KR101961959B1 - Colored photosensitive resin composition - Google Patents

Abstract

R1, R2는 각각 독립적으로 하기 화학식 2이고,
R3~R8은 각각 독립으로 수소원자, 할로겐, 또는 SO3-이고,
[화학식 2]

R9 는 하기 화학식 3이거나 질소 또는 산소 원자를 포함하는 헤테로환의 구조이고,
R10~R13는 각각 독립으로 수소원자, C1~C4의 선형 또는 비선형 알킬, 또는 SO3-이고,
[화학식3]

R14, R15는 각각 독립으로 수소원자이거나 C1~C8의 선형 또는 비선형의 알킬이며, R14, R15 모두 수소원자 일수 없다.
[화학식4]

R16은 C1~C8의 알킬이거나 하기 화학식 5로 표현되고,
R17는 C1~C8의 알킬 또는 페닐이고,
R18는 치환 또는 비치환된 디페닐설파이드기이며,
[화학식5]

R19는 C1~C4의 알킬이고,
R20는 C3~C8의 환의 구조이다.(A) comprises an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E) Soluble resin (B) has an acid value of 30 to 150 mgKOH / g, and the photopolymerization initiator (D) comprises a compound having a structure represented by the following formula (4), and the photosensitive resin composition A liquid crystal display element or an image pickup element including the color filter and the color filter.
[Chemical Formula 1]

R1 and R2 each independently represent the following formula (2)
R3 to R8 each independently represent a hydrogen atom, halogen, or SO3-,
(2)

R9 is a structure represented by the following formula (3), or a hetero ring structure containing a nitrogen or oxygen atom,
R10 to R13 each independently represent a hydrogen atom, C1 to C4 linear or non-linear alkyl, or SO3-,
(3)

R14 and R15 are each independently a hydrogen atom or a C1 to C8 linear or non-linear alkyl, and R14 and R15 are not both hydrogen atoms.
[Chemical Formula 4]

R16 is C1-C8 alkyl or represented by the following formula (5)
R17 is C1-C8 alkyl or phenyl,
R18 is a substituted or unsubstituted diphenylsulfide group,
[Chemical Formula 5]

R < 19 > is C1-C4 alkyl,
R20 is a C3 to C8 ring structure.

Description

COLORED PHOTOSENSITIVE RESIN COMPOSITION [0002]

The present invention relates to a colored photosensitive resin composition, a colored pattern formed from the composition, a color filter including the colored pattern, a liquid crystal display device having the same, and an imaging device.

Color filters are widely used in imaging elements, liquid crystal display elements, and the like, and their application range is rapidly expanding. A color filter used for a color liquid crystal display element, an image pickup element and the like is a system in which a colored photosensitive resin composition containing a coloring agent corresponding to each color of red, green and blue is applied uniformly by spin coating on a substrate on which a black matrix is pattern- The coating film formed by heating and drying (hereinafter also referred to as preliminary firing) may be exposed and developed, and if necessary, further heat curing (hereinafter also referred to as post-firing) may be repeated for each color, Color pixels are formed.

In recent years, color filters for liquid crystal displays (LCDs) have become increasingly large-sized as liquid-crystal displays are becoming increasingly demanded for constant definition, high definition, and high contrast. For example, Korean Patent Laid-Open No. 10-2010-0003699 discloses a coloring composition using a colorant comprising a chitosan dye. However, in order to obtain a color filter excellent in brightness and contrast ratio, development of a colored photosensitive resin composition containing dyes and pigments of other combinations other than those specifically disclosed in the above patent documents is required.

Korean Patent Publication No. 10-2010-0003699

The present invention provides a colored photosensitive resin composition for a color filter which can obtain a color filter excellent in brightness and contrast ratio in order to solve the above problems. An object of the present invention is to provide a colored photosensitive resin composition which has a high development speed and is excellent in sensitivity and adhesion so that there is no peeling of the pattern during the development process and excellent solvent resistance.

(A) comprises an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E) Wherein the alkali-soluble resin (B) has an acid value of 30 to 150 mgKOH / g, and the photopolymerization initiator (D) comprises a compound having a structure represented by the following formula (4).

 [Chemical Formula 1]

R1 and R2 each independently represent the following formula (2)

R3 to R8 each independently represent a hydrogen atom, halogen, or SO3-,

(2)

R9 is a structure represented by the following formula (3), or a hetero ring structure containing a nitrogen or oxygen atom,

R10 to R13 each independently represent a hydrogen atom, C1 to C4 linear or non-linear alkyl, or SO3-,

(3)

R14 and R15 are each independently a hydrogen atom or a C1 to C8 linear or non-linear alkyl, and R14 and R15 are not both hydrogen atoms.

