WO2016085075A1

WO2016085075A1 - Novel compound, photosensitive resin composition including same, and color filter

Info

Publication number: WO2016085075A1
Application number: PCT/KR2015/006309
Authority: WO
Inventors: 김형묵; 신나율; 신명엽
Original assignee: 삼성에스디아이 주식회사
Priority date: 2014-11-28
Filing date: 2015-06-22
Publication date: 2016-06-02
Also published as: KR20160064877A; TW201619169A; TWI589582B; KR101814673B1

Abstract

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

Description

【Specification】

[Name of invention]

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

Technical Field

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. ^"In one embodiment the other is to provide a photosensitive resin composition containing the additive 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).

One ]

In Chemical Formula 1 R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C 1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 heteroaryl group,

M is represented by the following formula (2) or (3),

[Formula 2]

[Formula 3]

In Chemical Formula 3,

A is a substituted or unsubstituted C6 to C20 aryl group.

R ¹ to R ⁴ are all hydrogen atoms, and R ⁵ to R ⁸ may each independently be a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

R ¹ to R ⁴ are all hydrogen atoms, R ⁶ is a hydrogen atom or a substituted or unsubstituted substituted C1 to C20 alkyl group, and R ⁸ may be a hydrogen atom or a substituted or unsubstituted C1 to C20 alkoxy group have.

Formula 1 may be represented by any one of the following Formula 4 to Formula 7.

[ 4]

[Formula 5]

[6]

[7]

In Formula 4 to Formula 7, ^' X ¹ is Ν, Ρ or Β,

X ² and X ³ are each independently 0, S, S (= 0) or S (= 0) ₂ ,

L ¹ is a substituted or unsubstituted C1 to C20 alkylene group,

L ² is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted

C6 to C20 arylene group,

R ⁹ to R ¹² are each independently a substituted or unsubstituted C1 to C20 alkyl group substituted or unsubstituted C2 to C20 heteroaryl group or cyano group,

M is represented by the following formula (2) or (3),

[Formula 2]

[Formula 3]

In Chemical Formula 3,

A is a substituted or unsubstituted C6 to C20 aryl group.

Formula 1 may be represented by one selected from the group consisting of Formula 8 to Formula 19.

[10]

[

[Formula 12]

[Formula 13]

[Formula 14]

The compound may be a yellow dye.

The yellow dye may have a maximum absorption region in the wavelength range of 400nm to 550nm.

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

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

Dipyrimethine-based boron compound according to an embodiment has excellent yellow spectral properties and high molar extinction coefficient and solubility in an organic solvent, can be used as a dye when preparing a photosensitive resin composition for color filters, including the dye The color filter 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 an example. As is presented, the invention is not limited thereby, but the invention is only defined by the scope of the claims set out below.

Unless stated otherwise in the specification, "substituted" to "substituted" means 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, "alkyl group" 'means a C1 to C20 alkyl group, specifically means a C1 to C15 alkyl group, "cycloalkyl group" means a C3 to C20 cycloalkyl group, specifically Means a C3 to C18 cycloalkyl group, "alkoxy group" means a C1 to C20 alkoxy group, specifically means a C1 to C18 alkoxy group, "aryl group" means a C6 to C20 aryl group,

Specifically, it refers to a C6 to C18 aryl group, 'an' alkenyl group 'means C2 to C20

It means an alkenyl group, and specifically, the C2 to mean a group C18 alkenyl, and "means an alkylene group '' is C1 to C20 alkylene, and specifically, means a C1 to C18 alkylene, _and" aryl group "means Means a C6 to C20 arylene group, specifically means a C6 to C16 arylene group.

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

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

Unless otherwise defined herein, “combination” means mixed or copolymerized. In addition, "copolymerization" 'means block copolymerization or random copolymerization,

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

Unless otherwise defined in the chemical formulas herein, when no chemical bond is drawn at the position where the chemical bond is to be drawn,

It means that it is combined.

Unless otherwise defined herein, "*" is the same or different atoms or It means a part linked with the formula.

In addition, unless otherwise defined in this specification, "maximum light absorption area" means the area (range) which shows the maximum absorbance. One embodiment provides a compound represented by Formula 1 below.

One]

In Chemical Formula 1,

1 to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 heteroaryl group,

M is represented by the following formula (2) or (3),

[Formula 2]

[Formula 3]

In Chemical Formula 3,

A is a substituted or unsubstituted C6 to C20 aryl group.

