KR102572680B1 - Red colored photosensitive resin composition, color filter and display device comprising the same - Google Patents

Abstract

The present invention includes a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E), wherein the colorant (A) includes a red pigment and a black pigment. As a red photosensitive resin composition, characterized in that the spectral transmittance at a wavelength of 430 to 590 nm is 20% or less, and the spectral transmittance at a wavelength of 635 to 780 nm is 70% or more and less than 90%, a color filter prepared using the same, and It relates to a display device including the color filter. The red photosensitive resin composition of the present invention is characterized in that it can solve the problem of lack of high color reproducibility and fairness of the conventional red photosensitive resin composition while replacing a polarizing plate in a display device.

Description

Red photosensitive resin composition, a color filter manufactured using the same, and a display device including the color filter

The present invention relates to a red photosensitive resin composition, a color filter manufactured using the same, and a display device including the color filter.

Recently, a flexible display device capable of displaying an image even if it is bent like paper by forming a display unit and wiring on a flexible substrate such as plastic, which is a flexible material, has recently been in the limelight.

Flexible display devices have a wide range of applications, from computer monitors and TVs to personal portable devices. In particular, Organic Light Emitting Display (OLED), unlike Liquid Crystal Display (LCD), Since it does not require a light source and can be implemented with a relatively thin thickness, research on organic light emitting devices is being actively conducted in relation to flexible display devices.

On the other hand, in order for the flexible display element to be applied in practice, it should be able to implement full color, have low power consumption, and be easily readable even outdoors when compared to various current display products.

In this sense, the organic light emitting device has become the most useful resource as a light source for a flexible display device because it has the possibility of realizing full color, low power consumption, and fast response speed. The current organic light emitting device includes an encapsulation barrier layer to protect the organic light emitting device from oxygen and moisture, and a polarizer to maintain a high contrast ratio for outdoor readability. need.

However, when a polarizing plate having a hard property is applied, a disadvantage in that flexibility of the flexible display device is reduced may occur. On the other hand, when the polarizer is not applied, external light is transmitted into the flexible display device and then reflected back out, mixing colors with light emitted from the original organic light emitting device, and the contrast ratio under the external light source is greatly reduced.

Accordingly, research to improve this has been actively conducted recently, and as an example, Korean Patent Publication No. 10-2013-0134494 proposes an ink composition containing a colorant including a green colorant and a yellow colorant, a binder resin, and a block isocyanate group, Korean Patent Publication No. 10-2013-0134498 proposes an ink composition containing a colorant including a red colorant and a green colorant, a binder resin, and a block isocyanate group. However, in the case of the prior art, the selection range of colorants is limited in implementing high color reproducibility, and the implementation of various color gamuts is insufficient, and in addition, fairness such as tearing and undercutting is lacking in pattern formation, so that continuous Improvements are desired in the art.

Republic of Korea Patent Publication No. 10-2013-0134494 Republic of Korea Patent Publication No. 10-2013-0134498

Accordingly, it is an object of the present invention to provide a red photosensitive resin composition for forming a pixel capable of solving the conventional lack of fairness and realizing high color reproducibility while replacing a polarizing plate.

In addition, an object of the present invention is to provide a color filter prepared using the red photosensitive resin composition and a display device including the color filter.

The present invention includes a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E), wherein the colorant (A) includes a red pigment and a black pigment. A red photosensitive resin composition is provided.

In one embodiment, the spectral transmittance at a wavelength of 430 to 590 nm may be 20% or less, and the spectral transmittance at a wavelength of 635 to 780 nm may be 70% or more and less than 90%.

Another embodiment may have a spectral transmittance of 80% or more and less than 90% at a wavelength of 635 to 780 nm.

In another embodiment, the red pigment is C.I. Pigment Red 179, C.I. Pigment Red 177, C.I. Pigment Red 209, C.I. Pigment Red 242 and C.I. It may be one or more selected from the group consisting of Pigment Red 254.

In another embodiment, the black pigment is a mixture of red, blue, and green pigments, C.I. Pigment Black 1, C.I. It may be at least one selected from the group consisting of pigment black 7, carbon black, organic black pigment, and titanium black.

Another embodiment may be that the black pigment is included in an amount of 0.5 to 10% by weight based on the total solid content of the colorant.

In another embodiment, the weight ratio of the red pigment to the black pigment may be 99.99 to 80:20 to 0.1.

Another embodiment is 10 to 80% by weight of the colorant (A), 5 to 80% by weight of the alkali-soluble resin (B), and 5 to 50% by weight of the photopolymerizable compound (C), based on the total weight of the solid content in the red photosensitive resin composition. The photopolymerization initiator (D) includes 0.1 to 40 parts by weight based on 100 parts by weight of the total solid content of the alkali-soluble resin (B) and the photopolymerizable compound (C), and the solvent (E) is the total weight of the red photosensitive resin composition It may be to include 25 to 80% by weight relative to.

In another embodiment, the colorant may further include a yellow pigment.

Another embodiment may include 3 to 30 parts by weight of the yellow pigment based on 100 parts by weight of the total amount of the red pigment and the black pigment.

Another embodiment is that the yellow pigment is C.I. Pigment Yellow 129, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139 and C.I. It may be one or more selected from the group consisting of Pigment Yellow 150.

Another embodiment may be that the acid value of the alkali-soluble resin is 30 to 150mgKOH / g and the glass transition temperature is 100 ℃ or more.

