KR20130135083A - Photoactive compound comprising phosphonate group and photosensitive resin composition comprising the same - Google Patents

Abstract

The present invention relates to a photoactive compound containing an oxime ester group and a phosphonate group at the same time, and a photosensitive resin composition containing the same. The photoactive compound is a new photoactive compound which can offer excellent developing properties and development residue properties without decreasing sensitivity and chemical resistance.

Description

Photoactive compound and the photosensitive resin composition containing the same {PHOTOACTIVE COMPOUND COMPRISING PHOSPHONATE GROUP AND PHOTOSENSITIVE RESIN COMPOSITION COMPRISING THE SAME}

The present application relates to a photoactive compound comprising an oxime ester group and a phosphonate group and a photosensitive resin composition comprising the same.

The present application relates to a photoactive compound comprising an oxime ester group and a phosphonate group and a photosensitive resin composition comprising the same.

The photosensitive resin composition may be applied to a substrate to form a coating film, and a specific portion of the coating film may be exposed by light irradiation using a photomask or the like, and then used to form a pattern by developing and removing the non-exposed portion. . Since such a photosensitive resin composition can be cured by irradiation with light, it is used for photocurable ink, photosensitive printing plate, various photoresist, color filter photoresist for LCD, photoresist for resin black matrix, or transparent photoresist.

Among them, the transparent photosensitive resin composition is used for column spacers, overcoats, and passivation membranes, and it is generally possible to use an alkali-soluble resin, a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and a solvent without using a colorant such as a pigment. Include.

Among them, the colored photosensitive resin composition is used for a color filter photoresist and a photoresist for a resin black matrix, and is usually a colorant of red, green, blue, and black, an alkali-soluble resin, a polymerizable compound having an ethylenically unsaturated bond, and photopolymerization. Initiator and solvent.

The photosensitive resin composition has been manufactured for the purpose of constituting liquid crystal display devices such as TVs and monitors in addition to the conventional notebooks and mobiles as the use of LCDs has been advanced and diversified. In addition, the demand for mechanically excellent physical properties is increasing. In the case of forming a pattern by a photo-lithography method or forming an insulating protective film through full exposure, a property that reacts quickly to light, that is, light sensitivity becomes a very important factor. In addition, the overcoat and the passivation film, which serve as a column spacer or a protective film serving as a support, should have excellent mechanical properties so that the liquid crystal display element is not damaged by external impact and exhibits original performance.

Therefore, the use of a photopolymerization initiator with excellent photosensitivity can solve these problems. When using a photoinitiator with excellent photosensitivity, sufficient sensitivity can be realized even with a small amount of photopolymerization initiator, thereby reducing the contamination of liquid crystals, increasing the residual film ratio of the pattern, and increasing the usable width of other raw materials when preparing the composition. It has the advantage of being.

Therefore, development of a photoinitiator which can absorb a UV light source efficiently even with a small amount of use, and is excellent in a sensitivity and a high temperature process characteristic is calculated | required.

Japanese Patent Laid-Open No. 61-118423

The problem to be solved by the present application is to overcome all the disadvantages of the conventional photopolymerization initiator, a novel photoactive compound that can exhibit the effect of excellent developability and development residue characteristics without degrading sensitivity and chemical resistance and comprising the same It is providing a photosensitive resin composition.

One embodiment of the present application provides a photoactive compound represented by the following Chemical Formula 1.

[Formula 1]

In Formula 1,

이고 나머지는 수소; 할로겐기; CN; OR; SR; COR; OCOR; NRR′; CONRR′; R, OR, SR, COR 및 OCOR로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 C₁~C₁₀의 알킬기; 및 C₁~C₁₀의 할로알킬기로 이루어진 군으로부터 선택되고,At least one of X ₁ and X ₂ is

And the other is hydrogen; A halogen group; CN; OR; SR; COR; OCOR; NRR '; CONRR '; R, OR, SR, COR, and substituted or unsubstituted by one or more substituents selected from the group consisting of unsubstituted C OCOR group of ₁ ~ C _10; And a C ₁ to C ₁₀ haloalkyl group,

Y is a direct link; Or a C ₁ to C ₁₅ alkylene group which is substituted or unsubstituted with at least one substituent selected from the group consisting of R, OR, SR, COR and OCOR,

M ₁ is an alkyl group of C ₁ ~ C ₈ ; Or an aryl group of C ₆ ~ C ₁₂ ,

R ₁ is a C ₁ ~ C ₈ alkyl group; Or an aryl group of C ₆ ~ C ₁₂ ,

A is a C ₆ to C ₂₀ aryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a halogen group, CN, R, OR, SR, COR, OCOR, NRR 'and CONRR',

R ₂ and R ₃ are each independently selected from the group halogen, CN, alkoxy group and C ₁ ~ C ₆ alkylthio group consisting of C ₁ ~ C ₆ alkyl group, C ₁ ~ C _6, the

m and n are each independently an integer of 0 to 3,

R and R 'are each independently selected from the group consisting of hydrogen, a C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ haloalkyl group and C ₇ ~ C ₁₃ arylalkyl group, wherein R and R' together ring Can be formed.

One embodiment of the present application is a photoactive compound represented by Formula 1; Alkali-soluble binder resins; Polymerizable compounds comprising ethylenically unsaturated bonds; And it provides a photosensitive resin composition comprising a solvent.

One embodiment of the present application provides a photosensitive material prepared using the photosensitive resin composition.

One embodiment of the present application provides an electronic device manufactured using the photosensitive resin composition.

The compound provided through the present application is excellent in the efficiency of generating radicals by efficiently absorbing ultraviolet rays, particularly ultraviolet rays of i-line (365 nm), and acting as an effective initiator for photopolymerization of various unsaturated groups, especially acrylic compounds, It has excellent film rate, mechanical strength, heat resistance, chemical resistance and developability.

Therefore, the photosensitive resin composition according to the present application is advantageous not only in the curing of the column spacer, the overcoat and the passivation material of the liquid crystal display element but also the high temperature process characteristic.

Advantages and features of the present application, and methods of achieving them will be apparent with reference to the embodiments described below in detail. However, the present application is not limited to the embodiments disclosed below, but will be implemented in various different forms, only the embodiments make the disclosure of the present application complete, and those skilled in the art to which the present application belongs. It is provided to fully inform the person having the scope of the invention, this application is defined only by the scope of the claims.

