WO2016175390A1

WO2016175390A1 - Novel compound, photosensitive resin composition containing same and color filter

Info

Publication number: WO2016175390A1
Application number: PCT/KR2015/008106
Authority: WO
Inventors: 정의수; 김규영; 김형묵; 박채원; 서혜원; 신명엽; 이영
Original assignee: 삼성에스디아이 주식회사
Priority date: 2015-04-30
Filing date: 2015-08-03
Publication date: 2016-11-03
Also published as: CN107428766A; CN107428766B; KR101881942B1; TWI576348B; TW201638095A; KR20160129619A

Abstract

Provided are a compound represented by a specific chemical formula, a photosensitive resin composition containing the same, and a color filter manufactured using the photosensitive resin composition.

Description

【Specification】

[Name of invention]

Novel compounds, photosensitive resin compositions and color filters comprising the same

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

Background Art

In the color filter made of the pigment-type photosensitive resin composition, there are limitations of brightness and contrast ratio resulting from the pigment particle size. In addition, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to satisfy such a demand, attempts have been made to implement color filters having improved color characteristics such as brightness and contrast ratio by preparing a photosensitive resin composition incorporating a dye that does not form particles instead of pigments.

Therefore, there is a need for research on a compound suitable as a dye used in the preparation of the photosensitive resin composition.

[Detailed Description of the Invention]

[Technical problem]

One embodiment is to provide novel compounds.

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.

Technical Solution

One embodiment of the present invention provides a compound represented by the following formula (1). -Ha ^

In Chemical Formula 1,

M is Cu, Zn, Co or Mo,

R ¹ to R ¹⁶ 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 group, or a substituted or unsubstituted group Substituted C6 to C20

It is an aryloxy group,

At least one of R ′ to R ¹⁶ is represented by the following Formula 2,

[Formula 2]

In Chemical Formula 2,

R ¹⁷ and R ¹⁸ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

Formula 2 may be represented by the following formula (3).

In Chemical Formula 3,

R ¹⁷ and R ¹⁸ are each independently a substituted or unsubstituted C1 to C20 alkyl group or Or a substituted or unsubstituted C6 to C20 aryl group.

At least one of R ¹ to R ¹⁰ may be represented by Formula 2, and at least one of R ¹ to R ¹⁶ may be represented by any one of Formulas 4 to 7.

[Formula 4]

In Chemical Formulas 6 and 7,

L ¹ is a substituted or unsubstituted C1 to C10 alkylene group,

R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group.

At least one of R 'to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by any one of Formula 4 to Formula 7, and at least one of the R ⁹ to R ¹² is One of Formulas 4 to 7 may be represented, and at least one of R ¹³ to R ¹⁶ may be represented by any one of Formulas 4 to 7.

At least one of R ¹ to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by Formula 2, and at least one of R ⁹ to R ¹² is represented by Formula 4 to Formula 7 It may be represented by any one of, and at least one of the R ¹³ to R ¹⁶ may be represented by any one of the formulas (4) to (7). At least one of R ¹ to R ⁴ is represented by Formula 2, and at least one of R ⁵ to R ⁸ is represented by any one of Formula 4 to Formula 7, At least one of R ⁹ to R ¹² may be represented by Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by any one of Formulas 4 to 7.

At least one of R ¹ to R ⁴ is represented by Formula ₂ , and R ⁵ to

At least one of R ⁸ is represented by Formula ₂ , wherein R ⁹ to R! At least one of ^two increase may be represented by Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by any one of Formula 4 to Formula 7.

At least one of R ′ to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by Formula 2, and at least one of R ⁹ to R ¹² is represented by Formula 2; At least one of R ¹³ to R ¹⁶ may be represented by Formula 2.

The compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 8 to 16.

[Formula 8]

[Formula 13]

[Formula 14]

15]

The compound may be a green dye.

The green dye may have a maximum transmittance in the wavelength range of 445nm to 560nm. have.

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

The photosensitive resin composition may further include a pigment.

The pigment may be a yellow pigment.

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

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

Advantageous Effects

Compound according to an embodiment has excellent green spectral properties and high molar absorption coefficient and excellent solubility in organic solvents, can be used as a dye when preparing a photosensitive resin composition for a green color filter, the color filter comprising the dye It can have excellent brightness and contrast ratio.

[Best form for implementation of the invention]

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

Unless stated otherwise in the specification, "substituted" to "substituted" means that at least one hydrogen atom of the functional group of the present invention is a halogen atom (F, Br, Cl or I), hydroxy group, nitro group, cyano group, 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, and are each independently C 1 to C 10 alkyl groups, amidino groups, 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 it means substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group.

Unless stated otherwise in the specification, an "alkyl group"'is a C1 to C20 alkyl group Means, specifically, a C 1 to C 15 alkyl group, "cycloalkyl group" means a C3 to C20 cycloalkyl group, specifically means a C3 to C18 cycloalkyl group, '' alkoxy group 'means C1 to C20 Means an alkoxy group, specifically means a C1 to C18 alkoxy group, "aryl group" means a C6 to C20 aryl group,

Specifically, it means a C6 to C18 aryl group, "alkenyl group" means a C2 to C20 alkenyl group, specifically means a C2 to C18 alkenyl group, '' alkylene group 'means a C1 to C20 alkylene group In addition, specifically, it means a C1 to C18 alkylene group, "arylene group" means a C6 to C20 arylene group, and specifically means a C6 to C16 arylene group.