In addition, the present invention provides a color filter prepared using the red photosensitive resin composition, and the color filter has high color reproducibility without using a polarizing plate.

In addition, the present invention provides a display device including the color filter.

One embodiment may include a red light source.

In another embodiment, the display device may be an organic light emitting device.

In another embodiment, the display device may be a flexible display device.

The red photosensitive resin composition of the present invention is characterized in that it can solve the problem of lack of high color reproducibility and fairness of the conventional red photosensitive resin composition for forming pixels while replacing a polarizing plate in a display device. In particular, the spectral transmittance at a wavelength of 430 to 590 nm is 20% or less (if the spectral transmittance exceeds 20%, there is a problem in that the color purity of red is lowered), and the spectral transmittance at a wavelength of 635 to 780 nm is 70% or more 90 It is characterized by less than %.

1 to 3 show transmittance according to wavelength as a result of Experimental Example 2. In particular, FIG. 2 is a graph showing the spectral transmittance at 430 to 590 nm according to the results of Experimental Example 1, and FIG. 3 is a graph showing the spectral transmittance at 635 to 775 nm according to the results of Experimental Example 1.

The present invention relates to a red photosensitive resin composition, a color filter manufactured using the same, and a display device including the color filter.

The present invention is a composition of a red photosensitive resin composition, and since the pigment dispersion composition includes a red pigment and a black pigment as essential components, colors can be implemented without using a polarizing plate, and in particular, a spectral transmittance in a specific range in a specific range of wavelengths It is characterized by

Hereinafter, the present invention will be described in detail.

Colorant (A)

The colorant may be included in an amount of 10 to 80% by weight, preferably 20 to 60% by weight, and more preferably 30 to 50% by weight, based on the total weight of solids in the red photosensitive resin composition.

The pigment (a1) included in the colorant essentially includes a red pigment and a black pigment. The weight ratio of the red pigment and the black pigment described above may be 99.9 to 80:20 to 0.1, preferably 99.99 to 90:10 to 0.5. Outside the above range, the spectral transmittance at a wavelength of 635 to 780 nm may be less than 70% or more than 90% (when the spectral transmittance is less than 70%, the external light reflection effect is good, but the visibility due to the decrease in luminance is poor, and the transmittance exceeds 90%). In case of , the luminance is good, but the external light reflection effect is insignificant).

As the black pigment usable in the present invention, black pigments used in the art may be used without particular limitation, for example, pigments in which red, blue and green are mixed, C.I Pigment Black 1 and 7, carbon black, organic black, Titanium black and the like may be used alone or in combination of two or more, preferably one selected from carbon black and organic black.

In the present invention, the black pigment may be 0.5 to 10% by weight based on the total weight of the solid content of the colorant, and the colorant refers to dyes and pigments included in the pigment dispersion composition. Based on the above, when the black pigment is less than 0.5% by weight, it is difficult to obtain the desired effect of preventing reflection of external light, and when it is greater than 10% by weight, problems may occur in visibility.

Hereinafter, the colorant will be described in detail.

pigment (a1)

The pigment (a1) essentially contains a red pigment and a black pigment.

The red pigments of the present invention are, for example, C.I. Pigment Red 177, C.I. Pigment Red 179, C.I. Pigment Red 202, C.I. Pigment Red 206, C.I. Pigment Red 207, C.I. Pigment Red 208, C.I. Pigment Red 209, C.I. Pigment Red 215, C.I. Pigment Red 216, C.I. Pigment Red 220, C.I. Pigment Red 224, C.I. Pigment Red 226, C.I. Pigment Red 242, C.I. Pigment Red 243, C.I. Pigment Red 245, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264 and C.I. It may be one or more selected from the group consisting of Pigment Red 265, among which C.I. Pigment Red 179, C.I. C.I. Pigment Red 177, Pigment Red 209, C.I. Pigment Red 242 and C.I. Pigment Red 254 is preferred.

The black pigment of the present invention is carbon black; organic black pigment; titanium black; and a pigment dispersion in which red, blue and green are mixed, C.I. Pigment Black 1, C.I. Pigment Black 7 or the like can be used.

More specifically, the black pigment may be used by preparing a colored dispersion obtained by mixing carbon black and two or more colored pigments and milling.

Usable carbon blacks include CHBK-17 from Mikuni Color Co.; Donghae Carbon Co., Ltd.'s cisto 5HIISAFHS, cisto KH, cisto 3HHAF-HS, cisto NH, cisto 3M, cisto 300HAF-LS, cisto 116HMMAF-HS, cisto 116MAF, cisto FMFEF-HS, cisto SOFEF, cisto VGPF, cisto SVHSRF-HS, and cisto SSRF; Diagram Black, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Diagram LR from Mitsubishi Chemical Corporation , #2700, #2600, #2400, #2350, #2300, #2200, #1000, #980, #900, MCF88, #52, #50, #47, #45, #45L, #25, #CF9 , #95, #3030, #3050, MA7, MA77, MA8, MA11, OIL7B, OIL9B, OIL11B, OIL30B, and OIL31B; PRINTEX-U, PRINTEX-V, PRINTEX-140U, PRINTEX-140V, PRINTEX-95, PRINTEX-85, PRINTEX-75, PRINTEX-55, PRINTEX-45, PRINTEX-300, PRINTEX-35, PRINTEX-25, PRINTEX-200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100, and LAMP BLACK-101; RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA, RAVEN-850, RAVEN-820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN-420, RAVEN-410, RAVEN- 2500ULTRA, RAVEN-2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, and RAVEN-1170.

