KR20180012094A - Photosensitive resin composition and color filter comprising same - Google Patents

Abstract

The present invention relates to a photosensitive resin composition and a color filter comprising the same. The photosensitive resin composition comprises a compound expressed by chemical formula 1 and a compound expressed by chemical formula 2, [(RSiO_(1.5))_n]. Therefore, the photosensitive resin composition lowers sensitivity and simultaneously increases brightness in forming a hole in a pattern.

Description

TECHNICAL FIELD [0001] The present invention relates to a photosensitive resin composition and a color filter including the same. BACKGROUND ART [0002]

The present invention relates to a photosensitive resin composition and a color filter including the same.

Recently, color filters are required to have high brightness and high contrast ratio. One of the main objectives of the display device development is to differentiate display device performance by improving color purity and to improve productivity in a manufacturing process.

Conventionally, a pigment type used as a coloring material of a color filter is present in a color photoresist in a particle dispersion state, and thus it has been difficult to control the luminance and contrast ratio according to the size and distribution of the pigment particles. In the case of pigment particles, multiple scattering of light occurs due to large particles that are aggregated in the color filter and are poorly soluble and dispersible. The scattering of the polarized light is regarded as a main factor for lowering the contrast ratio. Efforts have been made to improve the brightness and contrast ratio through ultrafiltration and stabilization of the pigment, but the degree of freedom in selecting a coloring material for implementing a color coordinate system for a high color purity display device is limited. In addition, the pigment dispersion method using the color materials, especially the pigments, already developed has reached a limit to improve the color purity, brightness and contrast ratio of the color filter using the pigment dispersion. Accordingly, development of a coloring material capable of improving color purity, color reproduction, luminance and contrast ratio, or a photosensitive resin composition containing the coloring material has been desired.

Japanese Unexamined Patent Publication No. 9-87534

The present invention relates to a photosensitive resin composition and a color filter manufactured using the same.

An embodiment of the present invention provides a photosensitive resin composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (2).

[Chemical Formula 1]

(2)

[(RSiO _1.5 ) _n ]

In formula (1)

L _A and L _B are the same or different and are each independently a direct bond; Or an alkylene group having 1 to 10 carbon atoms,

R _A to R _F are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen atom; A nitro group; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms,

R ₁ to R ₆ are the same or different and each independently hydrogen; heavy hydrogen; A halogen atom; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 6 carbon atoms; And a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms; Sulfonic acid group; Sulfonic acid ester groups; Sulfonic acid base; -SO ₂ NHR ₇ group; Is selected from the group consisting of and -SO ₂ NR ₈ R _9,

R ₇ to R ₉ are the same or different and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms,

X ₁ to X ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms,

At least one of X ₁ to X ₅ is an anionic group,

R _AA and R _BB are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms; A halogen atom; A nitro group; Phenoxy group; A carboxy group; Carboxy acid ester group; Carboxy acid base; An alkoxycarbonyl group; A hydroxy group; Sulfonic acid group; Sulfonic acid ester groups; Sulfonic acid base; -SO ₂ NHR '; And it is selected from the group consisting of -SO ₂ NR "R '",

a and b are the same or different and each independently represents an integer of 0 to 4,

When a and b are two or more, the structures in parentheses are the same or different from each other,

R ', R "and R" " are the same or different and each independently an alkyl group having 1 to 30 carbon atoms,

In formula (2)

n is an even number of 4 or more,

R is represented by - (L ₁ ) _{n 1} -R ₇ ,

A plurality of Rs are the same or different from each other,

L ₁ is a direct bond; -O-; -S-; Or an alkylene group having 1 to 30 carbon atoms,

n1 is an integer of 1 to 5,

When n1 is 2 or more, L1 is the same or different from each other,

; -N=C=O; -C=C-; 탄소수 1 내지 30의 치환 또는 비치환된 알킬기; 탄소수 6 내지 30의 아릴기; 또는 탄소수 1 내지 30의 헤테로고리기이다.R ₇ is hydrogen; heavy hydrogen; -OH; An epoxide group; -SH; -NH2;

; -N = C = O; -C = C-; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 1 to 30 carbon atoms.

In addition, one embodiment of the present invention provides a photosensitive material manufactured using the photosensitive resin composition and a color filter including the photosensitive material.

The photosensitive resin composition according to one embodiment of the present invention can lower the sensitivity and increase the luminance in realizing a hole in a pattern when forming a pattern for a color filter.

In addition, the photosensitive resin composition according to one embodiment of the present invention has excellent adhesion between the pattern and the substrate even at low sensitivity.

FIG. 1 shows the result of measurement of a color filter pattern using a photosensitive resin composition according to an embodiment of the present invention and a fine pattern adhesion force of a comparative example.
2 shows the results of measurement of chemical resistance of the color filter pattern using the photosensitive resin composition according to one embodiment of the present invention and the NMP chemical resistance of the comparative example.

