of R ¹ to R ⁴ may be represented by Chemical Formula 6-1 or Chemical Formula 6-2.

For example, two of R ¹ to R ⁴ may be represented by Chemical Formula 6-1 or Chemical Formula 6-2.

For example, any one of R ¹ and R ² and any one of R ³ and R ⁴ may be represented by Formula 6-1 or Formula 6-2.

When at least one of R ¹ to R ⁴ is represented by Chemical Formula 6-1 or Chemical Formula 6-2, solubility in an organic solvent becomes more excellent.

When at least one of R ¹ to R ⁴ is represented by Chemical Formula 6-1 or Chemical Formula 6-2, a compound represented by Chemical Formula 1 and a monomer may be copolymerized to form a polymer. For example, the monomer may be an ethylenically unsaturated monomer, in which case the polymer may be an acrylic polymer.

For example, the ethylenically unsaturated monomer may be an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid amino alkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound, or a combination thereof. have.

For example, the ethylenically unsaturated monomers include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzyl methyl ether; (Meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxy butyl Unsaturated carboxylic acid ester compounds such as (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, and phenyl (meth)acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; Vinyl cyanide compounds such as (meth)acrylonitrile; It may be an unsaturated amide compound such as (meth)acrylamide or a combination thereof.

At least one of R ¹ to R ⁴ is represented by the formula (6-1) or formula (6-2), an acrylic polymer that is a product of a polymerization reaction through copolymerization of the compound represented by the formula (1) and the ethylenically unsaturated monomer, It is excellent in heat resistance and processability, and can be very usefully used as a colorant in a photosensitive resin composition used for manufacturing color filters, such as a dye.

The compound represented by Formula 1 may be represented by any one of the following Formulas 7 to 21, but is not limited thereto.

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

The compound represented by Chemical Formula 1 may have a maximum absorbance in a wavelength range of 500 nm to 600 nm.

Another embodiment provides a photosensitive resin composition comprising the compound as a dye.

The dye may be a red dye or a blue dye.

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

Hereinafter, the components will be described in detail.

coloring agent

The colorant may further include an organic solvent-soluble dye in addition to the compound.

Examples of the organic solvent-soluble dye include a triarylmethane-based compound, anthraquinone-based compound, benzylidene-based compound, cyanine-based compound, phthalocyanine-based compound, azapophyrin-based compound, indigo-based compound, and the like.

The colorant may further include a pigment in addition to the compound.

The pigment may include a blue pigment, a violet pigment, a red pigment, a green pigment, a yellow pigment, and the like.

Examples of the blue pigment, 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, C.I. Blue Pigment 22, C.I. Blue Pigment 60, C.I. Blue Pigment 64, C.I. Blue pigment 80 or a combination thereof.

Examples of the violet pigment, C.I. Violet Pigment 1, C.I. Violet Pigment 19, C.I. Violet Pigment 23, C.I. Violet Pigment 27, C.I. Violet Pigment 28, C.I. Violet Pigment 29, C.I. Violet Pigment 30, C.I. Violet Pigment 32, C.I. Violet Pigment 37, C.I. Violet Pigment 40, C.I. Violet Pigment 42, C.I. Violet pigment 50 or a combination thereof.

Examples of the red pigment include perylene-based pigments, anthraquinone-based pigments, azo-based pigments, diazo-based pigments, quinacridone-based pigments, and anthracene-based pigments. Specific examples of the red pigments include perylene pigments, quinacridone pigments, naphthol AS, cicumin pigments, anthraquinone (sudan I, II, III, R), and bis azo ), benzopyran, and the like.

Examples of the green pigment, C.I. And halogenated phthalocyanine-based pigments such as pigment green 58.

Examples of the yellow pigment, C.I. Pigment Yellow 139, C.I. Pigment Yellow 138, C.I. Pigment yellow 150 and the like, and these may be used alone or in combination of two or more.

The pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.

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

The pigment of the solid content is 1% to 20% by weight relative to the total amount of the pigment dispersion, such as 8% to 20% by weight, such as 8% to 15% by weight, such as 10% to 20% by weight, such as 10% to 10% 15% by weight.

