TW201422645A - Styryl-based compound, coloring agent comprising styryl-based compound, photoresist resin composition comprising coloring agent, photosensitive material manufactured by using the photoresist resin composition, color filter comprising the same and display - Google Patents

Abstract

The present disclosure relates to a styryl-based compound, a coloring agent comprising the styryl-based compound, a photosensitive resin composition comprising the coloring agent, a photosensitive material manufactured by using the photosensitive resin composition, a color filter comprising the same and a display device having the color filter.

Description

a styrene-based compound, a coloring agent containing a styrene-based compound, a photoresist resin composition containing a coloring agent, a photosensitive material prepared using the photoresist resin composition, a color filter containing the same, and having the color filter Slice display Device

The present invention relates to a styrenic compound, a coloring agent comprising a styrenic compound, a photoresist resin composition comprising a coloring agent, a photosensitive material prepared using the photoresist resin composition, including color filtering thereof A sheet and a display device having a color filter.

The claims disclosed in the present invention claim priority from the Korean Intellectual Property Office on August 31, 2012, and the Korean Patent Application No. 10-2012-0096343, the entire contents of which is hereby incorporated by reference. In addition, the claims disclosed in the present invention claim priority from the Korean Intellectual Property Office on January 2, 2013, and the Korean Patent Application No. 10-2013-0000370, the entire contents of which is hereby incorporated by reference.

Recently, light sources of liquid crystal displays (LCDs), self-illuminating LEDs, or OLED devices have been widely used in place of current CCFLs, which do not emit light by a driver or via liquid crystal. In general, when an LED or OLED is used as the light source, it is not necessary to use a color filter because the LED or the OLED itself emits red, green, or blue light.

However, color filters typically achieve a high color reproduction range by improving the color purity of the light emitted by the light source of the LED or OLED. In particular, white light generated using an OLED source must be separated by a color filter.

Only the spectrum emitted from a light source and the absorption and transmission spectra of a color filter are appropriately combined to achieve improved luminescent color purity, light reproducibility, and brightness.

[Previous Technical Literature]

Korean Patent Application Publication No. 2001-0018075.

The present invention relates to a styrenic compound, a coloring agent comprising a styrenic compound, a photoresist resin composition comprising a coloring agent, a photosensitive material prepared using the photoresist resin composition, including color filtering thereof A sheet and a display device having a color filter.

The embodiment of the present invention provides a styrene-based compound represented by the following Chemical Formula 1.

Wherein n is an integer of 1 to 3, m is an integer of 1 to 4, X is NR or O, and R is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, and a substituted or 2 to 25 carbon atom or a group consisting of unsubstituted alkenyl groups; L1 is a directly bonded or substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; R1 and R2 are the same or different from each other, and are each independently Is hydrogen, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, and having 1 to 25 carbon atoms. a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, having 6 to a substituted or unsubstituted aryl group of 40 carbon atoms, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or One or more N, a substituted or unsubstituted heterocyclic group of O and S atoms; R3 is hydrogen, deuterium, halo, nitrile, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 25 carbon atoms a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; R 4 is hydrogen, hydrazine, halogen, nitrile a nitro group, a hydroxy group, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, having 1 to 25 carbons a substituted or unsubstituted alkoxy group of an atom, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted heterocyclic group including one or more N, O and S atoms; R5 is hydrogen , hydrazine, halogen, nitrile, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 25 carbon atoms, having 3 to 20 carbon atoms a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, containing 6 a substituted or unsubstituted aryl group of up to 40 carbon atoms, a substituted or unsubstituted propylene oxime group having 3 to 40 carbon atoms, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted acrylate group, a substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms, or one or more N, O and A substituted or unsubstituted heterocyclic group of the S atom.

Embodiments of the present invention provide a color former comprising a styrenic compound.

Embodiments of the present invention provide a photoresist resin composition comprising a colorant.

Embodiments of the present invention provide a photosensitive material produced using the photoresist resin composition.

Embodiments of the present invention provide a color filter that includes a photosensitive material.

Embodiments of the present invention provide a display device having a color filter.

According to an embodiment of the present invention, it is provided that the coloring agent has excellent heat resistance and/or has excellent solubility in an organic solvent.

According to an embodiment of the present invention, the photoresist resin composition can be obtained as an absorption or transmission spectrum suitable for a light source, and the result can be obtained with a higher color reproduction range, high luminance, high contrast range, and the like.

The photoresist resin composition according to the embodiment of the present invention has a high degree of crosslinking and excellent heat resistance. Therefore, according to an embodiment of the present invention, the color of the resist resin composition is slightly changed when it is treated by heat.

Figure 1 shows the absorption spectra of Chemical Formulas 1-1, 1-3, 1-5, and 1-7.

2 is a transmission spectrum of Chemical Formulas 1-1, 1-3, and 1-7.

3 is a transmission spectrum of Example 3 and Comparative Example 1.

4 is a transmission spectrum amplification of Example 3 and Comparative Example 1. Figure.

5 is a transmission spectrum of Example 4 and Comparative Example 2.

The contents of the present invention are explained in more detail below.

The present invention provides a styrene-based compound represented by Chemical Formula 1.

In the examples of the present invention, the styrene-based compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2.

Wherein n, M, R1 to R4, X, and L1 are the same as defined above, and R6 is hydrogen, deuterium, halogen, nitrile, nitro, hydroxy, substituted or unsubstituted having 1 to 25 carbon atoms. Alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, having 2 to 25 carbon atoms Substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted fluorenyl group, substituted or unsubstituted carbazole A substituted or unsubstituted heterocyclic group comprising one or more N, O and S atoms.

In an embodiment of the present invention, R1 and R2 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or not containing 6 to 40 carbon atoms. Substituted aryl, or substituted or unsubstituted aralkyl having 7 to 50 carbon atoms.

In an embodiment of the present invention, R1 and R2 are the same or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a group having 7 to 50 carbon atoms. Substituted or unsubstituted aralkyl.

In the present invention, when R1 and R2 are an amine substituent, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms. This styrene-based compound having a high molecular weight and thus has excellent heat resistance.

In an embodiment of the invention, R4 is a nitrile group, a substituted or unsubstituted alkyl group having 6 to 40 carbon atoms, the alkyl group being unsubstituted or substituted by one or more substituents selected from the group consisting of Free group of the following: halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine group, alkylamine group, carbazolyl, fluorenyl Group), a nitrile group, and a heterocyclic group including one or more N, O and S atoms, which are unsubstituted or substituted, or a heterocyclic group including one or more N, O and S atoms, the heterocyclic group Unsubstituted or substituted by one or more substituents selected from the group consisting of halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine group And an alkylamine group, a carbazolyl group, a fluorenyl group, a nitrile group, and a heterocyclic group including one or more N, O and S atoms.

In an embodiment of the invention, L1 is a linear or branched alkylene group having from 1 to 10 carbon atoms which is unsubstituted or substituted by one or more substituents selected from the group consisting of Group consisting of: halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine group, alkylamine group, carbazolyl, fluorenyl group An acryloyl group, an acrylate group, a nitrile group, and a heterocyclic group including one or more N, O and S atoms.