Unless stated otherwise in the specification, "(meth) acrylate"

Both "acrylate" and "methacrylate" mean possible, and "(meth) acrylic acid" means that both "acrylic acid" and "methacrylic acid" are possible.

As used herein, unless otherwise defined, "combination" means a combination or co-addition. "Co-polymerization" means block copolymerization or random copolymerization,

"Copolymer" means a block copolymer or a random copolymer.

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

Also, unless otherwise defined herein, 'means a moiety connected to the same or different atoms or formulas. It provides a compound represented by the following formula (1).

In Chemical Formula 1,

M is Cu, Zn, Co or Mo,

It is an aryloxy group,

At least one of R ¹ to R ¹⁶ is represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

The compound represented by Chemical Formula 1 has excellent green spectral characteristics and high molar extinction coefficient. Furthermore, the compound represented by Chemical Formula 1 may include a substituent represented by Chemical Formula 2, thereby exhibiting excellent solubility in organic solvents and excellent luminance when applied to a color filter.

In one embodiment, M may be Zn.

Formula 2 may be represented by the following formula (3).

In Chemical Formula 3,

The compound represented by Chemical Formula 1 according to an embodiment necessarily includes a substituent represented by Chemical Formula 2, for example, Chemical Formula 3, so that red-shift occurs, and thus, a case in which a conventional pigment such as a green pigment is applied The brightness is excellent.

In addition, unlike the compound represented by Formula 1 according to an embodiment, when the phthalocyanine-based dye compound includes an amide substituent, the solubility in an organic solvent is greatly reduced, but the compound represented by Formula 1 according to the embodiment is The solubility in an organic solvent can be greatly improved by including the substituent represented by Formula 2, for example, Formula 3.

At least one of R ¹ to R ¹⁶ may be represented by Formula 2, and at least one of R ¹ to R ¹⁶ may be represented by any one of Formulas 4 to 7.

[Formula 4]

5]

[Formula 6]

In Chemical Formulas 6 and 7,

L ¹ is a substituted or unsubstituted C1 to C10 alkylene group,

R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group.

For example, L ¹ is a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, a substituted or unsubstituted propylene group, a substituted or unsubstituted butylene group, a substituted or unsubstituted pentylene group, a substituted or unsubstituted And a substituted or unsubstituted hexylene group, a substituted or unsubstituted heptylene group, a substituted or unsubstituted octylene group, a substituted or unsubstituted nonylene group or a substituted or unsubstituted decylene group.

Compound according to one embodiment, in addition to the substituent represented by the formula (2), by further including a substituent represented by any one of the formulas (4) to (7), solubility in the organic solvent can be increased and the coloring power can be excellent.

For example, in Formula 1, at least one of R ¹ to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by any one of Formula 4 to Formula 7, R ⁹ to At least one of R ¹² may be represented by any one of Formulas 4 to 7, and at least one of R ¹³ to R ¹⁶ may be represented by any one of Formulas 4 to 7.

For example, in Formula 1, at least one of R ¹ to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by Formula 2, and at least one of R ⁹ to R ¹² . May be represented by any one of Formulas 4 to 7, and at least one of R ¹³ to R ¹⁶ may be represented by any one of Formulas 4 to VII.

For example, in Formula 1, at least one of R ¹ to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by any one of Formula 4 to Formula 7, R ⁹ to At least one of R ¹² may be represented by Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by any one of Formulas 4 to 7.

For example, in Formula 1, at least one of the R ¹ to R ⁴ is the formula 2, at least one of R ⁵ to R ⁸ is represented by Formula 2, at least one of R ⁹ to R ¹² is represented by Formula 2, and at least one of R ¹³ to R ¹⁶ is It may be represented by any one of Formula 4 to Formula 7. For example, in Formula 1, at least one of R ¹ to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by Formula 2, and at least one of R ⁹ to R ¹² May be represented by Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Formula 2.

For example, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 8 to 16, but is not necessarily limited thereto.

[Formula 8]

[Formula 15]

Since the compound according to one embodiment includes a substituent represented by Chemical Formula 2, for example, Chemical Formula 3, a more vivid color is expressed even in a small amount. It is possible to manufacture a display element having excellent color characteristics such as brightness and contrast ratio when used as a colorant. For example, the compound may be a colorant such as a dye such as a green dye such as a dye having a maximum transmittance in the wavelength range of 445 nm to 560 nm.

In general, dyes are the most expensive of the components used in color filters. Therefore, in order to achieve a desired effect such as high brightness or high contrast ratio, more expensive dyes have to be used. However, when using the compound according to the embodiment as a dye in the color filter, it is possible to achieve excellent color characteristics such as high brightness, high contrast ratio even in a small amount it is possible to reduce the production cost.

Furthermore, the compound according to the embodiment may further include a substituent represented by any one of Formulas 4 to 7 in addition to the substituent represented by Formula 2, for example, Formula 3, in this case, for the organic solvent Solubility and coloring power become more excellent.

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

For example, the photosensitive resin composition may include a compound according to the embodiment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

The compound according to one embodiment may serve as a colorant such as a dye such as a green dye in the photosensitive resin composition, thereby expressing excellent color characteristics.

The compound according to one embodiment may be included in an amount of 1 weight ⁰ /. 10 weight ⁰ /. For example, 3 weight ⁰ /. 7 weight ⁰ /. When the compound according to the embodiment is included in the above range, color reproduction and contrast ratio are excellent.