[Chemical Formula 4]

R16 is C1-C8 alkyl or represented by the following formula (5)

R17 is C1-C8 alkyl or phenyl,

R18 is a substituted or unsubstituted diphenylsulfide group,

[Chemical Formula 5]

R < 19 > is C1-C4 alkyl,

R20 is a C3 to C8 ring structure.

The present invention also provides a color filter comprising a colored pattern formed by forming the colored photosensitive resin composition in a predetermined pattern, followed by exposure and development.

Further, the present invention provides a liquid crystal display element and an imaging element including the color filter.

The color filter manufactured using the colored photosensitive resin composition of the present invention has high brightness and contrast ratio, has a high developing speed, and is excellent in adhesion.

Therefore, the colored photosensitive resin composition of the present invention can be very usefully used for the production of a color filter.

The present invention relates to a colored photosensitive resin composition comprising a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E).

Hereinafter, the colored photosensitive resin composition of the present invention will be described in detail by the constituent components.

The colorant (A)

The colorant may be a pigment (a2) or a further dye (a4) which contains, as an essential component, a dye (a1) composed of the following formula (1) and which is generally used in the art.

dyes( a1 )

The colorant of the present invention comprises a dye (a1) composed of the following formula (1) as an essential component.

 [Chemical Formula 1]

R1 and R2 each independently represent the following formula (2)

R3 to R8 each independently represent a hydrogen atom, halogen, or SO3-,

(2)

R9 is a structure represented by the following formula (3), or a hetero ring structure containing a nitrogen or oxygen atom,

R10 to R13 each independently represent a hydrogen atom, C1 to C4 linear or non-linear alkyl, or SO3-,

(3)

R14 and R15 are each independently a hydrogen atom or a C1 to C8 linear or non-linear alkyl, and R14 and R15 are not both hydrogen atoms.

The amount of the dye (a1) to be used is in the range of 1 to 40 parts by weight, more preferably 5 to 30 parts by weight, based on 100 parts by weight of the solid content of the colorant (A) to be used. If the content of the dye (a1) exceeds 40 parts by weight on the basis of the above-mentioned criteria, the cured product of the colored photosensitive resin composition tends to be low and reliability is difficult to secure. When the content of the dye (a1) is less than 1 part by weight, the effect of improving the contrast ratio and transmittance is difficult.

Pigment ( a2 )

The pigment (a2) may be any of various pigments used in printing ink, inkjet ink and the like. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, Anthanthrone pigments, indanthrone pigments, pravanthrone pigments, anthraquinone pigments, anthanthrone pigments, anthanthrone pigments, anthanthrone pigments, indanthrone pigments, , 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 Pigments, but are not limited thereto.

CI 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

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

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

CI Pigment Green 7, 10, 15, 25, 36, 47 and 58

CI Pigment Brown 28

These 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 Green 7, C.I. Pigment Green 36, C.I. Pigment selected from Pigment Green 58 can be preferably used.

The content of the pigment (a2) is in the range of 20 to 90% by weight, preferably 30 to 70% by weight based on the total weight of the solid content in the colorant (A). When the content of the pigment is in the range of 20 to 90% by weight, the viscosity is low, the storage stability is excellent, the dispersing efficiency is high and the storage stability is excellent.

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 dispersion (a3) by containing the pigment dispersant (a3). According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained have.

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 .

Pigment dispersant ( a3 )

The pigment dispersant (a3) 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 (a3), 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, and may be used in combination with acrylic dispersion.

The amount of the pigment dispersant (a3) to be used is in the range of 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 (a3). If the content of the dispersant (a3) exceeds 60 parts by weight, the viscosity may be increased. If the content of the dispersant (a3) is less than 5 parts by weight, it may be difficult to atomize the pigment or cause gelation after dispersion.

dyes( a4 )

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, heat resistance and solvent resistance.

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

Green dyes such as CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like.

CI Solvent Yellow 14, 16, 21, 56, 151, 79, 93 having excellent solubility in organic solvents in CI solvent dyes; CI Solvent Red 8, 49, 89, 111, 122, 132, 146, 179; CI Solvent Orange 41, 45, 62 is preferred, and CI Solvent Yellow 21, 79; CI Solvent Red 8, 122, 132; CI Solvent Orange 45, 62 is more preferred.