Hereinafter, the present invention will be described in more detail.

Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

According to one embodiment of the present invention, there is provided a photosensitive resin composition comprising the compound represented by Formula 1 and the compound represented by Formula 2.

As used herein, the term " substituted or unsubstituted " A halogen atom; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An arylalkenyl group; An aryl group; An aryloxy group; Aralkyl groups; An aralkenyl group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; Carbazole group; Acryloyl group; Acrylate groups; Ether group; A nitrile group; A nitro group; A hydroxy group; Cyano; Quot; means substituted or unsubstituted with at least one substituent selected from the group consisting of a heteroaryl group containing at least one of N, O, S, or P atoms and an anionic group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 2 to 25. Specific examples thereof include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group.

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30.

In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 20 carbon atoms, and in particular, it may be a cyclopentyl group or a cyclohexyl group.

In the present specification, examples of the halogen atom include fluorine, chlorine, bromine or iodine.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited and may be 6 to 40 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And may have from 10 to 40 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group or a fluorenyl group.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se, and the number of carbon atoms is not particularly limited. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 1 to 30. [ Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thiazolidinyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thiomorpholinyl group, an isothiazolyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl , A carbazole group, a benzocarbazole group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenazinyl group, an imidazopyridine group, a phenoxazinyl group, a phenanthroline group, a phenanthroline group, Phenothiazine group, imidazopyridine group, imidazophenanthridine group. A benzoimidazoquinazolinyl group, a benzoimidazophenanthridin group, and the like, but are not limited thereto.

In one embodiment of the present invention, the heterocyclic group has 3 to 60 ring members. In another embodiment, the heterocyclic group has 3 to 40 ring members. In one embodiment, the heterocyclic group has 3 to 20 ring members.

In the present specification, the heteroaryl group is an aromatic heterocyclic group containing O, N, S or P as a heteroatom, and the number of carbon atoms is not particularly limited, but may be 1 to 30 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group and a dibenzofuran And the like, but the present invention is not limited thereto. In the present specification, the description of the above-mentioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.

In this specification, an alkylene group means that there are two bonding sites in an alkane. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but may be 2 to 25 carbon atoms.

In this specification, the description of the aryl group can be applied except that the arylene group is a divalent group.

In the present specification, the description of the heteroaryl group can be applied except that the heteroarylene group is a divalent group.

In this specification, the meaning that adjacent groups combine with each other to form a substituted or unsubstituted ring means a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; Or a condensed ring thereof.

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

Specific examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. But are not limited to these.

In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. In the present specification, specifically, examples of the aromatic hydrocarbon ring include phenyl, naphthyl, anthracenyl, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, But are not limited to, cyclopentene, cyclopentene, cyclopentene, cyclopentene, cyclopentene, cyclopentene, cyclohexene,

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom. Specific examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, Azokane, thiocane, and the like, but are not limited thereto.

As used herein, an aromatic heterocyclic ring means an aromatic ring containing at least one heteroatom. Specifically, examples of the aromatic heterocycle include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole , Thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinoline, quinazoline, quinoxaline, naphthyridine And examples thereof include at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of pyridine, , Benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

In one embodiment of the present disclosure, L _A and L _B are the same or different from each other, and are each independently a direct bond; Or an alkylene group having 1 to 10 carbon atoms.

In one embodiment, L _A and L _B are each a propylene group.

In one embodiment of the present disclosure, R _A to R _F are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen atom; A nitro group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms.

In one embodiment, R _A through R _F are hydrogen.

According to one embodiment of the present disclosure, R ₁ to R ₆ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight or branched chain alkyl group having 1 to 6 carbon atoms, a sulfonic acid group, a sulfonic acid group, a -SO ₂ NHR ₇ group; Is selected from the group consisting of and -SO ₂ NR ₈ R _9,

R ₇ to R ₉ are the same or different and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present disclosure, R ₁ to R ₆ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 -C 6 linear or branched alkyl group, and a sulfonate group.

In one embodiment of the present specification, X ₁ to X ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms, and at least one of X ₁ to X ₅ is an anionic group.

In one embodiment of the present disclosure, the anionic group is ^{_{-OH, -SO 3 -, -SO 3}} H, -SO 3 - Z +, -CO 2 H, -O 2 - Z +, -CO 2 R a , -SO ₃ R _b and -SO ₃ NR _c R _d , Z ⁺ represents N (R _e ) ₄ ⁺ , Na ⁺ or K ⁺ , and R _a to R _e are each at least one selected from the group consisting of A substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms.

According to yet an embodiment of the present disclosure, the anionic groups are -SO ₃ ^- can be a Na ^{+ -} or -SO _3.