Unless defined otherwise, all terms (including technical and scientific terms) used herein may be used in a sense commonly understood by one of ordinary skill in the art to which this application belongs. In addition, terms that are defined in a commonly used dictionary are not ideally or excessively interpreted unless they are specifically defined clearly.

Hereinafter, the present application will be described in detail.

The inventors of the present application synthesized a compound having a structure containing both an oxime ester group and a phosphonate group in one molecule, and confirmed that the compound absorbs ultraviolet rays more efficiently than other photoinitiators and has excellent sensitivity and high temperature processing characteristics. .

Conventional photoactive compounds containing oxime ester groups have the following problems

As photoinitiators of the oxime ester structure, α-oxo oxime derivatives (JP-A-61-118423), photoinitiators using β-amino oximes (US Pat. No. 5,776,996) and the like have been developed.

However, among the oxime derivative compounds used as described above, the compounds initially developed have low photoinitiation efficiency and are not effective in absorbing UV light sources when the color characteristics are good. Compounds published after the late 1990s have significantly improved photoinitiation efficiency but do not fully satisfy the recently enhanced process time reductions. In particular, since the concentration of the pigment is high or the thickness of the coating film is not less than 2.5 占 퐉, the degree of curing of the thick film is not sufficiently satisfied. Therefore, there is a difficulty in forming a fine pattern and the formed pattern has critical dimension (CD) I can not satisfy you.

Conventionally known oxime derivative compounds have a disadvantage of low photoinitiation efficiency, poor processing time, weak mechanical strength, and poor storage stability.

The recently commercialized oxime ester photopolymerization initiators Irgacure OXE 01 and Irgacure OXE 02 from BASF Co., Ltd. have been significantly improved in sensitivity, and are being spotlighted for use in photosensitive resin compositions. However, these photopolymerization initiators are considerably expensive and cannot be used to give sufficient sensitivity in terms of economics, and the photopolymerization initiator itself has a disadvantage in poor storage stability.

The photoactive compound according to the embodiment of the present application has superior photoinitiation efficiency, shorter processing time, superior mechanical strength, superior economical advantages, and improved storage stability compared to the conventional oxime ester photopolymerization initiator. And, there is an advantage in developing. Moreover, it has the advantage of being excellent in sensitivity, having sufficient solubility with respect to the polymeric compound which has an ethylenically unsaturated bond, and being stable also over time. In addition, the efficiency of generating radicals by efficiently absorbing the ultraviolet rays of the i-line (365 nm), and excellent compatibility with the binder, has the advantage of excellent high temperature process characteristics.

One embodiment of the present application provides a photoactive compound represented by the following Chemical Formula 1.

[Formula 1]

일 수 있다. X₁ 이

일 수도 있고, X₂ 가

일 수도 있으며, X₁ 및 X₂ 모두

일 수도 있다. 상기

는 연결 부위를 의미한다.In the compound according to one embodiment of the present application, at least one of X < _{1 >} and X < ₂ &

Lt; / RTI > X ₁ is

Or X < ₂ >

, And both X ₁ and X ₂

Lt; / RTI > remind

Means a connection site.

인 경우,

를 제외한 나머지는 수소; 할로겐기; CN; OR; SR; COR; OCOR; NRR′; CONRR′; R, OR, SR, COR 및 OCOR로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 C₁~C₁₀의 알킬기; 및 C₁~C₁₀의 할로알킬기로 이루어진 군으로부터 선택되는 것일 수 있고, 바람직하게는 C₁~C₁₀의 알킬기일 수 있고, 더욱 바람직하게는 메틸기 또는 에틸기일 수 있다. Only one of X ₁ and X ₂

Quot;

Are hydrogen; A halogen group; CN; OR; SR; COR; OCOR; NRR '; CONRR '; R, OR, SR, COR, and substituted or unsubstituted by one or more substituents selected from the group consisting of unsubstituted C OCOR group of ₁ ~ C _10; And a C ₁ to C ₁₀ haloalkyl group, preferably a C ₁ to C ₁₀ alkyl group, more preferably a methyl group or an ethyl group.

In this case, the formula (1) may be one of the formulas (2) to (4).

 (2)

(3)

[Chemical Formula 4]

In the compound according to the embodiment of the present application, the substituents of Chemical Formulas 1 to 4 will be described in more detail as follows.

Y is a direct link; A C ₁ to C ₁₅ alkylene group; Or a C ₁ to C ₁₅ alkylene group substituted with one or more substituents selected from the group consisting of R, OR, SR, COR and OCOR, preferably an alkylene group of C ₂ to C ₆ , ethylene Group or propylene group is more preferable in view of solubility and compatibility.

M ₁ is an alkyl group of C ₁ ~ C ₈ ; Or a C ₆ -C ₁₂ aryl group, preferably a methyl group or an ethyl group.

R ₁ is a C ₁ ~ C ₈ alkyl group; Or a C ₆ -C ₁₂ aryl group, preferably a methyl group or a phenyl group. R ₁ is a part which is decomposed into radicals which are active species at the time of exposure, and is not particularly limited in structure, but the simpler the structure, the better the movement and the photoinitiation efficiency is improved.

The R ₂ and R ₃ may be each independently selected from the group consisting of a halogen group, CN, C ₁ ~ C ₆ alkyl group, C ₁ ~ C ₆ alkoxy group and C ₁ ~ C ₆ alkylthio group, Preferably it may be a C ₁ ~ C ₁₀ alkyl group, more preferably may be a methyl group or an ethyl group.

M and n may be each independently an integer of 0 to 3.

또는

일 수 있다.A may be a C ₆ ~ C ₂₀ aryl group unsubstituted or substituted with one or more groups selected from the group consisting of a halogen group, CN, R, OR, SR, COR, OCOR, NRR 'and CONRR', preferably May be a phenyl group unsubstituted or substituted with the substituent or a naphthyl group unsubstituted or substituted with the substituent. More specifically

or

Lt; / RTI >

R ₄ and R ₅ may be each independently selected from the group consisting of a halogen group, CN, C ₁ ~ C ₆ alkyl group, C ₁ ~ C ₆ alkoxy group and C ₁ ~ C ₆ alkylthio group, Preferably it may be an alkyl group of C ₁ ~ C ₆ , more preferably may be a methyl group or an ethyl group.

P may be an integer of 0 to 5, and q may be an integer of 0 to 7.