In an embodiment of the invention, R5 is hydrogen, hydrogen, acrylate group unsubstituted or substituted by one or more substituents selected from the group consisting of halo, alkyl, alkenyl , cycloalkyl, aryl, arylamine group, alkylamine group, carbazolyl, fluorenyl group, nitrile group, and including one or more N, O and a heterocyclic group of the S atom, a carbonyl group unsubstituted or substituted by one or more substituents selected from the group consisting of halo, alkyl, alkenyl, cycloalkyl, aryl , an arylamine group, an alkylamine group, a carbazolyl group, a fluorenyl group, a nitrile group, and a heterocyclic group including one or more N, O and S atoms, Or from one or more unsubstituted or substituted acryloyl groups, the substituents being selected from the group consisting of halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine Group), an alkylamine group, a carbazolyl group, a fluorenyl group, a nitrile group, and one or more N, O and a heterocyclic group of the S atom.

Examples of the substituent are described below, but are not limited thereto.

The term "substituted or unsubstituted" in the present invention means Substituted by a plurality of substituents selected from the group consisting of hydrazine, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, germyl, arylalkenyl, aryl , aryloxy, alkylthio, alkylthio, arylsulfonyl, boron, alkylamine group, aralkylamine group, arylamine group, Heteroaryl, carbazolyl, acryloyl, acrylate, ether, fluorenyl group, nitrile, nitro, hydroxy, cyano, and including one or more N, O, S or A P atom or a cyano group or a heterocyclic group having no substituent.

In the present invention, the alkyl group is a straight chain or a branched chain, and although not particularly limited, a carbon number of from 1 to 25 is preferred. For example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, and the like, but are not limited thereto.

In the present invention, the alkenyl group is a straight chain or a branched chain, and although not particularly limited, a carbon number of 2 to 25 is preferred. A preferred example is an alkenyl group in which the aryl group is substituted by a stylbenyl group, a styryl group, or the like, but is not limited thereto.

In the present invention, the alkoxy group is a straight chain or a branched chain, and although not particularly limited, a carbon number of from 1 to 25 is preferred.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 20 carbon atoms, particularly preferably a cyclopentyl group or a cyclohexyl group.

The propylene fluorenyl group in the invention is not particularly limited, but preferably has 3 to 40 carbon atoms, particularly methyl acrylate, ethyl acrylate, methyl acrylate, 3-(acrylenyloxy) propyl methacrylate. An ester, or an analog thereof, but is not limited thereto.

In the present invention, the halogen group includes fluorine, chlorine, bromine or iodine.

In the present invention, a fluorenyl group is a structure in which two cyclic organic compounds are linked via one atom, for example, including Or its analogues.

In the present invention, the fluorenyl group includes a structure of a fluorenyl group, and the fluorenyl group of the present invention is a bond which destroys a cyclic compound by one atom. a structure that connects two cyclic compounds, such as Or an analogue thereof.

In the present invention, the aralkyl group particularly has 6 to 49 carbon atoms in the aryl moiety and 1 to 44 carbon atoms in the alkyl moiety. Specific examples include benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3,5-dimethylbenzyl. , α-methylbenzyl, α,α-dimethylbenzyl, α,α-methylphenylbenzyl, 1-naphthylbenzyl, 2-naphthylbenzyl, p- Fluorobenzyl, 3,5-difluorobenzyl, α,α-ditrifluoromethylbenzyl, p-methoxybenzyl, m-methoxybenzyl, α-phenoxy Benzyl, α-benzyloxybenzylamino, naphthylmethyl, naphthylethyl, naphthylisopropyl, pyrrolylmethyl, pyrrolylethyl, aminobenzyl, nitrobenzyl, cyanide Benzomethyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl, etc., but is not limited thereto.

In the present invention, the aryl group may be a monocyclic aryl group or a fused ring aryl group.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, and a carbon number of 6 to 40 is preferred. Specifically, the monocyclic aryl group is, for example, a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but a carbon number of 10 to 40 is preferred. Specifically, the polycyclic aryl group is, for example, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, a fluorenyl group, a cryenyl group, a fluorenyl group, or the like, but is not limited thereto.

In the present invention, the heterocyclic group is a heterocyclic group including O, N or S as a hetero atom, and although not particularly limited, a carbon number of 2 to 40 is preferred. Examples of heterocyclic groups such as thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridyl, pyridazine , quinolyl, isoquinolyl, fluorenyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzothienyl, dibenzothiophene The group is a benzofuranyl group, a dibenzofuranyl group or the like, but is not limited thereto.

The alkylene group in the present invention is an alkane having two bonding points. The alkylene group may be linear, branched, or have a cyclic chain. The number of carbon atoms in the alkylene group is not particularly limited, but preferably 1 to 6 carbon atoms are preferred.

In an embodiment of the invention, n is one.

In an embodiment of the invention, the chemical formula X is O.

In an embodiment of the present invention, R1 and R2 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or not containing 6 to 40 carbon atoms. Substituted aryl, or substituted or unsubstituted aralkyl having 7 to 50 carbon atoms.

In an embodiment of the invention, R1 is a substituted or unsubstituted alkyl group having from 1 to 25 carbon atoms.

In an embodiment of the invention, R1 is substituted or unsubstituted methyl.

In the examples of the present invention, R1 is a methyl group.

In an embodiment of the invention, R1 is substituted or unsubstituted ethyl.

In an embodiment of the invention, R1 is ethyl.

In an embodiment of the invention, R1 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

In an embodiment of the invention, R1 is substituted or unsubstituted phenyl.

In an embodiment of the invention, R1 is phenyl.

In an embodiment of the invention, R1 is a substituted or unsubstituted aralkyl group having from 7 to 50 carbon atoms.

In an embodiment of the invention, R1 is substituted or unsubstituted benzyl.

In an embodiment of the invention, R1 is benzyl.

In an embodiment of the invention, R2 is a substituted or unsubstituted alkyl group having from 1 to 25 carbon atoms.

In an embodiment of the invention, R2 is a substituted or unsubstituted methyl group.

In the embodiment of the invention, R2 is a methyl group.

In an embodiment of the invention, R2 is substituted or unsubstituted ethyl.

In an embodiment of the invention, R2 is ethyl.

In an embodiment of the invention, R2 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

In an embodiment of the invention, R2 is substituted or unsubstituted phenyl.

In an embodiment of the invention, R2 is phenyl.

In an embodiment of the invention, R2 is a substituted or unsubstituted aralkyl group having from 7 to 50 carbon atoms.

In an embodiment of the invention, R2 is substituted or unsubstituted benzyl.

In an embodiment of the invention, R2 is benzyl.

In an embodiment of the invention, L1 is a substituted or unsubstituted alkylene group having from 1 to 10 carbon atoms.

In another embodiment, L1 is a linear or branched ethylene group.

In an embodiment of the invention, L1 is substituted or unsubstituted Linear or branched propylene group.

In an embodiment of the invention, L1 is a substituted or unsubstituted branched propylene group.

In another embodiment, L1 is a branched propylene group substituted with an acrylate group.

In an embodiment of the invention, L1 is an isopropylidene group substituted with a (meth) acrylate.

In an embodiment of the present invention, R3 of Chemical Formula 1 is hydrogen.

In the examples of the present invention, R4 in Chemical Formula 1 is a nitrile group.

In the examples of the present invention, R5 of Chemical Formula 1 is a substituted or unsubstituted carbonyl group.

In an embodiment of the present invention, R5 of Chemical Formula 1 is a substituted or unsubstituted acrylonitrile group.