The anionic group may have an anion itself, or may exist in the form of a complex with other cations. Therefore, depending on the number of the substituted anionic groups, the sum of the molecular total charges of the compound of formula (1) may vary. Since the amine group of the compound of the present invention has a cation, the sum of the total charges of the molecule may have an anion value of 0 minus one in the number of substituted anionic groups.

In one embodiment of the present specification, R ', R "and R'" are the same or different and each independently an alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L < ₁ > are the same or different and are each independently a direct bond; -O-; -S-; Or an alkylene group having 1 to 30 carbon atoms.

In one embodiment, L < ₁ > is -O-.

In one embodiment, L &_lt; ₁ > is a methylene group; An ethylene group; Or a propylene group.

In one embodiment of the present disclosure, R ₁ is selected from the group consisting of hydrogen; heavy hydrogen; -OH; An epoxide group; -SH; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 1 to 30 carbon atoms.

In one embodiment, R ₇ is -SH.

In one embodiment, R ₇ is an epoxide group.

In one embodiment, R ₇ is a phenyl group.

In one embodiment of the present invention, R may be represented by any one of the following formulas (2-a) to (2-e).

[Chemical Formula 2-a]

[Formula 2-b]

[Chemical Formula 2-c]

[Chemical Formula 2-d]

[Chemical Formula 2-e]

In one embodiment, R may be represented by any one of formulas (2-b) and (2-c).

In one embodiment of the present invention, the compound represented by Formula 2 may be SQ506 of Arakawa.

In one embodiment of the present invention, the compound represented by Formula 2 may be KBM-503 from Shin-etsu.

In one embodiment of the present invention, the photosensitive resin composition comprises a binder resin; Multifunctional monomers; Photoinitiators; And a solvent.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film made of a resin composition.

The binder resin may be a copolymer resin of a monomer having a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility. The binder resin may further include a binder generally used in the art.

In one embodiment, the binder resin may be an acrylic binder resin.

The multifunctional monomer which imparts the mechanical strength of the film is an unsaturated carboxylic acid ester; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And an acid anhydride.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (Meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl Hydroxypropyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl Methoxyethyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl Tocidyl ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) , Methyl [alpha] -hydroxymethyl acrylate, ethyl [alpha] -hydroxymethyl acrylate, propyl [alpha] -hydroxymethyl acrylate and butyl [alpha] -hydroxymethyl acrylate But, it is not limited thereto.

Specific examples of the aromatic vinyl monomers include aromatic vinyl monomers such as styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, Styrene, but are not limited thereto.

Specific examples of the unsaturated ethers may be 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 imide are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide But is not limited to these.

Examples of the acid anhydrides include maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.

The alkali-solubilizing monomer is not particularly limited as long as it contains an acid group, and examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene- (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, omega -carboxypolycaprolactone mono But it is not limited to these.

According to one embodiment of the present invention, the acid value of the binder resin is 50 to 130 KOH mg / g and the weight average molecular weight is 1,000 to 50,000.

The multifunctional monomer is a monomer that functions to form a photoresist phase by light. Specific examples thereof include propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxy ethylisocyanurate trimethacrylate, trimethyl 1 > is selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexa methacrylate. Species or a mixture of two or more species.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce crosslinking. For example, the photoinitiator is selected from the group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, and a oxime compound Or more.

The acetophenone compound may be at least one selected from the group consisting of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl- (4-morpholinophenyl) -butan-1-one, or 2- (4-bromo-benzyl-2-dimethylamino- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, and the like.

Examples of the biimidazole-based compounds include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) 4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like , But is not limited thereto.

The triazine-based compound may be at least one selected from the group consisting of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- (Trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl 2- {4- [2,4 Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2- epoxyethyl-2- {4- [ Yl] phenylthio} acetate, benzyl-2- {4- [2- (4-fluorophenyl) (Trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 3- {chloro-4- [ (Phenylthio) propionic acid, 2,4- bis (trichloromethyl) -s-triazine-6-yl] Methyl-6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1- Methylaminophenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like .

The oxime-based compound may be at least one selected from the group consisting of 1,2-octadione, -1- (4-phenylthio) phenyl, 2- (o-benzoyloxime) (Ciba Geigy, Shisei 124), ethanone, -Ethyl) -6- (2-methylbenzoyl-3-yl) -, 1- (O-acetyloxime) (Cajoo 242), N-1919 (Adeca), and the like.

The solvent is selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 Cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethylhexanoate, 2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, Methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl It may be at least one member selected from the group consisting of ethyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether. But is not limited thereto.

