KR20170078016A - Photosensitive resin composition, color filter, and image display apparatus comprising the same - Google Patents

Abstract

(상기 화학식 1 내 치환기는 명세서 내 정의한 바와 같다)The present invention relates to a photosensitive resin composition, a color filter, and an image display device including the same. More specifically, the present invention can improve the degree of curing, heat resistance and solvent resistance by including a photopolymerizable compound represented by the general formula (1).
[Chemical Formula 1]

(The substituents in the above formula (1) are as defined in the specification)

Description

TECHNICAL FIELD [0001] The present invention relates to a photosensitive resin composition, a color filter, and an image display device having the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to a photosensitive resin composition, a color filter, and an image display device having the same.

BACKGROUND ART [0002] Color filters are widely used in imaging devices, liquid crystal display devices, and the like, and their application range is rapidly expanding. A color filter used in a color liquid crystal display device, an image pickup device, or the like is generally formed by uniformly applying a photosensitive resin composition containing a colorant corresponding to each color of red, green and blue on a substrate on which a black matrix is patterned by spin coating (Hereinafter also referred to as "post-baking") is repeated for each color so as to obtain a pixel of each color As shown in FIG.

However, the conventional photosensitive resin compositions do not have sufficient degree of curing, heat resistance, and solvent resistance, and if they are post-baked, pattern short-circuiting and peeling may occur.

Korean Patent Laid-Open Publication No. 10-2013-0134689 discloses an ink composition capable of improving the contrast ratio by using a specific urethane-based multi-functional monomer, a color filter using the same, and a display device containing the same.

However, the above-mentioned prior art only recognizes that the contrast ratio is improved, but does not recognize any problems such as hardness and heat resistance.

Korean Patent Publication No. 10-2013-0134689 (Dec. 10, 2013, LG Chemical Co., Ltd.)

An object of the present invention is to provide a photosensitive resin composition excellent in curing degree, heat resistance and solvent resistance by containing a specific photopolymerizable compound.

Another object of the present invention is to provide a high-quality color filter which improves productivity and yield in a process through a photosensitive resin composition containing a specific photopolymerizable compound and has no pattern error, and an image display device having the same.

In order to accomplish the above object, the photosensitive resin composition according to one embodiment of the present invention comprises a photopolymerizable compound represented by the following general formula (1).

[Chemical Formula 1]

(In the formula 1,

And R < 2 > are each independently - (C = O) -NH-R3,

Wherein R 3 is selected from the group consisting of a C 1 to C 11 alkyl group, a C 3 to C 12 cyclic alkyl group, a C 6 to C 20 aryl group and a C 6 to C 20 heteroaryl group, wherein the alkyl group, the cyclic alkyl group, C11 alkyl group, C3-C12 cyclic alkyl group, C6-C20 aryl group, and C6-C20 heteroaryl group).

The photosensitive resin composition of the present invention contains a photopolymerizable compound having a urethane bond, thereby improving the degree of curing, heat resistance and solvent resistance.

Further, the color filter made of the photosensitive resin composition of the present invention and the image display device including the color filter have the effect of improving productivity and yield.

Hereinafter, preferred embodiments of the present invention will be described in detail.

<Photosensitive resin composition>

The photosensitive resin composition of the present invention comprises the photopolymerizable compound represented by the general formula (1), and may further include an alkali-soluble resin, a photopolymerization initiator, a colorant, and a solvent.

Alkali-soluble resin

The alkali-soluble resin according to the present invention is a component which imparts solubility to an alkali developing solution used in a development processing process for forming a pattern, and is polymerized including an ethylenically unsaturated monomer having a carboxyl group. The type of the ethylenically unsaturated monomer having a carboxyl group is not particularly limited, and examples thereof include monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid, and anhydrides thereof; mono (meth) acrylates of polymers having a carboxyl group and a hydroxyl group at both ends such as? -carboxypolycaprolactone mono (meth) acrylate, and the like, preferably acrylic acid and methacrylic acid. These may be used alone or in combination of two or more.

The alkali-soluble resin according to the present invention may further comprise at least one other monomer copolymerizable with the monomer. Methylstyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p- Aromatic vinyl compounds such as vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether and p-vinyl benzyl glycidyl ether; N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm N-substituted maleimide-based compounds such as methylphenyl maleimide, Np-methylphenyl maleimide, No-methoxyphenyl maleimide, Nm-methoxyphenyl maleimide and Np-methoxyphenyl maleimide; Propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, alkyl (meth) acrylates such as sec-butyl (meth) acrylate and t-butyl (meth) acrylate; (Meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6] decan- Alicyclic (meth) acrylates such as dicyclopentanyloxyethyl (meth) acrylate and isobornyl (meth) acrylate; Aryl (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate; 3- (methacryloyloxymethyl) -2-trifluoromethyl oxetane, 3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) 2- (methacryloyloxymethyl) oxetane, 2- (methacryloyloxymethyl) -4-trifluoromethyloxetane, and the like Unsaturated oxetane compounds; Unsaturated oxiranes such as glycidyl (meth) acrylate, 3,4-epoxycyclohexyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate and methyl glycidyl compound; A (meth) acrylate substituted with a cycloalkane having 4 to 16 carbon atoms, a dicycloalkane, or a tricycloalkane ring; And the like. These may be used alone or in combination of two or more.