In an embodiment of the present invention, R5 of Chemical Formula 1 is an acryloyl group substituted by an alkyl group.

In one embodiment of the present invention, R5 in Chemical Formula 1 is an acryloyl group substituted by a methyl group.

Further, Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-8 below, but is not limited thereto.

In the examples of the present invention, the maximum absorption wavelength (λ _max ) of the styrene-based compound ranges from 400 nm to 500 nm.

In one embodiment of the invention, the absorption of the styrenic compound The spectral range is from 350 nm to 500 nm.

Figure 1 shows the absorption spectra of Chemical Formulas 1-1, 1-3, 1-5, and 1-7. 1 can confirm that the maximum absorption wavelength (λ _max ) of the styrenic compound in one embodiment ranges from 400 nm to 500 nm. In this case, the photoresist resin composition appears green.

2 is a transmission spectrum of Chemical Formulas 1-1, 1-3, and 1-7.

3 is a transmission spectrum of Example 3 and Comparative Example 1.

4 is an enlarged view of a transmission spectrum of Example 3 and Comparative Example 1.

5 is a transmission spectrum of Example 4 and Comparative Example 2.

4 is a transmission spectrum of Example 3 and Comparative Example 1. In the examples of the present invention, the transmittance of the styrene-based compound is in the range of 90% to 100% at a wavelength of 500 nm to 800 nm.

Fig. 5 is an enlarged view showing transmission spectra of Example 4 and Comparative Example 2. As described above, it can be known that the brightness increases when green appears.

The styrenic compound of Chemical Formula 1 can be prepared by a structure having a carbazolyl group, a cyano group, and an acrylic group, which is obtained by reacting a starting material containing a tertiary amine structure, and a cyano group or an acrylic group. a compound such as NCCH ₂ COOH. An additional acrylic group may be introduced to the acrylic group as necessary.

According to an embodiment of the present invention, the styrenic compound may be bonded to other substituents by light or heat.

Embodiments of the present invention provide a color former comprising a styrenic compound.

The photoresist resin composition of the embodiment of the present invention includes a colorant comprising the styrene compound represented by Chemical Formula 1.

For a color filter using a pigment type resist resin composition containing only an existing pigment, the pigment having an absorption and transmission spectrum is suitable for a limited number of light sources, and it is not easy to finely adjust the absorption and transmission spectra.

According to the coloring agent of the embodiment of the present invention, the transmission spectrum can be simply fine-tuned.

In an embodiment of the present invention, the colorant is a dye type coloring agent composed of a styrene-based compound alone.

In an embodiment of the invention, the colorant comprises a styrenic compound, and one, two, or more additional colorants selected from the group consisting of pigments and dyes.

Specifically, according to an embodiment of the present invention, the styrene-based compound may be used singly as a coloring agent or as a coloring agent by mixing a styrene-based compound, a pigment other than a styrene-based compound, a dye, or a mixture thereof.

Specifically, in the present embodiment, the colorant is a dye including a mixed colorant of a styrene compound, and a dye not including a styrene compound. In another embodiment, the colorant is a dye/pigment blend of colorants including dyes and pigments of styryl based compounds. In another embodiment, the colorant is a dye/pigment mixed coloring agent comprising a dye of a styryl compound and a dye and pigment excluding a styrenic compound.

The color filter of the embodiment of the present invention uses a photoresist resin composition containing a styrene compound, and various dyes and pigments can be used. A suitable absorption and transmission spectrum of the light source is obtained, so that a range of high color reproduction range, high brightness, and high contrast can be achieved.

The pigment is a powdery coloring agent which is insoluble in water and an organic solvent.

A dye is a colorant dissolved in water and an organic solvent, dispersed to a single molecule, bonded to a molecule such as a fiber, and colored.

The "colorant" of the present invention is a pigment, a dye, or a mixture of a pigment and a dye.

The "colorant" of the present invention is a mixture of a styrenic compound and/or a colorant.

As the black pigment, it may be carbon black, graphite, metal oxide, or the like. Carbon blacks such as Cisto 5HIISAF-HS, 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 (made by Tokai Carbon Co., Ltd.), Tho Black II, Tho Black N339, Takuro SH, Tak H, LH, HA, SF, N550M, M, E Figure G, Figure R, Figure N760M, Figure LR, #2700, #2600, #2400, #2350, #2300, #2200, #1000, #980, #900, MCF88, #52, #50, #47, #45,#45L,#25,#CF9,#95,#3030, #3050, MA7, MA77, MA8, MA11, MA100, MA40, OIL7B, OIL9B, OIL11B, OIL30B, and OIL31B (Mitsubishi Chemical Co., Ltd. ), 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 (made by Evonik Degusa Co., Ltd.), RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN- 1000, RAVEN-890H, RAVEN-890, RAVEN-880 ULTRA, RAVEN-860 ULTRA, RAVEN-850, RAVEN-RAVEN-820, RAVEN-790 ULTRA, RAVEN-780 ULTRA, RAVEN-760 ULTRA, RAVEN-520, RAVEN -500, RAVEN-460, RAVEN-450, RAVEN-430 ULTRA, RAVEN-420, RAVEN-410, RAVEN-2500ULTRA, RAVEN 2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190 ULTRA, RAVEN-1170 (manufactured by Columbia Chemical Co., Ltd.), and mixtures or the like thereof. In addition, color-developing coloring agents such as Carmine 6B (CI12490), phenolphthalein green (CI74260), phenol blue (CI74160), ruthenium black (BASF K0084.K0086), and cyanine glycosides black Linol yellow (CI) 21090), Linol Yellow GRO (CI21090), benzidine yellow 4T-564D, Victoria Pure Blue (CI42595), CI Pigment Red 3,23,97,108,122,139,140,141,142,143,144,149,166,168,175,177,180,185,189,190,192,202,214,215,220,221,224,230,235,242,254,255,260,262,264,272, CI Pigment Green 7,10,36,37,58,CI Pigment Blue 1,1:2, 1:3,2,2:1,2:2,3,8,9,10,10:1,11,12,15,15:1,15:2,15:3 , 15:4, 15:6,16,18,19,22,24,24:1,53,56,56:1,57,58,59,60,61,62,64,CI Pigment Yellow 1,2,3,4 ,5,6,10,12,13,14,15,16,17,18,20,24,31,32,34,35,35:1,36,36:1,37,37:1,40 , 42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,125,126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214, CI pigment violet 1,19,23, 27, 29, 30, 32, 37, 40, 42, 50, or the like, in addition, white pigments, fluorescent pigments, and the like can also be used. As the cyanide-based mixed compound of the pigment, zinc can also be used as the material of the center metal.

In an embodiment of the invention, the colorant comprises one, two, or more additional colorants selected from the group consisting of styrenic compounds, pigments, and dyes, and colorants and benzene. The weight ratio of the vinyl compound ranges from 1:99 to 99:1. In another embodiment, the weight ratio of the colorant to the styrenic compound is from 3:97 to 97:3. In another embodiment, the weight ratio of the colorant to the styrenic compound is from 95:5 to 5:95. Among the foregoing, it is advantageous in that it has high transmittance.

In an embodiment of the invention, the pigment is PG58 or PY138.

In the examples of the present invention, the colorant is composed of PG58, which is a pigment and a styrene compound.

In the examples of the present invention, the colorant is composed of PG58 and PY138, which are pigments and styrene compounds.