R and R 'may each be selected from the group consisting of hydrogen, C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ haloalkyl group and C ₇ ~ C ₁₃ arylalkyl group, or R and R' together May form a ring. When R and R 'together form a ring, it may form a 5-membered, 6-membered or 7-membered ring, may be monocyclic or polycyclic, and may be aromatic, aliphatic ring, heteroaromatic or heteroaliphatic ring. have.

The halogen group may be fluorine, chlorine, bromine or iodine.

The aryl group may be a monocyclic aryl group or a polycyclic aryl group.

Specifically, when the aryl group is a monocyclic aryl group, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, and the like, but is not limited thereto.

In the case of the polycyclic aryl group, the aryl group may be, for example, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perrylenyl group, chrysenyl group, or fluorenyl group, but is not limited thereto.

The alkyl group may be straight, branched or cyclic. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, iso-pentyl group, neo-pentyl group, n-hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. may be, but is not limited thereto.

 The alkoxy group may be linear, branched or cyclic, and may be substituted or unsubstituted. Examples of the alkoxy group may be methoxy group, ethoxy group, n-propyloxy group, iso-propyloxy group, n-butyloxy group, cyclopentyloxy group and the like, but is not limited thereto.

The alkylene group may be linear or branched, and may be substituted or unsubstituted. Specific examples of the alkylene group include methylene, ethylene, propylene, isopropylene, butylene, t-butylene, but are not limited thereto.

The above "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents.

In the general formulas (1) to (4), the substituent is not particularly defined, or the substituent-free moiety may be hydrogen.

The photoactive compound of the present application represented by Chemical Formulas 1 to 4 includes an oxime ester group and a phenyl group or a naphthyl group in its structure, and includes a phosphonate group (-Y-PO (OM ₁ ) ₂ ). There is a characteristic.

The substituted or unsubstituted phenyl group or naphthyl group shifts the maximum UV absorption wavelength of the compound represented by Formulas 1 to 4 to about 340 nm, which is a long wavelength, i-line (λ = 365 nm), which is the maximum emission wavelength of a general mercury light source exposure machine. It acts to increase the sensitivity by absorbing light more efficiently.

In addition, the phosphonate group increases the solubility of the compound represented by the formula (1) to formula (4), and the solubility of the photosensitive resin composition in a high compatibility with the binder resin by forming a hydrogen bond with the alkali-soluble binder resin in the photosensitive resin composition. Improves volatility and lowers volatility. Due to such a structural feature, the photoactive compound according to the present application has higher sensitivity than the photoactive compound including the oxime ester disclosed in the prior art, has excellent solubility and has characteristics such as low volatility, and is added to the photosensitive resin composition as a photopolymerization initiator It is possible to improve sensitivity, chemical resistance, resistance to developing, hardenability and high-temperature process characteristics.

In the compounds according to one embodiment of the present application, specific examples of the compounds represented by Chemical Formulas 1 to 4 are shown below, but the present invention is not limited thereto.

[Chemical Formula 5]

 [Chemical Formula 6]

One embodiment of the present application is a photoactive compound represented by Formula 1; Alkali-soluble binder resins; Polymerizable compounds comprising ethylenically unsaturated bonds; And it provides a photosensitive resin composition comprising a solvent.

In one embodiment of the present application, the compound of Formula 1 may be a compound of Formula 2 to Formula 4. In addition, in one embodiment of the present application, the compound of Formula 1 to Formula 4 may be a compound of Formula 5 or Formula 6.

The photosensitive resin composition according to the exemplary embodiment of the present application has an effect of adjusting the viscosity by including a binder resin, and has an effect of enabling patterning using an alkaline developer. As the binder, those generally used in the art such as an alkali-soluble polymer resin may be used. Specifically, the alkali-soluble resin binder is a copolymer of a monomer containing an acid functional group and a monomer giving a film strength copolymerizable with the monomer, or a polymer reaction with an ethylenically unsaturated compound containing an epoxy group. It may be a compound prepared through.

The alkali-soluble resin binder used in the present application has an acid value of about 30 to 300 KOH mg / g, and when the acid value is less than 30 KOH mg / g, the phenomenon does not develop well and a clear pattern can not be obtained. , The washing property is excessively improved and the pattern can be detached, which is not preferable.

The weight average molecular weight of the alkali-soluble resin binder is preferably in the range of 1,000 to 200,000, more preferably may be in the range of 5,000 to 100,000. If the weight average molecular weight of the alkali-soluble binder resin is less than 1,000, the heat resistance and chemical resistance deteriorate. If the weight-average molecular weight of the alkali-soluble binder resin is more than 200,000, the solubility in the developing solution is lowered, so that development is not possible. Can not do it.

Non-limiting examples of the monomer containing an acid group include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, isoprene sulfonic acid, styrene sulfonic acid, 5-norbornene-2-carboxylic acid, mono 2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate, or mixtures thereof have.

Non-limiting examples of monomers copolymerizable with the monomer containing the acid group include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) ) Acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (Meth) acrylate, tetrahydroperpryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate , 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (Meth) acrylate Methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol ( Meta) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3, 3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydride Hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate, butyl α-hydroxymethyl acrylate, dicyclopentanyl (meth) acrylate, disc Pentenyl (meth) acrylate, dicyclopentanyl oxyethyl (meth) acrylate, dicyclopentenyl oxyethyl (meth) unsaturated carboxylic acid esters such as acrylate; Aromatic vinyls such as styrene, α-methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, (o, m, p) -chloro styrene; Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl glycidyl ether; N-vinyl tertiary amines, such as N-vinyl pyrrolidone, N-vinyl carbazole, and N-vinyl morpholine; Unsaturated imides such as N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide; Maleic anhydrides such as maleic anhydride and methyl maleic anhydride; Unsaturated glycidyl compounds such as allyl glycidyl ether, glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, or mixtures thereof.

As an ethylenically unsaturated compound containing the said epoxy group, allyl glycidyl ether, glycidyl (meth) acrylate, 3, 4- epoxycyclohexylmethyl (meth) acrylate, glycidyl 5-norbornene-2 One or more selected from the group consisting of -methyl-2-carboxylate (endo, exo mixture), 1,2-epoxy-5-hexene, and 1,2-epoxy-9-decene.

In the photosensitive resin composition according to the embodiment of the present application, the content of the binder resin may be 1 to 30% by weight based on the total weight of the photosensitive resin composition, but is not limited thereto. When the content of the binder resin is 1% by weight or more, the effect of patterning using an alkali aqueous solution is well effected, and the problem of difficulty in forming a pattern due to the lack of solubility in a developer is prevented. There is an effect that can prevent the loss of, and the viscosity of the entire solution is too high to prevent problems that may be difficult to coat.