The acid value of the alkali-soluble resin is preferably 20 to 200 (KOH mg / g), more preferably 30 to 150 (KOH mg / g). When the acid value of the alkali-soluble resin is within the above-mentioned range, an appropriate developing rate is ensured and the adhesion with the substrate is also excellent, so that the pattern is not easily short-circuited and no problem of precipitation of the dye or increase in viscosity occurs .

The weight average molecular weight of the alkali-soluble resin in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000. When the weight average molecular weight of the alkali-soluble resin is within the above range, the reduction of the film at the time of development can be prevented, and the missability of the pattern portion can be improved.

The molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the alkali-soluble resin is preferably 1.5 to 6.0, more preferably 1.8 to 4.0. When the molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) is within the above range, the developing property can be excellent.

The content of the alkali-soluble resin is not particularly limited and may be, for example, 10 to 80% by weight, preferably 10 to 70% by weight based on the total weight% of the solid content of the photosensitive resin composition. When the alkali-soluble resin is contained within the above range, the solubility in a developing solution is sufficient and pattern formation is easy, and the reduction of the film thickness of the pixel portion of the exposed portion at the time of development can be prevented.

In the present invention, the total solid content in the photosensitive resin composition means the total content of the remaining components excluding the solvent from the photosensitive resin composition.

Photopolymerization  compound

The photopolymerizable compound used in the photosensitive resin composition of the present invention includes a compound represented by the following general formula (1).

[Chemical Formula 1]

(In the formula 1,

And R &lt; 2 &gt; are each independently - (C = O) -NH-R3,

Wherein R 3 is selected from the group consisting of a C 1 to C 11 alkyl group, a C 3 to C 12 cyclic alkyl group, a C 6 to C 20 aryl group and a C 6 to C 20 heteroaryl group, wherein the alkyl group, the cyclic alkyl group, C11 alkyl group, C3-C12 cyclic alkyl group, C6-C20 aryl group, and C6-C20 heteroaryl group).

The alkyl group includes straight or branched alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, isobutyl, n-pentyl, n- n-decyl, and the like.

Cyclic alkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.

The aryl group may include phenyl, biphenyl, terphenyl, stilbenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, and the like.

Heteroaryl groups are intended to include a single ring or multi-ring system, e. G., A fused ring system. For example, thienyl, benzo [b] thienyl, naphtho [2,3-b] thienyl, thianthrenyl, furyl, dibenzofuryl, chromenyl, xanthenyl, thioxanthyl, Pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, pyrrolyl, imidazolyl, pyrrolyl, pyrazinyl, pyrimidinyl, , Phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl,? -Carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl , Phenanthryl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, phenoxazinyl, 7-phenanthryl, anthraquinon-2-yl (= 9,10-dioxo-9,10-dihydroanthracene Benzo [b] thienyl, 2-benzo [b] thienyl, 4-dibenzofuryl, 4,7-dibenzofuryl, 4-methyl Dibenzofuryl, 2-xanthenyl, 8-methyl-2-xanthenyl, 3-xanthenyl, 2-phenoxy 3-pyrrolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-pyrrolidinyl, Ethyl-4-imidazolyl, 2-ethyl-5-imidazolyl, 1H-tetrazol-5-yl, 3- pyrazolyl, , 1-propyl-4-pyrazolyl, 2-pyrazinyl, 5,6-dimethyl-2-pyrazinyl, 2-indolizinyl, Indolyl, 1-methyl-3-indolyl, 1,5-dimethyl-2-indolyl, 1-methyl-3-indazolyl, 2,7-dimethyl- Isoquinolyl, 3-methoxy-6-isoquinolyl, 2-methoxy-7-methyl-8-purinyl, Quinolyl, 2-methoxy-6-quinolyl, 6-phthalazinyl, 7-phthalazinyl, 1- Naphthyridin-2-yl, 2-quinoxalinyl, 6-quinoxalinyl, 2,3-dimethyl- 6-quinoxalinyl, 2,3-dimethyl 2-quinazolinyl, 6-quinolinyl, 6-quinolinyl, 6-quinolinyl, 6-quinolinyl, 2-pyrrolidinyl, 2-pyrrolidinyl, 3-carboxy-pyrrolidinyl, 6-pyrrolidinyl, Carbazolyl,? -Carbololin-3-yl, 1-methyl-? -Carbolin-3-yl, 1-methyl-? 3-acridinyl, 2-perimidinyl, 1-methyl-5-perimidinyl, 5-phenanthrolinyl, 6-acridinyl, 2-phenothiazinyl, 3-phenothiazinyl, 10-methyl-3- (4-isothiazolyl, Phenoxazinyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 4-methyl-3-furazanyl, .

The content of the photopolymerizable compound is preferably 5 to 50% by weight, more preferably 7 to 50% by weight based on the total weight% of the solid content of the photosensitive resin composition. When the photopolymerizable compound is contained within the above range, the strength and reliability of the pixel portion can be improved.

Light curing Initiator

The photopolymerization initiator according to the present invention is not particularly limited as long as it can polymerize the photopolymerizable compound, and examples thereof include acetophenone compounds, benzophenone compounds, triazine compounds, At least one compound selected from the group consisting of a sol-based compound, a thioxanthone compound, and an oxime ester compound can be used, and it is preferable to use an oxime ester compound.

Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy- 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1- (2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propane -1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

Specific examples of the benzophenone compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like. Specific examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4 Bis (trichloromethyl) -6- [2- (5-methylfuran-1-yl) Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan- Triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- L-methylethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

Specific examples of the imidazole-based compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbimidazole, 2,2'- 4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) (2-chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole, 2,2-bis (2,6-dichlorophenyl) -4,4'5,5'-tetraphenyl-1,2'-biimidazole or an imidazole compound in which the phenyl group at the 4,4 ', 5,5' position is substituted by a carboalkoxy group , Preferably 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetraphenylbiimidazole, 2,2-bis (2,6-dichlorophenyl) -4,4'5,5'-tetraphenyl-1,2'-biimidazole Specific examples of the thioxanthene compound include 2-isopropylthioxanthone, 2- 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propanedioxanthone.

Specific examples of the oxime ester compound include o-ethoxycarbonyl-α-oximino-1-phenylpropan-1-one, 1,2-octadione, (O-benzoyloxime), 1- (9-ethyl) -6- (2-methylbenzoyl- Irgacure OXE-02 (BASF), N-1919 (Adeca), NCI-831 (ADE), and CGI-124 Casa).

The photopolymerization initiator may further comprise a photopolymerization initiator. The photosensitive resin composition according to the present invention further contains a photopolymerization initiation auxiliary agent, whereby the sensitivity can be further increased and the productivity can be improved.

Examples of the photopolymerization initiator include at least one compound selected from the group consisting of an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group.

Specific examples of the amine compound include aliphatic amine compounds such as triethanolamine, methyldiethanolamine and triisopropanolamine; aliphatic amines such as methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid isoamyl, 2-ethylhexyl dimethylbenzoate, 2-dimethylaminoethyl benzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (Diethylamino) benzophenone, and the like, and it is preferable to use an aromatic amine compound.

Specific examples of the carboxylic acid compound include aromatic heteroacetic acid compounds, and aromatic thioacetic acid compounds such as phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like can be given.

Specific examples of the organic sulfur compound having a thiol group include 2-mercaptobenzothiazole, 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (3-mercaptobutyloxy Ethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -thione, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), tetraethyleneglycol bis (3-mercaptopropionate), and the like can be used. .

The content of the photopolymerization initiator is not particularly limited and may be, for example, 0.1 to 40% by weight, preferably 0.1 to 8 parts by weight based on the total weight% of the solid content of the photosensitive resin composition. When the content of the photopolymerization initiator is in the above range, the sensitivity of the photosensitive resin composition is increased and the exposure time is shortened, so that the productivity is improved and high resolution can be maintained, and the strength of the formed pixel portion and the smoothness on the surface of the pixel portion become good .

coloring agent

The colorant may comprise one or more pigments or one or more dyes.

Pigment

The pigment may be an organic pigment or an inorganic pigment generally used in the art. The above-mentioned pigments can be used in various kinds of pigments used in printing ink, ink jet ink and the like. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, And an anthanthrone pigment, an anthanthrone pigment, a pravanthrone pigment, a pyranthrone pigment, an anthanthrone pigment, an anthanthrone pigment, an anthanthrone pigment, an anthanthrone pigment, an anthanthrone pigment, a pyranthrone pigment, pyranthrone pigments, diketopyrrolopyrrole pigments, and the like.

Examples of the inorganic pigments include metallic compounds such as metal oxides and metal complex salts. Specific examples of the inorganic pigments include oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and carbon black Or composite metal oxides. Particularly, the organic pigments and inorganic pigments may be specifically classified into pigments in the Society of Dyers and Colourists, and more specifically, those having a color index (CI) number And pigments. However, it is not necessarily limited to these pigments. These pigments may be used alone or in combination of two or more kinds.

C.I. Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180 And 185

C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71C.I.

Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 208, 215, 216, 224, 242, 254, 255 and 264C.

Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38C.I.

Pigment Blue 15 (15: 3, 15: 4, 15: 6, etc.), 21, 28, 60, 64 and 76C.I.

Pigment Green 7, 10, 15, 25, 36, 47 and 58C.I

Pigment Brown 28C.I

Pigment Black 1 and Pigment Black 7 can be used as organic pigments or inorganic pigments generally used in the art. These pigments may be used alone or in combination of two or more.

The exemplified C.I. Among the pigment pigments, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Orange 38, C.I. Pigment Red 122, C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 208, C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Violet 23, C.I. Pigment Blue 15: 3, Pigment Blue 15: 6, C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment selected from Pigment Green 58 can be preferably used.

It is preferable to use a pigment dispersion in which the particle diameter of the pigment is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of the pigment includes a method of dispersing the pigment by adding a pigment dispersant. According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

Specific examples of the pigment dispersant include cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, polyester surfactants, and polyamine surfactants. These surfactants may be used singly or in combination of two or more thereof .

The pigment dispersant is added for maintenance of deagglomeration and stability of the pigment, and any of those generally used in the art can be used without limitation. (Hereinafter referred to as an acrylic dispersant) containing BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate). At this time, it is preferable to apply the acrylic dispersant prepared by a living control method as disclosed in Korean Patent Laid-Open Publication No. 2004-0014311. DISCLOSURE OF INVENTION It is an object of the present invention to provide an acrylic dispersant, 2000, DISPER BYK-2001, DISPER BYK-2070, and DISPER BYK-2150.