The photosensitive resin composition may further include a pigment, such as a yellow pigment. The yellow pigment has a C.I. Pigment Yellow 139, CI. Pigment yellow 138, I. Pigment yellow 150, etc. are mentioned, These can be used individually or in mixture of 2 or more types.

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

The pigment dispersion is a pigment, a solvent of the solid content and the pigment in the solvent A dispersant for uniformly dispersing may be included.

Pigments of the solid content is 1% to 20 weight ⁰ / weight relative to the pigment dispersion as a total amount., Such as 8 wt. ^_0/0 to 20 parts by weight ^_0/0, for example, 8 parts by weight ^_0/0 to 15 parts by weight ^_0/0, for example, 10 parts by weight ⁰ / ₀ to 20 may be included in a weight ^_0/0, for example, 10 parts by weight ^_0/0 to 15 parts by weight ^_0/0.

As the dispersant, non-dispersible dispersants, anionic dispersants, cationic dispersants, and the like may be used. Specific examples of the dispersant include polyalkylene glycols and esters thereof, polyoxyalkylenes, polyhydric alcohol ester alkylene oxide adducts,

Alcohols alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more thereof. .

Examples of commercially available products of the dispersant include, for example, DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPE BYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165,

DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182,

DISPERBYK-2000, DISPERBYK-2001, and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc. of EFKA Chemical Co., Ltd .; Zenspera Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, and the like; Or PB711, PB821 from Ajinomoto.

The dispersing agent may comprise from 1 weight ^_0/0 to 20% by weight relative to the total amount of the pigment dispersion. When the dispersant is included in the above range, it is possible to maintain an appropriate viscosity to excellent dispersibility of the photosensitive resin composition, thereby maintaining the optical, physical and chemical quality in the product application.

Examples of the solvent for forming the pigment dispersion include ethylene glycol acetate,

Ethyl salosolve, propylene glycol methyl ether acetate, ethyl lactate,

Polyethylene glycol, cyclonucleanone, propylene glycol methyl ether and the like can be used.

The pigment dispersion can comprise from 10 weight ⁰ /. To 20 parts by weight ^_0/0, for example, 12 to 18% by weight relative to the total photosensitive resin composition. remind

When the pigment dispersion is included in the above range, it is advantageous to secure process margins, color reproducibility and Contrast ratio is excellent.

The alkali-soluble resin may be an acrylic 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 including one or more acrylic repeating units.

The C1 ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxyl groups, and specific examples thereof may include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

The first ethylenically unsaturated monomer may comprise from 5 parts by weight ⁰ /. To 50 parts by weight ^_0/0, for example 10% to 40% by weight relative to the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer is an aromatic vinyl compound such as styrene, α-methylstyrene, vinylluene, vinylbenzylmethyl ether, etc .; Methyl (meth) acrylate,

Ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate,

Saturated carboxylic acid ester compounds such as cyclonuclear chamber (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 a 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 resin include (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer,

(Meth) acrylic acid / benzyl methacrylate / 2- hydroxyethyl methacrylate copolymer,

(Meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc. are mentioned, It is not limited to these, These can also be used individually or in combination of 2 or more types.

The weight average molecular weight of the alkali-soluble resin is 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 alkali-soluble resin is within the above range, the physical and chemical properties of the photosensitive resin composition are excellent, the viscosity is appropriate, and the adhesion to the substrate is excellent in the manufacture of the color filter.

The acid value of the alkali-soluble resin is 15 mgKOH / g to 60 mgKOH / g, such as

20 mgKOH / g to 50 mgKOH / g. When the acid value of alkali-soluble resin is in the said range, the resolution of a pixel pattern is excellent.

The alkali-soluble resin may be included in one weight ^_0/0 to 30% by weight, for example 1 weight ^_0/0 to 20 parts by weight ^_0/0 relative to the total photosensitive resin composition. alkali

When the soluble resin is included in the above range, it is excellent in developability in the production of color filters and crosslinkability is improved to obtain excellent surface smoothness.

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

Since the photopolymerizable compound has the ethylenically unsaturated double bond, the photopolymerizable compound may form a polymerized layer upon exposure in the pattern forming process, thereby forming a pattern having excellent heat resistance, light resistance, and chemical resistance.

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-butanedi di (meth) acrylate, 1,6-nucleic acid diol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate ， Pentaery tree

Tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol to hexa (meth) acrylate, dipentaerythr to di (meth) acrylate, dipentaerythr to tri (meth) acrylic Latent, dipentaerythritol penta (meth) acrylate,

The dipentaerythride is nucleated (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, trimethylol propane

Tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate and the like.

Examples of commercially available products of the photopolymerizable compound are as follows. remind

As an example of the monofunctional ester of (meth) acrylic acid, Toagosei Kagaku Kogyo Co., Ltd. Aronix M-101 ^® , Ml ll ^® , M-1 14 ^® etc .; KAYARAD TC-1 1 OS ^{® from} Nihon Kayaku Co., Ltd., TC-120S ^®, etc .; The V-158 ^® and V-2311 ^{® of} Osaka Yuki Chemical Co., Ltd. are mentioned. 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 ^®; Nihon Kayak Co., Ltd. KAYARAD HDDA ^® , HX-220 ^® , R-604 ^®, etc .; And V-260 ^® , V-312 ^® and V-335 HP ^{® from} Osaka Yuki Kagaku Kogyo Co., Ltd. Trifunctionality of the (meth) acrylic acid

Examples of esters include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-710 ^® , M-807 from Toagosei Kagaku Kogyo Co., Ltd. ^® , copper M-8060 ^®, etc .; Nihon

KAYARAD TMPTA ^® , DPCA-20 ^® , -30 ^® , -60 ^® , -120 ^{® from} Kayaku Co., Ltd .;

Osaka yukki Kayaku High School (main)社of V-295 ^®, East -300 ^®, East -360 ^®, East -GPT ^®, East -3PA ^®, Dong, and the like 400 ^®. The above products can be used alone or in combination of two or more.