Also, C.I. As an acid dye

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 Yellow dyes such as 1,1,1,2,2,2,2,2,2,23,28, 240,242, 243,251 and the like, such as, for example, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, ;

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;

Green dyes such as CI 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; CI Acid Red 92; CI Acid Green 27 is preferred.

As a C.I. direct dye,

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 , Yellow dyes such as 136, 138, and 141;

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;

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. As a modantoic dye

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

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;

Green dyes such as CI 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 additional dye (a4) in the colorant (A) is preferably 0.5 to 80 parts by weight, more preferably 0.5 to 60 parts by weight, and more preferably 1 to 50 parts by weight based on 100 parts by weight of the solid content of the colorant (A) The addition is particularly preferred. When the content of the additional dye (a4) in the above colorant (A) is in the above range, it is possible to prevent the problem of lowering the reliability of elution of the dye by the organic solvent after pattern formation, .

The content of the colorant (A) is preferably 5 to 60% by weight, and more preferably 10 to 45% by weight based on the solid content in the colored photosensitive resin composition. When the colorant (A) is contained in an amount of 5 to 60% by weight based on the above standard, the color density of the pixel is sufficient even when a thin film is formed, and the residue of the non- Do.

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

The alkali-soluble resin (B)

The alkali-soluble resin of the present invention is prepared by copolymerizing, as an essential component, an ethylenically unsaturated monomer (b1) having a carboxyl group in order to have solubility in an alkali developing solution used in a developing process for forming a pattern. In order to ensure compatibility with the dye (a2) and storage stability of the colored photosensitive resin composition, the acid value of the alkali-soluble resin (B) is preferably 30 to 150 mgKOH / g. When the acid value of the alkali-soluble resin (B) is less than 30 mgKOH / g, it is difficult to ensure a sufficient developing rate of the colored photosensitive resin composition. When the acid value exceeds 150 mgKOH / g, the adhesion with the substrate is decreased, , The dye in the colored photosensitive resin composition is precipitated or the storage stability of the colored photosensitive resin composition is lowered, and the viscosity tends to rise.

Specific examples of the ethylenically unsaturated monomer (b1) having a carboxyl group 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 of these dicarboxylic acids; (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both terminals such as? -carboxypolycaprolactone mono (meth) acrylate, and acrylic acid and methacrylic acid are preferable.

A hydroxyl group may be added to secure further developability of the alkali-soluble resin (B).

The ethylenically unsaturated monomer (b1) having a carboxyl group and the ethylenically unsaturated monomer (b2) having a hydroxyl group can be produced by copolymerizing an ethylenically unsaturated monomer (b1) having a carboxyl group and an ethylenically unsaturated monomer (b2) having a hydroxyl group in order to impart a hydroxyl group to the alkali- (B3) having a glycidyl group is further reacted with a copolymer of a glycidyl group-containing monomer and a glycidyl group-containing monomer. (B3) having a glycidyl group in addition to a copolymer of an ethylenically unsaturated monomer (b1) having a carboxyl group and an ethylenically unsaturated monomer (b2) having a hydroxyl group.

Specific examples of the butylenically unsaturated monomer (b2) having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl Hydroxy-3-phenoxypropyl (meth) acrylate, N-hydroxyethylacrylamide and the like, and 2-hydroxyethyl (meth) acrylate is preferable, and two or more kinds thereof can be used in combination.

Specific examples of the glycidyl group-containing monomer (b3) include butyl glycidyl ether, glycidyl propyl ether, glycidylphenyl ether, 2-ethylhexyl glycidyl ether, glycidyl butyrate, glycidyl methyl ether, Ethyl glycidyl ether, glycidyl isopropyl ether, t-butyl glycidyl ether, benzyl glycidyl ether, glycidyl 4-t-butyl benzoate, glycidyl stearate, aryl glycidyl ether, Methacrylic acid glycidyl ester, etc., and butyl glycidyl ether, aryl glycidyl ether, and methacrylic acid glycidyl ester are preferable, and two or more kinds may be used in combination.

The unsaturated monomers (b4) copolymerizable in the preparation of the alkali-soluble resin (B) are exemplified below, but are not limited thereto.

Specific examples of the polymerizable monomer (b4) having an unsaturated bond capable of copolymerization include styrene, vinyltoluene,? -Methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p- Aromatic vinyls such as vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m- vinyl benzyl glycidyl ether and p- compound;

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.

The monomers exemplified as the polymerizable monomer (b4) having an unsaturated bond capable of copolymerization may be used either individually or in combination of two or more.