The compound represented by the formula (1) is a dipyrimethine-based boron compound, has excellent yellow spectral characteristics and high molar extinction coefficient, and also has excellent solubility in organic solvents. Furthermore, since the compound represented by Formula 1 includes a cyano group at a fixed position, the dipyrimethine ligand is stable, and the heat resistance, chemical resistance, and processability of the compound represented by Formula 1 are excellent. Specifically, the dipyrimethine ligand is present in the imine form as shown in the following Formula X due to the aromatic stability of the pyridine ring (ie, two pyridine rings are linked by sp3 carbon), but fixed as the compound represented by Formula 1 above. If a cyano group is present in the above position, it is present in the form of a conjugated enamine (Formula Y).

[Formula X]

[Formula Y]

In this case, when the dipyridomethine ligand is present in the form of a conjugated enamine rather than an imine form, the desired spectrophotometer can be adjusted, and in view of fairness, the post-baking of the photosensitive resin composition at a temperature of 230 ^° C or higher The cyano group acts as a blocking group, resulting in excellent heat and chemical resistance.

In addition, in Chemical Formula 1, R ¹ to R ⁸ are not a substituted or unsubstituted aryl group. When the R ¹ to R ⁸ is a substituted or unsubstituted aryl group, it should be synthesized using a Pd-based catalyst, but the cost of the Pd-based catalyst is high and the economical efficiency is low, and the spectral peak is wide, so that the permeability should be high. Absorption occurs and luminance decreases, and solubility in organic solvents such as PGMEA is very low overall.

For example, R ¹ to R ⁴ are all hydrogen atoms, R ⁶ is a hydrogen atom or a substituted or unsubstituted substituted C1 to C20 alkyl group, and R ⁸ is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkoxy It may be a flag.

Formula 1 may be represented by any one of the following Formula 4 to Formula 7. 4]

In Chemical Formulas 4 to 7,

X ¹ is Ν, Ρ or Β,

X ² and X ³ are each independently 0, S, S (= 0), or S (= 0) ₂ ,

L ¹ is a substituted or unsubstituted C1 to C20 alkylene group,

L ² is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,

R ⁹ to R ¹² are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group, or a cyano group,

M is represented by the following formula (2) or (3),

[Formula 2]

[Formula 3]

In Chemical Formula 3,

A is a substituted or unsubstituted C6 to C20 aryl group.

For example, R ⁹ and R ¹² may each independently represent a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁰ and R ^{1 1} may each independently represent a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted group. It may be a C2 to C20 heteroaryl group or a cyano group.

As described above, the compound according to an embodiment may be a dipyrimethine-based boron compound, for example, the compound represented by Formula 1 may be a dipyrimethine-based boron fluoride compound or a dipyrimethetine-based catechol boron compound. .

The compound represented by Formula 1, for example, the dipyrimethine-based boron difluoride compound may be represented by any one selected from the group consisting of Formulas 8 to 15 below.

[Formula 8]

[Formula 9]

Formula

[Formula 12]

Formula

[15]

The compound represented by Formula 1, for example, the dipyrimethine-based catechol boron compound may be represented by any one selected from the group consisting of Formulas 16 to 19 below.

16]

Formula

Compound according to one embodiment includes a cyano group in a fixed position

As a dipyrimethine-based boron compound, a vivid color can be expressed even in a small amount, and when used as a colorant, it is possible to manufacture a display device having excellent color characteristics such as brightness and contrast ratio. For example, the compound may be a colorant such as a dye, such as a yellow dye, such as a dye having a maximum absorption region in the wavelength range of 400 nm to 550 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. 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, a pigment, an alkali-soluble resin, a photopolymerization ^'compound, a photopolymerization initiator and a solvent according to the embodiment-can. The compound according to the embodiment may serve as a colorant such as a dye such as a yellow dye in the photosensitive resin composition, thereby expressing excellent color characteristics.

The compounds according to the embodiment can be included as 0.1% by weight to 10 parts by weight ⁰ / with respect to the total amount of photosensitive resin composition, for example, 3 parts by weight ⁰ /. To 7% by weight. When the compound according to the embodiment is included in the above range, color reproducibility and contrast ratio are excellent.

The pigment may include a yellow pigment, a green pigment or a combination thereof, but is not limited thereto. For example, the pigment may be included in the photosensitive resin composition in the form of a pigment dispersion. The pigment dispersion may include a solid pigment, a solvent and a dispersant for uniformly dispersing the pigment in the solvent.

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

As the dispersant, a nonionic dispersant, an anionic dispersant, a cationic dispersant, or the like may be used. Specific examples of the dispersant include polyalkylene glycol and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene 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 dispersant 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,

DISPERBY-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, Solsperse24000GR, Solsperse 27000, Solsperse 28000, and the like; Or PB7U, PB821 from Ajinomoto.