The photopolymerizable compound may be used by treating with an acid anhydride in order to impart better developability.

The photopolymerizable compounds may be included as one weight ⁰ /. 15 to increase ⁰ /., For example 5% by weight to 10 parts by weight ^_0/0 relative to the total photosensitive resin composition. When a photopolymerizable compound is contained in the said range, hardening arises at the time of exposure in a pattern formation process, and it is excellent in reliability, and is excellent in developability to an alkaline developing solution.

The photopolymerization initiator is generally used in the photosensitive resin composition

As an initiator, an acetophenone type compound, a benzophenone type compound, a thioxanthone type compound, a benzoin type compound, an oxime type compound, or a combination thereof can be used, for example.

Examples of the acetophenone-based compound include 2,2'-dietospecific acetophenone, 2,2'-dibuspecial acetophenone, 2-hydroxy-2-methylpropiophenone and pt-butyltrichloro aceto Phenone, pt-butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholino Propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, and the like.

Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4 '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like. Can be.

Examples of the thioxanthone compound include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone etc. are mentioned.

Examples of the benzoin 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 and 2- (3 ', 4'- Dimethoxystyryl) -4,6-bis (trichloromethyl) -S-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -S-triazine ， 2- (p-Mexyphenyl) -4,6-bis (trichloromethyl) -S-triazine ， 2- (p-ryll) -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, etc. are mentioned. Examples of the oxime compounds include 0-acyl oxime compounds, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2, octanedione, 1- (eacetyloxime) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-

3-yl] ethanone, 0-ethoxycarbonyl-α-oxyamino-1-phenylpropane-1- may be used. Specific examples of the 0-acyl oxime 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-0-benzoate, 1- (4 ᅳ phenylsulfanylphenyl) -octane-1,2-disilver 2 -Oxime -0-benzoate, 1- (4-phenylsulfanylphenyl) -octane -1 -onoxime -0-acetate, 1- (4-phenylsulfanylphenyl) -butane-1-onoxime -0- Acetate and the like.

The photopolymerization initiator is a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound,

A biimidazole type compound etc. can be used.

The photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light and transferring energy after being excited.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercapto propionate pentaerythritol and tetrakis-3-mercapto propionate and dipentaerythryl tetrakis- 3-mercapto propionate, etc. are mentioned.

The photoinitiator may comprise from 0.01 weight% to 10 weight ^_0/0, for example, 0.1% by weight to 5 parts by weight ⁰ /. Relative to the total photosensitive resin composition. When the photopolymerization initiator is included in the above range, curing occurs during exposure in the pattern forming process to obtain excellent reliability, excellent heat resistance, light resistance and chemical resistance of the pattern, excellent resolution and adhesion, The fall of the transmittance | permeability can be prevented.

The solvent may be a material having compatibility with the compound, pigment, alkali-soluble resin, photopolymerizable compound and photopolymerization initiator according to one embodiment, but does not react.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, η-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; Glycols such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether

Ethers; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Methyl ethyl carbitle, diethyl carbye, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether, diethylene glycol

Carbyls such as diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Methyl ethyl ketone,

Ketones such as cyclonucleanone, 4-hydroxy-4-methyl-2-pentanone, methyl -η-propyl ketone, methyl -η-butyl ketone, methyl -η-amyl ketone and 2-heptanone; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, -η-butyl acetate and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxy acetic acid alkyl esters such as methyl oxy acetate, oxy ethyl acetate and oxy butyl acetate; Alkoxy acetate alkyl esters, such as methoxy methyl acetate, methoxy specialty ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxy propionic acid alkyl esters such as methyl 3-oxy propionate and ethyl 3-oxypropionate; 3-Messi

3-alkoxy propionic acid alkyl esters such as methyl propionate, ethyl 3-methoxy propionate, ethyl 3-ethoxy propionate and methyl 3-ethoxy propionate; 2-oxy propionic acid, such as 2-oxy methyl propionate, 2-oxy ethyl propionate and 2-oxy propionic acid propyl Alkyl esters; 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 2-oxy-2-methyl propionate, 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl methyl propionate, 2-ethoxy-2 Monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl propionic acid alkyls such as methyl methyl propionate; Esters such as ethyl 2-hydroxy propionate, ethyl 2-hydroxy-2-methyl propionate, ethyl hydroxy acetate, and methyl 2-hydroxy-3-methyl butanoate; Ketone acid esters such as ethyl pyruvate, and the like; and N-methylformamide, Ν, Ν-dimethylformamide, Ν-methylformanilade, Ν-methylacetamide, Ν, Ν-dimethylacetamide , N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dinuclear ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid High boiling point solvents, such as ethyl, diethyl oxalate, diethyl maleate, (gamma) -butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate, are mentioned.

Ethylene glycol, taking into account their compatibility and reactivity

Glycol ethers such as monoethyl ether; Ethylene glycol alkylether acetates such as ethyl salosolve acetate; Esters such as 2-hydroxy ethyl propionate; Carbyls such as diethylene glycol monomethyl ether; Propylene glycol alkylether acetates such as propylene glycol monomethylether acetate and propylene glycol propylether acetate can be used.