The acrylic dispersants exemplified above may be used alone or in combination of two or more.

As the pigment dispersant, other resin type pigment dispersants other than the acrylic dispersant may be used. The other resin type pigment dispersing agent may be a known resin type pigment dispersing agent, especially a polycarboxylic acid ester such as polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and their modified products, or free ) Oil-based dispersants such as amides formed by reaction of a polyester having a carboxyl group with poly (lower alkyleneimine) or salts thereof; Soluble resin or water-soluble polymer compound such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; Polyester; Modified polyacrylates; Adducts of ethylene oxide / propylene oxide, and phosphate esters. DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-160, BYK (trade name) 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; EFKA-4060, EFKA-4060, EFKA-4055, EFKA-4055, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 from Lubirzol; Hinoact T-6000, Hinoact T-7000, Hinoact T-8000; available from Kawaken Fine Chemicals; AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823 manufactured by Ajinomoto; FLORENE DOPA-17HF, fluorene DOPA-15BHF, fluorene DOPA-33, and fluorene DOPA-44 are trade names of Kyoeisha Chemical Co., In addition to the acrylic dispersant, other resin type pigment dispersants may be used alone or in combination of two or more, or may be used in combination with acrylic dispersion.

The content of the pigment dispersant is preferably 5 to 60 parts by weight, more preferably 15 to 50 parts by weight based on 100 parts by weight of the solid content of the pigment to be used. If the content of the pigment dispersant exceeds the above range, the viscosity may be high. If the content of the pigment dispersant is less than the above range, it may be difficult to atomize the pigment or gelation after dispersion.

dyes

The dye can be used without limitation as long as it has solubility in an organic solvent. It is preferable to use a dye which has solubility in an organic solvent and can ensure reliability such as solubility in an alkali developing solution, solubility in solvent and stability with time.

Examples of the dye include acid dyes having an acidic group such as sulfonic acid and carboxylic acid, salts of an acidic dye and a nitrogen-containing compound, sulfonamides of an acidic dye and derivatives thereof, and azo, Based acid dyes and derivatives thereof.

Preferably, the dye is a compound classified as a dye in a color index (published by The Society of Dyers and Colourists), or a known dye described in a dyeing note (coloring yarn).

Specific examples of the dye include C.I. As solvent dyes,

C.I. Yellow dyes such as Solvent Yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163;

C.I. Red dyes such as Solvent Red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179;

C.I. Orange dyes such as solvent orange 2, 7, 11, 15, 26, 41, 45, 56, 62;

C.I. Blue dyes such as Solvent Blue 5, 35, 36, 37, 44, 59, 67 and 70;

C.I. Violet dyes such as solvent violet 8, 9, 13, 14, 36, 37, 47, 49;

C.I. Green dyes such as Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like.

C.I. Solvent dye having excellent solubility in an organic solvent. Solvent Yellow 14, 16, 21, 56, 151, 79, 93; C.I. Solvent Red 8, 49, 89, 111, 122, 132, 146, 179; C.I. Solvent Orange 41, 45, 62; C.I. Solvent Blue 35, 36, 44, 45, 70; C.I. Solvent violet 13 is preferred and C.I. Solvent Yellow 21, 79; C.I. Solvent Red 8, 122, 132; C.I. Is more preferable.

Also, C.I. CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, Yellow dye;

CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88 , 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217 , 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349 Red dyes such as 382, 383, 394, 401, 412, 417, 418, 422, 426;

Orange dyes such as C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, , 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, , 335, 340 and the like;

Violet dyes such as C.I. Acid Violet 6B, 7, 9, 17, 19, 66 and the like;

Green dyes such as C.I. acid green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106,

CI Acid Yellow 42, which is excellent in solubility in organic solvents in acid dyes; C.I. Acid Red 92; C. I. Acid Blue 80, 90; C.I. Acid Violet 66; C.I. Acid Green 27 is preferred.

As CI direct dyes, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102 , 108, 109, 129, 136, 138, 141 and the like;

CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211 , 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

Orange dyes such as C.I. Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

CI Direct Blue 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113 , 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189 , 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210, 212, 213, 214, 222, 228, 229, 237, 238, 242, 243, 244, 245, 247, 248 , 250, 251, 252, 256, 257, 259, 260, 268, 274, 275 and 293;

Violet dyes such as C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

Green dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79,

Also, C.I. Yellow dyes such as C.I. Modatto Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65 as modaneto dyes;

CI Modal Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, Red dyes such as 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;

CI Modanato Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, dyes;

CI Modanito Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 43, 44, 48, 49, 53, 61, 74, 77, 83, and 84;

Violet colored dyes such as C.I. Modanth violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;

Green dyes such as C.I. Modatto Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43,

These dyes may be used alone or in combination of two or more.

The content of the colorant is preferably 5 to 60% by weight, and more preferably 10 to 45% by weight based on the total weight% of the solid content of the photosensitive resin composition. When the colorant is within the above range, the color density of the pixel is sufficient even when a thin film is formed, and the residue of the non-curing portion is not lowered during development, so that it is preferable that the residue is hardly generated.