In an embodiment of the invention, the dye has a solubility in propylene glycol methyl ether acetate (PGMEA) of 10% or more.

Embodiments of the present invention provide a photoresist resin composition comprising a colorant.

In an embodiment of the invention, the photoresist resin composition further comprises an adhesive resin, a polyfunctional monomer, a photoinitiator, and a solvent.

The adhesive resin is not particularly limited as long as the photoresist resin composition used for the film exhibits physical properties of strength and manufacturability.

As the adhesive resin, a copolymer resin of a polyfunctional monomer imparts mechanical strength, and a single monomer can be used to impart alkali solubility, and the adhesive is further included in the prior art.

The polyfunctional monomer imparts mechanical strength to the film, including any one or more of unsaturated carboxylic acid esters, aromatic vinyl compounds, unsaturated ethers, unsaturated quinone imines, and anhydrides.

Specific examples of the unsaturated carboxylic acid ester are selected from the group consisting of benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, and (meth) acrylate Ester, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (isobornyl) Methyl) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrafurfuryl (meth) acrylate, hydroxyethyl (methyl) Acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, decyl octyloxy 2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate Ester, 3-methoxybutyl (meth) acrylate, ethoxy diethylene glycol (meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol ( Methyl) acrylate, poly(ethylene glycol) methyl ether (meth) acrylate, phenoxy diglycol (meth) acrylate, p-nonyl phenoxy polyethylene glycol (methyl) Acrylate, p-nonylphenoxy polypropylene glycol (meth) acrylate, epoxy propyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1, 1, 1, 3, 3 , 3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, α - methyl hydroxy methacrylate, α-ethyl hydroxy methacrylate, α-propyl hydroxy methacrylate, and α-butyl hydroxy methacrylate, but is not limited thereto.

Specific examples of the aromatic vinyl monomer are selected from the group consisting of styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxy Styrene, and (o-, m-, p-)-chlorostyrene, but are not limited thereto.

Specific examples of the unsaturated ether are selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

Specific examples of the unsaturated quinone imine are selected from the group consisting of N-phenylmaleimide, N-(4-chlorophenyl)maleimide, N-(4-hydroxybenzene) Base) maleimide, and N-cyclohexylmaleimide, but is not limited thereto.

The acid anhydride includes maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride, and the like, but is not limited thereto.

The monomer which provides alkali solubility is not particularly limited as long as the single The body includes an acid group, for example, the monomer is preferably selected from the group consisting of one or more of the following: (meth)acrylic acid, crotonic acid, maleic acid, fumaric acid, monomethyl maleic acid , 5-northene-2-carboxylic acid, mono-2-((meth)propenyloxy)ethyl dicarboxylate, mono-2-((meth)acrylenyloxy)B The succinic acid ester, ω-carboxypolycaprolactone mono(meth)acrylate, but is not limited thereto.

In an embodiment of the present invention, the adhesive resin has an acid value of 50 to 130 KOH mg/g and a weight average molecular weight ranging from 1,000 to 50,000.

The polyfunctional monomer is a monomer that plays a role of forming a photoresist phase by light, and may specifically include one, two, or a mixture of a plurality selected from the group consisting of propylene glycol methacrylic acid. Ester, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxy Ethanol diacrylate, hydroxyethyl isocyanurate trimethacrylate, trimethyl propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol IV Methacrylate, and dipentaerythritol hexamethacrylate.

The photoinitiator is not particularly limited as long as it induces crosslinking by a radical generated by light, and practical examples are selected from the group consisting of one or more of the following: an acetophenone-based compound, a biimidazole-based compound. , a triazine-based compound, and an anthraquinone compound.

Acetophenone-based compounds such as 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one 4-(2-hydroxyl Ethyloxy)-phenyl-(2-hydroxy-2-propyl)one, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2 , 2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholinyl-1-propan-1-one, 2-phenyl 2--2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4) -morpholinylphenyl)-butan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropan-1-one, etc., but not limited thereto this.

Biimidazole compounds such as 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4 ',5,5'-肆(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4 ',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. Not limited to this.

Triazine-based compounds, for example, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 1,1,1,3,3 ,3-hexafluoro-3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid ethyl ester, ethyl-2-{4- [2,4-Bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetic acid methyl ester, 2-epoxyethyl-2-{4-[2,4-double (three Methyl chloromethyl)-s-triazin-6-yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6- Methyl]phenylthio}acetate, benzyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}methyl acetate, 3 -{Chloro-4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl) -S-triazin-6-yl]phenylthio}propanoid saddle, 2,4-bis(trichloromethyl)-6-p-methoxystyryl-s-triazine, 2, 4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino- 6-p-methoxystyryl-s-triazine, etc., but is not limited thereto. The mercapto compound may, for example, be 1,2-octanedione-1-(4-phenylthio)phenyl-2-(o-benzhydrylhydrazine) (manufactured by Ciba-Geigy Co., Ltd., CGI124), Ketone-1-(9-ethyl)-6-(2-methylbenzimidyl-3-yl)-1-(O-acetyl) (CGI242), N-1919 (made by ADEKA CORPORATION) ), its analogs, etc., but are not limited thereto.

The solvent system comprises one or more selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane. Hexacyclohexane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diglyme, diethylene glycol diethyl ether, diethylene glycol methyl ether, chloroform, dichloromethane 1,2-Dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, hexane, heptane, octane , cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methyl Oxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol diethyl ether acetate, 3-methoxybutyl acetate, ethyl-3-ethoxypropionate And ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but are not limited thereto.

In the embodiment of the present invention, the content of the coloring agent including the styrene-based compound is represented by Chemical Formula 1 as 5 to 60% by weight based on the total weight of the solid content of the resist resin composition, and the content of the adhesive resin. The content of the initiator is from 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is from 0.1% by weight to 50% by weight, from 1% by weight to 60% by weight.

The total weight of the solid component means that the photoresist resin composition does not include the total weight of the component parts of the solvent. The weight standard percentage means that the solid content based on the solid content and each composition can be determined using an analytical method commonly used in the related art, such as liquid chromatography or gas chromatography.

A green color filter having high luminance can be obtained within the foregoing range.

In an embodiment of the present invention, the photoresist resin composition further comprises one, two or more additives selected from the group consisting of: an optical sensitizer, a curing accelerator, a adhesion promoter, a surfactant, Antioxidants, thermal polymerization inhibitors, UV absorbers, dispersants, and leveling agents.

In the embodiment of the invention, the content of the additive is from 0.1% by weight to 20% by weight based on the total weight of the solid content of the photoresist resin composition.