Color pigments that can be mixed with the carbon black include carmine 6B (C.I. 12490), phthalocyanine green (C.I. 74260), phthalocyanine blue (C.I. 74160), Mitsubishi carbon black MA100, perylene black (BASF K0084. K0086), and cyanine black. , Linol Yellow (C.I.21090), Linol Yellow GRO (C.I. 21090), Benzidine Yellow 4T-564D, Mitsubishi Carbon Black MA-40, Victoria Pure Blue (C.I.42595), C.I. PIGMENT RED97, 122, 149, 168, 177, 180, 192, 215, C.I. PIGMENT GREEN 7, 36, C.I. PIGMENT 15:1, 15:4, 15:6, 22, 60, 64, C.I. PIGMENT 83, 139 C.I. PIGMENT VIOLET 23 and the like, and other white pigments and fluorescent pigments may also be used.

The carbon black is not particularly limited as long as it is a light-shielding pigment, and known carbon black can be used. Specific examples of the black pigment carbon black include channel black, furnace black, thermal black, and lamp black.

In addition, it may optionally contain a yellow pigment.

The yellow pigment is C.I. Pigment Yellow 138, C.I. Pigment Yellow 139 and C.I. It may be one or more selected from the group consisting of Pigment Yellow 150, preferably C.I. Pigment Yellow 139 and C.I. Pigment Yellow 150.

The yellow pigment may include 3 to 30 parts by weight based on 100 parts by weight of the total amount of the red pigment and the black pigment. When the yellow pigment is included within the above content range, the pigment content in the resist based on the solid content can be lowered, and it is preferable because it is advantageous for pattern adhesion and straightness in processability.

The content of the pigment (a1) may be 10 to 90% by weight, preferably 20 to 50% by weight based on the total weight of solids in the colorant (A). When the content of the pigment is in the range of 10 to 90% by weight based on the above, it is preferable because it is effective in increasing the contrast ratio with low viscosity, excellent storage stability, and high dispersion efficiency. It is preferable to use a pigment dispersion in which the particle size is uniformly dispersed as the pigment. One example of a method for uniformly dispersing the particle size of the pigment is a method of dispersing treatment by containing a pigment dispersant (a2), and according to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained. there is.

Pigment Dispersant (a2)

The pigment dispersant (a2) is added for deagglomeration and stability of the pigment, and generally used in the art may be used without limitation. Preferably, it is good to contain an acrylate-based dispersant (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 the living control method as suggested in Korean Patent Publication No. 2004-0014311, and the commercial product of the acrylate-based dispersant prepared through the living control method is DISPER BYK- 2000, DISPER BYK-2001, DISPER BYK-2070, and DISPER BYK-2150.

The above-exemplified acrylic dispersants may be used alone or in combination of two or more. As the dispersant (a2), other resin-type pigment dispersants may be used in addition to the above-described acrylic dispersants. The other resin-type pigment dispersants include known resin-type pigment dispersants, particularly polycarboxylic acid esters represented by polyurethanes and polyacrylates, unsaturated polyamides, polycarboxylic acids, and (partial) polycarboxylic acids. Amine salts, ammonium 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 ) an oily dispersant such as an amide formed by reaction of a polyester having a carboxyl group with a poly(lower alkyleneimine) or a salt thereof; water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinyl pyrrolidone; Polyester; modified polyacrylate; adducts of ethylene oxide/propylene oxide and phosphate esters; and the like. Commercially available cationic resin dispersants include, for example, BYK (Big) Chemie brand names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK- 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; BASF brand names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Trade names of Lubirzol: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10; Trade names of Kawaken Fine Chemical Co.: HINOACT T-6000, HINOACT T-7000, HINOACT T-8000; Trade names of Ajinomoto: AJISPUR PB-821, AJISPUR PB-822, AJISPUR PB-823; Trade names of Kyoeisha Chemical Co., Ltd.: FLORENE DOPA-17HF, FLORENE DOPA-15BHF, FLORENE DOPA-33, FLORENE DOPA-44 and the like. In addition to the above 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 an acrylic dispersant.

The amount of the dispersant (a2) 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 (a1) used. If the content of the dispersant (a2) exceeds 60 parts by weight based on the above, the viscosity may increase, and if it is less than 5 parts by weight, it may be difficult to atomize the pigment or cause problems such as gelation after dispersion.

Dye (a3)

The dye (a3) may optionally be included in the colorant. The dye (a3) may be additionally used without limitation as long as it has solubility in organic solvents. Preferably, it is preferable to use a dye capable of securing reliability such as solubility in an alkaline developing solution, heat resistance, and solvent resistance while having solubility in organic solvents. As the dye, acid dyes having an acid group such as sulfonic acid or carboxylic acid, salts of acid dyes and nitrogen-containing compounds, sulfonamides of acid dyes, and derivatives thereof may be used. Acid dyes of the system and their derivatives can also be selected. Preferably, the dye may be a compound classified as a dye in the color index (published by The Society of Dyers and Colourists) or a known dye described in a dyeing note (color dyeing yarn).

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

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. Among solvent dyes, C.I. Solvent Yellow 14, 16, 21, 56, 151, 79, 93 are preferred, with dual C.I. Solvent Yellow 21, 79; is more preferable

Also, C.I. C.I. 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, 1 78, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 2 51st The yellow dye of , etc. are mentioned.