In the present invention, the total solid content% by weight of the photosensitive resin composition means the total content of the remaining components excluding the solvent from the photosensitive resin composition.

solvent

The solvent may be any solvent as long as it is commonly used in the art.

Specific examples of the solvent include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether and ethylene glycol monobutyl ether; Diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol dipropyl ether and diethylene glycol dibutyl ether; Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, ethylene glycol monobutyl ether acetate and ethylene glycol monoethyl ether acetate; Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate; Propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether and propylene glycol monobutyl ether; Propylene glycol dialkyl ethers such as propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol ethyl methyl ether, propylene glycol dipropyl ether, propylene glycol propyl methyl ether and propylene glycol ethyl propyl ether; Propylene glycol alkyl ether propionates such as propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate, propylene glycol propyl ether propionate and propylene glycol butyl ether propionate; Butyldiol monoalkyl ethers such as methoxybutyl alcohol, ethoxybutyl alcohol, propoxybutyl alcohol and butoxybutyl alcohol; Butanediol monoalkyl ether acetates such as methoxybutyl acetate, ethoxybutyl acetate, propoxybutyl acetate and butoxybutyl acetate; Butanediol monoalkyl ether propionates such as methoxy butyl propionate, ethoxy butyl propionate, propoxy butyl propionate and butoxy butyl propionate; Dipropylene glycol dialkyl ethers such as dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether and dipropylene glycol methyl ethyl ether; Aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene; Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin; Examples of the solvent include methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxypropionate, methylhydroxyacetate, , Hydroxybutyl acetate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, propyl 3-hydroxypropionate, butyl 3-hydroxypropionate, Methyl methoxyacetate, methyl methoxyacetate, methyl methoxyacetate, ethyl methoxyacetate, propyl methoxyacetate, butyl methoxyacetate, ethoxyacetate, ethoxyacetate, ethoxyacetate, ethoxyacetate, propoxy Methyl acetate, ethyl propoxyacetate, propoxypropylacetate, butyl propoxyacetate, methyl butoxyacetate, ethyl butoxyacetate, butyl Methoxypropionate, ethyl 2-methoxypropionate, butyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, , Propyl 2-ethoxypropionate, butyl 2-ethoxypropionate, methyl 2-butoxypropionate, ethyl 2-butoxypropionate, propyl 2-butoxypropionate, butyl 2-butoxypropionate, Ethoxypropionate, propyl 3-ethoxypropionate, propyl 3-ethoxypropionate, butyl 3-ethoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, butyl 3-methoxypropionate, Propoxy propionate, methyl 3-butoxypropionate, ethyl 3-butoxypropionate, 3-butoxypropionic acid ethyl, 3-propoxypropionate, Esters such as ropil, 3-butoxy-propionic acid butyl; Cyclic ethers such as tetrahydrofuran and pyran; and cyclic esters such as? -butyrolactone. The solvents exemplified herein may be used alone or in combination of two or more.

The solvent may be an ester such as alkylene glycol alkyl ether acetates, ketones, butanediol alkyl ether acetates, butanediol monoalkyl ethers, ethyl 3-ethoxypropionate and methyl 3-methoxypropionate And more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, methoxybutyl acetate, methoxybutanol, ethyl 3-ethoxypropionate, 3-methoxypropionic acid Methyl and the like can be used.

The solvent may be contained in an amount of 60 to 90% by weight, preferably 70 to 85% by weight based on the total weight% of the photosensitive resin composition. When the solvent is within the above range, the coating property can be improved when applied with a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater), or an ink jet.

additive

The photosensitive resin composition according to the present invention may further contain additives as required. Specific examples thereof include at least one selected from dispersants, wetting agents, silane coupling agents, and anti-aggregation agents.

As the dispersing agent, a commercially available surfactant may be used. Examples of the surfactant include a silicone surfactant, a fluorinated surfactant, a silicon surfactant having a fluorine atom, and a mixture thereof. Examples of the silicone surfactant include a surfactant having a siloxane bond. As commercially available products, Toray Silicon DC3PA, Toray Silicone SH7PA, Toray Silicon DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone 29SHPA, Toray Silicone SH30PA, Polyether Modified Silicone Oil SH8400 (Toray Silicone Co., Ltd.), KP321 (Manufactured by Shin-Etsu Silicones), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460, TSF4460, TSF4460 . Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain. Concretely, it is possible to use a propylene glycol (trade name) FC430, a prolineate FC431 (manufactured by Sumitomo 3M Ltd.), Megapack (trade name) F142D, Megapack F171, Megapack F172, Megafac F173, Megafac F177, (Trade name) EF301, Eftop EF303, Eftop EF351, and Eftop EF352 (manufactured by Shin-Aitaku Kasei Co., Ltd.), Megapack F183, Megapack R30 1000, BM-1100 (product name) S381, Surfron S382, Surfron SC101, Surfron SC105 (manufactured by Asahi Glass Co., Ltd.), E5844 (manufactured by Daikin Fine Chemical Co., Ltd.) Manufactured by BMChemie). Examples of the silicone surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain. Specific examples thereof include Megapac (trade name) R08, Megapack BL20, Megapack F475, Megapack F477, Megapack F443 (manufactured by Dainippon Ink and Chemicals, Incorporated).