The content of the alkali-soluble resin (B) should satisfy the condition that the sum of the hydroxyl value of the alkali-soluble resin (B) and the photopolymerizable compound (C) is from 50 mgKOH / g to 250 mgKOH / g, By weight, preferably 10 to 70% by weight, based on the total weight of the composition. When the content of the alkali-soluble resin (B) is 10 to 80% by weight based on the above-mentioned criteria, the solubility in a developing solution is sufficient and pattern formation is easy. In the development, film reduction of the pixel portion of the exposed portion is prevented, It is preferable that the dropout property is improved.

Photopolymerization  The compound (C)

The photopolymerizable compound (C) is a compound capable of polymerizing under the action of the photopolymerization initiator (D) described below, and a monofunctional monomer, a bifunctional monomer or a polyfunctional monomer can be used, and preferably a bifunctional or more polyfunctional monomer Can be used.

Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate or N- But are not limited thereto.

Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) , Bis (acryloyloxyethyl) ether of bisphenol A or 3-methylpentanediol di (meth) acrylate, but are not limited thereto.

Specific examples of the polyfunctional monomer include trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol tri (Meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa ) Acrylate or dipentaerythritol hexa (meth) acrylate, but are not limited thereto.

The photopolymerizable compound (C) is preferably contained in an amount of 5 to 45% by weight, more preferably 7 to 45% by weight based on the total weight of the solid components in the colored photosensitive resin composition. When the photopolymerizable compound (C) is included in the range described above, it is preferable because the strength and smoothness of the pixel portion can be improved.

Light curing Initiator (D)

The photopolymerization initiator (D) includes a photopolymerization initiator (d1) having a structure represented by the following general formula (4).

[Chemical Formula 4]

R16 is C1-C8 alkyl or represented by the following formula (5)

R17 is C1-C8 alkyl or phenyl,

R18 is a substituted or unsubstituted diphenylsulfide group,

[Chemical Formula 5]

R < 19 > is C1-C4 alkyl,

R20 is a C3 to C8 ring structure.

The photopolymerization initiator (d1), which is a structure of the above formula (4), prevents photodermability and sensitivity deterioration caused by the dye, thereby exhibiting effective photopolymerization properties in a colored photosensitive resin composition containing a dye as a colorant.

In addition, the photopolymerization initiator (d2) other than those described above may be further used in combination within the range not impairing the effects of the present invention. Typically, it is preferable to use at least one compound selected from the group consisting of an acetophenone-based compound, a benzophenone-based compound, a triazine-based compound, a nonimidazole-based compound, and a thioxanthone-based compound.

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

Examples of the benzophenone compound include benzophenone, methyl 0-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, (Trichloromethyl) -6- [2- (5-methylfuran-2- (4-methoxystyryl) -1,3,5-triazine, Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan- , 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- ) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

Specific examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbimidazole, 2,2'-bis (2,3- Phenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) , 2,2'-bis (2,6-dichlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) Imidazole compounds in which 4'5,5'-tetraphenyl-1,2'-biimidazole or phenyl groups at 4,4 ', 5,5' positions are substituted by carboalkoxy groups. Among them, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- , 2,2-bis (2,6-dichlorophenyl) -4,4'5,5'-tetraphenyl-1,2'-biimidazole is preferably used do.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4- .

The photopolymerization initiator (D) may further comprise a photopolymerization initiator (d3) to improve the sensitivity of the colored photosensitive resin composition of the present invention. The colored photosensitive resin composition according to the present invention contains a photopolymerization initiation auxiliary (d3), whereby the sensitivity is further increased and the productivity can be improved.

As the photopolymerization initiation assistant (d3), for example, 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 can be preferably used.

As the amine compound, an aromatic amine compound is preferably used. Specific examples of the amine compound include aliphatic amine compounds such as triethanolamine, methyldiethanolamine and triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4- Dimethylaminobenzoic acid, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone ), 4,4'-bis (diethylamino) benzophenone, and the like.

The carboxylic acid compound is preferably an aromatic heteroacetic acid, and more specifically, it is preferably an aromatic heteroaromatic acid such as phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthio Acetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.

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-mercaptobutyloxyethyl) 1,3,5-triazine-2,4,6 (1H, 3H, 5H) -thione, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexacis (3-mercaptopropionate), and tetraethylene glycol bis (3-mercaptopropionate) .