The photosensitive resin composition according to the exemplary embodiment of the present application may include a crosslinkable compound, and specifically, a polymerizable compound including an ethylenically unsaturated bond may be used. More specifically, a crosslinkable compound including two or more unsaturated acrylic groups and a crosslinkable compound including three or more unsaturated acrylic groups may be used. As a specific example, ethylene glycol di (meth) acrylate, an ethylene group having 2 to 14 polyethylene glycol di (meth) acrylate, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, Pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 2-trisacryloyloxymethylethylphthalic acid, propylene glycol di (meth) acrylate with 2 to 14 propylene groups, dipentaerythritol penta A mixture of an acidic modification of (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate (trade name TO- 2348, TO-2349) compound obtained by esterifying polyhydric alcohols, such as (alpha), (beta)-unsaturated carboxylic acid; Compounds obtained by adding (meth) acrylic acid to a compound containing glycidyl groups such as trimethylolpropane triglycidyl ether acrylic acid adduct and bisphenol A diglycidyl ether acrylic acid adduct; ester compounds of a compound having a hydroxyl group or an ethylenic unsaturated bond such as a phthalic acid diester of? -hydroxyethyl (meth) acrylate and a toluene diisocyanate adduct of? -hydroxyethyl (meth) acrylate with a polyvalent carboxylic acid , Or adducts with polyisocyanates; (Meth) acrylic-acid alkylesters, such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate; And 9,9'-bis [4- (2-acryloyloxyethoxy) phenyl] fluorene, and may include one or more selected from the group consisting of, but are not limited to, those known in the art. Compounds can be used. In some cases, silica dispersions may be used for these compounds, for example, Nanocryl XP series (0596, 1045, 21/1364) and Nanopox XP series (0516, 0525) manufactured by Hanse Chemie.

In the photosensitive resin composition according to the embodiment of the present application, the content of the crosslinkable compound, specifically, the polymerizable compound including an ethylenically unsaturated bond may be 0.5 to 30% by weight based on the total weight of the photosensitive resin composition. However, the present invention is not limited thereto.

In the photosensitive resin composition according to the embodiment of the present application, non-limiting examples of the solvent include methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 2-ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclo Pentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, and dipropylene glycol monomethyl May contain one or more selected from the group consisting of ethers .

In the photosensitive resin composition according to the embodiment of the present application, the content of the solvent may be 40 to 95 wt% based on the total weight of the photosensitive resin composition, but is not limited thereto.

Photosensitive resin composition according to an embodiment of the present application is a transparent photosensitive resin composition, 0.1 to 5% by weight of the photoactive compound represented by the formula (1), 0.5 to 30% by weight of a polymerizable compound containing an ethylenically unsaturated bond, alkali soluble It may include 1 to 30% by weight of the binder resin and 40 to 95% by weight of the solvent.

The photosensitive resin composition according to the embodiment of the present application may further include a colorant.

In the photosensitive resin composition according to the embodiment of the present application, the coloring agent may be used one or more pigments, dyes or mixtures thereof. Specifically, as the black pigment, a metal oxide such as carbon black, graphite, titanium black, or the like may be used. Examples of carbon black include cysto 5HIISAF-HS, cysto KH, cysto 3HHAF-HS, cysto NH, cysto 3M, cysto 300HAF-LS, cysto 116HMMAF-HS, cysto 116MAF, cysto FMFEF-HS , Sisto SOFEF, Sisto VGPF, Sisto SVHSRF-HS and Sisto SSRF (Donghae Carbon Co., Ltd.); Diagram Black II, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Diagram LR, # 2700, # 2600, # 2400, # 2350, # 2300, # 2200, # 1000, # 980, # 900, MCF88, # 52, # 50, # 47, # 45, # 45L, # 25, # CF9, # 95, # 3030, # 3050, MA7, MA77, MA8, MA11, MA100, MA40, OIL7B, OIL9B, OIL11B, OIL30B and OIL31B (Mitsubishi Chemical Corporation); PRINTEX-25, PRINTEX-25, PRINTEX-55, PRINTEX-55, PRINTEX-45, PRINTEX-35, PRINTEX- 200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100 and LAMP BLACK-101 (Daegu; 890, RAVEN-880ULTRA, RAVEN-880ULTRA, RAVEN-850R, RAVEN-1080ULTRA, RAVEN-1080ULTRA, RAVEN-1080ULTRA, RAVEN-1080ULTRA, RAVEN-1040ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN- 820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN- RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, RAVEN-1170 (Colombia Carbon) or mixtures thereof. Examples of coloring agents that can be colored include carmine 6B (CI12490), phthalocyanine green (CI 74260), phthalocyanine blue (CI 74160), perylene black (BASF K0084. K0086), cyanine black, lino yellow (CI 21090) Linol Yellow GRO (CI 21090), Benzidine Yellow 4T-564D, Victoria Pure Blue (CI42595), CI PIGMENT RED 3, 23, 97, 108, 122, 139, 140, 141, 142, 143, 144, 149, 166, 168, 175, 177, 180, 185, 189, 190, 192, 220, 221, 224, 230, 235, 242, 254, 255, 260, 262, 264, 272; C.I. PIGMENT GREEN 7, 36, 58; C.I. PIGMENT blue 15: 1, 15: 3, 15: 4, 15: 6, 16, 22, 28, 36, 60, 64; C.I. PIGMENT yellow 13, 14, 35, 53, 83, 93, 95, 110, 120, 138, 139, 150, 151, 154, 175, 180, 181, 185, 194, 213; C.I. PIGMENT VIOLET 15, 19, 23, 29, 32, 37, etc. In addition, white pigments and fluorescent pigments can be used. As the phthalocyanine-based complex compound used as the pigment, a material having zinc as a central metal in addition to copper may be used.

In the photosensitive resin composition according to the embodiment of the present application, the content of the colorant may be 1 to 20% by weight based on the total weight of the photosensitive resin composition, but is not limited thereto.

The photosensitive resin composition according to one embodiment of the present application is a colored photosensitive resin composition, which comprises 0.1 to 5% by weight of a photoactive compound represented by the formula (1), 0.5 to 30% by weight of a polymerizable compound containing an ethylenically unsaturated bond, 1 to 30% by weight of a binder resin, 1 to 20% by weight of a colorant and 40 to 95% by weight of a solvent.