Among acid dyes, C.I. Acid Yellow, which has excellent solubility in organic solvents, is preferred.

Also as a C.I. direct dye,

C.I. 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.

Also, C.I. as modanto dye

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

These dyes can be used individually or in combination of two or more types, respectively.

Dispersing solvent (a4)

The dispersion solvent (a4) may be optionally included in the colorant, and the type is not particularly limited, and various organic solvents used in the art may be used.

Specifically, for example, 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 dimethyl ether, and diethylene glycol diethyl ether Diethylene glycol dialkyl ethers such as diethylene glycol dipropyl ether and diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, propylene glycol monomethyl ether acetate , alkylene glycol alkyl ether acetates such as propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate and methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, methyl ethyl Ketones such as ketones, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin, ethyl 3-ethoxypropionate, 3 - Cyclic esters, such as esters, such as methoxy methyl propionate, and (gamma)-butyrolactone, etc. are mentioned. Preferably, esters such as alkylene glycol alkyl ether acetates, ketones, ethyl 3-ethoxypropionate or methyl 3-methoxypropionate may be used, more preferably propylene glycol monomethyl ether acetate, propylene glycol mono Ethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate or methyl 3-methoxypropionate can be used.

The dispersion solvents may be used alone or in combination of two or more.

Alkali-soluble resin (B)

The alkali-soluble resin (B) must be soluble in the solvent of the present invention and have reactivity to the action of light or heat. In addition, any acrylic copolymer that functions as a binder resin for the colorant and is soluble in an alkaline developer may be used without particular limitation.

The alkali-soluble resin may be a copolymer of a carboxyl group-containing monomer and another monomer copolymerizable with the monomer. The carboxyl group-containing monomer may be, for example, an unsaturated carboxylic acid such as an unsaturated polycarboxylic acid having at least one carboxyl group in a molecule such as an unsaturated monocarboxylic acid, an unsaturated dicarboxylic acid, or an unsaturated tricarboxylic acid. The unsaturated monocarboxylic acid may be, for example, acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid. The unsaturated dicarboxylic acid may be, for example, maleic acid, fumaric acid, itaconic acid, citraconic acid and mesaconic acid. The unsaturated polyhydric carboxylic acid may be an acid anhydride, specifically maleic anhydride, itaconic acid anhydride and citraconic acid anhydride. In addition, the unsaturated polyvalent carboxylic acid may be a mono(2-methacryloyloxyalkyl) ester, for example, mono(2-acryloyloxyethyl) succinate, mono(2-methacryloyloxyethyl) succinate ), phthalic acid mono(2-acryloyloxyethyl) and phthalic acid mono(2-methacryloyloxyethyl). In addition, the unsaturated polyhydric carboxylic acid may be a mono(meth)acrylate of a dicarboxylic polymer at both ends, for example, ω-carboxypolycaprolactone monoacrylate and ω-carboxypolycaprolactone monomethacrylate. there is. The carboxyl group-containing monomers may be used alone or in combination of two or more. Specific examples of other monomers copolymerizable with the carboxyl group-containing monomer include styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, and m-methoxystyrene. Toxy styrene, p-methoxy styrene, o-vinylbenzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p- aromatic vinyl compounds such as vinylbenzyl glycidyl ether and indene; Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, i-propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, i-butyl acrylate, i-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, 2-hydroxy Ethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxy hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, allyl acrylate Rate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl meth acrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxy diethylene glycol acrylate, methoxy diethylene glycol methacrylate, methoxy triethylene glycol acrylate, methoxy triethylene glycol methacrylate Rate, methoxy propylene glycol acrylate, methoxy propylene glycol methacrylate, methoxy dipropylene glycol acrylate, methoxy dipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadienyl Acrylate, dicyclopentadienyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glycerol monoacrylate and glycerol monomethacrylate, etc. unsaturated carboxylic acid esters of; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethyl Unsaturated carboxyl such as aminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl acrylate and 3-dimethylaminopropyl methacrylate acid aminoalkyl esters; unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide; unsaturated amides such as acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide and N-2-hydroxyethylmethacrylamide; unsaturated imides such as maleimide, N-phenylmaleimide and N-cyclohexylmaleimide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; Polystyrene, polymethylacrylate, polymethylmethacrylate, poly-n-butylacrylate, poly-n-butylmethacrylate, polysiloxane having a monoacryloyl group or monomethacryloyl group at the end of the molecular chain of the polymer. Macromonomers etc. are mentioned. These monomers may be used alone or in combination of two or more.

Therefore, the alkali-soluble resin, for example, (meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / 2-hydroxyethyl ( meth)acrylate/benzyl(meth)acrylate copolymer, (meth)acrylic acid/methyl(meth)acrylate/polystyrene macromonomer copolymer, (meth)acrylic acid/methyl(meth)acrylate/polymethyl(meth)acryl Late macromonomer copolymer, (meth)acrylic acid/benzyl (meth)acrylate/polystyrene macromonomer copolymer, (meth)acrylic acid/benzyl (meth)acrylate/polymethyl (meth)acrylate macromonomer copolymer, (meth)acrylic acid/benzyl (meth)acrylate macromonomer copolymer, ) Acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / Polymethyl (meth)acrylate macromonomer copolymer, (meth)acrylic acid/styrene/benzyl (meth)acrylate/N-phenylmaleimide copolymer, (meth)acrylic acid/succinic acid mono(2-acryloyloxy)/ Styrene/benzyl(meth)acrylate/N-phenylmaleimide copolymer, (meth)acrylic acid/mono(2-acryloyloxyethyl) succinate/styrene/allyl(meth)acrylate/N-phenylmaleimide copolymer and (meth)acrylic acid/benzyl(meth)acrylate/N-phenylmaleimide/styrene/glycerol mono(meth)acrylate copolymers. The (meth)acrylate means acrylate or methacrylate.