The photopolymerization initiator (D) is contained in an amount of 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the alkali-soluble resin (B) and the photopolymerizable compound (C) contained in the colored photosensitive resin composition of the present invention . When the photopolymerization initiator (D) is contained within the above-described range, the photosensitive resin composition is highly sensitive and the exposure time is shortened, which is preferable because productivity can be improved and high resolution can be maintained. Further, in the case of using a composition having the above-described conditions, the strength and surface smoothness of the formed pixel portion can be improved.

When the photopolymerization initiator (d3) is further used, the amount of the photopolymerization initiator (D3) is preferably 0.1 to 40 parts by weight, more preferably 0.1 to 40 parts by weight, based on 100 parts by weight of the alkali- May be contained in an amount of 1 to 30 parts by weight. When the photopolymerization initiator (d2) is included in the above-described range, the sensitivity of the colored photosensitive resin composition becomes higher and the productivity of the color filter formed using the composition is improved.

Solvent (E)

As long as the solvent (E) is effective for dissolving other components contained in the colored photosensitive resin composition, a solvent used in a conventional photosensitive resin composition may be used without particular limitation, and in particular, an ether, an aromatic hydrocarbon, a ketone, , Esters, amides and the like can be preferably used.

The solvent (E) specifically includes 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 dipropyl ether and diethylene glycol dibutyl ether; Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate; 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; Esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as? -Butyrolactone.

The solvent (E) is preferably an organic solvent having a boiling point of 100 ° C to 200 ° C on the application and drying surface, more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl Lactate, butylacetate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like.

The above-exemplified solvents (E) may be used alone or in admixture of two or more, and they 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 colored photosensitive resin composition of the present invention . When the solvent (E) is included in the above-mentioned range, it is possible to improve the coating property when applied with a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater Can be obtained.

Additive (F)

The colored photosensitive resin composition of the present invention may contain, in addition to the above components, additives such as fillers, other polymer compounds, curing agents, pigment dispersants, adhesion promoters, ultraviolet absorbers, ) Can be used in combination.

The filler may be glass, silica, alumina, or the like, but is not limited thereto.

Specific examples of the other polymer compound include a curable resin such as an epoxy resin and a maleimide resin, a thermoplastic resin such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, polyurethane and the like But is not limited thereto.

The curing agent is used for increasing the curing depth and mechanical strength. Specifically, an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, and an oxetane compound may be used, but the present invention is not limited thereto. Specific examples of the epoxy compound include epoxy resins such as bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolak epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin, Alicyclic or aromatic epoxy compounds, butadiene (co) polymeric epoxides, isoprene (co) polymers other than the brominated derivatives, epoxy resins and brominated derivatives of such epoxy resins, A polymeric epoxide, a glycidyl (meth) acrylate (co) polymer, and triglycidylisocyanurate, but are not limited thereto. Specific examples of the oxetane compound include, but are not limited to, carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, and cyclohexanedicarboxylic acid bisoxetane. It is not.

The curing agent may be used together with a curing agent in combination with a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound. Specific examples of the curing auxiliary compound include polyvalent carboxylic acids, polyvalent carboxylic anhydrides, and acid generators. The carboxylic acid anhydrides may be those commercially available as an epoxy resin curing agent. Examples of commercially available epoxy resin curing agents include trade name (ADEKA HARDONA EH-700) (ADEKA INDUSTRIAL CO., LTD.), Trade name (RICACIDO HH) (Manufactured by Shin-Etsu Chemical Co., Ltd.).

The curing agent and the curing auxiliary compound exemplified above may be used alone or in combination of two or more.

The above-mentioned pigment dispersant may be a commercially available surfactant. Specifically, it may be a surfactant selected from the group consisting of silicone, fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants, have. More specifically, examples thereof include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine modified polyurethanes, polyethylene imines and the like. (Trade name: KP (Shinetsugaku Kagaku Kogyo Co., Ltd.), POLYFLOW (Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by TOKEM PRODUCTS CO., LTD.), MEGAFAC Asahi guard, Surflon (Asahi Glass Co., Ltd.), SOLSPERSE (Lubrisol), EFKA (Nippon Ink Chemical Industries Co., Ltd.), Flourad (Sumitomo 3M Co., Ltd.) (EFKA Chemicals), PB 821 (Ajinomoto), and Disperbyk-series (BYK-chemi).

Specific examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (2-aminoethyl) (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- Methoxysilane, 3-isocyanatepropyltrimethoxysilane, and 3-isocyanatepropyltriethoxysilane, or a mixture thereof.

The adhesion promoter may be included in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 2 parts by weight, based on the solid content of the composition.

Specific examples of the ultraviolet absorber include, but are not limited to, 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.