The photosensitive resin composition according to the exemplary embodiment of the present application may include, as necessary, a second photoactive compound, a curing accelerator, a thermal polymerization inhibitor, a dispersant, an antioxidant, a UV absorber, a plasticizer, an adhesion promoter, a filler, a surfactant, and the like, as necessary. It may further comprise one or two or more additives of.

When the additive is added, the amount of the second photoactive compound is preferably 0.1 to 5% by weight, and the amount of the other additive is 0.01 to 5% by weight.

Specifically, the second photoactive compound may be a triazine-based compound, a nonimidazole-based compound, an acetophenone-based compound, an O-acyloxime compound, a benzophenone compound, a thioxanthone compound, a phosphine oxide compound, ≪ / RTI > The second photoactive compound is more specifically 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine, 2,4-trichloromethyl- (4'-methoxystyryl) -6 -Triazine, 2,4-trichloromethyl- (piflonil) -6-triazine, 2,4-trichloromethyl- (3 ', 4'-dimethoxyphenyl) -6-triazine, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propanoic acid, 2,4-trichloromethyl- (4'-ethylbiphenyl) -6-tri Triazine compounds such as azine and 2,4-trichloromethyl- (4'-methylbiphenyl) -6-triazine;

Bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- , 5'-tetraphenylbiimidazole;

2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxy Methoxy) -phenyl (2-hydroxy) propyl ketone, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenyl acetophenone, 2-methyl- (4-methylthiophenyl) -2-mol Acetope such as polyno-1-propane-1-one (Irgacure-907) and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (Irgacure-369) Non-based compounds;

O-acyloxime compounds such as Irgacure OXE 01 and Irgacure OXE 02 from BASF;

Benzophenone compounds such as 4,4'-bis (dimethylamino) benzophenone and 4,4'-bis (diethylamino) benzophenone; Thioxanthone compounds such as 2,4-diethylthioxanthone, 2-chlorothioxanthone, isopropylthioxanthone and diisopropylthioxanthone;

2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis (2,6-dichlorobenzoyl) propylphosphine oxide Phosphine oxide-based compounds;

3,3'-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, 10,10'-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-Cl] Coumarin-based compounds such as -benzopyrano [6,7,8-ij] -quinolizin-11-one; and the like.

In the photosensitive resin composition according to an embodiment of the present application, examples of the curing accelerator, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimer Capto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate ), Pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tris (2-mercaptoacetate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate) , Trimethylolethane tris (2-mercaptoacetate), and trimethylolethane tris (3-mercaptopropionate) may include one or more selected from the group consisting of, but are not limited thereto. Known things for Pho Can.

In the photosensitive resin composition according to the embodiment of the present application, the thermal polymerization inhibitor, p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitroso It may include one or more selected from the group consisting of phenylhydroxyamine ammonium salt, N-nitrosophenylhydroxyamine aluminum salt and phenothiazine, but are not limited thereto, and those known in the art It may include.

In the photosensitive resin composition according to the embodiment of the present application, the dispersant may be a polymer type, nonionic, anionic, or cationic dispersant. Non-limiting examples of such dispersants include polyalkylene glycols and esters thereof, polyoxyalkylene polyhydric alcohols, esteralkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, carboxes Acid salts, alkylamide alkylene oxide adducts, alkylamines, and the like, and one or a mixture of two or more selected from these may be used, but is not limited thereto.

In the photosensitive resin composition according to the embodiment of the present application, non-limiting examples of the antioxidant are 2,2-thiobis (4-methyl-6-t-butylphenol) and 2,6-g, t- It may include one or more selected from butylphenol, but is not limited thereto.

In the photosensitive resin composition according to the embodiment of the present application, non-limiting examples of the ultraviolet absorber are 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole And it may include one or more selected from alkoxy benzophenone, but is not limited thereto.

In the photosensitive resin composition according to the embodiment of the present application, the surfactant may include MCF 350SF, F-475, F-488, F-552 (hereinafter referred to as DIC), but are not limited thereto. no.

Other plasticizers, adhesion promoters, fillers, and the like can also be used for all compounds that can be included in conventional photosensitive resin compositions.

One embodiment of the present application provides a photosensitive material including the photosensitive resin composition.

One embodiment of the present application provides a photosensitive material prepared using the photosensitive resin composition.

The photosensitive resin composition is present in a state in which at least a part of the solvent is removed or photocured by drying and / or curing in the photosensitive material.

On the other hand, the photosensitive resin composition according to the present application is used in a roll coater (curtain coater), curtain coater (curtain coater), spin coater (spin coater), slot die coater, various printing, deposition, etc., metal, paper, glass plastic substrate It can be applied on a support such as. It is also possible to apply it onto a support such as a film and then transfer it onto another support or coat it on a first support, transfer it to a blanket or the like, and transfer it to the second support again, and the application method is not particularly limited.

As a light source for hardening the photosensitive resin composition of this application, mercury vapor arc (arc), carbon arc, or Xe arc etc. which emit light of 250-450 nm in wavelength, etc. are mentioned, for example.

The photosensitive resin composition comprising the compound of the present application is a pigment dispersion type photosensitive material for manufacturing a TFT LCD color filter, a photosensitive material for forming a black matrix of a TFT LCD or an organic light emitting diode, a photosensitive material for forming an overcoat layer, a column spacer photosensitive material, a printed circuit board Although it is preferable to be used for photosensitive materials and other transparent photosensitive materials, it can also be used for photocurable paints, photocurable inks, photocurable adhesives, printing plates, PDP manufacture, etc., and the use is not specifically limited.

One embodiment of the present application provides an electronic device manufactured using the photosensitive resin composition.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Having described specific portions of the present application in detail, those skilled in the art will appreciate that these specific embodiments are merely preferred embodiments and that the scope of the present application is not limited thereto. Accordingly, the actual scope of the present application will be defined by the appended claims and their equivalents.

Hereinafter, an Example is given and this invention is demonstrated in detail. The following examples are provided to illustrate the present invention, and the scope of the present invention includes the ranges described in the following claims, their substitutions and changes, and is not limited to the examples.