As the dispersant, a nonionic dispersant, anionic dispersant, or cationic dispersant may be used. Specific examples of the dispersant include polyalkylene glycol and esters thereof, polyoxyalkylenes, polyalcohol esters alkylene oxide adducts, alcoholalkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, and carboxylic acids Salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more.

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

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

As the solvent for forming the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol (mono)methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like can be used.

Binder resin

The binder resin may include acrylic binder resin, cardo-based binder resin, or a combination thereof. For example, the binder resin may be an acrylic binder resin.

The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin comprising at least one acrylic repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or combinations thereof.

The first ethylenically unsaturated monomer may be included in an amount of 5% to 50% by weight, such as 10% to 40% by weight, based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomers include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzyl methyl ether; Methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxy butyl (meth)acrylate, benzyl (meth)acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth)acrylate and phenyl (meth)acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; Vinyl cyanide compounds such as (meth)acrylonitrile; Unsaturated amide compounds such as (meth)acrylamide; And the like, and these may be used alone or in combination of two or more.

Specific examples of the acrylic binder resin are (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid/benzylmethacrylate/2-hydroxyethyl methacrylate Acrylate copolymers, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymers, and the like, but are not limited thereto, and these may be used alone or in combination of two or more. have.

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

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

The cardo-based binder resin may include a repeating unit represented by Chemical Formula 22 below.

[Formula 22]

In Chemical Formula 22,

R ¹¹ and R ¹² are each independently a hydrogen atom or a substituted or unsubstituted (meth)acryloyloxyalkyl group,

R ¹³ and R ¹⁴ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

Z ¹ is a single bond, O, CO, SO ₂ , CR ¹⁵ R ¹⁶ , SiR ¹⁷ R ¹⁸ (where R ¹⁵ to R ¹⁸ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) or Formula 22-1 to any one of the linking group represented by Formula 22-11,

[Formula 22-1]

[Formula 22-2]

[Formula 22-3]

[Formula 22-4]

[Formula 22-5]

(In the above formula 22-5,

R ^a is a hydrogen atom, an ethyl group, C ₂ H ₄ Cl, C ₂ H ₄ OH, CH ₂ CH=CH ₂ or a phenyl group.)

[Formula 22-6]

[Formula 22-7]

[Formula 22-8]

[Formula 22-9]

[Formula 22-10]

[Formula 22-11]

Z ² is an acid dianhydride residue,

m1 and m2 are each independently an integer of 0-4.

The cardo-based binder resin may include a functional group represented by the following Chemical Formula 23 on at least one of both ends.

[Formula 23]

In Chemical Formula 23,

Z ³ may be represented by the following formulas 23-1 to 23-7.

[Formula 23-1]

(In the formula 23-1, R ^b and R ^c are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group, or an ether group.)

[Formula 23-2]

[Formula 23-3]

[Formula 23-4]

[Formula 23-5]

(In the formula 23-5, R ^d is O, S, NH, a substituted or unsubstituted C1 to C20 alkylene group, a C1 to C20 alkylamine group, or a C2 to C20 alkenylamine group.)

[Formula 23-6]

[Formula 23-7]

The cardo-based binder resin includes, for example, a fluorene-containing compound such as 9,9-bis(4-oxyranylmethoxyphenyl)fluorene; Benzenetetracarboxylic acid anhydride, naphthalenetetracarboxylic acid anhydride, biphenyltetracarboxylic acid anhydride, benzophenonetetracarboxylic acid anhydride, pyromellitic dihydrate, cyclobutanetetracarboxylic acid anhydride, perylenetetracarboxylic acid anhydride , Anhydrous compounds such as tetrahydrofuran tetracarboxylic dianhydride and tetrahydrophthalic anhydride; Glycol compounds such as ethylene glycol, propylene glycol, and polyethylene glycol; Alcohol compounds such as methanol, ethanol, propanol, n-butanol, cyclohexanol, and benzyl alcohol; Solvent compounds such as propylene glycol methyl ethyl acetate and N-methylpyrrolidone; Phosphorus compounds such as triphenylphosphine; And amine or ammonium salt compounds such as tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, and benzyltriethylammonium chloride.