The anti-aggregation agent may be, for example, sodium polyacrylate, but is not limited thereto.

In the present invention, the additive (F) may be contained in an amount of 0.01 to 15% by weight based on the total weight of the solid content in the colored photosensitive resin composition.

The process for producing the colored photosensitive resin composition of the present invention will be described as follows.

First, the pigment (a2) in the colorant (A) is mixed with the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, the pigment dispersant (a3), part or all of the alkali-soluble resin (B), or the dye (a4) may be mixed and dissolved or dispersed with the solvent (E).

The dye (a1), the remainder of the alkali-soluble resin (B), the photopolymerizable compound (C) and the photopolymerization initiator (D), if necessary, the additive (F) and the solvent (E) The colored photosensitive resin composition according to the present invention can be prepared.

The present invention also relates to a color filter including a color pattern formed by forming the colored photosensitive resin composition in a predetermined pattern, followed by exposure and development.

The color filter may be manufactured by a conventional method well known in the art.

The present invention also relates to a liquid crystal display element and an image pickup device including the color filter.

The liquid crystal display element and the image pickup element include configurations known to those skilled in the art, except that the color filter is provided. That is, the liquid crystal display element and the image pickup element to which the color filter of the present invention can be applied are all included in the present invention.

Hereinafter, the present invention will be described in more detail based on 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 Production Examples, Examples and Comparative Examples, "%" and "part" representing the content are based on weight unless otherwise specified.

Synthesis of dyes

Synthesis Example 1 Synthesis of Dye D1

20 parts by weight of Acid blue 80 was added to the reaction vessel, and 200 parts by weight of chloroform was added thereto, followed by stirring for 1 hour. After stirring, 9.7 parts by weight of N, N-dimethyl formamide was added and stirred for 1 hour. Then, 12.17 parts by weight of thionyl chloride was added and stirred for 3 hours. Then, 3.77 parts by weight of piperidine was added thereto, followed by stirring for 3 hours. Then, 20 parts by weight of triethylamine and 20 parts by weight of methanol were added to terminate the reaction. The reaction product was washed with distilled water several times, filtered, and the obtained solid was vacuum-dried at room temperature for 48 hours to obtain a dye D1.

Synthesis Example 2 Synthesis of Dye D2

20 parts by weight of Acid blue 80 was added to the reaction vessel, and 200 parts by weight of chloroform was added thereto, followed by stirring for 1 hour. After stirring, 9.7 parts by weight of N, N-dimethyl formamide was added and stirred for 1 hour. Then, 12.17 parts by weight of thionyl chloride was added and stirred for 3 hours. Thereafter, 3.23 parts by weight of diethylamine was added thereto, followed by stirring for 3 hours. Then, 20 parts by weight of triethylamine and 20 parts by weight of methanol were added to terminate the reaction. The reaction product was washed with distilled water several times, filtered, and the obtained solid was vacuum-dried at room temperature for 48 hours to obtain dye D2.

Preparation of pigment dispersion composition

<Pigment dispersion composition M1>

12.0 parts by weight of CI Pigment Blue 15: 6 as a pigment, 4.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 54 parts by weight of propylene glycol methyl ether acetate as a solvent and 30 parts by weight of propylene glycol monomethyl ether were added to a bead mill For 12 hours to prepare a pigment dispersion M1.

Synthesis of alkali-soluble resin

&Lt; Synthesis Example 3 &

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 13.0 parts of acrylic acid, 10 parts of benzyl methacrylate, 57.0 parts of 4-methylstyrene, 20 parts of methyl methacrylate and 3 parts of n-dodecyl mercapto were charged and replaced with nitrogen. Thereafter, the temperature of the reaction solution was elevated to 110 DEG C with stirring, and the reaction was carried out for 6 hours. The alkali-soluble resin thus synthesized had a solid dispersion value of 100.2 mgKOH / g and a weight average molecular weight Mw of about 15110 as measured by GPC.

&Lt; Synthesis Example 4 &

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 9.0 parts of acrylic acid, 10 parts of benzyl methacrylate, 54.0 parts of 4-methylstyrene, 20 parts of methyl methacrylate, 7.0 parts of 2-hydroxyethyl methacrylate and 3 parts of n-dodecyl mercapto were charged and replaced with nitrogen. Thereafter, the temperature of the reaction solution was elevated to 110 DEG C with stirring, and the reaction was carried out for 6 hours. The alkali-soluble resin thus synthesized had a solid dispersion value of 69.4 mgKOH / g and a weight average molecular weight Mw of about 13180 as measured by GPC.