<Examples>

Synthesis Example 1 Synthesis of Compound (5)

(1) Production of 1a

After dissolving 29.3 g of N-ethylcarbazole in 400 mL of dichloromethane, 21 g of aluminum chloride and 23.2 g of o-toluoyl chloride were slowly added in portions ranging from 0 to 10 ° C. After further stirring at this temperature for 30 minutes, the mixture was stirred at room temperature for 2 hours. Again, the temperature of the reaction solution was lowered to 0 to 10 ° C. and 21 g of aluminum chloride and 19 g of 3-chloropropionyl chloride were added slowly in the range of 0 to 10 ° C. It was further stirred at this temperature for 2 hours. The reaction was poured into a beaker of ice water, and then the organic layer was extracted, washed with saturated aqueous NaHCO ₃ solution, water was removed with anhydrous sodium sulfate, the solvent was removed under vacuum, and recrystallized from t-butyl methyl ether to acylate 1a. 51.6 g was obtained. (Yield: 85%) The measurement results using the 1H-NMR of 1a are as follows.

1 H NMR (500 MHz, CDCl ₃ , ppm): 1.47 (3H, t), 2.34 (3H, s), 3.55 (2H, t), 3.96 (2H, t), 4.40 (4H, q), 7.24-7.48 (6H, m), 8.12 (2H, doublet), 8.52 (1H, d), 8.66 (1H, d).

(2) Preparation of 1b

51 g of the compound 1a and 0.2 g of tetrabutylammonium bromide obtained in the above (1) were dissolved in 210 g of triethylphosphite, and then stirred at 120 ° C. for 6 hours under a nitrogen stream. The mixture was cooled to room temperature and the residual solvent was removed in vacuo. The residue was recrystallized in t-butyl methyl ether to give 54.8 g of compound 1b. (Yield: 86%) The measurement results using the 1H-NMR of 1b are as follows.

1 H NMR (500 MHz, CDCl ₃ , ppm): 1.31-1.38 (6H, m), 1.45-1.56 (3H, t), 2.21-2.32 (2H, m), 2.37 (3H, s), 3.38-3.48 ( 2H, m), 4.10-4.25 (4H, m), 4.42-4.51 (2H, m), 7.28-7.55 (6H, m), 8.18 (2H, dd), 8.54 (1H, d), 8.71 (1H, d).

(3) Preparation of Compound of Formula 1c

35.4 g of Compound 1b obtained in (2) was dissolved in 200 mL of ethanol and 50 mL of water, and then 7.3 g of hydroxyamine hydrochloride and 8.6 g of sodium acetate were added, and the temperature was raised to 80 ° C., followed by stirring for 3 hours. After the reaction was cooled to room temperature, 900 mL of ethyl acetate was added thereto, washed with a saturated aqueous NaHCO ₃ solution, the organic layer was removed with anhydrous magnesium sulfate, the solvent was removed under vacuum, and recrystallized with t-butylmethyl ether. 28 g of compound was obtained. (Yield: 77%) The measurement result using the 1H-NMR of Chemical Formula 3 is as follows.

1 H NMR (500 MHz, CDCl ₃ , ppm): 1.30-1.37 (6H, m), 1.43-1.50 (3H, t), 2.06-2.15 (2H, m), 2.35 (3H, s), 3.13-3.22 ( 2H, m), 4.10-4.23 (4H, m), 4.36-4.45 (2H, m), 7.25-7.46 (6H, m), 7.80 (1H, dd), 8.07 (1H, dd), 8.30 (1H, d), 8.50 (1 H, d).

 (4) Preparation of Compound of Formula 5

After dissolving 8.7 g of Compound 1c obtained in (3) in 100 mL of methylene chloride, the reaction solution was cooled to 0 to 10 ° C., and 1.6 g of acetyl chloride and 2.2 g of triethylamine were added thereto. After the reaction was stirred for 2 hours at this temperature, the reaction solution was washed twice with saturated aqueous NaHCO 3 solution, and then the organic layer was removed with anhydrous magnesium sulfate, and the solvent was removed in vacuo. Recrystallization was carried out in ethyl acetate / hexane (1/2) to obtain 8.0 g of the compound of formula (5). (Yield: 85%) The measurement results using the 1H-NMR of Chemical Formula 5 are as follows.

1 H NMR (500 MHz, CDCl ₃ , ppm): 1.30-1.38 (6H, m), 1.44-1.53 (3H, t), 1.96-2.11 (2H, m), 2.29 (3H, s), 2.36 (3H, s), 3.20-3.30 (2H, m), 4.07-4.22 (4H, m), 4.40-4.50 (2H, m), 7.26-7.48 (6H, m), 7.92 (1H, dd), 8.12 (1H, dd), 8.42 (1 H, d), 8.50 (1 H, d).

Synthesis Example 2 Preparation of Compound of Formula 6

(1) Production of 2a

After dissolving 19.5 g of N- (3-chloropropyl) -carbazole in 300 mL of dichloromethane, 11.2 g of aluminum chloride and 12.4 g of o-toluoyl chloride were slowly added in portions ranging from 0 to 10 ° C. After further stirring at this temperature for 30 minutes, the mixture was stirred at room temperature for 2 hours. Again, the temperature of the reaction solution was lowered to 0 to 10 ° C., and 11.2 g of aluminum chloride and 6.3 g of acetyl chloride were added slowly in the range of 0 to 10 ° C., and further stirred at this temperature for 2 hours. The reaction was poured into a beaker of ice water, the organic layer was extracted, washed with saturated aqueous NaHCO3 solution, water was removed with anhydrous sodium sulfate, the solvent was removed in vacuo and recrystallized from ethyl acetate to give 16.4 g of acylate 2a. . (Yield: 51%) The measurement results using the 1H-NMR of 2a are as follows.

1 H NMR (500 MHz, CDCl ₃ , ppm): 2.33-2.43 (5H, m), 2.71 (3H, s), 3.54 (2H, t), 4.59 (2H, t), 7.28-7.48 (4H, m) , 7.54 (2H, dd), 8.10 (1H, dd), 8.17 (1H, dd), 8.56 (1H, d), 8.70 (1H, d).

(2) Preparation of 2b

15 g of Compound 2a and 0.04 g of tetrabutylammonium bromide obtained in (1) were dissolved in 37 g of triethyl phosphite, followed by stirring at 150 ° C. for 24 hours under a nitrogen stream. After cooling the mixture to room temperature, the residual solvent was removed by vacuum. The residue was dissolved in 40 mL of dimethylacetamide, hydroxyamine hydrochloride was added to 3.9, and then heated to 65 ° C. and stirred for 6 hours. After the reaction was cooled to room temperature, 200 mL of ethyl acetate was added thereto, washed with a saturated NaHCO ₃ aqueous solution, the organic layer was removed with anhydrous magnesium sulfate, the solvent was removed under vacuum, and recrystallized with ethyl acetate. Got it. (Yield: 67%) The measurement results using the 1H-NMR of Chemical Formula 2b are as follows.