The dispersing agent is 1 part by weight ⁰ / with respect to the total amount of the pigment dispersion. To 20 may be included in a weight ^_0/0. 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 cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate,

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

The pigment dispersion is 10% by weight to the total amount of the photosensitive resin composition 30 may be included in a weight ^_0/0, for example, 10 parts by weight ^_0/0 to 25% by weight. remind

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

The alkali-soluble resin may be an acrylic resin.

The acrylic resin is a copolymer containing a C 1 ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith and at least one acrylic repeating unit.

The crab 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.

To the first ethylenically unsaturated monomer it may comprise from 5 parts by weight ^_0/0 to 50 parts by weight ^_0/0, for example, 10 parts by weight ⁰ /. To 40 parts by weight ^_0/0 with respect 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,

Unsaturated carboxylic 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; These etc. can be mentioned, These can be used individually or in mixture of 2 or more.

Specific examples of the acrylic binder resin

(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 Although these etc. are mentioned, It is not limited to these, You may use these individually or in mixture of 2 or more types. ᅳ

The weight average molecular weight of the alkali-soluble resin may be 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 when the color filter is manufactured.

The acid value of the alkali-soluble resin may be 15 mgKOH / g to 60 mgKOH / g, such as 20 mgKGH / 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 1% by weight to 30% by weight ⁰ /. For example, 1 weight ⁰ /. To 15 weight ⁰ /. When the alkali-soluble resin is included in the above range, excellent color filter manufacturer developability and crosslinkability can be improved to obtain excellent surface smoothness.

The photopolymerizable compound has at least one ethylenically unsaturated double bond

Monofunctional or polyfunctional esters of (meth) acrylic acid can be used.

The photopolymerizable compound may have an ethylenically unsaturated double bond, thereby forming a pattern having excellent heat resistance, light resistance, and chemical resistance by causing sufficient polymerization during exposure in a 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, neopentyl glycol di (meth) acrylate, 1,4 -Butanedi di (meth) acrylate, 1,6-nucleic acid di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) ) Acrylates, pentaerythritol, tetra (meth) acrylate, pentaerythres, nucleated (meth) acrylate, dipentaerythr, di (meth) arc Acrylate, dipentaerythritol the Erie the tree tri (meth) acrylate, di-pentaerythrityl tree 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 etc. are mentioned.

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

Examples of the monofunctional ester of (meth) acrylic acid include Aronix M-101 ^® , M-1 1 1 ^® , M-1 14 ^®, and the like manufactured by Toagosei Kagaku Kogyo Co., Ltd .; Nihon Kayak Co., Ltd.'s KAYARAD TC-11 OS ^® , 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-8100 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 compound may be incorporated with 1% to 15 increased ^_0/0, for example 5 parts by weight ^_0/0 to 10% by weight 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 the initiator, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, an oxime compound or a combination thereof can be used.

Examples of the acetophenone-based compound include 2,2'-diethoxy acetophenone, 2,2'-dibuoxy acetophenone, 2-hydroxy-2-methylpropiophenone and ρ-t-butyltrichloro Acetophenone, pt-butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl- ₍ (methylthio) phenyl) -2-morpholinopropane-1 -One, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, etc. are mentioned. .

Examples of the benzophenone-based compound, benzophenone, benzoyl benzoic acid, benzoyl Methyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4,4'- Dimethyl amino benzophenone, 4,4'- dichloro benzophenone, 3,3'- dimethyl- 2-methoxy benzophenone, etc. are mentioned.

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, 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-lryl) -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- ( ₀ -acetyloxime ) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, 0-ethoxycarbonyl-α-oxyamino-1-phenylpropane-1-one Etc. can 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-di silver 2-oxime-0-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1,2-dione 2 -Oxime-0-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oxime-0-acetate and 1-(4-phenylsulfanylphenyl)-butane-1-oxime-acetate Etc. can be mentioned.

The photopolymerization agent 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 absorbs light and enters an excited state _. It can also be used with photosensitizers that cause chemical reactions by delivery.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercapto propionate and pentaerythritol with tetrakis-3-mercapto propionate and dipentaerythryl tetrakis-

3-mercapto propionate, etc. are mentioned. ·

The photopolymerization initiator may be contained in the photosensitive resin composition with respect to the total amount of 0.01 ^_0/0 to 10 parts by weight ^_0/0, for example, 0.1% by weight to 5 parts by weight ⁰ /. When the photopolymerization initiator is included in the above range, curing is sufficiently performed upon 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, and due to unreacted initiator The fall of the transmittance can be prevented.