&Lt; Synthesis Example 5 &

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 3.5 parts of acrylic acid, 10 parts of benzyl methacrylate, 66.5 parts of 4-methylstyrene, 20 parts of methyl methacrylate and 3 parts of n-dodecyl mercapto were charged and replaced with nitrogen. Thereafter, the temperature of the reaction solution was elevated to 110 DEG C with stirring, and the reaction was carried out for 6 hours. The alkali-soluble resin thus synthesized had a solid dispersion value of 26.5 mgKOH / g and a weight average molecular weight Mw of about 16070 as measured by GPC.

&Lt; Synthesis Example 6 &

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 22.5 parts of acrylic acid, 10 parts of benzyl methacrylate, 47.5 parts of 4-methylstyrene, 20 parts of methyl methacrylate and 3 parts of n-dodecylmercapto were charged and replaced with nitrogen. Thereafter, the temperature of the reaction solution was elevated to 110 DEG C with stirring, and the reaction was carried out for 6 hours. The thus-synthesized alkali-soluble resin had a solid dispersion value of 172.3 mgKOH / g and a weight average molecular weight Mw of about 14850 as measured by GPC.

Preparation of colored photosensitive resin composition

&Lt; Example 1 >

22.50 parts of the pigment dispersion composition M1, 0.30 part of the dye D1, 15.15 parts of the resin of Synthesis Example 3, 5.05 parts of acrylateate of dipentaerythritol, 1.01 parts of Irgacure OXE01 (manufactured by BASF) 30.49 parts of monomethyl ether acetate, and 25.50 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Example 2 >

22.50 parts of the pigment dispersion composition M1, 0.30 part of the dye D1, 15.15 parts of the resin of Synthesis Example 4, 5.05 parts of acrylate of dipentaerythritol, 1.01 parts of Irgacure OXE01 (manufactured by BASF) 30.49 parts of monomethyl ether acetate, and 25.50 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Example 3 >

22.50 parts of the pigment dispersion composition M1, 0.30 part of the dye D2, 15.15 parts of the resin of Synthesis Example 4, 5.05 parts of acrylateate of dipentaerythritol, 1.01 parts of Irgacure OXE01 (manufactured by BASF) 30.49 parts of monomethyl ether acetate, and 25.50 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Comparative Example 1 &

22.50 parts of the pigment dispersion composition M1, 0.30 part of the dye D1, 15.15 parts of the resin of Synthesis Example 5, 5.05 parts of acrylate of dipentaerythritol, 1.01 parts of Irgacure OXE01 (BASF) 30.49 parts of monomethyl ether acetate, and 25.50 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Comparative Example 2 &

22.50 parts of the pigment dispersion composition M1, 0.30 part of the dye D1, 15.15 parts of the resin of Synthesis Example 6, 5.05 parts of the acrylate compound of dipentaerythritol, 1.01 parts of Irgacure OXE01 (manufactured by BASF) 30.49 parts of monomethyl ether acetate, and 25.50 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Comparative Example 3 &

22.50 parts of the pigment dispersion composition M1, 0.30 part of the dye D1, 15.15 parts of the resin of Synthesis Example 3, 5.05 parts of acrylate compound of dipentaerythritol, 1.01 part of Irgacure OXE02 (BASF) 30.49 parts of monomethyl ether acetate, and 25.50 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Comparative Example 4 &

22.5 parts of the above pigment dispersion composition M1, 15.15 parts of the resin of Synthesis Example 3, 5.05 parts of dipentaerythritol acrylate, 1.01 part of Irgacure OXE01 (manufactured by BASF), 30.49 parts of propylene glycol monomethyl ether acetate, And 25.50 parts by weight of glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Comparative Example 5 &

, 0.30 part of Solvent Blue 44 (trade name: Savinyl Blue GLS, manufactured by Clariant), 15.15 parts of the resin of Synthesis Example 3, 5.05 parts of acrylate of dipentaerythritol, Irgacure OXE01 (Manufactured by BASF), 30.49 parts of propylene glycol monomethyl ether acetate, and 25.50 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

Experimental Example  1: Manufacture of color filters

A color filter was prepared using the colored photosensitive resin compositions prepared in Examples 1 to 3 and Comparative Examples 1 to 5.