Among the alkali-soluble resins, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate / styrene copolymer, (meth) acrylic acid / methyl (meth) acrylate copolymer and ( A meth)acrylic acid/methyl (meth)acrylate/styrene copolymer is preferably used.

In addition, the alkali-soluble resin should have a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC) using tetrahydrofuran as an eluting solvent of 5,000 to 50,000, preferably 8,000 to 40,000, and more preferably 10,000 to 30,000. When the weight average molecular weight of the alkali-soluble resin is in the range of 5,000 to 50,000, the coating film hardness is improved, exhibits an excellent film remaining rate, and exhibits good solubility in the developing solution and improved resolution of the unexposed area. In addition, the acid value should be 50 to 150 (mgKOH/g), preferably 60 to 140, more preferably 80 to 130. Within the above acid value range, the solubility of the alkali-soluble resin in the developing solution is improved, so that the unexposed portion is easily dissolved and highly sensitive, so that a pattern of the exposed portion remains during development to improve the remaining film rate.

The alkali-soluble resin may be included in an amount of 5 to 80% by weight, preferably 10 to 60% by weight, based on the total weight of the solid content in the red photosensitive resin composition. If it is out of the above range, the remaining film rate and reliability may be deteriorated, and it may not be easy to form a pattern.

photopolymerization Compound (C)

The photopolymerizable compound is a compound that can be polymerized by active radicals, acids, etc. generated from a photopolymerization initiator by irradiation of light, and may be a monofunctional or multifunctional polymerizable compound depending on the number of functional groups. Examples of the monofunctional polymerizable compound include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate and N-vinylphy. Rolidone or the like. Examples of the bifunctional polymerizable compound include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, and triethylene glycol di(meth)acrylate. , bis(acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, butylene glycol dimethacrylate, hexanediol di(meth)acrylate, diethylene glycol di(meth) Acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, ethoxylate neo pentyl glycol diacrylate and propyloxylate neopentyl glycol diacrylate. As the trifunctional polymerizable compound, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, ethoxylate trimethylolpropane tri(meth)acrylate, propyloxylate trimethylolpropane tri(meth) ) acrylate, glycerylpropyloxylate triacrylate, and isocyanurate triarylate. Examples of the tetrafunctional polymerizable compound include pentaerythritol tetra(meth)acrylate and dimethylolpropane tetra(methyl)acrylate. Further, the 5-functional polymerizable compound may be dipentaerythritol penta(meth)acrylate, and the 6-functional photopolymerizable compound may be dipentaerythritol hexa(meth)acrylate. Among them, as the photopolymerizable compound, a difunctional or higher functional polymerizable compound may be preferably used, and a pentafunctional or higher functional polymerizable compound may be preferably used.

In addition, the photopolymerizable compound is included in 5 to 50% by weight, more preferably 7 to 45% by weight, based on the total weight of the solid content in the red photosensitive resin composition. When the photopolymerizable compound is included in the above range, strength or smoothness of the pixel portion may be improved.

light polymerization initiator (D)

The photopolymerization initiator in the present invention is a compound that generates radicals capable of initiating polymerization of the polyfunctional monomer of the photopolymerizable compound by exposure to radiation such as visible light, ultraviolet light, deep ultraviolet light, electron beam, and X-ray. Examples of such photopolymerization initiators include acetophenone-based compounds, benzophenone-based compounds, biimidazole-based compounds, triazine-based compounds, oxime ester-based compounds, and thioxanthone-based compounds. In this invention, a photoinitiator can be used individually or in mixture of 2 or more types, and it is preferable to use 1 or more types of oxime ester type compounds.

Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1-[4-(2-hydroxyl) Roxyethoxy) phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propan-1 -one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, etc. are mentioned.

Examples of the benzophenone-based compound include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra ( tert-butyl peroxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.

Specific examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichloro). Phenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole , 2,2'-bis(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 with a carboalkoxy group; and the like. Among these, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4' ,5,5'-tetraphenylbiimidazole, 2,2-bis(2,6-dichlorophenyl)-4,4'5,5'-tetraphenyl-1,2'-biimidazole are preferably used do.

Specific examples of the triazine-based 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-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2- yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine , 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl )-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine; and the like.

The oxime ester compounds include 1,2-Octanedione, 1-[4-(phenylthio) phenyl]-,2-(O-benzoyloxime), 1-[9-Ethyl-6-(2-methylbenzoyl)-9H- carbazol-3-yl]ethanone 1-(O-acetyloxime) and the like.

Examples of the thioxanthone-based compounds include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like. there is

In addition, the photopolymerization initiator (D) may further include a photopolymerization initiator (d1) in order to improve the sensitivity of the red photosensitive resin composition of the present invention. The red photosensitive resin composition according to the present invention contains the photopolymerization initiation auxiliary agent (d1), so that the sensitivity is further increased and the productivity can be improved.