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

Examples of the solvent include methane and alcohols such as 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 salosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Methyl ethyl carbitle, diethyl carbyl, 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 methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Methyl ethyl ketone, cyclonucleanone, 4-hydroxy-

Ketones such as 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 acetic acid alkyl esters such as methyl methoxy acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxy propionic acid alkyl esters, such as 3-oxy methyl propionate and 3-oxy ethyl propionate; 3-Methoxy methyl propionate, 3-methoxy 3-alkoxy propionic acid alkyl esters such as ethyl propionate, ethyl 3-ethoxy propionate and decyl 3-ethoxy propionic acid; 2-oxy propionic acid alkyl esters such as 2-oxy methyl propionate, 2-oxy ethyl propionate and 2-oxy propionic acid propyl; 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 methyl, 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl propionate methyl, 2-ethoxy- Monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl propionic acid alkyls such as 2-methyl ethyl propionate; Esters such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl propionate, ethyl hydroxy acetate, and 2-hydroxy-3-methyl butanoate; Ketone acid esters such as ethyl pyruvate, and the like; Ν-methylformamide, Ν, Ν-dimethylformamide, N-methylformanilade, Ν-methylacetamide, Ν, Ν-dimethylacetamide Ν-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dinuclear ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid Ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve

High boiling point solvents, such as acetate, are mentioned.

Of these, ethylene glycol is preferably considered in consideration of compatibility and reaction properties.

Glycol ethers such as monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve 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.

The solvent may be included in a balance, such as 30 wt% to 80 wt%, based on the total amount of the 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.

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 of these.

The epoxy compound may be included in an amount of 0.01 parts by weight to 20 parts by weight, such as 1 part by weight to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. 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 reactive substituent such as a 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 triacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, and γ-glycidoxy Cipropyl trimethoxysilane, β- (3,4-epoxycyclonuclear chamber) ethyltrimethoxysilane, and the like, and these may be used alone or in combination of two or more thereof.

The silane coupling agent may be included in an amount of 0.01 parts by weight 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® by BM Chemie, Inc .; Mecha Pack F 142D®, F 172®, F 173®, F 183®, etc. from Dai Nippon Inki Chemical Co., Ltd .; Prorad FC-135®, Copper FC-170C®, Copper FC-430®, Copper FC-431®, and the like from Sumitomo 3M Co., Ltd .; Saffron S-1 12®, copper S-1 13®, copper S-131®, copper S-141®, copper S-145® by Asahi Grass Co., Ltd .; Fluorine-based surfactants such as SH-28PA® copper -190®, copper -193®, SZ-6032®, SF-8428® from Toray Silicone Co., Ltd. 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 water 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.

Certain amounts of other additives, such as antioxidants and stabilizers, may be added.

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

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 photosensitive resin composition film is developed by using an aqueous alkali solution in water to be photosensitive.

A step of producing 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.

[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 examples of the present invention, and the present invention is not limited to the following Examples. Synthesis of Compound

Synthesis Example 1 Synthesis of Compound Represented by Chemical Formula 12

(1) Sodium hydride (2.24 g) was slowly added to 2-Pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 2-Bromo-3- (2-ethylhexyloxy) pyridine (4.58 g) was added thereto, followed by stirring while refluxing. After the reaction

In the extraction process, the mixture was neutralized with an acidic aqueous solution and separated by column chromatography to obtain a precursor ligand ([3- (2-Ethyl-hexyloxy) -lH-pyridin-2-ylidene] -pyridin-2-yl-acetonitrile). .

(2) 0.9 ⁷ g of the precursor ligand ([3- (2-Ethyl-hexyloxy) -lH-pyridin-2-yHdene] -pyridin-2-yl-acetonitrile) obtained in step (1) was added to dichloromethane (100 mL). After melting, triethylamine (3 mL) and Borontrifluoride diethyl etherate (4 mL) were added at room temperature and stirred. After completion of the reaction was separated by column chromatography to obtain a compound represented by the following formula (12).

'H NMR (300 MHz, CDC1 ₃ ) δ 0.93 (6H), 1.38 (9H), 4.00 (2H), 6.88 (1H), 6.96 (1H) 7.04 (1H), 7.72 (1H), 7.83 (2H), 8.19 (1H) Synthesis Example 2: Synthesis of Compound Represented by Formula (8)

(1) 2-Bromo-3-hydroxypyridine (5.19 g), Benzyl bromide (5.1 g), Potassium

Dissolve carbonate (4.84 g) in DMF and stir at 80 ^° C. After extraction with dichloromethane, column chromatography was melted to obtain 2-Bromo-3- (2-Benzyloxy) pyridine as an intermediate.