These solvents can be included in glass of quantification, such as 30 wt. ^_0/0 to 80% by weight relative to the total photosensitive resin composition. When the solvent is included in the above range, as the photosensitive resin composition has an appropriate viscosity, the processability in manufacturing the color filter is excellent.

The photosensitive resin composition according to another embodiment may further include an epoxy compound to improve adhesion to the substrate and the like.

As an example of the said epoxy compound, a phenol novolak epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol-A epoxy compound, an alicyclic epoxy compound, or a combination thereof is mentioned.

0.01 weight part of said epoxy compound with respect to 100 weight part of photosensitive resin compositions To 20 parts by weight, such as 0.1 parts by weight to 10 parts by weight. When the epoxy compound is included in the above range, it is excellent in adhesion, storage properties and the like.

In addition, the photosensitive resin composition may further include a silane coupling agent having a semi-aromatic substituent such as carboxyl group, methacryloyl group, isocyanate group, epoxy group, etc. in order to improve adhesion to the substrate.

Examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ-methacryloxypropyl trimethoxysilane, vinyl triacetic silane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, and γ-glycidoxy Cipropyl trimethoxysilane, (beta)-(3, 4- epoxycyclonuclear chamber) ethyltrimethoxysilane, etc. are mentioned, These can be used individually or in mixture of 2 or more types.

The silane 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 coupling agent is included in the above range, it is excellent in adhesion, shelf life and the like.

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

Examples of the surfactant include, but are not limited to, BM-1000 ^® , BM-1100 ^® , and the like by BM Chemie; Mecha packs F 142D ^® , F 172 ^® , F 173 ^® , F 183 ^®, etc. of Dai Nippon Inki Chemical Co., Ltd .; Prorad FC-135 ^® , FC-170C ^® , FC-430 ^® , East Κ 31 ^®, etc. of Sumitomo 3M Co., Ltd .; Asahi Grass Co., Ltd. Saffron S-112 ^® , S-113 ^® , S-131 ^® , S-141 ^® , S-145 ^®, etc .; Toray Silicone Co., Ltd. commercially available fluorine-based surfactants such as SH-28PA ^® , -190 ^® , -193 ^® , SZ-6032 ^® and SF-8428 ^® can be used.

The surfactant may be used in an amount of 0.001 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. If the surfactant is included in the above range, coating uniformity is ensured, staining does not occur, and

Wetting is excellent.

Moreover, the said photosensitive resin composition is in the range which does not inhibit physical property.

A certain amount of other additives such as antioxidants and stabilizers may be added.

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

The pattern forming process in the color filter is as follows. Applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing, or the like; Drying the coated photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; The exposed photosensitive resin composition film is developed with an aqueous alkali solution to be photosensitive.

Preparing a resin film; And heat-processing the said photosensitive resin film. Since the process conditions and the like are well known in the art, detailed descriptions thereof will be omitted herein.

[Form for implementation of invention]

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

Synthesis of Compound

Synthesis Example 1 Synthesis of 4- (Biphenyl-2-vIoxy) -3,5,6-trichloro-phthalonitrile

3,4,5,6-tetrachlorophthak itrile (5 g), 2-Phenylphenol (3.201 g), K ₂ C0 ₃ (3.898 g) and acetonitrile (50 ml) are added to a 100 ml polar flask and heated to reflux. After completion of the reaction, the mixture was filtered and washed with tetrahydrofuran to obtain a solid after concentration. The solid obtained at this time was washed several times with nucleic acid, filtered and dried in vacuo to obtain 4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile. Synthesis Example 2 Synthesis of 3,4,6-Trichloro-5-i2,6-dimethoxy-phenoxy) -phthalonitrile

In a 100 ml flask, add 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-dimethxoy phenol (7.21 g), K ₂ CO ₃ (3.898 g), N, N-Dimethylformamide (50rnl) at 70 ^° C Stir while heating. After reaction, extract with EA (ethyl acetate). Extraction and concentration, purification by column chromatography, concentration and vacuum drying yields 3,4,6-Trichloro-5- (2,6-dimethoxy-phenoxy) -phthalonitrile. Synthesis of (2-tert-Butyl-Dhenoxy) -3,5,6-trichloro-phthal () nitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-tert-Butylphenol (6.6 in a 100 ml flask Add K ₂ CO ₃ (3.898 g) and acetonitrile (50 ml) and reflux while heating. After reaction, extract with EA (ethyl acetate). Extraction, concentration, and purification by column chromatography, followed by concentration and vacuum drying to obtain 4- (2-tert-Butyl-phenoxy) -3,5,6-trichloro-phthalonitrile. Synthesis Example 4 Synthesis of 4- (4-tert-Butyl-phenoxy) -3,5,6-trichloro-phthaloiiitrile

3,4,5,6-tetrachk) iophthalonitrile (5g), 4-tert-Butylphenol (6.64g), K ₂ CO ₃ (3.898g) and acetonitrile (50ml) were added to a 100ml flask and refluxed. After reaction, extract with EA (ethyl acetate). After extraction, the resultant was concentrated, purified by column chromatography, concentrated and vacuum dried to obtain 4- (4-tert-Butyl-phenoxy) -3,5,6-trichloro-phthalonitrile. Synthesis Example 5 Synthesis of 3,4,6-Trichloro-5-i3-methyl-butoxy) -phthalonitrile