As the light-sensitizer, it is selected from the group consisting of one or more benzophenone-based compounds: benzophenone, 4,4-bis(dimethylamino)benzophenone, 4, 4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzylidene benzoate, 3,3-dimethyl 4-methoxybenzophenone, or 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; anthrone-based compound, such as 9-fluorenone, 2-chloro -9-fluorenone, 2-methyl-9-fluorenone; thioxanthone-based compounds such as thioxanthone, 2,4-diethylthiazinone, 2-chlorothiazinone, 1 - chloro-4-propoxythiazinone, isopropyl thioxanthone, or diisopropyl thioxanthone; an onion ketone compound, such as oxalyl ketone, or 2-methyl oxalyl ketone; Lanthanide compounds such as hydrazine, 2-methyl hydrazine, 2- Ethyl hydrazine, tert-butyl hydrazine, or 2,6-dichloro-9,10-fluorene; acridine compounds such as 9-phenyl acridine, 1,7-bis (9-acridine) Heptane, 1,5-bis(9-acridinylpentane), or 1,3-bis(9-acridinyl)propane; dicarbonyl compounds such as benzyl, 1,7,7- Trimethyl-bicyclo[2,2,1]heptane-2,3-dione, or 9,10-phenanthrenequinone; phosphite oxides such as 2,4,6-trimethylbenzamide Diphenylphosphine oxide, or bis(2,6-dimethoxybenzylidene)-2,4,4-trimethylphenyl oxide; benzoate compound, such as methyl-4 -(Dimethylamino)benzoate, methyl ethyl-4-(dimethylamino)benzoate, or 2-n-butoxyethyl-4-(dimethylamino)benzoate Amino synergist such as 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene)cyclohexanone, or 2 , 6-bis(4-diethylaminomethylene)-4-methyl-cyclopentanone; coumarin compounds such as 3,3-carbonylethene-7-(diethylamino)coumarin , 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzylidenyl-7-(diethylamino)coumarin, 3-benzylidene- 7-methoxy ,10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzopyran [6,7, 8]-quino-11-one; or chalcone compounds such as 4-diethylaminochalcone, 4-azid benzophenone, 2-benzylidene, and 3-methyl-β- Naphthotiazoline.

The curing accelerator is used for improving curability and mechanical strength, and specifically, is selected from the group consisting of one or more types: 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzopyrene Azothiazole 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-indole (3-mercaptopropionate), pentaerythritol ginseng (3- Mercaptopropionate, pentaerythritol-indole (2-mercaptoacetate), pentaerythritol-gin (2-mercaptoacetate), trimethylol Propane-gin (2-mercaptoacetate), and trimethylolpropane-gin (3-mercaptopropionate).

As the adhesion promoter used in the present invention, one or more methacryloxycarbonyl decane coupling agents may be used, and methacryloxypropyltrimethoxydecane, methyl group such as methacryloxypropyltrimethoxydecane may be selected or used. Propylene decyloxypropylmethyldimethoxydecane, methacryloxypropyltriethoxydecane, or methacryloxypropylmethyldimethoxydecane, and a Or a plurality of types of n-octyltrimethoxydecane may be selected or used as octyltrimethoxydecane, dodecyltrimethoxydecane, octadecyltrimethoxydecane, and the like.

The surfactant may be a lanthanide surfactant or a fluorosurfactant, specifically BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK- manufactured by BYK-Chemie GmbH. 306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, and the like are available as Lanthanide surfactants, and F-114, F-177, F-410, F-411, F-450, F-493, F-494, F manufactured by DIC (Japan Pharmaceutical Co., Ltd.) -443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF , F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF -1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132 TF1027SF, TF-1441, TF-1442, and the like can be used as the fluorine-based surfactant, however, the lanthanoid surfactant and the fluorine-based surfactant are not limited thereto.

The antioxidant is selected from the group consisting of one or more types of the following: a hindered phenol-based antioxidant, an amine-based antioxidant, a sulfur-based antioxidant, and a phosphine-based antioxidant, but is not limited thereto.

Specific examples of the antioxidant may include a phosphate-based heat stabilizer such as phosphoric acid, trimethyl phosphate, or triethyl phosphate, and a hindered phenol-based primary antioxidant such as 2,6-di-t-butyl-p-cresol , octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetra-bis[methylene-3-(3,5-di-t-butyl-4) -hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6- G-t-butylphenol, 4,4'-butylene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-third Butylphenol), bis[3,3-bis-(4'-hydroxy-3'-t-butylphenyl)butyrate]ethylene glycol ester; amine secondary antioxidant such as phenyl-α-naphthalene Amine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine, or N,N'-di-β-naphthyl-p-phenylenediamine; thio-based secondary antioxidant, Such as dilauryl disulfide, dodecyl thiopropionate, distearyl thiopropionate, mercapto benzene, or tetramethyl disulfide methyl carbamide Base-3-(lauryl)propionate]methane; or phosphite secondary antioxidant such as triphenyl phosphite, tris(nonylphenyl) phosphate, triisodecyl phosphite, phosphorous acid Bis(2,4-dibutylphenyl)pentaerythritol diphosphite, or (1,1'-biphenyl)-4,4'-bisbisphosphite tetra[2,4-bis(1,1- Dimethylethyl)phenyl]ester.

As the ultraviolet absorber, for example, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, or the like can be mentioned. The ultraviolet absorber is not limited thereto, and the usual ingredients can be used in the related art.

Examples of thermal polymerization inhibitors may include one or more selected from the group consisting of p-anisole, hydroquinone, catechol, tert-butylcatechol, N-nitrosobenzene Hydroxylamine ammonium salt, N-nitrosophenylhydroxylamine ammonium salt, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis (3 -methyl-6-tert-butylphenol), 2,2-methylbis(4-methyl-6-tert-butylphenol), 2-mercaptoimidazole, and thiazine, but are not limited thereto, and It may be included in the prior art.

The dispersant may be a method of preferentially treating the pigment by internally adding a dispersant to the pigment in the surface form, or a method of externally adding a dispersant to the pigment. As the dispersing agent, a compound type, a nonionic type, an anionic type, or a cationic type dispersing agent can be used, and a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, amphoteric surfactant, or Analog. These may be used singly or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of one or more of the following: polyalkylene glycol and esters thereof, polyoxyalkylene polyol, ester alkylene oxide adduct, alcohol alkylene oxide An adduct, a sulfonate, a sulfonate, a carboxylate, a carboxylate, an alkyl amidene oxide adduct, and an alkylamine, but is not limited thereto.

The leveling agent can be polymeric or non-polymeric. The leveling agent of the polymer may, for example, be polyethyleneimine or polyamine. a reaction product of an amine, an amine, and an epoxide, and a specific non-polymerizable sulfur-containing and non-polymerizable nitrogen-containing compound of the non-polymerized leveling agent, but is not limited thereto, and the common compound can be used. In related fields.

Embodiments of the present invention provide a photosensitive material produced using a photoresist resin composition.

More specifically, the film type or pattern type photosensitive material is formed by forming a photoresist resin composition of the present invention on a substrate by a suitable method.

The coating method is not particularly limited, and a spray coating method, a roll coating method, a spin coating method, or the like can be used, and a spin coating method is widely used. Further, in some cases, the residual solvent after the formation of the coating film is partially removed by pressure reduction.

According to an embodiment of the present invention, the light source of the cured photoresist resin composition may be, for example, a mercury vapor arc, a carbon arc, or a xenon arc, which emits light having a wavelength of from 250 nm to 450 nm, but is not limited thereto.

According to the photoresist resin composition of the present invention, a color filter of a thin film transistor liquid crystal display (TFT LCD), a photosensitive material for forming a black matrix of an organic light emitting diode, or a thin film electricity can be produced using a pigment dispersion type photosensitive material. Crystal liquid crystal display (TFT LCD), photosensitive material for forming an overcoat layer, photosensitive material for column spacers, photocurable coating, photocurable ink, photocurable adhesive, printing plate, for printed circuit A photosensitive material for a sheet, a photosensitive material for a plasma display panel (PDP), or the like photosensitive material, and the application is not particularly limited.

Embodiments of the present invention provide a color filter that includes a photosensitive material.