Examples of the wetting agent include glycerin, diethylene glycol, ethylene glycol, and the like, and may include at least one selected from the group.

Examples of the silane coupling agent include aminopropyltriethoxysilane,? -Mercaptopropyltrimethoxysilane and? -Methacryloxypropyltrimethoxysilane, and commercially available products include SH6062, SZ6030 (Toray-Dow (Manufactured by Corning Silicon co., Ltd.), KBE903 and KBM803 (manufactured by Shin-Etsu silicone co., Ltd.).

The anti-aggregation agent includes, for example, sodium polyacrylate.

<Color filter>

When the color filter of the present invention is applied to an image display apparatus, since it emits light by the light of the display apparatus light source, it is possible to realize more excellent light efficiency. In addition, since color light is emitted, color reproducibility is better, and light is emitted in all directions due to optical luminescence, so that viewing angle can also be improved.

The color filter includes a substrate and a pattern layer formed on the substrate.

The substrate may be a substrate of the color filter itself, or may be a portion where the color filter is placed on a display device or the like, and is not particularly limited. The substrate can be glass, silicon (Si), may be a silicon oxide (SiO _x) or a polymer substrate, the polymer substrate, such as polyether sulfone (polyethersulfone, PES), or polycarbonate (polycarbonate, PC).

The pattern layer may be a layer containing the photosensitive resin composition of the present invention, and may be a layer formed by applying the photosensitive resin composition and exposing, developing, and curing the composition in a predetermined pattern.

The pattern layer formed of the photosensitive resin composition may have a red pattern layer containing the red quantum dot particles, a green pattern layer containing the green quantum dot particles, and a blue pattern layer containing the blue quantum dot particles. During the light irradiation, the red pattern layer emits red light, the green pattern layer emits green light, and the blue pattern layer emits blue light.

In such a case, the emitted light of the light source is not particularly limited when applied to an image display apparatus, but a light source that emits blue light in terms of better color reproducibility can be used.

According to another embodiment of the present invention, the pattern layer may include only a pattern layer of two colors, that is, a red pattern layer, a green pattern layer, and a blue pattern layer. In such a case, the pattern layer further includes a transparent pattern layer not containing quantum dot particles.

In the case where only the pattern layer of two colors is provided, a light source that emits light having a wavelength that represents the remaining color that is not included can be used. For example, when a red pattern layer and a green pattern layer are included, a light source that emits blue light can be used. In such a case, red quantum dot particles emit red light and rust quantum dot particles emit green light, and the transparent pattern layer transmits blue light as it is and exhibits blue color.

The color filter including the substrate and the pattern layer as described above may further include a partition wall formed between the respective patterns, and may further include a black matrix. Further, it may further comprise a protective film formed on the pattern layer of the color filter.

<Image Display Device>

The present invention also provides an image display device including the color filter.

The color filter of the present invention is applicable not only to a general liquid crystal display device but also to various image display devices such as an electroluminescent display device, a plasma display device, and a field emission display device.

The image display apparatus of the present invention may include a color filter including a red pattern layer containing red QD particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue QDs. In such a case, the emitted light of the light source is not particularly limited when applied to an image display apparatus, but a light source that emits blue light is preferable from the viewpoint of superior color reproducibility.

According to another embodiment of the present invention, the image display apparatus of the present invention may include a color filter including only a pattern layer of two colors of a red pattern layer, a green pattern layer, and a blue pattern layer. In such a case, the color filter further includes a transparent pattern layer not containing quantum dot particles.

In the case where only the pattern layer of two colors is provided, a light source that emits light having a wavelength that represents the remaining color that is not included can be used. For example, when a red pattern layer and a green pattern layer are included, a light source that emits blue light can be used. In such a case, red quantum dot particles emit red light and rust quantum dot particles emit green light, and the transparent pattern layer transmits blue light as it is and exhibits blue color.

The image display apparatus of the present invention has excellent light efficiency, exhibits high luminance, excellent color reproducibility, and can have a wide viewing angle.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the embodiments of the present invention described below are illustrative only and the scope of the present invention is not limited to these embodiments. The scope of the present invention is indicated in the claims, and moreover, includes all changes within the meaning and range of equivalency of the claims. In the following Examples and Comparative Examples, "%" and "part" representing the content are on a mass basis unless otherwise specified.

Synthetic example  1. Synthesis of P-1

After 40 mmol (7.92 g) of gallic acid and 27.6 g of K ₂ CO ₃ were dissolved in DMF (80 ml), 3-methyl-3-butenyl bromide (40 ml) was slowly added dropwise thereto to obtain white ethyl 3,4,5- To obtain allyloxybenzoate. 1% NaOH aqueous solution was added to the obtained white solid, and the mixture was stirred for 30 minutes. The white solid was purified by silica gel column chromatography (ethyl acetate: normal hexane = 1: 6) to obtain 6.5 g (yield: 77%) of P-1.

Synthetic example  2. Synthesis of T-P-1

30 mmol of P-1, 10 mmol of bispentaerythritol, 0.1% by weight of sodium, 0.02% by weight of calcium and 20 g of para-toluenesulfonic acid monohydrate were dissolved in 200 ml of toluene, and the mixture was heated to 120 DEG C under a nitrogen stream, Respectively. After the reaction was completed, the reaction mixture was cooled to room temperature and 400 ml of toluene was added thereto. The organic layer was washed with 200 ml of purified water. Anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer was filtered and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (ethyl acetate: normal hexane = 1: 4) to obtain TP-1.