As the photopolymerization initiation aid (d1), 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 may be preferably used.

As the amine compound, it is preferable to use an aromatic amine compound, specifically, an aliphatic amine compound such as triethanolamine, methyldiethanolamine, and triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4- Isoamyl dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (common name: Michler's ketone) ), 4,4'-bis (diethylamino) benzophenone, etc. can be used.

The carboxylic acid compound is preferably an aromatic heteroacetic acid, specifically phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid Acetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc. are mentioned.

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)-trione, trimethylolpropanetris(3-mercaptopropionate), pentaerythritoltetrakis(3-mercaptobutyl rate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate), tetraethylene glycol bis (3-mercaptopropionate), etc. can

The photopolymerization initiator (D) is 0.1 to 40% by weight, preferably 1 to 30% by weight, based on the total solid weight of the red photosensitive resin composition of the present invention, based on the content of the alkali-soluble resin (B) and the photopolymerizable compound (C). weight percent may be included. When the amount of the photopolymerization initiator (D) is within the range of 0.1 to 40% by weight, the red photosensitive resin composition is highly sensitive and the exposure time is shortened, thereby improving productivity and maintaining high resolution. In addition, the strength of the pixel portion formed using the composition under the above-described conditions and the smoothness of the surface of the pixel portion may be improved.

In addition, in the case of the photopolymerization initiation aid (d1), 10 to 100% by weight, preferably 20 to 100% by weight, of the total photopolymerization initiator may be included. When the ratio of the photopolymerization initiation aid (d1) in the total photopolymerization initiator is less than 10% by weight, the decrease in sensitivity due to the dye cannot be overcome and the short circuit of the pattern is likely to occur during the developing process.

In addition, when the photopolymerization initiation auxiliary agent (d1) is further used, the photopolymerization initiation auxiliary agent (d1) is an alkali-soluble resin (B) and a photopolymerizable compound (C) based on the total solid weight of the red photosensitive resin composition of the present invention With respect to the content of 0.1 to 40% by weight, preferably 1 to 30% by weight may be included. When the amount of the photopolymerization initiation aid (d1) is within the range of 0.1 to 40% by weight, the sensitivity of the red photosensitive resin composition is further increased, and the productivity of a color filter formed using the composition is improved. Provides an effect.

Solvent (E)

The solvent is not particularly limited as long as it dissolves the red photosensitive resin composition, and in particular, ethers, aromatic hydrocarbons, ketones, alcohols, esters or amides are preferred. Specifically, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol di Butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol dipropyl ether and dipropylene glycol ethers such as dibutyl 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; Ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methyl Toxybutyl acetate, 3-methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol Monoacetate, diethylene glycol diacetate, diethylene glycol monobutyl ether acetate, propylene glycol monoacetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene carbonate, propylene carbonate and γ-buty Ester, such as rolactone, etc. are mentioned. The solvent may be used by mixing one or two or more selected from the group consisting of the exemplified solvents. In addition, the boiling point should be 100 to 200 ° C in terms of coating and drying properties, propylene glycol monomethyl ether acetate, Propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, butalactate, ethyl 3-ethoxypropionate and methyl 3-methoxypropionate are preferred.

The solvent may be included in an amount of 25 to 80% by weight, preferably 30 to 70% by weight, based on the total weight of the red photosensitive resin composition. In the above range, when applied with a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (or a die coater), and a Cjet, good coating properties may be exhibited.

Additive (F)

In the red photosensitive resin composition of the present invention, in addition to the above components, additives (F) such as fillers, other polymer compounds, curing agents, adhesion promoters, ultraviolet absorbers, and aggregation inhibitors are used in combination according to the needs of those skilled in the art within the range not impairing the object of the present invention. It is also possible to do

Specifically, glass, silica, alumina, etc. may be used as the filler, but is not limited thereto.

Examples of the other polymer compounds include curable resins such as epoxy resins and maleimide resins, thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, polyfluoroalkyl acrylates, polyesters, and polyurethanes. It may, but is not limited thereto.

The curing agent is used to increase deep curing and mechanical strength, and specifically, an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, etc. may be used, but is not limited thereto. The epoxy compound is specifically, bisphenol A-based epoxy resin, hydrogenated bisphenol A-based epoxy resin, bisphenol F-based epoxy resin, hydrogenated bisphenol F-based epoxy resin, noblock type epoxy resin, other aromatic epoxy resins, alicyclic epoxy resins, glycol Cidyl ester-based resins, glycidylamine-based resins, or brominated derivatives of these epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and their brominated derivatives, butadiene (co)polymer epoxides, isoprene (void) Polymer epoxides, glycidyl (meth)acrylate (co)polymers, triglycidyl isocyanurate, and the like may be used, but are not limited thereto. Specifically, the oxetane compound may be carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexane dicarboxylic acid bisoxetane, etc., but are limited thereto It is not.

The curing agent may be used in combination with a curing auxiliary compound capable of ring-opening polymerization of an epoxy group of an epoxy compound and an oxetane skeleton of an oxetane compound together with the curing agent. Specifically, polyvalent carboxylic acids, polyvalent carboxylic acid anhydrides, acid generators, and the like may be used as the curing auxiliary compound. The carboxylic acid anhydrides may be commercially available as epoxy resin curing agents. Examples of the commercially available epoxy resin curing agent include a trade name (Adeka Hadona EH-700) (manufactured by Adeka Kogyo Co., Ltd.), a trade name (Rika Siddo HH) (manufactured by Shinnippon Ewha Co., Ltd.), and a trade name (MH-700). (manufactured by Shin Nippon Ewha Co., Ltd.); and the like.