( ² ) Sodium hydride (2.2 ⁴ g) was slowly added to 2-Pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 2-Bromo-3- (2-Benzyloxy) pyridine (3.72 g), which is an intermediate obtained in the above step (1), was added thereto and stirred while refluxing. After the completion of the reaction, the mixture was neutralized with an acidic aqueous solution and extracted by column chromatography to obtain a precursor ligand.

(3) After dissolving 1.43 g of the precursor ligand obtained in step (2) in dichloromethane (100 mL), triethylamine (3 mL) and Borontrifluoride diethyl etherate (4 mL) were added thereto at room temperature, followed by stirring. After completion of reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following Chemical Formula 8.

[

MR NMR (300 MHz, CDC1 ₃ ) δ 5.33 (2Η), 6.79 (1Η), 7.00 (2H), 7.40 (3H), 7.52 (2H), 7.74 (1H), 7.83 (2H), 8.20 (1H) synthesis Example 3: Synthesis of Compound Represented by Formula 9

(1) Dissolve 2-Bromo-3-hydroxypyridine (5.19 g), l-Bromoethylbenzene (5.55 g) and Potassium carbonate (4.84 g) in DMF and stir at 80 ^° C. After extraction with dichloromethane _: Column chromatography _. To obtain an intermediate.

(2) Sodium hydride (2.24 g) was slowly added to 2-Pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 3.97 g of the intermediate obtained in the step (1) was added thereto, followed by stirring while refluxing. After extraction, in the extraction process

Neutralization using an acidic aqueous solution and separation by column chromatography yielded a precursor ligand.

(3) After dissolving 1.5 g of the precursor ligand obtained in the above step (2) in dichloromethane (100 mL), triethylamine (3 mL) and Borontrifluoride diethyl etherate (4 mL) in phase silver were added thereto and stirred. After the reaction was completed, column chromatography was performed to obtain a compound represented by the following formula (9).

[

GC-MS (DI) m / z: 349.13 Synthesis Example 4 Synthesis of Compound Represented by Chemical Formula 10

(1) Dissolve 2-Bromo-3 -hydroxypyridine (5.19 g), 1 -Bromo-2-methylpropane (4.1 1 g) and Potassium carbonate (4.84 g) in DMF and stir at 80 ^° C. After extraction with dichloromethane, an intermediate was obtained by column chromatography.

(2) Sodium hydride (2.24g) was slowly added to 2-Pyridine acetonitrile (L9g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 4.2 g of the intermediate obtained in the step (1) was added thereto, followed by stirring while refluxing. After the completion of the reaction, the mixture was neutralized with an acidic aqueous solution and extracted by column chromatography to obtain a precursor ligand.

(3) After dissolving 1.58 g of the precursor ligand obtained in step (2) in dichloromethane (100 mL), triethylamine (3 mL) and Borontrifluoride diethyl etherate (4 mL) were added thereto at room temperature, followed by stirring. After completion of reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following Chemical Formula 10.

'H NMR (300 MHz, CDC1 ₃ ) δ 1.14 (6H), 2.37 (1H), 3.87 (2H), 6.87 (1H), 6.98 (2H) _: 7.73 (1H), 7.85 (2H), 8.19 (1H)

. Synthesis Example 5 Synthesis of Compound Represented by Chemical Formula 1 1

(1) Dissolve 2-Bromo-3-hydroxypyridine (5.19 g), l-Bromo-4-methylpropane (5.02 g), and Potassium carbonate (4.84 g) in DMF and stir at 80 ^° C. After extraction with dichloromethane, an intermediate was obtained by column chromatography.

(2) Sodium hydride (2.24 g) was slowly added to 2-Pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 3.92 g of the intermediate obtained in the step (1) was added thereto, followed by stirring while refluxing. After the reaction, the extraction process

(3) After dissolving 1.48 g of the precursor ligand obtained in step (2) in dichloromethane (100 mL), triethylamine (3 mL) and Borontrifluoride diethyl etherate (4 mL) were added thereto at room temperature, followed by stirring. After completion of reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by Chemical Formula 1 1 below.