Add 3,4,5,6-tetrachlorophthal (3nitrile (5g), Isoamyl alcohol (5.9g), 1,8- Diazabicycloundec-7-ene (3.898g) and acetonitrile (50ml) in a 100ml flask After completion of reaction, extract with EA (ethyl acetate) Extraction and concentration column

Purification by column chromatography, concentration and vacuum drying give 3,4,6-Trichloro-5- (3-methyl-butoxy) -phthalonitrile. Synthesis 1 1 3,4,6-Trichloro- Synthesis of 5-i4-methoxy-phenoxyVphthalonitnle

Add 3,4,5,6-tetrachlorOphtlialomtrile (5 g), 4-methoxyphenol (3.201 g), K ₂ CO ₃ (6.64 g), acetonitrile (50 ml) in a 100 ml flask and reflux with heating. After reaction, extract with EA (ethyl acetate). After extraction, the mixture was purified by column chromatography, concentrated and vacuum dried to obtain 3,4,6-Trichloro-5- (4-methoxy-phenoxy) -phthalonitrile. Synthesis Example 7 Synthesis of Compound Represented by Chemical Formula 8

4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile (l.Og) of Synthesis Example 1, 3,4,6-Trichloro-5- (2,6) of Synthesis Example 2 in a 100 mL flask -dimethoxy-phenoxy) -phthalonitri ^

Add Diazabicycloundec-7-ene (0.38g), 1-pentane (7g), zinc acetate (0.15g) and put it at 140 ^° C. Stir while heating. After completion of reaction, the solution was concentrated and purified by column chromatography. The liquid obtained after purification is concentrated to give a solid. The crystallized solid is dried in vacuo to obtain a compound represented by the following formula (8).

[Formula 8]

Maldi-tof MS: 1647.95 m / z Synthesis Example 8 Synthesis of Compound Represented by Chemical Formula 9

4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile in Synthesis example 1 in lOOmL flask (l .Og), 3 of Preparation Example ^{2, 4, 6-Trichloro-} 5- (2, 6 -dimethoxy-phenoxy) -phthalonitrile ^

Add Diazabicycloundec-7-ene (() .58g), 1-pentane (14g), zinc acetate (() .23g) and stir while heating to 140 ^° C. After completion of reaction, the solution was concentrated and purified by column chromatography. The liquid obtained after purification is concentrated to give a solid. The crystallized solid was vacuum dried to obtain a compound represented by the following formula (9). [Formula 9]

Maldi-tof MS: 1631.91 m / z Synthesis Example 9 Synthesis of Compound Represented by Chemical Formula 10

Synthesis Example 1 in a flask lOOmL 4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile (0.5g), 3 of Preparation Example ^{^{2, 4, 6 -Trichloro-5-}} (2, 6- Add dimethoxy-phenoxy) -phthalonitrile (l. ⁴⁴ g ^ Diazabicycloundec-7-ene (0.58 g), 1-pentane (14 g) and zinc acetate (0.23 g) and stir while heating to 140 ^° C. Concentration and purification by column chromatography The purification of the obtained liquid is concentrated to give a solid The crystallized solid is dried in vacuo to obtain a compound represented by the following Chemical Formula 10.

Formula

Maldi-tof MS: 1615.86 m / z Synthesis Example 10 Synthesis of Compound Represented by Chemical Formula 11

Synthesis Example 4 in lOOmL flask, 4- (4-tert-Butyl- phenoxy) - 3, 5,6-trichloro- phthalonitrile (lg), prepared in Synthesis Example 2 3,4,6-Trichloro-5- (2,6 Add -dimethoxy-phenoxy) -phthalonitrile (0.33g), 1,8-Diazabicycloundec-7-ene (0.41 g), 1-pentanol (14g), zinc acetate (0.16g) and stir while heating to 140 ^° C . After completion of reaction, the solution was concentrated and purified by column chromatography. The liquid obtained after purification is concentrated to give a solid. The crystallized solid was dried in vacuo to obtain a compound represented by the following Chemical Formula 11.

Synthesis Example 11 Synthesis of Compound Represented by Chemical Formula 12

3,4,6-Trichloro-5- (3-methyl-butoxy) -phthalonitrile (lg) of Synthesis Example 5 and 3,4,6-Trichloro-5- (2,6-dimethoxy of Synthesis Example 2 in a 100 mL flask -phenoxy) -phthalomtrile ^

Add Diazabicycloundec-7-ene (0.48g), 1-pentane (14g), zinc acetate (0.19g) and stir while heating to 140 ^° C. After completion of reaction, the solution was concentrated and purified by column chromatography. The liquid obtained after purification is concentrated to give a solid. The crystallized solid was vacuum dried to obtain a compound represented by the following formula (12). 12]

Maldi-tof MS: 1401.77 m / z Synthesis Example 12 Synthesis of Compound Represented by Chemical Formula 13

4- (Biphenyl-2-yloxy) -3,5,6-trichloiO-phthalonitrile (lg) of Synthesis Example 1 3,4,6-Trichloro-5- (3-methyl-butoxy) of Synthesis Example 5 in a 100 mL flask -phthalonitrile (0.4g 3,4,6-Trichloro-5- (2,6-dimethoxy-phenoxy) -phthalonitrile (0.48g) of Synthesis Example 2, 1,8-Diazabicycloundec-7-ene (0.58g), 1 Add pentane (14 g), add zinc acetate (0.22 g) and stir while heating to 140 ^° C. After completion of reaction, concentrate and purify by column chromatography After purification, the obtained liquid is concentrated to give a solid. The crystallized solid was vacuum dried to obtain a compound represented by the following formula (13). [Formula 13]

Maldi-tof MS: 1565.89 m / z Synthesis Example 13: Synthesis of Compound Represented by Chemical Formula 14

In a 100 mL flask, 3,4,6-Trichloro-5- (2,6-dimethoxy-phenoxy) -phthalonitrile (lg), 1,8-Diazabicycloundec-7-ene (0.30 g) and 1-tan of Synthesis Example 2 were added. (7g), add zinc acetate (0.12g) and stir while heating to 140 ^° C. After reaction, concentrate the column

Purification by column chromatography. The liquid obtained after purification is concentrated to give a solid. The crystallized solid was vacuum dried to obtain a compound represented by the following formula (14).