When the cardo-based binder resin is used together with the aforementioned acrylic-based binder resin, it is possible to obtain a photosensitive resin composition having excellent adhesion and high resolution and high brightness characteristics.

The weight average molecular weight of the cardo-based binder resin may be 500 g/mol to 50,000 g/mol, such as 3,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the cardo-based binder resin is within the above range, the pattern is well formed without residue when manufacturing the color filter, and there is no loss of film thickness during development, and a good pattern can be obtained.

The cardo-based binder resin may have an acid value of 100 mgKOH/g to 140 mgKOH/g.

Photopolymerization compound

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

The photopolymerizable compound has the above ethylenically unsaturated double bond, and thus can form a pattern excellent in heat resistance, light resistance, and chemical resistance by causing sufficient polymerization during exposure in the 　 pattern forming process.

Specific examples of the photopolymerizable compound include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, and neopentyl glycol di (Meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, Pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylic Rate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy (meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylol propane tri(meth) )Acrylate, tris(meth)acryloyloxyethyl phosphate, and novolac epoxy (meth)acrylate　.

Examples of commercially available products of the photopolymerizable compound are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ^®, the same M-111 ^®, the same M-114 ^®; KAYARAD TC-110S ^® of Nihon Kayaku Co., Ltd., and TC-120S ^® of the same; Osaka yukki the like Kagaku Kogyo (main)社of ^{V-158 ®, V-2311} ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ^®, copper or the like M-240 ^®, the same M-6200 ^®; Nippon Kayaku (Note)社of KAYARAD HDDA ^®, copper HX-220 ^®, copper R-604 ^®, and the like; Osaka yukki the like Kagaku Kogyo Co., Ltd. of ^{社V-260 ®, V-} 312 ®, V-335 HP ®. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ^®, the same M-400 ^®, the same M-405 ^®, the same M-450 ^®, Dong M ^® -710, Dong M-8030 ^®, same M-8060 ^®, and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ^®, copper DPCA-20 ^{®, ®} copper -30, -60 ^® copper, copper ^® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ^®, copper ^® -300, -360 ^® copper, copper -GPT ^®, copper -3PA ^®, and the like copper -400 ^®. The above products may be used alone or in combination of two or more.

The photopolymerizable compound may be treated with acid anhydride in order to impart better developability.

Light polymerization Initiator

The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, for example, acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, oxime compounds, or combinations thereof Can be used.

Examples of the acetophenone-based compound, 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone, pt -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane-1 -One, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, and the like.

Examples of the benzophenone-based compound, benzophenone, benzoyl benzoate, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethyl amino)benzophenone, 4,4 And'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.

Examples of the thioxanthone-based compound include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- And chlorothioxanthone.

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

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3', 4'- Dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4, 6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis (Trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, and the like.

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

In addition to the compound, the photopolymerization initiator may use a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, a fluorene compound, and the like.

The photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light, becoming excited, and transmitting its energy.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, etc. Can be heard.

menstruum

The solvent may be used materials that have compatibility with a compound, a pigment, a binder resin, a photopolymerizable compound, and a photopolymerization initiator according to one embodiment, but do not react.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether, and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetate alkyl esters such as methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, and ethyl ethoxy acetate; 3-oxy propionic acid alkyl esters such as methyl 3-oxy propionate and ethyl 3-oxy propionate; 3-alkoxy propionic acid alkyl esters such as methyl 3-methoxy propionate, ethyl 3-methoxy propionate, ethyl 3-ethoxy propionate and methyl 3-ethoxy propionate; 2-oxy propionic acid alkyl esters, such as methyl 2-oxy propionate, ethyl 2-oxy propionate, and propyl 2-oxy propionic acid; 2-alkoxy propionic acid alkyl esters such as methyl 2-methoxy propionate, ethyl 2-methoxy propionate, ethyl 2-ethoxy propionate, and methyl 2-ethoxy propionate; 2-oxy-2-methyl propionic acid esters such as methyl 2-oxy-2-methyl propionate and ethyl 2-oxy-2-methyl propionate, methyl 2-methoxy-2-methyl propionate, and 2-ethoxy-2- Monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl propionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methyl propionate, ethyl hydroxy acetate, and methyl 2-hydroxy-3-methyl butanoate; And ketone acid esters such as ethyl pyruvate, and N-methylformamide, N,N-dimethylformamide, N-methylformanirad, N-methylacetamide, and N,N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzylethyl ether, dihexyl ether, acetylacetone, isophorone, capronic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid And high boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among these, ketones such as cyclohexanone are considered in consideration of compatibility and reactivity; Glycol ethers such as ethylene glycol monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