1 H NMR (500 MHz, CDCl ₃ , ppm): 1.21-1.39 (6H, m), 1.70-1.84 (2H, m), 2.11-2.26 (2H, m), 2.35 (3H, s), 2.56 (3H, s), 4.01-4.21 (4H, m), 4.49 (2H, t), 7.28-7.48 (4H, m), 7.56 (2H, dd), 8.04 (1H, dd), 8.40 (1H, s), 8.56 (1H, s).

(3) Preparation of Compound of Formula 6

3.1 g of acetic anhydride was added to a solution in which 10.4 g of Compound 2b obtained in (2) was dissolved in 70 mL of n-butyl acetate. The reaction mixture was stirred at 60 ° C for 3 hours, cooled to room temperature, and then washed with saturated NaHCO 3 aqueous solution. The organic layer was washed with anhydrous magnesium sulfate, and the solvent was removed under vacuum. Recrystallization was carried out in n-butyl acetate to obtain 5.9 g of the compound of formula (6). (Yield: 84%) The measurement results using the 1 H-NMR of the above formula (6) are as follows.

1 H NMR (500 MHz, CDCl ₃ , ppm): 1.22-1.41 (6H, m), 1.70-1.82 (2H, m), 2.15-2.29 (2H, m), 2.29 (3H, s), 2.36 (3H, s), 2.51 (3H, s), 4.01-4.21 (4H, m), 4.50 (2H, t), 7.28-7.58 (7H, m), 7.98 (1H, d), 8.11 (1H, d), 8.42 (1 H, s), 8.56 (1 H, s).

&Lt; Example 1 >

Preparation of colored photosensitive resin composition

Alkali-soluble acrylic binder {benzyl methacrylate / N-phenylmaleimide / styrene / methacrylic acid (molar ratio 60/10/12/18, Mw = 10000, 80 KOH mg / g)} 8 parts by weight, CI pigment red 177 43-49 parts by weight of a red mill base consisting of CI Pigment Red and 254, by weight of a polymerizable compound, dipentaerythritol hexa acrylate 16 parts by weight, 2.0 parts by weight of the compound of formula 5 prepared in Synthesis Example 1 as a photopolymerization initiator, and an organic solvent. 27-33 parts by weight of propylene glycol monomethyl ether acetate (PGMEA) was mixed for 3 hours using a shaker to prepare a photosensitive resin composition.

<Example 2>

Preparation of colored photosensitive resin composition

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Formula 6 prepared in Synthesis Example 2 was used instead of the compound of Formula 5 prepared in Synthesis Example 1 in Example 1.

&Lt; Comparative Example 1 &

A photosensitive resin composition was manufactured in the same manner as in Example 1, except that BAOX's OXE-02 compound was used instead of the compound of Formula 5 prepared in Synthesis Example 1 in Example 1.

Comparative Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that Comparative Compound 1 shown in Examples of Korean Patent Publication No. 10-2010-0092904 was used instead of the compound of Formula 5 prepared in Synthesis Example 1 in Example 1. Prepared.

<Experimental Example 2>

After spin-coating the prepared photosensitive resin composition on glass, a pre-bake or soft bake was performed at 100 ° C. for 100 seconds to remove an appropriate amount of a solvent to form a coating film having a thickness of about 2.2 μm. Subsequently, after cooling at room temperature, a linear pattern photomask having a line width of 40 µm was used for exposure at an exposure dose of 40 mJ / cm 2 under a high pressure mercury lamp. The exposed substrate was developed in a spray method in a 0.04% KOH aqueous solution at a temperature of 25 ° C. to confirm the time for the non-exposed part to be washed off, and is shown in Table 1 below.

As shown in Table 1, when the photoactive compound according to the present invention was applied, it showed an excellent effect of increasing the developing speed for the developing solution to enable rapid development compared with Comparative Examples 1 and 2.

Claims (21)

A photoactive compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
At least one of X ₁ and X ₂ is

And the other is hydrogen; A halogen group; CN; OR; SR; COR; OCOR; NRR '; CONRR '; R, OR, SR, COR, and substituted or unsubstituted by one or more substituents selected from the group consisting of unsubstituted C OCOR group of ₁ ~ C _10; And a C ₁ to C ₁₀ haloalkyl group,
Y is a direct link; Or a C ₁ to C ₁₅ alkylene group which is substituted or unsubstituted with at least one substituent selected from the group consisting of R, OR, SR, COR and OCOR,
M ₁ is an alkyl group of C ₁ ~ C ₈ ; Or an aryl group of C ₆ ~ C ₁₂ ,
R ₁ is a C ₁ ~ C ₈ alkyl group; Or an aryl group of C ₆ ~ C ₁₂ ,
A is a C ₆ to C ₂₀ aryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a halogen group, CN, R, OR, SR, COR, OCOR, NRR 'and CONRR',
R ₂ and R ₃ are each independently selected from the group halogen, CN, alkoxy group and C ₁ ~ C ₆ alkylthio group consisting of C ₁ ~ C ₆ alkyl group, C ₁ ~ C _6, the
m and n are each independently an integer of 0 to 3,
R and R 'are each independently selected from the group consisting of hydrogen, a C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ haloalkyl group and C ₇ ~ C ₁₃ arylalkyl group, wherein R and R' together ring Can be formed. The method according to claim 1,
Formula 1 is a photoactive compound, characterized in that any one of Formula 2 to Formula 4:
(2)

(3)

[Chemical Formula 4]

In Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4,
Y is a direct link; Or a C ₁ to C ₁₅ alkylene group which is substituted or unsubstituted with at least one substituent selected from the group consisting of R, OR, SR, COR and OCOR,
X ₁ or X ₂ is hydrogen; A halogen group; CN; OR; SR; COR; OCOR; NRR '; CONRR '; R, OR, SR, COR, and substituted or unsubstituted by one or more substituents selected from the group consisting of unsubstituted C OCOR group of ₁ ~ C _10; And a C ₁ to C ₁₀ haloalkyl group,
M ₁ is an alkyl group of C ₁ ~ C ₈ ; Or an aryl group of C ₆ ~ C ₁₂ ,
R ₁ is a C ₁ ~ C ₈ alkyl group; Or an aryl group of C ₆ ~ C ₁₂ ,
A is

or

ego,
R ₂ to R ₅ are each independently selected from the group halogen, CN, alkoxy group and C ₁ ~ C ₆ alkylthio group consisting of C ₁ ~ C ₆ alkyl group, C ₁ ~ C _6, the
m and n are each independently an integer of 0 to 3,
p is an integer from 0 to 5, q is an integer from 0 to 7,
R and R 'are each independently selected from the group consisting of hydrogen, a C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ haloalkyl group and C ₇ ~ C ₁₃ arylalkyl group, wherein R and R' together ring Can be formed. The method according to claim 1,
Wherein the photoactive compound represented by Formula 1 is represented by Formula 5 or Formula 6:
[Chemical Formula 5]