Formula

Maldi-tof MS: 1599.82 m / z Synthesis Example 14 Synthesis of Compound Represented by Chemical Formula 15

In an OOmL flask, (3,4,6-TrichknO-5- ( ^4- methoxy-phenoxy) -phthalonitrile (lg) of Synthesis Example 6, 3,4,6-Trichloro-5- (2,6) Add -dimethoxy-phenoxy) -phthalonitrile (0.50g), 1,8-Diazabicycloundec-7-ene (0.65g), 1-pentanol (14g), zinc acetate (0.26g) and stir while heating to 140 ^° C After completion of reaction, the mixture was concentrated and purified by column chromatography, and then the obtained liquid was concentrated to obtain a solid, and the crystallized solid was dried in vacuo to obtain a compound represented by the following Chemical Formula 15.

[Formula 15]

Maldi-tof MS: 1509.74 m / z Synthesis Example 15 Synthesis of Compound Represented by Chemical Formula 16

In a 100 mL flask, 4- (2-tert-Butyl-phenoxy) -3,5,6-trichloiO-phthalonitrile (lg) of Synthesis Example 3, 3, ⁴ , ^6- Trichloro-5- (2,6) of Synthesis Example 2 Add -dimethoxy-phenoxy) -phthalonitrile (0.33g), 1,8-Diazabicycloundec-7-ene (0.41 g), 1-pentanol (14g), zinc acetate (0.16g) and stir while heating to 140 ^° C . After completion of reaction, the solution was concentrated and purified by column chromatography. The liquid obtained after purification is concentrated to give a solid. The crystallized solid was vacuum dried to obtain a compound represented by the following formula (16). [Formula 16]

Maldi-tof MS: 1587.98 m / z Comparative Synthesis Example Synthesis of Compound Represented by Chemical Formula 17

In a 100 mL flask, 4- (2-sec-Butyl-phenoxy) -3,5,6-trichloro-phthalonitrile (lg), 1,8- Diazabicycloundec-7-ene (0.30 g), 1-pentanol (7 g), Add zinc acetate (() .12g) and stir while heating to 140 ^° C. After completion of reaction, the solution was concentrated and purified by column chromatography. The liquid obtained after purification is concentrated to give a solid. The crystallized solid was vacuum dried to obtain a compound represented by the following formula (17).

17]

Maldi-tofMS ： 1584.04 m / z

(Synthesis of Photosensitive Resin Composition)

Example 1

The components mentioned below were mixed with the compositions shown in Table 1 below to prepare a photosensitive resin composition according to Example 1.

Specifically, after dissolving the photopolymerization initiator in a solvent and stirred at room temperature for 2 hours, an alkali-soluble resin and a photopolymerizable compound were added thereto, followed by stirring at room temperature for 2 hours. Subsequently, a compound (compound represented by Formula 8) and a pigment (in the form of a pigment dispersion) prepared in Synthesis Example 7 were added as a colorant to the obtained semi-flour, followed by stirring at phase silver for 1 hour. The product was then filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

[Table 1],

(Unit: weight ⁰ /。)

Compounding Material Content Coloring Agent Salt Compound 7 of Synthesis Example 7 Pigment Dispersion Pigment Y 138 Pigment Dispersion 15.0

(A) / (B) -15/85 (w / w),

Molecular weight (Mw) = 22,000 g / mol

Alkali Soluble Resin 3.5

(A): methacrylic acid

(B): benzyl methacrylate

Photopolymerizable compound dipentaerythr to nucleoacrylate (DPHA) 8.0 photopolymerization initiator 1,2-octanedione 1.0

2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholine-4-

0.5 yl-phenyl) -butan-1-one

Solvent Cyclonuxanon 37.0

Propylene Glycol Monomethyl Ether

30.0 Acetate)

Total 100.00 Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 8 (compound represented by Formula 9) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 9 (compound represented by Formula 10) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 10 (compound represented by Formula 11) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Example 5 A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 1 (compound represented by Formula 12) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Example 6

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 12 (compound represented by Formula 13) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Example 7

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 13 (compound represented by Formula 14) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Example 8

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 14 (compound represented by Formula 15) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Example 9

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 15 (compound represented by Formula 16) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Comparative Example 1

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Comparative Synthesis Example 1 (compound represented by Formula 17) was used instead of the compound of Synthesis Example 7 (compound represented by Formula 8). Comparative Example 2 A photosensitive resin composition was prepared in the same manner as in Example 1 except that the composition shown in Table 2 was used instead of the composition shown in Table 1.