The color filter can be prepared using a photoresist resin composition including a styrene compound represented by Chemical Formula 1. The color filter can form a coating film on the substrate using the photosensitive composition, and exposes, develops, and cures the coating film.

The photoresist resin composition according to an embodiment of the present invention has excellent heat resistance, and some slight color change is caused by heat treatment. Therefore, when a color filter is manufactured, high reproducibility, high brightness, and high contrast can be provided even through a curing process.

The substrate may include a glass substrate, a tantalum wafer, a plastic material plate, polyethersulfone (PES), or polycarbonate (PC), or the like, and the kind thereof is not particularly limited.

The color filter may include a red pattern, a green pattern, a blue pattern, or a black matrix.

In another embodiment, the color filter further includes a cover layer.

To improve contrast, a black pattern on the crystal lattice, the so-called black matrix, can be placed between the color pixels of the color filter. Chromium can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and patterning using an etching process can be used. However, in consideration of the high cost, high reflectivity chromium and environmental pollution caused by the chromium waste liquid, a method and micromachining of a resin black matrix of a pigment dispersion can be used.

According to the black matrix of one embodiment of the present invention, a black pigment or a black dye as a colorant can be used. For example, carbon black may be used alone or carbon black and color pigment may be used in combination, and in this case, the strength or adhesiveness of the film may be improved even if the amount of the colorant is relatively increased without being lowered. Point because the coloring pigment lacks light blocking properties.

The present invention provides a display device comprising the color filter of the present invention.

The display device is any one of the following: a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor liquid crystal display (LCD-TFT) ), and cathode ray tube (CRT).

A display device according to an embodiment of the present invention has high color reproducibility, high brightness, and high contrast, and thus has high light blocking characteristics. Due to these characteristics, an elongated display device can be produced.

Moreover, in one embodiment of the invention, the display module itself can be elongated and the display can be maximized using the top sealing portion and the minimized module bottom.

The contents of the present invention will be described in detail with reference to the embodiments. However, it is to be understood that the following examples are for illustrative purposes only, and the scope of the present invention includes the scope of the claims and the substitution or modification thereof, and is not limited to the embodiment.

<Preparation example>

(1) Preparation of a compound represented by Chemical Formula 1-1:

1) Preparation of chemical formula 1b

5 grams of 1a (33.51 millimoles), 3.136 grams (36.866 millimoles) of cyanoacetic acid, and 0.571 grams (6.703 millimoles) of piperidine were placed in 110 milliliters of ethanol (EtOH) at 85 ° C The mixture was stirred for 8 hours, and 1 ml of hydrochloric acid (HCl) was added to the mixture, stirred for 30 minutes and cooled to room temperature. The precipitated solid was filtered and dried to give 3.985 g (8.43 mmol) of the compound represented by the formula 1b (yield: 55%).

The measurement results of 1b using ¹ H-NMR are shown below.

¹ H NMR (500MHz, acetone -d6, ppm): 8.10 (1H , S, CH), 8.03-7.99 (2H, D, ARH), 6.87-6.85 (2H, D, ARH), 3.14 (6H, S, CH3).

2) Preparation of chemical formula 1-1

1.5 g of 1b compound (6.937 mmol), 1.44 g (11.098 mmol) 1c, 1.648 g (6.601 mmol) of ethyl carbodiimide hydrochloride (EDC-HCl), and 0.169 g (1.387 mmol) of dimethylaminopyridine (DMAP) was placed in 40 ml of tetrahydrofuran (THF) at 0 to 4 ° C, and the mixture was stirred for 2 hours and then stirred at room temperature for 24 hours. 150 ml of water was added to the reaction mixture, and the result was extracted with 600 ml of dichloromethane (MC). The organic layer was subjected to removal of water in an organic layer by magnesium sulfate (MgSO ₄ ), and the solvent was removed in vacuo, using a column (hexane/ethyl acetate = 4/1) to give 1.140 g of the formula 1-1 ( 3.468 millimoles) compound. Recovery rate (50%).

The measurement results of Chemical Formula 1-1 using ¹ H-NMR are shown below.

¹ H NMR (500 MHz, acetone-d6, ppm): 8.10 (1H, S, CH), 8.01-7.99 (2H, D, ARH), 6.87-6.85 (2H, D, ARH), 6.10 (1H, S, CH2), 5.64 (1H, S, CH2), 4.55-4.53 (2H, M, CH 2), 4.46-4.44 (2H, M, CH 2), 3.16 (6H, S, CH 3), 1.92 (3H, S, CH 3).

(2) Preparation of a compound represented by Chemical Formula 1-2

2 g (9.249 mmol) of 1b compound, 3.963 g (18.4986 mmol) of 1e, 1.7736 g (9.246 mmol) of ethyl carbodiimide hydrochloride (EDC-HCl) were prepared in (1). And 0.227 g (1.859 mmol) of dimethylaminopyridine (DMAP) were stirred at 0 to 4 ° C in 40 ml of tetrahydrofuran (THF) for 2 hours, and then stirred at room temperature for 24 hours. 150 ml of water was added to the reaction mixture, and the product was extracted with 600 ml of dichloromethane (MC). The organic layer was subjected to magnesium sulfate to remove water of the organic layer, and the solvent was removed under vacuum, and purified using a column (hexane/ethyl acetate = 6/1) to give 2.67 g of the formula 1-2. Compound (6.474 mmol) Seoul). Recovery rate (70%).

The measurement results of Chemical Formula 1-2 using ¹ H-NMR are shown below.

¹ H NMR (500MHz, acetone -d6, ppm): 8.09 (1H , S, CH), 8.00-7.99 (2H, D, ARH), 6.87-6.85 (2H, D, ARH), 6.42-6.39 (1H, D, CH2), 6.22-6.19 (1H, Q, CH), 6.11 (1H, S, CH2), 5.97-5.95 (1H, D, CH 2), 5.64 (1H, S, CH2), 5.58-5.55 ( 1H, m, CH), 4.60-4.40 (4H, m, CH2), 3.16 (6H, S, CH3), 1.92 (3H, S, CH3).

(3)) Preparation of a compound represented by Chemical Formula 1-3

1) Preparation of chemical formula 2b

Will be 5 grams of 2a (28.21 millimoles), 2.640 grams (31.03 millimeters) The cyanoacetic acid of Mohr) and 0.480 g (5.642 mmol) of piperidine were placed in 110 ml of ethanol, and the mixture was stirred at 85 ° C for 8 hours. 1 ml of hydrochloric acid (HCl) was added to the mixture, and the product was stirred for 30 minutes, and then cooled to room temperature, and the precipitated solid was filtered and dried to give 4.135 g (16.93 mM) of compound 2b represented by the chemical formula. Recovery rate (60%).

The results of 2b measurement using ¹ H-NMR are as follows: ¹ H NMR (500 MHz, CDCl 3 , ppm): 8.08 (1H, S, CH), 7.96-7.94 (2H, D, ARH), 6.69-6.68 (2H , ARH), 3.49-3.45 (4H, Q, CH2), 1.25-1.22 (6H, T, CH3).