11]

GC-MS (DI) m / z: 343.17 Synthesis Example 6 Synthesis of Compound Represented by Chemical Formula 13

(1) Dissolve 2-Chloro-5- (chloromethyl) pyridine (3.22g), 1,4-Dihydroxybenzene (2.20g) and Potassium carbonate (3.04g) in DMF and stir at 80 ^° C. After completion of reaction

Extract with dichloromethane to obtain intermediates. (2) Dissolve the intermediate (3.53 g), l-Bromo-2-ethylhexane (3,84 g) and Potassium carbonate (2.3 g) obtained in the above step (1) in DMF, and stir at 80 ^° C. After the reaction, the mixture is extracted with dichloromethane to obtain an intermediate.

(3) Sodium in 2-Pyridine acetonitrile (L18g) dissolved in 1,4-Dioeze (50 mL).

hydride (1.2 g) was added slowly in phase silver and stirred for 30 minutes. Thereafter, 3.48 g of the intermediate obtained in the step (2) was slowly added thereto, followed by stirring under reflux. After the reaction

In the extraction process, the mixture was neutralized with an acidic aqueous solution and separated by column chromatography to obtain a precursor ligand.

(4) After dissolving 2.15 g of the precursor ligand obtained in step (3) in dichloromethane (50 mL), it was added to triethylamine (2.5 mL) and Borontrifluodde diethyl etherate (3.5 mL) 1 at room temperature, followed by stirring. After completion of reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following Chemical Formula 13.

13]

GC-MS (DI) m / z: 477.23 Synthesis Example 7 Synthesis of Compound Represented by Chemical Formula 14

(1) Dissolve 2-Chloro-5- (chloromethyl) pyridine (3.22g), Di (2-ethylhexyl) amine (4.90g) and Potassium carbonate (3.04g) in DMF and stir at 80 ^° C. After the reaction

Extract with dichloromethane to obtain intermediates.

(2) Sodium hydride (1.2 g) was slowly added to 2-Pyridine acetonitrile (18 g) dissolved in l, 4-Dioxane (100 mL) at room temperature and stirred for 30 minutes. Thereafter, 3.33 g of the intermediate obtained in the step (1) was slowly added thereto, followed by stirring under reflux. After the completion of the reaction, the mixture was neutralized with an acidic aqueous solution and separated by ¾ column chromatography to obtain a precursor ligand.

(3) 2.24 g of the precursor ligand obtained in step (2) was added to dichloromethane (50 mL). After dissolving, triethylamine (2.5mL) and Borontrifluoride diethyl etherate (3.5mL) were added thereto in phase silver and stirred. After completion of reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following Chemical Formula 14.

[14]

'H NMR (300 MHz, CDC1 ₃ ) δ 0.86 (12Η), 1.25 (16H), 1.43 (2Η), 2.16 (4Η), 3.40 (2Η), 6.89 (1Η), 7.54 (2Η), 7.68 (1Η) , 7.75 (1Η), 8.06 (1Η), 8.15 (1Η) Synthesis Example 8: Synthesis of Compound Represented by Chemistry 16.

(l) Sodium hydride (2.24 g) was slowly added to 2-Pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 2-Bromopyridine (2.55 g) was added thereto and stirred while refluxing. After completion of the reaction, the mixture was neutralized with an acidic aqueous solution and separated by column chromatography to obtain a precursor ligand (bis (2-pyridyl) acetonitrile).

(2) Dissolve 0.98 g of the precursor ligand (bis (2-pyridyl) acetonitrile) obtained in the above step (1) in dichloromethane (100 mL), and then add triethylamine (3 mL) and Borontrifluoride diethyl etherate (4 mL) at room temperature in order-stirring It was. After completion of the reaction, the residue was separated by column chromatography to obtain a dipyridomethane-based boron difluoride compound as a precursor.

(3) Dissolve the dipyridomethane-based boron compound (1.22 g), the precursor obtained in the above step (2), in 50 mL of dichloromethane, add solid aluminum chloride (1.7 g), and stir for about 5 minutes. Add melted Catechol (l.lg) and stir at room temperature. After completion of reaction, separation was performed by column chromatography to obtain a compound represented by the following formula (16). ᅳ

H NMR (300 MHz, CDC1 ₃ ) δ 6.85 (6H), 7.59 (2H), 7.69 (2H), 7.87 (2H) Synthesis Example 9: Synthesis of Compound Represented by Formula 17

The boron compound (1.22 g) obtained in Synthesis Process (2) of Synthesis Example 8 was dissolved in 50 mL of dichloromethane, and solid aluminum chloride (1.7 g) was added thereto, followed by stirring for about 5 minutes. After this, 4-tert-Butylpyrocatechol (1.67 g) dissolved in Acetonitrile was added and stirred at room temperature.

After completion of the reaction, the resultant was separated by column chromatography to obtain a compound represented by the following formula (17).