In one embodiment of the present invention, the content of the compound represented by Formula 1 is 0.1 to 50 parts by weight based on the total weight of the solid components in the photosensitive resin composition,

The content of the compound represented by the general formula (2) is 0.01 to 10 parts by weight,

The content of the binder resin is 1 part by weight to 60 parts by weight,

The content of the photoinitiator is 0.1 part by weight to 20 parts by weight,

The content of the polyfunctional monomer is 0.1 part by weight to 50 parts by weight.

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. The standards of parts by weight based on the solid content and the solid content of each component can be measured by general analytical means used in the art such as liquid chromatography or gas chromatography.

In one embodiment of the present invention, the photosensitive resin composition may further include at least one of a dye and a pigment.

Both dyes and pigments absorb the wavelengths of a desired range and act as a coloring agent. Dyes and pigments can be distinguished depending on the solubility in a solvent. The dye may be referred to as being easily soluble because of its high solubility in solvents, and the pigment may be referred to as being relatively insoluble and not easily soluble.

In addition, the dye may be at least one selected from the group consisting of an anthraquinone dye, a tetraazaporphyrin dye and a triarylmethane dye.

The anthraquinone dyes may be represented by the following formula (3).

(3)

In Formula 3,

R ₁₁ and R ₁₂ are each independently at least one selected from the group consisting of an amino group, an alkylamino group, a dialkylamino group, a phenylamino group and a diphenylamino group.

According to an embodiment of the present invention, the anthraquinone-based dye may be any one selected from the following compounds.

.

.

Further, according to one embodiment of the present invention, the tetraazaporphyrin-based dye may be selected from the following compounds.

.

.

Further, according to one embodiment of the present invention, the triarylmethane-based dye may be any one selected from the following compounds.

Further, in one embodiment of the present invention, the pigment is a blue pigment.

The blue pigments include, for example, CI Pigment Blue 15, CI Pigment Blue 15: 3, CI Pigment Blue 15: 4, CI Pigment Blue 15: 6, CI Pigment Blue 60 and the like as blue organic pigments .

In one embodiment, the pigment may comprise a copper phthalocyanine-based pigment.

The blue dye may include, for example, a methyl-based dye, an anthraquinone-based dye, an azo-based dye, a triarylmethane-based dye, a phthalocyanine-based dye and the like as a blue dye.

The blue pigments may include blue lakes, such as those obtained by laking blue pigments such as those described above with rake agents. Examples of the lubricating agent include, but are not limited to, tungstic acid, phosphoric acid, phosphoric acid, tungsten molybdic acid, tannic acid, lauric acid, 3,4,5-trihydroxybenzoic acid, ferricyanide, ferrocyanide Can be used.

Examples of specific blue lake pigments include CI Pigment Blue 1, CI Pigment Blue 1: 2, CI Pigment Blue 2, CI Pigment Blue 3, CI Pigment Blue 8, CI Pigment Blue 9, CI Pigment Blue 10, CI Pigment Blue 12, CI Pigment Blue 14, CI Pigment Blue 17: 1, CI Pigment Blue 18, CI Pigment Blue 19, CI Pigment Blue 24, CI Pigment Blue 24: CI Pigment Blue 62, CI Pigment Blue 56, CI Pigment Blue 56, CI Pigment Blue 61, CI Pigment Blue 61, CI Pigment Blue 62, CI Pigment Blue 63, CI Pigment Blue 78, .

In one embodiment of the present invention, the photosensitive resin composition further comprises a dispersant, and the dispersant may include a polymer comprising a repeating unit represented by the following formula (11) or a repeating unit represented by the following formula (12).

(11)

[Chemical Formula 12]

In formulas (11) and (12)

R ₃₀₁ and R ₄₀₁ are the same or different from each other, and each independently hydrogen; Or an alkyl group having 1 to 10 carbon atoms,

R ₃₀₂ , R ₃₀₃ , R ₄₀₂ and R ₄₀₃ are the same or different from each other, and each independently hydrogen; An alkyl group having 1 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 1 to 30 carbon atoms,

R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R ₄₀₃ are bonded to each other to form a substituted or unsubstituted ring,

Ar ₃ and Ar ₄ are the same or different and are each independently a direct bond; An alkylene group having 1 to 10 carbon atoms; _{- [CH (R 311) -CH} (R 312) -O] x -CH (R 313) -CH (R 314) - or _{- [(CH 2) y1 -O} ] z - (CH 2) y2 - a ≪ / RTI >

R ₃₁₁ to R ₃₁₄ are the same or different and each independently hydrogen; Or an alkyl group having 1 to 10 carbon atoms,

x is an integer of 1 to 18, and when x is 2 or more, the structures in parentheses are the same or different from each other,

y1 and y2 are the same or different and each independently represents an integer of 1 to 5,

z is an integer of 1 to 18, and when z is 2 or more, the structures in parentheses are the same or different from each other,

Q is a direct bond; An alkylene group having 1 to 10 carbon atoms; An arylene group having 6 to 30 carbon atoms; -CONH-; -COO-; And an ether group having 1 to 10 carbon atoms.