Specifically, each of the above-mentioned colored photosensitive resin compositions was coated on a glass substrate by spin coating, and then placed on a heating plate and held at a temperature of 100 캜 for 3 minutes to form a thin film. Then, a test photomask having a line / space pattern of 50 mu m was placed on the thin film and irradiated with ultraviolet rays at a distance of 100 mu m from the test photomask. 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, dried by blowing nitrogen gas, and heated in a heating oven at 230 ° C for 20 minutes to prepare a color filter.

The film thickness of the color filter prepared above was 2.3 탆.

Experimental Example  2: Measurement of color filter characteristics

The brightness, contrast ratio, developing speed and adhesion of the color filter prepared in Experimental Example 1 were measured and evaluated as follows. The results are shown in Table 1 below.

<Contrast Ratio and Brightness>

The contrast ratio and the luminance were measured using the same color filter except that the test photomask was not used in Experimental Example 1 above.

In the case of the contrast ratio, the substrate of the color filter was sandwiched between two sheets of polarizing plates, and the maximum and minimum values of light intensity transmitted through the front side deflector plate were measured while being illuminated with a fluorescent lamp (wavelength of 380 to 780 nm) -2000 luminance meter (KONICA MINOLTA), and the contrast ratio, which is a value obtained by dividing the maximum value by the minimum value, was calculated. For luminance, the luminance was measured using a colorimeter (OSP-200 manufactured by Olympus Corporation).

&Lt; Development speed >

The time taken for the unexposed area to completely dissolve in the developing solution at the time of development was measured.

&Lt; Adhesion >

When the generated pattern was evaluated through an optical microscope, the following pattern was evaluated as a degree of peeling phenomenon.

○: No pattern peeling

△: 1 to 3 pattern peeling

X: Pattern peeling 4 or more

Example Comparative Example NO One 2 3 One 2 3 4 5 Contrast ratio 6100 6200 5900 6000 5600 4900 3800 6200 Luminance 13.8 13.7 13.7 13.7 13.6 12.9 10.8 10.7 Development speed 15 18 18 68 9 19 21 14 Adhesiveness ○ ○ ○ ○ X ○ ○ ○

As can be seen from Table 1, the color photosensitive resin compositions according to Examples 1 to 3 exhibited higher brightness and contrast ratio, faster developing speed and better adhesion than Comparative Examples.

Claims (7)

(A) comprises an alkali soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E) The alkali-soluble resin (B) has an acid value of 30 to 150 mgKOH / g, and includes benzylmethacrylate and methylstyrene, and the photopolymerization initiator (D) comprises a compound having a structure represented by the following formula Resin composition:
[Chemical Formula 1]

R1 and R2 each independently represent the following formula (2)
R3 to R8 each independently represent a hydrogen atom, halogen, or SO3-,

(2)

R9 is a structure represented by the following formula (3), or a hetero ring structure containing a nitrogen or oxygen atom,
R10 to R13 each independently represent a hydrogen atom, C1 to C4 linear or non-linear alkyl, or SO3-,

(3)

R14 and R15 are each independently a hydrogen atom or a C1 to C8 linear or non-linear alkyl; R14 and R15 are not both hydrogen atoms;

[Chemical Formula 4]

R16 is C1-C8 alkyl or represented by the following formula (5)
R17 is C1-C8 alkyl or phenyl,
R18 is a substituted or unsubstituted diphenylsulfide group,
[Chemical Formula 5]

R &lt; 19 &gt; is C1-C4 alkyl,
R20 is a C3 to C8 ring structure. The method according to claim 1,
The colored photosensitive resin composition
(A), 10 to 80% by weight of an alkali-soluble resin (B) and 5 to 45% by weight of a photopolymerizable compound (C) in a proportion of 5 to 60% by weight, based on the solid weight of the colored photosensitive resin composition ;
0.1 to 40 parts by weight of a photopolymerization initiator (D) based on 100 parts by weight of the alkali-soluble resin (B) and the photopolymerizable compound (C);
And a solvent (E) in an amount of 60 to 90% by weight based on the total weight of the colored photosensitive resin composition. The method of claim 2,
The colored photosensitive resin composition according to claim 1, wherein the amount of the dye of formula (1) is 1 to 40 parts by weight based on 100 parts by weight of the solid content of the colorant (A). The method according to claim 1,
Wherein the sum of the hydroxyl value of the alkali-soluble resin (B) and the photopolymerizable compound (C) is 50 to 250 mgKOH / g. A color filter comprising a color pattern formed by forming a colored photosensitive resin composition according to any one of claims 1 to 4 in a predetermined pattern, followed by exposure and development. A liquid crystal display element comprising the color filter of claim 5. An imaging device comprising the color filter of claim 5.