GC-MS (DI) m / z: 369.16 Synthesis Example 10 Synthesis of Compound Represented by Chemical Formula 18

The boron compound (1.22 g) obtained in Synthesis Process (3) of Synthesis Example 4 was dissolved in 50 mL of dichloromethane, and solid aluminum chloride (1.7 g) was added thereto, followed by stirring for about 5 minutes. After this, 4-tert-Butylpyrocatechol (1.67 g) dissolved in Acetonitrile was added and stirred at room temperature. After completion of reaction, separation was performed by column chromatography to obtain a compound represented by the following formula (18). [

H NMR (300 MHz, CDC1 ₃ ) δ 1.15 (6H), 2.38 (1H), 3.87 (1H), 6.76 (1H), 6.85 (5H), 6.99 (1H), 7.57 (1H), 7.70 (1H), 7.85 (1H), 7.93 (1H) Synthesis Example 1 1 Synthesis of Compound Represented by Chemical Formula 19

The boron compound (1.22 g) obtained in Synthesis Process (2) of Synthesis Example 1 was dissolved in 50 mL of dichloromethane, and aluminum chloride (1.7 g) was added to the solid and stirred for about 5 minutes. After this, 4-tert-Butylpyrocatechol (1.67 g) dissolved in Acetonitrile was added and stirred at room temperature. After completion of the reaction, the resultant was separated by column chromatography to obtain a compound represented by the following formula (19).

[

GC-MS (DI) m / z: 441.34 Synthesis Example 12 Synthesis of Compound Represented by Chemical Formula 15 ^''

(1) Sodium in 2-Pyridine acetonitrile (1.9 g) dissolved in l, ^4- Dioxane (100 mL)

hydride (2.24 g) was added slowly at room temperature and stirred for 1 hour. After this, 2-Chloro-5- (chloromethyl) pyridine (l.OOg) was added thereto and stirred while refluxing. After the reaction

(2) 1.63 g of the precursor ligand obtained in step (1) was added to dichloromethane (lOOmL). After dissolving, triethylamine (3mL) and Borontrifluoride diethyl etherate (4mL) were added and stirred in silver. After completion of the reaction was separated by column chromatography to a precursor

A dipyridomethane-based boron difluoride compound was obtained.

[15]

NMR (300 MHz, CDC1 ₃ ) δ 3.36 (2Η), 4.26 (1Η), 6.93 (1H), 7.33 (2H), 7.51 (3H), 7.72 (2H), 7.85 (1H), 8.14 (1H), 8.66 (1H) Comparative Synthesis Example

10 £ polymerization reactor with reflux condenser and stirrer

After heating cyclonuxanone (Shiny) 100 g to 80 ^° C, 300 g of compound (12) prepared above, 300 g of benzyl methacrylate (Hitach), 106 g of methacrylic acid (gold) '-A solution of 92 g of azobisisobutyronitrile (wako) dissolved in 5000 g of cyclonucleanone (Shiny) was slowly added to a heated polymerization reactor for 3 hours. After completion

After stirring for 14 hours, a polymer including a repeating unit represented by the following Formula 20 was obtained. The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters was 9,800 g / mol.

(In Formula 20, a = 2, b = 2 and c = l.)

(Synthesis of Photosensitive Resin Composition)

Example 1

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

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 (a compound represented by Chemical Formula 3-1) and a pigment (in the form of a pigment dispersion) prepared in Synthesis Example 1 were added as a colorant to the obtained semi-flour and stirred at room temperature for 1 hour. The product was then filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

Table 1

(Unit: weight%)

Blending material loading colorant ᄋ 3 Ξ

Z Compound 5.0 of Synthesis Example 1

Pigment Y138 Pigment Dispersion 10.0 Pigment G58 Pigment Dispersion 15.0

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

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

Alkali Soluble Resin 3.0

(A): methacrylic acid

(B): benzyl methacrylate

Defend the defensive tree

Photopolymerizable Compound 7.0 acrylate (DPHA)

Photoinitiator 1,2-octanedione 1.0

Propylene Glycol

Solvent 59.0

Monomethyl Ether 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 2 (compound represented by Formula 8) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 3 (compound represented by Formula 9) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 4 (compound represented by Formula 10) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12).