In one embodiment, the dispersing agent may be contained in an amount of 0.5 to 50 parts by weight based on the total weight of the solid content in the resin composition.

According to one embodiment of the present invention, the resin composition may further comprise an antioxidant.

According to one embodiment of the present invention, the content of the antioxidant is 0.1 part by weight to 20 parts by weight based on the total weight of the solid content in the resin composition.

According to one embodiment of the present invention, the resin composition further comprises one or more additives selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersing agent and a leveling agent .

According to one embodiment of the present invention, the content of the additive is 0.1 to 20 parts by weight based on the total weight of the solid content in the resin composition.

The photo-crosslinking sensitizer may be at least one selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, Benzoate compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorene-based compounds such as 9-fluorenone, 2-chloro-9-proprenone and 2-methyl-9-fluorenone; Thioxanthone systems such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxytioxanthone, isopropylthioxanthone and diisopropylthioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; (9-acridinylpentane), 1,3-bis (9-acridinyl) propane, and the like Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide-based compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide; Benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis Amino-synergists such as methyl-cyclopentanone; (Diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl- -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- Pyran o [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylaminokalone and 4-azidobenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline, and the like.

As the curing accelerator, curing and mechanical strength are used, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2- mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate) (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) Nate) may be used.

Examples of the adhesion promoter used in the present invention include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane , And at least one selected from the group consisting of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like as the alkyltrimethoxysilane can be used. You can choose to use it.

Specifically, the silicone surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK- 307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK- BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380 and BYK-390. F-447, F-444, F-450, F-493, F-494, F-443, F-444, F- 484, F-470, F-471, F-472, F-474, F-475, F-477, F-478, F- TF-1127, TF-1126, TF-1127, TF-1127, TF-1129, TF-1126, TF-1130, TF- 1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like.

The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid type heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; Butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t- butylphenyl) propionate, tetrabis [methylene- Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di- 4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3- Hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-? -Naphthylamine, phenyl-? -Naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-? -Naphthyl- Secondary antioxidant; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethyl thiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Secondary antioxidant; (2,4-ditbutylphenyl) pentaerythritol diphosphite or (1, 2,4-dibutylphenyl) pentaerythritol diphosphite or bis (2,4-dibutylphenyl) (1,1'-biphenyl) -4,4'-diisopropylphosphonic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] -Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone may be used. Anything that is commonly used can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy (3-methyl-6-t-butylphenol), 2,2-dimethyl-2-pyrrolidone, But are not limited to, methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, And may include those generally known in the art.

The dispersant may be used either in a manner of internally adding to the pigment in the form of surface-treating the pigment in advance, or in a method of externally adding the pigment. As the dispersing agent, compound type, nonionic, anionic or cationic dispersing agent can be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic, amphoteric surfactants and the like. These may be used individually or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, Alkyl amide alkylene oxide adducts, and alkyl amines, but are not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamide amine, reaction products of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen- But are not limited to, compounds commonly used in the art may all be used.

An embodiment of the present disclosure provides a photosensitive resin composition comprising a compound represented by the following formula (15), a compound represented by the following formula (2), a dye and a dispersant, and the dye is a triarylmethane dye.

[Chemical Formula 15]

(2)

In the formula (15), the definitions of R ₁ to R ₆ , R _A to R _D , R _AA , R _BB and X ₁ to X _{5 and} the definitions of the formula (2) are as mentioned above.

One embodiment of the present invention provides a photosensitive material produced using the resin composition.

More specifically, a resin composition according to an embodiment of the present invention provides a photosensitive material in the form of a thin film or a pattern applied on a substrate in an appropriate manner.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. After the coating film is formed, a part of the residual solvent may be removed under reduced pressure as occasion demands.

Examples of the light source for curing the resin composition according to the present invention include, but are not limited to, a mercury vapor arc, a carbon arc, and an Xe arc that emits light having a wavelength of 250 nm to 450 nm.

The resin composition according to the present invention can be used as a pigment dispersing type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of an organic light emitting diode or a thin film transistor liquid crystal display (TFT LCD) And can be used for a photosensitive material for overcoat layer formation, a column spacer photosensitive material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printing wiring board and a photosensitive material for a plasma display panel (PDP) Is not specifically set.

According to an embodiment of the present invention, there is provided a color filter including the photosensitive material.

The color filter includes the above-described photosensitive resin composition. The photosensitive resin composition is coated on a substrate to form a coating film, and the color filter can be formed by exposing, developing, and curing the coating film.

The resin composition according to one embodiment of the present invention can provide a color filter capable of realizing a high luminance while lowering the sensitivity in realizing a hole in a pattern.