Other additives

The photosensitive resin composition is to prevent stains and spots when applied, to improve the leveling performance, and also to prevent the generation of residues due to undeveloped, malonic acid; 3-amino-1,2-propanediol; Silane coupling agents having reactive substituents such as carboxyl groups, methacryloyl groups, isocyanate groups, and epoxy groups; Leveling agents; Fluorine-based surfactants; Additives, such as a radical polymerization initiator, may be further included.

Examples of the silane-based coupling agent, trimethoxysilyl benzoic acid, γ-methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-glycine Oxidized propyl trimethoxysilane, β-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, and the like. These may be used alone or in combination of two or more.

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

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

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

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

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

A fluorine-based surfactant may be used as the surfactant, and examples of the fluorine-based surfactant include F-482, F-484, F-478, and F-554 of DIC, but are not limited thereto.

The surfactant may be used in 0.001 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included within the above range, coating uniformity is secured, staining does not occur, and wetting of the glass substrate is excellent.

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

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

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

Applying the photosensitive resin composition onto a support substrate by spin coating, slit coating, inkjet printing, or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; Developing the photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And heat-treating the photosensitive resin film. Since the conditions in the process are well known in the art, detailed descriptions thereof will be omitted.

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

(Synthesis of compounds)

Synthetic example 1: Synthesis of compound represented by formula (7)

3',6'-Dichlorospiro[3 H -2,1-benzoxathiol-3,9'-[9 H ]xanthene]-1,1-dioxide In 8.1g, 56g of 2-propanol and 2.9g of diethylamine were added at room temperature. Stir for 3 hours. Precipitation was obtained using ether, followed by drying to obtain intermediate 1. Into the N, N '-Dimethyl-1,6- hexanediamine 0.5 equivalents of water and the resultant intermediate 1 were reacted for one day at 80 ℃, to obtain a compound represented by the following formula (7) with a total of 47% yield.

[Formula 7]

Maldi-tof MS: 954 m/z

Synthetic example 2: Synthesis of compound represented by formula (8)

To the same manner as in the Synthesis Example 1, except for using the -Diethyl-1,6-hexanediamine 'N, N instead -Dimethyl-1,6-hexanediamine' N, N in the reaction of the Synthesis Example 1 and the formula The compound represented by 8 was obtained.

[Formula 8]

Maldi-tof MS: 982 m/z

Synthetic example 3: Synthesis of compound represented by formula (9)

Except for using 2- (ethylamino) ethanol instead of N, N '-Dimethyl-1,6- hexanediamine in the above Synthesis Example 1, in the same manner as in the above Synthesis Example 1 to obtain the intermediate 2. Using the catalytic amount of dibutyltin dilaurate and 1,6-Diisocyanatohexane in the obtained intermediate 2, a compound represented by the following formula (9) was obtained.

[Formula 9]

Maldi-tof MS: 1156 m/z

Synthetic example 4: Synthesis of compound represented by formula (10)

The compound represented by Chemical Formula 10 was obtained in the same manner as in Synthesis Example 3, except that suberoyl chloride was used instead of 1,6-Diisocyanatohexane of Synthesis Example 3.

[Formula 10]

Maldi-tof MS: 1126 m/z

Synthetic example 5: Synthesis of Compound Represented by Formula 11

The compound represented by Chemical Formula 11 was obtained in the same manner as in Synthesis Example 3, except that 1,3-Bis(isocyanatomethyl)-cyclohexane was used instead of 1,6-Diisocyanatohexane of Synthesis Example 3.