Synthetic example  3. Synthesis of B-1

To the reactor, 42.46 g (0.2885 mol) of methylbenzyl isocyanate and 109.08 g (0.8391 mol) of an acrylate monomer, 109.08 g (0.8391 mol) were added and the mixture was heated to 40 ° C and stirred with 0.15 g (0.00136 mol) of resorcinol . 0.06 g (9.5 × 0 ^-5 mol) of dibutyltin dilaurate (DBTDL) as a catalyst after complete dissolution was slowly added. Since an exothermic reaction occurs at this time, the temperature is controlled so as not to exceed 80 ° C. After the addition, the temperature was gradually raised and the reaction proceeded at 80 ° C for 6 hours. When the reaction temperature is higher than 85 ° C, it is important to maintain the reaction temperature at 80 ° C or less because an isocyanate group and a urethane group react with each other in addition to the main reaction to generate an allophanate group. After 6 hours, the mantle was removed and the mixture was gradually cooled with stirring to complete the synthesis reaction to obtain B-1.

Synthetic example  4. Synthesis of B-2

Synthesis Example 3 was repeated except that naphthyl isocyanate was used instead of methyl benzyl isocyanate to synthesize B-2.

Synthetic example  5. Synthesis of B-3

Synthesis was conducted in the same manner as in Synthesis Example 3, except that 3-methyl-2-butylisocyanate was used instead of methylbenzylisocyanate to obtain B-3.

Synthetic example  6. Synthesis of B-4

Synthesis Example 3 was repeated except that 2-octyl isocyanate was used instead of methyl benzyl isocyanate to obtain B-4.

Synthetic example  7. Synthesis of B-5

Synthesis Example 3 was repeated except that allyl isocyanate was used in place of methylbenzyl isocyanate to synthesize B-5.

Synthetic example  8. Synthesis of B-6

Example  1 to 6, Comparative Examples 1 to 5: Preparation of Photosensitive Resin Composition

(Parts by weight) Example Comparative Example One 2 3 4 5 6 One 2 3 4 5 Knife A 13.715 13.715 13.715 13.715 13.715 13.715 13.715 13.715 13.715 13.715 13.715 B-1 3.811 - - - - - - - - - - B-2 - 3.811 - - - - - - - - - B-3 - - 3.811 - - - - - - - B-4 - - - 3.811 - - - - - - - B-5 - - - - 3.811 - - - - - B-6 - - - - - 3.811 - - - - - B-7 - - - - - - 3.811 - - - B-8 - - - - - - - 3.811 - - - B-9 - - - - - - 3.811 - - B-10 - - - - - - - - - 3.811 - B-11 - - - - - - - - - - 3.811 Introduction C-1 0.915 0.915 0.915 0.915 0.915 0.915 0.915 0.915 0.915 0.915 0.915 C-2 0.457 0.457 0.457 0.457 0.457 0.457 0.457 0.457 0.457 0.457 0.457 D 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5 Article E-1 17,000 17,000 17,000 17,000 17,000 17,000 17,000 17,000 17,000 17,000 17,000 E-2 59.596 59.596 59.596 59.596 59.596 59.596 59.596 59.596 59.596 59.596 59.596 F 0.006 0.006 0.006 0.006 0.006 0.006 0.006 0.006 0.006 0.006 0.006

TEP-G (아사히기재공업㈜)
B-9:

A-TMMT ,(신나카무라 화학)
B-10: 에톡시레이트 디펜타에리트리톨 펜타아크릴레이트 (A-DPH-12E, 신나카무라화학)
B-11: 프로필록시레이트 트리메틸로프로판 트리아크릴레이트 (A-TMPT-6PO, 신나카무라화학)
C-1: 2-메틸-2-모르폴리노-1-(4-메틸티오페닐)프로판-1-온
C-2: 4,4'-비스(디에틸아미노)벤조페논
D: C.I. 피그먼트 블루 15:6
E-1: 3-에톡시프로피오네이트
E-2: 프로필렌글리콜 모노메틸에테르 아세테이트
F: 폴리에테르 변성 실리콘 오일 SH8400(토레이실리콘(주) 제조)A: Copolymer of methacrylic acid and benzyl methacrylate (ratio of methacrylic acid unit to benzyl methacrylate unit: 27:73, acid value: 83, weight average molecular weight in terms of polystyrene: 18,000)
B-1 to B-6: Compounds of Synthesis Examples 3 to 8
B-7: Propyloxylated dipentaerythritol pentaacrylate (A-DPH-6P, Shin-Nakamura Chemical)
B-8:

TEP-G (Asahi Kasei Kogyo Co., Ltd.)
B-9:

A-TMMT, (Shin Nakamura Chemical)
B-10: Ethoxylated dipentaerythritol pentaacrylate (A-DPH-12E, Shin-Nakamura Chemical)
B-11: Propyloxylate trimethylolpropane triacrylate (A-TMPT-6PO, Shin-Nakamura Chemical)
C-1: 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-
C-2: 4,4'-bis (diethylamino) benzophenone
D: CI Pigment Blue 15: 6
E-1: 3-ethoxypropionate
E-2: Propylene glycol monomethyl ether acetate
F: polyether-modified silicone oil SH8400 (Toray Silicone Co., Ltd.)