The substrate may be a plate such as a glass plate, a silicon wafer and a plastic substrate such as polyethersulfone (PES), 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, and a black matrix.

According to another embodiment, the color filter may further include an overcoat layer.

Between the color pixels of the color filter, a lattice-shaped black pattern called a black matrix can be arranged for the purpose of improving the contrast. As the material of the black matrix, chromium can be used. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectivity of chrome, and environmental pollution caused by a chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix according to one embodiment of the present invention can use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or a mixture of carbon black and a color pigment may be used. In this case, since the color pigment having insufficient light shielding property is mixed, the strength of the film or the adhesion to the substrate is lowered There is an advantage not to be.

A display device including the color filter according to the present invention is provided.

The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD) A liquid crystal display (LCD), and a cathode ray tube (CRT).

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

Compound synthesis

In order to prepare a photosensitive resin composition according to one embodiment of the present invention, Compound 1 was produced through the following Reaction Formula 1.

[Reaction Scheme 1]

5 g (8.710 mmol) of A-1, 8.233 g (34.838 mmol) of B-1 and 4.815 g (34.5838 mmol) of K ₂ CO ₃ were placed in 100 ml of NMP and stirred at 95 ° C for 12 hours. The solvent was then removed under reduced pressure, and 200 ml of water was added to the precipitate, followed by stirring for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 DEG C for 12 hours. The dry precipitate was then separated via column chromatography. (El uent-MC: MeOH)

As a result, Compound 1 (6 g, 3.322 mmol) was obtained, and the yield was 72%.

The results are as follows.

Ionization mode =: APCI +: m / z = 949 [M + H] +, Exact Mass: 948

The results of ¹ H-NMR measurement of the compound 1 are as follows.

^{1 H NMR (500MHz, DMSO,} ppm): 8.03 (m, 11H), 7.69 ~ 7.18 (m, 10H), 6.99 ~ 6.95 (t, 1H), 6.80 ~ 6.01 (dd, 1H), 5.93 ~ 5.85 (dd , 4.06-3.79 (m, 4H), 3.72-3.60 (m, 4H), 2.17-1.70 (m, 16H)

[Reaction Scheme 2]

As it is shown in Reaction Scheme 2, C-1 1.43g (2.732mmol ), B-1 2.99g (9.490mmol), K 2 CO 3 1.31 g (9.490 mmol) were added to 20 ml of NMP, and the mixture was stirred at 95 캜 for 12 hours. The solvent was then removed under reduced pressure, and 200 ml of water was added to the precipitate, followed by stirring for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 DEG C for 12 hours. The dry precipitate was then separated via column chromatography. (El uent-MC: MeOH)

As a result, 1.622 g (1.912 mmol) of Compound 2 was obtained, and the yield was 70%.

Ionization mode =: APCI +: m / z = 977 [M + H] +, Exact Mass: 976

[Reaction Scheme 3]

1.608 g (2.732 mmol) of D-1, 2.99 g (9.490 mmol) of B-1 and 1.31 g (9.490 mmol) of K ₂ CO ₃ were added to 20 ml of NMP and stirred at 95 ° C for 12 hours. The solvent was then removed under reduced pressure, and 200 ml of water was added to the precipitate, followed by stirring for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 DEG C for 12 hours. The dry precipitate was then separated via column chromatography. (El uent-MC: MeOH)

As a result, 1.526 g (1.622 mmol) of Compound 3 was obtained, and the yield was 59%.

Ionization mode =: APCI +: m / z = 963 [M + H] +, Exact Mass: 962

[Reaction Scheme 4]

289.5 g (7.388 mmol) of Acid Red, 8.1 g (25.8 mmol) of B-1 and 4.09 g (29.554 mmol) of K ₂ CO ₃ were placed in 100 ml of NMP and stirred at 95 ° C for 12 hours. The solvent was then removed under reduced pressure, Brine 100 was added to the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 DEG C for 12 hours.

As a result, 7.3 g (6.945 mmol) of a coloring material containing Compound 4 as a main product was obtained, and the yield was 94%.