TABLE 2

(Unit: weight ^_0/0)

Comparative Example 3

A photosensitive resin composition was prepared in the same manner as in Comparative Example 2 except that Pigment G36 pigment dispersion was used instead of Pigment G58 in the pigment dispersion. Evaluation: color coordinates, luminance, and contrast ratio measurements

The photosensitive resin composition prepared in Examples 1 to 9 and Comparative Examples 1 to 3 was applied to a glass substrate having a thickness of 1 mm by degreasing, and 9 (hot plate of TC The coating was dried for 2 minutes to obtain a coating, which was then exposed using a high pressure mercury lamp having a dominant wavelength of 365 nm.Then, the sample was dried in a hot air circulation drying furnace ^at 200 ^° C. for 5 minutes. Obtained. The pixel layer was measured in color coordinates (x, y), luminance (Y) and contrast ratio using a spectrophotometer (MCPD3000, Otsuka electronic Co., Ltd.), and are shown in Table 3 below.

TABLE 3

From Table 3, the photosensitive resin composition of Examples 1 to 9 containing the compound according to one embodiment as a dye is superior to the photosensitive resin composition of Comparative Examples 1 to 3 without containing the compound It can be seen that. As mentioned above, although preferred embodiment of this invention was described, this invention is not limited to this, It can be variously modified and implemented in a claim, the detailed description of an invention, and the range of an accompanying drawing. Naturally, it belongs to the scope of the invention.

Claims

Claims Claim 1 Compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

Μ is Cu, Zn, Co or Mo,

R 'to R ¹⁰ 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 group, or a substituted or unsubstituted group Substituted C6 to C20

An aryloxy group,

At least one of R ¹ to R ¹⁶ is represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

R ¹⁷ and R ¹⁸ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C2 aryl group.

[Claim 2]

According to claim 1,

Formula 2 is a compound represented by the following formula (3):

3]

In Chemical Formula 3,

[Claim 3]

The method of claim 1,

At least one of R ¹ to R ¹⁶ is represented by Formula 2,

At least one of the R ¹ to R ¹⁶ is a compound represented by any one of the following formula (4):

[Formula 4]

6]

7]

In Chemical Formulas 6 and 7,

L ¹ is a substituted or unsubstituted C1 to C 10 alkylene group

R ¹⁹ is a substituted or unsubstituted C1 to C 10 alkyl group. [Claim 4]

The method of claim 1,

At least one of R ¹ to R ⁴ is represented by Formula 2,

At least one of R ⁵ to R ⁸ is represented by any one of the following Chemical Formulas 4 to 7,

At least one of the R ⁹ to R ¹² is represented by any one of the following Formula 4 to Formula 7,

Wherein R ¹³ to at least one of the compounds represented by any of the following formulas ₄ to formula _(7):

[Formula 4]

5]

6]

In Chemical Formulas 6 and 7,

L ¹ is a substituted or unsubstituted C1 to C10 alkylene group

R ¹⁹ is a substituted or unsubstituted C 1 to C10 alkyl group.

[Claim 5]

The method of claim 1,

At least one of R ¹ to R ⁴ is represented by Formula 2, At least one of R ⁵ to R ⁸ is represented by Formula 2, at least one of R ⁹ to R ¹² is represented by any one of Formulas 4 to 7,

At least one of the R ¹³ to R ¹⁶ is a compound represented by any one of the following formula (4):

[Formula 4]

In Chemical Formulas 6 and 7,

L ¹ is a substituted or unsubstituted C1 to C10 alkylene group,

R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group.

[Claim 6]

The method of claim 1,

At least one of R ′ to R ⁴ is represented by Formula 2,

At least one of R ⁹ to R ¹² is represented by Formula 2,

At least one of R ¹³ to R ¹⁰ is a compound represented by any one of the following Formula 4 to Formula 7: [Formula 4]

In Chemical Formulas 6 and 7,

L ¹ is a substituted or unsubstituted C1 to C10 alkylene group,

R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group.

[Claim 7]

In that U term,

At least one of R ¹ to R ⁴ is represented by Formula 2, at least one of R ⁵ to R ⁸ is represented by Formula 2, and at least one of R ⁹ to R ¹² is represented by Formula 2 At least one of R ¹³ to R ¹⁶ may be represented by any one of the following Formulas 4 to 7:

[Formula 4]

[Formula 5]

[Formula 6]

CH.

CH ₃

[Formula 7]

In Chemical Formulas 6 and 7,

L ¹ is a substituted or unsubstituted C1 to C10 alkylene group

19 ι

R substituted or unsubstituted C1 to C10 alkyl group.

[Claim 8]

The method of claim 1,

At least one of R ¹ to R ⁴ is represented by Formula 2,

At least one of the R ^{5 To} R ^{8 Is} represented by the formula (2),

At least one of the R ⁹ to R ¹² is represented by the formula (2),

At least one of the R ¹³ to R ¹⁰ is a compound represented by the formula (2).

[Claim 9]

The method of claim 1,

The compound represented by Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 8 to 16.

[Formula 9]

WO 2016/175390 PCT / KR2015 / 008106

[Formula 14]

Formula

[Claim 10]

According to claim 1 i,

The compound is a green dye.

[Claim 1 11]

The method of claim 10,

The green dye has a maximum transmittance in the wavelength range of 445nm to 560nm. [Claim 12]

The photosensitive resin composition containing the compound of any one of Claims 1-1.

【Claim 13】

The method of claim 12,

The photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent. [Claim 14]

The method of claim 13,

The photosensitive resin composition further comprises a pigment.

【Claim 15】

The method of claim 14,

The pigment is a yellow pigment photosensitive resin composition. [Claim 16]

The color filter manufactured using the photosensitive resin composition of Claim 12.