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

The adhesion promoter is specifically, vinyltrimethoxysilane, vinyltriethoxysilane, vinyl tris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N -(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercapto propyltri Methoxysilane, 3-isocyanate propyltrimethoxysilane and 3-isocyanate propyltriethoxysilane may be used alone or in mixtures 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.

Specifically, the ultraviolet absorber may be 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotyriazole, alkoxybenzophenone, etc., but is not limited thereto.

The aggregation inhibitor may specifically use sodium polyacrylate, etc., but is not limited thereto.

The present invention provides a color filter made of the red photosensitive resin composition. A pattern may be formed by applying the red photosensitive resin composition on a substrate, photocuring, and developing.

First, the red photosensitive resin composition is applied onto a substrate or a layer comprising a solid content of the photosensitive resin composition, and then heated and dried to remove volatile components such as a solvent to obtain a smooth coating film.

The coating method may be carried out by spin coating, casting coating, roll coating, slit and spin coating, or slit coating. After coating, heat drying (prebaking) or vacuum drying is followed by heating to volatilize volatile components such as solvents. The heating temperature is 70 to 200°C, preferably 80 to 130°C. The coating film thickness after heating and drying is about 1 to 8 μm. The coating film is irradiated with ultraviolet rays through a mask in order to form a target pattern. At this time, it is preferable to use a device such as a mask aligner or a stepper so that parallel light rays must be uniformly irradiated to the entire exposure area, and to accurately align the mask and the substrate. When irradiated with ultraviolet rays, the portion irradiated with ultraviolet rays is cured. As the ultraviolet rays, g-rays (wavelength: 436 nm), h-rays, and i-rays (wavelength: 365 nm) may be used. The irradiation amount of ultraviolet rays may be appropriately selected as needed, but is not limited thereto in the present invention. When the cured coating film is brought into contact with a developing solution to dissolve the unexposed portion and developed, a cured product having a desired pattern shape can be obtained.

In addition, the present invention provides a display device including the color filter.

Hereinafter, preferred examples, comparative examples, and experimental examples are presented to aid understanding of the present invention, but these examples, comparative examples, and experimental examples are only illustrative of the present invention and do not limit the scope of the appended claims, It is obvious to those skilled in the art that various changes and modifications to the Examples, Comparative Examples, and Experimental Examples are possible within the scope and spirit of the present invention, and it is natural that such changes and modifications fall within the scope of the appended claims.

<Preparation of Pigment Dispersion Composition>

manufacturing example 1. Pigment Dispersion Composition A-1

As a pigment, C.I. 12.0 parts by weight of Pigment Red 177, 5.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 13.0 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent, propylene glycol methyl ether acetate 70.0 parts by weight were mixed/dispersed for 12 hours by a bead mill to prepare a pigment dispersion composition A-1.

manufacturing example 2. Pigment Dispersion Composition A-2

As a pigment, C.I. 12.0 parts by weight of Pigment Red 179, 5.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 13.0 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent, 70.0 parts by weight of propylene glycol methyl ether acetate The pigment dispersion composition A-2 was prepared by mixing/dispersing for 12 hours by a bead mill.

manufacturing example 3. Pigment Dispersion Composition A-3

As a pigment, C.I. 12.0 parts by weight of Pigment Red 254, 5.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 13.0 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent, 70.0 parts by weight of propylene glycol methyl ether acetate The pigment dispersion composition A-3 was prepared by mixing/dispersing for 12 hours by a bead mill.

manufacturing example 4. Pigment Dispersion Composition A-4

20.0 parts by weight of carbon black PBk7, 6 parts by weight of Ajispa PB821 (Ajinomoto Fine Techno Co., Ltd.) as a dispersant, and 74 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed/dispersed in a bead mill for 12 hours to obtain a pigment dispersion composition A -4 was prepared.

manufacturing example 5. Pigment Dispersion Composition A-5

As a pigment, C.I. 12.0 parts by weight of Pigment Yellow 139, 5.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 70 parts by weight of propylene glycol methyl ether acetate and 13 parts by weight of propylene glycol methyl ether as a solvent Mixed / By dispersing, a pigment dispersion composition A-5 was prepared.

synthesis example 1. Synthesis of alkali-soluble resin

In a flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet pipe, 120 parts by weight of propylene glycol monomethyl ether acetate, 80 parts by weight of propylene glycol monomethyl ether, 2 parts by weight of AIBN, 13.0 parts by weight of acrylic acid, and benzyl methacrylic acid were added. 10 parts by weight of latex, 57.0 parts by weight of styrene, 20 parts by weight of methyl methacrylate, and 3 parts by weight of n-dodecylmercapto were added, followed by nitrogen substitution. Thereafter, while stirring, the temperature of the reaction solution was raised to 110° C. and reacted for 6 hours. The solid acid value of the alkali-soluble resin thus synthesized was 100.2 mgKOH/g and the weight average molecular weight Mw measured by GPC was about 15110.