Experimental Example

Examples 1 to 4 and Comparative Examples 1 to 4 were produced in the ratios shown in Table 1 below. The administration unit of each composition is gram (g).

compound Binder resin Photoinitiator additive Photopolymerizable compound solvent Example 1 Compound 1 5.554 9.376 2.018 1.016 (A)
1.000 (B) 12.443 68.593 Example 2 Compound 2 5.890 9.040 2.018 1.016 (A)
1.000 (B) 12.443 68.593 Example 3 Compound 3 5.912 9.018 2.018 1.016 (A)
1.000 (B) 12.443 68.593 Example 4 Compound 4 5.982 8.948 2.018 1.016 (A)
1.000 (B) 12.443 68.593 Comparative Example 1 Compound 1 5.554 10.376 2.018 1.016 12.443 68.593 Comparative Example 2 Compound 2 5.890 10.040 2.018 1.016 12.443 68.593 Comparative Example 3 Compound 3 5.912 10.018 2.018 1.016 12.443 68.593 Comparative Example 4 Compound 4 5.982 9.948 2.018 1.016 12.443 68.593 Binder resin: Copolymer of benzyl methacrylate and methacrylic acid (mole ratio 70:30, acid number 113
KOH mg / g, a weight average molecular weight measured by GPC of 20,000, a molecular weight distribution (PDI) of 2.0,
Solids (SC) 25%, solvent PGMEA)
Photoinitiator: I-369 (BASF)
Photopolymerizable compound: DPHA (Japanese explosive)
Solvent: PGMEA (Propylene Glycol Mnomethyl Ether Acetate)
Additive: (A): DIC F-475
(B): SQ-506

Board Fabrication

The prepared compound was spin-coated on glass (5 x 5 cm) coated with SiN x and pre-baked at 110 ° C for 70 seconds to form a film. The distance between the substrate on which the film was formed and the photo mask was set to 300 mu m, and an exposure dose of 30 mJ / cm < 2 > was applied to the entire surface of the substrate using an exposure machine.

Subsequently, the exposed substrate was developed in a developing solution (KOH, 0.04%) for 55 seconds and post baked at 230 캜 for 20 minutes to prepare a substrate.

Hole size measurement

The inside length of the hole was measured at a ratio of 1000 times using a brown spectrophotometer (OSPSP200 manufactured by Olympus Optical Co., Ltd.).

Adhesion measurement

The substrate produced under the above conditions was measured with a brown spectrophotometer (OSPSP200 manufactured by Olympus Optical Co., Ltd.).

Size of hole (μm) Fine pattern adhesion (μm) Example 1 26.2 9 Example 2 26.1 8 Example 3 26.5 10 Example 4 26.2 9 Comparative Example 1 26.5 14 Comparative Example 2 26.3 16 Comparative Example 3 26.6 15 Comparative Example 4 26.4 14

As shown in Table 1, when the color filter was prepared using the photosensitive resin compositions of Examples 1 to 4 including both the compound represented by Formula 1 and the compound represented by Formula 2, I can see good things

The measurement results of the fine pattern adhesion are shown in FIG.

Claims (18)

1. A photosensitive resin composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (2)
[Chemical Formula 1]

(2)
_{[(RSiO 1. 5) n} ]
In formula (1)
L _A and L _B are the same or different and are each independently a direct bond; Or an alkylene group having 1 to 10 carbon atoms,
R _A to R _F are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen atom; A nitro group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms,
R ₁ to R ₆ are the same or different and each independently hydrogen; heavy hydrogen; A halogen atom; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 6 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms; Sulfonic acid group; Sulfonic acid ester groups; Sulfonic acid base; -SO ₂ NHR ₇ group; Is selected from the group consisting of and -SO ₂ NR ₈ R _9,
R ₇ to R ₉ are the same or different and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms,
X ₁ to X ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms, and at least one of X ₁ to X ₅ is an anionic group,
R _AA and R _BB are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms; A halogen atom; A nitro group; Phenoxy group; A carboxy group; Carboxy acid ester group; Carboxy acid base; An alkoxycarbonyl group; A hydroxy group; Sulfonic acid group; Sulfonic acid ester groups; Sulfonic acid base; -SO ₂ NHR '; And it is selected from the group consisting of -SO ₂ NR "R '",
a and b are the same or different and each independently represents an integer of 0 to 4,
When a and b are two or more, the structures in parentheses are the same or different from each other,
R ', R "and R"" are the same or different and each independently an alkyl group having 1 to 30 carbon atoms,
In formula (2)
n is an even number of 4 or more,
R is represented by - (L ₁ ) _{n 1} -R ₇ ,
A plurality of Rs are the same or different from each other,
L ₁ is a direct bond; -O-; -S-; Or an alkylene group having 1 to 30 carbon atoms,
n1 is an integer of 1 to 5,
When n1 is 2 or more, L1 is the same or different from each other,
R ₇ is hydrogen; heavy hydrogen; -OH; An epoxide group; -SH; -NH ₂ ;

; -N = C = O; -C = C-; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 1 to 30 carbon atoms. The method according to claim 1,
The anionic group is ^{_{-OH, -SO 3 -, -SO 3}} H, -SO 3 - Z +, -CO 2 H, -O 2 - Z +, -CO 2 R a, -SO 3 R b and -SO ₃ &_gt; NR &_lt; _c &_gt; R &_lt; _d &
Z ⁺ represents N (R _e ) ₄ ⁺ , Na ⁺ or K ⁺
R _a to R _e are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms. The photosensitive resin composition according to claim 1, wherein R is represented by any one of the following general formulas (2-a) to (2-e)
[Chemical Formula 2-a]