Experimental Example

A color filter was prepared using the photosensitive resin compositions prepared in Examples 1 to 6 and Comparative Examples 1 to 5.

Specifically, each of the photosensitive resin compositions was coated on a 2-inch-square glass substrate ("EAGLE XG", manufactured by Corning Inc.) by spin coating, then placed on a heating plate and held at a temperature of 100 ° C. for 3 minutes to form a thin film . Subsequently, a test photomask having a pattern for changing the transmittance in the range of 1 to 100% to a step-like pattern and a line / space pattern of 1 to 50 m was placed on the thin film and the distance between the test photomask and the test photomask was set to 100 m. Respectively. At this time, the ultraviolet light source was irradiated with a high pressure mercury lamp of 1 KW containing g, h and i lines at an illuminance of 100 mJ / cm 2, and no special optical filter was used. The thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes to develop. The glass plate coated with the thin film was washed with distilled water, and then blown with nitrogen gas, dried, and heated in a heating oven at 200 ° C for 25 minutes to prepare a color filter. The film thickness of the color filter prepared above was 2.0 mu m.

1. Adhesion evaluation

When the generated pattern was evaluated by an optical microscope, the following pattern was evaluated on the basis of the degree of peeling phenomenon, and it is shown in Table 2 below.

○: No pattern peeling

△: 1 to 3 pattern peeling

X: Pattern peeling 4 or more

2. Sensitivity evaluation

The photosensitive composition was applied on a glass substrate by spin coating, and then placed on a heating plate and held at a temperature of 100 캜 for 2 minutes to form a thin film. A test photomask having a 20-micrometer pattern was placed on the test photomask and irradiated with ultraviolet rays at an interval of 50 m. At this time, the ultraviolet light source was irradiated with a high pressure mercury lamp of 1 KW containing g, h and i lines at an illuminance of 50 mJ / cm 2, and no special optical filter was used. The thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes to develop. The glass plate on which the thin film was coated was washed with distilled water and observed with an optical microscope until a pattern of several micrometers remained.

3. Evaluation of pencil hardness

The pencil hardness was measured under a constant load of 1 kg using a pencil hardness tester (accuracy tester, Korea) in order to compare the surface hardness of each coated film on the color filter prepared above. A standard pencil (MITSUBISHI) was changed from 6B to 9H while maintaining a 45 degree angle, and scratch was applied to observe the change of the surface. (ASTM 3363-74) Each experimental value is shown in Table 2 after 5 measurements.

4. Evaluation of solvent resistance

The fabricated color filter was immersed in a heating oven at 230 캜 for 2 hours to compare and evaluate the color change before and after the evaluation. The formula to be used at this time is calculated by the following equation (1) representing the color change in the three-dimensional colorimetry defined by L *, a *, b *, and as the color change value is small, a reliable color filter can be manufactured .

When the value of DELTA E * ab is 3.0 or less, a person can not feel color difference.

Equation (1)

? Eab * = [(? L *) 2+ (? A *) 2+ (? B *) 2]

The results of the experimental values are shown in Table 2 below.

Adhesiveness Evaluation of Sensitivity Solvent resistance Pencil hardness Example 1 ○ 4 1.85 5 H Example 2 △ 6 2.24 4 H Example 3 ○ 4 1.93 5 H Example 4 ○ 4 1.74 5 H Example 5 △ 6 2.53 4 H Example 6 △ 6 2.60 4 H Comparative Example 1 △ 6 2.84 3 H Comparative Example 2 X 8 3.21 2 H Comparative Example 3 △ 6 2.90 3 H Comparative Example 4 X 10 3.34 1 H Comparative Example 5 X 8 3.09 2 H

As shown in Table 2, Examples 1 to 6 including a photopolymerizable compound having a urethane bond according to the present invention show excellent adhesion, sensitivity, solvent resistance and pencil hardness.

Claims (7)

1. A photosensitive resin composition comprising a photopolymerizable compound represented by the following formula (1)
[Chemical Formula 1]

(In the formula 1,
And R &lt; 2 &gt; are each independently - (C = O) -NH-R3,
Wherein R 3 is selected from the group consisting of a C 1 to C 11 alkyl group, a C 3 to C 12 cyclic alkyl group, a C 6 to C 20 aryl group and a C 6 to C 20 heteroaryl group, wherein the alkyl group, the cyclic alkyl group, C11 alkyl group, C3-C12 cyclic alkyl group, C6-C20 aryl group, and C6-C20 heteroaryl group). The method according to claim 1,
Wherein the photopolymerizable compound is a compound represented by one of the following formulas:

The method according to claim 1,
Wherein the alkali-soluble resin has an acid value of 20 to 200 mgKOH / g. The method according to claim 1,
Wherein the photosensitive resin composition comprises 5 to 50% by weight of a photopolymerizable compound based on the total weight% of the solid content of the photosensitive resin composition. The method according to claim 1,
Wherein the photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerization initiator, a colorant, and a solvent. A color filter made of the photosensitive resin composition according to any one of claims 1 to 5. An image display device comprising the color filter of claim 6.