[Formula 11]

Maldi-tof MS: 1182 m/z

Synthetic example 6: Synthesis of compound represented by formula (12)

Excess thionyl chloride was added to the compound of Formula 7 of Synthesis Example 1 to reflux to replace sulfonisu acid in the anion portion with sulfoyl chloride, and then reacted with 2 equivalents of trifluoromethanesulfonamide to obtain a compound represented by the following Formula 12.

[Formula 12]

Maldi-tof MS: 1216 m/z

Synthetic example 7: Synthesis of compound represented by formula (13)

The compound obtained by reacting in the same manner as in Synthesis Example 1 is reacted with isocyanatoethyl methacrylate in the chloroform solvent, except that 2-(ethylamino)ethanol is used instead of diethylamine in the starting material in Synthesis Example 1, and is represented by the following Chemical Formula 13 The compound was obtained.

[Formula 13]

Maldi-tof MS: 1296 m/z

Synthetic example 8: Synthesis of compound represented by formula (14)

The compound obtained by reacting in the same manner as in Synthesis Example 2 was reacted with isocyanatoethyl methacrylate in a chloroform solvent, except that 2-(ethylamino)ethanol was used instead of diethylamine in Synthesis Example 2 to obtain a compound represented by the following Chemical Formula 14 .

[Formula 14]

Maldi-tof MS: 1325 m/z

Synthetic example 9: Synthesis of Compound Represented by Formula 15

In the same manner as in the above Synthesis Example 1, except for using 1,4,7-Trimethyldiethylenetriamine in place of N, N '-Dimethyl-1,6- hexanediamine in the reaction of the Synthesis Example 1, and a compound represented by general formula (15) Got

[Formula 15]

Maldi-tof MS: 907 m/z

Synthetic example 10: Synthesis of Compound Represented by Formula 16

A compound represented by the following Chemical Formula 16 was obtained in the same manner as in Synthesis Example 3, except that Dicyclohexylmethane-4,4'-diisocyanate was used instead of 1,6-Diisocyanatohexane of Synthesis Example 3.

[Formula 16]

Maldi-tof MS: 1251 m/z

Synthetic example 11: Synthesis of Compound Represented by Formula 17

A compound represented by Chemical Formula 17 was obtained in the same manner as in Synthesis Example 8, except that acryloyl chloride was used instead of isocyanatoethyl methacrylate of Synthesis Example 8.

[Formula 17]

Maldi-tof MS: 1122 m/z

Synthetic example 12: Synthesis of Compound Represented by Formula 18

Except for using methacryloyl chloride instead of isocyanatoethyl methacrylate in Synthesis Example 8, the same method as in Synthesis Example 8 to obtain a compound represented by the following formula (18).

[Formula 18]

Maldi-tof MS: 1151 m/z

Synthetic example 13: Synthesis of Compound Represented by Formula 19

3',6'-Dichlorospiro[3 H -2,1-benzoxathiol-3,9'-[9 H ]xanthene]-1,1-dioxide 8.1g of 56g 2-propanol and 1.46g diethylamine and room temperature Stir for 3 hours. Precipitation was obtained using ether, followed by drying to obtain intermediate 1.

56g 2-propanol and 1.78g 2-(ethylamino) in 8.1g of 3',6'-Dichlorospiro[3 H -2,1-benzoxathiol-3,9'-[9 H ]xanthene]-1,1-dioxide ) Add ethanol and stir for 3 hours at room temperature. Precipitation was obtained using ether, followed by drying to obtain intermediate 2.

The intermediate to the first and to a mixture of intermediate 2 each by one equivalent of N, N '-Diethyl-1,6- hexanediamine 1 equivalent to yield the resultant compound reacted with acryloyl chloride to obtain a compound represented by the formula (19).

[Formula 19]

Maldi-tof MS: 1053 m/z

Synthetic example 14: Synthesis of Compound Represented by Formula 20

A compound represented by Chemical Formula 20 was obtained in the same manner as in Synthesis Example 13, except that methacryloyl chloride was used instead of the acryloyl chloride of Synthesis Example 13.