[Formula 2-b]

[Chemical Formula 2-c]

[Chemical Formula 2-d]

[Chemical Formula 2-e]

. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition comprises a binder resin; Multifunctional monomers; Photoinitiators; And a solvent. [4] The photosensitive resin composition according to claim 4, wherein the content of the compound represented by Formula 1 is 0.1 to 50 parts by weight based on the total weight of the solid content of the photosensitive resin composition,
The content of the compound represented by the general formula (2) is 0.01 to 10 parts by weight,
The content of the binder resin is 1 part by weight to 60 parts by weight,
The content of the photoinitiator is 0.1 part by weight to 20 parts by weight,
Wherein the content of the polyfunctional monomer is 0.1 part by weight to 50 parts by weight. The photosensitive resin composition according to claim 4, wherein the photosensitive resin composition further comprises at least one of a dye and a pigment. The photosensitive resin composition according to claim 6, wherein the dye is at least one selected from the group consisting of an anthraquinone dye, a tetraazaporphyrin dye and a triarylmethane dye. The photosensitive resin composition according to claim 7, wherein the anthraquinone dye is represented by the following formula (3)
(3)

In Formula 3,
R ₁₁ and R ₁₂ are each independently at least one selected from the group consisting of an amino group, an alkylamino group, a dialkylamino group, a phenylamino group and a diphenylamino group. [Claim 7] The photosensitive resin composition according to claim 7, wherein the anthraquinone dye is any one selected from the following compounds:

. The method of claim 7,
Wherein the tetraazaporphyrin-based dye is any one selected from the following compounds:

. The method of claim 7,
Wherein the triarylmethane-based dye is any one selected from the following compounds:

. The photosensitive resin composition according to claim 4, wherein the photosensitive resin composition further comprises a dispersant, and the dispersant comprises a polymer comprising a repeating unit represented by the following formula (11) or a repeating unit represented by the following formula (12)
(11)

[Chemical Formula 12]

In formulas (11) and (12)
R ₃₀₁ and R ₄₀₁ are the same or different from each other, and each independently hydrogen; Or an alkyl group having 1 to 10 carbon atoms,
R ₃₀₂ , R ₃₀₃ , R ₄₀₂ and R ₄₀₃ are the same or different from each other, and each independently hydrogen; An alkyl group having 1 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 1 to 30 carbon atoms,
R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R ₄₀₃ are bonded to each other to form a substituted or unsubstituted ring,
Ar ₃ and Ar ₄ are the same or different and are each independently a direct bond; An alkylene group having 1 to 10 carbon atoms; _{- [CH (R 311) -CH} (R 312) -O] x -CH (R 313) -CH (R 314) - or _{- [(CH 2) y -O} ] z - (CH 2) y - with ≪ / RTI >
R ₃₁₁ to R ₃₁₄ are the same or different and each independently hydrogen; Or an alkyl group having 1 to 10 carbon atoms,
x is an integer of 1 to 18, and when x is 2 or more, the structures in parentheses are the same or different from each other,
y is an integer from 1 to 5,
z is an integer of 1 to 18, and when z is 2 or more, the structures in parentheses are the same or different from each other,
Q is a direct bond; An alkylene group having 1 to 10 carbon atoms; An arylene group having 6 to 30 carbon atoms; -CONH-; -COO-; And an ether group having 1 to 10 carbon atoms. A photosensitive resin composition comprising a compound represented by the following formula (15), a compound represented by the following formula (2), a dye and a dispersant, wherein the dye is a triarylmethane dye:
[Chemical Formula 15]

(2)

In formula (15), the definitions of R ₁ to R ₆ , R _A to R _D , R _AA , R _BB and X ₁ to X _{5 and} the definitions of formula (2) are the same as in claim 1. 14. The method of claim 13,
Wherein the triarylmethane-based dye is any one selected from the following compounds:

. [14] The photosensitive resin composition according to claim 13, wherein the dispersant comprises a polymer comprising a repeating unit represented by the following formula (11) or a repeating unit represented by the following formula (12)
(11)

[Chemical Formula 12]

In formulas (11) and (12)
The R ₃₀₁ , R ₃₀₂ , R ₃₀₃ R ₄₀₁ , Ar ₃ , Ar ₄ , R ₃₁₁ to R ₃₁₄ , x, y, z and The definition of Q is the same as in claim 12. A photosensitive material produced by using the resin composition according to any one of claims 1 to 15. A color filter comprising the photosensitive material according to claim 16. A display device comprising a color filter according to claim 17.

Images