2) Preparation of Chemical Formulas 1-3

1.5 g of 2b (6.14 mmol) compound, 1.279 g of 2c (9.824 mmol), 1.450 g (7.614 mmol) of ethyl carbodiimide hydrochloride (EDC-HCl), and 0.150 Glucan (1.228 mmol) of dimethylaminopyridine (DMAP) was placed in 40 ml of tetrahydrofuran (THF) at 0 to 4 ° C, and the mixture was stirred for 2 hours, and then stirred at room temperature for 24 hours. 150 ml of water was added to the reaction mixture, and the product was extracted with 600 ml of dichloromethane (MC). The organic layer was subjected to magnesium sulfate to remove water of the organic layer, and the solvent was removed under vacuum, and purified using a column (hexane/ethyl acetate = 4/1) to give 1.439 g of the formula 1-3. Compound (4.060 mmol). Recovery rate (66%).

The results of the measurement of Chemical Formula 1-3 using ¹ H-NMR are as follows: ¹ H NMR (500 MHz, CDCl 3 , ppm): 8.02 (1H, S, CH), 7.91-7.89 (2H, D, ARH), 6.66-6.64 (2H, D, ARH), 6.14 (1H, S, CH2), 5.57 (1H, S, CH2), 4.51-4.49 (2H, M, CH2), 4.43-4.41 (2H, M, CH2), 3.45- 3.41 (4H, Q, CH2), 1.93 (3H, S, CH3), 1.22-1.19 (6H, T, CH3).

(4)) Preparation of a compound represented by Chemical Formula 1-4

2 g of 2b (8.187 mmol) compound obtained in (3), 2.055 g (9.006 mmol) of 2e, 1.736 g (9.006 mmol) of ethylcarbodiimide hydrochloride (EDC) -HCl), and 0.2 g (1.637 mmol) of dimethylaminopyridine (DMAP), placed in 40 ml of tetrahydrofuran (THF) at 0 to 4 ° C, and the mixture was stirred for 2 hours. Stir under temperature for 24 hours. 150 ml of water was added to the reaction mixture, and the product was extracted with 600 ml of dichloromethane (MC). The organic layer was subjected to magnesium sulfate to remove water of the organic layer, and the solvent was removed under vacuum, and purified using a column (hexane/ethyl acetate = 6/1) to give 3.102 g of the formula 1-4. Compound (6.825 mmol). Recovery rate (83%).

The results of the measurement of Chemical Formulas 1-4 using ¹ H-NMR are as follows: ¹ H NMR (500 MHz, CDCl 3 , ppm): 7.97 (1H, S, CH), 7.86-7.84 (2H, D, ARH), 6.62-6.60 (2H, D, ARH), 6.08 (2H, S, CH2), 5.54 (2H, S, CH2), 5.48-5.46 (1H, m, CH), 4.46-4.33 (4H, m, CH2), 3.41 3.37 (4H, Q, CH2), 1.88 (6H, S, CH3), 1.17.15 (6H, T, CH3).

(5) Preparation of a compound represented by Chemical Formula 1-5

1.5 g of 3a compound (4.407 mmol), 0.917 g (7.05 mmol) of 3b, 1.047 g (5.464 mmol) of ethyl carbodiimide hydrochloride (EDC-HCl), and 0.070 g (0.573 mmol) of dimethylaminopyridine (DMAP) The mixture was placed in 50 ml of tetrahydrofuran (THF), and the mixture was stirred at 0 to 4 ° C for 2 hours, and then stirred at room temperature for 24 hours. 150 ml of water was added to the reaction mixture, and the product was extracted with 700 ml of dichloromethane (MC). The organic layer was subjected to magnesium sulfate to remove water of the organic layer, and the solvent was removed under vacuum, and purified using a column (hexane/ethyl acetate = 4/1) to give 1.595 g of the formula 1-5. Compound (3.526 mmol). Recovery rate (80%).

The results of the measurement of Chemical Formula 1-5 using ¹ H-NMR are as follows: ¹ H NMR (500 MHz, CDCl 3 , ppm): 8.14 (1H, S, CH), 7.88-7.79 (2H, D, ARH), 7.39-7.31 (4H, m, ARH), 7.24-7.14 (6H, m, ARH), 6.97-6.88 (2H, D, ARH), 4.52-4.49 (2H, M, CH2), 4.43-4.40 (2H, M, CH2 ), 1.94 (3H, S, CH3).

(6) Preparation of a compound represented by Chemical Formula 1-7

1.25 g of 4a compound (3.393 mmol), 0.706 g of 4b (5.428 mmol), 0.806 g (4.207 mmol) of ethyl carbon two The imine hydrochloride (EDC-HCl), and 0.051 g (0.441 mmol) of dimethylaminopyridine (DMAP) were placed in 40 ml of tetrahydrofuran (THF), and the mixture was stirred at 0 to 4 ° C for 2 hours. The stirrer was stirred at room temperature for 24 hours. 150 ml of water was added to the reaction mixture, and the product was extracted with 600 ml of dichloromethane (MC). The organic layer was subjected to magnesium sulfate to remove water of the organic layer, and the solvent was removed under vacuum, and purified using a column (hexane/ethyl acetate = 4/1) to give 1.97 g of the formula 1-7. Compound (2.491 mmol). Recovery rate (73%).

The results of the measurement of Chemical Formula 1-7 using ¹ H-NMR are as follows: ¹ H NMR (500 MHz, CDCl 3 , ppm): 8.03 (1H, S, CH), 7.88-7.86 (2H, D, ARH), 7.35-7.32 (4H, t, ARH), 7.29-7.26 (2H, t, ARH), 7.19-7.17 (4H, D, ARH), 6.78-6.76 (2H, D, ARH), 6.13 (1H, S, CH2), 5.57 (1H, S, CH2), 4.74 (4H, S, CH2), 4.51-4.48 (2H, M, CH2), 4.42-4.40 (2H, M, CH2), 1.93 (3H, S, CH3).

<Examples 1 to 3 and Comparative Example 1> Comparison of color components of green photoresist resin composition

The results are shown in Table 1 below, based on comparison of the coloring compositions of the green photoresist resin compositions prepared in the respective Examples and Comparative Examples.

1) Weight ratio

Adhesive resin: a copolymer of benzyl methacrylate and methacrylic acid having a molar ratio of 70:30 and an acid value of 113 KOH mg/g as measured by GPC20,000 and molecular weight distribution (PDI) 2.0. The weight average molecular weight and solid content (SC) were 25%.

Solvent: propylene glycol monomethyl ether acetate (PGMEA)

Photoinitiator: I-369 (manufactured by BASF Corporation)

Polyfunctional monomer: diphenylpentaerythritol hexaacrylate (DPHA)

<Example 4 and Comparative Example 2> Comparison of color compositions of green photoresist resin compositions

The results of the coloring compositions of the green photoresist resin compositions prepared in the respective examples and comparative examples are shown in Table 2 below.

Adhesive resin: a copolymer of benzyl methacrylate and methacrylic acid having a molar ratio of 70:30, an acid value of 113 KOH mg/g, and a weight measured by GPC20,000, molecular weight distribution (PDI) 2.0. The average molecular weight and solid content (SC) were 25%.

<Example 5> Comparison of brightness (Y) and color coordinates (G _x , G _y )

The photoresist resin composition was spin-coated on a glass of 5×5 cm (manufactured by Corning Co., Ltd.) and the film was prebaked at 90 ° C for about 100 seconds, and the film formed between the mask and the substrate was 300 μm. A light of 40 mJ/cm ² was irradiated using a stepper (manufactured by HOYA-shott). The exposed substrate was exposed to a developing solution for 60 seconds (KOH, 0.05%), and dried at 230 ° C for 20 minutes to obtain a color pattern.