[Formula 20]

Maldi-tof MS: 1067 m/z

Synthetic example 15: Synthesis of Compound Represented by Formula 21

A compound represented by the following Chemical Formula 21 was obtained in the same manner as in Synthesis Example 13, except that isocyanatoethyl methacrylate was used instead of the acryloyl chloride of Synthesis Example 13.

[Formula 21]

Maldi-tof MS: 1154 m/z

compare Synthetic example 1: Synthesis of Compound Represented by Formula X

10 g of Compound A (CAS No. 77545-45-0) was added to the reactor and dissolved with 100 g of 2-propanol. After adding diethylamine 7.2g, the mixture was stirred at 80°C for 8 hours. The reaction was cooled and 800 mL of water was added to form a precipitate. The obtained precipitate was suction filtered and further washed with water. The filtrate was dried to obtain 9.9 g of a compound represented by Chemical Formula X (84% yield).

Maldi-tof MS: 478.2 m/z

Evaluation 1: Solubility

The compound represented by Chemical Formulas 7 to 21 and 0.5 g of the compound represented by Chemical Formula X are added to dilution solvents (MeOH, CH ₂ Cl ₂ , Cyclohexanone), respectively, and the solution is mixed rotor (MIXROTAR VMR-5 manufactured by iuchi Co., Ltd.) After stirring at 25 ℃, 100 rpm for 1 hour, the results of confirming the dissolved state of the compound (dissolved compound content) are shown in Table 1 below.

Solubility evaluation criteria

X: Solubility less than 1wt%

○: Solubility 1 wt% or more and less than 5 wt%

◎: Solubility more than 5wt%

Content of dissolved compound (% by weight) Chloroform Diacetone alcohol Formula 7 ○ ○ Formula 8 ○ ○ Formula 9 ○ ○ Formula 10 ○ ○ Formula 11 ○ ○ Formula 12 ○ ○ Formula 13 ◎ ◎ Formula 14 ◎ ◎ Formula 15 ○ ○ Formula 16 ○ ○ Formula 17 ◎ ◎ Formula 18 ◎ ◎ Formula 19 ◎ ◎ Formula 20 ◎ ◎ Formula 21 ◎ ◎ Formula X X X

(Synthesis of photosensitive resin composition)

Example One

The photosensitive resin composition according to Example 1 was prepared by mixing the components mentioned below with the composition shown in Table 2 below.

Specifically, after the photopolymerization initiator was dissolved in a solvent, the mixture was stirred at room temperature for 2 hours, and then an acrylic binder resin and a photopolymerizable compound were added thereto, followed by stirring at room temperature for 2 hours. Subsequently, a compound represented by Chemical Formula 13 and a pigment (in the form of a pigment dispersion) were added to the obtained reactant and stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

(Unit: weight%) Ingredients content coloring agent dyes Compound represented by formula (13) 5.0 Pigment dispersion Pigment Y138 Pigment dispersion 15.0 Alkali-soluble resin (A)/(B)=15/85(w/w),
Molecular weight (Mw) = 22,000 g/mol
(A): Methacrylic acid
(B): Benzyl methacrylate 3.5 Photopolymerizable compound Dipentaerythritol hexaacrylate (DPHA) 8.0 Photopolymerization initiator 1,2-octanedione 1.0 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one 0.5 menstruum Cyclohexanone 37.0 PGMEA (Propylene Glycol Monomethyl Ether Acetate) 30.0 Total 100.00

Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Formula 14 was used instead of the compound represented by Formula 13.

Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Chemical Formula 17 was used instead of the compound represented by Chemical Formula 13.

Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Formula 18 was used instead of the compound represented by Formula 13.

Comparative example One

A photosensitive resin composition was prepared in the same manner as in Example 1, except that a red pigment (SC-P541-4214, Toyo Co., Ltd.) was used instead of the compound represented by Formula 13.