[Chemical Formula 6]

A photoactive compound represented by the following formula (1);
Alkali-soluble binder resins;
Polymeric compounds containing ethylenically unsaturated bonds; And
A photosensitive resin composition comprising a solvent:
[Chemical Formula 1]

In Formula 1,
At least one of X ₁ and X ₂ is

And the other is hydrogen; A halogen group; CN; OR; SR; COR; OCOR; NRR '; CONRR '; R, OR, SR, COR, and substituted or unsubstituted by one or more substituents selected from the group consisting of unsubstituted C OCOR group of ₁ ~ C _10; And a C ₁ to C ₁₀ haloalkyl group,
Y is a direct link; Or a C ₁ to C ₁₅ alkylene group which is substituted or unsubstituted with at least one substituent selected from the group consisting of R, OR, SR, COR and OCOR,
M ₁ is an alkyl group of C ₁ ~ C ₈ ; Or an aryl group of C ₆ ~ C ₁₂ ,
R ₁ is a C ₁ ~ C ₈ alkyl group; Or an aryl group of C ₆ ~ C ₁₂ ,
A is a C ₆ to C ₂₀ aryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a halogen group, CN, R, OR, SR, COR, OCOR, NRR 'and CONRR',
R ₂ and R ₃ are each independently selected from the group halogen, CN, alkoxy group and C ₁ ~ C ₆ alkylthio group consisting of C ₁ ~ C ₆ alkyl group, C ₁ ~ C _6, the
m and n are each independently an integer of 0 to 3,
R and R 'are each independently selected from the group consisting of hydrogen, a C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ haloalkyl group and C ₇ ~ C ₁₃ arylalkyl group, wherein R and R' together ring Can form The method of claim 4,
Formula 1 is a photosensitive resin composition, characterized in that any one of the formula (2) to:
(2)

(3)

[Chemical Formula 4]

In Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4,
Y is a direct link; A C ₁ to C ₁₅ alkylene group unsubstituted or substituted with one or more substituents selected from the group consisting of R, OR, SR, COR and OCOR,
X ₁ or X ₂ is hydrogen; A halogen group; CN; OR; SR; COR; OCOR; NRR '; CONRR '; R, OR, SR, COR, and substituted or unsubstituted by one or more substituents selected from the group consisting of unsubstituted C OCOR group of ₁ ~ C _10; And a C ₁ to C ₁₀ haloalkyl group,
M ₁ is an alkyl group of C ₁ ~ C ₈ ; Or an aryl group of C ₆ ~ C ₁₂ ,
R ₁ is a C ₁ ~ C ₈ alkyl group; Or an aryl group of C ₆ ~ C ₁₂ ,
A is

or

ego,
R ₂ to R ₅ are each independently selected from the group halogen, CN, alkoxy group and C ₁ ~ C ₆ alkylthio group consisting of C ₁ ~ C ₆ alkyl group, C ₁ ~ C _6, the
m and n are each independently an integer of 0 to 3,
p is an integer from 0 to 5, q is an integer from 0 to 7,
R and R 'are each independently selected from the group consisting of hydrogen, a C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ haloalkyl group and C ₇ ~ C ₁₃ arylalkyl group, wherein R and R' together ring Can be formed. The method of claim 4,
(1) is represented by the following general formula (5) or (6): &lt; EMI ID =
[Chemical Formula 5]

[Chemical Formula 6]

The method of claim 4,
The alkali-soluble binder resin has an acid value of 30 to 300 KOH mg / g photosensitive resin composition, characterized in that. The method of claim 4,
The alkali-soluble binder resin has a weight average molecular weight of 1,000 to 200,000, the photosensitive resin composition. The method of claim 4,
Wherein the content of the photoactive compound is 0.1 to 5% by weight based on the total weight of the photosensitive resin composition. The method of claim 4,
The content of the alkali-soluble binder resin is 1 to 30% by weight based on the total weight of the photosensitive resin composition, the photosensitive resin composition. The method of claim 4,
The content of the polymerizable compound containing the ethylenically unsaturated bond is a photosensitive resin composition, characterized in that 0.5 to 30% by weight based on the total weight of the photosensitive resin composition. The method of claim 4,
The content of the solvent is a photosensitive resin composition, characterized in that 40 to 95% by weight based on the total weight of the photosensitive resin composition. The method of claim 4,
The photosensitive resin composition further comprises a colorant. The method according to claim 13,
The content of the colorant is a photosensitive resin composition, characterized in that 1 to 20% by weight based on the total weight of the photosensitive resin composition. The method of claim 4,
The photosensitive resin composition further comprises a second photoactive compound. 16. The method of claim 15,
The content of the second photoactive compound is a photosensitive resin composition, characterized in that 0.1 to 5% by weight based on the total weight of the photosensitive resin composition. The method of claim 4,
The photosensitive resin composition further includes one or two or more additives selected from the group consisting of a curing accelerator, a thermal polymerization inhibitor, a dispersing agent, an antioxidant, a ultraviolet absorber, a leveling agent, a photosensitizer, a plasticizer, an adhesion promoter, a filler, and a surfactant. The photosensitive resin composition characterized by the above-mentioned. 18. The method of claim 17,
The content of the additive is a photosensitive resin composition, characterized in that 0.01 to 5% by weight, respectively, based on the total weight of the photosensitive resin composition. The photosensitive material manufactured using the photosensitive resin composition of any one of Claims 4-18. The method of claim 19,
The photoresist is selected from the group consisting of a pigment dispersion photoresist for manufacturing a TFT LCD color filter, a photoresist for forming a black matrix of a TFT LCD or an organic light emitting diode, a photoresist for forming an overcoat layer, a column spacer photoresist and a photoresist for a printed circuit board. Photosensitive material characterized in that. An electronic device manufactured using the photosensitive resin composition of any one of claims 4 to 18.