A transmission spectrum having a visible light region in the range of 380 nm to 780 nm is obtained by a spectrometer through a color pattern. Using the obtained transmission spectrum and a C-light backlight, the tristimulus values (X, Y, Z values) were obtained using the following formula, and were calculated from the values of CIE 1931 coordinates x, y, Y using the following formula.

S: C light source

R: Mode transmission spectrum of green photoresist resin composition

: Color matching function

In Table 3 below, the color coordinates of the C light source were calculated using the green photoresist resin composition as shown in Table 3 below.

As shown in Table 3, it has a better effect in terms of brightness as compared with the comparative example. The increase in brightness compared to the comparative example is due to the increase in transmission from 450 nm to 680 nm.

<Example 6> Solubility

The solubility of each of the compounds 1-1 to 1-5 and 1-7 was measured using a propylene glycol methyl ether acetate (PGMEA) solvent as a standard, and the results are shown in Table 4 below.

Claims (22)

A styrenic compound represented by the following Chemical Formula 1: Wherein n is an integer of 1 to 3, m is an integer of 1 to 4, X is NR or O, and R is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, and a substituted or unsubstituted carbon having 2 to 25 carbon atoms a group consisting of substituted alkenyl groups; L1 is a direct bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; R1 and R2 are the same or different from each other, and are each independently Hydrogen, substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted with 1 to 25 carbon atoms or Unsubstituted alkoxy group, substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, having 6 to 40 a substituted or unsubstituted aryl group of a carbon atom, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted heterocyclic group of one or more N, O and S atoms; R3 is hydrogen, deuterium, halo, nitrile, nitro, hydroxy, substituted with 1 to 25 carbon atoms or An unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms; R 4 is hydrogen, An anthracene, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, a substituted or 6 to 40 carbon atom substituted or unsubstituted Substituted aryl, substituted or unsubstituted fluorenyl group, substituted or unsubstituted carbazolyl, substituted or unsubstituted hetero including one or more N, O and S atoms a cyclic group; and R5 is hydrogen, hydrazine, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, a substituted or 2 to 25 carbon atom substituted or unsubstituted Substituted alkenyl group, substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted propylene group having 3 to 40 carbon atoms, substituted or unsubstituted a fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted acrylate group, a substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms, or a Or a plurality of substituted or unsubstituted heterocyclic groups of N, O and S atoms. The styrene-based compound according to the first aspect of the invention, wherein the styrene-based compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2: Wherein N, M, R1 to R4, X, and L1 are the same as defined above, and R6 is hydrogen, deuterium, halogen, nitrile, nitro, hydroxy, substituted or unsubstituted having 1 to 25 carbon atoms. a substituted alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, having 2 to 25 carbon atoms Substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted fluorenyl group, substituted or unsubstituted anthracene Azolyl, substituted or unsubstituted heterocyclic group comprising one or more N, O and S atoms. The styryl compound according to claim 1, wherein R1 and R2 are the same or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, and contains 6 to 40 carbon atoms A substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms. The styrenic compound according to claim 1, wherein R4 is a nitrile group, a substituted or unsubstituted alkyl group having 6 to 40 carbon atoms, and the alkyl group is composed of one or more substituents. Unsubstituted or substituted, and the substituent is selected from the group consisting of: halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine group, alkylamine group, carbazole a group consisting of a fluorenyl group, a nitrile group, and a heterocyclic group comprising one or more N, O and S atoms, or a group of one or more N, O and a heterocyclic group of the S atom, which is unsubstituted or substituted by one or more substituents selected from the group consisting of: halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine Group consisting of an arylamine group, an alkylamine group, a carbazolyl group, a fluorenyl group, a nitrile group, and a heterocyclic group including one or more N, O, and S atoms. . The styrenic compound according to claim 1, wherein L1 is a linear or branched alkylene group having 1 to 10 carbon atoms, and the alkylene group is unsubstituted by one or more substituents. Or substituted, the substituent is selected from the group consisting of: halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine group, alkylamine group, carbazolyl, fluorenyl A group consisting of a fluorenyl group, an acryloyl group, an acrylate group, a nitrile group, and a heterocyclic group including one or more N, O, and S atoms. The styrenic compound according to claim 1, wherein R5 is hydrogen, hydrogen, or an acrylate group which is unsubstituted or substituted by one or more substituents selected from the group consisting of: a halogen group, an alkane Base, alkenyl, cycloalkyl, An aryl group, an arylamine group, an alkylamine group, a carbazolyl group, a fluorenyl group, a nitrile group, and a heterocyclic ring including one or more N, O and S atoms. a group consisting of a group, a carbonyl group unsubstituted or substituted by one or more substituents selected from the group consisting of: halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine ( An arylamine group), an alkylamine group, a carbazolyl group, a fluorenyl group, a nitrile group, and a heterocyclic group including one or more N, O, and S atoms, or From one or more unsubstituted or substituted propylene thiol groups selected from: halo, alkyl, alkenyl, cycloalkyl, aryl, arylamine group, alkylamino group A group consisting of an alkylamine group, a carbazolyl group, a fluorenyl group, a nitrile group, and a heterocyclic group including one or more N, O, and S atoms. The styrene-based compound according to the first aspect of the invention, wherein the styrene-based compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8. The styrenic compound according to claim 1, wherein the styrene compound has a maximum absorption wavelength (λ _max ) of from 400 nm to 500 nm. The styrenic compound according to claim 1, wherein the styrene compound has an absorption spectrum of from 350 nm to 500 nm. A coloring agent comprising the styrenic compound according to any one of claim 1 to claim 9. The coloring agent according to claim 10, wherein the coloring agent is composed of the styrene compound alone. The coloring agent according to claim 10, comprising: the styrenic compound, and one, two or more additional colorants are selected from the group consisting of pigments and dyes. The coloring agent according to claim 10, wherein the ratio of the molecular weight of the styrene compound and the coloring agent is from 1:99 to 99:1. A photoresist resin composition comprising the coloring agent of claim 10 of the patent application. The photoresist resin composition of claim 14, further comprising: an adhesive resin; a polyfunctional monomer; a photoinitiator; and a solvent. The photoresist resin composition according to claim 15, wherein the colorant is contained in an amount of 5 to 60% by weight based on the total weight of the solid content of the photoresist resin composition; The content of the resin is from 1% by weight to 60% by weight; the content of the initiator is from 0.1% by weight to 20% by weight; and the content of the polyfunctional monomer is from 0.1% by weight to 50% by weight. The photoresist resin composition according to claim 15, further comprising: one, two or more additives selected from the group consisting of: a light sensitizer, a curing accelerator, a adhesion promoter, a surfactant A group consisting of an antioxidant, a thermal polymerization inhibitor, a UV absorber, a dispersant, and a leveling agent. The photoresist resin composition according to claim 17, wherein the additive is contained in an amount of from 0.1% by weight to 20% by weight based on the total mass of the solid content of the resist resin composition. A photosensitive material prepared by the photoresist resin composition of claim 14 of the patent application. A color filter comprising the photosensitive material of claim 19 of the patent application. The color filter of claim 20, wherein the color filter comprises a red pattern, a green pattern, a blue pattern, and a black matrix. A display device comprising the color filter of claim 21 of the patent application.