Evaluation 2: luminance measurement

A photosensitive resin composition prepared in Examples 1 to 4 and Comparative Example 1 was applied to a thickness of 1 μm to 3 μm on a glass substrate having a thickness of 1 mm degreased and dried for 2 minutes on a hot plate at 90° C. To obtain a coating film. Subsequently, the coating film was exposed using a high-pressure mercury lamp having a main wavelength of 365 nm. Thereafter, the sample was obtained by drying in a hot air circulation drying furnace at 200° C. for 5 minutes. The pixel layer was measured by using a spectrophotometer (MCPD3000, Otsuka electronics) to measure color coordinates and luminance (Y), and the results are shown in Table 3 below. Luminance (Y) was calculated based on the color coordinate (Gy) value.

Luminance (Y) Example 1 14.1 Example 2 14.3 Example 3 14.2 Example 4 14.2 Comparative Example 1 13.9

From Table 3, the photosensitive resin composition of Example 1 to Example 4 containing the compound according to one embodiment as a colorant, compared to the photosensitive resin composition of Comparative Example 1 that does not contain the compound according to one embodiment and the brightness It can be seen that it exhibits heat resistance.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and detailed description of the invention and the accompanying drawings. Naturally, it is within the scope of the invention.

Claims (17)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
R ¹ to R ⁴ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R ⁵ and R ⁶ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
L ¹ is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, *-OC(=O)NH-*, *-O(C=O)-*, *- NR ^X -* or a combination thereof, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group,
X is represented by the following formula (X-1) or formula (X-2).
[Formula X-1]

[Formula X-2]

According to claim 1,
L ¹ is a compound represented by the following formula (2):
[Formula 2]

In Chemical Formula 2,
L ² to L ⁶ are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, *-OC(=O)NH-*, *-O( C=O)-* or *-NR ^X -*, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group, provided that L ² to L ⁶ are not all single bonds.
According to claim 2,
L ¹ is a substituted or unsubstituted C1 to C20 alkylene group.
According to claim 2,
L ¹ is a compound represented by the following formula (3):
[Formula 3]

In Chemical Formula 3,
L ⁷ to L ⁹ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, or a combination thereof.
The method of claim 4,
The L ⁷ to L ⁹ are each independently substituted or unsubstituted C1 to C10 alkylene group, a compound represented by the following formula 3-1 or the following formula 3-2:
[Formula 3-1]

[Formula 3-2]

In Chemical Formulas 3-1 and 3-2,
L ^a to L ^c are each independently a substituted or unsubstituted C1 to C5 alkylene group.
According to claim 2,
L ¹ is a compound represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
L ¹⁰ to L ¹² are each independently a substituted or unsubstituted C1 to C10 alkylene group.
According to claim 2,
L ¹ is a compound represented by the following formula (5):
[Formula 5]

In Chemical Formula 5,
L ¹³ and L ¹⁴ are each independently a substituted or unsubstituted C1 to C10 alkylene group,
R ^x is a substituted or unsubstituted C1 to C10 alkyl group.
According to claim 1,
At least one of R ¹ to R ⁴ is a compound represented by the following Formula 6-1 or Formula 6-2:
[Formula 6-1]

[Formula 6-2]

In Chemical Formulas 6-1 and 6-2,
R ⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
L ¹⁵ and L ¹⁶ are each independently a substituted or unsubstituted C1 to C10 alkylene group.
According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 7 to 21.
[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

According to claim 1,
The compound represented by Formula 1 is a compound having a maximum absorbance in the wavelength range of 500nm to 600nm.
A photosensitive resin composition comprising the compound of any one of claims 1 to 10 as a dye.
The method of claim 11,
The dye is a red dye or a blue dye photosensitive resin composition.
The method of claim 11,
The photosensitive resin composition further comprises a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
The method of claim 13,
The binder resin is a photosensitive resin composition comprising an acrylic binder resin, cardo-based binder resin or a combination thereof.
The method of claim 13,
The photosensitive resin composition further comprises a pigment.
The method of claim 13,
The photosensitive resin composition further comprises a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, or a combination of malonic acid, 3-amino-1,2-propanediol, vinyl group, or (meth)acryloxy group. Photosensitive resin composition containing.
A color filter manufactured using the photosensitive resin composition of claim 11.