Example 1 to 3 and comparative example 1-4. Preparation of red photosensitive resin composition

A red photosensitive resin composition was prepared with the composition and content (unit: parts by weight) shown in Table 1 below.

[Table 1]

Alkali-soluble resin (B): Synthesis Example 1

Photopolymerizable compound (C): dipentaerythritol hexaacrylate (KAYARD DPHA; manufactured by Nippon Kayaku Co., Ltd.)

Photopolymerization initiator (D): 2-O-benzoyloxime-1-[4-(phenylthio)phenyl]-1,2-octanedione (OXE-01; manufactured by BASF)

Solvent (E): Propylene glycol monomethyl ether acetate

Experimental example 1. Manufacture of color filters

A color filter was prepared using the red photosensitive resin composition prepared in Examples 1 to 3 and Comparative Examples 1 to 4.

Specifically, each of the red photosensitive resin compositions is coated on a 2-inch square glass substrate ("EAGLE XG" manufactured by Corning) by spin coating, and then placed on a heating plate and maintained at a temperature of 100 ° C. for 3 minutes to form a thin film. made it Subsequently, a test photomask having a pattern for changing the transmittance stepwise in the range of 1 to 100% and a 3 x 3 cm exposed part pattern was placed on the thin film, and ultraviolet rays were irradiated at a distance of 100 μm from the test photomask. . At this time, the ultraviolet light source was irradiated with an illuminance of 100 mJ/cm 2 using a 1KW high-pressure mercury lamp containing all of the g, h, and i lines, and no special optical filter was used. The UV-irradiated thin film was developed by immersing it in a KOH aqueous solution of pH 10.5 for 2 minutes. 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 200° C. for 25 minutes to prepare a color filter. The obtained film thickness was 3 μm. The film thickness was measured using a film thickness measuring device (DEKTAK 6M; manufactured by Veeco).

Experimental example 2. Spectroscopic measurements

Spectral transmittance in the visible light range of 380 nm to 780 nm using a colorimeter (OSP-200, manufactured by Olympus) after preparing a color filter in the same manner as in Experimental Example 1 except that the test photomask was not used. was measured, and the results are shown in Tables 2 and 3, and FIGS. 1 to 3.

[Table 2]

[Table 3]

Tables 2 and 3 and FIGS. 1 to 3 show the transmittance according to the wavelength according to the above experimental results.

As shown in FIG. 1, Comparative Examples 1 and 2, which did not contain the black pigment, exhibited a transmittance of 90% or more at a wavelength of 635 nm or more, but in Examples containing the black pigment, the transmittance was less than 90% at a wavelength of 635 nm or more. was

In addition, examples including the black pigment exhibited a transmittance of 20% or less at a wavelength of 430 nm to 590 nm.

On the other hand, in Comparative Examples 3 and 4 in which the black pigment is less than 0.5% by weight or more than 10% by weight based on the solid content of the colorant, the external light reflection prevention effect and visibility are insufficient.

Claims (13)

A colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E),
The colorant (A) is a red photosensitive resin composition containing a red pigment and a black pigment,
The black pigment is 0.5 to 10% by weight based on the solid content of the colorant,
The cured film prepared from the red photosensitive resin composition has a spectral transmittance of 20% or less at a wavelength of 430 to 590 nm, and a spectral transmittance at a wavelength of 635 to 780 nm is 70% or more and less than 90%. A red photosensitive resin composition for a color filter that does not contain delete The method of claim 1,
The red photosensitive resin composition, characterized in that the weight ratio of the red pigment and the black pigment is 99.99 ~ 80: 20 ~ 0.1. The method of claim 1,
With respect to the total weight of solids in the red photosensitive resin composition
10 to 80% by weight of a colorant (A);
Alkali-soluble resin (B) 5 to 80% by weight,
5 to 50% by weight of a photopolymerizable compound (C);
The photopolymerization initiator (D) includes 0.1 to 40 parts by weight based on 100 parts by weight of the total solid content of the alkali-soluble resin (B) and the photopolymerizable compound (C),
The red photosensitive resin composition, characterized in that the solvent (E) comprises 25 to 80% by weight based on the total weight of the red photosensitive resin composition. The method of claim 1,
The red photosensitive resin composition, characterized in that the colorant further comprises a yellow pigment. The method of claim 5,
The red photosensitive resin composition, characterized in that the yellow pigment comprises 3 to 30 parts by weight based on 100 parts by weight of the total content of the red pigment and the black pigment. The method of claim 1,
The red pigment is characterized in that it comprises at least one selected from the group consisting of CI Pigment Red 179, CI Pigment Red 177, CI Pigment Red 209, CI Pigment Red 242 and CI Pigment Red 254 A photosensitive resin composition. The method of claim 1,
The black pigment comprises at least one selected from the group consisting of red, blue and green pigments, CI Pigment Black 1, CI Pigment Black 7, carbon black, organic black and titanium black. A red photosensitive resin composition. The method of claim 5,
The red photosensitive resin composition, characterized in that the yellow pigment comprises at least one selected from the group consisting of CI Pigment Yellow 138, CI Pigment Yellow 139 and CI Pigment Yellow 150. A color filter prepared using the red photosensitive resin composition according to any one of claims 1 and 3 to 9 and not including a polarizing plate. A display device comprising the color filter of claim 10. The method of claim 11,
Characterized in that the display element is a flexible display element, the display element. The method of claim 11,
Characterized in that the display device is an organic light emitting device, the display device.