Example 5

The photosensitive resin composition was produced like Example 1 except having used the compound of Synthesis Example 5 (compound represented by Formula U) instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 6

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 6 (compound represented by Formula 13) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 7

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 7 (compound represented by Formula 14) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 8

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 16) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 9

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 17) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 10

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 18) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 1 1

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 19) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Example 12

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 15) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). 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 20) was used instead of the compound of Synthesis Example 1 (compound represented by Formula 12). Evaluation: color coordinates, luminance and contrast ratio measurements

The photosensitive resin composition prepared in Examples 1 to 12 and Comparative Example 1 was applied on a glass substrate having a thickness of 1 _mm and degreased, and dried on a hot plate at 90 ^° C. for 2 minutes. To obtain a coating film. Subsequently, the coating film was exposed by using a high pressure mercury lamp having a dominant wavelength of 365 nm. Obtained by drying in a hot air circulation drying furnace of 200 ^° C for 5 minutes. Pixel layer

Color coordinates (x, y), luminance (Y) and contrast ratio were measured using a spectrophotometer (MCPE> ³ 000, Otsuka electronic Co., Ltd.), and are shown in Table 2 below.

[Table 2]

Color coordinates (x, y) Luminance (Y) Contrast ratio Example 1 (0.276, 0.560) 61.9 14,950 Example 2 (0.272, 0.560) 62.0 14,980 Example 3 (0.269, 0.560) 62.5 15, 120 Example 4 (0.279, 0.560 62.4 15,020 Example 5 (0.278, 0.560) 62.3 14,970 Example 6 (0.274, 0.560) 62.3 15,030 Example 7 (0.272, 0.560) 62.2 15,200 Example 8 (0.268, 0.560) 62.3 14,990 Example 9 (0.279, 0.560) 62.2 15,040 Example 10 (0.276, 0.560) 62.1 14,960 Example 1 1 (0.275, 0.560) 62.1 15,060 Example 12 (0.272, 0.560) 62.2 14,990 Comparative Example 1 (0.279, 0.565) 60.2 13,900 From Table 2, it was confirmed that the photosensitive resin composition of Examples 1 to 12 containing the compound according to one embodiment as a dye exhibits superior color characteristics than the photosensitive resin composition of Comparative Example 1 not containing the compound Can be. As mentioned above, although preferred embodiment of this invention was described, this invention is not limited to this, It is possible to variously deform and implement within the range of a claim, a detailed description of an invention, and an accompanying drawing. Naturally, it belongs to the scope of the invention. ^'

Claims

[Range of request]

[Claim 11

Compound represented by the following formula (1):

One]

In Chemical Formula 1,

R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 heteroaryl group,

M is represented by the following formula (2) or (3),

[Formula 2]

In Chemical Formula 3,

A is a substituted or unsubstituted C6 to C20 aryl group.

[Claim 2]

The method of claim 1,

R ¹ to R ⁴ are all hydrogen atoms,

R ⁵ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group

[Claim 3]

The method of claim 1, R ¹ to R ⁴ are all hydrogen atoms,

R ⁶ is a hydrogen atom or a substituted or unsubstituted substituted C1 to C20 alkyl group,

R ⁸ is a hydrogen atom or a substituted or unsubstituted C 1 to C 20 alkoxy group. .

[Wind port 4]

The method of claim 1,

Formula 1 is a compound represented by any one of the following Formula 4 to Formula 7:

[Formula 4]

[Formula 7]

In Chemical Formulas 4 to 7,

X ¹ is N, P or B,

X ² and X ³ are each independently, o, S, S (= 0) or S (= 0) ₂ ,

L ¹ is a substituted or unsubstituted C1 to C20 alkylene group,

R ⁹ and R ′ ² are each independently a substituted or unsubstituted C 1 to C20 alkyl group, a substituted or unsubstituted C 2 to C 20 heteroaryl group, or a cyano group,

M is represented by the following formula (2) or (3),

3]

In Chemical Formula 3,

A is a substituted or unsubstituted C6 to C20 aryl group.

[Claim 5]

According to claim 11,

Formula 1 is a compound represented by any one selected from the group consisting of Formula 8 to Formula 15.

[Formula 8]

[Formula 9]

[

Formula

[Formula 12]

[

[Formula 14]

[Formula 15]

[Claim 6]

Formula 1 is a compound represented by one selected from the group consisting of Formula 16 to Formula 19.

16]

[Formula 17]

[

[Claim 7]

The method of claim 1,

The compound is a yellow dye.

[Claim 8]

The method of claim 17,

The yellow dye has a maximum absorption region in the wavelength range of 400nm to 550nm.

[Claim 9]

The photosensitive resin composition containing the compound of any one of Claims 1-8. [Claim 10]

The method of claim 9,

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

[Claim 111]

The color filter manufactured using the photosensitive resin composition of Claim 9.